The traditional methods for synthesizing imine-based epoxidized soybean oil (ESO) vitrimers often rely on organic solvents, leading to issues such as incomplete raw material conversion, increased production costs, and environmental concerns, contradicting the principles of green and sustainable chemistry. To overcome these challenges, we propose an innovative one-pot, solvent-free approach for synthesizing imine-linked ESO vitrimers via a melt reaction utilizing ESO, vanillin, and diamines. In this system, three distinct reactions can occur: phenolic hydroxy-epoxy, amino-aldehyde, and amino-epoxy. Our findings indicate that the first two reactions occur more readily and rapidly than the third, facilitating the successful synthesis of the vitrimers. We employed three different diamines to tailor the chemical structure and control properties of the ESO vitrimers; aromatic diamines produced rigid vitrimers with high strength but low ductility, while aliphatic diamines yielded flexible vitrimers with lower strength but higher ductility. All vitrimers exhibited rapid high-temperature stress relaxation and excellent reprocessability and thermal stability. Notably, these vitrimers demonstrated impressive adhesive properties, achieving lap shear strengths between 4.0 and 6.7 MPa when applied to various substrates, including wood, steel, and aluminum. Moreover, the dynamic imine bonds enable exceptional recyclability, removability, and reusability, with recycled ESO vitrimers even surpassing their virgin counterparts in mechanical and adhesive performance, underscoring the significance of this work in advancing sustainable adhesive materials with enhanced functionality and circularity.

中文翻译：

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用于可持续胶粘剂的亚胺基环氧化大豆油的一锅法无溶剂合成 Vitrimers


合成亚胺基环氧大豆油 （ESO） 维生素三聚体的传统方法通常依赖于有机溶剂，导致原材料转化不完全、生产成本增加和环境问题等问题，与绿色和可持续化学的原则相矛盾。为了克服这些挑战，我们提出了一种创新的单锅法、无溶剂方法，用于利用 ESO、香兰素和二胺通过熔融反应合成亚胺连接的 ESO vitrimer。在这个系统中，可能会发生三种不同的反应：酚羟基环氧、氨基醛和氨基环氧。我们的研究结果表明，前两个反应比第三个反应更容易和更快地发生，促进了三聚体的成功合成。我们采用了三种不同的二胺来定制 ESO vitrimers 的化学结构和控制特性;芳香族二胺产生强度高但延展性低的刚性 vitrimer，而脂肪族二胺产生强度较低但延展性较高的柔性 vitrimers。所有 vitrimers 均表现出快速的高温应力松弛以及出色的再加工性和热稳定性。值得注意的是，这些 vitrimers 表现出令人印象深刻的粘合性能，当应用于各种基材（包括木材、钢和铝）时，可实现 4.0 至 6.7 MPa 的搭接剪切强度。此外，动态亚胺键实现了卓越的可回收性、可移除性和可重用性，回收的 ESO vitrimers 在机械和胶粘剂性能方面甚至超过了原生 ESO vitrimer，强调了这项工作在推进具有增强功能和循环性的可持续胶粘剂材料方面的重要性。