Patent GB-637093-A (GB)
Title: Production of quinoneimine and quinone dyestuff images
IPC: G03C7/34
Filed: 1946-11-07
Abstract: A mixture of N-1-anthronyloxamic acid and N-4-anthronyloxamic acid is prepared by reducing anthraquinone-1-oxamic acid with aluminium powder in concentrated sulphuric acid.  Mixtures of 1- and 4-(41-N-hexadecylcarbamyl-x1-sulphobenzamido) -9-anthrone, 1- and 4-(41-N - methylcarbamyl - x1 - sulphobenzamido) - 9 - anthrone, 1 - acetylamino - 9 - anthrone - 2 - sulphonic acid and 4-acetylamino-9-anthrone-3-sulphonic acid, 9-anthrone-2- and 3-carboxylic acid phenyl esters and of the corresponding thiobutyl, and thiophenyl esters, N-methyl-1-acetylamino-9-anthrone-2-carboxylic acid and N-methyl - 4 - acetylamino - 9 - anthrone - 3 - carboxylic acid, N-phenyl-1-acetylamino-9-anthrone-2-carboxylic acid and N-phenyl-4-acetylamino-9-anthrone - 3 - carboxylic acid, 1 - acetylamino - 9 - anthrone-2-carboxylic acid and 4-acetylamino-9-anthrone-3-carboxylic acid, N-1- and N-4-anthronylsuccinamic acids, N-1- and N-4-anthronylphthalamic acids, 1- and 4 - (41 - palmitoylamino - x1 - sulphobenzamido) - 9 - anthrones, 1- and p  4-ethylamino-9-anthrones, 1- and 4-carboxymethylamino-9-anthrones, 1-dimethylamino-9-anthrone-2-carboxylic acid and 4 - dimethylamino - 9 - anthrone - 3 - carboxylic acid, 1- and 4-phenylamino-9-anthrones, 1- and 4-(41 - sulphophenylamino) - 9 - anthrones, 1 - diphenylamino - 9 - anthrone - 2 - carboxylic acid and 4 - diphenylamino - 9 - anthrone - 3 - carboxylic acid, 2- and 3-mercapto-9-anthrones, 2- and 3-methylmercapto-9-anthrones, 1- and 4-phenylmercapto-9-anthrones, 1- and 4-ethylmercapto-9-anthrones, 1- and 4-phenylcarbamyl-9-anthrones, 2- and 3-ethylcarbamyl-9-anthrones, 1-ethylsulphonyl-9-anthrone-2-carboxylic acid and 4-ethylsulphonyl - 9 - anthrone - 3 - carboxylic acid, 1 - phenylsulphonyl - 9 - anthrone - 2 - carboxylic acid and 4-phenylsulphonyl-9-anthrone-3-carboxylic acid, 2- and 3-methylsulphonyl-9-anthrones, 2- and 3-butylsulphonyl-9-anthrones, and 2- and 3-phenylsulphonyl-9-anthrones are similarly prepared.  1 - (41 - N - hexadecylcarbamyl - x1 - sulphobenzamido)-anthraquinone is prepared by reacting 1-aminoanthraquinone with excess sulphonated terephthalic acid and condensing the product with hexadecylamine. 1-(41-N-methylcarbamyl-x1-sulphobenzamido) -anthraquinone is similarly prepared.  10-Nitroanthrone-2-carboxylic acid is prepared by treating diphenylmethane-2 : 41-dicarboxylic acid with concentrated sulphuric acid and nitrating.  9-Acetoxy-2-anthroic acid is prepared by treating 9-anthrone-2-carboxylic acid with acetic anhydride and pyridine.  9 - ethylcarbonyldioxy - anthracene - 2 - carboxylic acid is prepared by reacting 9-anthrone-2-carboxylic acid with pyridine and ethyl chlorocarbonate. 9-Phenylcarbonyldioxy-anthracene-2-carboxylic acid is similarly prepared.  1 - Acetylamino - 9 - anthrone - 2 - sulphonic acid mixed with 4-acetylamino-9-anthrone-3-sulphonic acid is prepared by reducing 1-acetylaminoanthraquinone - 2 - sulphonic acid with sodium hydrosulphite.  9-Anthrone-2-carboxylic acid methyl ester is prepared by treating 9-anthrone-2-carboxylic acid with methanol and HCl. Anthraquinone-2-carboxylic acid thiobutyl ester is prepared by reacting anthraquinone-2-carboxylic acid chloride with the lead salt of butyl mercaptan.  Anthraquinone-2-carboxylic acid thiophenyl ester is prepared by reacting anthraquinone-2-carboxylic acid chloride with thiophenol.  N - Methyl - 1 - acetylaminoanthraquinone - 2 - carboxylic acid is prepared by acetylating 1 - methylaminoanthraquinone - 2 - carboxylic acid with acetic anhydride or acetyl chloride.  N - Phenyl - 1 - acetylaminoanthraquinone - 2 - carboxylic acid is similarly prepared.  N-4-Anthronylsuccinamic acid is prepared by reacting 4-aminoanthrone with succinic anhydride and pyridine. N-4-Anthronylphthamic acid is similarly prepared.  A mixture of 1- and 4-(41-acetylamino-21- and 31-sulphobenzamido)-9-anthrones is prepared by sulphonating 1 - p - acetylaminobenzoylaminoanthraquinone to obtain a mixture of 6-(4-acetylamino-2- and 3-sulphobenzamido)-anthraquinones and reducing with sodium hydrosulphite. 1-p-Acetylaminobenzoylaminoanthraquinone is prepared by acetylating 1-p-aminobenzoylaminoanthraquinone with acetic anhydride. 1-p-Aminobenzoylaminoanthraquinone is prepared by reducing 1-p-nitrobenzoylaminoanthraquinone with sodium sulphide. 1-p-Nitrobenzoylaminoanthraquinone is prepared by heating 1-aminoanthraquinone with p-nitrobenzoyl chloride in nitrobenzene.  1 - Dimethylaminoanthraquinone - 2 - carboxylic acid is prepared by treating 1-chloroanthraquinone-2-carboxylic acid with dimethylamine. 1 - Diphenylaminoanthraquinone - 2 - carboxylic acid is similarly prepared.  1 - (41 - Sulphophenylamino) - anthraquinone is prepared by reacting 1-bromoanthraquinone with sulphanilic acid. 2-Methoxy-9-anthrone is prepared by treating 2-(p-methoxybenzyl)-benzoic acid with concentrated sulphuric acid. 2-Phenoxy-9-anthrone is similarly prepared. 2-(p-Phenoxybenzyl)-benzoic acid is prepared by reducing 2-(p-phenoxybenzoyl)-benzoic acid with zinc and ammonium hydroxide. 2-(p-Phenoxybenzoyl)-benzoic acid is prepared by condensing diphenyl ether with phthalic anhydride in presence of anhydrous aluminium chloride.  1-Phenylcarbamylanthraquinone is prepared by condensing anthraquinone-1-carboxylic acid chloride with aniline.  1 - Ethylsulphonylanthraquinone - 2 - carboxylic acid is prepared by oxidizing 1-ethylmercaptoanthraquinone-2-carboxylic acid with fuming nitric acid.  1-Phenylsulphonylanthraquinone-2-carboxylic acid, 2-butylsulphonylanthraquinone, and 2-phenylsulphonylanthraquinone are similarly prepared.  2-Butylmercaptoanthraquinone is prepared by reacting 2-mercaptoanthraquinone with butyl chloride and alkali. 9-Phenylsulponyloxy-2-anthroic acid is prepared by reacting 9-anthrone-2-carboxylic acid with benzenesulphonyl chloride and pyridine.  9-Propylsulphonyloxy-2-anthroic acid is similarly prepared.  10-Sulpho-9-anthrone is prepared by treating anthrone with concentrated sulphuric acid.  10-Methoxyoxalyl-9-anthrone is prepared by reacting together anthrone and methyl oxalate in presence of sodium methoxide. 10-Phenoxyoxalyl-9-anthrone is similarly prepared. 9-Hydroxy-10-anthryloxalic acid is prepared by hydrolysing 10-methoxyoxalyl-9-anthrone with sodium hydroxide.  A mixture of 1- and 4-acetylamino-9-aminoanthracenes is prepared by reducing 1-acetylaminoanthracene and heating with ammonia under pressure.  A mixture of 1- and 4-stearoylamino-9-methylaminoanthracenes is similarly prepared.  1-Stearylaminoanthraquinone is prepared by heating together 1-aminoanthraquinone and stearoyl chloride in nitrobenzene.  9 - Diethylaminoanthracene - 2 - carboxylic acid is prepared by heating 9-anthrone-2-carboxylic acid with diethylamine under pressure.