Patent GB-820489-A (GB)
Title: New mixed chromium complexes of monoazo dyestuffs and process for their manufacture
IPC: C09B45/16
Filed: 1955-12-02
Abstract: The invention comprises mixed chromium complexes containing one atom of metal bound in complex union with two different monoazodyestuffs free from sulphonic acid groups, of which one is of formula <FORM:0820489/IV(c)/1> in which the benzene and/or naphthalene nucleus may contain substituents incapable of imparting water-solubility. Advantageously the second dyestuff is an o,o1-dioxy- or o-carboxy-o1-oxymonoazo-dyestuff free of sulphonic or carboxylic acid groups (except that required for metallization). Substituents for compounds of the above formula may be nitro, alkyl and alkoxy groups and halogen atoms.  The above second dyestuffs may contain halogen, alkyl, alkoxy, nitro, acylamino, sulphone amino and substituted amino substituents.  Specified or indicated azo components for the second dyestuff are 4-methyl-, -methoxy- and -chloro-, 4,6-dichloro-and -dinitro-, 4-methyl- and -chloro-5- and -6-nitro-, 4-nitro-6-chloro-, 6-nitro-4-acetylamino-, 4-nitro-6-acetylamino- and 4-, 5- and 6-nitro-2-aminophenols, 2-aminophenol-4- and -5-sulphonamides, 6-nitro- and -chloro-2-aminophenol - 4 - sulphonamides, 4 - chloro - 2 - aminophenol - 5 - sulphonamide, 4 - nitro - 2 - aminophenol - 6 - sulphonamide and the N-alkyl- and -aryl-derivatives of the sulphonamides, 2 - aminophenol - 4 - and - 5 - methyl-, -phenyl- and - benzyl-sulphones and 4-chloro-2-aminophenol-5- and -6- and 6-nitro-2-aminophenol - 4 - methyl - sulphones.  Specified and indicated coupling components for the second dyestuff are 4-methyl-, -isopropyl-, -tert.-amyl-, 2,4- and 3,4-dimethyl-, 4-acetylamino-3-methyl-, 4-methyl-2-acetylamino and 4-acetylamino-1-phenols, 1-benzoyl, -acetyl-, -n-butyryl- and carbomethoxy-amino-7-naphthols, 2-naphthol, 6-bromo- and methoxy-2-naphthols, 5-chloro- and 5,8-dichloro-1-naphthols, 1-naphthol-4- and -5-sulphonamides, 2-naphthol-6-sulphonamide and its -N-methyl-N-b -oxyethyl-derivative, barbituric acids, 1-phenyl-3-methyl-5-pyrazolone and its 21-, 31- and 41-chloro-, 31-sulphonamido- and 31- and 41-sulphonmethylamido - derivatives, 1,3 - diphenyl - 5 - pyrazolone, 2,4-dioxyquinoline, 5-chloro-8-oxyquinoline, acetoacetic acid anilide and o-, m- and p-chloranilides, 1-acetoacetylaminobenzene-3- and -4-sulphon- and -sulphonmethyl-amides and -2-, -3- and -4-methyl-sulphones. Advantageously the mixture to be metallized contains about 1 mol. proportion of each of two different dyestuffs.  Chroming is preferably effected with a chromium complex of an o-oxy-carboxylic acid in a neutral or aqueous medium, see Specification 637,404. The dyestuffs may also be made by treating metal-free dyestuffs in neutral or weakly alkaline solution with 1,1-chromium complexes of dyestuffs the starting materials being so chosen as to yield the products indicated above.  Preferably the metal-free dyestuff is of the above formula.  The dyestuffs dye materials of animal origin such as silk, leather and wool and fibres of superpoly-amides or -urethanes from a weakly alkaline to weakly acid bath.  In examples which illustrate the preparation of the dyestuffs and their use in dyeing wool in grey and brown shades 2-naphthol and 2-amino-benzoic acid and its 4-chloro- and -nitro-derivatives are the reactants used for the first dyestuff and for the second additional components used to those already specified are 2-aminobenzoic acid, 2-aminophenol - 4 - sulphon - methyl - and - isopropyl - amides and 1 - (41 - methyl) - phenyl - 3 - methyl-5-pyrazolone.  Specification 758,016 also is referred to.