Patent GB-793712-A (GB)
Title: New cobaltiferous dyestuffs of the benzene-monoazo-pyrazolone series
Inventor: HOWARD GEORGE FRANCIS
IPC: C09B45/20
Filed: 1955-07-06
Abstract: 1 - [21 - Methyl - 51 - (411 - methylbenzenesulphonyl)- and 31-(411-acetylaminobenzenesulphonyl) - aminophenyl] - 3 - methyl - 5 - pyrazolones are made by condensing 1-(21-methyl - 51 - aminophenyl) - and - (31 - aminophenyl) - 3 - methyl - 5 - pyrazolones with p - toluenesulphonyl and p-acetaminobenzenesulphonyl chlorides respectively.  The products are dyestuff intermediates (see Group IV (c)).ALSO:The invention comprises cobalt complexes of dyestuffs, free from sulphonic and carboxylic acid groups, of formula <FORM:0793712/IV (b)/1> where R1 is a benzene nucleus which may contain halogen, methyl, nitro and/or methoxy substituents, the nucleus being bound to the azo link ortho to the hydroxyl group, Y is a benzene nucleus which may be substituted by halogen, methyl, alkoxy or acylamino groups and residue Z may also contain a methyl group. 1,2-Complexes are preferred.  The dyestuffs are made by conventional methods by cobalting the dyestuffs obtained by diazotizing an appropriate aminophenol and coupling in alkaline solution with the pyrazolone component.  Specified aminophenols are 2-aminophenol and its 4-chloro, -methyl and -methoxy and 4- and 5-nitro derivatives. Specified coupling components are 1-[31-(411-methyl- and -chloro-, 211,511-dichloro- and 411-chloro-211,511-dimethylbenzenesulphonyl) - and 41-(benzenesulphonyl)-aminophenyl] - 3 - methyl - 5 - pyrazolones.  The metal-free dyestuffs may be mixed with o,o1-dihydroxymonoazo dyestuffs of the benzene naphthalene series which are free from sulphonic or carboxylic acid groups and the mixture cobalted.  Specified diazo components for the naphthalene dyestuffs are those indicated above and 2-amino-phenol-4-ethyl- and -isopropylsulphones and coupling components for these dyestuffs are b -naphthol, 6-bromo-b -naphthol, 1-acetyl-, -propionyl-, -benzoyl- and carbomethoxy- and -ethoxy-amino-7-naphthols and 5-chloro- and 5,8-dichloro-a -naphthols.  The dyestuffs dye animal fibres e.g. wool and silk, from neutral or weakly acid dye-baths and artificial fibres such as those of linear polyamides and -urethanes and fibres of natural and synthetic proteins.  They may also be used for colouring lacquers and varnishes.  In examples which illustrate the preparation of the dyestuffs and their use in dyeing certain of the above indicated materials in orange or brown shades additional specified components for dyestuffs of the above formula are 4-methyl-6-nitro-and 4,6-dichloro-2-aminophenols, 1-[21-methyl-51-(benzenesulphonyl) and -(411-methylbenzene-sulphonyl) - aminophenyl] -, - [41 - (411 - methyl-benzenesulphonyl)-aminophenyl]-, -[31-(311,411-dichlorobenzenesulphonyl) - aminophenyl] - and -[31-(411-acetylaminobenzenesulphonyl) - aminophenyl]-3-methyl- 5-pyrazolones an additional component for a naphthalene dyestuff being 2-aminophenol-4-sulphonamide.  In the Provisional Specification R1 is a benzene residue bound to the azo link ortho to the hydroxyl group and is free from sulphonamido and sulphonyl substituents, Y is as above and Z may also contain halogen or alkoxy substituents.