Controlled radical polymerization of styrene mediated by the C-phenyl-N-tert-butylnitrone/AIBN pair: Kinetics and electron spin resonance analysis

Sciannamea, Valérie; Catala, Jean-Marie; Jérôme, Robert; Detrembleur, Christophe

doi:10.1002/pola.21889

Article (Scientific journals)

Controlled radical polymerization of styrene mediated by the C-phenyl-N-tert-butylnitrone/AIBN pair: Kinetics and electron spin resonance analysis

Sciannamea, Valérie; Catala, Jean-Marie; Jérôme, Robert et al.

2007 • In Journal of Polymer Science. Part A, Polymer Chemistry, 45 (7), p. 1219-1235

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/4302

DOI
10.1002/pola.21889

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Sciannamea V 2007 JPS Polym Chem 1219.pdf

Publisher postprint (420.81 kB)

Request a copy

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

radical polymerization; nitroxide-mediated polymerization (NMP)

Abstract :

[en] Kinetics of the free radical polymerization of styrene at 110 degrees C has been investigated in the presence of C-phenyl-N-tert-butylnitrone (PBN) and 2,2'-azobis(isobutyronitrile) (AIBN) after prereaction in toluene at 85 degrees C. The effect of the prereaction time and the PBN/AIBN molar ratio on the in situ formation of nitroxides and alkoxyamines (at 85 degrees C), and ultimately on the control of the styrene polymerization at 110 degrees C, has been investigated. As a rule, the styrene radical polymerization is controlled, and the mechanism is one of the classical nitroxide-mediated polymerization. Only one type of nitroxide (low-molecular-mass nitroxide) is formed whatever the prereaction conditions at 85 degrees C, and the equilibrium constant (K) between active and dormant species is 8.7 x 10(-10) mol L-1 at 110 degrees C. At this temperature, the dissociation rate constant (k(d)) is 3.7 x 10(-3) s(-1), the recombination rate constant (k(c)) is 4.3 x 10(6) L mol(-1) s(-1), whereas the activation energy (E-a,E-diss), for the dissociation of the alkoxyamine at the chain-end is similar to 125 kJ mol(-1). Importantly, the propagation rate at 110 degrees C, which does not change significantly with the prereaction time and the PBN/AIBN molar ratio at 85 degrees C, is higher than that for the thermal polymerization at 110 degrees C. This propagation rate directly depends on the equilibrium constant K and on the alkoxyamine and nitroxide concentrations, as well.

Research center :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Sciannamea, Valérie; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Catala, Jean-Marie; Institut Charles Sadron, Strasbourg, France

Jérôme, Robert ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Detrembleur, Christophe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Language :

English

Title :

Controlled radical polymerization of styrene mediated by the C-phenyl-N-tert-butylnitrone/AIBN pair: Kinetics and electron spin resonance analysis

Publication date :

01 April 2007

Journal title :

Journal of Polymer Science. Part A, Polymer Chemistry

ISSN :

0887-624X

eISSN :

1099-0518

Publisher :

Wiley, Hoboken, United States - New Jersey

Volume :

Issue :

Pages :

1219-1235

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://www3.interscience.wiley.com/cgi-bin/fulltext/114123153/PDFSTART

Funders :

BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture [BE]
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
CGRI - Commissariat Général aux Relations internationales
CNRS - Centre National de la Recherche Scientifique [FR]

Commentary :

The authors acknowledge Journal of Polymer Science Part A-Polymer Chemistry (Wiley) for allowing them to archive this paper.

Available on ORBi :

since 16 January 2009

Statistics

Number of views

98 (5 by ULiège)

Number of downloads

1 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

Bibliography

Webster, O. W. Science 1991, 251, 887.
Frechet, J.M.-J. Science 1994, 263, 1710.
Matyjaszewski, K. ACS Symposium Series, Vol. 685: Controlled Radical Polymerization; American Chemical Society: Washington, DC, 1998.
Matyjaszewski, K. ACS Symposium Series, Vol. 768: Controlled Radical Polymerization; American Chemical Society: Washington, DC, 2000.
Solomon, D. H.; Rizzardo, E.; Cacioli, P. U.S. Patent 4,581,429, 1986.
Rizzardo, E. Chem Aust 1987, 54, 32.
Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym Sci 1993, 2, 66.
MacLeod, P. J.; Veregin, R. P. N.; Odell, P. G.; Georges, M. K. Macromolecules 1998, 31, 530.
Grimaldi, S.; Le Moigne, F.; Tordo, P.; Nicol, P.; Plechot, M. W.O. 96/24620, 1996.
Benoit, D. Polymérisation Radicalaire Contrôlée en Présence de Radicaux Nitroxides, Ph.D. Thesis; Université de Bordeaux: France, 1997.
Grimaldi, S.; Finet, J. P.; Le Moigne, F.; Zeghdaoui, A.; Tordo, P.; Benoit, D.; Fontanille, M.; Gnagnou, Y. Macromolecules 2000, 33, 1141.
Benoit, D.; Grimaldi, S.; Robin, S.; Finet, J. P.; Tordo, P.; Gnagnou, Y. J Am Chem Soc 2000, 122, 5929.
Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J Am Chem Soc 1999, 121, 3904.
Benoit, D.; Harth, E.; Fox, P.; Waymouth, R. M.; Hawker, C. J. Macromolecules 2000, 33, 363.
Hawker, C. J.; Bosmann, A. W.; Harth, E. Chem Rev 2001, 101, 3661.
Drockenmuller, E.; Catala, J.-M. Macromolecules 2002, 35, 2461.
Drockenmuller, E.; Lamps, J.-P.; Catala, J.-M. Macromolecules 2004, 37, 2076.
Knoop, C. A.; Studer, A. J Am Chem Soc 2003, 125, 16327.
Gibbons, O.; Caroll, W. M.; Aldabbagh, F.; Yamada, B. J Polym Sci Part A: Polym Chem 2006, 44, 6410.
Lagrille, O.; Cameron, N. R.; Lovell, P. A.; Blanchard, R.; Goeta, A. E.; Koch, R. J Polym Sci Part A: Polym Chem 2006, 44, 1926.
Nesvabda, P.; Kramer, A.; Steinmann, A.; Stauffer, W. PCT Interl. Appl. WO 99/03894, 1999.
Nesvabda, P.; Kramer, A.; Steinmann, A.; Stauffer, W. U.S. Patent 6,262,206, 2001.
Zink, M.-O.; Kramer, A.; Nesvabda, P. Macromolecules 2000, 33, 8106.
Grishin, D. F.; Semenycheva, L. L.; Kolyakina, E. V. Polym Sci Ser A 1999, 41, 401.
Grishin, D. F.; Semenycheva, L. L.; Sokolov, K. V.; Kolyakina, E. V. Polym Sci Ser B 2000, 42, 189.
Grishin, D. F.; Ignatov, S. K.; Razuvaev, A. G.; Kolyakina, E. V.; Shchepalov, A. A.; Pavlovskaya, M. V.; Semenycheva, L. L. Polym Sci Ser A 2001, 43, 989.
Kolyakina, E. V.; Semenycheva, L. L.; Grishin, D. F. Polym Sci Ser A 2001, 43, 1223.
Grishin, D. F.; Semenycheva, L. L.; Kolyakina, E. V. Russ J Appl Chem 2001, 74, 494.
Grishin, D. F.; Semenycheva, L. L.; Pavlovskaya, M. V.; Sokolov, K. V. Russ J Appl Chem 2001, 74, 1594.
Pavlovskaya, M. V.; Kolyakina, E. V.; Polyanskova, V. V.; Semenycheva, L. L.; Grishin, D. F. Russ J Appl Chem 2002, 75, 1868.
Grishin, D. F.; Semenycheva, L. L.; Bulgakova, S. A.; Mazanova, L. M.; Kolyakina, E. V. Polym Sci Ser A 2003, 45, 305.
Zaremski, M. Y.; Orlova, A. P.; Garina, E. S.; Olenin, A. V.; Lachinov, M. B.; Golubev, V. B. Polym Sci Ser A 2003, 45, 502.
Kolyakina, E. V.; Grishin, D. F.; Semenycheva, L. L.; Sazonova, E. V. Polym Sci Ser A 2004, 46, 10.
Golubev, V. B.; Zaremski, M. Y.; Orlova, A. P.; Olenin, A. V. Polym Sci Ser A 2004, 46, 295.
Grishin, D. F.; Semenycheva, L. L.; Kolyakina, E. V. Mendeleev Commun 1999, 6, 250.
Detrembleur, C.; Sciannamea, V.; Koulic, C.; Claes, M.; Hoebeke, M.; Jérôme, R. Macromolecules 2002, 35, 7214.
Sciannamea, V.; Guerrero-Sanchez, C.; Schubert, U. S.; Catala, J.-M.; Jérôme, R.; Detrembleur, C. Polymer 2005, 46, 9632.
Detrembleur, C. Developments of New Regulators for Controlled Radical Polymerization, Ph.D. Thesis; University of Liège: Belgium, 2001.
(a) Catala, J.-M.; Jousset, S.; Lamps, J.-P. Macromolecules 2001, 34, 8654;
(b) Grubbs, R. B. Chem Commun 2005, 80.
Xia, Q.; Grubbs, R. B. J Polym Sci Part A: Polym Chem 2006, 44, 5128.
Vanhoorne, P.; Meyer, R. V.; Detrembleur, C.; Jérôme, R. Eur Pat Appl EP1236742, 2002.
Detrembleur, C.; Teyssié, P.; Jérôme, R. Macromolecules 2002, 35, 1611.
Detrembleur, C.; Mouithys-Mickalad, A.; Teyssié, P.; Jérôme, R. E-Polymers [online computer file] 2002, Paper No. 4.
Detrembleur, C.; Claes, M.; Jérôme, R. ACS Symposium Series, Vol. 854: Advances in Controlled/Living Radical Polymerization; American Chemical Society: Washington, DC, 2003; p 496.
Vanhoorne, P.; Meyer, R.-V.; Detrembleur, C.; Jérôme, R. PCT Intl. Appl. W.O. 02/068478 A2, 2002.
Toru, N.; Takesi, A. U.S. Patent 6,242,546 B1, 2001.
Wertmer, H.; Simon, D.; Pfaender, R. PCT Intl. Appl. W.O. 2005/021630, 2005.
Detrembleur, C.; Gross, T.; Meyer, R. V. Eur Pat Appl E.P. 1,428,838 A1, 2002.
Detrembleur, C.; Rüdiger, C.; Meyer, R. V. Eur Pat Appl E.P. 1,428,837 A1, 2002.
Sciannamea, V.; Bernard, M.; Catala, J.-M.; Jérôme, R.; Detrembleur, C. J Polym Sci Part A: Polym Chem 2006, 21, 6299.
Iwamura, H.; Iwamura, M. Tetrahedron Lett 1970, 42, 3723.
Iwamura, M.; Inamoto, N. Bull Chem Soc Jpn 1970, 43, 856, 860.
Janzen, E. G. Ace Chem Res 1971, 4, 3126.
Moad, G.; Solomon, D. H. In The Chemistry of Free Radical Polymerization; Pergamon: Elmsford, NY, 1995; Chapter 3, p 54.
Buback, M.; Gilbert, R. G.; Hutchinson, R. A.; Klumperman, B.; Kuchta, F.-D.; Manders, B. G.; O'Driscoll, K. F.; Rusell, G.; Schweer, J. Macromolecular Chemistry and Physics 1995, 196(10), 3267.
Beuermann, S.; Buback, M. Prog Polym Sci 2002, 27, 191.
Fischer, H. J Polym Sci Part A: Polym Chem 1999, 37, 1885.
Goto, A.; Fukuda, T. Prog Polym Sci 2004, 29, 329.
Lacroix-Desmazes, P.; Lutz, J.-P.; chauvin, F.; Severac, R.; Boutevin, B. Macromolecules 2001, 34, 8866.
Lacroix-Desmazes, P.; Lutz, J.-P.; Boutevin, B. Macromol Chem Phys 2000, 201, 662.
Fukuda, T.; Terauchi, T.; Goto, A.; Ohno, K.; Tsujii, Y.; Miyamoto, T. Macromolecules 1996, 29(20), 6393.
Marque, S.; Fischer, H.; Baier, E.; Studer, E. J Org Chem 2001, 66, 1146.
Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403.
Bertin, D.; Gigmes, D.; Marque, S.; Tordo, P. Macromolecules 2005, 38, 2638.
Miura, Y.; Nakamura, N.; Taniguchi, I.; Ichikawa, A. Polymer 2003, 44, 3461.
Guillaneuf, Y.; Castignolles, P.; Charleux, B.; Bertin, D. Polym Prepr (Am Chem Soc Div Polym Chem) 2005, 46, 307.