Janvier Marine, Hollande Louis, Jaufurally Abdus Samad, Pernes Miguel, Ménard Raphaël, Grimaldi Marina, Beaugrand Johnny, Balaguer Patrick, Ducrot Paul-Henri, Allais Florent
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.
ChemSusChem. 2017 Feb 22;10(4):738-746. doi: 10.1002/cssc.201601595. Epub 2017 Feb 7.
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 (T =279-309 °C) and T 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 (T =319 °C and T =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.
一种可再生双环氧化合物SYR - EPO是通过化学酶合成途径由紫丁香树脂醇制备而成，紫丁香树脂醇是一种源自芥子酸的天然双酚。雌激素活性测试表明紫丁香树脂醇不会造成内分泌干扰。其缩水甘油化反应能以优异的产率和纯度得到SYR - EPO。然后，这种基于生物的安全环氧前体与传统的可再生二胺进行固化反应，以制备环氧胺树脂。对所得热固性材料进行了热性能和机械性能表征。这些新型树脂的热分析显示出优异的热稳定性（T = 279 - 309°C），玻璃化转变温度范围为73至126°C，几乎达到了在聚合物工业中广泛使用的双酚A二缩水甘油醚（DGEBA）所制得材料的性能（DGEBA/异佛尔酮二胺树脂的T = 319°C和T = 150°C）。在NaOH和HCl水溶液中的降解研究也突出了基于紫丁香树脂醇的树脂的稳定性，与双酚A（BPA）相似。所有这些结果无疑证实了紫丁香树脂醇作为BPA更绿色、更安全替代品的潜力。
