Patent GB-777050-A (GB)
Title: Metalliferous monoazo-dyestuffs and processes for their manufacture and use
IPC: C09B45/16
Filed: 1953-11-24
Abstract: The invention comprises chromium or cobalt compounds of monoazo dyestuffs which are free from sulphonic acid and carboxylic acid groups and are of the formula:- <FORM:0777050/IV(b)/1> wherein R is a benzene residue containing a hydroxyl group ortho to the azo linkage and R1 - OH is the residue of a 1 - naphthol mono - sulphonamide or mono - sulphonic acid aryl ester capable of coupling in the 2 - position, which monoazo dyestuffs contain a sulphonic acid aryl ester group or at least one mono - substituted sulphonamide group and at most one unsubstituted sulphonamide group, and which chromium or cobalt compounds contain less than one metal atom bound in complex union per molecule of dyestuff.  The metallized dyestuffs are prepared by treating the monoazo dyestuffs described above with a chromium- or cobalt-yielding agent in such a manner that the resulting complex contains less than one metal atom per mol of dyestuff.  Specified diazo components for use in the preparation of the monoazo dyes are 4 - methyl - or - methoxy - or - chloro - 2 - aminophenol, 4 - or 5 - nitro - 2 - aminophenol, 6 - acetylamino-4 - chloro- or - nitro - 2 - aminophenol, 5-or 6 - nitro - 4 - chloro- 2 -aminophenol, 4 - nitro - 6 - chloro - 2 - aminophenol, 6 - nitro - 4 - methyl - or - acetylamino - 2 - aminophenol, 3 - amino - 4 - hydroxy-acetophenone, 5 - nitro - 3 - amino - 4 - hydroxyacetophenone, 2 - aminophenol - 4 - carboxylic acid amide, 4:6 - dinitro - or - dichloro - 2 - aminophenol, 6 - nitro - or - chloro - 2 - aminophenol - 4 - sulphonamide, 6 - nitro - or - chloro - 2 - aminophenol - 4 - or - 5 - sulphonic acid - methylamide, 2 - aminophenol - 4 - or - 5 - sulphonic acid - methyl - or - ethyl- or -isopropyl - or - butyl - or - b  - hydroxyethyl - or -a  -methyl-b - hydroxyethyl - or - cyclohexyl - or phenyl - or - p - toyl - or p - chloro - phenyl - amide, 4 - chloro - or - nitro-2 - aminophenol - 6 - sulphonamide, 4 - chloro - or - methoxy - 2 - aminophenol - 5-sulphonamide and 2 - aminophenol - 4 - or - 5 - sulphonamide. Specified coupling components are 1 - naphthol - 8 - phenylamino-5 - sulphonic acid - methyl - or - phenyl - amide, 1 - naphthol - 3 - or - 4 - or - 5 - sulphonic acid - methyl - or - ethyl - or - isopropyl - or - n - butyl - or phenyl - or - 41 - chlorophenyl - amide, 1 - naphthol - 3 - or - 4 - or - 5 - sulphonic acid phenyl ester which may contain in the phenyl nucleus an alkyl group or a halogen atom, e.g. 1 - naphthol - 4 - sulphonic acid p-cresyl ester, 4 - chloro - 1 - naphthol - 8 - sulphonamide, 7 - chloro - 1 - naphthol - 3 - sulphonamide, 8 - chloro - 1 - naphthol - 5 - sulphonamide and 1 - naphthol - 3 - or - 4 - or 5 - sulphonamide.  The metallization is carried out in known manner preferably in a weakly acid to alkaline medium and using less than one atomic proportion of chromum or cobalt per molecular proportion of monoazo dye.  Suitable metallizing agents are complex chromium and cobalt compounds of aliphatic hydroxy - carboxylic or dicarboxylic acids such as oxalic, lactic, glycollic, citric and tartaric acids and complex chromium compounds of aromatic hydroxycarboxylic acids such as salicyclic acid and its 4, - 5 - or 6 - methyl derivatives.  Cobalt - yielding agents include cobalt acetate, cobalt sulphate and cobalt hydroxide.  The metallized monoazo dyes are suitable for dyeing and printing silk, leather, wool, superpolyamides and superpolyurethanes in red - blue tints.  In examples, cobalt and chromium complexes of monoazo dyestuffs which are obtained from certain of the components specified above are prepared. Specifications 637,404 is referred to.