Patent GB-951452-A (GB)
Title: Water-insoluble metalliferous triazole azo-dyestuffs and process for their manufacture
IPC: C09B45/34
Filed: 1960-05-20
Abstract: The invention comprises complex metal compounds of dyes of formula <FORM:0951452/C3/1> where A and B are residues of the benzene or naphthalene series and R is the residue of an arylide of an aromatic, or heterocyclic, o-hydroxycarboxylic acid or of an acylacetic acid, the residues being free from sulphonic or carboxylic acid groups. The dyes may be made in substance, on the fibre, or some other substratum, in conventional fashion from appropriate triazole diazo components, and coupling components corresponding to R, with metallization of the dyes thus obtained.  Metallization may accompany coupling.  Metallization of the preformed dyes may be effected in the presence of a dispersing agent or a detergent. Copper, cobalt and nickel are preferred metals.  Metallization with cobalt yielding agents is preferably effected in the presence of a compound of hexavalent chromium or other oxidizing agent. Representative of indicated arylides are those of 2,3-hydroxynaphthoic acid and its 6-substituted derivatives, 2-hydroxyanthracene-3-carboxylic acid, 3-hydroxydiphenylene oxide 2-carboxylic acid, 5-hydroxy 1,2; 11,21-benzocarbazole-4-carboxylic acid, aceto-acetic acid and terephthaloyl-bis-acetic acid.  Indicated substituents for the diazo components, which may be obtained as in Specification 944,843, are halogen atoms or alkyl, alkoxy, aryloxy, arylamino, trifluoromethyl, sulphonic acid amide or carboxylic acid amide groups.  The dyes are used to colour vegetable, animal and synthetic fibres, e.g. regenerated cellulose, wool, silk, polyamide, acetyl-cellulose and polyvinyl alcohol fibres.  Numerous examples are provided of the preparation of the dyes and their use in dyeing processes.  Green, brown and black shades are obtained.ALSO:Novel water-insoluble complex metal compounds of dyes of formula <FORM:0951452/D1-D2/1> where A and B are residues of the benzene or naphthalene series and R is the residue of an arylide of an aromatic series or heterocyclic o-hydroxycarboxylic acid or of an acrylacetic acid, the residues being free from sulphonic or carboxylic acid groups, are formed on the fibre by conventional methods.  Metallisation may be effected during, or after coupling, on the fibre the dyes being made from appropriate triazole diazo components and coupling components corresponding to R.  The metal yielding agent may be added either to the developing or the impregnation bath. Metallisation, after coupling, may be effected in a neutral or weakly acid or alkaline bath in the presence of detergents or dispersive agents, e.g. fatty alcohol, alkyl-phenol, alkyl-naphthol and fatty acid amide polyglycol ethers and fatty acid polyglycol esters.  The complexes are preferably those of copper, cobalt and nickel.  Representative of indicated arylides are those of 2,3-hydroxynaphthoic acid and its 6-substituted derivatives, 2-hydroxyanthracene-3-carboxylic acid, 3-hydroxy-diphenylene oxide-2-carboxylic acid, 5-hydroxy 1,2; 11, 21-benzocarbazole-4-carboxylic acid, acetoacetic acid and terephthaloyl-bis-acetic acid.  Indicated substituents for the diazo components which may be obtained as in Specification 944, 843, are halogen atoms or alkyl, alkoxy, aryloxy, arylamino, trifluoromethyl, sulphonic acid amide and carboxylic acid amide groups.  The dyes colour vegetable, animal and synthetic fibres e.g. regenerated cellulose, wool, silk, polyamide, acetylcellulose and polyvinyl alcohol fibres. Numerous examples are provided of the dyeing of cotton fibres, and other examples illustrate the colouring of wool, polyamide, polyvinyl alcohol and natural silk fibres.  Green, brown and black shades are obtained.