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Epoxy-free synthesis of aromatic dicyclocarbonates and the related strong epoxy hybrid non-isocyanate polyurethanes
Materials Today Communications ( IF 3.7 ) Pub Date : 2022-12-24 , DOI: 10.1016/j.mtcomm.2022.105263
Yuanmeng Wang , Xiangnan Liu , Yikun Wang , Jingbo Zhao

A new epoxy-free method for synthesizing aromatic five-membered cyclic carbonates (5CCs) was established, and several epoxy hybrid non-isocyanate polyurethanes (HNIPUs) with aromatic segments were prepared from them. First, two aromatic tetraols were synthesized from hydroquinone and bisphenol S with 3-chloro-1,2-propanediol in aqueous NaOH solution. Then, the aromatic 5CCs were prepared through a carbonylation reaction of the tetraols with diethyl carbonate in the presence of K2CO3. Six H2N- terminated polyhydroxyurethane prepolymers (PHUs) were prepared through bulk aminolysis polyaddition of the 5CCs with excessive hexamethylene diamine, and they were crosslinked with an aliphatic epoxy resin to obtain crosslinked HNIPUs. The HNIPUs were amorphous crosslinked hybrid PUs with high crosslinking extent. They showed excellent mechanical property with tensile strength up to 45.1 MPa and good toughness. Introducing aromatic segments increased the stiffness, glass transition temperature, intermolecular interactions, and mechanical properties, and also influenced the swelling properties of HNIPUs.



中文翻译:

芳族二环碳酸酯及相关强环氧杂化非异氰酸酯聚氨酯的无环合成

建立了一种无需环氧合成芳香族五元环状碳酸酯(5CCs)的新方法,并以其为原料制备了几种具有芳香链段的环氧杂化非异氰酸酯聚氨酯(HNIPUs)。首先,在 NaOH 水溶液中,用 3-氯-1,2-丙二醇从对苯二酚和双酚 S 合成了两种芳族四醇。然后,在 K 2 CO 3存在下,通过四醇与碳酸二乙酯的羰基化反应制备芳香族 5CC 。六个H 2通过 5CC 与过量六亚甲基二胺的本体氨解加聚制备 N- 封端聚羟基聚氨酯预聚物 (PHU),并将它们与脂肪族环氧树脂交联以获得交联 HNIPU。HNIPU 是具有高交联度的无定形交联杂化 PU。它们表现出优异的机械性能,抗拉强度高达 45.1  MPa,韧性好。引入芳族链段增加了刚度、玻璃化转变温度、分子间相互作用和机械性能,并且还影响了 HNIPU 的溶胀性能。

更新日期:2022-12-26
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