Crosslinking of styrene-butadiene rubber with polyurethanes bicapped with benzyocyclobutene

Summary A polyurethane prepared from 1,9-nonanediol and toluene-2,4-diisocyanate with M_n=11,840, was capped on both ends in a reaction with 4-(benzocyclobutenyl) methanol. The polyurethane was used to crosslink styrene-butadiene rubber through Diels-Alder reactions on the benzocyclobutene functionality. The synthesis and characterization of 4-(benzocyclobutenyl) methanol, a molecule not reported previously, is presented. The crosslinking reaction was carried out on intimate mixtures of the telechelic polyurethane and SBR at elevated temperature and pressure. Various physical properties of the crosslinked material were studied.Work done at the Department of Chemistry, University of Akron, Akron, OH 44325, USA