The Preparation and Polymerization of N, N' -Divinylureas

Abstract

Abstract A new synthetic route to N, N'-disubstituted-N, N'-divinylureas is described. The method involves the preparation of the disodium salts of N, N'-disub-stituted ureas, their conversion to the corresponding di-(β-dimethylaminoethyl) derivatives and the application of the Cope or the Hofmann reaction to these. 1,3-Divinylimidazolid-2-one (Va), l,3-divinylhexahydropyrimid-2-one (Vb), and N, N'-diphenyl-N, N'-diviflyIurea (Vc) have been prepared by this route. The two cyclic N, N'-divinylureas (Va and Vb) were polymerized, using a radical initiator, to heavily cross-linked polymers containing a significant proportion of residual N-vinyl groups. There is no apparent evidence from IR spectra for the bicyclic units which would be present if any cyclopolymer-ization had occurred. The diphenyl compound (Vc) could not be polymerized under a variety of conditions and initiators. An explanation is suggested for the inability of Va and Vb to cyclopolymerize.