Epoxy-polycarbonate blends catalyzed by a tertiary amine .1. Mechanism of transesterification and cyclization

Abstract

In the Bisphenol A base polycarbonate-Bisphenol A base epoxy blend system, the carbonate group can react with epoxide in the presence of a tertiary amine. The transesterification reactions convert the original aromatic/aromatic carbonate of PC to aromatic/aliphatic and aliphatic/aliphatic carbonates. IR spectroscopy shows an unknown major structure formed during the later stages of the transesterification reaction. The unknown structure was investigated by a model reaction using diphenyl carbonate and phenyl glycidyl ether leading to the formation of 4-(phenoxymethyl)-1,3-dioxolan-2-one (PMD), which has been identified by IR, UV, H-1 NMR, C-13 NMR, and mass spectroscopy. The mechanism of forming the cyclic carbonate is proposed to proceed through a zwitterion and a nucleophile attack of the aromatic/aliphatic or the aliphatic/aliphatic carbonate group.