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Thermal and mechanical properties of polymer networks prepared by the thiol-ene reaction of a vanillin/acetone condensate and its related compounds
European Polymer Journal ( IF 5.8 ) Pub Date : 2021-08-30 , DOI: 10.1016/j.eurpolymj.2021.110738
Risa Ohno 1 , Kaito Sugane 1 , Mitsuhiro Shibata 1
Affiliation  

A new bio-based diallyl compound, DADVAT, was synthesized by the allylation of 2,5-bis(4-hydroxy-3-methoxybenzylidene)acetone (DVAT), which had been prepared by the cross-aldol condensation of vanillin and acetone. The radical-initiated photothermal thiol–ene reactions of DADVAT/pentaerythritol tetrakis(3-mercaptopropionate) (S4P) at feed molar ratios of 1/1 and 2/1, DVAT/S4P, and trans,trans-dibenzylidene acetone (DBAT)/S4P at a molar ratio of 2/1 produced bio-based polymer networks (ptDADVAT-S4P-11, ptDADVAT-S4P-21, ptDVAT-S4P-21, and ptDBAT-S4P-21). The thermal and mechanical properties of the dual cured polymer networks were compared with those of thermally cured products (tbDADVAT-S4P-21 and tbDBAT-S4P-21) at a molar ratio of 2/1 using triethylamine as a basic catalyst for the nucleophilic thiol–ene reaction. ptDADVAT-S4P-11 displayed excellent thermal and mechanical properties compared to the other cured products. tbDADVAT-S4P-21 and tbDBAT-S4P-21 exhibited better thermal and mechanical properties than ptDADVAT-S4P-21 and ptDBAT-S4P-21, respectively, because the thiol–ene reaction of the enone and thiol groups is promoted by the basic catalyst rather than the radical initiators.



中文翻译:

香兰素/丙酮缩合物及其相关化合物的硫醇-烯反应制备的聚合物网络的热性能和机械性能

2,5-双(4-羟基-3-甲氧基亚苄基)丙酮(DVAT)是由香兰素和丙酮交叉羟醛缩合制备的,通过烯丙基化合成了一种新的生物基二烯丙基化合物DADVAT。DADVAT/季戊四醇四(3-巯基丙酸酯)(S4P)的自由基引发的光热硫醇-烯反应,进料摩尔比为 1/1 和 2/1、DVAT/S4P 和反式,反式-二亚苄基丙酮 (DBAT)/S4P 以 2/1 的摩尔比生成生物基聚合物网络(ptDADVAT-S4P-11、ptDADVAT-S4P-21、ptDVAT-S4P-21 和 ptDBAT-S4P-21)。双固化聚合物网络的热和机械性能与热固化产品(tbDADVAT-S4P-21 和 tbDBAT-S4P-21)以 2/1 的摩尔比使用三乙胺作为亲核硫醇的碱性催化剂进行比较-烯反应。与其他固化产品相比,ptDADVAT-S4P-11 显示出优异的热性能和机械性能。tbDADVAT-S4P-21 和 tbDBAT-S4P-21 分别比 ptDADVAT-S4P-21 和 ptDBAT-S4P-21 表现出更好的热性能和机械性能,因为碱性催化剂促进了烯酮和硫醇基团的硫醇-烯反应而不是自由基引发剂。

更新日期:2021-09-06
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