Amine Substitution Reactions of Brominated Poly(isobutylene-<i>c</i><i>o</i>-isoprene): New Chemical Modification and Cure Chemistry
作者:J. Scott Parent、Greg D. F. White、Ralph A. Whitney、William Hopkins
DOI:10.1021/ma0120106
日期:2002.4.1
Nucleophilic substitution reactions of brominated poly(isobutylene-co-isoprene) (BIIR) with amines are characterized through studies of a model compound, brominated 2,2,4,8,8-pentamethyl-4-nonene (BPMN), and analysis of BIIR cure rheology. Nucleophilic amines do not accelerate HBr elimination from the allylic bromide within BIIR but readily engage in N-alkylation reactions with this functional group. N-Alkylation and accompanying proton-transfer reactions are shown to be reversible, and the distribution of allylic bromide, ammonium bromide salts, and their corresponding amines is dictated by equilibrium thermodynamics. N,N-Dimethyloctylamine and N-methyloctadecylamine undergo a single N-alkylation reaction with BPMN, while octylamine forms bis-N-alkylation products that can be used to generate stable cross-linked BUR networks.