Patent GB-432020-A (GB)
Title: The manufacture of new azodyestuffs
IPC: C09B29/30
Filed: 1933-12-14
Abstract: Azo dyes are prepared by coupling a diazotized amine of the formula <FORM:0432020/IV/1> (wherein X stands for hydrogen or a monovalent substituent other than hydrogen and wherein the benzene nucleus may contain further substituents other than hydroxy groups) with a component of the formula <FORM:0432020/IV/2> (wherein Y stands for hydrogen, alkyl or aryl).  The products dye animal fibres yellowish-orange to bluish-red shades.  In examples or a table the following dyes are referred to: diazotized aniline-o-sulphonic acid, 2.4.5-trimethyl - 6 - sulphoaniline, 3-methyl-4-chloro-6-sulphoaniline and 4- (or 5-) -acylamino-2-sulphoaniline coupled with 1.8.6-acetylaminonaphthol-sulphonic acid; diazotized 2.4-dimethyl-6-sulphoaniline coupled with 1.8.6-acetylaminonaphtholsulphonic acid or the corresponding carbethoxyamino-, toluenesulphamino- or benzoylamino-derivatives or the N-methyl-, phenyl- or benzyl-derivatives; diazotized 2-methyl-4-chloro-6-sulphoaniline is coupled with 1.8.6 - methoxyacetylaminonaphthol-sulphonic acid; diazotized 2.4-dimethyl-6-sulphoaniline is coupled with 2.8.6- and 2.5.7-acetylaminonaphtholsulphonic acids and acetylmethylaminonaphthol sulphonic acids; diazotized aniline-o-sulphonic acid is coupled with 2.8.6-and p 2.5.7-acetylaminonaphthol sulphonic acids, and similarly diazotized 4-methyl-6-sulphoaniline, 4-chloraniline-2-sulphonic acid, 2-methyl-4-chloro-6-sulphoaniline and 3-chloro-4-methyl-6-sulphoaniline may be so coupled or coupled with 2.8.6-benzoylaminonaphthol-sulphonic acid or -carbalkoxyaminonaphthol sulphonic acid; diazotized 3- (or 4-) -acetylamino-6-sulphoaniline is coupled with 1.5.7-acetylaminonaphthol sulphonic acid or -benzoylaminonaphthol sulphonic acid, or 2.5.7- or 2.8.6 - acylaminonaphthol sulphonic acids; diazotized 2 - phenoxy - 4 - methyl - 5 - chlor-6-sulphoaniline, 2.4.5 - trimethyl - 3 - chlor - 6 - sulphoaniline, 2.3.5 - trimethyl - 4 - chloro - 6 - sulphoaniline, 3 - methyl - 4 - chloro - 6 - sulphoaniline, 3 - chloro - 6 - sulphoaniline and 2.4.5-trimethyl - 6 - sulphoaniline are coupled with 2.8.6 - acetylaminonaphtholsulphonic acid; diazotized 2 - phenoxy - 4 - methyl - 5 - chloro-6-sulphoaniline, 2.4.6 - trimethyl - 3 - chloro - 6 - sulphoaniline, 2.3.5 - trimethyl - 4 - chloro - 6 - sulphoaniline, 3 - methyl - 4 - chloro - 6 - sulphoaniline, 3 - chloro - 6 - sulphoaniline and 2.4.6-trimethyl - 6 - sulphoaniline are coupled with 2.5.7 - acetylaminonaphthol - sulphonic acid; diazotized 2.4 - dimethyl - 6 - sulphoaniline, 2-methoxy - 6 - sulphoaniline and 2 - methyl - 4 - chloro-6-sulphoaniline are coupled with 1.5.7-acetylaminonaphthol sulphonic acid; diazotized 2.4-dimethyl - 6 - sulphoaniline and 2-methyl-4-chloro-6-sulphoaniline are coupled with 2.8.6-benzoylaminonaphthol sulphonic acid and 2.8.6-acetylmethylaminonaphthol sulphonic acid.  The Provisional Specification relates to the coupling of the above diazo compounds with components of the formula <FORM:0432020/IV/3> wherein Y stands for hydrogen, alkyl or aryl and one of the Z's stands for a sulphonic acid group and the other for hydrogen.