Patent GB-963994-A (GB)
Title: Complex metal compounds of water-insoluble azo-dyestuffs and processes for their manufacture
IPC: D06P1/10
Filed: 1960-10-17
Abstract: The invention comprises complex metal compounds of water-insoluble azo-dyes of formula <FORM:0963994/C4-C5/1> wherein the quinoline radical may be substituted by halogen atoms or alkyl or alkoxy groups, R is the radical of an arylamide of an aromatic or heterocyclic o-hydroxycarboxylic acid or of an acylacetic acid free from sulphonic acid and carboxylic acid groups and n is 1 or 2. The dyes are prepared by coupling a diazotized 8-aminoquinoline, in substance or on the fibre (see Division D1) with an appropriate coupling component and treating the dye with a metallizing agent such as copper, cobalt, nickel, manganese, zinc, cadmium and iron salts. The dyes may be used to colour natural and synthetic polyamide, polyvinyl alcohol and preferably cellulose fibres in red to brown shades.  In Examples: (8) diazotized 8-aminoquinoline is added to an alkaline solution containing 1-(21,31 -hydroxynaphthoylamino) - 2 - methylbenzene, copper sulphate and triethanolamine to give the copper complex; (9) as in (8) but using 1 -(21,31-hydroxynaphthoylamino) -2-methoxy-benzene.ALSO:Natural and regenerated cellulose, natural and synthetic polyamide and polyvinyl alcohol fibres are dyed on the fibre in red to brown shades with complex metal compounds of water-insoluble azo dyes of formula <FORM:0963994/D1-D2/1> wherein the quinoline radical may be substituted by halogen atom of alkyl or alkoxy groups, R is the radical of an arylamide of an aromatic or heterocyclic o-hydroxy-carboxylic acid or of an acylacetic acid free from sulphonic and carboxylic acid groups and n is 1 or 2.  The dyings are obtained by coupling on the fibre in the usual manner in the presence of a metallising agent or by after-treatment of the dyeing with a metallising agent. Specified metallising agents are the salts and complex compounds of copper, cobalt, nickel, manganese, zinc, camium or iron.  In examples: (1) cotton yarn is impregnated with a solution of 2-(21, 31-hydroxy-naphtholamino)-naphthalene and the treated yarn developed in a bath containing diazotised 8-aminoquinoline and copper sulphate; (2) cotton fabric is padded on the foulard with a solution of 2, 3-hydroxynaphtholylaminobenzene, dried and developed on the foulard with a solution of diazotised 8-aminoquinoline, the dyed fabric is printed with a paste containing sodium-formaldehyde sulphoxylate, sodium benzyl-sulphanilate, potassium carbonate, anthraquinone paste, the potassium salt of the disulphonic acid of dimethyl-benzyl-phenylammonium chloride and starch tragacanth, steamed and finally treated with a solution containing nickel sulphate and aminoacetic acid to give a white discharge on a claret ground; (3) cotton fabric is dyed as in (2) on the foulard and after coppered with an aqueous copper sulphate solution; (4) woollen yarn is treated as in (1) to give a dyeing with the copper complex of 8-aminoquinoline --> 1-(21, 31-hydroxynaphthoylamino)-2-methyl-4-chlorobenzene, (5) natural silk is treated as in (1) to give a dyeing with the copper complex of 8-aminoquinoline --> 2, 3-hydroxynaphthoyl-aminobenzene; (6) polyamide yarn is impregnated with an aqueous solution containing 1-(21, 31-hydroxynaphthoylamino)-2-methoxy-benzene and 8-aminoquinoline, further treated in an aqueous solution of sodium nitrite and hydrochloric acid and finally treated with an aqueous solution containing copper sulphate and triethanolamine; (7) polyvinyl alcohol yarn is treated as in (7) to yield a dyeing with the dye specified in (5).  Many further dyeings on cellulose fibres are listed in a table, copper, nickel, cobalt, iron, manganese, zince and cadmium complexes being specified.