Synthesis of biobased polyols by thiol-ene coupling from vegetable oils

Macromolecules

Volumn 44, Issue 8, 2011, Pages 2489-2500

  Desroches, Myriam ^a   Caillol, Sylvain ^a   Lapinte, Vincent ^a   Auvergne, Rémi ^a   Boutevin, Bernard ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2-MERCAPTOETHANOL; BIOBASED; BOND RATIO; DIISOCYANATES; DOUBLE BONDS; DOUBLE-BOND ISOMERIZATION; EXPERIMENTAL PARAMETERS; FUNCTIONALIZATIONS; FUNCTIONALIZED; HEXAMETHYLENE DIISOCYANATE; HYDROXYL FUNCTIONS; INTRAMOLECULAR BONDS; IODINE TITRATION; IRRADIATION INTENSITY; MODEL STUDY; OPTIMIZED CONDITIONS; PHOTO-INITIATOR; POLYMER NETWORKS; RADICAL ADDITION; RAPESEED OIL; ROOM TEMPERATURE; SIDE REACTIONS; THERMAL PROPERTIES; THIOL-ENE COUPLING; THIOL-ENE REACTIONS; THIOL-ENES; THIOL/ENE; UV INTENSITY; UV LIGHT; VINYL GROUP;

BYPRODUCTS; CARBOXYLIC ACIDS; ESTERS; GRAFTING (CHEMICAL); IODINE; LUBRICATING OILS; OILSEEDS; OLEIC ACID; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES; UNSATURATED FATTY ACIDS; VEGETABLE OILS;

ALCOHOLS;

EID: 79955018189     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma102884w     Document Type: Article

References (49)

1. Gunstone, F. D. Eur. J. Lipid Sci. Technol. 2001, 103, 307-314
2. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411-2502
3. Zanetti-Ramos, B. G.; Lemos-Senna, E.; Soldi, V.; Borsali, R.; Cloutet, E.; Cramail, H. Polymer 2006, 47, 8080-8087
4. Yeganeh, H.; Hojati-Talemi, P. Polym. Degrad. Stab. 2007, 92, 480-489
5. Guo, A.; Javni, I.; Petrovic, Z. J. Appl. Polym. Sci. 2000, 77, 467-473
6. Harry-O'kuru, R. E.; Holser, R. A.; Abbott, T. P.; Weisleder, D. Ind. Crop. Prod. 2002, 15, 51-58
7. Hwang, H.-S.; Erhan, S. J. Am. Oil Chem. Soc. 2001, 78, 1179-1184
8. Dahlke, B.; Hellbardt, S.; Paetow, M.; Zech, W. J. Am. Oil Chem. Soc. 1995, 72, 349-353
9. Sharma, V.; Kundu, P. P. Prog. Polym. Sci. 2008, 33, 1199-1215
10. Petrovic, Z. S.; Zhang, W.; Javni, I. Biomarcomolecules 2005, 6, 713-719
11. Campos, L. M.; Killops, K. L.; Sakai, R.; Paulusse, J. M. J.; Damiron, D.; Drockenmuller, E.; Messmore, B. W.; Hawker, C. J. Macromolecules 2008, 41, 7063-7070
12. Boutevin, G.; Ameduri, B.; Boutevin, B.; Joubert, J. P. J. Appl. Polym. Sci. 2000, 75, 1655-1666
13. Justynska, J.; Hordyjewicz, Z.; Schlaad, H. Polymer 2005, 46, 12057-12064
14. Lowe, A. B. Polym. Chem. 2010, 1, 17-36
15. Schwab, A.; Gast, L.; Cowan, J. J. Am. Oil Chem. Soc. 1968, 45, 461-464
16. Lluch, C.; Ronda, J. C.; Galià, M.; Lligadas, G.; Càdiz, V. Biomacromolecules 2010, 11, 1646-1653
17. Turunc, O.; Meier, M. A. R. Green Chem. 2011, 13 (2) 314-320
18. Samuelsson, J.; Jonsson, M.; Brinck, T.; Johansson, M. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 6346-6352
19. Black, M.; Rawlins, J. W. Eur. Polym. J. 2009, 45, 1433-1441
20. Bexell, U.; Olsson, M.; Johansson, M.; Samuelsson, J.; Sundell, P.-E. Surf. Coat. Technol. 2003, 166, 141-152
21. Türünç, O.; Meier, M. A. R. Macromol. Rapid Commun. 2010, 31, 1822-1826
22. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
23. Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Chem. Soc. Rev. 2010, 39, 1355-1387
24. Kade, M. J.; Burke, D. J.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 743-750
25. Carlson, D.; Knight, A. R. Can. J. Chem. 1973, 51, 1410-1415
26. David, R. L. A.; Kornfield, J. A. Macromolecules 2008, 41, 1151-1161
27. Boutevin, B.; Hervaud, Y.; Moulédous, G. Polym. Bull. 1998, 41, 145-151
28. Gress, A.; Völkel, A.; Schlaad, H. Macromolecules 2007, 40, 7928-7933
29. Schapman, F.; Couvercelle, J. P.; Bunel, C. Polymer 1998, 39, 4955-4962
30. Lotti, L.; Coiai, S.; Ciardelli, F.; Galimberti, M.; Passaglia, E. Macromol. Chem. Phys. 2009, 210, 1471-1483
31. Passaglia, E.; Donati, F. Polymer 2007, 48, 35-42
32. Koo, S. P. S.; Stamenovic, M. M.; Prasath, R. A.; Inglis, A. J.; Du Prez, F. E.; Barner-Kowollik, C.; Van Camp, W.; Junkers, T. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1699-1713
33. Bantchev, G. B.; Kenar, J. A.; Biresaw, G.; Han, M. G. J. Agric. Food Chem. 2009, 57, 1282-1290
34. Samadi, A.; Andreu, I.; Ferreri, C.; Dellonte, S.; Chatgilialoglu, C. J. Am. Oil Chem. Soc. 2004, 81, 753-758
35. Danehy, J. P.; Oester, M. Y. J. Org. Chem. 1967, 32, 1491-1495
36. Roper, T. M.; Guymon, C. A.; Jönsson, E. S.; Hoyle, C. E. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 6283-6298
37. Claudino, M.; Johansson, M.; Jonsson, M. Eur. Polym. J. 2010, 46, 2321-2332
38. Walling, C.; Helmreich, W. J. Am. Chem. Soc. 1959, 81, 1144-1148
39. Coates, J. In Encyclopedia of Analytical Chemistry; Meyers, R. A., Ed.; John Wiley & Sons Ltd.: Chichester, 2000; pp 10815 - 10837.
40. Karol, T. J.; Sung, R. L. Reaction product of beta-mercaptoethanol and coconut oil as diesel fuel antiwear additive. U.S. Patent 06,710,650, 1986.
41. Christie, W. W.; Dobson, G. Eur. J. Lipid Sci. Technol. 2000, 102, 515-520
42. Destaillats, F.; Angers, P. Eur. J. Lipid Sci. Technol. 2005, 107, 767-772
43. Hoyle, C., E.; Lee, T. Y.; Roper, T. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 5301-5338
44. Griesbaum, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 273-287
45. Muizebelt, W. J.; Nielen, M. W. F. J. Mass Spectrom. 1996, 31, 545-554
46. Ferreri, C.; Costantino, C.; Perrotta, L.; Landi, L.; Mulazzani, Q. G.; Chatgilialoglu, C. J. Am. Chem. Soc. 2001, 123, 4459-4468
47. Lopes, R. V. V.; Loureiro, N. P. D.; Zamian, J. R.; Fonseca, P. S.; Macedo, J. L.; dos Santos, M. L.; Sales, M. J. A. Macromol. Symp. 2009, 286, 89-94
48. Lazzari, M.; Chiantore, O. Polym. Degrad. Stab. 1999, 65, 303-313
49. Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; Van Camp, W. Angew. Chem., Int. Ed. 2011, 50, 60-62