Patent GB-757541-A (GB)
Title: Metal complex forming azo dyestuffs
IPC: C09B45/00
Filed: 1954-02-19
Abstract: The invention comprises metallizable azo dyestuff containing at least one hydroxy group and one aldoxime or ketoxime group in o-position to each other, and their metal complexes.  The metal-free dyestuffs are made by coupling diazo components with coupling components either component containing the hydroxy and aldoxime or ketoxime groups. The dyestuffs may contain other metallizable groups such as o-hydroxy - carboxylic acid groups or hydroxy, alkoxy, carboxy, oxyacetic acid and amino groups in o, o1 position to an azo bridge.  The metal-free dyestuffs may also be obtained from dyestuffs containing an d -roxy - keto - or - aldehyde grouping by transformation to the corresponding oxime in conventional fashion.  Likewise the hydroxy group of the o hydroxy - oxime group ing may be obtained in conventional manner from a group which may be converted to a hydroxy group, e.g. a methoxy group, or exchanged for a hydroxy group, e.g. a halogen group.  The diazo component, if containing the oxime group may be chromed before diazotization and coupling is effected. Metallization may be effected in situ, on the fibre or in the dye-bath.  The metal-free dye-stuffs dye animal fibres.  Fibres of natural and regeneraated cellulose and synthetic films, and their metal complexes dye textile materials or may be used as pigments. Examples and a table illustrate the preparation of the metal-free dyestuffs, a copper complex of one of them and their use in dyeing cotton by after coppering and chromium processes in red, brown and blue shades, the diazo components used being 4, 41 - diaminodiphenyl and its 3, 31 - dihydroxy, - dicarboxy, and - dioxyacetic acid derivatives, 4, 41 - diaminodiphenyl urea - 3, 31 - dicarboxylic acid, 4 - amino - 31 - carboxy - 41 - hydroxyazobenzene --> 1 - amino - 2 - methoxy - 5 - methyl - benzene, 2 - hydroxy-5-(41-aminobenzoylamino)- and 5 - amino - 2 - methoxyacetophenone oximes, 1 - amino - 2, 5 - dichlorobenzene - 4 - sulphonic acid, 2 - hydroxyacetophenone oxime \sM 5 - (41 - aminobenzoylamino) - 2 - aminobenzoic acid --> 2 - (41 - aminobenzoylamino) - 5 - naphthol - 7 - sulphonic acid, 5 - (41 - aminobenzoylamino) - 2 - aminobenzoic acid --> 2 - hydroxy - acetophenone oxime, 4, 41 - diaminodiphenyl - 3, 31 - dicarboxylic acid --> 2, 8 - dihydroxynaphthalene - 3 - carboxylic acid and - 6 - sulphonic acid and 4, 41 - diaminodiphenyl - 3, 31 - dioxyacetic acid --> (2 mols.) 2 - amino - 5 - naphthol - 7 - sulphonic acid, and the coupling components are 2-hydroxyacetophenone oxime, res-aceto-, -propio- and -butyro-phenone oximes, resorcyl aldoxime, 2 - benzoylamino - 5 - naphthol - 7 - sulphonic acid, 1-phenyl - 3 - methyl - 5 - pyrazolone, 2, 6-dihydroxynaphthalene - 1 - aldoxime, 2 - hydroxy - 4 - methyl - and - amino - acetophenone oximes, mixed urea of 2 -amino - 5 - naphthol - 7 - sulphonic acid and 2 - hydroxy - 5 - amino - acetophenone oxime, salicylic acid, 3 - amino - 2 - phenol - 1 - carboxylic acid - 5 - sulphonic acid --> resacetophenone oxime, 2 - naphthol - 5 - sulphonic acid and 2 - hydroxybenzaldehyde (converted after coupling to the corresponding oxime).