Synthesis and Characterization of High-Performance, Bio-Based Epoxy–Amine Networks Derived from Resveratrol

• Published in: ACS sustainable chemistry & engineering 2020-09, Vol.8 (37), p.14137-14149
• Main Authors: Garrison, Michael D, Savolainen, Markku A, Chafin, Andrew P, Baca, Joshua E, Bons, Austin M, Harvey, Benjamin G
• Format: Article
• Language: English
• ISSN: 2168-0485; 2168-0485
• DOI: 10.1021/acssuschemeng.0c04816

Resveratrol is a sustainable and versatile bio-derived phenolic compound that has shown promise as a high glass-transition temperature (T g), flame-resistant building block for thermoset networks. In this study, three components of epoxy thermoset resins were synthesized from resveratrol: trans-resveratrol trisepoxy (1), dihydroresveratrol trisepoxy (2), and a trifunctional amine, 4,4′-((5-(4-(4-aminophenoxy)­phenethyl)-1,3-phenylene)­bis­(oxy))­dianiline (4). The epoxy monomers were low melting solids (mp < 80 °C) or thick oils consisting of primarily monomeric trisepoxides. Toxicity testing of 4 revealed that it was not mutagenic and had a low LD50 of 560 mg/kg, an aquatic toxicity of >2000 mg/L, and no cytotoxicity up to its solubility limit. The epoxy monomers were cured with 4,4′-methylenedianiline (3) and 4 to produce four epoxy–amine networks (A–D). Networks C and D, prepared with the resveratrol-derived aniline, contained up to 52.6% bio-based material. The moisture uptake, thermal stability, and dry/wet thermomechanical properties of the networks were measured. The networks had T g’s as high as 285 °C, approximately 110 °C higher than networks based on petroleum-derived bisphenol A (BPA). In addition, the resveratrol networks had char yields as high as 51 and 46% in nitrogen and air, respectively, compared to ca. 15 and 5%, respectively, for BPA-based networks. Overall, this study shows the advantages of resveratrol-based epoxy and amine monomers as components of sustainable, low-toxicity, high-temperature resin systems.