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Synthesis and Properties of High Thermally Stable and Organosoluble Poly(pyridine imide)s with Pendent Diethylaminophenyl Groups

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Abstract

A novel diamine monomer 4-(4-diethylaminophenyl)-2,6-bis(4-aminophenyl)pyridine (APAP) was successfully synthesized, and then a series of poly(pyridine imide)s was prepared from APAP with five commercial dianhydrides: pyromellitic dianhydride (PMDA), 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA), 4,4′-oxydiphthalic anhydride (ODPA), 3,3′,4,4′-benzophenone tetracarboxylic dianhydride (BTDA), and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) via a two-step solution polycondensation method. The structure of APAP was characterized by FT-IR, NMR, and MS. The resulting polymers have good solubility in polar solvents, such as NMP, DMF, and DMSO. Furthermore, they exhibited outstanding thermal stability. The glass transition temperature (Tg) of polymers range from 326 to 346 °C, and the temperature at 5 % and 10 % weight loss in the range of 527 °C to 570 °C and 550 °C to 601 °C, respectively. Moreover, they also presented excellent hydrophobicity with contact angels in the range of 88.4 ° to 94.0 °.

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References

  1. M. X. Ding, Prog. Polym. Sci., 32, 62 (2007).

    Article  CAS  Google Scholar 

  2. X. Z. Fang, Z. H. Yang, S. B. Zhang, L. X. Gao, and M. X. Ding, Polymer, 45, 2539 (2004).

    Article  CAS  Google Scholar 

  3. L. Yi, W. Huang, and D. Y. Yan, J. Polym. Sci. Part A: Polym. Chem., 55, 533 (2017).

    Article  CAS  Google Scholar 

  4. P. M. Hergenrother, K. A. Watson, J. G. Jr. Smith, J. W. Connell, and R. Yokota, Polymer, 43, 5077 (2002).

    Article  CAS  Google Scholar 

  5. D. J. Liaw, K. L. Wang, Y. C. Huang, K. R. Lee, J. Y. Lai, and C. S. Ha, Prog. Polym. Sci., 37, 907 (2012).

    Article  CAS  Google Scholar 

  6. L. Li, L. Shang, Y. Li, and C. Yang, Fiber. Polym., 18, 749 (2017).

    Article  CAS  Google Scholar 

  7. K. Kanosue, T. Shimosaka, J. Wakita, and S. Ando, Macromolecules, 48, 1777 (2015).

    Article  CAS  Google Scholar 

  8. G. M. Nisola, A. B. Beltran, E. Cho, M. Han, and W. J. Chung, Fiber. Polym., 12, 572 (2011).

    Article  CAS  Google Scholar 

  9. G. Yang, R. Zhang, H. Huang, L. Liu, L. Wang, and Y. Chen, Rsc Adv., 5, 67574 (2015).

    Article  CAS  Google Scholar 

  10. X. H. Huang, W. Huang, J. Y. Liu, L. L. Meng, and D. Y. Yan, Polym. Int., 61, 1503 (2012).

    Article  CAS  Google Scholar 

  11. J. Zhao, L. Peng, Y. L. Zhu, Y. J. Song, L. J. Wang, and Y. Z. Shen, Polymer, 91, 118 (2016).

    Article  CAS  Google Scholar 

  12. P. Wen, R. He, X. D. Li, and M. H. Lee, Polymer, 117, 76 (2017).

    Article  CAS  Google Scholar 

  13. C. J. Liu, X. L. Pei, M. Mei, G. Q. Chou, X. H. Huang, and C. Wei, High Perform. Polym., 28, 1114 (2016).

    Article  CAS  Google Scholar 

  14. A. Tundidor-Camba, C. A. Terraza, L. H. Tagle, D. Coll, P. Ortiz, and G. Pérez, Macromol. Res., 25, 1 (2017).

    Article  CAS  Google Scholar 

  15. C. J. Liu, X. L. Pei, X. H. Huang, C. Wei, and X. Y. Sun, Chinese J. Chem., 33, 277 (2015).

    Article  CAS  Google Scholar 

  16. R. Lei, L. X. Gao, R. Z. Jin, and X. P. Qiu, Chinese J. Polym. Sci., 32, 941 (2014).

    Article  CAS  Google Scholar 

  17. S. J. Zhang, Q. Q. Bu, Y. F. Li, C. L. Gong, X. Y. Xu, and H. Li, Mater. Chem. Phys., 128, 392 (2011).

    Article  CAS  Google Scholar 

  18. W. Feng, X. P. Zhou, and X. H. Yu, RSC Adv., 7, 35786 (2017).

    Article  Google Scholar 

  19. X. H. Huang, M. Mei, C. J. Liu, X. L. Pei, and C. Wei, J. Polym. Res., 22, 169 (2015).

    Article  CAS  Google Scholar 

  20. D. J. Liaw, K. L. Wang, and F. C. Chang, Macromolecules, 40, 3568 (2007).

    Article  CAS  Google Scholar 

  21. D. J. Liaw, K. L. Wang, F. C. Chang, K. R. Lee, and J. Y. Lai, J. Polym. Sci. Part A: Polym. Chem., 45, 2367 (2007).

    Article  CAS  Google Scholar 

  22. X. Xu, B. C. Chen, H. Li, X. H. Huang, and C. Wei, Chinese J. Chem., 35, 341 (2017).

    Article  CAS  Google Scholar 

  23. K. L. Wang, W. T. Liou, D. J. Liaw, and W. T. Chen, Dyes Pigment., 78, 93 (2008).

    Article  CAS  Google Scholar 

  24. W. Dong, Y. Guan, and D. Shang, Rsc Adv., 6, 21662 (2016).

    Article  CAS  Google Scholar 

  25. K. L. Wang, W. T. Liou, D. J. Liaw, and S. T. Huang, Polymer, 49, 1538 (2008).

    Article  CAS  Google Scholar 

  26. C. B. Wang, X. G. Zhao, D. B. Tian, D. M. Wang, C. H. Chen, and H. W. Zhou, Des. Monomers Polym., 20, 97 (2017).

    Article  CAS  PubMed  Google Scholar 

  27. X. Wang, Y. Li, S. Zhang, T. Ma, Y. Shao, and X. Zhao, Eur. Polym., 42, 1229 (2006).

    Article  CAS  Google Scholar 

  28. Y. Mansoori, S. V. Atghia, S. S. Sanaei, M. R. Zamanloo, G. Imanzadeh, and H. Eskandari, Polym. Int., 61, 1213 (2012).

    Article  CAS  Google Scholar 

  29. Y. Xing, D. Wang, H. Gao, and Z. H. Jiang, J. Appl. Polym. Sci., 122, 738 (2011).

    Article  CAS  Google Scholar 

  30. R. Hariharan and M. Sarojadevi, J. Appl. Polym. Sci., 102, 4127 (2006).

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 51563005), and the fund of Guangxi Natural Science Foundation (No. 2016GXNSFBA380009).

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Authors and Affiliations

  1. Key Laboratory of New Processing Technology for Nonferrous Metal & Materials, Ministry of Education, Collaborative Innovation Center for Exploration of Hidden Nonferrous Metal Deposits and Development of New Materials in Guangxi, School of Materials Science and Engineering, Guilin University of Technology, Guilin, 541004, China

    Xiaohua Huang, Hua Li, Chanjuan Liu, Limin Zang, Huanfu Zhou & Chun Wei

Authors
  1. Xiaohua Huang
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  2. Hua Li
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  3. Chanjuan Liu
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  4. Limin Zang
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  5. Huanfu Zhou
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  6. Chun Wei
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Correspondence to Xiaohua Huang or Limin Zang.

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Huang, X., Li, H., Liu, C. et al. Synthesis and Properties of High Thermally Stable and Organosoluble Poly(pyridine imide)s with Pendent Diethylaminophenyl Groups. Fibers Polym 20, 1109–1115 (2019). https://doi.org/10.1007/s12221-019-7731-0

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