Radical/cation transformation polymerization and its application to the preparation of block copolymers of p-Methoxystyrene and cyclohexene oxide

Macromolecules

Volumn 29, Issue 7, 1996, Pages 2354-2358

  Guo, Hai Qing ^a   Kajiwara, Atsushi ^a   Morishima, Yotaro ^a   Kamachi, Mikiharu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CATIONIC POLYMERIZATION; COPOLYMERIZATION; COPOLYMERS; ELECTRON TRANSPORT PROPERTIES; ETHERS; FREE RADICAL POLYMERIZATION; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; PARAMAGNETIC RESONANCE; STYRENE; SYNTHESIS (CHEMICAL);

BUTYL VINYL ETHER; CYCLOHEXENE OXIDE; ELECTRON TRANSFER REAGENT; METHOXYSTYRENE;

POLYMERIZATION;

EID: 0030109434     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma951096y     Document Type: Article

References (46)

1. Odian, G. Principles of Polymerization, 3rd ed.; John-Wiley & Sons: New York, 1991.
2. Bamford, C. H. Radical Polymerization. Encyclopedia of Polymer Science and Engineering; John-Wiley & Sons: New York, 1990; Vol. 13, p 708.
3. (a) Hirooka, M.; Yabuuchi, H.; Morita, S.; Kawasumi, S.; Nakaguchi, K. J. Polym. Sci., B 1967, 5, 47.
4. (b) Hirooka, M.; Yabuuchi, H.; Iseki, J.; Nakai, Y. J. Polym. Sci., A-1 1968, 6, 1381.
5. Barton, J.; Borsig, E. Complexes in Free Radical Polymerization; Elsevier: Amsterdam, 1988.
6. Kamachi, M. Adv. Polym. Sci. 1981, 38, 56.
7. (a) Otsu, T.; Yoshida, M. Makromol. Chem., Rapid Commun. 1982, 3, 127.
8. (b) Otsu, T.; Yoshida, M.; Tazaki, T. Makromol. Chem., Rapid Commun. 1982, 3, 133.
9. (c) Otsu, T.; Kuriyama, A. Polym. J. 1985, 17, 97.
10. (a) Mardare, D.; Matyjaszewski, K. Macromol. Rapid Commun. 1994, 15, 37.
11. (b) Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638.
12. (c) Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 645.
13. (d) Wayland, B. B.; Poezmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943.
14. (a) Moad, G.; Solomon, D. H.; Johns, S. R.; Willing, R. I. Macromolecules 1982, 15, 909.
15. (b) Solomon, D. H.; Rizzardo, E.; Cacioli, P. U.S. Patent 4,581,429, March 27, 1985.
16. (c) Rizzardo, E. Chem. Aust. 1987, 54, 32.
17. (d) Druliner, J. D. Macromolecules 1991, 24, 6079.
18. (e) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
19. (f) Veregin, R. P. N.; Georges, M. K.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 5316.
20. (g) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185.
21. (h) Hawker, C. j.; Hedrick, J. L. Macromolecules 1995, 28, 2993.
22. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
23. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
24. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
25. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
26. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
27. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
28. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
29. Examples for radical-promoted cationic polymerizations: (a) Bottcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289. (b) Sundell, P.-E.; Jönsson, S.; Hult, A. J. Polym. Sci., Part A: Polym. Chem. 1991, 29, 1525. (c) Timpe, H.-J.; Rajendran, A. G. Eur. Polym. J. 1991, 27, 77. (d) Yagci, Y.; Borbely, J.; Schnabel, W. Eur. Polym. J. 1989, 25, 129. (e) Timpe, H.-J. Pure Appl. Chem. 1988, 60, 1033. (f) Ledwith, A. Makromol. Chem., Suppl. 1979, 3, 348. (g) Ledwith, A. Polymer 1978, 19, 1217. (h) Abdul-Rasoul, F. A. M.; Ledwith, A.; Yagci, Y. Polymer 1978, 19, 1219.
30. Pappas, S. P.; Pappas, B. C.; Gatechair, L. R. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 77. (j) Pappas, S. P.; Jilek, J. H. Photogr. Sci. Eng. 1979, 23, 140. (k) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977. (l) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 2441. (m) Crivello, J. V.; Lam, J. H. W. Macromolecules 1977, 10, 1307.
31. Pappas, S. P.; Pappas, B. C.; Gatechair, L. R. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 77. (j) Pappas, S. P.; Jilek, J. H. Photogr. Sci. Eng. 1979, 23, 140. (k) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977. (l) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 2441. (m) Crivello, J. V.; Lam, J. H. W. Macromolecules 1977, 10, 1307.
32. Pappas, S. P.; Pappas, B. C.; Gatechair, L. R. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 77. (j) Pappas, S. P.; Jilek, J. H. Photogr. Sci. Eng. 1979, 23, 140. (k) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977. (l) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 2441. (m) Crivello, J. V.; Lam, J. H. W. Macromolecules 1977, 10, 1307.
33. Pappas, S. P.; Pappas, B. C.; Gatechair, L. R. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 77. (j) Pappas, S. P.; Jilek, J. H. Photogr. Sci. Eng. 1979, 23, 140. (k) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977. (l) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 2441. (m) Crivello, J. V.; Lam, J. H. W. Macromolecules 1977, 10, 1307.
34. Pappas, S. P.; Pappas, B. C.; Gatechair, L. R. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 77. (j) Pappas, S. P.; Jilek, J. H. Photogr. Sci. Eng. 1979, 23, 140. (k) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977. (l) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1978, 16, 2441. (m) Crivello, J. V.; Lam, J. H. W. Macromolecules 1977, 10, 1307.
35. (a) Kuwae, Y.; Kamachi, M. Bull. Chem. Soc. Jpn. 1989, 62, 2474.
36. (b) Kuwae, Y.; Kamachi, M. Bull. Chem. Soc. Jpn. 1986, 59, 2325.
37. Schepple, S. E.; Seltzer, S. J. Am. Chem. Soc. 1968, 90, 358.
38. Benaring, E. Ann. Chem. 1960, 631, 1.
39. ( 13) Crivello, J. V.; Lam, J. H. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 977.
40. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergaonn Press: New York, 1988.
41. (a) Kotaka, T.; Uda, T.; Tanaka, T.; Inagaki, H. Makromol. Chem. 1975, 176, 1273.
42. (b) Inagaki, H. Thin-Layer Chromatography. In Fractionation of Synthetic Polymers; Tung, L. H. Ed.; Marcel Dekker: New York, 1977.
43. Kennedy, J. P.; Marechal, E. Corbocationic Polymerization; John-Wiley: New York, 1982.
44. Battcher, A.; Hasebe, K.; Hizal, G.; Stelberg, P.; Yagci, Y.; Schnabel, W. Polymer 1991, 32, 2289.
45. Brandrup, J.; Immergut, E. H. Polymer Handbook, 3rd ed.; Wiley Interscience: New York, 1989; Chapter VIII.
46. Dawkins, J. V. Characterization and Solution Properties of Block Copolymers. In Block Copolymers; Allpor, D. C., Janes, W. H. Eds.; Applied Science Publishers Ltd.: London, 1973; p 546.