GB885042A - New naphthalene azo dyestuffs and metal complexes thereof - Google Patents

Abstract

The invention comprises dyes of formula <FORM:0885042/IV (c)/1> where R is the residue of a coupling component bearing OHo to N2, R1 is the residue of an organic compound, X is a bridge member containing at least two N atoms and n is 1 or 2, and their metal complexes. The dyes may be made by coupling a diazotised 1-halo-2-amino-6-nitronaphthalene-sulphonic acid with an azo component in o-position to a hydroxyl group, metallising if desired, and converting the nitro group into the bridge member by (a) reduction in the presence of a nitro compound to form an azo or azoxy link, (b) reducing the nitro to an amino group and condensing with a bis- or polyfunctional acylating agent in the presence of a primary or secondary amine, (c) reducing the nitro to an amino group and diazotising and coupling with an azo component, (d) reducing the nitro to an amino group, forming a phenyl urethane therefrom and treating with a primary amine to yield a urea or (e) reducing the nitro to an amino group and treating with a phenyl urethane of a primary amine, the products being metallised if required. The dyes may also be made by conversion of the 6-nitro group of the naphthalene sulphonic acid into the group R1-X followed by diazotisation and coupling and, if desired, metallisation. Where R contains a coupling position the dye, before conversion of the nitro group, may be coupled with a diazotised amine such as anthranilic acid. Representative of compounds specified corresponding to R are 4-methylphenol, 1-naphthol-4-sulphonic acid, 2-naphthol, 1-chloro-2-acetylamino-5-naphthol-7-sulphonic acid, 1-phenyl-3-methyl-5-pyrazolone and the saponified dye 1-chloro-2-amino-5-benzenesulphonylhydroxynaphthalene - 7 - sulphonic acid 1,5-dihyroxynaphthalene-7-sulphonic acid. Residue R1-X may contain metallisable groups dyes of the following formula being indicated <FORM:0885042/IV (c)/2> where n is 1 or 2 and representative of compounds from which R2 is derived are 2-methoxy-aniline and 2 - ethoxy - 1 - naphthylamine - 6 - sulphonic acid and of R3 are 4-methylphenol, 2-naphthol-3,6 - disulphonic acid and 1 - (41,81 - disulphonaphthyl - [21]) - 3 - methyl - 5 - pyrazolone. Specified polyfunctional acylating agents are phosgene, fumaric acid dichloride, terephthalic acid dichloride and cyanuric chloride. Copper complexes are preferred. The metal-dyes colour fibres of native and regenerated cellulose. The halogen-atom is readily labile so that, in some cases, the dyes may be metallised on the fibre. Examples are provided of the preparation of the dyes and their copper and nickel complexes. The use of the metal-dyes in colouring processes is also exemplified, green and blue shades being obtained.