The thiol-ene (click) reaction for the synthesis of plant oil derived polymers

European Journal of Lipid Science and Technology

Volumn 115, Issue 1, 2013, Pages 41-54

  Türünç, Oǧuz ^a   Meier, Michael A R ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Double bond; Fatty acid; Polymer chemistry; Renewable raw materials; Thiol ene

Indexed keywords

EID: 84872384532     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201200148     Document Type: Review

References (63)

1. 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.
2. Posner, T., Beiträge zur Kenntniss der ungesättigten Verbindungen. II. Ueber die Addition von Mercaptanen an ungesättigte Kohlenwasserstoffe. Ber. Dtsch. Chem. Ges. 1905, 38, 646- 657.
3. Marvel, C. S., Chambers, R. R., Polyalkylene Sulfides From Diolefins and Dimercaptans. J. Am. Chem. Soc. 1948, 70, 993- 998.
4. Walling, C., Helmreich, W., Reactivity and reversibility in the reaction of thiyl radicals with olefins. J. Am. Chem. Soc. 1959, 81, 1144- 1148.
5. Testa, A. C., Photosensitized cis-trans isomerization of methyl oleate. J. Org. Chem. 1964, 29, 2461- 2962.
6. Hoyle, C. E., Lee, T. Y., Roper, T., Thiol-enes: Chemistry of the past with promise for the future. J. Polym. Sci. A Polym. Chem. 2004, 42, 5301- 5338.
7. Griesbaum, K., Problems and possibilities of the free-radical addition of thiols to unsaturated compounds. Angew. Chem. Int. Edit. 1970, 9, 273- 287.
8. Pryor, W. A., Coco, J. H., Daly, W. H., Houk, K. N., Radical generation from polymolecular reactions of closed shell molecules. Molecule-assisted homolysis (MAH). Hydrogen atom transfer from a Diels-Alder adduct to an alkene. J. Am. Chem. Soc. 1974, 96, 5591- 5593.
9. Nuyken, O., Volkel, T., Telechelics via addition of dithiols onto alkadienes. 1. Radical mechanism. Makromol. Chem. Rapid Commun. 1990, 11, 365- 373.
10. Nuyken, O., Volkel, T., Pohlmann, T., Telechelics via addition of dithiols onto diolefins. 3. Heat-resistant polysulfides from 1, 3-benzenedithiol and norbornadiene macromol. Chem. Phys. 1991, 192, 1959- 1968.
11. Klemm, E., Sensfuß, S., Holfter, U., Schütz, H., Untersuchungen zur linearen thiol-en photopolymerisation. Makromol. Chem. 1990, 191, 2403- 2411.
12. Klemm, E., Sensfuß, S., Investigations on the mechanism of autoinitiation in thiol en-polymerization. Makromol. Chem. 1991, 192, 159- 164.
13. Biermann, U., Butte, W., Koch, R., Fokou, P. A., et al., Initiation of radical chain reactions of thiol compounds and alkenes without any added initiator: Thiol-catalyzed cis/trans isomerization of methyl oleate. Chem. Eur. J. 2012, 18, 8201- 8207.
14. Boutevin, B., Hervaud, Y., Moulédous, G., Grafting phosphonated thiol on hydroxy telechelic polybutadiene. Polym. Bull. 1998, 41, 145- 151.
15. Kozhushkov, S. I., Brandl, M., de Meijere, A., Surprisingly facile addition of thiols to the double bonds of bicyclopropylidene and other methylenecyclopropanes. Eur. J. Org. Chem. 1998, 1998, 1535- 1542.
16. Samuelsson, J., Jonsson, M., Brinck, T., Johansson, M., Thiol-ene coupling reaction of fatty acid monomers. J. Polym. Sci. A Polym. Chem. 2004, 42, 6346- 6352.
17. Lou, F.-W., Xu, J.-M., Liu, B.-K., Wu, Q. et al., Highly selective anti-Markovnikov addition of thiols to vinyl ethers under solvent- and catalyst-free conditions. Tetrahed. Lett. 2007, 48, 8815- 8818.
18. Uygun, M., Tasdelen, M. A., Yagci, Y., Influence of type of initiation on thiol-Ene "click" chemistry. Macromol. Chem. Phys. 2010, 211, 103- 110.
19. ten Brummelhuis, N., Diehl, C., Schlaad, H., Thiol-ene modification of 1, 2-polybutadiene using UV light or sunlight. Macromolecules 2008, 41, 9946- 9947.
20. Gress, A., Völkel, A., Schlaad, H., Thio-click modification of poly[2-(3-butenyl)-2-oxazoline]. Macromolecules 2007, 40, 7928- 7933.
21. Sun, J., Schlaad, H., Thiol-ene clickable polypeptides. Macromolecules 2010, 43, 4445- 4448.
22. Bertin, A., Schlaad, H., Mild and versatile (bio-)functionalization of glass surfaces via thiol-ene photochemistry. Chem. Mater. 2009, 21, 5698- 5700.
23. Madaan, N., Terry, A., Harb, J., Davis, R. C. et al., Thiol-ene-thiol photofunctionalization of thiolated monolayers with polybutadiene and functional thiols, including thiolated DNA. J. Phys. Chem. C. 2011, 115, 22931- 22938.
24. Rissing, C., Son, D. Y., Thiol-ene reaction for the synthesis of multifunctional branched organosilanes. Organometallics 2008, 27, 5394- 5397.
25. Killops, K. L., Campos, L. M., Hawker, C. J., Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry. J. Am. Chem. Soc. 2008, 130, 5062- 5064.
26. Kolb, H. C., Finn, M. G., Sharpless, K. B., Click chemistry: Diverse chemical Function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004- 2021.
27. Kade, M. J., Burke, D. J., Hawker, C. J., The power of thiol-ene chemistry. J. Polym. Sci. A Polym. Chem. 2010, 48, 743- 750. Hoyle, C. E., Bowman, C. N., Thiol-ene click chemistry. Angew. Chem. Int. Ed. 2010, 49, 1540- 1573.
28. Barner-Kowollik, C., Inglis, A. J., Has click chemistry lead to a paradigm shift in polymer material design? Macromol. Chem. Phys. 2009, 210, 987- 992. Lodge, T. P., A virtual issue of macromolecules: "Click chemistry in macromolecular science". Macromolecules 2009, 42, 3827- 3829.
29. Iha, R. K., Wooley, K. L., Nystroem, A. M., Burke, D. J. et al., Applications of orthogonal "click" chemistries in the synthesis of functional soft materials. Chem. Rev. 2009, 109, 5620- 5686.
30. Koo, S. P. S., Stamenović, M. M., Prasath, R. A., Inglis, A. J. et al., Limitations of radical thiol-ene reactions for polymer-polymer conjugation. J. Polym. Sci. A Polym. Chem. 2010, 48, 1699- 1713.
31. Metzger, J. O., Fats and oils as renewable feedstock for chemistry. Eur. J. Lipid Sci. Technol. 2009, 111, 865- 876. Metzger, J. O., Bornscheuer, U., Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl. Microbiol. Biotechnol. 2006, 71, 13- 22.
32. Türünç, O., Meier, M. A. R., in: N. T. Dunford (Ed.), Food and Industrial Bioproducts and Bioprocessing Wiley-Blackwell, Oxford, UK 2012.
33. 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.
34. Metzger, J. O., Organic reactions without organic solvents and oils and fats as renewable raw materials for the chemical industry. Chemosphere 2001, 43, 83- 87.
35. Metzger, J. O., Riedner, U., Free-radical additions to unsaturated fatty-acids. Fat Sci. Technol. 1989, 1, 18- 23.
36. Koenig, N., Swern, D., Organic sulfur derivatives. 1. Addition of mercaptoacetic acid to long-chain monounsaturated compounds. J. Am. Chem. Soc. 1957, 79, 362- 365.
37. Koenig, N., Swern, D., Organic sulfur derivatives. 2. Sulfides, sulfoxides and sulfones from thiols and 10-undecenoic acid. J. Am. Chem. Soc. 1957, 79, 4235- 4237.
38. Koenig, N., Sasin, G., Swern, D., Organic sulfur derivatives. 5. Preparation and properties of some long-chain mercapto acids and related compounds. J. Org. Chem. 1958, 23, 1525- 1530.
39. Schwab, A., Gast, L., Free radical addition of hydrogen sulfide and thiols to linseed oil and methyl oleate. J. Am. Oil Chem. Soc. 1968, 45, 461- 464.
40. Schwab, A., Gast, L., Cowan, J., Free radical addition of hydrogen sulfide to conjugated and nonconjugated methyl esters and to vegetable oils. J. Am. Oil Chem. Soc. 1970, 47, 371-.
41. Bexell, U., Olsson, M., Johansson, M., Samuelsson, J., Sundell, P.-E., A tribological study of a novel pre-treatment with linseed oil bonded to mercaptosilane treated aluminium. Surf. Coat. Tech. 2003, 166, 141- 152.
42. Bexell, U., Olsson, M., Sundell, P. E., Johansson, M. et al., A ToF-SIMS study of linseed oil bonded to mercapto silane treated aluminium. Appl. Surf. Sci. 2004, 231-232, 362- 365.
43. Bexell, U., Berger, R., Olsson, M., Grehk, T. M. et al., Bonding of vegetable oils to mercapto silane treated metal surfaces: Surface engineering on the nano scale. Thin Solid Films 2006, 515, 838- 841.
44. Bantchev, G. B., Kenar, J. A., Biresaw, G., Han, M. G., Free radical addition of butanethiol to vegetable oil double bonds. J. Agric. Food Chem. 2009, 57, 1282- 1290.
45. Black, M., Rawlins, J. W., Thiol-ene UV-curable coatings using vegetable oil macromonomers. Eur. Polym. J. 2009, 45, 1433- 1441.
46. Chen, Z., Chisholm, B. J., Patani, R., Wu, J. F. et al., Soy-based UV-curable thiol-ene coatings. J. Coat. Technol. Res. 2010, 7, 603- 613.
47. Stemmelen, M., Pessel, F., Lapinte, V., Caillol, S. et al., 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. J. Polym. Sci. A Polym. Chem. 2011, 49, 2434- 2444.
48. 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.
49. Boutevin, B., Chaib, M., Robin, J.-J., Synthesis of monodispers macromolecular diisocyanate. Polym. Bull. 1991, 26, 177- 179.
50. Ameduri, B., Berrada, K., Boutevin, B., Bowden, R. D., Synthesis of telechelic monodispersed diols. Polym. Bull. 1992, 28, 497- 503.
51. Ameduri, B., Berrada, K., Boutevin, B., Bowden, R. D., Synthesis of a telechelic monodispersed mercapto-alcohol. Polym. Bull. 1993, 31, 1- 7.
52. Türünç, O., Meier, M. A. R., Fatty acid derived monomers and related polymers via thiol-ene (click) additions. Macromol. Rapid Commun. 2010, 31, 1822- 1826.
53. Lluch, C., Lligadas, G., Ronda, J. C., Galià, M., Cadiz, V., " Click" synthesis of fatty acid derivatives as fast-degrading polyanhydride precursors. Macromol. Rapid Commun. 2011, 32, 1343- 1351.
54. 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. A Polym. Chem. 2011, 49, 2407- 2416.
55. 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. A Polym. Chem. 2012, 50, 1766- 1782.
56. Vilela, C., Cruciani, L., Silvestre, A. J. D., Gandini, A., Reversible polymerization of novel monomers bearing furan and plant oil moieties: A double click exploitation of renewable resources. RSC Adv. 2012, 2, 2966- 2974.
57. 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.
58. Türünç, O., Meier, M. A. R., Thiol-ene vs. ADMET: A complementary approach to fatty acid-based biodegradable polymers. Green Chem. 2011, 13, 314.
59. Quinzler, D., Mecking, S., Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization. Angew. Chem. Int. Ed. 2010, 49, 4306 -4308. Cole-Hamilton, D. J., Nature's polyethylene. Angew. Chem. Int. Ed. 2010, 49, 8564- 8566.
60. Türünç, O., Montero de Espinosa, L., Meier, M. A. R., Renewable polyethylene mimics derived from castor oil. Macromol. Rapid Commun. 2011, 32, 1357- 1361.
61. Kreye, O., Türünç, O., Sehlinger, A., Rackwitz, J., Meier, M. A. R., Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction. Chem. Eur. J. 2012, 18, 5767- 5776.
62. Pirrung, M. C., Sarma, K. D., Multicomponent reactions are accelerated in water. J. Am. Chem. Soc. 2003, 126, 444- 445.
63. Ates, Z., Thornton, P. D., Heise, A., Side-chain functionalisation of unsaturated polyesters from ring-opening polymerisation of macrolactones by thiol-ene click chemistry. Polym. Chem. 2011, 2, 309- 312.