Bisalkylation Theory of Neoprene Vulcanization
Abstract Among the organic compounds that are recommended for use with magnesia and zinc oxide as vulcanizing agents for Neoprene are ethylenethiourea (2-imidazolidinethione), p,p′-diaminodiphenylmethane and the di-o-tolylguanidine salt of dicatechol borate. In the absence of sulfur, these agents in combination with zinc oxide do not vulcanize natural rubber. This points up a marked difference in the way these elastomers vulcanize. Although a major structural difference is the chlorine atom in Neoprene in place of the side methyl group in natural rubber, the small amount of tertiary allylic chlorine formed by 1,2-polymerization is the important functional difference. The labile chlorine amounts to about 1.5 per cent of the total chlorine in a general-purpose Neoprene made at 40° C, such as Neoprene Type W used in this work. In Neoprene latex, this active chlorine is gradually liberated, and the polymer becomes cross-linked. This paper demonstrates the importance of the labile chlorine in the vulcanization of dry Neoprene, accounts for the difference in the vulcanization of Neoprene and natural rubber, and suggests a bisalkylation theory of Neoprene vulcanization.