Mechanistic aspects of ligated anionic living polymerization (LAP) - the case of (meth)acrylic ester monomers

Wang, Jin-Shan; Jérôme, Robert; Teyssié, Philippe

doi:10.1002/poc.610080404

Request a copy

Article (Scientific journals)

Mechanistic aspects of ligated anionic living polymerization (LAP) - the case of (meth)acrylic ester monomers

Wang, Jin-Shan; Jérôme, Robert; Teyssié, Philippe

1995 • In Journal of Physical Organic Chemistry, 8, p. 208-221

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/197109

DOI
10.1002/poc.610080404

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Wang JS 1995 J Phys Org Chem 8, 208.pdf

Publisher postprint (1.19 MB)

Request a copy

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

anionic polymerization

Abstract :

[en] The recently developed 'ligated' technique has proved to be very successful in promoting living anionic polymerization of (meth)acrylic ester monomers. The efficient ligands discovered to date include mu, sigma and mu-sigma dual types. The roles of these ligands in the control of livingness and stereoregularity of anionic polymerization of (meth)acrylates are discussed in detail. There is convincing evidences that both ligation thermodynamics (electron density redistribution and steric hindrance in the formed active complex) and kinetics (how fast and in which way ligation occurs) are very critical in promoting the livingness. Moreover, steric hindrance appears to be a determining factor maintaining the process 'living' under more demanding conditions.

Research Center/Unit :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Wang, Jin-Shan; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

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

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

Language :

English

Title :

Mechanistic aspects of ligated anionic living polymerization (LAP) - the case of (meth)acrylic ester monomers

Publication date :

1995

Journal title :

Journal of Physical Organic Chemistry

ISSN :

0894-3230

eISSN :

1099-1395

Publisher :

John Wiley & Sons, Inc

Volume :

Pages :

208-221

Peer reviewed :

Peer Reviewed verified by ORBi

Funders :

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

Available on ORBi :

since 20 May 2016

Statistics

Number of views

121 (5 by ULiège)

Number of downloads

3 (2 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Webster O.W., Hertler W.R., Sogah D.Y., Farham W.B., Babu T.V.R. J. Am. Chem. Soc. 1983, 105:5706.
Sogah D.Y., Hertler W.R., Webster O.W., Cohen G.M. Macromolecules , 1987; 1987, 20:1473.
Reetz M.T. (1988) New Methods for the Anionic Polymerization of ?-Activated Olefins. Angewandte Chemie International Edition in English 27:994.
Sivram S., Dhal P.K., Kashikar S.P., Khishi R.S., Shinde B.M., Baskaran D. Polym. Bull. 1991, 25:77.
Collins S., Ward D.G. J. Am. Chem. Soc. 1992, 114:5460.
Inoue S., Aida T., Kuroki M., Hosokawa Y. (1990) Living polymerizations of acrylic monomers with aluminioporphyrin. Makromolekulare Chemie. Macromolecular Symposia 32:255.
Yasuda H., Yamamoto H., Takemoto Y., Yamashita M., Yokota K., Miyake S., nakaamure A. (1993) Novel synthesis of high molecular weight polymers with extremely low polydispersity by the unique initiation properties of organo-lanthanide complexes. Makromolekulare Chemie. Macromolecular Symposia 67:187.
Mardare D., Matyjaszewski K. Macromolecules 1994, 27:645.
Hatada K., Ute K., Tanaaka K., Okamoto Y., Kityama T. Polym. Bull. 1986, 18:1037.
Ballard D.G.H., Bowles R.J., haddleton D.M., Richards S.N., Sellens R., Twose D.L. Macromolecules 1992, 25:5907.
Wang J.S., Teyssié, Heim, Vuillemin B. Fr. Pat. 1994, 94:6891.
Lochmann L., Rodova M., Trekoval J. J. Polym. Sci., Polym. Chem. Ed. 1974, 12:2091.
Lochmann L., Trekoval J., U.S. Pat. 4,056,580 and 4,238,588, (1980).; 1977.
Lochmann L., Trekoval J. J. Polym. Sci., Polym. Chem. Ed. 1979, 17:1727.
Dvoranek L., Vlcek P. Polym. Bull. 1993, 31:393.
Ouhadi T., Forte R., Jéôme R., Fayt R., Teyssié Lux. Pat. 1984, 85:627.
1988.
Fayt R., Forte R., Jacobs C., Jérôme R., Ouhadi T., Teyssié, Varshney S.K. Macromolecules 1987, 20:1442.
Varshney S.K., Hautekeer J.P., Fayt R., Jérôme R., Teyssié Macromolecules 1990, 23:2618.
Varshney S.K., Jérôme R., Bayard, Jacobs C., Fayt R., Teyssié Macromolecules 1992, 25:4457.
Bayard, Fayt R., Teyssié, Varshney S.K., Fr. Pat. 91,09172; 1991.
Bayard, Jérôme R., Teyssié, Varshney S.K., Wang J.S. Polym. Bull. 1994, 32:381.
Jérôme R., Forte R., Varshney S.K., Fayt R., Teyssié Recent Advances in Mechanistic and Synthetic Aspects of Polymerization , edited by, M. Fontanille, A. Guyot, NATO ASI Series; 1987, 101.
Teyssié, Fayt R., Hautekeer J.P., Jacobs C., Jérôme R., Leemans L., Varshney S.K. (1990) New prospects for “living” anionic polymerization of (meth) acrylic esters. Makromolekulare Chemie. Macromolecular Symposia 32:61.
Wiles D.M. Structure and Mechanism in Vinyl Polymerization , edited by, T. Tsuruta, K. F. O'Driscoll, Marcel Dekker, New York; 1969, 233.
Müller A.H.E. Anionic Polymerization: Kinetics, Mechanisms, and Synthesis , edited by, J. E. McGrath, ACS Symposium Series, No. 16, American Chemical Society, Washington, DC; 1981, 441.
Müller A.H.E. Recent Advances in Anionic Polymerization , edited by, T. E. Hogen‐Esch, J. Smid, Elsevier, New York; 1987, 205.
Vancea L., Bywater S. Macromolecules 1981, 14:1321.
Vancea L., Bywater S. Macromolecules 1981, 14:1776.
Wang J.S., PhD Thesis, University of Liège; 1993.
Wang J.S., Jérôme R., Warin R., Teyssié Macromolecules 1993, 26:6776.
Wang J.S., Jérôme R., Warin R., Teyssié Macromolecules 1994, 27:1691.
Wang J.S., Jérôme R., Warin R., Zhang H., Teyssié Macromolecules 1994, 27:3376.
Wang J.S., Jerôme R., Teyssié Macromolecules 1994, 27:4896.
Wang J.S., Jérôme R., Warin R., Teyssié Macromolecules 1993, 26:1402.
Lochmann L., Lim D. J. Organomet. Chem. 1973, 50:9.
Lochmann L., Trekoval J. J. Organomet. Chem. 1975, 99:329.
Long T.E., Allen R.D., McGrath J.E. Recent Advances in Mechanistic and Synthetic Aspects of Polymerization , edited by, M. Fontanille, A. Guyot, NATO ASI Series, No. 215; 1987, 79.
Taft R.W. Rates and Equilibria of Organic Reactions, edited by, J. E. Leffler, E. Grunewald, Wiley, New York; 1963.
Antoun S., Wang J.S., Jérôme R., Teyssié, Polymer; .
Wang J.S., Jérôme R., Teyssié.
Jacobs C., Varshney S.K., Hautekeer J.P., Fayt R., Jérôme R., Teyssié Macromolecules 1990, 23:4024.
Anderson B.C., Andrews G.D., Arthur P., Jacobson H.W., Melby L.R., Playtis A.F., Sharkey W.H. Macromolecules 1991, 14:1599.
Lochmann L., Janata M., Machova L., Vlcek P., Müller A.H.E. Polym. Prep. 1988, 29:2.
Janata M., Lochmann L., Müller A.H.E. Die Makromolekulare Chemie 1990, 191:2253.
Power P.P. Acc. Chem. Res. 1988, 21:147.
Jackman L.M., Lange B.C. J. Am. Chem. Soc. 1981, 103:4494.
Jackman L.M., Szovernyi N. J. Am. Chem. Soc. 1976, 99:4954.
House H.O., Prahu A.V., Phillips W.V. J. Org. Chem. 1976, 41:1209.
Busch D.H. Chem. Rev. 1993, 93:847.
Kitayama T., Shinozaki T., Sakamotok T., Yamamoto M., Hatada K. (1989) Living and highly syndiotactic polymerization of methyl methacrylate and other methacrylates by tert-butyllithiumtrialkylaluminium in toluene. Die Makromolekulare Chemie 15:167.
Varshney S.K., Jacobs C., Hautekeer J.P., Fayt R., Jérôme R., Teyssié Macromolecules 1991, 24:4997.
Wang J.S., Teyssié.
Dejong F., Reinhoudt D.N. Adv. Phys. Org. Chem. 1980, 17:279.
Kunkel D., Müller A.H.E., Janata M., Lochmann L. (1992) The role of association/complexation equilibria in the anionic polymerization of (meth)acrylates. Makromolekulare Chemie. Macromolecular Symposia 60:315.
Kunkel D., Müller A.H.E., Janata M., Lochmann L. Polym. Prep. 1991, 31:301.
Szwarc M. (1983) Living polymers and mechanisms of anionic polymerization. Adv. Polym. Sci. 49:1.
Wang J.S., Zhang H., Jérôme R., Teyssié, Macromolecules; .
Hogen‐Esch T.E. (1993) Stereochemistry of anionic vinyl polymerization. Makromolekulare Chemie. Macromolecular Symposia 67:43.
Hogen‐Esch T.E., paper presented at Frontier in Polymerization, Liège, October 6–8; 1993.
Wang J.S., Jérôme R., Warin, Teyssié Macromolecules 1993, 26:5984.
Hatada K., Kitayama T., Ute K. Prog. Polym. Sci. 1989, 13:189.
Kitayama T., Zhang Y.J., Hatada K. Polym. Bull. 1994, 32:439.
Wang J.S., Jérôme R., Warin R., Teyssié Macromolecules 1994, 27:4902.
Yuki H., Hatada K., Adv. Polym. Sci.; 1979.
Coleman B.D., Fox T.G. J. Chem. Phys. 1963, 38:1065.
Varshney S.K., Gao Z.S., Zhong X.F., Eisenberg A. Macromolecules 1994, 27:1076.
Baumgarten J.L., Müller A.H.E., Hogen‐Esch T.E. Macromolecules 1991, 24:353.
Bovey F.A. High Resolution NMR of Macromolecules, Academic Press, New York; 1972.
Moras D., Weiss R. (1973) Etude structurale des cryptates. IV. Structure cristalline et moléculaire du cryptate de lithium C14H28N2O4.LiI. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 29:400.
Hogen‐Esch T.E., Smid J. J. Am. Chem. Soc. 1966, 88:307.
Smid J. Angew. Chem., Int. Ed. Engl. 1972, 2:112.
O'Brien D.M., Russell C.R., Hart A.J. J. Am. Chem. Soc. 1979, 101:633.
Wang J.S., Teyssié, Heim, Vuillemin, Fr. Pat. 94, 01767; 1994.
Wang J.S., Bayard, Jérôme R., Baylac L., Patin M., Teyssié Macromolecules 1994, 27:4615.
Wang J.S., Jérôme R., Bayard, Patin M., Teyssié Macromlecules 1994, 27:4635.
Hautekeer J.P., Varshney S.K., Fayt R., Jérôme R., Teyssié Macromolecules 1990, 23:3893.
Wang J.‐S., Heim P., Vuillemin B., Teyssié P., Bayard P., Euro. Pat. EP 93402418.3; 1993.
1992.
Forte R., Ouhadi T., Fayt R., Jérôme R., Teyssié J. Polym. Sci., Polym. Chem. 1990, 28:2233.
Teyssié, Fayt R., Jacobs C., Jérôme R., Leemans L., Varshney S.K. Polym. Prepr. (ACS Polym. Chem. Div.) 1988, 28(2):52.
Leemans L., PhD Thesis, University of Liege; 1994.
Ghitti G., PhD Thesis, University of Liege; 1994.
Harrats C., PhD Thesis, University of Liege; 1994.
Wang J.‐S., Heim, Vuillemin B., Teyssié, Bayard, Eur. Pat. 93 402418.3; 1993.
Wang J.S., Jérôme R., Bayard, Teyssie Macromolecules 1994, 27:4908.
Jérôme R., Bayard, Varshney S.K., Jacobs Ch., Teyssié, Thermoplastics Elastomers; .
Antolin K., Lamps J.P., Rempp P., Gnanou Y. Polymer 1990, 31:967.
Gnanou Y., Rempp P. Die Makromolekulare Chemie 1988, 189:1997.
Varshney S.K., Bayard, Jacobs C., Jérôme R., Fayt R., Teyssié Macromolecules 1990, 23:3893.
Maus C., PhD Thesis, University of Liège; 1994.
Teyssié, in paper presented at Frontier in Polymerization, Liège, October; 1993, 6-8.
Teyssié Makromol. Chem., Makromol. Symp. , 227; 1994, 88.