[en] The cobalt mediated radical polymerization (CMRP) of vinyl chloride (VC) in the presence of bis(acetylacetonato)cobalt(II) (Co(acac)2) as a controlling agent is presented for the first time. Using an alkyl-Co(III) compound (R0–(CH2–CHOAc)<4–Co(acac)2; R0 = (H3C)2(OCH3)C–CH2–C(CH3)(CN)–) as an initiator, the bulk polymerization under non-isotherm conditions is controlled. 1H NMR spectra of the resulting PVC show that the CMRP process does not significantly affect the level of defects compared to a PVC prepared by a conventional free radical polymerization at the same temperature. Using the same alkyl-cobalt(III) compound, the copolymerization of VC and VAc is controlled at 40 °C provided that enough VAc (about 40 mol%) is present in the polymerization medium to moderate the VC polymerization. In line with reactivity ratios, VC is preferentially incorporated in the polymer at the early stages of the polymerization, leading to copolymers with a high VC content at moderate conversions. This is the first report of a CMRP of VC and of the synthesis of well-defined statistical PVC-co-PVAc copolymers by this technique.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Piette, Yasmine; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Debuigne, Antoine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Bodart, Vincent; Solvin SA
Poli, Rinaldo; Université de Toulouse et Institut Universitaire de France > (Laboratoire de Chimie de Coordination (Toulouse)
Detrembleur, Christophe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Cobalt-mediated radical (co)polymerization of vinyl chloride and vinyl acetate
Publication date :
October 2012
Journal title :
Polymer Chemistry
ISSN :
1759-9954
eISSN :
1759-9962
Publisher :
Royal Society Chemistry, Cambridge, United Kingdom
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique CNRS - Centre National de la Recherche Scientifique The IUF The "Agnece National de la Recherche"
L. L. Semenycheva D. F. Grishin Russ. J. Appl. Chem. 2003 76 851 858
K. Endo N. Kaneda H. Waku Polymer 1999 40 6883 6886
V. Percec A. V. Popov E. Ramirez-Castillo O. Weichold J. Polym. Sci., Part A: Polym. Chem. 2003 41 3283 3299
Polymer Handbook, ed., J. Brandrup, E. H. Immergut, and, E. A. Grulke, Wiley, New York, 4th edn, 1999
D. Braun J. Vinyl Addit. Technol. 2005 11 86 90
G. David C. Boyer J. Tonnar B. Ameduri P. Lacroix-Desmazes B. Boutevin Chem. Rev. 2006 106 3936 3962
T. Wannemacher D. Braun R. Pfaendner Macromol. Symp. 2003 202 11 23
R. Pfaendner, T. Wannemacher and D. Braun, PCT Int. Appl., WO 02/38632, Ciba Specialty Chemicals Hoding Inc., 2002
D. F. Grishin L. L. Semenycheva M. V. Pavlovskaya K. V. Sokolov Russ. J. Appl. Chem. 2001 74 1594 1599
V. Sciannamea R. Jerome C. Detrembleur Chem. Rev. 2008 108 1104 1126
A. D. Asandei V. Percec J. Polym. Sci., Part A: Polym. Chem. 2001 39 3392 3418
V. Percec A. V. Popov E. Ramirez-Castillo M. Monteiro B. Barboiu O. Weichold A. D. Asandei C. M. Mitchell J. Am. Chem. Soc. 2002 124 4940 4941
V. Percec A. V. Popov E. Ramirez-Castillo J. Polym. Sci., Part A: Polym. Chem. 2004 43 287 295
V. Percec A. V. Popov E. Ramirez-Castillo J. F. J. Coelho J. Polym. Sci., Part A: Polym. Chem. 2005 43 773 778
V. Percec A. V. Popov E. Ramirez-Castillo O. Weichold J. Polym. Sci., Part A: Polym. Chem. 2004 42 6364 6374
V. Percec T. Guliashvili A. V. Popov E. Ramirez-Castillo J. Polym. Sci., Part A: Polym. Chem. 2005 43 1478 1486
V. Percec T. Guliashvili A. V. Popov E. Ramirez-Castillo J. F. J. Coelho L. A. Hinojosa-Falcon J. Polym. Sci., Part A: Polym. Chem. 2005 43 1649 1659
J. F. J. Coelho A. M. F. P. Silva A. V. Popov V. Percec M. V. Abreu P. M. O. F. Goncalves M. H. Gil J. Polym. Sci., Part A: Polym. Chem. 2006 44 3001 3008
V. Percec A. V. Popov E. Ramirez-Castillo L. A. Hinojosa-Falcon J. Polym. Sci., Part A: Polym. Chem. 2005 43 2276 2280
M. J. Sienkowska V. Percec J. Polym. Sci., Part A: Polym. Chem. 2009 47 635 652
V. Percec M. J. Sienkowska J. Polym. Sci., Part A: Polym. Chem. 2009 47 628 634
V. Percec T. Guliashvili J. S. Ladislaw A. Wistrand A. Stjerndahl M. J. Sienkowska M. J. Monteiro S. Sahoo J. Am. Chem. Soc. 2006 128 14156 14165
M. J. Sienkowska B. M. Rosen V. Percec J. Polym. Sci., Part A: Polym. Chem. 2009 47 4130 4140
B. M. Rosen V. Percec Chem. Rev. 2009 109 5069 5119
T. Hatano B. M. Rosen V. Percec J. Polym. Sci., Part A: Polym. Chem. 2010 48 164 172
C. M. R. Abreu P. V. Mendonça A. C. Serra J. F. J. Coelho A. V. Popov G. Gryn'ova M. L. Coote T. Guliashvili Macromolecules 2012 45 2200 2208
C. J. Hawker A. W. Bosman E. Harth Chem. Rev. 2001 101 3661 3688
W. A. Braunecker K. Matyjaszewski Prog. Polym. Sci. 2007 32 93 146
M. Ouchi T. Terashima M. Sawamoto Chem. Rev. 2009 109 4963 5050
G. Moad E. Rizzardo S. H. Thang Aust. J. Chem. 2009 62 1402 1472
S. Yamago Chem. Rev. 2009 109 5051 5068
B. B. Wayland G. Poszmik S. L. Mukerjee M. Fryd J. Am. Chem. Soc. 1994 116 7943 7944
C.-H. Peng J. Scricco S. Li M. Fryd B. B. Wayland Macromolecules 2008 41 2368 2373
S. Li B. D. Bruin C.-H. Peng M. Fryd B. B. Wayland J. Am. Chem. Soc. 2008 130 13373 13381
A. Debuigne R. Poli C. Jerome R. Jerome C. Detrembleur Prog. Polym. Sci. 2009 34 211 239
A. Debuigne J.-R. Caille C. Detrembleur R. Jerome Angew. Chem., Int. Ed. 2005 44 3439 3442
A. Debuigne J.-R. Caille R. Jerome Angew. Chem., Int. Ed. 2005 44 1101 1104
A. Debuigne J.-R. Caille R. Jerome Macromolecules 2005 38 5452 5458
C. Detrembleur A. Debuigne R. Bryaskova B. Charleux R. Jerome Macromol. Rapid Commun. 2006 27 37 41
S. Maria H. Kaneyoshi K. Matyjaszewski R. Poli Chem.-Eur. J. 2007 13 2480 2492
R. Poli Angew. Chem., Int. Ed. 2006 45 5058 5070
K. M. Smith W. S. McNeil A. S. Abd-El-Aziz Macromol. Chem. Phys. 2010 211 10 16
M. Hurtgen C. Detrembleur C. Jérôme A. Debuigne Polym. Rev. 2011 51 188 213
L. E. N. Allan M. R. Perry M. P. Shaver Prog. Polym. Sci. 2012 51 188 213
R. Poli, Organometallic-Mediated Radical Polymerization, in Polymer Science: A Comprehensive, ed., K. Matyjaszewski, and, M. Möller, Elsevier, Amsterdam, 2012, vol. 3, pp. 351-375
H. Kaneyoshi K. Matyjaszewski Macromolecules 2006 39 2757 2763
A. Debuigne N. Willet R. Jerome C. Detrembleur Macromolecules 2007 40 7111 7118
A. Debuigne R. Poli J. De Winter P. Laurent P. Gerbaux J.-P. Wathelet C. Jerome C. Detrembleur Macromolecules 2010 43 2801 2813
M. Hurtgen J. Liu A. Debuigne C. Jérôme C. Detrembleur J. Polym. Sci., Part A: Polym. Chem. 2012 50 400 408
A. Debuigne J. Warnant R. Jerome I. Voets A. de Keizer M. A. Cohen Stuart C. Detrembleur Macromolecules 2008 41 2353 2360
A. Debuigne C. Michaux C. Jerome R. Jerome R. Poli C. Detrembleur Chem.-Eur. J. 2008 14 7623 7637
A. Debuigne C. Jérôme C. Detrembleur Angew. Chem., Int. Ed. 2009 48 1422 1424
M. Hurtgen A. Debuigne C. Jerome C. Detrembleur Macromolecules 2010 43 886 894
M. Hurtgen A. Debuigne C.-A. Fustin C. Jerome C. Detrembleur Macromolecules 2010 44 4623 4631
A. Debuigne Y. Champouret R. Jerome R. Poli C. Detrembleur Chem.-Eur. J. 2008 14 4046 4059
K. S. Santhosh Kumar Y. Gnanou Y. Champouret J.-C. Daran R. Poli Chem.-Eur. J. 2009 15 4874 4885
A. Debuigne R. Poli R. Jerome C. Jerome C. Detrembleur ACS Symp. Ser. 2009 1024 131 147
G. Moad and D. H. Solomon, The Chemistry of Free Radical Polymerization, Pergamon, 1995
H. A. Sarvetnick Polyvinyl Chloride 1969 14
PVC Handbook, ed., C. E. Wilkes, J. W. Summers, and, C. A. Daniels, Hanser Verlag, München, 2005
T. P. Davis D. Kukulj D. M. Haddleton D. R. Maloney Trends Polym. Sci. 1995 3 365 373
A. Gridnev J. Polym. Sci., Part A: Polym. Chem. 2000 38 1753 1766
A. A. Gridnev S. D. Ittel Chem. Rev. 2001 101 3611 3659
G. Moad and D. H. Solomon, The Chemistry of Radical Polymerization, Second Fully Revised Edition, Elsevier, 2006
A. D. Asandei V. Percec J. Polym. Sci., Part A: Polym. Chem. 2001 39 3392 3418
W. H. Starnes Jr J. Polym. Sci., Part A: Polym. Chem. 2005 43 2451 2467
G. M. Benedikt R. J. Cozens B. L. Goodall L. F. Rhodes M. N. Bell A. C. Kemball W. H. Starnes, Jr Macromolecules 1997 30 10 21
M. F. Darricades-Llauro A. Michel A. Guyot H. Waton R. Petiaud Q. T. Pham J. Macromol. Sci., Chem. 1986 23 221 269
V. Percec A. V. Popov E. Ramirez-Castillo J. F. J. Coelho L. A. Hinojosa-Falcon J. Polym. Sci., Part A: Polym. Chem. 2004 42 6267 6282
V. Percec E. Ramirez-Castillo L. A. Hinojosa-Falcon A. V. Popov J. Polym. Sci., Part A: Polym. Chem. 2005 43 2185 2187
J. Purmova K. F. D. Pauwels W. Van Zoelen E. J. Vorenkamp A. J. Schouten M. L. Coote Macromolecules 2005 38 6352 6366
C. J. M. Van Den Heuvel A. J. M. Weber Makromol. Chem. 1983 184 2261 2273
J.-T. Xu Q. Wang F. Wu Z.-Q. Fan Eur. Polym. J. 2005 41 115 120
G. M. Benedikt B. L. Goodall L. F. Rhodes A. C. Kemball Macromol. Symp. 1994 86 65 75
T. Hjertberg E. M. Sorvik Polymer 1983 24 673 684
V. Percec A. V. Popov E. Ramirez-Castillo J. Polym. Sci., Part A: Polym. Chem. 2004 43 287 295
H. Kaneyoshi K. Matyjaszewski Macromolecules 2005 38 8163 8169
R. Z. Greenley J. Macromol. Sci., Chem. 1980 14 445 515
G. C. Laurier K. F. O'Driscoll P. M. Reilly J. Polym. Sci., Polym. Symp. 1985 72 17 26
R. Z. Greenley, Polymer Handbook, 3rd edn, 1989, p. II/153
