Abstract
Thermoplastic polyurethane based on renewable resource was synthesized from hydroxylated hemp seed oil. Before hydroxylation, the cold-pressed hemp seed oil was initially epoxidized and then hydroxylated in the presence of catalyst using water, ethanol and butanol. The hydroxylated hemp seed oil was used along with 1,1′-methanediylbis(4-isocyanatobenzene), linear polyester diol from caprolactone monomer (CAPA 2200), and chain extender from resorcinol-based aromatic diol (HER™) to prepare seven different polyurethane elastomers. The structural changes in the modified oils and in the newly synthesized TPUs were characterized using FTIR. Similarly, the structural changes during the TPU polymerization at isothermal temperature were monitored by real-time FTIR. The thermal stabilities and the degradation behavior of the synthesized TPUs were investigated using TG and TG-FTIR studies. The presence of hydroxylated hemp seed oil in the TPU structure has decreased the thermal stabilities and also altered the degradation mechanism.
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Eceiza A, Martin MD, de la Caba K, Kortaberria G, Gabilondo N, Corcuera MA, Mondragon I. Thermoplastic polyurethane elastomers based on polycarbonate diols with different soft segment molecular weight and chemical structure: mechanical and thermal properties. Polym Eng Sci. 2008;48:297–306.
Desroches M, Escouvois M, Auvergne R, Caillol S, Boutevin B. From vegetable oils to polyurethanes: synthetic routes to polyols and main industrial products. Polym Rev. 2012;52:38–79.
Hepburn C. Polyurethane elastomers. 2nd ed. London: ElsevierApplied Science; 1991.
Campanella A, Bonnaillie LM, Wool RP. Polyurethane foams from soyoil-based polyols. J Appl Polym Sci. 2009;112:2567–78.
Zlatanic A, Lava C, Zhang W, Petrovic ZS. Effect of structure onproperties of polyols and polyurethanes based on different vegetable oils. J Polym Sci A Polym Chem. 2004;42:809–19.
Miao S, Zhang S, Su Z, Wang P. A novel vegetable oil-lactate hybrid monomer for synthesis of high-Tg polyurethanes. J Polym Sci A Polym Chem. 2010;48:243–50.
Lligadas G, Ronda JC, Galià M, Càdiz V. Plant oils as platform chemicals for polyurethane synthesis: current state-of-the-art. Biomacromolecules. 2010;11:2825–35.
Sharma V, Kundu PP. Condensation polymers from natural oils. Prog Poly Sci. 2008;33:1199–215.
Lligadas G, Ronda JC, Galià M, Cadiz V. Oleic and undecylenic acids as renewable feedstocks in the synthesis of polyols and polyurethanes. Polymer. 2010;2:440–53.
Ronda JC, Lligadas G, Galià M, Cádiz V. Vegetable oils as platform chemicals for polymer synthesis. Eur J Lipid Sci Technol. 2011;113:46–58.
Guo A, Cho Y, Petrović ZS. Structure and properties of halogenated and nonhalogenated soy-based polyols. J Polym Sci A Polym Chem. 2000;38:3900–10.
Mutlu H, Meier AR. Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol. 2010;112:10–30.
Lligadas G, Ronda JC, Galià M, Cadiz V. Plant oils as platform chemicals for polyurethane synthesis: current state-of-the-art. Biomacromolecules. 2010;11:2825–35.
Fridrihsone A, Stirna U, Lazdiņa B, Misāne M, Vilsone D. Characterization of polyurethane networks structure and properties based on rapeseed oil derived polyol. Eur Polym J. 2013;49:1204–14.
Petrović ZS, Cvetković I, Hong DP, Wan X, Zhang W, Abraham T, Malsam J. Polyester polyols and polyurethanes from ricinoleic acid. J Appl Polym Sci. 2008;108:1184–90.
Keller A. Compounding and mechanical properties of biodegradable hemp fibre composites. Compos Sci Technol. 2003;63:1307–16.
Dhakal HN, Zhang ZY, Richardson MOW. Effect of water absorption on the mechanical properties of hemp fibre reinforced unsaturated polyester composites. Compos Sci Technol. 2007;67:1674–83.
Hepworth DG, Hobson RN, Bruce DM, Farrent JW. The use of unretted hemp fibre in composite manufacture. Compos Appl Sci. 2000;31:1279–83.
Yuanjian T, Isaac DH. Impact and fatigue behaviour of hemp fibre composites. Compos Sci Technol. 2007;67:3300–7.
Kong X, Liu G, Curtis JM. Novel polyurethane produced from canola oil based poly(ether ester) polyols: synthesis, characterization and properties. Eur Polym J. 2012;48:2097–106.
Yeganeh H, Mehdizadeh MR. Synthesis and properties of isocyanate curable millable polyurethane elastomers based on castor oil as a renewable resource polyol. Eur Polym J. 2004;40:1233–8.
Duquesne S, Le Bras M, Bourbigot S, Delobel R, Camino G, Eling B, Lindsay C, Roels T. Thermal degradation of polyurethane and polyurethane/expandable graphite coatings. Polym Degrad Stab. 2001;74:493–9.
Zhang Y, Xia Z, Huang H, Chen H. A degradation study of waterborne polyurethane based on TDI. Polym Test. 2009;28:264–9.
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The authors wish to express their sincere thanks to the Management and Principal of the Kamaraj college of Engg. and Tech., K. Vellakulam Post—625701 for their support. Also the authors would like to thank Mr. Herfried Lammer, Area manager, Wood Carinthian Competence Centre, St. Veit an der Glan, Austria, and other faculty members of the organization.
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Surender, R., Mahendran, A.R., Wuzella, G. et al. Synthesis, characterization and degradation behavior of thermoplastic polyurethane from hydroxylated hemp seed oil. J Therm Anal Calorim 123, 525–533 (2016). https://doi.org/10.1007/s10973-015-4856-x
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DOI: https://doi.org/10.1007/s10973-015-4856-x