GB783730A - Improvements in colour photographic processes and materials - Google Patents

Abstract

Azo dyes used as elimination couplers in colour photographic masking procedure are represented by the formul <FORM:0783730/IV (b)/1> <FORM:0783730/IV (b)/2> especially where R1, R2, R3 and R4 are alkyl or acyl groups containing solubilizing groups such as sulphuric or carboxylic groups, and where R2 represents a group for rendering the coupler non-diffusing in the photographic layer; thus in formula I, R3 may be phenyl or sulphophenyl, R4 methyl, sulphobenzamido or carboxybenzamido, and R2 laurylphenyl, oxyoctadecyl, oxydodecyl or butylphenoxyphenyl. In formula II R1 may be sulphobenzamidoethyl, dicarboxyphenyl, disulphobenzamido, sulphobenzamido, sulphophenyl, carboxybenzamidoethyl, carboxyphenyl, dicarboxyphenoxyacetamidoethyl, carboxyphenylsulphonamidoethyl, carboxyethyl or carboxychlorophenyl; and R2 dodecyloxycarbonylphenyl, amyloxycarbonylnaphthyl, dodecyloxycarbonylnaphthyl, diamylphenoxyethoxycarbonylphenyl and the corresponding naphthyl, dodecyloxycarbonylnaphthyl, ethoxyethoxyethoxyethoxycarbonylnaphthyl, ethoxyethoxyethoxycarbonylnaphthyl, dodecyloxyphenyl or palmitylamidonaphthyl. For the styryl dyes, which are not further described, the <FORM:0783730/IV (b)/3> group of formula I is replaced by <FORM:0783730/IV (b)/4> where R5 is an arylene group and R2 is the group described above. Specifications 545,448, 553,196, 553,229, 553,230, 599,377, 617,247, 649,660, 680,488 and 755,655, [all in Group XX], are referred to.ALSO:For azo dyes, used as elimination couplers in colour photographic washing procedure, of structure <FORM:0783730/IV (a)/1> in which R1 is a solubilizing and R2 a non-diffusing group the preparations of intermediates are: (1) phenyl-1-hydroxy-2-naphthoate is reacted with ethylene diamine to produce 1 - hydroxy - 2 - naphthylamidoethylamine and the latter is reacted with phthalic anhydride to produce the corresponding orthocarboxy carbonamide or with (2) the metacarbonyl chloride of benzene sulphonyl chloride or with (3) 1-carbonyl chloride benzene 3.5-disulphonyl chloride with subsequent hydrolysis to produce the corresponding meta and 3.5-sulpho carbonamides respectively; (4) 3-amino-2-naphthoic acid is reacted with (a) n-amyl alcohol, (b) n-dodecyl alcohol, (c) 2,4-diamyl-b -hydroxyethoxybenzene; or (d) 2-amino-benzoic acid is reacted with n-amyl alcohol in presence of dry hydrogen chloride in each case to produce the corresponding aminoesters, and such are diazotized and coupled with the naphthol intermediates of preparations 1-3. Specifications 545,448, 553,196, 553,229, 553,230, 599,377, 617,247, [all in Group XX], 649,660, 680,488, and 755,655, [Group XX], are referred to.