GB888598A - Diazotype material - Google Patents

Abstract

The invention comprises a diazonium compound of the general formula <FORM:0888598/IV (b)/1> where R1 is a substituted or unsubstituted cyclohexyl group, R2 is a substituted or unsubstituted alkyl group containing up to 3 carbon atoms, R3 is an alkyl group, R4 is a hydrogen atom or a substituent and X is an anion. Such compounds are employed in diazotype materials (see Group XX) and may be prepared, e.g. by alkylating and reducing o-nitro-phenol alkylating the o-alkoxy aniline produced, first with cyclohexyl bromide or cyclohexanone and methyl formate and then with another alkylating agent, e.g. dimethyl sulphate treating the product with nitrous acid to obtain a product with a nitroso group or nitrating or coupling the product with diazotised 2,5-dichloroaniline and reducing the nitroso, nitro or azo compound obtained to an amino compound and diazotizing the latter by treatment with nitrous acid. The diazonium compound may be obtained as a double salt, e.g. by precipitation with zinc chloride or sodium borofluoride. The preparation is described in examples of 4-N-n-propyl-N-cyclohexylamino-3-methoxy-benzene diazonium chloride, zinc, chloride double salt (1); 4-N-methyl - N - cyclohexylamino - 3 - methoxy - 6 - chlorobenzene diazonium chloride, zinc chloride double salt (II) and 4-N-methyl-N-cyclohexyl-amino-3-ethoxy-benzene diazonium chloride, zinc chloride double salt (III). Other specific diazonium compounds mentioned include 4-(N - hydroxyethyl - N - cyclohexylamino) - 3 - n - propoxybenzene diazonium chloride, zinc chloride double salt, 4-N-n-propyl-N-(41 methylcyclohexyl) amino - 3 - methoxy - 6 - chloro - benzene diazonium chloride, zinc chloride double salt, 4 - N - methyl - N - cyclohexylamino - 3 - ethoxy - 6-methyl benzene diazonium chloride cadmium chloride double salt, 4-N-methyl-N-cyclohexyl-amino - 3 - n - butoxy - 6 - bromobenzene di - azonium borofluoride, 4-N-methyl-N-cyclohexyl-amino - 3 - ethoxy - 6 - ethoxybenzene diazonium p-chlorobenzene sulphonate. o-Methoxy-N-cyclohexyl-N-n-propyl-aniline is obtained by reacting o-anisidine with cyclohexyl bromide and reacting the product with propyl bromide. 5 - chloro - 2 - methoxy - N - cyclohexyl - N-methylaniline is obtained by reacting 5-chloro-2-methoxyaniline with cyclohexanone and methyl formate at elevated temperature and pressure and treating with dimethyl sulphate the 5-chloro-2-methoxy-N-cyclohexyl aniline thus obtained. 2 - ethoxy - N - cyclohexyl - N - methylaniline is obtained by reacting o-phenetidine with cyclohexyl bromide and methylating the product. Specification 967,629 is referred to.