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Fatty Acid Derived Monomers and Related Polymers Via Thiol-ene (Click) Additions

  1. Oĝuz Türünç1,2,
  2. Michael A. R. Meier1,*

Article first published online: 21 JUL 2010

DOI: 10.1002/marc.201000291

Issue

Macromolecular Rapid Communications

Macromolecular Rapid Communications

Volume 31, Issue 20, pages 1822–1826, October 18, 2010

Additional Information

How to Cite

Türünç, O. and Meier, M. A. R. (2010), Fatty Acid Derived Monomers and Related Polymers Via Thiol-ene (Click) Additions. Macromolecular Rapid Communications, 31: 1822–1826. doi: 10.1002/marc.201000291

Author Information

  1. 1

    Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Golm, Germany

  2. 2

    University of Applied Sciences, Emden/Leer, Constantiaplatz 4, 26723 Emden, Germany

*Institute of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, 14476 Golm, Germany; Internet: www.meier-michael.com.

Publication History

  1. Issue published online: 21 JUL 2010
  2. Article first published online: 21 JUL 2010
  3. Manuscript Received: 5 MAY 2010

Funded by

  • German Federal Ministry of Food, Agriculture, and Consumer Protection

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Keywords:

  • castor oil;
  • fatty acids;
  • polyesters;
  • renewable raw materials;
  • thiol-ene click

Graphical Abstract

Thumbnail image of graphical abstract

Clicking renewable resources: The castor oil derived platform chemical methyl 10-undecenoate is a very suitable starting material for thiol-ene click reactions. Different functional groups can thus be introduced in an efficient manner to yield renewable monomers. Their polymerization leads to plant oil derived polyesters with good thermal properties, which could probably substitute existing fossil resource based materials.

Abstract

Thiol-ene additions of methyl 10-undecenoate, a castor oil derived renewable platform chemical, were studied with the goal of preparing a set of renewable monomers. Good to excellent yields were obtained for these solvent and initiator free thiol-ene additions. The resulting monomers were then polymerized using TBD as a catalyst, to linear as well as hyperbranched polyesters that also contain thio-ether linkages. All thus prepared polymers were fully characterized (NMR, GPC, DSC, and TGA) and the results of these investigations will be discussed within this contribution. The thermal analysis of these polymers revealed melting points in the range from 50 to 71 °C. Moreover, no significant weight loss was observed below 300 °C.

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