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

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 (M_n) of PATMC decreased rapidly with the increase of IPPL or Sn(Oct)₂ concentration. The highest molecular weight (M_n = 48,700 g/mol) of PATMC with the polydispersity of 1.31 was obtained at 0.1 wt% concentration of IPPL for 48 h. Postpolymerization oxidation reactions to epoxidize the unsaturated bonds of the PATMC were also achieved. The epoxide-containing polymers could afford facilities for further modification.