Patent GB-880658-A (GB)
Title: Metal-containing azo dyestuffs derived from cyanonaphthalene
Filed: 1960-01-18
Abstract: The invention comprises dyes of formula <FORM:0880658/IV (c)/1> where R is a carbocyclic or heterocyclic radicle containing one to three 5- to 6-membered nuclei in which X is in the o-position to the azo bridge and which may contain further substituents, X is 0 or C00, R1 is the residue of a 4-cyanonaphthalene in which O is in the 2-position and the azo link in the 1-position, Me is Cu, Co or Cr and n is 1 or 2.  The dyes are made by conventional processes by metallising dyes obtained by coupling appropriate diazo, diazoazo or tetrazo compounds with a 4-cyano-2-naphthol or by coupling a diazotised 1-amino-4-cyano-2-naphthol with appropriate coupling components. Indicated as values for R are diphenyl, azobenzene, benzene, naphthalene, stilbene, and diphenylurea.  Illustrative of specified diazo components for use with a cyano coupling component are 2-aminophenol and its 4-chloro, nitro and sulphonamide derivatives, 3-amino-4-phenol-thylsulphone, 6-chloro-4-amino-1,3-dimethoxybenzine, 2-aminophenol-4-sulphonic acid, 2-amiline-1-carboxylic acid, 4-acetylamino-2-amiline-1-carboxylic acid and sulphonamido-phenyl - 1 amino - 2 - hydroxy - and - carboxy - benzenes substituted at the N-atom of the sulphonamide group by, e.g. alkyl, arakyl and phenyl groups or by ring-closed alkyl groups to form, e.g. morpholine or piperazine residues, and 2-ethoxy-1-naphthylamine and its 6-sulphonic acids.  Specified tetrazo components are 4,41-diamino-3,31-dihydroxy-diphenyl, 4,41-diamino-3,31-dimethoxy-diphenyl and diphenylurea and 4,41-diamino-3,31-dicarboxy-diphenyl or-stilbene. 2 - amino - 5 - arylazophenols and - anisoles, 2 - amino-4-arylazophenols and 1-amino-2-methoxy-4-arylazonaphthalene sulphonic acids may also be used.  Components requiring metallisation via oxidation, or by replacement of halogen or sulphonic acid groups, may also be used typical being 1 - amino - 2 - halobenzenes, aniline - 2 - sulphonic acids, 4,41-diaminodiphenyl and 4,41-diamino-3,31-dichlorodiphenyl. Representative of specified components for coupling with 1-diazo-4-cyano-2-naphthol are resorcinol, 3-alkoxy-phenols, 1,5-dihydroxynaphthalene, 5-acetamino-2 - naphthol, 5 - methanesulphonylamino - 2 - naphthol, 2-naphthol and its sulphuric acids and their amides and sulphones, 1-phenyl-3-methyl and - carboxy - 5 - pyrazolone, 1 - phenyl - (41 - sulphophenyl) - 3 - methyl - 5 - pyrazolone, 1 - (31 - aminophenyl) - 3 - methyl - 5 - pyrazolone and 1 - (61 - sulphonaphthyl - [21]) - 3 - methyl - 5-pyrazolone.  The metal-free dyes colour animal and vegetable materials, e.g. wool, silk, cotton, regenerated cellulose, leather and synthetic polyamide and -usethanes. Dyeings on vegetable fibres may be after-coppered and those on animal fibres may be chromed.  Metallisation may be effected in admixture with other metallisable dyes.  Examples are provided of the preparation of the dyes and their use in colouring processes red, blue and grey shades being obtained.  Specifications 381,602, 484,597, 660,447, 721,495 and 790,386 are referred to.  Reference has been directed by the Comptroller to Specifications 637,404, 753,987 and 758,016.