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Photocurable, Thermally Reprocessable, and Chemically Recyclable Vanillin-Based Imine Thermosets
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-11-10 , DOI: 10.1021/acssuschemeng.0c06248 Yunsheng Xu 1 , Karin Odelius 1 , Minna Hakkarainen 1
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-11-10 , DOI: 10.1021/acssuschemeng.0c06248 Yunsheng Xu 1 , Karin Odelius 1 , Minna Hakkarainen 1
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Two vanillin-based photocurable, thermally reprocessable, and chemically recyclable imine thermosets were successfully designed. The vanillin vitrimer resins were synthesized through a protocol with a two-step reaction: methacrylation and imination with diamine or triamine. The obtained vinyl ester resins with imine bonds and vinyl groups could be photocured into thermosets in 10 min at room temperature. The cured thermosets had good solvent resistance against common solvents, good thermal stability up to about 250 °C as measured by thermogravimetry, and high storage modulus (1.6–3.4 GPa as determined by dynamic mechanical analysis). Owing to the reversibility of the imine bond, both thermosets exhibited typical vitrimer behavior including stress relaxation and thermal reprocessability, while their activation energy for the imine exchange reaction and recovery ratio of tensile stress after reprocessing varied due to different cross-linking densities. Furthermore, both thermosets could be chemically recycled in hexylamine through an imine exchange reaction. The presented new strategy, thus, paves the way for production of fast-curing, chemically and thermally stable, but still thermally reprocessable and chemically recyclable imine vitrimers from abundant biobased building blocks.
中文翻译：
光固化，可热再加工和化学可回收的基于香草醛的亚胺热固性塑料
成功设计了两种基于香兰素的可光固化，可热再加工和可化学回收的亚胺热固性塑料。香兰素三聚体树脂是通过一种具有两步反应的方案合成的：甲基丙烯酸酯化和二胺或三胺的亚胺化。所获得的具有亚胺键和乙烯基的乙烯基酯树脂可以在室温下10分钟内光固化成热固性树脂。固化的热固性塑料对普通溶剂具有良好的耐溶剂性，通过热重分析法测得的良好热稳定性，高达约250°C，并且具有很高的储能模量（通过动态力学分析确定为1.6-3.4 GPa）。由于亚胺键的可逆性，两个热固性树脂均表现出典型的vitrimer行为，包括应力松弛和热再加工性，亚胺交换反应的活化能和后处理后拉应力的恢复率因交联密度的不同而不同。此外，两种热固性塑料都可以通过亚胺交换反应在己胺中进行化学循环。因此，提出的新策略为从丰富的生物基构件生产快速固化，化学和热稳定，但仍可热再加工和化学可循环利用的亚胺三聚体铺平了道路。
更新日期：2020-11-23
中文翻译：
光固化，可热再加工和化学可回收的基于香草醛的亚胺热固性塑料
成功设计了两种基于香兰素的可光固化，可热再加工和可化学回收的亚胺热固性塑料。香兰素三聚体树脂是通过一种具有两步反应的方案合成的：甲基丙烯酸酯化和二胺或三胺的亚胺化。所获得的具有亚胺键和乙烯基的乙烯基酯树脂可以在室温下10分钟内光固化成热固性树脂。固化的热固性塑料对普通溶剂具有良好的耐溶剂性，通过热重分析法测得的良好热稳定性，高达约250°C，并且具有很高的储能模量（通过动态力学分析确定为1.6-3.4 GPa）。由于亚胺键的可逆性，两个热固性树脂均表现出典型的vitrimer行为，包括应力松弛和热再加工性，亚胺交换反应的活化能和后处理后拉应力的恢复率因交联密度的不同而不同。此外，两种热固性塑料都可以通过亚胺交换反应在己胺中进行化学循环。因此，提出的新策略为从丰富的生物基构件生产快速固化，化学和热稳定，但仍可热再加工和化学可循环利用的亚胺三聚体铺平了道路。
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