Exchange of substituents between (macro)alkoxyamines and (macro)RAFT agents (ESARA): A bridge between nitroxide-mediated and RAFT controlled radical polymerization techniques

Macromolecules

Volumn 42, Issue 16, 2009, Pages 5953-5964

  Favier, Arnaud ^a,b   Luneau, Benoit ^a   Vinas, Jérôme ^a   Laissaoui, Nasrine ^a   Gigmes, Didier ^a   Bertin, Denis ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

^b Vifor (International) Inc   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYAMINES; CONTROL AGENT; CONTROLLED RADICAL POLYMERIZATION; EXPERIMENTAL CONDITIONS; LOW MOLECULAR WEIGHT COMPOUNDS; MACRO-RAFT AGENT; NEW TOOLS; NITROXIDE MEDIATED POLYMERIZATION; NITROXIDES; POLYMER ARCHITECTURE; POLYMER DESIGNS; PROOF OF CONCEPT; RADICAL PROCESS; RAFT AGENTS; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION;

AMINES; ATOM TRANSFER RADICAL POLYMERIZATION; BLOCK COPOLYMERS; FREE RADICAL POLYMERIZATION;

POLYMERS;

EID: 68949171914     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9006939     Document Type: Article

References (41)

1. Advances in Controlled/Living Radical Polymerization; Matyjaszewski, K., Ed; American Chemical Society, ACS Symposium Series 854: Washington, DC, 2003.
2. Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3745.
3. Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
4. Solomon, D. H.; Rizzardo, E.; Cacioli, P. US 4,581,429, 1986.
5. Hawker, C. J.; Bosnian, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
6. Fischer, H. Chem. Rev. 2001, 101, 3581-3610.
7. Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. WO 98/01478, 1998.
8. Corpart, P.; Charmot, D.; Biadatti, T.; Zard, S. Z.; Michelet, D. WO 98/58974, 1998.
9. Moad, G.; Rizzardo, E.; Thang, S. H. Aust, J. Chem. 2005, 58, 379-410.
10. Wager, C.; Haddleton, D. M.; Bon, S. A. F. Eur. Polym, J. 2004, 40, 641-645.
11. Venkatesh, R.; Yajjou, L.; Koning, C. E.; Klumperman, B. Macromol. Chem. Phys. 2004, 205, 2161-2168.
12. Shi, Y.; Fu, Z.; Yang, W. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2069-2075.
13. Li, C.; Shi, Y.; Fu, Z. Polym. Int. 2006, 55, 25-30.
14. Wang, S.; Cheng, Z.; Zhu, J.; Zhang, Z.; Zhu, X. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 5318-5328.
15. Bernaerts, K. V.; Du Prez, F. E. Prog. Polym. Sci. 2006, 31, 671-722.
16. Beyou, E.; Chaumont, P.; Chauvin, F.; Devaux, C.; Zydowicz, N. Macromolecules 1998, 31, 6828-6835.
17. Perrier, S.; Takolpuckdee, P.; Mars, C. A. Macromolecules 2005, 58, 2033-2036.
18. Ao, Y.; He, J.; Han, X.; Liu, Y.; Wang, X.; Fan, D.; Xu, J.; Yang, Y. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 374-387.
19. Vinas, J.; Chagneux, N.; Gigmes, D.; Trimaille, T.; Favier, A.; Bertin, D. Polymer 2008, 49, 3639-3647.
20. Favier, A.; Charreyre, M.-T.; Chaumont, P.; Pichot, C. Macromolecules 2002, 55, 8271-8280.
21. Chauvin, F.; Dufils, P. E.; Gigmes, D.; Guillaneuf, Y.; Marque, S. R. A.; Tordo, P.; Bertin, D. Macromolecules 2006, 39, 5238-5250.
22. Barner-Kowollik, C.; Quinn, J. F.; Morsley, D. R.; Davis, T. P. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1353-1365.
23. (a) Le Mercier, C.; Acerbis, S.; Bertin, D.; Chauvin, F.; Gigmes, D.; Guerret, O.; Lansalot, M.; Marque, S.; Le Moigne, F.; Fischer, H.; Tordo, P. Macromol. Symp. 2002, 182, 225-247.
24. (b) Benoit, D.; Grimaldi, S.; Robin, S.; Finet, J.-P.; Tordo, P.; Gnanou, Y. J. Am. Chem. Soc. 2000, 122, 5929-5939.
25. (c) Diaz, T.; Fischer, A.; Jonquieres, A.; Brembilla, A.; Lochon, P. Macromolecules 2003, 36, 2235-2241.
26. (d) Schierholz, K.; Givehchi, M.; Fabre, P.; Nallet, F.; Papon, E.; Guerret, O.; Gnanou, Y. Macromolecules 2003, 36, 5995-5999.
27. (e) Couvreur, L.; Lefay, C.; Belleney, J.; Charleux, B.; Guerret, O.; Magnet, S. Macromolecules 2003, 36, 8260-8267.
28. (f) Nicolas, J.; Charleux, B.; Guerret, O.; Magnet, S. Macromolecules 2004, 37, 4453-4463.
29. (g) Nicolas, J.; Dire, C.; Mueller, L.; Belleney, J.; Charleux, B.; Marque, S. R. A.; Bertin, D.; Magnet, S.; Couvreur, L. Macromolecules 2006, 39, 8274-8282.
30. (h) Phan, T. N. T.; Bertin, D. Macromolecules 2008, 41, 1886-1895.
31. Guillaneuf, Y.; Gigmes, D.; Marque, S. R. A.; Astolfi, P.; Greci, L.; Tordo, P.; Bertin, D. Macromolecules 2007, 40, 3108-3114.
32. Favier, A.; Charreyre, M.-T. Macromol. Rapid Commun. 2006, 27, 653-692.
33. Bertin, D.; Gigmes, D.; Marque, S. R. A.; Tordo, P. Macromolecules 2005, 38, 2638-2650.
34. Lai, J. T.; Filla, D.; Shea, R. Macromolecules 2002, 35, 6754.
35. Bathfield, M.; D'Agosto, F.; Spitz, R.; Charreyre, M.-T.; Delair, T. J. Am. Chem. Soc. 2006, 128, 2546-2547.
36. For this macromolecular application, it should be noted that since the concentration of chain-ends in polymer samples is generally low, the reacting alkoxyamines or RAFT agents could be used in large excess to optimize the functionalization yield without any prohibitive added cost. In addition, this excess can also be recovered and "recycled" after isolation of the polymer.
37. 1H NMR could not be used for the quantification of the dithiobenzoate chain-ends and thus for the determination a number average MW since the peaks corresponding to the dithiobenzoate chain-ends overlapped the broad peaks of PS (7-8 ppm).
38. Skvortsov, A. M.; Gorbunov, A. A. Polym. Sci, U.S.S.R. 1980, 22, 2893-2902.
39. Petit, C.; Luneau, B.; Beaudoin, E.; Gigmes, D.; Bertin, D. J. Chromatogr. A 2007, 1163, 128-137.
40. 34 to (i) irreversibly terminated chains via combination, (ii) intermediate radicals, or (iii) irreversible termination products of IR - did appear on the UV chromatograms of the starting PS-DB. It means that at least part of these chains contains a chromophore absorbing at λ-304 nm, unlike terminated PS chains. In addition, it seemed that the former lost their chromophore upon reaction with MAMA - SGI.
41. Favier, A.; Charreyre, M.-T.; Pichot, C. Polymer 2004, 45, 8661-8674.