NOVEL POTENTIALLY BIODEGRADABLE POLYURETHANES FROM BIO-BASED POLYOLS

Authors

  • Dragana Radojčić Kansas Polymer Research Center, Pittsburg State University, 1204 Research Road, Pittsburg, KS, 66762
  • Mihail Ionescu Kansas Polymer Research Center, Pittsburg State University, 1204 Research Road, Pittsburg, KS, 66762
  • Zoran S. Petrović Kansas Polymer Research Center, Pittsburg State University, 1204 Research Road, Pittsburg, KS, 66762

DOI:

https://doi.org/10.7251/COMEN1301009R

Abstract

Completely bio-based polyols, suitable for the preparation of rigid polyurethanes were synthesized from polyglycerol, lactic acid and fatty acids. Lactic units were introduced into the polyol structure by the ring opening addition of L-lactide to hydroxyl groups, in the presence of the titanium(IV) isopropoxide catalyst. To address the incompatibility issue of simple lactide–(poly)glycerol polyols with isocyanates, vegetable oil-based fatty acids were introduced into the polyol structure. Cast thermosetting polyurethane resins were prepared by reacting polyols with diphenylmethane diisocyanate. Polyurethanes were crosslinked glassy amorphous materials with tensile strength of ~ 60 MPa, flexural modulus of 0.9 - 2.3 GPa and notched Izod impact resistance of 30 - 80 J/m. These polyurethanes are potentially biodegradable.

References

[1] M. Desroches, M. Escouvois, R. Auvergne, S. Caillol, B. Boutevin, From Vegetable Oils to Polyurethanes: Synthetic Routes to Polyols and Main Industrial Products. Polymer Reviews, 52−1 (2012) 38–79.

[2] M. Ionescu, Chemistry and technology of polyols for polyurethanes. Rapra Technology, Ltd.:Shawbury, Shrewsburty, Shropshire, UK, 2005.

[3] Y. Ikada, H. Tsuji, Biodegradable polyesters for medical and ecological applications. Macromolecular Rapid Communications. 21−3 (2000) 117–32.

[4] W. R. Grase, A Method of Preparing a Biodegradable Foam of Cross-linked Polyurethane. GB Patent 1517826; 1978.

[5] S. Miao, S. Zhang, Z. Su, P. Wang. A Novel Vegetable Oil – Lactate Hybrid Monomer for Synthesis of High-T g Polyurethanes. 48 (2010) 243–50.

[6] S. Min-Hyo, C. In-Ja, Polymeric composition for solubilizing poorly water soluble drugs and process for preparation thereof. WO 0112718(A1); 2001.

[7] K. S. Chul, C. Eun Ok, Copolymeric micelle drug composition for the preparation thereof. WO 9710849(A1) 1997.

[8] Z. Wang, L. Yu, M. Ding, H. Tan, J. Li, Q. Fu, Preparation and rapid degradation of nontoxic biodegradable polyurethanes based on poly(lactic acid)-poly(ethylene glycol)-poly(lactic acid) and l-lysine diisocyanate. Polymer Chemistry. 2−3 (2011) 601.

[9] G. T. Howard, Biodegradation of polyurethane: a review. International Biodeterioration & Biodegradation. 49−4 (2002) 245–52.

[10] R. Adhikari, P. A. Gunatillake Biodegradable injectable polyurethanes: Synthesis and eva-luation for orthopaedic applications. Biomaterials. 28 (2008) 3762.

[11] J. R. Russell, J. Huang, P. Anand, K. Kucera, A. G. Sandoval, K. W. Dantzler, et al. Biodegradation of polyester polyurethane by endophytic fungi. Applied and environmental microbiology. 77−17 (2011) 6076–84.

[12] R. L. Shogren, Z. Petrovic, Z. Liu, S. Z. Erhan, Biodegradation Behavior of Some Vegetable Oil-Based Polymers. Journal of Polymers and the Environment. 12−3 (2004) 173–8.

[13] J. M. Cangemi, A. M. Santos, C. Dos, S. Neto, Chierice GO. Biodegradation of polyurethane derived from castor oil. Polímeros. 18−3 (2008) 201–6.

[14] G. T. Howard. Polyurethane Biodegradation. In: Singh SN, editor. Microbial Degradation of Xenobiotics. Berlin, Heidelberg: Springer Berlin Heidelberg; 2012.

[15] Y. D. Kim, S. C. Kim Effect of chemical structure on the biodegradation of polyurethanes under composting conditions. Polymer Degradation and Stability. 62−2 (1998) 343–52.

[16] Z. Petrovic, Polyurethanes from Vegetable Oils. Polymer Reviews. 48−1 (2008) 109–55.

Downloads

Published

2013-06-01