Epoxy derived from heteroaromatic compounds and its properties are seldom reported. In this work, two model epoxy monomers (EP-B and EP-F) were synthesized from isophthalic acid and 2,5-furandicarboxylic acid. After curing with 4,4-diaminodiphenylmethane (DDM) in a stoichiometric quantity of 2:1, their properties were comparatively investigated, especially the formation and role of hydrogen bonding in them were identified. Results obtained from differential scanning calorimetry (DSC), dynamic thermomechanical analysis (DMA), fluorescence emission spectra, and static contact angle measurements showed that the cured EP-F/DDM system exhibited unexpected performance in higher glass transition temperature (T_g), fluorescence intensity, and hydrophilicity. And temperature-dependent Fourier transform infrared (FT-IR) analysis further confirmed that it was the more hydrogen bonding in the cured EP-F/DDM, involved with the oxygen heteroatoms in the furan ring, which led to its better properties. This work gives us some new insights into the role of electronegative heteroatoms in epoxy resin synthesized from heteroaromatic compounds.

中文翻译：

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芳香和杂芳族化合物衍生的环氧树脂性能的比较研究：氢键的作用

很少报道衍生自杂芳族化合物的环氧树脂及其性质。在这项工作中，由间苯二甲酸和2,5-呋喃二甲酸合成了两种模型环氧单体（EP-B和EP-F）。在化学计量比为2：1的4,4-二氨基二苯甲烷（DDM）固化后，对它们的性能进行了比较研究，尤其是确定了氢键的形成和作用。从差示扫描量热法（DSC），动态热机械分析（DMA），荧光发射光谱和静态接触角测量获得的结果表明，固化的EP-F / DDM系统在较高的玻璃化转变温度（T _g），荧光强度和亲水性。依赖温度的傅立叶变换红外光谱（FT-IR）分析进一步证实，固化后的EP-F / DDM中的氢键更多，与呋喃环中的氧杂原子有关，从而使其具有更好的性能。这项工作使我们对由杂芳族化合物合成的环氧树脂中负电性杂原子的作用有了新的认识。