Synthesis, characterization and ring-opening polymerization of a novel six-membered cyclic carbonate bearing pendent allyl ether group

Abstract

A novel six-membered cyclic carbonate with pendent allyl ether group, 5-allyloxy-1,3-dioxan-2-one (ATMC), was synthesized from glycerol, and the corresponding polycarbonate, poly(5-allyloxy-1,3-dioxan-2-one) (PATMC) was further synthesized by ring-opening polymerization in bulk at 120°C. Two kinds of catalyst, tin(II) 2-ethylhexanoate (Sn(Oct)2) and immobilized porcine pancreas lipase on silica particles (IPPL), were employed to perform the polymerization. The structures of the novel monomer and the resulting functional polymers were confirmed by FTIR, 1H NMR, 13C NMR, GPC and DSC. The molecular weight (Mn) of PATMC decreased rapidly with the increase of IPPL or Sn(Oct)2 concentration. The highest molecular weight (Mn=48,700g/mol) of PATMC with the polydispersity of 1.31 was obtained at 0.1wt% concentration of IPPL for 48h. Postpolymerization oxidation reactions to epoxidize the unsaturated bonds of the PATMC were also achieved. The epoxide-containing polymers could afford facilities for further modification.