Synthesis and characterization of polyisobutylene telechelic prepolymers with epoxide functionality

摘要

Syntheses of novel polyisobutylene telechelic prepolymers with various types of epoxide functionality, including aliphatic glycidyl ether, phenyl glycidyl ether, non-glycidyl aliphatic epoxide, and cycloaliphatic epoxide have been developed. The polyisobutylene prepolymers with aliphatic and phenyl glydicyl ether functionalities were achieved by reaction of primary alcohol-terminated and phenol-terminated polyisobutylene, respectively, with epichlorohydrin. Exo-olefin epoxide-terminated polyisobutylene was synthesized by direct epoxidation of exoolefin-terminated polyisobutylene with a strong oxidizing agent, meta-chloroperoxybenzoic acid. The cycloaliphatic epoxide-terminated polyisobutylene was obtained by nucleophilic substitution of primary bromide endfunctional polyisobutylene with a pre-formed potassium cyclohex-3-enecarboxylate salt, followed by epoxidafion with meta-chloroperoxybenzoic acid. H-1 NMR and MALDI-TOF mass spectrometry analyses demonstrated that the functionality for all types of epoxide prepolymers was 2.0. Gel permeation chromatography (GPC) analysis showed that targeted molecular weight and narrow molecular weight distribution were achieved for these prepolymers and no polymer chain degradation or coupling occurred during post-polymerization modifications.