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一种受阻酚连接的二苯甲酮杂化化合物作为潜在聚合物抗老化剂的合成、表征及评价

Synthesis, Characterization, and Evaluation of a Hindered Phenol-Linked Benzophenone Hybrid Compound as a Potential Polymer Anti-Aging Agent.

作者信息

Wang Shenshuai, Huang Yingjie, Sun Weiye, Lin Xufeng

机构信息

Department of Chemistry, Zhejiang University, Hangzhou 310058, China.

出版信息

Antioxidants (Basel). 2024 Jul 24;13(8):894. doi: 10.3390/antiox13080894.

Abstract

Hindered phenol antioxidants and benzophenone UV absorbers are common polymer additives and often used in combination applications to enhance the anti-aging performance of polymer materials. This study primarily aims to incorporate hindered phenol and benzophenone structures into a single molecule to develop a multifunctional polymer additive with good anti-aging performance. Thus, a novel potential polymer anti-aging agent, namely 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid 3-(4-benzoyl-3-hydroxyphenoxy)propyl ester (), was synthesized using 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 3-bromo-1-propanol, and 2,4-dihydroxybenzophenone as raw materials by two-step procedure. The structure of compound was characterized by nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), Fourier-transform infrared (FT-IR) spectroscopy, and X-ray single crystal diffraction. Its thermal stability and UV resistance were assessed using thermogravimetric analysis (TGA) and UV absorption spectroscopy (UV). The compound as an additive was incorporated into the preparation of polyolefin elastomer (POE) films. The anti-aging performance of POE films was evaluated by measuring parameters such as oxidation induction time, melt flow index, transmittance, and infrared spectra of the artificially aged POE films. The results indicate that the compound exhibits a promising anti-aging performance in both thermo-oxidative aging and ultraviolet aging tests of POE films and is a potential polymer anti-aging agent.

摘要

受阻酚类抗氧化剂和二苯甲酮类紫外线吸收剂是常见的聚合物添加剂,常用于组合应用中以提高聚合物材料的抗老化性能。本研究主要旨在将受阻酚和二苯甲酮结构引入到单个分子中,以开发一种具有良好抗老化性能的多功能聚合物添加剂。因此,以3-(3,5-二叔丁基-4-羟基苯基)丙酸、3-溴-1-丙醇和2,4-二羟基二苯甲酮为原料,通过两步法合成了一种新型潜在聚合物抗老化剂,即3-(3,5-二叔丁基-4-羟基苯基)丙酸3-(4-苯甲酰基-3-羟基苯氧基)丙酯()。通过核磁共振(NMR)、高分辨率质谱(HRMS)、傅里叶变换红外(FT-IR)光谱和X射线单晶衍射对化合物的结构进行了表征。使用热重分析(TGA)和紫外线吸收光谱(UV)评估了其热稳定性和抗紫外线性能。将化合物作为添加剂掺入聚烯烃弹性体(POE)薄膜的制备中。通过测量人工老化的POE薄膜的氧化诱导时间、熔体流动指数、透光率和红外光谱等参数,评估了POE薄膜的抗老化性能。结果表明,化合物在POE薄膜的热氧化老化和紫外线老化试验中均表现出良好的抗老化性能,是一种潜在的聚合物抗老化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2be6/11351231/901015e5207e/antioxidants-13-00894-g0A1.jpg

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