GB423736A - Manufacture of azo-dyestuffs insoluble in water - Google Patents

Abstract

Azo dyes insoluble in water are made in substance, on the fibre or on a substratum by coupling a diazo compound with a 3-hydroxy-1 : 2-benzofluorenone, which may contain substituents in the nuclei not containing the hydroxy group. Olive to black shades are obtained. In examples: (1) diazotized 1-amino-4-benzoylamino-5-methoxy-2-chlorobenzene is coupled with 3-hydroxy-1 : 2-benzofluorenone; (2) cotton is grounded with the same coupling component and developed with diazotized 1-amino-2-methyl-4-chlorobenzene. Additional components specified in a table are 1-amino-2-methoxy- or phenoxy-5-chlorobenzene, 2 : 5-dichloraniline, 1-amino-2-methyl-4-nitrobenzene, 4-amino-3 : 2<1>-dimethylazobenzene, dianisidine (after treated with copper); 3-hydroxy-6-methyl- or 7-chloro-1 : 2-benzofluorenone. 3-Hydroxy-6-methyl-1 : 2-benzofluorenone is made by condensing 1-methoxynaphthalene in the 4-position with 2- p-toluenesulphamino-4-methylbenzoylchloride, splitting off the p-toluenesulpho group from the ketone thus obtained, diazotizing the amino compound and boiling to form the benzofluorenone compound which is then saponified to the hydroxy compound. 3 - Hydroxy - 7 - chloro - 1 : 2 - benzofluorenone is made by condensing 1-methoxynaphthalene with 2 : 5-dichlorobenzoylchloride, replacing the chlorine atom in oposition to the CO-group in the ketone thus obtained by an amino group, diazotizing, boiling and saponifying. The Specification as open to inspection under Sect. 91 comprises also examples in which viscose, silk and wool are treated with 3-hydroxy-1 : 2-benzofluorenone and developed respectively with tetrazotized 4 : 4<1>-diamino-3 : 3<1>-dichlorodiphenyl, diazotized 1-amino-2-chloro-5-trifluoromethylbenzene and diazotized 1-amino-2-methyl-3-chlorobenzene. The following additional components are also specified in a table : 1-amino-2-chloro-4-nitrobenzene, 1-amino-2-methoxy-4-nitrobenzene, o-chloraniline, 1-amino-2-methyl-3- or 5-chlorobenzene, 1-amino-3-methyl-2 : 4-dichlorobenzene, 1-amino-4-benzoylamino-2 : 5 - dichlorobenzene, 1-amino-2-(2<1> : 5<1> - dichlorophenoxy) - 5 - chlorobenzene, 1-amino-3-benzoylbenzene, 3-amino-carbazole, 2-amino-1 : 6-dibromonaphthalene, 1-amino-2-(2<1>-chlorophenoxy)-5-chlorobenzene, o-nitraniline, 1-amino-4-methyl-2-nitrobenzene, 1-amino-2-diphenylsulphone, 1-aminoanthraquinone; 3-hydroxy - 1 : 2 : 6 : 7 - dibenzofluorenone. This subject-matter does not appear in the Specification as accepted.