Skip to main content

Bisphthalonitrile-based Thermosets as Heat-resistant Matrices for Fiber Reinforced Plastics

Abstract

This review focuses on the processes involved in producing heat-resistant matrices for fiber reinforced plastics (FRP) by polymerization of the resins consisting of phthalonitrile monomers and comonomers, and the specifics of fiber reinforced plastics fabrication technologies. Polymerization behaviors observed in the presence of various types of initiators and in different temperature modes are reviewed. Fabrication methods and mechanical properties of FRPs based on phthalonitrile resins with various reinforcing materials are discussed. Properties of glass fiber reinforced plastics (GFRP) and carbon fiber reinforced plastics (CFRP) obtained through curing of different phthalonitriles are compared.

This is a preview of subscription content, access via your institution.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. D. S. Kiva, Aviats.-Kosm. Tekh. Tekhnol. 6 (113), 5 (2014).

    Google Scholar 

  2. M. Asim, N. Saba, M. Jawaid, M. Nasir, M. Pervaiz, and O. Y. Alothman, Curr. Anal. Chem. 14, 185 (2018).

    Article  CAS  Google Scholar 

  3. A. Pizzi and C. C. Ibeh, “Phenol-Formaldehydes,” in Handbook of Thermoset Plastics, Ed. by H. Dodiuk (William Andrew Publ., New York, 2014), p. 13.

    Google Scholar 

  4. B. Bulgakov, D. Kalugin, A. Babkin, I. Makarenko, A. Malakho, A. Kepman, V. Avdeev, N. Garadja, and A. Rogozin, Can. J. Chem. Eng. 94, 46 (2016).

    Article  CAS  Google Scholar 

  5. G. Gibson, in Brydson’s Plastics Materials, Ed. By M. Gilbert (Butterworth Heinemann, Oxford, 2017), p. 773.

    Google Scholar 

  6. G. Cicala, S. Mannino, A. Latteri, G. Ognibene, and G. Saccullo, Adv. Polym. Technol. 37, 1868 (2018).

    Article  CAS  Google Scholar 

  7. ASM Handbook, Ed. by D. B. Miracle and S. L. Donaldson (ASM Int., Novelty, OH, 2001), Vol. 21.

  8. M. Bauer, R. Wurzel, C. Uhlig, and J. Bauer, US Patent No. 20080119630 (2008).

  9. Chemistry and Technology of Cyanate Ester Resins, Ed. by I. Hamerton (Springer Netherlands, Heidelberg, 2012).

    Google Scholar 

  10. C. Uhlig, M. Bauer, J. Bauer, O. Kahle, A. C. Taylor, A. J. Kinloch, React. Funct. Polym. 129, 2 (2018).

    Article  CAS  Google Scholar 

  11. A. V. Babkin, E. M. Erdni-Goryaev, A. V. Solopchenko, and A. V. Kepman, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 58, 54 (2015).

    CAS  Google Scholar 

  12. S. E. Evsyukov, T. Pohlmann, and H. D. Stenzenberger, Polym. Adv. Technol. 26, 574 (2015).

    Article  CAS  Google Scholar 

  13. A. V. Babkin, E. B. Zodbinov, B. A. Bulgakov, A. V. Kepman, and V. V. Avdeev, Eur. Polym. J. 66, 452 (2015).

    Article  CAS  Google Scholar 

  14. M. Ji, in Advanced Polyimide Materials, Ed. by S.‑Y. Yang (Elsevier, Amsterdam, 2018), p. 93.

    Google Scholar 

  15. H. R. Lubowitz and C. H. Sheppard, US Patent No. 5116935 (1992).

  16. K. L. Mittal, Polyimides and Other High Temperature Polymers: Synthesis, Characterization and Applications (CRC Press, Boca Raton, 2009).

    Book  Google Scholar 

  17. H. D. Stenzenberger, in High Performance Polymers (Springer-Verlag, Heidelberg, 2018), p. 165.

    Google Scholar 

  18. K. M. Zia, H. N. Bhatti, and I. Ahmad Bhatti, React. Funct. Polym. 67, 675 (2007).

    Article  CAS  Google Scholar 

  19. A. Atiqah, M. Mastura, B. Ali, M. Jawaid, and S. Sapuan, Curr. Org. Synth. 14, 233 (2017).

    Article  CAS  Google Scholar 

  20. R. H. Pater, Polym. Eng. Sci. 31, 20 (1991).

    Article  CAS  Google Scholar 

  21. T. M. Keller and J. R. Griffith, US Patent No. 4234712A (1980).

  22. T. M. Keller and J. R. Griffith, US Patent No. 4259471A (1979).

  23. S. B. Sastri and T. M. Keller, J. Polym. Sci., Part A: Polym. Chem. 37, 2105 (1999).

    Article  CAS  Google Scholar 

  24. T. M. Keller, US Patent No. 5003039A (1991).

  25. T. M. Keller, J. Polym. Sci., Part A: Polym. Chem. 26, 3199 (1988).

    Article  CAS  Google Scholar 

  26. Phthalonitrile Resins and Composites: Properties and Applications, Ed. by M. Derradji, J. Wang, and M. Liu (Elsevier, Amsterdam, 2018).

    Google Scholar 

  27. C. E. Dent and R. P. Linstead, J. Chem. Soc. 1934, 1027 (1934).

  28. J. R. Griffith, J. G. O’Rear, and T. R. Walton, in Advanced Chemistry, Ed. by N. A. J. Platzer (Am. Chem. Soc., New York, 1975), p. 458.

    Google Scholar 

  29. T. M. Keller and J. R. Griffith, ACS Symp. Ser. 132, 25 (1980).

    Article  CAS  Google Scholar 

  30. T. M. Keller, J. Polym. Sci., Part A: Polym. Chem. 26, 3199 (1988).

    Article  CAS  Google Scholar 

  31. B. A. Bulgakov, A. V. Babkin, P. B. Dzhevakov, A. A. Bogolyubov, A. V. Sulimov, A. V. Kepman, Y. G. Kolyagin, D. V. Guseva, V. Y. Rudyak, and A. V. Chertovich, Eur. Polym. J. 84, 205 (2016).

    Article  CAS  Google Scholar 

  32. B. A. Bulgakov, A. V. Sulimov, A. V. Babkin, A. V. Kepman, A. P. Malakho, and V. V. Avdeev, J. Appl. Polym. Sci. 134, 44786 (2017).

    Article  CAS  Google Scholar 

  33. H. Sheng, X. Peng, H. Guo, X. Yu, C. Tang, X. Qu, and Q. Zhang, Mater. Chem. Phys. 142, 740 (2013).

    Article  CAS  Google Scholar 

  34. F. Zhao, R. Liu, C. Kang, X. Yu, K. Naito, X. Qu, and Q. Zhang, RSC Adv. 4, 8383 (2014).

  35. X. Peng, H. Sheng, H. Guo, K. Naito, X. Yu, H. Ding, X. Qu, and Q. Zhang, High Perform. Polym. 26, 837 (2014).

    Article  CAS  Google Scholar 

  36. X.-Y. Yu, K. Naito, C. Kang, X.-W. Qu, and Q.‑X. Zhang, Macromol. Chem. Phys. 214, 361 (2013).

    Article  CAS  Google Scholar 

  37. Y. Han, D. Tang, G. Wang, Y. Guo, H. Zhou, W. Qiu, and T. Zhao, Eur. Polym. J. 111, 104 (2019).

    Article  CAS  Google Scholar 

  38. Y. Han, G. Wang, W. Qiu, Y. Guo, Y. Sun, Y. Zhang, H. Zhou, and T. Zhao, Asian J. Org. Chem. 7, 2511 (2018).

    Article  CAS  Google Scholar 

  39. R. Y. Ting, T. M. Keller, T. R. Price, and C. F. Poranski, in Cyclopolymerization and Polymers with Chain-Ring Structures, Ed. by G. B. Butler and J. E. Kresta (Am. Chem. Soc, Washington, DC, 1982), p. 337.

  40. T. M. Keller and J. R. Griffith, US Patent No. 4223123 (1980).

  41. T. M. Keller and J. R. Griffith, Chem. Informationsdienst 10, (1979). https://doi.org/10.1002/chin.197926203

  42. N. B. McKeown, J. Mater. Chem. 10, 1979 (2000).

    Article  CAS  Google Scholar 

  43. A. W. Snow, J. R. Griffith, and N. P. Marullo, Macromolecules 17, 1614 (1984).

    Article  CAS  Google Scholar 

  44. K. Jia, R. Zhao, J. Zhong, and X. Liu, J. Mater. Sci.: Mater. Electron. 21, 708 (2010).

    CAS  Google Scholar 

  45. M. J. Sumner, M. Sankarapandian, J. E. McGrath, J. S. Riffle, and U. Sorathia, Polymers 43, 5069 (2002).

    Article  CAS  Google Scholar 

  46. T. M. Keller, T. R. Price, and J. R. Griffith, Am. Chem. Soc., Div. Org. Coat. Plast. Chem., Coat. Plast. Prepr. Pap. Meet. 43, 804 (1980).

  47. S. B. Sastri and T. M. Keller, J. Polym. Sci., Part A: Polym. Chem. 36, 1885 (1998).

    Article  CAS  Google Scholar 

  48. V. E. Terekhov, O. S. Morozov, E. S. Afanaseva, B. A. Bulgakov, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, Mendeleev Commun. 30, 671 (2020).

    Article  CAS  Google Scholar 

  49. J. A. Hinkley, J. Appl. Polym. Sci. 29, 3339 (1984).

    Article  CAS  Google Scholar 

  50. T. M. Keller and D. D. Dominguez, Polymers 46, 4614 (2005).

    Article  CAS  Google Scholar 

  51. D. D. Dominguez, H. N. Jones, and T. M. Keller, Polym. Compos. 25, 554 (2004).

    Article  CAS  Google Scholar 

  52. S. B. Sastri, J. P. Armistead, and T. M. Keller, Polym. Compos. 17, 816 (1996).

    Article  CAS  Google Scholar 

  53. W. O. Siegl, Org. Chem. 42, 1872 (1977).

    Article  CAS  Google Scholar 

  54. G. Yu, C. Liu, X. Li, J. Wang, X. Jian, and C. Pan, Polym. Chem. 3, 1024 (2012).

    Article  CAS  Google Scholar 

  55. M. Warzel and T. Keller, Polymers 34, 663 (1993).

    Article  CAS  Google Scholar 

  56. K. Zeng, K. Zhou, W. R. Tang, Y. Tang, H. F. Zhou, T. Liu, Y. P. Wang, H. B. Zhou, and G. Yang, Chin. Chem. Lett. 18, 523 (2007).

    Article  CAS  Google Scholar 

  57. H. Zhou, A. Badashah, Z. Luo, F. Liu, and T. Zhao, Polym. Adv. Technol. 22, 1459 (2011).

    Article  CAS  Google Scholar 

  58. T. Carnelley, Philos. Mag. Ser. 13 (79), 112 (1882).

    Article  Google Scholar 

  59. V. V. Aleshkevich, A. V. Babkin, and V. V. Avdeev, IOP Conf. Ser.: Mater. Sci. Eng. 683, 12023 (2019).

  60. Z.-Q. Zhang, S. Uth, D. J. Sandman, and B. M. Foxman, J. Phys. Org. Chem. 17, 769 (2004).

    Article  CAS  Google Scholar 

  61. S. A. Iling, I. I. Ponomarev, V. V. Kuznetsov, B. V. Lokshin, V. V. Korshak, and S. V. Vinogradova, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 32, 1588 (1983).

  62. X. Chen, J. Liu, Z. Xi, S. Shan, H. Ding, X. Qu, and Q. Zhang, High Perform. Polym. 29, 1209 (2017).

    Article  CAS  Google Scholar 

  63. J. Wang, C. Chen, X. Chen, H. Wang, X. Yu, Y. Ma, K. Naito, and Q. Zhang, High Perform. Polym. 30, 1114 (2018).

    Article  CAS  Google Scholar 

  64. K. Zeng, K. Zhou, S. Zhou, H. Hong, H. Zhou, Y. Wang, P. Miao, and G. Yang, Eur. Polym. J. 45, 1328 (2009).

    Article  CAS  Google Scholar 

  65. J. Z. Ma, K. Cheng, J. B. Lv, C. Chen, J. H. Hu, K. Zeng, and G. Yang, Chin. J. Polym. Sci. 36, 497 (2018).

    Article  CAS  Google Scholar 

  66. A. Lyubimtsev, S. Vagin, S. Syrbu, and M. Hanack, Eur. J. Org. Chem. 2007, 2000 (2007).

    Article  CAS  Google Scholar 

  67. J. Wang, J. Hu, K. Zeng, and G. Yang, RSC Adv. 5, 105038 (2015).

  68. Y. Hu, Z. Weng, Y. Qi, J. Wang, S. Zhang, C. Liu, L. Zong, and X. Jian, RSC Adv. 8, 32899 (2018).

  69. Y. Yang, Z. Min, and L. Yi, Polym. Bull. 59, 185 (2007).

    Article  CAS  Google Scholar 

  70. B. Zhang, Z. Luo, H. Zhou, F. Liu, R. Yu, Y. Pan, Y. Wang, and T. Zhao, High Perform. Polym. 24, 398 (2012).

    Article  CAS  Google Scholar 

  71. X. Zou, M. Xu, K. Jia, and X. Liu, J. Appl. Polym. Sci. 131, 41203 (2014).

    Google Scholar 

  72. D. Augustine, D. Mathew, and C. P. Reghunadhan Nair, Polymers 60, 308 (2015).

    Article  CAS  Google Scholar 

  73. M. Wang, L. Wei, and T. Zhao, Eur. Polym. J. 41, 903 (2005).

    Article  CAS  Google Scholar 

  74. W. E. Douglas and A. S. Overend, Eur. Polym. J. 29, 1513 (1993).

    Article  CAS  Google Scholar 

  75. W. E. Douglas and A. S. Overend, Polymers 34, 1544 (1993).

    Article  CAS  Google Scholar 

  76. K. Balaraman and V. Kesavan, Synthesis 2010, 3461 (2010).

    Article  CAS  Google Scholar 

  77. S. Ji, P. Yuan, J. Hu, R. Sun, K. Zeng, G. Yang, Polymer 84, 365 (2016).

    Article  CAS  Google Scholar 

  78. P. Yuan, S. Ji, J. Hu, X. Hu, K. Zeng, G. Yang, Polymer 102, 266 (2016).

    Article  CAS  Google Scholar 

  79. Z. Liu, Y. Liu, W. Peng, Z. Lu, B. Liang, Y. Liu, C. Li, J. Hu, K. Zeng, and G. Yang, J. Appl. Polym. Sci. 136, 48134 (2019).

    Article  CAS  Google Scholar 

  80. J. Lv, Z. Liu, R. Li, Y. Liu, J. Hu, K. Zeng, and G. Yang, Thermochim. Acta 683, 178446 (2020).

    Article  CAS  Google Scholar 

  81. H. J. P. De Lijser and D. R. Arnold, J. Phys. Chem. A 102, 5592 (1998).

    Article  CAS  Google Scholar 

  82. J. R. Shelton and C. W. Uzelmeier, J. Am. Chem. Soc. 88, 5222 (1966).

    Article  CAS  Google Scholar 

  83. R. H. Poirier, E. J. Kahler, and P. Benington, J. Org. Chem. 17, 1437 (1952).

    Article  CAS  Google Scholar 

  84. T. M. Keller, Chem. Mater. 6, 302 (1994).

    Article  CAS  Google Scholar 

  85. M. Laskoski, D. D. Dominguez, and T. M. Keller, J. Polym. Sci., Part A: Polym. Chem. 43, 4136 (2005).

    Article  CAS  Google Scholar 

  86. M. Laskoski, M. B. Schear, A. Neal, D. D. Dominguez, H. L. Ricks-Laskoski, J. Hervey, and T. M. Keller, Polymers 67, 185 (2015).

    Article  CAS  Google Scholar 

  87. M. Laskoski, A. Neal, T. M. Keller, D. Dominguez, C. A. Klug, and A. P. Saab, J. Polym. Sci., Part A: Polym. Chem. 52, 1662 (2014).

    Article  CAS  Google Scholar 

  88. D. D. Dominguez and T. M. Keller, Polymers 48, 91 (2007).

    Article  CAS  Google Scholar 

  89. M. Laskoski, D. D. Dominguez, and T. M. Keller, in Fire and Polymers IV, Ed. by C. A. Wilkie and G. L. Nelson (ACS, New York, 2005), p. 378.

    Google Scholar 

  90. D. D. Dominguez and T. M. Keller, High Perform. Polym. 18, 283 (2006).

    Article  CAS  Google Scholar 

  91. H. Zhang, T. Liu, W. Yan, Y. Su, H. Yu, Y. Yang, and Z. Jiang, High Perform. Polym. 26, 1007 (2014).

    Article  CAS  Google Scholar 

  92. M. Laskoski, D. D. Dominguez, and T. M. Keller, Polymers 48, 6234 (2007).

    Article  CAS  Google Scholar 

  93. F. Zhao, R. Liu, X. Yu, K. Naito, X. Qu, and Q. Zhang, J. Appl. Polym. Sci. 132, 42606 (2015).

    Article  CAS  Google Scholar 

  94. L. Zong, C. Liu, S. Zhang, J. Wang, and X. Jian, Polymers 77, 177 (2015).

    Article  CAS  Google Scholar 

  95. L. S. Zong, C. Liu, Y. Guo, J. Y. Wang, and X. G. Jian, RSC Adv. 5, 77027 (2015).

  96. Y. Zu, L. Zong, J. Wang, and X. Jian, Polymers 172, 372 (2019).

    Article  CAS  Google Scholar 

  97. Y. Liu, P. Ji, Z. Zhang, X. Yu, K. Naito, and Q. Zhang, High Perform. Polym. 31, 1075 (2019).

    Article  CAS  Google Scholar 

  98. C. Liu, J. Wang, E. Lin, L. Zong, and X. Jian, Polym. Degrad. Stab. 97, 460 (2012).

    Article  CAS  Google Scholar 

  99. C. Liu, E. Lin, L. Zong, C. Liu, G. Yu, J. Wang, F. Hu, Z. Weng, and X. Jian, Polym. Bull. 75, 1037 (2018).

    Article  CAS  Google Scholar 

  100. H. Wang, J. Wang, H. Guo, X. Chen, X. Yu, Y. Ma, P. Ji, K. Naito, Z. Zhang, and Q. Zhang, Polym. Chem. 9, 976 (2018).

    Article  CAS  Google Scholar 

  101. Z. Zhang, Z. Li, H. Zhou, X. Lin, T. Zhao, M. Zhang, and C. Xu, J. Appl. Polym. Sci. 131, 40919 (2014).

    Google Scholar 

  102. A. V. Babkin, E. B. Zodbinov, B. A. Bulgakov, A. V. Kepman, and V. V. Avdeev, Polym. Sci., Ser. B 58, 298 (2016).

    Article  CAS  Google Scholar 

  103. B. A. Bulgakov, A. V. Babkin, A. A. Bogolyubov, E. S. Afanas’eva, and A. V. Kepman, Russ. Chem. Bull. 65, 287 (2016).

    Article  CAS  Google Scholar 

  104. M. Laskoski, A. Neal, M. B. Schear, T. M. Keller, H. L. Ricks-Laskoski, and A. P. Saab, J. Polym. Sci., Part A: Polym. Chem. 53, 2186 (2015).

    Article  CAS  Google Scholar 

  105. P. B. Dzhevakov, R. F. Korotkov, B. A. Bulgakov, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, Mendeleev Commun. 26, 527 (2016).

    Article  CAS  Google Scholar 

  106. K. S. Belsky, A. V. Sulimov, B. A. Bulgakov, A. V. Babkin, and A. V. Kepman, Data Br. 13, 10 (2017).

    Article  Google Scholar 

  107. B. A. Bulgakov, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, in Proceedings of VII International Baekeland Symposium, Tarragona, Spain, 2019 (Tarragona, 2019), P-36.

  108. B. A. Bulgakov, A. V. Sulimov, A. V. Babkin, D. V. Afanasiev, A. V. Solopchenko, E. S. Afanaseva, A. V. Kepman, and V. V. Avdeev, Mendeleev Commun. 3, 257 (2017).

    Article  CAS  Google Scholar 

  109. B. Bulgakov, A. Sulimov, A. Babkin, I. Timoshkin, A. Solopchenko, A. Kepman, and V. Avdeev, J. Compos. Mater. 51, 4157 (2017).

    Article  CAS  Google Scholar 

  110. V. E. Terekhov, V. V. Aleshkevich, E. S. Afanaseva, S. S. Nechausov, A. V. Babkin, B. A. Bulgakov, A. V. Kepman, and V. V. Avdeev, React. Funct. Polym. 139, 34 (2019).

    Article  CAS  Google Scholar 

  111. V. E. Terekhov, V. V. Aleshkevich, E. S. Afanaseva, S. S. Nechausov, A. V. Babkin, B. A. Bulgakov, A. V. Kepman, and V. V. Avdeev, Data Br. 28, 104858 (2020).

    Article  CAS  Google Scholar 

  112. B.-G. Sun, Q. Lei, Y. Guo, H.-Q. Shi, J.-B. Sun, K.‑X. Yang, H. Zhou, Y.-Q. Li, N. Hu, H. Wang, and S.-Y. Fu, Composites, Part B 166, 681 (2019).

    Article  CAS  Google Scholar 

  113. R. Y. Ting and H. C. Nash, Polym. Eng. Sci. 21, 441 (1981).

    Article  CAS  Google Scholar 

  114. M. Laskoski, J. S. Clarke, A. Neal, and T. M. Keller, Macromol. Chem. Phys. 218, 1700207 (2017).

    Article  CAS  Google Scholar 

  115. M. V. Yakovlev, O. S. Morozov, E. S. Afanaseva, B. A. Bulgakov, A. V. Babkin, and A. V. Kepman, React. Funct. Polym. 146, 104409 (2020).

    Article  CAS  Google Scholar 

  116. M. Laskoski, A. R. Shepherd, W. Mahzabeen, J. S. Clarke, T. M. Keller, U. Sorathia, J. Polym. Sci., Part A: Polym. Chem. 56, 1128 (2018).

    Article  CAS  Google Scholar 

  117. A. Medjahed, M. Derradji, A. Zegaoui, R. Wu, and B. Li, Mater. Sci. Technol. 35, 661 (2019).

    Article  CAS  Google Scholar 

  118. B. A. Bulgakov, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, RF Patent No. 2695606S1 (2019).

  119. B. A. Bulgakov, A. V. Babkin, E. S. Afanasieva, and A. V. Kepman, in Proceedings of Conference “Proceedings of the Thermosetting Resins., Berlin Germany, 2018 (Berlin, 2018), p. 127.

  120. D. Augustine, D. Mathew, and C. P. R. Nair, Polym. Int. 62, 1068 (2012).

    Google Scholar 

  121. D. Augustine, D. Mathew, and C. Reghunadhan Nair, Polym. Int. 64, 146 (2015).

    Article  CAS  Google Scholar 

  122. C. Yin, L. Sheng, Y. Yang, G. Liang, S. Xing, J. Zeng, and J. Xiao, RSC Adv. 8, 38210 (2018).

  123. I. A. Timoshkin, V. V. Aleshkevich, E. S. Afanas’eva, B. A. Bulgakov, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, Polym. Sci., Ser. C 62, 172 (2020).

    Article  CAS  Google Scholar 

  124. B. A. Bulgakov, K. S. Belsky, S. S. Nechausov, E. S. Afanaseva, A. V. Babkin, A. V. Kepman, and V. V. Avdeev, Mendeleev Commun. 28, 44 (2018).

    Article  CAS  Google Scholar 

  125. A. V. Babkin, A. V. Sulimov, B. A. Bulgakov, and A. V. Kepman, in SAMPE Conference Proceedings (Soc. Adv. Mater. Proc. Eng., The United States, 2017), p. 713.

  126. S. B. Sastri, J. P. Armistead, T. M. Keller, and U. Sorathia, Polym. Compos. 18, 48 (1997).

    Article  CAS  Google Scholar 

  127. Z. Chen, H. Guo, H. Tang, X. Yang, M. Xu, and X. Liu, J. Appl. Polym. Sci. 129, 2621 (2013).

    Article  CAS  Google Scholar 

  128. X. Yang, K. Li, M. Xu, and X. Liu, Composites, Part B 155, 425 (2018).

    Article  CAS  Google Scholar 

  129. Z. Wu, S. Wang, L. Zong, N. Li, J. Wang, and X. Jian, High Perform. Polym. 30, 720 (2018).

    Article  CAS  Google Scholar 

  130. X. Li, F. Zhou, T. Zheng, Z. Wang, H. Zhou, H. Chen, L. Xiao, D. Zhang, and G. Wang, Polymers 11, 54 (2019).

    Article  PubMed Central  CAS  Google Scholar 

  131. X. L. Yang, K. Li, M. Z. Xu, and X. B. Liu, Chin. J. Polym. Sci 36, 106 (2018).

    Article  CAS  Google Scholar 

  132. L. Chen, D. X. Ren, S. J. Chen, H. Pan, M. Z. Xu, and X. B. Liu, eXPRESS Polym. Lett. 13, 456 (2019).

    Article  CAS  Google Scholar 

  133. Y. Luo, M. Xu, H. Pan, K. Jia, and X. Liu, Polym. Eng. Sci. 56, 150 (2016).

    Article  CAS  Google Scholar 

  134. D. Ren, K. Li, L. Chen, S. Chen, M. Han, M. Xu, and X. Liu, Composites, Part B 177, 107419 (2019).

    Article  CAS  Google Scholar 

  135. D. Ren, Y. Lei, H. Pan, L. Yan, M. Xu, and X. Liu, J. Appl. Polym. Sci. 135, 45881 (2018).

    Article  CAS  Google Scholar 

  136. D. Ren, L. Chen, Y. Yuan, K. Li, M. Xu, and X. Liu, Polymers 10, 1128 (2018).

    Article  PubMed Central  CAS  Google Scholar 

  137. Y. Zou and X. Liu, J. Appl. Polym. Sci. 129, 130 (2013).

    Article  CAS  Google Scholar 

  138. G. Wang, Y. Han, Y. Guo, J. Sun, S. Wang, H. Zhou, and T. Zhao, Eur. Polym. J. 113, 1 (2019).

    Article  CAS  Google Scholar 

  139. G. Wang, Y. Han, Y. Guo, S. Wang, J. Sun, H. Zhou, and T. Zhao, Ind. Eng. Chem. Res. 58, 9921 (2019).

    Article  CAS  Google Scholar 

  140. G. Wang, Y. Guo, Y. Han, Z. Li, J. Ding, H. Jiang, H. Zhou, and T. Zhao, High Perform. Polym. 32, 3 (2020).

    Article  CAS  Google Scholar 

  141. M. Wang and Y. Ning, ACS Appl. Mater. Interfaces 10, 11933 (2018).

    Article  CAS  PubMed  Google Scholar 

  142. Y. Zu, F. Zhang, D. Chen, L. Zong, J. Wang, and X. Jian, Polymer 198, 122490 (2020).

    Article  CAS  Google Scholar 

  143. M. Derradji, A. Zegaoui, A. Medjahed, A. Q. Dayo, J. Wang, Y. B. Arse, W. Liu, and Y.-G. Liu, Polym. Compos. 40, E912 (2019).

    Article  CAS  Google Scholar 

  144. M. Derradji, A. Zegaoui, Y.-L. Xu, A. Wang, A. Q. Dayo, J. Wang, W. Liu, Y.-G. Liu, and K. Khiari, Nucl. Instrum. Methods Phys. Res., Sect B 421, 13 (2018).

    CAS  Google Scholar 

  145. A. Medjahed, M. Derradji, A. Zegaoui, R. Wu, B. Li, Y. Wang, L. Hou, J. Zhang, and M. Zhang, Adv. Eng. Mater. 21, 1800779 (2019).

    Article  CAS  Google Scholar 

  146. M. Derradji, A. Mouloud, D. Trache, A. Zegaoui, A. Medjahed, A. F. Tarchoun, and W. Bessa, High Perform. Polym. 32, 550 (2020).

    Article  CAS  Google Scholar 

  147. G. A. Eid, A. I. Kany, M. M. El-Toony, A. M. Madbouly, I. I. Bashter, and F. A. Gaber, Arab J. Nucl. Sci. Appl. 46, 226 (2013).

    Google Scholar 

  148. Belgin E. Eren, G. A. Aycik, A. Kalemtas, A. Pelit, D. A. Dilek, and M. T. Kavak, Radiat. Phys. Chem. 115, 43 (2015).

    CAS  Google Scholar 

  149. R. F. Gibson, Principles of Composite Material Mechanics (CRC Press, Boca Raton, 2016).

    Book  Google Scholar 

Download references

Funding

This work was financially supported by the Russian Foundation for Basic Research (project code 19-13-50529).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to B. A. Bulgakov.

Rights and permissions

Reprints and Permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bulgakov, B.A., Morozov, O.S., Timoshkin, I.A. et al. Bisphthalonitrile-based Thermosets as Heat-resistant Matrices for Fiber Reinforced Plastics. Polym. Sci. Ser. C 63, 64–101 (2021). https://doi.org/10.1134/S1811238221010021

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1811238221010021