A molecular dynamic simulation of crosslinking of bisphenol and triazine by united atom model: A polycyanurate model

Chemistry Letters

Volumn 40, Issue 3, 2011, Pages 309-311

  Ikeno, Taketo ^a   Tsubuku, Makoto ^a   Katagiri, Masayuki ^a   Tsujimoto, Tomoo ^a  

^a MITSUBISHI GAS CHEMICAL COMPANY INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951867974     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.309     Document Type: Article

References (45)

1. Chemistry and Technology of Cyanate Ester Resins, ed. by I. Hamerton, Blackie Academic and Professional, Glasgow, 1994.
2. I. Hamerton, J. N. Hay, Polym. Int. 1998, 47, 465.
3. M. Gaku, K. Suzuki, K. Nakamichi, U.S. Patent 4110364, 1978.
4. M. Gaku, N. Nagai, Y. Osaki, U.S. Patent 4287014, 1981.
5. I. Hamerton, B. J. Howlin, P. Klewpatinond, H. J. Shortley, S. Takeda, Polymer 2006, 47, 690.
6. I. Hamerton, B. J. Howlin, P. Klewpatinond, S. Takeda, Polymer 2002, 43, 4599.
7. R. D. Allington, D. Attwood, I. Hamerton, J. N. Hay, B. J. Howlin, Comput. Theor. Polym. Sci. 2001, 11, 467.
8. A. S. Deazle, I. Hamerton, C. R. Heald, B. J. Howlin, Polym. Int. 1996, 41, 151.
9. I. Hamerton, C. R. Heald, B. J. Howlin, J. Mater. Chem. 1996, 6, 311.
10. R. D. Allington, D. Attwood, I. Hamerton, J. N. Hay, B. J. Howlin, Polymer 2003, 44, 793.
11. O. Georjon, G. Schwach, J.-F. Gerard, J. Galy, M. Albrand, R. Dolmazon, Polym. Eng. Sci. 1997, 37, 1606.
12. P. V. Komarov, C. Yu-Tsung, C. Shih-Ming, P. G. Khalatur, P. Reineker, Macromolecules 2007, 40, 8104.
13. V. Varshney, S. P. Patnaik, A. K. Roy, B. L. Farmer, Macromolecules 2008, 41, 6837.
14. P.-H. Lin, R. Khare, Macromolecules 2009, 42, 4319.
15. H. B. Fan, M. M. F. Yuen, Polymer 2007, 48, 2174.
16. C. Wu, W. Xu, Polymer 2006, 47, 6004.
17. C. Wu, W. Xu, Polymer 2007, 48, 5440.
18. C. Wu, W. Xu, Polymer 2007, 48, 5802.
19. S. Yu, S. Yang, M. Cho, Polymer 2009, 50, 945.
20. T. C. Clancy, S. J. V. Frankland, J. A. Hinkley, T. S. Gates, Polymer 2009, 50, 2736.
21. J. L. Tack, D. M. Ford, J. Mol. Graphics Modell. 2008, 26, 1269.
22. I. Yarovsky, E. Evans, Polymer 2002, 43, 963.
23. M. Doi, OCTA. http://octa.jp. Particularly, COGNAC Ver. 7.0 in OCTA2006 was used for the MD simulations.
24. The program was available from JSOL Corporation.
25. L. J. Kasehagen, C. W. Macosko, Polym. Int. 1997, 44, 237.
26. I. Hamerton, A. M. Emsley, B. J. Howlin, P. Klewpatinond, S. Takeda, Polymer 2003, 44, 4839.
27. S. Okumoto, S. Yamabe, J. Org. Chem. 1999, 64, 4742.
28. Since the united atom model was used, the methyl group in bisphenol A and bisphenol E, the benzyl CH group in bisphenol E, and the CH group of the benzene ring were treated as one unit. The united atom model and all the Dreiding force field parameters were embedded in J-OCTA and were used without any change. Dreiding force field: S. L. Mayo, B. D. Olafson, W. A. Goddard, J. Phys. Chem. 1990, 94, 8897.
29. r = 2.3). The low polarity of polycyanurates leads to their high insulation properties. And the Tg value of polycyanurates is over 250 °C. At such high temperature, the small electronic effect of polycyanurates should be negligible. Furthermore, the structure difference of bisphenol A and bisphenol E is only one methyl group on the methylene linkage. Therefore, the electronic effect was not considered in this calculation.
30. The number of molecules in the simulation was determined by the available computer resources. A larger number would provide better results.
31. H. C. Andersen, J. Chem. Phys. 1980, 72, 2384.
32. H. C. Andersen, J. Comput. Phys. 1983, 52, 24.
33. S. Nosé, J. Chem. Phys. 1984, 81, 511.
34. S. Nosé, Mol. Phys. 1984, 52, 255.
35. W. G. Hoover, Phys. Rev. A 1985, 31, 1695.
36. Although the cyanate is usually cured at 400500K and the cyanate resin is partially decomposed over about 700 K, it was necessary to perform the simulation at a high temperature to achieve a high ratio of the CO bond formation.
37. By changing the cutoff, the rate of crosslinking could be controlled.
38. In this simulation, after the assignment of new Dreiding force field parameters, MM relaxation was performed and then the previous velocity was restored. It was confirmed that the amorphous structures used for the Tg calculations did not have any internal strain.
39. 23
40. M. Parrinello, A. Rahman, Phys. Rev. Lett. 1980, 45, 1196.
41. M. Parrinello, A. Rahman, J. Appl. Phys. 1981, 52, 7182.
42. 23
43. g was determined based on the peak value of tan δ.
44. A. V. Lyulin, N. K. Balabaev, M. A. J. Michels, Macromolecules 2003, 36, 8574.
45. Supporting Information is available electronically on the CSJJournal Web site, http://www.csj.jp/journals/chem-lett/index.html