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ACID ANTHRAQUINONE DYES
CHAPTER I I
ACID ANTHRAQUINONE DYES W. Schoenauer, F. Benguerel, and J. Benz SAND OZ L T D . , SWITZERLAND
I. Dyes Derived from l-Aminoanthraquinone-2-sulfonic Acid . . 59 A. Coplanar Condensation Products of Bromaminic Acid with Aromatic Amines . . . . . . . . . . . 63 B. Condensation Products of Bromaminic Acid with 0,0' -Disubstituted Aniline Derivatives . . . . . . . - 7 5 C. Condensation Products of Bromaminic Acid with Aliphatic Amines 78 D. Dyes Containing Two Anthraquinone Moieties . . . . 8 1 E. Reactive Dyes Derived from Bromaminic Acid . . . . 84 F . Condensation Products of Bromaminic Acid with Other Nucleophiles 86 I I . Diaminodihydroxyanthraquinonesulfonic Acids . . . . 8 7 I I I . Dyes Formed by Sulfonation of a Dye Base . . . . . 88 A. Symmetrically Substituted 1,4-Diaminoanthraquinones . . 88 B. Unsymmetrically Substituted 1,4-Diaminoanthraquinones . .108 C. 1,4-Diaminoanthraquinones Substituted in the 2- and in the 2- and 3-Positions . . . . . . . . . .114 D. 1-Amino-4-arylaminoanthraquinones with a Substituent other t h a n a Sulfonie Acid Group in the 2-Position . . . . .118 E . l-Hydroxy-4-aminoanthraquinones . 122 F . 1,5-Diaminoanthraquinones . 123 G. Reactive 1,4-Disubstituted Anthraquinone Dyes 124 H . Heterocyclic Anthraquinone Derivatives 124 J . Dianthrimides and Carbazoles . 129
The acid anthraquinone dyes are important members of every commercial range of acid dyes, a class which finds its major uses in the dyeing of wool, synthetic polyamides, and silk. Along with the anthraquinone types, the acid ranges consist for the most part of monoazo and disazo dyes. Derivatives of other chromophoric systems such as nitrodiphenylamine, diazine, and triphenylmethane are of minor importance. The predominant acid anthraquinone dyes are the blues, which range in shade from reddish blue to blue-green. Blue azo dyes are available for the aforenamed fibers, but they do not match anthraquinone blues in brilliance, nor in some cases in lightfastness. The blue 2:1 premetallized 57
ACID ANTHRAQUINONE DYES W. Schoenauer, F. Benguerel, and J. Benz SAND OZ L T D . , SWITZERLAND
I. Dyes Derived from l-Aminoanthraquinone-2-sulfonic Acid . . 59 A. Coplanar Condensation Products of Bromaminic Acid with Aromatic Amines . . . . . . . . . . . 63 B. Condensation Products of Bromaminic Acid with 0,0' -Disubstituted Aniline Derivatives . . . . . . . - 7 5 C. Condensation Products of Bromaminic Acid with Aliphatic Amines 78 D. Dyes Containing Two Anthraquinone Moieties . . . . 8 1 E. Reactive Dyes Derived from Bromaminic Acid . . . . 84 F . Condensation Products of Bromaminic Acid with Other Nucleophiles 86 I I . Diaminodihydroxyanthraquinonesulfonic Acids . . . . 8 7 I I I . Dyes Formed by Sulfonation of a Dye Base . . . . . 88 A. Symmetrically Substituted 1,4-Diaminoanthraquinones . . 88 B. Unsymmetrically Substituted 1,4-Diaminoanthraquinones . .108 C. 1,4-Diaminoanthraquinones Substituted in the 2- and in the 2- and 3-Positions . . . . . . . . . .114 D. 1-Amino-4-arylaminoanthraquinones with a Substituent other t h a n a Sulfonie Acid Group in the 2-Position . . . . .118 E . l-Hydroxy-4-aminoanthraquinones . 122 F . 1,5-Diaminoanthraquinones . 123 G. Reactive 1,4-Disubstituted Anthraquinone Dyes 124 H . Heterocyclic Anthraquinone Derivatives 124 J . Dianthrimides and Carbazoles . 129
The acid anthraquinone dyes are important members of every commercial range of acid dyes, a class which finds its major uses in the dyeing of wool, synthetic polyamides, and silk. Along with the anthraquinone types, the acid ranges consist for the most part of monoazo and disazo dyes. Derivatives of other chromophoric systems such as nitrodiphenylamine, diazine, and triphenylmethane are of minor importance. The predominant acid anthraquinone dyes are the blues, which range in shade from reddish blue to blue-green. Blue azo dyes are available for the aforenamed fibers, but they do not match anthraquinone blues in brilliance, nor in some cases in lightfastness. The blue 2:1 premetallized 57