Green polymer chemistry: One-pot, metal-free synthesis of macromonomer via direct polycondensation of lactic acid and its radical polymerization to graft and comb polymers

Abstract

A new and simple method of one-pot two-stage poly(lactic acid) (PLA) macromonomer synthesis has been developed. The first stage of the reaction is a direct polycondensation of lactic acid (LA) without a catalyst to PLA, and the second stage is a ring-opening addition of PLA to glycidyl methacrylate (GMA) to afford a PLA macromonomer with a methacryloyl polymerizable group (GMA-Macro). Both reactions are performed consecutively in one pot. This method produced GMA-Macro with high functionality in high yields and thus far seems the simplest and probably the cheapest way to prepare PLA macromonomers. Furthermore, the method is metal-free, offering considerable advantages for biomedical and pharmaceutical applications. GMA-Macro has been shown to be useful for the preparation of PLA graft copolymers in solution or in miniemulsion and of PLA comb polymers in solution. LA is a biobased renewable feedstock. Thus, this method provides a good opportunity to conduct ‘green polymer chemistry’.