Highly Efficient Anionic Ring-Opening Reactions of Epoxide Triggered by Phosphide

Abstract Potassium diphenyl phosphide (KPPh2), which forms a highly nucleophilic phosphide anion, was used as an initiator for the anionic ring-opening polymerization of glycidyl phenyl ether (GPE). GPE was selected as a model compound for the practical application of various glycidyl-type epoxy resins. MALDI-TOF MS analysis of the resulting polymer clarified the presence of a diphenyl phosphine moiety at initiation, confirming that the anionic polymerization was initiated by nucleophilic attack of the phosphide anion on the epoxide. In addition, compared to various basic catalysts such as phosphines and amines, KPPh2 catalyzed the ring-opening addition of epoxide with o-cresol much more efficiently, demonstrating its potential for application to epoxy–phenol curing systems.