Grafting onto a renewable unsaturated polyester via thiol-ene chemistry and cross-metathesis

European Polymer Journal

Volumn 49, Issue 4, 2013, Pages 843-852

  Kolb, Nicolai ^a   Meier, Michael A R ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Malonate; Methyl 10 undecenoate; Olefin cross metathesis; Passerini; Renewable polyester; thiol ene

Indexed keywords

MALONATES; METHYL 10-UNDECENOATE; OLEFIN CROSS-METATHESIS; PASSERINI; THIOL-ENES;

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; SODIUM COMPOUNDS;

GRAFTING (CHEMICAL);

EID: 84875211985     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2012.09.017     Document Type: Article

References (33)

1. M.A.R. Meier, J.O. Metzger, and U.S. Schubert Plant oil renewable resources as green alternatives in polymer science Chem Soc Rev 36 11 2007 1788 1802
2. U. Biermann, U. Bornscheuer, M.A.R. Meier, J.O. Metzger, and H.J. Schäfer Oils and fats as renewable raw materials in chemistry Angew Chem Int Ed 50 17 2011 3854 3871
3. N. Kolb, and M.A.R. Meier Monomers and their polymers derived from saturated fatty acid methyl esters and dimethyl carbonate Green Chem 14 9 2012 2429 2435
4. J. Samuelsson, M. Jonsson, T. Brinck, and M. Johansson thiol-ene coupling reaction of fatty acid monomers J Polym Sci Part A Polym Chem 42 24 2004 6346 6352
5. O. Türünç, and M.A.R. Meier Fatty acid derived monomers and related polymers via thiol-ene (Click) additions Macromol Rapid Commun 31 20 2010 1822 1826
6. M. Stemmelen, F. Pessel, V. Lapinte, S. Caillol, J.P. Habas, and J.J. Robin A fully biobased epoxy resin from vegetable oils: from the synthesis of the precursors by thiol-ene reaction to the study of the final material J Polym Sci Part A Polym Chem 49 11 2011 2434 2444
7. O. Turunc, and M.A.R. Meier thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers Green Chem 13 2 2011 314 320
8. M. Desroches, S. Caillol, R. Auvergne, and B. Boutevin Synthesis of pseudo-telechelic diols by transesterification and thiol-ene coupling Eur J Lipid Sci Technol 114 1 2012 84 91
9. M. Desroches, S. Caillol, R. Auvergne, B. Boutevin, and G. David Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling Polym Chem 3 2 2012 450 457
10. O. Turunc, M. Firdaus, G. Klein, and M.A.R. Meier Fatty acid derived renewable polyamides via thiol-ene additions Green Chem 14 9 2012 2577 2583
11. A. Rybak, and M.A.R. Meier Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry Green Chem 9 12 2007 1356 1361
12. A. Rybak, and M.A.R. Meier Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact Green Chem 10 10 2008 1099 1104
13. R. Malacea, C. Fischmeister, C. Bruneau, J.-L. Dubois, J.-L. Couturier, and P.H. Dixneuf Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile Green Chem 11 2 2009 152 155
14. M.A.R. Meier Metathesis with oleochemicals: new approaches for the utilization of plant oils as renewable resources in polymer science Macromol Chem Phys 210 13-14 2009 1073 1079
15. H. Mutlu, and M.A.R. Meier Unsaturated PA X,20 from renewable resources via metathesis and catalytic amidation Macromol Chem Phys 210 12 2009 1019 1025
16. X. Miao, R. Malacea, C. Fischmeister, C. Bruneau, and P.H. Dixneuf Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain bifunctional and amino acid compounds Green Chem 13 10 2011 2911 2919
17. X. Miao, C. Fischmeister, P.H. Dixneuf, C. Bruneau, J.L. Dubois, and J.L. Couturier Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis Green Chem. 2012
18. C. Jiménez-Rodriguez, G.R. Eastham, and D.J. Cole-Hamilton Dicarboxylic acid esters from the carbonylation of unsaturated esters under mild conditions Inorg Chem Commun 8 10 2005 878 881
19. M.R.L. Furst, R.L. Goff, D. Quinzler, S. Mecking, C.H. Botting, and D.J. Cole-Hamilton Polymer precursors from catalytic reactions of natural oils Green Chem 14 2 2012 472 477
20. H. Mutlu, and M.A.R. Meier Castor oil as a renewable resource for the chemical industry Eur J Lipid Sci Technol 112 1 2010 10 30
21. N. ten Brummelhuis, C. Diehl, and H. Schlaad Thiol-ene modification of 1,2-polybutadiene using UV light or sunlight Macromolecules 41 24 2008 9946 9947
22. R.L.A. David, and J.A. Kornfield Facile, efficient routes to diverse protected thiols and to their deprotection and addition to create functional polymers by thiol-ene coupling Macromolecules 41 4 2008 1151 1161
23. L.M. Campos, K.L. Killops, R. Sakai, J.M.J. Paulusse, D. Damiron, and E. Drockenmuller Development of thermal and photochemical strategies for thiol-ene click polymer functionalization Macromolecules 41 19 2008 7063 7070
24. A. Gress, A. Völkel, and H. Schlaad Thio-click modification of poly[2-(3-butenyl)-2-oxazoline] Macromolecules 40 22 2007 7928 7933
25. K. Kempe, R. Hoogenboom, and U.S. Schubert A green approach for the synthesis and thiol-ene modification of alkene functionalized poly(2-oxazoline)s Macromol Rapid Commun 32 18 2011 1484 1489
26. L. Montero de Espinosa, K. Kempe, U.S. Schubert, R. Hoogenboom, and M.A.R. Meier Side-chain modification and grafting onto via olefin cross-metathesis Macromol Rapid Commun 2012 10.1002/marc.20120048
27. A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs A general model for selectivity in olefin cross metathesis J Am Chem Soc 125 37 2003 11360 11370
28. J.A. Love, J.P. Morgan, T.M. Trnka, and R.H. Grubbs A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile Angew Chem Int Ed 41 21 2002 4035 4037
29. M.B. Dinger, and J.C. Mol Degradation of the first-generation grubbs metathesis catalyst with primary alcohols, water, and oxygen. formation and catalytic activity of ruthenium(II) monocarbonyl species Organometallics 22 5 2003 1089 1095
30. A. Dondoni The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry Angew Chem Int Ed 47 47 2008 8995 8997
31. J. Sun, and H. Schlaad Thiol-ene clickable polypeptides Macromolecules 43 10 2010 4445 4448
32. L. Banfi, and R. Riva The passerini reaction Organic reactions 2004 John Wiley & Sons, Inc.
33. O. Kreye, T. Tóth, and M.A.R. Meier Introducing multicomponent reactions to polymer science. Passerini reactions of renewable monomers J Am Chem Soc 133 6 2011 1790 1792