GB407206A - Manufacture of azo-dyestuffs - Google Patents

Abstract

Azo dyes; azo dyes, forming on the material; cellulose acetate, dyeing; regenerated celluloses, dyeing.--Azo dyes are produced in substance or on the fibre by coupling a diazotized aryl ether of 2-amino-4-methoxy-5-acetylaminophenol with an arylide of 2 : 3-oxynaphthoic acid. The dyeings are violet to blue-violet and particularly fast to light, to chlorine and to kier-boiling. The following examples are specified: (1) the dyestuff 2-amino-4-methoxy-5-acetylamino-1 : 1<1>-diphenylether --> the p-anisidide of 2 : 3-oxynaphthoic acid is produced in substance; (2) cotton yarn, impregnated with a solution of the 2<1>-methyl-4<1>-methoxyanilide of 2 : 3-oxynaphthoic acid containing sodium hydroxide and turkey red oil, is developed to a pure violet dyeing of particularly good fastness to light in a neutralized solution of diazotized 2 -amino - 4 - methoxy - 5 - acetyl - amino - 2<1> - methyl - 1 : 1<1> - diphenylether; a similar dyeing is obtained with the use of the 2<1> : 4<1> - dimethoxy - 5<1> - chloranilide of 2 : 3 oxynaphthoic acid and a blue-violet dyeing with the use of the p-anisidide of 2 : 3-oxynaphthoic acid; (3) wool yarn, impregnated with a solution of the anilide of 2 : 3-oxynaphthoic acid containing sodium hydroxide and turkey red oil, is developed in a neutralized solution of diazotized 2-amino-4 : 4<1>-dimethoxy-5-acetylamino-1 : 1<1>-diphenylether, rinsed and soaped to obtain a fast pure violet dyeing; a similar dyeing is obtained with the use of the p-anisidide of 2 : 3-oxynaphthoic acid; (4) cotton yarn, impregnated with a solution of the o-anisidide of 2 : 3-oxynaphthoic acid containing sodium hydroxide, turkey red oil and formaldehyde, is developed in a neutralized solution of diazotized 2-amino-4-methoxy-5-acetylamino - 4<1> - methyl - 1 : 1<1> - diphenylether, rinsed and soaped to obtain a fast bluish violet dyeing; violet dyeings are also obtained with the use of the 2<1>-methyl-4<1>-methoxyanilide of 2 : 3-oxynaphthoic acid and by the similar production on the fibre of the dyestuffs 2-amino-4 - methoxy - 5 - acetylamino - 2<1> - chloro - 1 : 1<1> - diphenylether --> the b -naphthylamide or the 2<1> : 4<1>-dimethoxy-5<1>-chloranilide of 2 : 3-oxynaphthoic acid; the process is also applicable in piece-dyeing and in printing and the dyestuffs may also be produced upon other fibres, such as wool, silk and artificial silks of the viscose, cuprammonium and cellulose acetate types; in the application to wool the process of Specification 310,758, [Class 15 (ii)], may be employed. Specifications 202,984, 294,883, [both in Class 15 (ii)], and 383,064 also are referred to. Aryl ethers of 2-amino-4-methoxy-5-acetylaminophenol are obtained by reducing the nitro groups in the condensation products of 1-chloro-2-nitro-4-methoxy-5-amino- or acetylaminobenzene with phenol or its nuclear substitution products, such as o-, m- or p-cresol, o-, m- or p-chlorophenol, a chlorocresol, a dichlorophenol, a monoalkylether of hydroquinone, resorcinol or pyrocatechol or chloroguaiacol, after acetylation, if necessary, of the amino group.