Precision design of ethylene- and polar-monomer-based copolymers by organometallic-mediated radical polymerization

Nature Chemistry

Volumn 6, Issue 3, 2014, Pages 179-187

  Kermagoret, Anthony ^a   Debuigne, Antoine ^a   Jérôme, Christine ^a   Detrembleur, Christophe ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE; ETHYLENE DERIVATIVE; ORGANOMETALLIC COMPOUND; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; POLYMERIZATION;

ETHYLENES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POLYMERIZATION; POLYMERS;

EID: 84895170476     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1850     Document Type: Article

References (67)

1. Burkhart, R. D. & Zutty, N. L. Copolymerization studies. III. Reactivity ratios of model ethylene copolymerizations and their use in Q-e calculations. J. Polym. Sci. A 1, 1137-1145 (1963).
2. Mayo, F. R. & Lewis, F. M. Copolymerization. I. A basis for comparing the behavior of monomers in copolymerization; the copolymerization of styrene and methyl methacrylate. J. Am. Chem. Soc. 66, 1594-1601 (1944).
3. Espí, E., Salmerón, A., Fontecha, A., García, Y. & Real, A. I. Plastic films for agricultural applications. J. Plast. Film Sheeting 22, 85-102 (2006).
4. Franssen, N.M. G., Reek, J. N. H. & de Bruin, B. Synthesis of functional 'polyolefins': state of the art and remaining challenges. Chem. Soc. Rev. 42, 5809-5832 (2013)
5. Ghiass, M. & Hutchinson, R. A. Simulation of free radical high-pressure copolymerization in a multizone autoclave: model development and application. Polym. React. Eng. 11, 989-1015 (2003).
6. Filley, J., McKinnon, J. T., Wu, D. T. & Ko, G. H. Theoretical study of ethylene-vinyl acetate free-radical copolymerization: reactivity ratios, penultimate effects, and relative rates of chain transfer to polymer. Macromolecules 35, 3731-3738 (2002). (Pubitemid 34590351)
7. 2. Ind. Eng. Chem. Res. 48, 1384-1390 (2009).
8. Boffa, L. S. & Novak, B. M. Copolymerization of polar monomers with olefins using transition-metal complexes. Chem. Rev. 100, 1479-1493 (2000).
9. Nakamura, A., Ito, S. & Nozaki, K. Coordination-insertion copolymerization of fundamental polar monomers. Chem. Rev. 109, 5215-5244 (2009).
10. Liu, S. & Sen, A. Living/controlled copolymerization of acrylates with nonactivated alkenes. J. Polym. Sci. A 42, 6175-6192 (2004). (Pubitemid 40002593)
11. Ito, S. et al. Coordination-insertion copolymerization of allyl monomers with ethylene. J. Am. Chem. Soc. 133, 1232-1235 (2011).
12. Berkefeld, A. et al. Functional group tolerant polymerization catalysis. Polym. Prepr. 51, 367 (2010).
13. Nakamura, A. et al. Ortho-phosphonebenzenesulfonate: a superb ligand for palladium-catalyzed coordination-insertion copolymerization of polar vinyl monomers. Acc. Chem. Res. 46, 1438-1449 (2013).
14. II) alkyl complexes: identification of problems connected with copolymerizations of these monomers with ethylene. J. Am. Chem. Soc. 127, 5132-5146 (2005). (Pubitemid 40523473)
15. Ito, S., Munakata, K., Nakamura, A. & Nozaki, K. Copolymerization of vinyl acetate with ethylene by palladium/alkylphosphine-sulfonate catalysts. J. Am. Chem. Soc. 131, 14606-14607 (2009).
16. II) complexes. J. Am. Chem. Soc. 127, 1854-1869 (2005). (Pubitemid 40229168)
17. Wu, F., Foley, S. R., Burns, C. T. & Jordan, R. F. Acrylonitrile insertion reactions of cationic palladium alkyl complexes. J. Am. Chem. Soc. 127, 1841-1853 (2005). (Pubitemid 40229167)
18. Kochi, T., Noda, S., Yoshimura, K. & Nozaki, K. Formation of linear copolymers of ethylene and acrylonitrile catalyzed by phosphine sulfonate palladium complexes. J. Am. Chem. Soc. 129, 8948-8949 (2007). (Pubitemid 47171828)
19. Rünzi, T., Fröhlich, D. & Mecking, S. Direct synthesis of ethylene-acrylic acid copolymers by insertion polymerization. J. Am. Chem. Soc. 132, 17690-17691 (2010).
20. II) complexes. Organometallics 31, 8505-8515 (2012).
21. Friedberger, T., Wucher, P. & Mecking, S. Mechanistic insights into polar monomer insertion polymerization from acrylamides. J. Am. Chem. Soc. 134, 1010-1018 (2012).
22. Leicht, H., Göttker-Schnetmann, I. & Mecking, S. Incorporation of vinyl chloride in insertion polymerization. Angew. Chem. Int. Ed. 52, 3963-3966 (2013).
23. Szabo, M. J. et al. Polar copolymerization by a palladium-diimine-based catalyst. Influence of the catalyst charge and polar substituent on catalyst poisoning and polymerization activity. A density functional theory study. Organometallics 23, 5565-5572 (2004).
24. Sen, A. & Borkar, S. Perspective on metal-mediated polar monomer/alkene copolymerization. J. Organomet. Chem. 692, 3291-3299 (2007). (Pubitemid 46899100)
25. 2C=CHX. Angew. Chem. Int. Ed. 47, 2538-2542 (2008).
26. Liu, S., Elyashiv, S. & Sen, A. Copper-mediated controlled copolymerization of methyl acrylate with 1-alkenes under mild conditions. J. Am. Chem. Soc. 123, 12738-12739 (2001). (Pubitemid 33140423)
27. Venkatesh, R. & Klumperman, B. Olefin copolymerization via controlled radical polymerization: copolymerization of methyl methacrylate and 1-octene. Macromolecules 37, 1226-1233 (2004).
28. Venkatesh, R., Harrisson, S., Haddleton, D. M. & Klumperman, B. Olefin copolymerization via controlled radical polymerization: copolymerization of acrylate and 1-octene. Macromolecules 37, 4406-4416 (2004).
29. Venkatesh, R., Vergouwen, F. & Klumperman, B. Atom transfer radical copolymerization of a-olefins with methyl acrylate: determination of activation rate parameters. Macromol. Chem. Phys. 206, 547-552 (2005). (Pubitemid 40811976)
30. Tanaka, K. & Matyjaszewski, K. Controlled copolymerization of n-butyl acrylate with nonpolar 1-alkenes using activators regenerated by electron transfer for atom-transfer radical polymerization. Macromolecules 40, 5255-5260 (2007). (Pubitemid 47210148)
31. Liu, S., Gu, B., Rowlands, H. A. & Sen, A. Controlled random and alternating copolymerization of methyl acrylate with 1-alkenes. Macromolecules 37, 7924-7929 (2004).
32. Venkatesh, R., Staal, B. B. P. & Klumperman, B. Olefin copolymerization via reversible addition-fragmentation chain transfer. Chem. Commun. 1554-1555 (2004). (Pubitemid 38969097)
33. Gu, B., Liu, S., Leber, J. D. & Sen, A. Nitroxide-mediated copolymerization of methyl acrylate with 1-alkenes and norbornenes. Macromolecules 37, 5142-5144 (2004).
34. Mishima, E., Tamura, T. & Yamago, S. Controlled copolymerization of 1-octene and (meth)acrylates via organotellurium-mediated living radical polymerization (TERP). Macromolecules 45, 8998-9003 (2012).
35. Bryaskova, R. et al. Copolymerization of vinyl acetate with 1-octene and ethylene by cobalt-mediated radical polymerization. J. Polym. Sci. A 45, 2532-2542 (2007). (Pubitemid 46910855)
36. Borkar, S. & Sen, A. Controlled copolymerization of vinyl acetate with 1-alkenes and their fluoro derivatives by degenerative transfer. J. Polym. Sci. A 43, 3728-3736 (2005). (Pubitemid 41482335)
37. Poli, R. Relationship between one-electron transition-metal reactivity and radical polymerization processes. Angew. Chem. Int. Ed. 45, 5058-5070 (2006).
38. Debuigne, A., Poli, R., Jérôme, C., Jérôme, R. & Detrembleur, C. Overview of cobalt-mediated radical polymerization: roots, state of the art and future prospects. Prog. Polym. Sci. 34, 211-239 (2009).
39. Hurtgen, M., Detrembleur, C., Jérôme, C. & Debuigne, A. Insight into organometallic-mediated radical polymerization. Polym. Rev. 51, 188-213 (2011).
40. Allan, L. E. N., Perry, M. R. & Shaver, M. P. Organometallic mediated radical polymerization. Prog. Polym. Sci. 37, 127-156 (2012).
41. III) adducts as initiators. Chem. Eur. J. 14, 4046-4059 (2008).
42. Gospodinova, N., Terlemezyan, L., Hihailov, M., Men, H. U. & Du, K. B. Microstructure of ethylene-(vinyl acetate) copolymers prepared by emulsion copolymerization. Eur. Polym. J. 28, 961-967 (1992).
43. Savant, D. M., Reddy, D. V., McCord, E. F. & Rinaldi, P. L. 2D NMR studies of poly(ethylene-co-vinyl acetate-co-carbon monoxide). Macromolecules 40, 4199-4210 (2007). (Pubitemid 47012575)
44. Ibrahim, B., Katritzky, A. R., Smith, A. & Weiss, D. E. Carbon-13 nuclear magnetic resonance spectroscopy of polymers. I. High resolution carbon-13 nuclear magnetic resonance spectroscopy. Tacticity studies on poly(vinyl acetate) and monomer distribution analysis in ethylene-vinyl acetate copolymers. J. Chem. Soc. Perkin Trans. 2 1537-1542 (1974).
45. Sung, H. N. & Noggle, J. H. Carbon-13 NMR of poly(vinyl acetate) and ethylene-vinyl acetate copolymer. J. Polym. Sci. Polym. Phys. Ed. 19, 1593-1602 (1981). (Pubitemid 12445581)
46. Usami, T. & Takayama, S. Fine-branching structure in high-pressure, lowdensity polyethylenes by 50.10 MHz carbon-13 NMR analysis. Macromolecules 17, 1756-1761 (1984).
47. Britton, D., Heatley, F. & Lovell, P. A. Chain transfer to polymer in free-radical bulk and emulsion polymerization of vinyl acetate studied by NMR spectroscopy. Macromolecules 31, 2828-2837 (1998). (Pubitemid 128557251)
48. McCord, E. F., Shaw, W. H. Jr & Hutchinson, R. A. short-chain branching structures in ethylene copolymers prepared by high-pressure free-radical polymerization: an NMR analysis. Macromolecules 30, 246-256 (1997). (Pubitemid 127574347)
49. Britton, D. J., Lovell, P. A., Heatley, F. & Venkatesh, R. Chain transfer to polymer in emulsion copolymerizations. Macromol. Symp. 175, 95-104 (2001).
50. 2-mediated polymerization so much better? Macromolecules 46, 4303-4312 (2013).
51. Debuigne, A. et al. Key role of intramolecular metal chelation and hydrogen bonding in the cobalt-mediated radical polymerization of N-vinyl amides. Chem. Eur. J. 18, 12834-12844 (2012).
52. Brandrup, J., Immergut, E. H. & Grulke, E. A. Polymer Handbook 4th edn (Wiley, 1999).
53. g of two different types of aqueous polymers. Macromol. Chem. Phys. 203, 2481-2487 (2002).
54. Debuigne, A., Jérôme, C. & Detrembleur, C. Isoprene-assisted radical coupling of (co)polymers prepared by cobalt-mediated radical polymerization. Angew. Chem. Int. Ed. 48, 1422-1424 (2009).
55. Debuigne, A. et al. Interpolymer radical coupling: a toolbox complementary to controlled radical polymerization. Prog. Polym. Sci. 37, 1004-1030 (2012).
56. Debuigne, A. et al. Cobalt-mediated radical coupling (CMRC): an unusual route to midchain-functionalized symmetrical macromolecules. Chem. Eur. J. 16, 1799-1811 (2010).
57. Poli, R. Radical Coordination chemistry and its relevance to metal-mediated radical polymerization. Eur. J. Inorg. Chem. 1513-1530 (2011).
58. Leblanc, A. et al. Homo- and copolymerizations of (meth)acrylates with olefins (styrene, ethylene) using neutral nickel complexes: a dual radical/catalytic pathway. Macromolecules 44, 3293-3301 (2011).
59. Mori, Y., Sumi, H., Hirabayashi, T., Inai, Y. & Yokota, K. Synthesis of sequenceordered copolymers. 4. Glass transition and melting temperatures of sequenceordered and unordered ethylene-vinyl alcohol and ethylene-vinyl acetate copolymers. Macromolecules 27, 1051-1056 (1994).
60. Qi, X-J., Li, Z., Fu, Y., Guo, Q-X. & Liu, L. Anti-spin- delocalization effect in Co-C bond dissociation enthalpies. Organometallics 27, 2688-2698 (2008).
61. Van, C. K., Van, S. V., Vansteenkiste, P., Reyniers, M-F. & Waroquier, M. Ab initio study of free-radical polymerization: polyethylene propagation kinetics. Chem Phys Chem 7, 131-140 (2006).
62. Aggarwal, S. L. & Sweeting, O. J. Polyethylene: preparation, structure, and properties. Chem. Rev. 57, 665-742 (1957).
63. Grau, E., Broyer, J-P., Boisson, C., Spitz, R. & Monteil, V. Free ethylene radical polymerization under mild conditions: the impact of the solvent. Macromolecules 42, 7279-7281 (2009).
64. Grau, E., Broyer, J-P., Boisson, C., Spitz, R. & Monteil, V. Unusual activation by solvent of the ethylene free radical polymerization. Polym. Chem. 2, 2328-2333 (2011).
65. Boaen, N. K. & Hillmyer, M. A. Post-polymerization functionalization of polyolefins. Chem. Soc. Rev. 34, 267-275 (2005). (Pubitemid 40444407)
66. Prinos, J., Bikiaris, D., Theologidis, S. & Panayiotou, C. Preparation and characterization of LDPE/starch blends containing ethylene/vinyl acetate copolymer as compatibilizer. Polym. Eng. Sci. 38, 954-964 (1998). (Pubitemid 128597843)
67. Debuigne, A., Caille, J-R. & Jérôme, R. Synthesis of end-functional poly(vinyl acetate) by cobalt-mediated radical polymerization. Macromolecules 38, 5452-5458 (2005). (Pubitemid 41028113)