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Glycerol-modified poly(ε-caprolactone): an biocatalytic approach to improve the hydrophilicity of poly(ε-caprolactone)

  • Soma Chakraborty
  • James Nicolas M. Pagaduan
  • Zara Kryzel A. Melgar
  • Steffen Seitz
  • Kai Kan
  • Hiroharu Ajiro
Original Paper
  • 13 Downloads

Abstract

Novel poly(ε-caprolactone) (PCL)–glycerol polyester was synthesized in one step in the presence of Novozym 435 under mild reaction conditions. The objective of the study was to investigate the feasibility of enhancing the hydrophilicity of PCL by condensing it with glycerol through biocatalytic approach. Effect of reaction time, glycerol-to-CL ratio and CL-to-toluene ratio was studied. The 1H NMR and GPC results established that self-condensation of CL units and condensation of CL with glycerol units take place simultaneously. When the glycerol content was 10 and 20 mol% with regard to CL, condensation continued for 6 h; further extension of reaction time resulted in the cleavage of ester linkages. When the glycerol content was increased to 40 mol%, the condensation of CL–glycerol units was accomplished in 4 h; however, the reaction had to get extended beyond 6 h for complete condensation of CL–CL units. The study revealed that the crystallinity and the melting temperature (Tm) of the products altered with an increase in the glycerol content. Furthermore, TGA and contact angle values of water on PCL and its glycerol derivative films revealed that the water uptake capacity of PCL too increased significantly with the increase in glycerol content, rendering PCL more hydrophilic.

Keywords

Glycerol Poly(ε-caprolactone) Novozym 435 Condensation 

Notes

Acknowledgements

The authors would like to acknowledge the Loyola Schools faculty grant for scholarly work committee for financial support and Mr. Adam Ferry for performing some of the experiments. This work was partly supported by JST PRESTO “Molecular Technology” under the direction of Prof. Takashi Kato.

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Soma Chakraborty
    • 1
  • James Nicolas M. Pagaduan
    • 1
  • Zara Kryzel A. Melgar
    • 1
  • Steffen Seitz
    • 2
  • Kai Kan
    • 2
    • 3
  • Hiroharu Ajiro
    • 2
    • 3
    • 4
  1. 1.Department of ChemistryAteneo de Manila UniversityManilaPhilippines
  2. 2.Graduate School of Materials ScienceNara Institute of Science and TechnologyIkomaJapan
  3. 3.Institute for Research InitiativesNara Institute of Science and TechnologyIkomaJapan
  4. 4.JST PRESTOKawaguchiJapan

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