GB858590A - New benzene-monoazo-benzene dyestuffs and their metal complexes - Google Patents

Abstract

The invention comprises dyes of formula: <FORM:0858590/IV (c)/1> where R1 is a hydrogen or halogen atom, an alkyl, alkoxy, alkoyl, aroyl, carboxylic acid amide or sulphonic acid amide group which may be substituted by one or two aliphatic, aromatic or heterocyclic radicals, R2 is alkyl and R3 and R4 are hydrogen atoms or alkoylamino or carbalkoxylamino groups, one of R3 and R4 being hydrogen and the other an alkoyl- or carbalkoxylamino group, and their metal complexes in which one metal ion is combined with one or two radicals of a complex-forming compound, at least one of which is that of a dye of the above formula while the other may also be that of another complex-forming coloured or colourless compound. They are made by coupling a diazotised aniline derivative corresponding to R1 with the appropriate phenol and, if desired, converting the products, alone or in admixture with other complex-forming monoazo dyes, into metal complexes in which one metal ion is combined with one or two dye radicals and, if desired, reacting the complexes with complex-forming coloured or colourless compounds. Representative of specified diazo components are: 1- methoxy-, 1, 4- diethoxy- and 1-methoxy-4- methyl- 2- aminobenzenes, 1- methoxy -2-aminobenzene -4- sulphonic acid amide and N-methyl, N- methyl -N- 2- hydroxyethyl and N-21-chlorophenyl derivatives thereof, 1- methoxy -2-aminobenzene -4- sulphonic acid pyrrolidide, 1-methoxy -2- aminobenzene -4- carboxylic acid amide and N, N- dimethyl, N- cyclohexyl and N-(31- methoxy)- propyl derivatives thereof and 3-amino -4- aceto- and benzophenones. Specified coupling components include 1-methyl, -amyland -cyclohexyl -3- acetylamino -4- phenols, 1-hydroxy -4-(N- acetyl, -isovateryl, -carbopropoxy, -carbo- (21- ethoxy)- ethoxy)- aminobenzenes and their derivatives substituted in the 2 or 3 positions by methyl, amyl or cyclohexyl groups. The 1, 1-metal complexes may be reacted with colourless complex forming compounds as in Specification 692,073. The dyes dye wool, silk, leather and poly-amide and -urethane fibres. They also colour organic solutions and plastic masses e.g. cellulose esters and ethers and may be used in spin dyeing of acetate silk. Cobalt and chromium are specified metals. Examples are provided of the preparation of the dyes and their complexes and the use of the latter to dye wool in red or violet shades. Specification 793,136 also is referred to.