EPA-600/2-77-023g
February 1977
Environmental Protection Technology Series
INDUSTRIAL PROCESS PROFILES FOR
ENVIRONMENTAL USE: Chapter 7.
Organic Dyes and Pigments
Industry
Industrial Environmental Research Laboratory
Office of Research and Development
U.S. Environmental Protection Agency
Cincinnati, Ohio 45268
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RESEARCH REPORTING SERIES
Research reports of the Office of Research and Development, U.S. Environmental
Protection Agency, have been grouped into five series. These five broad
categories were established to facilitate further development and application of
environmental technology. Elimination of traditional grouping was consciously
planned to foster technology transfer and a maximum interface in related fields.
The five series are:
1. Environmental Health Effects Research
2. Environmental Protection Technology
3. Ecological Research
4. Environmental Monitoring
5. Socioeconomic Environmental Studies
This report has been assigned to the ENVIRONMENTAL PROTECTION
TECHNOLOGY series. This series describes research performed to develop and
demonstrate instrumentation, equipment, and methodology to repair or prevent
environmental degradation from point and non-point sources of pollution. This
work provides the new or improved technology required for the control and
treatment of pollution sources to meet environmental quality standards.
This document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia 22161.
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EPA-600/2-77-023g
February 1977
INDUSTRIAL PROCESS PROFILES
FOR ENVIRONMENTAL USE
CHAPTER 7
ORGANIC DYES AND PIGMENTS INDUSTRY
by
Thomas R. Steadman and Eleanor W. Helper
BatteH e-Columbus
Columbus, Ohio 43201
T. Parsons, G.E. Wilkins, and N.P. Phillips
Radian Corporation
Austin, Texas 78766
Contract No. 68-02-1319
Project Officer
Alfred B. Craig
Metals and Inorganic Chemicals Branch
Industrial Environmental Research Laboratory
Cincinnati, Ohio 45268
INDUSTRIAL ENVIRONMENTAL RESEARCH LABORATORY
OFFICE OF RESEARCH AND DEVELOPMENT
U.S. ENVIRONMENTAL PROTECTION AGENCY
CINCINNATI, OHIO 45268
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DISCLAIMER
This report has been reviewed by the Industrial Environmental Research
Laboratory - Cincinnati, U.S. Environmental Protection Agency, and approved
for publication. Approval does not signify that the contents necessarily
reflect the views and policies of the U.S. Environmental Protection Agency,
nor does mention of trade names or commercial products constitute endorsement
or recommendation for use.
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TABLE OF CONTENTS
CHAPTER 7
Page
INDUSTRY DESCRIPTION 1
Raw Material s 3
Products 4
Companies 10
Env i ronmenta 1 Impact 10
Bibl iography 12
INDUSTRY ANALYSIS 13
Process No. 1. Nitroso Dyes (C.I. 10.005, 10006, 10020) 65
Process No. 2. Nitro Dyes (C.I. 10316) 66
Process No. 3. Nitro Dyes (C.I. 10338, 10345) 67
Process No. 4. Azo Dyes and Pigments 69
Process No. 5. Stilbene Dyes 73
Process No. 6. Selected DI- and Triarylmethane
Dyes from Various Intermediates 76
Process No. 7. Triarylmethane Dyes (C.I. 42500, 42536,
42760, 42780) 79
Process No. 8. Triarylmethane Dyes (C.I. 42555, 42561,
42595, 42600, 44025, 44090) 82
Process No. 9. Triarylmethane Dyes (C.I. 43820, 43830)
and a Methine Dye (C.I. 48000) 85
Process No. 10. Triarylmethane Dyes and Pigments
(C.I. 44040, 44054) and an Acridine Dye (C.I. 46005) 87
Process No. 11. Xanthene Dyes (C.I. 45100, 45350) 90
Process No. 12. Halogenation of Dyes 93
Process No. 13. Quinacridone Pigment (C.I. 46500) 95
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TABLE OF CONTENTS (Continued)
CHAPTER 7
Page
Process No. 14. Quincline Dyes 96
Process No. 15. Sulfonation of Dyes 98
Process No. 16. Polymethine Dyes 100
Process No. 17. Thiazole Dyes and Pigments 102
Process No. 18. Formation of Pigments from
Selected Dyes 104
Process No. 19. Azine Dyes (C.I. 50204, 50240, 50400, 50415) 106
Process No. 20. Oxazine Dyes and Pigments 109
Process No. 21. A Thiazine Dye (C.I. 52015) 112
Process No. 22. Sulfur Dyes (C.I. 53000, 53830, 69705) 114
Process No. 23. Alizarin (C.I. 58000). 117
Process No. 24. Pyranine (C.I. 59040) 118
Process No. 25. Pyrathrone (C.I. 59700) 119
Process No. 26. Benzanthrone Dyes 121
Process No. 27. Isoviolanthrone Dyes (C.I. 60000, 60015) 124
Process No. 28. Anthraquinone Dyes and Pigments (Aminolysis) .... 126
Process No. 29. Anthraquinone Dyes (Methylation)(C.I. 60755,
61105) 128
Process No. 30. Anthraquinone Dyes (C.I. 60756, 62020,
62025, 62070) 12g
Process No. 31. Anthraquinone Dyes (Amide Formation)
(C.I. 61725, 63365, 65049, 68420) 131
Process No. 32. Anthraquinone Dyes (Nitration of
Diaminoanthraquinones) (C.I. 62030, 64500) 133
Process No. 33. Anthraquinone Dyes (C.I. 63010) 135
IV
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TABLE OF CONTENTS (Continued)
CHAPTER 7
Page
Process No. 34. Anthraquinone Dyes (Anthracarbazoles)
(C.I. 65230, 69500, 69525) 137
Process No. 35. Anthraquinone Dyes (Anthrapyrazoles)
(C.I. 70315, 70320) 138
Process No. 36. Anthraquinone Dyes (an Oxazole and a
a Thiazole Type)(C.I. 67000, 67300) 140
Process No. 37. Anthraquinone Dyes and Pigments
(Anthracarbazoles) (C.I. 69015, 69025) 141
Process No. 38. Anthraquinone Dyes and Pigments--
Indanthrone and Flavanthrone (C.I. 69800, 70600) 143
Process No. 39. Anthraquinone Dyes (Anthracarbazoles)
(C.I. 70800, 70805, 71050) 144
Process No. 40. Cyclic Imide Dyes and Pigments
(C.I. 71100, 71110) 146
Process No. 41. Perylene Vat Dyes and Pigments
(C.I. 71129, 71145, and 3,4,9,10-Perylenetetra-
carboxyl ic Anhydride) 147
Process No. 42. Indigoid Dye (C.I. 73000) 149
Process No. 43. Indigoid Dye (C.I. 73300) 150
Process No. 44. Indigoid Dye and Pigment
(C.I. 73395, 73410) 151
Process No. 45. Indigoid Dyes and Pigments 153
Process No. 46. Indigoid Dye (C.I. 73670) 155
Process No. 47. Phthalocyanine Dyes and Pigments
(C.I. 74160, 74240, 74260, 74460) 157
Process No. 48. Finishing Steps for Pigment or
Dry Production 160
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TABLE OF CONTENTS_(ConcTudPfr)_
CHAPTER 7
Page
Appendix A - Raw Materials Used to Manufacture Organic
Dyes, Pigments and Their Intermediates 163
Appendix B - Dyes and Pigments Manufactured in the United
States in 1973, Listed in Numerical Order by Color
Index Numbers ' 169
Appendix C - Dyes and Pigments Manufactured in 1973 Listed
in Alphabetical Order by Manufacturer 181
Appendix D - Location of Plants Manufacturing Dyes,
Pigments or Intermediates, Listed Alphabetically by
Name of the Manufacturer 249
Appendix E - Locations of Dye and Pigment Manufacturing
PI ants Li sted by Regi on 337
VI
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LIST OF FIGURES
CHAPTER 7
Figure Page
1-1 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Acenaphthene 15
1-2 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Aniline 116
1-3 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Anthranilic Acid. . . 19
1-4 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Benzaldehyde 19
1-5 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Benzenesulfonic
Acid 19
1-6 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Carbazole 20
1-7 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Chlorobenzene. ... 20
1-8 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: £-Chlorobenzenesul-
fonic Acid. .......... 25
1-9 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: £-Chloronitrobenzene. 27
VI1
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LIST OF FIGURES (Continued)
CHAPTER 7
Figure Page
1-10 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: o-Chlorobenzoic Acid. 30
1-11 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Chlorobenzoic Acid. 30
1-12 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: m-Chlorobenzoyl
Chloride ........................... 30
1-13 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: cnCresol ....... 30
1-14 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: m-Cresol ....... 31
1-15 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Cresol ....... 31
1-16 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: 2,4-Diaminotoluene. . 31
1-17 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Dichlorobenzene. . 31
1-18 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: j^-Dichlorobenzene. . 32
1-19 Snythesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Diphenylarnine. ... 33
vm
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LIST OF FIGURES (Continued)
CHAPTER 7
Fi gure Page
1-20 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Hydroquinone 33
1-21 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: £-Hydroxybenzoic
Acid 34
1-22 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Isophthalic Acid. . . 34
1-23 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Naphthalene 34
1-24 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: 1-Naphthol 42
1-25 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Nitrobenzene 43
1-26 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: £-Nitrophenol. ... 46
1-27 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Nitrophenol. ... 47
1-28 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: nv-Nitrotoluene. ... 47
1-29 Synthesis of Various Intermediates for Dyes and Pigment Produc-
tion from Purchased Starting Material: p_-Nitrotoluene. ... 48
IX
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LIST OF FIGURES (Continued)
CHAPTER 7
Figure Page
1-30 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Nitrotoluene. ... 50
1-31 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Phenol 51
1-32 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Materials: p_~ and p_-Phenol-
sulfonic Acid 51
1-33 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Materials: p_- and p_-Phenol-
sulfonic Acid 51
1-34 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Phthalic Anhydride. 52
1-35 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Resorcinol 60
1-36 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Salicylic Acid. ... 60
1-37 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Toluene 60
1-38 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p^-Toluenesulfonic
Acid 61
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LIST OF FIGURES (Continued)
CHAPTER 7
Figure Page
1-39 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: p_-Toluenesulfonyl
Chloride 62
1-40 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: 1,2,4 Trichloro-
benzene 63
1-41 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: Trimellitic Anhydride. 63
1-42 Synthesis of Various Intermediates for Dye and Pigment Produc-
tion from Purchased Starting Material: m-Xylene 63
2-1 Flow Chart for the Production of Selected Nitroso and Nitro
Dyes and Pigments from Various Intermediates 64
2-2 Flow Chart for the Production of Selected Azo Dyes and Pigments
from Various Intermediates 68
2-3 Flow Chart for the Production of Selected Stilbene Dyes and
Pigments from Various Intermediates 72
2-4 Flow Chart for the Production of Selected Diarylmethane and
Triarylmethane Dyes and Derived Pigments from Various
Intermediates 75
2-5 Flow Chart for the Production of Selected Triarylmethane Dyes
and Pigments from Various Intermediates 78
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LIST OF FIGURES (Continued)
CHAPTER 7
Figure Page
2-6 Flow Chart for the Production of Selected Triaryl methane Dyes
and Pigments from Various Intermediates ........... 81
2-7 Flow Chart for the Production of Selected Triaryl methane and
Methane Dyes from Various Intermediates ........... 84
2-8 Flow Chart for the Production of Selected Triaryl methane and
Acridine Dyes and Pigments from Various Intermediates. ... 86
2-9 Flow Chart for the Production of Selected Xanthene Dyes and
Pigments from Various Intermediates ............. 89
2-10 Flow Chart for the Production of Dyes and Pigments by Halo-
genation of Selected Dyes ..... . ............ 92
2-11 Flow Chart for the Production of a Quinacridone Pigment and
Selected Quinoline Dyes from Various Intermediates ...... 94
2-12 Flow Chart for the Production of Dyes and Pigments by Sulfona-
tion of Selected Dyes and Pigments .............. 97
2-13 Flow Chart for the Production of Selected Polymethine Dyes
from Various Intermediates .................. 99
2-14 Flow Chart for the Production of Selected Thiazole Dyes and
Pigments from Various Intermediates ............. 101
2-15 Flow Chart for the Production of Pigments from Selected Dyes. . 103
2-16 Flow Chart for the Production of Selected Azine Dyes from
Various Intermediates .................... 107
x
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LIST OF FIGURES (Continued)
CHAPTER 7
Figure Page
2-17 Flow Chart for the Production of Selected Oxazine Dyes and
Pigments from Various Intermediates ............. 108
' 2-18 Flow Chart for the Production of a Thiazine Dye from Various
Intermediates ........................ HI
2-19 Flow Chart for the Production of Selected Sulfur Dyes from
Various Intermediates .................... 113
2-20 Flow Chart for the Production of Miscellaneous Vat Dyes and
Pigments Based on Anthraquinone and Pyrene ....... ... 116
2-21 Flow Chart for the Production of Benzanthrone Dyes from
Various Intermediates .................... 120
2-22 Flow Chart for the Production of Isoviolanthrone Dyes from
Various Intermediates ................... 123
2-23 Flow Chart for the Production of Anthraquinone Dyes and
Pigments by Aminolysis of Various Intermediates ....... 125
2-24 Flow Chart for the Production of Selected Anthraquinone Dyes
and Pigments from Various Intermediates ........... 127
2-25 Flow Chart for the Production of Selected Anthraquinone Dyes
and Pigments from Various Intermediates ........... 130
2-26 Flow Chart for the Production of an Anthraquinone Dye from
Various Intermediates .................... 134
xm
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LIST OF FIGURES (Concluded)
CHAPTER 7
Figure Page
2-27 Flow Chart for the Production of Selected Anthraquinone Dyes
from Various Intermediates - Anthraquinonecarbazoles and
Anthrapyrazoles 136
2-28 Flow Chart for the Production of Selected Anthraquinone Dyes
and Pigments from Various Intermediates 139
2-29 Flow Chart for the Production of Selected Anthraquinone Dyes
and Pigments from Various Intermediates 142
2-30 Flow Chart for the Production of Selected Cyclic Imide and
Perylene Vat Dyes and Pigments from Various Intermediates. . 145
2-31 Flow Chart for the Production of Selected Indigoid Dyes and
Pigments from Various Intermediates. . . 148
2-32 Flow Chart for the Production of Selected Indigoid Dyes and
Pigments from Various Intermediates 152
2-33 Flow Chart for the Production of Selected Phthalocyanine
Dyes and Pigments from Various Intermediates 156
2-34 Flow Chart for Finishing Steps for Pigment or Dye Production. 159
xiv
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LIST OF TABLES
Table Page
1 Classification of Dyes and Pigments in Colour Index
Categories .......................... 5
2 Glossary of Terms Used in Diagrams for Synthesis of
Intermediates ........................ T4
A-l Raw Materials Used to Manufacture Organic Dyes, Pigments
and Their Intermediates ................... 164
B-l Dyes and Pigments By Color Index Number in Numerical Order. . . 170
C-l Dyes and Pigments Manufactured in 1973 ............. 182
D-l Location of Plants Manufacturing Dyes, Pigments or Inter-
D-589h mediate, Listed Alphabetically by Name of the Manufacturer. . 249
E-l Locations of Dye and Pigment Manufacturing Plants ....... 338
xv
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ACKNOWLEDGEMENTS
This document was prepared for EPA by Batelle Columbus Laboratories under
Contract No. 68-02-1323, Task No. 26. The contributions of Dr. Thomas
R. Steadman and Mrs. Eleanor W. Helper in preparation of this catalog
entry are gratefully acknowledged.
Helpful review comments from C. Fred Gurnham were received and incor-
porated into this chapter.
xvi
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ORGANIC DYES AND PIGMENTS
INDUSTRY DESCRIPTION
The organic dyes and pigments industry is engaged in the conversion
of purchased organic chemicals, usually cyclic benzenoids, into more complex
intermediates and ultimately into dyes and pigments. The distinction between
these intermediate compounds and dyes or pigments is arbitrary since many of
the intermediates may be dyes themselves.
In the past the dyes and pigments industry started with benzene,
naphthalene and other raw materials derived directly from coal tar. In
those times, for example, aniline was produced and used almost entirely
within the industry. Aniline can no longer be regarded in this light. Only
8 percent of the total production of aniline is used to make dyes and pig-
ments. ' Today aniline and even some of the more complex intermediates are
purchased by dye and pigment producers from sources outside the industry.
A total of forty-eight processes have been judged necessary to
summarize the operations carried out in manufacturing dyes and pigments.
A general description of the operations in this industry includes the fol-
(2)
lowing five steps. '
Step 1. Introduction of substituents on aromatic ring
(benzene, toluene, naphthalene, napththol, and
anthraquinone). These are usually one-step
processes such as sulfonation, nitration, halo-
genation, Friedel-Crafts alkylation or oxidation.
Step 2. Replacement of substituents with more reactive
groups which cannot be introduced directly,
such as OH, NH2, CH, OR, SR, and MRR'.
Step 3. Further development of functional groups in
reactions specific for particular dyes.
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Step 4. Combination of intermediates to form products
with skeletal dye structure. This step includes
such processes as condensation,, coupling, and
dimerization.
Step 5. Dye and pigment formation.
Detailed discussions of these operations are given in the ac-
companying process descriptions, flow sheets, and diagrams for synthesis
of intermediates. Steps 1 through 3 and some examples of Step 4 are
described in the synthesis diagrams or Chemical Trees. Steps 4 and 5 are
covered in the Process Descriptions and flow sheets.
No single producer of dyes and pigments employs all forth-eight
of the processes described in the Process Descriptions, because individual
organizations manufacture only limited numbers and kinds of colors. The
organic dyes and pigments industry sells more than 1000 different products.
Perhaps as many as another 1000 products are made en route to the final
products. The industry is comprised of fifty-eight individual companies
(3 4}
with facilities at eighty-seven locations. ' '
In 1973, total United States production of dyes and pigments was
nearly 354 million pounds. Sales were almost 328 million pounds with a
total value of about $701 million, corresponding to an average unit value
of $2.14 per pound. This high unit value for dyes and pigments provides
a key to understanding the industry's basic business approach. Obviously,
large inventories are too costly, and, in consequence, the industry is
forced to make its products in relatively small batch operations. Such
operations are, of course, labor intensive. No further information is
available regarding variations in the size of manufacturing facilities and
the approximate number of employees.
The geographic locations of plants are various, but the great
(3 4}
majority of the operations are located on the Eastern seaboard. ' ' Many
small plants are located in New England because of the historic importance
there of the textile industry which uses two-thirds of the dyes produced.
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The migration of the textile industry to the southern states has led to the
location of some dye manufacturing operations there. The greatest number
of plants, some of them large, are located in New Jersey, probably because
these locations offered suitable means for disposing of the large volumes
of waste streams involved. The large companies with relatively unusual
locations are the Allied Chemical Corporation (Buffalo, New York) and the
American Color and Chemical Corporation (Lock Haven, Pennsylvania, among
other locations).
Industry growth in dye production over the last ten years averaged
slightly less than 4 percent annually, and the long-term growth rate is
expected to continue in the range of 3 to 4 percent per year.
Pigments are far fewer in number than the dyes (only about one-
tenth as many) and have a higher average unit value. Industry has recently
been replacing some of the more expensive dyes with pigments in some textile
applications. For the next five years, the yearly growth rate is expected
to be around 5 percent.
No information is available about the dye and pigment industry
practices in respect to steam and power generation on-site.
Raw Materials
A list of raw materials purchased by the Organic Dyes and Pigments
Industry is shown in Appendix A. They are classified as organic and inor-
ganic. Many of the raw materials listed were formerly produced exclusively
by the Organic Dyes and Pigments Industry for use largely within the industry.
An excellent example is the case of aniline. In the past nearly all the
aniline was made by the organic dyes and pigments industry for use within
the industry. Today only 8 percent of the output of aniline in the United
States is used to make dyes and pigments.^ '
It is important to note that many of the intermediates used in
making dyes and pigments are toxic in nature. Even more important is the
point that some dye and pigment intermediates are carcinogenic. The two
most notorious such intermediates are benzidine and 2-naphthylamine. Today,
benzidine, because of its carcinogenic properties, is manufactured in the
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United States only by the Allied Chemical Corporation, and 2-naphthylamine
is not made by any company in the United States. For most applications
where 2-naphthylamine was formerly required, 2-amino-l-naphthalenesulfonic
acid serves as a safe and adequate replacement material.
Products
The two main classes of products from this industry are dyes and
pigments. Two technical terms for pigments are toners and lakes. "Toners"
are full strength organic or metallo-organic colors not containing any
inorganic pigment or carrier. "Lakes" are combinations of a dye with an
inorganic base or carrier, usually alumina hydrate.
For purposes relating to applications of colors, these products
are classified according to the chemical and physical properties which
relate to the use of the products. It is this kind of classification which
is used by the United States Tariff Commission annual publication, "Synthetic
Organic Chemicals, United States Production and Sales." Such a classification
is not helpful for the purpose of this report. Instead, the dyes and pigments
are classified according to the nature of their chemical structure, because
this reflects the nature of the processes involved in making the colors.
The twenty-four classifications adopted are listed in Table 1. This classi-
fication system is essentially the same as that used by the standard reference
work, The Colour Index.^ ' Assignment of a unique five-digit number known
as the Colour Index (C.I.) Constitution Number is made based strictly on the
chromophore structure. The range of C.I. Numbers for each key colorant
group is given in Table 1. Arrangement within each class is established
according to the following principles:
1. Simpler colorants precede more complex compounds.
2. Aliphatic compounds are listed before aromatics,
which appear in the order - benzene, naphthalene,
anthracene, and.heterocyclic.
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Table 1. CLASSIFICATION OF DYES AND PIGMENTS IN COLOUR INDEX CATEGORIES
Class C. I. Number Chrotnophore
Nitroso 10000-10299 -N=0
(Quinone Oximes)
Auxochrome Applications
Wallpaper, rubber color-
ation, textile printing,
interior aqueous paints
Toxicity Information
Pigment Green B(C.I.
10006) - acute oral
LD50 > 10 g/kgW
Nitro
10300-10999
-NO,
Hydroxyl and amino
groups
Sulfonated nitro dyes
and pigments - wool,
silk, paper, printing
ink, transparent lac-
quer, external drug and
cosmetic colorant.
Unsulfonated nitro-
diarylamines - yellow
and orange disperse
dyes for synthetic
fibers.
Unsulfonated nitro
dyes - pigments, fungi-
cides, insecticides,
explosives.
Acid yellow 1 (C.I.
10316) - consult
latest Government
regulations before
using in food, drugs,
or cosmetics.(")
Azo
Monoazo
Disazo
Trisazo
Polyazo
Azoic
11000-39999 -N=N-
11000-19999
20000-20999
30000-34999
350QO-36999
37000-39999
Usually hydroxyl Very wide range of ap-
or amino plication. Natural
and synthetic fiber
dyes, pigments, sol-
vent Jyes and various
non-textile applica-
tions .
Some azo dyes have
produced cancer in
rats and are con- ,-,*
sidered carcinogenic.
(Mixtures of inter-
mediates - Not
finished dyes)
Stilbene
40000-40799
-N=N-
azo
and/or
-N=N-
i
0
azoxy
Direct dyes, fluores-
cent dyes, secondary
uses as leather, lake-
forming or solvent
dyes.
Some azo dyes have
produced cancer in
rats and are con- , ..
sidered carcinogenic:-''
Carotenoid
40800-40999
Polyene chain of at
least 18 carbon atoms
with conjugated double
bonds
Natural carotenoids
(C.I. 75110-75135)
Synthetic carotenoids
important food dyes
Food dyes - assumed
non-toxic.
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Table 1. CLASSIFICATION OF DYES AND PIGMENTS IN COLOUR INDEX CATEGORIES (Continued)
Class
Dipheny line thane
(Ketone Imines)
(Aur amines)
Triarylme thane
C . I . Number
41000-41999
42000-44999
Chromophore
XC=NH
^
Quinoid grouping ap-
Auxochrome Applications
Dyeing wool, silk,
leather, acrylic fibers,
cotton, paper, and jute
Two or three auxo- Basic, acid, direct,
Toxicity Information
Auramine (C, -,H0,,N0C1)
1 / f.2. J
recognized as a car-
Peacock Blue Lake
1
pearing as:
C=Ar=NH or
chromes usually in
para-position to
the methane C atom.
mordant, cosmetic, and
solvent dyes.
Pigments of phospho-
molybdotungstic acid
lake type.
(from C.I. 42090) -
low toxicityW mala-
chite Green (C.I.
42000) - oral LD (rab-
bits) = 75 mg/kg(6')
C.I. 42040: LDiQQ iv
in mice 3 mg/kgt°J
C.I. 42780: probably
low human toxicity.C"'
Xan thene
45000-45999
R R
(R = H, alkyl, or aryl)
The usual auxo-
chromes in
position to
methane C atom.
In general, dyeing
natural fibers.
Hydroxy derivatives
mordant dyes
C.I. 45010- Carcino-
genic (°)
C.I. 45350: LD orally.,.
in rabbits 2.5 g/kg(6)
C.I. 45380: LD orally
in guinea pigs
5.0 g/kgW
Acridine
46000-46999
Amino or alkyl-
amino groups in
aryl groups in
pajra-position to
the C ai.oiii of
methane residue.
Broad applications in
trade sales and indus-
trial paints as tints,
metal-lies, and blends
with other pigments.
Especially suitable for
leather and plastic;
also to some extent in
textiles, silk, cellu-
lose, and industrial
antiseptic.
C.I. 46000: LD s.c.
in mice 250 mg/kg.
Quinoline
47000-47999
2-(2-quinolyl)-l,3-indandione
Drug and cosmetic color,
food dye (Europe),
paper.
Sulfonated compounds
valuable as acid wool
dyes .
Methine and poly-
methine
48000-48999
Conjugate chain of car-
bon atoms terminated
by an ammonium group
and, in addition, a
nitrogen, sulfur or
oxygen atom, or an
equivalent unsaturated
group
Important for use in
photography as sensi-
tizers.
-------
Table 1. CLASSIFICATION OF DYES AND PIGMENTS IN COLOUR INDEX CATEGORIES (Continued)
Class
Thiazole
I. C. Number
49000-49399
Chromophore
Auxo chrome
Applications
Toxicity Information1
May be used as direct
cotton dyes; the ori-
ginal Ingrain colors .
Used in printing to
obtain colored dis-
charges .
Indamine
Indophenol
49400-49699
Quinonoid Nucleus:
Intermediates in the
preparation of sulfur
dyes and in color
photography.
49700-49999
Azine
50000-50999
Pyrazine
o
Groups in meta
position to the
nitrogen .
Wool, silk, and mor-
danted cotton dyes.
Nonsulfonated dyes
panting anTas colors
for fats, oils, and
lacquers .
C.I. 50040: Ln5Q iv
for rabbits
C. I^lo*8 mild
sensitized)
Oxazine
rhia^ine
51000-51999
Oxazine:
/N\
Amino groups and
hydroxyl groups in
meta position to
the oxygen.
Wool and mordanted cot-
ton dyes. Also used
for leather and solvent
dyes .
^2000-52999 Thiazine Ring:
Croups introduced
meta to the sulfur
atom.
Medicinal usage, vat
dyes, and microscopic
stains .
C.I. 5^015: Human
toxicity - prac-,,.
tically nontoxic' '
Sulfur
53000-54999 Indeterminate
Dyes for cellulosic
fibers .
Lactone
55000-55999
.
—
Hydroxyl group
(Lactone Ring)
Dyes for chrome -mor
danted wools .
Aminoketone
56000-56999
Amino group or sub-
stituted amino
group .
Vat dyes for wool
Hydroxyketone
57000-57999
C=0
Hydroxyl group
Mordant dyes
-------
Table 1. CLASSIFICATION OF DYES AND PIGMENTS IN COLOUR INDEX CATEGORIES (Concluded)
Class
Anthraquinone
I . C . Number Chromophore Auso chrome
58000-72999 ^Q_0 NH, , OH, NHR, NR, ,
— NHCOR, OR
Applications
Wide variety of uses.
Vat, acid, mordant, dis-
perse, solvent dyes and
pigments . Also used in
cosmetics and in micro-
biological stains.
Toxicity Information
Some may cause local
sensitivity as an
allergen. (°- '*
Indigo id
73000-73999
-C-C=C-C-
NH or S
Dyeing and printing of
cellulosic and animal
fibers .
Indigo carmine
(C.I. 73015) consult
latest government
regulations before
using in fwds, drugs,
cosmetics.'
oo
Fhthalocyanine
74000-74999
C-N
C=N
Pigments and vat dyes .
N-C
*.
N
\ X
N-C
Other categories not considered in this catalogue entry:
Natural Organic 75000-75999
Oxidation Bases
Inorganic Pigments
76000-76999
77000-77999
Data are those which were readily available in standard
reference books. The information is not comprehensive.
When toxicity information for a specific dye is given,
it should not be construed to apply to other dyes of
the same category.
-------
3. The dyes are arranged according to primary functional
groups - ami no, hydroxy, or both ami no and hydroxy.
Within each subgroup further categorizations are made. In addition to
providing the manufacturers with a practical and necessary coding system,
utilization of the Colour Index system allows ready characterization of
a color product based on its manufacturing code alone.
The complete list of products (Appendix B) considered is derived
from the United States Tariff Commission report, "Synthetic Organic Chemicals,
United States Production and Sales, 1972", with additional information from
the preliminary data published from the same source for 1973. This list
includes only the dyes and pigments to which a Colour Index number has been
assigned and for which a chemical structure is known. Many commercially
sold colors are proprietary in nature and their structures are not public
information.
Appendix C lists alphabetically the manufacturers of dyes, pigments,
and intermediates, and shows the dyes and pigments which they reported as
products from their plants to the United States Tariff Commission in 1973.
The azo, anthraquinone, and stilbene groups of compounds from the
classifications of products in Table 1 account for two-thirds of the total
(2)
manufacturing production of dyes. ' Approximately two-thirds of the dye
production is consumed by the textile industry, one-sixth by the paper in-
dustry and the remainder is used for the production of pigments, dyeing of
leather and coloring of plastics. About half of the organic pigments pro-
duction is consumed by the printing industry; other major markets include
(3\
surface coatings, plastics, textiles, and paper. '
Because of the many different uses, methods of application and
service requirement, this industry sells thousands of products available
as pastes, powders, lumps, concentrated solutions, and dispersions. About
two-thirds of the pigment production is sold in the form of a concentrated
dispersion or paste.
-------
Companies
As mentioned above fifty-eight (58) companies are engaged in the
manufacture of dyes, pigments, and/or intermediate materials with plants at
eighty-seven (87) locations. These companies and their locations are listed
alphabetically in Appendix D. The list is derived from the United States
Tariff Commission Report, "Synthetic Organic Chemicals, United States Pro-
(-3)
duction and Sales, 1972"K ', and the corresponding preliminary data for 1973.
Geographic locations were taken from the 1974 Directory of Chemical Producers,
(4)
United Statesv ' with additional reference to more recent information
directly from industry sources. No information is available regarding the
manufacturing capacities of these companies. Some of these companies make
dyes, pigments, and/or intermediates at more than one location. The various
plants are listed according to geographic location in Appendix E. There is
no doubt that New Jersey has the highest concentration of dye and pigment
manufacturing operations, with a total of 30 of the 87 plants (34.5 percent)
and six of the top seven manufacturers being represented in the area: Allied
Chemical Corporation, American Cyanamid Company, E.I. duPont de Nemours &
Company, GAP Corporation, Toms River Chemical Corporation and American Color
and Chemical Corporation. Of these six leading manufacturers with New Jersey
locations, four have plants located elsewhere as well. The remaining
seventh large manufacturer, ICI United States, Inc., has its only colors
manufacturing plant in Massachusetts. These top seven manufacturers are
considered to account for close to 90 percent of organic dye and pigment
production.
Environmental Impact
Organic dyes and pigments manufacture is characterized by emissions
of solid, liquid, and gaseous wastes. Some of the gaseous emissions which
have been indicated are nitrogen oxides, sulfur oxides, hydrogen sulfide,
hydrogen chloride, and organic vapors including amines, phosgene, and for-
maldehyde. Solid wastes are often in the form of distillation residues,
particulates recovered in baghouses, filter paper, and activated carbon.
10
-------
Although all three types of waste streams are generated in dye
manufacturing, the most serious emission problems are those presented by
large volumes of toxic liquid wastes. Liquid wastes originate from chemical
reaction by-products; physical separations such as crystallization, filtra-
tion, and washing; and from equipment cleaning procedures. These liquid
waste streams consist of brine solutions and dilute streams of acids and
bases contaminated with toxic and/or explosive organic compounds which are
often highly colored dyes or intermediates. The waste solutions also contain
metals or metal salts used as catalysts for various reactions. The specific
compositions of waste streams vary widely with the dye or pigment manufactured
and cannot be adequately represented by a typical composition. Although an
accurate assessment and characterization of the wastes produced in this in-
(2)
dustry is needed, none was available from the open literature. '
Some companies have found it unprofitable to install needed waste
disposal and control facilities and have elected to terminate operation of
the offending process. Thus, GAP Corporation has recently stopped their
manufacture of copper phthalocyanine (C.I. 74160) in part because of the
formidable waste disposal problems associated with the manufacture of this
IQ\
high quality blue pigment.v '
On the other hand, the Allied Chemical Corporation, after a survey
of the waste effluent problems at its dye manufacturing facility in Buffalo,
New York, elected about five years ago to spend $40 million over a period of
several years to cope with the effluents in an ecologically acceptable way.
11
-------
Bibliography
(1) Chemical Marketing Reporter, 204 (27), 9 (1973).
(2) A Study of Hazardous Waste Materials, Hazardous Effects and
Disposal Methods. Booz-Allen Applied Research, Inc., Bethesda,
Maryland, July 1973.
(3) Synthetic Organic Chemicals, United States Production and Sales,
1972, United States Tariff Commission, TC Publication 681, Washington,
D. C., 1974, pp 55-100.
(4) Directory of Chemical Producers, United States of America, Chemical
Information Services, Stanford Research Institute, Menlo Park,
California, 1974.
(5) Colour Index, Third Edition, Volume 4, The Society of Dyers and
Colourists, Yorkshire, England, 1971.
(6) The Merck Index, Eighth Edition, Merck & Co., Inc., Rahway, New
Jersey, 1968.
(7) Sax, N. Irving, Dangerous Properties of Industrial Materials, Fourth
Edition, Van Nostrand Reinhold Company, New York, 1975.
(8) Industry source, private communication to Battelle.
12
-------
INDUSTRY ANALYSIS
To obtain information regarding the processes used by the organic
dyes and pigments industry in a brief time span has been very difficult.
Most of the information obtained is based on that found in the Colour Index.
This basic compendium has not been cited in any of the process descriptions
in the interest of brevity, and the reference to it here serves instead.
Further, more extensive searching would doubtlessly bring to light a great
deal more information. In particular, recourse to reports gathered by
American and British intelligence teams from German companies at the end of
hostilities in World War II in 1946 would no doubt be of special value. The
amount of information available from these sources and from original pub-
lications would be manifestly much greater than what is presented here.
Because secondary sources have been used, both the process descriptions and
flow sheets are necessarily incomplete. No EPA Source Classification Code
exists for any of the processes described since this industry has not yet
been considered in the NEDS system.
Diagrams describing synthesis of intermediate chemicals, process
flowsheets, and process descriptions follow. Figures 1-1 through 1-42 pro-
vide a series of diagrams illustrating the progressive steps required to
transform purchased starting materials into a great variety of intermediate
chemical compounds used in making dyes and pigments. Table 2 contains a
glossary of terms used in preparing the diagrams of the synthesis of inter-
mediate compounds.
Forty-eight different processes were identified in summarizing
the operations carried out by the industry. These processes are presented
in process flow charts (Figures 2-1 through 2-48) and in the corresponding
process descriptions. The processes describe mainly operations which con-
vert intermediates into dyes or pigments.
An attempt was made to link the intermediate compounds described
in the synthesis diagrams to the 48 defined processes. The number of the
dye-making process in which a particular intermediate is used is printed
above that chemical in the synthesis diagrams. There are also sequences in
the synthesis diagrams which are defined in the process descriptions and
process flow charts. To indicate these common processing sequences, the
process number is printed above the chemical synthesis arrow.
13
-------
Table 2. GLOSSARY OF TERMS USED IN DIAGRAMS FOR SYNTHESIS OF INTERMEDIATES
Aa Anthranilic acid
AcCl Acetyl chloride
Ac20 Acetic anhydride
ANBS Ami no nitrobenzenesulfoni.c
acid
AMS a-Methyl styrene
AP Aminophenol
AT Ami notoluene
BOA 3-Hydroxyanthracene-2-
carboxylic acid
BON 3-Hydroxy-2-naphthoic acid
CA Chloracetic acid
CH Cyclohexanone
DAT Diami notoluene
DCB Dichlorobenzene
DEABH 4,4'-bis (Diethyl ami no)
benzhydrol
DMA Dimethyl am" line
EA Ethanolamine
EO Ethylene oxide
EtOH Ethanol
EtCl Ethyl ene chloride
HAc Acetic acid
Hyd Hydrolysis
J Acid 6-Amino-l-naphthol-3-
sulfonic acid
MAA Methylacetoacetate
MDEA 4,4'-Methylene-bis-(N,N-
diethyl aniline)
NBC Nitrobenzoyl chloride
NDA 4-Ni troso-di methylani1i ne
NDS Naphthalenedisulfonic acid
NEA 4-Nitroso diethylaniline
Nitr'n Nitration
NP Nitrosophenol
Oxid'n Oxidation
PABA 4-Aminobenzoic acid
Red'n Reduction
SAA Sulfoanthranilie acid
Sap'n Saponifi cation
Sulfon'n Sulfonation
TASA Toluenesulfonamide
Tosyl Cl 4-Toluene sulfonyl chloride
VCN Acrylonitrile
14
-------
Acenaphthene
Oxid'n k
w
CH2(COC1)2^
Nanhfhalir — i
anhydride
5,7-tfiketo-IH-
cyclopenta-[
phenalene
NH
MeNH2
Oxi d
cd]-
( Process 41)
^ Naphthalimide
k. N-Moi-hul n^nhthal imidp
fl
thalene-tetra-
carboxylic acid
(Process 40)
FIGURE 1-1. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
ACENAPHTHENE
-------
Aniline
VCN
Diketene
>3-Anilino-
propionitrile
(Process 4)
> Acetoacetanilide
Process 15)
Baking .
H2S04
[Figure 1-25]
Sulfanilic acid
Acetanilide
(Process 4)
HNO,, 0NH,
4-(4'-Ami nophenylazo)
benzenesulfonic acid
(Process 4)
HNO,
Orthanilic acid
6-Anrino-3,4-azo-dibenzene-
sulfonic acid
t- N-Acetylsulfanilyl chloride
(Process 4) (Process 4)
HNOg.Red'n ^ 4_Hydrazinobenzene- D1ketene *3-Methyl-l-(4-su1fophenyl)-
sulfonic acid
N,N-Dibenzylsulfani1ic acid
5-pyrazolone
VCN
. p» 11-uydiiueui.y idieidiii i m
nPlUo ^ , mi-j f rnnrnf-Tni 1 i An
4-
4-Nitroacetanilide -r-
n 1 f\ \ *— •
Process 12)
—.y W 7 d-rHf-hlnr-n.-iroi-.-jnil i Ho
e
-H2° »
NaOH
;aOH " *
ed'n .
H,0
2-Nitroaniline
4-Ni troani 1
(a)
(Process 12)
b) Br2—^2,6-Oibrono-4-mtro-
aniline
4'-Aminoacetanilide
2,4-Dichloroaniline
FIGURE l-2a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED MATERIAL: ANILINE
-------
Aniline
(Cont'd) (Process 4)
[Figure l-2a]
nBuOH
PCI.
EO
EtOH
HCT
(Process 19)
4-Phenylazoani1i ne
-> N-Butylaniline-
VCN
EO
—> 3-(N-Butylanilino)-
propionitrile
__ fc, N-Butyl-N-(2-hydroxyethy1)-
aniline
HC1
-> N-Butyl-N-(2-chloroethyl)-
aniline
(Process 9)
4-[Butyl (2-chloroethyl) amino] benzaldehyde
-> 2-Anilino-
ethanol
ETC1
(Processes 6-10)
*N-Ethyl-N-(2-hydro-
aniline)
HC1
-> N-ethyl aniline
-M-(2-Chloroethyl)-
N-ethylaniline
4-[Ethyl (2-chloroethyl)amino]-
benzaldehyde
VCN
-> 3-(N-Ethy1anilino) proprionitrile
EtOH HH (Processes 6,8,10)
"""' HCV N,N-Diethylaniline
HNO,
CH-0
-> N,N-Diethyl-p-nitrosoaniline
(Process 6)
->• 4,4'-Bis(diethy1amino) benzophenone
(Processes 6,7)
->4,4'-Methylenebis
[N,N-diethylaniline]
,
(Process 8)
->4,4'-Bis(diethylamino)-
benzhydrol
[Figure l-2c] „„,
(Procrss 15)
JCHgCT ^ N-PErthy lS-SN-phe'nyl - -2^4 >• Ethyl benzyl ani 1 i ne-
benzylamine sulfonic acid
FIGURE l-2b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PRUCHASED STARTING
MATERIAL: ANILINE (Continued)
• . ^ 4,4'-Bis(diethylamino)-
benzhydrol,2,7-naphth-
ai enesulfonate salt
(Process 6)
2'6'ffDS—> 4,4'-Bis(Diethylamino)-
benzhydrol,2,6-naphth-
.(Process 8) alenesulfonate salt
kjiZM§_L^~3i'[(B~diethy1aiTiinophenyl )-
methyl]-2,7-naphtha1enedisulfonic acid, leuco form
(Processes 6,8)
'i i f*
>4-(Diethylamino-)benza1dehyde
-------
CO
Aniline
(Cont'd)
0 M*0" ^ H.^lhul...!! VCN
{Figure 1-2DJ
(Process 42)
LHoO ft» Am"Hnnmnth-mn
^,
AC->0 ., [
>- • fr I
CH3OH ^
H2S04
E0 *
^
NaHS03 sulfonic acid
Ac.,0 b4,4'-Isopropylidene-
dianiline
.,..,, (Process 4)
mlz ^ 4-Phenylazoani 1 ine
(Process 22)
S. , ^9 A1 . ThinHi.7milinn
(Process 6)
3-(N-Methylanilino)- -~2- ». 4-[(2-Cyanoethyl )-
proprionitrile w methyl amino]-benzal-
dehyde
-Methylacet-
anilide
(Processes 6,7,8,10)
CHoO
COC1,
N-(2-Hydroxyethyl)-
N-Methylaniline
Red'n
N-Methyl-4' nitroacet-
anilide
•p-Nitroso-N,N-dimethyl- ^2^
H20
aniline
(Processes 6,7)
->4,4'-Methylenebis [N,N-
dimethylanil ine]
(Processes 6,7)
->4,4'-Bis (dimethylamino)
benzophenone
(Process 6) NnA rH
>N-(2-Chloroethyl)-N- „• ^n
methyl anil ine "24
4'-Amino-N-Methyl-
acetanilide
p-Ditnethylamino-
benzaldehyde
(Process 9)
4-[(2-Chloroethylmethyl)-
ami no] benzaldehyde
4,41-Thiodianiline
FIGURE l-2c. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
ANILINE (Continued)
-------
Anthranilic acid
CA
-> N-Carboxymethyl-
anthranilic acid
CH,0
RecTfr
N-Methylanthranilic
acid
(Process 43)
HN02 ^ 2,2'-Dithiodibenzoic
2 *2 acid
(Process 15)
»5-Sulfoanthrani1ic
acid
AcoO
(Process 43)
4-Hydroxy- 1 1 -methyl -
carbostyril
(Process 43)
(Process 43)
*2-Mercaptobenzoic
acid
(2-Carboxymethyl-
mercapto) benzole
acid
» 3(2H)-Thio-
naphthenone
FIGURE 1-3. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: ANTHRANILIC ACID
(Process 6)
Benzaldehyde
HNO-,
3-Ni trobenzaldehyde
Oxid'n
->• 3-Nitrobenzoic acid
PClr
3-Nitrobenzoyl chloride
-J acld
7-{3-nitrobenzamido)-4-
hydroxy-2-naphthalene-
sulfonic acid
7-(3-aminobenzamido)-4-
hydroxy-2-naphthalene-
sulfonic acid
FIGURE 1-4. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL: BENZALDEHYDE
Benzene-
sulfonic acid
HNO,
3-Nitrobenzene-
sulfonic acid
Red'n
In, NaOH
Red'rv
4,4'-Diamino-2-21-biphenyl-
disulfonic acid
->• Metanilic acid
2-Nitrobenzene-
sulfonic acid
Red'n
->• 2-Aminobenzene sulfonic
acid
FIGURE 1-5. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
BENZENESULFONIC ACID
-------
Carbazole
EtCl
-> 9-Ethylcarb-
azole
HNO-
-> 3-Nitro-9-
ethyl-carbazole
(Process 20)
3-Aniino-9-ethyl-
carbazole
FIGURE 1-6. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING
MATERIAL: CARBAZOLE
Chlorobenzene
ClS03H
In, H20
INi
o
MeS03H
HN03
HN03
H2S04
^H-v,muruuen£eiiK ^
sulfonyl chloride
NH3 „
HN03
4-roethylsulfone
w^ 1 rhl rtvrt *? Ih
— ^ i-unioro-t*" w
nitrobenzene
•f
l-Chloro-4-
nitrobenzene
(Process 3)
h 1 rhloro -° 4 fc
di nitrobenzene
4-Chlorobenzene-
sulfinic acid
4-Chlorobenzene-
sulfonamide
4-Chloro-2-nitro-
benzenesulfonyl chloride
© [Figure l-7b]
(?) [Figure l-7e]
FIGURE 1-7a SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: CHLOROBENZENE
-------
l-Chloro-2-nitro-
benzene
(Cont'd)
[Figure l-7a]
Zn
!,3'-Dichlorobenzi-
dine dihydrochloride
jClSOgH
Process 22)
M^ ,
iNaOH
4-Chloro-3-nitrobenzene
sulfonyl chloride
NH,
bis-(2-Nitrobenzene)
disulfide
2-Aminobenzene-
sulfonic acid
-> o_-Nitrophenol
0NH0
jMeNH,
H^8'
>4-Chloro-3-nitro-
benzenesulfon-
amide
•4-Chloro-3-ni trobenzene-
sulfonanilicie
•4-Chloro-N-methyl-3-
nitrobenzenesulfon-
amide
-»-4-Chloro-N,N dimethyl-
3 nitrobenzenesulfon-
ami de
-Nitrobenzene-
sulfonic acid
Red'n
iMeSOjJi
4-ChToro-3-nitro-
phenylmethyl-
sulfone
•NaOH
|(feOH
i [Figure 1-7c]
[Figure l-7d]
FIGURE 1-7b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING
MATERIAL: CHLOROBENZENE (Continued)
-------
J-Chloro-2-
nitrobenzene
(Cont'd)
0
[Figure 1-7b]
(Process 15)
2-Methoxynitro-
benzene
Red'n
IN3
ro
Alk
4-Methoxy-3-nitro-
benzenesulfom'c
acid
3-Amino-4-methoxy-
benzenesulfom'c
acid
o-Anisidine
|HN0
>4,4'-Cyclohexy1-
idenedi-(5-
anisidine
t4-Nitro-o_-
anisidine
5-Nitro-o-
anisidine
Ac,0
Aceto-o- HNO
anisidide
-3—*-4-Nitro-2-acetoaniside
& 5-nitro-2-acetoanisidide
CH20_
NaHSO,
• p_-Anisidinomethane-
~~ sulfonic acid
(Process 15)
3-Ami no-4-methoxy-
benzenesulfonic acid
5-Ami no-4-methoxy-
2-nitrobenzene-
sulfonic acid
(Process 8)
5,5'-Ureylenebis
(4-methoxy-2-ni trobenzene-
sulfonic acid)
^Iketene >. Acetoacet.£.
anisidide
5,5'-Ureyl-
enebis-(2-
araino-4-
methoxy-
benzene-
sulfonic
acid)
HN0
Zn.NaOH
H2S04
->o-Dianisidine
4-Nitro-£-anisidine
^
-> 2,4-Di<
Diaminoanisole
dihydrochloride
PCI.
• 3,3"-Dihydroxy-V ,4 "-
bi-2-naphtho-o-anisidide
FIGURE l-7c. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED
STARTING MATERIAL: CHLOROBENZENE (Continued)
-------
l-Chloro-2-
ni trobenzene
(Cont'd)
[Figure l-7b]
(Process 45)
2-Chloroaceta
nilide
DiketenVAcetoacet-2-
chloroanilide
•2-Ch1oro-4-nitro -J&n-
acetanilide NaOH
2-Chloro-4-nitroam'1ine
(Process 15)
2-Nitroaniline —2-
4-Chloro-3-nitro-
benzenesulfonic
acid
(Process 40)
o-Phenylenediamine SJ-S
(Process 4)
,2,3-Benzo-
triazole
FIGURE l-7d. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM STARTING MATERIAL:
CHLOROaENZENE, (Continued)
-------
]-Chloro-2,4-d1nitro
benzene (Cont'd)
[Figure l-7a]
NaOH
HaHSO,
NH
NaOH
MeOH
Part'l
Red'n
-*> 2,4-Dinitrophenol -Red'n
2,4-Diaminophenol-
dihydrochloride
2,4-Dinitro-
benzenesulfonic
acid
Red'n
-> 2,4-Diaminobenzene-
sulfonic acid
(Process 12)
—2 &>3-Chloro-4,6-dinitro-
benzene sulfonic acid
(Process 12)
2,4-Dinitroaniline-r-^-2
I o
Methoxy-2,4-
di nitrobenzene
Part'l
Red'n
2-Chloro-5-nitroaniline
4-Chloro-3-ni troani1ine
4-Chloro-l ,3-phenylenediamine
2-Chloro-4,6-dinitro-
ani line
2',4'-Dim'troacetanilide
3-Nitro-o
anisidine
EtCl
->3-Nitro-N-ethyl-2-
anisidine
4-SAA
->3-{2-Carboxy-4-
sulfophenyl)-
3-ethyl-l-(5-
nitro-2-anisyl)
triazine
FIGURE l-7e. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED
STARTING MATERIAL: CHLOROBENZENE (Continued)
-------
jj-Chlorobenzene-
sulfonic acid
HNO,
H2S04
4-Ch1oro-3 nitrgbenzene-
sulfonic acid
MeOH
HN00
ro
en
NaHS0
NaOH
MeOH
NaOH
Red'n
4-Methoxy-3-nitro- •
benzenesulfonic
acid
5-n-Butylsulfonamido
-2-nitroanisole
(Process 4)
4-Chloro-3,5 dinitro-
benzenesulfonic
acid
PCI
3—
Red'n
4-Methoxy-3-ni trobenzene-"'Buf!lH2-
sulfonyl chloride
fr- 4-n-Butylsulfonamido-
-anisfdine
Red'n
NaOH
2-Chloro-l ,3-phenylene-
diamine-5-sulfonic
acid
2,6-Dinitro-4-phenol-
sulfonic acid
Part'1
Red'n
3-Anrino-4-hydroxy-5-nitro-
benzenesulfonic acid
2-Ni tro-p_-benzene-
disulfonic acid
2-Nitro-4-methoxy-
benzenesulfom'c
acid
2-Nitro-4-hydroxy-
benzenesulfonic
acid
Red'n
Red'n
2-Amino-£-benzene
disulfonic acid
3-Amino-4-methoxy- (a) [Figure 8bJ
benzenesulfonic
acid
Red'n
->• 2-H.ydrox.ymet-
anilic acid
(Process 4)
HNO,
4-Chlorometanilic —
acid Na2S03
(Process 4)
Diketene
4-Ch1oro-3-hydrazino-
benzenesulfonic acid
*-l-(2-Chloro-5-sulfophenyl)-
J-methyl-5-pyrazoione
FIGURE l-8a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED
STARTING MATERIAL: £-CHLOROBENZENESULFONIC ACID
-------
3-Ami no-4-methoxy-
benzenesulfonic acid
(Continued) [Figure 1-8a]
COCj_,
Base'
Tosyl Cl
N,N'-Carbony1-bis (4-
methoxymetanilic
acid)
3-(Amino-4-tosy1)-4-
methoxybenzenesulfonic
acid
HNQ,
2-Ni tro-5-ami no-4-methoxy-
benzenesulfonic acid
Red'n
2,5-Diamino-4-methoxybenzene-
sulfonic acid
5-acetamide-2-amino-4-methoxy-
benzene sulfonic acid
FIGURE l-8b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING
MATERIAL: p_-CHLOROBENZENESULFONIC ACID (Continued)
-------
p-Chloroni trobenzene
MeS03H
Red'n
C1503H
NaOH
'MeOH
4-Chloro-3-(methylsul-
fonyl)ni trobenzene
£-Chioroaniline
Diketene
-> Acetoacet-£-chloro-
! anilide
! BON, PCU
j *-+. 4'-Chloro-3-hydroxy-2-
I naphthanilide
HNO,
(Process 4)
; HN°2 ,
Red'n
(Process 15)
H2S04
4-Chloro-3-nitroani1ine
(Process 4)
4-Chlorophenylhydrazine Dlketene »
l-(4-Ch1orophenyl)-3-
methyl-2-pyrazolin-5-one
2-Amlno-5-chlorobenzene-
sulfonic acid
5-Chloro-2-hydrazinoben-
zenesulfonic acid-
(Process 4)
HN02
• -, -
^d n
(Process 4)
Diketene
l-(4-Chloro-2-sulfo-
phenyl)-3-methy1pyrazo1one
-> 2-Chloro-5-nitroben- Zn> H2-
zenesulfonyl chloride
2-Ch1oro-5-nitrobenzenesulfinic acid
-> 4-Methoxynitro-
benzene
Red'"
p_-Anisidine
(9) [Figure 1-9b]
ig^ 3.Nitro-£-anisidine
Process 15)
_Ac20_
->£-Acetanisidide
2-Nitroaceto-£- -Mrr
anisidide NaOH
2-Nitro-£-
anisidine
RON Pf*l
' 3 *3-Hydroxy-2-naphtho-£-anisidide
FIGURE 1-9a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL-
p-CHLORONITROBENZENE
-------
g-Chloro-
ni tro-
benzene
(Cpnt'd)
[Figure 1-9a]
Oleum
ro
CO
2-Chloro-5-nitro-
benzenesulfonic acid
p_-nitro-
Jamne__„ 5-Nitr0-2-(£-nitroani- -BsLlL
lino)-benzenesulfonic j
acid :
benzenesulfonic acid
~* j-Amino-2-(p_-aitrinoani-
lino)benzenesulfonic
acid
(Process 3)
Toluidine ..
^
!( Process 3)
0NH2
NH3
Red'n ^
UNO,
^
(Process 3)
o-Anisidine
Partial
Red'n
5M4<-«« o « /+.^i,.,- j;«*\ Red n ^
benzenesulfonic acid
ZAnil-inrt ^ MT +vnKrtrt R6U T\ ^
-Mni 1 1 no-D-m troDen- "^
zenesulfonic acid
2 .Ami nn-R-ni +-vnhor»^onzi_ R6Q 0 ^
sulfonic acid
PC13
6-Chlorometanilic acid
2Thln^n 1 T rl-ini trnhon „,.§-., ... ^
zenesulfonic acid
7-1 n-flnisiHinnl-fi-m tro-
nitrobenzenesulfonic acid
5-Amino-2-(jD-toluidino)-
henzenesulfonic acid
(Process 20)
5-Amino-2-anilinobenzene-
sulfonic acid
2,5-Diaminobenzenesul-
fonic acid
5-Acetami do-2-ami noben-
zenesulfonic acid
2-Amino-5-nitrobenzene-
sulfonyl chloride
2-Ami no-N-ethyl-5-ni tro-
benzenesulfonali de
3,5-Oinitro-2-hydroxyben-
zenesulfonic acid
3-Amino-2-hydroxy-5-ni-
trobenzenesulfonic acid
AcCl
N-ethyl-
am'line
Partial
Red'n
[Figure l-9c]
FIGURE l-9b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED
STARTING MATERIAL: p-CHLORONITROBENZENE (Continued)
-------
IN5
10
D-Chloro-
ni tro-
benzene
(Cont'd)
NaOH
[Figure l-9b]
EtOH
4-Etho ^nitro-
benzene
Red'n (Process 45)
Ke° " &• £-Phenetidine-
(Process 12)
3,4-Dichloro-
nitrobenzene
Red'n
. £-Nitroaniline
fe-
NaOH
Red'n
Ac~Q
BON.PCl-
3,4-Dichloroaniline
-4-nitrophenol
-Nitro-t-pheneti dine
p-Acetophenetidide
^
Red'n,
3-Amino-£-acetophenet1de
>3'-[Oi(2-hydroxyethyl)]- —
amino-£-acetophenetidide
3'-[Di(2-acetoxyethy1 )-amino]-
£-acetophenetidide
Acetoaceto-£-phenetidide
3-Hydroxy-2-naphtho-£-phenetidide
2-C
aniline
(Process 12)
Br-
2-CMoro-4,S-dinitro- ^
(Process! 2) 2"Bromo"5"cll1oro"4"nitroaniline
— 2 M- 2-6-Dichloro-4-nitroaniline
Red'n
->• 2-Chloro-4-phenylenediamine sulfate
->• £-Phenylenediamine
5COC1
— — - -- -
4'-Ami nobenzanilide
2-Amino-6-chloro-4-
nitrophenol
FIGURE l-9c. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED
STARTING MATERIAL: p-CHLORONITROBEMZENE (Continued)
-------
P_-Ch1orobenzoic acid - HNO
3 ^ 2-Ch1oro-5-nitrobenzoic
HC1 acid
*• 3-Carboxy-4-chloroben- —— *>• N-[(3-Carboxy-4-chloro-
zenesulfonyl chloride benzene)-su1fonyl] anth-
ranilic acid
FIGURE 1-10. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
o-CHLOROBENZOIC ACID
HNO (Process 3)
2-Chlorobenzoic acid 2^3 *• 4-Chloro-3,5-dinitro-
benzoic acid
FIGURE 1-11. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
£-CHLOROBENZOIC ACID
4-Chloroani-
m-Chlorobenzoyl chloride -^^ > 3,4'-Dich1orobenzanilide
FIGURE 1-12. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
m-CHLOROBENZOYL CHLORIDE
(Process 9)
o-Cresol C02 *• 2,3-Cresotic acid
FIGURE 1-13. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
O-CRESOL
-------
o-Cresol
3-Methoxy toluene
Nltr'n
2-Nitro-3-methoxyto1uene
Red'n
2-Methylanisidine
BON
3-Hydroxy- 2 '-me thy 1 -
2-naphth-4-anisidide
FIGURE 1-14. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: m-CRESOL
CO
£-Cresol
HNQ,
-fiX-
2-Nitro-4-cresol
MeC1
4-Methoxy-3-
nitrotoluene
Red'n
4-Cresidine
i-Red'n fr 2-Amino-4-cresol
FIGURE 1-15. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: £-CRESOL
2,4 Diaminotoluene
0x1 d n
8-Amino-7-methyl-2-
phenazinol
FIGURE 1-16. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
2,4-DIAMINOTOLUENE
(Process 15)
Oleum
HNO-,
Red'n
o-Dichlorobenzene
->. 3,4-Dichloro-
benzenesulfonic
acid
->4,5-Dichloro-2-nitro-
benzenesulfonlc acid
2-Amino-4-5-dich1oro-
benzenesulfonic acid
FIGURE 1-17. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL-
o-DICHLOROBENZENE
-------
ft-Dichlorobenzene
(Process 8)
CoCl,
•>2,5-Dichlorobenzoic
acid
,HN03
->2,5-Dichloronitro-
benzene
Red'n
(Process 45)
2,5-Dichloroaniline
(Process 15)
Oleum
(Process 4)
-> 2,5-Dichlorosulf- nl"u2
anilic acid Red'n
2,5-Dichloro-4-hydra-
zi nobenzenesulfoni c
acid
(Process 4)
Diketene
l-(2,5-Dichloro-4-
sulfophenyl)-3-
methy1-5-pyrazolone
MeOH
NaOH
CO
ro
i NaOH
NH,
->4-Chloro-2-nitro-
am'sole
->4-Chloro-2-nitro-
phenol
->4-Chloro-2-nitro-
aniline
Red'n
HNO-,
Red'n
-> 3-Chloro-o-
anisidine
BOM
5' -Chloro-3-hydroxy-
2-naphtho-c^-anisidide
4-An111no-2-nitro-
anisole
3-Anilino-o-anisidine
Red'n
4-Chloro-2,6-
dinitrophenol
2-Ann'no-4-chloro-6
nitrophenol
(Process 15)
2-Amino-4-chloro-
phenol
2-Amino-4-chloro-
phenol-5-sulfonic
acid
4-Chloro-o-pheny1 -
enediamine
FIGURE 1-18 SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION
PURCHASED STARTING MATERIAL: £-DICHLOROBEN7ENF
-------
Diphenylamine
44IP
N(4-Anilinophenyl)-4-
quinone imine
FIGURE 1-19. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: DIPHENYLAMINE
Hydroquinone
CO
GO
EtOH
HC1 *• H
MeOH .
HC1 * *
0NH0
4-Diethoxybenzene -^3-
2' ,5'-Diethoxy-4'-nitro-
benzanilide
4-Dimethoxybenzene —3-
2,5-Dimethoxy-4-
nitroacetanilide
4-Chloro-2,5-dimethoxy-
aniline
2,5-Diethoxyni tro-
benzene
Red'n
2,5-Diethoxy-
aniline
0COC1
-*2',5'-Diethoxy- —3-
benzanilide
Red'n
4'-Amino-2',5'-Diethoxy-
benzanilide
?,5-Dimethoxynitro-
benzene
Red'n
2,5-Dimethoxy-
aniline
2,5-Dimethoxy-
acetanilide
IT) "[See below]
£-Anilinopheno1
2,5-Dimethoxy-4- 2
nitroaniline LULI2
4-Chloro-2,5-dimethoxy-
nitrobenzene
Red'n
BON
PCI:
Diketene
4!-Chloro-3-hydroxy-
2',5'-dimethoxy-2-
naphthanilide
4'-Chloro-2' ,5'-dimethoxy-
acetoacetanilide
2,5-Dimethoxy- (VJ)
aniline [See above]
(cont'd)
0COC1
2' ,5'-Dimethoxy-
benzenesulfonami de
->2' ,5'-Dimethoxybenz-
anilide
HN03_
2' ,5'-Dimethoxy-4'-nitro-
benzenesul f onami de
2',5'-Dimethoxy-4'-nitro-
benzani-lide
Recf n
Red'n
ino-2' ,5'-dimethoxy-
benzenesul fonami de
4'-Annno-2' ,5'-dimethoxy-
benzanilide
FIGURE 1-20. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: HYDROQUINONE
-------
j>-Hydroxybenzoic acid
4-Anisic acid
4-Anisoyl chloride
HNO,
4-Methoxy-3-nitrobenzoic
acid
PCI-
4-Methoxy-3-nitrobenzoyl
chloride
4-methoxy-3-nitrobenza-
nii de
3Amino-4-methoxybenze-
FIGURE 1-21. SYNETHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
P-HYOROXYBENZOIC ACID
HNO,
Isophthalic
acid
-> 5-Nitroiso-
phthalic
acid
Red'" ». 5-Aminoisophthalic
acid
FIGURE 1-22. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING
MATERIAL: ISOPHTHALIC ACID
GO
Naphthalene
HNO,,
1-Nitronaphthalene
Fe
->• 1-Naphthylamine
BON
PCI
3-Hydroxy-N-l-
3 naphthyl-2-naph-
thamide
(Process 15)
^0^—^ 4-Amino-l-naphthalene- oNa^°3
sulfonic acid or HNU2
4-Hydroxy-l-naph-
thalenesulfonic
acid
(Processes 8,10)
N-Ethyl-1-naphthylamine
*• N-Ethyl-N-1-
naphthyl-4-
nitrobenzamide
[Figure l-23b|
Red'n
> N-Ethyl-N-1-naph-
thyl-4-amino-
benzamide
FIGURE l-23a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE
-------
(Process 15)
(Process 44)
(Process 44)
(Process 44)
co
en
iiapii ma * CMC
(Cont'd)
[Figure l-23a]
1
<0
[Figun
t^jf-— •»» i--uapuu!a lent buiiumc —
Vvarm acid
f i
J) (f
e l-23c] [Figu
- — s — »• ^-wapntnaiene suironyi
chloride
(Process 44)
pri
. . ^ . th. Ninh-fhn
1(2H)
NaOH (Process 1)
nau" fc. o N-irihthnl
fmU'j ~ r iLiii...- o n- nkth 1 1 rt«^
•'••• ~o w y-ni cro-i.-napnuna i ene-
sulfonic acid
+
8-Nitro-2-naphthalene-
sulfonic acid
i(-n
ni,v,l . p Rro4.nmj
(Process 15)
01eum ft. " fi W-inhth-ilr-np
disulfonic acid
(Process 15) i
""SO. i, o 7 MTnhthTlonr-
disulfonic acic
r
5)
re l-23c]
: p- i-napniinyi mercapian -
[2,l-b]thiophen-
-one
'• • i hb fl*^i fPlmiv^n 1 *1T 'f 1
P VJx 1' iQure 1 *tJ f J
sulfonic acid
^ p Ami nri ? n "i nh t h jT 1 ono
sulfonic acid
do-2-naphthol
HNO-, ^ q Niti-n ° 7 mnhthjT
lenedisulfonic
acid
(Process 8)
amino)benzhydrol-2,
6-naphthalene-
disulfonate
Process 2)
M^OT k. 4 Mitrn ° 7 mnh
thalenedisulfonic
acid
(Process 8)
DEABH k . .1 hirfniothui
amino)benzhydrol ,-
2,7-naphthalene
disulfonate
(Process 8)
phenyl )methyl ]-2 ,7-
naphthalenedi sulfonic
acid
~ t ^' ^-IMd^llLliy 1 LMK
acetic acid
NaOH . , Ami no 6
naphthol
NaOH . . . ^ ?
naphthol
fc> 3 Ami no 2 7
naphthalene-
disulfonic acid
1 ht A^niniti-n0
7-naphthalene-
disulfonic acid
[Figure l-23c]
FIGURE l-23b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
-------
4,5-Dinitro-2,7- Q^
naphthalene- [Figure l-23b]
di sulfonic
acid
(Cont'd)
4,5-Dianiino-2,7-naph-
thalenedisulfonic
acid
— 2 — 3
4-Amino-5-hydroxy-2,
7- naphtha! ene-
disulfonic acid
0COC1
HNCL
T-
22
4-Benzaniide-5-hydroxy-2,7-naph-
thalenedisulfonic acid
4-Chloro-5-hydroxy-2,7-naph-
thalenedisulfonic acid
alene
(Cont'd)
(Process 15)
cglS4 »
1-Naphthalene sulfonic-
acid
) [Figure l-23b]
(Process 15)
H0SO
4
1,6-Naphthalenedisulfonic
acid
[Figure l-23b]
[Figure 1-23d]
OJ
en
4-Acetamide-5-hydroxy-2,7-
naphthalenedisulfonic acid
8-Nitro-1,6-naph-
thalenedisulfonic
acid
8-Amino-l,6-naph-
thalenedisulfonic
acid
4-Hydroxy-2,5-naph-
thalenedisulfonic acid
(Process 15)
01 euro
Fe
8-Ami no-1,3,6-naph-
tha! enetri sulfonic
acid
NaOH
4-Amino-5-hydroxy-2,7-
naphthalenedisulfonic-
acid
, -
1,3,6-Naphthalene-
trisulfonic acid
HNO,
Tosyl Cl
0COC1
8-Nitro-l,3,6-
naphthalene-
trisulfonic acid
4-p-Tolylsulfonamido-
5-hydroxy-2,7-naphthalene-
disulfonic acid
8-Ainino-l-naphtho1-3,6-
disulfonic acid-4-toluene-
sulfonic acid
4-Benzaniido-5-hydroxy-2,7-
naphthalenedisulfonic acid
8-Amino-l-naphtho1-3,6-disulfonic
acid-benzene sulfonate
FIGURE 1-23C
"
-g^ 5.Hydroxy-2>4,7-naph-
thai enetri sulfonic
acid
SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
4,5-Dihydroxy-2,7-naphthalene-
disulfonic acid
-------
1-Naphthalene-
sulfonic
acid
(Cont'd)
©
[FIGURE l-23cj
(Process 15)
Oleum .
1,5-Naphthalene-
disulfonic acid
CO
• pi» i , j uinj'UfUAj- ~|
naphthalene
disulfonic acid
(Process 15) HNn
Oleum ^ 1 3 r fjaphth HN03 p
alene trisulfonic
acid
5 Ami no » A. — h v/Hvrw \/ —
2,8-naphthalene-
disulfonic acid
HN03 Fe
° fc. T Mitr-n 1 "; e
naphthalenedi-
sulfonic acid
P* 1,3 UUiyUFUAJT-
naphthalene
Fe
naphthalene
trisulfonic
acid
naphthalene- 1 ,7
disulfonic acid
-fc- 3-Amino-l ,5 Naph-
thalene-disul-
fonic acid
ftti A Ami nA 1 T flow ^
5-Naphtha-
lene tri-
sulfonic
acid
HNO,
5-Nitro-l-naph-
thalene sulfonic
acid
+
8-Nitro-l-naphth-
alenesulfonic
acid
4-Nitro-l,5-
naphthalene di-
sulfonic acid
-Ami no 1,5-
naphthalene-
disulfonic
acid
NaOH
Fe
— ^ u-niii i HU- i -najjn- —
thalenesul-
fonic acid
thalenesul-
fonic acid
^ i-Hiiniiu-o-
naphthol
(Process 15)
Oleum . . . , ,
^ if-HrninO"! ,D-
naphthalene-
disulfonic
l-Amino-5-hy-
droxy-1-na-
phthalene
sulfonic acid
tr i -niiniiu "
-------
8-Amino-l-
naphthalene-
sulfom'c acid
4AT
[Figure l-23d]
CO
CO
HNOn
8-p-Toluidino
1-naphthalene-
sulfonic acid
8-Hydroxy-l-na-
phthalenesulfonic
acid
(Process 15)
4-Hydroxy-l ,5-
naphthalene-
disulfonic acid
FIGURE l-23e. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
-------
(Process 15)
2-Naphthol 03) -r
(Cont'd>[Figure ,.235,1
OJ
to
acid
3-Hydroxy-5-
sulfon-2-naph-
thoic acid
(Process 15) (Process 1) (Process 15)
PC1
^3—*• 3-Hydroxy-N-(2-
tft hydroxyethyl)-
2-naphthamide
3-Amino-2-naph-
thoic acid
PCI.
3-Hydroxy-2-
naphthanilide
2-Naphthol-6-
sulfonic acid
naphtha!enedi-
sulfonic acid
2-Naphthol-8-
sulfonlc acid
'(Process 15)
; H-SO. ^
(19)
[Figure l-23g]
3-Hydroxy-2,7-
naphthalene-
disirlfonic
actd
H0
NaOH
NaOH-
6-V
naphtha1ene-
sulfonic acid
i^M%> 6-Amino-2-
naphthalene-
sulfonic acid
3,5-Dihydroxy-
2-naphthoic
acid
2—»» 2-Hydroxy-3-
carboxy-HH-
benzo-
carbazole
-4-Anisidl'n^2-Hydroxy-llH-
benzo-
carbazole-3-
carboxy-4-
anisdide
2,8-Dihydroxy-
6-naphthalene-
su'ifonic acid
• 7-Ami no-1-
naphthol-
3-sulfonic
acid
AcCl
6-Acetamido-4-
hydroxy-2-
naphthalene-
sulfonic acid
5,7-C
2-naphthalene-
sulfonic acid
0-6-
methoxy-2-
naphthalene-
sulfonic acid
5-Amino-6-methoxy-
2-naphthalene-
sulforvic acid
FIGURE l-23f. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
-------
2-Naphthol Q9)
(Continued)
[Figure 1-23f]
C1S03H » 2-Hydroxy-l-
naphthalene-
sulfonic acid
2-Amino-l-naph-
thalene-sulfonic
acid
(Process 15)
Oleum
2-Amino-l,3,6-
naphthalene-
trisulfonic
acid
aOU
hydroxy-2,
7-naph-
thalene-
disulfonic
acid
. NaOH
H^SO,,
6-Amino-l,3-
naphthalene-
disulfonic
acid
6-Amino-l-
naphthol- [Figure 1-231]
3-sulfonic
acid
-JS.
O
2-Naphthylamine
[Figure l-23h]
(Process 1)
i-Nitroso-2-
naphthol
NaHSO-,
4-Aroino-3-hydroxy-
1-naphthalene-
sulfonic acid
HNO,
4-Amino-3-hydroxy-
7-nitro-1-naph-
thalene-sulfonic
acid
({Process 4)
I HN00
EtOH
H2S04
2-Ethoxyna-
phthalene
C1SO,H
CS0
6-Ethoxy-2-naph-
thalenesulfonic
acid
HNO,
^
Uaphth-U.Z-rt)
(I ,Z,3)-oxa-
diazole-5-
sulfonic acid
/-5-nitro-
2-naphthalene-
sulfonic acid
Red'n
3-F
naph-
thalene-
sulfonic
acid
5-Amino-6-
ethoxy-2-
naphthalene-
sulfonic
acid
FIGURE l-23g. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
-------
2-Naphthylamine -
(Continued)
[Figure l-23g]
BON
PCI.
3-Hydroxy-N-2-
naphthyl-2-
naphthamide
(Process 15)
Q1eum
7-Amino-2-Naph-
thalenesulfonfc
acid
(Process 15)
OTeuffl
7-Amino-l,3-
naphthalenedi-
sulfonic acid
NaOH
7-Ami no-1-
naphthol-
3-sulfonic
acid
JNH.
7-Amino-2-Naph-
thalenesulfonic
acid
(Process 15)
Oleum
SO.,
S00
PABA
>-6-Amino-l,3-
naphthalene-
disulfonic
acid
SO,,
NaOH
-+• 6-Anilino-l-
naphthol-3-
sulfonic acid
6-(£-Carboxy-
anilino)-4-
hydroxy-2-naph-
thalenesulfonic
acid
6-Amino-l-naphthol-
3-sulfonic acid
4-Amino-l-naph-
thalene-disulfbnic
acid
(Process 15)
01 eum .
>6-ArviTino-l-
naplithol-3-
sulfonic acid-
2-Amino-1,5-
naphthalene-
disu>fonie
acid
FIGURE l-23h. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
-------
6-Ami no-1- (21)
naphthol-3- [Figure l-23g]
sulfonic acid
(Cont'd)
AcCl
3NBC
4NBC
COC1,
0COC1
7-Acetamido-4-
hydroxy-2-
naphthalene-
sulfonic acid
7- (3-N i trobenzanri do) -
4-hydroxy-2-naph-
thalenesulfonic
acid
7-(4-Aminobenz-
amido)-4-hydroxy-
2-naphthalene-
sulfonic acid
7, 7'-Ureylene-bis-
(4-hydroxy-2-naph-
thalenesulfonic
acid
7-Benzamido-4-hydroxy-
2-naphthalenesulfonic
acid
Red'n
7-(3-Aminobenz-
amido)-4"-
hydroxy-2-naph-
thalenesulfom'c
acid
4NBC
7-[3-(4-Nitro-
benzamido)-
benzamido]-4-
hydroxy-2-
naphthalene-
sulfonic acid
Red'n
7-[3-(4-Aminobenz-
amidoj-benzamido]-
4-hydroxy-2-naph-
thalenesulfom'c
acid
FIGURE l-23i. SYNTHESIS OF VARIOUS INTERMEDIATES HOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NAPHTHALENE (Continued)
1-Naphthol
(Process 15}
Oleum
l-Hydroxy-2,4,7-
naphthalenetri-
sulfonic acid
Red'n
(Process 2)
-> 1-Hydroxy-2,7,naph-
tha lenedisulfonic
acid
FIGURE 1-24. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING
MATERIAL: 1-NAPHTHOL
-------
N1trobenzene
,Kal » Phenyl hydroxyl- -JsQSL
Azoxybenzene
Red'n
->Phenylazobenzene —*——
•Phenylhydroazo-
benzene
HC1
-> Benzidine sulfate
-> bis-Acetoxybenzidine
K3,3'-Dinitro-bis-acetoxy-
benzidine
3,3'-Dianrino-bis-
acetoxybenzidine
H+
.1 n
2U
3,3'-Oiamino-benzidine
(Process 15) (Process 15}
Baking »,3.Su1fot>enzi-,jine ffa£™9 ^3,3'-Disulfobenzidine
24
U>
[(Process 15)
Oleum M M.J trnhpnTpnp Red'n _ .,.,.___-,; ...
sulfonic acid
-
W Micuani i it. aciu
t LL. 1 ^^r^Ti-i^hi/l mf»f" ani T 1 f" — - —
acid
» ?J .— . -k.T.flrotami Hnhon^nno- .!r"^
sulfonic acid
&,5'-HreyTerrebis (2-nitro-
benzenesuVfonic acid)
Red'n fc 0 ?i ni>iilfr>KrnTirHnr
— ^3- Di ethyl ami no-
phenol
MMH
nlTUo ^ M fci r\-*A4-h^/l /I ni+-v*nrn ^
Phenetidine
k. =; -Aminn.?; ni ti-n COCTo ^
benzenesulfonic
acid
^ ." . hi T 1' in-nuTonohte
^ D,J -ureyieneoTS
( 2-ami nobenzene-
sulfonic acid)
fProcess 12)
fCll ». l-Chloro-3-nitrobenzene(22^ [Figure T-25bJ
^ [Figure T-25c}
FIGURE l-25a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NITROBENZENE
-------
l-Chloro-3-nitro-
. Red'n
benzene (Cont'd) [Figure l-25a]
3-Chloroaniline i HN02-
I Cu2Cl2
-> 1 ,3-Dichlorobenzene
HNO,
24
(Process 3)
2,4-Dichloronitro-
benzene
eOH
->2-Methoxy-4-chloronitro-
benzene
->4-Chloro-
2-anisidine
Red'n.
2,4-Dichloroaniline
EO
>3'-Chloro-3-hydroxy-2-naphthalide
N-(3-Chlorophenyl) diethanolamine
FIGURE l-25b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: NITROBENZENE (Continued)
-------
Nitrobenzene Q3)
(Cont'd) [Figure l-25a]
H2S04
1,3-Dinitrobenzene-r^^3-
cn
NaHSO,
Red ' n
> 4-Amino-2-ni tro-
benzenesulfonic
acid
3-Nitroaniline
-M°2 + 3-Ni trophenol
->3'-NHrobenz-
anilide-41-
sulfonlc acid
^3'-Nitroacetanilide
Red'n
->3'-Amlnobenzani1ide-
4'-sulfonic acid
^3..to1noacet.
am'lide
°
Acetoacet-0-
toluidide
• ,
. 3-Ni troani sole
-i Red'l3-Hetho*yaniline
EtCl,
>3-N,N-Diethyl-
anisidine
EO
2-(3-Nitroanilino) Red'V2-(3-Aminoani1ino)
ethanol ethanol
4 NBC
->3,3'-Mnitrobenz-
anilide
HCOOH
3-Nitroform-
anilide
Red'n..
Red'n
3,3'Oiaminobenzanilide
3 Aminoformanilide
BON
aino-2-nitro-
bervzene sulfonic
add
'3
gcocj
^-3-Hydroxy-3'-nitro-2-naphthanilide
-fcS'-Nitrobenzanilide- Red'n » 3'-Aminobenzani1ide-4'-
•1,3-Phenylene--
diamine
HGOOH
4'-sulfonic acid
Diformyl-3-phenylene-
diamine
HNO,
sulfonic acid
->4-Nitro diformyl- -2—
3-phenylene-
di amine
4-ftitro-3-
phenylene-
di amine
[Process 15)
4 ^4,6-Diamino-l ,3-benzene-
sulfonic acid
FIGURE 1-25C. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FKOM
PURCHASED STARTING MATERIAL: NITROBENZENE (Continued)
-------
£-Nitrophenol
Cl
Red'n
2-Aminophenol
Benzoxazolone
2-Methylbenzoxazole
HNOo
-> 6-Nitrobenzoxazo.lone:
^5-Nitro-2-Methyl-
benzoxazole
SaP'n
Dlisobutylen^ 2.Nitro.4.(1 >} ^3.
tetramethyl butyl )-
phenol
AMS
H2S04
C1SO,H
Red'n
-d ,1 ,3,3-
tetramethy 1 butyl )-
phenol
-> 4- K,<<-Dimethyl benzyl)
2-nitrophenol
2-Nitro-4-phenolsulfonyl-
chloride
e.e'-Oiamino-m.m'-biphenol
MeNH?
2-Ami no-4-(of.,°c-Dimethyl benzyl )-
phenol
-> 2-Nitro-4-(N,methylsulf-
amoyl) phenol
Red'n
• 2-Amino-5-
nitro phenol
2-Ami no-4-1N-methyl -
sulfamoyl) phenol
FIGURE 1-26. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: o-NITROPHENOL
-------
£-Nitrophenol
Red'n
->• 4-Aminophenol
EO
(Process 12)
2-(£-nitrophenoxy)-
ethanol hydrocWoride
2,6-di bromo-4-ni tro-
phenol
2.4 DAT
_Ac2Q_
Red'n
Intermediate quinonimine ——
Oxid'n
4-N-Acetylaminophenol
2-(p_-Anrinophenoxy)-etha-
nol hydrochloride
HNO,
H+
(Process 4)
8-Amino-7-methyl-2-
phenazinol
2-Nitro-4-Nacetyl-
amlnophenol
4-Amino-2-nitrophenol
FIGURE 1-27. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
J-NITROPHENOL
»-Nitro-
"toluene
Red'n
3-ToTuidtne
MeCt
—BM03_> 3-Chlorotoluene
CuCl,
W-Methyl-3-toluidine
M-Ethyl-3-toTufdine
VCN
PCI
4-[(2-Cyanoethy1)-
ethylamino]-
toluidine
4-[(2-Cyanoethyl)-
ethylamino]-2-
tolualdehyde
4-Chloro-2-toluene- • Red'" » 4-Chloro-2-
sulfonyl chloride
CA
toluene-
mercaptide
C4-Ch1oro-2-tolylmereapto)-
acettc acid
(Process 4)
-> H-BenzyT-N-ethyl-
3-toluidine
FIGURE 1-28 SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: m-NITROTOLUENE
-------
o-Nitrotoluene
Red'n
(Process 19)
2-Toluidine
(Process 12)
do ^
2-Chl oro-6-ni trotol uene
4-Ch1oro-2-nitroto1uene
BON
PC}
BOA
4-NP
Red'n
Diketene
HMO,
H2S04
HAc
Red'n
Red'n
3-Hydroxy-2-naphth-2-
toluidide
3-Hydrpxy-2-ant:hro-2-to-
luidide
4-{4-Aniino-3-to1uidino)
phenol
(Process 4)
Aceto acet-2-toluidide
6-Nitro-2-to1uidine
+
4-Nitro-2-to1uidine
2-Acetotoluidide
(Process 45)
5-Chloro-2-to1uidine
-> 6-Ch1oro-2-toluidine
-> (24) [Figure l-29b]
BON
(Process 4)
(Process 4)
Diketene
4'-Chioro-3-hydroxy-2-
naphtho-2-toluidide
3-Ch1oro-2-methy1-
phenylhydrazine
l-(6-Chloro-2-tolyl)-3-
methyl-5-pyrazolene
FIGURE l-29a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYES AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: o-NITROTOLUENE
-------
o.-Acetotoluidide (Q)
(Cont'd) [F1gure !_
(Process 12)
Cl,
UD
HNQ-
4-Chloro-2-acetotolui- Saponifi-
dide atlon
T NaOH
i KMnO,
4-Nitro-2-aeetotoluidfde
Rerf'n
-> 4-Chloro-2-toluiaine
MeOH
Red'n
—BON ^ 4'-Chloro-3-hydroxy-2-
naphtho-2-toluidide
JDiketenc^ Acetoaceto-4-chloro-2-
toluidide
—yNP-3 ^ 5-Ch1oro-4-nitro-2-to-
luidine
JCOCT ^ 6'-Methyl-4'-nitro-3-
benzanisidide
6-Methyl-4-nitro-3-
anisidine
4'-Amino-&'-methyl-3-
benzanlsidlde
4-Ghloroanthranil Ic
acid
4-Amino-2-acetotolufdide
EtOH
4-(N-N-Diethy1amine)-
2-acetotoluidfde
_J201_NaOH> 2-Amino-5-N, N-diethyl-
ami rrotol uene
4-Nitro-2-toluidine
HCOOH
5-Nitro-2-formo-to1ui-
dide
Red'n
5'-Amino-2-formo-to1ui-
dide
FIGURE l-29b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: o-NITKOTOLUENE (Continued)
-------
|J n 1 1.1 \j LU i UCMC
CT!
O
— • p- •* loiuiuine-
(Process 15) (Process 5)
Oleum k r Nitrn o
toluene-
sulfonic
acid
(Process 12)
^ ' 9 fe. *> Thl nr*n
• • c ^ c-cn loro-
4-nitro-
toluene
CISO^H^. c MJ*«~ o
o — ^ y-INlLrO-t-
toluene-
sulfonyl
chloride
Cr03 . . ,t
benzalde-
hyde
T j »• J-Hydroxy-i;-napntho-
4-toluidi;de
Diketene. . .
^ MCetOaCet-**-
toluidide
ttUH ^ ., r*(-.,i M p huHrrwx/
ethyl -4-tol ui di ne
HAr
"^r hn ArotA 4 tnlii-iH-irlo
>
Tosyl C 1 ^ H Tr,^vi4.r.i.M*j^rimi
(Process 15)
Baking ^ f nminr. -i tniiinno
"2^4 sulfonic acid
nitUo ^^ o fj 2 -i-y-r,-. /l -f-nliiTrlinrk
i. cA3 ^ j-iNi tro-'r-to i u lui ne
"2iu4
(Process 17)
^ ? (A Anri n Anhnn\/1 ^ T
methyl benzathi azol e
Red n . r nm1-nn o ..tnlnnnr.
sulfonic acid
Red'n k ., fhinro-1-tolui-
dine
^^^ ik 5 Nitro-2-toluene-
sulfonamide
"^' hi M rhlni-nnthi/l W ^"S^'"?^^dk
^ n-tn luroeiny i -n- c. .,,-.1, <» ^
ethyl -4-tolui- NUR
(Process 12) d1ne
^ ' 1 Ik T Thl rtt-n rt ->/-,->+• r» HoU w
t ^ o-Ln.i oro-4-aceto~ c ^
toluidide
HNO, . o Ki, „ . ., H00
toluidide
Ac?° fc ^ Nitrn 4 nrPtn Red'n k
toluidide
(Process 17)
Oleum b -> /a anrinnDhenvn
6-methyl - 7-benza-
thiazole-sulfonic
acid
(Process 15)
Baking ^ 6-Amino-4-chloro-
H2S04 3-toluenesulfonic
acid
Red'n » 5-Amino-2-toluene-
sulfonamide
L4-(2-Chloroethyl)
ethylaminej-2-tolu-
aldehyde
3-Chloro-4-toluidine
Nitro-4-toluidene
3'-Ainino-4-aceto-
toluidide
FIGURE 1-30. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
2-NITROTOLUENE
-------
Phenol
HN00
4-Nitrosophenol
2-Toluidine^ 4.(4._Amino-3'-toluidi-
no)-phenol
H-4-
l6n
4-Cyclohexyl -phenol
J§SP_3H
2_Am1no_4_ ( methyl sul-
fonyl )- phenol
FIGURE 1-31. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYES AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL: PHENOL
^-Phenolsulfonic -,-HN-3-
acid
£-Pheno1su1fonic
acid
4-Hydroxy-3-nitro-
benzenesulfonic
acid
Red'n
3-Amino-4-hydroxy-
benzenesulfonic
acid
(Process 15)
Phenol--2,4»disulfonic-
acid
HNO,
4-Hydroxy-5-nitro-l,3-benzene-
disulfonic acid
HNO,
Red'n
Day* 4- ' I
•Picric acid -„*[.,_ ^Picramlc
Red'n
acid
• 5-Amino-4-hydroxy-
1,3-benzenedisulfonic
acid
FIGURES 1-32 and 1-33. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIALS-
o- and £-PHENOLSULFONIC ACID
-------
Phthalic
anhydride
2-Nitrophthalic anhydride
en
rv>
SP1 MNfi Fa HP1
"u * £„ ^^^d.-rhl nvr»hr»nTmfl ^ ... rT , . , A, *? f A Phi nvn 1 -- *• kn
A1U3 benzoic acid H2b°4 nitrobenzoyl) Na(JH
benzoic acid
benzoyl ) benzoic acid "^tUg benzoxazolyl)-
benzoic acid
1 ? DPR 4TASA
i 5 L. uuu fcm 9 f? T Hi^hl nvriSoinTniv/l \ fe>1*?i-nirhl nvn «. ••• •• . ,
i 3 benzoic acid anthraquinone
+ (Process
2,3-Dichloro- NH,
anthraquinone
Pp^"? k?.M-Mothvlh(>n7nvl^- h. (2?J fFinuro l-^dhl
2^d llvHvr»w^T nitt-n^ , ,R ,„",„ L1,
benzoyl) benzoic
acid
(Process 36)
9 & Bb ° Aminn ?-hvHrnyv-
anthraquinone
H00
amide)-2-chloro- NaOH
„„] anthraquinone
^2-Amino-S-chloro- Br, fc
anthraquinone
— fe» l-AHiino-2"*
chloro anthra
quinone
2-Amino-l-bromo-
3-chloroanthra-
quinone
IA1C1-
5H
benzoic acid
Anthraquinone
(26) [Figure l-34c]
acid
FIGURE l-34a. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE
-------
~2-(4 Methylbenzoyi;
benzole acid
(Cont'd)
CO
(Process 12)
/CN C12 „ ,„ Oxid'n
fe i"ci, fa* v i i Phi nt* n fL v* > *j 1 1 fci?(4pT»*Knv\/
IFigure l-34a] rie thy 1 -benzoyi) Jln 4 3-chloro-
bsnzoic acid benzoyl)-
benzoic acid
2Ph1 nynnn fhrjirrMip- ,;„.,, K™ ' ^ T-lturlrn-
Oleum „ rnrhnY,. -, Red
'n .
— • — ™ — ^ c. -uaruoxy-j- ( ^
chloroanthra- Zn.Ni.j
quinone
.......... 2-Toluidine^ , u,,^ ,
', 2-carboxylic acid cene-2-carboxyl ic anthro-2-
acid toluidide
H9SO. HNO, HMO, pn
k ° Mrf-hvl k ° Mofhul 1 3 *. i m.-^.... o r^l-l1^
anthraquinone nitroanthra-
quinone
l-Nitro-2-anthra-
qui none-carboxyl
chloride
2Mof-hul Tnthrn . ftt 1 Phlnrn ? ,
£ Q »• l-HILIU-t- p»
3 anthraquinone-
Cflrhnxylic arid
Na?S HNO
r~, w 1 Ami nn *^ mnf h^/1
(Process 25) anthraquinone
^U *. n 01 r\^ J.I...1 n
l-Nitro-2
anthra-
qui none-
carboxyl
chloride
I k
, ., _ ^.
quinone-1- methyl- I'-bianthra-
hydrazine anthraquinone quinone
FIGURE l-34b. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
-------
Anthraquinone
(Process 15)
2\ Oleum
.
{Figure l-34a]
cn
U 1 GUm
HNO
sulfonic acid
2-Anthraquinone-
sulfonic acid
quinone
(Figure 1-
-H23) (Figure 1-
N* ^
»QO->
IMj-
(Process 34)
• 1-Aniinoanthra-
quinone
1,8-Dinitro-
anthraquinone
Na0S
{Figure 1-
1,8-Oiamino-
anthraquinone
(Process 28)
anthraquinone
-fc-l-Ainino-5-nitro-
anthraquinone
0COC1
M-Nitro-5-benzamide-
anthraquinone
2*2- ^ l-Amino-5-benzamido-
anthraquinone
(Process 32)
,5-Diamino-anthraquinone
(Process 12)
C1
Process 26)
Zn
or Al
(Process 39)
1,4,5,8 Tetra-
chloroanthraqui none
(Process 26)
> Anthrol
>,H-Benz (de)
anthracen-7-
one (benzan-
throne
HNO-,
ReTn
->• 3-Amino-
benzanthrone
Ac00
— - ^-3-Acetamino-
benzanthrone
HNO-,
H2S04
3-Acetamino-2-
nitrobenz-
anthrone
2-Hydroxy-
benzanthrone
(Process 12)
>>3-Chlorobenzan throne
(Process 12)
k12 ^.3,9-Dichlorobenzanthrone
(Process 12) (Process 34)
"T.p ^. 3-Bromobenzanthrone
(Process 12) (Process 34)
^rr ji ^ 3,9-Dibromobenzanthrone
nitrobenzanthrone
->2-Methoxy-
benzanthrone
HN_0,_
Red^n
(Process 26)
FIGURE l-34c.
~y -»• 3-Benzoyl-benzanthrone
A I \j I ^
SYNTHESIS Of VARIOUS INTERMEDIATES FOR OYE AN!) PI WENT PIJO'lUCTinfi FROM
PURCHASED STARTING MATERIAL: PIITHAUC ANHYDRIDE (Continued)
-------
1-Anthraquinone
sulfonlc acid
(Cont'd)
(Process 15)
O''eui
[Figure l-34c]
en
en
Hg
HNO,
IHCT
1,8-Anthraquinone-
disulfonic acid
1,5-Anthraquinone- (Process 28)
disUlfonic acid m
Oxid'n
Ca(OH),,
1,8- Dicnloroanthra-
quinone
1,8-Dihydroxyanthra-
quinone
(Process 32)
1,5-Diaininoanthraquinone
(Process 33)
> 1,5-Dihydroxyanthra- Oleum *• 1,5-Dihydroxy-
quinone anthraquinone-2,
6-disulfonic acid
(Process 33)
l,5-Dihydroxy-4,8 -^§ti ».
dinitroanthra-
quinone-2,6-
disulfonic acid
4,8-Diamino-l ,5-dihydroxy-
anthraquinone-2,6 disulfonic
acid
(Process 33)
^>
.MeOH
->1,5-Dimethoxy-
anthraquinone
HNO,
H2S04
1,5-Dimethoxy-4,8-
dinitroanthraquinone
NaC10
HC1
1,5-Dichloro-
anthraquinone
1,5-bis-(Dinitro-
phenoxy)-4,8-di-
nitroanthraquinone
1,5-Diphenoyx-
anthraquinone
HNO-
H2S04
1,5-Dihydroxy-4,8-
di ni troanthraquinone
,5-Diamino-4,8-dihydroxyanthraquinone
->• 5-Ni tro-1-anthraqui none-
sulfonic acid
HC1
l-Chloro-5-
nitroanthraquinone
Red'n
l-Amino-5-chloro-
anthraquinone
8-Nitro-l anthraquinone-
sulfonic acid
[Figure l-34e]
NaCIO,,
HC1
->• l-Chloro-8-nitro
anthraquinone
FIGURE l-34d. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
Red'n
• l-Amino-8-chloro-
anthraquinone
-------
(Process 12)
1-Anthraquinone
sulfonic acid
(Cont'd)
(Process 28)
T'NaB'rS > 1-Methylamino- —^ H-Bromo-4-methyl- | ftcg° M-Bromo-4-(N-ntethylacetamido)-
{Figure 1-34d]
en
en
MeONa
NaCIO.
HC1
•NaCIO,,
anthraquinone
ami noanthraqui none
anthraquinone
(Process 28)
4-To1uidinVl-(N-Methy1amino)-
4-£-toluidino-
anthraquinone
acetamido)-
4-£-tolu1d-
inoanthra-
quinone
->l-Methoxyanthraquinone
1-Amino-anthraquinone- —
i
NH3 (Process 28)
HNO-
->l-Chloroanthraquinone
[Figure 1-34H]
(Process 28)
l-Chloro-4-nitro--|Aa • »• N-(4-Nitro-1-
Red'n
anthraquinone
anthraquinonyl)-
anthranilic acid
(Process 23)
wu
^•3 > 1 -Ami no-4-ni tro-
anthraquinone
>N-(4-Amino-l-
anthraquinonyl)
anthranilic
acid
0COC1
Red'n
(Process 37)
l-Amino-4-
benzamido-
anthraquinone
>l-Nitro-4-
benzamido-
anthraquinone
SOC12.
l-Benzamido-4-chloroanthraquinone
HBr
©[Figure l-34f]
>• 1-Bromoanthraquinone
FIGURE l-34e. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
-------
1-Anthraquinone ® Ca(OH)2 , Hvdroxv anthra HNO, fc
sulfonic acid - Z * ™7™™ I l-Hydroxy-4-nitro-
(cont'd) [Figure 1-34e) quinone | anthraquinone
(Process 12)
Br
H.-2———^ l-Bromo-4-hydroxy-
^^ anthraquinone
(Process 12)
> l-Chloro-4-hydroxy-
anthraquinone
FIGURE l-34f. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
-------
-2-Anthraqui none-
sulfonic acid
(Conf d)
tn
CO
~~~ ^ C*& n *• ^ H"+t»- ->-"""
[Figure l-34c]
I
sul fonic acid
i
(Process 15)
Oleum , r
Hq r '^ *?" v'111 u . . _
quinone-disul
fonic acid
Na2S
h. d
^ H
(Process 15)
_ Oleum , c. flnthramiinn
NaOH 0
lAlo
- > 2-Hydroxy- _ r
anthracene riau"
r ,nH, (Process 15)
2 k. i - ,v, , Oleunl -
+ 1 ,5-Uihydrox.y- •
anthraquinone
rteOH
HO
O" Hi ami nn 1 *> -, ^ fa
dihydroxy-anthra- 2 24
quinone-2,6-di-
sulfonic acid
Ca(OH)2
r ^ »o-,'\n tnraqu i nOiic - - ^ £.,U-UIH^UI UAJ' ai
disu) fonic acfd quinone
(Process 28)
NaClO, NH.,
•3 W 7,-Phlnv-n k. o A^.J —
anthraquinone
Process 23)
NaOH , 7 n-i'Kw^ynvw-
a;ithraquinone
(alizarin)
anthraquincne
Oxld'n i o 4 Tr1
hydroxy-
anthraquinone
(purpurin)
- - — - ™w
>• 1,4,5,8-Tex
h,ydroxy-a
quinone
ithra-
( Process 12)
(Process 12)
(Process 15)
Oleum .
roccss 28)
Nh'4OH
w
w
-> u. j»~ . 2 Toluidine^
o-Hydroxy- — ~ — - ^
anthracene- ^^3
2-carboxyl ic
acid
HNO,
1 ,5-Dihydroxy v, ,.*. >
anthraquinot e 24
2,6-disulfonic
acid
tra-
nthra-
2 -Ami no- 1 ,3-
dichloroanthra-
quinone
2-Amino-l ,3-
dibrornoanthra-
quinone
3-Amino-2 -anthra-
quinone-sul fonic
acid
l-Amino-2,4-
dihydroxy-
anthraquinone
3-Hydroxy-:-
anthro-2-
toluidide
1 ,5-Dihydroxy
4,8-dinito-
anthraquinone
2,6-disul-
fonic acid
FIGURE l-34g. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
-------
(Process 311
1-Aminoanthra- ^ 0COC1
quinone [Figure l-34c), '
,
(Cont'd) [Figure l-34e]'
(Process 12)
•>1-Benzamido- -^2^3 $
anthraquinone
l-Benzamido-4-
chloroanthraqui none
]MUcj£i4>1.Anthroqu1nonyl. _HJ%_
en
oxamic acid
Red'n
> 4-Nitro-l-anthro-
quinonvloxamic
acid
Na,S
->1-Amino-4-nitro- 2£2£!-
anthraquinone
• 1-Nitro-4-benzamjdo-
anthraqulnone
(Process 12)
ac
(Process 37)
—^l-Amino-4-benzamido-
anthraquinone
(Process 28)
-H-Amino-2,4-
dibromoanthra-
quinone
aj^2 >> l-Amino-4-anilino-2-
bromoanthraquinone
(Process 28)
lp-tolu1d1n^l.An|1no.2.bron|0.
4-£-toluidino-
anthraquinone
(Process 15)
Oleum .
(Process 12)
C10
(Process 15)
Oleum
>l-Amino-2,4-
dichloro-
anthraquinone
NaOH
H20
l-Amino-2-chloro-4-
hydroxyanthraquinone
(Process 12)
•^l-Amino-2-anthra- -5^2 ^l-Amino-4-bromo-2--
quinonesulfonic anthraquinone-
4-ANBS
acid
sulfonic acid
5-ANBS
NaOH
4TASA
(Process 35)
NaNO,
HC1
• 1-Anthraquinonyl-
hydrazine
(Process 35)
NaHSO, . . .
NaOH '
(1-Anthraquinonyl]
1,2-hydrazine-
sulfonic acid
l-Amino-2-bromo-
anthraquinonyl-4-£
toluidinesulfonic acid
•l-Nitro-4-(3-amino
4-sulfoanilino)-2-
anthraquinone-
sulfonic acid
•l-Nitro-4-(4-amino-
3-sulfoanilino)-2-
anthraquinone-
sulfonic acid
Red'n
Red'n
->-l-Amino-4-(3-amino-
4-sulfoanilino)-
2-anthraquinone-
sulfonic acid
^ l-Amino-4-(4-amino-
3-sulfoanilino-2-
anthraquinone-
sulfonic acid
•l-Amino-2-bromo-4-
hydroxyanthraqu i none
• 1-Ami no-4-£-tol uene-
sulfamido-2-anthracene-
sulfonic acid
FIGURE 1-34H. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM
PURCHASED STARTING MATERIAL: PHTHALIC ANHYDRIDE (Continued)
-------
(Process 11) JPr?cess 12)
Resorcinol -r-^^ig », 4-Chlororesorcinol
3-Anilinophenol
FIGURE 1-35. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL: RESORCINOL
cr>
° Salicylic acid _,J!§2^4—». 2-Anisic acid
—3 *• 5-Nitrosalicylic acid Red " *• 5-Aminosalicylic acid
FIGURE 1-36. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL: SALICYLIC ACID
(Process 12) (Process 3)
Toluene ^2 *• 4-Chlorotoluene —3 » 4-Chloro-2-nitrotoluene
+
4-Ch1oro-3-nitrotoluene
FIGURE 1-37. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
TOLUENE
-------
p-To! uenesul fonic acid
HNO,
(Process 12)
(Process 15)
3-Ni tro-4-to!uenesul -
fonic acid
3-Chloro-4-toluenesul -
fonic acid
To!uene-2,4-disulfonic
acid
NaOH
Red'n
HNO,
KMnO,
4-Sulfoanthranilic acid
4,4'-Diamino-5,5'-di-
methy1-2,2'-biphenyldi-
sulfonic acid
3,5-Dinitro-4-toluene-
sulfonic acid
(Process 11)
4-Formyldisulfonic acid
Red'n
FIGURE 1-38 SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
£-TOLUENESULFONIC ACID
3,5-Diamino-4-toluene-
sulfonic acid
-------
(Process 12)
fi- Toluenesulfonyl chlor-
ide
3-Chloro-4-toluenesul-
fonyl chloride
H,n
*_ W"
Red'n
Oxid'n .
c-.
t\3
3-Chloro-4-toluenesul-
fonic acid
2-Amino-5-chloro-4-tolu-
enesulfonic acid
5-Nitro-2-chloro-4-sul
fobenzoic acid
-> 2-Chlorotoluene
(Process 6)
2-Chlorobenzaldehyde
2-Chloro-4-ch1orosul-
fonyl benzoic acid
HNO,
Red'n
(Process 12)
Clo
NH,
5-Ch1oro-2-nitro-4-to1u-
enesulfonic acid
5-Amino-2-chloro-4-sul-
fobenzoic acid
2-Chlorobenzylidene
chloride
2-Formyl benzene sulfonic
acid
2-Chloro-4-sulfamoylben-
zoic acid
FIGURE 1-39. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
2-TOLUENESULFONYL CHLORIDE
-------
1,2,4-Trichloro-
benzene
»2,4,5-Trich1oro-
nitrobenzene
Red'n
MeOH
2,4,5-Trichloroaniline
4,5-Dichloro-2-methoxy-
nitro-benzene
MeOH_
NaOH
5-Chloro-2,4 Dimethoxy-
nitrobenzene
Red'n
5-Chloro-2,4-di- IPJ-
methoxyaniline
5'-Chloro-3-hydroxy-2'-,
4'-dimethoxy-2-
naphthanillde
FIGURE 1-40. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION
PURCHASED STARTING MATERIAL: 1,2,4, TRICHLOROBENZENE
CTi
CJ
HNO-
Trimemtic
anhydride
mell i tic
acid
n A, HN09
Red'n & 5 Aminotri 2
mellitic acid
(Process 11)
-$> 5-Hydroxytri-
mel litic acid
FIGURE 1-41. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
TRIMELLITIC ANHYDRIDE
m-Xylene
HN03 Red'n Diketene (Process 4)
^—*• 2,4:Dimethyl- ^S-Q ^ 2,4-Difiiethy]- u1Keiene—^ 2,4-Dimethyl-
nitrobenzene aniline acetoacetanilide
FIGURE 1-42. SYNTHESIS OF VARIOUS INTERMEDIATES FOR DYE AND PIGMENT PRODUCTION FROM PURCHASED STARTING MATERIAL:
m-XYLENE
-------
CTt
-t*
PROCESS NO. 1:
NITROSO DYES AND PISMENTS: C.I. 10005,
10006, IOOM
NaNO?
NaOH
Ice
HZS04
eSO,
or NaHSO,
Nitrosation,
Filtration
o
(Flgurt 2-1S)
1A
C.I. 10005
10006
10020
PROCESS NO. 2:
NITRO OYES: C.I. 10316
NaN02
NaOH
H2S04
Ice
Nitrosation
2A
Nitration, Filtration
2B
C.I. 10316
o
rFljurt 2-34)
PROCESS NO. 3:
NITRO DYES: C.I. 10338, 10345, 10395
Replacement Reaction,
nitration
3A
C.I. 10338
10345
10395
FIGURE 2-1. FLOW CHART FOR THE PRODUCTION OF SELECTED NITROSO AND NITRO DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 1
NITROSQ DYES (C.I . 10005. 10006, 10020)
1. Function - This process serves to transform either 2-naphthoT (C.I. 10005
and 10006) or 2-naphtho1-6-su1fonic acid (C.I. 10020) into a color product.
The pigment formation process step serves to make the intermediate dye into
a very insoluble material which can serve as a pigment. A simple stirred
reactor made of stainless steel serves for carrying out the necessary reactions
2. Input Material^ - The required materials for making these colors are shown
in Exhibit 1. Ice is required to cool the nitrosation reactions.
EXHIBIT 1
Color Index No. 10005 10006 10020 10020:1
Component
2-naphthol x x
sodium nitrite x x x x
sulfuric acid x x x x
ferrous sulfate x x x
sodium bisulfite x x
barium chloride x
2-naphthol~6-sulfonic acid x x
3. Ogerating Parameters - The sequence of reactions is carried out in a stirred
reaction vessel under atmospheric pressure. The nitrosation reactions must
be carried out at 0-5°. Reactor sizes are not known.
4- Utilvtigs. - Water, refrigeration and electricity are needed, but the required
amounts are not known. /
5- Waste Streams - Inevitably, through errors in operation, • nitrogen oxide
fumes escape into the air. Solutions of inorganic salts are discharged
when the dye or pigment is recovered. The ions in these solutions may
include the toxic barium ion (C.I. 10020:1). Nitrogen oxide fumes are
generally allowed to escape into the air from a tall stack or pipe.
Usually no effort has been made to control fluid effluents.
References - Pigment Handbook, Edited by Temple C. Patton, John Wiley
Sons, New York~(1973), Volume I, Chapter I-D-a, "Pigment Green B"
(C. G. Inman), pp 435-440.
65
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 2
NITRO DYES (C.I. 10316)
1. Function - This process serves to introduce a nitro group at the 2- and 4-
positions on l-naphtho1-7-sulfonic acid. The objective is most readily
achieved by first nitrosating the preferred main starting material.
Simple stainless steel stirred reactors are used throughout the process.
2. Input Materials - The principal starting material is l-naphthol-2,7-disu1fonic
acid. The other input materials are: nitric acid, sodium nitrite, sulfuric
acid, sodium hydroxide, ice, and water. The quantities required are not
known. It should be recognized that the nitrosation reaction must be carried
out at 0 to 5°.
3. Operating Parameters - Conditions for this process were not given in the
readily accessible literature. The nitrosation reaction would very likely
be carried out at 0-5°C because this is usually the case.
4. Utilities - Electricity, steam,refrigeration and water are required, but
the amounts needed are not known'.
5. Haste Streams - The nitrosation reaction may lead to the emission of
nitrogen oxide fumes if operations are not carried out carefully. Isolation
of the intermediate nitroso compound results in an aqueous effluent laden
with inorganic salts. Nitration of the intermediate also entails the
emission of nitrogen oxides which are difficult to control by water
scrubbing.
6. EPA Source Classification Code -
~1 • References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume 1, p 405.
66
-------
ORGANIC DYES AND PIGMENTS PROCESS N0._3.
NITRO DYES (C.I. 10338, 10345)
1. Function - The process involves the substitution of an arylamino moiety for
chlorine substituted on the ortho position of an aryl nitro compound. This
chlorine is highly activated, so that the replacement reaction goes readily.
The product is always a yellow dye. The reactions involved can be satis-
factorily carried out in steel reactors open to the air. Good stirring is
necessary.
2. Input Materials - The required input materials are shown in the matrix below
(Exhibit 1).The quantities of these materials needed to make 100 pounds of
each dye could not be found in standard texts on dyes.
EXHIBIT 1
Color Index No. 10338 10345 10395
Component
anilinex
4-chloro-3-nitrobenzenesulfonyl
chloride x
£-aminophenol x
l-chloro-2,4-dinitrobenzene x
4-chloro-395,dinitrobenzoic acid x
5-amino-2-ani1inobenzene-
sulfonic acid x
3- Operating Parameters - No data are available on the detailed conditions under
which the process is operated. However, the reactions are likely to be
somewhat exothermic. The process is always carried out batch-wise in stirred
reactors under atmospheric pressure.
4- Uti1ities - Electricity, steam, and water are needed, but the amounts required
are not known.
5- Haste Streams - The principle waste product from making these dyes is a
brine contaminated with small amounts of organic substances.
6. EPA Source Classification Code -
7« References - The Chemistry of Synthetic Dyes and Pigments, Edited by
H. A. Lubs, Reinhold Publishing Company, 1955, "Miscellaneous Dyes"
(S. E. Krahler), pp 255-256.
67
-------
PROCESS NO. 4:
AZO DYES AND DERIVED PIGMENTS: C.I. 11000-36300
CouplIng
I
48
Pigments 1| Dyes
[Figure 2-15] ( 2 ) (Figure 2-34]
* Weakly basic anilines only.
FIGURE 2-2. FLOW CHART FOR THE PRODUCTION OF SELECTED AZO DVES AND PIGMENTS FROM VARIOUS INTERMEDIATES
68
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 4
AZO DYES AND PIGMENTS
1. Function - Azo dyes and pigments are the most numerous of the various classes
of organic dyes and pigments. The two principle starting materials are
first an arylamine, and second, an arylamine, a phenolic compound or naphthol
ether, or a compound with a reactive methylene group. These starting
materials are sometimes much modified by the presence of other substituents.
A frequently encountered substituent group is the sulfonic acid moiety.
The equipment needed for making these dyes is simple. A well stirred
batch tank suffices for the reactor. Filter presses are generally used
for recovering the finished products and tray driers for drying the dye
and pigment presscakes.
2. Input Materials - The principle input materials are both too numerous and
highly varied to be listed here. Sodium nitrite, hydrochloric acid, sulfuric
acid and sodium hydroxide are the important auxiliary starting materials.
Some of the starting materials are either highly carcinogenic or very toxic,
and must therefore be handled with stringent precautions. Two of the most
notorious of the carcinogenic starting materials are benzidine and
yS-naphthylafFtine. The effect of exposure to these chemicals is highly
insidious because the cancer is not detected until many years after
exposure. Today» ^-naphthylamine is not manufactured in the United States.
The starting materials are usually employed in ratios dictated by the
chemical stoichiometry.
A specific example of quantities used to manufacture an azo dye,
chrome Blue Black U, is given in Exhibit 1.
3. Operating Parameters - No quantitative data are available on the required
utilities. Note should be taken that the diazotization of amines must be
carried out at Q-5°C with highly effective stirring to avoid localized
overheating. Accordingly, the reactors used are simple batch tanks with
effective stirrers. Ice is usually employed to attain the needed low
temperature for the diazotization step.
4- UtT1ities - Electricity, water, and refrigeration are needed, but the amounts
required are not known.
5- Waste Streams - The main waste products are inorganic salts dissolved in
the aqueous effluents. Varying amounts of organic materials (both starting
materials and products) are also contained in these liquids. Occasionally,
nitrogen oxides are emitted in the course of the diazotization step. For
the specific example used above of the manufacture of 1800 Ib of chrome Blue
Black U there is a waste stream of 2810 Ib of aqueous solution contaminated
with organic compounds created.
6. EPA Source Classification Code -
69
-------
Azo Dyes and Pigments Process No. 4
Page Two
EXHIBIT 1.
MATERIALS USED FOR MAKING 1800 LB
CHROME BLUE BLACK U
Beta-naphthol 730 Ib.
Sodium hydroxide (40%) 600 Ib.
Water 10,000 Ib.
Hydrochloric acid (20%) 500 Ib.
1 -amino-2-naphtho1-4-sulfuric acid 1,200 Ib.
Sodium chloride 200 Ib.
Copper sulfate hydrate 15 Ib.
Sodium nitrite 365 Ib.
70
-------
Azo Dyes and Pigments Process No. 4
Page Three
References - (a) Fierz-David, H. E. and Blangey, L., Fundamental Processes
of Dye Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), Chapter II, pp 239-297.
(b) The Chemistry of Synthetic Dyes and Pigments, Edited by H. A. tubs,
Reinhold Publishing Co. (1955), Chapter 3, "Azo Dyes" (S. N. Boyd, H. E.
Woodward and J. F. Laucius), pp 96-98. (c) Venkataraman, K. , The Chemistry
of Synthetic Dyes, Academic Press, New York (1952), Volume I, pp 210-220,
480-621, 650-704, (d) Booz-Allen Applied Research, Inc., A Study of Hazar-
dous Waste Materials, Hazardous Effects and Disposal Methods, National
Technical Information Service, Springfield, Va. (1973), p. 338.
71
-------
PROCESS NO. 5: STILKIK WES AM P1GKRTS: C.I. WOOO-40645
C.I. 40645
Revised 5/16/75
(Figure 2-341
FIGURE 2-3. FLOW CHART FOR THE PRODUCTION OF SELECTED STILBENE DVES AND PIfiWNTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 5
STILBENE DYES
1. Function - Although stilbene dyes are classified chemically as azo type
dyes, the manufacturing process for making them is distinctly different
from that used to make conventional azo products. The principal organic
starting material is 5-nitro-p_-toluene sulfonic acid, but cyanuric chloride,
certain arylamines and benzaldehyde are also required for specific stilbene
dyes. All of these dyes are made in a stirred, batch reactor constructed
of iron and fitted with a reflux condenser.
2. Input Materials - A laboratory procedure for making C.I. 40000 is given
in Fierz-David and Blangey. About 1.3 pound of sodium 5-nitro-p_-toluene-
sulfonate and 0.41 pound of sodium hydroxide is required per pound of
C.I. 40000. The other required raw materials and the respective dyes made
from them are shown in Table 1.
3. Operating Parameters - The reactions for making these dyes are carried out
at relatively low temperatures with water as the medium. The reaction
for making C.I. 40000 takes place at 65 to 75°C. The reactor capacity
needed is projected to be 1.3 gallon per pound of finished dye.
4- Utilities - Electricity, water, and steam are required, but no information
is available as to the necessary amounts.
5. Waste Streams - The waste streams from the manufacture of stilbene dyes
are almost entirely brines containing small amounts of organic materials
(both starting materials and finished dyes). The manufacture of C.I. 40645
might also result in the emission of nitrogen oxides.
6. EPA Source Classification Code -
7- References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of
Dye Chemistry, Translated from the Fifth Austrian Edition by
P. U. Vittums Interscience Publishers, Inc., New York (1949),
p. 297; The Chemistry of Synthetic Dyes and Pigments. Edited by H. A. Lubs.
Reinhold Publishing Co. (1955), Chapter 3, "Azo Dyes" (H. E. Woodward),
pp 119-121; Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume I, pp 628-636.
73
-------
Stil bene
Page Two
Dyes
Process No. 5
Table 1. RAW MATERIALS USED FOR MAKING STILBENE DYES
Component
5-nitro-o-toluenesulfonic acid
sodium hydroxide
formaldehyde
glycerol
glucose
sodium sulfide
aniline
3-(4'-amino phenylazo) benzenesulfonic
acid
4-(4'-amino phenylazo) benzenesulfonic
acid
4-(4'-ami no-2'-methylphenylazo)-
benzenesulfonic acid
3-(4'-ami no-5'-methoxy-2'-methy1 -
phenylazo) benzenesulfonic acid
4-(4'-aminonaphthylazo) benzene-
sulfonic acid
naphthionic acid
sodium nitrite, sulfuric acid
phenyl isocyanate
cyanuric chloride
diethanolamine
ammonia
2-amino-l-naphthalenesulfonic acid
Derived Dyes
all stilbene dyes
all stilbene dyes
40001, 40630
40002
40002, 40300
40003
40045, 40621, 40622
40210
40215
40220
40260
40290
40300
40300,
40600
40621,
40622
40630
40645
40645
40622, 40130
74
-------
PROCESS NO. 6:
DIARYLMETHANE AND TR1ARYLMETHANE DYES AW> DERIVED PIGMENTS: C.I. 41000, 41001. 42000-42170, 42595, «2640-«2735
CS1
O
Condensation
68
1
r T
'Pb02
NH3
HOAc
Na2S04
ZnCl2
HjCi-04
^
/ Leuco \
I Dye 1
I (Solution) /
T
t A t
Oxidation, CrystalU- ^^ roieuinH _ Sulfonation
zatlon. Filtration IWaterr^ F11t
6C
41000, 41001
*
I
7^
/ Trisi
1 fona
1 Leuco
fphn,"| I
HOAc .,, ,1m. Oxidation,
C.I. 42000-42090 H2S°4 t^"- F"tr
4?inn.j?i7n. mm
. 42595 u J 1
42640-42735 J
V
6E
C.I. 42053, 42095,
42655
IFtgurt 2-151
O
(Figure 2-341
FIGURE 2-4. FLOW CHART FOR THE PRODUCTION OF SELECTED DIARVLMETHANE AND TR1ARYLMETHANE DYES AND DfRIVED PIGMENTS
FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 6
SELECTED DI- AND TRIARYLMETHANE DYES
FROM VARIOUS INTERMEDIATES
Function - Several basic dyes can be made by a primary reaction between an
aromatic amine (usually disubstituted on the nitrogen) and either formaldehyde
or a benzaldehyde compound. Two of the dyes (C.I. 41000 and 41001) require
only a single process step, a condensation reaction. All others require a
second process step following the condensation reaction. This second process
step may be either an oxidation reaction or a sulfonation reaction. These
dyes are all characterized by having one or more basic nitrogen moieties in
the finished product. Insoluble pigments are made from some of these dyes by
a reaction with dye precipitants, (cf. Process No. 18).
The processing equipment is all very simple. The primary reaction
vessels are stirred, batch reactors with a glass lining and the products
are recovered with ordinary filter presses.
2. Input Materials - The principal input materials are:
Organi c
Formaldehyde
N,N-Dimethyl aniline
o-Ch1orobenza1dehyde
Benzaldehyde
N,N-Diethylaniline
4-Formyl-m-benzenedisu1fonic acid
jD-hydroxybenzal dehyde
N-Ethyl-N-phenylbenzyl ami ne
<=<-(N-Ethylanilino)-m-toluenesulfonic acid
N-Ethyl-o^toluidine
•X.-N- (Ethyl -rn-tol uidi no) -m- to! uenesul f oni c aci d
Acetic acid
Potassium antimony tartrate
Quebracho extract
Sulfanilic acid
Inorganic
Ammonia Phosphorus trichloride
Sulfur Alumina hydrate
Sodium chloride Lead peroxide
Ammonium chloride - Sulfuric acid
Zinc chloride Oleum
Sodium hydroxide Sodium dichromate
Sodium carbonate
76
-------
2 Process No. 6
3. Operating Parameters - The operating parameters vary, depending on the
exact nature of the dye being manufactured. The condensation of dimethyl
(or diethyl) aniline with formaldehyde to make C.I. 41000 (or 41001) is
promoted with a small amount of sulfanilic acid as catalyst. Heating the
mixture of organic and inorganic ingredients for making the dyes entails
very careful temperature control, achievable only with a liquid heat
transfer agent. Ammonia is used in the reactor at 0.5 psig. The condensation
of N- and ring-substituted anilines with benzaldehyde or substituted
benzaldehydes takes place at reflux temperatures and requires long reaction
times (12 hours or longer). Oxidation of the leuco base to the dye is
carried out at Q°C, using ice to cool the reaction mixture on reaction
conditions.
4- Utilities - Electricity, refrigeration, liquid heat transfer system, steam
and water are needed, but the amounts required are not known for any of
the dyes.
5. Waste Streams - The manufacture of C.I. 41000 and 41001 entails the use of
ammonia, and the formation of hydrogen sulfide. These pollutants must be
contained, and in a well-run plant, the hydrogen sulfide is recovered as
sodium sulfide for use as a reducing agent for making other dyes.
The lead ion introduced in oxidizing leuco bases to the dyes is precipitated
as lead suIfate, a solid waste product.
The liquid effluents are brines contaminated with small amounts of organic
materials.
6. EPA Source Classification Code -
?• References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of
Dye Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), p. 137, Chapter E,
298-308; The Chemistry of Synthetic Dyes andPigments, Edited by
H. A. tubs, Reinhold Publishing Co. (1955), Chapter 5, "Miscellaneous Dyes",
(S. E. Krahler), pp 281-283; Venkataraman, K., TheChemistry of Synthetic
Dyes. Academic Press, New York (1952), Volume II, pp 705-706, 711-716.
77
-------
PROCESS NO. 7: TRIARTUCTHANE DYES AND PIGMENTS: C.I. 42500-42536, 42760-42780
00
f C.I. 42535
2 ) (Figure Z-34]
FIGURE 2-5. FLOW CHART FOR THE PRODUCTION OF SELECTED TRIARYLMETHANE DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 7
TRIARYLMETHANE DYES (C.I. 42500, 42536, 42760. and 42780)
1. Function - The manufacture of certain triarylmethane dyes depends primarily
on a controlled oxidation of aniline, a substituted aniline or a mixture of
selected arylamines. Secondary transformations on the primary product are
carried out to produce some of the dyes. Stirred batch reaction vessels
with glass linings serve for making these products. The dyes are separated
from the reaction mixtures with standard filter presses. Some of these dyes are
sulfonated to form still other dyes (ct. Process No. 15).
2. Input Materials - The starting materials needed for making these dyes are
shown by the matrix below (Exhibit 1). No reliable information is available
as to the quantities or raw materials needed.
3. Operating Parameters - The oxidation of arylamines with nitrobenzene is
started at 60° and the temperature gradually raised to 140°, whereupon a
highly exothermic reaction begins. The temperature of the reactor is controlled
by stopping the heat input and spraying the vessel with cold water. The
reaction mixture is then allowed to reach a temperature of 170°, with the
temperature rise not exceeding 2° per hour. The total batch time is 24
hours. The conversion of C.I. 42500 to other dyes requires heating 460
parts of the intermediate dye with 2400 parts of aniline and 8.5 parts of
benzoic acid for one hour at 180-182°. The excess aniline is removed by
vacuum distillation. Information is not available on the details of other
steps in making various dyes.
4- Utilities^ - Electricity, water, and steam are needed to make these colors, but
the amounts required are not known.
5- Waste Streams - Air oxidation of arylamines results in all three types of
waste streams. Nitrobenzene oxidation results only in solid and liquid
wastes. The solid wastes are sludges containing large amounts of metal
ions (copper, zinc and/or iron). The gaseous wastes from air oxidations
could contain significant and hazardous amounts of toxic arylamines. The
liquid wastes would be mainly brines contaminated with varying amounts of
organic substances, many of which are highly colored.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press,
New YoriTTl952K Volume II, pp 717-719, 723-724.
79
-------
Page Two Process No. 7
EXHIBIT 1
STARTING MATERIALS FOR SELECTED TRIARYLMETHANE
DYES AND PIGMENTS
Color Index No. 42500 42510 42520 42535 42536 42760 42775 42780
Component
aniline x x x x x
4,4'-methylenedianiline x x x
nitrobenzene x x x x x
ferric chloride x x x
o-toluidine x x x
jD-toluidine x x
4,4'-methylenedi-p_-toluidine x
hydrochloric acid xxxxxxxx
air x
N,N-dimethylam'line x x
phenol x x
sodium chloride • x x
copper sulfate x x
benzyl chloride x
benzoic acid x x
sulfuric acid x
80
-------
PROCESS MO. 8: TRIARYLHETHANE DYES AND PIOCNTS: 42555-42600. 44025, 44090
00
[POC13]-*-
Nipttthol
or N«plitha
lenedisul-
fonlc
Acid
C.I. 44025,
44090
Revise 5/16/75
FIGURE 2-6. FLOW CHART FOR THE PRODUCTION OF SELECTED TRIARYLMETHANE DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 8
TRIARYLMETHANE DYES (C.I. 42555,
42561. 42595, 42600. 44025. and 44090)
1. Function - The triarylmethane dyes in this group also require an N,N-
dialkylarylamine and formaldehyde among the primary starting materials, as
in the case of some of the dyes made with Process No. 6. This process
differs from Process No. 6 in respect to other important starting materials,
which include phosgene 2,7-naphthalene disulfonic acid and 2-naphthol-3,6
(or 6,8)-disulfonic acid. Stirred batch reaction vessels lined with glass
are needed for these reactions. Some of these dyes are converted to pigments
with a dye precipitant (cf. Process No. 18).
2. Input Materials - The preparation of the ketone intermediate ("Michler's
ketone") from phosgene and N,N-dimethyl aniline (N,N-diethylaniline is used
to make a tetraethyl analog) requires 4 moles of the organic base for each
mole of phosgene. The excess base serves to bind the liberated hydrogen
chloride, and it is subsequently recovered. The yield of ketone is 76%
of theoretical. The matrix below (Exhibit 1) shows the starting materials
necessary to make the several dyes. The amounts of materials needed to make
100 pounds of these dyes is not known.
3. Operating Parameters - The reaction to make Michler's ketone is started at
20° and the temperature increased over a period of 90 hours to 80°. All
reactions are operated under atmospheric pressure.
4. Utilities - Electricity, water, and steam are needed to make these colors,
but the amounts required are not known.
5. Waste Streams - The use of phosgene may lead to small amounts of gaseous
emissions. The use of lead peroxide as oxidizing agent results in a lead
sulfate precipitate which must be recovered and a brine which contains lead.
A solid distillation residue is encountered in making intermediate ketones.
All other effluents are brines containing small amounts of organic materials,
6. EPA Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume I, pp 136-137; Volume II, pp 721-722;
Fierz-David, H. E. and Blangey, [_., Fundamental Processes of Dye Chemistry
Translated from the Fifth Austrian Edition by P. W. Vittum, Interscience
Publishers, Inc., New York (1949), Chapter E, pp 306-307.
82
-------
Page Two Process No. 8
EXHIBIT 1
STARTING MATERIALS FOR MAKING SELECTED TRIARYLMETHANE
DYES AND PIGMENTS
Color Index No. 42555 42561 42595 42600 44025 44090
Components
phosgene x x x x
dimethyl aniline x x x
zinc chloride x x x x
phosphorus oxychloride x x x
N-methy1-N-phenylbenzyl amine x
sulfuric acid x x
sodium chloride x x
N-ethyl-1-naphthylamine x
diethylaniline x x x
formaldehyde x x
2,7-naphthalenedisulfonic acid x
lead peroxide x x
2-naphthol-3,6(or 6,8)-
disulfonic acid x
83
-------
PROCESS NO. 9: TRIARYINE THANE DYES: C.I. 43820, 43830
AND A METHINE DYE: C.I. 48000
H2S04 I
I NaCH r "^
[N Oxidesj
f 2 \ (Figur* 2-341
* p-ibutylU-chloroethjHaminol&enzalJenyde - C.I. 48000
1
!
» A
1 ' A
Condensation, Oxidation, rwaOHl..^^ Condensation,
Filtration Ofl L"avmr^ Filtration nn
"" 98
C.I. 43820, 43830 i
| C.I. 48000
Revised 5/19/75
FIGURE 2-7. FLOW CHART FOR THE PRODUCTION OF SELECTED TRIARYLHETHANE AND METHANE DYES FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 9
TRIARYLMETHANE DYES (C.I. 43820, 43830)
AND A METHINE DYE (C.I. 48000)
1• Function - The manufacture of these three dyes share in common the use of a
substituted benzaldehyde compound as one of the starting materials. Only a
single process step is involved in their manufacture. The two triphenyl-
methane dyes differ from those made by processes 6 and 7 in that no organic
base is involved in their manufacture. A glass-lined vessel is required in
the manufacture of the two triarylmethane dyes. The reaction vessel used
in making C.I. 48000 can be made of iron. All reactions are run at less than
100° at atmospheric pressure.
2. InputMaterials - The needed raw materials are shown below (Exhibit 1). The
amounts required are not known.
EXHIBIT 1. STARTING MATERIALS NEEDED TO MAKE C.I. 43820,
43830, and 48000
Color Index No. 43820 43830 48000
Components
o_-formylbenzenesulfonic acid x
2,3-cresotic acid x x
sulfuric acid x x
sodium nitrite x x x
2,6-dichlorobenzaldehyde x
£- [butyl(2-chloroethyl)ami no] benzaldehyde x
ethyl cyanoacetate x
sodium hydroxide x
3. Qpejrating Parameters - No information could be found regarding reaction
conditions.
4. Utilities - In the absence of information regarding reaction conditions, the
required utilities cannot be identified with certainty. Electricity, steam,
and water are probably needed.
5. Waste Streams - The use of nitrogen oxides in making the two triphenylmethane
dyes would likely lead to some noxious gas emissions. Brines containing
small amounts of organic materials would arise from making each of the
three dyes.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by
H. A. Lubs, Reinhold Publishing Company (1955), Chapter 5, "Miscellaneous
Dyes" (S. E. Krahler), pp 249-285.
85
-------
PROCESS MO. 10:
OTES «NO PISCNTS: C.I. 44040, 44045
ACRIDINE DYE: C.I. 4600S
Condensation, Nitro-
sation, Oxidation, Hy-
drolysis 105
[Figure 2-34]
C.I. 46005
Revised 5/19/75
FIGURE Z-8. FLOW CHART FOR THE PRODUCTION OF SELECTED TRIARYLMETHANE AND ACRIDINE DYES AND PIGMENTS
FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 10
TRIARYLMETHANE DYES AND PIGMENTS (C.I. 44040
"AND 44045) AND AN ACRIDINE DYE (C.I. 46005)
1. Function - The manufacture of triarylmethane dyes by this process shares in
common with Process Numbers 6 and 8 the use of formaldehyde and an N,N-
dialkylaniline as starting materials. However, the chemical operations are
somewhat different even though the final products fall into the same general
chemical classification. As before, simple stirred batch reaction vessels
with a glass lining are adequate for this process chemistry. The primary
raw materials (formaldehyde, an N,N-dialkyl-aniline and an N-alkyl-N-aralkyl-
aniline) are condensed in two successive process steps.
2. Input Materials - The starting materials needed to make these dyes are shown1
in the matrix below (Exhibit 1). No information could be obtained on the
amounts required to make 100 pounds of these colors. No information regarding
the required proportions of starting materials is available in readily
accessible literature.
3. Operating Parameters - No information could be found regarding operating
parameters.
4. Uti 1 Hi es - It is surmised that electricity, steam, and water are needed
to make these colors. The amounts needed are not known.
5. Waste Streams - The noxious gas emission from the manufacture of these dyes
and pigments will always consist of nitrogen oxides and small amounts of
formaldehyde. The liquid effluents will be brines containing heavy metal ions
(lead, zinc, or chromium). Solid wastes will be distillation residues from the
condensation of formaldehyde with the N,N-dialkylanilines, and precipitated
lead sulfate.
6. EPA Source Classification Code -
7. References - None.
87
-------
Page Two Process No. 10
EXHIBIT 1
RAW MATERIALS NEEDED TO MAKE C.I. 44040, 44045 and
46005
Color Index No. 44040 44045 46005
Components
formaldehyde x x
dimethyl aniline x x x
sodium dichromate x x
sulfuric acid x x
N-ethyl-1-naphthylamine x
sodium nitrite x x
N-phenyl-1-naphthylamine x
zinc chloride x
formaldehyde x
lead peroxide x
hydrochloric acid x
iron x
88
-------
PROCESS NO. 11: XANTHENE DVES MO PIGMENTS: C.I. 45100-45350
CXI
Nad
H2SO,
Fed 3
NaOH
Water
Condensation, Cycllza-
tion, Oxidation
11A
C.I. 45100
|F19ure 2-15]
(Figure 2-15]
C.I. 45160,
45175
0
(Figure 2-101
C.I. 45170
45350
C.I. 45180
IF1jor« 2-341
FIGURE 2-9. FLOW CHART FOR THE PRODUCTION OF SELECTED XANTHENE DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 11
XANTHENE DYES (C.I. 45100-45350)
1 • Function - This process for making dyes results directly in
only six individual organic chemical species. The process for making these
colors may involve as many as three steps.
Certain other related dyes and pigments are made from these species by
halogenation (cf Process No. 13). The required reactions are carried out
under atmospheric pressure in stirred batch reaction vessels lined with
glass.
2. Input Materials - The starting materials needed to make these dyes and pigments
are shown in the matrix below (Exhibit 1). The quantities needed to make
100 pounds of the dyes are not known.
EXHIBIT 1. STARTING MATERIALS NEEDED TO MAKE XANTHENE
DYES
Color Index No. 45100 45160 45170 45175 45180 45350
Component
4-formyl-m-benzenedi-
sulfonic acid x
m-jdi ethyl ami nophenol x x x x
xsulfuric acid x x x x x x
ferric chloride x
^3-ethylamino-^-cresol x
^phthalic anhydride x x x x
^ethanol x x
alumina hydrate x
o-dichlorobenzene x
4 5-hydroxytrimellitic acid
resorcinol x
3. Operating Parameters - The initial condensation reaction to make C.I. 45100
is carried out at 100° over a period of 18 hours with 30% sulfuric acid.
Cyclization of the intermediate product is accomplished with 90% sulfuric
acid in 2 hours. The initial condensation reaction to make the other dyes
is carried out with a 100% stoichiometric excess of the acid component which
is later recovered. The aminophenol is added gradually to the other component
at 150-180° over a period of 3 hours. Cyclization of the intermediate
product is accomplished with 78% sulfuric acid at 175-180° in 3 hours time.
No information is available about the quantities of starting materials per
pound of product or the size of equipment used. The finished dye is salted
out of the drowned reaction mixture with sodium chloride.
90
-------
Page Two Process No. 11
4. Utilities - Electricity, steam, and water are required, but the amounts
needed are not known.
5. Waste Streams - The waste streams are mainly brines contaminated with small
amounts of organic chemicals, some of which are highly colored. A sludge
of iron oxide will also result from the use of ferric chloride as an oxidation
reagent.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 746, 750-755.
91
-------
Solvent
PROCESS NO. 12: HALOGENATION OF DYES: C.I. AS SHOWN BELOW
4 ) [Figures 2-9. 2-20, 2-21, 2-22, 2-29, 2-31]
Halogenation
12A
I
MjlFlgure 2-15]
C.I. 45370:1 59710
45380 59815
45410 60005
45425:1 60010
45430 67895
59105 69815
59300 71205
59705 73065
1
Halogenation
12B
C.I. 69810
69825
[Figure 2-341
Revised 5/22/75
FIGURE 2-10. FLOW CHART FOR THE PRODUCJION OF DYES AND PIGMENTS BY HALOGENATION OF SELECTED DYES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 12
HALOGENATION OF DYES
1• Function - The substitution of chlorine, bromine, or iodine for hydrogen in
in a dye molecule often has an important and desirable effect on the
properties of a dye, as well as an influence on the properties of a pigment
made from the halogenated dye. The halogenated product is obtained by
treating the simple dye itself with halogen or a halogen carrying compound
under suitable conditions. The reactions involved can usually be operated
in iron equipment provided that moisture is rigorously excluded. Glass-
lined equipment is often used, however. Water scrubbers are generally used
to trap the effluent hydrogen halide which is formed in most cases.
2. Input Materials - The principal input materials are a halogen (chlorine,
bromine, or iodine, or a compound which functions as a halogen source
(typically, sulfuryl chloride), and a solvent medium for the reaction,
such as nitrobenzene, sodium hydroxide in water or alcohol solution,
chlorosulfonic acid, sulfuric acid, trichlorobenzene, molten aluminum
chloride, and the like. This process can usually be operated in iron
equipment provided that moisture is rigorously excluded. Batch reactors
are used in all instances. Only half of the halogen used appears in the
product. The remaining amount is converted to the hydrogen halide. When
sulfuryl chloride is used, both sulfur dioxide and hydrogen chloride are
by-products.
3. Operating Parameters. - Halogenations are generally carried at temperatures
in the range of 40 to 55°C. However, a few cases require much higher temper-
atures in the range of 155-190°C. No information is available regarding the
size of equipment used.
- 4- Utilities - Electricity, steam, and water are needed, but the amounts required
are not known.
5- WasteT...Streams. - The waste streams are principally aqueous solutions of hydrogen
halide. When the halogenation is done in the presence of sodium hydroxide,
the hydrogen halide is of course transformed to the sodium halide. Bromine
and iodine are both so valuable that the by-product halides are carefully
recovered. The waste streams are usually contaminated with small amounts
of highly colored products.
6- EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press,
New York 71952), Volume II, pp 940, 965, 971-2, 1126, 1132-1133.
93
-------
PROCESS NO. 13:
QUINACRIDONE PIGMENT:
C.I. 46500
[Oleum}**-
Aniline
Halogenatlon
13A
Amtnatlon
13B
CycHzatton
13C
'C.I. 46500
PROCESS NO, 14:
QUINOLINE DYES: C.I. 47000,
47005, 47020, 47023, 47035
jZnCl2T—^
Condensation
14A
C.I. 47000
47023
[Figure 2-34)
2-12)
(T)
(Figure 2-151
47000:Qutnald1ne
47005:Quinaldine
47020: 3-Hydroxy-2-methylquinoline
47023:«-8romo-3-hydroxy-2-methylquinoltne
47035:8-Naphthoqulnaldine
Revised 5/19/75
FIGURE 2-11. FLOW CHART FOR THE PRODUCTION OF A QUINACRIDONE PIGMENT AND SELECTED QUINOLINE DYES
FROK VARIOUS INTERMEDIATES
94
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 13
QUINACRIDONE PIGMENT (C.I. 46500)
1. Function - The manufacture of this pigment is a very isolated process. The
intermediates are not used to make any other dyes or pigments. There are
three steps in the process: (1) halogenation of terephthalic acid, (2)
reaction of aniline with the 2,5-dihaloterephthalic acid and (3) cyclization
of the 2,5-dianilinoterephthalic acid to the finished pigment. The reactions
are all carried out in batch type stirred reaction vessels made of iron.
2. Input Materials - The halogen used may be either bromine or chlorine.
Bromine is a more costly halogen, but the use of bromine leads to better
yields and milder reaction conditions. The necessary raw materials are:
aniline, halogen (chlorine, bromine, iodine or sulfuryl chloride), terephthalic
acid, phosphoric anhydride, and phosphoric acid. No data could be found on
amounts of materials used per unit of product.
3. Operating Parameters - The exact conditions used by industry for the manu-
facture of quinacridone pigment are not given in the literature.
4. Utilities - No information is available regarding the required utilities.
5. Waste Streams - The waste streams from the manufacture of this pigment
are brines containing small amounts of organic chemicals, and strongly
acidic wastes from the halogenation and cyclization steps.
6. EPA Source Classification Code -
1• References - Labana, S. S. and Labana, L. L., Chem. Rev. 67 (1), 1-18
95
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 14
QUINOLINE DYES
1. Function - The manufacture of quinoline dyes involves the condensation of
phthalic anhydride with the active methyl group on a 2-methylquinoline
compound. The chemistry involved is not related to any which has been
previously described, even though condensations with phthalic anhydride
were involved in Process No. 10, but the condensation reaction step is
similar to that employed in Process No. 10. The reactors are stirred batch
vessels with a glass lining.
2. Input Materials - The principal starting materials are phthalic anhydride
and a 2-methylquinoline compound as shown in Table I below.
TABLE I. QUINOLINE COMPOUNDS NEEDED FOR VARIOUS DYES
Dye C.I. No. Quinoline Compound
47000 quinaldine
47005 quinaldine
47020 3-hydroxy-2-methylquinoline
47023 4-bromo-3-hydroxy-2-methylquinoline
47035 ^-naphthoquinaldine
Zinc chloride is used to catalyze the condensation reaction. No information
is available as to the quantities of starting materials used per unit of
product.
3. Operating Parameters - The condensation reaction takes place at 220°C. No
solvent is required.
4. Utilities - A hot liquid heat transfer system is required, together with
electricity and water in unknown amounts.
5- Haste Streams - No reliable information could be adduced from readily
accessible literature regarding the waste streams. It seems likely that
the dyes are salted out, and in consequence the only waste streams would
be brines contaminated with small amounts of organic materials, some of
which are highly colored.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by
H. A. Lubs, Reinhold Publishing Co. (1955), Chapter 5, "Miscellaneous
Dyes" (S. E. Krahler) pp 261-263; Venkataraman, K., The Chemistry of
Synthetic Dyes, Academic Press, New York (1952), Volume II, p 1197.
96
-------
PROCESS NO. 15: SULFONATION OF DYES AND PIGMENTS: C.I. AS SHOWN BELOW
•-N
3 ) IF1gur«s 2-S. 2-11, 2-16, 2-17]
Oleum or
Ice
NaCI
JU(OH)3_
Inter-
mediate
Dye
or Pigment
Sulfonation
15A
C.I. 42780
47005
47020
47035
48005
50405
50420
51320
59101
59106
59826
60725
61530
61565
61585
61800
62080
62105
63000
63615
64515
65005
68215
69501
69805
69826
69840
70801
73015
73336
73361
73671
74104
74180
74200
o
[Figure 2-341
Revised 5/20/75
FIGURE 2-12. FLOW CHART FOR THE PRODUCTION OF DYES AND PIGMENTS BY SULFONATION OF SELECTED OYES AND PIGMENTS
97
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 15
SULFONATIQN OF DYES
!• Function - Over thirty dyes cari be treated in a single process step with either
sulfuric acid or oleum, and one or more sulfonic acid groups introduced into
the dye molecule. The product of such a sulfonation often shows desirable
properties not found in the parent dye. Stirred batch reactors made of
iron or steel are usually satisfactory for these reactions.
2. Input Materials - The principal input materials required are: oleum (or
concentrated sulfuric acid) and the antecedent dye. In most instances,
the sulfonated dye must be converted to the sodium salt by brine washing
and some of the dyes can be made into pigments by forming other salts
which are insoluble (cf Process No. 18). A large excess of oleum (or
sulfuric acid) is generally used. In a typical case, 500 pounds of 16
percent oleum is used for the sulfonation of 100 pounds of dye. In a few
cases, boric acid is used to catalyze the sulfonation. The finished reaction
mixture is diluted by pouring it into an ice-water slurry, thereby pre-
cipitating the product.
3. Operating Parameters - The important processing variables are: (1) nature
of the sulfonation reagent and (2) reaction temperature. Some dyes can be
sulfonated at 20 to 30°C with a sulfuric acid concentration as low as
80 percent. Other dyes may require oleum at a concentration as high as
15 to 20 percent and a significantly higher reaction temperature. No
further data are available on reaction parameters.
4. Utilities - Electricity, refrigeration, steam and water are required, but
the amounts needed are not known.
5. Waste Streams - The principal waste streams are dilute sulfuric acid and
brine solutions. Both of these will be contaminated with small amounts of
organic chemicals, some of which will be highly colored. The waste dilute
acid may find use in many plants and be discharged ultimately as a brine,
but it could also be advantageously concentrated and reused. Sulfur
trioxide emissions may result in some operations from the use of oleum as
sulfonating reagent.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by H. A. tubs
Reinhold Publishing Co. (1955), Chapter 5, "Miscellaneous Dyes" (S. E.
Krahler), p 282; Chapter 7, "Anthraquinone Acid Dyes" (E. C. Buxbaum),
pp 394-397; Chapter 10, "Phthalocyanine Dyes" (W. S. Struve), pp 609-610.
98
-------
PROCESS NO. 16:
POLYMETHINE DYES: C.I. 48013, 48015, 48020, 48035, 48040, 43055, 48070, 48100
1,3,3-
Trimethyl-
2-methylene-
indoline
IHOAC!^
Condensation [NaClJ ™ Condensation
16A 16E
. C.I. 48035, 48055, 48070, 48100 ,
C.I. 48013, 48015, 48020,
48040
Revised 5/20/75
2 ) (Figure 2-34]
f\
* Compounds condensed with 1,3,3-trimethy1-A '"-indoline acetaldehyde: -
48035: 2-Methylindole
48055: 2,4-Oimethyoxyaniline
48070: Sodium formate
48100: 1,2,3,4-Tetrahydrocarbazole
»* Compounds condensed with 1,3,3-trfmethyl-2-methyleneindoline:-
48013: p-Oiethylaminobenzaldehyde
48015: p- [ (2-Chl oroethy 1 Jmethy 1 ami no ] berual dehyde
48020: 4-[(2-Chloroethyl)ethy 1 ami no]-£-tolualdehyde
48040: l-Methyl-2-phenyl-3-indolecarboxyaldehyde
FIGURE 2-13. FLOW CHART FOR THE PRODUCTION OF SELECTED ?OLYME'HINE OYES FROM VARIOUS INTERMEDIATES
99
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. Jl
POLYMETHINE DYES
1. Function - These dyes are made in a single process step by condensing two
organic chemicals selected as shown in Table 1:
TABLE 1. POLYMETHINE DYES
Components Dye C.I. Number
Mo D —*^—•—•—'—' ™
1,3,3-trimethyl- !'-" 2-methylindole 48035
indoline acetaldehyde 2,4-dimethoxyaniline 48055
sodium formate 48070
1,2,3,4-tetrahydrocarbazole 48100
1,3,3-trimethyl-2- £~diethylaminobenzaldehyde 48013
methylenei ndoline JD- [(2-chloroethyl)methylami no]-
benzaldehyde 48015
4-[(2-chloroethyl)ethyl ami no]-
benzaldehyde 48020
1-methyl-2-phenyl-3 indole-
carboxaldehyde 48040
Stirred batch reactors made of iron are adequate for carrying out the required
reactions.
2. Input Materials - In addition to the principal starting materials shown in
Table 1 above, 20 percent sulfuric acid is used as condensation for the dyes
made from 1 ,3,3-trimethyl-^,°c_ indoline acetaldehyde and glacial acetic
acid as condensation catalyst for dyes made from 1,3,3-trimethyl~2-methylene-
indoline. All dyes are salted out of the reaction mixture and filtered
from the mother liquors. No data could be found on the amounts of starting
materials needed,
3- Opera ting Parameters - The only reference to operating parameters gave 100°C
as the temperature for the condensation reaction in making C.I. No. 48015.
4. Utilities - Electricity, steam, and water are needed, but the amounts
necessary are not known.
5. Waste Streams - The only pollution problems in making these dyes would arise
from the discharge of acidic brines containing small amounts of organic
chemicals, some of which would be highly colored.
6. EPA Source Classification Code -
7- References - The_Jhemi^try of Synthetic Dyes and Pigments, Edited by H. A. Lubs,
Reinhold Publishing Co. 0955) /"Chapter 5, "Miscellaneous Dyes" (S. E.
Krahler), p 250.
100
-------
PROCESS NO. 17: THIAZOLE DYES AND PIGMENTS: C.I. 49000-49010
4 Salt
of Oehydro-
toluidine
Sulfonlc
Acid
C.I. 49000
Revised 5/22/75
2 ) (Figure 2-34]
FIGURE 2-14. FLOW CHART FOR THE PRODUCTION OF SELECTED THIAZOLE DYES AND PIGMENTS FROH VARIOUS INTERMEDIATES
101
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 17
THIAZOLE DYES AND PIGMENTS
1. Function - This class of dyes is represented by only three products, C.I.
No. 49000, 49005, and 49010. The two principal starting materials are
j>toluidine and sulfur. Depending on the specific color being made, the
number of processing steps ranges from two to four. In respect to the method
of manufacture, these dyes are closely related to the sulfur dyes (cf.
Process No. 21). The processing equipment for the primary reaction between
the two principal starting materials is a stirred iron vessel with a jacket
to permit controlled heating at temperatures in the range of 150-250°C. The
necessary sulfonation is carried out in an iron vessel fitted with a stirrer
and a stearn coil. Esterifications with methanol would require a glass-lined
pressure vessel which could operate at 500 psi.
2. Input Materials - Table 1 shows the amounts of starting materials needed to
make 100 pounds of C.I. 49000.
TABLE 1. RAW MATERIALS NEEDED FOR 100 POUNDS OF C.I. 49000
Component Amount, pounds
£-toluidine 82.3
sulfur 53.8
. sodium carbonate 0.8
sulfuric acid 115
66 percent oleum 77
20 percent aqueous ammonia 19.2
ice 192
water 500
The reaction would also produce 31.3 pound of dehydro-p_~toluidine sulfonic
acid as the ammonium salt, which on methylation would yield C.I. 49005.
3. Operating Parameters - The fusion of sulfur with p_-toluidine is carried out
at 180 to 220°C over a period of 13 hours under atmospheric pressure.
Sulfonation of the cooled5 solidified melt from the fusion reaction is done
at 20 to 30° with good cooling.
4. Utilities - A hot liquid heat transfer system is necessary, together with
electricity, refrigeration, steam5 and water in unknown amounts.
5. Haste Streams - The principal emission problem arises from the evolution of
hydrogen sulfide in the fusion reaction. In a well-run plant, this toxic
gas would be absorbed in sodium hydroxide for use elsewhere in the manu-
facture of dyes as a reducing agent. Other waste streams would be dilute
sulfuric acid and an ammoniacal brine contaminated with small amounts of
organic materials, some of which would be highly colored.
6- JLPA Source C1ass ification Code -
7- R6.t§L?Jlc_§l. ~ Fierz-David, H. E. and Blangey, L., Fundamental Processesjpf
Qy_§LJ^emj_stry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience "Publishers, Inc.,, New York (1949), pp 332-335.
102
-------
PROCESS NO. 18: FORMATION OF PIGMENTS FROM SELECTED DYES
1) (Figures 2-1. 2-2, 2-4, 2-6. 2-8-2-11. 2-14]
Precipitation,
Filtration
13A
C.I. 10020
Various Azo
41000
42025
42040
42045
42090
42090
42140
42555
42575
42595
42600
42640
42650
1
42750:1
Pigments 44040:2
44045:2
45160:1
45170:2
45170:3
45175:1
45370:2
45380
45380
45410:2
45425:
45430:
47005
49005:1
o
[Figure 2-341
Revised 5/20/75
FIGURE 2-15. FLOW CHART FOR THE PRODUCTION OF PIGMENTS FROM SELECTED DYES
103
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 18
FORMATION OF PIGMENTS FROM SELECTED DYES
1. Function - A variety of dyes are too easily soluble in water and/or organic
solvents to function satisfactorily as pigments. Many such dyes can be
combined in simple fashion with another chemical to make a satisfactory
pigment having the requisite low solubility characteristics. The process
step of combining the dye and a dye precipitant is easily carried out in a
large vat made of steel, with good stirring to insure completion of the
reaction involved.
2. Input Materials - The starting materials, other than the dye, used to make
pigments from dyes are selected from the list in Table 1.
TABLE 1. STARTING MATERIALS WHICH COMBINE WITH DYES
TO YIELD PIGMENTS
alumina
aluminum sulfate
barium chloride
calcium chloride
ferrous sulfate
sodium chloride
manganese chloride
strontium chloride
resin
quebracho extract
phosphomolybdic acid
phosphotungstic acid
potassium antimonyl tartrate
Neither alumina nor resin combine chemically with the selected dye to form
an insoluble complex as do the other substances. These two materials function
as adsorbtive agents.
3- QPeJ3J;ij1.3_£arJm?ters - The reacting solutions are general ly heated to a
temperatuVe between 50 and 75°, combined at a prescribed rate and the product
slurry cooled to obtain the desired crystalline form of the product.
4. Utilities - Electricity, steam, and water are required in unknown amounts.
5. Waste Streams - The waste products are all brines containing organic chemicals,
some of which are highly colored. The brines may also contain residual
amounts of metal ions when metal salts are used as precipitants. It should
be noted that barium ion is very toxic.
6. EPA Source Classification Code -
7. References - Pigment Handbook, Edited by T. C. Patton, John Wiley & Sons (1973),
"Pigment Green B, I-D-a" (C. G. Inman), pp 435-438; "Helio Bordeaux BL, I-D-c-6"
(G.G. Kositzke), pp 487-489; "Persian Orange Lake, I-D-c-7" (M. J. Dunn), pp
491-492;"Red Lake C, I-D-c-8" (R. Benemelis, pp 493-496; "Lithol Red, I-D-c-9-i"
(T.E. Ludwig), pp 497-504; "Rubines, I-D-c-9-ii" (T.E. Ludwig), pp 505-514;
"Rubine G Pigment, I-D-c-9-iii, pp 515-518; ''Permanent Red 2B, I-D-c-10-i,
pp 519-524; "BON Maroon, I-D-c-10-ii" (C.H. Bernhard), pp 525-529;
104
-------
Page Two
Process No. 18
"Pigment Scarlet 3B Lake, I-D-c-11", (T.A. Langstroth); "Scarlet 2R Lake,
I-D-c-12" (T.C. Patton); "Basic Dye Pigments, Fugitive, I-D-f-1", (J. B.
Arnold), pp 599-604; "Basic Dye Pigments, Permanent, I-D-f-2" (V. Oliver),
pp 605-616, "Peacock Blue Lake, I-D-h" (T. C. Patton), pp 625-627.
105
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 19
AZINE DYES (C.I. 50204, 50240, 50400, and 50415)
1 • Function - The manufacture of the azine dyes depends on the oxidation of
aniline and selected arylamines under specific conditions. The reaction
conditions and components are somewhat different from those used in Process
No. 6 for the manufacture of triarylmethane dyes from arylamines by oxidative
reactions. The literature available does not tell whether or not simple iron
vessels can be used for the fusion reactions used to make these dyes. The
hydrochloric acid salts of amines would likely corrode iron at the elevated
temperatures used and make necessary the use of glass-lined reactors.
2. Input Materials - The matrix below (Exhibit 1) shows the chemicals needed to
make the dyes in this category:
EXHIBIT 1 . COMPONENTS NEEDED TO MAKE SELECTED AZINE DYES
Color Index 50204 50240 50400 50415
Components
p-phenyazoaniline x x
aniline x x x x
toluene-2,5-diamine x
o-toluidine x
hydrogen chloride x x x x
sodium dichromate x
nitrobenzene x x x
ferrous chloride x x
iron (powder) x
No information is available on the amounts of these materials needed.
3. Operating Parameters - The first step in making C,I. 50420 requires diazoti-
zation of p_-toluidine, a reaction which must be carried out at 0 to 5°. The
intermediate diazo compound is allowed to couple with toluene-2,5-diamine.
The operating parameters for the remaining steps in the process are not
available. The oxidation of aniline to make C.I. 50415 is accomplished by
fusing aniline with aniline hydrochloride and nitrobenzene in the presence of
ferric chloride at 160 to 180°C. p_-Phenylazoaniline is fused with aniline
hydrochloride in the presence of ferrous chloride and nitrobenzene to give
C.I. 50204 or 50400. The details of the procedure which determine the exact
dye obtained are not available from published literature.
4- ytjlities - Electricity, steam, and water are needed, but the amounts required
are not known.
5. Waste Streams - The aqueous effluents from washing the dyes would contain
chlbrideVTron, and chromium ions, as well as small amounts of organic materials
many of which would be highly colored. In a well-run plant the metal ions
would be precipitated and allowed to settle in a pond as a sludge.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments. Edited by H A I uh<;
Reinhold Publishing Co. (1955), Chapter 5, "Miscellaneous Dyes" (S E Krahler?'
pp 239 241-244; Venkataraman, K., The Chemistry of SyntheticDyes. Academ c
Press, New York (1952), Volume II, pp 766-767, 773-776.
106
-------
PROCESS NO. 19: AZINE DYES: C.I. 50204, 50240. 50400, 50405, 50415, 50420
C.I. 50240
Revised 5/19/75
2 ) (Figure 2-341
FIGURE 2-16. FLOW CHART FOR THE PRODUCTION OF SELECTED AZIHE DYES FROM VARIOUS INTERMEDIATES
107
-------
PROCESS NO. 20: OXAZINE DYES AND PIGMENTS: C.I. 51004, 51175, 51300, 51319
JO
NaNOp
HO *
Mater
Ice
ZnCl-,
EtOH
5-Am1no-
2-anilino-
benzenesul-
fonic
Acid
I ' I
Nitrosati'on,
Condensation
20A
\
i
_£
TAcONaT
K12 U»
L»S02C1J
T
t 9,
Condensation,
Cycllzation
20B
1
c
[M«0 "1 ap
OieumJ^
t
J [Figure 2-12]
C.I. 51004,
51175
1
1 C.I. 51319
1 i
\
A
Condensation,
Sulfonatlon
20C
' C.I. 51300
[Figure 2-341
Revised 5/20/75
FIGURE 2-17. FLOW CHART FOR THE PRODUCTION OF SELECTED OXAZINE DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 20
QXAZINE DYES AND PIGMENTS
1. Function - These dyes all involve the condensation of a substituted aniline
compound with a substituted phenolic compound (or a phenol ether), followed
by an oxidative reaction which brings about the formation of an oxazine ring
system. The chemical structure of these dyes is conceptually related to
those for the azine (cf. Process No. 19), and thiazine dyes (cf Process
No. 21). Stirred batch reactors with a glass lining are necessary for most
of the reactions involved in making these products.
2. Input Materials - The starting materials for the several products are shown
in the matrix below (Exhibit 1).
EXHIBIT 1. STARTING MATERIALS FOR OXAZINE DYES AND AN
OXAZINE PIGMENT (C.I. 51004, 51175, 51300
and 51319)
Components 51004 51175 51300 51319
N,N-diethyl anisidine
(or phenetidine) x
sodium nitrite x x
hydrochloric acid x x
ice x x
rn-di ethyl ami nophenol x
water x x x
ethanol x
zinc chloride x
5-amino-2~anilino-
benzenesulfonic acid x
magnesium oxide x
2-naphthol x
N,N-dimethylaniline x
3-amino-9-ethylcarbazo1e x x
chloranil x x x x
sodium acetate x x
magnesium oxide x
oleum x
benzenesulfonyl chloride x x
o-dichlorobenzene x x
3. Operating Parameter^ - Information on operating parameters could be found
only for C.I. 51319. To make this pigments chloranil is condensed with
3-amino-9-ethy1carbazole in o-dichlorobenzene as the reaction medium, using
anhydrous sodium acetate as catalyst. The reaction requires 7 hours at
60 to 115°C. The condensation product is cyclized to the pigment with
benzenesulfonyl chloride at 180°C. The crude pigment is washed and filtered,
109
-------
Page Two ' Process No. 20
4. Uti1ities - Electricity, steam, and water are required, but the amounts
needed are not known.
5. Waste Streams - Liquid wastes result from the manufacture of all these
products. These wastes are brines containing small amounts of organic
materials, some of which are highly colored. In addition, the wash liquors
from making C.I. 51319 contain significant amounts of benzenesulfonic acid.
Hydrogen chloride is also evolved in the manufacture of this pigment, and
it is usually scrubbed out from the reactor effluent with water. The use
of oleum in making C.I. 51300 leads to a waste stream containing sulfur
trioxide which must be controlled.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic pyes, Academic
Press, New York (1952); Volume II, pp 781, 786-788.
110
-------
PROCESS NO. 21: THIAZINE DYE: C.I. 52015
N,N-
Dimethyl-
£-phenyl-
enediamine
Na2S203 -
Mn02
ZnClo
, «J
Oxidation, Cyclization.
Precipitation.
Filtration
21A
C.I. 52015
2 ) [Figure 2-34j
Revised 5/20/75
FIGURE Z-18. FLOW CHART FOR THE PRODUCTION OF A THIAZINE DYE FROM VARIOUS INTERMEDIATES
111
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 21
A THIAZINE DYE (C.I. 52015)
1 • Function - The chemical structure of this dye is conceptually related to
the structures for azine dyes (Process No. 20) and oxazine dyes and pigments
(Process No. 19). The use of hydrochloric acid and zinc chloride requires
that the reactor used be glass-lined.
2. Input Materials - The following chemicals are required to make 125 pounds
of C.I. 52015, which contains 20 percent water (i.e., TOO pounds of dye):
water 505 gallons
50 percent zinc chloride 657 pounds
sodium chloride 1250 "
sodium nitrite 16 "
manganese dioxide 82 "
sulfuric acid 230
aluminum sulfate 125 "
sulfuric acid 230
concentrated hydrochloric
acid " 88 "
sodium dichromate 188 "
dimethylaniline 66 "
£-ami nodimethyl aniline 88 "
62 percent nitric acid 66 "
sodium thiosulfate 173 "
3. Operating Parameters - The main reaction involved in making this dye takes
place smoothly at 70 to 85CC. Only small amounts of the dye are made in a
single batch because rapid heating of the reaction mixture is necessary during
processing.
4- Utilities - Electricity, steam, and water are needed, but the amounts
required are not known.
5. Waste Streams - All the waste streams are brines containing also manganese,
chromium, zinc, and aluminum ions. The thiosulfate used is partly converted
to dithionate in the waste effluents.
6. EPA Source Classification Code -
7. References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of Dye
Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), pp 311-314; The Chemistry of
Synthetic Dyes and Pigments, Edited by H. A. Lubs, Reinhold Publishing Co.
(1955), Chapter 5, "Miscellaneous Dyes" (S. E. Krahler), pp 266-268;
Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press, New York,
(1952), Volume II, pp 791-794.
112
-------
PROCESS NO. 22: SULFUR DYES: C.I. 53000 - 53830, 69705
Revised 5/20/75
[Figure 2-341
FIGURE 2-19. FLOW CHART FOR THE PRODUCTION OF SELECTED SULFUR DYES FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 22
SULFUR DYES (C.I. 53000-53830, and 69705)
1. Function - Some of the sulfur dyes share in common with the thiazole dyes
(Process No. 17) the use of sulfur at high temperatures as an important
processing step. Other sulfur dyes use either sodium sulfide in combination
with sulfur, or sodium sulfide together with a solvent as the reagent
material. Besides the variety of pure organic chemicals used as substrate
materials, cellulose of one kind or another can be converted to a sulfur dye.
If iron vessels are used for the reactors, they may be corroded rapidly in
the case of some dyes. Glass-lined vessels are preferred in these few
instances. Good agitation is necessary for making all the sulfur dyes.
2. Input Materials - Besides cellulose (for C.I. 53000) and 53001, twenty-eight
organic chemical species are used to make twenty-seven specific dyes.
The chemicals employed are listed in Table 1.
Many of the organic chemicals in Table 1 are used alone. Some are used
either alone or in combination with one or more other compounds, and some
are used only in combinations. The sulfurizing reagents are: (1) sulfur
alone, (2) sodium sulfide and water or an organic solvent or (3) sodium
sulfide and sulfur in combination. Copper sulfate is occasionally also
a component of the reaction mixture.
3. Operating Parameters - The mixture of starting materials is heated for varying
periods of time (10 to 48 hours). When a solvent is not employed, the reaction
temperature ranges from 95° to 350°C. With a solvent, temperatures are generally
in the range of 84 to 124°C, with the temperature usually being that at which
the solution boils. Reaction vessels vary in size from 300 to 2000 gallons.
4- Utilities - In addition to a hot liquid heat transfer system, electricity,
steam, and water are needed in unknown amounts.
5- Waste Streams - The sulfurization step generates hydrogen sulfide, which must
be scrubbed from the reactor effluent. The resulting sodium sulfide can be
recycled. Sodium thiosulfate can be recovered from the manufacture of sulfur
dyes with aqueous sodium sulfide as the sulfurizing reagent. Recovery of
this valuable byproduct is an important factor in the economics of manu-
facturing several sulfur dyes. The aqueous effluents from making sulfur
dyes are brines containing inorganic sulfur compounds and small amounts of
organic chemicals, some of which may be highly colored.
6. EPA Source Classification Code -
7. References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of
Dye Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), pp 337-338; The Chemistry of
Synthetic Dyes and Pigments, Edited by H. A. Lubs, Reinhold Publishing Co.,
(1955), Chapter 6, "Sulfur Dyes" (N. M. Bigelow and 0. Stallman), pp 302-334;
Venkatararnan, K., The_ Chemistry o_f S^jithetic Dyes, Academic Press, New York,
(1952), Volume II,""pp 1059-1109".
114
-------
Page Two
Table 1.
Process No. 22
ORGANIC CHEMICALS NEEDED FOR MAKING SULFUR DYES
Intermediate
2,'4'-dinitroacetanilide
phthalic anhydride
5'-amino-o-formotol uidide
aniline
toluene-2,4-diamine
N ,N'-£- phenylenebi sformami de
N,N'-2,4-toly1ylenebisformamide
benzidine
2- (g-ami nopheny1)-6-methyl benzothi azol e
2,4-dinitrophenol
£-ami nophenol
picric acid (or picramic acid)
£~anilinopheno1
£-(2,4-dinitroanilino)phenol
p_-(2,4~dini troani 1 ino)phenol
phenol
£-2-naphthylaminophenol
4,4!-iminodiphenol
decacyclene
tri ni trodecacyclene
£- (4-amino-m-to!uidino)phenol
£-(£-dimethylaminoanilino)phenol
N-(p_-anil inophenyl )-£-quinone imine
8-anilino-5-(£~hydroxyanilino)-1-naphtha!enesulfoni
£-(3-carbazolylamino)phenol
3,6-diamino-2,7-dimethy1acridan
8-ami no-7-methyl-2-phenazinol
1,2,4-trichloro-7-methyl-3 H-isophenothiazin-3-one
sulfur
sodium sulfide
^
sodium chloride
ethylene glycol
butyl alcohol
sodium hydroxide
cyclohexanol
ethylene glycol monomethyl ether
hydrochloric acid
sulfuric acid ,
Glycerol
2-(chloromethyl) anthraqulnone
sodium hypochlorite
C.I. Number
53010
53010
53040
53040
53050,
53090
53120
53160
53160
53185,
53190
53195,
53228
53235,
53246
53290
53290
53290
53320
53325
53340
53430
53450
c acid
53630
53680
53720
53830
53055, 53090
53190, 53195, 53196
53196, 53205
53246
53570, 53571
various
various
various
53228
53290
53050
53228
53228
53430
53320, 53325
53830
69705
69705
53630
53055, 53160
115
-------
Flgurt 2-20. Flow chart for the production of miscellaneous vat dyes and pignents based on anthraqulnone and pyrene
CTi
PROCESS SB. 23:
AUIAR1K: C.I. 58000
(S«cio3 "I
NaOH I .^
Water P^
(jjaCl, HC1J
Hydrolysis, Oxidation:
200*, 150 psi
23A
C.I. 58000
PROCESS NO. 24:
PYRAN1NE: C.I. 59040
Hydrolysis
24A
C.I. 59040
(Figure 2-341
PROCESS NO. 25:
PYRANTHRONE DYE: C.I. 59700
|Cu Powder
1Pyridine
~
H
[KOH 1 ^
1-CuHgOHj"^
[NaOCl]
Dimerization
25A
Cycllzation
2 SB
Purification
25C
C.I. 59700
(T) IFl9"r« 2-101
Revised 5/22/75
FIGURE 2-20. FLOW CHART FOR THE PRODUCTION OF MISCELLANEOUS VAT DYES AND PIGMENTS
BASED ON ANTHRAQUINONE AND PYRENE
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 23
ALIZARIN (C. I. 58000)
1. Function - Alizarin is itself an important vat dye, and also serves as an
intermediate for making other dyes. Its manufacture depends on a combination
of hydrolysis and a controlled oxidation of 2-anthraquinone sulfonic acid.
A stirred autoclave capable of operating at 200° and 150 psi is required
for carrying out the reaction. The reaction mixture is highly corrosive
and requires the use of a nickel-lined vessel.
2. Input Materials - The materials required to make 100 pounds of alizarin
are shown in Table 1.
TABLE 1. MATERIALS NEEDED TO MAKE 100 POUNDS OF ALIZARIN
Compound Amount, in pounds
Sodium 2-anthraquinonesulfonic Acid 133
Sodium Hydroxide 382
Sodium Chlorate 40
Water 115 (Gallons)
50 Percent Sulfuric Acid As Required
3. 0£ej2a_^ng__Pa£ajnele_rs_ - The reaction mixture is heated at 185°C for
48 to 72 hours under an autogeneous gauge pressure of 75 to 90 psi.
Batches of alizarin as large as 2500 kg have been made in a single operation,
It is estimated that a 10,000 gallon autoclave would be used for such a
large batch.
4- Utilities - Electricity, steam, water and a hot liquid heat transfer system
are needed. The required amounts of utilities are not known.
Waste Streams - All the waste streams from the manufacture of alizarin
are brines containing sodium sulfite and small amounts of organic materials,
some of which are highly colored.
EPA Source Classification Code -
Re_ferences^ - Fierz-David, H. E., and Blangey, L., Fundamental Processes^
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 24
PYRANINE (C.I. 59040)
1. Function - The manufacture of this single dye depends on the conversion of
one of the four sulfonic acid groups in pyrene-1,3,6,8-tetrasulfonic
groups to an hydroxyl group by simple hydrolysis. Although this type of
reaction alone is not used-to make other dyes, it is used to make certain
dye intermediates and hydrolysis of the sulfonic acid group in sodium
anthraquinone-2-sulfonate is one of the reactions involved in the manufacture
of alizarin. A version of this reaction is used today to make resorcinol
from benzene-1,3-disulfonic acid. An ordinary iron vessel fitted with a
reflux condenser should serve admirably for the production of this dye.
2. Input Materials - The only input materials needed are pyrene-1,3,6,8-
tetrasulfonic acid and 15-20 percent sodium hydroxide solution. The
process requires 144 pounds of sodium 1,3,6,8-pyrenetetrasulfonate,
82 pounds of sodium hydroxide and 50 gallons of water to make 100 pounds
of the dye. The reflux time of 18 hours given in the literature is
probably longer than is really necessary.
3. Operating Parameters - The process operates under atmospheric pressure at
the boiling point of 15-20 percent caustic soda.
4. Utilities - Electricity, steam and water are needed in unknown quantities.
5. Waste Streams - The only waste stream is an aqueous effluent containing
sodium sulfite. In a well run plant, this material might be freed of
the organic materials contained in it and used in other processes for
its reducing power.
6. EPA Source Classification Code -
1• References - Tietze, E., and Bayer, 0., Annalen 540, 205 (1939).
118
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 25
PYRANTHRQNE (C.I. 59700)
1. Function - This dye can be made from either l-chloro-2-methylanthraquinone
or pyrene as the principal organic starting material. The availability of
pyrene may have greatly diminished in recent years owing to the decline in
the volume of chemicals recovered from coal tar distillates. The corrosive
nature of the chemicals involved in the several process steps indicates
that stirred vessels with a glass-lining would be required.
2. Input Materials - The materials required to make 100 pounds of dye contained
in 110 pounds of product are as follows:
l-chloro-2-methylanthraquinone 142 pounds
p_-dichlorobenzene 407 "
copper powder 77 "
pyridine 46 "
sodium carbonate 68 "
sodium hydroxide 59 "
isobutyl alcohol _ 417
Nearly all of the p_-dichlorobenzene would be recovered.
3. Operating Parameters - The dimerization of the l-chloro-2-methylanthraquinone
takes place at 150-160°C in 6 hours. Cyclization to the dye requires 3 hours
at the same temperature. No information is available regarding the size of
equipment used.
4- Utilities - No information is available about the utilities required.
5. Waste Streams - The principal waste streams from the manufacture of this dye
would be brines containing small amounts of organic chemicals.
6. EPA Source Classification Cod^e -
1- References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of Dye
Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), p 223; The Chemistry of
Synthetic Dyes and Pigments, Edited by H. A. Lubs, Reinhold Publishing Co.
(1955), Chapter 7, "Anthraquinone Dyes and Intermediates", (M. A. Perkins),
pp 450-453; Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press,
New York (1952), Volume II, pp 951-952.
119
-------
PROCESS NO. 26'. BeNZANTIIRONl OVtS: C.I. 59100. 59BOO, 59826, 598SO. 71200
no
o
t!!2S04 "I
Ft Powder (-*•»-
Jater I
Reduction. Condensa-
tion. 135"
)(figure 2-341
NOME 2-2}. FLOW CHART TOR Tllf PRODUCTION Of B.ENZANTHRONE OVES FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 26
BENZANTHRONE DYES
1. Function - The manufacture of these dyes depends on the modification in
several ways of a primary intermediate, benzanthrone. These dyes are closely
related to the isoviolanthrone dyes made by Process No. 27, and all of them
require benzanthrone as the principal organic raw material. The reaction to
make this intermediate can be carried out in an iron vessel with good stirring.
All the other reactions can also be done in similar iron vessels
except for a nitration in acetic acid, which must be done in a stainless
steel reactor.
2. Input Materials - To make 100 pounds of benzanthrone (25A) contained in 116
pounds of product, the following materials are required in the amounts shown
in Table 1.
TABLE 1. MATERIALS NEEDED TO MAKE 100 POUNDS OF
BENZANTHRONE
anthraquinone 104 pounds
glycerol 57.1
96% sulfuric acid 729
water 69.5
iron powder 79.1
wasfwate?^ j small, unknown quantities
The product is purified by vacuum distillation. In the alkali fusion reaction
(25C) for converting benzanthrone to C.I. 59800, the following materials are
used, but the amounts necessary to make 100 pounds of dye are not specified
in standard textbooks on dyes:
naphthalene (solvent) sodium hydroxide
benzanthrone anhydrous sodium acetate
potassium hydroxide
The alkali treatment of benzanthrone (25F, 256 and 251) to make 100 pounds
of C.I. 59825 requires the following materials in the amounts specified
(Table 2}i
TABLE 2. MATERIALS NEEDED TO CONVERT BENZANTHRONE TO
100 POUNDS OF C.I. 59825
benzanthrone 125 pounds
90% potassium hydroxide 312.5 "
anhydrous sodium acetate 37.5 "
isobutyl alcohol 240.6
water 413 gallons
12% sodium hypochlorite 50 pounds
water 158.5 gal Ions
96% sulfuric acid 2667 pounds
water 148 gallons
manganese dioxide 128 pounds
sodiumiJbls..ulfite_^ amount unknown
/liricEtorobenzene^ 1580 pounds
'-methyl p-toluenesulfonate 163.3 pounds
anhydrous potassium carbonate 120 pounds
121
-------
Page Two Process No. 26
Methyl sulfate is probably used today instead of methyl £-toluenesulfonate.
The amounts of materials needed in the remaining reactions are not given
in the standard texts on dyes. The other required input materials are
shown in Table 3.
TABLE 3. OTHER RAW MATERIALS NEEDED TO MAKE SELECTED
BENZANTHRONE DYES
Component C.I. Number
aluminum chloride 59100
benzoyl chloride 59100
acetic acid 59850
nitric acid 59850
ethylene dibromide 71200
3. Operating Parameters - The reaction for converting anthraquinone and glycerol
to benzanthrone (25A) begins at 125° and is highly exothermic. The temperature
is maintained at 135° for an hour by cooling the kettle. The alkali fusion
reaction (25B) of benzanthrone to make C.I. 59800 starts at 180° and the
mixture is kept at 225 to 230° for 1 to 1.5 hours. The alkali treatment of
benzanthrone (25F) to make dibenzanthronyl takes place at 112° for 1 to 4
hours. Oxidation of the dibenzanthronyl to the diketo compound (25G) takes
place at 25-30° in 4 hours time. The methylation of the dihydroxy compound
(251) (obtained by reducing the diketo compound with boiling sodium bisulfite)
requires 4 hours at 210°. Operating parameters for the other reactions are
not readily accessible.
4. Utilities - A liquid heat transfer system is necessary for heating the
alkali fusion vessel and the methylation reactor. Electricity, steam, and
cooling water are also required. The amounts needed are not known.
5. Haste Streams - The treatment of benzanthrone with alkali results in the
formation of hydrogen gas which can be flared in order to dispose of it
safely. It is not considered to be a pollution problem. The solvents used
in these processes (acetic acid, naphthalene, isobutyl alcohol, trichlorobenzene
and nitrobenzene) are all too valuable to discard and are recovered to the
full extent possible. Purification of dibenzanthrone inevitably leads to
a distillation residue which constitutes a solid waste disposal problem.
The iron used in making benzanthrone itself would probably end up as an
oxide sludge. Liquid wastes are encountered in all the process steps involved
in making these dyes. These wastes would be brines with excess alkali,
manganese ion, or aluminum ion. They would also contain organic substances.
Solutions containing manganese ion would be economically worth recovering
for their manganese content if there was a sufficient quantity of them.
6- EPA Source C1 a s s i f i c a t i o n Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by H. A.
Lubs, Reinhold Publishing Co". (1955), Chapter 7, "Anthraquinone Dyes and
Intermediates" (F. B. Stilmar and M. A. Perkins) pp 377-379, 382-385;
Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press, New York
(1952), Volume II, pp 958-971.
122
-------
PROCESS NO. 27: ISOVIOLADTHRONE DYES: C.I. 60000, 60015
[~Na2S 1
C12 L-»»
LWaterJ
Chlorination, Sulfide
Formation
27A
A
3,3'-
Dibenzan-
thronyl
Sulflde
fEtOHl
|_MaOHJ *^
Oesulfurization
27B
I
C.I. 60000
MnOg
NaHS03
K2C03
Oxidation,
Methylation
27C
J
C.I. 60015
2 } [Figure 2-34]
CO [Figure 2-101
Revised 5/22/75
FIGURE 2-22. FLOW CHART FOR THE PRODUCTION OF ISOVIOLANTHRONE OYES FROM VARIOUS INTERMEDIATES
123
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 27
ISOVIOLANTHRQNE DYES (C.I. 60000 and 60015)
1. Function - The isoviolanthrone dyes are closely related to the violanthrone
products made by Process No. 26. Both classes of dyes have similar structures
and depend on the benzanthrone as the principal organic chemical starting
material. The equipment for carrying out the first process step (27A)t
chlorination of benzanthrone, requires equipment which resists corrosion by
water, chlorine, and hydrochloric acid at 100°. Glass-lined vessels and glass
pipe would be necessary for handling the reaction mixture. The two other
process steps for making these dyes could probably be carried out in iron
reactors fitted with efficient stirrers.
2. Input Materials - The raw materials for making these dyes are listed in
Table 1.
TABLE 1. STARTING MATERIALS NEEDED TO MAKE
ISOVIOLANTHRONE DYES, C.I. 60000 and 60015
Components Color Index Number
lomponents 60000 60015
benzanthrone x x
sodium sulfide x x
ethanol x x
sodium hydroxide x x
suIfuric acid x
manganese dioxide x
sodium bisulfite x
methyl sulfate x
potassium carbonate x
No information could be found regarding the quantities of raw materials
needed to make 100 pounds of the dyes.
3. Qperating Parameters - 3-Bromobenzanthrone is converted to the dibenzanthronyl
sulfide by heating it with sodium sulfide. On adding sodium hydroxide to the
sulfide, it cyclizes to isoviolanthrone. No details of the operating
parameters could be found.
4- Utilities - Electricity, steam, and cooling water are necessary utilities
but the amounts required are not known.
5. Haste Streams - The chlorination of benzanthrone leads to a waste stream of
of dilute hydrochloric acid which would be difficult to dispose of safely
and economically. Formation of dibenzanthronyl sulfide results in a waste
brine. The desulfurization of the sulfide would generate a waste stream of
sodium sulfide which could be recycled. The oxidation and methylation of
C.I. 60000 would generate a waste stream containing manganous sulfate which
could perhaps be economically recovered for its manganese values. The manu-
facture of C.I. 60015 would also generate quantities of brines containing
small quantities of organic compounds.
6. EPA Source Classification Code -
?• References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 974-975.
124
-------
PROCESS NO. 28: ANTHRAQUINONE DYES AND PIGMENTS (AMINOLVSES): C.I. AS SHOWN BELON
rv>
en
Leuco-
1.4.5,8-
tetrahydro-
xyanthra-
quinone
C.I.
60710
60725
61100
61115
61500
61505
61551
61552
61555
61565
C.I. 60505 61710
60725 61800
61125 62015
61135 62045
61200 62055
61205 62073
61211 62080
61525 62100
61565 62125
61585 62S60
63615
64515
65005
67895
68210
68700
69005
690)5
69500
69525
C.I. 60505
C.I. 60767
61705
61710
C.I. 62500
62560
o
Revised 5/20/75
[Figure 2-34)
FIGURE 2-23. FLOW CHART FOR THE PRODUCTION OF ANTHRAQUINONE DYES AND PIGMENTS
BY AMINOLYSIS OF VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 28
ANTHRAQUINONE DYES AND PIGMENTS (AMINOLYSES)
1. Function - A number of dyes and pigments are made by the reaction of ammonia
or an organic amine with an appropriately substituted anthraquinone compound.
In the substrate anthraquinone compound, the incoming nitrogen moiety
replaces an activated (1) hydroxyl, (2) halogen (3) sulfonic acid or (4)
nitro group.
2. Input Materials - The required organic amines are selected from among approxi-
mately twenty (20) chemicals, of which about half are purchased outside the
industry. The amines range in complexity from ammonia and methylamine to
ami no-substituted polycyclic compounds, including anthraquinone derivatives.
The other part of the dye molecule always is an anthraquinone compound
carrying the replaceable substituent usually (but not always) in the eC-position.
The substituent being replaced by nitrogen is usually a halogen (chlorine
or bromine).
3. Operating Parameters - The displacement of halogen, hydroxyl, and nitro
groups in the of-position of an anthraquinone compound generally proceeds
under relatively milder conditions (40-125°C) than those needed for the
displacement of a sulfonic acid group (125-150°C). The displacement of
halogen is usually carried out in an aqueous medium, with an acid receptor
present to neutralize the hydrogen halide which is formed. The acid receptor
can be an excess of the organic amine or an alkali metal carbonate. Displace-
ments of halogen are sometimes characterized by the use of copper acetate
as catalyst. Displacements of hydroxyl are frequently catalyzed with boric
acid and are done with the amine as the reaction medium. No information is
available on the size of equipment used to make these dyes.
4- Utilities - Electricity, steam, and cooling water are the necessary utilities.
No information is available on the amounts required.
5. Waste Streams - The waste streams from the process steps used to make these
dyes are water and brines containing small amounts of organic chemicals.
Manganese dioxide and other oxidizing agents lead to wastes containing heavy
metals which are usually worthwhile recovering for the metal values.
6. EPA Source Classification Code -
7. References - Fierz-David, H. E. and Blangey, L., Fjjnd_amenJ:aJ_ Processes of Dye
Chemistry, Translated from the Fifth Austrian Edition by P. W. "Vitturn,
Interscience Publishers, Inc., New York (1949), pp 317-318; The Chemistry of
Synthetic Dyes and Pigments, Edited by H. A. Lubs, Reinhold Publishing CoV"
(1955), Chapter 7~, "Anthraquinone Dyes and Intermediates", (F. B. Stilmar and
M. A. Perkins, E. C. Buxbaum), pp 351-352, 359-363, 372-375, 397-402, 412-415;
Venkataraman, K., The Chemistry of Synthetic Dyes, Academic Press, New York
(1952), Volume II, pp 835-844, 848-851.
126
-------
plater
Ke2S0
L*cetone_
PROCESS NO. 29:
ANTHRAQUINONE DYES: C.I. 60755, 61105
PROCESS NO. 30:
ANTHRAQUINOKE DYES: C.I. 60756. 62020,
62025, 62070
Halogen-
ated
Anthraquln-
one Com-
pound
Methy
i
P12 "1
lation j M&QH H9^* Methy
29A LH2S°i
C.I. 60755 '
I
x
f Mnd2 I
atfon |(C.I. 62020 (•*" Condensation
29B L °"1y' J 30*
C.I. 61105 1
v Revised
C.I. 60756, 62020,
62025, 62070
5/20/75
o
(Figure 2-341
FIGURE E-24. FLOW CHART FOR THE PRODUCTION OF SELECTED ANTHRAQUIHONE DYES AND PI6MEMTS
FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 29
ANTHRAQUINONE DYES (METHYLATION) (C.I. 60755, 61105)
1. Function - The manufacture of these two dyes involves the treatment of the
substrate anthraquinone compound with a methylating reagent. In one case
(C.I. 60755), an hydroxyl group is methylated, and in the other case, an
amino group is methylated. The reagents for making C.I. 60755 are relatively
noncorrosive materials, so that stirred iron vessels are adequate. The use
of chlorine in making C.I. 61105 necessitates the use of glass-lined
equipment.
2. Input Materials - The starting materials needed to make these dyes are shown
in Table 1.
TABLE 1. STARTING MATERIALS NEEDED TO MAKE C.I. 60755 and 61105
C.I. Number Starting Materials
60755 4-aminoxanthopurpurin
water
dimethyl sulfate
acetone
61105 chlorine
methanol
sulfuric acid
3. Operating Parameters - No information is available regarding operating
parameters.
4- Uti 1 ities - No information is available regarding the needed utilities
because the reaction conditions are unknown. However, it is very probable
that electricity, cooling water, and steam are needed.
5. Haste Streams - The waste streams from the manufacturing of these dyes are
brines containing small amounts of organic chemicals.
6. EPA Source Classification Code -
7. References - None.
128
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 30
ANTHRAQUINQNE DYES (C.I. 60756, 62020, 62025 and 62070)
1. Function - The manufacture of these four dyes involves the replacement of
active chlorine substituents in the oC-position of an anthraquinone compound.
In the case of two of the dyes, the displacing moiety is a phenoxy group,
and in a third dye, the displacing moiety is the sulfonic acid group. In
the case of the fourth dye, two halogens are replaced in a single process
step—one by a sulfonic group and the other by a phenoxy group. To make
C.I. 62020, a stirred vessel capable of operation at 40 psi is required. A
glass-lined vessel would be desirable to withstand corrosion by chloride
and sulfite salts.
2. Input Materials - The starting materials are listed below in Exhibit 1.
EXHIBIT 1. STARTING MATERIALS NEEDED TO MAKE
C.I. 60756, 62020, 62025 and 62070
Comoonents Color Index Number
components -^^ ^^020 62025~"62070
l-amino-2-bromo-4-h.ydroxy-
anthraquinone x
phenol xxx
sodium hydroxide x x
1,4-diamino-2,3-dichlor-
anthraquinone x x
sodium sulfite x x
manganese dioxide x
l-amino-2-bromo-4-(2-sulfo-£-
toluidino) anthraquinone x
3. Operating Parameters - To make C.I. 62020, one heats 1 part of 2,3-dichloro-
1,4-diaminoanthraquinone with 5.5 parts of phenol, 3 parts of sodium sulfite,
0.25 parts of manganese dioxide and 10 parts of water at 140°. The gauge
pressure developed would be only 40 psi. The yield of dye was not reported.
Information about the manufacture of the other dyes could not be obtained
from standard texts on dye technology.
4. Utilities - Electricity, steam, and cooling water are required. No infor-
mation about the amounts needed could be obtained.
5- Waste Streams - The only waste streams from making these dyes would be brines
containing small amounts of organic chemicals, and in some instances, small
amounts of heavy metal ions such as manganese which could not be economically
recovered.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes. Academic
Press, New York (1952), Volume 2, p 850.
129
-------
CO
o
PROCESS NO. 31:
ANTHWQU1NONE DYES AND PIGMENTS: C.I. 61725,
63365, 65049, 65430, 68420
1-Mno-
Anthra-
l quinone I
Aromatic
Carboxylic
Acid
Chloride
C.I. 61725, 63365. 65049,
65430. 68420
PROCESS NO. 32:
ANTHRAQU1NONE DYES: C.I. 62030, 64500
Nitration
32A
I ' C.I. 62030
O
[Figure 2-341
ftxalicl
U;d k-
1_H2S04J
Acylation, Nitration
32B
Hydrolysis, Reduction
32C
C.I. 64500
Revised 5/20/75
FIGURE 2-25. FLOW CHART FOR THE PRODUCTION OF SELECTED ANTHRAQUINONE DYES AND PIGMENTS
FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 31
ANTHRAQUINONE DYES (AMIDE FORMATION) (C.I. 61725, 63365,
65Q49 and 68420)
1• Function - These dyes are all amides of aminoanthraquinone compounds.
They are made quite simply by the reaction of an aromatic carboxylic
acid chloride with the selected ami no compound at temperatures from
50 to 160°. An acid acceptor (typically sodium carbonate) is sometimes
used. An inert organic solvent is required as the reaction medium.
The reactor should be glass-lined. Good stirring is necessary.
2. Input Materials - The necessary principal raw materials and their
relationship to the product dyes are shown in the matrix below
(Exhibit 1).
EXHIBIT 1. RELATIONSHIP OF PRINCIPAL STARTING MATERIALS
TO PRODUCTS
Color Index Number
Starting Materials 61725 63365 65049 68420
Benzoyl Chloride
Anisoyl Chloride
Phthaloyl Chloride
1,9-Anthrapyrinidine-2-carboxyl
Chloride
1,5-Diaminoanthraquinone
1,5-Diamino~4,8-dihydroxyanthra-
quinone
1-Aminoanthraquinone
The inert organic solvent is typically a high boiling material in which
the starting materials dissolve well. Frequently used materials are:
nitrobenzene, £-dichlorobenzene and trichlorobenzene. To make 100 pounds
of C.I. 61725, the following raw materials are needed:
1,5-Diaminoanthraquinone 69.6 pounds
Benzoyl Chloride 41.1 pounds
p_-Dichlorobenzene 1,392.0 pounds
Virtually all of the p_-dichlorobenzene is recovered. An acid receptor
is not used. In consequence, the evolved hydrogen chloride must be
trapped in a water scrubber.
3. Operating Parameters - The reaction is run at temperatures between 50 and
150° C. Because of the heat evolved, it may be necessary to cool the
reacting mixture as the starting materials are combined.
131
-------
Process No 31 (continued) Page Two
4. Utilities - Electricity, steam, and cooling water are required, but no
data are available regarding the necessary amounts.
5. Waste Stream - The waste stream from making these dyes would always be a
brine containing small amounts of organic materials.
6. EPA Source Classification Code -
?• References - Fierz-David, H.E., and Blangey, L., Fundamental Processes of
Dye Chemistry. Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), pp 322-323.
The Chemistry of Synthetic Dyes and Pigments. Edited by H. A. Lubs.
Reinhold Publishing Company (1955), Chapter 7, "Anthraquinone Dyes and
Intermediates" (F. B. Stilmar and M. A. Perkins), pp 363-4, 422.
132
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 32
ANTHRAQUINONE DYES (NITRATION OF DIAMINOANTHRAQUINONES)
(C.I. 62030 and 64500)
1. Function - The dyes made by this process are related to those made by
Process Number 30 in that dyes in both groups depend on the use of a
selected diaminoanthraquinone compound as a principal starting material.
This process may have only one step, as in making C.I. 62030, or
it may require as many as four steps, as in making C.I. 64500. The
process equipment for making these dyes would necessarily
be a glass-lined vessel fitted with an efficient stirrer and means for
heating and cool ing.
2. Input Materials - The two principal organic chemicals required are
1,4-diaminoanthraquinone (C.I. 62030) and 1.5-diaminoanthraquinone
(C.I. 64500). The inorganic materials used are: nitric acid, sulfuric
acid, oxalic acid, and sodium sulfide. No quantitative information could
be found regarding the manufacture of these dyes.
3. Operating Parameters - No information could be found in the available
texts on dyes regarding the conditions for making these products.
4- Utilities - Electricity, steam, and cooling water are necessary utilities,
but no data could be found on the amounts required.
5. Waste Streams - The nitration step in making each of these dyes is apt to
lead to small amounts of gaseous emissions (nitrogen oxides). In a well-
run plant, these would be minimal and could be contained by suitable
scrubbers. The reduction with sodium sulfide on the intermediate nitro
compound in making C.I. 64500 might generate further gaseous emissions
(hydrogen sulfide). These too can be well controlled.
The principal liquid waste streams would be spent acid fromthe nitration.
These acids are diluted with water and the sulfuric acid could be
concentrated and recovered. More nitrogen oxide emissions would be
generated in this concentration step.
6. EPA Source Classification Code -
7- References - No references to making these products could be found in the
standard texts on dyes.
133
-------
PROCESS NO. 33: ANTHRAQUINONE DYE: C.I. 63010
1,5-di-
hydroxy-
anthraquin-
Sul fonation
60
1,5-
Dihydroxy-
anthraquin
one-2,6-Oi
sulfonic
Acid
Water
NaOH
Na2S
Nitration, Reduction
33A
C.I. 63010
2 ) [Figure 2-341
Revised 5/20/75
FIGURE 2-26. FLOW CHART FOR THE PRODUCTION QF AN ANTHRAQUIN0NE DYE FROM VARIOUS INTERMEDIATES
134
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 33
ANTHRAQUINONE DYES (C. I. 63010)
1. Function - This single dye is made by a three-step process involving first
the sulfonation of 1,5-dihydroxyanthraquinone, followed by nitration of the
intermediate 1 ,5-dihydroxyanthraquinone-2,6-disulfonic acid and reduction
of the two nitro groups so introduced. The process steps for introducing
the nitro groups and reducing them to amino groups are similar to those
used in Process No. 31. All the steps in the process can be carried out
in iron vessels with good agitation.
2. Input Materials - The necessary raw materials are: 1 ,5-dihydroxyanthraquinone,
oleum, nitric acid, sulfuric acid, sodium hydroxide, and sodium sulfide.
No information was available on the amounts of starting materials used in
the process.
3- Ojperating Parameters - No information was available regarding reaction
conditions in the standard texts on dyes.
4- Uti1ities - No information is available regarding the needed utilities
because the reaction conditions are unknown. However, it is very probable
.that electricity, cooling water, and steam are needed.
5. Waste Streams - All the steps in the process may lead to small amounts of
gaseous emissions: sulfur oxides, nitrogen oxides and hydrogen sulfides.
In a well-run plant, these emissions can be held to very low levels. The
liquid effluents are mainly spent acids. The byproduct elemental sulfur
from the reduction of the nitro groups is easily recovered for other uses
in the plant.
6. EPA Source Classification Code -
?• Refej^ences - Venkataraman, K., The Chemistry of SyntheticDyes, Academic
Press, New York (1952), Volume II, pp 848,885.
135
-------
OJ
PWKISS W. 34: WTXRWJuiHOtECARBAZOLE D¥ES: C.I. 65230, 69500, 69525
PROCESS NO. 35: ANTHRAPYRAZOLE DYES: C.I. 73015, 70320
C.I. 65230
I CuO
(Naphthalene
N»2C03
•H
Condensation
34B
Cyclization
34C
C.I. 69500, 69525
NaOH
DUzotUation
35A
Reduction
35B
Cyclization,
Dimerization
35C
IKOH
JEt Tosylate
Ethylation
35D
' C.I. 70315
O
(Figure 2-34)
Revised 5/20/75
FIGURE 2-27. FLOW CHART FOR THE PRODUCTION OF SELECTED ANTHRAQUINONE DYES FROM VARIOUS INTERMEDIATES
ANTHRAQUINONECARBAZOLES AND ANTHRAPYRAZOLES
-------
ORGANIC DYES AND PIGMENTS
PROCESS NO. 34
ANTH_RAQUINONE _DYES (ANTHRACARBAZOLES) (C.I. 65230,
69500 and 69T251
2.
Function - The dyes in this category have much in common with the products
made by Process Numbers 36 and 38. They are all made by the condensation
of a brominated or chlorinated polycyclic keto compound with one or more
polycyclic compound earring an ami no group. The dyes made by these three
processes differ mainly in regard to the exact nature of the starting
materials. Glass-lined vessels fitted with an efficient stirrer and a
reflux condenser serve for carrying out the necessary reactions.
Input Materials - The three dyes made by this process respectively require
the raw materials shown in the matrix below (Exhibit I).
EXHIBIT I. RAW MATERIALS NEEDED TO MAKE ANTHRACARBAZOLE DYES
Co 1 or Index Number
Component
1-Aminoanthraquinone
3-Bromobenzanthrone
3 ,-9-di bromobenzanthrone
Tetrabromopyranthrone
Aminoviolanthrone
Copper oxide
Nitrobenzene
Naphthalene
Sodium acetate
Sodium carbonate
Potassium hydroxide
Isobutyl alcohol
4.
7,
69500
x
X
X
X
X
X
X
X
X
X
X
69525
X
X
X
X
X
X
X
No information could be found on the amounts of materials necessary to make
100 pounds of the dyes.
3. Operating Parameters - The condensation of the brominated compound with the
ami no compounds is carried out at a high temperature in the range of
210-220°. The cyclization of the intermediate anthrimide in making C.I. 69500
and 69525 is accomplished at 108°.
Utilities^ - A liquid heat transfer system is needed, together with electricity,
steam, and cooling water to carry out the various process steps. The amounts
of these utilities needed are not known.
Waste Streams - No liquid effluents would result from the manufacture of
these dyes. Solid wastes containing copper salts and sodium bromide would
have economic value and could be recovered if enough material were processed
on a single occasion. Distillation residues from the recovery of the organic
solvents could best be disposed of by incineration.
6. EPA Source Classification Code -
References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
New York (1952), Volume II, pp 967, 930.
Dress
137
-------
... DYES__AND_PJ6MENJS Pj^LsAJJL_ Jl
ANTHRAQUINONE DYES (ANTHRAPYRAZOLES):
1C.I. 70315 and 70320)
1. Function - These dyes are a relatively simple elaboration of the anthra-
quinone structure and are made from 1-amino-anthraquinone as the principal
organic raw material.
2. Input Materials - The following starting materials are needed to make both
dyes:
1-aminoanthraquinone
sulfuric acid
sodium nitrite
sodium bisulfite
sodium hydroxide
ethyl alcohol
In addition, either diethyl sulfate or ethyl tosylate is required to convert
C.I. 70315 to C.I. 70320. No quantitative information could be found regarding
the input materials.
3. Operating Parameters - The diazotisation of 1-aminoanthraquinone is done at
15-35° in sulfuric acid with 40 percent nitrosylsulfuric acid made from
sodium nitrite and sulfuric acid. The reaction takes four hours. Reduction
of the diazo compound to a hydrazine is done at 20-70° with sodium bisulfite,
followed by ring closure to the pyrazolanthrone with 100 percent sulfuric
acid at 90-95°. No further information could be found regarding the reaction
parameters.
4- Utilities - Electricity, cooling water, and steam are needed, but the amounts
necessary are not known.
5. Waste Streams - A waste stream of spent acid would result from the diazotization
step. Nitrogen oxides might be evolved in the course of the diazotization.
The sodium sulfite used to reduce the diazo compound might be a source of
sulfur dioxide emissions. A brine containing small amounts of organic
materials would be a byproduct in eyelizing the hydrazine compound to the
anthrapyrazole.
•
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes arid Pigments, Edited by H. A.
Lubs, Reinhold Publishing Co. (1955), Chapter 7, "Anthraquinone Dyes and
Intermediates" (F. B. Stilmar) pp 468-470; Venkataraman, K., The Chemistry
of Synthetic Dyes, Academic Press, New York (1952), Volume II, pp 993-994.
138
-------
PROCESS NO. 36:
ANTHRAQUINONE OYES: C.I. 67000, 67300
PROCESS NO. 37
ANTHRAQUINONE DYES AND PIGMENTS:
C.I. 69015, 69025
CO
2-Amino-
3-hydroxy-
anthraqutn
one
0-0C12"
H2S"4
Condensation
Cyclization
36C
y>
[H2S041
Water U»-
NaOCl J
Reduction
360
r C.I. 67300
Water
H,S04
Oleum
NaHSO,
Oxidative Cjclization,
Purification
37B
C.I. 67000
o
(Figure 2-341
C.I. 69015. 69025
Revised 5/20/75
FIGURE 2-28.
FLOW CHART FOR THE PRODUCTION OF SELECTED ANTHRAQUINONE DYES AND PIGMENTS FROM
VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 36
ANTHRAQUINONE DYES (AN OXAZOLE AND A THIAZOLE TYPE)
(C.I. 67000 and 67300)
1• Function - These two dyes possess structural similarities in common, and both
are made from aminoanthraquinone compounds. Batch type reaction vessels made
of iron and fitted-with good stirrers should serve for carrying out both
reactions. The vessel for making C.I. 67300 must also have a reflux
condenser and provision for heating the reaction mixture to 220°. The vessel
for making C.I. 67000 also must have a cooling coil to remove the heat
generated by a moderately exothermic first reaction. The cyclization
reaction is carried out with heating.
2. Input Materials - To make C.I. 67300, the following materials are required:
2,6-diaminoanthraquinone
benzotrichloride
sulfur
naphthalene
cuprous chloride (catalyst)
The naphthalene serves only as solvent and is recovered. To make C.I. 67000,
the following materials are required:
l-nitro-2-anthraquinone carbonyl chloride
2-ami no-3-hydroxyanthraqui none
pyridine
sulfuric acid
sodium sulfide
a- di chlorobenzene
3. Operating Parameters - In making C.I. 67300, the reaction mixture is heated
at 220° for 10 hours. In making C.I. 67000, the reaction between the amino-
anthraquinone and the acid chloride is exothermic. The cyclization of the
resulting amide to the desired oxazole is carried out in p_-dichlorobenzene as
solvent at 140° in 5 hours. No further information on the operating
parameters for making these dyes could be found.
4. Utilities - A liquid heat transfer system is necessary in making C.I. 67300.
Electricity, steam, and cooling water are also necessary utilities for making
these colors. The amounts needed are not known.
5- Waste Streams - .Solid wastes arise in the form of distillation residues
obtained in recovering the pyridine and solvent materials. They would likely
be dealt with by incineration. The liquid effluents would be brines, spent
sulfuric acid and a sodium thiosulfate solution containing small amounts of
organic chemicals. The spent acid and the sodium thiosulfate could be
economically recovered. ,
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 911-912, 1115-1116.
140
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 37
ANTHRAQUINONE DYES AND PIGMENTS (ANTHRACARBAZOLES)
(C.I. 69015 and 69025)
1. Function - The dyes made by this process have a structural similarity to
the dyes made by Process Numbers 33 and 38. They differ mainly in regard
to the nature of the starting materials. The reactions are best carried
out in glass-lined vessels fitted with efficient stirrers and a reflux
condenser.
2. Input Materials - Both products depend on l-benzamido-5-chloroanthraquinone
as one of the two principal starting materials. To make C.I. 69015, this
compound is combined with l-amino-4-benzamidoanthraquinone. The other
product is made by combining this same compound with l-amino-5-benzamido-
anthraquinone. The other raw materials needed are:
sodium acetate
copper (powder) or cuprous chloride
nitrobenzene
sodium dichromate
sulfuric acid
sodium bisulfite
No information ris available on the amounts of materials necessary to make
100 pounds,, of these products.
3. Operating Parameters - The condensation of the two principal raw materials is
carried out at the boiling point of nitrobenzene, 211°. The cyclization
reaction to form the dye is accomplished with sulfuric acid containing a very
small amount of sulfur trioxide. The reaction requires 6-10 hours to complete.
No further information was available regarding the operating parameters.
4. Utilities - A liquid heat transfer system is necessary, together with
electricity and cooling water in unknown amounts.
5. Waste Streams - The principal waste streams from the manufacture of these
colors are more or less concentrated solutions of sulfuric acid, containing
small amounts of organic chemicals. Other liquid effluents are aqueous
solutions containing salt, copper ion, chromium ion and sulfate ion.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by H. A.
Lubs, Reinhold Publishing Co. (1955)/Chapter 7, "Anthraquinone Dyes and
Intermediates", (M. S. Whelen), pp 461-465; Venkataraman, K., The Chemistry
of Synthetic Dyes, Academic Press, New York (1952), Volume II, pp 901-903.
141
-------
PROCESS NO. 38:
ANTHRAQUINONE DYES AND PIGMENTS: C.I. 69800, 70600
PROCESS NO. 39:
ANTHRAQUINONE DYES-ANTHRACARBAZOLES: C.I. 70800. 70805. 71050
ro
KOH
Iwater
NaNO
C.I. 69800
Alkali Fusion. 215-220°
38A
Slater "I
laOH I ^
razs204r^
t2soS J
Product Purification,
Filtration
38B
C.I. 69800
O
[Figure 2-10)
C.I. 70600
Mater
TiCl,
or
SbClt
Condensation,
Filtration
C.I. 70600
O
(Figure 2-34)
C.I. 70800, 70805, 71050
Revised 5/22/75
FIGURE 2-29. FLOW CHART FOR THE PRODUCTION OF SELECTED ANTHRAQUINONE DYES AND PIGMENTS FROM
VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 38
ANTHRAQUINONE DYES AND PIGMENTS--INDANTHRONE AND
FLAVANTHRONE (C.I. 69800 and 70600]
!• Function - These two important colors are made from 2-aminoanthraquinone as
the principal organic chemical starting materials. The manufacture of C.I.
69800 is carried out in an iron vessel capable of being heated to a high
temperature. The manufacture of C.I. 70600 must be done in a glass-lined
vessel with a reflux condenser and an efficient stirrer. This vessel also
must be heated to a high temperature.
2. Input Materials - Both colors are based on 2-aminoanthraquinone. For the
case of C.I. 60800, materials necessary to make 100 pounds of the color are
shown in Table 1.
TABLE 1. STARTING MATERIALS NEEDED TO MAKE 100 POUNDS OF
C.I. 69800
sodium nitrate 25.0 pounds
potassium hydroxide 2.94 "
sodium hydroxide ' 1.30 "
sodium hydrosulfite 57.0 "
sulfuric acid 33.0
water 793 gallons
In the case of C.I. 70600, no information could be found regarding the
amounts of materials necessary to make 100 pounds of the color. The list of
materials required is as follows:
2-aminoanthraquinone
nitrobenzene
titanium tetrachloride or
antimony pentachloride
3. Operating Parameters - To make C.I. 69800 from 2-aminoanthraquinone, the
fusion reaction must be done starting at 180° and finishing at 225° over a
period of 2-3 hours. Careful temperature control is imperative to obtain
the best possible yield of product. The treatment of 2-aminoanthraquinone
at 100-175° with titanium tetrachloride is reported to give a good yield of
C.I. 70600.
4- Utilities - A hot liquid heat transfer system is needed, together with
electricity, steam, and water in unknown amounts.
5. Waste Streams - The waste products from making these colors are all aqueous
solutions. The two streams from making C.I. 69800 are strongly alkaline.
One of the streams contains sodium sulfate as well.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 931-938, 988-990.
143
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 39
ANTHRAQUINONE DYES (ANTHRACARBAZOLES) (C.I. 70800, 70805,
and
1. Function - These three dyes are closely related to the anthracarbazole dyes
made by Process Numbers 33 and 36. One of the starting materials, 1-
ami noanthraqui none, is used both in Process Number 33 and to make C.I. 71050
(Process Number 38). Otherwise, different starting materials are used in
the three processes. As in the related processes, the reactions involved
are best carried out in glass-lined vessels fitted with a reflux condenser
and an efficient stirrer.
2. Input Materials - The starting materials needed to make these dyes are shown
in the matrix below (Exhibit 1). The amounts of these materials needed to
make 100 pounds of a dye are not available in the accessible literature.
EXHIBIT 1. STARTING MATERIALS NEEDED TO MAKE
ANTHRACARBAZOLE DYES C.I. 70800,
70805 and 71050
Starting Materials Color Index Number
70800 70805 71050
1 ,4-di ami noanthraqui none x
1-chloro (or bromo)-anthraquinone x x
aluminum chloride x x x
picoline x x
1 ,5-diaminoanthraquinone x
sodium hypochlorite x
copper x
sodium chloride x
nitrobenzene x
1 -ami noanthraqui none x
1 ,4,5,8-tetrachloroanthraquinone x
3. Opera ti ng Parameters - The reaction to form C.I- 70800 is carried out at 135°.
The formation of C.I. 71050 requires the condensation of 1 -ami noanthraqui none
(4 moles) with one mole of 1 ,4,5,8- tetrachloroanthraquinone at 205° over a
period of 36 hours, using nitrobenzene as solvent, sodium carbonate to
neutralize the evolved hydrogen chloride and copper powder as catalyst.
Cyclization to desired dye is done with aluminum chloride and sodium chloride
at 160° in 2-3 hours. No further information on operating parameters is
available.
4. Uti 1 i t i es - A hot liquid heat transfer system is needed, together with
electricity, steam, and water.
5. Waste Streams - A solid waste would be generated as a distillation residue
in recovering the nitrobenzene. Brines containing copper and aluminum ions
and small amounts of organic compounds would be obtained in washing the dyes.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 906-907.
144
-------
-Ca-
en
PROCESS NO. 40:
CYCLIC IHIDE DYES AND PIGMENTS: C.I. 71100-71110
Ipyrldine
lor HOAc
(Water
EtOH
IKOH
Amide Formation and
Filtration
40A
C I 71100-71110
PROCESS NO. 41:
PERYIENE VAT DYES AND PIGMENTS: C.I. 71129-71145 AND 3,4,9,10-PERYLENETETRACARBOXYLIC ANHYDRIDE
[NaOH
... ,
A'k»11 Fuslon
41A
3,4,9,10 Perylene-
tetracarboxylic
Anhydride '
C .1. 71129
C.I. 71130
Revised 5/21/75
(Figure 2-341
FIGURE 2-30. FLOW CHART FOR THE PRODUCTION OF SELECTED CYCLIC IMIDE AND PERYLENE VAT DYES AND
PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 40
CYCLIC IMIDE DYES AND PIGMENTS (C.I. 71100-71110)
1- Function - These colors are not related to any others. Although only a
single process step is required to make them from the two required starting
materials, further treatment of the primary product (C.I. 71110) is necessary
to obtain the other two products. The necessary condensation reactions to
make the primary product can best be carried out in a closed reaction vessel
made of 316 stainless steel. Subsequent treatments to make the other two
colors can be done in steel vessels fitted with efficient stirrers and a
reflux condenser.
2. Input Materials - The materials needed to make 100 pounds of C.I. 71110 are
shown in Table 1 below.
TABLE 1. STARTING MATERIALS NEEDED FOR 100 POUNDS OF C.I. 71110
1,4,5,8-naphthalene tetracarboxylic acid 68 pounds
Oj-phenylenediamine 27.6 "
acetic acid 459
To make 100 pounds of C.I. 71105, the starting materials shown in Table 2
are needed.
TABLE 2. STARTING MATERIALS NEEDED FOR 100 POUNDS OF C.I. 71105
C.I. 71110 169.5 pounds
potassium hydroxide 339 "
ethanol 1695
This process step simultaneously yields about 69 pounds of C.I. 71100.
3. Operating Parameters - The reaction of the primary starting materials takes
place over a period of 6-7 hours at 120° (2° above the boiling point of
the solvent medium), necessitating the use of the vessel slightly above
atmospheric pressure. The treatments with the potassium hydroxide in
alcohol take place at 75° over a period of one hour.
4- Utilities - Electricity, steam, and water are required in unknown quantities.
5. Waste Streams - Small amounts of solid wastes result from distillation
residues obtained in the recovery of acetic acid and ethanol. Aqueous streams
containing organic chemicals result from washing the finished colors. These
liquid effluents would contain acetic acid, o-phenylenediamine, ethanol,
and potassium hydroxide among other materials.
6. EPA Source Classification Code -
7. References - Venkataraman, K., TheChemistry of Synthetic Dyes. Academic
Press, New York (1952), Volume II, pp 1191-1192.
146
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 41
PERYLENE VAT DYES AND PIGMENTS (C.I. 71129-71145 AND
3,4,9,10-PERYLENETETRACARBOXYLIC ANHYDRIDE)
1- Function - These colors are not related to any other class of colors. Their
manufacture depends primarily on the conversion of the starting material to
C.I. 71129. The other products are chemical modifications of this color.
All the process steps for making these colors can be carried out in iron
vessels fitted with stirrers.
2. Input Materials - The seven colors all depend on first making C.I. 71129
from sodium hydroxide and naphtha!imide. This color serves as an inter-
mediate which reacts with other chemicals to make the other products as
shown in Table 1.
TABLE 1. AUXILIARY CHEMICALS REQUIRED TO MAKE PERYLENE VAT
DYES AND PIGMENTS
Color Index No. Auxiliary Chemicals
71130 dimethyl sulfate
sodium carbonate
71135 £-chloroaniline
water
71137 3,5-dimethylaniline
water
71140 p_-anisidine
water
71145 £-phenetidine
water
3,4,9,10-perylene-
tetracarboxylic anhydride water
3. Operating Parameters - No information is available on the operating parameters
for the process steps.
4. Utilities - Electricity, steam, and water are needed in unknown quantities.
5. Haste Streams - Liquid effluents containing alkali, sodium sulfate, and
organic compounds result from making these colors.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 949-950.
147
-------
PROCESS NO. 42:
INOIGOIO DYE: C.I. 73000
PROCESS NO. 43:
1NDIGOID DYES: C.I. 73000, 73410
PROCESS NO. 44:
1NDIGOID DYES AND PIGMENTS C.I. 73395, 73410
CO
C.I. 73000
Ice
HC1
NaN02
Na2S
NaOH
Diazotisation, Substi-
tution, Alkylation
43A
Water
[NaOH _
Alkali Fusion,
Oxidation
436
C.I. 73300
(Figure 2-101
o
H
[L-
IdCHjCOOH
Acid Chloride Formation
Reduction, Alkylation
44A
Acid Chloride Formation,
Cyclization, Oxidation
44B
[Figure 2-341
C.I. 73395
73410
Revised 5/23/75
FIGURE 2-31. FLOW CHART FOR THE PRODUCTION OF SELECTED INOIGOID DYES AND PIGMENTS FROM VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 42
INDIGOID DYE (C.I. 73000)
1. Function - This dye is a classical material -- indigo. It is the progenitor
of a large number of related materials, some of which are made by Process
Numbers 42, 43, 44, and 45. Indigo is made in two process steps, the first
of which (42A) can best be carried out in a steel autoclave, and the second
(42B) in a steel fusion vessel.
2. Input Materials - Although the quantities of starting materials for making
C.I. 73000 are given in the reference cited below, internal inconsistencies
in the information were found. The raw materials are listed in Table 1.
TABLE 1. RAW MATERIALS NEEDED TO MAKE C.I. 73000
aniline
sodium hydroxide
sodium cyanide
potassium hydroxide
sodium amide
water
air
hydrochloric acid
ice
3. Operating Parameters - The reaction between aniline and sodium cyanide is
carried out under a carbon dioxide pressure of 45 psi, at 50-90° for 30
minutes. The resulting nitrile is hydrolyzed at 110° in 90 minutes, the
unchanged aniline extracted with hot benzene and the solution of alkali phenyl-
glycinate evaporated to dryness. The dried alkali phenylglycinate is fused
with sodium amide and caustic alkali at 220° for 5-6 hours and discharged
into an ice-water slurry.
4. Utilities - Electricity, refrigeration, compressed air, steam, water, and
a hot liquid heat transfer system are required. The amounts of the various
utilities needed are not known.
5. Haste Streams - The waste streams of caustic alkali must be recovered in the
interest of good economy. Waste wash waters are obtained containing small
amounts of salts and organic compounds.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 1013-1016.
149
-------
ORGANIC DYES AND PIGMENTS
PROCESS NO. 43
INDIGOID DYE(C.I. 73300)
Function - This dye, thiolndigo, is structurally related to the indigoid dyes
made by Processes 42, 44, and 45. C.I. 73300 is the sulfur analog of C.I.
73000. The manufacture of thioindigo requires two process steps. The first
step (43A) is done in an open stainless steel vessel fitted with an efficient
stirrer, and the second step (43B) must be carried out in a steel vessel
which can be evacuated and heated as well.
Input Materials - The quantities of material needed to make 100 pounds of
C.I. 73300 are shown in Table 1 below.
TABLE 1. STARTING MATERIALS NEEDED TO
C.I. 73300
MAKE 100 POUNDS OF
anthranilic acid 16.2 pounds
water 750 gallons
sodium nitrite 81.2 pounds
hydrochloric acid (33.3% HC1) 538
sodium sulfide 200 "
iron borinzo 235.3 "
sulfur 197.2
chloroacetic acid 122.4
sodium hydroxide 482.6 "
sodium carbonate 129 "
sulfuric acid 200
ice 1176
3. Operating Parameters - The conversion of anthranilic acid to the intermediate
o-(carboxymethyl) mercaptobenzoic acid (43A) requires about 4 hours at
various temperatures ranging from 0 to 100°. Fusion of this intermediate
(43B) with caustic involves first grinding the reacting materials in a ball
mill and then heating the mixture in an evacuated vessel 2-3 hours at 205°.
4. Utilities - Electricity, water, steam, refrigeration, a vacuum system and a
hot oil heat transfer system are needed. The amounts of utilities required
are not known.
5. Haste Streams - The sodium hydroxide waste streams must not be discharged,
but rather must be recovered for recycling in the interests of economy. Some
dilute alkali solutions are inevitably discharged. They also contain sodium
chloride and small amounts of organic chemicals. The diazotization step (43A)
inevitably leads to small emissions of nitrogen oxides.
6. EPA Source Classification Code -
7. References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of Dye
Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), pp 330-331; Venkataraman, K.,
The Chemistry of Synthetic Dyes, Academic Press, New York (1952), Volume II,
pp 1031-1032.
150
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 44
INDIGOID DYE AND PIGMENT (c. i. 73395 and 73410)
1. Function - These two colors are members of the thioindigo family of colors,
and are closely related to the dyes made by Process Numbers 42, 43, 45, and
46. Although the basic chemical structure of these dyes is the same as that
for the dyes made by Process Numbers 43 and 45, the process is different
in chemical details. Two process steps are involved. The corrosive nature
of the materials involved dictates the use of glass-lined reaction vessels.
Good stirring is needed for all of the reactions, and provision must be
made for the trapping of hydrogen chloride evolved in both process steps.
2. Input Material^ - The starting materials common to the manufacture of these
two colors are shown in Table 1.
TABLE 1. STARTING MATERIALS COMMON TO THE MANUFACTURE OF
C.I, 73395 and 73410
phosphorus pentachloride
phosphorus trichloride
zinc dust
sulfuric acid
aluminum trichloride
chloroacetic acid
air
In addition to these materials, 4-chloro-2,5-dimethylbenzenesulfonic acid
is needed to make C.I. 73395, and 2-naphthalenesulfonic acid to make C.I.
73410. The amounts needed to make 100 pounds of these colors could not be
ascertained,
3. Operating Parameters - No information could be obtained regarding the
conditions for the process steps.
4- Utilities - Electricity, water, steam, and compressed air are the needed
utilities, but the amounts required are unknown.
5. Haste Streams - The effluents from the manufacture of these dyes are dilute
hydrochloric acid, phosphorus oxychloride, aqueous zinc chloride solution and
aluminum chlorohydrate solution. Solid waste residues would be formed from
the distillation of various intermediate materials.
6. EPA Source Classification Code -
7. References - The_Chemistry of Synthetic Dyes and Pigments, Edited by H. A.
Lubs, ReinholcTPubTTshing Co7~0955), Chapter 8, "Indigoid Dyes" (A. J.
Johnson), pp 567-568; Venkataraman, K., The Chemistry of Synthetic Dyes,
Academic Press, New York (1952), Volume II, pp 1034, 1036.
151
-------
SPOCESS ',0. 45:
INDIGCID :V£S AND PIGMENTS: C.I. 73310, 73312, 73335,
73360, 73385, 73390
0C1
Water
Ice
CaC03
Herz Reaction,
Hydrolysis
Amino-
thlol
Inter-
mediate
NaN02
Na2S4
Air
Alkylation,
Cyclization
458
C.I. 73310 73385
73312 73390
73335
73360
PROCESS flO. 16:
INDIGOID DYE: C.I. 73670
Chlorine,
Bromine
Oxidation, Bromination
Chlorination
46A
9-Chloro-
naphtho[l
2-bJthio-
pnen(2H)-
one
5-Bromo-
2-chloro-
3-pseudo-
indolene
C.I. 73670
[Fioure 2-34]
Revised 5/21/75
FIGURE 2-32. FLOW CHART FOR THE PRODUCTION OF SELECTED INDIGOID DYES ANO PIGMENTS FROM VARIOUS INTERMEDIATES
152
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 45
INDIGQID DYES AND PIGMENTS
1. Function - The six thioindigoid colors made by this process are structurally
related to the colors made by Process Numbers 42, 43, and 44. Two process
steps are needed to make these products. The corrosive nature of the materials
used necessitates the use of glass-lined equipment. Because low temperatures
are involved in two of the steps (one of which is a diazotization) ice is
used in substantial quantities. Good stirring is required in all the reactions
which are carried out.
2. Input Materials - The starting materials common to the manufacture of the
seven colors are shown in Table 1.
TABLE 1. STARTING MATERIALS COMMON TO THE MANUFACTURE OF SIX
THIOINDIGO COLORS
sulfur chloride sodium tetrasulfide
chlorobenzene sodium cyanide
ice cuprous chloride
water sodium bicarbonate
chloroacetic acid calcium carbonate
zinc dust sodium chloride
sodium hydroxide sulfuric acid
hydrochloric acid
sodium nitrite
In addition to these starting materials, a principal organic starting
material is used for each of the six colors, as shown in Table 2.
TABLE 2. PRINCIPAL ORGANIC STARTING MATERIALS FOR SIX
THIOINDIGO COLORS
Organic Starting Material C.I. Number
o-chloroaniline 73310
2,5-dichloraniline 73312
£-phenetidine 73335
o-toluidine 73360
4-chloro-o-toluidine 73385
5-chloro-p_-toluidine 73390
No information could be obtained about the quantities of materials needed
to make 100 pounds of any of these colors.
3. Operating Parameters - Temperature conditions for the several reactions range
from 0 to 70°. No significant further information could be found regarding
the reaction conditions.
4- Utilities - The utilities needed are: electricity, refrigeration, steam,
compressed air, vacuum, and water. No information was available as to the
amounts required.
153
-------
Page Two Process No. 45
5. Waste Streams - The liquid waste streams from making these colors include:
brines contaminated with varying amounts of organic chemicals, a brine
containing cyanide ion and certain amounts of organic chemicals. A solid
waste of copper sulfide would result from Process Step 43B.
6. EPA Source Classification Code -
7. References - The Chemistry of Synthetic Dyes and Pigments, Edited by H. A.
tubs, Reinhold Publishing Co. (1955), Chapter 8, "Indigoid Dyes" (A. J.
Johnson) p 566; Venkataraman, K.5 The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 1026-1028, 1033, 1034.
154
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 46
INDIGOID DYE (C.I. 73670)
1. Function - The molecule of this dye is a hybrid. One-half is made from indigo
(C.I. 73000, Process No. 42) and the other half is a specially made inter-
mediate structurally related to the thioindigo colors. Glass-lined vessels
fitted with efficient stirrers are needed for the two processing steps.
2. Input Materials - The starting materials needed to make this dye are shown
in Table 1.
TABLE 1. STARTING MATERIALS NEEDED TO MAKE C.I. 73670
indigo nitric acid
water sodium carbonate
sodium dichromate 9-chloronaphtho[l ,2-b]thiophen
bromine (2H-one)
chlorine
hydrochloric acid
chlorobenzene
Not enough information about the reactions could be found to determine how
much of these materials is needed to make 100 pounds of the dye.
3. Operating Parameters - One of the reaction steps is exothermic and must be
maintained below 17° to obtain a high yield. Another reaction requires a
temperature of 125° with chlorobenzene (b.p. 132°) as solvent. No other
information could be found about operating parameters.
4. Utilities - Electricity, steam, refrigeration, and water and required in
unknown quantities.
5. Haste Streams - The waste streams are brines containing small amounts of
"organic chemicals. One of the brine streams (from step 46A) would likely
contain chromium ion.
6. EPA Source Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 1024, 1029, 1030.
155
-------
PKX2SS HO. 47: PHTHALOCVAttlNC DYES W«0 PIGMENTS: C.I. 741M,74240,742«0,74460
cn
CTl
IFIguie 2-341
Revised 5/20/75
FIGURE 2-33. FLOU CHART FOR THE PRODUCTION OF SELECTED PHTHALOCVANINE DYES AND PIGMENTS FROM
VARIOUS INTERMEDIATES
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 47
PHTHALOCYANINE DYES AND PIGMENTS
(C.I. 74160, 74240, 74260, and
7446Q)
1. Function - The four phthalocyanine colors are all based on a unique primary
intermediate, copper phthalocyanine, (C.I. 74160) which itself finds wide
use as a high quality blue pigment. The chemical modification by chlorination,
(47A) chlorosulfonation (47D) or chloromethylation (47G), gives rise to
the other three colors. Chlorination of copper phthalocyanine is akin to
the halogenation of dyes as practiced in Process No. 12. The chlorosulfonation
process step is related to the sulfonation of dyes as described in Process
No. 15. Steel equipment serves for makinq C.I. 74160 (47A) and carrying out
the pigment finishing steps (478 and 47C). Steel equipment would also serve
for the process steps (47D, E, Fs G, and H) involved.
2. Input Materials - The starting materials needed to make the primary inter-
mediate, C.I. 74160, are listed in Table 1.
TABLE 1. STARTING MATERIALS NEEDED TO MAKE C.I. 74160
phthalic anhydride
urea
copper sulfate
ammonium molybdate
The amounts required to make 100 pounds of the pigment are not available.
In Table 2, the starting materials needed to convert C.I. 74160 to the other
three colors are listed.
TABLE 2. STARTING MATERIALS FOR CONVERTING C.I. 74160 TO
OTHER COLORS
C.I. 74240 C.I. 74260
bis-chloromethyl ether chlorine
alkyl thiourea compound aluminum chloride
aluminum chloride sodium chloride
triethylamine ferric chloride (or cupric
chloride)
C.I. 74460
chlorosulfonic acid
sulfuric acid
2~arnino-4-nitrobenzenesulfonic acid
sodium sulfide
2-amino~4-nitrobenzenesulfonic acid
ammonia
3. Operating Parameters - The condensation of phthalic anhydride with urea is
carried out at a temperature in the vicinity of 160-200°C. The reaction is
quite exothermic in the early stages. The chlorination of C.I. 74160 is
done at 155-190° and the finished, hot melt of chlorinated pigment in the
aluminum chloride-sodium chlorideeutectic is quenched with cold water. The
chlorosulfonation (47D) of C.I. 74160 is done at 30°, with 9 parts of chloro-
sulfonic acid for each part of C.I. 74160. Four sulfonyl chloride groups
are introduced into each pigment molecule. No further information is avail-
able regarding the operating parameters involved in making these colors.
157
-------
Page Two Process No. 47
4- Utilities - Electricity, steam, water, and a hot liquid heat transfer system
are needed. The amounts of utilities required are not known.
5. Waste Streams - The processing of phthalocyanine products results in relatively
large amounts of waste sulfuric acid contaminated with small amounts of
the bright blue pigment. Other steps in the process yield brines containing
aluminum ion and small amounts of organic chemicals. The reduction step
with sodium sulfide (47E) results in a waste stream of sodium thiosulfate
which may be recovered economically.
6. EPA Classification Code -
7. References - Venkataraman, K., The Chemistry of Synthetic Dyes, Academic
Press, New York (1952), Volume II, pp 1128-1133, 1135-1136, 1139.
158
-------
PROCESS NO. 48:
[Figures 2-1 to 2-33]
CJl
[Resin
[Surfactant
Dye
or
P i gwen t
Presscake
or Slurry
Pigment
Dispersion
or Dye
Solution
Finished
Dye or
Pigment
Revised 5/20/75
FIGURE 2-34. FLOW CHART FOR FINISHING STEPS FOK PIGMENT OR OVE PRODUCTION
-------
ORGANIC DYES AND PIGMENTS PROCESS NO. 48
FINISHING STEPS FOR PIGMENT OR DYE PRODUCTION
1. Function - The physical form of a dye or pigment plays an important part in
the sale of the material. In the case of pigments, crystal size surface and
shape have an enormous influence on the color quality and performance of a
given pigment. These qualifications for a pigment can be greatly influenced
by the finishing steps. Of special importance in the manufacture of pigments
is the transfer of a pigment from a water borne phase to an oil borne phase.
At least 67 percent of the total production of pigments is sold in this form.
The equipment used in pigment flushing is simple but specifically designed
for the purpose. Many pigments are flushed in the tank where they are made,
using high speed stirrers. Others are flushed in powerful mixers designed
with "sigma" blade agitators. Vacuum is often needed in this operation.
Such mixers range in size from 2 to 1000 gallons. Drying and grinding of
dyes and pigments are time-honored finishing steps for both dyes and
pigments. This approach to finishing is being used less and less because
of the inherent problems in the processing. Wet grinding is growing in
favor, especially in connection with the growth in the use of water-based
paints. Both ball and hammermills are used for the dry grinding of colors.
Wet grinding is done only in ball mills. Dried dyes are often mixed with
diluents and dispersants for purposes of standarization. Uniformity from
batch to batch is, thus, achieved.
2. Input Materials - The data for a typical case are shown in Table 1 below.
Surface active agents are sometimes needed.
TABLE 1. MATERIALS REQUIRED TO FLUSH 100 POUNDS OF C.I. 74160
C.I. 74160 press-cake, 29.7% solids
Press-cake, Organic Phase, Pigment, Hater
pound pound pound Introduced Removed
First charge 16.84 42.93 50 118.4 104.4
Second charge 16.84 28.79 50 118.4 108.6
Vacuum stripping -- 113.47 -- -- 21.2
Totals 185.19 100 236.8 234.2
Flushed pigment concentration = 35 percent
Moisture content = 0.9 percent
For the dry grinding of a dye or pigment, it is essential to mix the color
with an inorganic, water soluble salt (sodium chloride, calcium chloride,
or sodium sulfate) in an amount equal to 2 to 10 times the weight of the
color.
3- Operating Parameters - The flushing operation can be carried out rapidly and
conveniently. The temperatures employed are generally in the vicinity of
40 to 50°. Grinding is always done at ambient temperatures.
4- Utilities - The required utilities are vacuum, water, electricity, and steam.
The amounts of these utilities needed are not known. However, the power
requirements for flushing (as high as 500 hp) can be surprisingly large
because of the heavy paste consistency of many finished pigment dispersions.
160
-------
Page Two Process No- 48
WasteStreams - The aqueous waste from the flushing of a pigment may contain
varying amounts of organic materials. Dry grinding gives rise to
considerable amounts of brines which may contain organic chemicals. Dry grinding also
leads to much air pollution due to finely divided solids "flying about".
EPA Source ClassificationCode -
References - Fierz-David, H. E. and Blangey, L., Fundamental Processes of
Dye Chemistry, Translated from the Fifth Austrian Edition by P. W. Vittum,
Interscience Publishers, Inc., New York (1949), Chapter III-O, pp 377-378;
Pigment Handbook, Edited by T. C. Patton, John Wiley and Sons, Inc., New York
T1973), Volume III, "Pigment Flushing, III-F" (T. A. Langstroth), pp 447-455;
"Improving the Physical Properties of Pigments, III-A-C" (W. Carr),
pp 29-35.
161
-------
APPENDIX A
RAW MATERIALS USED TO MANUFACTURE ORGANIC DYES,
PIGMENTS AND THEIR INTERMEDIATES
163
-------
TABLE A-l
RAW MATERIALS USED TO MANUFACTURE ORGANIC DYES,
PIGMENTS AND THEIR INTERMEDIATES
acetic acid
acetic anhydride
acenaphthene
acetaldehyde
acetone
acrylonitrile
alky! thioreas
m-aminobenzoic acid
p_-aminobenzoic acid
sec-amylanrine
di-t>amyl phenol
aniline
anthranilic acid
antimony potassium tartrate
benzaldehyde
benzenesulfonic acid
benzoic acid
benzotrichloride
benzoyl chloride
benzenesulfonic acid
benzyl chloride
n-butyl alcohol
i_so-butyl alcohol
ivbutylamine
p_-t-butyl phenol
carbazole
cellulose waste
chloroacetic acid
chloram'l
chlorobenzene
Organic
p_-chlorobenzenesulfonic acid
p_-chl oroni trobenzene
o_-chlorobenzoic acid
p_-chlorobenzoic acid
m-chlorobenzoyl chloride
4_-chloro-3-nitrobenzoic acid
p_-chlorophenol
£-chlorophenol
p_-chloro toluene
£-chlorotoluene
p_- ch 1 oro-»£,=c,e£- tri f 1 uoroto 1 uene
(p_-chlorobenzotri fluoride)
m-cresol
o-cresol
£-cresol
cyanuric chloride
cyclohexyl alcohol
cyclohexylamine
cyclohexanone
2,4-diaminotoluene
p_-di chlorobenzene
p_-di chlorobenzene
diethanolamine
diethylamine
diketene
dimethyl sulfate
dimethyl amine
diphenylamine
£-dodecyl aniline
ethanol
ethanolamine
164
-------
ethyl amine
ethyl chloride
ethyl cyanoacetate
ethyl sodium oxalacetate
ethyl orthoformate
ethyl amine
ethylene dibromide
ethylene glycol
ethylene oxide
formaldehyde (as formalin)
formami de
formic acid
glucose (corn sugar)
glycerol
glycine
hematin
hydrazine
hydroquinone
p_-hydroxybenzoic acid
isophthalic acid
isopropyl amine
logwood extracts
mesitylene
methanesulfonic acid
methyl acetoacetate
methy!amine
methyl isopropyl ketone
methyl mercaptan
methyl sulfate
methylene dianiline
a-methylstyrene
morpholine
naphthalene
1-naphthol
nitrobenzene
m-nitrobenzoic acid
p_-nitrobenzoyl chloride
p_-nitrophenol
£-nitrophenol
m-nitrotoluene
oi-nitrotoluene
_p_-nitro toluene
oxalic acid
o-phenetidine
£-phenetidine
phenol
l-phenol-3-sulfonic acid
l-phenol-4-sulfonic acid
N-phenylanthranilic acid
phthalic anhydride
iso-propylamine
pyrene
pyridine
quebracho extract
resorcinol
salicylic acid
sodium acetate
sodium formate
terephthalic acid
tetrachloroethane
tetrachlorophthalic anhydride
thiourea
toluene
o-toluenesulfonic acid
165
-------
£-toluenesulfonic acid
£-toluenesulfonyl chloride
1,2,4-trichlorobenzene
trimellitic anhydride
urea
m-xylene
j>xylene
2,4-xylenol (2,4-dimethyl phenol)
xylenes, mixed isomers
166
-------
Inorganic
alumina hydrate
aluminum acetate
aluminum chloride
aluminum sulfate
ammonia
ammonium bisulfite
ammonium chloride
ammonium molybdate
barium chloride
boric acid
bromine
calcium carbonate (limestone)
calcium chloride
calcium oxide (lime)
carbon dioxide
chlorine
chlorosulfonic acid
chromium fluoride
chromium formate
chromium sulfate
cobalt acetate
copper (powder)
copper ferrocyanide
cuprous chloride
cupric chloride
cupric oxide
cupric sulfate
ferric chloride
ferrous sulfate
hydrochloric acid
iodine
iron (scrap)
lead carbonate (basic)
lead peroxide
magnesium oxide
manganese chloride
manganese dioxide
nickel acetate
Raney nickel catalyst
oleum
phosgene
phosphomolybdic acid
phosphorus oxychloride
phosphorus pentachloride
phosphorus trichloride
phosphotungstic acid
potassium carbonate (anhydrous)
potassium hydroxide
potassium permanganate
sodium bisulfite
sodium carbonate
sodium chlorate
sodium chloride
sodium cyanide
sodium dichromate
sodium hyposulfite
sodium hydroxide
sodium nitrite
sodium sulfide
sodium sulfite
sodium thiosulfate
stannous chloride
167
-------
strontium chloride
sulfamic acid
sulfur
sulfur monochloride
suIfuric acid
sulfur chloride
sulfuryl chloride
thionyl chloride
zinc
zinc chloride
168
-------
APPENDIX B
DYES AND PIGMENTS MANUFACTURED IN THE UNITED
STATES IN 1973, LISTED IN NUMERICAL ORDER BY
COLOR INDEX NUMBERS
169
-------
TABLE i-J OYES AND PIGMENTS Bf COLOR INDEX NUMBER IN NUMERICAL ORPER
COLOR
INDEX DYE OR PI3MENT NAHE
10005 MORDANT GR5EN <*
10006 PIGMENT GREEN a
10030 ACID GREEN 1
D+C GREEN 8
10316 EXT. D«-C YELLOH 7
ACID YELLO* 1
10338 DISPERSE YELLOW <(2
103U5 DISPERSE YELLOW 1
10395 ACIC BROWN 1
11000 SOLVENT YELLOW 1
PIGMENT YELLOW 98
11005 DISPERSE ORANGE 3
HOlIt BASIC
12390 PIGMENT RED 17
12395 PIGMENT Rt D 13
12"t20 PIGMENT RED 7
12"»i»0 PIGMENT RED 10
121*60 PIGMENT RED 9
121*65 PIGMENT RED 15
12<*80 PIGMENT BPQWN 1
12<*85 PIGMENT RED li.6
121*90 PIGMENT RED 5
12515 PIGMENT RED 176
12i90 DISPERSE YELLOH 8
12710 PIGMENT YELLOW 10
12715 SOLVENT RED 8
12775 PIGMENT GREEN 10
12790 DISPERSE YELLOW 5
13010 ACID DYE 0
13025 ACID ORANGE 52
13058 D + C RED 39
13065 EXT. 0 + C YELLOH 1
ACID YELLOW 36
13060 *CIO ORANGE 5
13090 ACID ORANGE 1
COLOR
INDEX DYE OR PIGMENT NAME
13011 ACID GRANGE 1
13035 ACID YELLOW 63
13150 AGIO GRANGE 50
13225 MORDANT BSOHN 13
13250 MORDANT BROWN 33
13265 MORDAKT BROWN "»9
13360 MORDANT DYE 0
13361 ACID GREEN 35
13390 ACID BLUE 92
131*25 ACID GREEN 12
13900 AGIO YELLOH 99
SOLVENT YELLOH 19
13906 ACID YELLOW 151
13920 DIRECT YELLOW 8
13950 DIRECT YELLOH 27
It025 MORDANT YELLOW 1
1"*030 MORDAhT ORANGE 1
11*055 MORDANT YELLOW 1<*
11*110 MORDANT YELLOH 20
li»130 MORDANT YELLOH 5
11*135 MORDANT YELLOH 36
11*155 DIRECT GREEN 28
11*170 ACID YELLOH 65
11*250 MORDANT BROWN 19
11*270 ACID GRANGE 6
11*625 ACID BROWN 6
11*6^0 MORDANT SLACK 3
li(6i»5 MORDANT BLACK 11
11*700 FD*C RED i*
I
-------
:OLOR
INDEX
TA81EB-1. DYES AND PIGMENTS BY COLOR INDEX NUKBER IN NUMERICAL OROCS <30NTINUEC)
COLOR
DYE OR PIGMENT NA-U IN3EX DYE OR PIGMENT NAME
COLOR
INDEX
15670
15705
15710
15711
15800
15620
13825
15826
15850
1S860
15865
15880
15970
15985
15995
16055
15105
15150
16180
15185
16230
16255
16260
16500
16575
16580
16600
17025
17045
17065
17200
17235
DtC RED 12
D+C RED 11
SODIUM PIGHENT RED 1*9
CALCIUM PliHHNT RE3 49
BARIUM PIGMENT REO 49
MORDANT VIOLET 5
MORDANT BLACK 17
MORDANT BLACK 1
ACID BLACK 52
PIGMENT BROHN 5
OtC RED 31
PIGMENT RED 64
PIGMENT RED 55
PIGMENT REO 58
PIGMENT RED 77
CALCIUM PIGMENT RE3 57
0*C RED 7
0+C RED 6
PIGMENT REO 52
PIG CENT RED 48
PIGMENT RED 63
O+C REO 34
ACIO ORANGE 12
D»C YELLOH 6
FO-t-C YELLOW 6
ACIO ORANGE 31
ACIO VIOLET 56
LAKE PIGMENT RED 65
MORDANT RE3 9
LAKE ACIO REO 26
ACID REO 26
ACID REO 17
LAKE ACID REO 17
ACIO RED 27
FO»C RED 2
0+C REO 2
ACID ORANGE 10
ACIO YELLOH 18
ACIO VIOLET 58
SOLVENT RE3 35
MORDANT BLACK 9
ACID REO 176
ACIO VIOLET 3
ACIO VIOLET 6
ACIO VIOLET 1
ACID RED 37
ACID REO 32
ACID REO 33
D+C RED 33
MORDANT GREEN 36
17590 MORDANT BROWN 40
17755 ACID RED 137
17757 REACTIVE ORANGE 16
17820 DIRECT RED 123
17908 REACTIVE REO 8
17916 REACTIVE BLACK 1
17995 ACIO REO 133
18050 ACID REO 1
18055 ACIO VIOLET 7
18065 ACID RED 35
18073 ACID REO 138
180 75 ACID VIOLET 12
18096 REACTIVE VIOLET 4
18097 REACTIVE VIOLET 5
18105 REACTIVE REO it
18110 ACID RED 106
18158 REACTIVE REO 1
18159 REACTIVE RED 3
18160 MORDANT BLACK 38
18165 ACID BLACK 60
18690 ACIO YELLOH 121
18595 ACIO YELLOH 4
18710 MORDANT YELLOW 30
18732 ACID ORANGE 60
1871*0 ACIO ORANGE 72
187^5 ACID ORANGE 7
-------
03LOR
INDEX
T«U B-I. WES AND PIGMENTS BY COLOR INDEX NUIBER IN NUMERICAL ORDER IOONTINUECI
COLOR
DYE OR PIGMENT M4ME INDEX DYE OR PIGHENT NAME
COLOR
INDEX
ro
22370 OIREOT ORAMSE 1
22375 DIREOT ORANGE 1
221.10 DIRECT YELL3W 23
22<*30 DIRECT OKA'IGE 1
22!*&0 OIREOT VIOLET 27
221.80 OIREOT VIOLET 22
22570 DIRECT VIOLET 1
22590 OIREOT BLUE 2
22870 ACID ORANGE 63
22880 MORDANT YELLOM 25
22890 AGIO REO 97
22895 ACID ORANGE 56
22910 ACID YELLOW 1.2
23050 OIREOT REO 1.6
23155 OIREOT BLUE 98
23266 ACID RED Hi
23285 ACID REO 93
23365 DIRECT ORASGE 6
23370 DIRECT ORAMGE 18
23375 DIRECT ORANGE 6
23500 OIREOT RED 2
23630 OIREOT REO 39
23635 ACID RED 111*
23790 DIREOT BLUE 25
23850 DIRECT BLUE 14
23900 ACID YELLOW 1*1*
23910 ACID REO 89
2"»065 DIRECT BLUE 136
2^100 DIRECT REO 7
21.125 ACID RED 128
2U140 DIREOT SLUE 8
2M75 DIREOT SLUE 151
21*280 DIRECT BLUE 22
21*1.00 DIRECT OLUE 15
2i*l*01 DIREOT BLUE 218
21.1*10 DIRECT BLUE 1
21*1.11 OIREOT BLUE 76
21.810 ACID REO 131.
2i*890 OIREOT YELLOW fc
2W895 DIRECT YELLOW 12
250^0 DIRECT BLACK 71
25100 MORDANT YELLOW IS
25135 ACID YELLOW 38
25200 DIREOT ORANSE 73
25275 DIRECT REO 120
25300 DIRECT YELLOW 26
25380 DIRECT REO 75
251.00 DIRECT VIOLET 62
251.10 DIRECT VIOLET 1*7
26070 DISPERSE YELLOW 23
26100 n + 0 RCD 17
26105 SOLVENT RED 2^
26120 SOLVENT RED 26
26125 SOLVENT RED 27
26150 SOLVENT BLACK 3
26207 ACID RED 350
26360 ACID BLUE 113
26370 ACID BLACK 21.
261*01 ACID BLUE 120
26*10 ACID BLUE 11?
26520 MORDANT ORANGE 6
2655D ACID ORANGE 51
26900 ACID REO 151
26905 A SID RED 66
27070 4013 BLACK 26
27075 ACID BLACK 26
27200 ACID REO 115
27201 ACID RED 115
27290 ACID RED 73
27580 DIRECT RED 16
27700 DIRECT BLACK 17
27720 DIRECT BLACK 51
27855 DIRECT VIOLET 7
27885 DIRECT VIOLET 9
27905 DIRECT VIOLET 51
Z7925 DIRECT SLUE 67
28160 DIRECT REO 81
PIGMENT DIRECT REO 81
28210 DIRECT REO 153
28215 DIRECT REO 127
28230 DIRECT RED 117
28240 DIRECT BLACK 127
28255 DIRECT ORANGE 7<«
28280 DIRECT GREEN 38
28360 DIRECT REO 152
29000 DIRECT YELLOM <*i»
29005 DIRECT YELLOH 1*1
29025 DIRECT YELLOW 50
29060 DIRECT YELLOW 31*
29065 DIRECT REO 79
29090 DIRECT ORANGE 83
29100 DIRECT RED 31
29105 DIRECT VIOLET 1 fc
29110 DIRECT REO 11»9
29120 DIRECT VIOLET 66
29125 DIRECT VIOLET i»8
29150 DIRECT ORANGE 26
29155 DIRECT ORANGE 29
29156 DIRECT ORANGE 102
29160 DIRECT REO 23
291&6
29175
29180
29115
29190
29200
29210
29225
30015
3001*5
30120
301i»0
3011.5
30220
30235
3031*5
30280
30295
30315
31560
31565
31575
31600
316S5
31930
31.010
31.015
31*01.5
31*095
31.090
31*11*0
31.11*6
31.170
3*200
31.215
34220
31.260
35005
35255
351*35
35660
35760
35780
35790
35870
36200
36300
37000
OYE OR PIGMENT NAME
DIRECT RED 1*
DIRECT BROWN 112
DIRECT RED 62
DIRECT REO 73
DIRECT RED 21.
DIRECT RED 26
DIRECT RED 72
DIRECT RED 122
DIRECT REO 83
DIRECT BLACK 78
DIRECT BROWN 1
DIRECT BROWN 151*
DIRECT BROWN 6
DIRECT BROWN 95
DIRECT GREEN 39
DIRECT BLACK 38
DIRECT BLACK I*
DIRECT GREEN 1
DIRECT GREEN 6
DIRECT GREEN 8
DIRECT BLACK 9
DIRECT SLACK 9
DIRECT BLACK 2
DIRECT BLACK so
DIRECT BLACK 36
DIRECT BLUE 26
DIRECT BLUE 126
DIRECT BROWN 32
DIRECT GREEN 25
DIRECT BLUE 120
DIRECT BLUE 120
DIRECT BLUE 71
DIRECT SLUE 71.
DIRECT BLACK 56
DIRECT BLUE 78
DIRECT BLUE si
DIRECT- BLUE 75
DIRECT GREEN 51
DIRECT BROWN <*<»
DIRECT BLACK 19
DIRECT BLACK 22
DIRECT BROWN 31
DIRECT RED 8b
DIRECT RED 80
DIRECT REO 32
DIRECT BLACK 75
DIRECT BROWN 106
DIRECT BROWN 7i»
BASE AZOIC OIAZOIC 1.1.
SALT AZOIC DIAZ QIC «*<*
-------
:OLOR
INDEX
TWUB-1. WES *NO PIGMENTS B
-------
TABU B-l. DVES AN3 PIGN-NTS 8V COtOR INDEX NUMBER IN NUH-RICAL ORDER C30MTINOEO)
:OLOR
INDEX CYE OR PIGMENT NA-IE
42095 ACID GREEN 5
42100 AGIO GR£tN 9
42140 BASK 3LUE 5
42170 ACID GREEN 22
PTA PIGMENT VIOLET 1
'+3500 9*310 RED 9
1*2510 BASIS VIOLET !<•
PMA PIGMENT VIOLET 9
SOLVENT RED ifl
43520 PIGMENT BASIC VIDL-T Z
BASIS VIOLET 2
42535 BASIC VIOLET 1
FUGITIVE PIGMENT VIOLET s
PTA PIGMENT VICLET 3
PMA PIGMENT VIOLET 3
SOLVENT VIOLET 8
1*2536 8ASIC VIOLET 13
1.2555 BASIC VIOLET 3
SOLVENT VIOLET 9
S»2561 AGIO Bi.UE 31*
42595 BASIC SLUE T
SOLVENT BLUE 5
PTA PI3MENT BLUE 1
PMA PIGMENT BLUE 1
42600 PTA PIGMENT BLUE 14
PMA PIGMENT BLUE 14
BASIC VIOLET 4
42640 ACID VIOLET 49
FO + C VIOLET 1
42645 ACID BLUE 15
42650 ACIO VIOLET 17
42655 ACID BLUE 90
42660 ACIC BLUE 83
42735 ACID BLUE 104
LAKE AIID BLUE 104
42750 PIGMENT BLUE 19
'42760 SOLVENT BLUE 23
42775 SOLVENT BLUE 3
42780 LAKE A3ID 3LUE 93
ACIO B.UE 93
43820 MORDANT BLUE 3
43830 MORDANT BLUE 1
44025 ACIO GREEN 16
44040 BASK BLUE 11
SOLVENT BLUE 6
PTA PIGMENT BLUE 19
PMA PISMENT BL"E 10
44045 PTA PIGMENT BLUE 2
PM» PIGMENT BLUE 2
SOLVENT BLUE 4
COLOR
INDEX DYE OR PIGMENT NAME
BASIC BLUE ?6
44090 ACID G*EtN 50
45100 A3ID RED 52
45160 LAKE PIGMENT RED 81
BASIC RED 1
PTA PIGMENT Rf'D 81
PMA PIGMENT RED 81
FUGITIVE PIGMENT RED 81
45170 PMA PIGMENT VIOLET 1
FUGITIVE PIGMENT VIOLET 1
SOLVENT RED <»9
SOLVENT RED 35
0»C RED 37
D+C RED 19
BASIC VIOLET 10
45175 BASIC VIOLET 11
45180 MORDANT RED 27
45350 0*C YELLOW 7
0+S YELLOW 8
ACID YELLOW 73
45370 D*C DRANG-: 5
45380 0*C RED 21
0*: RED 22
PIGMENT RED 9D
ACID RED 37
45410 0*3 RED 27
D*C RED 28
45425 D+C ORANGE 10
45430 0 + C RED 3
FD+C RED 3
46005 BASIC ORANGE 14
46500 PIGMENT VIOLET 19
47000 D4C YELLOW 11
SOLVENT YELLOW 33
47005 D+C YELLOW 1C
ACIO YELLOW 3
47020 DISPERSE YELLOW 54
47023 DISPERSE YELLOW 64
47035 DIRECT YELLOW 5
48000 DISPERSE YELLOW 31
48013 BASIC VIOLET 16
48015 BASIC RED 13
48020 BASIC VIOLET 7
48035 BASIC ORANGE 21
480 to BASIC ORANGE 22
48055 BASIC YELLOW 11
48070 BASIC RED 12
48100 3ASIC YELLOW 23
49000 DIRECT YELLOW 59
t9005 BASIC YELLOW 1
COLOR
INDEX OYE OR PIGMENT NAME
PMA PIGMENT GREEN 2
PTA PIGMfNT GREEN 2
49010 DIRECT YELLOW 7
50204 BASIC BRIGHTENER 0
502itQ BASIC RED 2
50400 SOLVENT SLUE 7
50405 ACIO 6LUE 20
50415 SOLVENT BLACK 5
SOLVENT BLACK 7
50420 ACID BLACK 2
51004 BASIC BLUE 4
BASIC BLUE 3
51175 BASIC BLUE 6
51300 DIRECT BLUE 106
51319 PIGMENT VIOLET 23
51320 DIRECT BLUE 108
52015 BASIC BLUE 9
53030 LEUCO SULFUR BROWN 1
53001 SOLUBILIZtO SULFUR BROWN 1
53010 LEUCO SULFUR YELLOW 9
53040 LEUCO SULFUR YELLOW 1
53050 SULFUR ORANGE 1
53055 SULFUR BROWN 10
LEUCO SULFUR BROWN 10
53056 SOLUBILIZED SULFUR 8ROWN 10
53090 LEUCO SULFUR BROWN 26
SULFUR BROHN 26
53120 LEUCO SULFUR YELLOW 2
53160 SULFUR YELLOW 4
LEUCO SULFUR YELLOW 4
53185 LEUCO SULFUR BLACK 1
SULFUR BLACK 1
53186 SOLUBILIZED SULFUR BLACK 1
53190 LEUCO SULFUR BLACK 10
53195 SULFUR BLACK 2
LEUCO SULFUR SLACK 2
53196 SOLUBILIZED SULFUR BLACK 2
53205 SULFUR BLACK 5
53228 LEUCO SULFUR RED 10
53235 SULFUR BLUE 5
LEUCO SULFUR BLUE 1
53246 LEUCO SULFUR BROWN 14
SULFUR BROWN 14
53290 LEUCO SULFUR BLACK 11
LEUCO SULFUR BLACK 11
53320 SULFUR BROHN 52
53325 SULFUR BROHN 60
53430 SULFUR BLUE 9
53440 SULFUR BLUE 7
LEUCO SULFUR BLUE 7
-------
IOLOR
INDEX
TABLE B-l. DYES ANO PIGMENTS BY COLO* IMOEX NUMBER IN NUMERICAL ORDER CONTINUED)
COLOR
DYE OR PIGHENT NA1- INDEX DYE OR PIGMENT NAME
COLOR
INDEX
53441 SOLU9ILIZE3 SULFUR 3LUE 7
531*50 LEUCO SULF'JR 6LJ£ 13
33570 LEUC3 SULFJR G^E-IN 3
53571 LEUCO SULF'JR G»££N 2
SULFUR GREEN 2
53630 VAT SLUE 4.3
53680 LEUCO SULF'JR BROHN ?0
53720 SULFUR RED S
33731 SULFUR 3ROH* 1?
53830 LEUC3 SULFJR R;0 5
SULFUS RED 5
58000 MORDANT REO 11
LAKE PIGMENT REO 83
58005 MORCANT RE.3 3
58055 PTA 3I3MENT BLUE 7
PMA PIGMENT BLUE 7
LAKE FIGKEST VIOLET 5
59040 EXT. D»C GREEN 1
59100 VAT YELLOH it
59101 SCLU3ILIZE3 VAT YELLOW
-------
TW.E8-1. DYES AND PIGMENTS HV COLOR INOEK NUMBER IN NUMERICAL ORDER {CONTINUED)
:OLOR
INDEX DYE OR PIGMENT NA'I;
71200 VAT BLUE 16
71205 VAT SLUE 53
73000 VAT BLJE 1
D»C BLUE 6
73015 FD + C BLUE 2
ACID 8LUE 7D NONE
NONE VAT BROHN 31 NONE
NONE VAT BROHN 29 NONE
NONE VAT BROHN 28 NONE
NOSt VAT BROHN 20 NONE
NOME VAT BROHN 13 NONE
NONE VAT BROHN 12 NONE
NONE VAT BLACK 13 NONE
NONE VAT BLACK 22 NONE
NOME VAT BLACK 3<» NONE
NOME VAT BLACK 52 NONE
NOME VAT BLACK 38 NONE
NONE VAT BLACK 37 NONE
NONE PIGMENT YELLOH 76 NONE
NONE VAT VIOLET 21 NONE
NONE VAT RED 12 NONE
NOME VAT RED 52 NONE
NOME VAT RED 16 NONE
NONE VAT YELLOH 15 NONE
NOME VAT YELLOH 33 NONE
NONE VAT YELLOH 22 NONE
NOME VAT YELLOH li» NONE
NONE LEUCO SULFUR BROHN 82 NONE
NONE LEUCO SULFUR BROHN 81 NONE
NOSE SOLVENT YELLOW 13 NONE
NONE SOLVENT YtLLOH «»0 NONE
NONE SOLVENT YELLOH <*5 NONE
NOSE SOLVENT YELLOW »*<» NONE
NO-4F SOLVENT YELLOH <*3 NONE
NOSE SOLVENT YELLOH 1,2 NONE
NONE MORDANT BLACK 26 NONE
NOME MORDANT BLACK 3 NONE
NOME MORDANT 9ROHN 70 NONE
NONE MORDANT BROHN 63 NONE
NOME MORDANT ORANGE 8 NONE
NONE MORDANT RED 6». NONE
NOME 10ROANT YELLOH 29 NONE
NOME HORDANT 3LUE 19 NUNE
NOME INGRAIN BLUE 3 NONE
NONE FLUORESCENT BRIGHTENER 159 NONE
DYE CR "IGMENT SAME
FLUORESCENT SRIGHTENER 158
FD+C RED -»0
SOLVENT REO 66
SOLVENT REO 33
SOLVENT RED <»0
SOLVENT ORANGE 51
SOLVENT ORANGE * 8
SOLVENT ORANGE 20
SOLVENT ORANGE 31
SOLVENT ORANGE 25
SOLVENT ORANGE 2
-------
COLOR
INDEX
TABLE B-l. DYES AN3 PIGMENTS BT COLOR INDEX NUMBER IN NUMERICAL ORDER CONTINUED)
COLOR
DYE OS PIGHENT MA-li INDEX DYE OR PIGMENT NAME
COLOR
INDEX
NONE SOLU9ILIZEQ SULFUR 3RONN 37 NONE
HONE LEUCO SULFJR BPOWN 37 NONE
NONE LEUCO SULFUR BLUE 3 NONE
N3NE SULFUR BLUE 8 NONE
NONE LEUCO SULFUR GPEHN IF NOSE
NONE SULFUR GREEN 1L NONE
HONE PIGMENT GREEN 38 NONE
NONE PIGMENT GREEN <.D NONE
NOSE PIGMENT BROWN 32 NOME
NONE AGIO YELLOH i,9 NONE
NONE ACID YELLOH 59 NONE
HONE ACID YELLOW 19 NOSE
HONE ACID YELLOH 79 NONE
HONE ACID YELLOH 12k NONE
MONE AGIO YELLOW ll«s NONE
HONE ACID YELLOH 152 NONE
tfONE ACID YELLOH 17«» NONE
NONE ACID YELLOH 159 NONE
NONE ACID YELLOH 135 NONE
K3NE ACID YELLOW 129 NONE
NDNE ACID YELLOH 128 NONE
NONE ACID YELLOH 127 NONE
NONE ACID ORANGE 2 NONE
H3NE ACID YELLOH 198 NONE
NONE ACID YELLOH 190 NONE
NONE ACID YELLOH 179 NONE
N3NE ACID YELLOH 175 NONE
NONE AGIO BLUE 69 NONE
NONE ACID 8LUE f>3 NONE
MONE ACID BLUE 122 NONE
NONE ACID BLUE IBS NONE
S3NE ACID BLUE 198 NONE
NONE D+C BLUE 179 NONE
NONE ACID VIOLET 29 NONE
NONE ACID VIOLET 76 NONE
NONE ACID RED 337 NONE
MONE ACID RED 339 NCNE
NONE ACID RED 299 NONE
M3NE ACID RED 278 NONE
(I3NE ACID RED 277 NONE
HONE ACID RED 266 NONE
NONE ACID RED 225 NONE
NONE ACID RED 213 NONE
HONE ACID RED 212 NONE
MONE ACID RED 211 NONE
MONE ACID RED 119 NONE
H3NE ACID RED 100 NONE
MONE ACIC RED 167 NONE
HONE ACID RED 175 NONE
MONE ACIO RED 178 NONE
ACID RED 182
ACIO REO 191
ACID REO 19*)
ACIO RED 37
ACID ORANGE 136
ACID ORANGE 132
ACID ORANGE 6i»
4SID ORANGE 62
ACIO ORANGE 69
ACIO ORANGE 128
ACIO ORANGE 119
ACID ORANGE 116
ACIO ORANGE 86
ACID BLACK 29
ACID BROWN 351.
ACID BROWN 2t7
BASIC BLUE 76
BASIC BLUt 75
BASIC BLUE 69
BASIC BLUE 60
BASIC VIOLET 2<»
BASIC VIOLET 15
BASIC ORANGE
-------
TABLES-!. DYES AN3 PIGNUTS f>¥ COLOR INOP( NUMBER IN NUMERICAL ORDER CONTINUED)
COLOR
INDEX
NONE
NONE
MONE
CO
NONE
NONE
MONE
N3NE
HONE
NONE
(ONE
NONE
NONE
NONE
N3NE
NONE
NONE
«ONE
siONE
NONE
NONE
NONE
NONE
HONE
HONE
NONE
NDNE
HONE
HONE
NONE
MONE
NONE
NONE
NONE
NONE
NONE
NONE
MONE
NONE
NONE
HONE
NONE
MONE
NONE
MONE
NONE
MONE
NONE
NONE
DYE OR PIGMENT
REACTIVE BLUE 29
REACTIVE BLUE 25
REACTIVE BROHN 17
REACTIVE BROWN 3.0
REACTIVE 8-WHtl 9
REACTIVE G«EEN 6
REACTIVE BLUE 9i
REACTIVE BLUE 90
REACTIVE BLUE 89
REACTIVE BLUE 71
REACTIVE BLJE 3
REACTIVE VIOLET 1
REACTIVE RED 105
REACTIVE RED 9<»
REACTIVE RED 8£
REACTIVE RED 58
REACTIVE R£D 55
REACTIVE RED t
BLUE 121
BLUE 120
BLUE 119
BLUE 118
BLUE 117
BLUE 116
BLUE 112
BLUE 109
BLUE 102
BLUE 95
BLUE 9*
BLUE 87
BLUE. 85
BLUE 81
BLUE 79
-------
TABLE B-l . DYES AND
Bf COLOR INDEX NUMBER IN NUMERICAL ORDER CONTINUED)
—1
i-O
COLOR
INDEX
N3NE
N3NE
NONE
NONE
NONE
NONE
NONE
NONE
HONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
HONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
DYE 3<
DISPEP.SE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DIS°ERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPENSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
PI51ENT S^
SLUE 73
REO 3?
RE3 30
REO 21
ORAMGf 98
O^iNG? 9
-------
APPENDIX C
DYES AND PIGMENTS MANUFACTURED IN 1973
LISTED IN ALPHABETICAL ORDER BY MANUFACTURER
181
-------
TABLE C-l.
OTiS AMO PlS^E'iT? 1ANUFACTURED IN 1973 ICONTINUEO)
ALLIAN3E CH£II;IL» INC.
DYE OR PIGMENT NAME
03
•&ZOIC
•AZOIC
&ZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
•SASE
"3ASE
36SE
•3ASE
SALT
SALT
SALT
SALT
SALT
SALT
SALT
SALT
SALT
3AUT
SALT
SALT
SALT
SALT
SALT
SALT
SALT
SALT
'AZOIC
'AZOIC
'AZOIC
'AZOIC
YELLOH I
YELLOK 1
YELLOH 2
YELLOH 2
ORANGE 3
ORANGE 3
RED 1
RED 1
REO Z
RED 2
BLUE 3
AZOIC OIAZOIC
AZOIC OIAZOIC
AZOIC OIAZOIC
AZOIC DIAZOIC
A70IC DIAZOIC
AZOIC DIAZOIC
AZOIC DIAZOIC
AZOIC DIAZOIC
AZOIC DIAZOIC
AZOIC DIAZOIC
AZOIC OISZOIC
AZOIC OIAZOIC
AZOIC CIAZOIC
AZOIC OIAZOIC
AZOIC OISZOIC
AZOIC OlftZOIC
AZOIC CIAZOIC
AZOIC DIflZOIC
AZOIC OIAZOIC
AZOIC OIAZOIC
AZOIC OIAZOIC
AZOIC OIAZOIC
COUPLING 3
COUPLING 15
COUPLING 18
COUPLING 35
k
28
1
3
5
8
9
10
11
I.Z
13
ZQ
28
32
3*»
35
<»i
-------
TABLE C-l .
OYES AND PIG*E-»TS MANUFACTURED IN 1973 (CONTINUED)
ALLIED CHECICA. CORPORATION
3Y£ OR PIGMENT NAME
CO
CO
ACID
ACID
ACID
ACID
ACIO
ACID
ACID
ACID
ACID
ACIO
ACID
•ACID
acio
ACID
ACID
ACIO
ACID
ACID
ACID
•ACID
ACID
ACID
•ACID
»A~ID
ACID
ACIO
ACID
ACID
ACID
ACIO
ACIO
ACIO
ACIO
ACIO
ACID
ACID
ACID
ACID
ACID
•ACID
ACID
ACID
ACID
ACIO
ACID
ACIO
ACIO
ACIO
DYE 0
YELLOW 3
YELLOW 17
YELLOW 23
YELLOW 34
YELLOW 36
YELLOW 38
YELLOW 40
YELLOW 54
YELLOW 63
YELLOW 73
YELLOW 76
YELLOW 134
YELLOW 159
ORANGE 2
ORANGE 6
ORANGE 7
ORANGE 8
ORANGE 10
ORANGE 13
ORANGE 34
ORANGE l»5
ORANGE 53
ORANGE 64
ORANGE 86
ORANGE 116
RED 1
REO 14
RED 17
YELLOH 18
REO 27
37
73
85
88
114
115
115
137
167
182
RED
REO
REO
REO
REO
RED
RED
REO
REO
RED
VIOLET 3
VIOLET S
VIOLET 7
VIOLET 49
VIOLET 76
BLUE 1
BLUE 7
COLOR
INDEX DYE OR PIGMENT NAME
13010 ACID BLUE 9
47005 ACID BLUE 20
16965 ACID BLUE 25
1911.0 ACID BLUE 34
18890 ACID BLUE 40
13065 »ACID BLUE 43
25135 ACID BLUE 45
18950 'ACID BLUE 62
19010 40ID BLUE 74
13095 ACID BLUE 78
45.350 ACID BLUE 92
1?850 ACID BLUE 104
NONE ACID BLUE 113
NONE ACID BLUE 118
NCNE ACID BLUE 120
14270 ACID BLUE 145
1B510 ACID BLUE 230
15575 ACID GREEN 1
U230 ACIO GREEN 3
15970 ACID GREEN 9
20170 ACID GREEN 12
22195 ACID GREEN 16
13025 ACID GREEN 25
NONE ACID BROWN 14
NCNE ACIO BLACK 1
NONE ACID BLACK 2
18050 ACIO BLACK 24
14720 DIRECT BROWN 2
16180 ACIO BLACK 52
16255 ACID BLACK 107
16185 3ASIC BRIGHTENER 0
17045 BASIC YELLOW 2
27290 BASIC YELLOW 11
22245 3ASIC YELLOW 13
15620 BASIC YELLOW 21
23635 BASIC ORANGE 1
27201 BASIC ORANGE 2
27200 BASIC ORANGE 21
17755 BASIC RED 2
NONE BASIC REO 13
NONE BASIC REO 14
16580 BASIC RED 46
16600 BASIC VIOLET 1
18055 BASIC BLUE 9
42640 "BASIC BLUE 21
NONE BASIC BLUE 22
42045 BASIC GREEN 1
43080 BASIC GREEN 4
:OLOR
INDEX
42090
50i05
62055
42561
62125
63000
63010
62045
73015
62105
13390
42735
26360
26410
36400
63070
62073
10020
42085
43100
1 3425
44025
61570
20195
20470
50420
26370
22311
15711
NONE
50204
41000
48055
NONE
NONE
11320
11270
48035
50240
48015
NONE
NONE
42535
53015
NONE
NONE
43040
42000
DYE OR PIGMENT NA
BASIC' BROWN 1
BASIC BROWN 4
DIRECT OYE 0
DIRECT YELLOW 4
DIRECT YELLOW 5
DIRECT YELLOW 6
DIRECT YELLOW a
DIRECT YELLOW 11
DIRECT YELLOW 13
DIRECT YELLOW 38
DIRECT YELLOW 44
DIRECT YELLOW 84
DIRECT YELLOW 103
DIRECT YELLOW 106
DIRECT YELLOW 107
DIRECT ORANGE 1
DIRECT ORANGE 1
DIRECT ORANGE 1
DIRECT ORANGE 6
DIRECT ORANGE 6
DIRECT ORANGE a
DIRECT ORANGE 8
DIRECT ORANGE 15
DIRECT ORANGE 15
DIRECT ORANGE 26
DIRECT ORANGE 34
DIRECT ORANGE 34
DIRECT ORANGE T2
DIRECT ORANGE 103
DIRECT REC 1
DIRECT REO 2
DIRECT REC 4
DIRECT REC 13
DIRECT RED 16
DIRECT REC 23
DIRECT REC 24
DIRECT RED 36
DIRECT REC 28
DIRECT REC 31
•DIRECT REO 32
DIRECT REC 37
DIRECT REO 72
DIRECT REC 73
DIRECT REC 80
DIRECT RED 81
DIRECT REO 83
DIRECT VIOLET 7
DIRECT VIOLET 9
COLOR
INDEX
21000
21010
22165
24890
47035
40001
13930
40000
24895
19555
29000
NONE
NONE
40300
NONE
22370
22430
22375
233E5
23375
22130
221<-0
40002
40003
39150
40215
40220
NONE
29156
22310
23500
29165
22155
27680
29160
29185
39190
23120
39100
35790
22240
29200
29160
35780
28160
39225
27855
27865
•LAST LISTED IN 1972
-------
TABLE C-1.
OYES AND PISM^fS MANUFACTURED IN 1973 (CONTINUED)
ALLIED OHEHIC4L CORPORATIOH (CONTINUED!
co
DYE OR PIGMENT NAME
DIRECT VIOLET 48
DIRECT VIOLET 51
DIRECT BLUE 1
DIRECT BLUE 2
DIRECT SLUE 6
DIRECT BLUE 8
DIRECT SLUE 14
DIRECT BLUE 15
DIRECT SLUE 2?
DIRECT BLUE 25
DIRECT BLUE 71
DIRECT SLUE 76
DIRECT BLUE 78
DIRECT BLUE 80
DIRECT BLUE 191
DIRECT BLUE 218
DIRECT GREEN i
DIRECT GREEN 6 .
Di^CT 8ROWN 31
DIRECT BROWN 74
DIRECT 9ROHN 95
DIRECT BROWN 154
DIRECT BROWN 218
DIRECT BLACK 2
DIRECT SLACK t>
DIRECT BLACK 9
DIRECT BLACK 9
DIRECT BLACK 38
DIRECT SLACK 51
DIRECT 3LACK 56
DIRECT SLACK 78
BIRECT BLACK eo
DIRECT SLACK 95
DIRECT BLACK 190
DISPERSE BLUE 73
!70*C 8LUE 1
FD«-C BLUE 2
FO*C RED 2
FO*C RED 3
FD*C RED ifO
FO*C VIOLET 1
FQ*C YELLOW 5
?Q*C YSLLOH 6
0»C BLUE 6
0+G GREEN 5
0*C GREEN 6
0*C ORANGE §
30235 SOLVENT YELLOl! 5G
27720 SOLVENT ORANGE i
3i>170 SOLVEMT ORANGE 3
30015 SOLVENT ORANGE 7
31608 SOLVENT ORANGE 23
NONE SOLVENT ORANGE 31
NONE SOLVENT RED 2k
NONE SOLVENT RED 26
42090 SOLVENT RED 27
73015 SOLVENT RED 68
16185 SOLVENT RED 74
i»Eif3G SOLVENT RED 75
NONE 'SOLVENT VIOLET 17
I>26'f0 SOLVENT BLUE 7
19140 SOLVENT BLUE 12
15985 SOLVENT BLUE 16
73000 SOLVENT BLUE 38
61570 SOLVENT 3LUE 43
61565 SOLVENT BLUE 74
15510 SOLVENT GREF.N 3
45170 SOLVENT BLACK 3
DOLOR
INDEX DYE OR PIGMENT NAME
45380 SOLVENT BLACK 5
45*10 SOLVENT BLACK 7
17200 SOLVENT BLACK 12
45170 SOLVENT BLACK 13
60725 VAT YELLOH 1
47000 aVAT ORANGE 15
59040 VAT VIOLET 10
13065 VAT BLUE 1
18821 VAT BLUE 20
14055 PIGMENT YELLOH 1
14110 PIGHENT YELLOW 3
20110 PIGMENT YELLOW 4
13225 PIGMENT YELLOW 65
20150 PIGMENT YELLOH 73
13255 PIGMENT YELLOVj 12
1J710 PIGMENT YELLOt! 14
16500 PIGMENT YELLOW. 17
14645 PIGMENT YELLOH 83
15705 PIGMENT YELLOH ft
11165 PIGMENT YELLOV! 108
12055 "PIGMENT YELLOW 123
21240 PIGMENT ORANGE 1
47000 PIGMENT ORANGE 13
NONE PIGMENT ORANGE 15
NONE PIGHENT ORANGE 16
NONE PIGMENT ORANGE 43
NONE 'PIGHENT VAT ORANGE 3
11021 PIGMENT VAT ORANGE 4
11920 PIGMENT RED 2
11270 PIGMENT RED 18
12140 PIGMENT RED 38
NONE PIGMENT RED 41
NONE PIGMENT RED 48
26105 "PIGMENT RED 63
26120 PIGMENT RED 64
26125 PIGMENT RED 87
NONE PIGMENT RED 88
NONE PIGMENT RED 122
NONE PIGMENT RED 123
NONE PIGMENT RED lea
50400 PIGMENT RED 179
61200 PIGMENT RED 190
NONE PIGMENT RED 198
NONE PIGMENT VIOLET 19
NONE PIGMENT VIOLET 23
63005 PIGMENT VIOLET 31
61565 PIGMENT VIOLET 36
26150 PIGMENT VIOLET 38
COLOR
INDEX
50415
50415
NONE
NONE
70600
6902S
60000
73008
59300
11680
11718
11665
11740
1173S
2109Q
21095
211G5
21100
7060E
68420
65049
11725
21110
21130
21160
71105
59308
59710
12310
12350
21120
21200
15665
15880
15800
73310
73312
73915
71145
59300
71130
73390
46500
51319
60010
73365
73395
•LIST LISTED IN 1972
-------
TABLE C-l. DYES AMD PIGMENTS MANUFACTURED IN 1973 (CONTINUED)
ALLIED CHEMICAL CORPORATION IC3NTINUED»
COLOR
3YE CR PIGMENT NAM£ INDEX
ALPHA PIGMENT SLUE 15 74160
BETA PIGMENT BLUE 15 7tl6D
HIGHEST BLUE ZZ 69810
•PIGMENT BLUE 35 21180
?IGMENT GREEM T 7*,Z60
PIG^NT GREEN 36 7i»160
PIGMENT BROWN 5 1E800
PIGHENT BROHN 26 711Z9
LAKE ACID Y£LLOH 23 19H»Q
LAKE PIGMENT VIOLET 5 58055
NATURAL BLUE 1 75780
00
•LiST LISTED IN 1972
-------
TABLE C-l. DYES «MO PIGMENTS MANUFACTURED IN 1973
»H£RICAW COLOR 4ND CHEMICAL CORPORATION
CXI
3YE OR PIGMENT NfiH£
43ID YELLOW 17
»;iD YELLCW 23
»:io YELLOH 3«
a:io YELLOH 4?
5CID YELLOW 41.
a;iD YELLCW 54
&DID YELLCW 53
4CID YELLCW 124
»3IO YELLOW 151
SDIO YELLOH 159
»3ID C^SNGE 1
aCIO ORANGE 1
SCIO OR9NGE 7
&CID ORANGE 8
»3I3 ORANGE 31
a:io ORANGE SD
a;io ORANGE 50
»3IO ORANGE 1I&
4CIO FED -
:io RED
CIO RED
35
37
66
85
DID RED 89
Old RED 99
CIO RED 137
31!) RED 151
ACID RED 182
ACID VIOLET 7
4CID BLUE 35
aCIO BLUE 1,5
SCID BLUE 113
4CID BLUE 113
»CID BLUE 158
ACID BLUE 153
ACID BROWN 14
»5ID BLACK 1
DIRECT 8ROHN 2
»3ID BLACK 52
3aSE AZOIC CIAZOIC 1*
SALT AZOIC CIAZOIC 1
SALT AZOIC DIAZOIC 3
SALT AZOIC OIAZOIC 5
COLOR
INDEX
1P965
19140
1R893
22910
23900
19010
13095
NONE
13906
NONE
13090
13091
1E510
15575
15995
13150
18732
NONE
14710
18065
1701,5
26905
2221,5
23910
23285
17755
26900
NONE
18055
62055
63010
2H3&0
261,10
1L880
15050
20195
201,70
22311
15711
37151
37135
37010
371Z5
OY; OR
SALT AZCIC OIAZOIC 6
SALT AZOIC OIAZOIC 8
SALT AZOIC DIAZOIC 9
SALT AZOi; DIAZOIC 11
SALT AZOIC PIAZOIC 12
SALT AZOIC DIftZOIC 13
SALT AZOIC DI4ZOIC 1"*
SALT AZOIC OIAZOIC k9
DIRECT YELLOW i,
OIRLCT YELLOW 11
•DIRFCT YZLLOW 12
DIRECT YELLOW 21
DIRECT YELLOW 26
DIRECT YELLOW 3*,
DIRECT YELLOW (,<,
DIRECT YELLOW 50
DIRECT YELLOW 81,
DIRECT YELLOW 105
DIRECT YELLOW 106
"DIRECT ORANGE 1
•DIRECT ORANGE 1
'DIRECT ORANGE 1
DIRECT ORANGE 10
DIRECT ORANGE 15
DIRECT 3R4NGE 15
DIRECT GRANGE 29
DIRECT ORANGE 39
DIRECT ORANGE 72
DIRECT RED 2
DIRECT RED 10
DIRECT RED 23
DIRECT PEO 2<»
DIRECT RED 26
DIRECT RED 79
DIRECT RED 80
DIRECT RED 81
DIRECT RED 83
'DIRECT VIOLET 9
DIRECT BLUE 1
DIRECT BLUE 2
DIRECT BLUE 6
»DIRECT BLUE Ik
DIRECT BLUE 76
COLOR
INDEX DYE OR PIGMENT NAME
37025 DIRECT BLUE 80
37110 DIRECT BLLE 86
37040 DIRECT SLUE 100
37085 DIRECT BLUE 120
37105 DIRECT BLUE 120
.17130 DIRECT BLLE 191
37151 DIRECT BLUE 218
37050 DIRECT GREEN 1
21,390 DIRECT GREEN 6
1(0000 DIRECT BRCWN 1
24695 DIRECT BROWN 31
IJ0045 DIRECT BROWN 40
25300 DIRECT 8RCWN 46
29060 *DIRECT BRCWN 74
29000 DIRECT BROWN 95
29025 DIRECT BLACK 4
NONE DIRECT BLACK 9
NONE DIRECT BLACK 9
40300 *DIRECT BLACK 19
22370 DIRECT BLACK 22
22430 »OIRECT BLACK 36
22375 »OIRECT BLACK 37
23370 DIRECT PLACK 38
40002 DIRECT SLACK 51
40003 DIRECT BLACK 78
29155 DIRECT BLACK 80
40215 DIRECT BLACK 190
NONE DISPERSE YELLOW 3
23500 'DISPERSE YELLOW 5
22145 DISPERSE YELLOH 23
29160 DISPERSE YELLOH 33
29185 DISPERSE YELLOW 34
29190 DISPERSE YELLOW 42
29065 'DISPERSE YELLOH 54
35780 DISPERSE YELLOH 66
28160 DISPERSE YELLOW lie
29225 DISPERSE GRANGE 3
2/885 DISPERSE ORANGE 5
24410 DISPERSE ORANGE 16
22590 DISPERSE ORANGE 17
NONE 'DISPERSE ORANGE 25
23850 DISPERSE ORANGE 29
24411 DISPERSE ORANGE 58
COLOR
INDEX
NONE
74180
NONE
34085
34090
NONE
24401
30280
30295
30045
35660
NONE
NONE
36300
30145
30245
31560
315E5
35265
35435
31665
NONE
30235
27720
30015
31600
NONE
11855
12790
26070
NONE
NONE
10338
47020
NONE
NONE
11005
11100
NONE
NONE
NONE
NONE
NONE
•taST LISTED IN 1972
-------
TA31E C-1.
DYES AND PIGMENTS MANUFACTURED IN 1973 (CONTINUED)
AMERICAN COLO* «ND CHE1ICAL CORPORATION (CONTINUED)
CO
DYE OR PIGMENT NAME
DISPERSE ORANGE 89
DISPERSE ORASGE 90
DIS°E<;SE ORANGE 91
DISPERSE RED 1
DISPERSE RED 5
DISPERSE RED 7
DISPERSE RED 11
3ISrEPSE RED 13
DISPERSE RED 17
DISPERSE RED 55
DISPERSE RED 60
•DISPERSE RED 65
DISPERSE RED 135
DISPERSE RED ll»0
DISPERSE VIOLET 1
DISPERSE VIOLET 4
DISPERSE VIOLET 27
DISPERSE GLUE 1
DIS=ER3E SLUE 3
DISPERSE SLUE 7
DISPERSE 8LUE 6
-------
TABLE C-l.
DYES AND piGiE^rs HANUFACTUREP IN 1973 ICONTINUEOS
AMERICAN CVANAMIO COMPANY
oo
CO
DYE OR PIGNUT NAHX
*:iD YELLOW i
•S3 to YE.LLOM -3- ,-,-
S3ID YELLOW 23
V3-I.O •.•YetL.QW 1,2
•4G.I.O -YELLOW 54
«r~I'Oi -YELLOW 15L
JSJD 'ORANGE 5
£3IO-:.OR,ANGE 7-
rs.ltr ORANGE » •;
J310-GRANGE ID
S3XD ORANGE Zl,
*A3IQ:ORANG£ 6l»
5'3ID .ORANGE 6'9
5CID RED -1 ' -
&3IO REO 26
43ID RED 73
4.3.1 a RED. ss
310 RED 151
TIG VIOLET 3
31.0 VIOLET 6
3IO~VIOLET 49
:iO BLUE 7 -
310 BLUE 1,5
:iD GREEN 1
310 GREEN 3
310 GREEN 9
CIO GREEN 50
010 GROWN 14
31 D BROWN 96
CIO BROWN 97
CID BROWN 93
310 BROWN 351,
310 BLACK 1
310 BLACK 2
'DIRECT 8ROHN Z
•ACID BLACK 48
ACID BLACK 92
BASIC 5RIGHTENER 0
3ASIC YELLOW 2
3ASIC YELLOW 11
36SIC YELLOW 31,
3ASIC YELLOW 37
BASIC YELLOW 1,1
3ASIC ORANGE i
3ASIC ORANGE Z
3ASIC ORANGE Zl
3ASIC ORANGE 31
COLOR
INDEX DYE OR "IGHENT NAME
10316 9ASIC RED 12
<«7005 BASIC R-3 It
19140 BASI3 RED 22
2Z910 9ASIC RtO 30
190^0 3ASI3 VIOLET 1
139.0& 3ASIO VIOLET 10
NONE; 3ASI3 VIOLET 11
13080 BASIC VIOLET 18
155,10 3ASI3 BLUE 3
BA-SIC 3LUf 6
84SIC 9LUE 9
20170 BASIC 3LUE 5U
NCNE j 3ASIC BLUE 76
NONE,. 3ASIC GREEN 1
18050 8ASI3 GREEN 4>
16150 3ASIC BROWN 1
27290 3ASIC 3ROWM k
15&20 DIRECT YELLOW I*
Z6900 DIRECT YELLOW
-------
TABLE C-l .
OYES AND PISI'IIS MANUFACTURED IN 1973 (CONTIMUEOI
AMERICAN CYASi-nO COMPANY (CONTINUED)
CO
COLOR
OTE OR PIG-HENT NAME INDEX
SOLVENT BLUE frD NONE
SOLVENT BLUE 89 NONE
SOLVENT GREEN 1 1.2000
SOLVENT BROHN 12 31010
SOLVENT BROHN 20 NONE
SOLVENT BROMM 38 NONE
SOLVENT BLACK 5 SOM5
SOLVENT BLACK 7 50*15
SOLVENT BLACK 26 NONE
LEUCO SULFUR YELLOH Z 53120
•LEUCO SULFUR YELLO* IE NONE
•SULFUR 9LU£ 5 53235
SULFUR BLUE 7 53V.O
LEUCO SULFUR BLUE 7 539 15630
CALCIUM PIGMENT RED "»9 15630
•SODIUM PIGMENT RED <»9 15630
•3ARIUM PIGMENT RED 53 15585
•PTA PIGMENT RED 81 <»5l&0
.PIGMENT RED 122 73915
FUGITIVE PIGMENT VIOLET 3 <»2535
PTA PIGMENT VIOLET 3 !»2535
PIGMENT VIOLET 23 51319
ALPHA PIGMENT BLUE 15 7<«160
BETA PIGMENT BLUE 15 71.160
PTA PIGMENT GREEW 2 *20«.0
PTA PIGMENT GREEN 2 ".9005
PTA PIGMENT GREEN «. 1.2000
PIGMENT GREEN 7 7*260
PI GHENT GREEN 36 7<«160
NATURAL RED 6 75330
•LAST LISTED I* 1972
-------
TABLE C-l.
OYES A!0 PISH-STS MANUFACTURED IN 1973 «CONTINU£0>
AMERICAN HO£CHST COLORATION
•-'• " • COLOR~
DYE OR PIGMENT NAME INDEX
• SID YELLOW "190 NONE '•
1.5-ID. BLUE 215 NON'E1''1
AZOIC5SLUE 3 NONE
AZOTIC BR-OHN 9 NONE '
ftZOIC SLi^K 1 NONE
•Azoic 'COUPLING 7 3756-5'5
AVZOIC -COURLWG 13 37%95 ' «
A Z"OIC COUPLING 35 376i5 "'
'HZ3IC COUPLING 107 37107
BA-S.3JC .,Blj.Ut' 3 SlO'Dif
otsPERSt YE'LLOH 58 NONE/
DISPERSE;. YELLOH 68 NONE '-'
DISPERSE ORANGE <*2 NONE '
DISPERSE BLUE. 79 NONE
'DISPERSE. BLUi' 95 NONE,
DISPERSE BLUE 152 NONE",;
REACTIVE YELLOW 13 18990
REACTIVE YELL3H 15 NONE
REACTIVE YELLOW 17 NONE
REACTIVE ^YELLOW 2<« NONE
REACTIVE YELLOW 31 NONE
REACTIVE YELLOW 37 NONE
REACTIVE YELLOH %H NONE
REACTIVE ORANGE 16 17757
REACTIVE ORANGE 50 NONE
REACTIVE REO 21 NONE
REACTIVE REO 9i» NONE
REACTIVE RED 105 NONE
REACTIVE VIOLET <» 18096
REACTIVE VIOLET 5 18097
REACTIVE BLUE 19 61200
REACTIVE BLUE 21 NONE
REACTIVE BLUE 38 NONE
REACTIVE BLUE 89 NONE
REACTIVE BLUE 90 NONE
'REACTIVE BLUE 91 NONE
REACTIVE BLACK 5 20505
VAT YELLOH 1) 59100
'SOLUBILIZEO VAT YELLOH <* 59101
tfAT ORANGE 1 59105
'SOLUBILIZED VAT ORANGc 1 59106
VAT ORANGE 3 59300
VAT ORANGE S 73335
SOLUBILIZEO VAT ORANGE 5 73336
VAT ORANGE 7 71105
VAT RED 1 73360
SOLUBILIZEO VAT RE3 1 73361
VAT REO IU 71110
DYE OR PIGMENT NAME
VAT REO 15
VAT RED <»1
VAT VIOLET 2
VAT VIOLET 3
VAT VI3LET 13
VAT 3LUE. ?
50LU8ILIZED VAT BLUE 6
VAT BLUf 67
VAJ GREtN 9
VAT BROWN 5
VAT BROHN 57
VAT BLACK 1
SOLUBILIZEO VAT BLACK 1
"IGHENT YELLOH 1
PIGMENT YELLOH 3
PIGMENT YELLOH 98
PIGMENT YELLOH 12
PIGMENT YELLOH 13
PIGMENT YELLOW !<•
3IGMENT YELLOW 17
PIGMENT YELLOH 83
»?IGMENT YELLOW 10
PIGMENT YELLOH 16
PIGMENT YELLOH 97
PIGMEMT ORANGE 5
'IGMENT ORANGE 16
'PIGMENT ORANGE 38
'PIGMENT ORANGE <»3
PIGMENT VAT ORANGE 3
PIGMENT VAT ORANGE 7
"IGMENT REO 7
PIGMENT RED 9
PIGMENT RED as
PIGMENT RED 112
" IGMENT RED 12-2
PIGMENT RED 1".6
PIGMENT RED H.9
PIGMENT REO 170
'IGMENT RED 176
PIGMENT REO 181
PIGMENT VAT RED is
PIGMENT VIOLET 23
=>IGMENT VIOLET 36
PIGMENT VIOLET 7
-------
TABLE C-l-
OTiS AW) PISHE1IS MANUFACTURED IN i<)T3 (CONTINUEOI
A»3LLO COLORS, INC.
3YE OR PIGMENT NAM£
PIGMENT YFLLOH iz
PIGMENT VELLOM 13
PIGHENT VELLOM i<»
BARIUM PIGMENT RED
-------
TABLE C-1 .
DY£S AND PIG-I^TS MANUFACTURED IN 1973 (CONTINUEDt
ATLANTIC CHEHIC6L INDUSTRIES. INC.
no
AGIO YE
ACID
SCIO
acio
ACIO
'•ACID
AGIO
ACID
ACID
•ACID
ACID
ACID
ACIO
ACID
ACIO
ACID
ACID
ACID
ACIO
ACID
ACID
ACID
ACID
•ACIO
ACID
•ACID
ACIO
ACIO
•ACID
ACID
ACID
ACID
ACIO
ACID
ACID
ACIO
ACIO
•ACIO
ACID
ACIO
ACIO
ACIO
•ACIO
ACIO
ACIO
E OR PIGIENT
DYE 0
YELLOW 11
YELLOW 17
YELLOW 34
YELLOW 38
YELLOW 40
YELLOW 65
YELLOW 124
YELLOW 151
ORANGE 7
ORANGE 8
ORANGE 10
ORANGc 52
ORANGE 60
ORANGE 63
ORANGE 116
RED 1
RED 4
RED 14
RED 17
YELLOH 18
RED 26
RED 37
RED 57
RED 66
RED 73
RED 80
RED 88
RED 89
RED 97
RED 99
RED 111
RED 11 It
REO 115
RED 115
RED 119
RED 137
RED 151
RED 167
RED 182
RED 186
VIOLET 7
VIOLET 34
VIOLET 3k
VIOLET 43
BLUE 7
BLUE 25
BLUE 27
CCLOR
INDEX
13010
16820
1^965
18890
25135
16950
1^170
NONE
13906
15510
15575
16230
13035
16732
22670
NONE
18050
11.710
It720
16180
16255
16150
170
-------
TABLE C-l.
DYES AND PI3H3NTS MANUFACTURED IN 1973 (CONTINUED)
ATLANTIC CH£-u;«L INDUSTRIES. INC. (CONTINUED)
DYE OR PIGMENT NAME
to
CO
•DIRECT
•DIRECT
DIRECT
'DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
102
ORANGE 1
ORANGE 1
ORANGE 26
ORANGE 29
ORANGE 31.
ORANGE 3 it
ORANGE 37
ORANGE 37
ORANGE 39
ORANGE 72
ORANGE
RED 2
RED l(
RED 7
RED 10
RED 15
RED 20
RED 23
RED 21.
RED 26
RED 31
RED 39
RED 1.5
RED 62
RED 72
RED 73
RED 75
RED 79
RED 80
RED 81
RED 83
RED 8".
RED 100
RED 122
RED 123
RED 127
BLACK 127
RED 1"»9
RED 153
VIOLET 1
VIOLET 7
VIOLET 9
VIOLET li.
VIOLET 51
VIOLET 56
BLUE 1
BLUE 8
BLUE !«•
COLOR
INDEX OYE OR PIGMENT NAME
221.30 DIRECT BLUE 15
22375 DIRECT EiLUE 22
29150 DIRECT BLUE 2
-------
TABLE C-J.
DYES AND FIG^MT? MANUFACTURED IN 19/3 (CONTINUED)
BASF HYANOOTT£ 30NPORATION
3VE OR PIGMENT NAM£
»:iD YELLOW 19
3»sic YELLOW 13
3ASIC YELLOW 23
3ASIC YELLOW 2<»
3CSIC YELLOW 25
3ASIC ORANGE UO
3ASIC ORANGE H
3ASIC RED 1
36SIC RED 29
9ASIC RED 51
3ASIC BLUc <«1
3ASIC 3LU£ 5i»
DISPERSE YELLOW 56
DISPERSE YELLOW 6i>
DISPERSE RED 60
3ISPERSE RED 91
DISPERSE BLUE 87
DISPERSE BLUE 9*s
DISPERSE BLUE 1<>8
BETA PI5MENT BLUE 15
GREEN 7
COLOR
INDEX
NONE
NONE
i.8100
11<*80
HUSO
NONE
NONE
<»5160
111*60
NONE
11052
NONE
W023
60756
NONE
NONE
NONE
NONE
7<»1&0
7W60
-------
TABLE C-l.
DYES A.O Fis-i;<
-------
TABLE C-1 •
3YiS AND PISHHNIS MANUFACTURED IN 1973 (CONTINUED)
3E*NCOL3RS-PDU;HK"EPSIE, IMC.
DYE OR PIGMENT NAM£
ACID YELLOW 17
ACID YELLOW 23
ACID YELLOW 3<»
4CID ORANGE 7
ACID ORANGE 8
ACID ORANGE 10
ACID RED <•
AGIO RED ll»
ACID YELLOH 18
ACID RED 26
ACID RED 88
ACID BLUE 29
SCID BLUE 113
ACID GREEN 20
ACID BLACK 1
DIRECT YELLOM ZB
'DIRECT RED 81
H3RCANT YELL3K 1
10RDANT YELLOH 8
M3RDANT YELL3H !«.
tOROANT YELLOW Z6
13RDANT YELLOH 36
•1DRDANT ORANGE 1
»10RDANT ORANGE 4
MDROANT ORAN3E 6
HDROANT RED 7
•ORDANT R£0 9
•MORDANT RED &"»
HDROANT VIOLET 5
13ROANT SLUE 9
MORDANT GREEN 36
10RDANT BROW.H 12
10RDANT BROHN 18
13RDANT BROMV 33
MDRDANT BROWN lf9
HDRDANT 8ROHN 70
MORDANT BLACK 19
13ROANT BLACK 38
OXIDATION BASE 21
COLOR
INDEX
13965
191ltO
18890
1J510
15575
16230
16255
16150
1F620
201.60
26360
20<»95
20470
19555
23160
li»025
18821
1<»055
22880
11*135
11.030
1891.0
26520
18760
16105
NCNE
15670
1^855
17235
11290
20150
13250
13265
NCNE
12200
16160
765l»0
•UST LISTED IH 1972
-------
TABLE C-l- OYiS AND PIG^t-US MANUFACTURED IN 1973 (CONTINUED)
BffROtN, INC., S?APHIC ARTS PRODUCTS DIVISION
COLOR
OYE OR PIGMENT NAME INDEX
PIGMENT YELLOW 1Z 21090
PIGMENT RED <»8 us&s
8ARIUM PIGMENT RED i»9 15630
CALCIUM PIGMEHT REO i»9 i;:630
BARIUM PIGMENT RED 53 1?585
CALCIUM PIGMENT R£3 57 1E850
PMA PIGMENT RED 81 <»5160
PIGMENT RED 90 U?380
»?MA PIGMENT VIDLET 3 1.2535
PHA PIGMENT SLUE 1 «595
BETA PIGMENT BLUE 15 7U160
LAKE PIGMENT BLUE Zk
VD
•LAST LISTED IN 197Z
-------
TABLE C-l . DYES AID PIGHEMTS MANUFACTURED IN 1973 (CONTINUED)
CO
DTE OR PIGMENT NAME
ftCID BLUE 93
BASIC RED 9
BASIC VIOLET 1
SOLVENT BLUE 23
PIGMENT YELL3H 1
PIGMENT YfLLOH 3
•PIGMENT Y3LLOH 4
'PIGMENT YELLOW 7
-------
TABLE C-l .
Ot£S ANO PIG<1S^TS MANUFACTURED IN 1973
-------
TABLE C-1 •
DYES AN3
:I3A-G€IGY S
3YE OR PIGMENT NAME
FLUORESCENT 3RiGHT£N£R i
FLUORESCENT dRI&HT£NER Z2
FLUORESCENT aRIGHTcNtR Z'-t
FLUORESCENT 3RiGHT£NER ws
FLUORESCENT BRIGHTENEK 5
-------
TABLE C-l. OVES ASO PISME1TS MANUFACTURED IN 1973 (CONTINUED)
CINCINNATI MIH;RON CHEMICALS, INC.
DYE OR PIGMENT NAME
FLUORESCENT BRIGHTENER 2« <*06ZZ
FLUORESCENT BRIGHTENER 68 NONE
ro
O
-------
TABLE C-l .
DYES AND PIGMENTS HANUFA3TUREO IN 1973 (CONTINUED)
CROMPTON + KNOWLES CORPORATION, ALTHOUSE DIVISION
ro
O
ro
BYE OR PIGMENT NAME
S3ID YELLOW 19
A3io YELLOW 23
CIO YELLOW 40
310 YELLOW 55
»
310 YELLOW 128
310 YELLOW 151
3ID YELLOW 159
JID ORANGE 86
:iD ORANGE 116
*A3io RED as
AGIO RED 114
A3ID RED 119
A3IO RED 138
»OCIO RED 182
&CID PEO 299
ACID BLUE 40
ACID BLUE 62
JSCID BLUE 113
ACID GREEN 19
H3ID BROWN 239
ACID BLACK 107
BASIC YELLOW 11
BASIC YELLOW 13
BASIC ORANGE 21
BASIC RED 14
BASIC VIOLET 16
BASIC 8LUE 3
•BASIC BLUE 21
'DIRECT YELLOW 11
DIRECT YELLOW 34
DIRECT YELLOW 50
DIRECT YELLOW 105
DIRECT YELLOW 106
'DIRECT ORANGE 1
'3IRECT ORANGE 1
'DIRECT ORANGE 1
DIRECT ORANGE 39
DIRECT RED 80
'DIRECT RED 81
DIRECT RED 83
'DIRECT BLUE 8
DIRECT BLUE 76
DIRECT BLUE 80
DIRECT BLUE 86
DIRECT BLUE 98
DIRECT BLUE 100
DIRECT BLUE 191
DIRECT BLUE 218
COLOR
INDEX
NONE
18950
NONE
13906
NCNE
NONE
NCNE
22245
23635
NONE
16073
NONE
NONE
62125
62045
26360
20<»'»0
NCNE
NONE
46055
NONE
4B035
NONE
4*013
51004
NONE
40000
29060
29025
NONE
40300
22370
22430
22375
40215
35780
28160
29225
24140
24411
NONE
74180
23155
NONE
NONE
24401
3YE OR PIGMENT NAME
DIRECT BLACK 22
3IRECT BLACK 38
DISPERSE YELLOW 3
DISPERSE YELLOW 23
DISPERSE YELLOW 54
DISPERSE RED 60
DISPERSE RED 65
DISPERSE RED 177
DISPERSE VIOLET 28
DISPERSE BLUE 56
FD+C BLUE 1
FO.+ C BLUE 2
FO+C RED 2
FO+C RED 3
FD*C RED 4
FO*C YELLOW 5
FD+C YELLOW 6
D+C GREEN 5
0»C RED 36
D+C YELLOW 7
COLOR
INDEX
35435
30235
Ilfl55
25070
47020
60756
NONE
NONE
61102
53285
42090
73015
15165
45430
14700
19140
15985
51570
12085
45350
»L»ST LISTED IN 197Z
-------
TABLE C-l .
DYES AND PIGI^T? MANUFACTURED IN 1973 (CONTINUEDI
0»E SPECIALTIES, INC.
ro
O
DYE OR PIGMENT NAME
3SSIC ORANGE 2
34SIC RED 9
34SIC VIOLET 1
3ASIC VIOLET 2
34SIC VIOLET 3
BASIC VIOLET if
3&SIC VIOLET 13
3SSIC VIOLET llf
3ASIC BLUE 1
34SIC BLUE 2
3ASIC 3LUE 5
3&SIC SLUE 7
3«SIC BLUE 11
3ASIC 3LUE 26
BASIC GSEEN 1
3ASIC GREEN <>
3ASIC GREEN 7
34SIC BROWN it
SOLVENT YELLOW 3k
SOLVENT OSANGE 3
SOLVENT RED 41
SOLVENT RED *9
SOLVENT REO 69
SOLVENT VIOLET 8
SOLVENT VIOLET 9
SOLVENT BLUE <>
SOLVENT BLUE 5
SOLVENT SLUE 6
SOLVENT BLUE 23
SOLVENT GREEN 1
SOLVENT BROW 12
SOLVENT BLACK 5
SOLVENT BLACK T
COLOR
INDEX
11Z70
1.2500
<»2S5S
".2600
i»2536
1*2025
i»2595
1*1*01.5
1*301*0
1*2000
NONE
21010
1.1000
11270
1.2510
lf5170
NONE
1.2535
1.2555
<« 1*01.5
1.2595
1>1*01>0
42760
1.2000
21010
50<»15
501.15
-------
TABLE C-l. OfES Ai« PTSH-STS NANUF6CTUREO IN 1973 (CONTINUED!
£. I. JOPONT D£ KhHOURS » COMPANY, INC.
DYE OR PIGMENT NAHE
f"O
o
43X0
4:10
*4CID
ACID
4310
43ID
43ID
43ID
-1310
•4310
ACID
4310
4310
43ID
-•'4310
4310
63ID
4CID
4310
4310
4cin
*S3IO
43ID
SCIO
S3IO
4310
4CID
4310
4CIO
»43IO
4CIO
43ID
4310
4CIO
4310
•4310
4CID
4CIO
4310
»43ID
HCID
ftCIO
ACIO
ACIO
ACIO
ACID
DYE 0
DYE 0
YELLOW 17
YELLOW 36
YELLOW 1,0
YELLOW i»9
YELLOW iZ
BASIC ORANGE 25
3ASIC 3RANGE 26
BASIC ORANGE 39
BASIC RED 1
BASIC RED 2
BASIC REO 12
BASIC REO lit
BASIC i5170
1.5175
NONE
DYE OR PIGMENT NAME
BASIC VIOLET 16
3ASIC VIOLET 2<»
3ASIC BLUE 3
3ASIC BLUE It
BASIC BLU; 7
•3ASIC BLUE 9
3ASIC BLUE 21
BASIC BLUE 22
BASIC BLUE 26
BASIC BLUE 35
BASIC BLUE 77
BASIC BLUE 82
BASIC BLUE 87
BASIC BLUE 91,
BASIC BLUE 97
BASIC GREtN 1
BASIC GREEN 3
BASIC GREtN <»
BASIC BROWN 1
BASIC BROWN I.
"DIRECT DYE 0
DIRECT YELLOW !>
DIRECT YELLOW 6
DIRECT YELLOW 11
DIRECT YELLOW 12
DIRECT YELLOW 23
DIRECT YELLOW 28
DIRECT YELLOW 29
DIRECT YELLOW l»it
"DIRECT YELLOW 50
»DIRECT YELLOW 63
DIRECT YELLOW 8I»
DIRECT YELLOW 119
DIRECT YELLOW 120
DIRECT YELLOW 127
DIRECT YELLOW 131
DIRECT YELLOW 137
•DIRECT ORANGE 8
•DIRECT ORANGE 8
DIRECT ORANGE 15
DIRECT ORANGE 15
DIRECT ORANGE 31.
DIRECT ORANGE 3*.
DIRECT ORANGE 39
DIRECT ORANGE 59
DIRECT ORANGE 73
DIRECT ORANGE 7<.
»OISECT ORANGE 79
COLOR
INOtX
^8013
NONt
51001.
51001.
<»2595
52Q15
NONE
NONF
NONE
NONE
NONE
NONE
NONE
NONE
NONE
<«2000
21000
21010
22165
21.890
4(0001
(.0000
2i»895
NONE
19555
19556
29000
29025
NONE
NONf
NONE
NONE
NONE
NONE
NONE
22130
2211.0
1.0002
t.0003
1.0215
1.0220
1.0215
NONE
25200
28255
NONE
•LAST LISTED IN 1972
-------
TABLE C-l . DYES AND PIGNUTS MANUFACTURED IN 1973 (CONTINUED}
E. I. OUPONT K MF.NOURS + COMPANY, INC. (CONTINUEDI
DYE OR PIGMENT NAME
O
cn
3IR£CT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
•DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
•DIRECT
DIRECT
•DIRECT
•DIRECT
DIRECT
DIRECT
81
88
102
2
15
23
37
33
9
22
51
67
99
ORANGE
ORANGE
ORANGE
RED 1
RED
RED
RED
RED 25
RED 28
RED
RED
RED 72
RED 81
RED 117
RED 236
RED 238
VIOLET
VIOLET
VIOLET
VIOLET
VIOLET
BLUE 1
BLUE 2
BLUE 6
BLUE 8
BLUE 15
BLUE 74
BLUE 78
SLUE 80
BLUE 86
BLUE 104
BLUE 120
8LUE 120
BLUE 125
BLUE 143
BLUE 199
BLUE 218
BLUE 263
GREEN 1
GREEN 6
GREEN 26
GRLEN 27
GREEN 38
GREEN 47
BROWN 31
BROHN 74
BROWN 95
BROWN 111
COLOR
INDEX DYE OR PI3MENT NAME
NONE DIRECT BROWN 154
NONE DIRECT ELACK 9
29156 DIRECT BLACK 9
22310 DIRECT PLACK 51
2,3500 'DISPERSE YELLOW 2
27640 DISPERSE YELLOW 3
29160 DISPERSE YELLOH 23
29190 DISPERSE YELLOW 32
22120 DISPERSE YELLOW it2
22240 DISPERSE YELLOW 54
23630 DISPERSE YELLOW 64
29200 DISPERSE YELLOW 67
28160 DISPERSE YELLOH 131
28230 'DISPERSE ORANGE 3
NONE DISPERSE DRANGE 25
NONE DISPERSE ORANGE 41
27885 DISPERSE ORANGE 44
22480 DISPERSE ORANGE 62
27905 DISPERSE ORANGE 75
NONE DISPERSE ORANGE 98
NONE DISPERSE RED 1
24410 DISPERSE RED 11
22590 DISPERSE RED 13
NONE DISPERSE RED 17
24140 DISPERSE RED 55
2<»400 DISPERSE RED 59
34146 DISPERSE RED 60
34200 DISPERSE RED 65
NONE DISPERSE RED 135
7^180 DISPERSE RED 140
NONE DISPERSE RED 161
3-*085 DISPERSE RED 162
34090 DISPERSE RED 211
34010 DISPERSE VIOLET 17
NONE DISPERSE VIOLET 26
NONE DISPERSE VIOLET 27
24401 DISPERSE VIOLET 28
NONE 'DISPERSE BLUE 3
30280 DISPERSE BLUE 7
30295 DISPERSE BLUE 56
34045 DISPERSE tJLUE 60
NONE 'DISPERSE 3LU^ 61
28280 DISPERSE BLUE 62
NONE DISPERSE BLUE 64
35660 DISPERSE BLUE 109
36300 DISPERSE BLUE 132
30145 DISPERSE BLUE 133
NONE DISPERSE SLUE 150
;OLOR COLOR
INDEX OYE OR PIGMENT NAME INDEX
30120 DISPERSE CLUE 165 NONE
31560 DISPERSE BLUE 172 NONE
31565 DISPERSE BROWN 2 NONf
27720 DISPERSE GROWN 14 NONF
NONE DISPERSE cLACK 1 11365
11855 FLUORESCENT ORIGHTENER 28 40622
26070 FLUORESCENT BRIGHTENER 102 NONE
NONE MORDANT RfO 27 45180
10338 MORDANT bROWN 1 20110
47020 MORDANT BROWN 18 20150
47023 MORDANT BROWN 49 13265
NONE MORDANT BROWN 70 NONE
NONE MORDANT BLACK 1 15710
11005 »SOLVENT YELLOW 2 11020
>JONE SOLVENT YELLOW 14 '12055
NONE SOLVENT YELLOW 47 NONE
NONE SOLVENT ORANGE 24 NONE
NONE SOLVENT ORANGE 25 • NONE
NONE SOLVENT RED Z4 26105
NONE SOLVENT RED 33 NONE
11110 SOLVENT RED 49 45170
62015 SOLVENT RED 69 NONE
11115 'SOLVENT VIOLET 8 42535
11210 SOLVENT BLUE 4 44045
NONE SOLVENT BLUE 36 61551
NONE SOLVENT BLUE 37 NONE
60756 SOLVENT BLUE 38 NONE
NONE SOLVENT BLUE 57 NONE
NONE SOLVENT BROWN 19 NONE
NONE SOLVENT BROWN 20 NONE
NONE SOLVENT BROWN 22 NONE
NONE SOLVENT BLACK 5 50415
NONE SOLVENT BLACK 17 NONt
NONE VAT OYE 0 7Q315
62025 VAT YELLOH 3 61725
NONE VAT YELLOW 22 NONE
61102 »VAT ORANGE 1 59105
61505 VAT ORANGE 2 59705
62500 VAT ORANGE 3 59300
63285 VAT ORANGF 4 59710
NONE VAT ORANGE 9 59700
NONE VAT OR5NGE 11 70805
»)ONE VAT RED 12 NONE
NONE VAT RED 13 70320
NONE VAT RED 16 NONE
NONE *VAT RED 23 71130
NONE VAT RED 32 71135
NONE VAT RED 52 NONE
•L4ST LISTED IN 1972
-------
TABU C-l .
S¥£S AN3 PIGM-->JTS MANUFACTURED IU 1973 (CONTINUED)
£. I. DUPCNf 0- NEMOUkS » COMPANY, IMC. {CONTINUED*
ro
o
01
3YE OR PIGMENT NAME
»»T VIOLET 1
VAT VI3LET 9
VST VJ3LET 10
**T VIOLET 13
*VST VI3LET 1?
¥«T SLUE l>
*T»T BLUE 6
VAT BLUE 11
¥»T BLUE 12
VAT BLUE 11.
»»T BLJE 16
VAT BLUE 18
*AT BLUE 20
tf«T BLUE 60
t»AT GREEN i
MAT GREEN 3
VAT GF.EEN S
tfAT GREEN 20
VST S^OHN 1
VAT SRQHN 3
VAT BROWN isO
VAT BLS;K 13
*AT SLACK 25
VAT BLSCK 27
PIGMENT YELLOW i
»I6MEN? YELLOW 7i>
«9IGMENT YELLOH 12
»»IS«ENT YELLOM 14
*PIG^ENT ORANGE is
'IGf'ENT RED 15
3IGf£NT RED 22
'IGVENT RED 23
'IGMENT REO 3
»I5«EHT RED 6
•'IG^ENT RED 38
OIGHENT a.~.o 1.8
3ALCIUM PIGMENT REO 57
»IGHENT REO 58
>HA PISHENT RED si
STA PI31ENT RED 81
>TA PIGHEKT VI3LET i
?1A PIGMENT VIOLET 3
SIGMENT VIOLET 19
FIGMENT VIOLET 31
>1A PIGMENT BLVZ i
»JU PIGMENT SLUE i^
»TA PIGHENT BLUE i
-------
TABLE C-]
DYES AND FIGM^MTS MANUFACTURED IN 1973 (CONTINUED*
EASTMAN KODAK 33MPSNY
ro
o
are OR PIGMENT NAM;
BASIC SLUE 75
DISPERSE YELLOW 23
DISPERSE YELLOW 33
DISPERSE YELLOW 31.
DISPERSE YELLOrf 42
DISPERSE YELLOW 85
DISPERSE YELLOW 86
DISPERSE YELLOW 87
DISPERSE YELLOW 88
DISPERSE YELLOW 89
DISPERSE ORANGE 3
OIS°ERSE ORANGE 5
DISPERSE ORANGE 17
9ISC-ERSE ORANGE 25
DISPERSE GRANGE 57
DISPERSE GRANGE 58
DISPERSE ORANGE 59
DISPERSE RED 1
DISPERSE RED 5
DISPERSE RED 17
DISPERSE RED 21
DISPERSE RED 30
DISPERSE RED 35
DISPERSE RED 60
DISPERSE RED 65
DIS°ER5E RED 85
DISPERSE RED BS
DISPERSE RED 117
DISPERSE RED 136
DISPERSE RED 137
DISPERSE P.ED 138
DISPERSE VIOLET 27
DISPERSE VIOLET l»l
DISPERSE VIOLET kZ
•3ISPERSE VIOLET i»3
DISPERSE VIOLET HI*
DISPERSE BLUE 3
DISPERSE BLUE 1 >»
DISPERSE BLUE 27
DISPERSE BLUE 62
DISPERSE BLUE 6"»
DISPERSE BLUE 79
DIS°ERSE BLUE 102
DISDERSE BLUE 112
DISPERSE BLUE 117
DISPERSE BLUE 118
DISPERSE BLUE 119
DISPERSE BLUE 120
COLO1?
INDEX
NONE
26070
NONE
NONE
10338
NONE
NONE
NONE
NONE
NONE
11005
11100
NONE
NONE
NONE
NONE
NONE
11110
11215
11210
NONE
NONE
NONE
60756
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NOME
NONE
61505
61500
60767
NONE
NONE
NONE
3YT OR PIGMENT NAME
DISPERSE BLUE 121
OISPERS- BLUE 123
DISPERSE 3ROMN 2
DISPERSE BROHN 5
'DISPERSE BROHN 7
DISPERSE BLACK 9
DISPERSE BLACK 33
DISPERSE BLACK 34
20LOR
INDEX
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
•L»ST LISTED IN 1972
-------
TA8LE C-».
0ȣS
-------
TABLE C-l.
DYES AMO PIGMENTS MANUFACTURED IN 1973 (CONTINOCDl
GAP
OYE OR PIGHENT NAHi
ro
O
VO
CID
cio
CIO
DID
DID
CID
CID
cio
CIO
:io
cio
;io
CID
CIO
CID
CIO
;io
DID
310
CIO
CIO
»
CID
10
CIO
CID
CIO
CIO
CID
CIO
CID
CID
CIO
CIO
CIO
CIO
CIO
CIO
CIO
CIO
CIO
CID
CID
CID
ID
CIO
CIO
CIO
OYE 0
YELLOW 23
YELLOW 25
YELLOW 29
YELLOW 36
YELLCW 38
YELLOW *2
YELLOW **
YELLOW 76
YELLOW 99
YcLLCW 121
YELLCW 135
YELLCH 151
YELLOW 159
ORANGE 1
GRANGE 1
ORANGE 7
ORANGE 8
ORANGE ID
ORANGE 2*
ORANGE 56
ORANGE 60
GRANGE 63
ORANGE 72
ORANGE 7*
ORANGE 115
RED 1
RED *
RED M
YELLOW 18
RED 32
RED 35
RED 37
RED 52
REO 73
RED 85
RED 88
REO 89
REO 97
REO 11*
REO 115
REO 115
REO 133
REO 137
REO 192
REO 186
REO 350
VIOLET 1
COLOR
INDEX 3YE OR PIGMENT NAHE
13010 ACID VIOLET 7
191510 ACIO 8LU£ 78
1L575 ACID SLUE 83
16230 ACIO SLUE ID*
20170 ACIO SLUr 113
22895 ACIO 8LU£ 120
18732 ACID 3LUE 158
22870 ACID BLUE 158
187*0 0+C BLUl 179
187*5 ACIO GREEN 3
HONE *ACID GREEN 5
18050 ACIO GREEN 9
1*710 ACIO GREEN 12
1*720 ACIO GREEN 16
It255 ACIO GREEN 20
17065 ACID GREEN 22
18065 ACID GREEN 25
170*5 ACID GREEN 50
*6100 ACIO 8R3HS 1
27290 ACID BROWN 6
222*5 ACID BROHN 1*
1?620 ACIO BRDrfN 31
23910 ACIO 8RD*N 152
22890 ACID BROWN 158
23635 *ACID BRCWM 2*3
27201 ACID BLACK 1
27200 ACID OLACK 2*
17995 ACID BLAC< 29
17755 DIRECT BROWN 2
NONE ACIO BLACK 52
16810 »ACID BLACK 107
26207 ACIO BLACK 108
17025 AZOID RED 2
COLOR
INDEX OYE OR PIGMENT NAHE
18055 AZOIC RED 2
18075 AZOIC RED 73
*2650 AZOIC RED 7*
16055 AZOIC BLUl 3
16260 AZOIC BLUE 7
*20*5 AZOIC BLUL 7
*2080 AZOIC BROKN 9
*2090 AZOIC BROWN 2o
*26*5 AZOIC BLACK *
62055 AZOIC BLACK 15
61530 AZOIC DIAZOIC 2<«
&2125 BASE AZOIC OIAZOIC *
62130 BASE AZOIC OIAZOIC 5
63010 BASE AZOIC OIAZOIC 10
620*5 'BASE AZOIC DIAZOIC 28
SOME BASE AZOIC OIAZOIC *8
62105 SALT AZOIC DIAZOIC 1
*2660 SALT AZOIC OIAZOIC 3
*2735 SALT AZOIC OIAZOIC 5
26360 SALT AZOIC DIAZOIC 6
26*00 SALT AZOIC OIAZOIC 8
1*880 SALT AZOIC DIAZOIC 9
15050 SALT AZOIC DIAZOIC 10
NONE "SALT AZOIC OIAZOIC 12
*2085 SALT AZOIC DIAZOIC 13
*2095 SALT AZOIC OIAZOIC 28
*2100 SALT AZOIC DIAZOIC 3t
13*25 SALT AZOIC OIAZOIC 35
**025 SALT AZOIC DIAZOIC 36
20*95 'SALT AZOIC OIAZOIC 37
*2170 'SALT AZOIC DIAZOIC *2
&1570 SALT AZOIC DIAZOIC *9
**090 SALT AZOIC OIAZOIC 121
10395 »AZOIC COUPLING 2
1*625 »AZOIC COUPLING *
20195 AZOIC COUPLING 13
HONE AZOIC COUPLING 1&
NONE AZOIC COUPLING 16
NONE AZOIC COUPLING 19
NONE AZOIC COUPLING 20
20*70 BASIC YELLOW 11
26370 BASIC YELLOH 13
NONE BASIC ORANGE 1
22311 BASIC ORANGE 2
15711 BASIC ORANGE 1*
NONE BASIC ORANGE 21
NONE BASIC ORANGE 22
37530 BASIC «ED 13
COLOR
INDEX
37120
NONE
NONE
NONE
37505
37155
NONE
NONE
NONE
NONE
37155
37210
37125
37120
37151
37235
37135
37010
37125
37025
37110
370*0
371ZO
37105
37130
37151
37100
37255
37275
37035
37150
37050
NONt
37505
37560
37595
37600
37520
375*5
37530
*8055
NONE
11320
11270
* 60 05
*8035
*BO*0
*8015
•L»ST LISTED IN
-------
TABLE C-l .
OY£S ASD PISMEilTr fANUFACTUREO IN 1973 (CONTINUED)
SAP CCHPORATID'I (CONTINUEDI
DYE OR RICHEST NAME
IN5
O
BASIC
3ASIC
3ASIC
3ASIC
3ASIC
3ASIC
3ASIC
SAS-IC
36SIG
3&SIC
3ASIC
3ASIC
BASIC
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
^DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
3IRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
3IRECT
RED 11*
RED 15
RED 13
RED 49
VIOLET 7
VIOLET 10
VIOLET IS
SLUE 1
BLUE. 3
81U£ 53
9ROHN 1
3RD MM 2
BROWN 4
DYE 0
YELLOW it
YELLOW 5
YELLOW 6
YELLOW 8
YELLON 11
YELLOW 12
YELLOW 27
YELLOW Za
YELLOW 29
YELLOW 44
YELLOW 5C
YELLOW S'.j
YELLOW 106
ORANGE 3
ORANGE 3
ORANGE 11
ORANGE 15
ORANGE 15
ORANGE 26
ORANGE 34
ORANGE 34
ORAMGE 37
ORANGE 37
ORAMGE 39
ORANGE 59
ORANGE 73
ORANGE 81
ORANGE 83
ORANGE 102
*£D 1
RED 20
RED 23
RED 25
RED 31
COLOR
INDEX
NONE
NONE
11085
NONE
Mi 020
45170
1*6013
42G25
51004
NONE
21000
21030
21010
22165
24890
47035
1,0001
13920
4000G
24895
13950
19555
19556
29000
29025
NONE
40300
22130
22140
NONE
40002
40003
29150
40215
40220
40260
40265
40215
NONE
25200
NONE
29090
29156
22310
15075
29160
29190
29100
OYE OR
DIRECT
DIRECT
DIREST
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
JIRECT.
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
OIRECT
DIRECT
OIRECT
DIRECT
DIRECT
OIRECT
D I RE C T
DIRECT
'DIRECT
OIRECT
DIRECT
OIRECT
DIRECT
DIRECT
DIRECT
DIRECT
3IRCCT
OIRECT
DIRECT
OIRECT
DIRECT
OIRECT
DIRECT
PIGHLNT NAH
RED 37
RED 39
RED 72
RED 75
RED .76
RED 81
RED 11.1
RED 123
VIOLET 9
VI3LF.T 47
BLUE 1
BLUE 2
BLUE 6
BLUE 8
BLUE 15
BLUE 25
BLUE 71
BLUE 76
BLUE 80
BLUE 86
BLUE 96
BLUE 136
BLUE 191
BLUE 199
BLUE 218
GREEN 1
GREEN 6
SREFN 38
Gf^ttN 39
GRCEN 47
BROWN 1
BROWN 31
BROHN 32
BROWN 44
BROWN 95
BROWN 106
BROHN 111
BLACK 4
BLACK 17
BLftCK 22
BLACK 3fl
BLACK 51
BLACK 75
DISPERSE: YELLOW i
DISPERSE YELLOW 3
DISPERSE YELLOW 5
DISPERSE YELLOW 23
DISPERSE YELLOW 31
COLOR COLOR
INDEX OYE OR PIGMENT NAME INDEX
22240 DISPERSE YELLOH 33 NONE
23fr30 DISPERSE YELLOH i»2 10336
29200 DISPERSE YELLOH 54 47020
,253«0 DISPERSE ORANGE 3 11005
12245 'DISPERSE CRANGE 3 11005
2S160 DISPERSE ORANGE 5 11100
40290 DISPERSE ORANGE 17 NONE
17820 DISPERSE ORANGE 29 NONE
27865 DISPERSE RED 1 11118
25410 DISPERSE RED'4 60755
24410 DISPERSE RED 5 11215
22590 'DISPERSE RED 7 11150
NONE DISPERSE RED 11 62015
24140 DISPERSE RED 13 11115
24400 DISPERSE RED 15 60710
23790 DISPERSE RED 17 11210
34140 DISPERSE RED 55 NONE
24411 DISPERSE RED 59 NONE
NONE DISPERSE RED 60 6Q756
74180 DISPERSE KEO 86 NONE
23155 DISPERSE RED 167 NONE
24065 DISPERSE VIOLET 1 61100
NONE DISPERSE VIOLET
-------
TABLE C-l. OYES AMD PIGMENTS MANUFACTURED IN 1973 (CONTINUED!
GAF CORPORATION (CONTINUED!
COLOR
DYE OR PIGMENT NAME INDEX
M3ROANT RED 7 167&0
H3RDANT SLUE 1 i.3830
H3RDANT BLUE 3 1.3820
H3ROANT BLUE 9 H-855
M3ROANT BROWS 1 20110
M3RDANT BROWN 15 14870
H3ROANT BROWN 19 11,350
N3ROANT BROWN 21 19600
fOROANT BROWN 33 13350
MORDANT BROWN 1»0 17590
H3ROANT BLACK 1 1?710
M3ROANT BLACK 11 14645
MORDANT BLACK 17 1E705
SOLVENT YELLOH 2 11020
SOLVENT YELLON 13 NONE
SOLVENT YELLOW ft 12055
SOLVENT YELLON 19 13900
SOLVENT YELLOW 29 21230
SOLVENT YELLOW 43 NONE
SOLVENT YELLOW 47 NONE
SOLVENT ORANGE 3 11270
SOLVENT ORANGE 5 1871.5
SOLVENT ORANGE 7 1211.0
SOLVENT ORANGE 20 NONE
SOLVENT RED 3 12715
SOLVENT RED 22 21250
33LVENT RED 21. 26105
SOLVENT RED 33 NONE
SOLVENT RED 35 4F170
SOLVENT RED 35 16260
33LVENT RED 1.0 NONE
SOLVENT R£0 49 45170
SOLVENT BLUE 9 NCNE
SOLVENT BLUE 11 61525
SOLVENT BLUE 38 NONE
SOLVENT GREEN 2 NCNE
SOLVENT GREEN 3 61565
S3LVENT BROWN 11 NONE
SOLVENT BROWN t2 21010
VAT DYE 0 7G3t5
VAT YELLOW 2 67300
VAT YELLOW I* 59100
S3LUBILIZED VAT YELLOH 10 6E430
VAT ORANGE 1 59105
VAT ORANGE 2 59705
VAT ORANGE 3 59300
»VAT ORANGE 7 71105
VAT ORANGE 9 59700
OYS OR PIGMtNT NAME
VAT ORANGE 15
VAT RED 10
VAT R£0 13
VAT RED li.
VAT RED 29
VAT RED 32
VAT VIOLET 1
VAT VIOLET 9
VAT VIOLET 13
VAT BLUE: 4
VAT 8LU: 6
VAT BLUE 11
VAT BLUE. 11.
VAT BLUE 16
VAT 3LUE 18
VAT BLUt 20
VAT BLUE 26
VAT BLUE 29
VAT BLUE 39
*VAT BLUE 53
VAT GREEN 1
VAT GREEN 3
VAT GREEN 8
VAT GREEN 9
VAT BROWN 1
SOLU8ILIZED VAT BROWN
VAT BROWN 3
VAT 3ROWN 20
VAT BLACK 9
VAT BLACK 25
VAT BLACK 27
*VAT SLACK 37
VAT SLACK 38
PI GHENT YELLOW 13
PIGMENT YELLOH 1*
PIGMENT YELLOW 17
PIGMENT ORANGE 16
PIGMENT RED 5
PIGMENT RED 22
PIGMENT RED 38
•PIGMENT RED 41
PIGMENT RED 1.8
PMA PIGMENT RED 79
?MA PIGMENT RED 81
?TA PIGMENT RED 81
PIGMENT RED 190
»MA PIGMENT VIOLET 1
PTA PIGMENT VIOLET 1
"OLOR
INDEX
69025
67000
70320
71110
7111*0
71135
bOOlO
60005
68700
59800
69825
69615
&9S10
71200
59815
59800
60015
MONE
71205
59825
69500
71050
59850
70800
70301
59015
NONE
65230
69525
69005
NONE
NONE
21100
21095
21105
21160
12i<90
12315
21120
21200
15865
NONE
1.5160
1.5160
7111.0
1.5170
l>2170
DYE OR PIGMENT NAME
PMA PI3HENT VIOLET 3
PIGMENT VIOLET 23
PMA PISMENT BLUE 1
»PTA OIGIENT BLUE i
PMA PIGMENT BLUE 2
PTA PIGMENT BLUE 9
PMA PIGMENT BLUE ii»
PTA PIGMENT BLUE 11.
ALPHA PIGCENT BLUE 15
BETA PIGMENT BLUE 15
PIGMENT BLUE 25
PIGMENT BASIC BLUE 1
•PMA PIGMENT GREEN 1
PMA PIGMENT GREEN 2
PMA PIGMENT GREEN z
•PTA PIGMENT GREEN 2
•PTA PIGMENT GREEN 2
FUGITIVE FIGMENT GREEN «.
'PIGMENT GREEN 7
PIGMENT GREEN 36
PIGMENT BROWN 28
COLOR
INDEX
1.2535
51319
1.2595
4.2595
(.1.01.5
1.2025
1.2600
1.2600
71.160
71.160
21180
i.2025
1.201.0
'1.201.0
49005
1.231.0
1.9005
1.2000
74160
69015
»L»ST LISTED IN 1972
-------
TABLE C-l . DY£S MO PlG^TS MANUFACTURED IN 1973 (CONTINUED)
HERCULES, INS.
ro
DYE OR PIGMENT NAME
•ORDANT GREES 4
OIGMENT YELLOW i
SIGMENT YELL3W 3
^IGMENT YELL3H 5
»IG»:ENT YELLOW 6
PIGMENT .YELLOW 49
SIG1ENT YcLLJH 73
SIG':GMENT YELLOW 13
SIG*ENT YELL3H 14
°IGMENT YELL3H 17
OIG-ENT YEILLOH 76
"IG1ENT OR4N5E 1
»IG-IGMENT RED 13
»IG«ENT RED 17
=>IGM£NT RED 18
?>IGUENT RED 22
PIGMENT REO 23
SDOIUf PIGMENT RED 112
DARK PIGMENT RED 1
LIG"T PIGMENT RED 1
3IG*ENT RED 3
OIGMENT RED <»
»IG«ENT RED i»6
»I5HENT RiO 52
34RIUM PIGMENT RED 53
C1LCIUM PIGHiNT REO 5^
DOLCILH PIGMENT RED 57
PI6WENT RED 58
'IG^ENT ^£0 63
>HA PIG1ENT RE3 61
TA PI3HENT RE3 81
"'IGMENT RED 90
»1A PIGMSMT VIOLET 1
i»TA PIGMENT VIOLET I
»FJ6ITIV£ PIGMENT VIOLET 3
»1A PIGMENT VIOLET 3
=>TA PIGMENT VIOLET 3
»1A PIGMENT BLUE 1
COLOR
IKOEX
10005
ueso
11710
11660
11765
11738
11741
11770
Z1090
21100
21095
21105
NONE
11725
12060
12075
21110
21160
12310
12<»60
12395
12390
12350
12315
12355
12370
12070
12070
12120
12085
15865
15860
15585
11*830
15850
15825
15880
<»51&0
1.5160
-------
TABLE C-].
DYES A,NO PI5H-:*TS NANUFACTURtO IN 1973 (CONTINUED)
ICI UNITED STATES, INC.
ro
CO
DYE OR PIGMENT NAME
4010 RED 50
»»:io VIOLET 31.
*:iD VIOLET l»3
ASID BLUE 25
ADIO BLUE <»0
•ACID BLUE l»3
AGIO BLUE <»7
AGIO BLUE 78
4SIO BLUE 81
4310 GREEN 25
AGIO GREEN i»l
ACID BLACK 1.8
DIRECT SLUE 87
DISPERSE BLUE 35
'DISPERSE BLUE 72
REACTIVE YELLOrf 1
R-ACTIVE YELLOW «t
REACTIVE YELLOW 7
REACTIVE YELLOW 18
REACTIVE YELLOW *>2
REACTIVE YELLOW 86
REACTIVE ORANGE 1
REACTIVE ORANGE k
REACTIVE ORANGE 12
REACTIVE ORANGE 13
REACTIVE ORANGE 1<»
REACTIVE RED 1
REACTIVE RED 2
REACTIVE RED 3
REACTIVE RED 5
REACTIVE RED 8
REACTIVE RED 11
REACTIVE RED 29
REACTIVE RED 31
REACTIVE RED 33
REACTIVE RED l»3
REACTIVE RED 58
REACTIVE VIOLET 1
REACTIVE BLUE 3
REACTIVE BLUE <*
REACTIVE BLUE 5
REACTIVE BLUE 25
REACTIVE BLUE 71
•REACTIVE GREEN 6
REACTIVE BROUN 9
REACTIVE BROWN 10
REACTIVE BROWN 17
REACTIVE BLACK 9
COLOR
INDEX
6P215
60730
62055
62125
63000
62085
62105
61.515
61570
62560
65005
71.200
NONE
60725
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NONE
18158
NONE
16159
NONE
17908
NONE
NONE
NONE
NONE
NOME
NCNE
NONE
NONE
61205
61205
NONE
NCNE
NONE
NONE
NONE
NONE
NONE
OYE OR PIGMENT NAME
INGRAIN BLUE 1
INGRAIN BLUC 3
•SOLVENT RED 52
»SOLV£NT VIOLET 13
•SOLVENT VIOLET Ik
•SOLVENT SLUE 11
SOLVENT BLUE 13
VAT YELLOW 2
•SOLUaiLIZEO VAT YELLOW t>
•VAT ORANGE 1
VAT ORANGE 2
VAT ORANGE 9
VAT ORANGE 15
VAT RED 1
VAT VIOL-:T i
VAT VIOLET 9
VAT VIOLET 13
VAT BLUE 5
VAT BLUE. 11
VAT GR£=N 1 ;
•SOLUBILIZEO VAT GREEN 1
VAT GREEN 3
•SOLU9ILIZEO VAT GREEN 3
•VAT BROWN 1
VAT BROWN 3
VAT BROWN 28
•VAT BLACK 25
VAT BLACK 27
VAT BLACK 3"*
»?IGM£NT YELLOW 1
•PIGMENT YELLOW <»9
COLOR
INDEX
NONE
68210
60725
61705
61?25
62080
67300
59101
59105
59705
59700
69025
73360
60010
60005
68700
59825
69815
59825
59826
69500
69531
70800
69015
NONE
69525
69005
NONE
11680
11765
»L»ST LISTED IM 1972
-------
TABLE C-l.
DYES ANO PIG1ESTS MANUFACTURED IN 1973 (CONTINUED!
KEHAN££ OIL 30-4PANY, HARSHA H CHEMICAL COMPANY DIV.
ro
DTE OR PIGMENT NAME
»3IO VIOLET 29
ftllD VIOLET <»3
ASID VIOLET i»9
&:iO GREEN 25
"DIRECT 9ROHN 2
DIRECT YELLOH 26
DIRECT YELLOW *»!»
DIRECT YELLOW 50
DIRECT ORANGE 26
DIRECT ORANGE 72
DIRECT ORANGE 7<»
DIRECT RED 2*
DIRECT RED 26
DIRECT RED 31
DIRECT RED 80
DIRECT RED 81
DIRECT RED 83
DIRECT SLUE 2
'DIRECT BLUE 6
DIRECT BLUE 76
DIRECT BLUE 80
DIRECT BLUE 126
•DIRECT BROWN 95
•DIRECT BLACK 38
DIRECT BLACK 80
DISPERSE RED 15
DISPERSE VIOLET 1
DISPERSE BLUE 3
DISPERSE BLUE 7
•DISPERSE BLUE 9
rtDROANT GREEN >*
MDROANT BLACK 13
SOLVENT VIOLET 13
S3LVENT GREEN 3
PIGMENT YELLOW 1
PIGHENT YELL3H 3
PIGMENT YELLOW 12
PIGMENT YELLOW 13
PIGMENT YELL3H i<»
PIGMENT ORANGE 16
PIGMENT RED 2
PIGMENT RED 5
09RK PIGMENT RED 1
LIGHT PIGMENT *EO 1
PIGMENT RED 3
PIGMENT RED 6
PIGMENT RED <»0
PIGMENT RED <*6
COLOR
INOE.X
NONE
60730
61570
22311
2?300
29000
29025
29150
NONE
28255
29185
29190
29100
35780
2816D
29225
22590
NONE
2*1*11
NONE
3 "*0 10
30235
31600
60710
61100
61505
62500
NONE
10005
&3615
60725
61565
11680
11710
21090
21100
21095
21160
12310
12070
12070
12120
12090
12170
15865
DYE OR PIGMiNT NAME
= IGM£NT RED 52
CALCIUM PIGMENT RED 5
-------
TABLE C-) •
DYES AND
INNONT ;
MANUFACTURE IN 1973 (CONTINUED)
IN3
CT!
OrE OR PIGMENT NAME
DIRECT BLUE 86
DISPERSE YELL CM 3
DIS°ER3E YELLOH 5
DISPERSE YELLOW 23
DISPERSE YELLOW 33
DISPERSE YELLQrf 3U
DISPERSE YELLOW 42
DISPERSE YELLOH 54
DISPERSE ORANGE 17
DISPERSE ORANGE 30
DISPERSE ORANGE 59
DISPERSE RED 1
DISPERSE P.EO 5
'DISPERSE RED 11
•DISPERSE RED 13
DISPERSE RED 15
DISPERSE RED IT
DISPERSE RED 31
•DISPERSE RED 54
•DISPERSE RED 55
DISPERSE RED 65
DISPERSE RED 78
•DISPERSE RED 176
DISPERSE RED 177
DISPERSE RED 178
DISPERSE RED 179
DISPERSE RED 180
DISPERSE VIOLET I
•DISPERSE VIOLET it
DISPERSE VIOLET 27
DISPERSE BLUE 1
DISPERSE 3LUE 3
DISPERSE OtUE 7
•DISPERSE BLUE 27
•DISPERSE BLUT 54
DISPERSE BLUE »6
•DISPERSE auur TS
•DISPERSE PtO£ 95
*MSPE6S€ BLUZ Ifr*
•DISPERSE bLUE 1FZ
PISHEM Y£tL3l* 12
PIGMENT YtLLOH 13
PIGMENT YELLOK i".
>I&MENT- YELLOH ir
PIGMENT ORANGE 13
OIGMENT ORANGE ie
PI GHENT ORANGE 31.
.'IGHENT RED 5
COLOR
INDEX
74180
11855
12790
Z6070
NONE
NONE
10333
i»7020
NONE
NONE
NONE
11110
11215
62015
11115
60710
11210
11250
NONE
NONE
NONE
NONE
NONE
NONE
NONE
NCNE
NONE
61100
61105
NONE
61505
6Z500
60767
NONE
63265
NONE
NONE
NONE
NONE
21090
ZUOO
?t095
2110*
21110
21160
^1115
121.90
DYE OR PIGMENT NANE
RED
17
38
PIGMENT
aIGM£NT *£D
PIGMENT RED ts
3ARIUM PIGMENT RED 53
•PIGM£NT
-------
TABLE C-l .
OfiS *^D PlGHiNTS >< ANUFACTUREO IN 1973 (CONTINUED)
KEYSTOSi CCILCH WCSKSt INC.
0*E OR PIGMENT NffM£
HORDANT GREEN i»
PIGMENT YELLOW 3
PIGMENT ORANGE 1
PIGMENT RED 2
"IGMENT Rc.0 10
PIGMENT RED 13
PIGMENT RED 3
PIGMENT RED 6
PTA PIGMENT RED 81
PI&MENT GREEN 8
PIGMENT BROHN 3
LAKE PIGMENT ORANGE
LAKE ACID *EO Z6
LAKE ACID BLUE 10<>
17
CCLO*
I^OcX
10005
11710
11725
1?313
13395.
1Z1ZO
12090
•»5160
10006
Z1010
15510
16150
rsj
-------
TABLE C-l. DYES ANO PISMEtfTS MANUFACTURED IN 1973 (CONTINUED)
H. KOHSSTAKM + COMPANY, INC.
IN3
DTE OR PIGMENT NAM£
FD+C BLUE 1
FD+C BLUE 2
FD + C RED 2
FD + C RED 3
FD + C RED it
RED i»0
YELLOW 5
FD+C YELLOW 6
D+S BLUE 1
D+C BLUE 6
3 + C GREEN 5
3+C GREEN 6
3 + C GREEN 8
3 + C OR4NGE *
3 + C RED 2
3+C RED 3
D+C REO 6
3 + C RED 7
3+0 RED 8
3+C RED 9
D+C RED 10
0+C RED 11
3+C RED 12
3+C RED 17
3+C REO 19
D+C RED 21
3+: REO 22
3+C REO 30
3+C RED 31
3+C REO 33
3+C RCO 3i
3*C- RED 36
3+C YELLOVT 51
D+C YELUOH 6
3+C YELLOW 7
3+C YELLOW S
3+C YELLOW W
3 + C YELLOW 11
ȣXT. 0+C GREEN 1
iXT. D + C VELLC* 1
iXT. &*C YtLLDH 7
PIGMENT YELL3H 1
PIGMENT Y£LL3W 3
PI&HENT YELLOW 12
PIGMENT YELLOW Ik
PIGMENT O^ANSE 13
PIGMENT REO 3
PICMEKT «cO *
COLOR
INDEX
73015
16185
1^700
NONE
15985
73000
61570
61565
10020
15510
16185
158SO
15850
15585
15585
15630
15630
15630
26100
i»5170
1*5380
1*5380
73360
15800
17200
15880
12085
15985
1)5350
1.5350
470 (t5
5981.0
13065
10318
11680
11710
21090
21095
21110
12120
12085
3YE OR PIGMENT NAME
PIGMENT ^SD 6
3ARIUM PIGMENT SED <»9
SODIUM PIGMENT RED l»9
3ARIUM PIGMENT RED 53
•SODIUM PIGMENT RED 53
:ALCIUM PIGMENT RED 57
OIGMENT *ED 63
PMA PIGMENT REO 81
PTA PIGMENT RED 81
FUGITIVE PIGMENT VIOLET
PMA PIGMENT VIOLET 3
?TA PI5MENT VIOLET 3
»MA PIGMENT BLUE 1
°TA PIGMENT BLUE 2
PMA PIGMENT 8LUE 9
'MA PIGMENT GREEN 2
=>MA PIGMENT GREEN 2
PTA PIGMENT GREE:N 2
PTA PIGMENT GREEN 2
«MA PIGMENT GREEN i<
»PTA PIGMENT GREEN it
= IGMENT BROWN 3
LAKE AGIO YELLOW 23
"LAKE PIGMENT ORANGE 17
LAKE PIGMENT RED 60
LAKE PIGMENT REO 83
LAKE PIGMENT VIOLET 5
LAKE PIGMENT BLUE 2
-------
TABLE c-i-
DYES AMD PIGMEMIS MANUFACTURED IN 1973 (CONTINUED)
0. LEV£< COMPANY. INC.
OTE OR "IGHENT NAM£
PIGMENT BASIC YELLDH Z
PIGMEVT 3'SIC YELLOW 37
PIS'tNT OIRE3T YELL3W 6
DIRECT YELLOH 11
ACID D^ANGi 8
.PKS PIGMENT ^£3 81
PIGMENT DIRECT RED at
:P-(» PIGMENT VI3LET 9
P1A PIG1ENT 8LJE 7
•P.TA PIGHENT BLUE 7
PTA PIGMENT BLUE 10
PIGMENT ACID B10WN li»
•CAKE -ACID SLUE 93
LAKE ACID 8tUE 10I»
COLOR
INDEX
mOOO
1*1001
1.0001
1E575
<»5160
<»Z510
58055
58055
<*i»0i»0
-30195
<»2735
ro
CXI
•LAST LISTED IM 1972
-------
TABLE C-l.
OYIS ArtO PIGM£
-------
TABLE C-1 . OYES A»40 PIG1ESFS SANUFACTUREO IN 1973 (CONTINUED)
MASTIN-HARIETM CHEHKALSj SOOVECO DIVISION
ro
IN)
o
COLOR
Jit OR PIGMENT NAM£ INDEX
DISPERSE YELLOW l»2 10338
•DISPERSE YELLOW 5i» 1,7020
DISPERSE YELLOW 123 NONE
•DISPERSE ORANG; 5 11100
DISPERSE ORANGE 9
-------
TAJLC e-i-
OVES AND PIGNUT? MANUFACTURED IN 1973 (CONTINUED)
OTTO 6. MAYt I)li.
DYE OR PIGMENT HMZ
DISPERSE ORANGE 77
DISPERSE ORANGE 78
DISPERSE ORANGE 79
DISPERSE ORANGE 80
DISPERSE BLUE 79
DISPERSE BLUE 109
OIS°£RSE BLUE 156
•ViT VIOLET 1
V4T VIOLET 9
VST BLUE 18
VAT BLUE aO
VAT GREEN 1
VAT GREEN 3
VAT GREEN 9
VAT BROWN 1
VAT BROWN 11
VAT BROHN 13
VAT BLACK 9
VAT BLACK Z5
VAT BLACK 37
COLOR
INDEX
NONE
NONE
NPNE
NONE
NONE
NONE
NONt
60010
60005
59815
59800
59825
69500
59850
70800
NONE
NONE
65Z30
69525
69005
ro
•LAST LISTED IN 197Z
-------
TABLE C-l .
OYES ASO PlGH-fTS MANUFACTURED IN 1973 (CONTINUED)
MAX HA*X COLOR » CHEMICAL COMPANY
DYE OR PIGMENT NAM;
ACIO VELLCH Z3
M3RDANT RED 9
"IGNENT B&SIC YELLOW 2
'IGMENT ORANGE 16
= IGMENT RED 23
'IGMENT RtO
-------
TABLE C-l . DYES A*t3 PISMENTS MANUFACTURED IN 1973 (CONTINUED!
MOBAY CHEMICAL CO., V£RON« DIVISION
DTE OR PIGMENT NAM£
ro
1X3
co
4310
ACID
ACID
ACID
*CID
ACID
•»CIO
ACID
ACID
ACID
ACIO
ACID
ACID
ACID
*cio
ACID
ACID
»CID
ACIO
•ACID
ACID
»cio
ACID
•ACID
4CID
icio
ACID
»CID
»CID
ACID
ACID
»CIO
scio
•ACID
ACID
»cio
JCID
ACID
4CIO
•»cio
»CID
ACID
ACIO
ACID
ACID
ACID
ACID
ACID
YELLOW 11
YELLOW 17
YELLOW 19
YELLOW 23
YELLOW i»0
YELLOW 42
YELLOW 44
YELLOW 49
YELLOW 5if
YELLOW 59
YELLOW 79
YELLOW 99
YELLOW 151
YELLOW 159
YELLOW i?i»
ORANGE 7
ORANGE 9
ORANGE 10
ORANGE 60
ORANGE 116
RED 1
RED If
RED 73
RED 85
RED lllf
RED 151
RED 186
RED 225
R£0 266
RED 277
RED 278
RED 337
VIOLET 7
BLUE 7
BLUE 25
8LUE 27
BLUE ifO
BLUE 158
BLUE 158
BLUE 198
BLUE 203
BLUE 221
GREEN 25
GREEN ifl
GREEN 84
BLACK 52
BLACK 139
BLACK 17Z
COLOR
INDEX
1K820
18965
NONE
19140
18950
22910
23900
NONE
19010
NONE
NONE
13900
13906
NONE
NONE
15510
15575
16230
18732
NONE
18050
14710
27290
22245
23635
26900
18810
NONE
NONE
NONE
NONE
NONE
18055
42080
62055
61530
62125
14880
15050
NONE
NONE
NONE
61570
62560
NONE
15711
NONE
NONE
3Y- OR ">IGMtNT NA
AZOIC
3ASIC
3ASIC
3ASIC
3ASIC
9ASIC
BASIC
•3.ASIC
3ASIC
3ASIC
3ASIC
BASIC
3ASIC
9ASIC
3ASIC
3 ASIC
3ASIC
BASIC
BASIC
3ASIC
3ASIC
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
3IRE.CT
DIRECT
DIRECT
DIRECT
3IRE3T
DIRECT
DIRECT
DIRtCT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
•DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
DIRECT
3ROWN 9
YrLLOH 11
YtuLOH 13
YELLON 21
YELLOW 28
YELLOH 29
ORANGE 21
3RANGE 27
ORANGE 28
RED 13
RED 14
RED 18
RED 23
VIOLET 16
BLUE 1
SLUE 5
BLJE 45
BLUE 47
BLUE 69
GREEN 4
BLACK 9
YELLOH 4
Y-LLOH 11
YELLOW 44
YELLOW 50
YELLOW 84
VELLON 132
ORANGE 29
OSANGE 67
ORANGE 72
ORANGE 73
ORANGE 78
ORANGE 80
ORANGE 81
RED 4
RED 23
RED 24
RED 26
RED 79
RiD 80
RED 81
RED 83
RED 95
RED 122
RED 139
RED 209
RED 212
BLUE 1
COLOR COLOR
INDEX DYE OR PIGMENT N/SNE INDEX
NONE "DIRECT 9LUE 2 22590
48055 DIRECT SLUE 15 2lflfOO
NONE DIRECT BLUE 76 2lf
-------
TABLE C-l . DYES AND PIGNUTS MANUFACTURED IN 1973 (CONTINUED)
MOBAY CHEMICAL CO., VERONA DNISI3N (CONTINUED)
3YE OR PIGMENT NAM£
MORDANT BLACK 9
•mOANT BLACK 11
VAT YELLOW Z
VAT YELLOH It
VAT YELLOH 33
VAT ORANGE 1
VAT ORANGE 15
VAT VIOLET 21
VAT GREEN 32
VAT BROWN 3
COLOR
INDEX
16500
DYE OR PIGMENT NAME
67300
59100
NONE
59103
69025
NONE
NONE
69015
ro
•LAST LISTED IN 1972
-------
PO
rv>
in
TABLE C-l . 0ȣS A'JO PIS1S1TS MANUFACTURED IN 1973 tCONTIMUEOI
HORTON-NORHI;H ;>RODUCTS, INC.
COLOR
OYE OR PIGMENT NAM£ INDEX
SOLVENT YELLOH 107 NONE
SOLVENT RED !&<» NONE
SOLVENT RiO 165 NON£
SOLVENT VIOLET 13 60725
SOLVENT VIOLET Ut 61705
SOLVENT SLUE 98 NONE
SOLVENT BLUE 1DO NONE
SOLVENT GREEN 3 61565
-------
TABLE C-l • DYJS AMD PISS^TS MANUFACTURED IN 1973 (CONTINUED)
NYANZA, INC.
DYE OR PIGMENT NAM£
4CIO DYE 0
»CIO YELLOW 11
»CID YELLOW 17
1CID YELLOW 19
iCID YELLOW 99
•4SID ORANGE 51
tCIO ORANGE 60
»:iO ORANGE 74
»43IO ORANGE 86
H'lO ORANGE 115
ACID RED
-------
ro
TABLE C-l. DYES AMD PIG.IiHTS MANUFACTURED IN 1973 (CONTINUED)
PASSAIC COLOR t CHEMICAL COMPANY
DYE OR PIGMENT NAME
A5ID ORANGE 12
ACID RED 73
AGIO SLACK 53
8&SIC ORANGE 1
BASIC ORANGE 2
B4SIC 3^0>
-------
TABLE C-l•
DYsS AND PIGHi^lTS MANUFACTURED IN 1973 (CONTINUED!
"FISTti CH-HIDJL, INC.
DVE OR PIGMENT NAM£
AZOIC
»ZOIC
AZOIC
AZOIC
AZOIC
»ZOIC
AZOIC
AZOIC
•AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
(kZOIC
AZOIC
AZOIC
AZOIC
AZOIC
AZOIC
COUPLING 2
COUPLING 3
COUPLING 7
COUPLING 8
COUPLING 10
COUPLING 11
COUPLING 12
COUPLING lit
COUPLING 15
COUPLING 17
COUPLING 18
COUPLING 19
COUPLING 20
COUPLING 21
COUPLING 2fc
COUPLING 29
COUPLING 3>t
COUPLING 35
COUPLING 3
COLOR
INDEX
37505
37575
37565
37525
37510
37535
37550
37558
37600
37515
37520
37545
37530
37526
375<»0
37527
37531
37615
NONE
ro
C»
•LIST LISTED IN 1972
-------
TABLE C-I
DȣS &HO PIGMiNlS MANUFACTURED IN 1973 (CONTINUED)
PP3 IN3USTRI£S, MC.
OYE OR PIGMENT NAM;
PIGMENT YELLOW 3
PIGHENT RED 3
BARIUM PIGMENT RED t
»M» PIGHENT VIOLET 3
COLOR
INDEX
11710
12120
1&630
ro
ro
»L*3T LISTED IN 1972
-------
TABLE C-J. DYES AMD PIGHcNTS MANUFACTURED IN 1973 (CONTINUED*
RI3GENAT COLOR » CHEMICAL
ro
CO
o
COLOR
DYE OR PIGMENT NAN£ INDEX
PIGMENT YELLON 1 11680
PIGMENT YELLOW 12 21090
PIGMENT YELLOW !<• 21095
PIGMENT YELLOW i? 21105
PIGMENT ORANGE 13 21110
DARK PIGMENT RED 1 12070
PIGMENT R£0 * 12085
PIGMENT RED <»8 15865
BARIUM PIGMENT RED l»9 15630
CALCIUM PIGMENT REO <*9 15630
•PIGMENT RrD 52 15860
BARIUM PIGMENT RED 53 issss
CALCIUM PIGMENT RE3 57 15850
PTA PIGMENT RED 81 1(5160
PIGMENT RFO 90 l»5380
»PTA PIGMENT VI3LET 1 1.2170
FUGITIVE PIGMENT VIDLET 3 l»2535
P1A PIGMENT VI3LET 3 i»2S35
•PTA PIGMENT VIDLET 3 «535
•PTA PIGMENT 8LU£ 1 l»2595
BETA PIGMENT SLUE 15 71*160
PIGMENT BLUE 19 <»2750
•PTA PIGMENT GREEN Z *.20'»0
»PTA PIGMENT GREEN Z ".9005
•PTA PIGMENT GREEN <» i.2000
LAKE PIGMENT BLUE Zk
-------
TABLE C-1•
OYES AND
SANDOZ-HANOER.
ro
OJ
BYE OR PIGMENT NAME
FLUORESCENT BRIGHT£N£R l»9
FLUORESCENT BRIGHTENER 52
SDLVENT BLUE 3
PIGMENT YELLOW 1
PIGMENT YELLOW 12
PIGMENT YELLOH IV
PIGMENT YELLOH 85
PIGMENT ORANGE 13
PIGHENT RED 5
PIGMENT RED 7
PIGMENT RED 9
PIGMENT REO 17
PIGMENT REO <»8
»PTA PIGMENT RED 81
PIGMENT BLUE 25
P1A PIGMENT GREEN 1
P1A PIGHENT GREEN 2
P1A PIGMENT GRatN 2
•PTA PIGMENT GREEN Z
»PTA PIGHENT GREEN 2
PIGHENT BROHK 1
LAKE PIGMENT VIOLET 5
ITS HANUFACTUREO IN 1973 (CONTINUED!
INC.
COLOR
INDEX
NCNE
NCNE
1(2775
11680
21090
21095
NCNE
21110
12
-------
TABLE C-l. DYES MO PIGMENTS MANUFACTURED IN 19f3 (CONTINUED!
WILLIAMS COMPANY
COLOR
PYE OR PIGMENT NAH£ INDEX
PIGMENT SLUE 19
ro
OJ
-------
TABLE C-l.
OYtS A40 PIGHE>ITS HANUF»CTUREO IN 1973 »CONTINUED>
S3J-TEX CHENIC4L COMPANY, INC.
COLO*
DYE OR RICHEST N4H£ INDEX
LEUCO SULFUR YELLOW 9 530tO
SULFUR OR4NGH 1 53050
SULFUR RED 5 53830
'LEUCO SULFUR B.UE 7 53i*l»Q
L£UCO SULFUR b^OHN 1 53000
SDLUeiUZED SULFUR BROWN 1 53001
LiUCO SULFUR B?OHN 10 53055
LEUCO SULFUR B^OHN 30 53630
SULFUR 8RCHN 35 53090
*L£UCO SULFUR B^OMN Z6 53090
LEUCO SULFUR BU4CK 1 53185
SOLUBILIZtQ SULFUR BLACK 1 53186
ro
CO
CO
•t»ST LISTED IN 1972
-------
TABLE C-l. OViS A^D PIGM£>*rS MANUFACTURED IN 19?3 (CONTINUED)
STANCE 30MPANY
COLOR
DYE OR PIGMENT NAME INDEX
FO*C REO 3 16185
FO + C RED 3 ^Si.30
F3 + C REO <» Hf700
FO+C VELLCH 5 191UO
FO + C VEL4.0H $ 1E985
ro
CO
-------
TABLE C-l. OYiS A 40 PI3HH>lrS HANUFACTURFO IN 1973 (CONTINUED!
STERLING DRUG INC., HILTON-DAVIS CHEMICAL COMPANY
OJ
en
COLO?
DYE OR PIGMENT NAME INDEX
»»CIO YELLOW 4 18695
D YELLOW 17 18965
SID YELLOW 73 4?353
SID RED 1 16050
IIO RED 87 45380
;iD RED 88 1E620
310 VIOLET 17 42550
3ID VIOLET 49 42640
CIO BLUE 7 ",2080
HO BLUE 9 42090
IIP GREEN 15 44025
»ZOIC YELLOW 1 37613
AZOIC YELLOW 1 37090
AZOIC RED 1 37559
»ZOIC RED 1 37090
AZOIC RED 6 37520
»ZOIC RED 6 37090
AZOIC BLUE 3 NONE
3ASE AZOIC DIAZOIC 4 37310
3ASE AZOIC OIAZOIC 6 37110
3ASE AZOIC CIAZOIC 12 37105
SALT AZOIC OIAZOIC I 37135
SALT AZOIC OIAZOIC 3 37010
SALT AZOIC DIAZOIC 5 37125
SALT AZOIC DIAZOIC 9 37040
SALT AZOIC DIAZOIC 13 37105
SALT AZOIC DIAZOIC 13 37130
SALT AZOIC OIAZOIC 26 37151
•SALT AZOIC DIAZOIC 48 37235
AZOIC COUPLING 7 37555
3ASIC VIOLET 3 42555
3ASIC BLUE 1 1*2025
BASIC BLUE 5 4211,0
3ASIC BLUE 7 42595
3ASIC 9LUE 11 44040
31S-IC 31UE 25 440',5
3IRECT YELLOW 11 40000
DIRECT RED 80 35780
•3IRECT BLUE 85 74180
DISPERSE YELLOW 54 47020
FLUORESCENT SRIGHTENER 9 40521
FLUORESCENT BRIGHTENER za 40522
FLUORESCENT 3RIGHTENER 125 NONE
FLUORESCENT BRIGHTENER 128 NONE
FLUORESCENT 3RIGHTENER 138 NONE
FO+C BLUE 1 42090
F3*C BLUE 2 73015
FO + C RED 2 16185
3YF OR PIGMENT NAME
FD+C RED 3
FO+C VIOLET 1
FD+C YELLOW 6
0+C GREEN B
0+C RED 22
»0+C RED 39
FIGMENT YELLOW i
PIGMENT YELLOW 74
PIGMENT YELLOW 12
PIGMENT YELLOW 13
PIGMENT YELLOW 14
PIGMENT YELLOW 17
PIGMENT ORANGE 5
PIGMENT ORANGE 16
PIGMENT ORANGE 34
PIGMENT RED 5
PIGMENT RED 23
LIGHT PIGMENT RED 1
PIGMENT RED 3
'IGMENT RED 4
BARIUM PIGMENT RED 49
:ALCIUM PIGMENT RED 49
SODIUM PIGMENT RED 49
BARIUM PIGMENT RED 53
JALCIUM PIGMENT RED 54
CALCIU1 "IGMENT RED 57
»TA PIGMENT RED 81
»IGMENT RED 90
PMA PIGMENT VIOLET 3
PHA PIGMENT BLUE 10
ALPHA PIGMENT BLUE 15
BETA PIGMENT BLUE 15
LAKE PIGMENT BLUE 24
30LOR
INDEX
45430
42640
15985
10020
45380
13058
11680
11741
21090
21100
21095
21105
12075
21160
21115
12490
12355
12070
12120
12085
15630
15630
15630
15585
14830
15850
45160
45380
42535
44040
74160
74160
42090
•L»ST LISTED IN 1973
-------
TABLE C-l-
OV£S AND RISKS-OS MANUFACTURED IN 1373 (CONTINUED!
STERLING DPJG INC., THOH4SSET COLORS DIVISION
DTE OR PIGMENT NAHE
D + C 0&4NGE 4
D + C 054HGE 5
0 + C ORANGE 10
0*C R£D 3
D+C RED 6
0*C RE3 7
B*C RE3 9
D+C REO 12
0»C RE3 13
a+C RE3 19
0+C RE3 21
8»C REO Z7
»D»C RED 38
0+C REO 30
0+0 REO 36
0+C YELLOW 51
»LPHA PIGMENT 8LUE 15
BtTA PIGMENT BLUE 15
!»I6K£NT GREEN T
COLOR
INDEX
1E510
<»5370
15850
15850
1T585
15630
If630
"*E170
i.5380
1*51*10
73360
74160
74160
74260
IND
CO
•L»ST LISTED IN 197Z
-------
TABLE C-1 •
OYJS AND PIGMEMTS 'UHuFACTURtD IN 1973 (CONTINUED)
SUM CH£,1ICAL 3D9
S30IUM PIGMENT RED i>9
PIGMENT R£0 52
BARIUM PIGMENT RED 53
CALCIUM PIGMENT REO 57
PIGMENT R£0 63
PIGMENT RED 77
PMA PIGMENT REO 61
COLOR
INDEX
1E51Q
1,5370
12075
15850
15850
15585
15585
15630
15630
15630
15630
<*5170
<*5380
15880
11680
11710
11720
11738
21090
21100
21095
21105
12060
12075
21110
21160
21115
12395
12390
12315
12355
12360
12070
12070
12120
12085
21120
15865
1E630
15630
15630-
1E860
15585
15850
15880
15626
U5160
DY-: OR 3IG-MENT NAME
3TJ aI3M£NT R£0 81
°IGM£NT ^ED 122
=MA PISMiNT VIOLET 1
3TA 'IS^iNT VIOLET 1
?MA PIGMiNT VIOLET 3
3IGMENT VIOLET 19
FIGMENT VIOLET 23
=M« PIGMtNT BLUE 1
ALPHA PISMENT BLUE 15
3ETA PIGMENT BLUE 15
"IGMENT SLUE 25
»IGM£NT GREEN 7
*PIGM£NT GREEN 10
'IGMENT GREEN 36
•PIGMENT GREEN 38
»aIGMENT 9ROWN 5
LAKE PIG1ENT RED 60
LAKE PIGMENT RED 81
30LOR
INDEX
<»5160
73915
",5170
t2170
1,2535
1,6500
51319
1,2595
71,160
71,160
21180
7H260
12775
71,160
NONE
15800
16105
1,5160
•L»ST LISTED IM
-------
TABLE C-l-
OYiS ANO PIGMENTS MANUFACTURED IN 1973 (CONTINUcOl
SYNALLOY CORPORATION, BLAf.KMAN-UHLER CHEMICAL OIV.
CO
oo
DYE Of PIGMENT NAME
AZOIC YELLOW 2
4ZOIC YELLOW 2
tzoic YELLOW 3
4ZOIC YELLOW 3
AZOIC YELLOW 3
4ZOIC ORANGE 3
»ZOIC ORANGE 3
JZOIC ORANGE IB
AZOIC ORANGE 10
AZOIC RED 1
AZOIC RED 1
AZOIC RED 2
AZOIC RED 2
AZOIC RED 6
AZOIC RED 6
AZOIC VIOLET 1
4ZOIC VIOLET 1
AZOIC BLUE 3
AZOIC BROWN ?
AZOIC 3ROWN 7
AZOIC BROWN 9
AZOIC BROWN 10
AZOIC 9ROWN 10
AZOIC BLACK 4
3ASE AZOIC OIAZOIC 2
3ASE AZOIC DIAZOIC 3
3ASE AZOIC DIAZOIC 4
3ASE AZOIC DIAZOIC 10
3ASE AZOIC CIAZOIC 12
3ASE AZOIC CIAZOIC 13
3ASE AZOIC DIAZOIC 28
3ASE AZOIC DIAZOIC 32
3ASE AZOIC DIAZOIC 44
SALT AZOIC OIAZOIC 1
SALT AZOIC OIAZOIC Z
SALT AZOIC OIAZOIC 3
SALT AZOIC OIAZOIC 5
SALT AZOIC OIAZOIC 6
SALT AZOIC CIAZOIC 8
SALT AZOIC DIAZOIC 9
SALT AZOIC DIAZOIC 10
SALT AZOIC DIAZOIC 11
SALT AZOIC DIAZOIC 12
SALT AZOIC DIAZOIC 13
*SALT AZOIC OIAZOIC 20
SALT AZOIC DIAZOIC 28
SALT AZOIC DIftZOIC 35
SALT AZOIC OIAZOIC <»1
COLO-?
INDEX
37610
3T1ZO
37610
37553
37090
37558
37010
37505
37050
37558
37090
37530
371ZO
37520
37090
37505
37165
NONE
37600
37120
NONE
37550
37120
NONE
37005
37010
37210
37120
37105
37130
37151
37090
37000
37135
37005
37010
37125
37025
37110
37040
37120
37085
37105
37130
37175
37151
37255
37165
3Y.T OR PIGMENT NAME
SALT AZOIC DIAZOIC <*"*
•SALT AZOIC OIAZOIC i>8
SALT AZOIC DIAZOIC IGMENT YELLOW 13
PIGM£NT YELLOW 14
PIGMENT YELLOW 17
PIGMENT ORANGE 34
'IGMENT RED 23
PIGMENT VIOLET 23
9£TA PIGMENT BLUE 15
PIGMENT BROWN 5
COLOR
INDEX
37000
37235
37050
37505
37575
37560
37610
37565
37525
37535
37550
37558
37600
37605
37515
37520
3751.5
37530
37526
37527
37531
37615
37585
NONE
10338
47023
11100
NONE
60755
62015
21100
21095
21105
21115
12355
51319
74160
15800
•UST LISTED IN 197Z
-------
TABLE C-).
DYES AND PIGMHTS NANUF&CTUREO IN 1973 (CONTINUED)
TENNECO, IMC.« 3AL/I.NK DIVISION
DYE OR PIGMENT NAME
*3IGMENT YELLOH 5
°IGMENT YELtOH 6
'IGHENT YELLOH 73
SIGMENT YELLOW 12
'IGMENT YELLOW 1*»
3IGMENT R?D 3
34RIUM PIGMENT RED i»9
'IGHENT RtD 52
3HSIUH PIGMENT RED 53
C4LCIUM PIGMENT REO 57
»1A PIGMENT tflOLET 3
3ETA PIGMENT BLUE 15
»IGMENT GREEN 7
COL 03
INDEX
11660
11670
1173S
31093
21D95
12120
15630
15860
1E585
15850
i.2535
7i»160
71.Z60
IN5
CO
•L4ST LISTED IN 1972
-------
TABLE C-l. DYES AMD PIGME1H MANUFACTURED IN 1973 (CONTINUED)
T01S RIVER CUBICAL CORPORATION
DYE OR PIGMENT NAME
PO
-pa
o
4:10
&OID
4310
43ID
43ID
43io
4310
4310
43ID
ACIO
4CID
S3io
43ID
5310
6310
63ID
»43IO
&3IO
4CIO
4CIO
4310
4010
4310
45ID
4310
5010
4310
4310
4310
4310
4310
4310
43ID
6.3 ID
4310
*CID
43ID
43ID
4010
»»3IO
4310
4CIO
4310
4310
4310
«4GIO
4310
4310
YELLOW II*
YELLOW 17
YELLOW 23
YELLOW 29
YELLOW 36
YELLOW i»0
YELLOW 5<»
YELLOW 65
YELLOW 76
YELLOW 99
YELLOW ill*
YELLOW 127
YELLOW 128
YELLOW 129
YELLOW 151
YELLOW 153
YELLOW 1?!*
YELLOW 179
ORANGE 7
ORANGE 8
ORANGE 10
ORANGE 2It
CHANGE 51
ORANGE 60
ORANGE 62
ORANGE 63
ORANGE 7<»
ORANGE 76
ORANGE 86
ORANGE 116
ORANGE 119
REO 1
REO it
RE 3 17
YELLOW 18
REO 37
REO 57
REO 73
REO 88
RED 99
PEO 11*
REO 131*
REO 137
RED 151
REO 167
REO 179
RED 183
RED 191
COLOR
INDEX
18960
1*965
1911*0
18900
13065
Ic950
19010
1".170
18650
13900
NONE
NONE
NONE
NONE
13906
NONE
NONE
NONE
15510
1557-3
16230
20170
26550
18732
NONE
22870
1871(5
18870
NONE
NONE
NONE
18050
1"710
16180
16255
1701)5
NONE
27290
15620
23285
23635
21.810
17755
26900
NONc
19351
18800
NONE
DYc. OR PIGMENT NAHE
ACID RED 191,
ACID RED 201
ACID RED 212
ACID RED 213
ACID RE3 266
ACID RED 299
ACID REO 309
ACID REO 337
ACID VIOLET 3
ACID VIOLET 6
ACID VIOLET 7
ACID VIOLET 1,9
4CIO BLUE 23
ACID BLUE 25
ACIO BLUE M
»»CID BLUE i»3
4CID BLUE 95 DIRECT YELLOW 133
61570 DIRECT ORANGE 15
13361 DIRECT ORANGE 15
NONE DIRECT ORANGE 26
NONE DIRECT ORANGE 29
20195 DIRECT ORANGE 61
NONE DIRECT ORANGE 72
NONE DIRECT ORANGE 73
NONE 'DIRECT ORANGE 110
NONE 'DIRECT REO 1
20<.70 DIRECT RED 2
27070 DIRECT REO it
27075 DIRECT RED 16
22311 DIRECT RED 23
65005 DIRECT REC 2
-------
TABLE C-l •
OTiS AO FISM5NTS MANUFACTURED IN 1973 (CONTINUED!
TOMS RI*ER IHE'UCAL CORPORATION (CONTINUED)
ro
DYE OR PIGMENT NAf£
DIRECT RED 79
DIRECT RED 8D
DIRECT RED 81
DIRECT RED S3
DIRECT RtO 122
DIRECT RED 239
DIRECT VIOLET 3
DIRECT VIOLET 66
DIRECT 3LUE 1
•DIRECT BLUE 2
DIRECT BLUE i*
DIRECT BLUE 25
DIRECT BLUE 67
DIRECT BLUE 71
DIRECT 3LUE 75
DIRECT BLUE 76
DIRECT BLUE 78
DIRECT BLUE 80
DIRECT BLUE S6
DIRECT BLUE 91
DIRECT BLUE 98
DIRECT 9Ll<£ 130
DIRECT BLUE 120
DIRECT BLUE 126
DIRECT BLUE 151
DIRECT BLUE 160
DIRECT BLUE 189
DIRECT BLUE 21B
"DIRECT GR-EN 1
'DIRECT GREEN 6
*DIRECT GREEN 8
DIRECT GREEN 25
DIRECT GRIEN 27
DIRECT GREEN 28
DIRECT GREEN 51
JIRT.CT GREEN 49t
'DIRECT: BROWN 1
•DIRECT- BROWN 95
DIRECT BROWN 111
DIRECT SLACK 19
DIRECT BLACK 22
•DIRECT SLACK <.*
DIRECT BLACK 51
DIRECT BLACK 56
DISPERSE YELLOK 3
DISPERSE YELLOH fr
DISPERSE YELLOW 23
3ISP£RS£ YELLOW 33
COLOR
INDEX
29065
3F780
26160
29225
29210
NONE
27885
29120
21*1.10
22590
23850
23790
27925
31*11.0
31-220
21*1.11
31.200
NONE
7H81)
NONE
23155
3<*085
31*090
31*010
21*175
NONE
NONE
21*1.01
30280
30295
30315
3<*0 <»5
NONE
1".155
3W60
NONE
NOME
30H.3
NONE
35255
351.35
NOME
27720
3-.17&
11855
12690
26(T70
NONE
OYt OR PIGMENT NAM
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE
DISPERSE;
DISPERSE
DISPERSE
DISPERSE
IE ACTIVE
?EftCTIVi
•REACT IV t
REACTIVE
REACTIVE
REACTIVE
REACTIVE
REACTIVE
REA6TIV-
REACTIVE
YELLOW «
YELLOW 50
YELLOW 5i»
DRANGE 3
ORANGE 21
ORANGE 25
ORANGE 30
ORANGE 37
ORANGE 38
DRANGE 78
RED 1
RED "»
RED 15
RED 17
RED 30
RED 35
RED 60
RED 65
RED 73
RED 78
VIOLET 1
VIOLET 27
VIOLET 28
VIOLET 57
BLUE 1
BLUE 3
BLUE 7
BLUE 55
BLUE 56
BLUE 6".
BLUE 73
SLUE 79
BLUE 85
BLUE 125
BROW 1
BLACK 1
BLACK 2
BLACK 2
YLLLOW 2
YiLLOW 3
YflLOW 6
ORANGE 5
ORANGE 11
RED U
RED 55
RED 86
BLUE 2
BLUE 5
30LOR
INDEX
10338
NONE
1.7020
11005
NONE
NONE
NONE
NONE
NONE
NONE
11110
60735
60710
11210
NONE
NONE
60756
NONE
NONE
NONE
61100
NONE
6 1102
NONE
61.500
61505
62?00
NONE
63285
NONE
NONE
NONE
NONE
NONE
11152
11365
11255
37185
NONE
NONE
NONE
NONE
NONE
1810-5
NONE
NONE
61211
61205
DYE OR PIGMENT NAKE
REACTIVE ELUE 7
REACTIVE BLACK 1
FLUORESCENT BRIGHTENER l»5
MORDANT DYE 0
•MORDANT DYE 1
MORDANT YELLOW 5
MORDANT YELLOW 30
MORDANT ORANGE 1
MORDANT ORANGE 6
MORDANT ORANGE 8
MORDANT RED 7
MORDANT BPOWN 1
MORDANT BROWN 33
•MORDANT BROWN 63
MORDANT SLACK 1
MORDANT BLACK 3
MORDANT BLACK tl
MORDANT BLACK 17
MORDANT BLACK 26
VAT DYE 0
VAT YELLOW 2
VAT YELLOW H*
VAT YELLOW 33
VAT ORANGE 1
VAT ORANGE 2
VAT ORANGE 7
VAT ORANGE 9
VAT ORANGE 15
VAT RED 13
VAT RED 15
VAT VIOLET 1
VAT VIOLET 9
VAT VIOLET 13
VAT BLUE 6
VAT BLUE 11
VAT BLUE lif
VAT BLUE 18
WT BLUE 20
•VAT GREEK 1
VAT GREEN 3
VAT GREEN 9
VAT BROWN 1
VAT BROWN 3
VAT BR&HN 11
VAT BROWN 57
•VAT BLACK 9-
VAT SLACK 22
VAT BLACK 25
COLOR
INDEX
17916
NONE
13360
19350
18710
11*030
26520
NONE
18760
20110
132EO
NONE
15710
1461-0
li»6«.5
15705
NONE
70315
67300
NONE
NONE
59105
597C5
71105
59700
69025
70320
71100
60010
60005
687 CO
69825
69815
69810
59815
59800
59825
69500
598^50
70800
69015
NONE
NONE
65230
NONE
69525
»L»ST LISTED IH 1972
-------
TA8LE C-l. DT-S AMD PIGMS^TS MANUFACTURED IN 1973 «CONTINU£0»
TDSS RItfER C4E-UCAL CORPORATION (CONTINUED)
COLOR
OYE OR PIGMENT NAHc INDEX
tf»T BLACK 27 69D05
*3IGMENT VAT 3RANGE 3 59300
PIGMENT RED m NONE
»ftLPH4 PIGHEMT BLUE IS /'.ISO
»3IG,«ENT BLUE 6^ 69825
PIGMENT GREEN T 74360
ro
4=-
ro
*U»ST LISTED IN 197Z
-------
TABLE C-1.
DYES ANO PIGI^TS MANUFACTURED IN 1973 (CONTINUED)
PAJL UHLICM » jOfcpANY, INC.
INJ
-pa
CO
DVE OR PIGMENT NAM£
PIGMENT ORANGE 2
PIGMENT RED 17
'PIGMENT RED 23
PIGMENT RED 3
PIGMENT RtD <»
BARIUH PIGMENT *ED i»9
PMA PIGMENT RED 81
PTA PIGMENT *ED 81
FUGITIVE PIGMENT VIOLET i
PSA PIGMENT VIOLET 1
FUGITIVE PIG'lEST VIOLET 3
PHA PIGMENT VI3LET 3
P*IA PIGMENT BLUE 1
PMA PIGMENT BLUE 9
PMA PIGMENT GREEN 1
PMA PIGMENT GREEN Z
PMA PIGMENT GREEN 2
LAKE PIGMENT RED 83
LAKE PIGNENT VIOLET 5
NATURAL RCO &
COLOR
INDEX
12060
1Z390
12355
12120
12065
15630
1.5160
i»5160
i»5170
-------
TABLE C-l
DY£S AND PIGSHTS 1ANUFACTU RED IN 1973 (CONTINUED)
UNIDENTIFIED
|>YE OR PIGMENT NAME
AZOIC YELLOW 2
A'ZOIC YELLOW 2
AZOIC ORANGE 3
»ZOIC ORANGE 3
AZOIC RED 1
AZOIC RED 1
AZOIC RED 2
AZOIC RED Z
AZOIC RED 6
AZOIC RED 6
AZOIC BLUE 3
AZOIC BROWN 3
AZOIC BROWN 3
AZOIC BROWN 9
PIGMENT YELLOH i»>
PIGMENT RED 1Z2
PIGMENT BLUE 27
COLOR
INDEX
37610
371EO
37558
37010
37558
37090
37530
371ZO
3?520
37090
NONE
37600
37010
NONE
21095
73915
77510
ro
-------
ro
-F=>
cn
TABLE C-l.
DYES A<0 PIG1E1TS MANUFACTURED IN 1973 (CONTINUED)
UNITED MERCHANTS AND MFR. , ROMA CHEMICAL-COLOR DItf.
DfE OR PIGMENT NAM;
PIGMENT YELLOW 12
PIGMENT YELLOW 13
PIGMENT YELLOH ll»
PIGMENT YELLON 17
PIGMENT ORANGE 16
PIGMENT ORANGE 3k
PIGMENT REO 5
PIGMENT RED ZZ
PIGMENT RED 23
BETA PIGMENT BLUE 15
PIGMENT BROWN 5
COLOR
INDEX
Z1090
21100
21095
21105
21160
21115
12>>90
12315
13355
74160
15800
-------
TABLE C-l .
3TES AS3 PIGIE'US 1ANUFACTURED IN 1973 (CONTINUED)
HASNER-JENKIN33N COMPANY
OYE OR PIGSEST NAME
ftCIO YELLOW 33
FD*C BLUE 1
FD + C BLUE Z
FD*C GREEN 3
F3+C RE3 Z
FO*C RED 3
FO + C RED
-------
TABLE C-l • OY£S AMO PIGM^-US MANUFACTURED IN 1973 (CONTINUED)
J. S. YOUNG COMPANY, YOUNG ANALINE WORKS, INC., SUBSIDIARY
DYE OR PIGMENT NAHE
ACID YELLOU 19
A3IO YELLOW 23
AGIO YELLOW 55
ASIO ORANGE 7
ACID ORANGE 10
ACID ORANGE 2".
ACID ORANGE 1.5
ACID GRANGE lib
ACID RED 1
ACID RED *
ACID RED 1".
ACID RED 33
ACID RED 73
ACIO RED 85
ACIO RED 88
ACID RED 99
ACID RED 106
ACIO RED 151
ACID VIOLET 3
ACID VIOLCT 6
ACIO BLUE 29
ACIO BLUE 92
ACID BLUE 113
ACID BROWN lit
ACID BROWN 53
ACID BROHN 93
ACIO BLACK 1
ACID SLACK 29
ACIO 3LACK
-------
APPENDIX D
LOCATION OF PLANTS MANUFACTURING DYES, PIGMENTS
OR INTERMEDIATES, LISTED ALPHABETICALLY BY NAME
OF THE MANUFACTURER
249
-------
TABLE D-1
ALLIANCE CHEMICAL COMPANY, INC.
Plant: 33 Avenue P
Newark, New Jersey 07105
Office: Linden Avenue
Ridgefield, New Jersey 07657
Azoic dyes
Azoic components
250
-------
TABLE D-2. ALLIED CHEMICAL CORPORATION
Morristown, New Jersey 07960
Specialty Chemicals Division
P.O. Box 1069
Buffalo, New York 14240
Aminoazo xylene toluene hydrochloride
4-Amino-5-hydroxy-2,7-naphthalenedisulfonic acid,
monosodium salt
8-Amino-l,3,6-naphthalenetrisulfonic acid,
disodium salt
2-Amino-5-nitrobenzenesulfonic acid
4-Amino-4'-nitro-2,2'-stilbenedisulfonic acid, disodium salt
m-[(p-Aminophenyl) azo.] benzenesulfonic acid
p-[(p-Aminophenyl)azol benzenesulfonic acid, sodium salt
tert-Amyl p-naphthol
Anilinomethanesulfonic acid, sodium salt
Benzidine sulfate
N-Benzyl-N-ethyl-m-to! uidine
4,4'-Bis (dimethylaminophenyl) methane-2-sulfonic acid, sodium salt
4-Chlorometanilic acid
4-Chloro-3-nitrobenzenesulfonic acid
4-Chloro-3-nitrobenzenesulfonic acid, potassium salt
Copper phthalocyaninedisulfonic acid
p-([2-Cyanoethyl] methyl ami no) benzaldehyde
3,6-Diacetylamino acridine
3,3'-Dichlorobenzidine dihydrochloride
p-(Diethyl ami no) benzaldehyde
N,N-Diethyl aniline
4,5-Dihydroxy-2,7-naphthalenedisulfonic acid, sodium salt
p-Dimethy1 aminobenzaldehyde
N,N-Dimethylaniline
Di-trichloromethyl copper phthalocyanine
Dyes
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
Food, drug and cosmetic colors
Mordant dyes
Solvent dyes
Sulfur dyes
Vat dyes
N-Ethylaniline
Ethyl benzyl am'line sul f oni c acid
N-Ethyl-N-phenylbenzyl amine
rt-(N-Ethyl-m-toluidino)-m-toluenesulfonic acid
Isatin
Isobutyl /^-naphthol
251
-------
,10-dianhydride
,10-diimide
TABLE D-2. (Continued)
Leuco-1,4-diaminoanthraquinone
N-Methyl aniline
2-Methylindole
7- (and 8)-Nitronaphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
5-Nitro-o-toluenesulfonic acid
3,4,9,10-Perylenetetracarboxyli c-3,4:9
3,4,9,10-Perylenetetracarboxyli c 3,4:9
ji-(Phenylazo) aniline hydrochloride
Phthalide
Quinaldine
Quinizarin
2,2'-5,5'-Tetramethyl-4,41-diamino triphenylmethane
6,6'-Thiodimetanilic acid
1,3,3-Trimethyl-2-methyleneindoline
1,3s3-Trimethyl-2-methylene indoline omega aldehyde
Violanthrone
Harmon Colors
P.O. Box 14
Hawthorne, New Jersey 07507
Manufactures a variety of dyes
550 Belmont Avenue
Haledon, New Jersey 07508
Dyes
[Phthalocyaninato (2-)] copper
252
-------
TABLE D-3. AMERICAN COLOR AND CHEMICAL CORPORATION*
100 East 42nd Street
New York, New Yor£J0017
Colors Department
Mt. Vernon Street
Lock Haven, Pennsylvania 17745
1-Aminoanthraquinone and salt
3-Ami no-4~ethoxyacetani1i de
N-(4~Amino-3-methoxy~l-anthraquinonyl)-p-toluenesulfonamide
2-Amino-(p-nitrophenylazo) naphthalene
5-Aminosalicyclic acid
o-Anisidine
o-Anisidinomethanesulfonic acid
7H-Benz (de) anthracen-7-one
Benzotriazole
3,3' ,4,4!-Biphenyltetramine
2-Bromo-6-chloro-4-nitroaniline
2-Bromo-4,6-dinitroanil ine
o-Chloroaniline
1-Chioro™ 2-methylanthraqui none
4-Chloro-2~nitroam'line
l-Chloro-2~nitrobenzene
o-(4-Chloro-3-nitrobenzoyl) benzoic acid
4-Chloro-2-nitrotoluene
4-Chlororesorcinol
1,5 (and 1,8)-Diaminoanthraquinone
2,6-Diaminoanthraquinone
3,4'-Diami nobenzani1i de
9,10-Dihydro-9,10-dioxo-2,6-anthracenedisulfoni c acid
9,10-Dihydro~9,10~dioxo-2,6-anthracenedisulfonic acid, sodium salt
9,10-Dihydro-9S10-dioxo-l-anthracenesulfonic acid
9910-Dihydro-9,10-dioxo-l-anthracenesulfonic acid, sodium salt
9,10~Dihydro~5~nitro-9,10-dioxo-l-anthracenesulfonic acid
9,10-Dihydro-l-nitro-9,10-dioxo-2-anthroic acid
1,5-Dihydroxy-4,8-dinitroanthraquinone
2,4-Dinitroaniline
1,5 (and 138)-Dinitroanthraquinone
Acid dyes
Azoic coupling components
Azoic diazo components
Direct dyes
Disperse dyes
Mordant dyes
Solvent dyes
Vat dyes
* Owned by North American Phillips Corporation
** Formerly part of Intermediates Division, Tenneco, Inc.
253
-------
TABLE D-3. (Continued)
4-Ethoxy-3-nitroacetani1ide
1-Hydroxyanthraquinone
4-Hydroxymetanilic acid
Leuco quinizan'n
l-(Methylamino) anthraquinone
£r(3-Methy1-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
p_-Nitroaniline
p-Nitroaniline
5-Oxo-1 -CE.-SU!fophenyl)-2-pyrazol ine-3-carboxyl ic acid
Quinizarin
2-Quinizarinsulfonic acid
Resorcinol, monoacetate
Beaufort, South Carolina 29902
7-Amino-4-hydroxy-2-naphthalenesulfonic acid, sodium salt
3-Hydroxy-2,7-naphthalenedisulfonic acid
7-Hydroxy-l,3-naphthalenedisulfonic acid
7,7'-Ureylenebis (4-hydroxy-2-naphthalenesu1fonic acid)
Paterson, New Jersey 07524
Dyes
Disperse dyes
Reading, Pennsylvania 19604
12th and Bern Streets
Acid dyes
Direct dyes
Disperse dyes
254
-------
TABLE D-4. AMERICAN CYANAMID COMPANY
Berdan Avenue
Wayne, New Jersey 07470
Organic Chemicals Division
Bound Brook, New Jersey 08805
N-Acetylsulfanilyl chloride
1-Aminoanthraquinone and salt
2-Aminoanthraquinone and salt
6-Amino-3'4'-azodi (benzenesulfonic acid)
1-Amino-4-benzamidoanthraquinone
1-Amino-5-chloroanthraquinone
2-Amino-5-ch1oro-4-ethy1benzenesulfonic acid
3~Amino-6-chloropyridazine
2-Amino-5-chloro-p-toluenesulfonic acid
4-Amino-3~hydroxy-l-naphthalenesulfonic acid
2-Ami no-4-methylpyrimi di ne
2-Ami no-5-methyl-1,3,4-thi adi azol e
2-Amino-l,5-naphthalenedisulfonic acid
2-Amino-1-naphthalenesulfonic acid
4-Ami no-1-naphthalenesulfoni c aci d
£-[(fi-Aminopheny]) azo] benzenesulfonic acid
2-Aminopyrimidine
4-Ami no-QL~ to! uenesulf oni c acid
Aniline
Aniline hydrochloride
Anilinomethanesulfonic acid
Anilinomethanesulfonic acid, sodium salt
7H-Benz (de) anthracen-7-one
Benzothiazole
2-Benzothiazolethiol, sodium salt
o-Benzoylbenzoic acid
(4,4'~Bi-7H-benz [de] anthracen)-7,7'-dione
3-Bromo-7H-benz (de) anthracen-7-one
1-Chioroanthraqui none
2-Chloroanthraqui none
Chloro-7H-benz (de) anthracen-7-one
2-Chlorobenzenesulfonami de
o-(£-Chlorobenzoyl) benzoic acid
1-Chioro-2-methylanthraqui none
1-Chioro-5-nitroanthraquinone
[(4-Chloro-o-tolyl) thio] acetic acid
j)-Cresol
454'-Diamino-2,2'-biphenyldisulfonic acid
4,4'-Diamino-3s3'-dimethyltriphenylmethane
4,4'-Di ami no-2,2'-sti1benedi sulfoni c aci d
4s5'-Dibenzamido-l ,1'-iminodianthraquinone
1,5-Dibenzoylnaphthalene
Dichlorobenzanthrone
255
-------
TABLE D-4. (Continued)
3-(Diethyl ami no) propiophenone
NjN-Diethyl aniline
9510~Dihydro-9,10-dioxo-l-anthracenesulfonic acid, sodium salt
16,17-Dihydroxyviolanthrone
N,N-Dimethy! aniline
2,2:~DimethyUl ,1 '~bianthraquinone
N 5N-Dimethyl-p-ni trosoani1i ne
4,4'-Dinitrostilbene-2,2'-disulfonic acid
Diphenylamine
1»3-Dipheny1-2-thiourea
2,5-Dithiobiurea
Acid dyes
Azoic coupling components
Basic dyes
Direct dyes
Disperse dyes
Mordant dyes
Oxidation bases
Solvent dyes
Sulfur dyes
Vat dyes
N-Ethyl aniline
&- Ethyl phenol
N-(Hydroxymethyl) phthalamide
3~Hydroxy-2,7-naphthalenedisulfonic acid, disodium salt
7-Hydroxy-l,3-naphthalenedisulfonic acid, disodium salt
6~Hydroxy-2-naphthalenesulfonic acid, sodium salt
N-(2-Hydroxy~]-naphthyl) acetamide
Hydroxynitroviolanthrone
2-Kydroxy-4-sulfo-l-naphtha!enediazoniurn hydroxide, inner salt
1,1'-Iminobis (4-aminoanthraquinone)
1,1'-Iminobis (4-benzamidoanthraquinone)
1,1!-Iminobis-4-nitroanthraquinone
N-Isopropylaniline
Isoviolanthrone
Leuco-154-diaminoanthraquinone
Leuco quinizarin
1-(Methyl ami no) anthraquinone
N-Methyl aniline
2-Methy 1anthraquinone
£-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
3-Methy]-l-phenyl-2-pyrazolin-5-one
2-Naphthalenesulfonic acid, sodium salt
2-Naphthol
(2-Naphthylthio) acetic acid
1-Nitroanthraquinone
Nitrobenzene
jn-Nitrobenzenesulfonic acid, potassium salt
jI-Nitrosodiphenylamine
5-Nitro~o~to1uenesulfonic acid
l-[(7-Oxo-7H-benz [de] anthracen-3-yl) amino] anthraquinone
256.
-------
TABLE D-4. (Continued)
3-Oxy--4-methy]-6-chlorothionaphthalene
j>(Phenylazo) aniline
£-(Phenylazo) aniline hydrochloride
N,N'-p-Phenylenebis (acetamide)
3-Pi peridinopropiophenone hydrochloride
Quinizarin
Sulfanilic acid
Tetrahydroxysuccinic acid
1,1'-Thiobis (2-naphthol)
4,4'-Thiodiani1ine
Thiosemicarbazide
Toluene-2,4'diamine
j>Toluenesulfonic acid
o-Toluidine hydrochloride
£-(_£-To!uoyl) benzoic acid
4-(.o_-Tolyazo)~.o,-toluidine
Violanthrone
4-(2,5-Xylylazo)-jo-toluidine
Benzothiazole
2-Benzothiazolethiol, sodium salt
o-Benzoylbenzoic acid
r4,4'-Bi~7H-benz [de] anthracen)-7,7'-dione
3-Bromo-7H-benz (de) anthracen-7-one
1-Chioroanthraqui none
2-Chloroanthraquinone
Chloro-7H-benz (de) anthracen-7~one
p-Chlorobenzenesulfonamide
o-(2-Chlorobenzoyl) benzoic acid
T- Chi oro-2-meth.ylanthraqui none
1-Chioro-5-nitroanthraquinone
[(4-Chloro-o-tolyl) thio] acetic acid
jD-Cresol
4,4'-Diamino-2s2'~biphenyldisulfonic acid
4s4'-Diamino-3,3'-dimethyltriphenylmethane
4,4'-Diamino-2,2l-stilbenedisulfonic acid
4s5'-Dibenzamido-l,1'-iminodianthraquinone
1,5-Dibenzoylnaphthalene .
Dichlorobenzanthrone
3-(Di ethyl ami no) propi ophenone
N,N-Diethy]aniline
9,10-Dihydro~9»10~dioxo-l-anthracenesulfonic acid, sodium salt
16,17-Dihydroxyvi olanthrone
N,N-Dimethy1aniline
2,2'-Dimethyl-l,1'-bianthraquinone
N,N-Dimethyl~p-nitrosoani 1 ine
4,4'-Dirritrosti1bene-2,2'-disulfonic acid
Diphenylamine
257
-------
TABLE D-4. (Continued)
1,3-Dipheny1-2~thiourea
2,5-Dithiobiurea
Acid dyes
Azoic coupling components
Basic dyes
Direct dyes
Disperse dyes
Mordant dyes
Oxidation bases
Solvent dyes
Sulfur dyes
Vat dyes
N-Ethylaniline
jj-Ethyl phenol
N-(Hydroxymethyl) phthalamide
3-Hydroxy-2,7-naphthalenedisulfonic acid, disodium salt
7-Hydroxy-l,3-naphthalenedisulfonic acid, disodium salt
6-Hydroxy-2-naphtha1enesulfonic acid, sodium salt
N-(2-Hydroxy-1-naphthyl) acetami de
Hydroxynitroviolanthrone
2-Hydroxy-4-sulfo-l-naphthalenediazonium hydroxide, inner salt
1,1'-Iminobis (4-aminoanthraquinone)
1,1'-Iminobis (4-benzamidoanthraquinone)
1,1'-Iminobis-4-nitroanthraquinone
N-Isopropylani1i ne
Isoviolanthrone
Leuco-1,4-diaminoanthraquinone
Leuco quinizarin
l-(Methylamino) anthraquinone
N-Methylaniline
2-Methy!anthraquinone
N,N'-Methylenebi sacryl ami de
£-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
3-Methyl-1-phenyl-2-pyrazoli n-5-one
2-Naphthalenesulfonic acid, sodium salt
2-Naphthol
(2-Naphthylthio) acetic acid
1-Nitroanthraquinone
Nitrobenzene
m-Nitrobenzenesolfonic acid, potassium salt
£-Ni trosodi phenylyami ne
5-Nitro-o.-to1uenesulfonic acid
l-[(7-Oxo-7H-benz [de] anthracen-3-yl) amino] anthraquinone
258
-------
TABLE D-4. (Continued)
3-Oxy-4-methyl-6-chlorothionaphthal ene
jl-(Phenylazo) aniline
p_-(Phenylazo) aniline hydrochloride
N,N'-.EL-Phenylenebis (acetamide)
3-Piperidinopropiophenone hydrochloride
Quinizarin
Sulfanilic acid
Tetrahydroxysuccim'c acid
1 ,l'-Thiobis (2-naphthol)
4s4'-Thiodiani1ine
Thiosemicarbazide
Toluene--2,4-diamine
2-Toluenesulfonic acid
o-Toluidine hydrochloride
o-(£-Toluoyl) benzoic acid
4-(o.-Tolyazo)-o-toluidine
Viol enthrone
4-(2,5-Xylylazo)-o-toluidine
Damascus, Virginia 24236
Dyes
Mordant dyes
Solvent dyes
Sulfur dyes
3-Methoxypropioni tri1e
p-Nitrosophenol
Marietta, Ohio 45750
P.O. Box 388
o-Anisic acid
3,7-Diaminodibenzothiophenedisulfonic acid, 5,5-dioxide, disodium salt
§7(Diethyl ami no) phenol
2,2' - Di hydroxy-4-rnethoxybenzophenone
m-Dimethoxybenzene
2,4-Dimethoxybenzoic acid
m-(Dimethyl ami no) phenol
Dyes
Acid dyes
Basic dyes
Direct dyes
Fluorescent brightening agents
Solvent dyes
o-(2-Hydroxy-p-anisoyl) benzoic acid
2-Hydroxy-4-methoxybenzophenone
2-HydrQxy-4-methoxy-2'-carboxybenzophenone
259
-------
TABLE D-4. (Continued)
2-Hydroxy-4-methoxy-2'-methylbenzophenone
2-Hydroxy-4-methoxy-5-sulfobenzophenone trihydrate
2-Hydroxy-4-octyloxobenzophenone
Metanilic acid
3-Methylbenzo (f) quinoline
2-Methylbenzo (h) quinoline
4,4'-Methylenebis (N,N-diethyl aniline)
4,4'-Methylenebis (N,N-dimethylaniline)
5~Nitro-o-anisidine
2-Nitrodiphenylamine
Quinaldine
Willow Island, West Virginia 26196
Aniline
Dyes
Fluorescent brightening agents
o_-Ethoxybenzoic acid
Nitrobenzene
Optical brighteners
6-Hydroxy-2-naphthalenesu1fonic acid, sodium salt
3-Hydroxy-2-naphthoic acid
R salt
2-Naphthol
Pigments Division
Bound Brook, New Jersey 08805
Carbazole violet
Dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
Willow Island, West Virginia 26190
Dyes
Toners and lakes
A new 3-hydroxy-2-naphthoic acid plant is under construction,
260
-------
TABLE D-5. AMERICAN HOECHST CORPORATION
(Owned by Farbwerke Hoechst of West Germany)
Route 202-206 North
Somerville, New Jersey 08876
See also: Sou-Tex Chemical Company, Inc., owned with
Casella Farbwerke Mainkur of West Germany
Dyes and Pigments Division
P.O. Box 268
Coventry, Rhode Island 02816
Acetoacetanilide
Acetoaceto-o_-anisidide
Acetoacet-o-chlorani1i de
Acetoacet-o_-to1uidide
Acetoacet-m-xylidide
f-(4-Amino-2,5-dimethoxyphenylsulfonyl) ethyl Sulfate
-Amino-4-methoxyphenyl -hydroxyethyl sulfone
3-Aminophenyl- -hydroxyethyl sulfone
4-Aminophenyl- -hydroxyethyl sulfone
4,4'-Bisacetoacet-o-toluidide
Carbazole violet
1,5-Dibenzoylnaphthalene
2,5-Dichloro-4-(3-methy1-5-oxo-2-pyrazolin-1-yl) benzenesulfonic acid
4-(N,N-Diethylamino) benzenediazonium zinc chloride
{D-Dimethylaminobenzenediazonium chloride-zinc chloride
Disodium 2,7-dihydroxynaphthalene-3,6-disu1fonate
Acid dyes
Azoic dyes and components
Disperse dyes
Fiber-reactive dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
Vat dyes
N,N'-Ethylene-bis-acetoacetamide
"I-Cfir (^-Hydroxyethyl sulfonyl) phenyl]-3-methy1-5~pyra2tolOne
1,4,5,8-Naphthalenetetracarboxylic acid
l-Phenyl-3-carbethoxy-5-pyrazolone
Sodium N,N-dimethylsulfanilate
l-(j3-Sulfophenyl)-3-carboxy-5-pyrazolone
£-Tolyl-3-methyl-5-pyrazolone
Products N.E.C.
1 -Butyl -3-j3-tolyl sul fonyl urea
261
-------
TABLE D-5. (Continued)
4-(N-Ethyl-N-benzylamino) benzenediazonium semizinc chloride
4-(N-Ethyl-N-[2-hydroxyethyl]amino) benzenediazonium semizinc chloride
4-(N-Methyl-N-[2-hydroxyethyl]amino) benzenediazonium semizinc chloride
4-(N-Morpholyl)-2,5-diethoxybenzenediazonium semizinc chloride
4-(N-Morpholyl)-2,5-dimethoxybenzenediazonium zinc chloride
262
-------
TABLE D-6. APOLLO COLORS* INC.
899 Skokie
Northbrook, Illinois 60062
Pigments
263
-------
TABLE D-7. ATLANTIC CHEMICAL INDUSTRIES, INC.
10 King!and Road
P.O. Box 216
Nutley, New Jersey 07110
Atlantic Chemical Corporation, subsidiary
Nutley, New Jersey 07110
8-Amino-2-naphthol
j)-[(jD-Aminophenyl) azo] benzenesulfonic acid
2-(j^-Aminophenyl)-6-methyl-7-benzothiazolesulfonic acid and salt
16-Ami novi olenthrone
Anilinomethanesulfonic acid
Anilinomethanesulfonic acid, sodium salt
o-Anisidinomethanesulfonic acid
7H-Benz (de) anthracen-7-one
m-Chloroaniline hydrochloride
5"'-Chloro-3-hydroxy-2-naphtho-o,-toluidide
N-[(5-Chloro-2-methoxyphenyl) azo] sarcosine
5-Chloro-o-toluidine ^hydrochloride
N-[(5-Chloro-CL-tolyir azo] sarcosine
1,4-Diaminoanthraquinone
4,4'-Diamino-2,2'-biphenyldisulfonic acid
Dibenzo [b,def] chrysene-7,14-dione
Dioxy R salt
1,4-Di-j>.-toluidinoanthraquinone
Acid dyes
Azoic coupling components
Azoic diazo components
Azoic dyes and components
Basic dyes
Direct dyes
Disperse dyes
Mordant dyes
Solvent dyes
Vat dyes
3-Hydroxy-2,7-naphthalenedisulfonic acid
4-Hydroxy-l-naphthalenesulfonic acid
3-Hydroxy-2-naphthanilide
3-Hydroxy-2-naphth~o-anisidide
3-Hydroxy-2-naphtho-o-phenetidide
3-Hydroxy-2-naphtho-o-toluidide
Leuco-1,4-diaminoanthraquinone
4-Methoxymetanilic acid
264
-------
TABLE D-7.(Continued)
16- Ni trovi ol an throne
Primulinesulfonic acid
2,2'-Tolidinedisulfonic acid
jl-Toluenesulfonic acid, ethyl ester
7,7'-Ureylenebis (4-hydroxy-2-naphtha1enesulfonic acid)
Violanthrone
2,4-Xylidine acetate
General and Compounded Products
Pyrotechnic dyes
265
-------
TABLE D-8. BASF WYANDOTTE CORPORATION
(Merger of BASF Corporation and Wyandotte Chemicals
Corporation)
100 Cherry Hill Road
Parsipanny, New Jersey 07054
Colors and Chemicals Group
100 Cherry Hill Road
Parsipanny, New Jersey 07054
4330 Chesapeake Drive
Charlotte, North Carolina 28208
Dyes
[Phthalocyaninato (2-)] copper
Pigments
Kearny, New Jersey
Dyes
About 15 various colors
-------
TABLE D-9. BENZENOID ORGANICS, INC.
P.O. Box 156, Route 140
Bellingham, Massachusetts 02019
Dyes
Acid dyes
Direct dyes
Mordant dyes
Vat dyes
General and Compounded Products
Cyclic intermediates
267
-------
TABLE D-10. BERNCOLORS-POUGHKEEPSIE, INC,
75 North Water Street
P.O. Box 29
Poughkeepsie, New York 12602
Dyes
Acid dyes
Basic dyes
Direct dyes
Mordant dyes
268
-------
TABLE D-ll. BORDEN, INCORPORATED
50 West Broad Street
Columbus, Ohio 43215
*
Levey Division
630 Glendale-Mil ford Road
Cincinnati, Ohio 45215
Dyes
[Phthalocyaninato (2-)] copper
*Levey Division was recently purchased by Borden from Cities Service
Company, Inc., and combined with Graphic Arts Products. (Personal
communication from Borden spokesman, 3/15/75.)
269
-------
TABLE D-12. CHEMETRON CORPORATION
111 East Wacker Drive
Chicago, Illinois 60601
Pigments Division
491 Columbia Avenue
Holland, Michigan 49423
471 Howard Avenue
Holland, Michigan 49423
6-Amino-4-chloro-m-toluenesulfonic acid
2-Amino-5-chloro-p-toluenesulfonic acid
6-Amino-m-toluenesulfonic acid
Carbazole violet
Basic dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
General and Compounded Products
Dispersions for plastics (chip, paste, crumb, and powder)
Flushed pigments
Organic pigment toners
5th Avenue and 24th Street
P.O. Box 2166
Huntington, West Virginia 25722
. 2-Amino-5-chloro-jD-toluenesulfonic acid
2-Amino-l-naphthalenesulfonic acid
Carbazole violet
2-Ch1oro-4-nitroani1ine
Acid dyes
Basic dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
General and Compounded Products
Flushed pigments
Organic pigment toners
270
-------
TABLE D-13. CHILDS PULP COLORS, INC.
5 Albany Street
P.O. Box 3217
Springfield, Massachusetts 01101
Acid dyes
Toners and lakes
271
-------
TABLE D-14-. CIBA-GEIGY CORPORATION
(Owned by CIBA-Geigy Ltd., Basle, Switzerland)
Saw Mill River Road
Ardsley, New York 10502
See also: Toms River Chemical Corporation, owned by
Ciba-Geigy Corporation, 80%, and Sandoz Ltd., 20%
Dyestuffs and Chemicals Division
Greensboro, North Carolina 27400
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
Fluorescent brightening agents
Vat dyes
General and Compounded Products
Pigments, printing, and binders
Industrial Chemicals Division
Mclntosh, Alabama 36553 (bulk chemicals)
4,4'-Diamino~2,2'-stilbenedisulfonic acid
4,4'-Dinitrosti1bene-2,2'-disulfonic acid
Di-n-octadecyl (3,5-di-tert-butyl-4-hydroxybenzyl)
phosphonate
Dyes
Fluorescent brightening agents
Solvent dyes
Toners and lakes
Pentaerythritol tetrakis (3,5-di-tert-butyl-4-hydroxyhydrocinnamate)
Sarcosine
Surface-active agents
N-(Coconut oil acyl) sarcosine
Fatty acid-diethanolamine condensates
Capric acid-diethanolamine condensate
Coconut oil acid-diethanolamine condensate
Oleic acid-diethanolamine condensate
Stearic acid-diethanolamine condensate
Imidazoline derivatives
2-(8-Heptadecenyl)-l-(2-hydroxyethyl)-2-imidazoline
2-Heptadecyl-l-(2-hydroxyethyl)-2-imidazoline
1 -(2~Hydroxyethyl)-2-tridecy1 -2-imidazoli ne hydrochloride
l-(2-Hydroxyethyl)-2-undecyl-2-imidazoline
272
-------
TABLE D-14. (Continued)
N-Lauroyl sarcosine
N-Lauroyl sarcosine, sodium salt
Naphthalenesulfonic acids and salts
Butylnaphthalenesulfonic acid, sodium salt
N-Oleoylsarcosine and sodium salt
Polyethylene glycol dioleate
Polyethylene glycol monolaurate
Polyethylene glycol mono-oleate
Polyethylene glycol monostearate
Polyethylene glycol sesquiester of castor oil acids
N-Stearoylsarcosine, sodium salt
Sulfosuccinic acid, bis (2-ethylhexyl) ester, sodium salt
Triallyl cyanurate
General and compounded products
Absorbers, ultraviolet
(Tinuvin©P, 327, 320, 326, 328)
Antimicrobial agent for deodorant soaps and anti-bacterial products
(Irgason® DP300)
273
-------
TABLE D-15. CINCINNATI MILACRON INC.
4701 Marburg Avenue
Cincinnati, Ohio 45209
Cincinnati Milacron Chemicals Inc., subsidiary
West Street
Cincinnati, Ohio 45215
Dyes
Fluorescent brightening agents
1 i ferone
274
-------
TABLE D-16. CROMPTON & KNOWLES CORPORATION
345 Park Avenue
New York, New York 10022
Chemicals Group
Route 208,
Fair Lawn, New Jersey 07410
Gibraltar, Pennsylvania 19524
Dyes
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
Food, drug and cosmetic colors
Toners and lakes
Reading, Pennsylvania 19603
Dyes
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
275
-------
TABLE D-17. DAY-GLO COLOR CORPORATION*
(Formerly Switzer Brothers, Inc.)
4732 St. Clair Avenue
Cleveland, Ohio 44103
Dyes
Fluorescent brightening agents
General and compounded products
Fluorescent pigments
9314 East Fern Street
South El Monte, California 91733
Dyes
Fluorescent brightening agents
General and compounded products
Fluorescent pigments
* Not listed by Synthetic Organic Chemicals in either
1972 or 1973.
276
-------
TABLE D-18. E.I. DU PONT DE NEMOURS & COMPANY, INC.
1007 Market Street
Wilmington, Delaware 19898
Organic Chemicals Department
Dyes and Chemicals Division
Wilmington, Delaware 19898
Deepwater, New Jersey 08023
2-Amino-jD-benzenedisul fonic acid
4-Amino-l-naphthalenesulfonic acid, sodium salt
2-(p-Ami nophenyl)-6-methylbenzothi azol e
2-Amino-3,5-xylenesulfonic acid
8-Anilino-l-naphthalenesulfonic acid, sodium salt
o-Anisidine
2.-Anisidine
Anthranilic acid
7H-Benz (de) anthracen-7-one
N-Benzyl-N-ethyl-m-toluidine *
N,N-Bis (cyanoethyl) aniline
4,4'-Bis (diethylamino) benzophenone
4,4'-Bis (dimethyl ami no) benzophenone
p-Butylaniline
2-tert-Butylanthraqui none
m_-Chloroaniline
o-Chloroaniline
£-Chloroaniline
2-Chloro-N,N-diethyl-4-nitroaniline
4-Chlorometanilic acid
2-Chloro-4-ni troani1i ne
4-Chloro-2-nitroaniline
1-Chioro-2-ni trobenzene
1-Chioro-4-ni trobenzene
4-Chloro-3-ni trobenzenesulfonami de
2-Chl oro-5-ni trobenzenesulfoni c acid
2-Chloro-4-nitrotoluene
2-Chloro-6-ni trotoluene
4-Chloro-2-nitrotoluene
6-Chloro-2-nitrotoluene
3- Ch 1 oro-_o- to! ui di ne
3-Chloro-j>-toluidine
5-Chloro-£-toluidine
2-Chloro-£-xylene
Decahydronaphthalene
2,4-Diaminobenzenesulfonic acid
2,5-Di chloroani1i ne
3,4-Dichloroaniline
277
-------
TABLE D-18. (Continued)
1 ,4-Dichloro-2-nitrobenzene
2-Diethylaminoethyl methacrylate
N,N-Diethy1aniline
N,N-D1 ethyl cyclohexyl ami ne
N, N-Di ethyl -m-tolui dine
N ,N- Dimethyl ani 1 i ne
2,4-Dinitro toluene
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
Fluorescent brightening agents
Mordant dyes
Solvent dyes
Toners and lakes
Vat dyes
3-(Ethylamino)-p-toluenesulfonic acid
N-Ethylanil ine
3-(N-Ethylanilino) propionitrile
2-Ethyl anthraqui none
Ethyl chloride
N-EthyI-1-naphthylamine
N-Ethyl -N- phenyl benzyl ami ne
N- Ethyl -rn- to! ui dine
N-Ethyl -£-tolui dine
3-(N-Ethyl-iTHtoluidino) propionitrile
N-Methyl ani line
S-(N-Methylanilino) propionitrile
4 ,4' -Methyl enebi s ( N ,N-dimethyl ani 1 i ne)
1-Naphthylamine
2- Ni tro-j>ani si di ne
4-Nitro-£~anisidine
oi-Nitroanisole
jp_-Nitroanisole
_£-Nitrobenzoic acid
£-Nitrophenol
m-Nitro toluene
jo-Nitro toluene
£-Nitroto1uene
Nitrotoluenes, mixed
5-Nitro-o-toluenesulfonic acid
5-Ni tro-o- tol ui di ne
4,4'-Oxydianil ine
jD-(Phenylazo) aniline hydrochloride
278
-------
TABLE D-18. (Continued)
enedi ami ne
p_- Phenyl enedi ami ne
Pi peri dine
Primuline base
Quinizarin
1,2,3,4-Tetrahydronaphthalene
Toluene-2,4-diamine
m_-Toluidine
o-To!uidine
_p_-Toluidine
To!uidines, mixed
4-(o-Tolyazo)-
-------
TABLE D-19. DYE SPECIALTIES, INC.
26 Journal Square
Jersey City, New Jersey 07306
4,4'-Bis (dimethyl ami no) benzophenone
N,N-Diethyl aniline
N,N-Dimethylani1i ne
Dyes
Basic dyes
Solvent dyes
Triphenyl methane dyes
280
-------
TABLE D-20. EASTMAN KODAK COMPANY
343 State Street
Rochester, New York 14650
Eastman Chemical Products, Inc., subsidiary
P.O. Box 431
Kingsport, Tennessee 37662
Tennessee Eastman Company, division
P.O. Box 511
Kingsport, Tennessee 37662
Acetanilide
Acetic acid
Acetic anhydride
p-Benzoquinone
Diketene
2^5-Dimethoxyaniline
£-Dimethoxybenzene
Dimethyl-1,4-cyclohexanedicarboxylate
1,8-Diphenoxyanthraquinone
Dyes
*
Disperse dyes
2-(N-Ethylanilino) ethanol
Hydroquinone
N-Isopropylaniline
jD-Methoxyphenol
Methyl acetoacetate
j3-Tol uhydroqui none
m_-Tolyldiethanol ami ne
General and compounded products
Cationic dyes
A new multimillion-dollar plant is under construction which will
increase capacity for disperse dyes by one-third; completion
was scheduled for early 1974.
281
-------
TABLE D-21 . FABRICOLOR INCORPORATED
24-1/2 Van Houten Street
Paterson, New Jersey 07505
Acid dyes
Basic dyes
Direct dyes
Disperse dyes
282
-------
TABLE D-22 . FOSTER-HEATON COMPANY*
16 East Fifth Street
Paterson, New Jersey 07524
Dyes
Solvent dyes
*
Not listed by Synthetic Organic Chemicals in either 1972 Or 1973
edition.
283
-------
TABLE D-23. GAP CORPORATION
140 West 51st Street
New York, New York 10020
Chemical Division
P.O. Box 337
Calvert City, Kentucky 42029
Carbazole violet
Dimethyl amine
Methyl amine, mono
P.O. Box 12
Linden, New Jersey 07036
Alkylphenols, mixed
1-Aminoanthraquinone and salt
2-Aminoanthraquinone and salt
N-(4-Amino-l-anthraquinonyl) anthranilic acids
l-Amino-5-benzamidoanthraquinone
4'-Ami nobenzani1i de
2-(m~Aminobenzoyl)-o_-acetanisidide
1 -Ami no-2-bromo-4-j3- to 1 ui di noanthraqui none
2-Ami no-3-chloroanthraqui none
o-(3-Amino-4-chlorobenzyl) benzoic acid
1-Amino-2,4~dibromoanthraquinone
l-Amino-9,10-dihydro-9',10-dioxo-2-anthracene-sulfonic acid
1-Ami no-9,10-dihydro-9,10-dioxo-4-p-toluenesul fonamido 2-anthracenesulfonic
acid, sodium salt
1-Ami no-4-hydroxyanthraqui none
2-Amino-3-hydroxyanthraquinone
5-Aminoisophthalic acid
N-(4-Ami no-3-methoxy-l-anthraquinonyl)-p-toluenesulfonamide
4'-Ami no~N-methylacetani1i de
6~Aminonaphth [2,3-c] acridan-5,8,14-trione
5- (and 8).-Amino-2-naphthol
2-(4-Amino-l-naphthylazo)-4-(l,1,3,3-tetramethyl) phenol
2-Ami no-5-nitrobenzenesulfonic acid
2-(p-Aminophenoxy) ethanol hydrochloride
p-Aminophenyl benzyl ether
N-(4~Amino-3-sulfoanthraquinonyl) anthranilic acid
2-Amino-4-(l ,1,3.,3-tetramethylbutyl) phenol
2-Ami no-4-(l,1,3,3-tetramethylbutyl) phenol hydrochloride
4-Amino-j]>- tol uenesul f oni c acid
16-Ami novi olanthrone
Anthraflavic acid
Anthraquinone
N,N'-(1,5-Anthraquinonyl-ene) di anthranilic acid
284
-------
TABLE D-23. (Continued)
N,N'-(1,5-Anthraquinonylene) dioxamic acid
Anthrarufin
4',4'''-Azobis (4-biphenylcarboxylic acid)
]-Benzamido-4-chloroanthraqui none
l-Benzamido-5-chloroanthraquinone
7H-Benz (de) anthracen-7-one
Benzenesulfinic acid, sodium salt
Benzyl p-nitrophenyl ether
3,3'-Bianthra (1 ,9-cd) pyrazole-6,61(2H,2'H)-dione
(4,4'-Bi-7H-benz [de] anthracen)-7,7'-dione
1,4-Bis-(l-anthraquinonylamino) anthraquinone
Bis (1-anthraquinonylamino) violanthrene
3-Bromo-7H-benz (de) anthracen-7-one
1-Bromo-4-(N-methylacetamido) anthraquinone
1-Bromo-4-methylami noanthraqui none
5'-(o.-Carboxybenzoyl )-2'-chloro-oxani lie acid
H- Chioroaniline
1-Chioroanthraquinone
2-Chloroanthraquinone
4-(j>Chlorobenzamido) anthraquinone-1,2-acridone
Chloro-7H-benz (de) anthracen-7-one
£-Chlorobenzenesulfom'c acid
4-Chloro-3,5-dinitrobenzoic acid
1-Chioro-2-methylanthraqui none
l-Chloro-3-nitrobenzene
£.-(4-Chloro-3-nitrobenzoyl) benzoic acid
Chromium formate
Chrysazin
1,4-Diaminoanthraquinone
1,5-Diaminoanthraquinone
2,6-Di ami noanthraqui none
1,4-Diamino-5-nitroanthraquinone
2,4-Dianilino-l-hydroxyanthraquinone
1,5-Dibenzamidoanthraquinone
4,5'-Dibenzamido-l,1'-iminodianthraquinone
3,9-Dibromo-7H-benz (de) anthracen-7-one
2,3-Dibromo-2-butene-l ,4-diol
Dibromoviolanthrone
2,6-Di-tert-butyl-4-nonylphenol
1,5-Dichloroanthraquinone
1,8-Dichloroanthraquinone
2,5-Dichlorobenzoyl chloride
2,5-Dichloro-3-nitrobenzoate, ammonium salt
2,5-Dichloro-3-nitrobenzoic acid
2,5-Dichloro-3-nitrobenzoic acid, ammonium salt
2,5-Dichloro-3-nitrobenzoic acid, iminodi-2,2'-ethanol salt
2-(2,4-Dichlorophenoxy) ethanol
2',5'-Diethoxybenzanilide
£.-Diethoxybenzene
2,5-Diethoxy-4-morpholinobenzenediazonium-.p_-chlorobenzenesulfonate
285
-------
TABLE D-23. (Continued)
j>-Diethyl aminobenzenediazoniurn chloride-zinc chloride
7-Di ethyl ami no-4-methylcoumari n
9,IO-Dihydro-9,10-dioxo-l,5-anthracenedisulfonic acid, disodium salt
9,10~Dihydro-9,10-dioxo-l,8-anthracenedisulfonic acid, potassium salt
9JO~Dihydro-9,lQ~dioxo-2,6-anthracenedisulfonic acid
9,10-Dihydro-9,10-dioxo-2,6-anthracenedisulfonic acid, sodium salt
9,10-Dihydro-9,10-dioxo-l-anthracenesulfonic acid
9,10-Dihydro-9,10-dioxo-l-anthracenesulfonic acid, sodium salt
9,10-Dihydro-l-nitro-9,10-dioxo-2-anthroic acid
1,4-Dihydroxy-2-butanone
1,8-Dihydroxy-4,5-dinitroanthraquinone
6,7-Dihydroxy-2-naphthalenesulfonic acid
3,5-Dihydroxy-2--naphthoic acid
16,17-Dihydroxyviolanthrone
16,17-Dimethoxyviolanthrone
2,2'-Dimethyl-1,1'-bianthraquinone
N,N-Dimethylsulfanilic acid
1,4-Di-p-toluidinoanthraquinone
Disperse dyes
[Phthalocyaninato (2-)] copper
Solvent dyes
Toners and lakes
Vat dyes
Q-Formylbenzenesulfonic acid
4'-(2-Hydroxyethoxy) acetani1ide
N-Hydroxymethylacrylami de terpolymer
3~Hydroxy-2-methylcinchoninic acid
3-Hydroxy-2,7-naphthalenedisulfonic acid, disodium salt
],1 '-Iminobis (4-aminoanthraquinone)
1,1'-Iminobis (5-benzamidoanthraquinone)
1,1'-Iminodianthraquinone
Isethionic acid
Isoviolanthrone
Leuco-134-diaminoanthraquinone
Leuco tetrahydroxyanthraquinone
1-Methoxyanthraquinone
l-(Methylamino) anthraquinone
l-(Methylamino)-4-p-toluidinoanthraquinone
N-Methyl-4'-ni troacetani1ide
N-Methyl-p-nitroani1i ne
2-Methyl-1-ni troanthraqui none
N-Methyltaurine
3-Methyl-6--(p-toluidino)-7H-dibenz (f,ij) isoquinoline-2,7 (3H)-dione
1,3,6-Naphthalenetrisulfonic acid
Naphthalimide
2-(4-Nitro-2-anthraquinonyl) anthra (2,3-d)-oxazole-5,10-dione
286
-------
TABLE D-23 . (Continued)
m-Nitrobenzenesulfonic acid, sodium salt
2-(m-Nitrobenzoyl)-o-acetanisidide
5-Nitroisophthalic acid
3-Nitro-1,5-naphthalenedisulfonic acid
4-Nitronaphthalic anhydride
4'-(jD-Nitrophenyl) acetophenone
2-(£-Nitropheny1)-l-octadecyl-5-benzimidazolesulfonic acid
5-Nitro-o-toluenesulfonanilide
5-Nitro-£-toluenesulfonyl chloride
16-Nitroviolanthrone
l-[(7-Oxo-7H-benz [de] anthracen-3-yl) amino] anthraquinone
1 ,T-[(7-Oxo-7H-benz [de] anthracen-3,9-ylene) diimino] dianthraquinone
3,4,9,10-Perylenetetracarboxyli c aci d
3,4,9,10-Perylenetetracarboxylic 3,4:9,10-diimide
• 4'-Phenylacetophenone
2-Phenylanthra [2,3-d] oxazole-5,10-dione
2,2'-([Phenyl] imino) diethanol
[Phthalocyaninato (2-)] aluminum
[Phthalocyaninato (2-1)] cobalt
Polybromochloro [phthalocyaninato (2-)] copper
Quinizarin
Sarcosine
Sodium m-nitrobenzenesulfonate
Tetrabromo-8,16-pyranthrenedione
1,3,6,8-Tetrabromopyrene
1,4,5,8-Tetrachloroanthraquinone
Tetrachloroviolanthrone
1,4,5,8-Tetrakis (1',1'',1 " ',T '''-anthraquinonylamino) anthraquinone
3,3'-Thiobis [7H-benz (de) anthracen-7-one]
p-Toluenesulfonic acid, 2-chloroethyl ester
N^ ,N^,N^-Tri chloromelami ne
1,2,4-Trihydroxyanthraquinone
Products N.E.C.
4-(4-Pyrrolidinyl-m-tolylazo) benzenesulfonic acid
15 Market Street
Paterson, New Jersey 07501
Carbazole violet
Dyes
Toners and lakes
Riverside Avenue
Rensselaer, New York 12144
5-Acetamido-2-aminobenzenesulfonic acid
j)-Acetanisidide
3'-Ami noacetani1i de
4'-Aminoacetanilide
287
-------
TABLE D-23. (Continued)
5-Amino-2-(j3-aminoanilino) benzenesulfonic acid
7-(j>Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
2-Amino-jj-benzenedisul foni c aci d
jD-Aminobenzoic acid, butyl ester
1-Amino-2-bromo~4-hydroxyanthraquinone
2-Amino-4-chlorophenol
4'-Amino-21,5'-diethoxybenzanilide
p-Amino-N-ethyl-N-1-naphthylbenzamide
2-Amino-N-ethy1-5-nitrobenzenesulfonanilide
4-Ami no~3-hydroxy~1-naphthalenesulfoni c aci d
3-Amino-l,5-naphthalenedisulfonic acid
7-Amino-l,3-naphthaVenedisulfonic acid
5-Amino-2-naphthalenesulfonic acid
8-Ami no-2-naphthol
2-Ami no-4-ni trophenol
2-Amino-5-nitrophenol
4-Amino-4'-nitro-2,2l-sti1benedisulfonic acid
£>-[(£-Ami nophenyl) azo] benzenesulfonic acid
5-Ami no~o-toluenesulfonani1i de
7-Anilino~4-hydroxy-2-naphthalenesulfonic acid
nv-Anilinophenol
3-Ani1i nopropi oni tri1e
o-Anisidinomethanesulfonic acid
Anthra [1,9-cd] Pyrazol-6 (2H)-one
(1-Anthraquinonyl)-l ,2-hydrazinedisulfonic acid, disodium salt
l-(4-Benzamido-255-diethoxyphenyl)-3-[methyl-3-(2-sulfoethyl) triazene]
N-(4-Benzamido-6-methoxy-m-tolyl)-N-(methylazo) glycol
Benzo (b) thiophen-3 (2H) one
£-Benzoylbenzoic acid
N9N'~Bis (l-chloro-2-anthraquinonyl)-4',4'''-azobis-4-biphenylcarboxamide
4,4'-Bis (diethylamino) benzhydrol
4,4'-Bis (diethylamino) benzhydrol, 2,6-naphthalenesulfonate
3'-[Bis (2-hydroxyethyl) ami no] acetanilide
2-Bromo~4'-nitroacetophenone
Carbazole violet
N,N'-Carbonylbis (4-methoxymetanilic acid)
N5N'-Carbonylbis (4-methoxy-6-nitrometanilic acid)
3-Carboxy-2 (and 4)-hydroxybenzenediazonium sulfate
o-[(Carboxymethyl) thio] benzoic acid
3-(2-Carboxy-4-sulfophenyl)-3-ethyl-l-(5-nitro-£-anisyl) triazine
4-Chloro-o-anisidine hydrochloride
£-(0-Chlorobenzoyl) benzoic acid
288
-------
TABLE D-23. (Continued)
4,4'-(£-Chlorobenzylidene) di-2,5-xy1idine
2-Chlo?o-l,4-di ethoxy-5-ni trobenzene
5-Chloro-2,4-dimethoxyaniline
4-Chloro-N,N-dimethyl-3-nitrobenzenesul fonamide
2-Chloro-4,6-di ni troani 1 i ne
N-(2-Chloroethyl)-4-(2-chloro-4-nitrophenylazo)-N-ethylaniline
[4-(2-Chloroethyl) ethyl ami no] o-tolualdehyde
N-(2-Chloroethyl)-N-ethylani1i ne
j3-[(2-Chloroethyl) methylamino] benzaldehyde
4-Chloro-3-hydrazinobenzenesulfonic acid
4-Chloro-5-hydroxy-2,7-naphthalene disulfonic acid
4-Chlorometanilie acid
6-Chlorometani1ic acid
5-Chloro-2-methoxybenzenediazoniurn chlori de
4-Chloro-3-{3-methyl-5-oxo-2-pyrazolin-l-y1) benzenesulfonic acid
4-Chloro-3-nitrobenzenesulfonamide
4-Chloro-3-nitrobenzenesulfonic acid
4-Chlororesorcinol
l-(5-Chloro-j)-tolyl)-l-tetrazene
[(4-Chloro-Oj-tolyl) thio] acetic acid
4-Chl oro-t*, «><,«<-tri f 1 uoro-3-ni trotol uene
4-([2-Cyanoethyl] ethyl ami no)-o-to!ualdehyde
j>([2-Cyanoethyl] methylamino) benzaldehyde
4-Decyloxy-2-hydroxybenzophenone
4,4'-Diamino-2J2'-stilbenedisulfonic acid
3,5-Diamino-j>toluenesulfonic acid
1,5-Dibenzoylnaphthalene
2,5-Dichloro-4-hydrazinobenzenesulfonic acid
2,5-Dichloro-4-(3-methyl-5-oxo-2-pyrazoli n-1-yl) benzenesulfoni c aci d
2,6-Dichloro-4-nitroaniline
N-[(2,5-Dichlorophenyl)azo]-N-ethyl-5-sulfoanthranilic acid
1 - (2,5- Di chlorophenyl)-3-tri azi necarboni tri1e
2,6-Dichlorotoluene
£-(Diethyl ami no) benzaldehyde
N, N-Di ethyl-j3-ni trosoani 1 i ne
N,N-Di ethyl -4- nitroso~rn-pheneti dine
N, N-Di ethyl-m-pheneti di ne
4-(2,3-Dihydro-3-oxobenzo [b] thiophen-2-yl-methyl idene)-m-benzenedisulfonic acid
jTh Di methoxybenzene
_£-Dimethyl aminobenzaldehyde
N,N-Dimethyl-3-nitro-£-toluenesulfonamide
N-([4-(Dimethylsulfamoyl)-_o_-tolyl] azo)-N-methyl-5-sulfoanthranilie acid
f-(2,4-Dinitroanilino) phenol
,4'-Dinitrostilbene-2,2'-disulfonic acid
3,5-Dinitro-_p_-tol uenesul fonic acid
1,5-Diphenoxyanthraquinone
289
-------
TABLE D-23. (Continued)
Acid dyes
Azoic coupling components
Azoic diazo components
Azoic dyes and components
Basic dyes
Direct dyes
Disperse dyes
Fluorescent brightening agents
Mordant dyes
[Phthalocyaninato (2-)] copper
Solvent dyes
Toners and lakes
ot-(N-Ethyl anil ino)-mr-toluenesulfonic acid
3-Ethyl-2-[3-(3-ethyl-2-benzothiazolinylidene) pentadienyl] benzothiazolium
iodide
2-Ethylhexyl cyanoacetate
3-(N-Ethyl-m-toluidino) propionitrile
4-Formyl-m-benzenedisuifonic acid
jD-Hydrazinobenzenesulfonic acid
4-Hydrazino-m-toluenesulfonic acid
2-Hydroxy-4-methoxybenzophenone
8-Hydroxy-l-naphthalenesulfonic acid
4-Hydroxy-2-naphthalenesulfonic acid, benzene sulfonate, sodium salt
N-(7-Hydroxy-l-naphthyl) acetamide
4-Hydroxy-7-(p_-nitrobenzamido)-2-naphthalene-$ulfonic acid
2-Hydroxy-4-octyloxobenzophenone
Metanilanilide
4-Methoxymetanilic acid
3-Methylbenzo (f) quinoline
4,4'-Methylenebis (N,N-diethylaniline)
4,4'-Methylenebis (N,N-dimethylaniline)
4,4'-Methylenebis (N,N-dimethyl-3-nitroanil-ine)
2-Methylindole-3-carboxyaldehyde
mr(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
j>(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
4-(3-Methyl-5-oxo-2-pyrazoli n-1-yl)-m-toluenesulfoni c aci d
1-Methyl-2-phenyli ndole
1-Methyl-2-pheny1i ndole-3-carboxaldehyde
N-Methyl-5-sulfoanthranilic acid
l-Naphthol-3-sulfonamide
Naphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
1-Naphthylamine hydrochloride
3'-Nitroacetanilide
4'-Nitroacetani1i de
3'-Ni tro-p-acetani si dide
4'-Nitrobenzani1i de
3'-Nitrobenzenesulfonanilide
ni-Nitrobenzenesulfonyl chloride
6-Nitro-2-benzoxazolinone
7- (and 8)-Nitronaphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
290
-------
TABLE D-23. (Continued)
3 (and 5)-Nitrosalicylic acid
4-Nitrostilbene
5-Nitro-£-toluenesulfonic acid
4'-Nitro-jD-tol uenesul fono-o-toluidide
4-Nitro-o-tol uidine
5-Oxo-l-T£-sulfopheny1)-2-pyrazoline-3-carboxylic acid
£-(Phenylazo) aniline hydrochloride
l-Phenyl-3-carbethoxy-5-pyrazolone
m-Phenylenedi ami ne
2,4-Quinolinediol
4-4"-Sulfonyldiphenol
2,2',4,4'-Tetrahydroxybenzophenone
2,2'-Thiobis (5-nitrobenzenesulfonic acid)
6,6'-Thiodimetanilic acid
Toluene-2,4-diamine
Toluene-2,4-disulfonic acid
p_-Tol uenesul fono-o_-tol uidide
N-^-Tolylazo) sarcosine
4-(o-Tolyazo)-o-toluidine
4-(o.-Tolylazo)-.g-toluidine hydrochloride
2,3,3-Trimethyl-3H-indole
1,3,3-Trimethyl-i ndoli neacetaldehyde
1,3,3-Trimethyl-2-methyleneindoline
7,7'-Ureylenebis (4-hydroxy-2-naphthalenesulfonic acid)
Violanthrone
4-(Xylylazo) xylidine, mixed
Products N.E.C.
Cationic dyes
291
-------
TABLE D-24. HERCULES INCORPORATED
910 Market Street
Wilmington, Delaware 19899
Coatings & Specialty Products Department
P.O. Box 231
Glens Falls, New York 12801
Dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
292
-------
TABLE D-25. PHILIP A. HUNT CHEMICAL CORPORATION
Roosevelt Place
Palisades Park, New Jersey 07650
Way!and Chemical Division
Industrial Circle, P.O. Box "0"
Lincoln, Rhode Island 02865
4-Methyl-1-phenyl-3-pyrazoli di none
1-Phenyl-3-pyrazoli di none
Industrial Dyestuff Company, subsidiary
Massasoit Avenue, P.O. Box 4249
East Providence, Rhode Island 02914
1-Ally1-3-(2-hydroxyethy1)-2-thiourea
2-(N-(2,4-Di-tert-amylphenoxyacetyl) amido)-4,6-
dichloro-5-methylphenol
£-Diazo-N,N-dimethylaniline-l-amino-8-naphthol-
3-sulfonate-6-sulfonic acid, sodium salt
2-Diethylaminobenzenediazonium chloride-zinc chloride
N,N-Diethyltoluene-2, 5-diamine, monohydrochloride
6,7-Dihydroxy-2-naphthalenesulfonic acid
-Dimethylaminobenzenediazonium chloride-zinc chloride
-(2',6'-Dimethylmorpholinyl) benzenediazonium
chloride-zinc chloride
j3-(Ethyl (2-hydroxyethyl) amino) benzenediazonium
chloride-zinc chloride
N-Ethyl-N-hydroxyethyl-£-phenylenediamine sulfate
N-B-Hydroxyethyl-2, 4-dihydroxybenzamide
j2.-C(2-Hydroxyethyl) methylamino) benzenediazonium
chloride-zinc chloride
3-Hydroxy-N-(2-hydroxyethyl)-2-naphthamide
3-Hydroxy-N-(3-N-morpholinopropyl)-2-naphthamide
j£-Hydroxypheny1 urea
N-Methyl-N-^-hydroxyethyl-£-phenylenediamine sulfate
Sodium formaldehyde bisulfite
293
-------
TABLE D-26. ICI UNITED STATES INC.
(Owned by Imperial Chemical Industries Limited)
(London, England)
Wilmington, Delaware 19899
Dyes & Textile Chemicals Division
New Murphy Road & Concord Pike
Wilmington, Delaware 19899
Dighton, Massachusetts 02715
333 Main Street
N,N-Dibenzylsulfanilic acid
Dyes
Acid dyes
Fiber-reactive dyes
Vat dyes
294
-------
TABLE D-27. INDOL CHEMICAL CO., INC.*
Leffert Street
Carteret, New Jersey 07008
(Phthalocyaninato (2-)) copper
Toners and Takes **
Products N.E.C.
Organic pigments, azo reds and violets
Organic pigments, benzidine yellows
Organic pigments, dianisidine blue and orange
Organic pigments, phthalocyanine blue and green
Organic pigments, thioindigo pigments
* Not listed by Synthetic Organic Chemicals in 1972 or 1973
** An expansion is under construction which will increase capacity
for azoic and phthalo dry pigments by 25%; completion of the 500-
thousand-dollar plant is scheduled for early 1974.
295
-------
TABLE D-28. INDUSTRIAL COLOR INC.*
Industry Avenue
Post Office Box 944
Joliet, Illinois 60434
Dyes
Toners and lakes
Pigments
Benzidine yellow
Red lake C
*Not listed by Synthetic Organic Chemicals in 1972 or 1973
296
-------
TABLE D-29 . INMONT CORPORATION
(Formerly Interchemical Corporation)
1133 Avenue of the Americas
New York, New York 10036
150 Wagaraw Road
Hawthorne, New Jersey 07506
2-Amino-j)-benzenedisulfonic acid
l-Amino-2-bromo-4-hydroxyanthraquinone
l-Amino-2, 4-dibromoanthraquinone
3-Ami no-4-methoxybenzami de
3-Ami no-4-methy 1 benzami de
4-Chloro-3-nitrobenzenesulfonamide
1,5 (and 1 ,8)-Dinitroanthraquinone
1,5 (and l,8)-Diphenoxyanthraquinone
Direct dyes
Disperse dyes
(Phthalocyaninato (2-)} copper
Toners and lakes
Eos in
Fluorescein
Hexadecachlorophthalocyanine
3-(N-(2-Hydroxyethyl ) anilino) propionitrile
4-Hydroxy-l -methyl carbostyri 1
3-Hydroxy-2-methy!cinchoninic acid
3-Hydroxy-4-(phenylazo)-2-naphthoic acid
4-Hydroxy-2-quinaldinic acid
Leuco-1, 4-diaminoanthraquinone
Leuco quinizarin
Leuco tetrahydroxyanthraquinone
N-Methylanthranilic acid
N-Methyl-4-hydroxyquino1one-2
6-Nitro-2-aminobenzothiazole
Quinizarin
297
-------
TABLE n-ao. KEWANEE OIL COMPANY
40 Morris Avenue
Bryn Mawr, Pennsylvania 19010
Harshaw Chemical Company, division
1945 East 97th Street
Cleveland, Ohio 44106
Pigment and Ceramic Department
3415 Bardstown Road
Louisville, Kentucky 40218
2-Chloroquinizarin
1,4-Diaminoanthraquinone
2,6-Dichloro-4-nitroaniline
Acid dyes
Direct dyes
Disperse dyes
Mordant dyes
(Phthalocyaninato (2-)} copper
Solvent dyes
Toners and lakes
Leuco-1, 4-diaminoanthraquinone
Leuco quinizarin
Quinizarin
2-Quinizarinsulfonic acid
General and Compounded Products
Alizarin dyes
Anthracene chrome dyes
Anthraquinone dyes
Diphenyl dyes
Inorganic pigments and dyes
Phthalocyanine dyes, blues and greens
Toluidine reds
Textile Color Department
P.O. Box 848
Lowell, North Caroline 28098
Acid dyes
Direct dyes
Disperse dyes
Mordant dyes
298
-------
TABLE D-31 . KEYSTONE COLOR WORKS, INC.
151 West Gay Avenue
York, Pennsylvania 17403
Dyes
Toners and lakes
299
-------
TABLE D-32. H. KOHNSTAMM & CO., INC.
161 Avenue of the Americas
New York, New York 10013
Lois and Lemuel Avenues
Camden, New Jersey 08105
Alumina, activated, calcined and hydrated
Aluminum hydroxide
6-Hydroxy-2-naphthalenesulfonic acid, sodium salt
Sulfanilic acid and salts
Pigments Division
537 Columbia Street
Brooklyn, New York 11231
Dyes
Food, drug and cosmetic colors
Toners and lakes
Lois and Lemuel Avenues
Camden, New Jersey 08105
Dyes
Toners and lakes
300
-------
TABLE D-33. C. LEVER COMPANY, INC,
736 Dunks Ferry Road
Cornwells Heights, Pennsylvania 19020
Philadelphia, Pennsylvania 19133
Dyes
Toners and lakes
301
-------
TABLE D-34. MAGRUDER COLOR COMPANY, INC.
One Virginia Street
Newark, New Jersey 07114
Dyes
[Phthalocyaninato (2-)] copper
Toners and lakes
302
-------
TABLE D-35. MARTIN MARIETTA CORPORATION
(Consolidation of American-Marietta and
The Martin Company)
277 Park Avenue
New York, New York 10017
Martin Marietta Chemicals
277 Park Avenue
New York, New York 10017
Sodyeco Division
P.O. Box 10098
Charlotte, North Carolina 28201
Sodyeco, North Carolina 28100
3-Amino-9-ethy1carbazole
o-Aminophenol
JD-Aminophenol
2-Bromo-6-chloro-4-nitroani1ine
2-Bromo-4,6-dinitroaniline
l-Chloro-2,4-dinitrobenzene
4-Chloro-l,3-phenylenediamine
2-Chloro-l, 3-phenylenediamine-5-sulfonic acid
2,2'-Diaminodiphenyl disulfide
4,4'-Diaminodiphenyldisulfide
2,6-Dibrorno-4-nitroaniline
Difurfurylidene pentaerythrito!
2,4-Dinitroaniline
2,4-Dinitrophenol
Disperse dyes
Sulfur dyes
Toners and lakes
Vat dyes
9-Ethylcarbazole
3-Nitro-9-ethylcarbazole
^.-Nitrophenol
m-Nitro-D-phenylenediamine
4-Nitro-T,2-phenylenediamine
4-Ni trophtha1imi de
£.-Nitrosophenol
jD-Phenhlenediamine
Picric acid
Sodium picramate
1,3,6,8-Tetranitrocarbazole
Products N.E.C.
Violet Pigment 23 Base (C.I. No. 51319)
303
-------
TABLE D-36. MAX MARX COLOR AND CHEMICAL COMPANY
192 Colt Street
Irvington, New Jersey 07111
Dyes
Azoic dyes and components
Toners and lakes
General and Compounded Products
Pyrazolone Intermediates
304
-------
TABLE D-37. OTTO B. MAY, INC.
(Owned 80% by Cone Mi "Ms Corporation)
52 Amsterdam Street
Newark, New Jersey 07105
]-Aminoanthraquinone and salt
1-Amino-4-benzamidoanthraquinone
l-Amino-5-benzamidoanthraquinone
1-Amino-2-chloroanthraquinone
1-Amino-5-chloroanthraquinone
1-Amino-8-chloroanthraquinone
2-Amino-3-chloroanthraquinone
Anthra [1,9-cd] pyrazol-6 (2H)-one
3-(l-Anthraquinonylamino~7H-benz(dejanthracen)-7-dione
1-Benzamido-5-chloroanthraquinone
7H~Benz (de) anthracen-7-one
(3s3'-Bi-7H-benz [de] anthracen)-7,7'-dione
(4,4'~Bi-7H-benz [de2 anthracen)-7,7'-dione
1,4-Bis-(1-anthraquinonylamino) anthraquinone
3-Bromo-7H-benz (de) anthracen-7-one
l-[(9-Bromo-7-oxo-7H-benz [de] anthracen-3-yl)
ami no]-anthraquinone
1-Chioroanthraquinone
1-Chioro-5-nitroanthraquinone
l-Chloro-8-nitroanthraquinone
4,5'-Dibenzamido-1, 1'-iminodianthraquinone
3,9-Dibromeo-7H-benz (de) anthracen-7-one
7,16-Dich1oro-6,]5-dihydro-5?9,14,18-anthrazinetetrone
9.10-Dihydro-9s 10-dioxo-l-anthracenesulfonic acid
9,10-Dihydro-9s 10-dioxo-l-anthracenesulfonic acid,
sodium salt
9,10-Dihydro-5-nicro-9, 10-dioxo-l-anthracenesulfonic acid
16,17-Dihydroxyviolanthrone
16,17-Dirnethoxyviolanthrone
10,10'-Dinitro (3,3'-bi-7H-henz[de]anthracen)-7,7'-dione
Dyes
Azoic diazo components
Vat dyes
1,1 -Iminobis (4~aminoanthraquinone)
1,1 -Iminobis (4-benzamidoanthraquinone)
1,1 -Iminobis (5-benzarnidoanthraquinone)
1,1 -Irninobis-4-nitroanthraquinone
1,1 -Iminodianthraquinone
Isoviolanthrone
Leuco-1,4-diaminoanthraquinone
S-Methylisothiourea sulfate
1-Nitroanthraquinone
m-Nitrobenzenesulfonic acid, sodium salt
16-Nitroviolanthrone
l-[(7-Oxo-7H-benz[de] anthracen-3-yl) amino]
anthraquinone
305.
-------
TABLE D-37. (Continued)
1,1'-[7-Oxo-7H-benz [de] anthracen-3,9-y1ene) diimino] dianthraquinone
Quinizarin
Violanthrone
306
-------
.TABLE D-38. MEDICAL CHEMICAL CORPORATION*
1713 20th Street
Santa Monica, California 90404
Dyes
Basic dyes
*Not listed by Synthetic Organic Chemicals in 1972 or 1973
307
-------
TABLE D-39. MOBAY CHEMICAL CORPORATION
(formerly Baychem Corporation)
owned by Bayer A6 of Leverbusen, West Germany
Penn Lincoln Parkway West
Pittsburgh Pennsylvania 15205
Verona Division
(Formerly Verona Corporation)
Springfield Road, P.O. Box 385
Union, New Jersey 07083
Bayonne, New Jersey 07002 (2 Plants)
169 West 52nd Street and Hobart Avenue and 2nd Street
2-(.p_-Aminoani 1 ino)-5-nitrobenzenesulfonic acid
7-(£-Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
8-Amino-2~naphthol
l-Amino-6-naphthol hydrochloride
l-Amino-7-naphthol hydrochloride
4-Amino-2-nitrophenol
5-Ce-Aminophenylazo)salicylic acid
Anilinomethanesulfonic acid
Ot-Anisidinomethanesulfonic acid
4-Chloro-2-nitroaniline
2,6-Diaminoanthraquinone
4»8~Diaminoanthrarufin
3,4'-Diaminobenzanilide
2,4-Diaminophenol dihydrochloride
4,4'-Diamino-2s2'-stilbenedisulfonic acid
1,5-Dibenzoylnaphthalene
2,5-Dichloro-4-3-methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
1,4-Dichloro-2-nitrobenzene
2,5-Dichlorosulfanilic acid
9s10-Dihydro-93 10-dioxo-2,6-anthracenedisulfonic acid
9JO-Dihydro-93 10-dioxo-2,6-anthracenedisulfonic acid, sodium salt
195-Dihydroxy-4}8-dinitroanthraquinone
2,5-Dimethyl-4-chlorophenyl mercaptoacetic acid
1,5-Diphenoxyanthraquinone
1,4-Di~£-toluidinoanthraquinone
Dyes
Acid dyes
Cat ionic dyes
Direct dyes
Disperse dyes
Fiber-reactive dyes
Fluorescent brightening agents
Ingrain dyes
Mordant dyes
Vat dyes
2-Ethyl-2-phenylmalonic acid, diethyl ester
308
-------
TABLE D-39. (Continued)
o-Formylbenzenesulfonic acid
4-Hydroxymetanilamide
8-Hydroxy-l-naphthalenesulfonic acid
Metanilamide
3-Methyl-l-(6-chloro-3-sulfophenyl)-5-pyrazolone
3-Methyl-l-(2,5-dichlorosulfanilic)-5-pyrazolone
3-Methyl-l-(4-methylphenyl)-5-pyrazolone, tech.
mr(3-Methyl-5-oxo-2-pyrazolin-]-yl) benzenesulfonamide
p-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenasulfonic acid
I-Methyl-1-pheny1-2-pyrazoli n-5-one
Naphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
7-(and8)-Nitronaphth (1,2-d) (1,2,3) oxadiazole-5- sulfonic acid
l-(m-Nitrophenyl)-5-oxo-2-pyrazoline-3-carboxylic acid
5-Oxo-l-(3-Aminopheny1)-2-pyrazoline-3-carboxy1ic acid
5-Oxo-l-phenyl -2-pyrazoli ne-3-carboxylic aci d
5-Oxo-l-(jD-sulfophenyl)-2-pyrazoline-3-carboxylic acid
5-Oxo-l-(_R.-sulfotolyl)-2-pyrazoline-3-carboxylic acid
Phenylhydrazine hydrochloride
j2.-Toluenesulfonic acid, ethyl ester
£.-Toluenesulfonic acid, methyl ester
m.-Toluidinomethanesulfonic acid
o_-Tol u i di nomethanes u 1 f on i c acid
j>-Tolyl-3-methyl-5-pyrazolone
1,3,3-Trimethyl-indolineacetaldehyde
l,3,3-Trimethyl-2-methyleneindoline
7,7'-Ureylenebis (4-hydroxy-2-naphthalenesulfonic acid)
Charleston, South Carolina 29411
P.O. Box 10288
2-(j)-Aminoanilino)-5-nitrobenzenesulfonic acid
7-(£-Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
8-Amino-2-naphthol
l-Amino-6-naphthol hydrochloride
l-Amino-7-naphthol hydrochloride
4-Amino-2-ni trophenol
Anilinomethanesulfonic acid
4-Chloro-2-nitroaniline
Dyes
Acid dyes
Cationic dyes
Direct dyes
Disperse dyes
Fiber-reactive dyes
Vat dyes
309
-------
TABLE D-39. (Continued)
8-Hydroxy-l-naphthalenesuIfonic acid
Metanilamide
3-Methyl-l-(6-chloro-3-sulfophenyl)-5-pyrazolone
3-Methyl-l-(2,5-dichlorosulfanilic)-5-pyrazolone
3-Methyl-]-(4-methylphenyl)-5~pyrazolone, tech.
nv-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonamide
j3-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
3-Methyl-l-pheny1-2-pyrazolin-5-one
Naphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
7-(and 8)-Nitronapth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
5-Oxo-l-(3-Aminophenyl)-2-pyrazoline-3-carboxylic acid
5-Oxo-l-phenyl-2-pyrazoline-3-carboxylic aci d
5-Oxo-l-(p-sulfophenyl)-2-pyrazoline-3-carboxylic acid
5-Oxo-l-(p-sulfotolyl)-2-pyrazoline-3-carboxylic acid
Sarcosine
_p_-Tolyl -3-methyl »5-pyrazolone
310
-------
TABLE D-40. MORTON-NORWICH PRODUCTS, INC.
110 North Wacker Drive
Chicago, Illinois 60606
Morton Chemical Company, division
110 North WAcker Drive
Chicago, Illinois 60606
335 McLean Boulevard
Paterson, New Jersey 07504
Dyes
Disperse dyes
Fluorescent brightening agents
Solvent dyes
Toners and lakes
311
-------
TABLE D-41. NYANZA INC.
Magunco Road
Ashland, Massachusetts 01721
7-(p-Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
3-Amino-5-chloro~2~nydroxybenzenesulfonic acid
2-Amino-4-chloro-6-nitrophenol
7-Amino-4-hydroxy-2-naphthalenesulfonic acid, sodium salt
4'-Amino-N-methylacetani1ide
8-Amino-2-naphthol
3'-Amino-oxam'lic acid
£-(£-Aminophenyl)azo] benzenesulfonic acid
6-Anilino-4-hydroxy-2-naphthalenesulfonic acid
7-Anilino-4-hydroxy-2-naphthalenesulfonic acid
8-Anilino-l-naphthalenesulfonic acid
Anthrarufin
7H-Benz (de) anthracen-7-one
l-Chloro-2-methylanthraquinone
4-Chloro-3-nitrobenzenesulfonamide
2-Chloro-5-nitrobenzenesulfonic acid
1,4-Diaminoanthraquinone
194-Diamino-2,3-dichloroanthraquinone
1,5-Dibenzoylnaphthalene
2,5-Dichloro-4-(3-methyl-5-oxo~2-pyrazolin-l-yl) benzenesulfonic acid
2,5-Dichlorosulfanilic acid
1,5 (and l,8)-Dihydroxyanthraquinone
2,2'-Dimethyl-1,1'-bianthraquinone
1,4-Di-p-toluidinoanthraquinone
Dyes
Acid dyes
Direct dyes
Mordant dyes
Oxidation bases
Solvent dyes
Vat dyes
4-Hydroxymetanilamide
8-Hydroxy-l-naphthalenesulfonic acid, y-sultone
N-(7-Hydroxy-l-naphthyl) acetamide
1,1'-Iminobis (4-aminoanthraquinone)
7,7'-Iminobis (4-hydroxy-2-naphthalenesulfonic acid)
Metanilamide
4-Methoxymetanilie acid
m_-(3-Methyl~5-oxo-2-pyrazolin-1 -y 1) benzenesulfonamide
_pj-(3-Methyl-5-oxo-2-pyrazolin-l-yl)benzenesulfonic acid
4-(3-Methyl-5-oxo-2-pyrazolin-l-ylJ-m-toluenesulfonic acid
Naphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
3-Nitro-p-toluenesulfonic acid
Pyranthrone
Quinizarin
4-Sulfoanthranilic acid
7,7'-Ureylenebis (4-hydroxy-2-naphthalenesulfonic acid)
312
-------
TABLE D-42 . PASSAIC COLOR & CHEMICAL COMPANY
28-36 Paterson Street
Paterson, New Jersey 07501
Dyes
Acid dyes
Basic dyes
Solvent dyes
313
-------
TABLE D-43. PFISTER CHEMICAL, INC.
Linden Avenue
Ridgefield, New Jersey 07657
Charlotte, North Carolina 28213
General and Compounded Products
Azogen printing colors
Ridgefield, New Jersey 07657
3-Ami no-j).-an i san i 1 i de
2-Aniino-5-nitrothiazole
Benzanilide
4-Benzoy1-2,5-diethoxyan i1i ne
Bromoresorcylic acid
N'-Butyl-4-methoxymetanilamide
4-Chloro-o-anisidine
5-Chloro-2,4-dimethoxyaniline
4'-Chloro-3-hydroxy-2',5'-dimethoxy-2-naphthanilide
5'-Chloro~3-hydroxy-2',4'-dimethoxy-2-naphanilide
3'-Ch1oro-3-hydroxy-2-naphthanilide
4'-Chloro-3~hydroxy-2-naphthanilide
5'-Chloro--3-hydrcxy-2-naphth-j>-anisidide
4'-Ch1oro-3-hydroxy-2-naphtho-o_-toluidide
5'-Chloro-3~hydroxy-2-naphtho-o-tolui di de
5-Chlorosalicylanilide
4-Chloro-g-toluidine
5-Chloro-o^toluidine
2,5-Dimethoxyaniline
3-Hydroxy-2',5'-dimethoxy-2-naphthanilide
3-Hydroxy-2-naphthanilide
3-Hydroxy-2-naphth-o_-anisidide
3-Hydroxy~2-naphth-_p_-anisidide
3-Hydroxy-2-naphtho1c acid
3-Hydroxy-2-naphthoic acid, sodium salt
3-Hydroxy-2-naphtho-orphenetidide
3-Hydroxy-2-naphtho-^-phenetidide
3-Hydroxy-2~naphtho-£-toluidide
3-Hydroxy-2~naphtho-_£-toluidide
3-Hydroxy-2-naphtho-2',4'-xyli di de
3-Hydroxy-N-l-naphthyl-2-naphthanride
3-Hydroxy-M-2-naphthyl-2-naphthamide
3-Hydroxy-3'-nitro-2-naphthanilide
4~Methy1-7-diethyl aminocoumarin
2-Methy'l-5-nitroaniline
5-Nitro-o.-toluidine
2-Nitro-4-trifluoromethyl chlorobenzene
Resorcinol monohydroxy ethyl ether
Salicylanilide
5-Sulfoisophthalic acid, 1,3-dimethyl ester, potassium salt
5-Sulfoisophthalic acid, 1,3-dimethyl ester, sodium salt
5-Sulfoisophthalic acid, potassium salt
314
-------
TABLE D-43.(Continued)
5-Sulfoisophthalic acid, sodium ammonium salt
5-Sulfoisophthalic acid, sodium salt
Terephthaloyl-bis-acetyl-bis-5-chloro-2,4-dimethoxyaniline
2,2'-Terephthaloylbis (5'-chloro-2',4'-dimethoxyacetanilide)
4-(jD-Tolyazo)-o-toluidine
Trihydroxydiphenyl
315
-------
TABLE D-44. PPG INDUSTRIES INC.
(Formerly Pittsburgh Plate Glass Company)
One Gateway Center
Pittsburgh, Pennsylvania 15222
Pigments*
*Plant location not identified.
316
-------
TABLE D-45. RIDGWAY COLOR AND CHEMICAL
75 Front Street
Ridgway, Pennsylvania 15853
Pigments
317
-------
TABLE D-46. SANDOZ-WANDER, INC.
(Owned by Sandoz Ltd. of Switzerland)
Route 10
East Hanover, New Jersey 07936
See also: Toms River Chemical Corporation
Colors and Chemicals Division
Route TO, East Hanover, New Jersey 07936
Dyes
Toners and lakes
Fair Lawn, New Jersey 07410
Dyes
Fluorescent brightening agents
Paterson, New Jersey 07500
Dyes
Toners and lakes
318
-------
TABLE D-47. THE SHERWIN-WILLIAMS CO.
101 Prospect Avenue
Cleveland, Ohio 44101
Sherwin-Williams Chemicals Division
P.O. Box 6520
Cleveland, Ohio 44101
11541 South Champlain Avenue
Chicago, Illinois 60628
2-Amino-l-naphthalenesulfonic acid
2-Nitro-p-cresol
2-Ni tro-p-tolui di ne
Alkali blue pigment
St. Bernard, Ohio 45217
N-Acetylanthranilic acid
Anthranilamide
Anthranilic acid
N-Benzyldimethylamine
6-Bromo-5-chlorobenzoxazolone
p-Cresidine
2,6-Dibromo-4-nitrophenol
2,6-Dichloro-2-nitroaniline
Sodium 4-chlorophthalate
Tolyltriazole
319
-------
TABLE D-48. SOU-TEX CHEMICAL COMPANY,
INCORPORATED
(Owned by Casella Farbwerke Mainkur
of VJest Germany and American Hoechst
Corporation)
East Catawba Avenue
Mount Holly, North Carolina 28120
Dyes
Direct dyes
Disperse dyes
Sulfur dyes
Vat dyes
Soluble vat ester dyes
320
-------
TABLE D49. STANGE CO.
342 North Western Avenue
Chicago, Illinois 60612
Dyes
Food, drug and costmetic colors
321
-------
TABLE D-50. STERLING DRUG INC.
90 Park Avenue
New York, New York 10016
The Hilton-Davis Chemical Company, division
2235 Langdon Farm Road
Cincinnati, Ohio 45237
Cincinnati, Ohio 45237
Acetoacet-o-ani si dide
4,4'-Bis (diethylamino) benzophenone
4,4'-Bis (dimethylamino) benzhydrol
4,4'-Bis (dimethylamino) benzophenone
N,N-Diethylaniline
mh-(Dimethylamino) benzoic acid
Dyes
Acid dyes
Azoic coupling components
Azoic diazo components
Basic dyes
Direct dyes
Fluorescent brightening agents
Food, drug and cosmetic colors
[Phthalocyaninato (2-)] copper
Solvent dyes
Toners and lakes
N-Ethylaniline
N-Ethyl-N-pheny1benzylamine
4s4!-Methylenebis (N,N-dimethylaniline)
nv-Nitrobenzoic acid
Salicylic acid, technical
Thomasset Colors Division
120 Lister Avenue
Newark, New Jersey 07105
Dyes
Food, drug and cosmetic colors
[Phthalocyaninato (2-)] copper
Toners and lakes
Hexadecachlorophthalocyanine
6-Hydroxy-2~naphthalenesulfonic acid, sodium salt
322
-------
TABLE D-51 . SUN CHEMICAL CORPORATION*
200 Park Avenue
New York, New York 10017
Chemicals Group
411 Sun Avenue
Cincinnati, Ohio 45232
Pigments Division East
441 Tompkins Avenue
Staten Island, New York 10305
185 Foundry Street
Newark, New Jersey 07105
Perylene
Quinacridone
Rosebank, New York 10305
Dyes
Food, drug and cosmetic colors
General and Compounded Products
Azo pigments
Copper phthalocyanine pigments
Pigments Division West
4526 Chickering Avenue
Cincinnati, Ohio 45232
General and Compounded Products
Azo pigments
Copper phthalocyanine pigments
Flushed colors
*Sun Chemical recently purchased azo pigments technology from
Sherwin Williams Company (personal communication from
Sherwin-Williams spokesman, 3/20/75).
323
-------
TABLE D-52. SYNALLOY CORPORATION
P.O. Box 5627
Spartanburg, South Carolina 29301
Blackman Uhler Chemical Division
Spartanburg, South Carolina 29301
l-Amino-6-naphthol
]-Amino-6,7-naphthol
8-Amino-2-naphthol
6-Benzoylamino-4-methoxy-m-toluidine
4-n-Butyl sulfonamido-o-anisidine
4-Chloro-3-aminobenzotrifluoride
4-Chloro-o-anisidine
4-Chloro-2-nitrotoluene
4-Chloro-3-nitrotoluene
4-Chloro-_o_-toluidine
5-Chloro-£-toluidine
6-Chloro-rn-toluidine
4-Diethyl sulfonamido-ci-anisidine
Dyes
Azoic dyes and components
Disperse dyes
3-Hydroxy»2-naphthani 1 i de
3~Hydroxy-2-naphthoic acid
5-Nitro-o-anisidine
5-Nitro-£-toluidine
Sarcosine
4-(o-Tolyazo)-o_-toluidine
General and Compounded Products
Pigments for textiles
324
-------
TABLE D-53. TENNECO CHEMICALS, INC.
(See: Tenneco, Inc.)
Tenneco Inc.
Tenneco Building
Post Office Box 2511
Houston, Texas 77001
Tenneco Chemicals, Inc.
(A Tenneco Company)
Park 80 Plaza West
Saddlebrook, New Jersey 07662
Cal/Ink Division*
600 California Street
San Francisco, California 94108
Dyes
Toners and lakes
*Chemical Week (March 26, 1975, p. 23) reported that Tenneco will sell all
the U.S. assets of Cal/Ink Division to Flint Ink Corporation of Detroit
as of May 31, 1975.
325
-------
TABLE D-54. TOMS RIVER CHEMICAL CORPORATION
(79% owned by Ciba-Geigy Corporation and
21% by Sandoz Ltd.)
P.O. Box 71
Toms River, New Jersey 08753
See also: Ciba-Geigy Corporation
All production is for captive use only.
3-[(2-Acetamido-4-aminophenyl) azo]-l,5-naphthalene-disulfonic acid
S'-Aminoacetanilide
4'-Aminoacetanilide
l-Amino-4-(3-amino-4-sulfoanilino)-9, 10-dihydro-9,10-dioxo-2-anthracenesulfonic acid
1-Amino-4-(4-amino-3-sulfoam"lino)-9,10-dihydro-9,10-dioxo-2-anthracenesulfonic acid
2-(p-Aminoanilino)-5-nitrobenzenesulfonic acid
1-Aminoanthraquinone and salt
2-Aminoanthraquinone and salt
1-Ami no-4-benzami doanthraqui none
l-Amino-5-benzamidoanthraquinone
7-(m-Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
7-(jo-Aminobenzamido)-4-hydroxy-2-naphthalenesulfonic acid
3'-Aminobenzanilide-4'-sulfonic acid
2-Ami no-ji-benzenedi sulfonic acid
N-(4-Amino-3-bromo4-anthraquinonyl)-j3-toluidinesu1fonic acid
l-Amino-4-bromo-9,10-dihydro-9,10-dixox-2~ anthracenesulfonic acid and sodium salt
1-Amino-2-bromo-4-hydroxyanthraquinone
1-Ami no-2-brome-4-p-tolui di noanthraqui none
1-Amino-5-chloroanthraquinone
5-Amino-2-chlorobenzoic acid
1-Amino-2-chloro-4-hydroxyanthraquinone
3-Amino-5-chloro-2-hydroxybenzenesulfonic acid
2-Amino-£-cresol
1-Ami no-2,4-di bromoanthraqui none
1-Amino-2,4-dichloroanthraquinone
5-Amino-4,5'dihydroxy-3,4'-[(2-methoxy-5-methyl-p-phenylene) bis (azo)]-di-2,7-
naphthalenedisulfonic acid, 5'-benzenesulfonate
2-Amino-4-(a,a-dimethylbenzyl) phenol
5-Amino-4-hydroxy-m-benzenedisulfonic acid
1-Amino-4-hydroxy-2-methoxyanthraquinone
4-Amino-5-hydroxy-2,7-naphthalenedisulfonic acid, benzenesulfonate
4-Amino-3-hydroxy-l-naphthalenesulfonic acid
6-Amino~4-hydroxy-2-naphthalenesulfonic acid, sodium salt
7-Amino-4-hydroxy-2-naphthalenesulfonic acid, sodium salt
2-(2-Amino-5-hydroxy-7-sulfo-l-naphthylazo)-5-nitrobenzoic acid
1-(6-Amino-l-hydroxy-3-sulfo-2-naphthylazo)-6-nitro-2-naphthol-4-sulfonic acid
5-Amino-6-methoxy.-2-naphthalenesulfonic acid
m-(4-Amino-3-methoxyphenylazo) benzenesulfonic acid
4_[(4_Amino-5-methoxy-o-tolyl) azo]-4-hydroxy-2,7-naphthalenedisulfOnic acid,
benzenesulfonate
326
-------
TABLE D-54. (Continued)
3-[)4-Amino-5-methoxy-p_-tolyl) azo]-l,5-naphthalened1sulfonic acid
7-[(4-Amino-5-methoxy-£-tolyl) azo]-l,3-naphthalenedisulfonic acid
4-Amino-4'-(3-methyl-5-oxo-2-pyrazolin-lyl) 2,2'-stilbenedisulfonic acid
2-Amino-4-(methylsulfonyl) phenol
3-Amino-l,5-naphthalenedisulfonic acid
3-Amino-2,7-naphthalenedisulfonic acid
6-Amino-l,3-naphthalenedisulfonic acid
7-Amino-l,3-naphthalenedisulfonic acid
5-Amino-2-naphthalenesulfonic acid
5 (and 8)-Amino-2-naphthalenesulfonic acid
6-Amino-2-naphthalenesulfonic acid
8-Amino-l-naphthalenesulfonic acid
8-Amino-2-naphthol
2-Amino-5-nitrobenzenesulfonic acid
2-Amino-4-nitrophenol
4-Amino-4'-nitro-2,2'-stilbenedisulfonic acid
2-Aminophenol
m.-[(p-Aminophenyl) azo] benzenesulfonic acid
jj.-[(p-Aminophenyl) azo] benzenesulfonic acid
7-(4-Aminopheny1azo)-l,3-naphthalenedisulfonic acid
5-(p-Aminophenylazo) salicylic acid
2-(p-Aminophenyl)-6-methyl-7-benzothiazolesulfonic acid and salt
5-Amino-£-toluenesulfonic acid
5-Amino-2-(£-toluidino) benzenesulfonic acid
m-(4-Amino-3-tolylazo) benzenesulfonic acid
3-(4-Amino-p_-tolylazo)-l ,5-naphthalenedisulfonic acid
7-(4-Amino-o.-tolyazo)-l,3-naphthalenedisulfonic acid
7-Anilino-4-hydroxy-2-naphthalenesulfonic acid
Anilinomethanesulfonic acid
Anilinomethanesulfonic acid, sodium salt
o-Anisidinomethanesulfonic acid
F-(o.-Anisidino)-5-nitrobenzenesu1fonic acid
Anthraf'l»avic acid-
Anthra [1,9-cd] pyrazol-6 (2H)-one
Anthraquinone
N,N'-(l,5-Anthraquinonylene) dianthranilic acid
Anthrarufin
4' ,4' "-Azobis (4-biphenylcarboxylic acid)
1-Benzami do-5-chloroanthraquinone
4-Benzamido-5-hydroxy-2,7-naphthalenedisulfonic acid
7-Benzamido-4-hydroxy-2-naphthalenesulfonic acid
7H-Benz (deT) a'nthyiaceH-7-:0ne
3,3'-Bianthra (1,9-cd) pyrazole-6'(2H,2'H)-dione
1,4-Bis-(l-anthraquinonylamino) anthraquinone
Bis (chlorosulfonyl) phthalocyaninedisulfonic acid, copper derivative
4,4-Bis (diethylamino) benzhydrol salt, 2,7-naphthalenedisulfonic acid mixture
4-Bis ([2-diethylaminophenyl]"methyl)-2,7-naphthalenedisulfonic acid, leuco form
4,4'-Bis (£-hydroxyphenylazo)-2,2I-stilbene-disulfonic acid
3-Bromo-7H-benz (de) anthracen-7-one
327
-------
TABLE D-54 (Continued)
2-Bromo-4,6-dinitroaniline
Carbazole violet
N-[(3-Carboxy-4-chlorophenyl)-sulfonyl] anthranilic acid
1-Chioroanthraqui none
2-Chloroanthraquinone
Chloro-7H-benz (de) anthracen-7-one
1-Chiorobenzene-4-methylsulfone
p-Chlorobenzenesulfinic acid
3-Chloro-4,6-dinitrobenzenesulfonic acid
1-Chloro-2-methylanthraquinone
4-Chloro-N-methyl-3-nitrobenzenesulfonamide
4-Chloro-3-(methylsulfonyl) nitrobenzene
1-Chioro-5-nitroanthraquinone
2-Chloro-5-nitrobenzenesulfinic acid
4-Chloro-3-nitrobenzenesulfonamide
4-Chloro-3-nitrobenzenesu1fonanil ide
2-Chloro-5-nitrobenzenesulfonic acid
4-Chloro-3-nitrobenzenesulfonic acid
2-Chloro-5-nitrobenzoic acid
4-Chloro-3-nitrophenyl methyl sulfone
l-(p-Ch1orophenyl)-3-methyl-2-pyrazolinc-5-one
2-Chloro-5-sulfamoylbenzoic acid
l-(6-Chloro-p_-tolyl)-3-methyl-2-pyrazolin-5-one
Chrysazin
3'-[Di (2-acetoxyethyl) amino]-p-acetophenetidide
1,4-Diaminoanthraquinone
1,5-Diaminoanthraquinone
1,5 (and l,8)-Diaminoanthraquinone
2,6-Di ami noanthraqui none
3,4-Diaminobenzani1ide
2,4-Diaminobenzenesulfonic acid
2,5-Diaminobenzenesulfonic acid
4,8-Dianrino-9,10-dihydro-!,5-dihydroxy-9,10-dioxo-2,6-anthracenedisulfonic acid
4,4'-Diamino-2,2l-stilbenedisulfonic acid
1,5-Dibenzamidoanthraquinone
4,5'-Dibenzamido-1, 1'-iminodianthraquinone
Dibenzo[ b.def] chrysene-7,14-dione
1,5-Dibenzoylnaphthalene
3,9-Dibromo-7H-benz(de) anthracen-7-one
1,5-Di chloroanthraqui none
1,8-Dichloroanthraquinone
2,5-Dichloro-4-(3-methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
2,5-Dichloro-4-sulfobenzenediazonium sulfate
3-[(p-Diethylamino) phenylazo]-!H-l,2,4-triazole
6,15-Dihydro-5,9,14i,18-anthrazinetetrone
9,10-Dihydro-9,10-dioxo-l,5-anthracenedisulfonic acid
9»10-Dihydro-9,10-dioxo-l,5-anthracenedisulfonic acid, disodium salt
9,10-Dihydro-9,10-dioxo-l,5 (and l,8)-anthracene-disulfonic acid
9,10-Dihydro-9,10-dioxo-l,5(and l,8)-anthracene-disulfonic acid, sodium salt
328
-------
TABLE D-54. (Continued)
9,10-Dihydro-9910-dioxo-l,8-anthracenedisulfonic acid, potassium salt
9,10-Dihydro-9,10-dioxo'-2,6-anthracenedisu1fonic acid
9,10-Dihydro~9,10-dioxo~2,6-anthracenedisulfonic acid, sodium salt
9,10-Dihydro~9,10-diQxo-l-anthracenesulfonic acid
9,10-Dihydro-9,ld'-dioxo-T^anthracenesulfonic acid, sodium salt
9JO-Dihydrb-5-nitrb-9,fO-dioxo-l-anthracenesulfonic acid
9,10-Dihydro-!-nitro-9,10-dioxo-2-anthroic acid
1,5 (and l»8)-Dihydroxyanthraquinone
l,5-Dihydroxy-4,8-dinitroanthraquinone
l,8-Dihydroxy-4,5-dinitroanthraquinone
1,5 (and l,8)-Dimethoxyanthraquinone
4-(
-------
TABLE D-54. (Continued)
5-Hydroxy-l-naphthalenesulfonic acid
6-Hydroxy-2-naphthalenesulfonic acid, sodium salt
N-(7-Hydroxy-l-naphthyl) acetamide
l-(2-Hydroxy-l-naphthylazo)-6-nitro-2-naphthol-4-sulfonic acid
2-Hydroxy-5-nitrometanilic acid
l-(2-Hydroxy-4-nitrophenylazo)-2-naphthol
3-[4-(4'-Hydroxyphenylazo)-2,5-dimethoxyphenylazo] benezenesulfonic acid
^'-([ot-Hydroxy-ji-sulfobenzylidene] bis [(3-methyl-ji-phenylene) (ethylimino)])
di-m-toluenesulfonic acid
1,1'-Iminobis (4-aminoanthraquinone)
1,1'-Iminobis (5-benzamidoanthraquinone)
7,7'-Iminobis (4-hydroxy-2-naphthalenesulfonic acid)
1,1 '-Iminobis-4-nitroanthraquinone
1,1'-Iminodianthraquinone
Isoviolanthrone
Leuco-1,4-diaminoanthraquinone
Leuco quinizarin
Leuco tetrahydroxyanthraquinone
Metanilic acid
4,4'-Methylenebis (N,N-diethylaniline)
m-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
£-(3-Methyl-5-oxo-2-pyrazolin-l-yl) benzenesulfonic acid
4-(3-Methyl-5-oxo-2-pyrazolin-l-yl)-mrtoluenesulfonic acid
1-Naphthalenesulfonic acid
1-Naphthalenesulfonic acid, sodium salt
1,4,5,8-Naphthalenetetracarboxylic acid
Naphth (1,2-d) (1,2,3) oxadiazole-5-sulfonic acid
3'-Nitroacetanilide
4'-Nitroacetanilide
5-Nitroanthranilic acid
m-Nitrobenezenesulfonic acid
4'-Nitro-4-biphenylcarboxylic acid
3-Nitro-l,5-naphthalenedisulfonic acid
7-(and 8)-Nitronaphth (1,2-d) (1,2,3) oxadiazole-5- sulfonic acid
2-(4-Nitrophenyl)-(2H)-naphtho (1,2-d) triazole-6,8-disulfonic acid
4-Nitro-4'-[5-sulfo-2H-naphthol (1,2-d) triazol-2-yl]-2,2'-stilbenedisulfonic acid
3-Nitro-^p_-toluenesulfonic acid
5-Nitro-p_-toluenesulfonic acid
5-Nitro-2-£-toluidinobenzenesulfonic acid
Oxalacetic acid, diethyl ester, (£.-sulfophenyl)hydrazone
5-Oxo-l-(3-Aminophenyl)-2-pyrazoline-3-carboxylic acid
l-[(7-Oxo-7H-benz [de] anthracen-3-yl) amino] anthraquinone
l,l'-[(7-Oxo-7H-benz [de] anthracen-3,9-ylene) diimino] dianthraquinone
Phthalocyaninetetrasulfonyl chloride, copper derivative
Pyranthrone
Quinizarin
Salicylic acid, ammonium chromium complex
Salycylic acid, sodium chromium complex
5-Sulfamoylanthranilic acid
4-Sulfoanthranilic acid
^<*-[(£-Sulfobenzylidene) bis [(3-methyl-p-phenylene) (Ethylimino)]] di-m-toluene-
sulfonic acid
N,5'-Sulfonyldianthranilic acid
330
-------
TABLE, D-54. (Continued)
Tetrabromo-8,16-pyranthrenedi one
3,3'-Thiobis [7H-benz (de) anthracen-7-one]
Toluene-2,4-diamine
p_-Toluidinomethanesulfonic acid
T,7'-Ureylenebis (4-hydroxy-2-naphthalenesulfonic acid)
2,2'-Vinylenebis (benzimidazole)
Violanthrone
Products N.E.C.
2-Chloro-5-n i trobenzenes ulfony1 chlori de
4-Hydroxyacetan i1i de
N-(4-Hydroxymetanilyl) anthranilic acid
N-(7-Hydroxy-l-naphthyl) benzamide
3'-([7-Hydroxy-l-naphthyl]carbamoyl) acetani1i de
3-(3-Methyl-5-oxo-2pyrazolin-l-yl)-l,5- naphthalenedisulfonic acid
2-(Methylsulfony1)-4-nitroaniline
1,5-Naphthalenedisulfonic acid
2,7-Naphthalenedisulfonic acid
331
-------
TABLE D-55. PAUL UHLICH & COMPANY,
INCORPORATED
90 West Street
New York, New York 10006
Hastings-on-Hudson, New York 10706
Dyes
Toners and lakes
332
-------
TABLE D-56. UNITED MERCHANTS & MANUFACTURERS, INC.
1407 Broadway
New York, New York 10018
Roma Chemical - Color Division
749 Quequechan
Fall River, Massachusetts 02723
•
Dyes
Toners and Lakes
General and Compounded Products
Pigment dispersions
Pigment press cakes
Textile printing inks
333
-------
TABLE D-57. WARNER-JENKINSON COMPANY
(Formerly known as Warner-Jenkinson
Manufacturing Company)
2526 Baldwin Street
St. Louis, Missouri 63106
Dyes
Food, drug and costmetic colors
<£-(N-Ethyl anilino)-p-toluenesulfonic acid
£.-Hydrazinobenzenesulfonic acid
3-Hydroxy-2,7-naphthalenedisulfonic acid, disodium salt
6-Hydroxy-2-naphthalenesulfonic acid, sodium salt
334
-------
TABLE D-58. THE J.S. YOUNG COMPANY
2731 Boston Street
Baltimore, Maryland 21224
Young Aniline Works, Inc., subsidiary
Balitmore Maryland 21224
Dyes
Acid dyes
Direct dyes
Mordant dyes
335
-------
APPENDIX E
LOCATIONS OF DYE AND PIGMENT
MANUFACTURING PLANTS
LISTED BY REGION
337
-------
TABLE E-l
LOCATIONS OF DYE AND PIGMENT
MANUFACTURING PLANTS
New Jersey (30 plants)
1. Alliance Chemical Company
Newark, New Jersey 07105
*2. Allied Chemical Corporation
Specialty Chemicals Division
Haledon, New Jersey
*3. American Color and Chemical Corporation
Paterson, New Jersey
*4. American Cyanamid Company
Organic Chemicals Division
Bound Brook, New Jersey
5. Atlantic Chemical Industries, Inc.
Atlantic Chemical Corporation, subsidiary
Nutley, New Jersey
6. BASF Wyandotte Corporation
Colors and Chemicals Group
Kearny, New Jersey
*7. E.I. duPont deNemours & Company, Inc.
Organic Chemicals Department
Dyes and Chemical Division
Deepwater, New Jersey and Newark, New Jersey
8. Dye Specialties, Inc.
Jersey City, New Jersey
9. Fabricolor Inc.
Paterson, New Jersey
*10. Foster-Heaton Company
Paterson, New Jersey
11. GAF Corporation
Chemical Division
Paterson, New Jersey and Linden, New Jersey
12. Indol Chemical Company, Inc.
Carterest, New Jersey
13. Inmont Corporation
Hawthorne, New Jersey
14. H. Kohnstamm and Company, Inc.
Pigments Division
Camden, New Jersey
* Plants belonging to companies considered to be among the seven leading
manufacturers.
338
-------
14- Magruder Color Company, Inc.
Newark, New Jersey
15. Max Marx Color and Chemical Company
Irvington, New Jersey
16. Otto B. May, Inc.
Newark, New Jersey
17. Mobay Chemical Corporation
Verona Division
Bayonne, New Jersey (2 plants)
18. Morton-Norwich Products, Inc.
Morton Chemical Company, division
Paterson, New Jersey
19. Passaic Color and Chemical Company
Paterson, New Jersey
20. Pfister Chemical Inc.
Ridgefield, New Jersey
21. Sandoz-Wander, Inc.
Color and Chemicals Division
Fair Lawn, New Jersey
East Hanover, New Jersey
Paterson, New Jersey
22. Sterling Drug Inc.
Thomasset Colors Division
Newark, New Jersey
23. Sun Chemical Corporation
Pigments Division East
Newark, New Jersey
*24- Toms River Chemical Corporation
Toms River, New Jersey
* Plants belonging to companies considered to be among the
seven leading manufacturers.
339
-------
Ohio-West Virginia-Kentucky (11 plants)
*1. American Cyanamid Company
Organic Chemicals Division
Marietta, Ohio
Willow Island, West Virginia
2. Borden, Inc.
Borden Chemical Division
Graphic Arts Products Division
Cincinnati, Ohio
3. Chemetron Corporation
Chemicals Group
Pigments Division
Huntington, West Virginia
4. Cincinnati Milacron, Inc.
Cincinnati Milacron Chemicals Inc., subsidiary
Cincinnati, Ohio
5. Day-Glo Color Corporation
Cleveland, Ohio
*6. GAP Corporation
Chemical Division
Calvert City, Kentucky
7. Kewanee Oil Company
Harshaw Chemical Company, division
Pigment and Ceramic Department
Louisville, Kentucky
8. The Sherwin-Williams Company
Sherwin-Williams Chemicals Division
St. Bernard, Ohio
9. Sterling Drug Inc.
The Hilton-Davis Chemical Company, division
Cincinnati, Ohio
10. Sun Chemical Corporation
Pigments Division West
Cincinnati, Ohio
* Plants belonging to companies considered to be among the seven leading
manufacturers.
340
-------
North Carolina - South Carolina (9 plants)
*1. American Color and Chemical Corporation
Beaufort, South Carolina
2. BASF Wyandotte Corporation
Colors and Chemicals Group
Charlotte, North Carolina
3. Ciba-Geigy Corporation
Dyestuff and Chemicals Division
Greensboro, North Carolina
4. Kewanee Oil Company
Harshaw Chemical Company Division
Textile Color Department
Lowell, North Carolina
5. Martin-Marietta Corporation
Martin Marietta Chemicals
Sodyeco Division
Sodyeco, North Carolina
6. Mobay Chemical Corporation
Verona Division
Charleston, South Carolina
7. Pfister Chemical Inc.
Charlotte, North Carolina
8. Sow-Tex Chemical Company, Inc.
Mount Holly, North Carolina
9. Synalloy Corporation
Blackman Uhler Chemical Division
Spartanburg, South Carolina
* Plants belonging to companies considered to be among the seven
leading manufacturers.
341
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Massachusetts-Rhode Island (8 plants)
1. American Hoechst Corporation
Dyes and Pigments Division
Coventry, Rhode Island
2. Benzenoid Organics, Inc.
Bellingham, Washington
3. Childs Pulp Colors, Inc.
Springfield, Massachusetts
4. Philip A. Hunt Chemical Corporation
Wayland Chemical Division
Lincoln, Rhode Island
Industrial Dyestuff Co., subsidiary
East Providence, Rhode Island
*5. ICI United States Inc.
Dyes and Textiles Chemicals Division
Dighton, Massachusetts
6. Nyanza Inc.
Ashland, Massachusetts
7. United Merchants and Manufacturers, Inc,
Roma Chemical - Color Division
Fall River, Massachusetts
* Plants belonging to companies considered to be among the seven
leading manufacturers.
342
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New York (7 plants)
*1. Allied Chemical Corporation
Specialty Chemicals Division
Buffalo, New York
2. Berncolors-Poughkeepsie, Inc.
Poughkeepsie, New York
*3. GAP Corporation
Chemical Division
Rensselaer, New York
4. Hercules Inc.
Coatings and Specialty Products Department
Glens Falls, New York
5. H. Kohnstamm and Company, Inc.
Pigments Division
Brooklyn, New York
6. Sun Chemical Corporation
Chemicals Group
Pigments Division East
Rosebank, New York
7. Paul Uhlich and Company, Inc.
Hastings-on-Hudson, New York
Plants belonging to companies considered to be among the seven
leading manufacturers.
343
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Pennsylvania (7 plants)
*1. American Color and Chemical Corporation
Lock Haven, Pennsylvania
Reading, Pennsylvania
2. Crompton and Knowles Corporation
Chemicals Group
Gibraltar, Pennsylvania
Reading, Pennsylvania
3. Keystone Color Works, Inc.
York, Pennsylvania
4. C. Lever Company, Inc.
Cornwells Heights, Pennsylvania
5. Ridgway Color and Chemical
Ridgway, Pennsylvania
Illinois (4 plants
1. Apollo Colors Inc.
Northbrook, Illinois
2. Industrial Color Inc.
Joliet, Illinois
3. The Sherwin-Williams Company
Sherwin-Williams Chemicals Division
Chicago, Illinois
4. Stange Company
Chicago, Illinois
California (3 plants)
1. Day-Glo Color Corporation
South El Monte, California
2. Medical Chemical Corporation
Santa Monica, California
3. Tenneco Inc.
Cal/Ink Division
San Francisco, California
* Plants belonging to companies considered to be among the seven leading
manufacturers.
344
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Miscellaneous Locations (8 plants)
1. Ciba-Geigy Corporation
Industrial Chemicals Division
Mclntosh, Alabama
2. The J. S. Young Company
Young's Aniline Works, Inc., subsidiary
Baltimore, Maryland
3. Chemetron Corporation
Chemicals Group
Pigments Division
Holland, Michigan
4. Warner-Jenkinson Company
St. Louis, Missouri
*5. E.I. duPont deNemours & Company, Inc.
Organic Chemicals Department
Dyes and Chemical Division
Manati, Puerto Rico
6. Eastman Kodak Company
Eastman Chemical Products, Inc., subsidiary
Tennessee Eastman Company, division
Kingsport, Tennessee
7. American Cyanamid Company
Organic Chemicals Division
Damascus, Virginia
8. PPG Industries, Inc.
unknown location
Plants belonging to companies considered to be among the seven leading
manufacturers.
345
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TECHNICAL REPORT DATA
(Please read Instructions on the reverse before completing)
i. REPORT
2.
3. RECIPIENT'S ACCESSION-NO.
EPA-600/2-77-023q
4. TITLfc AND SUBTITLE
Industrial Process Profiles for Environmental Use:
Chapter 7» Organic Dyes and Pigments Industry
5. REPORT DATE
February 1977
6. PERFORMING ORGANIZATION CODE
7. AUTHOr.(S)
Thomas R. Steadman and Eleanor W. Helper (Battelle-Col.
T.Parsons, G.E.Wilkins, and N,P. Phillips
8. PERFORMING ORGANIZATION REPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS
Radian Corporation
8500 Shoal Creek Boulevard
P.O. Box 991*8
Austin, Texas 78766
10. PROGRAM ELEMENT NO.
1AB015
11. CONTRACT/GRANT NO.
68-02-1319/Task 3
12. SPONSORING AGENCY NAME AND ADDRESS
Industrial Environmental Research Laboratory
Office; of Research and Development
U.S. ENVIRONMENTAL PROTECTION AGENCY
Cincinnati, Ohio 1*5268
13. TYPE OF REPORT AND PERIOD COVERF.D
Initial: 8/75-11/76
14. SPONSORING AGENCY CODE
EPA/600/12
1S. SUPPLEMENTARY NOTES
16. ABSTRACT
The catalog of Industrial 'Process Profiles for Environmental Use was developed as an
aid in defining the environmental impacts of industrial activity in the United States.
Entries for each industry are in consistent format and form separate chapters of the
study. The organic dyes and pig.ritnts industry is engaged in the conversion of
purchased organic chemicals, usually eyelid benzenoids, into more complex intermediate
and ultimately into dyes and pigments. Forty-two chemical trees, thirty-four process
flow sheets, and forty-eight process descriptions have been prepared to characterize
the industry. Within eac?i process description available data have been presented on
input materials, operating parameters, utility requirements, and waste streams.
Data related to the subject matter, including company, product, and raw material
data, are included as appendices.
17.
KEY WORDS AND DOCUMENT ANALYSIS
DESCRIPTORS
Pollution
Organic Dyes
Pigments
Cyclic Benzenoids
Dyes
Organic Pigments
Process Description
18. DISTRIBUTION STATEMENT
Release to the public
b.lDENTIFIEHS/OPUN ENDED TERMS
Process Assessment"
Air Pollution Control
Water Pollution Control
Solid Waste Control
Stationary Sources
Organic Chemical Industry
Synthetic Dyes
19. SECURITY CLAbS (Tins Report)
_ Unclasjn" fied
__ __
20. SECURITY CLASS (Tills page)
Unclassified
f.PA Form ?22'i-l IS
COSATI l-'ield/Oroup
07C
11C
13B
21. NO.
362
22. PRICE
346
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