GB816991A - Dyestuffs of the benzene-monoazo-naphthalene series and metal derivatives thereof - Google Patents

Abstract

The invention comprises dyestuffs of formula <FORM:0816991/IV (c)/1> where R1 and R2 are amino, acylamino and alkyl- and aryl-sulphonylamino, except that R2 is not amino when R1 is acylamino, R3 and R4 are H or alkyl or hydroxyalkyl or 1-4 C atoms or form a heterocyclic ring with N and X is H, Cl or Br and their metal complexes. The compounds are made by diazotizing a 5-nitro-4-X-2-aminophenol and coupling with an appropriate naphthol in which R2 may have all the stipulated values save NH2, the 5-nitro group is then reduced to NH2 with subsequent acylation if desired and R2 may be obtained as NH2 on hydrolysis of an appropriate dyestuff in which it is an acylamino residue. Specified as coupling components are 1-acetylamino-3,6-disulphonyl chloride-8-naphthol or derivatives derived therefrom by reaction with ammonia, dimethyl-, ethyl-, isopropyl-, ethanol-, diethanol- and butyl-amines, morpholine and piperidine and those specified in Specification 811,521. Specified for R2 are acetyl-, propionyl-, butyryl-, benzoyl-, methylsulphonyl-ethylsulphonyl- and benzenesulphonyl-amino groups. Indicated for R3 and R4 are H, methyl, ethyl, propyl, isopropyl, butyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, morpholino and piperidino. Metals indicated are those of atomic weights 52-66, e.g. copper, nickel, iron, cobalt and especially chromium. Mixtures of metal compounds may be used for metallizing. Diazotization and/or coupling and/or metallization may be effected in substance, on a substratum, or in situ. The dyestuffs dye wool or nylon from a neutral or slightly acid bath and silk, leather, cellulose ethers and esters, polyesters, regenerated proteins and polyacrylonitriles. They also colour artificial resins, organic solvents, stains, varnishes and lacquers. In examples which illustrate the preparation of the dyestuffs and their chromium complexes and the use of the latter in the dyeing of wool in red-blue and green-blue shades: (1) the dyestuff 4-chloro-5-nitro - 2 - aminophenol --> 1 - acetylamino-3,6 - di - (N,N - dimethylsulphamyl) - 8 - naphthol is chromed and the nitro group reduced; in (2) the actylamino group of the dyestuff of (1) is hydrolysed; (3) is as (1) but using 1-benzoylamino - 3,6 - disulphamyl - 8 - naphthol as coupling component; (4) is as (1) using 5-nitro-2-aminophenol and 1-acetylamino-3,6-di (hydroxyethylsulphamyl) - 8 - naphthol as components; in (5) the amino group of the benzene nucleus of dyestuff (4) is acetylated; and in (6) the acetylamine group of dyestuff (4) is hydrolysed. Specification 775,005 also is referred to.