Investigation of methyl methacrylate and vinyl acetate polymerization promoted by Al(iBu)3/2,2'-bipyridine and Al(iBu)3/2,2'-bipyridine/TEMPO complexes

Granel, Claude; Jérôme, Robert; Teyssié, Philippe; Jasieczek, C. B.; Shooter, A. J.; Haddleton, D. M.; Hastings, J. J.; Gigmes, D.; Grimaldi, S.; Tordo, P.; Greszta, D.; Matyjaszewski, K.

doi:10.1021/ma980006x

Article (Scientific journals)

Investigation of methyl methacrylate and vinyl acetate polymerization promoted by Al(iBu)3/2,2'-bipyridine and Al(iBu)3/2,2'-bipyridine/TEMPO complexes

Granel, Claude; Jérôme, Robert; Teyssié, Philippe et al.

1998 • In Macromolecules, 31 (21), p. 7133-7141

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/14953

DOI
10.1021/ma980006x

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Granel C 1998 Macromolecules 7133.pdf

Publisher postprint (150.43 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 :

polymerization; (meth)acrylate; vinyl acetate

Abstract :

[en] Results of methyl methacrylate (MMA) and vinyl acetate (VOAc) polymerization using the Al(iBu)3/2,2‘-bipyridine/TEMPO initiating system at room temperature failed to confirm the “living” radical mechanism reported earlier. Several species apparently propagate without control in a normal free radical process and only above a critical initiator concentration. No evidence was found for the penta- and hexacoordinated aluminum species previously suggested, but high conversion to an alkoxyamine was observed. Additionally, mixing Al(iBu)3 and BIPY promotes a variety of reactions involving alkyl and hydride transfers to the aromatic rings forming reduced BIPY products, along with a persistent organoaluminum radical. All these results illustrate that the process is considerably more complicated than postulated before. Conversely, at −78 °C, a single active species excluding the participation of TEMPO has been put in evidence, displaying some “living” characteristics. Several experiments support its anionic nature, as previously suggested by Ikeda.

Research Center/Unit :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Chemistry
Materials science & engineering

Author, co-author :

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

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

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

Jasieczek, C. B.; University of Warwick, UK > Department of Chemistry

Shooter, A. J.; University of Warwick, UK > Department of Chemistry

Haddleton, D. M.; University of Warwick, UK > Department of Chemistry

Hastings, J. J.; University of Warwick, UK > Department of Chemistry

Gigmes, D.; Centre de Saint Jérôme, Marseille, France > Laboratoire de Structure et Réactivité des Espèces Paramagnétiques

Grimaldi, S.; Centre de Saint Jérôme, Marseille, France > Laboratoire de Structure et Réactivité des Espèces Paramagnétiques

Tordo, P.; Centre de Saint Jérôme, Marseille, France > Laboratoire de Structure et Réactivité des Espèces Paramagnétiques

Greszta, D.; Carnegie Mellon University, Pittsburgh, USA > Department of Chemistry

Matyjaszewski, K.; Carnegie Mellon University, Pittsburgh, USA > Department of Chemistry

Language :

English

Title :

Investigation of methyl methacrylate and vinyl acetate polymerization promoted by Al(iBu)3/2,2'-bipyridine and Al(iBu)3/2,2'-bipyridine/TEMPO complexes

Publication date :

20 October 1998

Journal title :

Macromolecules

ISSN :

0024-9297

eISSN :

1520-5835

Publisher :

Amer Chemical Soc, Washington, United States - Washington

Volume :

Issue :

Pages :

7133-7141

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.acs.org/doi/pdf/10.1021/ma980006x
http://pubs.acs.org/doi/suppl/10.1021/ma980006x/suppl_file/ma980006x_s.pdf

Funders :

BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
Elf Atochem

Available on ORBi :

since 19 June 2009

Statistics

Number of views

63 (1 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

(a) Solomon, D. H.; Rizzardo, E.; Cacioli, P. U.S. Patent 4 581 429,1986.
(b) Moad, G.; Solomon, D. H. Aust. J. Chem. 1990, 43, 215.
(a) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
(b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends. Polym. Sci. 1994, 2, 66.
(a) Hawker, C. J.J. Am. Chem. Soc. 1994, 116, 11185.
(b) Puts, R. D.; Sogah, D. Y. Macromolecules 1996, 29, 3323.
(c) Hawker, C. J.; Barclay, G. G.; Orellana, A.; Dao, J.; Devonport, W. Macromolecules 1996, 29, 5245.
(d) Bon, S. A. F.; Bosveld, M.; Klumperman, B.; German, A. L. Macromolecules 1997, 30, 324.
(e) Catala, J. M.; Bubel, F.; Oulad Hammouch, S. Macromolecules 1995, 28, 8441.
(f) Fukuda, T.; et al. Macromolecules 1996, 29, 6393.
(g) Greszta, D.; Matyjaszewski, K. Macromolecules 1996, 29, 7661.
(h) Hawker, C. J. Trends. Polym. Sci. 1996, 4, 183.
(a) Georges, M. K.; et al. Macromolecules 1996, 29, 8992.
(b) Grimaldi, S.; Finet, J.-P.; Zeghdaoui, A.; Tordo, P.; Benoit, D.; Gnanou, Y.; Fontanille, M.; Nicol, P.; Pierson, J.-P. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997, 38 (1), 651
(c) Benoit, D.; Grimaldi, S.; Finet J.-P.; Tordo, P.; Fontanille, M.; Gnanou, Y. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997, 38 (1), 729.
Wayland, B. B.; Poszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943.
Arvanitopoulos, L. D.; Greuel, M. P.; Harwood: H. J. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1994, 32 (2), 549.
(a) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721.
(b) Ando, T.; Kato, M.; Kamigaito, M.; Sawamoto, M. Macromolecules 1996, 29, 1070.
(a) Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
(b) Wang, J. S.; Matyjaszewski, K. Macromolecules 1995, 28, 7901.
(c) Percec, V.; Barboiu, B. Macromolecules 1995, 28, 7970.
(d) Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J., Shooter, A. J. Macromolecules 1997, 30, 2190.
Granel, C.; Dubois, Ph.; Jérôme, R.; Teyssié, Ph. Macromolecules 1996, 29, 8576.
Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 645.
Mardare, D.; Matyjaszewski, K.; Coca, S. Macromol. Rapid Commun. 1994, 15, 37.
Mardare, D.; Matyjaszewski, K. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1993, 34 (2), 566.
Barron, A. In Coordination Chemistry of Aluminum; Robinson, G. H., Ed.; VCH: New York, 1993; p 158.
Kaim, W. Acc. Chem. Res. 1985, 18, 160.
Van Koten, G.; Jastrzebski, J. T. B. H.; Vrieze, K. J. Organomet. Chem. 1983, 49, 250.
Kaim, W. J. Organomet. Chem. 1980, C5, 201.
Davies, A. G.; Florjanczyk, Z.; Lusztyk, E.; Lusztyk, J. J. Organomet. Chem. 1982, 229, 215.
Skowronska-Ptasinska, M.; Starowieyski, K. B.; Pasynkiewicz, S. J. Organomet. Chem. 1977, 141, 149.
Kuruki, M.; Watanabe, T.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1991, 113, 5903.
(a) Kitayama T., Shinozaki T., Masuda E., Yamamoto M., Hatada K., Polym. Bull. 1988, 20, 505.
(b) Wang J. S., Jérôme R., Teyssié Ph., J. Phys. Org. Chem. 1995, 8, 208.
(a) Ballard, D. G. H.; Bowles, R. G.; Haddleton, D. M.; Richards, S. N.; Sellens, R.; Twose, D. L. Macromolecules 1992, 25, 5907.
(b) Mardare, D.; Coca, S.; Dimonie, M.; et al. Macromol. Rapid Commun. 1992, 13, 283.
(a) Ikeda, M.; Hirano, T.; Tsuruta, T. Makromol. Chem. 1971, 127, 150.
(b) Ikeda, M.; Hirano, T.; Nkayama, S.; Tsuruta, T. Makromol. Chem. 1974, 175, 2775.
Korshun, A.; Mazurek, V.; Shorohkodov, S. Makromol. Chem. 1979, 180, 2265.
(a) Haddleton, D. M.; Hastings, J. J.; Howarth, O. W.; Tann, S. M. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1994, 35 (2), 566.
(b) Haddleton, D. M.; Jasieczek, C. B.; Shooter, A.; Hastings, J. J.; Howarth, O. W. A. P. M. E. 1995 (Vassar, USA).
Shimomura, T.; Töile, K. J.; Smid, J.; Szwarc, M. J. Am. Chem. Soc. 1967, 89, 796.
Schmitt, B. J.; Schulz, G. V. Eur. Polym. J. 1975, 11, 119.
Kitayama, T.; Masuda, E.; Yamaguchi, M.; Nishiura, T.; Hatada, K. Polym. J. 1992, 24(8), 817.
Comprehensive Organometallic Chemistry, 1st ed.; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, England, 1982; Vol. 1, p 608.
Benn, R.; Rufinska, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 861.
(a) Kaim, W. Z. Naturforsch. 1982, 37B, 783,
(b) Kaim, W. J. Organomet. Chem. 1981, 222, C17.
Sharp, J. H., Symons, M. C. R. In Ions and Ions Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley-Interscience: New York, 1972; Vol 1, p 177.
White, D.; Matyjaszewski, K. J. Macromol. Sci., Pure. Appl. Chem. 1997, A31(1), 221.
Cohen, A. H.; Hoffman, B. M. Inorg. Chem. 1974, 13, 1484.
Kristoff, J. S.; Shriver, D. F. Inorg. Chem. 1973, 12, 1788.
(a) Beckwith, A. L. J.; Bowry, V. W.; et al. J. Chem. Soc., Chem. Commun. 1986, 1003.
(b) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. H. J. Am. Chem. Soc. 1992, 114, 4983.
French Pat. 1,602,517, 1968, and US Pat. 3,851,015, 1974, to S. N. Elf Aquitaine. French Pat. 2,142,123, 1971, and US Pat. 3,949,018, 1976, to Aquitaine Total.,
Ueda, N.; Kamigaito, M.; Sawamoto, M. Polym. Prepr., Jpn. (Engl. Ed.) 1996, 45 (6-12), E622.