GB904852A - Colour couplers and photographic silver halide emulsions containing them - Google Patents

Abstract

The invention comprises colour couplers of formula <FORM:0904852/IV (b)/1> or <FORM:0904852/IV (b)/2> where X is halogen; Y is C1-18 alkyl, alkoxy, alkylthi or alkylthio or alkylseleno, or aryl, aryloxy, arylthio or arylseleno; Z, Z1 and Z2 are hydrogen, halogen, or a group as defined for Y; and J is an acylamino group, preferably containing an aromatic radical, and preferably of the formula: <FORM:0904852/IV (b)/3> where R is C1-20 alkyl; Q and Q1 are each hydrogen or C1-6 alkyl;, k, m and p are each 0 or 1; and l, n and q are each 0, 1 or 2. The group J may be any of those customarily present in the 3-position of 1-aryl-5-pyrazolone colour couplers, such as are disclosed in Specifications 547,064, 680,474, 680,488 and 843,497. Many specific examples of suitable Y, Z, Z1, Z2 and R groups are given. The colour couplers are prepared by converting a suitably substituted aniline hydrochloride to the phenylhydrazine, reacting with ethyl b -ethoxy-b -iminopropionate to form the substituted 1-phhenyl-3-amino-5-pyrazolone, and acylating with an acyl chloride. The following couplers are prepared in this way:- <FORM:0904852/IV (b)/4> and details are given for the preparation of the intermediate phenylhydrazines and 1-phenyl-3-amino-5-pyrazolones in which the phenyl is substituted as follows: 4,6-dichloro-2-methoxy, 4,6-dichloro-2-methyl, 6-chloro-2,4-dimethyl, and 2-methoxy-5-methyl. 1 - (6-Chloro-2,4-dimethylphenyl)-3-(3-nitrobenzamido) - 5 - pyrazolone is prepared by reaction of 3-nitrobenzoyl chloride on p the appropriate amino-pyrazolone. Starting materials: 4,6-Dichloro-2-methoxy-aniline hydrochloride is obtained by reaction between o-anisidine hydrochloride and SO2Cl2. 2,6-Dichloro-4-methoxyaniline hydrochloride is obtained by reacting p-nitrosophenol with a saturated solution of HCl in methanol. 4,6-Dichloro-2-methylaniline is prepared by the hydrolysis of 4,6-dichloro-2-methylacetanilide, itself prepared from o-acetotoluidide, sodium acetate, acetic acid, iron powder and chlorine. 6 - Chloro-2,4-dimethylaniline is prepared similarly from 6-chloro-2,4-dimethylacetanilide, itself prepared from 2,4-dimethylacetanilide, sodium acetate, acetic acid, iron powder and chlorine. 2-Methoxy-5-methylacetanilide is obtained by acetylation of 2-methoxy-5-methylaniline, and is treated with SO2Cl2 to give 2-methoxy-5-methyl-3,4,6-trichloroacetanilide, which is then hydrolysed to 2-methoxy-5-methyl-3,4,6-trichloroaniline. Specifications 541,589, 581,772 and 599,919 also are referred to.ALSO:Reference is made to the production of 4-phenylazo derivatives of the compounds of formula <FORM:0904852/IV (b)/1> or <FORM:0904852/IV (b)/2> where X is halogen; Y is C1-18 alkyl, alkoxy, alkylthio or alkylseleno, or aryl, aryloxy, arylthio or arylseleno; Z, Z1 and Z2 are hydrogen halogen, or a group as defined for Y; and J is an acylamino group (see Group IV(b)). Specifications 541,589, 547,064, 581,772, 599,919, 680,474, 680,488 and 843,497 are referred to.