Patent GB-760085-A (GB)
Title: Improvements relating to metallisable disazo dyestuffs and to coppered dyeings obtainable therewith
IPC: C09B31/02
Filed: 1954-10-05
Abstract: Compounds of formula <FORM:0760085/IV(b)/1> where Q is NH, NHCO, NHCONH or <FORM:0760085/IV(b)/2> Ph is a m- or p-phenylene radicle which may be substituted, Cy is a 1,3,5-triazinyl residue, Z1 is a residue of an amine and Z2 is halogen or a residue of an amine, are made by reacting appropriate molar quantities of naphthols such as 2 - (41 - aminophenylamino) -, -(41 - amino - 31 - carboxyphenylamino) -, - (31 - and 41 - aminobenzoylamino)-, -(41-chloro- and -methyl-31-aminobenzoylamino)- and -(41-aminophenylureido) - 5 - naphthol - 7 - sulphonic acids and 2 - (31 - and 41 - aminophenyl) - 511 - hydroxy - 4,5 : 111,211 - naphthathiazole - 711 - sulphonic acids or their alkali metal salts in aqueous solution with cyanuric halides and amines.  Specified amines are aniline, 3-aminobenzene-1-carboxylic acid, 4-aminobenzene-1-sulphonic acid and its amide, 5-amino-2-phenol-1-carboxylic acid, 2-(41-aminophenylamino)-2-naphthol-7-sulphonic acid, diethylamine, ethylene diamine, dihydroxyethylamine and mono- and di-ethanolamine. The products are dyestuff intermediates, cf. Group IV (c).ALSO:The invention comprises dyestuffs of formula <FORM:0760085/IV(b)/1> where R is a benzene residue containing the OH and COOH groups in #s-position to each other, X is a direct link, -NH-CO-Ph-or -CO-Ph-, where Ph is a m- or p-phenylene radicle which may be substituted, Y is H or SO3H, Q is -NH-, -NH-CO-, -NH-CO-NH- or <FORM:0760085/IV(b)/2> Ph is a m- or p-phenylene radicle which may be substituted, Cy is a 1, 3, 5-triazinyl radicle, Z1 is a substituted amine radicle and Z2 is a halogen atom or an amino group which may be substituted.  They are made by diazotizing an appropriately substituted amino - naphthalene - azo - benzene dyestuff and coupling in an alkaline medium, optionally with compounds such as pyridine and alkanolamine bases, with the necessary 3-substituted-8-naphthol-6-sulphonic acid.  Specified subsituents for R and Ph are halogen, alkyl alkoxy, carboxy and sulphonic acid groups.  Preferred starting aminomonoazo dyestuffs are obtained from amino - 2 - phenol - 1 - carboxylic acids, e.g. 5 - or 3 - amino - 2 - phenol - 1 - carboxylic acids and their 3 - or 5 - sulphonic acids and 5 - amino - 3 - chloro - or - methyl - 2 - phenol - 1 - carboxylic acids, by diazotizing and coupling with 1 - amino - 2 - naphthoxyacetic acid or a 6 - or 7 - sulphonic acid thereof in an acidic medium.  The amino - 2 - phenol - 1 - carboxylic acids may be replaced by an appropriate aminobenzoyl derivative of phenol - #s - carboxylic acids or aminophenol - #s - carboxylic acids such compounds specified being 31 - and 41 - amino -, 41 - amino - 31 - methyl - and 31 - amino - 41 - methyl - 4 - hydroxybenzophenone - 3 - carboxylic acids, 3 - and 4 - aminobenzoyl - and 3 - amino - 4 - methyl - chloro - and - methoxy - benzoyl derivatives of the above amino - phenol - #s - carboxylic acids and also 3 - and 5 - (31 - aminobenzoyl - amino) - 2 - phenol - 1 - carboxylic acid - 41 - sulphonic acids.  Coupling components may be made by reacting, e.g. 2 - (41 - aminophenylamino) -, - (41 - amino - 31 - carboxyphenylamino) -, - 31 - and 41 - aminobenzoylamino) -, - (41 - chloro - and - methyl - 31 - aminobenzoylamino) - and - (41 - amino - phenyl - ureido) - 5 - naphthol - 7 - sulphonic acids and 2 - (31 - and 41 - aminophenyl) - 511 - hydroxy - 4, 5 : 111, 211 - naphthothiazole - 711 - sulphonic acids in the form of their alkali metal salts in aqueous solution with cyanuric chloride and with the replacement of a further halogen atom of the product by an amine at raised temperature and preferably of both halogen atoms by amines of the benzine series. The dyestuffs dye cellulose fibres blue to greenish-blue shades which may be after-coppered.  Examples are provided illustrating the proportion of the dyestuffs from certain of the above specified components amines used in the condensation with cyanuric chloride and the 2 - substituted - 5 - naphthol - 7 - sulphonic acid being aniline, 3 - aminobenzene - 1 - carboxylic acid, 4 - aminobenzene - 1 - sulphonic acid and its amide, 5 - amino - 2 - phenol - 1 - carboxylic acid, 2 - (41 - aminophenylamino) - 2 - naphthol-7-sulphonic acid, diethylamine, ethylene diamine, dihydroxyethylamine and mono - and di - ethanolamine and an additional component used corresponding to R being 5 - (41 - amino - 31 - methylbenzylamino) - 2 - phenol - 1 - carboxylic acid.