Skip to main content
Log in

Synthesis, characterization and degradation behavior of thermoplastic polyurethane from hydroxylated hemp seed oil

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 1
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. 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.

    Article  CAS  Google Scholar 

  2. 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.

    Article  CAS  Google Scholar 

  3. Hepburn C. Polyurethane elastomers. 2nd ed. London: ElsevierApplied Science; 1991.

    Google Scholar 

  4. Campanella A, Bonnaillie LM, Wool RP. Polyurethane foams from soyoil-based polyols. J Appl Polym Sci. 2009;112:2567–78.

    Article  CAS  Google Scholar 

  5. 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.

    Article  CAS  Google Scholar 

  6. 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.

    Article  CAS  Google Scholar 

  7. 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.

    Article  CAS  Google Scholar 

  8. Sharma V, Kundu PP. Condensation polymers from natural oils. Prog Poly Sci. 2008;33:1199–215.

    Article  CAS  Google Scholar 

  9. 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.

    Article  CAS  Google Scholar 

  10. 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.

    Article  CAS  Google Scholar 

  11. 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.

    Article  CAS  Google Scholar 

  12. Mutlu H, Meier AR. Castor oil as a renewable resource for the chemical industry. Eur J Lipid Sci Technol. 2010;112:10–30.

    Article  CAS  Google Scholar 

  13. 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.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. 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.

    Article  Google Scholar 

  16. Keller A. Compounding and mechanical properties of biodegradable hemp fibre composites. Compos Sci Technol. 2003;63:1307–16.

    Article  CAS  Google Scholar 

  17. 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.

    Article  CAS  Google Scholar 

  18. Hepworth DG, Hobson RN, Bruce DM, Farrent JW. The use of unretted hemp fibre in composite manufacture. Compos Appl Sci. 2000;31:1279–83.

    Article  Google Scholar 

  19. Yuanjian T, Isaac DH. Impact and fatigue behaviour of hemp fibre composites. Compos Sci Technol. 2007;67:3300–7.

    Article  CAS  Google Scholar 

  20. 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.

    Article  CAS  Google Scholar 

  21. 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.

    Article  CAS  Google Scholar 

  22. 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.

    Article  CAS  Google Scholar 

  23. Zhang Y, Xia Z, Huang H, Chen H. A degradation study of waterborne polyurethane based on TDI. Polym Test. 2009;28:264–9.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Arunjunai Raj Mahendran.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-015-4856-x

Keywords

Navigation