US 4,048,153 AGranted

Azo dyes having an optionally substituted 1-azo-3-nitro-4-arylaminophenyl nucleus

AssigneeSandoz Ltd.

InventorDaniel Van Assche

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Abstract

Water-soluble azo dyes of the formula ##STR1## in which R.sub.1 signifies an aromatic or heterocyclic radical which may be substituted, R.sub.2 has one of the significances of 1 or is the radical of a coupling component, for example, a radical of a coupling component bearing an active methylene group, And the molecule contains 1 or 2 sulfo groups, And the ring A may be further substituted, And processes for their synthesis. These dyes are useful for the dyeing and printing of a variety of organic materials including natural and synthetic polyamide fibers, e.g., wool, and paper. The obtained dyeings and prints exhibit good fastness to light and wet treatments as well as to gas fumes and rubbing, and dyeings obtained in combination with blue dyes, for example blue cationic anthraquinone dyes, exhibit good resistance to catalytic fading.

A compound of the formula ##STR146## wherein R.sub.2 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, substituted phenoxyphenyl, anilinophenyl, substituted anilinophenyl, phenylsulfinylphenyl, substituted phenylsulfinylphenyl, substituted phenylsulfonylphenyl, phenylazophenyl, substituted phenylazophenyl or ##STR147## wherein each substituent of substituted phenyl, substituted naphthyl, substituted phenoxyphenyl, substituted anilinophenyl, substituted phenylsulfinylphenyl, substituted phenylsulfonylphenyl, and substituted phenylazophenyl is independently alkyl of 1 to 12 carbon atoms, alkyl of 1 to 12 carbon atoms substituted by halo, hydroxy, cyano, phenyl or naphthyl, alkoxy of 1 to 4 carbon atoms, sulfoalkoxy of 1 to 4 carbon atoms, phenylsulfonyl, naphthylsulfonyl, phenoxy, naphthyloxy, halo, nitro, alkoxycarbonyl wherein the alkoxy radical has 1 to 4 carbon atoms, sulfo, --CONH.sub.2, carboxy, phenyl, naphthyl, cyclohexyl, alkylsulfonyl of 1 to 12 carbon atoms, phenylsulfonyloxy, p-tolylsulfonyloxy, benzoyloxy, trifluoromethyl, trichloromethyl, ##STR148## wherein R.sub.9 is hydrogen, halo or alkoxy of 1 to 4 carbon atoms,

R.sub.10 is methyl or phenyl,
each R' is independently hydrogen, alkyl of 1 to 4 carbon atoms, phenyl, naphthyl or cyclohexyl, and
each R" is independently hydrogen or alkyl of 1 to 4 carbon atoms,
R.sub.4 is hydrogen, alkyl of 1 to 12 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, carboxy or alkoxycarbonyl wherein the alkoxy radical has 1 to 4 carbon atoms,
R.sub.5 is ##STR149## each R.sub.8 is independently hydrogen acetamido, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or naphthyl, alkoxy of 1 to 4 carbon atoms, phenyl, naphthyl, sulfo, halo, nitro or ##STR150## wherein each R' is independently hydrogen, alkyl of 1 to 4 carbon atoms, phenyl, naphthyl or cyclohexyl, and
m is 0, 1 or 2,
wherein each halo is independently chloro, bromo, fluoro or iodo,
with the proviso that the molecule contains 1 to 2 sulfo groups.

5 more elements

Abstract

Claims25