title: Syringaresinol: A Renewable and Safer Alternative to Bisphenol A for Epoxy-Amine Resins.
abstract: 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 Tgranging 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.
authors.affiliation: Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres, 51110, Pomacle, France.|Institut Jean-Pierre Bourgin, INRA/AgroParisTech/CNRS/Université Paris-Saclay, Route de Saint-Cyr, 78026, Versailles, France.
authors.forename: Marine
authors.initials: M
authors.lastname: Janvier
authors.affiliation: Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres, 51110, Pomacle, France.|UMR1145 GENIAL, INRA/AgroParisTech, 1 avenue des Olympiades, 91744, Massy, France.
authors.forename: Louis
authors.initials: L
authors.lastname: Hollande
authors.affiliation: Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres, 51110, Pomacle, France.|Institut Jean-Pierre Bourgin, INRA/AgroParisTech/CNRS/Université Paris-Saclay, Route de Saint-Cyr, 78026, Versailles, France.
authors.forename: Abdus Samad
authors.initials: AS
authors.lastname: Jaufurally
authors.affiliation: UMR614 FARE, URCA/INRA, 2 Esplanade Roland Garros, 51686, Reims, France.
authors.forename: Miguel
authors.initials: M
authors.lastname: Pernes
authors.affiliation: Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres, 51110, Pomacle, France.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Ménard
authors.affiliation: Institut de Recherche en Cancérologie de Montpellier, INSERM/Université de Montpellier, 208 rue des Apothicaires, 34298, Montpellier, France.
authors.forename: Marina
authors.initials: M
authors.lastname: Grimaldi
authors.affiliation: UMR614 FARE, URCA/INRA, 2 Esplanade Roland Garros, 51686, Reims, France.
authors.forename: Johnny
authors.initials: J
authors.lastname: Beaugrand
authors.affiliation: Institut de Recherche en Cancérologie de Montpellier, INSERM/Université de Montpellier, 208 rue des Apothicaires, 34298, Montpellier, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Balaguer
authors.affiliation: Institut Jean-Pierre Bourgin, INRA/AgroParisTech/CNRS/Université Paris-Saclay, Route de Saint-Cyr, 78026, Versailles, France.
authors.forename: Paul-Henri
authors.initials: PH
authors.lastname: Ducrot
authors.affiliation: Chaire ABI, AgroParisTech, CEBB 3 rue des Rouges Terres, 51110, Pomacle, France.|UMR 782 GMPA, INRA/AgroParisTech/CNRS/Université Paris-Saclay, Avenue Lucien Brétignières, 78850, Thiverval-Grignon, France.
authors.forename: Florent
authors.initials: F
authors.lastname: Allais
mesh_terms: D000588:Amines; D001559:Benzhydryl Compounds / Q000737:chemistry; D004853:Epoxy Resins / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D055772:Green Chemistry Technology / Q000379:methods*; D017705:Lignans / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis; D000098826:Bisphenol A Compounds
chemical_list: D000588:Amines; D001559:Benzhydryl Compounds; D004853:Epoxy Resins; D005663:Furans; D017705:Lignans; D010636:Phenols; D011108:Polymers; C042192:syringaresinol; C006780:bisphenol A; D000098826:Bisphenol A Compounds
keywords: DGEBA; bisepoxide; bisphenol A; resin; syringaresinol