High-performance bio-based epoxies from ferulic acid and furfuryl alcohol: synthesis and properties

Abstract

The lignin derivative ferulic acid was directly functionalized to diepoxy which could be co-cross-linked with furfuryl alcohol-derived monoepoxy to achieve high-performance bio-based thermosets. The development of high-performance bio-based epoxy as a sustainable alternative to fossil-sourced bisphenol A epoxy has great significance. In this work, ferulic acid-based diepoxy (FAE) was facilely synthesized through a direct reaction with epichlorohydrin. After cross-linking, its thermal and mechanical properties are comparable with or even higher than those of bisphenol A epoxy. The carbon–carbon double bond in the framework of the FAE was also exploited to further upgrade its properties via the Diels–Alder reaction with a synthesized glycidyl ether of furfuryl alcohol (GEFA). The chemical structures of FAE and GEFA, curing kinetics, and the Diels–Alder reaction were characterized in detail. The glass transition temperature of FAE-GEFA systems reached ∼250 °C. This work provides a simple way to achieve high-performance thermosets from ferulic acid, and also offers a promising sustainable alternative to bisphenol A epoxy.