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Preparation and characterization of poly (ether ether ketone)s containing benzimidazolone units

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Abstract

A series of novel poly(ether ether ketone)s containing benzimidazolone groups (PNBEEKs) with precise structures in high yields were synthesized from various stoichiometric ratio mixtures of benzimidazolone, 4,4′-dihydroxybenzophenone and 4,4′-difluorobnzophenone via a C–N/C–O coupling reaction process using sulfolane as a solvent. The reaction was carried out at 210 °C in the presence of anhydrous potassium carbonate. The structures of the resulted polymers were characterized by means of FT-IR, 1H NMR spectroscopy, 13C NMR spectroscopy, and elemental analysis, and the results were largely consistent with the proposed structure. XRD studies revealed that the incorporation of benzimidazolone groups increased the crystallinity of the resulted polymers. At the same time, as the benzimidazolone unit content in the copolymer increased, the solvent resistance properties and thermal properties of the prepared polymers improved. The polymers showed high glass transition temperatures (Tg = 126–221 °C) and high thermal stability (Td5% = 497–593 °C in nitrogen, 466–588 °C in air). Moreover, the resulted polymers showed good fluorescence properties and the fluorescence emission peak was 435 nm.

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Acknowledgments

This work was supported by the Scientific Research Fund of Sichuan Provincial Education Department (No. 16ZB0146), the Technology Innovation Talent Funding Project of Sichuan province (No. 2016080), the National Training Program of Innovation and Entrepreneurship for Undergraduates (No. 201510619021), the Doctoral Research Fund of Southwest University of Science and Technology (No. 13zx7133) and the Opening Foundation of Engineering Research Center of Biomass Materials, Ministry of Education (Southwest University of Science and Technology) (No. 13zxbk05).

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Authors and Affiliations

  1. Engineering Research Center of Biomass Materials, Ministry of Education, School of Material Science and Engineering, Southwest University of Science and Technology, Mianyang, 621010, China

    Jiaao Feng, Yewei Xu, Yi Sun, Shangyan Wen, Yonglin Lei & Jichuan Huo

  2. Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang, 621900, China

    Jiaao Feng & Lin Zhang

  3. Joint Laboratory for Extreme Conditions Matter Properties, Southwest University of Science and Technology and Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang, 621010, China

    Jiaao Feng, Yewei Xu & Lin Zhang

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  1. Jiaao Feng
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  2. Yewei Xu
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  3. Yi Sun
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  4. Shangyan Wen
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  5. Yonglin Lei
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  6. Lin Zhang
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  7. Jichuan Huo
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Correspondence to Yewei Xu or Jichuan Huo.

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Feng, J., Xu, Y., Sun, Y. et al. Preparation and characterization of poly (ether ether ketone)s containing benzimidazolone units. J Polym Res 23, 247 (2016). https://doi.org/10.1007/s10965-016-1132-0

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  • DOI: https://doi.org/10.1007/s10965-016-1132-0

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