Imine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate units with the amine groups of hexamethylenediamine (HMDA). The synthesized product was used in formulations containing ethylene glycol phenyl ether methacrylate (EGPMA) as a reactive diluent for the customization of final material properties and cured by exposure to ultraviolet (UV)-light using suitable radical photoinitiators or else with temperature using a radical thermal initiator. Materials with glass transition temperatures (T_gs) ranging from 70 to 90 °C were prepared, showing good thermal stability and mechanical and thermomechanical properties. The evaluation of their vitrimeric characteristics revealed that all materials achieved a stress-relaxation factor (σ = 0.37σ₀) in less than 130 s at 160 °C, with photocured materials exhibiting faster relaxation rates. The catalytic effect of phosphine oxide groups in imine metathesis has also been evidenced. All prepared materials could be mechanically recycled and completely solubilized in a two-step degradation process, putting evidence of their potential use for carbon fiber-reinforced composites (CFRCs). In addition, they demonstrated promising self-repairing abilities. Finally, as a proof of concept, it was established that these formulations could be effectively processed using a Digital Light Processing three-dimensional (3D) Printer (DLP), resulting in the fabrication of complex shapes with high resolution.

中文翻译：

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通过光固化和热固化程序获得的生物基亚胺 Vitrimer ─用于 3D 打印的有前途的材料

由合成的源自生物基香草醛的二亚胺-二甲基丙烯酸酯单体制备了基于亚胺的玻璃体。首先，合成以香草醛为原料的甲基丙烯酸酯衍生物。二亚胺衍生物是通过两个香草醛甲基丙烯酸酯单元的醛基与六亚甲基二胺（HMDA）的胺基缩合合成的。合成的产品用于含有乙二醇苯醚甲基丙烯酸酯（EGPMA）作为活性稀释剂的配方中，用于定制最终材料性能，并通过使用合适的自由基光引发剂暴露于紫外线（UV）光或使用自由基热引发剂在温度下进行固化。发起者。制备的材料玻璃化转变温度（T _g s）范围为70至90°C，表现出良好的热稳定性以及机械和热机械性能。对玻璃体特性的评估表明，所有材料在 160 °C 下不到 130 秒的时间内就达到了应力松弛因子 (σ = 0.37σ ₀ )，其中光固化材料表现出更快的松弛速率。氧化膦基团在亚胺复分解反应中的催化作用也已得到证实。所有制备的材料都可以机械回收，并在两步降解过程中完全溶解，证明它们在碳纤维增强复合材料（CFRC）方面的潜在用途。此外，它们还表现出了良好的自我修复能力。最后，作为概念验证，确定可以使用数字光处理三维 (3D) 打印机 (DLP) 有效处理这些配方，从而制造出高分辨率的复杂形状。