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Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry
Macromolecular Chemistry and Physics ( IF 2.5 ) Pub Date : 2021-07-03 , DOI: 10.1002/macp.202100146 Maddalen Puyadena 1 , Itxaso Calafel 1 , Estíbaliz González de San Román 2 , Loli Martin 3 , Alba González 1 , Lourdes Irusta 1
Macromolecular Chemistry and Physics ( IF 2.5 ) Pub Date : 2021-07-03 , DOI: 10.1002/macp.202100146 Maddalen Puyadena 1 , Itxaso Calafel 1 , Estíbaliz González de San Román 2 , Loli Martin 3 , Alba González 1 , Lourdes Irusta 1
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Taking advantage of the reversible Diels–Alder (DA) reaction, a simple strategy to obtain recyclable epoxy resins is presented. For this purpose, blends of furan-functionalized and nonfunctionalized epoxy resin are prepared. After the addition of diamine and bismaleimide, blends are heated at 150 °C for 5 min, where the permanent amine/epoxy reaction has taken place and upon cooling to room temperature the reversible DA reaction has happened, giving rise to a dual permanent/nonpermanent network. Both reactions are confirmed by Fourier-transform infrared (FTIR) and 13C-crosspolarization, magic-angle spinning (CP/MAS) nuclear magnetic resonance (NMR). Modulated differential scanning calorimetry (MDSC) shows that the epoxy/amine and bismaleimide/amine curing reaction take place, after the DA reaction, simultaneously with the retroDA reaction and before the bismaleimide homopolymerization. Therefore, under the appropriate curing conditions, the Michael's addition and the bismaleimide homopolymerization do not avoid the formation of a hybrid network, as stated in other reports. The reversibility of the DA reaction in three consecutive cycles is confirmed by DSC. Finally, the dual-cured sample is reprocessed three times without significant loss of mechanical properties.
中文翻译：
基于 Diels-Alder 化学的同时双重永久/可逆交联可回收环氧树脂
利用可逆的狄尔斯-阿尔德 (DA) 反应，提出了一种获得可回收环氧树脂的简单策略。为此，制备了呋喃官能化和非官能化环氧树脂的混合物。添加二胺和双马来酰亚胺后，共混物在 150 °C 下加热 5 分钟，其中发生永久性胺/环氧树脂反应，冷却至室温后发生可逆 DA 反应，产生双重永久性/非永久性网络。两种反应均通过傅里叶变换红外 (FTIR) 和13C-交叉极化、魔角旋转 (CP/MAS) 核磁共振 (NMR)。调制差示扫描量热法 (MDSC) 显示环氧/胺和双马来酰亚胺/胺固化反应发生在 DA 反应之后，与逆 DA 反应同时发生，在双马来酰亚胺均聚之前。因此，在适当的固化条件下，迈克尔加成和双马来酰亚胺均聚并不能避免混合网络的形成，如其他报道所述。DSC 证实了连续三个循环中 DA 反应的可逆性。最后，双固化样品再加工 3 次，机械性能没有显着损失。
更新日期：2021-09-07
中文翻译：
基于 Diels-Alder 化学的同时双重永久/可逆交联可回收环氧树脂
利用可逆的狄尔斯-阿尔德 (DA) 反应，提出了一种获得可回收环氧树脂的简单策略。为此，制备了呋喃官能化和非官能化环氧树脂的混合物。添加二胺和双马来酰亚胺后，共混物在 150 °C 下加热 5 分钟，其中发生永久性胺/环氧树脂反应，冷却至室温后发生可逆 DA 反应，产生双重永久性/非永久性网络。两种反应均通过傅里叶变换红外 (FTIR) 和13C-交叉极化、魔角旋转 (CP/MAS) 核磁共振 (NMR)。调制差示扫描量热法 (MDSC) 显示环氧/胺和双马来酰亚胺/胺固化反应发生在 DA 反应之后，与逆 DA 反应同时发生，在双马来酰亚胺均聚之前。因此，在适当的固化条件下，迈克尔加成和双马来酰亚胺均聚并不能避免混合网络的形成，如其他报道所述。DSC 证实了连续三个循环中 DA 反应的可逆性。最后，双固化样品再加工 3 次，机械性能没有显着损失。
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