由 -环丁烷-1,2-二羧酸开发的内置热裂解基团的可回收热固性塑料。
A recyclable thermoset with built-in thermocleavable group developed from a -cyclobutane-1,2-dicarboxylic acid.
机构信息
Department of Chemistry, University of North Dakota, Grand Forks, ND 58202, USA.
Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58102, USA.
出版信息
Chem Commun (Camb). 2022 Aug 4;58(63):8850-8853. doi: 10.1039/d2cc01502a.
A novel class of recyclable thermoset has been developed from -3,4-diphenylcyclobutane-1,2-dicarboxylic acid (CBDA-4) due to its thermocleavability at high temperature. This key CBDA-4 building block was synthesized from β--cinnamic acid using a [2+2] photocycloaddition reaction. CBDA-4 was subsequently linked with glycerol esterification to give a thermoset with of 68 °C. The thermoset was heated to 300 °C to analyze its degradation. A key intermediate was successfully obtained after purification of the degraded polymer. NMR, FT-IR, HRMS, and single crystal X-ray diffraction confirmed the intermediate was glycerol cinnamate, which was the result of splitting cyclobutane in the polymer backbone at high temperature. Glycerol cinnamate was readily hydrolyzed reforming the starting materials glycerol and -cinnamic acid to complete the recycling loop.
已开发出一类新型可回收热固性材料，其原料为 -3,4-二苯基环丁烷-1,2-二羧酸（CBDA-4），这是由于其在高温下可热解。该关键 CBDA-4 构建块是由 β-肉桂酸使用[2+2]光环加成反应合成的。随后，将 CBDA-4 与甘油酯化，得到玻璃化转变温度为 68°C 的热固性材料。将热固性材料加热至 300°C 以分析其降解情况。在对降解聚合物进行纯化后，成功获得了一种关键中间体。NMR、FT-IR、HRMS 和单晶 X 射线衍射证实该中间体为甘油肉桂酸，这是聚合物主链中环丁烷在高温下分裂的结果。甘油肉桂酸很容易水解，重新生成起始材料甘油和肉桂酸，从而完成了回收循环。
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