Patent GB-771331-A (GB)
Title: Improvements in or relating to disazo dyestuffs
IPC: C09B31/02
Filed: 1954-12-16
Abstract: The invention comprises dyestuffs of formula <FORM:0771331/IV(b)/1> where R is a benzene or naphthalene residue containing a metallizable group ortho to the az olink, Z is H1, Cl or SO3H, one W is CH3 and the other is (linked to A via an azo link (a) a residue of formula <FORM:0771331/IV(b)/2> where R1 is H, alkyl, cyloalkyl, aralkyl or aryl, R11 is H or alkyl, and 2 is as above, (b) the residue of an aliphatic or heterocyclic component containing the grouping -C(OH)=CH-, or (c) a phenol, naphthol or naphthol sulphonic acid residue free of acylamino groups coupled in ortho position to the OH group, and where R additionally contains an alkyl-sulphonyl, cycloralkylsulphonyl, aralkylsulphonyl or arylsulphonyl group the other W may also be a residue of formula <FORM:0771331/IV(b)/3> where 2 is as before.  The invention also includes metal complexes of the above dyestuffs.  The metal free dyestuffs are made by diazotizing, preferably indirectly, an amine corresponding to the first of the above formulae in which one W is CH3 and the other NH2 and coupling, preferably in weakly alkaline medium, with an appropriate azo component.  Metallization is effected on the fibre or in substance in conventional position, copper and nickel dyestuffs being preferred. Dyeing properties may be better if a mixture of dyestuffs is used. The dyestuffs before and after metallization dye cotton fibres of regenerated cellulose in orange, red to violet shades.  Examples and a table are provided illustrating the preparation of the dyestuffs, their copper and nickel complexes and the use of the latter in dyeing cotton and regenerated cellulose, components used corresponding to R being 1 - hydroxy - 2 - amino - 4 - methyl -, - ethyl -, - benzyl -, - cyclohexyl - and - (41 - methyl phenyl - sulphonyl - benzenes, 1 - hydroxy - 2 - amino - benzene - 4 - sulphuric acid and its amide and methyl and phenyl amides, 1 - hydroxy - 2 - amino - 4 - chlorobenzene, 1 - hydroxy - 2 - amino - 4 - sulpho-and - methyl sulphonyl - 6 - chlorobenzenes anthranilic acid, 2 - amino - 4 - and - 5 - methyl - sulphonyl - 1 - carboxylic acids, 1 - methoxy - 2 - amino - benzene - 4 - sulphonic acid, 1 - carboxymethoxy - 2 - amino - 4 - methyl sulphonyl - benzene, 1 - amino - 2 - naphthol - 4 - sulphonic acid and 3 - amino - naphthalene - 2 - carboxylic acid, components used corresponding to the 2 - benzoylamino - 5 - naphthol - 7 - sulphonic acid being 2 - (31 - methyl 1 41 - amino) - and - (41 - methyl - 31 - amino) - benzoylamino - and 1 - chloro - and - sulpho - 2 - (31 - methyl - 41 - amino) - benzoylamino - 5 - naphthol - 7 - sulphonic acids and the end components used are 2 - carboethoxy -, - benzoyl - (31 - methyl - 41 - amino) - and - 31 and 41 - amino) - benzoyl-, cinnamoyl -, - phenylaectyl -, - phenoxy - acetyl -, -acetyl - and - crotonyl - amino - 5 - naphthol - 7 sulphonic acid, 2 - naphthol and its 4 and 6 - mono - and 3, 6 - and 6, 8 - disulphonic acids, 1 - naphthol - 4 - mono - and 3, 8 - di - sulphonic acids, 2 - carboethoxyamino - 8 - naphthol - 6 - sulphonic acid, 2 - acetyl -, - carboethoxy -, - benzoyl - and - cinnamyl - 5 - naphthol - 1, 7 - disulphonic acids, 1 - chloro - 2 - benzoyl - and - carboethoxy - amino - 5 - naphthol - 7 - sulphonic acids, 4 - methyl - and 2 - sulphonaphthyl (2) - carbamic acid (31 - 4 - dimethyl - 1 - phenyl, 5 - hydroxy - 7 - sulpho - and - sulphamido - ) and (41 - acetyl -, - propionyl and - benzoylamino) - phenylamides and - carbamic acid methyl -, dimethyl -, propyl -, cyclohexyl -, benzyl -, phenyl - and - (41 - phenyl) phenyl - amides 5 - hydroxy - 1, 7 - disulphonaphthyl (2) - and 8 - hydroxy - 6 - sulphonaphthyl (2) - carbamic acid (41 - acetylamino) phenylamides, barbituric acid, 1 - acetylamino - 7 - naphthol, acetoacetylaminobenzene, 1 - phenyl - 3 - methyl - 5 - pyrazolone and its 31 sulphonic acid, 1 - (41 - hydroxyl) phenyl-3 - methyl - 5 - pyrazolone - 31 - carboxylic acid and 1 - [41 - amino - and - (411 acetyl - aminophenyl)] phenyl - 3 - methyl - 5 - pyrazolones.