Patent GB-211752-A (GB)
Title: Manufacture of azo-dyestuffs
IPC: C09B35/35
Filed: 1923-04-25
Abstract: Azo dyes are obtained by coupling, either in substance or on the fibre, tetrazotized diaminoazo compounds with arylamides of 2 : 3-oxynaphthoic acid, for example, anilides, chloranilides, anisidides, phenetidides, a -or b -naphthalide, or 2 : 3-oxynaphthoyl-aminothiazole.  The dyestuffs prepared in substance yield lakes by the usual processes; the shades on the fibre are rendered faster to light by after-treatment with copper sulphate. The diamino compounds used are particularly those having at least one amino group in the p-position to the azo group and are therefore obtained by coupling diazotized nitroamines or monoacyldiamines, such as m- and p-nitranilines, chlornitranilines, nitrotoluidines, nitroanisidines, nitro-aminothiophenol-methylethers, nitronaphthylamines or the corresponding monoacyldiamines, with middle components such as m-toluidine, p-xylidine, p-cresidine, acetyl-m-toluylene-diamine, and a -naphthylamine and its derivatives coupling in the 4-position, and reducing or saponifying the products. In an example the dyestuff from tetrazotized p-aminobenzene-azo-p-cresidine and 2 : 3-oxynaphthoic-p-phenetidide is prepared in the presence of turkey-red oil; it yields lakes by the usual processes; cotton impregnated with 2 : 3-oxynaphthoic-a -naphthalide is dyed black by developing with tetrazotized p-aminobenzene-azo-1-naphthylamine.  A table is given of the shades of dyeings from the following arylides:-anilide, a -naphthalide, p-phenetidide, p-anisidide, and the diaminoazo compounds from the following pairs of compounds:-p-nitraniline and m-toluidine, or acetyl-m-toluylenediamine, or p-cresidine, or 4-chlor-1 : 2-anisidine or a -naphthylamine or tetrahydro-a -naphthylamine; 2-chlor-4-nitraniline and acetyl-m-toluylene diamine or p-cresidine; 2 : 5-dichlor-4-nitraniline and acetyl-m-toluylene diamine or p-cresidine; 2 : 6-dichlor-4-nitraniline and p-cresidine or 4-nitro-1 : 2-anisidine; 5-nitro-1 : 2-toluidine and p-cresidine; 5-nitro-1 : 2 anisidine and p-cresidine; 4-nitro-2-amino-1-thiophenol-methyl ether and p-cresidine; 2-nitro-1 : 4-phenylenediamine (1 mol.) and p-cresidine (1 mol.). Specifications 13766/12 and 100,804 are referred to.  Nitroaminothiophenol-methylethers may be prepared by condensing methyl mercaptan with a dinitro-chlorbenzene and partially reducing the product.ALSO:Black shades, fast to light, and chlorine are produced upon the fibre by impregnating with arylamides of 2 : 3-oxynaphthoic acid, for example, anilides, chloranilides, anisidides, phenetidides, a - or b -napthalide, or 2 : 3-oxynaphthoyl-aminothiazole; and developing with tetrazotized diaminoazo compounds; the shades are rendered faster to light by after-treatment with copper sulphate. The diamino compounds used are particularly those having at least one amino group in the para position to the azo group and are therefore obtained by coupling diazotized nitro amines or monoacyldiamines, such as m- and p-nitraniline, chlornitranilines, nitrotoluidines, nitroanisidines, nitroaminothiophenol-methylethers, nitronaphthylamines, or the corresponding monacyldiamines, with middle components such as m-toluidine, p-xylidine, p-cresidine, acetyl-m-toluylene-diamine, and a -naphthylamine and its derivatives coupling in the 4-position and reducing or saponifying the products.  In an example, cotton impregnated with 2 : 3-oxynaphthoic-a -naphthalide is dyed black by developing with tetrazotized p-aminobenzene-azo-1-naphthylamine.  A table is given of the shades of dyeings from the following arylides :-anilide, a -naphthalide, p-phenetidide, p-anisidide, and the diaminoazo compounds obtainable from the following pairs of compounds :-p-nitraniline and m-toluidine, or acetyl-m-toluylenediamine, or p-cresidine, or 4-chlor-1 : 2-anisidine or a -naphthylamine or tetrahydro-a -naphthylamine; 2-chlor-4-nitraniline and acetyl-m-toluylene diamine or p-cresidine; 2 : 5-dichlor-4-nitraniline and acetyl-m-toluylene-diamine or p p-cresidine; 2 : 6-dichlor-4-nitraniline and p-cresidine or 4-nitro-1- : 2-anisidine : 5-nitro-1 : 2 toluidine and p-cresidine; 5-nitro-1 : 2-anisidine and p-cresidine; 4-nitro-2-amino-1-thiophenol-methyl ether and p-cresidine; 2-nitro-1 : 4-phenylenediamine (1 mol) and p-cresidine (1 mol). Specifications 13766/12 and 100,804 are referred to.