Patent GB-892382-A (GB)
Title: New anthraquinone vat dyestuffs and process for their manufacture
Filed: 1959-05-26
Abstract: 2 : 4 - di - (p - or m - carboxyphenylamino - 6 - cholor sym trizine is made by reacting 2 molecular proportions of 4- or 3-aminobenzoic acid with cyanuric chloride.  2 - (p - carboxyphenylamino) - 6 - chloro - sym - triazine having in the 4-position a m-carboxyphenylamino, a p-sulpho-phenylamino, a phenylamino or a cyclohexylamino group is made by condensing in equimolecular proportions p-aminobenzoic acid, cyanuric chloride and m-aminobenzoic acid, sulphanilic acid, aniline or cyclohexylamine.  2- (p - or m - carboxyphenylamino) - 4 - amino - 6-chloro-sym-triazine is made by reacting 2-amino-4 : 6-dichloro-sym-triazine with one molecular proportion of 4- or 3-aminobenzoic acid.  The p-isomer may also be made by reacting together in equimolecular proportions cyanuric chloride, 4- aminobenzoic acid and ammonia.  2 - (p - carboxyphenylamino - 6 - chloro - sym - triazing having in the 4-position a dimethylamino, a diethylamino, a phenyl or a phenoxy group is made by reacting 4-aminobenzoic acid with a 4 : 6-dichloro-sym-triazine having in the 2-position a dimethylamino, a diethylamino, a phenyl or a phenoxy group.  2 : 4 - bis - (p - carboxyphenyl) - 6 - hydroxy - sym - triazine and 2 - (p - carboxyphenyl) - 4 : 6 - di-hydroxy-sym-triazine are made by oxidising with potassium permanganate 2 : 4-bis-(p-tolyl)-6 - hydroxy - sym - triazine and 2 - (p - tolyl) - 4 : 6-dihydroxy-sym-triazine, respectively.ALSO:The invention comprises anthraquinone vat dyestuffs which contain at least one aroylamino group and at least one group of the formula <FORM:0892382/IV (c)/1> bound directly or through an amino bridge to the aroyl residue of the aroylamino group, and where X is chlorine, hydroxy, amino or a substituted or unsubstituted hydrocarbon substituent bound to the carbon atom of the triazine nucleus through an oxygen, sulphur or nitrogen atom or directly.  The dyestuffs are made by reacting an amino-anthraquinone which may contain fused-on carbocyclic or heterocyclic rings is reacted with a reactive derivative of an aryl carboxylic acid which contains at least one group of the formula (1) above bound directly or through an amino bridge, and, when a dichloro-triazine ring is present, optionally condensing one of the chlorine atoms with an amine, alcohol, phenol or mercaptan, or by reacting a dyestuff of the formula A-NH-CO-Aryl-NH2 with a compound of the formula <FORM:0892382/IV (c)/2> where A is the residue of an anthraquinone dyestuff and Aryl is a benzene residue.  The anthraquinone vat dyestuffs may be derived from amino-anthraquinones and substitution derivatives thereof, anthraquinone-acridone, dianthrimide-carbazoles, isothiazoleanthrone, anthrapyrimidine, anthrapyridone, aminoflavanthrone, oxdiale-anthraquinone, acedianthrone, dibenzanthrone, iso-dibenzanthrone, anthanthrone, dibenzpyrene quinone or benzanthrone.  The aryl carboxylic acid derivative which is reacted with the amino-anthraquinone may be of the formula <FORM:0892382/IV (c)/3> where n is 1 or 2.  Examples are given.  The dyestuffs dye and print textile materials of natural or regenerated cellulose by vatting methods or in conjunction with an alkali and heat treatment.