Biobased epoxidized vegetable oils and its greener epoxy blends: A review

Polymer - Plastics Technology and Engineering

Volumn 49, Issue 15, 2010, Pages 1581-1590

  Tan, S G ^a   Chow, W S ^a  

^a SCHOOL OF MATERIALS AND MINERAL RESOURCES ENGINEERING   (Malaysia)

Author keywords

Bio based resin; Conversion efficiency; Epoxidation; Epoxidized vegetable oils; Epoxy blends

Indexed keywords

BIO-BASED; BIO-BASED RESIN; CATALYTIC EPOXIDATION; CATALYZED EPOXIDATION; CONVERSION RATES; ENVIRONMENTALLY-FRIENDLY; EPOXIDATION METHODS; EPOXIDIZED VEGETABLE OIL; EPOXY BLENDS; GREEN MATERIALS; POLYMER INDUSTRIES;

CONVERSION EFFICIENCY; ION EXCHANGE; LUBRICATING OILS; NATURAL POLYMERS; POLYMERS; RENEWABLE ENERGY RESOURCES; RESINS; VEGETABLE OILS;

EPOXIDATION;

EID: 78649917176     PISSN: 03602559     EISSN: 15256111     Source Type: Journal    
DOI: 10.1080/03602559.2010.512338     Document Type: Review

References (57)

1. Miyagawa, H.; Misra, M.; Drzal, L.T. Fracture toughness and impact strength of anhydride-cured biobased epoxy. Polym. Eng. Sci. 2005, 45,487-495.
2. Miyagawa, H.; Jurek, R.J.; Mohanty, A.K.; Misra, M.; Drzal, L.T. Biobased epoxy/clay nanocomposites as a new matrix for CFRP. Compos. Pt. A 2006, 37, 54-62.
3. Mohamed, A.S.; Shanmugam, N.; Muthukaruppan, A. Synthesis and characterization of bismaleimide-modified, soy-based epoxy matrices for flame-retardant application. High Perform. Polym. 2010, 22, 328-344.
4. Bo, L.; Yang, L.T.; Dai, H.H.; Yi, A.H. Kinetic studies on oxirane cleavage of epoxidized soybean oil by methanol and characterization of polyols. J. Am Oil Chem Soc. 2008, 85, 113-117.
5. Meyer, P.P.; Techaphattana, N.; Manundawee, S.; Sangkeaw, S.; Junlakan, W.; Tongurai, C. Epoxidation of soybean oil and jatropha oil. Thammasat Int. J. Sc. Tech. 2008, 13, 1-5.
6. Jue, L.; Wool, R.P. Additive toughening effects on new bio-based thermosetting resins from plant oils. Compos. Sci. Technol. 2008, 68,1025-1033.
7. Park, S.J.; Jin, F.L.; Lee, J.R. Effect of biodegradable epoxidized castor oil on physicochemical and mechanical properties of epoxy resins. Macromol. Chem, Phys. 2004, 205, 2048-2054.
8. Jin, F.L.; Park, S.J. Thermal and rheological properties of vegetable oil-based epoxy resins cured with thermally latent initiator. J. Ind. Eng. Chem. 2007, 13, 808-814.
9. Cheong, M.Y.; Ooi, T.L.; Ahmad, S.; Wan, M.Z.W.Y.; Kuang, D. Synthesis and characterization of palm-based resin for UV coating. J. Appl. Polym. Sci. 2009, 111, 2353-2361.
10. Ortiz, R.A.; Lopez, D.P.; Cisneros, M.L.G.; Valverde, J.C.R.; Crivello, J.V. A Kinetic study of the acceleration effect of substituted benzyl alcohols on the cationic photopolymerization rate of epoxidized natural oils. Polymer, 2005, 46, 1535-1541.
11. Dinda, A.; Patwardhan, A.V.; Goud, V.V.; Pradhan, N.C. Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalyzed by liquid inorganic acids. Bioresour Technol. 2008, 99, 3737-3744.
12. Goud, V.V.; Pradhan, N.C.; Patwardhan, A.V. Epoxidation of Karanja (Pongamia Glabra) oil by H2O2. J. Am. Oil Chem. Soc. 2006,83,635-640.
13. Gerbase, A.E.; Gregorio, J.R.; Martinelli, M.; Brasil, M.C.; Mendes, A.N.F. Epoxidation of soybean oil by the methyltrioxorhenium-CH2-Cl2/H2O2 catalytic biphasic system. J. Am. Oil Chem. Soc. 2002, 79, 179-181.
14. Clayton, A.M. Epoxy Resins: Chemistry and Technology, CRC Press: Boca Raton, FL, 1988, p 1-4.
15. Chandrashekhara, K.; Sundararaman, S.; Flanigan, V.; Kapila, S. Affordable composites using renewable materials. Mater. Sci. Eng. A. 2005,412,2-6.
16. Gunstone, F.D.; Fred, B.P. Lipid Technologies and Applications, CRC Press: Boca Raton, FL, 1997, p 765.
17. Amar, K.M.; Manjusri, M., Lawrence, T.D. Natural Fibers, Biopolymers and Biocomposites, CRC Press: Boca Raton, FL, 2005, pp. 20-21.
18. Ratna, D.; Banthia, A.K. Rubber toughened epoxy. Macromol. Res. 2004,12,11-21.
19. Khot, S.N.; John, J.L.; Erde, C.; Shantaram, S.M.; George, I.W.; Giuseppe, R.P.; Selim, H.K.; Richard, P.W. Development and application of triglyceride-based polymers and composites. J. Appl. Polym. Sci. 2001, 82, 703-723.
20. Yusof, B.; Yew, F.K. Global Oils & Fats Business Magazine. Vol. 6. GOFB: Malaysia, 2009, pp 1-8.
21. Frank, R.C.; Luc, P.; Arnaldo, W. A Global Overview of Vegetable Oils with Reference to Biodiesel: A Report for the IEA Bioenergy Task 40. UK, Imperial College, 2009, 10.
22. Hiroaki, M.; Robert, J.J.; Amar, K.M.; Manjusri, M.; Lawrence, T.D. Biobased epoxy/clay nanocomposites as a new matrix for CFRP. Composites: Part A. 2006, 37, 54-62.
23. Van, D.V.H.A.M.; Mkamilo, G.S. Cereals and Pulses (Plant Resources of Tropical Africa 1). Africa, PROTA, 2006, 69.
24. Yusof, B. Palm oil and its global supply and demand prospects. Oil Palm Indust. Econ. J. 2002, 2, 1-10.
25. Rosli, W.D.; Kumar, R.N.; Mek Zah, S.; Hilmi, M.M. UV radiation curing of epoxidized palm oil-cycloaliphatic diepoxide system induced by cationic photoinitiator for surface coating. Euro. Polym. J. 2003, 39,593-600.
26. Cai, C.S.; Dai, H.H.; Chen, R.S.; Su, C.X.; Xu, X.Y.; Zhang, S.; Yang, L.T. Studies on the kinetics of in situ epoxidation of vegetable oils. Eur. J. Lipid Sci. Technol. 2008, 110, 341-346.
27. Xu, J.Y.; Liu, Z.S.; Erhan, S.Z.; Carriere, C.J. A potential biodegradable rubberviscoelastic properties of a soybean oil-based composite. J. Am. Oil Chem. Soc. 2002, 79, 593-596.
28. Klass, M.; Warwel, S. (1999). Complete and partial epoxidation of plant oils by lipase-catalyzed perhydrolysis. Indust. Crops Prod. 1999,9,125-132.
29. Cai, S.F.; Wang, L.S.; Fan, C.L. Catalytic epoxidation of a technical mixture of methyl oleate and methyl linoleate in ionic liquids using MoO(O2)2.2QOH (QOH1/48-quinilinol) as catalyst and NaHCO3 as Co-Catalyst. Molecules 2009, 14, 2935-2946.
30. Hilker, I.; Bothe, D.; Pruss, J.; Warnecke, J. Chemo-enzymatic epoxidation of unsaturated plant oils. Chem. Eng. Sci. 2001, 56, 427-432.
31. Gerhard, K.; Johannes, T.P.D. Recent Developments in the Synthesis of Fatty Acid Derivatives, AOCS Press: USA, 1999, p 157.
32. Stepanski, M.L.; Glukhan, E.N.; Torubarov, A.L. New technology for production of epoxidized vegetable oils. Russia, Shosse Entusiastiv 2005, 1.
33. Goud, V.V.; Patwardhan, A.V.; Pradhan, N.C. Studies on the epoxidation of Mahua Oil (Madhumica Indica) by hydrogen peroxide. Biores. Technol. 2006, 97, 1365-1371.
34. Gurbanov, M.S.; Mamedov, B.A. Epoxidation of flax oil with hydrogen peroxide in a conjugate system in the presence of acetic acid and chlorinated cation exchanger KU-2 8 as catalyst. Russ. J. Appl. Chem. 2009, 82, 1483-1487.
35. Sinadinovic-Fiser, S.; Jankovic, M.; Petrovic, Z.S. Kinetics of in situ epoxidation of soybean oil in bulk catalyzed by ion exchange resin. J. Am. Oil Chem. Soc. 2001, 78, 725-731.
36. Mungroo, R.; Pradhan, N.C.; Goud, V.V.; Dalai, A.K. Epoxidation of canola oil with hydrogen peroxide catalyzed by acidic ion exchange resin. J. Am. Oil Chem. Soc. 2008, 85, 887-896.
37. Petrivic, Z.S.; Zlatanic, A.; Lava, C.C.; Sinadinovic-Fiser, S. Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids kinetics and side reactions. Eur. J. Lipid Sci. Technol. 2002, 104,293-299.
38. Gerbase, A.E.; Petzhold, C.L.; Costa, A.P.O. Dynamic mechanical and thermal behavior of epoxy resins based on soybean oil. J. Am. Oil Chem. Soc. 2002, 79, 797-802.
39. Goud, V.V.; Patwardhan, A.V.; Dinda, S.; Pradhan, N.C. Epoxidation of Karanja (Pongamia Glabra) oil catalyzed by acidic ion exchange resin. Eur. J. Lipid Sci. Technol. 2007, 109, 575-584.
40. Rosana, C.S.S.; Luciano, R.S.L.; Thiago, B.B.; Maria, G.N.; Marta, R.S.N. Chemo-enzymatic epoxidation of sunflower oil methyl esters. J. Braz. Chem, Soc. 2009, 20, 1473-1477.
41. Ursula, B.; Wolfgang, F.; Siegmund, L.; Wilfried, L.; Guido, M.; Jurgen, O.M.; Mark, R.K.; Hans, J.S.; Manfred, P.S. New syntheses with oils and fats as renewable raw materials for the chemical industry. Angew. Chem. Int. Ed. 2000, 39, 2206-2224.
42. Vlcek, T.; Petrovic, Z.S. Optimization of the chemoenzymatic epoxidation of soybean oil. J. Am. Oil Chem. Soc. 2006, 83, 247-252.
43. Tellez, G.L.; Santiago, E.V.; Lopez, S.H. Characterization of linseed oil epoxidized at different percentages. Superficies y Vacio. 2009, 22, 5-10.
44. 1H NMR. Eur. J. Lipid Sci. Technol. 2007, 109, 1186-1193.
45. Maiti, S.K.; Dinda, S.; Nandi, M.; Bhaumik, A.; Bhattacharyya, R. Selective epoxidation of olefins catalyzed by oxodiperoxomolybdenum (vi) complexes immobilized over highly ordered 2D-hexagonal mesoporous silica. J. Mol. Catal. A Chem. 2008, 287, 135-141.
46. Sobczak, J.M.; Ziolkowski, J.J. Molybdenum complex-catalysed epoxidation of unsaturated fatty acids by organic hydroperoxides. Applied Catalysis A: General. 2003, 248, 261-268.
47. Park, S.J.; Jin, F.L.; Lee, J.R. Synthesis and thermal properties of epoxidized vegetable oil. Macromol. Rapid Commun. 2004, 25, 724-727.
48. Jin, F.L.; Park, S.J. Impact-strength improvement of epoxy resins reinforced with a biodegradable polymer. Mater. Sci. Eng. A. 2008, 478,402-405.
49. Jin, F.L.; Park, S.J. Thermomechanical behavior of epoxy resins modified with epoxidized vegetable oils. Polym. Int. 2008, 57, 577-583.
50. Ratna, D. Mechanical properties and morphology of epoxidized soyabean-oil-modified epoxy resin. Polym. Int. 2001, 50, 179-184.
51. Raghavachar, R.; Letasi, R.J.; Kola, P.V.; Chen, Z.; Massingill, J.L. Rubber-toughening epoxy thermosets with epoxidized Crambe oil. J. Am. Oil Chem. Soc. 1999, 76, 511-516.
52. Miyagawa, H.; Mohanty, A.K.; Misra, M.; Drzal, L.T. Thermo-physical and impact properties of epoxy containing epoxidized linseed oil, Part 1: Anhydride-cured epoxy. Macromol. Mater. Eng. 2004, 289, 629-635.
53. Miyagawa, H.; Mohanty, A.K.; Misra, M.; Drzal, L.T. Thermo-physical and impact properties of epoxy containing epoxidized linseed oil, Part 2: Amine-cured epoxy. Macromol. Mater. Eng. 2004, 289, 636-641.
54. Yue, S.; Hu, J.F.; Huang, H.; Fu, H.Q.; Zeng, H.W.; Chen, H.Q. Synthesis, properties and application of a novel epoxidized soybean oil-toughened phenolic resin. Chin. J. Chem. Eng. 2007, 15, 418-423.
55. Munoz, J.C.; Ku, H.; Cardona, F.; Rogers, D. Effects of catalysts and post-curing conditions in the polymer network of epoxy and phenolic resins: Preliminary results. J. Mater. Process. Technol. 2008, 202, 486-492.
56. Park, S.J.; Jin, F.L.; Lee, J.R. Thermal and mechanical properties of tetrafunctional epoxy resin toughened with epoxidized soybean oil. Mater. Sci. Eng. A 2004, 374, 109-114.
57. Tan, S.G. Preparation and Characterization of Thermal-Curable Epoxy Blends. Dissertation (B.Eng) Universiti Sains Malaysia: Malaysia, 2009, 1-124.