From plant oils to plant foils: Straightforward functionalization and crosslinking of natural plant oils with triazolinediones

European Polymer Journal

Volumn 65, Issue , 2015, Pages 286-297

  Türünç, Oʇuz ^a   Billiet, Stijn ^a   De Bruycker, Kevin ^a   Ouardad, Samira ^a   Winne, Johan ^a   Du Prez, Filip E ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Alder ene reaction; Crosslinking; Fatty acid functionalization; Plant oils; TAD chemistry

Indexed keywords

FATTY ACIDS; MOLECULES; OIL SHALE; SYNTHESIS (CHEMICAL); VEGETABLE OILS;

ALDER ENE REACTIONS; CHEMICAL CROSS-LINKING; FUNCTIONALIZATION REACTIONS; FUNCTIONALIZATIONS; NATURAL PLANTS; PLANT OIL; POLYMER NETWORKS; TRIAZOLINEDIONES;

CROSSLINKING;

EID: 84925674289     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2014.12.013     Document Type: Article

References (42)

1. P. Anastas, and N. Eghbali Green chemistry: principles and practice Chem Soc Rev 39 1 2010 301 312
2. PlasticsEurope. Plastics - The Facts 2013; 2013.
3. J.O. Metzger Fats and oils as renewable feedstock for chemistry Eur J Lipid Sci Technol 111 9 2009 865 876
4. 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
5. L. Montero de Espinosa, and M.A.R. Meier Plant oils: the perfect renewable resource for polymer science?! Eur Polym J 47 5 2011 837 852
6. N. Kolb, M. Winkler, C. Syldatk, and M.A.R. Meier Long-chain polyesters and polyamides from biochemically derived fatty acids Eur Polym J. 51 2014 159 166
7. M. Firdaus, and M.A.R. Meier Renewable co-polymers derived from vanillin and fatty acid derivatives Eur Polym J 49 1 2013 156 166
8. H. Baumann, M. Bühler, H. Fochem, F. Hirsinger, H. Zoebelein, and J. Falbe Natural fats and oils - renewable raw materials for the chemical industry Angew Chem, Int Ed Engl 27 1 1988 41 62
9. K. Visek Amines, fatty, Kirk-Othmer encyclopedia of chemical technology 2000 John Wiley & Sons, Inc.
10. M.R. Infante, L. Pérez, M.C. Morán, R. Pons, M. Mitjans, and M.P. Vinardell Biocompatible surfactants from renewable hydrophiles Eur J Lipid Sci Technol 112 1 2010 110 121
11. K. Kosswig Surfactants Ullmann's encyclopedia of industrial chemistry 2000 Wiley-VCH Verlag GmbH & Co. KGaA
12. H. Wagner, R. Luther, and T. Mang Lubricant base fluids based on renewable raw materials: their catalytic manufacture and modification Appl Catal A 221 1-2 2001 429 442
13. M.P. Schneider Plant-oil-based lubricants and hydraulic fluids J Sci Food Agric 86 12 2006 1769 1780
14. F.N. Jones Alkyd resins Ullmann's encyclopedia of industrial chemistry 2003 Wiley-VCH Weinheim
15. J.A. Melero, J. Iglesias, and G. Morales Heterogeneous acid catalysts for biodiesel production: current status and future challenges Green Chem 11 9 2009 1285 1308
16. P. Gallezot Metal catalysis in the conversion of biosustainable resources A.J. Renouprez, Catalysis by metals 1997 Springer Berlin 201 221
17. K. Weissermel, and H.J. Arpe Industrial organic chemistry 1998 Wiley-VCH Weinheim
18. A. Guo, D. Demydov, W. Zhang, and Z. Petrovic Polyols and polyurethanes from hydroformylation of soybean oil J Polym Environ 10 1-2 2002 49 52
19. D. Quinzler, and S. Mecking Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization Angew Chem Int Ed 49 25 2010 4306 4308
20. O. Türünç, and M.A.R. Meier Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers Green Chem 13 2 2011 314
21. T.T.T. Ho, T. Jacobs, and M.A.R. Meier A Design-of-Experiments Approach for the Optimization and Understanding of the Cross-Metathesis Reaction of Methyl Ricinoleate with Methyl Acrylate ChemSusChem 2 8 2009 749 754
22. O. Türünç, M. Firdaus, G. Klein, and M.A.R. Meier Fatty acid derived renewable polyamides via thiol-ene additions Green Chem 14 9 2012 2577
23. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 11 2001 2004 2021
24. C. Barner-Kowollik, F.E. Du|Prez, P. Espeel, C.J. Hawker, T. Junkers, and H. Schlaad "Clicking" polymers or just efficient linking: what is the difference? Angew Chem Int Ed 50 1 2011 60 62
25. J. Hong, Q. Luo, X. Wan, Z.S. Petrovic, and B.K. Shah Biopolymers from vegetable oils via catalyst- and solvent-free "click" chemistry: effects of cross-linking density Biomacromolecules 13 1 2012 261 266
26. C. Vilela, A.J.D. Silvestre, and A. Gandini Thermoreversible nonlinear diels-alder polymerization of furan/plant oil monomers J Polym Sci, Part A: Polym Chem 51 10 2013 2260 2270
27. S. Billiet, K. De Bruycker, F. Driessen, H. Goossens, V. Van Speybroeck, and J.M. Winne Triazolinediones enable ultrafast and reversible click chemistry for the design of dynamic polymer systems Nat Chem 6 9 2014 815 821
28. S. Rout, and G. Butler Crosslinking of diene polymers via 'ENE' reaction with bistriazolinediones Polym Bull. 2 8 1980 513 520
29. T.C.S. Chen, and G.B. Butler Chemical reactions on polymers. 111. Modification of Diene Polymers via the Ene Reaction with 4-Substituted-1,2,4-triazoline-3,5-diones J Macromol Sci Pure Appl Chem 16 3 1981 757 768
30. G.B. Butler Triazolinedione modified polydienes Ind Eng Chem Prod RD 19 4 1980 512 528
31. P.L. Golas, and K. Matyjaszewski Marrying click chemistry with polymerization: expanding the scope of polymeric materials Chem Soc Rev 39 4 2010 1338 1354
32. Koon-Wah Leong, and Georg B. Butler Chemical reactions on polymers II: modification of diene polymers with triazolinediones via the ene reaction J Macromol Sci, Chem A14 3 1980 287 319
33. A.G. Williams, and G.B. Butler J Org Chem 45 1980 1232 1239
34. B.T. Gillis, and J.D. Hagarty The reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with conjugated dienes J Org Chem 32 2 1966 330 333
35. I.K. Korobitsyna, A.V. Khalikova, L.L. Rodina, and N.P. Shusherina 4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis (review) Chem Heterocycl Compd 19 2 1983 117 136
36. U. Shah, J. Lay Jr., and A. Proctor Significance of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in the GC-MS identification of conjugated fatty acid positional isomers J Am Oil Chem Soc 90 1 2013 155 158
37. A. Biswas, H.N. Cheng, S. Kim, and Z. Liu Modified triglyceride oil through reactions with phenyltriazolinedione J Am Oil Chem Soc 91 1 2014 125 131
38. A.C. Testa Photosensitized cis - trans isomerization of methyl oleate J Org Chem 29 8 1964 2461 2462
39. U. Biermann, W. Butte, R. Koch, P.A. Fokou, O. Türünç, and M.A.R. Meier Initiation of radical chain reactions of thiol compounds and alkenes without any added initiator: thiol-catalyzed cis/trans isomerization of methyl oleate Chem - A Eur J 18 26 2012 8201 8207
40. U. Biermann, J.O. Metzger, and M.A.R. Meier Acyclic triene metathesis oligo- and polymerization of high oleic sun flower oil Macromol Chem Phys 211 8 2010 854 862
41. S. Ohashi, and G.B. Butler Ene reaction of triazolinediones with alkenes. 2. Kinetics and substituent effects J Org Chem 45 17 1980 3472 3476
42. V.D. Kiselev, I.I. Shakirova, D.A. Kornilov, H.A. Kashaeva, L.N. Potapova, and A.I. Konovalov Homo-Diels-Alder reaction of a very inactive diene, bicyclo [2,2,1]hepta-2,5-diene, with the most active dienophile, 4-phenyl-1,2,4-triazolin-3,5-dione. Solvent, temperature, and high pressure influence on the reaction rate J Phys Org Chem 26 1 2013 47 53