Copolyesters containing terephthalic and bio-based furanic units by melt-polycondensation

Abstract

5,5′-Isopropylidene-bis(ethyl 2-furoate), a monomer prepared from bio-based ethyl 2-furoate, was reacted with dimethyl terephthalate and ethan-1,2-diol (ED) by melt polycondensation in order to obtain copolyesters containing both terephthalate and furoate units. The conventional two-step method involving (i) the formation of a hydroxyethyl-terminated oligomer by reaction of starting diester mixture with excess ED and (ii) a polycondensation step with elimination of ED was used to obtain high molar mass copolyesters. Copolymers of various compositions were synthesized and characterized by 1H NMR, DSC, and TGA. For all compositions, the degree of randomness, determined by 1H NMR, was close to 1, reflecting a random distribution of terephthalic and furanic ester units in polymer chains. The resulting materials are amorphous polymers (Tg = 70-80°C) with good thermal stability. © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.