New biobased epoxy materials from cardanol

European Journal of Lipid Science and Technology

Volumn 116, Issue 1, 2014, Pages 63-73

  Jaillet, Fanny ^a   Darroman, Emilie ^a   Ratsimihety, Amédée ^a   Auvergne, Rémi ^a   Boutevin, Bernard ^a   Caillol, Sylvain ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Cardanol; CNSL; Epoxidation; Epoxy resins; NMR

Indexed keywords

ANACARDIUM OCCIDENTALE;

EID: 84891629808     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201300193     Document Type: Article

References (48)

1. Tuck, C. O., Perez, E., Horvath, I., Sheldon, R. A., Poliakoff, M., Valorization of biomass: deriving more value from waste. Science 2012, 337, 695-699.
2. Gandini, A., The irruption of polymers from renewable resources on the scene of macromolecular science and technology. Green Chem. 2011, 13, 1061-1083.
3. Koike, T., Progress in development of epoxy resin systems based on wood biomass in Japan. Polym. Eng. Sci. 2012, 52, 701-717.
4. Aouf, C., Nouailhas, H., Fache, M., Caillol, S. et al., Multi-functionalization of gallic acid. Synthesis of a novel bio-based epoxy resin. Europ. Pol. J. 2013, 49, 1185-1195.
5. Brazinha, C., Barbosa, D. S., Crespo, J. G., Sustainable recovery of pure natural vanillin from fermentation media in a single pervaporation step. Green Chem. 2011, 13, 2197-2203.
6. Carrier, M., Loppinet-Serani, A., Denux, D., Lasnier, J. M. et al., Thermogravimetric analysis as a new method to determine the lignocellulosic composition of biomass. Biomass Bioenergy 2011, 35, 298-2307.
7. Balachandran, V. S., Jadhav, S. R., Vemula, P. K., John, G., Recent advances in cardanol chemistry in a nutshell: from a nut to nanomaterials. Chem. Soc. Rev. 2012, 42, 427-438.
8. Ionescu, M., Wan, X., Biliç, N., Petrović, Z. S., Polyols and rigid polyurethane foams from cashew nut shell liquid. J. Pol. Env. 2012, 20, 647-658.
9. Campaner, P., D'Amico, D., Longo, L., Stifani, C., Tarzia, A., Cardanol-based novolac resins as curing agents of epoxy resins. J. Appl. Pol. Sci. 2009, 114, 3585-3591.
10. Pillai, C. K. S., Prasad, V. S., Sudha, J. D., Bera, S. C., Menon, A. R. R., Polymeric resins from renewable resources. Synthesis and characterization of flame retardant prepolymers from cardanol. J. Appl. Pol. Sci. 1990, 41, 2487.
11. Keil, H., Wasserman, D., Dawson, C. R., The relation of hypersensitiveness to poison ivy and to cashew nut shell liquid. Science 1945, 102, 279-2280.
12. Phani Kumar, P., Paramashivappa, R., Vithayathil, P. J., Subba Rao, P. V., Srinivasa, R., Process for isolation of cardanol from technical cashew (anacardium occidentale) nut shell liquid. J. Agric. Food Chem. 2002, 50, 4705-4708.
13. Carioca, J. O. B., Vasconcelos, G. F. C., Abreu, R. F., Monteiro, A., Process of purification of cashew nut shell liquid (CNSL) for isolation of cardanol. CTF, 2nd Mercosur Congress on Chemical Engineering, 2005, Brazil.
14. Sultania, M., Rai, J. S. P., Srivastava, D., Process modeling, optimization and analysis of esterification reaction of cashew nut shell liquid (CNSL)-derived epoxy resin using response surface methodology. J. Haz. Mater. 2011, 185, 1198-1204.
15. Tyman, J. H. P., Long-chain phenols IV: quantitative determination of the olefinic of the component phenols in cashew nut-shell. J. Chromatogr. 1975, 111, 277-284.
16. More, A. S., Pasale, S. K., Honkhambe, P. N., Wadgaonkar, P. P., Synthesis and characterization of organo-soluble poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing pendant pentadecyl chains. J. Appl. Pol. Sci. 2011, 121, 3689-3695.
17. Sudhakar, M. A., Wadgaonkar, P. P., US Patent 2009076314, 2009.
18. Kim, Y. H., Won, K., Kwon, J. M., Jeong, H. S. et al., Synthesis of polycardanol from a renewable resource using a fungal peroxidase from Coprinus cinereus. J. Macromol. Cat. B Enzymatic. 2005, 34, 33-38.
19. Suresh, K. I., Kishanprasad, V. S., Synthesis, structure, and properties of novel polyols from cardanol and developed polyurethanes. Ind. Eng. Chem. Res. 2005, 44, 4504-4512.
20. Lespinasse, R., Prouvost, B., Stenson, P., US Patent 0315591, 2011.
21. Yadav, R., Srivastava, D., Synthesis and properties of cardanol-based epoxidized novolac resins modified with carboxyl-terminated butadiene-acrylonitrile copolymer. J. Appl. Pol. Sci. 2009, 114, 1670-1681.
22. Huong, N. L., Nieu, N. H., Tan, T. T. M., Griesser, U., Cardanol-phenol-formaldehyde resins. Thermal analysis and characterization. Ang. Makromol. Chem. 1996, 243, 77-85.
23. Sultania, M., Rai, J. S. P., Srivastava, D., Studies on the synthesis and curing of epoxidized novolac vinyl ester resins from nenewable resource material. Eur. Pol. J. 2010, 46, 2019-2032.
24. Unnikrishnan, K. P., Thomas Thachil, E. B. Y., Studies on the modification of commercial epoxy resins using cardanol-based phenolic resins. J. Elastomers Plast. 2008, 40, 271-286.
25. Vernekar, S. P., Epoxy compound of cashew nut shell liquid as a stabilizer for polyvinyl-chloride. Ind. J. Technol. 1980, 18, 170.
26. Baker, N. F., Epoxy Resin Compositions, US Patent 824 302, 1955.
27. Agarwal, R. K., Bammel, B. D., Fristad, W. E., Rossier, G. W. et al., US Patent 0104212, 2003.
28. Kanehashi, S., Yokoyama, K., Masuda, R., Kidesaki, T. et al., Preparation and characterization of cardanol-based epoxy resin for coating at room temperature curing. J. Appl. Pol. Sci. 2013, doi: 10.1002/app.39382.
29. Patel, M. B., Patel, R. G., Patel, V. S., Effects of reactive diluent diepoxidized cardanol and epoxy fortifier on curing kinetics of epoxy resin. J. Therm. Anal. 1989, 35, 47-457.
30. Greco, A., Brunetti, D., Renna, G., Mele, G., Maffezzoli, A., Plasticizer for poly(vinyl chloride) from cardanol as a renewable resource material. Pol. Degrad. Stab. 2010, 95, 2169-2174.
31. Suresh, K. I., Rigid polyurethane foams from cardanol: synthesis, structural characterization, and evaluation of polyol and foam properties. ACS Sustain. Chem. Eng. 2013, 1, 232-242.
32. Tan, T. T. M., Cardanol-lignin-based epoxy resins: synthesis and characterization. J. Polym. Mater. 1996, 13, 195-199.
33. Kim, Y. H., An, E. S., Park, S. Y., Song, B. K., Enzymatic epoxidation and polymerization of cardanol obtained from a renewable resources and curing of epoxide-containing polycardanol. J. Macromol. Cat. B Enzymatic. 2007, 45, 39-44.
34. May, C. A. Epoxy Resins, Chemistry and Technology, Marcel Dekker, New York/Basel 1988, pp. 1-6.
35. Dodds, E. C., Lawson, W., Synthetic strogenic agents without the phenanthrene nucleus. Nature 1936, 137, 996-996.
36. Gore, A. C. Endocrine Disturbing Chemicals-Contemporary Endocrinology, Humana Press, Totowa, NJ 2007, 100-125.
37. O'Connor, J. C., Chapin, R. E., Critical evaluation of observed adverse effects of endocrine active substances on reproduction and development, the immune system, and the nervous system. Pure. Appl. Chem. 2003, 75, 2099-2123.
38. Okada, H., Tokunaga, T., Liu, X., Takayanagi, S. et al., Direct evidence revealing structural elements essential for the high binding ability of bisphenol A to human estrogen-related receptor-γ. Environ. Health. Persp. 2008, 116, 32-38.
39. Vom Saal, F. S., Myers, J. P., Bisphenol A and risk of metabolic disorders. J. Am. Med. Assn. 2008, 300, 1353-1355.
40. Vom Saal, F. S., Hughes, C., An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment. Environ. Health. Persp. 2005, 113, 926-933.
41. Lee, H., Neville, K., Handbook of Epoxy Resins, McGraw-Hill Publishing Company, NY 1967, pp. 4.1-4.70.
42. Psomiadou, E., Arvanitoyannis, I., Yamamoto, N., Edible films made from natural resources; microcrystalline cellulose (MCC), methylcellulose (MC) and corn starch and polyols-Part 2. Carb. Pol. 1996, 31, 193-204.
43. López, O. V., Lecot, C. J., Zaritzky, N. E., García, M. A., Biodegradable packages development from starch based heat sealable films. J. Food Eng. 2011, 105, 254-263.
44. Ionescu, M., Petrovic, Z. S., Phenolation of vegetable oils. J. Serb. Chem. Soc. 2011, 76, 591-606.
45. Pchelka, B. K., Loupy, A., Petit, A., Improvement and simplification of synthesis of 3-aryloxy-1, 2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism. Tetrahedron 2006, 62, 10968-10979.
46. Sachinvala, N. D., Winsor, D. L., Menescal, R. K., Ganjian, I. et al., Sucrose-based epoxy monomers and their reactions with diethylenetriamine. J. Pol. Sci. Part A Pol. Chem. 1998, 36, 2397-2413.
47. Won, Y. G., Galy, J., Gérard, J. F., Pascault, J. P. et al., Internal antiplasticization in copolymer and terpolymer networks based on diepoxides, diamines and monoamines. Polymer 1990, 31, 1787-1792.
48. Pan, X., Sengupta, P., Webster, D. C., High biobased content epoxy-anhydride thermosets from epoxidized sucrose esters of fatty acids. Biomacromolecules 2011, 12, 2416-2428.