Patent GB-759353-A (GB)
Title: Manufacture of water-insoluble azo-dyestuffs from 2:3-hydroxynaphthoic acid arylides
IPC: C09B33/02
Filed: 1952-05-26
Abstract: The invention comprises water-insoluble dyestuffs of formula <FORM:0759353/IV(c)/1> where R and R1 are aromatic radicles free of groups imparting solubility in water and X is an alkyl or esterified carboxyl group.  They are made by coupling in substance, on the fibre or on a substratum suitable for producing lakes on appropriate 2, 3-hydroxynaphthoic acid arylide with a diazo- or diazo-azo-compound free of groups imparting solubility in water other than the diazo group.  Preferred diazo-azo-compounds are those of formula <FORM:0759353/IV(c)/2> where A and B may be substituted and especially those where B contains a sulphonic acid group.  The arylides are made by condensing 2, 3-hydroxynaphthoic acid or a functional derivative thereof with an appropriate amino-azo-dyestuff. The arylides are novel and dye vegetable fibres in reddish to greenish yellow tints.  The amino-azo-dyestuffs are made by coupling an appropriate aminophenyl-pyrazolone with a diazotized amine in a neutral to feebly alkaline medium.  When produced in substance the dis-azo dyestuffs yield pigments.  Advantageously they are produced on the fibre by processes used in the production of ice colours.  The preparation of certain of the monoazo starting arylides is described in detail and examples and tables are provided of the preparation of the dyestuffs and their use in dyeing processes the arylides used and/or prepared being derived from 2, 3-hydroxynaphthoic acid or functional derivatives thereof and the following pyrazolones: - 1 - 31 - aminophenyl) - 3 - methyl - 4 - (11 - methoxy - 411 - and - 511 - chloro - , 211 - metyl - 411 - chloro - and 211 - trifluoromethyl - 411 - chloro - benzene - 111 - azo) -, (311 - chlorobenzene - 111 - azo) - and - (naphthalene - 111 - azo) -, 1 - (31 - aminophenyl) - 3 - carboethoxy - 4 - (211 - methyl - 411 - chloro - benzene - 111 - azo) - and 1 - (41 - aminophenyl) - 3 - methyl - 4 - (311 - chloro - and 211 - methyl - 411 - chloro-benzene - 111 - azo) - 5 - pyrazolone the diazo - and diazo - azo - components with which they are coupled being 1 - amino - 4 - (21 - methoxy - 51 - nitro - and 21,41 - dimethoxy-51 - nitro - benzene - 11 - azo) - 2 - ethoxy - naphthalene, 1 - amino - 4 - (21 - methyl-51 - nitro - and 21 - chloro - 51 - nitro - benzene - 11 - azo) - 2 ethoxynaphthalene - 6 - sulphonic acid, 1 - amino - 4 - (21 - methyl - 51 - nitro - benzene - 11 - azo) - 7-methoxynaphthalene, 1 - amino - 4 - (21, 51 - dichloro - and 21 - methoxy - 51 nitro - benzene - 11 - azo) - 2 - methoxynaphthalene-6-sulphonic acid, 1 - amino - 2 - (41 - nitro - 21 - chlorobenzene - 11 - azo) - 3 - methoxy - 4 - methylbenzene, 1 - amino - 4 - (41 - nitro-benzene - 11 - azo) - 2, 5 - diamethoxybenzene, p-nitraniline, 1 - amino - 2,5 - dichlorobenzene, 1 - aminoanthraquinone, 4 - aminodiphenylamine, 4 - amino - 3 - methoxydiphenylamine, 1 - amino - 2 - methoxy - 4 - benzoylamino - 5 - methylbenzene, 1 - amino-4-chloro - 2 - methylbenzene, 1 - amino - 4 - nitro - 2 - methoxybenzene and 1 - amino - 4 - benzoylamino - 2, 5 - diethoxybenzene.  In the examples cotton is dyed in red, brown, green, black, blue and orange shades.  Specification 367,907 is referred to.