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

Abstract

AbstractBiomass 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.