Etherification of biobased resveratrol with ethylene carbonate and its crosslinked polymethacrylates

Abstract

Biobased polyphenols have been widely studied for their renewable and non-toxic properties, and their thermoplastic/thermosetting materials have also been reported. However, most biobased polyphenols have high melting points and resistance to common solvents, which greatly hinder their applications in organic reactions and material synthesis. Herein, a trihydroxyethyl resveratrol (TER) with a relatively low melting point was prepared by an etherification of biobased resveratrol with ethylene carbonate, and TER trimethacrylate (TTM) was synthesized further from TER and methacryloyl chloride in the presence of triethylamine. TER and TTM were characterized by FTIR, NMR, ESI-MS, and DSC. Free radical curing reaction of TTM was conducted at different initiator dosages, and three crosslinked networks (TER-Ans) were obtained. The conversion rate, crosslinking density, Tg, Tα, mechanical properties, and contact angles were influenced highly by the initiator dosages. At the best initiator dosage of 1 wt% BPO, TER-A2 with the highest crosslinking density (42129.3 mol/m3) and the maximum tensile strength (14.3 MPa) was obtained. Green etherification and hydroxylethylation were established to prepare sustainable crosslinked polymethacrylate materials from biobased resveratrol.