Patent GB-475221-A (GB)
Title: Improvements in vulcanization of rubber
IPC: C08K5/00
Filed: 1936-11-13
Abstract: The vulcanization of rubber is accelerated by the addition to the mix of compounds of the general formula <FORM:0475221/IV/1> where AR is an ortho aromatic radical, R is an alkane group containing not more than two carbon atoms and Y is a halogen atom. The preferred compounds are those in which AR is a member of the benzene or naphthalene series, R is CH2, and Y is chlorine. The compounds are prepared by acting on the corresponding thiazyl 1-thio methylene hydrin with a phosphorus halide, or upon the sodium derivative of the corresponding mercaptoarylene thiazole with a di-halogen alkyl compound.  In examples, (1) benzothiazyl 1-thio methylene hydrin and phosphorus trichloride are reacted together to give benzothiazyl 1-thio chloro methane; (2) sodium benzothiazyl mercaptide and ethylene dichloride are refluxed in aqueous alcoholic solution to give beta chloro ethyl benzothiazyl sulphide.  This compound appears to exist in two crystalline forms.  A list of alternative thiazoles is given of which the following are typical, 1-mercapto-5-nitro-benzothiazole, 1-mercapto-6-ethyl benzothiazole, and 1-mercapto-alpha naphtha-thiazole.  As examples of halogen compounds other than chlorine which may be prepared in accordance with the present invention there are bromo-methylbenzothiazyl sulphide, and beta brom ethyl-5-nitro-benzothiazyl sulphide.  The accelerators of the present invention may be used either alone or in conjunction with organic basic nitrogen containing accelerators such as diphenylguanidine di-o-toyl guanidine, urea, ammonia, dibenzyl amine, butyl ammonium oleate, the poly ethylene poly amines, and neutral salts of diphenylguanidine such as the phthalate and succinate.  Examples are given to show the efficiency of the accelerators of the invention in a rubber mix.  The alkylene aryl thiazyl 1-thio hydrins may be prepared by reacting a soluble alkaline salt of a 1-mercapto-aryl thiazole with an alkylene halogen hydrin as an example, the preparation of ethylene benzothiazyl 1-thio hydrin is described.ALSO:The vulcanization of rubber is accelerated by the addition to the mix of compounds of the general formula <FORM:0475221/V/1> where AR is an ortho aromatic radical, R is an alkane group containing not more than two carbon atoms, and Y is a halogen atom.  The preferred compounds are those in which AR is a member of the benzene or naphthalene series.  R is CH2, and Y is chlorine.  The compounds are prepared by acting on the corresponding thiazyl 1-thio methylene hydrin with a phosphorus halide, or upon the sodium derivative of the corresponding mercapto thiazole with a dihalogen alkyl compound.  In examples: (1) benzothiazyl 1-thio methylene hydrin and phosphorus trichloride are reacted together to give benzothiazyl 1-thio chloro methane; (2) sodium benzothiazyl mercaptide and ethylene dichloride are refluxed in aqueous alcoholic solution to give beta chloro ethyl benzothiazyl sulphide.  This compound appears to exist in two crystalline forms.  A list of alternative thiazoles is given of which the following are typical: 1 - mercapto - 5 - nitro - benzothiazole, 1 - mercapto - 6 - ethyl - benzothiazole, and 1 - mercapto-alpha naphtha thiazole.  As examples of halogen compounds other than chlorine which may be prepared in accordance with the present invention, there are bromo-methyl benzothiazyl sulphide, and beta bromo ethyl-5-nitro-benzothiazyl sulphide.  The accelerators of the present invention may be used either alone or in the presence of organic basic nitrogen containing accelerators such as diphenyl-guanidine and its neutral salts such as the phthalate and succinate, di-o-tolyl guanidine, urea, ammonia, dibenzylamine butyl ammonium oleate, and the poly ethylene poly amines.  Examples are given to show the efficiency of the accelerators of the invention in a rubber mix.