Structure鈥揂ctivity Relationships and Structural Design Optimization of a Series of p-Hydroxycinnamic Acids-Based Bis- and Trisphenols as Novel Sustainable Antiradical/Antioxidant Additives
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- 作者：Armando F. Reano ; Julie Ch茅rubin ; Aur茅lien M. M. Peru ; Qiao Wang ; Tiphaine Cl茅ment ; Sandra Domenek ; Florent Allais
- 刊名：ACS Sustainable Chemistry & Engineering
- 出版年：2015
- 出版时间：December 7, 2015
- 年：2015
- 卷：3
- 期：12
- 页码：3486-3496
- 全文大小：538K
- ISSN：2168-0485
文摘
Chemo-enzymatic synthesis and screening of a library of renewable saturated and unsaturated bis- and trisphenols deriving from p-hydroxycinnamic acids (i.e., p-coumaric acid, ferulic acid, and sinapic acid) and biobased diols/triol (i.e., isosorbide, 1,4-butanediol, glycerol) showed that these compounds were potent antioxidants/antiradicals. To optimize their antiradical activities, we assessed the structure鈥揳ctivity relationships (SAR) of these phenolics focusing on the internal diol/triol linker, the degree of methoxylation on the aromatic rings, and the C鈺怌 double bond of the 伪,尾-unsaturated esters. We found that methoxylation degree and the unsaturation were critical for antiradical activity while the nature of the diol had a small impact. Indeed, SAR revealed that, for saturated compounds, the higher the methoxylation degree, the higher the antiradical activity; on the other hand, unexpectedly, the presence of the unsaturation had a negative impact on the activity. The antiradical activities of these bis- and trisphenols were then compared to that of Irganox 1010, a widely used antioxidant additive in polypropylene. The optimized compounds, i.e. those deriving from sinapic acid and with saturated esters, proved as effective while being 100% biobased and obtained through a more sustainable synthetic pathway. Thermal analyses (TGA) demonstrated that these bis- and trisphenols exhibit high thermal stability and that their Td5% can be easily tailored by playing with the structure of the bisphenol core. p-Hydroxycinnamic acids-based bis- and trisphenols are thus promising easily accessible, eco-friendly, and biocompatible antiradical additives for a sustainable approach to the stabilization of polymers in packaging and other applications.