Living anionic polymerization of N-methacryloylazetidine: Anionic polymerizability of N,N-dialkylmethacrylamides

Macromolecules

Volumn 43, Issue 1, 2010, Pages 107-116

  Suzuki, Takashi ^a   Kusakabe, Jun Ichi ^a   Kitazawa, Keita ^a   Nakagawa, Takeshi ^a   Kawauchi, Susumu ^a   Ishizone, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

APPARENT RATE CONSTANT; CONJUGATION EFFECTS; DOUBLE BONDS; LIVING ANIONIC POLYMERIZATION; MONOMER STRUCTURES; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; NMR DATA; NMR SPECTRUM; POLYMERIZATION RATES; RING SIZES;

ACTIVATION ENERGY; CHEMICAL BONDS; FREE RADICAL POLYMERIZATION; LIVING POLYMERIZATION; MOLECULAR WEIGHT DISTRIBUTION; MONOMERS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RATE CONSTANTS; ZINC;

ANIONIC POLYMERIZATION;

EID: 73649087582     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma901984d     Document Type: Article

References (55)

1. (a) Davis, T. P.; Haddleton, D. M.; Richards, S. N. J. Macromol. Sci., Rev. Macromol. Chem. 1994, C34 (2), 243.
2. (b)Collins, S.; Ward, D. G.; Suddaby, K. H. Macromolecules 1994, 27, 7222.
3. (c) Baskaran, D.; Müller, A. H. E.; Kolshom, H.; Zagala, A. P.; Hogen-Esch, T. E. Macromolecules 1997, 30, 6695.
4. (d) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721.
5. (e) Hatada, K.; Kitayama, T. Polym. Int. 2000, 49, 11.
6. (f) Webster, O. W. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2855.
7. (g) Baskaran, D. Prog. Polym. Sci. 2003, 28, 521.
8. (h) Hsieh, H. L.; Quirk, R. P. Anionic Polymerization; Marcel Dekker: New York, 1996.
9. Otsu, T.; Inoue, M.; Yamada, B.; Mori, T. J. Polym. Sci., Polym. Lett. Ed. 1975, 13, 505.
10. (a) Sato, T.; Miyamoto, J.; Otsu, T. J. Polym. Sci., Polym. Chem. Ed 1984, 22, 3921.
11. (b) Guo, Y.; Feng, F.; Miyashita, T. Macromolecules 1999, 32, 1115.
12. (c) Zhang, J.; Liu, W.; Nakano, T.; Okamoto, Y. Polym. J. 2000, 32, 694.
13. (a) Breslow, D. S.; Hulse, G. E.; Matlack, A. S. J. Am. Chem. Soc. 1957, 79, 3760.
14. (b) Kennedy, J. P.; Otsu, T. J. Macromol. Sci., Rev. Macromol. Chem. 1972, C6, 237.
15. (c) Otsu, T.; Yamada, B.; Itahashi, M.; Mori, T. J. Polym. Sci., Polym. Chem. Ed. 1976, 14, 1347.
16. Xie, X.; Hogen-Esch, T. Macromolecules 1996, 29, 1746.
17. Kobayashi, M.; Okuyama, S.; Ishizone, T.; Nakahama, S. Macromolecules 1999, 32, 6466.
18. (a) Kobayashi, M.; Ishizone, T.; Nakahama, S. Macromolecules 2000, 33, 4411.
19. (b) Kobayashi, M.; Ishizone, T.; Nakahama, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4611.
20. (c) Ishizone, T.; Yashiki, D.; Kobayashi, M.; Suzuki, T.; Ito, M.; Nakahama, S. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1260.
21. Ito, M.; Ishizone, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4832.
22. (a) Sogah, D. Y.; Hertler, W. R.; Webster, O. W.; Cohen, G. M. Macromolecules 1987, 20, 1473.
23. (b) Freitag, R.; Baltes, T.; Eggert, M. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 803.
24. Yokota, K.; Oda, J. Kogyo Kagaku Zasshi 1970, 73, 224.
25. Butler, G. B.; Myers, G. R. J. Macromol. Sci., Chem. 1971, A5, 135.
26. Kodaira, T.; Aoyama, F. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 897.
27. Otsu, T.; Yamada, B.; Mori, T.; Inoue, M. J. Polym. Sci., Polym. Lett. Ed. 1976, 14, 283.
28. Zábranský, J.; Houska, M.; Kálal J. Makromol. Chem. 1985, 186, 247.
29. Kodaira, T.; Tanahashi, H.; Hara, K. Polym. J. 1990, 22, 649.
30. Watanabe, N.; Sakakibara, Y.; Uchino, N. Kogyo Kagaku Zasshi 1969, 72, 1349.
31. Okamoto, Y.; Yuki, H. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 2647.
32. Suzuki, T.; Kusakabe, J.; Ishizone, T. Macromolecules 2008, 41, 1929.
33. (a) Stamm, H. J. Prakt. Chem. 1999, 341, 319.
34. (b) Lin, P.; Bentz, G.; Stamm, H. J. Prakt. Chem. 1993, 335, 23.
35. (c) Ham, G. E. J. Org. Chem. 1964, 29, 3052.
36. (d) Iwakura, Y.; Nabeya, A. J. Org. Chem. 1960, 25, 1118.
37. (e) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
38. Miyake, G.; Caporaso, L.; Cavallo, 1.; Chen, E. Y.-X. Macromolecules 2009, 42, 1462.
39. (a) Anet, F. A. L.; Osyany, J. M. J. Am. Chem. Soc. 1967, 89, 352.
40. (b) Boggs, G. R.; Gerig, J. T. J. Org. Chem. 1969, 34, 1484.
41. (c) Otani, Y.; Nagae, O.; Naruse, Y.; Inagaki, S.; Ohno, M.; Yamaguchi, K.; Yamamoto, G.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2003, 125, 15191.
42. (d) Ohwada, T. Yakugaku Zasshi 2001, 121, 65.
43. (e) Fong, C. W.; Grant, H. H. Aust. J. Chem. 1981, 34, 2307.
44. (f) Spell, H. L. Anal. Chem. 1967, 39, 185.
45. (g) Brown, H. C.; Tsukamoto, A. J. Am. Chem. Soc. 1961, 83, 4549.
46. (h) Rank, A.; Allen, L. C.; Mislow, K. Angew. Chem., Int. Ed. Engl 1970, 9, 400.
47. N,NMR is 1.3-1.5. This is probably due to the larger hydrodynamic volume of polar poly(M4)s in DMF solution compared to the nonpolar polystyrene standards.
48. n = 1.10). This is probably due to trace amount of impurities in the monomer and the lowered concentration of propagating chain end.
49. Ozaki, H.; Hirao, A.; Nakahama, S. Macromol. Chem. Phys. 1995, 196, 2099.
50. Ishizone, T.; Yoshimura, K.; Hirao, A.; Nakahama, S. Macromolecules 1998, 31, 8706.
51. (a) Baskaran, D.; Müller, A. H. E.; Sivaram, S. Macromolecules 1999, 32, 1356.
52. (b) Kunkel, D.; Müller, A. H. E.; Janata, M.; Lochmann, L. Makromol. Chem., Macromol. Symp. 1992, 60, 315.
53. Ishizone, T.; Hirao, A.; Nakahama, S. Macromolecules 1993, 26, 6964.
54. In terms of a-carbon chemical shifts, we have not seen any relationship with the anionic polymerizability, as can be seen in Figure 7. This will be discussed in the forthcoming paper.
55. Hirao, A.; Takenaka, K.; Packrisamy, S.; Yamaguchi, K.; Nakahama, S. Makromol. Chem. 1985, 186, 1157.