Self-Healing, Recyclable, and Degradable Biobased Epoxy Vitrimers with Dual-Dynamic Imine and Disulfide Bonds

IF 4.7 2区化学 Q2 MATERIALS SCIENCE, MULTIDISCIPLINARY

ACS Applied Polymer Materials Pub Date : 2025-09-18 DOI:10.1021/acsapm.5c02716

Yongzhen Wang, , , Wen Shao*, , , Lijun Chen, , , Xiaoyao Sang, , , Junfeng Zhou*, , and , Jiajia Wang*,

{"title":"Self-Healing, Recyclable, and Degradable Biobased Epoxy Vitrimers with Dual-Dynamic Imine and Disulfide Bonds","authors":"Yongzhen Wang, , , Wen Shao*, , , Lijun Chen, , , Xiaoyao Sang, , , Junfeng Zhou*, , and , Jiajia Wang*, ","doi":"10.1021/acsapm.5c02716","DOIUrl":null,"url":null,"abstract":"<p >Biobased epoxy vitrimers have been proven to be ideal substitutes for achieving reprocessable and recyclable epoxy resins with environmental sustainability. However, constructing a fully biobased epoxy vitrimer with good reprocessability and degradability under mild conditions remains a challenge. In this work, a fully biobased epoxy monomer (FCE) containing dual-dynamic covalent imine and disulfide bonds was easily synthesized from biomass-derived 5-hydroxymethylfurfural and cystamine (CA) through epoxidation and aldehyde-amine condensation. FCE was then further cured with different amines, including CA, isophorondiamine (IPDA), diethyltoluenediamine (DETDA), and tris(2-aminoethyl)amine (TAEA). All of these as-prepared epoxy resins showed high thermal resistance and good mechanical stability. The 5% weight loss temperature for these epoxy resins was around 285–309 °C, with a storage modulus of 2.03–2.86 GPa under room temperature. In particular, the fully biobased epoxy vitrimer (FCE-CA) cured with CA exhibited rapid self-healing and excellent reprocessing ability due to its higher content of dynamic bonds. And the reprocessed epoxy matrix exhibited mechanical strength similar to that of the original one. Furthermore, due to the introduction of imine and disulfide bonds, the epoxy vitrimer could be easily degraded when treated with acid or dithiothreitol. This work offers a facile and green strategy for fabricating recyclable and degradable biobased epoxy vitrimers with excellent integrated properties.</p>","PeriodicalId":7,"journal":{"name":"ACS Applied Polymer Materials","volume":"7 19","pages":"13236–13246"},"PeriodicalIF":4.7000,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Polymer Materials","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsapm.5c02716","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

Abstract

Biobased epoxy vitrimers have been proven to be ideal substitutes for achieving reprocessable and recyclable epoxy resins with environmental sustainability. However, constructing a fully biobased epoxy vitrimer with good reprocessability and degradability under mild conditions remains a challenge. In this work, a fully biobased epoxy monomer (FCE) containing dual-dynamic covalent imine and disulfide bonds was easily synthesized from biomass-derived 5-hydroxymethylfurfural and cystamine (CA) through epoxidation and aldehyde-amine condensation. FCE was then further cured with different amines, including CA, isophorondiamine (IPDA), diethyltoluenediamine (DETDA), and tris(2-aminoethyl)amine (TAEA). All of these as-prepared epoxy resins showed high thermal resistance and good mechanical stability. The 5% weight loss temperature for these epoxy resins was around 285–309 °C, with a storage modulus of 2.03–2.86 GPa under room temperature. In particular, the fully biobased epoxy vitrimer (FCE-CA) cured with CA exhibited rapid self-healing and excellent reprocessing ability due to its higher content of dynamic bonds. And the reprocessed epoxy matrix exhibited mechanical strength similar to that of the original one. Furthermore, due to the introduction of imine and disulfide bonds, the epoxy vitrimer could be easily degraded when treated with acid or dithiothreitol. This work offers a facile and green strategy for fabricating recyclable and degradable biobased epoxy vitrimers with excellent integrated properties.

Abstract Image

查看原文本刊更多论文

自愈，可回收，可降解的生物基环氧树脂与双动态亚胺和二硫键

生物基环氧树脂已被证明是实现可再加工和可回收的具有环境可持续性的环氧树脂的理想替代品。然而，构建一种在温和条件下具有良好可再加工性和可降解性的全生物基环氧玻璃体仍然是一个挑战。以5-羟甲基糠醛和半胺（CA）为原料，通过环氧化和醛胺缩合，制备了一种具有双动态共价亚胺和二硫键的全生物基环氧单体（FCE）。然后用CA、异磷二胺（IPDA）、二乙基甲苯二胺（DETDA）和三（2-氨基乙基）胺（TAEA）等不同的胺进一步固化FCE。所制备的环氧树脂具有较高的耐热性和良好的机械稳定性。5%失重温度为285 ~ 309℃，室温下的存储模量为2.03 ~ 2.86 GPa。特别是用CA固化的全生物基环氧玻璃体（FCE-CA），由于其较高的动态键含量，表现出了快速的自愈和优异的再加工能力。再加工后的环氧树脂基体的机械强度与原始环氧树脂基体相近。此外，由于引入了亚胺和二硫键，当酸或二硫苏糖醇处理时，环氧玻璃聚合物很容易被降解。这项工作为制造具有优异综合性能的可回收和可降解的生物基环氧树脂提供了一种简单和绿色的策略。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

ACS Applied Polymer Materials Multiple-

CiteScore

7.20

自引率

6.00%

发文量

810

期刊介绍： ACS Applied Polymer Materials is an interdisciplinary journal publishing original research covering all aspects of engineering, chemistry, physics, and biology relevant to applications of polymers. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrates fundamental knowledge in the areas of materials, engineering, physics, bioscience, polymer science and chemistry into important polymer applications. The journal is specifically interested in work that addresses relationships among structure, processing, morphology, chemistry, properties, and function as well as work that provide insights into mechanisms critical to the performance of the polymer for applications.