Patent GB-421610-A (GB)
Title: Manufacture of azo-dyestuffs insoluble in water
IPC: C09B29/28
Filed: 1933-06-26
Abstract: Azo dyes; lakes; azo dyes, forming upon the material; printing.--Azo dyestuffs, insoluble in water, are manufactured by coupling, in substance, on the fibre or on substrata, a diazo-, tetrazo- or diazo - azo - compound with a 1-hydroxy-3 : 5-diarylaminobenzene (obtainable by condensing phloroglucinol with the appropriate aminoaryl compound), only such components being used as do not contain any group lending solubility.  In examples: (1) cotton yarn is impregnated with a solution of 1-hydroxy-3 : 5-diphenylaminobenzene or the corresponding di-(4<1>-methylphenylamino)- or di - (2<1> - 4<1> - dimethylphenylamino) - compounds, and developed with diazotized 1-amino-2 : 5-dichlorobenzene, yielding yellow-brown dyeings; (2) an orange-brown dyeing is similarly obtained from 1 - hydroxy - 3 : 5 - di - (4<1> - methoxyphenylamino) - benzene and diazotized 1 - amino - 2 - (4<1> - chlorophenoxy) - 5 - chlorobenzene; the same coupling component yields a deep reddish-brown dyeing with tetrazotized 4 : 4<1>-diamino-3 : 3<1>-dichlorodiphenyl and a brownish garnet with diazotized 4 - amino - 3 : 2<1> - dimethylazo-benzene.  The Specification as open to inspection under Sect. 91 comprises also the following subject-matter: (a) the first dyestuff of (2) above may be prepared by the nitrosamine printing process, by printing with a mixture prepared from an alkali salt of the nitrosamine of 1-amino-2-(4<1>-chlorophenoxy)-5-chlorobenzene and an alkali salt of 1-hydroxy-3 : 5-di-(4<1>-methoxyphenylamino)-benzene; (b) wool is grounded with a caustic soda solution of 1-hydroxy-3 : 5-di-(4<1>-chlorophenylamino)-benzene and developed with diazotized 1-amino-2-phenoxy-5-chlorobenzene, yielding a yellow-brown dyeing; (c) in an additional example the dyestuff 1-amino-2-chloro - 4 - nitrobenzene --> 1 - hydroxy - 3 : 5-di-(4<1>-methylphenylamino)-benzene is prepared in substance, and yields a brown lake when mixed with substrata; (d) a table gives the shades obtained from additional dyestuffs, the following additional components being specified: diazo-components: 1-amino-3-chlorobenzene, 1-amino-2-methoxy-4-nitrobenzene, 1-amino-2-methoxy-5-(diethylaminosulphonyl)-benzene, 1-amino-2-methoxy-5-chlorobenzene, 4-amino-4<1>-methoxydiphenylamine, 1-amino-2 : 4 : 5-trichlorobenzene, 1-aminoanthraquinone, 2-amino - 1 : 6 - dibromonaphthalene, 1 - amino - 2 - (2<1> : 5<1> - dichlorophenoxy) - 5 - chlorobenzene, 1 - amino - 2 - chloro - 5 - trifluoromethylbenzene, 1-amino-4-benzoylamino-2 : 5-diethoxybenzene, 1-amino-3-benzoylbenzene, 1-amino-2-methyl-5 - (carbonyl - [1<1> - amino - 2<1> : 5<1> - dimethoxy - benzene])-benzene, 3-aminocarbazole, 4 : 4<1>-diamino-3 : 3<1>-dimethoxydiphenyl, 1-amino-4-benzoylamino-2 : 5-dichlorobenzene, 1-amino-3 - methyl - 2 : 4 - dichlorobenzene, 1 - amino - 2 - phenylsulphonylbenzene; coupling components: 1 - hydroxy - 3 : 5 - di - (4<1>-ethoxyphenylamino) - benzene, 1-hydroxy-3 : 5-di-(4<1>-phenoxyphenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (3<1> - 4<1> dichlorophenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (3<1> - methylphenylamino) - benzene, 1-hydroxy-3 : 5-di-(2<1>-methyl-4<1>-chlorophenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (2<1> - methoxy - 4<1> - chlorophenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (4<1> - acetylaminophenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (naphthyl - 2<1> - amino) - benzene, 1 - hydroxy - 3 : 5 - di - (quinolyl - 6<1> - amino) - benzene, 1 - hydroxy - 3 : 5-di-(4<1>-chloro-3<1>-nitrophenylamino)-benzene, 1 - hydroxy - 3 : 5 - di - (4<1> - [4<11> - methoxyphenylamino] - phenylamino) - benzene, 1 - hydroxy - 3 : 5 - di - (3<1> - methoxynaphthyl - 2<1>-amino)-benzene. This subject-matter does not appear in the Specification as accepted.