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Synthesis and characterization of polyhydroxyamide copolymers as precursors of polybenzoxazoles

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Abstract

Polyhydroxyamide (PHA) and its copolymers were synthesized via low-temperature solution polycondensation of 3,3′-dihydroxybenzidine (DHB) with terephthaloyl chloride (TPC) and/or isophthaloyl chloride (IPC) in N,N-dimethylacetamide (DMAc) with the aid of lithium chloride (LiCl). The synthesized PHA copolymers were characterized by 1H-NMR spectroscopy, FT-IR spectroscopy, and thermogravimetric analyzer (TGA) in order to understand the relations between the chemical structures and the solubility and thermal properties of PHA copolymers. Thermal cyclization of PHA copolymers and the formation of polybenzoxazoles (PBOs) were investigated using FT-IR spectroscopy and TGA. The solubility test revealed that PHA copolymers containing IPC content over 20 mol% were readily dissolved in a variety of polar amide solvents with the aid of LiCl. TGA results showed that the thermal cyclization temperature, the thermal degradation temperatures of PHA copolymers and the thermal stabilities and the char yields of converted PBO copolymers were significantly reduced by the inclusion of meta-structure in the main chain especially when the IPC content was higher than 25 mol%.

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References

  1. J. F. Wolfe and F. E. Arnold, Macromolecules, 14, 909 (1981).

    Article  CAS  Google Scholar 

  2. M. E. Hunsaker, G. E. Price, and S. J. Bai, Polymer, 33, 2128 (1992).

    Article  CAS  Google Scholar 

  3. S. H. Hsiao and Y. H. Huang, Eur. Polym. J., 40, 1127 (2004).

    Article  CAS  Google Scholar 

  4. T. Fukumary, Y. Saegusa, T. Fujigawa, and N. Nakashima, Macromolecules, 47, 2088 (2014).

    Article  Google Scholar 

  5. T. Kitagawa, K. Yabuki, A. C. Wright, and R. J. Young, J. Mater Sci., 49, 6467 (2014).

    Article  CAS  Google Scholar 

  6. M. Ueda, H. Sugita, and M. Sato, J. Appl. Polym. Sci., 24, 1019 (1986).

    Article  CAS  Google Scholar 

  7. G. C. Eastmond, Macromolecules, 29, 1382 (1996).

    Article  CAS  Google Scholar 

  8. C. W. Lin, S. L. C. Hsu, and A. C. M. Yang, Polymer, 53, 1951 (2012).

    Article  CAS  Google Scholar 

  9. S. H. Hsiao and L. R. Dai, J. Appl. Polym. Sci., 37, 2129 (1999).

    Article  CAS  Google Scholar 

  10. D. H. Baik, H. Y. Kim, and S. W. Kantor, Fiber. Polym., 3, 91 (2002).

    Article  CAS  Google Scholar 

  11. Y. Imai, K. Itoya, and M. A. Kakimoto, Macromol. Chem. Phys., 201, 2251 (2000).

    Article  CAS  Google Scholar 

  12. S. L. C. Hsu and W. C. Chen, Polymer, 43, 6743 (2002).

    Article  CAS  Google Scholar 

  13. D. H. Baik, E. K. Kim, and M. K. Kim, Text. Sci. Eng., 40, 13 (2003).

    CAS  Google Scholar 

  14. H. Zhang, R. J. Farris, and P. R. Westmoreland, Macromolecules, 36, 3944 (2003).

    Article  CAS  Google Scholar 

  15. K. I. Kukukawa, Y. Shibasaki, and M. Ueda, Macromolecules, 37, 8256 (2004).

    Article  Google Scholar 

  16. H. Wang, S. Liu, T. S. Chung, H. Chen, Y. C. Jean, and K. P. Pramoda, Polymer, 52, 5127 (2011).

    Article  CAS  Google Scholar 

  17. M. Hasegawa, N. Suyama, N. Shimoyama, H. Aoki, T. Nunokawa, and T. Kimura, Polym. Int., 60, 1240 (2011).

    Article  CAS  Google Scholar 

  18. M. H. Jee, J. Y. Lee, and D. H. Baik, Text. Sci. Eng., 49, 324 (2012).

    Article  CAS  Google Scholar 

  19. Y. Yoshioka, Open Surf. Sci. J., 4, 1 (2012).

    Article  CAS  Google Scholar 

  20. E. G. Chatzi, S. L. Tidrick, and J. L. Koenig, J. Appl. Polym. Sci., 26, 1585 (1988).

    Article  CAS  Google Scholar 

  21. A. Mavrich, F. Fondeur, H. Ishida, J. L. Koenig, and H. D. Wagner, J. Adhesion, 46, 91 (1994).

    Article  CAS  Google Scholar 

  22. D. S. Yoon, J. K. Choi, and B. W. Jo, Polymer, 29, 493 (2005).

    CAS  Google Scholar 

  23. J. S. Lee, M. H. Jee, and D. H. Baik, Text. Sci. Eng., 47, 7 (2010).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Advanced Organic Materials & Textile System Engineering, Chungnam National University, Daejeon, 305-764, Korea

    Chan Sol Kang, Min Jung Paik, Chae Won Park & Doo Hyun Baik

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  1. Chan Sol Kang
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  2. Min Jung Paik
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  3. Chae Won Park
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  4. Doo Hyun Baik
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Correspondence to Doo Hyun Baik.

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Kang, C.S., Paik, M.J., Park, C.W. et al. Synthesis and characterization of polyhydroxyamide copolymers as precursors of polybenzoxazoles. Fibers Polym 16, 239–244 (2015). https://doi.org/10.1007/s12221-015-0239-y

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  • DOI: https://doi.org/10.1007/s12221-015-0239-y

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