Protocatechualdehyde-based epoxy vitrimer with low dielectric, excellent flame retardancy, and recyclability

IF 6.5 2区材料科学 Q1 CHEMISTRY, APPLIED

Progress in Organic Coatings Pub Date : 2024-10-02 DOI:10.1016/j.porgcoat.2024.108819

Hui Yang , Guoming Yuan , Zhijun Liu , Yanhan Tao , Panpan Yang , Kun Wu , Jun Shi , Peiwei Hong , Li Yang

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Abstract

Conventional bisphenol A epoxy resins cannot meet the requirements of the new generation of electronic/electrical industries in terms of dielectric properties and flame retardancy and are challenging to reprocess after molding, resulting in waste of resources and environmental hazards. Therefore, a tetrafunctional active ester curing agent (TIE) was successfully synthesized by a one-pot method using biomass protocatechualdehyde as raw materials, followed by curing DGEBA to prepare an epoxy vitrimer (TIE/DGEBA). MHHPA/DGEBA was chosen for comparison since the –OH was also absent after curing. The results showed that TIE/DGEBA had good combinatorial performance, thanks to the unique structure of TIE, including active ester units, siloxane chains, and aromatic Schiff base groups. TIE/DGEBA possessed a lower dielectric constant (2.9 vs. 4.0) compared to MHHPA/DGEBA, which was attributed to the synergistic effect of the less-polar siloxane chain segments, bulky benzene structure, and lower cross-linking density (1971 vs. 733 mol/cm³) of TIE/DGEBA. The aromatic Schiff base not only imparted good thermal stability (T_30% = 418.0 vs. 422.2 °C) to TIE/DGEBA but ensured that it allowed for recycling and reprocessing. After solvent recycling, the resin can be remolded without significant change in tensile strength (53.0 vs. 46.3 MPa). TIE/DGEBA displayed better flame retardancy with higher residual weight (28.2 % vs. 5.5 %), lower total heat release (29.6 vs. 43.5 kJ/g), and good resistance to thermal oxidization. The structural and performance characteristics of TIE/DGEBA offer a strategy for designing multifunctional epoxy-based materials in electrical/electronic applications.

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具有低介电值、优异阻燃性和可回收性的原代邻苯二甲酸环氧树脂玻璃基聚物

传统的双酚 A 环氧树脂在介电性能和阻燃性能方面无法满足新一代电子/电气行业的要求，成型后的再加工也具有挑战性，造成资源浪费和环境危害。因此，我们以生物质原邻苯二甲醛为原料，采用一锅法成功合成了四官能团活性酯固化剂（TIE），然后固化 DGEBA，制备出环氧树脂三聚体（TIE/DGEBA）。选择 MHHPA/DGEBA 作为对比，是因为固化后也不存在 -OH。结果表明，TIE/DGEBA 具有良好的组合性能，这要归功于 TIE 的独特结构，包括活性酯单元、硅氧烷链和芳香族席夫碱基团。与 MHHPA/DGEBA 相比，TIE/DGEBA 的介电常数较低（2.9 对 4.0），这归因于 TIE/DGEBA 的低极性硅氧烷链段、笨重的苯结构和较低的交联密度（1971 对 733 mol/cm3）的协同效应。芳香族席夫碱不仅为 TIE/DGEBA 带来了良好的热稳定性（T30% = 418.0 vs. 422.2 °C），还确保了其可回收和再加工。溶剂回收后，树脂可以重新成型，拉伸强度（53.0 对 46.3 兆帕）不会发生显著变化。TIE/DGEBA 的阻燃性更好，残余重量更高（28.2% 对 5.5%），总放热量更低（29.6 kJ/g 对 43.5 kJ/g），并且具有良好的抗热氧化性。TIE/DGEBA 的结构和性能特点为设计电气/电子应用中的多功能环氧基材料提供了一种策略。

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来源期刊

Progress in Organic Coatings 工程技术-材料科学：膜

CiteScore

11.40

自引率

15.20%

发文量

577

审稿时长

48 days

期刊介绍： The aim of this international journal is to analyse and publicise the progress and current state of knowledge in the field of organic coatings and related materials. The Editors and the Editorial Board members will solicit both review and research papers from academic and industrial scientists who are actively engaged in research and development or, in the case of review papers, have extensive experience in the subject to be reviewed. Unsolicited manuscripts will be accepted if they meet the journal''s requirements. The journal publishes papers dealing with such subjects as: • Chemical, physical and technological properties of organic coatings and related materials • Problems and methods of preparation, manufacture and application of these materials • Performance, testing and analysis.