[en] The organometallic-mediated radical polymerization (OMRP) of vinyl acetate (VAc) and its OMR copolymerization (OMRcoP) with tert-butyl 2-trifluoromethylacrylate (MAF-TBE) mediated by Co(SAL)2 (SAL = 2-formylphenolato or deprotonated salicylaldehyde) produced relatively well-defined PVAc and poly(VAc-alt-MAF-TBE) copolymers at moderate temperature (<40 ◦C) in bulk. The resulting alternating copolymer was characterized by 1H-, 13C- and 19F-nuclear magnetic resonance (NMR) spectroscopies, and by size exclusion chromatography. The linear first-order kinetic plot, the linear evolutions of the molar mass with total monomer conversion, and the relatively low dispersity (Đ~1.55) of the resulting copolymers suggest that this cobalt complex provides some degree of control over the copolymerization of VAc and MAF-TBE. Compared to the previously investigated cobalt complex OMRP mediators having a fully oxygen-based first coordination sphere, this study emphasizes a few peculiarities of Co(SAL)2: a lower ability to trap radical chains as compared to Co(acac)2 and the absence of catalytic chain transfer reactions, which dominates polymerizations carried in the presence of 9-oxyphenalenone cobalt derivative.
Research Center/Unit :
CESAM Complex and Entangled Systems from Atoms to Materials (CESAM) Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Banerjee, Sanjib; Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, Montpellier, France
Bellan, Ekaterina V.; University of Toulouse, CNRS, Laboratoire de Chimie de Coordination, France
Gayet, Florence; University of Toulouse, CNRS, Laboratoire de Chimie de Coordination, France
Debuigne, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Poli, Rinaldo; University of Toulouse, CNRS, Laboratoire de Chimie de Coordination, France > Institut Universitaire de France, Paris, France
Améduri, Bruno; Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, Montpellier, France
Ladmiral, Vincent; Institut Charles Gerhardt, Ingénierie et Architectures Macromoléculaires, Montpellier, France
Language :
English
Title :
Bis(formylphenolato)cobalt(II)-mediated alternating radical copolymerization of tert-butyl 2-trifluoromethylacrylate with vinyl acetate
Publication date :
December 2017
Journal title :
Polymers
ISSN :
2073-4360
Publisher :
MDPI Publishing, Basel, Switzerland
Volume :
9
Issue :
12
Pages :
705
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique ANR - Agence Nationale de la Recherche
Matyjaszewski, K. Atom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives. Macromolecules 2012, 45, 4015-4039
David, G.; Boyer, C.; Tonnar, J.; Améduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Use of iodocompounds in radical polymerization. Chem. Rev. 2006, 106, 3936-3962
Lopez, G.; Thenappan, A.; Ameduri, B. Synthesis of Chlorotrifluoroethylene-Based Block Copolymers by Iodine Transfer Polymerization. ACS Macro Lett. 2015, 4, 16-20
Asandei, A.D. Photomediated Controlled Radical Polymerization and Block Copolymerization of Vinylidene Fluoride. Chem. Rev. 2016, 116, 2244-2274
Taton, D.; Destarac, M.; Zard, S.Z. Macromolecular Design by Interchange of Xanthates (MADIX): Background, Design, Scope, and Applications. In Handbook of RAFT Polymerization; Barner-Kowollik, C., Ed.; Wiley-VCH:Weinheim, Germany, 2008; pp. 373-421
Barner-Kowollik, C. Handbook of RAFT Polymerization; Wiley-VCH: Weinheim, Germany, 2008
Hill, M.R.; Carmean, R.N.; Sumerlin, B.S. Expanding the Scope of RAFT Polymerization: Recent Advances and New Horizons. Macromolecules 2015, 48, 5459-5469
Zetterlund, P.B.; Thickett, S.C.; Perrier, S.; Bourgeat-Lami, E.; Lansalot, M. Controlled/Living Radical Polymerization in Dispersed Systems: An Update. Chem. Rev. 2015, 115, 9745-9800
Poli, R. Relationship between one-electron transition metal reactivity and radical polymerization processes. Angew. Chem. Int. Ed. Engl. 2006, 45, 5058-5070
Hurtgen, M.; Detrembleur, C.; Jerome, C.; Debuigne, A. Insight into Organometallic-Mediated Radical Polymerization. Polym. Rev. 2011, 51, 188-213
Poli, R. Organometallic Mediated Radical Polymerization. In Polymer Science: A Comprehensive Reference; Matyjaszewski, K., Möller, M., Eds.; Elsevier BV: Amsterdam, The Netherlands, 2012; Volume 3, pp. 351-375
Poli, R. New phenomena in organometallic-mediated radical polymerization (OMRP) and perspectives for control of less active monomers. Chem. Eur. J. 2015, 21, 6988-7001
Debuigne, A.; Jerome, C.; Detrembleur, C. Organometallic-mediated radical polymerization of 'less activated monomers': Fundamentals, challenges and opportunities. Polymer 2017, 115, 285-307
Detrembleur, C.; Debuigne, A.; Hurtgen, M.; Jerome, C.; Pinaud, J.; Fevre, M.; Coupillaud, P.; Vignolle, J.; Taton, D. Synthesis of 1-Vinyl-3-ethylimidazolium-Based Ionic Liquid (Co)polymers by Cobalt-Mediated Radical Polymerization. Macromolecules 2011, 44, 6397-6404
Debuigne, A.; Morin, A.N.; Kermagoret, A.; Piette, Y.; Detrembleur, C.; Jérôme, C.; Poli, R. Key Role of Intramolecular Metal Chelation and Hydrogen Bonding in the Cobalt-Mediated Radical Polymerization of N-Vinyl amides. Chem. Eur. J. 2012, 18, 12834-12844
Debuigne, A.; Poli, R.; Jérôme, C.; Jérome, R.; Detrembleur, C. Overview of cobalt-mediated radical polymerization: Roots, state of the art and future prospects. Prog. Polym. Sci. 2009, 34, 211-239
Wayland, B.B.; Poszmik, G.; Mukerjee, S. Living radical polymerization of acrylates by organocobalt porphyrin complexes. J. Am. Chem. Soc. 1994, 116, 7943-7944
Kaneyoshi, H.; Matyjaszewski, K. Radical (Co)polymerization of vinyl chloroacetate and N-vinylpyrrolidone mediated by bis(acetylacetonate)cobalt derivatives. Macromolecules 2006, 39, 2757-2763
Santhosh Kumar, K.S.; Gnanou, Y.; Champouret, Y.; Daran, J.-C.; Poli, R. Radical Polymerization of Vinyl Acetate with Bis(tetramethylheptadionato)cobalt(II): The Cohabitation of Three Different Mechanisms. Chem. Eur. J. 2009, 15, 4874-4885
Bellan, E.V.; Thevenin, L.; Gayet, F.; Fliedel, C.; Poli, R. Catalyzed Chain Transfer in Vinyl Acetate Polymerization mediated by 9-Oxyphenalenone Cobalt(II) complexes. ACS Macro Lett. 2017, 6, 959-962
Améduri, B. Controlled Radical (Co)polymerization of Fluoromonomers.Macromolecules 2010, 43, 10163-10184
Demarteau, J.; Ameduri, B.; Ladmiral, V.; Mees, M.A.; Hoogenboom, R.; Debuigne, A.; Detrembleur, C. Controlled Synthesis of Fluorinated Copolymers via Cobalt-Mediated Radical Copolymerization of Perfluorohexylethylene and Vinyl Acetate. Macromolecules 2017, 50, 3750-3760
Tyson, G.N.; Adams, S.C. The configuration of some cupric, nickelous and cobaltous complexes by means of magnetic measurements. J. Am. Chem. Soc. 1940, 62, 1228-1229
Cotton, F.A.; Holm, R.H. Magnetic investigations of spin-free cobaltous complexes 3. On the existence of planar complexes. J. Am. Chem. Soc. 1960, 82, 2979-2983
Banerjee, S.; Domenichelli, I.; Ameduri, B. Nitroxide-Mediated Alternating Copolymerization of Vinyl Acetate with tert-Butyl-2-trifluoromethacrylate Using a SG1-Based Alkoxyamine. ACS Macro Lett. 2016, 5, 1232-1236
Banerjee, S.; Ladmiral, V.; Debuigne, A.; Detrembleur, C.; Rahaman, S.M.W.; Poli, R.; Améduri, B. Organometallic-Mediated Alternating Radical Copolymerization of tert-Butyl-2-trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof. Macromol. Rapid Commun. 2017, 38, 1700203
Patil, Y.; Ameduri, B. Advances in the (Co)polymerization of Alkyl 2-Trifluoromethacrylates and 2-(Trifluoromethyl)acrylic Acid. Prog. Polym. Sci. 2013, 38, 703-739
Tillet, G.; Boutevin, B.; Ameduri, B. Chemical reactions of polymer crosslinking and post-crosslinking at room and medium temperature. Prog. Polym. Sci. 2010, 36, 191-217
Banerjee, S.;Wehbi, M.; Manseri, A.; Mehdi, A.; Alaaeddine, A.; Hachem, A.; Ameduri, B. Poly(vinylidene fluoride) Containing Phosphonic Acid as Anticorrosion Coating for Steel. ACS Appl. Mater. Interfaces 2017, 9, 6433-6443
Soulestin, T.; Dos Santos Filho, P.M.; Ladmiral, V.; Lannuzel, T.; Domingues Dos Santos, F.; Ameduri, B. Ferroelectric fluorinated copolymers with improved adhesion properties. Polym. Chem. 2017, 8, 1017-1027
Maria, S.; Kaneyoshi, H.; Matyjaszewski, K.; Poli, R. Effect of Electron Donors on the Radical Polymerization of Vinyl Acetate Mediated by Co(acac)2: Degenerative transfer versus reversible homolytic cleavage of an organocobalt(III) complex. Chem. Eur. J. 2007, 13, 2480-2492
Debuigne, A.; Champouret, Y.; Jérôme, R.; Poli, R.; Detrembleur, C. Mechanistic Insights into Cobalt Mediated Radical Polymerization (CMRP) of Vinyl Acetate via Cobalt(III) Adducts as Initiators. Chem. Eur. J. 2008, 14, 4046-4059
Kharas, G.; Kohn, D.H. Characterization of copolymers of vinyl acetate with ethyl α-cyanocinnamate. J. Polym. Sci. Part A Polym. Chem. 1984, 22, 577-582
Kharas, G.; Kohn, D.H. Copolymerization of vinyl acetate with benzylidenemalononitrile. J. Polym. Sci. Part A Polym. Chem. 1984, 22, 583-588
Kochi, T.; Nakamura, A.; Ida, H.; Nozaki, K. Alternating Copolymerization of Vinyl Acetate with Carbon Monoxide. J. Am. Chem. Soc. 2007, 129, 7770-7771
Patil, Y.; Améduri, B. First RAFT/MADIX radical copolymerization of tert-butyl 2-trifluoromethacrylate with vinylidene fluoride controlled by xanthate. Polym. Chem. 2013, 4, 2783-2799