A novel benzimidazole moiety-containing benzoxazine: Synthesis, polymerization, and thermal properties
Po Yang
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China
National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, China
Search for more papers by this authorCorresponding Author
Yi Gu
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, ChinaSearch for more papers by this authorPo Yang
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China
National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, China
Search for more papers by this authorCorresponding Author
Yi Gu
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China
State Key Laboratory of Polymeric Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, ChinaSearch for more papers by this authorAbstract
A novel benzoxazine-containing benzimidazole moiety (P-PABZ) was synthesized from 2-(4-aminophenyl)-1H-benzimidazole-5-amine and characterized. With the aid of differential scanning calorimetry and in situ Fourier transform infrared, we found the thermal polymerization of P-PABZ in bulk started around 140 °C and its favored polymerization pathway. Compared to the benzoxazine derived from 4,4′-diamine diphenyl methane (P-MDA), P-PABZ exhibited lower processing temperature, and the corresponding polymers had higher glass transition temperature and enhanced thermal stability. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
REFERENCES AND NOTES
- 1 Holly, F. W.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1875–1879.
- 2 Burke, W. J. J. Am. Chem. Soc. 1949, 71, 609–612.
- 3 Burke, W. J.; Smith, R. J. Am. Chem. Soc. 1952, 74, 602–605.
- 4 Burke, W. J.; Waynestephens, C. J. Am. Chem. Soc. 1952, 74, 1518–1520.
- 5 Burke, W. J.; Murdock, K. C.; Grace, E. J. Am. Chem. Soc. 1954, 76, 1677–1679.
- 6 Ning, X.; Ishida, H. J. Polym. Sci. Part B: Polym. Phys. 1994, 32, 921–927.
- 7 Dunkers, J.; Zarate, E. A.; Ishida, H. J. Phys. Chem. 1996, 100, 13514–13520.
- 8 Macko, J. A.; Ishida, H. Macromol. Chem. Phys. 2001, 202, 2351–2359.
- 9 Macko, J. A.; Ishida, H. Polymer 2001, 42, 227–240.
- 10 Macko, J. A.; Ishida, H. Polymer 2001, 42, 6371–6383.
- 11 Su, Y. C.; Chang, F. C. Polymer 2003, 44, 7989–7996.
- 12 Wang, C. F.; Wang, Y. T.; Tung, P. H.; Kuo, S. W.; Lin, C. H.; Sheen, Y. C.; Chang, F. C. Langmuir 2006, 22, 8289–8292.
- 13 Liao, C. S.; Wang, C. F.; Lin, H. C.; Chou, H. Y.; Chang, F. C. J. Phys. Chem. C 2008, 112, 16189–16191.
- 14 Ishida, H.; Allen, D. J. J. Polym. Sci. Part B: Polym. Phys. 1996, 34, 1019–1030.
- 15 Ishida, H.; Low, H. Y. Macromolecules 1997, 30, 1099–1106.
- 16 Liu, X.; Gu, Y. J. Appl. Polym. Sci. 2002, 84, 1107–1113.
- 17 Sudo, A.; Kudoh, R.; Nakayama, H.; Arima, K.; Endo, T. Macromolecules 2008, 41, 9030–9034.
- 18
Dunkers, J.;
Ishida, H.
J. Polym. Sci. Part A: Polym. Chem.
1999,
37,
1913–1921.
10.1002/(SICI)1099-0518(19990701)37:13<1913::AID-POLA4>3.0.CO;2-E CAS Web of Science® Google Scholar
- 19 Sudo, A.; Hirayama, S.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 479–484.
- 20 Sudo, A.; Kudoh, R.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 1724–1729.
- 21 Andreu, R.; Reina, J. A.; Ronda, J. C. J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 6091–6101.
- 22 Zuniga, C.; Larrechi, M. S.; Lligadas, G.; Ronda, J. C.; Galia, M.; Cadiz, V. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 1219–1227.
- 23 Herrera, P. V.; Ishida, H. J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 5871–5881.
- 24 Kiskan, B.; Koz, B.; Yagci, Y. J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 6955–6961.
- 25 Agag, T.; Arza, C. R.; Maurer, F. H. J.; Ishida, H. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 4335–4342.
- 26 Ergin, M.; Kiskan, B.; Gacal, B.; Yagci, Y. Macromolecules 2007, 40, 4724–4727.
- 27 Chernykh, A.; Agag, T.; Ishida, H. Polymer 2009, 50, 3153–3157.
- 28 Sudo, A.; Mori, A.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 2183–2190.
- 29 Chung, I. S.; Park, C. E.; Ree, M.; Kim, S. Y. Chem. Mater. 2001, 13, 2801–2806.
- 30 Gao, G. Q.; Dong, L.; Liu, X. Y.; Ye, G. D.; Gu, Y. Polym. Eng. Sci. 2008, 48, 912–917.
- 31 Lin, C. H.; Chang, S. L.; Hsieh, C. W.; Lee, H. H. Polymer 2008, 49, 1220–1229.
- 32 Sponton, M.; Larrechi, M. S.; Ronda, J. C.; Galia, M.; Cadiz, V. J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 7162–7172.
- 33 Lin, C. H.; Chang, S. L.; Lee, H. H.; Chang, H. C.; Hwang, K. Y.; Tu, A. P.; Su, W. C. J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 4970–4983.
- 34 Liu, Y. L.; Lin, G. C.; Wu, C. H. J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 949–954.
- 35 Agag, T.; Jin, L.; Ishida, H. Polymer 2009, 50, 5940–5944.
- 36 Jubsilp, C.; Damrongsakkul, S.; Takeichi, T.; Rimdusit, S. Therm. Acta 2006, 447, 131–140.
- 37 Ishida, H.; Rodrigues, Y. Polymer 1995, 36, 3151–3158.
- 38 Allen, D. J.; Ishida, H. Polymer 2007, 48, 6763–6772.
- 39 Ning, X.; Ishida, H. J. Polym. Sci. Part A: Polym. Chem. 1994, 32, 1121–1129.
- 40 Wang, Y. X.; Ishida, H. Polymer 1999, 40, 4563–4570.
- 41 Endo, T.; Sudo, A. J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 4847–4858.