GB737103A - Improvements in and relating to sulphobenzamides and sulphopropionamides and their use as colour couplers - Google Patents

Abstract

The invention comprises compounds of the general formula R-CONH-Y or R-CONH-D-Y, wherein R is a mononuclear 2-sulpho-1-aryl group of the benzene series or a b -sulphoethyl group, D is an arylene group of the benzene series and Y is a group containing a coupling function, i.e. a grouping which enables the compound to couple, during photographic development of a silver salt, with the oxidation products of the developing agent to form a coloured substance. Typical coupling functions are phenolic hydroxyl groups and reactive methylene groups. The invention comprisses also the preparation of these compounds by reacting a 2-sulphobenzoic anhydride (which may be substituted by chlorine, bromine, methyl, methoxy or phenoxy) or a b -sulphopropionic anhydride with a compound of the general formula Y-NH2, where Y has the same meaning as above, or by reacting a 2-sulphobenzoic anhydride with a compound of the formula H2N-D-Y. In example (1), o-sulphobenzoic anhydride is reacted with 1-phenyl - 3 - {31 - [511 - amino - 211 - (2,4 - di - tert. - amylphenoxy) - benzamido] - benzamido} - 5-pyrazolone to give <FORM:0737103/IV (b)/1> Other examples are given in which o-sulphobenzoic anhydride is reacted with the appropriate amine to yield <FORM:0737103/IV (b)/2> <FORM:0737103/IV (b)/3> <FORM:0737103/IV (b)/4> <FORM:0737103/IV (b)/5> <FORM:0737103/IV (b)/6> <FORM:0737103/IV (b)/7> <FORM:0737103/IV (b)/8> <FORM:0737103/IV (b)/9> <FORM:0737103/IV (b)/100> and b -sulphopropionic anhydride is reacted with the appropriate amine to yield <FORM:0737103/IV (b)/111> <FORM:0737103/IV (b)/122> and <FORM:0737103/IV (b)/133> 1 - Phenyl - 3 - {31 - [511 - amino - 211 - (2,4 - di - tert. - amylphenoxy) - benzamido] - benzamido} - 5-pyrazolone is made by reacting 1-phenyl-3-amino-5-pyrazolone with m-nitrobenzoyl chloride, reducing the product and reacting with 2 - (21,41 - diamylphenoxy) - 5 - nitrobenzoyl chloride and again reducing. The amine used in (2) is prepared by reacting a -(2-methoxybenzoyl) - 4 - amino - 2 - methoxyacetanilide with 2 - (21,41 - di - tert. - amylphenoxy) - 5 - nitrobenzoyl chloride and reducing the nitro group to amino, and the amine used in (3) is prepared similarly from 1-hydroxy-N-(41-aminophenethyl) - 4 - chloro - 2 - naphthamide and 2 - (21,41 - di - tert. - amylphenoxy) - 5 - nitrobenzoyl chloride followed by reduction. Specifications 478,985, 599,919, 737,104 and 737,105 are referred to.