Synthesis, characterization and properties of polyimides derived from a symmetrical diamine containing bis-benzimidazole rings

Synthesis, characterization and properties of polyimides derived from a symmetrical diamine containing bis-benzimidazole rings
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含双苯并咪唑环的对称二胺衍生的聚酰亚胺的合成、表征和性能

DOI:
10.1016/j.polymdegradstab.2012.03.010
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发表时间:
2012-06-01
影响因子:
5.9
通讯作者:
Xu, Qian
Xu, Qian
中科院分区:
化学2区
文献类型:
--
作者:
Liu, Junpeng;Zhang, Qinghua;Xu, Qian

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以2,2 '-对苯撑双(5-硝基苯并咪唑)为原料,通过对苯二甲酰氯与4-硝基-1,2-苯二胺反应,高产率地合成了一种新的含双苯并咪唑环的芳香杂环二胺单体2,2'-对苯撑双(5-氨基苯并咪唑)(PBABI)。用红外光谱、核磁共振氢谱、碳谱和元素分析等方法研究了二胺单体的组成和结构。以芳香族二酐3,3 ′,4,4 ′-联苯四甲酸二酐、4,4 ′-氧代二苯二甲酸酐、二苯甲酮四甲酸二酐和均苯四甲酸二酐为原料,通过两步法合成了一系列主链含双苯并咪唑环的聚酰亚胺。采用X射线衍射和差示扫描量热法研究了聚酰亚胺,揭示了它们基本上是无定形的。这些聚酰亚胺具有高达560摄氏度的热稳定性(重量损失5%)和高于450摄氏度的玻璃化转变温度。此外,这些高性能聚合物还具有优异的机械性能,在没有任何拉伸的情况下,拉伸强度为120-180 MPa,拉伸模量为4.83-5.79 GPa。聚酰亚胺的刚性棒状结构和大分子链间的氢键作用是其优异性能的主要原因。(C)2012爱思唯尔有限公司保留所有权利。
A new aromatic heterocyclic diamine monomer containing bis-benzimidazole rings, 2,2'-p-phenylene-bis(5-aminobenzimidazole) (PBABI), was synthesized from 2,2'-p-phenylene-bis (5-nitrobenzimidazole) with high yield via the reaction between 4-nitro-1,2-phenylenediamine and terephthalyl chloride. The composition and structure of the resulting diamine monomer were studied by means of FTIR, H-1 and C-13 NMR and elemental analysis. A series of polyimides holding bis-benzimidazole rings in main chain were produced by reacting PBABI with the aromatic dianhydrides 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, benzophenone tetracarboxylic dianhydride and pyromellitic dianhydride via a conventional, two-step procedure. X-ray diffraction and differential scanning calorimetry were employed to investigate the polyimides, revealing them essentially amorphous. The polyimides possess thermal stabilities of up to 560 degrees C for a 5% weight loss and glass transition temperatures above 450 degrees C. In addition, these high performance polymers have excellent mechanical properties, exhibiting tensile strengths of 120-180 MPa and tensile moduli of 4.83-5.79 GPa without any stretching. The rigid-rod structure of polyimides and the hydrogen bonding of their inter-macromolecular chains are most likely responsible for the outstanding properties of the polyimides. (C) 2012 Elsevier Ltd. All rights reserved.