ω-Pentandecalactone polymerization and ω-pentadecalactone/ Îμ -caprolactone copolymerization reactions using organic catalysts

Macromolecules

Volumn 45, Issue 8, 2012, Pages 3356-3366

  Bouyahyi, Miloud ^a   Pepels, Mark P F ^a   Heise, Andreas ^b   Duchateau, Rob ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b DUBLIN CITY UNIVERSITY   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,5 ,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE; ACTIVE CATALYST; BENZYL ALCOHOL; BINARY SYSTEMS; CAPROLACTONE; CATALYTIC BEHAVIOR; COMONOMER CONTENT; COPOLYMERIZATION REACTIONS; EXPERIMENTAL CONDITIONS; FEED COMPOSITIONS; KINETIC STUDY; LINEAR RELATION; MONOMER CONCENTRATION; N-HETEROCYCLIC; N-HETEROCYCLIC CARBENES; ORGANIC CATALYSTS; PENTADECALACTONE; POLYMERIZATION MECHANISMS; POLYMERIZATION REACTION; RANDOM COPOLYMER; TOLUENE SOLUTION;

CATALYSTS; COPOLYMERS; KINETIC THEORY; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; THERMOANALYSIS; TOLUENE;

COPOLYMERIZATION;

EID: 84860213488     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma3001675     Document Type: Article

References (50)

1. Vert, M.; Li, S.; Spenlehauer, G.; Guerin, P. J. Mater. Sci.: Mater. Med. 1992, 3, 432
2. Chiellini, E.; Sunamoto, J.; Migliaresi, C.; Ottenbrite, R. M.; Cohn, D., Eds.; Biomedical Polymers and Polymer Therapeutics; University of Pisa: Pisa, Italy, 2002.
3. Vert, M. Angew. Makromol. Chem. 1989, 166, 155
4. Carothers, W. H.; Dorough, G. L. J. Am. Chem. Soc. 1930, 52, 711
5. Ishihara, K.; Ohara, S.; Yamamoto, H. Science 2000, 290, 1140
6. Takasu, A.; Makino, T.; Yamada, S. Macromolecules 2010, 43, 144
7. Liu, C.; Liu, F.; Cai, J.; Xie, W.; Long, E. T.; Turner, S. R.; Lyons, A.; Gross, R. A. Biomacromolecules 2011, 12, 3291
8. Dubois, P.; Coulembier, O.; Raquez, J.-M. Handbook of Ring-Opening Polymerization; Wiley-VCH: Weinheim, 2009.
9. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147
10. Dove, A. P. Chem. Commun. 2008, 6446
11. Labet, M.; Thielemans, W. Chem. Soc. Rev. 2009, 38, 3484
12. Albertsson, A.-C.; Varma, K. I. Biomacromolecules 2003, 4, 1466
13. Nakayama, Y.; Watanabe, N.; Kusaba, K.; Sasaki, K.; Cai, Z.; Shiono, T.; Tsutsumi, C. J. Appl. Polym. Sci. 2011, 121, 2098
14. Wang, Y.; Kuniko, M. Macromol. Symp. 2005, 224, 193
15. van der Mee, L.; Helmich, F.; de Bruijn, R.; Vekemans, J. A. J. M.; Palmans, A. R. A.; Meijer, E. W. Macromolecules 2006, 39, 5021
16. Namekawa, S.; Suda, S.; Uyama, H.; Kobayashi, S. Int. J. Biol. Macromol. 1999, 25, 145
17. Bisht, K. S.; Henderson, L. A.; Gross, R. A. Macromolecules 1997, 30, 2705
18. Focarete, M. L.; Scandola, M.; Kumar, A.; Gross, R. A. J. Polym. Sci., Part B: Polym. Phys. 2001, 39, 1721
19. de Geus, M.; van der Meulen, I.; Goderis, B.; van Hecke, K.; Dorschu, M.; van der Werff, H.; Koning, C. E.; Heise, A. Polym. Chem. 2010, 1, 525
20. van der Meulen, I.; Geus, M. D.; Antheunis, H.; Deumens, R.; Joosten, E. A. J.; Koning, C. E.; Heise, A. Biomacromolecules 2008, 9, 3404
21. Ceccorulli, G.; Scandola, M.; Kumar, A.; Kalra, B.; Gross, R. A. Biomacromolecules 2005, 6, 902
22. Kumar, A.; Kalra, B.; Dekhterman, A.; Gross, R. A. Macromolecules 2000, 33, 6303
23. Wu, J.; Yu, T.-L.; Chen, C.-T.; Lin, C.-C. Coord. Chem. Rev. 2006, 250, 602
24. O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215
25. Wheaton, C. A.; Hayes, P. G.; Ireland, B. J. Dalton Trans. 2009, 4832
26. Ajellal, N.; Carpentier, J.-F.; Guillaume, C.; Guillaume, M. S.; Helou, M.; Poirier, V.; Sarazin, Y.; Trifonov, A. Dalton Trans. 2010, 39, 8363
27. Lebedev, B.; Yevstropov, A. Makromol. Chem. 1984, 185, 1235
28. Zhong, Z.; Dijkstra, P. J.; Feijen, J. Macromol. Chem. Phys. 2000, 201, 1329
29. Jedliriski, Z.; Juzwa, M.; Adarnus, G.; Kowalczuk, M. Macromol. Chem. Phys. 1996, 197, 2923
30. Van der Meulen, I.; Gubbels, E.; Huijser, S.; Sablong, R.; Koning, C. E.; Heise, A.; Duchateau, R. Macromolecules 2011, 44, 4301
31. Chuma, A.; Horn, H. W.; Swope, W. C.; Pratt, R. C.; Zhang, L.; Lohmeijer, B. G. G.; Wade, C. G.; Waymouth, R. M.; Hedrick, J. L.; Rice, J. E. J. Am. Chem. Soc. 2008, 130, 6749
32. Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2006, 128, 4556
33. Dove, A. P. R; Pratt, C.; Lohmeijer, B. G. G.; Culkin, D. A.; Hagberg, E. C.; Nyce, G. W.; Waymouth, R. M.; Hedrick, J. L. Polymer 2006, 47, 4018
34. Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813
35. Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2010, 43, 2093
36. Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M. Chem.- Eur. J. 2010, 16, 13805
37. Pratt, R. C.; Nederberg, F.; Waymouth, R. M.; Hedrick, J. L. Chem. Commun. 2008, 114
38. Strandman, S.; Gautrot, J. E.; Zhu, X. X. Polym. Chem. 2011, 2, 791
39. Duda, A.; Kowalski, A.; Penczek, S.; Uyama, H.; Kobayashi, S. Macromolecules 2002, 11, 4266
40. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 8574
41. This behavior is in agreement with the conclusions reported by previous reports, demonstrating that the efficiency of the ROP of Îμ -CL is sensitive to the steric nature of the carbene catalyst. For example, see: Nyce, G. W.; Glauser, T.; Connor, E. F.; Mock, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046
42. Schuchardt, U.; Vargas, R. M.; Gelbard, G. J. Mol. Catal. A: Chem. 1995, 99, 65
43. Allegra, G.; Bassi, I. W. Adv. Polym. Sci. 1969, 6, 549
44. Kamiya, N.; Sakurai, M.; Inoue, Y.; Chujo, R. Macromolecules 1991, 24, 3888
45. Coulembier, O.; Mespouille, L.; Hedrick, J. L.; Waymouth, R. M.; Dubois, P. Macromolecules 2006, 39, 4001
46. Kim, B. J.; White, J. L. J. Appl. Polym. Sci. 2003, 88, 1429
47. Huijser, S. Synthesis and characterization of biodegradable polyesters. PhD Thesis, Eindhoven, 2009.
48. Daswani, P.; Rheinhold, F.; Ottink, M.; Staal, B.; Van Herk, A. Eur. Polym. J. 2012, 48, 296
49. Kurzer, F.; Douraghi-Zadeh, K. Chem. Rev. 1967, 67, 107-152
50. Quast, H.; Ross, K.-H.; Philipp, G.; Hagedorn, M.; Hahn, H.; Banert, K. Eur. J. Org. Chem. 2009, 3940-3952