Synthesis and chemoselective crosslinking of functionalized polyesters from bio-based epoxides and cyclic anhydrides

Biomass derivable epichlorohydrin undergoes ring-opening copolymerization with either succinic or itaconic anhydride (both biosourcable) under standard laboratory conditions using metal-based or an entirely organic initiator to form highly functionalized, low molecular weight polyesters. The linear polyesters obtained from epichlorohydrin and itaconic anhydride contain both alkyl chlorides and α,β-unsaturated esters and can be crosslinked to form insoluble resins by treatment with di- to tetra-functional amines and thiols. Crosslinking with amines predominately occurs through the alkyl chlorides whilst crosslinking with thiols occurs through the α,β-unsaturated esters allowing the synthesis of insoluble polyester derived resins with complementary and controllable functionalities.