Synthesis and characterization of high-performance polyimides based on 6,4′-diamino-2-phenylbenzimidazole

Authors

  • Qingming Xia,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Junpeng Liu,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Jie Dong,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Chaoqing Yin,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Yuxuan Du,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Qian Xu,

    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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  • Qinghua Zhang

    Corresponding author
    1. State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
    • State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai, 201620, People's Republic of China
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Abstract

A new synthesis route was developed to produce the diamine monomer containing benzimidazole units, 6,4′-diamino-2-phenylbenzimidazole (BIA), which was easily prepared by the reduction of 6,4′-dinitro-2-phenylbenzimidazole synthesized via a reaction between 4-nitro-1,2-phenylenediamine and 4-nitrobenzoyl chloride. The composition and structure of the products were confirmed by Fourier transform infrared, NMR, and elemental analysis. A series of polyimides were prepared by the polycondensation of BIA and various dehydrates, pyromellitic dianhydride, 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, and benzophenone tetracarboxylic dianhydride via a traditional two-step procedure. The polyimides exhibit excellent thermal stability up to 540°C and high glass transition temperature (Tg) in the range of 382–409°C. The polyimide films are tough and flexible and possess good mechanical properties of tensile strength of 222–232 MPa and modulus of 3.1–5.6 GPa without stretching. The polyimides are amorphous state in wide-angle X-ray diffraction patterns, whereas small-angle X-ray diffraction patterns show the existence of molecular aggregation. The rigid-rod structure and intermacromolecular hydrogen bond are likely responsible for the excellent properties of the polyimides. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013

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