Cationic ring-opening polymerization of 1,3-benzoxazines: Mechanistic study using model compounds

Macromolecules

Volumn 43, Issue 10, 2010, Pages 4562-4572

  Chutayothin, Papinporn ^a   Ishida, Hatsuo ^a  

^a Case Western Reserve University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINE; BENZOXAZINE MONOMERS; CATIONIC RING OPENING POLYMERIZATION; CRUDE PRODUCTS; H NMR SPECTRA; INITIATION MECHANISM; MANNICH BASE; MECHANISTIC STUDIES; METHYLENE BRIDGE; MODEL COMPOUND; RETENTION TIME;

CATIONIC POLYMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PROTONATION; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

COMPLEXATION;

EID: 77952522071     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma901743h     Document Type: Article

References (43)

1. Ning, X.; Ishida, H. J. Polym Sci., Chem. Ed. 1994, 32, 1121-1129
2. Ishida, H.; Low, H. Y. Macromolecules 1997, 30, 1099-1106
3. Ishida, H.; Ohba, S. Polymer 2005, 46, 5588-5595
4. Ghosh, N. N.; Kiskan, B.; Yagci, Y. Prog. Polym. Sci. 2007, 32, 1344-1391
5. Knop, A.; Pilato, L. A. Phenolic Resins: Chemistry, Applications and Performances, Future Directions; Springer-Verlag: Berlin, 1985,; Chapter 9.
6. Chernykh, A.; Liu, J. P.; Ishida, H. Polymer 2006, 47, 7664-7669
7. Takeichi, T.; Kano, T.; Agag, T. Polymer 2005, 46, 12172-12180
8. Chernykh, A.; Liu, J. P.; Ishida, H. Polymer 2006, 47, 7664-7669
9. Agag, T.; Takeichi, T. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1878-1888
10. Kiskan, B.; Yagci, Y.; Ishida, H. J. Polym. Sci.; Part A: Polym. Chem. 2008, 46, 414-420
11. Nagai, A.; Kamei, Y.; Wang, X. S.; Omura, M.; Sudo, A.; Nishida, H.; Kawamoto, E.; Endo, T. J. Polym. Sci.; Part A: Polym. Chem. 2008, 46, 2316-2325
12. Velez-Herrera, P.; Doyama, K.; Abe, H.; Ishida, H. Macromolecules 2008, 41, 9704-9714
13. Chou, C. I.; Liu, Y. L. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 6509-6517
14. Chernykh, A.; Agag, T.; Ishida, H. Polymer 2009, 50, 382
15. Chernykh, A.; Agag, T.; Ishida, H. Polymer 2009, 50, 3153-3157
16. Chernykh, A.; Agag, T.; Ishida, H. Macromolecules 2009, 42, 5121-5127
17. Guth, G. Ph.D. Thesis, University of Mulhouse, 1981.
18. Schwob, M. J., Ph.D. Thesis, University of Mulhouse, 1983.
19. McDonagh, A. F.; Smith, H. J. Org. Chem. 1968, 33, 8-12
20. Riess, G.; Schwob, M. J.; Guth, G.; Roche, M.; Lande, B., Advances in Polymer Synthesis; Culbertson, M. B.; Mcgrath, E. J., Eds.; Plenum: New York, 1985; pp 27 - 49. This mechanism was first proposed by Burke
21. Burke, W. J. J. Am. Chem. Soc. 1949, 71, 609-612
22. Burke, W. J.; Bishop, J. L.; Glennie, E. L.; Bauer, W. N., Jr. J. Org. Chem. 1965, 30, 3423-3427) but later refined by Riess et al
23. Dunkers, J.; Ishida, H. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1913-1921
24. Wang, Y. X.; Ishida, H. Polymer 1999, 40, 4563-4570
25. Sudo, A.; Kudoh, R.; Nakayama, H.; Arima, K.; Endo, T. Macromolecules 2008, 41, 9030-9034
26. Hayakawa, T.; Osanai, Y.; Niizeki, K.; Haba, O.; Ueda, M. High Perform. Polym. 2000, 12, 237-246
27. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4 th ed.; Butterworth-Heinemann: Boston, MA, 1998.
28. Dunkers, J.; Ishida, H. Spectrochim. Acta 1995, 51A, 855-867
29. Ishida, H. U.S. Patent 5,543,516, 1996.
30. Ishida, H.; Roduriguez, Y. J. Appl. Polym. Sci. 1995, 58, 1751-1760
31. Wang, R. X.; You, X. Z.; Meng, Q. J.; Mintz, E. A.; Bu, X. R. Synth. Commun. 1994, 24, 1757-1760
32. Yudin, L. G.; Blokhin, A. V.; Bundel, Yu. G.; Simkin, B. Ya.; Terenin, V. I. Zh. Org. Khim. 1983, 19, 2361-2366
33. Joglekar, S. J.; Samant, S. D. J. Indian Chem. Soc. 1988, 65, 110-111
34. Li, C.; Lobkovsky, E.; Porco, J. A., Jr J. Am. Chem. Soc. 2000, 122, 10484-10485
35. Wan, X.-H.; Zhou, H.-B.; Xie, R.; Zhang, D.; Feng, X.-D.; Zhou, Q.-F. Chem. Res. Chin. Univ. 1999, 15, 182-187
36. Norte, M.; Rodriguez, M. L.; Fernandez, J. J.; Eguren, L.; Estrada, D. M. Tetrahedron 1988, 44, 4973-4980
37. Wolfrom, M. L.; Koos, E. W.; Bhat, H. B. J. Org. Chem. 1967, 32, 1058-1060
38. Chary, K. P.; Mohan, G. H.; Iyengar, D. S. Chem. Lett. 1999, 11, 1223-1224
39. Pethrick, R. A.; Thomson, B. Br. Polym. J. 1986, 18, 171-180
40. Dargaville, T. R.; De Bruyn, P. J.; Lim, A. S. C.; Looney, M. G.; Potter, A. C. J. Polym. Sci. Part A: Polym Chem. 1997, 35, 1389-1398
41. Hemvician, K.; Laobuthee, A.; Chirachanchai, S.; Ishida, H. Polym. Degrad. Stab. 2002, 76, 1-15
42. Brunovska, Z.; Liu, J. P.; Ishida, H. Macromol. Chem. Phys. 1999, 200, 1745-1752
43. Liu, X.; Gu, Y. Sci. Chin., Ser. B 2001, 44, 552-560