화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.24, No.5, 409-414, May, 2016
DOI10.1007/s13233-016-4061-1  Export Citation
Synthesis and Characterization of a Lateral Phthalonitrile Functionalized Main-Chain Polybenzoxazine Precursor
Jian Zheng1, 2, †, Yan Zhang1, 2, Ying Wang1, 2, Jianqun Gan1, 2, Lu Shen1, 2, FuBin Luo1, 2, Liyan Liang1, 3, Kun Wu1, 3, and Mangeng Lu1, 3, †
  • 1Key Laboratory of Cellulose and Lignocellulosics Chemistry, Guangzhou institute of Chemistry, Chinese Academy of Sciences, Chinese Academy of Sciences, Guangzhou, 510650, P. R. China
  • 2University of Chinese Academy of Sciences, Beijing, 100039, P. R. China
  • 3, China
E-mail:,
A lateral phthalonitrile functionalized main-chain polybenzoxazine precursor has been successfully synthesized. The structure was characterized by proton nuclear magnetic resonance (1H NMR) and Fourier transform infrared (FTIR). The formation of benzoxazine rings were confirmed by the characteristic resonances observed at about 4.55 (C-CH2-N) and 5.30 ppm (N-CH2-O) and the absorbance at 950 cm-1 of benzene attached with an oxazine ring. The curing behavior was monitored by differential scanning calorimetry (DSC) and in situ FTIR. The completion of polymerization was proved by the disappearance of the band located at 950 cm-1 in FTIR. Thermogravimetric analysis (TGA) was used to investigate the thermal stability, and the results indicated that the thermal stability of the cured polymer gained significant improvement than that without phthalonitrile functionalization.
Keywords:phthalonitrile;polybenzoxazine;main-chain;high-performance
  1. Holly FW, Cope AC, J. Am. Chem. Soc., 66, 1875 (1944)
  2. Ning X, Ishida H, J. Polym. Sci. A: Polym. Chem., 32(6), 1121 (1994)
  3. Ning X, Ishida HS, J. Polym. Sci. B: Polym. Phys., 32(5), 921 (1994)
  4. Ishida H, Rodriguez Y, Polymer, 36(16), 3151 (1995)
  5. Dunkers J, Zarate EA, Ishida H, J. Phys. Chem., 100(32), 13514 (1996)
  6. Ishida H, Low HY, Macromolecules, 30(4), 1099 (1997)
  7. Ishida H, Krus CM, Macromolecules, 31(8), 2409 (1998)
  8. Low HY, Ishida H, J. Polym. Sci. B: Polym. Phys., 36(11), 1935 (1998)
  9. Su YC, Chen WC, Ou KL, Chang FC, Polymer, 46(11), 3758 (2005)
  10. Takeichi T, Kano T, Agag T, Polymer, 46(26), 12172 (2005)
  11. Lin CH, Cai SX, Leu TS, Hwang TY, Lee HH, J. Polym. Sci. A: Polym. Chem., 44(11), 3454 (2006)
  12. Wang CF, Wang YT, Tung PH, Kuo SW, Lin CH, Sheen YC, Chang FC, Langmuir, 22(20), 8289 (2006)
  13. Qu L, Xin Z, Langmuir, 27(13), 8365 (2011)
  14. Liu J, Lu X, Xin Z, Zhou CL, Langmuir, 29(1), 411 (2013)
  15. Chernykh A, Liu JP, Ishida H, Polymer, 47(22), 7664 (2006)
  16. Velez-Herrera P, Doyama K, Abe H, Ishida H, Macromolecules, 41(24), 9704 (2008)
  17. Liu YF, Zhao SS, Zhang HL, Wang M, Run MT, Thermochim. Acta, 549, 42 (2012)
  18. Liu YL, Yu JM, Chou CI, J. Polym. Sci. A: Polym. Chem., 42(23), 5954 (2004)
  19. Kumar KSS, Nair CPR, Radhakrishnan TS, Ninan KN, Eur. Polym. J., 43, 2504 (2007)
  20. Kim HJ, Brunovska Z, Ishida H, Polymer, 40(23), 6565 (1999)
  21. Kim HJ, Brunovska Z, Ishida H, Polymer, 40(7), 1815 (1999)
  22. Agag T, Takeichi T, Macromolecules, 34(21), 7257 (2001)
  23. Keller TM, J. Polym. Sci. A: Polym. Chem., 25, 2569 (1987)
  24. Keller TM, J. Polym. Sci. A: Polym. Chem., 26, 3199 (1988)
  25. Keller TM, Polymer, 34, 952 (1993)
  26. Warzel ML, Keller TM, Polymer, 34, 663 (1993)
  27. Burchill PJ, J. Polym. Sci. A: Polym. Chem., 32(1), 1 (1994)
  28. Sastri SB, Keeler TM, J. Polym. Sci. A: Polym. Chem., 37(13), 2105 (1999)
  29. Sumner MJ, Sankarapandian M, McGrath JE, Riffle JS, Sorathia U, Polymer, 43(19), 5069 (2002)
  30. Zhao X, Lei YJ, Zhao R, Zhong JC, Liu XB, J. Appl. Polym. Sci., 123(6), 3580 (2012)
  31. Keller TM, Price TR, J. Macromol. Sci. Part A: Chem., 18, 931 (1982)
  32. Sastri SB, Keller TM, J. Polym. Sci. A: Polym. Chem., 36(11), 1885 (1998)
  33. Li WT, Zuo F, Jia K, Liu XB, Chin. Chem. Lett., 20, 348 (2009)
  34. Keller TM, Polym. Prepr., 33, 422 (1992)
  35. Burchill PJ, J. Polym. Sci. A: Polym. Chem., 32(1), 1 (1994)
  36. Zeng K, Zhou K, Zhou SH, Hong HB, Zhou HF, Wang YP, Miao PK, Yang G, Eur. Polym. J., 45, 1328 (2009)
  37. Zhou SH, Hong HB, Zeng K, Miao PK, Zhou HF, Wang YP, Liu T, Zhao CN, Xu GL, Yang G, Polym. Bull., 62(5), 581 (2009)
  38. Amir B, Zhou H, Liu F, Aurangzeb H, J. Polym. Sci. A: Polym. Chem., 48(24), 5916 (2010)
  39. Badshah A, Kessler MR, Heng Z, Zaidi JH, Hameed S, Hasan A, Polymer Chemistry, 4, 3617 (2013)
  40. Xu MZ, Liu MD, Dong SH, Liu XB, J. Mater. Sci., 48(23), 8108 (2013)
  41. Zhang ZB, Li Z, Zhou H, Lin XK, Zhao T, Zhang MY, Xu CH, J. Appl. Polym. Sci., 131, 1366 (2014)
  42. Brunovska Z, Ishida H, J. Appl. Polym. Sci., 73(14), 2937 (1999)
  43. Brunovska Z, Lyon R, Ishida H, Thermochim. Acta, 357, 195 (2000)
  44. Zuo F, Liu XB, J. Appl. Polym. Sci., 117(3), 1469 (2010)
  45. Chen BK, Chiu TM, Tsay SY, J. Appl. Polym. Sci., 94(1), 382 (2004)
  46. Lin CH, Chang SL, Shen TY, Shih YS, Lin HT, Wang CF, Polym. Chem., 3, 935 (2012)
  47. Keller TM, Chem. Mater., 6, 302 (1994)
  48. Chaisuwan T, Ishida H, J. Appl. Polym. Sci., 117(5), 2559 (2010)