Synthesis of new polyurethanes from vegetable oil by thiol-ene coupling

Green Materials

Volumn 1, Issue 1, 2013, Pages 16-26

  Caillol, Sylvain ^a   Desroches, Myriam ^a   Carlotti, Stéphane ^b   Auvergne, Rémi ^a   Boutevin, Bernard ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Click chemistry; Green polymers; Renewable resources; Sustainable materials

Indexed keywords

ALCOHOLS; DIFFERENTIAL SCANNING CALORIMETRY; MATERIALS PROPERTIES; MIXTURES; POLYMERIZATION; SIZE EXCLUSION CHROMATOGRAPHY; SOYBEAN OIL; TENSILE TESTING; THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS;

CLICK CHEMISTRY; GREEN POLYMERS; HYDROXYL FUNCTIONS; RENEWABLE RESOURCE; STEP-GROWTH POLYMERIZATIONS; SUSTAINABLE MATERIALS; THERMAL AND MECHANICAL PROPERTIES; THIOL-ENE COUPLING;

POLYURETHANES;

EID: 85041644299     PISSN: 20491220     EISSN: 20491239     Source Type: Journal    
DOI: 10.1680/gmat.12.00001     Document Type: Article

References (60)

1. Koopmans, R. J. R&D challenges for the 21st century. Soft Matter 2006, 2, 537–543.
2. Gonzalez-Paz, R. J.; Lluch, C.; Lligadas, G.; Ronda, J. C.; Galia, M.; Cadiz, V. A green approach toward oleic and undecylenic acid-based polyurethanes. Journal of Polymer Science Part A: Polymer Chemistry 2011, 49, 2407–2416.
3. Biermann, U.; Bornscheuer, U.; Meier, M. A. R.; Metzger, J. O.; Schaefer, H. J. New developments for the chemical utilization of oils and fats as renewable raw materials. Angewandte Chemie-International Edition 2011, 50, 3854–3871.
4. Biermann, U.; Meier, M. A. R.; Butte, W.; Metzger, J. O. Cross-metathesis of unsaturated triglycerides with methyl acrylate: synthesis of a dimeric metathesis product. European Journal of Lipid Science and Technology 2011, 113, 39–45.
5. Meier, M. A. R.; Metzger, J. O.; Schubert, U. S. Plant oil renewable resources as green alternatives in polymer science. Chemical Society Reviews 2007, 36, 1788–1802.
6. Guner, F. S.; Erciyes, A. T.; Kabasakal, O. S.; Yagci, Y. New aspects on the modification of triglyceride oils. Recent Research Development in Oil Chemistry 1998, 2, 31–51.
7. Pfister, D. P.; Xia, Y.; Larock, R. C. Recent advances in vegetable oil-based polyurethanes. ChemSusChem 2011, 4, 703–717.
8. Cramail, H.; Boyer, A.; Cloutet, E.; Alfos, C. Novel method for preparing polyols by means of thiolation and products such as those obtained. 2009, FR2951166.
9. Cramail, H.; Boyer, A.; Cloutet, E.; Alfos, C. Novel castor oil derivatives and method for the production thereof. 2009, FR2950052.
10. Cramail, H.; Boyer, A.; Cloutet, E.; Bakhiyi, R.; Alfos, C. Novel method for preparing polyols and products obtained. 2009, FR2950051.
11. Lligadas, G.; Ronda, J. C.; Galia, M.; Cadiz, V. Oleic and undecylenic acids as renewable feedstocks in the synthesis of polyols and polyurethanes. Polymer 2010, 2, 440–453.
12. Scott Pattison, E. (ed.) Fatty acids and their industrial applications. New York: Marcel Dekker Inc, 1968.
13. Zanetti-Ramos, B. G.; Lemos-Senna, E.; Soldi, V.; Borsali, R.; Cloutet, E.; Cramail, H. Polyurethane nanoparticles from a natural polyol via miniemulsion technique. Polymer 2006, 47, 8080–8087.
14. Tu, Y-C.; Suppes, G. J.; Hsieh, F-H. Thermal and mechanical behavior of flexible polyurethane-molded plastic films and water-blown foams with epoxidized soybean oil. Journal of Applied Polymer Science Part A: Polymer Chemistry 2009, 111, 1311–1317.
15. Hablot, E.; Zheng, D.; Bouquey, M.; Avérous, L. Polyurethanes based on castor oil: kinetics, chemical, mechanical and thermal properties. Macromolecular Materials and Engineering 2008, 293, 922–929.
16. Liu, D.; Tian, H.; Zhang, L.; Chang, P. R. Structure and properties of blend films prepared from castor oil-based polyurethane/soy protein derivative. Industrial & Engineering Chemistry Research 2008, 47, 9330–9336.
17. Yeganeh, H.; Hojati-Talemi, P. Preparation and properties of novel biodegradable polyurethane networks based on castor oil and poly(ethylene glycol). Polymer Degradation and Stability 2007, 92, 480–489.
18. Gunstone, F. D. Chemical reactions of fatty acids with special reference to the carboxyl group. European Journal of Lipid Science and Technology 2001, 103, 307–314.
19. Stempfle, F.; Quinzler, D.; Heckler, I.; Mecking, S. Long-chain linear C19 and C23 monomers and polycondensatres from unsaturated fatty acid esters. Macromolecules 2011, 44, 4159–4166.
20. Schneider, M. P. Plant-oil-based lubricants and hydraulic fluids. Journal of the Science of Food and Agriculture 2006, 86, 1769–1780.
21. Corma, A.; Iborra, S.; Velty, A. Chemical routes for the transformation of biomass into chemicals. Chemical Reviews 2007, 107, 2411–2502.
22. Hwang, H-S.; Erhan, S. Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point. Journal of the American Oil Chemists Society 2001, 78, 1179–1184.
23. Cheong, M. Y.; Ooi, T. L.; Ahmad, S.; Yunus, W. M. Z. W.; Kuang, D. Synthesis and characterization of palm-based resin for UV coating. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2009, 111, 2353–2361.
24. Hu, Y. H.; Gao, Y.; Wang, D. N.; Hu, C. P.; Zu, S.; Vanoverloop, L.; Randall, D. Rigid polyurethane foam prepared from a rape seed oil based polyol. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2002, 84, 591–597.
25. Dahlke, B.; Hellbardt, S.; Paetow, M.; Zech, W. Polyhydroxy fatty acids and their derivatives from plant oils. Journal of the American Oil Chemists’ Society 1995, 72, 349–353.
26. Erhan, S. Z.; Adhvaryu, A.; Sharma, B. K. Poly(hydroxy thioether) vegetable oil derivatives useful as lubricant additives, US2006/0009365, USA, 2006.
27. Ionescu, M.; Petrović, Z.; Wan, X. Ethoxylated soybean polyols for polyurethanes. Journal of Polymers and the Environment 2007, 15, 237–243.
28. Sharma, B. K.; Adhvaryu, A.; Erhan, S. Z. Friction and wear behavior of thioether hydroxy vegetable oil. Tribology International 2009, 42, 353–358.
29. Hüseyin Esen, S. H. K.; Lu, G. Photolytic and free-radical polymerization of cinnamate esters of epoxidized plant oil triglycerides. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2003, 89, 3882–3888.
30. Miao, S.; Zhang, S.; Su, Z.; Wang, P. A novel vegetable oil-lactate hybrid monomer for synthesis of high-Tg polyurethanes. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2010, 48, 243–250.
31. Erhan, S. Z.; Sharma, B. K.; Liu, Z.; Adhvaryu, A. Lubricant base stock potential of chemically modified vegetable oils. Journal of Agricultural and Food Chemistry 2008, 56, 8919–8925.
32. Sharma, V.; Kundu, P. P. Condensation polymers from natural oils. Progress in Polymer Science 2008, 33, 1199–1215.
33. Petrovic, Z. S.; Zhang, W.; Javni, I. Structure and properties of polyurethanes prepared from triglyceride polyols by ozonolysis. Biomarcomolecules 2005, 6, 713–719.
34. Bantchev, G. B.; Kenar, J. A.; Biresaw, G.; Han, M. G. Free radical addition of butanethiol to vegetable oil double bonds. Journal of Agricultural and Food Chemistry 2009, 57, 1282–1290.
35. Eisner, A.; Perlstein, T.; Ault, W. Methanesulfonic acid-catalyzed additions IV. Additions to methyl linoleate. Journal of the American Oil Chemists’ Society 1964, 41, 557–558.
36. Schwab, A.; Gast, L.; Cowan, J. Free radical addition of hydrogen sulfide and thiols to linseed oil and methyl oleate. Journal of the American Oil Chemists’ Society 1968, 45, 461–464.
37. Wasson, J. I. Compositions containing and process for preparing stabilized unsaturated fatty oils, US 2522476 (S. O. D. Company), USA, 1950.
38. Samuelsson, J.; Jonsson, M.; Brinck, T.; Johansson, M. Thiol-ene coupling reaction of fatty acid monomers. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2004, 42, 6346–6352.
39. Stemmelen, M.; Pessel, F.; Lapinte, V.; Caillol, S.; Habas, J. P.; Robin, J. J. 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. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2011, 49, 2434–2444.
40. Hoyle, C. E.; Lee, T. Y.; Roper, T. Thiol-enes: chemistry of the past with promise for the future. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2004, 42, 5301–5338.
41. Campos, L. M.; Killops, K. L.; Sakai, R.; Paulusse, J. M. J.; Damiron, D.; Drockenmuller, E.; Messmore, B. W.; Hawker, C. J. Development of thermal and photochemical strategies for thiol-ene click polymer functionalization. Macromolecules 2008, 41, 7063–7070.
42. Cramer, N. B.; Reddy, S. K.; Cole, M.; Hoyle, C. E.; Bowman, C. N. Initiation and kinetics of thiol-ene photopolymerizations without photoinitiators. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2004, 42, 5817–5826.
43. Black, M.; Rawlins, J. W. Thiol-ene UV-curable coatings using vegetable oil macromonomers. European Polymer Journal 2009, 45, 1433–1441.
44. Sharma, B. K.; Adhvaryu, A.; Erhan, S. Z. Synthesis of hydroxy thio-ether derivatives of vegetable oil. Journal of Agricultural and Food Chemistry 2006, 54, 9866–9872.
45. Bexell, U.; Berger, R.; Olsson, M.; Grehk, T. M.; Sundell, P. E.; Johansson, M. Bonding of vegetable oils to mercapto silane treated metal surfaces: surface engineering on the nano scale. Thin Solid Films 2006, 515, 838–841.
46. Türünç, O.; Meier, M. A. R. Fatty acid derived monomers and related polymers via thiol-ene (click) additions. Macromolecular Rapid Communications 2010, 31, 1822–1826.
47. Desroches, M.; Caillol, S.; Lapinte, V.; Auvergne, R.; Boutevin, B. Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules 2011, 44, 2489–2500.
48. ten Brummelhuis, N.; Diehl, C.; Schlaad, H. Thiol-Ene modification of 1,2-polybutadiene using UV light or sunlight. Macromolecules 2008, 41, 9946–9947.
49. David, R. L. A.; Kornfield, J. A. Efficient routes to diverse protected thiols and to their deprotection and addition to create functional polymers by thiol-ene coupling. Macromolecules 2008, 41, 1151–1161.
50. Lotti, L.; Coiai, S.; Ciardelli, F.; Galimberti, M.; Passaglia, E. Thiol-ene radical addition of L-cysteine derivatives to low molecular weight polybutadiene. Macromolecular Chemistry and Physics 2009, 210, 1471–1483.
51. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angewandte Chemie, International Edition 2001, 40, 2004–2021.
52. Desroches, M.; Boutevin, B.; Caillol, S.; Auvergne, R. Synthesis of pseudo telechelic diols by trans-esterification and thiol-ene coupling from vegetable oil derivatives. European Journal of Lipid Science and Technology 2012, 114, 84–91.
53. Myriam, D.; Sylvain, C.; Bernard, B. Method for functionalizing natural fatty substances. FR 1002738, 2010, WO2012001315, 2012.
54. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. Cis trans isomerization of polyunsaturated fatty acid residues in phospholipids catalyzed by thiyl radicals. Journal of the American Chemical Society 2001, 123, 4459–4468.
55. Roper, T.; Guymon, C. A.; Jönsson, E. S.; Hoyle, C. E. Influence of the alkene structure on the mechanism and kinetics of thiol-alkene photopolymerizations with real-time infrared spectroscopy. Journal of Applied Polymer Science, Part A: Polymer Chemistry 2004, 42, 6283–6298.
56. Walling, C.; Helmreich, W. Reactivity and reversibility in the reaction of thiyl radicals with olefins. Journal of the American Chemical Society 1959, 81, 1144–1148.
57. Coates, J. Encyclopedia of Analytical Chemistry (Meyers, R. A. (ed)). Chichester: John Wiley & Sons Ltd, 2000, 10815–10837.
58. Danehy, J. P.; Oester, M. Y. Oxidation of organic divalent sulfur by iodine. I. Alternative pathways for thiols as determined by structure. Journal of Organic Chemistry 1967, 32, 1491–1495.
59. Chattopadhyay, D. K.; Webster, D. C. Thermal stability and flame retardancy of polyurethanes. Progress in Polymer Science 2009, 34, 1068–1133.
60. Shieh, Y. T.; Chen, H. T.; Liu, K. H.; Twu, Y. K. Thermal degradation of MDI-based segmented polyurethanes. Journal of Applied Polymer Science, Part A: Polymer Chemistry 1999, 37, 4126–4134.