Patent GB-613130-A (GB)
Title: Process for preparation of arylides of ortho-hydroxy carboxylic acids and of azo dyestuffs therefrom
IPC: C09B39/00
Filed: 1946-01-28
Abstract: An arylide is prepared by condensing an ortho-hydroxy carboxylic acid of naphthalene, anthracene, carbazole, benzocarbazole, diphenylene oxide, diphenylene sulphide, fluorene or fluorenone, with an aromatic amine of the general formula <FORM:0613130/IV(b)/1> in which R2 is a radical of the benzene series free from water-solubilizing groups and linked directly through a carbon atom of the benzene ring with the nitrogen atom of both the amino and morpholine groups.  For example, the acid or its sodium salt may be condensed with the aromatic amine in the presence of an inert solvent and a condensing agent, e.g. phosphorus trichloride.  The acid may also be condensed in the form of its acid halide or ester.  Examples are given of (1) the condensation of the sodium salt of 2-hydroxy-3-naphthoic acid with 4-(21-amino-41-trifluoro-methyl-phenyl)-morpholine; (2) the condensation of 2-hydroxydiphenylene oxide-3-carboxylic acid with 4-p-aminophenyl morpholine; (3) the condensation of (a) 2-hydroxycarbazole-3-carboxylic acid with 4 - (21 - nitro - 41 - aminophenyl) - morpholine, (b) 2,3-hydroxy-naphthoic acid with 4-p-aminophenyl morpholine and (c) 2-hydroxy-anthracene-3-carboxylic acid with 4-p-aminophenyl morpholine.  Specification 518,989 is referred to.ALSO:An arylide is prepared by condensing an ortho-hydroxy carboxylic acid of naphthalene, anthracene, carbazole, benzocarbazole, diphenylene oxide, diphenylene sulphide, fluorene or fluorenone, with an aromatic amine of the general formula <FORM:0613130/IV (c)/1> in which R2 is a radical of the benzene series free from water-solubilizing groups and linked directly through a carbon atom of the benzene ring with the nitrogen atom of both the amino and morpholine groups.  When coupled with aromatic diazo compounds free from water-solubilizing groups, water-insoluble azo dyestuffs are formed.  When used in dyeing or printing, the films are treated with a paste or liquid containing the arylide and then developed with an aromatic diazo compound free from water-solubilizing groups; alternatively, the fibres are treated with a paste containing the arylide and a stabilized aromatic diazo compound (the diazo portion of which is free from water-solubilizing groups) and the colour developed in an acid ager.  Examples are given of (1) the condensation of the sodium salt of 2-hydroxy-3-naphthoic acid with 4-(21-amino-41-trifluoro-methyl-phenyl)-morpholine; (2) the condensation of 2-hydroxy-diphenylene oxide-3-carboxylic acid with 4-p-aminophenyl morpholine; (3) the condensation of (1) 2-hydroxy-carbazole-3-carboxylic acid with 4-(21-nitro-41-aminophenyl) - morpholine, (b) 2,3 - hydroxynaphthoic acid with 4-p-aminophenyl morpholine, and (c) 2-hydroxy-anthracene-3-carboxylic acid with 4-p-aminophenyl morpholine; (4) the dyeing of cotton by preparing the cotton with the arylide of (3) (c) and developing the colour with the diazo compound from 3-amino - 5 - benzoylamino - 1,4 - hydroquinone diethyl ether; (5) dyeing cotton as in (4) but using the diazo compound from 3-amino-4-chlorobenzotrifluoride; (6) printing cotton with a mixture containing the arylide obtained by condensing 2-hydroxyphenylene oxide-3-carboxylic acid with 4-(21-nitro-41-aminophenyl)-morpholine, and the stabilized diazo compound of 3 - amino - N,N - diethyl - 4 - methoxybenzene sulphonamide, and developing the print in an acid ager; (7) printing cotton with a mixture containing the arylide of (3) (b) and the stabilized tetrazodiamino compound of dianisidine, and developing in an acid ager; and (8) the preparation of a lake from diazotized 2-amino-5-nitro-anisol and 2-hydroxy-3-naphthoyl-p-amido-phenyl morpholine.  Specification 518,989 is referred to.