Patent GB-962986-A (GB)
Title: Water-insoluble metalliferous azo-dyestuffs and process for their manufacture
IPC: C09B45/00
Filed: 1960-09-08
Abstract: Amines of formula: <FORM:0962986/C1/1> wherein A is a benzene residue and B is a benzene or naphthalene residue, both A and B being free from water-solubilising groups, are prepared by treating a compound of formula: <FORM:0962986/C1/2> with hydrogen in the presence of a hydrogenation catalyst. The amines are used in the preparation of azodyes (see Divisions C4 and D1).  In an example 2-(21-amino-41-acetylamino-51-methylphenyl) - benztriazole -1- oxide is suspended in methanol and treated at 85 DEG C. and 60 atmospheres pressure with hydrogen in the presence of Raney nickel to yield 2-(21-amino-41-acetyl-amino -5- methylphenyl)-benztriazole.  Further compounds specified are 2-(21-aminonaphthyl-11) -benztriazole, 2-(21-amino -41- acetylamino -51-methylphenyl)-benztriazole, 2-(21-amino -41-methoxy -51- benzoylaminophenyl) -6- methoxybenztriazole, 2-(21-amino-41-methoxy-51-acetylaminophenyl) -6- methyl-benztriazole, 2-(21-amino -41- methoxy -51- methylphehyl)-benztriazole or -6-methyl-benztriazole, 2-(21-amino-41, 51-diethoxyphenyl) -6- methoxybenztriazole, 2-(21-amino-41-methoxy -5- acetylaminophenyl) -6- chlorobenztriazole and 2-(21-amino -41-methoxy -51- methylphenyl) -6- trifluoro-methyl-benztriazole.ALSO:The invention comprises water-insoluble metal complexes of azo dyes of formula <FORM:0962986/C4-C5/1> wherein A is a benzene residue, B is a benzene or naphthalene residue, R is an arylide of an aromatic or heterocyclic ortho-hydroxycarboxylic acid or of an acylacetic acid, the residues A, B and R being free from water-solubilizing groups and n is 1 or 2.  The complexes are prepared by coupling a diazonium compound of an amine of formula <FORM:0962986/C4-C5/2> with a suitable arylide a metallizing with a copper, cobalt or nickel compound the mono- or dis-azo dye formed.  The complexes may be used to dye natural and regenerated cellulose, acetyl-cellulose, wool, silk, synthetic polyamide and polyvinyl alcohol fibres in red, green, brown and black shades.  In an example, 2-(21-amino-41 - methoxy - 51 - methylphenyl) - benztriazole is diazotized and added in aqueous solution to an aqueous suspension of 1-(21,31-hydroxynaphthoylamino)-naphthalene containing acetic acid, sodium acetate and an oleyl alcohol-ethylene oxide condensation product, the coupling mixture neutralized with sodium hydroxide and treated with an aqueous solution of copper sulphate and triethanolamine.ALSO:Complex metal compounds of water-insoluble azo dyes are prepared on the fibre by coupling 1 or 2 mols of a diazorium compound of an amine of formula:-  <FORM:0962986/D1-D2/1> wherein A is a benzene residue and B is a benzene or naphthalene residue with 1 mole of an arylide of an aromatic or heterocyclic ortho-hydroxycarboxylic acid or an acylacetic acid and treating the dyeing with a metallising agent which may be added to the impregnation or developing bath.  The metallising may also be carried out after the coupling in a second bath which is neutral, weakly alkaline or weakly acid and may contain a dispersing agent and/or detergent.  Specified metallising agents are salts of cobalt, copper or nickel and complex compounds of these metals with hydroxyalkylamines, amino-acids, hydroxycarboxylic acids or alkali metal phosphates.  The complexes may be formed on natural and regenerated cellulose, acetyl-cellulose, wool, silk and synthetic polyamide or polyvinyl alcohol fibre to give red, green, brown and black shades.  In an example cotton yarn is impregnated with a solution containing 1-(21, 31-hydroxynaphthoylamino) naphthalene and developed in a bath containing a diazonium compound of 2-(21-amino-41-methoxy-51-acetylaminophenyl) -6-methylbenztriazole and copper sulphate to give a currant dyeing.  Many further examples are specified.