Photographisches Verfahren zur Herstellung ein- und mehrfarbiger Bilder nach dem Farbstoffentwicklungsverfahren unter Verwendung von Halogensilberemulsionsschichten

Compounds of formula X-Ar(Z1)n-R-S-Y(Z1)p where X is nitro or amino, R is an alkylene group of preferably not more than 5 carbon atoms, Z1 is alkyl, preferably lower alkyl, or halogen, e.g. chlorine, n is 0, 1 or 2, p is 0, 1, 2 or 3 and Y is a 2,5-dihydroxyphenyl group which may be diacylated may be made by alkylating appropriate mercapto-hydroquinones in the presence of an alkali with the requisite haloalkyl derivative of a nitroaryl compound, acylating the product and/or reducing the nitro group if desired. Ar may be a benzene or naphthalene residue. 2-mercapto-hydroquinone or -toluhydroquinone is refluxed with p-nitrophenethyl bromide in methanolic sodium hydroxide under nitrogen to yield p-nitrophenethyl-thio-hydroquinone or-thiotoluhydroquinone respectively which is acetylated to the diacetate before reduction of the nitro group to an amino group or immediately reduced to the corresponding amine. 2,5-Bis-acetoxyphenylthioaniline is made by treating p-nitro-thiophenol with benzoquinone in ethanol and acetylating and reducing the product. The above products are used in the preparation of dye developers (see Groups IV(c) and XX). Specifications 804,971, 804,972, 811,579, 853,478 and 853,479 are referred to. ALSO: The invention comprises a compound of formula or where X2 is a coupling component residue, a Y - S - R - Ar1 - (Z1)n radical or a Y-S-Ar1-(Z1)n radical, X3 is a coupling component residue or a Y-S-Ar1-(Z2)n radical, Y is a 2,5-dihydroxyphenyl group or an alkyl or halogen substituted derivative thereof, R is an alkylene group, Z1 is alkyl or halogen, Z2 is alkyl, alkoxy or halogen, n is 0, 1 or 2, Ar is an aryl nucleus, m is 0 or 1 and X1 is a coupling component residue. They are made by diazotising compounds of formula (Z1)n-Ar (NH2)-R - S - Y1, (Z2)n - Ar (NH2) - S - Y1, Y1-S-R-Ar (Z1)n-N = N-X1-NH2 and Y1-S-Ar (Z2)n-N = N-X1-NH2 and coupling, preferably at a pH of not above 9, with an appropriate component. The hydroxy groups in Y1 of the coupling component are protected, e.g. by acylation, before coupling is effected and liberated at the end of the reaction. Alternatively compounds of formula HS-R-Ar ( (Z1)n-N = N-X1(-N = N-X2)m or HS-Ar (Z2)n-N = N-X1(-N = N-X3)m may be reacted with appropriate p-benzoquinones. R preferably contains no more than 5 carbon atoms and the ethylene radical is especially preferred. When alkyl groups Z1 and Z2 are present they are preferably of low molecular weight.