Vinylogous Urethane Vitrimers,Advanced Functional Materials

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Vinylogous Urethane Vitrimers
Advanced Functional Materials ( IF 18.5 ) Pub Date : 2015-03-13 , DOI: 10.1002/adfm.201404553
Wim Denissen ₁ , Guadalupe Rivero ₂ , Renaud Nicolaÿ ₃ , Ludwik Leibler ₃ , Johan M. Winne ₁ , Filip E. Du Prez ₁

Affiliation

Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross‐linked. As an alternative to the use of transesterification chemistry, we explore catalyst‐free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m‐xylylene diamine, and tris(2‐aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress‐relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation.

中文翻译：

乙烯基氨基甲酸乙酯三聚体

陶瓷微粉是一类新型的高分子材料，具有非常吸引人的性能，因为它们可以被重新加工成任何形状，同时又可以永久交联。作为使用酯交换化学方法的替代方法，我们探索了含乙烯基氨基甲酸酯的无催化剂转氨作用，作为三聚体的交换反应。首先，对模型化合物的动力学研究表明，在良好的温度范围内，乙烯基类氨基甲酸酯发生了氨基转移反应，而没有副反应。接着，聚（插烯氨酯）与≈2.4GPa的储能模量和玻璃化转变温度高于80℃网络通过的环己烷二甲醇bisacetoacetate，本体聚合制备的米苯二甲胺和三（2-氨基乙基）胺通过溶解度，应力松弛和蠕变实验检查了这些网络的胶体性质。在不使用任何催化剂的情况下，在170°C下观察到的松弛时间短至85 s。此外，通过连续的磨削/压缩成型循环，该网络最多可回收四次，而不会造成明显的机械或化学降解。

更新日期：2015-03-13

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