Patent GB-449263-A (GB)
Title: Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series
Filed: 1934-12-24
Abstract: Anthraquinone vat-dyes are prepared by reacting a carboxylic acid halide derivative of a 1(N).2-pyridonoanthraquinone with an aromatic amino compound containing at least one cyclically bound keto group. The carboxylic acid halide radicle may be a substituent in the pyridonoanthraquinone nucleus and/or in any substituent aryl radicle; amides are formed or in cases where the amino compounds may contain an o-hydroxyl, -mercapto or -amino group azoles may be formed.  In examples: (1) 1(N).2- pyridonoanthraquinone - Py3 - carboxylic acid chloride (derived by saponifying the product of example 3 of Specification 445,467 and treating the Py3-carboxylic acid with thionyl chloride) is condensed with 1- and 2 - aminoanthraquinones (yellow shades), 1-amino-4-benzoylaminoanthraquinone (orange), 1 - amino - 5 - benzoylaminoanthraquinone (yellow), 1.4- and 1.5-diaminoanthraquinones (yellow), 1.2-diaminoanthraquinone (orange), p-diaminoanthrarufin(reddish-brown), 2-amino-3-mercaptoanthraquinone (reddish-yellow), 2-amino - 3 - hydroxyanthraquinone (yellow) 4-and 5-amino-1.9-anthrapyrimidines (yellow); (2) 1(N).2-pyridonoanthraquinone-3-carboxylic acid chloride (prepared by treatment of 1-acetylamino-3-methylanthraquinone-2-aldehyde with potassium acetate, oxidation of the methyl group in the product to form the corresponding acid and treatment of this acid with thionyl chloride) is condensed with 1 - aminoanthraquinone (yellow), 1 - amino - 5 - benzoylaminoanthraquinone (reddish-yellow); (3) N-methyl-1(N).2-pyridonoanthraquinone - Py3 - carboxylic acid chloride (prepared by saponifying the ester of example 7 of Specification 445,467 and treating the acid with thionyl chloride) is condensed with 1-aminoanthraquinone (yellow), 1-amino-4- and -5-benzoylaminoanthraquinones (orange and reddish - yellow), 1.5 - diaminoanthraquinone (yellow, 2 - amino - 3 - hydroxyanthraquinone (yellow); (4) Py4-(p-tolyl)-1(N).2-pyridonoanthraquinone - Py3 - carboxylic acid chloride (derived by saponifying the ester of example 5 of Specification 445,467 and treating with thionyl chloride) is condensed with 1-amino-5-benzoylaminoanthraquinone (yellow) and with 1.5-diaminoanthraquinone (yellow); (5) N-methyl - Py4 - phenyl - 1(N).2 - pyridonoanthraquinone-Py3-carboxylic acid (derived from the ester of example 8 of Specification 445,467 by saponifying and treating with thionyl chloride) is condensed with 1 - aminoanthraquinone (yellow) and 1-amino-5-benzoylaminoanthraquinone (yellow); (6) Py4-(p-carboxyphenyl)-1(N).2 - pyridonoanthraquinone (derived by oxidizing the product of example 6 of Specification 445,467 and treating it with thionyl chloride) is condensed with 1-aminoanthraquinone (yellow), 1 - amino - 5 - benzoylaminoanthraquinone (yellow), 1.5-diaminoanthraquinone (yellow); (7) the chloride of N-methyl-Py4-(p-carboxyphenyl)-1(N).2-pyridonoanthraquinone (derived by the action of thionyl chloride on the acid of example 9 of Specification 445,467) is condensed with 1-aminoanthraquinone (yellow) and 1-amino-5-benzoylaminoanthraquinone (yellow); (8) the chloride of N - methyl - Py4-(p-carboxyphenyl)-1(N).2-pyridonoanthraquinone - Py3 - carboxylic acid (prepared by saponifying the ester of example 10 of Specification 445,467 and treating the acid with thionyl chloride) is condensed with 1 - aminoanthraquinone (yellow) and 1-amino-5-benzoylaminoanthraquinone (yellow); (9) the chloride of Py4-(2<1>.4<1>-dicarboxyphenyl)-1(N).2 - pyridonoanthraquinone (prepared by oxidizing the corresponding dimethylderivative of example 6 of Specification 445,467 and treating the dicarboxylic acid with thionyl chloride) is condensed with 1-amino-5-benzoylaminoanthraquinone (yellow); (10) 4 - chloro - N - methyl - Py4 - phenyl - 1(N).2 - pyridonoanthraquinone-Py3-carboxylic acid chloride (from the ester of example 11 of Specification 445,467 by saponifying and treatment with thionyl chloride) is condensed with 1-amino-5-benzoylaminoanthraquinone (yellow); (11) the chloride of N - (p-carboxyphenyl) - Py4-(p-methylphenyl)-1(N).2-pyridonoanthraquinone (from the acid of example 12 of Specification 445,467 by treatment with thionyl chloride) is condensed with 1 - amino - 5 - benzoylaminoanthraquinone (yellow); (12) Py4 - methyl - 1(N).2 - pyridonoanthraquinone - Py3 - carboxylic acid chloride (prepared by condensing 1 - amino - 2 - acetylanthraquinone with diethylmalonate, saponifying and treating with thionyl chloride) is condensed with 1-amino-5-benzoylaminoanthraquinone (yellow).