GB1084487A - Diazonium salt and diazotype copying material containing same - Google Patents

Abstract

The invention comprises diazonium salts of the formula <FORM:1084487/C2/1> in which R1 denotes a hydroxyalkyl radical of 2-4 carbon atoms, R2 denotes an aryloxyalkyl or arylthioalkyl radical, R3 denotes hydrogen or an alkyl, alkoxy or o -hydroxyalkoxy group, R4 denotes hydrogen or halogen or an alkyl or alkoxy group and X denotes an anion. The compounds may be prepared by known methods, as in the following examples: (1) A compound of the formula <FORM:1084487/C2/2> is prepared from the corresponding compound unsubstituted in the p-position to the substituted amino group by a process involving nitration, reduction of the nitro group to an amino group, conversion of the amine into a fluoroborate and diazotization. Similarly obtainable are the corresponding compounds in which (a) an ethoxy or hydroxyethoxy group replaces the methoxy group, (b) a hydrogen atom replaces the chlorine atom, (c) a phenylthioethyl group or a naphthoxyethyl group replaces the phenoxyethyl group, (d) a phenoxypropyl group replaces the phenoxyethyl group, (e) a b -hydroxypropyl group replaces the hydroxyethyl group, and (f) the phenoxyethyl group is substituted by chlorine in the 4position. (2) A compound of the formula <FORM:1084487/C2/3> is prepared by forming an azo dyestuff from 4-nitro-benzene diazonium chloride and 1-N-(b - hydroxyethyl - b - phenoxyethyl) amino-2,5 - diethoxybenzene, reducing the free base of the dye to yield 1-N-(b -hydroxyethyl-b -phenoxyethyl) amino - 2,5 - diethoxy - 4 - aminobenzene, diazotizing the latter and converting the diazo compound into its stannic chloride salt. (3) A compound of the formula <FORM:1084487/C2/4> is prepared by reacting 2-toluidine with bromethyl-phenylether to yield 1-N-(b -phenoxyethyl)amino-2-methylbenzene, reacting this product with ethylene oxide to yield 1-N-(b -hydroxyethyl - b - phenoxyethyl) amino - 2 - methylbenzene, reacting the latter with diazotized p-nitraniline and reducing the azo dyestuff so obtained to yield 1-N-(b -hydroxyethyl - b - phenoxyethyl) amino - 2 - methyl-4-aminobenzene, which is finally diazotized and the diazo compound is converted into its cadmium chloride salt. The products are useful in diazo-type photography.