Vegetable-based building-blocks for the synthesis of thermoplastic renewable polyurethanes and polyesters

European Journal of Lipid Science and Technology

Volumn 115, Issue 1, 2013, Pages 61-75

  More, Arvind S ^a,b   Maisonneuve, Lise ^a,b   Lebarbé, Thomas ^a,b   Gadenne, Benoit ^c   Alfos, Carine ^c   Cramail, Henri ^a,b  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITÉ BORDEAUX 1   (France)

^c Institut des Corps Gras   (France)

Author keywords

Methyl oleate; Methyl undecenoate; Thermoplastic polyesters; Thermoplastic polyurethanes; Vegetable oils

Indexed keywords

EID: 84870889882     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201200172     Document Type: Article

References (53)

1. Tschan, M. J.-L., Brulé, E., Haquette, P., Thomas, C. M., Synthesis of biodegradable polymers from renewable resources. Polym. Chem. 2012, 3, 836- 851.
2. Belgacem, M. N., Gandini, A., (Eds.), In Monomers, Polymers and Composites From Renewable Resources, Elsevier, Amsterdam 2008.
3. Williams, C. K., Hillmyer, M. A., Polymers from renewable resources: A perspective for a special issue of polymer reviews. Polym. Rev. 2008, 48, 1- 10.
4. Dodds, D. R., Gross, R. A., Chemicals from biomass. Science. 2007, 318, 1250- 1251.
5. Meier, M. A. R., Metzger, J. O., Schubert, U. S., Plant oil renewable resources as green alternatives in polymer science. Chem. Soc. Rev. 2007, 36, 1788- 1802.
6. Gandini, A., Polymers from renewable resources: A challenge for the future of macromolecular materials. Macromolecules 2008, 41, 9491- 9504.
7. Vennestrøm, P. N. R., Osmundsen, C. M., Christensen, C. H., Taarning, E., Beyond petrochemicals: The renewable chemicals industry. Angew. Chem. Int. Ed. 2011, 50, 10502- 10509.
8. Biermann, U., Friedt, W., Lang, S., Lühs, W. et al., New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew. Chem. Int. Ed. 2000, 39, 2206- 2224.
9. Biermann, U., Bornscheuer, U., Meier, M. A. R., Metzger, J. O., Schäfer, H. J., Oils and fats as renewable raw materials in chemistry. Angew. Chem. Int. Ed. 2011, 50, 3854- 3871.
10. De Espinosa, L. M., Meier, M. A. R., Plant oils: The perfect renewable resource for polymer science. Eur. Polym. J. 2011, 47, 837- 852.
11. Lligadas, G., Ronda, J. C., Galià, M., Càdiz, V., Plant oils as platform chemicals for polyurethane synthesis: Current state-of-the-art. Biomacromolecules 2010, 11, 2825- 2835.
12. Pfister, D. P., Xia, Y., Larock, R. C., Recent advances in vegetable oil-based polyurethanes. ChemSusChem 2011, 4, 703- 717.
13. Xia, Y., Larock, R. C., Vegetable oils based polymeric materials: Synthesis, properties and applications. Green Chem. 2010, 12, 1893- 1909.
14. Petrović, Z. S., Cvetkovic, I., Hong, D., Wan, X. et al., Polyester polyols and polyurethanes from ricinoleic acid. J. Appl. Polym. Sci. 2008, 108, 1184- 1190.
15. Petrović, Z. S., Cvetkovic, I., Hong, D., Wan, X. et al., Vegetable oil-based triols from hydroformylated fatty acids and polyurethane elastomers. Eur. J. Lipid Sci. Technol. 2010, 112, 97- 102.
16. Desroches, M., Caillol, S., Auvergne, R., Boutevin, B., David, G., Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling. Polym. Chem. 2012, 3, 450- 457.
17. Lee, C. S., Ooi, T. L., Chuah, C. H., Ahmad, S., Rigid polyurethane foam production from palm oil-based epoxidized diethanolamides. J. Am. Oil Chem. Soc. 2007, 84, 1161- 1167.
18. Zlatanić, A., Petrović, Z. S., Dusek, K., Structure and properties of triolein-based polyurethane networks. Biomacromolecules 2002, 3, 1048- 1056.
19. Desroches, M., Escouvois, M., Auvergne, R., Caillol, S., Boutevin, B., From vegetable oils to polyurethanes: Synthetic routes to polyols and main industrial products. Polym. Rev. 2012, 52, 38- 79.
20. Guo, A., Javni, I., Petrovic, Z. S., Rigid polyurethane foams based on soybean oil. J. Appl. Polym. Sci. 2000, 77, 467- 473.
21. Petrović, Z. S., Zhang, W., Javni, I., Structure and properties of polyurethanes prepared from triglyceride polyols by ozonolysis. Biomacromolecules 2005, 6, 713- 719.
22. Bähr, M., Mülhaupt, R., Linseed and soybean oil-based polyurethanes prepared via the non-isocyanate route and catalytic carbon dioxide conversion. Green Chem. 2012, 14, 483- 489.
23. Rybak, A., Fokou, P. A., Meier, M. A. R., Metathesis as a versatile tool in oleochemistry. Eur. J. Lipid Sci. Technol. 2008, 110, 797- 804.
24. Biermann, U., Metzger, J. O., Meier, M. A. R., Acrylic triene metathesis oligo- and polymerization of high oleic sunflower oil. Macromol. Chem. Phys. 2010, 211, 854- 862.
25. Desroches, M., Caillol, S., Lapinte, V., Auvergne, R., Boutevin, B., Synthesis of biobased polyols by thiol-ene ciupling from vegetable oils. Macromolecules 2011, 44, 2489- 2500.
26. Hojabri, J., Kong, X., Narine, S. S., Functional thermoplastics from linear diols and diisocyanates produced entirely from renewable lipid sources. Biomacromolecules 2010, 11, 911- 918.
27. Kong, X., Narine, S. S., Physical properties of polyurethanes plastic sheets produced from polyols from canola oil. Biomacromolecules 2007, 8, 2203- 2209.
28. Lligadas, G., Ronda, J. C., Galià, M., Càdiz, V., Poly(ether urethane) networks from renewable resources as candidate biomaterials: Synthesis and characterization. Biomacromolecules 2007, 8, 686- 692.
29. Lligadas, G., Ronda, J. C., Galià, M., Càdiz, V., Novel silicon-containing polyurethanes from vegetable oils as renewable resources: Synthesis and properties. Biomacromolecules 2006, 7, 2420- 2426.
30. Lligadas, G., Ronda, J. C., Galià, M., Càdiz, V., Polyurethane networks from fatty-acid-based aromatic triols: Synthesis and characterization. Biomacromolecules 2007, 8, 1858- 1864.
31. Rybak, A., Meier, M. A. R., Cross-metathesis of fatty acid derivatives with methyl acrylate: Renewable raw materials for the chemical industry. Green Chem. 2007, 9, 1356- 1361.
32. Rybak, A., Meier, M. A. R., Cross-metathesis of oleyl alcohol with methyl acrylate: Optimization of reaction conditions and comparison of their environmental impact. Green Chem. 2008, 10, 1099- 1104.
33. Türünc, O., Meier, M. A. R., Fatty acid derived monomers and related polymers via thiol-ene (click) additions. Macromol. Rapid Commun. 2010, 31, 1822- 1826.
34. Quinzler, D., Mecking, S., Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization. Angew. Chem. Int. Ed. 2010, 49, 4306- 4308.
35. 2 and swelling studies by in situ IR spectroscopy of vegetable-based epoxidized oils as polyurethane precursors. Polym. Chem. 2012, 3, 525- 532.
36. 2 and carbonation studies of epoxidized fatty acid diesters: Towards novel precursors for polyurethanes synthesis. Green Chem. 2010, 12, 2205- 2213.
37. Palaskar, D. V., Boyer, A., Cloutet, E., Alfos, C., Cramail, H., Synthesis of biobased polyurethane from oleic and ricinoleic acids as the renewable resources via the AB-type self-condensation approach. Biomacromolecules 2010, 11, 1202- 1211.
38. Palaskar, D. V., Boyer, A., Cloutet, E., Le Meins, J. F. et al., Original diols from sunflower and ricin oils: Synthesis, characterization, and use as polyurethane building blocks. J. Polym. Sci. Polym. Chem. 2012, 50, 1766- 1782.
39. More, A. S., Palaskar, D. V., Cloutet, E., Gadenne, B. et al., Aliphatic polycarbonates and poly(ester carbonate)s from fatty acid derived monomers. Polym. Chem. 2011, 2, 2796- 2803.
40. More, A. S., Gadenne, B., Alfos, C., Cramail, H., AB type polyaddition route to thermoplastic polyurethanes from fatty acid derivatives. Polym. Chem. 2012, 3, 1594- 1605.
41. Maisonneuve, L., Lebarbé, T., Nguyen, N., Gadenne, B. et al., Hydroxyl telechelic building blocks from fatty acid methyl esters for the synthesis of poly(ester/amide urethane)s with versatile properties. Polym. Chem. 2012, 3, 2583- 2595.
42. Cramail, H., Boyer, A., Cloutet, E., Alfos, C., WO 2011045536, 2011.
43. Cramail, H., Boyer, A., Cloutet, E., Alfos, C., WO 2011030075, 2011.
44. Cramail, H., Boyer, A., Cloutet, E., Bakhiyi, R., Alfos, C., WO 2011030076, 2011.
45. González-Paz, R. J., Lluch, C., Lligadas, G., Ronda, J. C. et al., A green approach toward oleic- and undecylenic acid-derived polyurethanes. J. Polym. Sci. Polym. Chem. 2011, 49, 2407- 2416.
46. Lluch, C., Ronda, J. C., Galiá, M., Lligadas, G., Cádiz, V., Rapid approach to biobased telechelics through two one-pot thiol-ene click reactions. Biomacromolecules 2010, 11, 1646- 1653.
47. Perrin, D. D., Armarego, W. L. F., Purification of Laboratory Chemicals, Pergamon Press, New York 1989.
48. Ngo, H., Jones, K., Foglia, T., Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α, ω-dicarboxylic acids. J. Am. Oil Chem. Soc. 2006, 83, 629- 634.
49. Trzaskowski, J., Quinzler, D., Bährle, C., Mecking, S., Aliphatic long-chain C20 polyesters from olefin metathesis. Macromol. Rapid Commun. 2011, 32, 1352- 1356.
50. Türünç, O., de Espinosa, L. M., Meier, M. A. R., Renewable polyethylene mimics derived from castor oil. Macromol. Rapid Commun. 2011, 32, 1357- 1361.
51. Sormana, J. L., Meredith, J. C., High-throughput discovery of structure-mechanical property relationship of segmented poly(urethane urea)s. Macromolecules 2004, 37, 2186- 2195.
52. Mattia, J., Painter, P., A comparison of hydrogen bonding and order in a polyurethane and poly(urethane urea) and their blends with poly(ethylene glycol). Macromolecules 2007, 40, 1546- 1554.
53. Braun, D., Cherdron, H., Rehahn, M., Ritter, H., Voit, B., Polymer Synthesis: Theory and Practice: Fundamentals, Methods, Experiments, Springer-Verlag, Berlin Heidelberg 2005.