Biobased and Aromatic Reversible Thermoset Networks from Condensed Tannins via the Diels−Alder Reaction

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• 作者：Antoine Duval ; Guillaume Couture ; Sylvain Caillol ; Luc Avérous
• 刊名：ACS Sustainable Chemistry & Engineering
• 出版年：2017
• 出版时间：January 3, 2017
• 年：2017
• 卷：5
• 期：1
• 页码：1199-1207
• 全文大小：564K
• ISSN：2168-0485

文摘

Thermo-reversible networks were obtained for the first time from tannins, an aromatic biobased polyphenol, by reacting furan-bearing tannins and telechelic oligomers with maleimide end groups, using the Diels−Alder (DA) reaction. Condensed tannins from mimosa (Acacia mearnsii) were functionalized with furfuryl glycidyl ether and thoroughly characterized by ¹H, ³¹P NMR, and FTIR spectroscopy. The accessibility of the grafted furan groups was confirmed by a model reaction with N-methylmaleimide. Different cross-linked networks were then obtained by DA reaction with three PPO and PPO-b-PEO-b-PPO oligomers and evidenced by FTIR spectroscopy. The thermal properties of the obtained networks were evaluated with differential scanning calorimetry (DSC) and thermogravimetric analysis. Then, the reversibility of the cross-linking was shown by a quick return to the liquid state upon heating at 120 °C. The retro Diels−Alder reaction was studied by size exclusion chromatography and DSC.