Anionic polymerization of alkyl (meth)acrylates using metal-free initiators: Effect of ion pairing on initiation equilibria

Macromolecules

Volumn 32, Issue 9, 1999, Pages 2865-2871

  Baskaran, D ^a   Chakrapani, S ^a   Sivaram, S ^a   Hogen Esch, Thieo E ^b   Müller, Axel H E ^c  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; ANIONIC POLYMERIZATION; INITIATORS (CHEMICAL); MOLECULAR WEIGHT DISTRIBUTION; REACTION KINETICS; SALTS;

DIETHYLPHENYLMALONATE; ETHYLFLUORENE; FLUORENE; TETRABUTYLAMMONIUM; TETRAHYDROFURAN;

POLYMETHYL METHACRYLATES;

EID: 0032653513     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma981638m     Document Type: Article

References (66)

1. (a) Glusker, D. L.; Galluccis, R. A.; Evans, R. A. J. Am. Chem. Soc. 1964, 86, 187.
2. (b) Schreiber, H. Makromol. Chem. 1956, 36, 86.
3. (c) Kawabata, N.; Tsuruta, T. Makromol. Chem. 1985, 86, 231.
4. (d) Fait, B. A. Eur. Polym. J. 1967, 3, 523.
5. Webster, O. W.; Hertler, W. R.; Sogah, D. Y.; Farnham, W. B.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 105, 5706.
6. Reetz, M. T.; Ostarek, R. J. J. Chem. Soc., Chem. Commun. 1988, 213.
7. (b) Reetz, M. T. Angew. Chem. 1988, 100, 1026.
8. (c) Reetz, M. T.; Hutte, S.; Goddard, R.; Minet, U. J. Chem. Soc., Chem. Commun. 1995, 275.
9. (d) Reetz, M. T.; Hutte, S.; Goddard, R. Z. Naturforsck. 1995, 415.
10. (e) Broska, D.; Fieberg, A.; Heibel, C.; Bandermann, F. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997, 38 (1), 471.
11. (f) Zagala, A. P.; Hogen-Esch, T. E. Macromolecules 1996, 29, 3038.
12. (g) Baskaran, D.; Müller, A. H. E. Macromolecules 1997, 30, 1869.
13. (h) Baskaran, D.; Müller, A. H. E.; Kolshorn, H.; Zagala, A. P.; Hogen-Esch, T. E. Macromolecules 1997, 30, 6695.
14. (i) Zagala, A. P.; Dimov, D.; Hogen-Each, T. E. Makromol. Chem. Macromol. Symp., in press.
15. (j) Zagala, A. P. Dissertation, University of Southern California, 1996.
16. (a) Varshney, S. K.; Jerome, R.; Bayard, P.; Jacobs, C.; Fayt, R.; Teyssie, Ph. Macromolecules 1992, 25, 4457.
17. (b) Johann, C.; Müller, A. H. E. Makromol. Chem., Rapid Commun. 1981, 2, 687.
18. (c) Lochmann, L.; Kolarik, J.; Doskocilova, D.; Vozka, S.; Trekoval, J. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 1727.
19. (d) Lochmann, L.; Trekoval, J. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 1727.
20. (e) Wang, J. S.; Jerome, R.; Bayard, Ph.; Patin, M.; Teyssie, Ph.; Vuillemin, B.; Heim, Ph. Macromolecules 1994, 27, 4635.
21. (f) Wang, J. S.; Bayard, Ph.; Jerome, R.; Varshney, S. K.; Teyssie, Ph. Macromolecules 1994, 27, 4890.
22. (g) Baskaran, D.; Chakrapani, S.; Sivaram, S. Macromolecules 1995, 25, 7315.
23. (h) Baskaran, D.; Sivaram, S. Macromolecules 1997, 30, 1550.
24. (a) Yasuda, H.; Yamamota, H.; Yamashita, M.; Yokata, K.; Nakamura, A.; Miyake, S.; Kai, Y.; Kanehisa, N. Macromolecules 1993, 26, 7134.
25. (b) Yasuda, H.; Yamamoto, H.; Yokota, K.; Miyake, S.; Nakamura, A. J. Am. Chem. Soc. 1992, 114, 4908.
26. (a) Kitayama, T.; Shinozaki, T.; Sakamoto, T.; Yamamoto, M.; Hatada, K. Makromol. Chem., Suppl. 1989, 167, 15.
27. (b) Ballard, D. G. H.; Bowlers, R. J.; Haddleton, D. M.; Richards, S. N.; Sellens, R.; Twose, D. L. Macromolecules 1992, 25, 5907.
28. (c) Schlaad, H.; Schmitt, B.; Mueller, A. H. E., Angew. Chem., Int. Ed. Engl. 1998, 37, 1289.
29. (a) Sivaram, S.; Dhal, P. K.; Kashikar, S. P.; Khisti, R. S.; Shinde, B. M.; Baskaran, D. Macromolecules 1991, 24, 1698; Polym. Bull. 1991, 25, 77.
30. (a) Sivaram, S.; Dhal, P. K.; Kashikar, S. P.; Khisti, R. S.; Shinde, B. M.; Baskaran, D. Macromolecules 1991, 24, 1698; Polym. Bull. 1991, 25, 77.
31. (b) Raj, D. J. A.; Wadgaonkar, P. P.; Sivaram, S. Macromolecules 1992, 25, 2774.
32. (c) Baskaran, D.; Chakrapani, S.; Sivaram, S. Proc. APME 1995, 31.
33. (d) Bandermann, F.; Beckelmann, D.; Broska, D.; Fieberg, A.; Roloff, T.; Wolters, D. Macromol. Chem. Phys. 1995, 196, 2335.
34. (e) Broska, D.; Fieberg, A.; Bandermann, F. Des. Monom. Polym. 1998, 1, 37.
35. (f) Pietzonka, T.; Seebach, D. Angew. Chem. 1993, 105 (5), 741.
36. (g) Börner, H. G.; Heitz, W. Macromol. Chem. Phys. 1998, 199, 1815.
37. Janata, M.; Müller, A. H. E., unpublished results.
38. Reetz, M. T.; Hutte, S.; Goddard, R. J. Phys. Org. Chem. 1995, 8, 231.
39. (a) Warzelhan, V.; Höcker, H.; Schulz, G. V. Makromol. Chem. 1978, 179, 2221.
40. (b) Lassalle, D.; Boileau, S.; Sigwalt, P. Eur. Polym. J. 1977, 13, 591.
41. (a) Quirk, R. P.; Bidinger, G. P. Polym. Bull. 1989, 22, 63.
42. (b) Quirk, R. P.; Kim, J. S. J. Phys. Org. Chem. 1995, 8, 242.
43. n values are only approximate and should be considered with limitation.
44. (a) Müller, A. H. E. Dissertation, University of Mainz, 1976.
45. (b) Glusker, D. L.; Lyslofe, I.; Stiles, E. J. Polym. Sci. 1961, 49, 315.
46. (c) Gerner, F. J.; Hocker, H.; Müller, A. H. E.; Schulz, G. V. Eur. Polym. J. 1984, 20 (4), 439.
47. (d) Müller, A. H. E.; Warzelhan, V.; Höcker, H.; Löhr, G.; Schulz, G. V. Prepr., IUPAC Int. Symp. on Macromol., Dublin 1977, 31.
48. (e) Königsmann, H.; Müller, A. H. E. Manuscript in preparation.
49. (f) Fieberg, A.; Broska, D.; Feibel, C.; Bandermann, F. Des. Monom. Polym. 1998, 1, 285.
50. (a) Kantlehner, W.; Haug, E.; Mergen, W. W.; Speh, P.; Maier, T.; Kapassakalidis, Brauner, H. J. Synthesis 1983, 904.
51. (b) Fujisawa, T.; Tajima, K.; Sato, T. Bull. Chem. Soc. Jpn. 1983, 56, 3529.
52. The cation exchange reaction carried out at 30°C resulted in an immediate disappearance of initiator color, 3a (maroon) and 3b (wine red), whereas at -40°C, the intensity of the initiator color did not change in both the cases.
53. Similar results were obtained in the polymerization of n-BA using tetrabutylammonium salts of diethylmalonate (1b), carbozole, and triphenylmethane at 0°C (Baskaran, D.; Sivaram, S., unpublished results).
54. (a) Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1981, 46, 4327.
55. (b) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
56. Baskaran, D.; Müller, A. H. E. Manuscript under preparation.
57. (a) Lochmann, L.; Trekoval, J.; Müller, A. H. E. Makromol. Chem. 1984, 185, 1819.
58. (b) Müller, A. H. E.; Lochmann, L.; Trekoval, J. Makromol. Chem. 1986, 187, 1473.
59. (a) Chang, C. J.; Hogen-Esch, T. E. Tetrahedron Lett. 1976, 323.
60. (b) Hogen-Esch, T. E. J. Phys. Inorg. Chem. 1977, 153.
61. (a) Johann, C.; Müller, A. H. E. Makromol. Chem., Rapid Commun. 1981, 2, 687.
62. (b) Hogen-Esch, T. E.; Smid, J. J. Am. Chem. Soc. 1966, 88, 318.
63. (a) Figueruelo, J. E. Makromol. Chem. 1970, 131; 63.
64. (b) Löhr, G.; Schulz, G. V. Makromol. Chem. 1973, 172, 137.
65. Fuoss, R. M. J. Am. Chem. Soc. 1958, 80, 5059.
66. Kunkel, D.; Müller, A. H. E.; Janata, M.; Lochmann, L. Makromol. Chem., Macromol. Symp. 1992, 60, 315.