Patent GB-784138-A (GB)
Title: Manufacture of cobalt and chromium complexes of monoazo dyestuffs
IPC: C09B45/14
Filed: 1954-04-14
Abstract: The invention comprises cobalt or chromium compounds which contain two monoazo-dyestuffs bound in a complex in which the ratio of the number of atoms of cobalt or chromium to the dyestuff molecules is less than 1 : 1, and advantageously 1 : 2, the dyestuffs being 0,01-dioxy-monoazo-dyestuffs free of SO3H and COOH groups and one is of formula HO-R1-N=N-P2-R2-X-A, where R1 is a benzene residue bound to the azo link oto the OH group and which contains an -SO2NH2 group, P2 is a 5-pyrazolone residue bound to the azo link in the 4-position, R2 is a benzene residue, X is <FORM:0784138/IV (b)/1> n is an integer and A is an aliphatic residue containing more than one C atom or a benzene residue, the other dyestuff corresponding to the above formula or being an o,o1-dioxy-monoazo dyestuff of the benzene-azo-naphthalene series free of SO3H or COOH groups.  The starting dyestuffs are made by conventional processes and metallization is effected in the usual way.  The group R2-X-A may be bound to the 3-position of the pyrazolone through a -CO-NH-group but preferably is bound directly to the 3-, or advantageously the 1-, position.  Specified pyrazolones are 5-pyrazolone-3-carboxylic acid anilide-31- and -41-sulphonphenylamides and -41-phenylsulphone, -3-carboxylic acid - N - (31 - p - toluenesulphonylaminophenyl)-amide 1-phenyl-5-pyrazolone-3-carboxylic acid amide-31- and -41-sulphonic acid anilides, 1-(41 p-toluenesulphonylaminophenyl)-5-pyrazolone-3 - carboxylic acid anilide, 3 - phenyl - 5 - pyrazolone - 31\h - and - 41 - sulphonic acid anilides and phenyl esters, 21-methyl-1,3-diphenyl-5-pyrazolcne-311-sulphonic acid anilide, 1-(31-and 41-benzenesulphonyl-amino- and -oxyphenyl, -ethanesulphonyloxyphenyl and -benzoylaminophenyl) and -(21, 31- and 41-phenoxyphenyl) - 3 - methyl - 5 - pyrazolones, 1 - phenyl-3 - methyl - 5 - pyrazolone - 21 -, - 31 - and - 41 - sulphonic acid anilides and phenyl esters, -31-sulphon - butyl -, - cyclohexyl - and - p - tolyl - amides, -31- and -41-carboxylic acid diethyl-amides and -phenyl- and -benzyl-sulphones and -31-carboxylic acid isopropyl- and phenyl-amides and 1-(21-chloro- and -methyl-phenyl)-3-methyl-5-pyrazolone-41- and -51-sulphonic acid anilide.  The diazo components containing the -SO2NH2 group may contain substituents such as Cl, Me, OMe, NO2, COMe and MeCONH groups.  Preferred diazo components are 2 aminophenol - 6 - nitro - 4 -, - 4 - nitro - 6 -, - 4 - chloro-5-and -6-sulphonamides and particularly 2-aminophenol-4- and -5-sulphonamides.  Advantageously the benzene-azo-naphthalene dyestuff contains a sulphonamide group. Preferred complexes are those containing two identical dyestuffs of formula <FORM:0784138/IV (b)/2> where R and B are benzene residues, P2 is a 5-pyrazolone residue bound to the azo link in the 4-position and Z is -NHCO-, -SO2-, -NHSO2- or -O-SO2-.  The complexes dye animal materials such as silk, leather and especially wool, and superpoly-amides and -urethanes and polyacrylonitrile from weakly alkaline, neutral or weakly acid baths. Examples are provided illustrating the preparation of the complexes and their use in dyeing wool in red and yellow tints, the components used being certain of those already specified and 1 - (21 - methyl - 51 - sulphon - N - isopropylaminophenyl)-, -(31-sulphon-N-methylanilido)-, -(31- sulphon - N - ethyl - and - diethyl - aminophenyl) -, - (31 - p - toluenesulphonylaminophenyl)- and -(41-o-methylphenoxy-, -benzoyl-and -p-tolylsulphonyl-phenyl)-3-methyl-5-pyrazolones, the dyestuff 2-aminophenol-4-sulphonmethylamide --> 1-acetylamino-7-naphthol being used in a mixed dyestuff. Specifications 637,404, 693,245, 699,976, 706,370 and 709,495 are referred to.