화학공학소재연구정보센터
Macromolecular Research, Vol.28, No.1, 74-81, January, 2020
Synthesis and Properties of Benzoxazine Monomers Bearing Both 3-Methyltetrahydrophtalimide and Nitrile Groups: Para-Para vs. Ortho-Ortho
E-mail:
Two 3-methytetrahydrophtalimide-functional benzoxazine monomers containing nitrile group have been prepared in order to achieve the basic design rules for developing high-performance thermosets via multifunctional benzoxazines. The chemical structures of the two new synthesized benzoxazine monomers have been confirmed by 1H NMR, 13C NMR and FT-IR. Besides, the polymerization behavior has been studied by using DSC and in situ FT-IR. In addition, the thermal stability and flame retardant properties of the resulting polybenzoxazines have also been investigated using TGA and MCC. The polybenzoxazine based on ortho-3-methytetrahydrophtalimide functional benzoxazine containing ortho-nitrile group exhibits excellent thermal stability and low flammability, with a Td10 of 378 °C and a HRC value of 180 J/(g K).
  1. Holly FW, Cope AC, J. Am. Chem. Soc., 66, 1875 (1994)
  2. Ning X, Ishida H, J. Polym. Sci. A: Polym. Chem., 32(6), 1121 (1994)
  3. Kiskan B, Yagci Y, in Thermosets, 2nd ed., Elsevier, Chap.17, pp543-576 2018.
  4. Kiskan B, React. Funct. Polym., 129, 76 (2018)
  5. Parnklang T, Boonyanuwat K, Mora P, Ekgasit S, Rimdusit S, eXPRESS Polym. Lett., 13, 65 (2019)
  6. Zegaoui A, Derradji M, Ma R, Cai WA, Liu WB, Wang J, Zhang LL, J. Appl. Polym. Sci., 135, 46283 (2018)
  7. Xu QY, Zeng M, Chen JB, Zeng SG, Huang YW, Feng ZJ, Xu QQ, Yan CJ, Gu Y, React. Funct. Polym., 122, 158 (2018)
  8. Sun BG, Yang KX, Lei Q, Shi HQ, Li YQ, Hu N, Fu SY, Compos. Part A, 112, 11 (2018)
  9. Schafer H, Hartwig A, Koschek K, Polymer, 135, 285 (2018)
  10. Chen CH, Lin CH, Hon JM, Wang MW, Juang TY, Polymer, 154, 35 (2018)
  11. Xiong X, Ren R, Cui X, Chen P, Polym. Test., 72, 232 (2018)
  12. Sun L, Zhang K, Min CY, Liu YQ, Wang YT, Zhang JX, Li SJ, Thermochim. Acta, 668, 1 (2018)
  13. Chaisuwan T, Ishida H, J. Appl. Polym. Sci., 101(1), 548 (2006)
  14. Zhang K, Liu J, Ohashi S, Liu XY, Han ZW, Ishida H, J. Polym. Sci. A: Polym. Chem., 53(11), 1330 (2015)
  15. Zhang K, Qiu J, Li S, Shang Z, Wang J, J. Appl. Polym. Sci., 134, 45408 (2017)
  16. Jin L, Agag T, Ishida H, Eur. Polym. J., 46, 354 (2010)
  17. Liu YL, Chen YJ, Polymer, 45(6), 1797 (2004)
  18. Zhang K, Yu XY, Macromolecules, 51(16), 6524 (2018)
  19. El-Mahdy AF, Kuo SW, Polym. Chem., 9, 1815 (2018)
  20. Kolanadiyil SN, Bijwe J, Varma IK, React. Funct. Polym., 73(11), 1544 (2013)
  21. Cao GP, Chen WJ, Liu XB, Polym. Degrad. Stabil., 93, 739 (2008)
  22. Ji SC, Yuan P, Hu JH, Sun R, Zeng K, Yang G, Polymer, 84, 365 (2016)
  23. Wang DX, Li B, Zhang YH, Lu ZJ, J. Appl. Polym. Sci., 127(1), 516 (2013)
  24. Zhang H, Lu Z, e-Polym., 10 (2010)
  25. Singh AS, Shukla SK, Pandey AK, Tripathi DN, Prasad NE, Polym. Bull., 75(8), 3781 (2018)
  26. Kim HJ, Brunovska Z, Ishida H, Polymer, 40(23), 6565 (1999)
  27. Zhang K, Shang ZK, Evans CJ, Han L, Ishida H, Yang SF, Macromolecules, 51(19), 7574 (2018)
  28. Zhang K, Liu Y, Han L, Wang J, Ishida H, RSC Adv., 9, 1526 (2019)
  29. Han L, Zhang K, Ishida H, Froimowicz P, Macromol. Chem. Phys., 218, 160056 (2017)
  30. Dunkers J, Ishida H, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 51, 1061 (1995)
  31. Han L, Iguchi D, Gil P, Heyl TR, Sedwick VM, Arza CR, Ohashi S, Lacks DJ, Ishida H, J. Phys. Chem. A, 121(33), 6269 (2017)
  32. Augustine D, Mathew D, Nair CPR, Polymer, 60, 308 (2015)
  33. Sastri SB, Keller TM, J. Polym. Sci. A: Polym. Chem., 36(11), 1885 (1998)
  34. Zhang K, Tan XX, Wang YT, Ishida H, Polymer, 168, 8 (2019)
  35. Hamerton I, Thompson S, Howlin BJ, Stone CA, Macromolecules, 46(19), 7605 (2013)