Patent GB-788157-A (GB)
Title: Metal complexes of pyrazolone monoazo-dyestuffs and process for making them
IPC: C09B45/14
Filed: 1954-05-04
Abstract: The invention comprises cobalt or chromium compounds which contain two identical or not identical monoazo dyestuffs which are free of sulphonic and carboxylic acid groups and both of which contain an aromatically bound SONH2 group and are of formula: <FORM:0788157/IV (b)/1> where R1 is a benzene residue bound to the azo group in o-position relatively to the OH group and R2 is H or an alkyl or benzene residue and R3 is a benzene residue, and at least one of the aromatic residues in the dyestuff molecule has a substituent not imparting solubility in water, or two monoazo deystuffs of which one is of the above formula and the other is an o,o1-dioxymonoazo dyestuff of the benzene-azo-naphthalene series free of sulphonic and carboxylic acid groups, and in which the ratio of the number of metal atoms to dyestuff molecules is less than 1 : 1 and is advantageously about 1 : 2.  The substituent not imparting water solubility may be a nitro, alkoxy or aryl group or a halogen atom.  Preferred dyestuffs of the above formula are those of formula: <FORM:0788157/IV (b)/2> containing one of the above groups not imparting solubility in water and especially those of formula: <FORM:0788157/IV (b)/3> where one X is H and the other an alkyl residue or a halogen atom, advantageously a chlorine atom, and n is an integer, advantageously 1.  They are made by conventional methods by treating appropriate mixtures of dyestuffs with chromium or cobalt yielding agents.  The metalfree dyestuffs are also made by usual methods.  Specified diazo components for compounds of the above formul  are 4-chloro-, 4- and 5-nitro, 4,6 - dichloro-, and 4 - nitro - 6 - chloro - 2-aminophenols, 6 - chloro - and nitro - 2-aminophenol - 4 - sulphonamides, 4 - chloro-, nitro-, methyl - and methoxy - 2 - aminophenol - 5 - and 6 - sulphonamides and 2-aminophenol - 4 - or 5 - sulphonamides the last two compounds being preferred.  Coupling components specified for dyestuffs of the above formul  are 1,3 - diphenyl - 5 - pyrazolone-21-, 31 - and 41 - sulphonamides, 3 - phenyl - and 1,3 - diphenyl - 5 - pyrazolones, 3 - (31-and 41 - methyl-, 41 - tert. butyl-, 21-, 31-and 41 - chloro-, 41 - fluoro-, trifluoromethyl-and ethoxy - and 21,51 - dichloro - phenyl - 5-pyrazolones, 1 - (21 - methyl - 51 - chlorophenyl)-, (21-, 31 - and 41 - chlorophenyl) - and (31-nitrophenyl) - 3 - phenyl - 5 - pyrazolones, 1-phenyl - 3 - (31 - chlorophenyl) - 5 - pyrazolone and 1 - (41 - chlorophenyl) - 3 - (21 - chlorophenyl)-5-pyrazolones. Specified diazo components for the benzene-azo-naphthalene dyestuffs are 5 - chloro-, 6 - acetylamino - 4-nitro - and 4 - acetylamino - 6 - nitro - 2-aminophenols, 2 - aminophenyl - 4 - methylsulphone - and 4 - and 5 - sulphonic acid - N-methyl-, ethyl-, b  - oxyethyl - and phenylamides and other diazo components listed above.  Azo components specified are 5-chloro- and 5,8-dichloro - 1 - naphthol, 2 - naphthol, 6 - bromo-, 6 - and 7 - methoxy - and 8 - acetyl-, butyryl-, benzoyl - carbomethoxy - and carboethoxyamino-2-naphthols. The metal dyestuffs dye silk, leather, wool and fibres of superpolyamides, superpolyurethanes and polyacrylonitrile from alkaline, neutral or weakly acid baths.  Examples are given of the preparation of the metallized dyestuffs and their use in dyeing wool and nylon in red and yellow shades additional dyestuff components used to those specified above being 1-methyl-, (21-methoxyphenyl) and (21 - methyl - 51 - chlorophenyl)-3 - (41 - chlorophenyl) - 5 - pyrazolones.  Specifications 637,404, 693,245 and 709,495 also are referred to.