Patent GB-210217-A (GB)
Title: Manufacture of azo-dyestuffs
Filed: 1922-11-23
Abstract: Insoluble azo dyestuffs are prepared, in substance or on the fibre, by coupling a diazo compound, not containing a sulphonic or carboxylic group, with a diacylacetyl compound of the formula Y.CO.CH2.CO.NH.X.NH.CO.CH2.CO.Y. where Y is any aliphatic or aromatic radicle and X is an aromatic residue, for example an aryl or diaryl residue, or a residue of the general formula <FORM:0210217/2/1> wherein R, R1 are the same or different aryl residues united by Z, which may be O, S, -CH2-, -CO-, -NH-, -NH.CO-, -N=N, <FORM:0210217/2/2> or the like.  These second components may be made by heating together, advantageously in a solvent or diluent, an acylacetic ester and a diamine of the formula NH2.X.NH2 where X has the above defined meaning; for example two molecular proportions of acetoacetic ester or a homologue or analogue thereof such as benzoylacetic ester may be condensed with p-phenylene diamine, a naphthalene diamine, a diaminoanthraquinone, benzidine and its derivatives, thioaniline, diaminodiphenylether, diaminodiphenylmethane, diaminodiphenylamine, diaminoazobenzene, diaminoazoxybenzene, diaminodiphenylurea, or aminobenzoylphenylenediamine.  Useful diazo components are aniline and its homologues, anisidines, chlor-and nitro-anilines, chlor-and nitro-toluidines, chlor-and nitro-anisidines, naphthylamines, aminoanthraquinones, aminoazo compounds, and diamines.  The dyestuffs are useful for production of greenish-yellow to orange-brown lakes and pigments.  According to examples insoluble yellow lake dyestuffs are produced from 2 : 5-dichloraniline and diacetoacetyl-o-tolidide, o-chloraniline and dibenzoylacetylbenzidide, and from 5-chlor-2-toluidine and diacetoacetyl-4 : 41-diaminobenzophenone.  A table is given showing the tints of the dyes obtainable from the following diazo components:-aniline, o-toluidine, o-, m-, and p-chloraniline, 2 : 5-dichloraniline, 4- or 5-chlor-2-toluidine, 2- or 3-chlor-4-toluidine, 4- or 5-chlor-2-anisidine, 4-chlor-2-nitroaniline, o-nitro-aniline, 3-nitro-4-toluidine, 5-nitro-2-toluidine, 4-or 5-nitro-2-anisidine, 3-nitro-4-anisidine, 4-nitro-1-naphthylamine, p - amino-acetanilide, o - amino - diphenylether, a - or b -aminoanthraquinone, 3-aminocarbazole, o-aminoazotoluene, aminoazo - p - cresol - methylether, p - aminobenzeazo-dimethylaniline, m-nitrobenzene-azo-m-toluidine, p-chlorbenzene-azo-p-cresidine, benzene-azo-1-naphthylamine, o-chlorbenzene-azo-1-naphthylamine, 2 : 5-dimethoxybenzene-azo-1-naphthylamine, o-anisol-azo-1-naphthylamine, p-methoxybenzene-azo-1-amino-2-naphthol-methyl-or ethylether, p-aminobenzene-azo-1-naphthylamine, dianisidine, 4 : 41-diaminodiphenylamine, and o : o1-dichlorbenzidine; and from the following second components:-diacetoacetyl- or dibenzoylacetyl-benzidide, diacetoacetyl- or dibenzoylacetyl-o-toluidide, diacetoacetyl-o : o1-dichlorbenzidide, diacetoacetyl-dianisidide, diacetoacetyl-4 : 41-diaminobenzophenone, diacetoacetyl-4 : 41-diamino-3 : 31-ditolymethane, diacetoacetyl-4 : 41-diaminoazobenzene, diacetoacetyl-4 : 41-diaminoazoxybenzene, and diacetoacetyl-4 : 41-diamino-diphenylurea.ALSO:Fast-greenish-yellow, yellow, orange, orange-brown &c. shades are produced on the fibre by impregnating with a diacylacetyl-diamino-compound and dyeing or printing with diazo compounds not containing sulphonic or carboxylic-groups, or by printing by the nitrosamine process.  The diacylacetyl compounds are of the general formula Y. CO. CH2. CO. NH. X NH. CO. CH2. CO. Y where Y is any aliphatic or aromatic radicle and X is an aromatic residue, for example aryl or diaryl, or a residue of the formula <FORM:0210217/15/1> where R, R1 are the same or different aryl residues united by Z which may be O, S, -CH2-, -CO-, -NH-, -NH.CO-, -N = N-, <FORM:0210217/15/2> , <FORM:0210217/15/3> , <FORM:0210217/15/4> , or the like.  As diazo components may be used aniline and its homologues, anisidines, chlor - and nitro - anilines, chlor - and nitro - toluidines, chlor - and nitro - anisidines, naphthylamines, amino - anthraquinones, aminoazo compounds, and diamines.  The diacylacetyldiamino compounds may be derived from two molecular proportions of acetoaetic ester or a homologue or analogue thereof such as benzoylacetic ester, and p-phenylenediamine, a naphthalene diamine, diamino-anthraquinone, benzidine and its derivatives, thioaniline, diamino-diphenylether, diamino-diphenyl-methane, diamino-diphenylamine, diamino-azobenzene, diaminoazoxybenzene, diamino-diphenylurea, or aminobenzoyl-phenylenediamine.  Examples are given of the dyeing of yarn by the use of the following pairs of components :-diacetoacetyl-o-tolidide and 5-chlor-2-toluidine or o-chlor-anilide or o-nitro-aniline, dibenzoylacetyl-o-tolidide and 2-chlor-4-toluidine, diacetoacetyl - 4 : 41 - diamino-azoxybenzene and o-chloraniline, diacetoacetyl-4 : 41-diamino-azobenzene and o-nitro-aniline.  The tints of a large number of dyestuffs are tabulated.