Abstract The development of high-performance biomass-derived epoxy thermosets with excellent flame resistance is vital to various applications (i.e., composites, coatings and adhesives). Herein, a difunctional epoxy monomer bis(2-methoxy-4-(oxiran-2-ylmethyl)phenyl) phenyl phosphate (BEU-EP) was synthesized from abundant and biobased eugenol. In addition, BEU-EP was cured by 4,4′-diaminodiphenyl methane (DDM) and the cured resin diglycidyl ether of bisphenol A (DGEBA)/DDM was used as a reference. Results indicated that BEU-EP/DDM not only showed a 58.1%, 28.8% and 35.1% increase in residual char (at 700 °C), flexural and storage modulus (at 30 °C) compared with DGEBA/DDM, but also exhibited excellent flame resistance and smoke suppression. BEU-EP/DDM passed V-0 rating (in UL-94 testing) with limiting oxygen index (LOI) of 38.4% and greatly decreased the peak heat release rate (pHRR) and total smoke production (TSP) by 84.9% and 80.5%, respectively. The mechanism analysis confirmed that the phosphorus-containing group and aromatic structure from BEU-EP contributed both the gas and condensed-phase flame retardation of BEU-EP/DDM network. This work provides an efficient and scalable route for synthesizing biobased epoxy thermosets with high integrated performance and superior flame resistance.

中文翻译：

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具有优异阻燃性的生物基含磷环氧树脂的简便合成

摘要 开发具有优异阻燃性的高性能生物质衍生环氧热固性材料对于各种应用（即复合材料、涂料和粘合剂）至关重要。在此，从丰富的生物基丁香酚合成了双官能环氧单体双（2-甲氧基-4-（环氧乙烷-2-基甲基）苯基）苯基磷酸酯（BEU-EP）。此外，BEU-EP通过4,4'-二氨基二苯基甲烷（DDM）固化，并以双酚A（DGEBA）/DDM的固化树脂二缩水甘油醚作为参考。结果表明，与 DGEBA/DDM 相比，BEU-EP/DDM 不仅显示出 58.1%、28.8% 和 35.1% 的残余炭（700 °C 下）、弯曲和储能模量（30 °C 下）增加，而且还表现出优异的阻燃性和抑烟性。BEU-EP/DDM 通过了 V-0 等级（在 UL-94 测试中），极限氧指数 (LOI) 为 38。4%，峰值热释放率 (pHRR) 和总烟雾产量 (TSP) 分别降低了 84.9% 和 80.5%。机理分析证实，BEU-EP 中的含磷基团和芳族结构对 BEU-EP/DDM 网络的气相和凝聚相阻燃都有贡献。这项工作为合成具有高综合性能和卓越阻燃性的生物基环氧热固性材料提供了一种有效且可扩展的途径。