OJOPM  Vol.5 No.1 , January 2015
Modified Vegetable Oil Based Additives as a Future Polymeric Material—Review
Polymeric materials from renewable resources have attracted a lot of attention in recent years. The development and utilization of vegetable oils for polymeric materials are currently in the spotlight of the polymer and chemical industry, as they are the largest renewable platform due to their universal wide availability, ingrained biodegradability, low cost, and excellent environmental aspects (i.e., low ecotoxicity and low toxicity toward humans). These excellent natural characteristics are now being taken advantage of in research and development, with vegetable oil derived polymers/polymeric materials/composites being used in numerous applications including paints and coatings, adhesives, and nanocomposites. The aim of this review paper is to give a fundamental description of the various vegetable oil applications in polymer materials and its recent developments. Particular emphasis will be placed on study and main application of triglyceride based additive for polymer and to give the reader an insight into the main developments is discussed.

Cite this paper
Samarth, N. and Mahanwar, P. (2015) Modified Vegetable Oil Based Additives as a Future Polymeric Material—Review. Open Journal of Organic Polymer Materials, 5, 1-22. doi: 10.4236/ojopm.2015.51001.

[1]   Wool, R.P. and Sun, X.S. (2005) Polymers and Composite Resins from Plant Oils in Bio-Based Polymers and Composites. Elsevier Academic Press, Burlington, 6-113.

[2]   Belgacem, M.N. and Gandini, A. (2008) Materials from Vegetable Oils: Major Sources, Properties and Applications. Monomers, Polymers and Composites from Renewable Resources, Chapter 3, 39-66.

[3]   Lu. Y. and Larock, R.C. (2009) Novel Polymeric Materials from Vegetable Oils and Vinyl Monomers: Preparation, Properties and Applications. ChemSusChem, 2, 136-147.

[4]   Xia. Y. and Larock, R.C. (2010) Vegetable Oil-Based Polymeric Materials: Synthesis, Properties, and Applications. Green Chemistry, 12, 1893-1909. http://dx.doi.org/10.1039/c0gc00264j

[5]   Khot, S.N., Lascala, J.J., Can, E., Morye, S.S., Williams, G.I., Palmese, G.R., et al. (2001) Development and Application of Triglyceride-Based Polymers and Composites. Journal of Applied Polymer Science, 82, 703-723.

[6]   Hui, Y.H. (1995) Bailey’s Industrial Oil and Fats Products, Edible Oil and Fat Products: General Application. 5th Edition, Vol. 1, Wiley, Blackwell, 19-44.

[7]   Guner, F.S., Yagci. Y. and Erciyes, A.T. (2006) Polymers from Triglyceride Oils. Progress in Polymer Science, 31, 633-670. http://dx.doi.org/10.1016/j.progpolymsci.2006.07.001

[8]   Habib, F. and Bajpai, M. (2011) Synthesis and Characterization of Acrylated Epoxidized Soybean Oil for UV-Cured Coatings. Chemistry & Chemical Technology, 5, 317-326.

[9]   Ronda, J.C., et al. (2011) Vegetable Oils as Platform Chemicals for Polymer Synthesis. European Journal of Lipid Science and Technology, 113, 46-58. http://dx.doi.org/10.1002/ejlt.201000103

[10]   Montero de Espinosa, L. and Meier, M.A.R. (2011) Plant Oils: The Perfect Renewable Resource for Polymer Science?! European Polymer Journal, 47, 837-852.

[11]   Kayode, A., Christian, P., Adib, K. and Mikael, S. (2011) Mechanical and Viscoelastic Properties of Soybean Oil Thermoset Reinforced with Jute Fabrics and Carded Lyocell Fiber. Journal of Applied Polymer Science, 122, 2855- 2863. http://dx.doi.org/10.1002/app.34360

[12]   Muturi, P., Wang, D. and Dirlikov, S. (1994) Epoxidized Vegetable Oils as Reactive Diluents I. Comparison of Vernonia, Epoxidized Soybean and Epoxidized Linseed Oils. Progress in Organic Coatings, 25, 85-94.

[13]   Ratna, D. and Banthia, A.T. (2000) Epoxidized Soybean Oil Toughened Epoxy Adhesive. Journal of Adhesion Science and Technology, 14, 15-25. http://dx.doi.org/10.1163/156856100742087

[14]   Dirlikov, S.K., Frischinger, I., Islam, M.S. and Graham, J. (1990) Vernonia Oil: A New Reactive Monomer. Polymer Engineering & Science, 62, 217-221.

[15]   Mohanty, A.K., Misra, M., Drzal, L.T., et al. (2005) Natural Fibers, Biopolymer and Biocomposites. CRC Press, Boca Raton, 20-21.

[16]   Bo, L., Yang, L.T., Dai, H.H. and Yi, A.H. (2008) Kinetic Studies on Oxirane Cleavage of Epoxidized Soybean Oil by Methanol and Characterization of Polyols. Journal of the American Oil Chemists’ Society, 85, 113-117.

[17]   Meyer, P.P., Techaphattana, N., Manundawee, S., Sangkeaw, S., Junlakan, W. and Tongurai, C. (2008) Epoxidation of Soybean Oil and Jatropha Oil. Thammasat International Journal of Science and Technology, 13, 1-5.

[18]   Rosli, W.D., Kumar, R.N., Mek, Z.S. and Hilmi, M.M. (2003) UV Radiation Curing of Epoxidized Palm Oil-Cycloa- liphatic Diepoxide System Induced by Cationic Photoinitiator for Surface Coatings. European Polymer Journal, 39, 593-600. http://dx.doi.org/10.1016/S0014-3057(02)00241-0

[19]   Klass, M. and Warwel, S. (1999) Complete and Partial Epoxidation of Plant Oils by Lipase-Catalyzed Perhydrolysis. Industrial Crops and Products, 9, 125-132.

[20]   Xu, J.Y., Liu, Z.S., Erhan, S.Z. and Carriere, C.J. (2002) A Potential Biodegradable Rubber—Viscoelastic Properties of a Soybean Oil-Based Composite. Journal of the American Oil Chemists’ Society, 79, 593-596.

[21]   Hiroaki, M., Robert, J.J., Amar, K.M., Manjusri, M. and Lawrence, T.D. (2006) Biobased Epoxy/Clay Nanocomposites as a New Matrix for CFRP. Composites Part A: Applied Science and Manufacturing, 37, 54-62.

[22]   Hilker, I., Bothe, D., Pruss, J. and Warnecke, J. (2001) Chemo-Enzymatic Epoxidation of Unsaturated Plant Oils. Chemical Engineering Science, 56, 427-432.

[23]   Barrett, L.W., Sperling, L.H. and Murphy, C.J. (1993) Naturally Functionalized Triglyceride Oils in Interpenetrating Polymer Networks. Journal of the American Oil Chemists’ Society, 70, 523-534.

[24]   Qureshi, S., Manson, J.A., Sperling, L.H. and Murphy, C.J. (1983) In: Carraher, C.E. and Sperling, L.H., Eds., Polymer Application of Renewable Resources Materials. Plenum Press, New York, 249-271.

[25]   United States Department of Agriculture (2012) Oilseeds: World Markets and Trade Archives.

[26]   Corma, A., Iborra, S. and Velty, A. (2007) Chemical Routes for the Transformation of Biomass into Chemicals. Chemical Reviews, 107, 2411-2502. http://dx.doi.org/10.1021/cr050989d

[27]   Biermann, U., Bornscheuer, U., Meier, M.A.R., Metzger, J.O. and Schafer, H.J. (2011) Oils and Fats as Renewable Raw Materials in Chemistry. Angewandte Chemie International Edition, 50, 3854-3871.

[28]   Battersby, N.S., Pack, S.E. and Watkinson, R.J. (1992) A Correlation between the Biodegradability of Oil Products in the CEC L-33-T-82 and Modified Sturm Tests. Chemosphere, 24, 1998-2000.

[29]   Shashidhara, Y.M. and Jayaram, S.R. (2010) Vegetable Oils as a Potential Cutting Fluid—An Evolution. Tribology International, 43, 1073-1081. http://dx.doi.org/10.1016/j.triboint.2009.12.065

[30]   Matthew, T.S., Nader, S., Bigyan, A. and Lambert, A.D. (2007) Influence of Fatty Acid Composition on the Tribological Performance of Two Vegetable-Based Lubricants. Journal of Synthetic Lubrication, 24, 101-110. http://dx.doi.org/10.1002/jsl.32

[31]   Joseph, P.V. (2007) Study of Some Non-Edible Vegetable Oils of Indian Origin for Lubricant Application. Journal of Synthetic Lubrication, 24, 181-197. http://dx.doi.org/10.1002/jsl.39

[32]   Sivasankaran, G.A. (1988) Jojoba-Oil-Based Two Stroke Gasoline Engine Lubricant. Tribology International, 21, 327- 333. http://dx.doi.org/10.1016/0301-679X(88)90109-0

[33]   Bhatnagar, A.H. (2006) HFRR Studies on Methyl Ester of Non Edible Vegetable Oils. Energy & Fuels, 20, 1341-1344.

[34]   Singh, A.K., et al. (2006) Metal Working Fluids from Vegetable Fluids. Journal of Synthetic Lubrication, 123, 167- 176. http://dx.doi.org/10.1002/jsl.19

[35]   Loredana, P. (2008) Base Stock Oils for Lubricants from Mixtures of Corn Oil and Synthetic Diesters. Journal of the American Oil Chemists’ Society, 85, 71-76. http://dx.doi.org/10.1007/s11746-007-1156-z

[36]   Borden, G.W. and Smith, O.W. (1997) Radiation Curable Inks and Coatings. US Patent No. 4025477.

[37]   Kirschenbauer, H.G. (1960) Fats and Oils: An Outline of Their Chemistry and Technology. Reinhold, New York.

[38]   Williams, G.I. and Wool, R.P. (2000) Composites from Natural Fibers and Soy Oil Resins. Applied Composite Materials, 7, 421-423. http://dx.doi.org/10.1023/A:1026583404899

[39]   Bunker, S.P. and Wool, R.P. (2002) Synthesis and Characterization of Monomers and Polymers for Adhesives from Methyl Oleate. Journal of Polymer Science Part A: Polymer Chemistry, 40, 451-458.

[40]   Larock, R.C., Dong, X.Y., Chung, S., Reddy, C.K. and Ehlers, L.E. (2001) Preparation of Conjugated Soybean Oil and Other Natural Oils and Fatty Acids by Homogeneous Transition Metal Catalysis. Journal of the American Oil Chemists’ Society, 78, 447-453. http://dx.doi.org/10.1007/s11746-001-0284-1

[41]   Meiorin, C., Aranguren, M.I. and Mosiewicki, M.A. (2012) Vegetable Oil Based Thermoset Copolymers with Shape Memory Behavior and Damping Capacity. Polymer International, 64, 735-742. http://dx.doi.org/10.1002/pi.3231

[42]   Meiorin, C., Aranguren, M.I. and Mosiewicki, M.A. (2012) Smart and Structural Thermosets from Cationic Copolymerization of a Vegetable Oil. Journal of Applied Polymer Science, 124, 5071-5708.

[43]   Li, F.K. and Larock, R.C. (2003) Synthesis, Structure and Properties of New Tung Oil-Styrene-Divinylbenzene Copolymers Prepared by Thermal Polymerization. Biomacromolecules, 4, 1018-1025. http://dx.doi.org/10.1021/bm034049j

[44]   Mosiewicki, M.A., Arciprete, G.A., Aranguren, M.I. and Marcovich, N.E. (2009) Polyurethane Foams Obtained from Castor Oil Based Polyol and Filled with Wood Flour. Journal of Composite Materials, 43, 3057-3072.

[45]   Wik, V.M., Aranguren, M.I. and Mosiewicki, M.A. (2011) Castor Oil-Based Polyurethanes Containing Cellulose Nanocrystals. Polymer Engineering & Science, 51, 1389-1396.

[46]   La Scala, J. and Wool, R.P. (2002) Effect of FA Composition on Epoxidation Kinetics of TAG. Journal of the American Oil Chemists’ Society, 79, 373-378. http://dx.doi.org/10.1007/s11746-002-0491-9

[47]   Petrovic, Z.S., Zlatanic, A., Lava, C.C. and Sinadinovic-Fiser, S. (2002) Epoxidation of Soybean Oil in Toluene with Peroxoacetic and Peroxoformic Acids—Kinetics and Side Reactions. European Journal of Lipid Science and Technology, 104, 293-299.

[48]   Lu, J., Khot, S. and Wool, R.P. (2005) New Sheet Molding Compounds Resins from Soybean Oil. I. Synthesis and Characterization. Polymer, 46, 71-80.

[49]   Anderson, D.F. and Mckenzie, D.A. (1970) Mechanism of the Thermal Stabilization of Poly(vinyl chloride) with Metal Carboxylates and Epoxy Plasticizers. Journal of Polymer Science Part A-1: Polymer Chemistry, 8, 2905-2922.

[50]   Helena, W., Rolf, L. and Theo, M. (2001) Lubricant Base Fluids Based on Renewable Raw Materials Their Catalytic Manufacture and Modification. Applied Catalysis A: General, 221, 429-442.

[51]   Ravasio, N., et al. (2002) Environmetal Friendly Lubricants through Slective Hydrogenation of Rapeseed Oil over Supported Copper Catalyst. Applied Catalysis A: General, 233, 1-6.

[52]   Piyush, S.L. (2007) Green Approach for the Preparation of Biodegradable Lubricant Base Stock from Epoxidised Vegetable Oil. Applied Catalysis B: Environmental, 69, 207-212.

[53]   Adhvaryu, A. (2004) Tribological Studies of Thermally and Chemically Modified Vegetable Oils for Use as Environmentally Friendly Lubricants. Wear, 257, 359-367.

[54]   Mehta, B., Kathalewar, M. and Sabnis, A. (2014) Benzyl Ester of Dehydrated Castor Oil Fatty Acid as Plasticizer for Poly(vinyl chloride). Polymer International, 63, 1456-1464.

[55]   Frye, A.H. and Horst, R.W. (1959) The Mechanism of Poly(vinyl chloride) Stabilization by Barium, Cadmium, and Zinc Carboxylates. I. Infrared Studies. Journal of Polymer Science, 40, 419-431.

[56]   Benaniba, M.T., Belhaneche-Bensemrab, N. and Gelbard, G. (2001) Stabilizing Effect of Epoxidized Sunflower Oil on the Thermal Degradation of Poly(Vinyl Chloride). Polymer Degradation and Stability, 74, 501-505.

[57]   Benanibaa, M.T., Belhaneche-Bensemrab, N. and Gelbardc, G. (2003) Stabilization of PVC by Epoxidized Sunflower Oil in the Presence of Zinc and Calcium Stearates. Polymer Degradation and Stability, 82, 245-249.

[58]   Lerke, G., Lerke, I. and Szymanski, W. (1983) Stabilization of Gamma-Irradiated Poly(vinyl chloride) by Epoxy Compounds. III. Conjugated Double Bonds and Degree of Unsaturation in Gamma-Irradiated PVC-Stabilizer Mixtures. Journal of Applied Polymer Science, 28, 519-529. http://dx.doi.org/10.1002/app.1983.070280208

[59]   Housel, S.D. (1985) Additives Help Hold Color in Gamma-Sterilized PVC. Plastics Engineering, 47-49.

[60]   Troitskii, B.B., Troitskaya, L.S. and Denisova, V.N. (1988) Prept. Int. 31 Microsymp Macromolecules “Polyvinyl Cholride”, Prague, 69.

[61]   Wypych, J. (1986) Polyvinyl Chloride Stabilization. Elsevier, Amsterdam.

[62]   Owen, E.D. (1984) Degradation and Stabilization of PVC. Elsevier Applied Science Publishers, London, 21-80.

[63]   Okieimen, F.E. and Ebhoaye, J.E. (1993) Thermal Dehydrochlorination of PVC in the Presence of Rubber Seed Oil. Die Angewandte Makromolekulare Chemie, 206, 11-20.

[64]   Okieimen, F.E. (2002) Studies in the Utilisation of Epoxidized Vegetable Oils as Thermal Stabiliser for Poly(vinyl chloride). Industrial Crops and Products, 15, 71-75. http://dx.doi.org/10.1016/S0926-6690(01)00097-8

[65]   Okieimen, F.E. and Ebhoaye, J.E. (1993) Studies in the Thermal Degradation of Poly(Vinyl Chloride). Journal of Applied Polymer Science, 48, 1853-1858. http://dx.doi.org/10.1002/app.1993.070481019

[66]   Badra, B. and Mohamed, T.B. (2008) Effects of Epoxidized Sunflower Oil on the Mechanical and Dynamical Analysis of the Plasticized Poly(vinyl chloride). Journal of Applied Polymer Science, 107, 3442-3450.

[67]   Taghizadeh, M.T., Nalbandi, N. and Bahadori, A. (2008) Stabilizing Effect of Epoxidized Sunflower Oil as a Secondary Stabilizer for Ca/Hg Stabilized PVC. Express Polymer Letters, 2, 65-76.

[68]   Randles, S.J. and Wright, M. (1992) Environmentally Considerate Ester Lubricants for the Automotive and Engineering Industries. Journal of Synthetic Lubrication, 9, 145-161.

[69]   Naughton, F.C. (1974) Production, Chemistry, and Commercial Applications of Various Chemicals from Castor Oil. Journal of the American Oil Chemists Society, 51, 65-71.

[70]   Gast, L.E., Croston, C.B., Schneider, W.J. and Teeter, H.M. (1954) Synthetic Lubricants from Polyhydroxystearic Acids. Journal of Industrial and Engineering Chemistry, 46, 2205-2208. http://dx.doi.org/10.1021/ie50538a056

[71]   Becker, R. and Knorr, A. (1996) An Evaluation of Antioxidants for Vegetable Oils at Elevated Temperatures. Lubrication Science, 8, 95-117. http://dx.doi.org/10.1002/ls.3010080202

[72]   Uosukainen, E., Linko, Y.Y., Lamasa, M., Tervakangas, T. and Linko, P. (1998) Transesterification of Trimethylolpropane and Rapeseed Oil Methyl Ester to Environmentally Acceptable lubricants. Journal of the American Oil Chemists’ Society, 75, 1557-1563. http://dx.doi.org/10.1007/s11746-998-0094-8

[73]   Johansson, L.E. and Lundin, S.T. (1979) Copper Catalysts in the Selective Hydrogenation of Soybean and Rapeseed Oils: I. The Activity of the Copper Chromite Catalyst. Journal of the American Oil Chemists’ Society, 56, 974-980.

[74]   Sinadinovic-Fiser, S., Jankovic, M. and Petrovic, Z.S. (2001) Kinetics of in Situ Epoxidation of Soybean Oil in Bulk Catalyzed by Ion Exchange Resin. Journal of the American Oil Chemists’ Society, 78, 725-731.

[75]   Adhvaryu, A. and Erhan, S.Z. (2002) Epoxidized Soybean Oil as a Potential Source of High-Temperature Lubricants. Industrial Crops and Products, 15, 247-254. http://dx.doi.org/10.1016/S0926-6690(01)00120-0

[76]   Padwa, A. and Murphree, S.S. (2006) Epoxides and Aziridines—A Mini Review. Arkivoc, 3, 6-33.

[77]   Rios, L.A., Weckes, P.P., Schuster, H. and Hoelderich, W.F. (2005) Resin Catalyzed Alcoholysis of Epoxidized Fatty Esters: Effect of the Alcohol and the Resin Structures. Applied Catalysis A: General, 284, 155-161.

[78]   Lathi, P.S. and Mattiasson, B. (2007) Green Approach for the Preparation of Biodegradable Lubricant Base Stock from Epoxidized Vegetable Oil. Applied Catalysis B: Environmental, 69, 207-212.

[79]   Fox, N.J. and Stachowiak, G.W. (2007) Vegetable Oil-Based Lubricants—A Review of Oxidation. Tribology International, 40, 1035-1046. http://dx.doi.org/10.1016/j.triboint.2006.10.001

[80]   Campanella, A., Rustoy, E., Baldessari, A. and Baltanas, M.A. (2010) Lubricants from Chemically Modified Vegetable Oils. Bioresource Technology, 101, 245-254.

[81]   Wu, X., Zhang, X., Yang, S., Chen, H. and Wang, D. (2000) The Study of Epoxidized Rapeseed Oil Used as a Potential Biodegradable Lubricant. Journal of the American Oil Chemists’ Society, 77, 561-563.

[82]   Hwang, H. and Erhan, S.Z. (2001) Modification of Epoxidized Soybean Oil for Lubricant Formulations with Improved Oxidative Stability and Low Pour Point. Journal of the American Oil Chemists’ Society, 78, 1179-1184.

[83]   Hwang, H. and Erhan, S.Z. (2006) Synthetic Lubricant Basestocks from Epoxidized Soybean Oil and Guerbet Alcohols. Industrial Crops and Products, 23, 311-317.

[84]   Bialecka-Florjanczyk, E. and Florjanczyk, Z. (2007) Solubility of Plasticizers, Polymers and Environmental Pollution. Chapter 22, Thermodynamics, Solubility and Environmental Issues, 397-407.

[85]   Rahman, M. and Brazel, C.S. (2004) The Plasticizer Market: An Assessment of Traditional Plasticizers and Research Trends to Meet New Challenges. Progress in Polymer Science, 29, 1223-1248.

[86]   Baltacioglu, H. and Balkose, D. (1999) Effect of Zinc Stearate and/or Epoxidized Soybean Oil on Gelation and Thermal Stability of PVC-DOP Plastigels. Journal of Applied Polymer Science, 74, 2488-2498.

[87]   Krauskopf, L.G. and Godwin, A. (2005) Plasticizers. In: Wilkes, C.E., Summers, J.W. and Daniels, C.A., Eds., PVC Handbook, Hanser, Munich, 173-193.

[88]   Wypych, G. (2004) Handbook of Plasticizers. Chem Tech, Toronto, New York, 687.

[89]   Vieira, M.G.A., Silva, M.A.D., Santos, L.O.D. and Beppu, M.M. (2011) Natural-Based Plasticizers and Biopolymer Films a Review. European Polymer Journal, 47, 254-263.

[90]   Suarez Palacios, O.Y., et al. (2014) Multicriteria Optimization of Production Conditions for a New Phthalate-Free PVC Plasticizer. Journal of Industrial and Engineering Chemistry, 20, 1985-1992.

[91]   Formo, M.W. (1995) Industrial Use of Soybean Oil. In: Barnes, P.J. and Associates, Eds., Proceedings of the 21st World Congress of the International Society of Fat Research (ISF), The Hague, Barnes, P.J. and Associates, Hague, 519-527.

[92]   Boussoum, M.O., Atek, D. and Belhaneche-Bensemra, N. (2006) Interactions between Poly(vinyl chloride) Stabilised with Epoxidised Sunflower Oil and Food Stimulants. Polymer Degradation and Stability, 91, 579-584.

[93]   Karmalm, P., Hjertberg, T., Jansson, A., Dahl, R. and Ankner, K, (2009) Network Formation by Epoxidised Soybean Oil in Plastisol Poly(Vinyl Chloride). Polymer Degradation and Stability, 94, 1986-1990.

[94]   da Silva, M.A., Vieira, M.G.A., Maçumoto, A.C.G. and Beppu, M.M. (2011) Polyvinylchloride (PVC) and Natural Rubber Films Plasticized with a Natural Polymeric Plasticizer Obtained through Polyesterification of Rice Fatty Acid. Polymer Testing, 30, 478-484.

[95]   Greco, A., Brunetti, D., Renna, G., Mele, G. and Maffezzoli, A. (2010) Plasticizer for Poly(vinyl chloride) from Cardanol as a Renewable Resource Material. Polymer Degradation and Stability, 95, 2169-2174.

[96]   Fenollar, O., Garcia-Sanoguera, D., Sanchez-Nacher, L., Lopez, J. and Balart, R. (2010) Effect of the Epoxidized Linseed Oil Concentration as Natural Plasticizer in Vinyl Plastisols. Journal of Materials Science, 45, 4406-4413.

[97]   Al-Mulla, E.A.J., Wan Yunus, W.M.Z., Bt Ibrahim, N.A. and Rahman, M.Z.A. (2010) Properties of Epoxidized Palm Oil Plasticized Polytlactic Acid. Journal of Materials Science, 45, 1942-1946.

[98]   Tsujimoto, T., Uyama, H. and Kobayashi, S. (2010) Synthesis of High-Performance Green Nanocomposites from Renewable Natural Oils. Polymer Degradation and Stability, 95, 1399-1405.

[99]   Bhabhe, M.D. and Athawale, V.D. (1997) Chemoenzymatic Synthesis of Oil-Modified Acrylic Monomers as Reactive Diluents for High Solids Coatings. Progress in Organic Coatings, 30, 207-211.

[100]   Rakotonirainy, A.M. and Padua, G.W. (2001) Effects of Lamination and Coating with Drying Oils on Tensile and Barrier Properties of Zein Films. Journal of Agricultural and Food Chemistry, 49, 2860-2863.

[101]   Wold, C.R. and Soucek, M.D. (2000) Viscoelastic and Thermal Properties of Linseed Oil-Based Ceramer Coatings. Macromolecular Chemistry and Physics, 201, 382-392.

[102]   Deffar, D., Teng, G. and Soucek, M.D. (2001) Comparison of Titanium-Oxo-Clusters Derived from Sol-Gel Precursors with TiO2 Nanoparticles in Drying Oil Based Ceramer Coatings. Macromolecular Materials and Engineering, 286, 204-215. http://dx.doi.org/10.1002/1439-2054(20010401)286:4<204::AID-MAME204>3.0.CO;2-4

[103]   Mosiewicki, M.A. and Aranguren, M.I. (2013) A Short Review on Novel Biocomposites Based on Plant Oil Precursors. European Polymer Journal, 49, 1243-1256.

[104]   Hong, C.K. and Wool, R.P. (2005) Development of a Bio-Based Composite Material from Soybean Oil and Keratin Fibers. Journal of Applied Polymer Science, 95, 1524-1538.

[105]   Dahlke, B., Larbig, H., Scherzer, H.D. and Poltrock. R. (1998) Natural Fiber Reinforced Foams Based on Renewable Resources for Automotive Interior Applications. Journal of Cellular Plastics, 34, 361-379.

[106]   Blacker, J.J., Lee, K.Y. and Bismarck, A. (2011) Hierarchical Composites Made Entirely from Renewable Resources. Journal of Biobased Materials and Bioenergy, 5, 1-16.

[107]   Lligadas, G., Ronda, J.C., Galia, M. and Diz, V.C. (2013) Renewable Polymeric Materials from Vegetable Oils: A Per- spective. Materials Today, 16, 337-343.

[108]   Adekunle, K. et al. (2011) Mechanical and Viscoelastic Properties of Soybean Oil Thermoset Reinforced with Jute Fabrics and Carded Lyocell Fiber. Journal of Applied Polymer Science, 122, 2855-2863.

[109]   Chandrashekhara, K., Sundararaman, S., Flanigan, V. and Kapila, S. (2005) Affordable Composites Using Renewable Materials. Materials Science and Engineering: A, 412, 2-6. http://dx.doi.org/10.1016/j.msea.2005.08.066

[110]   Husic, S., Javni, I. and Petrovic, Z.S. (2005) Thermal and Mechanical Properties of Glass Reinforced Soy-Based Polyurethane Composites. Composites Science and Technology, 65, 19-25.

[111]   Henna, P.H., Kessler, M.R. and Larock, R.C. (2008) Fabrication and Properties of Vegetable-Oil-Based Glass Fiber Composites by Ring-Opening Metathesis Polymerization. Macromolecular Materials and Engineering, 293, 979-990.

[112]   Ray, D., Ghorui, S., Bandyopadhyay, N.R., Sengupta, S. and Kar, T. (2012) New Materials from Maleated Castor Oil/Epoxy Resin Blend Reinforced with Fly Ash. Industrial & Engineering Chemistry Research, 51, 2603-2608.

[113]   Pfister, D.P. and Larock, R.C. (2012) Cationically-Cured Natural Oil-Based Green Composites: Effect of the Natural Oil and the Agricultural Fiber. Journal of Applied Polymer Science, 123, 1392-1400.

[114]   Karlheinz, Hill. (2000) Fats and Oils as Oleochemical Raw Materials. Pure and Applied Chemistry, 72, 1255-1264.

[115]   Falbe, J. (1987) Surfactants in Consumer Products: Theory, Technology, Applications. Springer, Heidelberg, 475.

[116]   Belgacem, M.N. and Gandini, A. (2008) Monomers, Polymers and Composites from Renewable Resources. Elsevier, Amsterdam, 154-178.

[117]   Hreczuch, W. (2001) Ethoxylated Rapeseed Oil Acid Methyl Esters as New Ingredients for Detergent Formulations. Tenside Surfactants Detergents, 38, 72-79.

[118]   Konwar, U., Karak, N. and Mandal, M. (2009) Mesua ferrea L. Seed Oil Based Highly Thermostable and Biodegradable Polyester/Clay Nanocomposites. Polymer Degradation and Stability, 94, 2221-2230.

[119]   Mulazim, Y., Cakmakc, E. and Kahraman, M.V. (2011) Preparation of Photo Curable Highly Hydrophobic Coatings Using a Modified Castor Oil Derivative as a Sol-Gel Component. Progress in Organic Coatings, 72, 394-401.

[120]   Sharmin, E., Akram, D., Ghosal, A., Rahman, O., Zafar, F. and Ahmad, S. (2011) Preparation and Characterization of Nanostructured Biohybrid. Progress in Organic Coatings, 72, 469-472.

[121]   Qureshi, S., Manson, J.A., Michel, J.C, Hertzberg, R.W. and Sperling, L.H. (1984) In: Labana, S.S. and Dickie, R.A., Eds., Characterization of Highly Crosslinked Polymers, ASC Symposium Series 243, American Chemical Society, Washington DC, 8.

[122]   Fernandez, A.M., Manson, J.A. and Sperling, L.H. (1986) Simultaneous Interpenetrating Networks Based on Vernonia Oil Polyesters and Polystyrene: II. A Comparison of the Reactivities of Vernonia Oil and Castor Oil toward the Formation of Polyesters. In: Carraher, C. and Sperling, L.H., Eds., Renewable Resource Materials, Plenum Press, New York, 177-186. http://dx.doi.org/10.1007/978-1-4613-2205-4_15

[123]   Frischinger, I. and Dirlikov, S. (1991) Two-Phase Interpenetrating Epoxy Thermosets That Contain Epoxidized Triglyceride Oils. Interpenetrating Polymer Networks, 25, 517-538.

[124]   Crivello, J.V. and Narayan, R. (1992) Epoxidized Triglycerides as Renewable Monomers in Photoinitiated Cationic Polymerization. Chemistry of Materials, 4, 692-699. http://dx.doi.org/10.1021/cm00021a036

[125]   Vereshagin, A.G. and Novitskaya, G.V. (1965) The Triglyceride Composition of Linseed Oil. Journal of the American Oil Chemists Society, 42, 970-974. http://dx.doi.org/10.1007/BF02632457

[126]   Mahendran, A.R., Wuzella, G., Aust, N., Kandelbaue, A. and Müllera, U. (2012) Photo Crosslinkable Modified Vegetable Oil Based Resin for Wood Surface Coating Application. Progress in Organic Coatings, 74, 697-704.

[127]   Basturk, E., Inan, T. and Gungora, A. (2013) Flame Retardant UV-Curable Acrylated Epoxidized Soybean Oil Based Organic-Inorganic Hybrid Coating. Progress in Organic Coatings, 76, 985-992.

[128]   de Luca, M.A., Martinelli, M., Jacobi, M.M., Becker, P.L. and Ferrao, M.F. (2006) Ceramer Coatings from Castor Oil or Epoxidized Castor Oil and Tetraethoxysilane. Journal of the American Oil Chemists’ Society, 83, 147-151.

[129]   de Luca, M.A., Martinelli, M. and Barbieri, C.T. (2009) Hybrid Films Synthesised from Epoxidised Castor Oil, γ-Gly- cidoxypropyltrimethoxysilane and Tetraethoxysilane. Progress in Organic Coatings, 65, 375-380.

[130]   Becchi, D.M., de Luca, M.A., Martinelli, M. and Mitidieri, S. (2011) Organic-Inorganic Coatings Based on Epoxidised Castor Oil/APTES/TEOS. Journal of the American Oil Chemists’ Society, 88, 101-109.

[131]   Martinelli, M., de Luca, M.A., Bechi, D.M. and Mitidieri, S. (2009) Hybrid Films Based on Hydroxylated Castor Oil and Titanium(IV) Isopropoxide. Journal of Sol-Gel Science and Technology, 52, 202-209.

[132]   Bechi, D.M., de Luca, M.A., Martinellia, M. and Mitidieri, S. (2013) Organic-Inorganic Coatings Based on Epoxidized Castor Oil with APTES/TIP and TEOS/TIP. Progress in Organic Coatings, 76, 736-742.

[133]   Gachter, R. (1987) Plastics Additives Handbook. 2nd Edition, Hanser Publishers, Munich, 282.

[134]   Mathur, A.M., Narayanan, V. and Scranton, A.B. (1998) UV Curable Epoxidized Oils with Vinylethers as Reactive Diluents. Proceedings of the 1998 Radtech International Conference, 486.

[135]   Sanchez, C., Soler-Illia, G.J.A.A., Ribot, F., Lalot, T., Mayer, C.R. and Cabuil, V. (2001) Designed Hybrid Organic- Inorganic Nanocomposites from Functional Nanobuilding Blocks. Chemistry of Materials, 13, 3061-3083.

[136]   Uyama, H., Kuwabara, M., Tsujimoto, T., Nakano, M., Usuki, A. and Kobayashi, S. (2003) Green Nanocomposites from Renewable Resources: Plant Oil-Clay Hybrid Materials. Chemistry of Materials, 15, 2492-2494.

[137]   Tsujimoto, T., Uyama, H. and Kobayashi, S. (2003) Green Nanocomposites from Renewable Resources: Biodegradable Plant Oil-Silica Hybrid Coatings. Macromolecular Rapid Communications, 24, 711-714.

[138]   Zhang, J., Hu, S., Zhan, G., Tang, X. and Yu, Y. (2013) Biobased Nanocomposites from Clay Modified Blend of Epoxidized Soybean Oil and Cyanate Ester Resin. Progress in Organic Coatings, 76, 1683-1690.

[139]   Miyagawa, H., Misra, M., Drzal, L.T. and Mohanty, A.K. (2005) Biobased Epoxy/Layered Silicate Nanocomposites: Thermophysical Properties and Fracture Behavior Evaluation. Journal of Polymers and the Environment, 13, 87-96.

[140]   Miyagawa, H., Mohanty, A.K., Burgueno, R., Drzal, L.T. and Misra, M. (2007) Novel Biobased Resins from Blends of Functionalized Soybean Oil and Unsaturated Polyester Resin. Journal of Polymer Science Part B: Polymer Physics, 45, 698-704. http://dx.doi.org/10.1002/polb.21059

[141]   Miyagawa, H., Mohanty, A.K., Drzal, L.T. and Misra, M. (2005) Nanocomposites from Biobased Epoxy and Single- Wall Carbon Nanotubes: Synthesis, and Mechanical and Thermophysical Properties Evaluation. Nanotechnology, 16, 118-124. http://dx.doi.org/10.1088/0957-4484/16/1/024

[142]   Adekunle, K., Akesson, D. and Skrifvars, M. (2010) Biobased Composites Prepared by Compression Molding with a Novel Thermoset Resin from Soybean Oil and a Natural-Fiber Reinforcement. Journal of Applied Polymer Science, 116, 1759-1765.

[143]   Mustata, F., Tudorachi, N. and Rosu, D. (2011) Curing and Thermal Behavior of Resin Matrix for Composites Based on Epoxidized Soybean Oil/Diglycidyl Ether of Bisphenol A. Composites Part B: Engineering, 42, 1803-1812.

[144]   Kuriakose, A.P. and Varghese, M. (2003) Use of Rice Bran Oil and Epoxidized Rice Bran Oil in Carbon Black-Filled Natural Rubber-Polychloroprene Blends. Journal of Applied Polymer Science, 90, 4084-4092.

[145]   Fu, C., Zhang, B., Ruan, C., Hua, C., Fua, Y. and Wang, Y. (2010) Improved Hydrolytic Stability Of Poly(DL-Lactide) with Epoxidized Soybean Oil. Polymer Degradation and Stability, 95, 485-490.

[146]   Japon, S., Boogh, L., Leterrier, Y. and Manson, J.A.E. (2000) Reactive Processing of Poly(Ethylene Terephthalate) Modified with Multifunctional Epoxy-Based Additives. Polymer, 41, 5809-5818.

[147]   Ali, F., Young, W., Chang, Y.W., Kang, S.C. and Yoon, J.Y. (2009) Thermal, Mechanical and Theological Properties of Poly(Lactic Acid)/Epoxidized Soybean Oil Blends. Polymer Bulletin, 62, 91-98.

[148]   Zhan, G.Z., Zhao, L., Hu,S., Gan, W.J., Yu, Y.F. and Tang, X.L. (2008) A Novel Biobased Resinepoxidized Soybean Oil Modified Cyanate Ester. Polymer Engineering and Science, 48, 1322-1328. http://dx.doi.org/10.1002/pen.21096

[149]   Xu, Y.Q., You, M., Qu, J.P. and Qu, J.P. (2009) Melt Rheology Of Poly(lactic acid) Plasticized by Epoxidized Soybean Oil. Wuhan University Journals Press, 14, 349-354.

[150]   Zhang, X., Dieu Do, M., Lusiana, K. and Qiao, G.G. (2010) Wheat Gluten-Based Renewable and Biodegradable Polymer Materials with Enhanced Hydrophobicity by Using Epoxidized Soybean Oil as a Modifier, Carbohydrate Research, 345, 2174-2182. http://dx.doi.org/10.1016/j.carres.2010.07.020

[151]   Rana, S., Karak, N., Cho, J.W. and Kim, Y.H. (2008) Enhanced Dispersion of Carbon Nanotubes in Hyperbranched Polyurethane and Properties of Nanocomposites. Nanotechnology, 19, Article ID: 495707.

[152]   Cakmakli, B., et al. (2004) Synthesis and Characterization of Polymeric Linseed Oil Grafted Methyl Methacrylate or Styrene. Macromolecular Bioscience, 4, 649-655.

[153]   Biswas, A., Adhvaryu. A., Gordon, S.H., Erhan, S.Z. and Willett, J.L. (2005) Synthesis of Diethylamine-Functionalized Soybean Oil. Journal of Agricultural and Food Chemistry, 53, 9485-9490.