Vegetable oils as platform chemicals for polymer synthesis

European Journal of Lipid Science and Technology

Volumn 113, Issue 1, 2011, Pages 46-58

  Ronda, Juan Carlos ^a   Lligadas, Gerard ^a   Galià, Marina ^a   Cádiz, Virgínia ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Polyesters; Polyurethanes; Thermosetting polymers; Vegetable oils

Indexed keywords

GLYCINE MAX; HELIANTHUS;

EID: 78651462945     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201000103     Document Type: Review

References (63)

1. Bozell, J. J., Patel, M. K., ACS Symposium Series 921, American Chemical Society, Washington, DC 2006.
2. Biermann, U., Friedt, W., Lang, S., Luhs, W., et al., New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew. Chem., Int. Ed. 2000, 39, 2206- 2224.
3. Güner, F. S., Yagci, Y., Erciyes, A. T., Polymers from triglyceride oils. Prog. Polym. Sci. 2006, 31, 633- 670.
4. Sharma, V., Kundu, P. P., Addition polymers from natural oils. A review. Prog. Polym. Sci 2006, 31, 983- 1008.
5. Sharma, V., Kundu, P. P., Condensation polymers from natural oils. Prog. Polym. Sci. 2008, 33, 1199- 1215.
6. Erhan, S. Z., Bagby, M. O., Polymerization of vegetable oils and their uses in printing inks. J. Am. Chem. Oil Soc. 1994, 71, 1223- 1226.
7. Lu, Y., Larock, R. C., Novel polymeric materials from vegetable oils and vinyl monomers: Preparation, properties and applications. ChemSusChem 2009, 2, 136- 147.
8. Sacristan, M., Ronda, J. C., Galià, M., Cádiz, V., Silicon-containing soybean oil-based copolymers. Synthesis and properties. Biomacromolecules 2009, 10, 2678- 2685.
9. Li, F., Hanson, M. V., Larock, R. C., Soybean oil-divinylbenzene thermosetting polymers: Synthesis, structure, properties and their relationships. Polymer 2001, 42, 1567- 1579.
10. Eren, T., Kusefoglu, S. H., Synthesis and polymerization of the bromoacrylated plant oil triglycerides to rigid, flame-retardant polymers. J. Appl. Polym. Sci. 2004, 91, 2700- 2710.
11. Jain, P., Choudhary, V., Varma, I. K., Flame retarding epoxies with phosphorus. J. Macromol. Sci., Polym. Rev. 2002, 42, 139- 183.
12. Lu, S. Y., Hamerton, I., Recent developments in the chemistry of halogen-free flame retardant polymers. Prog. Polym. Sci. 2002, 27, 1661- 1712.
13. Kashiwagi, T., Gilman, J. W., in: Grand, A. F., Wilkie, C. A. (Eds.), Fire Retardancy of Polymeric Materials, Marcel Dekker, New York 2000, pp. 353- 390.
14. Liu, Y.-L., Hsiue, G.-H., Lee, R.-H., Chiu, Y.-S., Phosphorus-containing epoxy for flame retardant. III: Using phosphorylated diamines as curing agents. J. Appl. Polym. Sci. 1997, 63, 895- 901.
15. Wilkie, C. A., Morgan, A. B. (Eds.), Fire Retardancy of Polymeric Materials, CCR Press, London 2009.
16. Loupy, A., Microwaves in Organic Synthesis, Wiley VCH, Weinheim 2002.
17. Bogdal, D., Prociak, A., Microwave Enhanced Polymer Chemistry and Technology, Blackwell Publishing, Ames, Iowa 2007.
18. Sinnwell, S., Ritter, H., Recent advances in microwave-assisted polymer synthesis. Aust. J. Chem. 2007, 60, 729- 743.
19. Wiesbrock, F., Hoogenboom, R., Schubert, U. S., Microwave-assisted polymer synthesis: State-of-the-art and future perspectives. Macromol. Rapid Commun. 2004, 25, 1739- 1764.
20. Hoogenboom, R., Schubert, U. S., Microwave-assisted polymer synthesis: Recent developments in a rapidly expanding field of research. Macromol. Rapid Commun. 2007, 28, 368- 386.
21. Bardts, M., Gonsior, N., Ritter, H., Polymer synthesis and modification by use of microwaves. Macromol. Chem. Phys. 2008, 209, 25- 31.
22. Sacristan, M., Ronda, J. C., Galià, M., Cádiz, V., Rapid soybean oil copolymers synthesis by microwave-assisted cationic polymerization. Macromol. Chem. Phys. 2010, 211, 801- 808.
23. Zhang, D., Crivello, J. V., Stoffer, J. O., Polymerizations of epoxides with microwave energy. J. Polym. Sci., Part B Polym. Phys. 2004, 42, 4230- 4246.
24. Lidström, P., Tierney, J., Wathey, B., Microwave assisted organic synthesis-a review. Tetrahedron 2001, 57, 9225- 9283.
25. Hayes, B. L., " Microwave Synthesis: Chemistry at the Speed of Light", CEM Publishing, Matthews, NC 2002.
26. Stange, H., Greiner, A., Microwave-assisted free radical copolymerizations of styrene and methyl methacrylate. Macromol. Rapid Commun. 2007, 28, 504- 508.
27. Schenck, G. O., Zur theorie der photosensibilisierten reaction molekularem sauerstoff. Naturwissenschaften 1948, 35, 28- 29.
28. 2 (1Ag)] in photosensitised oxidation reactions. Acc. Chem. Res. 2006, 39, 797- 804.
29. Hui, S.-P., Yoshimura, T., Murai, T., Chiba, H., Kurosawa, T., Determination of regioisomeric hydroperoxides of fatty acid cholesterol esters produced by photosensitized peroxidation using HPLC. Anal. Sci. 2000, 16, 1023- 1028.
30. Samadi, A., Martinez, L. A., Miranda, M. A., Morera, I. M., Mechanism of lipid peroxidation photosensitized by tiaprofenic acid: Product studies using linoleic acid and 1, 4-cyclohexadienes as model substrates. Photochem. Photobiol. 2001, 73, 359- 365.
31. Frimer, A. A., The reaction of singlet oxygen with olefins: The question of mechanism. Chem. Rev. 1979, 79, 359- 387.
32. Montero de Espinosa, L., Ronda, J. C., Galià, M., Cádiz, V., A new route to acrylate oils: Crosslinking and properties of acrylate triglycerides from high oleic sunflower oil. J. Polym. Sci., Part A Polym. Chem. 2009, 47, 1159- 1167.
33. Montero de Espinosa, L., Ronda, J. C., Galià, M., Cádiz, V., A straightforward strategy for the efficient synthesis of acrylate phosphine-oxide-containing vegetable oils and their crosslinked materials. J. Polym. Sci., Part A Polym. Chem. 2009, 47, 4051- 4063.
34. Kornblum, N., DeLaMare, H. E., The base catalyzed decomposition of a dialkyl peroxide. J. Am. Chem. Soc. 1951, 73, 880- 881.
35. Ohloff, G., Singlet oxygen: A reagent in organic synthesis. Pure Appl. Chem. 1975, 43, 481- 502.
36. Montero de Espinosa, L., Ronda, J. C., Galià, M., Cádiz, V., A new enone-containing triglyceride derivative as precursor of thermosets from renewable resources. J. Polym. Sci., Part A Polym. Chem. 2008, 46, 6843- 6850.
37. Montero de Espinosa, L., Ronda, J. C., Galià, M., Cádiz, V., Quinoline-containing networks from enone and aldehyde triglyceride derivatives. J. Polym. Sci., Part A Polym. Chem. 2010, 48, 869- 878.
38. der Steen, M. V., Stevens, C. V., Undecylenic acid: A valuable and physiologically active renewable building block from castor oil. ChemSusChem 2009, 2, 692- 713.
39. Schwendeman, J. E., Church, A. C., Wagener, K. B., Synthesis and catalyst issues associated with ADMET polymerization. Adv. Synth. Catal. 2002, 344, 597- 613.
40. Wagener, K. B., Brzezinska, K., Anderson, J. D., Younkin, T. R., et al., Kinetics of acyclic diene metathesis (ADMET) polymerization. Influence of the negative neighboring group effect. Macromolecules 1997, 30, 7363- 7369.
41. Baughman, T. W., Wagener, K. B., Recent advances in ADMET polymerization. Adv. Polym. Sci. 2005, 176, 1- 42.
42. Shultz, G. V., Zakharov, L. N., Tyler, D. R., Transition-metal-containing polymers by ADMET: Polymerization of cis-Mo(CO)4(Ph2P(CH2)3CH=CH2)2. Macromolecules 2008, 4, 5555- 5558.
43. Terada, K., Berda, E. B., Wagener, K. B., Sanda, F., Masuda, T., ADMET polycondensation of diketopiperazine-based dienes. Polymerization behavior and effect of diketopiperazine on the properties of the formed polymers. Macromolecules 2008, 41, 6041- 6046.
44. Montero de Espinosa, L., Ronda, J. C., Galià, M., Cádiz, V., Meier, M. A. R., Fatty acid derived phosphorus-containing polyesters via acyclic diene metathesis polymerization. J. Polym. Sci., Part A Polym. Chem. 2009, 47, 5760- 5771.
45. Montero de Espinosa, L., Meier, M. A. R., Ronda, J. C., Galià, M., Cádiz, V., Phosphorus-containing renewable polyester-polyols via ADMET polymerization. Synthesis, functionalization and radical cross-linking. J. Polym. Sci., Part A Polym. Chem. 2010, 48, 1649- 1660.
46. Lligadas, G., Ronda, J. C., Galià, M., Cádiz, V., Synthesis and properties of thermosetting polymers from a phosphorous-containing fatty acid derivative. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5630- 5644.
47. 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.
48. Sumerlin, B. S., Vogt, A. P., Macromolecular engineering through click chemistry and other efficient transformations. Macromolecules 2010, 43, 1- 13.
49. Wu, P., Feldman, A. K., Nugent, A. K., Hawker, C. J., et al., Efficiency and fidelity in a click-chemistry route to triazole dendrimers by the copper(I)-catalyzed ligation of azides and alkynes. Angew. Chem., Int. Ed. 2004, 43, 3928- 3932.
50. Meldal, M., Tornøe, C. W., Chem. Rev. 2008, 108, 2952- 3015.
51. Iha, R. K., Wooley, K. L., Nystrom, 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.
52. Becer, C. R., Hoogenboom, R., Schubert, U. S., Click chemistry beyond metal-catalyzed cycloaddition. Angew. Chem., Int. Ed. 2009, 48, 4900- 4908.
53. Yu, B., Chan, J. W., Hoyle, C. E., Lowe, A. B., Sequential thiol-ene/thiol-ene and thiol-ene/thiol-yne reactions as a route to well-defined mono and bis end-functionalized poly(N-isopropylacrylamide). J. Polym. Sci., Part A Polym. Chem. 2009, 47, 3544- 3557.
54. Hensarling, R. M., Doughty, V. A., Chan, J. W., Patton, D. L., " Clicking" polymer brushes with thiol-yne chemistry: Indoors and out. J. Am. Chem. Soc. 2009, 131, 14673- 14675.
55. Hoyle, C. E., Bowman, C. N., Thiol-ene click chemistry. Angew. Chem., Int. Ed. 2010, 49, 1540- 1573.
56. Hoogenboom, R., Thiol-yne chemistry: A powerful tool for creating highly functional materials. Angew. Chem., Int. Ed. 2010, 49, 3415- 3417.
57. Rosen, B. M., Lligadas, G., Hahn, C., Percec, V., Synthesis of dendrimers through divergent iterative thio-bromo "click" chemistry. J. Polym. Sci., Part A Polym. Chem. 2009, 47, 3931- 3939.
58. Vazquez-Dorbatt, V., Tolstyka, Z. P., Chang, C. W., Maynard, H. D., Synthesis of a pyridyl disulfide end-functionalized glycopolymer for conjugation to biomolecules and patterning on gold surfaces. Biomacromolecules 2009, 10, 2207- 2212.
59. Pounder, R. J., Stanford, M. J., Brooks, P., Richards, S. P., Dove, A. P., Metal free thiol-maleimide 'click' reaction as a mild functionalisation strategy for degradable polymers. Chem. Commun. 2008, 41, 5158- 5160.
60. Witczak, Z. J., Lorchak, D., Nguyen, N., A click chemistry approach to glycomimetics: Michael addition of 2, 3, 4, 6-tetra-O-acetyl-1-thio-β-d-glucopyranose to 4-deoxy-1, 2-O-isopropylidene-l-glycero-pent-4-enopyranos-3-ulose, a convenient route to novel 4-deoxy-(1 → 5)-5-C-thiodisaccharides. Carbohydr. Res. 2007, 342, 1929- 1933.
61. Becer, C. R., Babiuch, K., Pilz, D., Horning, S., et al., Clicking pentafluorostyrene copolymers: Synthesis, nanoprecipitation, and glycosylation. Macromolecules 2009, 42, 2387- 2394.
62. Goethals, E. J., Telechelic Polymers: Synthesis and Applications, CCR Press, Boca Raton, FL 1989.
63. Lluch, C., Ronda, J. C., Galià, M., Lligadas, G., Cádiz, V., Rapid approach to biobased telequelics through two one-pot thiol-ene click reactions. Biomacromolecules 2010, 11, 1646- 1653.