Synthesis, Characterization, and Cross-Linking Strategy of a Quercetin-Based Epoxidized Monomer as a Naturally-Derived Replacement for BPA in Epoxy Resins
Synthesis, Characterization, and Cross-Linking Strategy of a Quercetin-Based Epoxidized Monomer as a Naturally-Derived Replacement for BPA in Epoxy Resins
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DOI：
10.1002/cssc.201600392
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发表时间：
2016-08-23
期刊：
影响因子：
8.4
通讯作者：
Wooley, Karen L.
中科院分区：
文献类型：
--
作者：
Kristufek, Samantha L.;Yang, Guozhen;Wooley, Karen L.
天然多酚化合物槲皮素经过官能化和交联以提供坚固的环氧网络。使用微波辅助反应，将槲皮素选择性地甲基化，并用缩水甘油醚部分进行功能化，得到所需的单体 (Q)。这种槲皮素衍生单体用纳迪克甲基酸酐（NMA）处理以获得交联网络（Q-NMA）。将这种天然衍生网络的热性能和机械性能与传统的二缩水甘油醚双酚 A 衍生对应物 (DGEBA-NMA) 进行比较。 Q-NMA 具有与 DGEBA-NMA 相似的热性能 [即玻璃化转变 (T-g) 和分解 (T-d) 温度] 和相当的机械性能（即杨氏模量、储能模量）。然而，它在高温下具有较低的拉伸强度和较高的弯曲模量。应用天然衍生的可持续化合物来替代市售的石化环氧树脂，对于减少这些材料对环境的影响非常有意义。 Q-NMA 是各种特种工程应用中替代双酚 A 型环氧树脂的有吸引力的候选者。
The natural polyphenolic compound quercetin was functionalized and cross-linked to afford a robust epoxy network. Quercetin was selectively methylated and functionalized with glycidyl ether moieties using a microwave-assisted reaction on a gram scale to afford the desired monomer (Q). This quercetin-derived monomer was treated with nadic methyl anhydride (NMA) to obtain a cross-linked network (Q-NMA). The thermal and mechanical properties of this naturally derived network were compared to those of a conventional diglycidyl ether bisphenol A-derived counterpart (DGEBA-NMA). Q-NMA had similar thermal properties [i.e., glass transition (T-g) and decomposition (T-d) temperatures] and comparable mechanical properties (i.e., Young's Modulus, storage modulus) to that of DGEBA-NMA. However, it had a lower tensile strength and higher flexural modulus at elevated temperatures. The application of naturally derived, sustainable compounds for the replacement of commercially available petrochemical-based epoxies is of great interest to reduce the environmental impact of these materials. Q-NMA is an attractive candidate for the replacement of bisphenol A-based epoxies in various specialty engineering applications.