Synthesis and characterization of amphiphilic block copolymers with allyl side-groups

The synthesis of a new cyclic carbonate monomer containing an allyl group was reported and its biodegradable amphiphilic block copolymer, poly(ethylene glycol)-block-poly(L-lactide-co-5-methyl-5-allyloxycarbonyl-propylene carbonate) [PEG-b-P(LA-co-MAC)] was synthesized by ring-opening polymerization (ROP) of L-lactide (LA) and 5-methyl-5-allyloxycarbonyl-1,3-dioxan-2-one (MAC) in the presence of poly (ethylene glycol) as a macroinitiator, with diethyl zinc as a catalyst. ¹³C NMR and ¹H NMR were used for microstructure identification of the copolymers. The copolymer could form micelles in aqueous solution. The core of the micelles is built of the hydrophobic P(LA-co-MAC) chains, whereas the shell is set up by the hydrophilic PEG blocks. The micelles exhibited a homogeneous spherical morphology and unimodal size distribution. By using the cyclic carbonate monomer containing allyl side-groups, crosslinking of the PEG-b-P(LA-co-MAC) inner core was possible. The adhesion and spreading of ECV-304 cells on the copolymer were better than that on PLA films. Therefore, this biodegradable amphiphilic block copolymer is expected to be used as a biomaterial for drug delivery and tissue engineering. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5518-5528, 2007