Syringaresinol: A Renewable and Safer Alternative to Bisphenol A for Epoxy‐Amine Resins

• Published in: ChemSusChem 2017-02, Vol.10 (4), p.738-746
• Main Authors: Janvier, Marine, Hollande, Louis, Jaufurally, Abdus Samad, Pernes, Miguel, Ménard, Raphaël, Grimaldi, Marina, Beaugrand, Johnny, Balaguer, Patrick, Ducrot, Paul‐Henri, Allais, Florent
• Format: Article
• Language: English
• Subjects: Amines; Benzhydryl Compounds - chemistry; bisepoxide; bisphenol A; DGEBA; Epoxy Resins - chemical synthesis; Furans - chemistry; Green Chemistry Technology - methods; Lignans - chemistry; Phenols - chemistry; Polymers - chemical synthesis; resin; syringaresinol
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201601595

A renewable bisepoxide, SYR‐EPO, was prepared from syringaresinol, a naturally occurring bisphenol deriving from sinapic acid, by using a chemo‐enzymatic synthetic pathway. Estrogenic activity tests revealed no endocrine disruption for syringaresinol. Its glycidylation afforded SYR‐EPO with excellent yield and purity. This biobased, safe epoxy precursor was then cured with conventional and renewable diamines for the preparation of epoxy‐amine resins. The resulting thermosets were thermally and mechanically characterized. Thermal analyses of these new resins showed excellent thermal stabilities (Td5 %=279–309 °C) and Tg ranging from 73 to 126 °C, almost reaching the properties of those obtained with the diglycidylether of bisphenol A (DGEBA), extensively used in the polymer industry (Td5 %=319 °C and Tg=150 °C for DGEBA/isophorone diamine resins). Degradation studies in NaOH and HCl aqueous solutions also highlighted the robustness of the syringaresinol‐based resins, similar to bisphenol A (BPA). All these results undoubtedly confirmed the potential of syringaresinol as a greener and safer substitute for BPA. A natural and safe alternative: A bisepoxide monomer prepared from syringaresinol, a natural bisphenolic starting material showing no endocrine disruption, is reacted with different diamines to afford renewable epoxy‐amine resins. The thermal and mechanical properties of these resins are compared to diglycidyl bisphenol A (DGEBA)‐IPDA epoxy resin for potential substitution in advanced material applications.