Synthesis of elastomeric networks from maleated soybean-oil glycerides by thiol-ene coupling

European Polymer Journal

Volumn 48, Issue 12, 2012, Pages 2040-2049

  Echeverri, D A ^a   Cadiz V ^b   Ronda, J C ^b   Rios, L A ^a  

^a UNIVERSIDAD DE ANTIOQUIA   (Colombia)

^b UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Elastomers; Maleate; Monoglycerides; Soybean oil; Thiol ene; UV curable systems

Indexed keywords

MALEATE; MONOGLYCERIDES; SOYBEAN OIL; THIOL-ENES; UV-CURABLE SYSTEM;

CURING; ELASTOMERS; MATERIALS PROPERTIES;

OILSEEDS;

EID: 84868203707     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2012.09.004     Document Type: Article

References (30)

1. J.C. Ronda, G. Lligadas, M. Galià, and V. Cádiz Vegetable oils as platform chemicals for polymer synthesis Euro J Lipid Sci Technol 113 1 2011 46 58
2. A. Gandini, and M.N. Belgacem Monomers, polymers and composites from renewable resources 2008 Elsevier Amsterdam
3. 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
4. Y. Lu, and R.C. Larock Novel polymeric materials from vegetable oils and vinyl monomers: preparation, properties, and applications ChemSusChem 2 2 2009 136 147
5. M. Black, and J.W. Rawlins Thiol-ene UV-curable coatings using vegetable oil macromonomers Eur Polym J 45 5 2009 1433 1441
6. P. Mazo, D. Estenoz, M. Sponton, and L. Rios Kinetics of the transesterification of castor oil with maleic anhydride using conventional and microwave heating J Am Oil Chem Soc 89 7 2012 1355 1361
7. V. Sharma, and P.P. Kundu Addition polymers from natural oils. A review Prog Polym Sci 31 11 2006 983 1008 (Pubitemid 44738011)
8. E. Can, S. Küsefoglu, and R.P. Wool Rigid, thermosetting liquid molding resins from renewable resources. I. Synthesis and polymerization of soy oil monoglyceride maleates J Appl Polym Sci 81 1 2001 69 77 (Pubitemid 32495938)
9. E. Can, S. Küsefoglu, and R.P. Wool Rigid thermosetting liquid molding resins from renewable resources. II. Copolymers of soybean oil monoglyceride maleates with neopentyl glycol and bisphenol A maleates J Appl Polym Sci 83 5 2002 972 980 (Pubitemid 34011339)
10. E. Can, R.P. Wool, and S. Küsefoglu Soybean and castor oil based monomers: synthesis and copolymerization with styrene J Appl Polym Sci 102 3 2006 2433 2447 (Pubitemid 44619621)
11. E. Can, R.P. Wool, and S. Küsefoglu Soybean- and castor-oil-based thermosetting polymers: mechanical properties J Appl Polym Sci 102 2 2006 1497 1504 (Pubitemid 44518322)
12. 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 (Pubitemid 40002608)
13. 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
14. C.E. Hoyle, T.Y. Lee, and T. Roper Thiol-enes: chemistry of the past with promise for the future J Polym Sci Part A: Polym Chem 42 21 2004 5301 5338
15. Kade MJ, Burke DJ, Hawker CJ. The power of thiol-ene chemistry. J Polym Sci Part A: Polym Chem 2010;48(4):743-750.
16. Wu JF, Fernando S, Weerasinghe D, Chen Z, Webster DC. Synthesis of soybean oil-based thiol oligomers. ChemSusChem 2011;4(8):1135-1142.
17. Desroches M, Caillol S, Lapinte V, Auvergne Rm, Boutevin B. Synthesis of bio-based polyols by thiol-ene coupling from vegetable oils. Macromolecules 2011;44(8):2489-2500.
18. C.E. Hoyle, A.B. Lowe, and C.N. Bowman Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis Chem Soc Rev 39 4 2010 1355 1387
19. Yagci Y, Jockusch S, Turro NJ. Photoinitiated polymerization: advances, challenges, and opportunities. Macromolecules 2010;43(15):6245-6260.
20. H. Esen, S. Küsefoglu, and R. Wool Photolytic and free-radical polymerization of monomethyl maleate esters of epoxidized plant oil triglycerides J Appl Polym Sci 103 1 2007 626 633 (Pubitemid 44832277)
21. J.G. Homan, X.-H. Yu, T.J. Connor, and S.L. Cooper Castor oil based UV-curable polyurethane-acrylate interpenetrating networks J Appl Polym Sci 43 12 1991 2249 2257
22. S. Chakrapani, and J.V. Crivello Synthesis and photoinitiated cationic polymerization of epoxidized castor oil and its derivatives J Macromol Sci A 35 1 1998 1 20 (Pubitemid 128565375)
23. D. Echeverri, F. Cardeño, and L. Rios Glycerolysis of soybean oil with crude glycerol containing residual alkaline catalysts from biodiesel production J Am Oil Chem Soc 88 4 2011 551 557
24. C. Chatgilialoglu, A. Altieri, and H. Fischer The kinetics of thiyl radical-induced reactions of monounsaturated fatty acid esters J Am Chem Soc 124 43 2002 12816 12823 (Pubitemid 35216005)
25. C. Chatgilialoglu, A. Samadi, M. Guerra, and H. Fischer The kinetics of Z/E isomerization of methyl oleate catalyzed by photogenerated thiyl radicals Chem Phys Chem 6 2 2005 286 291 (Pubitemid 40379870)
26. Claudino M, Johansson M, Jonsson M. Thiol-ene coupling of 1,2-disubstituted alkene monomers: the kinetic effect of cis/trans-isomer structures. Eur Polym J 2010;46(12):2321-2332.
27. C. Ferreri, A. Samadi, F. Sassatelli, L. Landi, and C. Chatgilialoglu Regioselective cis-trans isomerization of arachidonic double bonds by thiyl radicals: the influence of phospholipid supramolecular organization J Am Chem Soc 126 4 2004 1063 1072 (Pubitemid 38140736)
28. González-Paz RJ, Lluch C, Lligadas G, Ronda JC, Galià M, Cádiz V. A green approach toward oleic- and undecylenic acid-derived polyurethanes. J Polym Sci Part A: Polym Chem 2011;49(11):2407-2416.
29. A.F. Jacobine Thiol-ene photopolymerization J.P. Fouassier, J.F. Rabek, 1993 Chapman and Hall London 219 268
30. D.W. Van Krevelen, and P.J. Hoftyzer Properties of polymers: their estimation and correlation with chemical structure 1976 Elsevier Amsterdam