GB429320A - Improvements in and relating to vulcanization of rubber - Google Patents

Abstract

Compounds useful as vulcanization accelerators are prepared by the interaction of a water soluble salt of an alkyl or aryl dithiocarbamic acid and an aryl alkyl ketone in which the carbon atom of the alkyl group which is alpha to the carbonyl radical is substituted by a single halogen atom. The products have the general formula <FORM:0429320/IV/1> where X is an aromatic radical substituted or not, R is an alkyl group, and D is a thiocarbamyl group of the structure <FORM:0429320/IV/2> in which R1 and R2 may be like or unlike radicals or may together form a closed chain. Dithiocarbamates mentioned which may be employed are derived from the following amines, dimethyl-, diethyl-, dibutyl-, dicyclohexyl-, methylcyclohexyl-, ethylcyclohexyl-, phenylcyclohexyl, di-isoamyl-, dibenzyl-, ethylphenyl-, cyclohexyl-, di-tetrahydrofurfuryl-, methylnaphthyl-, and dipropylamine and piperidine. Halogen derivatives of arylalkylamines mentioned are:--chloracetophenone, a -chlor-ethylphenyl ketone, a -chlor-propylphenyl ketone, bromacetophenone, a -brom-butylphenyl ketone, chlor-methylnaphthyl ketone, brom-methylnaphthyl ketone, a -chlor-ethylnaphthyl ketone, a -chlor-ethyl-p-chlor-phenyl ketone, chlor-methyl-o-nitrophenyl ketone, chlor-methyl-o-methoyxphenyl ketone, chlor - methyl - o - nitro - m - chlorphenyl ketone, chlor - methyl - p - ethylphenyl ketone, brom - methyl - p - hydroxyphenyl ketone, chlor - methyl - p - aminophenyl ketone, chlor - methyl - 1 - hydroxy - 2 - naphthyl ketone. The reaction is preferably carried out in aqueous acetone solution.ALSO:Compounds useful as vulcanization accelerators are prepared by the interaction of a water soluble salt of an alkyl or aryl dithiocarbamic acid and an aryl alkyl ketone in which the carbon atom of the alkyl group which is alpha to the carbonyl radical is substituted by a single halogen atom. The products have the general formula <FORM:0429320/V/1> where X is an aromatic radical substituted or not, R is an alkyl group, and D is a thiocarbamyl group of the structure <FORM:0429320/V/2> , in which R1 and R2 may be like or unlike radicals or may together form a closed chain. Dithiocarbamates mentioned which may be employed are derived from the following amines: dimethyl-, diethyl-, dibutyl-, dicyclohexyl, methylcyclohexyl-, ethylcyclohexyl-, phenylcyclohexyl, di-isoamyl-, dibenzyl-, ethylphenyl-, cyclohexyl, di-tetrahydrofurfuryl-, methylnaphthyl-, and dipropylamine and piperidine. Halogen derivatives of arylalkylamines mentioned are: chloracetophenone, a -chlor-ethylphenyl ketone, a -chlor propyl phenyl ketone, brom-acetophenone, a -brom-butylphenyl ketone, chlor-methylnaphthyl ketone, brom-methylnaphthyl ketone, a -chlor-ethylnaphthyl ketone, a -chlor-ethyl p-chlor-phenyl ketone, chlor-methyl-o-nitrophenyl ketone, chlor-methyl-o-methoxyphenyl ketone, chlor - methyl - o - nitro - m - chlor - phenyl ketone, chlor - methyl - p - ethylphenyl ketone, brom - methyl - p - hydroxy - phenyl ketone, chlor - methyl - p - aminophenyl ketone, chlormethyl - 1 - hydroxy - 2 - naphthyl ketone. The reaction is preferably carried out in aqueous acetone solution.