Patent GB-771309-A (GB)
Title: Manufacture of new cobalt-containing monoazo-dyestuffs
IPC: C09B45/20
Filed: 1952-12-12
Abstract: 2 - Amino - 1 - oxybenzene - 4 - sulphonic acid N - phenylamide - 31 - sulphonic acid amide is made by treating 1-chloro-2-nitrobenzene-4-sulphonic acid chloride with 1-aminobenzene-3-sulphuric acid amide to yield 1-chloro-2-nitrobenzene-4-sulphonic acid N-phenylamide-31-sulphonic acid amide the chlorine of which is hydrolysed by means of an alkali or alkaline earth metal hydroxide and the nitro group of which is reduced to an amino group.  2-Amino-1-oxybenzene-5-sulphonic acid N-phenylamide-31-sulphonic acid amide is made by reacting 1,2-benzoxazolone-5-sulphonyl chloride with 1-aminobenzene-3-sulphonic acid amide and splitting the oxazolone ring in the resultant 1,2-benzoxazolone-5-sulphonic acid N-phenylamide-31-sulphonic acid amide with an alkali metal hydroxide. The sulphonamides are dyestuff intermediates of Group IV (c).ALSO:The invention comprises cobalt compounds which contain one or two monoazo dyestuffs which are free of sulphonic or carboxylic acid groups and at least one of which is of formula <FORM:0771309/IV(b)/1> where R1 is a benzene residue bound to the azo linkage in ortho-position to the hydroxyl group, R2 is the residue of an azo component bound to the azo linkage in a position vicinal to a hydroxy group or an amino-naphthalene residue bound to the azo linkage in a position vicinal to the amino group and X is an aryl residue containing a substituent of formula <FORM:0771309/IV(b)/2> where Z1 and Z2 are H or an aliphatic residue containing at most 6 carbon atoms.  The monoazo dyestuffs may be made by coupling a appropriate aminonaphthalene or azo component with the required orthooxy-diazo compound.  Residue R1 may contain OH in the 1-position and the sulphonamide group in the 4-, 5- or 6- position and may contain further substituents not capable of salt formation e.g. a halogen atom or nitro group. Residue X may be a naphthalene or advantageously a benzene residue which contains a suphonamide group e.g. a sulphonic acid alkyl- or oxyalkylamide group and advantageously a -SO2NH2 group and, if desired, substituents such as a methyl group or a chlorine atom.  Specified diazotisable amines are 2-aminophenol - 4 - sulphonic acid - N - 11-naphthylamide - 41 - sulphonic acid amide, 2 - aminophenol - 6 - chloro - 4 - sulphonic acid - phenylamide - 31 - sulphonic acid amide, 2 - aminophenol - 6 - nitro - 4 - sulphonic acid - phenylamide, - 41 - sulphonic acid amide, 2 - aminophenol - 4 - or -5 - sulphonic acid phenylamide - 31 - sulphonic acid methyl-, b - oxyethyl- and dimethylamide and -41-sulphonic acid - isopropyl- and - n - butylamide and especially 2 - aminophenol - 4 - or - 5 - sulphonic acid phenylamide - 21 -, - 31 - and - 41 - sulphonic acid amide.  Specified azo-components are b -naphthylamine, 1 - aminonaphthalene - 4 - sulphonic acid amide, 4 - methyl-, 3, 4-dimethyl-, 4-tert-amyl- and 4-acetyl-amino-1 - oxybenzene, 4 - methyl - 2 - acetylamino - 1 - oxy benzene, resorcinol, b -naphthol and its 6- sulphonic acid amide, 2, 6-dioxynaphthalene, 2-oxy - 6 - bromo - and -methoxy - naphthalene, 1 - oxy - 4 - methyl - 5 chloro- and -5, 8 dichloro-naphthalee, 1 - acetyl-, - n - butyryl- and-benzyl - amino - 7 - oxynaphthalene, 3 -methyl- and -phenyl - 5 - pyrazolone, 1 - n - butyl-, -phenyl - and -(21, 31- or 41-chloro)-phenyl-3-methyl - 5 - pyrazolone, 5-pyrazolone-3-carboxylic acid amide, 5-pyrazolone - 3 - carboxylic acid - N - methyl-, -ethyl-, -isopropyl-, sec butyl-, tert. butyl-, -n-butyl-, -(21, 31- and 41-chloro)- phenyl-, -phenyl- and -tolyl-amides, 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid amide, barbituric acid, 2, 4-dioxyquinoline, acetacetic acid amide, acetoacetic acid N - methyl-, -n -butyl-, -phenyl-, -(21-, 31- and 41-chloro)-phenyl - and - dimethyl - amides and benzoylacetic acid amide and phenylamide.  Cobalting is effected in conventional fashion to yield dyestuffs which per atom of cobalt may contain 1 or 2 molecules of dyestuff.  Dyestuffs derived from #s, #s1-dioxy monoazo-dyestuffs preferably contain 1 atom of metal per two molecules of dyestuff and especially valuable are such dyestuffs derived from the same monoazo dyestuff.  The dyestuffs dye plastic masses, resins, waxes and lacquers and especially silk, leather, wool and materials made from superpoly-amides or -urethanes.  Dyeing is effected in weakly alkaline to weakly acid baths.  Examples are provided of the use of certain of the above specified components in the preparation of cobalt complexes and the use of the latter in conventional dyeing processes, an additional specified diazo component being obtained from 2-aminophenol - 4 - sulphonic acid - 21 - chloranilide - 51 - suphonic acid methylamide.  In the examples wool and superpolyamides are dyed in various tints ranging from yellow to red and blue.  Specifications 637,404, 699,976, 709,495, 716,753 and 724,157 are referred to.