Patent GB-804974-A (GB)
Title: Improvements relating to process for preparing dye developers
Inventor: BLOUT ELKAN ROGERS
IPC: C09B1/26
Filed: 1955-03-09
Abstract: The invention comprises dye developers and a process of making them by the combination of a dye containing a hydroxyl, primary amino, secondary amino, carboxyl, or sulpho group with a developer compound containing an aryl nucleus substituted by at least two substituents selected from hydroxyl, amino, and substituted amino groups so that the resulting compound is capable of developing exposed silver halide and having a further substituent, which process comprises forming, between said dye and said developer compound, a bond through which the colour characteristics of the dye unit are maintained substantially free from the influence of the developer unit by the reaction of said hydroxyl, primary or secondary amino, carboxyl or sulpho group of the dye with the further substituent of the developer compound.  In particular, dyes containing hydroxy or primary or secondary amino with compounds of the formul : <FORM:0804974/IV (c)/1> or <FORM:0804974/IV (c)/2> or <FORM:0804974/IV (c)/3> where D1 is a group containing an aryl nucleus substituted by at least two substituents selected from hydroxy, amino, and/or substituted amino so that the resulting compound is capable of developing exposed silver halide, R4 is hydrogen or alkyl, R5 is chlorine, a group of the formula: <FORM:0804974/IV (c)/4> hydroxy, amino, aryloxy, alkoxy, alkylamino, or alkyl.  Other methods of building up these molecules are referred to generally. One of the hydroxy, amino, or substituted amino groups of D1 may be acylated, and said acyl group removed by hydrolysis subsequently.  Examples of suitable bonds joining dye and developer units are a covalent bond, and the groups -CO-, -CH2.CONH-, -CJ2-(where J is hydrogen, alkyl, or aryl), -SO2-, -B-, (where B is a bivalent hydrocarbon residue, e.g. alkylene or arylene), -NJ-B-, -SO2-B-SO2-, -CO-B-, -CO-B-CO-, -alkylene -NH-NH-alkylene-, -B-O-, -O-P(OH)-O-, -O-B-O-, -SO3-B-NH-, or the bivalent residue of a hydroaromatic or heterocyclic ring.  In examples: (1) O - monobenzoyl - hydroquinonylamino - dichloro - s - triazine is reacted with p - aminoazobenzene, giving after hydrolysis of a chlorine atom, 2 - hydroquinonylamino - 4 - (p - phenylazo - anilino) - 6 - hydroxy - s - triazine, or with dimethoxy - diphenyl - disazo - bis - 8 - amino - 1 - naphthol - 5,7 - disodium sulphonate, 1 - amino-4 - (p - aminophenylamino) - anthraquinone - 2 - sodium sulphonate; 4 - amino - 41 - sulphoazobenzene, or 4,8 - diamino - 1,5 - dihydroxyanthraquinone; (2) gentisic acid chloride, homogentisic acid chloride or homogentisic acid lactone is reacted with 1,4-bis-(beta-aminoethylamino) - anthraquinone, or with 1 - amino - 4 - (p - aminoanilino) - anthraquinone-2-sulphonic acid; (3) homogentisic acid chloride dibenzoate is reacted with 1-phenyl-3-amino-4-phenylazo - 5 - pyrazolone, followed by hydrolysis; (4) chloroacetamido-hydroquinonone monobenzoate is reacted with 1,4-bis-(beta-aminoethylamino)- or 1,4-bis-(beta-hydroxyethylamino)-anthraquinone or with 1-amino-4-(p - aminoanilino) - anthraquinone - 2 - sodium sulphonate.  Other examples of developer unit D1 are 3,4 - dihydroxyphenyl, 1 - hydroxy - 4 - aminophenyl, 1 - hydroxy - 4 - methylaminophenyl, 1,2,3 - trihydroxyphenyl, and 1 - hydroxy - 2 - aminonaphthyl. Specifications 804,973 and 804,975 are referred to.