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Trans‐limonene dioxide, a promising bio‐based epoxy monomer
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2021-01-12 , DOI: 10.1002/pol.20200822 Louis Schutz 1 , Forouzan Kazemi 1 , Elby Mackenzie 1 , Jean‐Yves Bergeron 2 , Eric Gagnon 2 , Jerome P. Claverie 1
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2021-01-12 , DOI: 10.1002/pol.20200822 Louis Schutz 1 , Forouzan Kazemi 1 , Elby Mackenzie 1 , Jean‐Yves Bergeron 2 , Eric Gagnon 2 , Jerome P. Claverie 1
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Vast quantities of the natural terpene (R)‐limonene can be collected from food waste. Epoxidation of its two double bonds provides limonene dioxide (LDO), a difunctional epoxy monomer. However, LDO is a mixture of four isomers, two of which (trans‐LDO) are actually difunctional while the others (cis‐LDO) have one epoxide group which is significantly less reactive, as revealed by Fourier transformed infrared spectroscopic analysis of formulations cross‐linked with polyethylene imine. These results are also confirmed when preparing epoxy formulations using respectively cis or trans isomers. From DFT calculations, the reactivity of each epoxide group of LDO has been assessed in model reactions with primary and secondary amines, in the presence of amine or alcohol hydrogen‐bond donors. The kinetics of cross‐linking has also been probed by differential scanning calorimetry. As measured by dynamic mechanical analysis, the resulting epoxy resins based on trans isomers have a storage modulus of ca 1GPa at room temperature and a glass transition temperature (Tg) of 70°C. These results demonstrate that trans LDO is a promising bio‐based epoxy monomer, which could be used as an alternative to petroleum‐based epoxy monomers.
中文翻译：
反式二氧化烯，一种有前途的生物基环氧单体
可以从食物垃圾中收集大量的天然萜烯（R）-柠檬烯。它的两个双键的环氧化提供了二功能环氧丙烷（LDO）。然而，LDO是四种异构体的混合物，其中两个（反式-LDO）实际上是双官能的，而其他的（顺式-LDO）具有一个环氧基团，其反应性明显较低，这通过傅立叶变换红外光谱分析发现与聚乙烯亚胺连接。当分别使用顺式或反式制备环氧配方时，也证实了这些结果异构体。根据DFT计算，在存在胺或醇氢键供体的情况下，在与伯胺和仲胺的模型反应中评估了LDO的每个环氧基的反应性。还通过差示扫描量热法探讨了交联的动力学。如通过动态力学分析测量，基于所得到的环氧树脂的反式异构体具有的储能模量CA在室温下1GPa和玻璃化转变温度（T克的70℃）。这些结果表明，反式LDO是一种很有前途的生物基环氧单体，可以用作石油基环氧单体的替代品。
更新日期：2021-02-15
中文翻译：
反式二氧化烯，一种有前途的生物基环氧单体
可以从食物垃圾中收集大量的天然萜烯（R）-柠檬烯。它的两个双键的环氧化提供了二功能环氧丙烷（LDO）。然而，LDO是四种异构体的混合物，其中两个（反式-LDO）实际上是双官能的，而其他的（顺式-LDO）具有一个环氧基团，其反应性明显较低，这通过傅立叶变换红外光谱分析发现与聚乙烯亚胺连接。当分别使用顺式或反式制备环氧配方时，也证实了这些结果异构体。根据DFT计算，在存在胺或醇氢键供体的情况下，在与伯胺和仲胺的模型反应中评估了LDO的每个环氧基的反应性。还通过差示扫描量热法探讨了交联的动力学。如通过动态力学分析测量，基于所得到的环氧树脂的反式异构体具有的储能模量CA在室温下1GPa和玻璃化转变温度（T克的70℃）。这些结果表明，反式LDO是一种很有前途的生物基环氧单体，可以用作石油基环氧单体的替代品。
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