Poly(urethane) synthesized from 9-ethoxy-1,10-octadecanediol obtained by modification of palm oil oleic acid

Bunbun Bundjali, Muhammad Masykuri, Fitri Widya Hartanti, I Made Arcana


Poly(urethane) (PU) as a prepolymer was prepared by polymerization of the diol compound (9-ethoxy-1,10-octadecanediol) and 4,4-methylen-bis phenyl isocyanate (MDI) under nitrogen atmosphere at 85 °C. The 9-ethoxy-1,10-octadecanediol was obtained by several reaction steps, i.e. epoxydation of oleic acid obtained from palm oil, ring-opening of oleic acid epoxide, and reduction of oleic acid ester. All compounds obtained in this work were characterized by chemical structure analysis (FTIR and 1H NMR), supported by analysis of iodine value, acid value, and hydroxyl value determined by titration methods and thermal analysis, especially for poly(urethane). The 9-ethoxy-1,10-octadecanediol as the diol compound for preparation of poly(urethane) was analyzed by FTIR, supported by hydroxyl numbers determined by titration. Poly(urethane-urea) (PUU) was obtained by addition of ethylene diamine as chain extender to poly(urethane). The thermal stability of poly(urethane-urea) is higher than that of poly(urethane). The addition of ethylene diamine as chain extender in poly(urethane) can improve the intrinsic viscosity of polymer to form poly(urethane-urea). These results are supported by chemical structure analysis.


9-ethoxy-1,10-octadecanediol; oleic acid; palm oil; poly(urethane-urea); synthesis

Full Text:



Arcana, I.M., Bundjali, B., Hasan, M., Hariyawati, K., Mariani, H., Anggraini, S.D. & Ardana, A., Study on Properties of Poly(urethane-ester) Synthesized from Prepolymers of ε-Caprolactone and 2,2-Dimethyl-1,3-Propanediol Monomers and Their Biodegradability, Journal of Polymer and the Environment, 18(3), pp. 188-195, 2010.

Arcana, I.M., Bundjali, B., Zulfikar, M.A. & Hariyawati, K., The Effect of the Soft Segment of Prepolymers on Properties of Poly(urethane-ester) and Its Biodegradability, Polymer International, 60(10), pp. 1535-1540, 2011.

Lee, J.S., Cho, Y.S., Lee, J.W., Kim, H.J., Pyun, D.G., Park, M.H., Yoon, T.R., Lee, H.J. & Kuroyanagy, Y., Preparation of Wound Dressing using Hydrogel Polyurethane Foam, Trens Biomater Artif Organs, 15(1), pp. 4-6, 2001.

Eisenbach, C.D. & Nefzger, H., Handbook of Polymer Synthesis, Marcel Dekker Inc., New York, pp. 685, 1992.

Brydson, J.A., Plastic Materials, Butterworth Heinemann Ltd., Oxford, pp. 756, 1995.

Chen, Z., Zhang, R., Kodama, M. & Nakaya, T.J., Preparations and Properties of A Novel Grafted Segmented Polyurethane-bearing Glucose Groups, Biomater. Sci. Polym. Ed., 10(9), pp. 901, 1999.

Nicholson, J.W., Chemistry of Polymers, ed. 2, The Royal Society of Chemistry, Cambridge, pp. 19, 1997.

Pigott, K.A., Kirk-Othmer Encyclopedia of Chemical Technology, A Wiley-Interscience Publication, John Wiley and Sons Inc., New York, pp. 21-58, 1996.

Basiron, Y., Palm Oil and Its Global Supply and Demand Prospects, Oil Palm Industry Economic Journal, 2(1), pp. 1-10, 2002.

Van Gelder, J.W., Greasy Palms: European Buyer of Indonesian Palm Oil, Friends of Earth Report, London, pp. 18-25, 2004.

Schuster, H., Rios, L.A., Weckes, P.P. & Hoelderich, W.F., Heterogeneous Catalysts for the Production of New Lubricants with Unique Properties, Applied Catalysis A: General, 348(2), pp. 266-270, 2008.

Piazza, G.J., Nunez, A. & Foglia, T.A., Epoxidation of Fatty Acids, Fatty Methyl Esters, and Alkenes by Immobilized Oat Seed Peroxygenase, Journal of Molecular Catalyst B: Enzymatic, 21(3), pp. 143-151, 2003.

Pages, X. & Alfos, C., Synthesis of New Derivatives from Vegetable Sunflower Oil Methyl Esters via Epoxidation and Oxirane Opening, Oleagineux, Corps Gras, Lipides, 8(2), pp. 122-125, 2001.

Saeed, A. & Ashraf, Z., Sodium Borohydride Reduction of Aromatic Carboxylic Acids via Methyl Esters, J. Chem. Sci., 118(5), pp. 419-423, 2006.

Jaffrennou, B., Portal, J., Mechin, F. & Pascault, J.P., Nanostructured Poly(urethane)s and Poly(urethane-ureas) from Reactive Solutions of Poly[styrene-b-butadiene-b-(methyl methacrylate)]-triblock Copolymers, European Polym. J., 44(11), pp. 3439-3455, 2008.

Xia, W., Budge, S.M. & Lumsden, M.D., 1H-NMR Characterization of Epoxides Derived from Polyunsaturated Fatty Acids, J. Am. Oil Chem. Soc., 93(4), pp. 467-478, 2016.

Moser, B.R. & Erhan, S.Z., Preparation and Evaluation of A Series of α-hydroxy Ethers from 9,10-epoxystearates, Eur. J. Lipid Sci. Technol., 109(3), pp. 206-213, 2007.

DOI: http://dx.doi.org/10.5614%2Fj.math.fund.sci.2018.50.1.2


  • There are currently no refbacks.

View my Stats

Creative Commons License
This work is licensed under a Creative Commons Attribution-NoDerivatives 4.0 International License.