Patent GB-732419-A (GB)
Title: Process for the preparation of polyazo dyestuffs
IPC: C09B31/30
Filed: 1953-07-01
Abstract: The invention comprises dyestuffs containing at least two sulphonic acid groups and of formula <FORM:0732419/IV (c)/1> where A and B are radicles of the benzene and naphthalene series, the nucleus I may be further substituted by methyl, methoxy or acylamino groups, the azo groups are in paraposition to each other and <FORM:0732419/IV (c)/2> is the residue of a hydroxynaphthalene-mono-, -di-, or -trisulphonic acid, of a sulphonated or unsulphonated 5-pyrazolone or of 1-hydroxy-4-methylbenzene and their completely coppered compounds in which OCH3 has been split off.  Dyestuffs of the above formula may be made by coupling 1 mol. of a diazo compound of an amine of formula <FORM:0732419/IV (c)/3> with 1 mol. of a copper complex of the requisite monoazo naphthalene derivative.  These dyestuffs may be coppered on the fibre or in substance with the usual copper-yielding agents.  The aminodisazo starting dyestuffs may be made as in the parent patent and those specified therein may be used in the present process. Coppered coupling components may be made for instance by diazotizing 1-chloro-2-amino-5-hydroxy - naphthalene - 7 - sulphuric acid, coupling, preferably in alkaline aqueous solution, with a coupling component corresponding to R2 and treating the o-chloro-o1 - hydroxy compound thus obtained, as in Specification 388,332 and a copper salt at e.g. 90 DEG  C. in the presence of glycerine and sodium hydroxide.  R2 is preferably a residue of 1-hydroxynaphthalene-4- and -5-sulphonic acids, -3,6-, -3,8- and -4,8-disulphonic acids and -3,5,7- and -3,6,8-trisulphonic acids, 2-hydroxy-naphthalene-4-, -6- and -7-sulphonic acids and -3,6- and -6,8-disulphonic acids, 1-phenyl-3-methyl-5-pyrazolone and its 21,31 and 41-sulphonic and 31-carboxylic acids, 1-(61-chloro) -phenyl-3-methyl-5-pyrozolone-31-sulphonic acid, 1-(21-methyl)-phenyl - 3 - methyl - 5 - pyrazolone - 41 - sulphonic acid, 1-phenyl-5-pyrazolone-3-carboxylic acid and 1-hydroxy-4-methylbenzene.  The coupling of the aminodiazo dyestuff and final coppering are effected as in the parent patent.  The incompletely coppered dye-stuffs dye cotton and regenerated cellulose fibres in grey to olive-green shades. In examples: (1) diazotized 2-aminonaphthalene-6,8-, -3,6-, -4,8- or -5,7-di- and -1-, -5-, -6- and -8-mono-sulphonic acids, 1-amino-naphthalene-3,6-, -3,8- and 4,8-di- and -4-, -5-, -6-, -7- and -8-monosulphonic acids, 1-aminobenzene-2,4- and -2,5-di- and -2-, -3- and -4-monosulphonic acids, 1-aminobenzene-2-methylbenzene-4- and -5-sulphonic acid, 1 - amino - 2,4 - dimethylbenzene - 6-sulphonic acid, 1-amino-3-carboxy-4-hydroxy-benzene-5-sulphonic acid and dehydrothio-p-toluidine-mono- and -di-sulphonic acids are coupled with 1-amino-3-methyl-, -2-methoxy-, -2,5-dimethyl, -dimethoxy or -diethoxy-, -3-acetylamino- and -2-methoxy-5-acetylamino-benzene, 1-aminonaphthalene and 1-amino-2-methoxy and -2-ethoxynaphthalene, further diazotizing and coupling with 1-amino-2-methoxy-5-methyl-, -acetylamino-, -propionylamino-, -formyl-, -benzyl- and -carbethoxyamino-benzene and 1-amino-2-methoxy- and -2,5-dimethoxybenzene, and diazotizing the product and coupling with a copper complex derived from 2-hydroxynaphthalene-4-, -6- and -7-sulphuric acid and 1-hydroxynaphthalene-3-, -4- and -5-sulphonic acid; (2) diazotized 1-aminonaphthalene-7-sulphonic acid, 1-amino- or 2-aminonaphthalene, aniline, 1-amino-3- or -4-methyl- or -2,5-dimethylbenzene, 1-amino-4-hydroxybenzene-3-carboxylic acid, 1-amino-4 - hydroxy - 5 - methylbenzene - 3 - carboxylic acid, 1 - aminobenzene - 4 - mono - and -2,5-di-carboxylic acid and 1-amino-2-carboxybenzene-4- and -5-sulphonic acids are coupled with 1-aminonaphthalene-6- or -7-sulphonic acid, the products diazotized and coupled with the end components of (1) and the product diazotized and coupled with the copper complexes of (1), (3) an aminodisazo-dyestuff of (1) is coupled with a copper complex derived from the above specified pyrazolones and the products thus obtained completely coppered; in (4) completely coppered dyestuffs are obtained using certain of the above specified components an additional initial component being 1-amino-2,5 - dimethylbenzene - 3 - sulphonic acid and in (5) cotton is dyed in conventional fashion with one of the above dyestuffs.