Abstract—

A novel monomer for the synthesis of polyimides, 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride was developed. The synthesis was carried out in three stages: the reaction of nucleophilic nitro substitution of 4-nitrophthalonitrile with 5‑methylresorcinol (orcinol) potassium salt and subsequent hydrolysis of the nitrile groups have afforded 5‑methyl-1,3-phenylene-bis-4-oxyphthalic acid, dehydration of which has given the corresponding dianhydride. A series of new thermoplastic high molecular weight polyetherimides based on 5-methyl-1,3-phenylene-bis-4-oxyphthalic acid dianhydride and several aromatic diamines of various structures were synthesized by the method of one-stage catalytic polycondensation in a benzoic acid melt. Inherent viscosity and weight-average molecular mass of the polyetherimides have been of 0.28‒1.20 dL/g and (33‒114) × 10³, respectively. The polyetherimides have been soluble in chloroform, THF, DMF, DMAA, N-methylpyrrolidone, and DMSO and have revealed film-forming properties. According to the DSC and wide-angle X-ray scattering data, the polyetherimides have been found completely amorphous, the glass transition temperature being in the 185–307°C range.

中文翻译：

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基于 5-甲基-1,3-亚苯基-双-4-氧邻苯二甲酸二酐的新型聚醚酰亚胺：合成及理化性质

摘要-

开发了一种用于合成聚酰亚胺的新型单体 5-甲基-1,3-亚苯基-双-4-氧邻苯二甲酸二酐。合成分三个阶段进行：4-硝基邻苯二甲腈与 5-甲基间苯二酚（orcinol）钾盐的亲核硝基取代反应，随后腈基水解得到 5-甲基-1,3-亚苯基-双-4 -氧邻苯二甲酸，脱水得到相应的二酐。以5-甲基-1,3-亚苯基-双-4-氧邻苯二甲酸二酐和几种不同结构的芳香族二胺为原料，在苯甲酸中采用一步催化缩聚的方法合成了一系列新型热塑性高分子量聚醚酰亚胺。熔化。聚醚酰亚胺的特性粘度和重均分子量为0.28-1。³、分别。聚醚酰亚胺可溶于氯仿、THF、DMF、DMAA、N-甲基吡咯烷酮和 DMSO，并显示出成膜性能。根据 DSC 和广角 X 射线散射数据，发现聚醚酰亚胺完全无定形，玻璃化转变温度在 185-307°C 范围内。