Preparation of chitosan-based macromolecular antioxidant with high-efficiency free radical scavenging ability to improve the antioxidative properties of styrene-butadiene rubber/silica composites

IF 6.5 2区 材料科学 Q1 MATERIALS SCIENCE, COMPOSITES
Xiaojiang Xie , Lihao Wu , Jingwei He , Fang Liu
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Abstract

To address the disadvantages of traditional rubber antioxidants with low molecular weight such as easy migration, poor extraction resistance, low thermal stability and antioxidant efficiency, in this work, we first prepared an antioxidant containing primary and secondary antioxidant groups (MC-MPA) through thiol-ene click reaction between N-(4-aminophenyl)maleimide (MC) and 3-mercaptopropionic acid (MPA). Then, we synthesized a chitosan-based macromolecular antioxidant with long-chain alkene, aromatic secondary amine, and thioether groups (COS-UC-MC-MPA) by sequentially grafting functional compounds 10-undecanonyl chloride (UC) and antioxidant MC-MPA onto natural macromolecular polymer chitosan (COS). The free radical scavenging ability of COS-UC-MC-MPA was assessed by using 2,2-Diphenyl-1-picrylhydrazyl (DPPH), and the results demonstrated that COS-OC-MC-MPA has high scavenging rate of 76.5 % for DPPH free radicals after 1 min of contact with DPPH dimethyl sulfoxide solution, showing excellent free radical scavenging ability. In addition, the results of accelerated thermo-oxidative aging test, thermogravimetric (TG) test, kinetic analysis of thermal-oxidative degradation, extraction resistance test, and volatilization resistance test indicated that COS-UC-MC-MPA with superior migration resistance and volatilization resistance could effectively enhance the antioxidative properties, thermal stability and thermal-oxidative stability of rubber composites. Moreover, the results of rubber processibility analysis (RPA) test and scanning electron microscopy (SEM) implied that the addition of COS-UC-MC-MPA is also conductive to improving the dispersibility of silica in rubber matrix. This study supplies a new perspective for the preparation of environmentally friendly and highly efficient macromolecular antioxidants for rubber composites.

制备具有高效自由基清除能力的壳聚糖基高分子抗氧化剂以改善丁苯橡胶/二氧化硅复合材料的抗氧化性能
针对传统低分子量橡胶防老剂易迁移、耐萃取性差、热稳定性低、防老效率低等缺点,本研究首先通过N-(4-氨基苯基)马来酰亚胺(MC)和3-巯基丙酸(MPA)之间的硫醇-烯点击反应制备了一种含有一级和二级防老基团的防老剂(MC-MPA)。然后,我们将功能化合物 10-十一烷酰氯(UC)和抗氧化剂 MC-MPA 依次接枝到天然大分子聚合物壳聚糖(COS)上,合成了具有长链烯基、芳香族仲胺和硫醚基团的壳聚糖基大分子抗氧化剂(COS-UC-MC-MPA)。用 2,2-二苯基-1-苦基肼(DPPH)对 COS-UC-MC-MPA 的自由基清除能力进行了评估,结果表明 COS-OC-MC-MPA 与 DPPH 二甲亚砜溶液接触 1 分钟后,对 DPPH 自由基的清除率高达 76.5%,表现出优异的自由基清除能力。此外,加速热氧化老化试验、热重(TG)试验、热氧化降解动力学分析、耐萃取试验和耐挥发试验的结果表明,COS-UC-MC-MPA 具有优异的耐迁移性和耐挥发性,能有效提高橡胶复合材料的抗氧化性、热稳定性和热氧化稳定性。此外,橡胶加工性分析(RPA)测试和扫描电子显微镜(SEM)的结果表明,COS-UC-MC-MPA 的添加还有利于提高白炭黑在橡胶基体中的分散性。这项研究为制备用于橡胶复合材料的环保型高效高分子抗氧化剂提供了新的视角。
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来源期刊
Composites Communications
Composites Communications Materials Science-Ceramics and Composites
CiteScore
12.10
自引率
10.00%
发文量
340
审稿时长
36 days
期刊介绍: Composites Communications (Compos. Commun.) is a peer-reviewed journal publishing short communications and letters on the latest advances in composites science and technology. With a rapid review and publication process, its goal is to disseminate new knowledge promptly within the composites community. The journal welcomes manuscripts presenting creative concepts and new findings in design, state-of-the-art approaches in processing, synthesis, characterization, and mechanics modeling. In addition to traditional fiber-/particulate-reinforced engineering composites, it encourages submissions on composites with exceptional physical, mechanical, and fracture properties, as well as those with unique functions and significant application potential. This includes biomimetic and bio-inspired composites for biomedical applications, functional nano-composites for thermal management and energy applications, and composites designed for extreme service environments.
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