GB753987A - Monoazodyestuffs, metallised and unmetallised, and processes for their preparation - Google Patents

Abstract

The invention comprises metallized and unmetallized monoazo dyestuffs which in their metal-free state correspond to the formula <FORM:0753987/IV(c)/1> wherein R is the residue of a coupling component which is free of sulphonic or carboxylic acid groups and possesses ortho to -N=N- an enolic or phenolic hydroxy group, y is hydroxy or alkoxy and the nucleus I may bear further substituents. The dyes are prepared by diazotizing a 1-hydroxy - 2 - aminobenzene - morpholylsulphonamide and coupling, in neutral or alkaline medium, with for example a 3-methyl-5-pyrazolone, acetoacetylaminoalkane or acetoacetylamino- or hydroxy-aryl derivative of the benzene or naphthalene series. The dyes may be metallized to give the chromium or cobalt derivatives by known methods, the preferred metallized dyes having one atom of metal to two molecules of the monoazo compound. The metallized dyes give yellow, brown-yellow, orange, red, bordeaux violet and grey shades on wool and silk. They also dye leather and synthetic polyamide fibres. In examples (1-41) monoazo dyes and their chromium and/or cobalt complexes are prepared using the following components; diazo components:- - 1 - hydroxy - 2 - aminobenzene - 4 - or - 5 - morpholylsulphonamide, 1 - hydroxy - 2 - aminobenzene - 6 - bromo - or - chloro - or - nitro- or - methyl - 4 - morpholylsulphonamide, 1 - hydroxy - 2 - amino - 4 - chlorobenzene - 5 - morpholylsulphonamide and 1 - hydroxy - 2 - amino - 4 - chloro - or - methyl - or - tert. butyl - benzene - 6 - morpholylsulphonamide: coupling components:-3 - methyl - 5 pyrazolone, 1 - phenyl - or - (31 - or 41 chloro) - phenyl - or - (21 : 51 - dichloro) - phenyl - or - (31 - ethyl) - phenyl - or - (41 - methyl) - phenyl or (31 - chloro - 41 - methyl) - phenyl - or - (51 : 61 : 71 : 81 - tetrahydro) - naphthyl (11) or (21) - or decahydronaphthyl (21) - 3 - methyl - 5 - pyrazolone, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonamide, 1 - phenyl - or - (41 - methyl) - phenyl - 3 - methyl - 5 - pyrazolone - 31 - methylsulphonamide, 1 - (41 - chloro) - phenyl - 3 - methyl - 5 - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 41 - sulphonic acid - (311 - sulphamido) - phenylamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonic acid - (311 - methoxy) - propylamide or - (211 - hydroxy) - ethylamide, acetoacetylaminobenzene, 1 - acetoacetylamino - 3 - chloro - or - sulphamido - or - 3 - cyano - 4 - methyl - benzene, 1 - or 2 - acetoacetylaminonaphthalene, 1 - acetoacetylaminooctane, 1 - hydroxy - 2 - acetylamino - 4 - methyl or 1 - hydroxy - 2 - propionylamino - 4 - tert. butyl - or 1 - hydroxy - 2 : 4 dimethyl - benzene, 2 - hydroxynaphthalene, 1 - carboethoxyamino - or - acetylamino - or - carbo - (21 - ethoxy) - ethoxyamino - 7 - hydroxynaphthalene, 2 - hydroxynaphthalene - 6 - sulphonamide and 1 - hydroxy - 5 : 8 - dichloronaphthalene.