Living anionic polymerization of N-methacryloyl-2-methylaziridine: Polymerizable N,N-dialkylmethacrylamide

Macromolecules

Volumn 41, Issue 6, 2008, Pages 1929-1936

  Suzuki, Takashi ^a   Kusakabe, Jun Ichi ^a   Ishizone, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHEMICAL ANALYSIS; FREE RADICAL POLYMERIZATION; MOLECULAR WEIGHT DISTRIBUTION; MONOMERS;

AZIRIDINE MOIETIES; POSTPOLYMERIZATION;

ANIONIC POLYMERIZATION;

EID: 41749120093     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma702615u     Document Type: Article

References (44)

1. (a) Davis, T. P.; Haddleton, D. M.; Richards, S. N. J. Macromol. Sci., Rev. Macromol. Chem. 1994, C34, 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. (a) Otsu, T.; Inoue, M.; Yamada, B.; Mori, T. J. Polym. Sci., Polym. Lett. Ed. 1975, 13, 505.
8. (b) Sato, T.; Miyamoto, J.; Otsu, T. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 3921.
9. (c) Guo, Y.; Feng, F.; Miyashita, T. Macromolecules 1999, 32, 1115.
10. (d) Zhang, J.; Liu, W.; Nakano, T.; Okamoto, Y. Polym. J. 2000, 32, 694.
11. (a) Breslow, D. S.; Hulse, G. E.; Matlack, A. S. J. Am. Chem. Soc. 1957, 79, 3760.
12. (b) Kennedy, J. P.; Otsu, T. J. Macromol. Sci., Rev. Macromol. Chem. 1972, C6, 237.
13. (c) Otsu, T.; Yamada, B.; Itahashi, M.; Mori, T. J. Polym. Sci., Polym. Chem. Ed. 1976, 14, 1347.
14. Xie, X.; Hogen-Esch, T, E. Macromolecules 1996, 29, 1746.
15. (a) Kobayashi, M.; Okuyama, S.; Ishizone, T.; Nakahama, S. Macromolecules 1999, 32, 6466.
16. (b) Kobayashi, M.; Ishizone, T.; Nakahama, S. Macromolecules 2000, 33, 4411.
17. (c) Ito, M.; Ishizone, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 4832.
18. (d) Ishizone, T.; Yashiki, D.; Kobayashi, M.; Suzuki, T.; Ito, M.; Nakahama, S. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1260.
19. (a) Sogah, D. Y.; Hertler, W. R.; Webster, O. W.; Cohen, G. M. Macromolecules 1987, 20, 1473.
20. (b) Freitag, R.; Baltes, T.; Eggert, M. J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 803.
21. Yokota, K.; Oda, J. Kogyo Kagaku Zasshi 1970, 73, 224.
22. Butler, G. B.; Myers, G. R. J. Macromol. Sci., Chem. 1971, A5, 135.
23. Kodaira, T.; Aoyamà, F. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 897.
24. Kodaira, T.; Tanahashi, H.; Hara, K. Polym. J. 1990, 22, 649.
25. Although we have also carried out the anionic polymerizations of N,N-dimethylmethacrylamide and AW-dibutylmethacrylamide under the various conditions, no polymeric products have been virtually obtained.
26. Okamoto, O.; Yuki, H. J. Polym. Sci., Polym. Chem. Ed. 1981, 19, 2647.
27. (a) Stamm, H. J. Prakt. Chem. 1999, 547, 319.
28. (b) Lin, P. Y.; Bentz, G.; Stamm, H. J. Prakt. Chem. 1993, 335, 23.
29. (c) Ham, G. E. J. Org. Chem. 1964, 29, 3052.
30. (d) Iwakura, Y.; Nabeya, A. J. Org. Chem. 1960, 25, 1118.
31. (e) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
32. Preliminary results of polymerization of 1 have been reported in the IUPAC-PSK30 conference in Busan, Korea in 2006. Suzuki, T.; Kusakabe, J.; Ishizone, T. Macromol. Symp. 2007, 249-250, 412.
33. (a) Fayt, R.; Forte, R.; Jacobs, C.; Jerome, R.; Ouhadi, T.; Teyssié, Ph.; Varshney, S. K. Macromolecules 1987, 20, 1442.
34. (b) Varshney, S. K.; Hautekeer, J. P.; Fayt, R.; Jérôme, R.; Teyssié, Ph. Macromolecules 1990, 23, 2618.
35. (a) Ozaki, H.; Hirao, A.; Nakahama, S. Macromol. Chem. Phys. 1995, 196, 2099.
36. (b) Ishizone, T.; Yoshimura, K.; Hirao, A.; Nakahama, S. Macromolecules 1998, 31, 8706.
37. Acyl substitution toward the pendant moieties of the resulting polymer might partially occur, when the polymerization was quenched with methanol instead of isopropanol. After the termination, the resulting methoxide found to attack toward the carbonyl groups on the polymers but not the hindered isopropoxide.
38. 13C NMR spectra were overlapped and complicated.
39. Kunkel, D.; Müller, A. H. E.; Janata, M.; Lochmann, L. Makromol. Chem. Macromol. Symp. 1992, 60, 315.
40. Baskaran, D.; Müller, A. H. E.; Sivaram, S. Macromolecules 1999, 32, 1356.
41. (a) Iwakura, Y.; Nabeya, A.; Nishiguchi, T. Yuki Gosei Kagaku Kyokaishi 1968, 26, 101.
42. (b) Fanta, P. E.; Deutsch, A. S. J. Org. Chem. 1958, 23, 72.
43. In the organic chemistry, it has been reported that the ring-opening reactions between N-acyl-2-methylaziridines and several nucleophiles proceed not regioselectively (ref 13). We could not estimate the ratio of x and (1 - x) for the product in Scheme 3.
44. Hirao, A.; Takenaka, K.; Packrisamy, S.; Yamaguchi, K.; Nakahama, S.; Makromol. Chem. 1985, 186, 1157.