Patent GB-448131-A (GB)
Title: Manufacture of azo-dyestuffs
Filed: 1934-12-03
Abstract: Azo dyes are made by combining a diazotized base with a pyrazolone of the general formula <FORM:0448131/IV/1> where R and R1 stand for aryl radicals, at least one of which contains one or more groups lending solubility in water, e.g. SO3H or COOH.  They dye wool in an acid bath yellow to red tints of very good fastness properties.  By using components containing groups capable of being chromed, e.g. OH, COOH or arylsulphamino in o-position to the amino group, or COOH or arylsulphamino in o-position to OH dyes are obtained which may be after-chromed on the fibre.  In examples, dyes from the following components are described: 1 - amino - 4 - toluene - 3 - sulphanilide, aniline, sulphanilic acid, anthranilic acid, 1-amino-2-naphthol-4-sulphonic acid, o-aniline-sulphonic acid, 4-chloro-2-aminophenol-6-sulphonic acid, 4 - chloro - 2 - aminophenol, 4 - toluidine - 3 - sulphonic acid, p-aminobenzoic acid, m-aminobenzenesulphanilide, 2 - naphthylamine - 1 - sulphonic acid, o-tolidine, o-chloraniline, 4 : 4<1>-diaminotriphenylmethane, Cleve's acid, o- and p-toluidine, p-anisidine, benzidine, 6-nitro-2-aminophenol-4-sulphonic acid, o-aminophenol, o - aminophenol - 4 - sulphonic acid, 4 - nitro - 2 - aminophenol, 3 - nitro - 5 - amino - 2 - hydroxy - 1 - benzoic acid, 4 : 6-dinitro-2-aminophenol, 5-amino - 2 - hydroxy - 1 - benzoic acid, 4 - chloraniline - 2 - sulphonic acid, benzidine - 3 : 3<1> - dicarboxylic acid, 1 - amino - 3 - sulphonyl - (4<1>-hydroxy-3<1>-carboxyanilido)-benzene, 3-chloro-2 - aminobenzene - 1 - carboxylic acid; 1 - (4<1>-, 3<1>- or 2<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1 - (2<1> - chloro - 4<1> - sulphophenyl) - 3 - phenyl or (4<11> - carboxyphenyl) - 5 - pyrazolone, 1 - (2<1>-hydroxy - 3<1> - carboxy - 5<1> - sulphophenyl) - 3 - phenyl- or 3-(4<11>-chloro- or carboxyphenyl)-5-pyrazolone, 1-(2<1>-diphenylsulphone-4<1>-sulpho-4<11>-hydroxy -3<11>-carboxy)-3-phenyl or 3-(4<111>-chlorophenyl)-5-pyrazolone, 1-(4<1>-hydroxy-3<1>-carboxy-5<1>-sulphophenyl) -3-phenyl-5-pyrazolone, 1-phenyl-3-(4<1>-carboxyphenyl)-5-pyrazolone, 1 - (2<1>-sulpho-1<1>-naphthyl)-3-phenyl-5-pyrazolone, 1 - (2<1>-chloro-5<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1 - (4<1>-sulphophenyl)-3-(4<11> - carboxyphenyl) - 5 - pyrazolone, 1 - (2<1>-methyl-4<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1 - (2<1> : 5<1>-dichloro-4<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1 - (2<1>-nitro-4<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1-(4<1>-nitro-2<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1 - (2<1>- or 3<1>-sulphophenyl)-3-(4<11>-chlorophenyl)-5-pyrazolone, 1-(2<1>-chloro-5<1>-sulphophenyl)-3-(4<11>-chloro- or methylphenyl)-5-pyrazolone, 1-(3<1>-sulphophenyl)-3-(2<11>-naphthyl)-5-pyrazolone, 1-(1<1>-sulpho-2<1>-naphthyl)-3-phenyl-5-pyrazolone, 1 - (4<1> - sulphophenyl) - 3 - (4<11>-methylphenyl)-5-pyrazolone, 1-(2<1>-chloro-6<1>-methyl - 4<1> - sulphophenyl) - 3 - phenyl - 5 - pyrazolone, 1-(4<1>-chloro-2<1>-sulphophenyl)-3-(b -naphthyl) -5-pyrazolone, 1-(4<1>-phenoxy-3<1>-sulphophenyl)-3-phenyl-5-pyrazolone. Specification 436,516 is referred to.  The Specification as open to inspection under Sect. 91 comprises also the following tabulated examples: 6-nitro-2-aminophenol-4-sulphonic acid or 4-sulpho-2-aminobenzene-1-carboxylic acid --> 1 - phenyl - 3 - (4<1> - carboxyphenyl)-5-pyrazolone, 5-nitro-2-aminophenol or 6-nitro-4-chloro-2-aminophenol --> 1-(2<1> : 4<1>-dichloro-6<1>-sulphophenyl) - 3 - phenyl - 5 - pyrazolone, 4-methyl-6-nitro-2-aminophenol --> 1-(2<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 5-nitro-2-aminophenol --> 1-(2<1> : 4<1>-dimethyl-6<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1-(2<1>-sulphophenyl)-3-phenyl-5-pyrazolone, 1-(2<1>-chloro-5<1>-sulphophenyl)-3-phenyl-5-pyrazolone or 1-(2<1>-methyl-4<1>-chloro-6<1>-sulphophenyl) -3-phenyl-5-pyrazolone, 4 - chloro - 2 - aminophenol - 6 - sulphonic acid --> 1-(2<1>-chloro-5<1>-sulphophenyl)-3-phenyl-5-pyrazolone. This subject-matter does not appear in the Specification as accepted.