Emulsion and controlled miniemulsion polymerization of the renewable monomer γ-methyl-α-methylene-γ-butyrolactone

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 46, Issue 17, 2008, Pages 5929-5944

  Qi, Genggeng ^a   Nolan, Michael ^a   Schork, F Joseph ^b   Jones, Christopher W ^a  

^a Georgia Institute of Technology   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

Biomass; Copolymerization; Dispersed polymerization; Emulsion polymerization; Levulinic acid; Living polymerization; RAFT; Renewable chemical; Renewable resources

Indexed keywords

BIOMASS; DISPERSED POLYMERIZATION; LEVULINIC ACID; LIVING POLYMERIZATION; RAFT; RENEWABLE CHEMICAL; RENEWABLE RESOURCES;

ABS RESINS; ACRYLIC MONOMERS; ACRYLICS; CHEMICAL REACTIONS; COPOLYMERIZATION; EMULSIFICATION; EMULSION POLYMERIZATION; ESTERS; MONOMERS; NUCLEATION; POLYMERIZATION; POLYMERS; RATE CONSTANTS; STYRENE;

FREE RADICAL POLYMERIZATION;

EID: 51049116624     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.22909     Document Type: Article

References (84)

1. Hoffmann, H. M. R.; Rabe, J. Angew Chem Int Ed Engl 1985, 24, 94-110.
2. Grieco, P. A. Synth-Stuttg 1975, 2, 67-82.
3. Manzer, L. E. Appl Catal A 2004, 272, 249-256.
4. Stansbury, J. W.; Antonucci, J. M. Dent Mater 1992, 8, 270-273.
5. Park, B. K.; Nakagawa, M.; Hirota, A.; Nakayama, M. J Antibiot 1988, 41, 751-758.
6. Akkapeddi, M. K. Macromolecules 1979, 12, 546-551.
7. Pittman, C. U.; Lee, H. J Polym Sci Polym Chem 2003, 41, 1759-1777.
8. Trumbo, D. L. Polym Bull 1991, 26, 271-275.
9. Akkapeddi, M. K. Polymer 1979, 20, 1215-1216.
10. Lee, C.; Hall, H. K. Macromolecules 1989, 22, 21-25.
11. Koinuma, H.; Sato, K.; Hirai, H. Makromol Chem Rapid 1982, 3, 311-315.
12. Brandenburg, C.; Butler, E. P.; Erkenbrecher, C.; King, R.; Hutchins, C.; Puts, R. D. U.S. Patent 20,030,130,414, July 10, 2003.
13. Brandenburg, C.; Manzer, L.; Subramanian, P. WO 028529, March 31, 2005.
14. Brandenburg, C. J. WO 048220, Jun 12, 2003.
15. Okumura, A.; Muro, M.; Nakamura, K.; Hayashi, S.; Irie, K. JP 09236715, 1997.
16. Okimoto, Y.; Hatakeyama, H. JP 154,072, 2007.
17. Schwind, H.; Hauch, D.; Hasskerl, T.; Dorn, K.; Hoepp, M. DE 1 1,950,182, 1996.
18. Lemonidou, A. A.; Lopez, L.; Manzer, L. E.; Barteau, M. A. Appl Catal A 2004, 272, 241-248.
19. Suenaga, J.; Sutherlin, D. M.; Stille, J. K. Macromolecules 1984, 17, 2913-2916.
20. Brandenburg, C.; Dean, D. M.; Hofmann, G. H.; Puts, R. D.; Flexman, E. A.; Tarburton, K. R. EP Patent 1,297,069, 2003.
21. Brandenburg, C. J. U.S. Patent 230019, Jan 31, 2004.
22. Schork, F.; Luo, Y.; Smulders, W.; Russum, J.; Butte, A.; Fontenot, K. Polym Part 2005, 175: 129-255.
23. Otsu, T.; Yoshida, M. Makromol Chem-Rapid 1982, 3, 127-132.
24. Georges, M. K.; Moffat, K. A.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Polym Mater Sci Eng 1993, 69, 305.
25. Wang, J.; Matyjaszewski, K. J Am Chem Soc 1995, 117, 5614-5615.
26. Chiefari, J.; Chong, Y.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T.; Mayadunne, R.; Meijs, G.; Moad, C; Moad, G.; Rizzardo, E.; Thang, S. Macromolecules 1998, 31, 5559-5562.
27. Chong, Y. K.; Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1999, 32, 2071-2074.
28. Mitsukami, Y.; Donovan, M. S.; Lowe, A. B.; McCormick, C. L. Macromolecules 2001, 34, 2248-2256.
29. Cunningham, M. F. Prog Polym Sci 2002, 27, 1039-1067.
30. Biasutti, J. D.; Davis, T. P.; Lucien, F. P.; Heuts, J. P. A. J Polym Sci Part A: Polym Chem 2005, 43, 2001-2012.
31. Nguyen, T. L. U.; Eagles, K.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. J Polym Sci Part A: Polym Chem 2006, 44, 4372-4383.
32. Kanagasabapathy, S.; Claverie, J.; Uzulina, I. Polym Prepr 1999, 40, 1080-1081.
33. Monteiro, M. J.; De Barbeyrac, J. Macromolecules 2001, 34, 4416-4423.
34. Prescott, S. W.; Ballard, M. J.; Rizzardo, E.; Gilbert, R. G. Macromolecules 2002, 35, 5417-5425.
35. Ferguson, C. J.; Hughes, R. J.; Pham, B. T. T.; Hawkett, B. S.; Gilbert, R. G.; Serelis, A. K.; Such, C. H. Macromolecules 2002, 35, 9243-9245.
36. Smulders, W.; Monteiro, M. J. Macromolecules 2004, 37, 4474-4483.
37. Smulders, W.; Jones, C.; Schork, F. Macromolecules 2004, 37, 9345-9354.
38. Smulders, W. W.; Jones, C. W.; Schork, F. J. AIChE J 2005, 51, 1009-1021.
39. de Brouwer, H.; Tsavalas, J. G.; Schork, F. J.; Monteiro, M. J. Macromolecules 2000, 33, 92399246.
40. Butte, A.; Storti, G.; Morbidelli, M. Macromolecules 2001, 34, 5885-5896.
41. Tsavalas, J. G.; Schork, F. J.; de Brouwer, H.; Monteiro, M. J. Macromolecules 2001, 34, 3938-3946.
42. Lansalot, M.; Davis, T. P.; Heuts, J. P. A. Macromolecules 2002, 35, 7582-7591.
43. Russum, J. P.; Jones, C. W.; Schork, F. J. Macromol Rapid Commun 2004, 25, 1064-1068.
44. Russum, J. P.; Barbre, N. D.; Jones, C. W.; Schork, F. J. J Polym Sci Part A: Polym Chem 2005, 43, 2188-2193.
45. Qi, G.; Jones, C. W.; Schork, J. F. Ind Eng Chem Res 2006, 45, 7084-7089.
46. Qi, G. G.; Jones, C. W.; Schork, F. J. Macromol Rapid Commun 2007, 28, 1010-1016.
47. Russum, J. P.; Jones, C. W.; Schork, F. J. AIChE J 2006, 52, 1566-1576.
48. Russum, J. P.; Jones, C. W.; Schork, F. J. Ind Eng Chem Res 2005, 44, 2484-2493.
49. Luo, Y. W.; Cui, X. F. J Polym Sci Part A: Polym Chem 2006, 44, 2837-2847.
50. Barner-Kowollik, C.; Buback, M.; Charleux, B.; Coote, M. L.; Drache, M.; Fukuda, T.; Goto, A.; Klumperman, B.; Lowe, A. B.; McLeary, J. B.; Moad, G.; Monteiro, M. J.; Sanderson, R. D.; Tonge, M. P.; Vana, P. J Polym Sci Part A: Polym Chem 2006, 44, 5809-5831.
51. Guo, T. Y.; Tang, D.; Song, M.; Zhang, B. J Polym Sci Part A: Polym Chem 2007, 45, 5067-5075.
52. Luo, Y. W.; Liu, B.; Wang, Z. H.; Gao, J.; Li, B. G. J Polym Sci Part A: Polym Chem 2007, 45, 2304-2315.
53. Zhang, Q. H.; Zhan, X. L.; Chen, F. Q.; Shi, Y.; Wang, Q. Y. J Polym Sci Part A: Polym Chem 2007, 45, 1585-1594.
54. Bowes, A.; McLeary, J. B.; Sanderson, R. D. J Polym Sci Part A: Polym Chem 2007, 45, 588-604.
55. Yang, L.; Luo, Y.; Li, B. J Polym Sci Part A: Polym Chem 2006, 44, 2293-2306.
56. Chou, Y. J.; El-Aasser, M. S.; Vanderhoff, J. W. J Dispersion Sci Technol 1980, 1, 129-150.
57. Gilbert, R. G. Emulsion Polymerization: A Mechanistic Approach; Academic: London, 1995.
58. Landfester, K.; Antonietti, M. Macromol Rapid Commun 2000, 21, 820-824.
59. Quinn, J. F.; Rizzardo, E.; Davis, T. P. Chem Commun 2001, 1044-1045.
60. Miniemulsion homopolymerizations of MeMBL were prepared in a typical manner. However, analysis of the resulting polymerization suggested strongly that primarily homogeneous nucleation occurred, rather than droplet nucleation that would be expected for a true miniemulsion. For such polymerizations, we describe them as "mini-emulsions" using quotations, to denote the difference from our later copolymerization studies with styrene, where droplet nucleation appears to play a more significant role.
61. Wu, X. Q.; Schork, F. J. J Appl Polym Sci 2001, 81, 1691-1699.
62. Mouran, D.; Reimers, J.; Schork, F. J. J Polym Sci Part A: Polym Chem 1996, 34, 1073-1081.
63. Priest, W. J. J Phys Chem 1952, 56, 1077-1082.
64. Fitch, R. M.; Prenosil, M. B.; Sprick, K. J. J Polym Sci Polym Symp 1969, 95-118.
65. Arai, M.; Arai, K.; Saito, S. J Polym Sci Part A: Polym Chem 1979, 17, 3655-3665.
66. Cox, R. A.; Wilkinson, M. C.; Creasey, J. M.; Goodall, A. R.; Hearn, J. J Polym Sci Part A: Polym Chem 1977, 15, 2311-2319.
67. Song, Z. Q.; Poehlein, G. W. J Colloid Interface Sci 1989, 128, 501-510.
68. Chen, C. Y.; Piirma, I. J Polym Sci Part A: Polym Chem 1980, 18, 1979-1993.
69. Song, Z. Q.; Poehlein, G. W. J Polym Sci Part A: Polym Chem 1990, 28, 2359-2392.
70. Munro, D.; Goodall, A. R.; Wilkinson, M. C.; Rändle, K.; Hearn, J. J Colloid Interface Sci 1979, 68, 1-13.
71. Lovell, P. A.; El Aasser, M. S. Emulsion Polymerization and Emulsion Polymers; Wiley: Chichester, 1997.
72. Qi, G.; Schork, F. J. Langmuir 2006, 22, 9075-9078.
73. Luo, Y.; Tsavalas, J.; Schork, F. J. Macromolecules 2001, 34, 5501-5507.
74. Chong, Y.; Krstina, J.; Le, T.; Moad, G.; Postma, A.; Rizzardo, E.; Thang, S. Macromolecules 2003, 36, 2256-2272.
75. Chiefari, J.; Mayadunne, R.; Moad, C.; Moad, G.; Rizzardo, E.; Postma, A.; Skidmore, M.; Thang, S. Macromolecules 2003, 36, 2273-2283.
76. Zhou, G. C.; Harruna, II. Anal Chem 2007, 79, 2722-2727.
77. Geelen, P.; Klumperman, B. Macromolecules 2007, 40, 3914-3920.
78. Nomura, M.; Tobita, H.; Suzuki, K., Eds.; Polymeric Microspheres Science and Technology; Kyoto university press: Kyoto, 2007.
79. Luo, Y.; Wang, R.; Yang, L.; Yu, B.; Li, B.; Zhu, S. Macromolecules 2006, 39, 1328-1337.
80. Kelen, T.; Tudos, F. J. Macromol Sci Chem 1975, A9, 1-27.
81. Fineman, M.; Ross, S. D. J Polym Sci 1950, 5, 259-262.
82. Mahdavian, A. R.; Abdollahi, M.; Mokhtabad, L.; Bijanzadeh, H. R.; Ziaee, F. J Appl Polym Sci 2006, 101, 2062-2069.
83. Luo, Y. W.; Liu, X. Z. J Polym Sci Part A: Polym Chem 2004, 42, 6248-6258.
84. Moad, G.; Solomon, D. H. Chemistry of Radical Polymerization, 2nd ed.; Elsevier: Oxford, 2006.