Potential Lignin-Derived Alternatives to Bisphenol A in Diamine-Hardened Epoxy Resins
Potential Lignin-Derived Alternatives to Bisphenol A in Diamine-Hardened Epoxy Resins
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DOI：
10.1021/acssuschemeng.8b03340
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发表时间：
2018-11-05
影响因子：
8.4
通讯作者：
Epps, Thomas H., III
中科院分区：
文献类型：
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作者：
Nicastro, Kaleigh H.;Kloxin, Christopher J.;Epps, Thomas H., III
这项工作详细介绍了木质素衍生的双愈创木酚的合成和表征，作为二胺固化环氧树脂中石油衍生双酚A （BPA）的替代品。木质素甲氧基数量的变化有利于系统的化学和热机械操作，以双愈创木酚为基础的热固性材料达到理想的性能。本文采用酸催化亲电芳取代的方法，以取代的生物衍生羟基苄醇和苯酚为原料，合成了10种甲氧基数量和区域异构体含量不同的双愈创木酚（包括结构异构体），然后用氧环烷官能团进行功能化。这些双愈创木酚二缩水甘油醚随后用模型二胺固化。所有固化的生物衍生树脂的玻璃化转变温度（T-g’s）均在100℃以上，损失率在300℃以上为5%，室温玻璃化储存模量在2.0 GPa以上，这些数值与双酚A二甘油酯（BADGE/DGEBA）固化树脂相当。此外，通过控制甲氧基基团的相对数量和区域异构体的含量，可以很容易地调节最终固化的树脂T-g's（111-151℃）和高温橡胶模量（15-46 MPa），证明了这些生物激发材料的多功能性和稳健性。
This work details the synthesis and characterization of potentially lignin-derived bisguaiacols as alternatives to petroleum-derived bisphenol A (BPA) in diamine-cured epoxy resins. The variations in the number of methoxy groups of lignin facilitate the systematic chemical and thermomechanical manipulation of bisguaiacol-based thermosets to achieve desirable properties. Herein, ten bisguaiacols (including structural isomers), differing in the number of methoxy groups and regioisomer content, were synthesized from substituted bioderivable hydroxybenzyl alcohols and phenols by acid-catalyzed electrophilic aromatic substitution approaches and then functionalized with oxirane groups. These bisguaiacol diglycidyl ethers were subsequently cured with a model diamine. All cured bioderivable resins had glass transition temperatures (T-g's) above 100 degrees C, 5 wt % loss temperatures above 300 degrees C, and room-temperature glassy storage moduli above 2.0 GPa, values that were comparable to bisphenol A diglycidyl ether (BADGE/DGEBA) cured resins. Furthermore, final cured resin T-g's (111-151 degrees C) and high-temperature rubbery moduli (15-46 MPa) were easily tuned by manipulating the relative number of methoxy moieties and the regioisomer content, demonstrating the versatility and robustness of these bioinspired materials.