Epoxy−Polycarbonate Blends Catalyzed by a Tertiary Amine. 1. Mechanism of Transesterification and Cyclization

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, 1 H NMR, 13 C 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.