Synthesis of polybutadiene-polylactide diblock copolymers using aluminum alkoxide macroinitiators. Kinetics and mechanism

Macromolecules

Volumn 33, Issue 20, 2000, Pages 7395-7403

  Wang, Yunbing ^a   Hillmyer, Marc A ^a  

^a University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; ALUMINUM COMPOUNDS; MOLECULAR WEIGHT DISTRIBUTION; POLYBUTADIENES; POLYMERIZATION; SYNTHESIS (CHEMICAL);

LACTIDE POLYMERIZATION; MACROINITIATORS; POLYLACTIDES;

BLOCK COPOLYMERS;

EID: 0034300484     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0007177     Document Type: Article

References (50)

1. Bates, F. S.; Fredrickson, G. H. Annu. Rev. Phys. Chem. 1990, 41, 525-557.
2. Hsieh, H. L.; Quirk, R. P. Anionic Polymerization, Principles and Practical Applications; Marcel Dekker: New York, 1997; p 307.
3. See: Controlled Polymer Synthesis by Cationic Polymerization. Sawamoto, M. In Matyjaszewski, K., Ed.; Cationic Polymerization; Marcel Dekker: New York, 1996; p 381.
4. For a recent example see: Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627-1628.
5. Risse, W.; Grubbs, R. H. Macromolecules 1989, 22, 1558-1562.
6. Syntheis of Block Copolymers by Transformation Reactions. Schué, F. In Allen, G., Bevington, J. C., Eds.; Comprehensive Polymer Science; Pergamon: Oxford, 1989; Vol. 6, p 359.
7. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
8. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
9. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
10. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
11. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
12. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
13. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
14. Acar, M. H.; Matyjaszewski, K. Macromol. Chem. Phys. 1999, 200, 1094-1100. Matyjaszewski, K. Macromol. Symp. 1998, 132, 85-101. Kajiwara, A.; Matyjaszewski, K. Macromolecules 1998, 31, 3489-3493. Coca, S.; Paik, H. J.; Matyjaszewski, K. Macromolecules 1997, 30, 6513-6516. Yoshida, E.; Sugita, A. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 2059-2068. Neubauer, A.; Poser, S.; Arnold, M. J. Macromol. Sci., Pure Appl. Chem. 1997, A34, 1715-1725. Nomura, R.; Narita, M.; Endo, T. Macromolecules 1996, 29, 3669-3673. Nomura, R.; Endo, T. Macromolecules 1995, 28, 1754-1757.
15. Mecerreyes, D.; Moineau, G.; Dubois, P.; Jerome, R.; Hedrick, J. L.; Hawker, C. J.; Malmstrom, E. E.; Trollsas, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1274-1276. Weimer, M. W.; Scherman, O. A.; Sogah, D. Y. Macromolecules 1998, 31, 8425-8428.
16. Mecerreyes, D.; Moineau, G.; Dubois, P.; Jerome, R.; Hedrick, J. L.; Hawker, C. J.; Malmstrom, E. E.; Trollsas, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1274-1276. Weimer, M. W.; Scherman, O. A.; Sogah, D. Y. Macromolecules 1998, 31, 8425-8428.
17. Schmidt, S. C.; Hillmyer, M. A. Macromolecules 1999, 32, 4794.
18. For related rubber modified block copolymers containing a polylactone segment other than PLA see: Hsieh, H. L.; Wang, W. ACS Symp. Ser. 1985, 286, 161.
19. For a recent example see: Kurcok, P.; Dubois, P.; Sikorska, W.; Jedlinski, Z.; Jérôme, R. Macromolecules 1997, 50, 5591-5595.
20. For an application in polymerizations see: Kricheldorf, H. R.; Kreiser-Saunders, I. Polymer 1994, 35, 4175-4180. Carter, K. R.; Richter, R.; Kricheldorf, H. R.; Hedrick, J. L. Macromolecules 1997, 30, 6074-6076.
21. For an application in polymerizations see: Kricheldorf, H. R.; Kreiser-Saunders, I. Polymer 1994, 35, 4175-4180. Carter, K. R.; Richter, R.; Kricheldorf, H. R.; Hedrick, J. L. Macromolecules 1997, 30, 6074-6076.
22. Ropson, N.; Dubois, P.; Jérôme, R.; Teyssie, P. Macromolecules 1995, 28, 7589-7598.
23. Kowalski, A.; Duda, A.; Penczek, S. Macromolecules 1998, 31, 2114-2122.
24. Dubois, P.; Jacobs, C.; Jérôme, R.; Teyssie, P. Macromolecules 1991, 24, 2266.
25. Mark, J. E., Ed.; Physical Properties of Polymers Handbook; American Institute of Physics: New York, 1996; Chapter 12, p 153.
26. Gilman, H.; Cartledge, F. K. J. Organomet. Chem. 1964, 2, 447.
27. Pangborn, A. B.; Giardello, A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
28. Hillmyer, M. A.; Bates, F. S. Macromolecules 1996, 29, 6994.
29. Allgaier, J.; Poppe, A.; Willner, L.; Richter, D. Macromolecules 1997, 30, 1582-1586.
30. Morton, M.; Fetters, L. J.; Inomata, J.; Rubio, D. C.; Young, R. N. Rubber Chem. Technol. 1976, 49, 303.
31. Quirk, R. P.; Ma, J.-J. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 2031.
32. Dubois, Ph.; Jérôme, R.; Teyssié, Ph. Polym. Bull. 1989, 22, 475.
33. Degee, P.; Dubois, P.; Jerome, R. Macromol. Chem. Phys. 1997, 198, 1973-1984.
34. Duda, A. Macromolecules 1996, 29, 1399.
35. 0 investigated by SEC.
36. Duda, A.; Penczek, S. Macromolecules 1990, 23, 1636-1639.
37. Penczek, S.; Duda, A.; Szymanski, R. Macromol. Symp. 1998, 132, 441.
38. Jacobs, C.; Dubis, Ph.; Jérôme, R.; Tessié, Ph. Macromolecules 1991, 24, 3027.
39. Kricheldorf, H.; Kreiser-Saunders, I. Polymer 1994, 35, 4175.
40. Barakat, I.; Dobois, Ph.; Jérôme, R.; Tessié, Ph. J. Polym. Sci., Polym. Chem. 1993, 31, 505.
41. For a recent discussion of ceiling temperatures and equilibrium monomer concentrations, see: Ishizone, T.; Ohnuma, K.; Okazawa, Y.; Hirao, A.; Nakahama, S. Macromolecules 1998, 31, 2797.
42. This induction period has been observed before in aluminum alkoxide-initiated polymerizations of lactide. See ref 15. In our experiments, the induction period may be related to the low solubility of L in toluene at low temperatures (i.e., during the heating period).
43. Duda, A.; Penczek, S. Macromolecules 1995, 28, 5981.
44. Duda, A.; Penczek, S. Makromol. Chem., Macromol. Symp. 1991, 47, 127.
45. Duda, A.; Penczek, S. Makromol. Rapid Commun. 1994, 15, 559.
46. Eguiburu, J. L.; Fernandez-Berridi, M. J.; Cossio, F. P.; San Román, J. Macromolecules 1999, 32, 8252.
47. We also expect a higher degree of aggregation in toluene than in a coordinating solvent such as THF.
48. Wang, Y.; Hillmyer, M. A., unpublished results.
49. About 80% of the third ethyl groups were converted into aluminum alkoxides at ξ = 3 after 1 h at room temperature. The addition of L resulted in the conversion of the remaining ethyl groups to aluminum alkoxide species.
50. Fast reversible deactivation by aggregation of active centers is a necessary requirement for the kinetic analysis given in eq 7 (rapid preequilibrium).