Patent GB-372338-A (GB)
Title: Manufacture of new azo-dyestuffs
IPC: C09B29/20
Filed: 1930-12-30
Abstract: Azo dyes are made by combining a diazo-, diazoazo- or tetrazoazo compound of the benzene series which may contain one or more alkyl, alkoxy, aryloxy, aroylamino, phenylamino or nitro groups or halogen as substituents, or a tetrazo-compound of the diphenyl series which may contain alkyl, alkoxy, nitro groups or halogen, or a diazo, diazoazo or tetrazoazo-compound of the naphthalene series, or a diazo-compound of the anthraquinone series, with an arylamide of the formula: <FORM:0372338/IV/1> where both X's mean methyl groups, or one X = methyl and the other X = chlorine, n = 1 or 2 and where R stands, in case n = 1, for a benzene or naphthalene nucleus which may be substituted by alkyl, alkoxy, halogen or a nitro group, or for a carbazole nucleus, and in case n = 2, for a benzene or diphenyl nucleus which may be substituted by alkyl, alkoxy, halogen or a nitro group, or for a naphthalene or carbazole nucleus.  The dyestuffs may be prepared in substance and used for lakes or on the fibre, such as cotton, wool, natural or regenerated cellulose, or ethers or esters of cellulose.  Brown to black shades are produced suitable for batic dyeing.  In examples, dyeings are produced on cotton, acetate silk, agfa viscose and wool by the ice-colour method using the following components: diazo components:--2 : 5-dichloraniline, 4- or 5-nitro-2-methoxyaniline, 3 : 2<1> - dimethyl - 4 - aminoazobenzene, 4 - nitro - 2 - or 3-methyl - 1 - aniline, dianisidine, 3 : 3<1>-dichlorobenzidine, 2 : 2<1> : 5<1>-or 3 : 2<1> : 5<1> - trimethoxy-4 : 4<1> - diaminoazobenzene, 2 : 5-dimethoxy-2<1>-methyl-4 : 4<1>-diaminoazobenzene, 3 : 2<1>-dimethoxy-4-aminoazobenzene, 4-benzoylamino-3-methoxy-6-chloroaniline, 2<1>-ethoxybenzeneazo-4-aminonaphthalene, m-chloraniline, 4- or 5-chlor-2-methyl-1-aniline, 4 - amino - 4<1> - methoxydiphenylamine, o-nitraniline, 2 - nitro - 4-methyl - 1 - aniline, 1-aminoanthraquinone, 4<1>-nitro-2 : 5-dimethoxy-4 - aminoazobenzene, 5 - chlor - 2 - phenoxy - 1 - aniline, 4-benzoylamino-3-methyl-6-methoxy-1-aminobenzene, 2 - nitro - 4 - methoxy - 1 - aniline, 2 : 4 : 5-trichloraniline, 2 : 5-dichlor-4-methyl-1-aniline, 4-chlor-2-nitraniline, a -naphthylamine, 4 - aminobenzeneazo-4<1> - aminonaphthalene, 2 - amino - 4 - chloro - diphenylether, 5 - chlor - 2 - methoxy - 1 - aniline, 4 - amino - 3 - ethoxy - 4<1> - phenoxy - 6 - methylazobenzene, 4 - amino-4<1>-benzoylamino - 3 - methoxy-2<1> : 5<1>-diethoxy-6-methylazobenzene, 4-amino-4<1>-phenylaminoazobenzene, 4-amino-3-ethoxy-4<1>-chloro-6-methylazobenzene, 4 : 4<1>-diamino-2 : 5-dimethoxy-2<1>-chloroazobenzene, tolidine, 4 : 4<1>-diamino-3 : 3<1> dimethoxy - 6 - nitrodiphenyl; coupling components:--the 4 - hydroxy - 1 : 2 - dimethyl - 5 - benzoyl derivatives of a - or b -naphthylamine, 2 : 5-dimethoxyaniline, aniline, 2 : 4-dimethylaniline, o-anisidine, m- or p-toluidine, m-chloraniline, 1 - amino - 2 - methoxy - 5 - chlorbenzene, 1-amino-2-methoxy-5-nitrobenzene, 1-amino-4-methoxynaphthalene, 2 - amino - 1 - methyl - naphthalene, 1 - amino - 5 - chlornaphthalene, 1-amino - 5 - nitronaphthalene, 1 : 5 - diaminonaphthalene, p-phenylenediamine, dianisidine, tolidine and 2-nitrobenzidine; the 4-hydroxy-1-chloro-2-methyl-5-benzoyl derivatives of aniline, 1 - amino - 2-methyl - 4 - or 5 - chlorobenzene, a -naphthylamine, 1-amino-2-methoxy - 4-chlorobenzene, p - chloraniline, p - phenylenediamine, 1 : 4 - diamino - 2 - methyl - 5 - methoxybenzene, 1 : 5 - diamino - naphthalene, 1 : 4 - diamino-2-methoxy - 5 - chlorobenzene, 1 : 4 - diamino-2 : 5- dimethylbenzene, and 2 : 2<1>-dichlorobenzidine, the 4-hydroxy-2-chloro-1-methyl-5-benzoyl derivatives of 1-amino-2-methyl-4-chlorobenzene, 1 : 4 - diamino - 2 : 5 - dimethylbenzene, aniline, 1-amino-2 : 5-dimethoxybenzene, b -naphthylamine, 3-aminocarbazole, p-phenylenediamine, 1 : 4-diamino-2-methyl-5-chlorobenzene, 1 : 4-diamino-2 : 5-dimethoxybenzene, 1 : 4-diamino-2 - methoxy - 5 - chlorobenzene, 1 : 5 - diaminonaphthalene, 3 : 6-diaminocarbazole.  1 : 2-Substituted -4- hydroxybenzene-5 - carboylaminoaryls above referred to are made by condensing the appropriate 1 : 2-substituted-4-hydroxybenzene-5-carboxylic acids (c.f. Specification 347,407) with a monamine or diamine of the benzene, naphthalene or carbazole series, or with a diamine of the diphenyl series, e.g. according to Specification 358,477.