Research Paper

Polymers from renewable resources: Bulk ATRP of fatty alcohol-derived methacrylates

  1. Gökhan Çayli1,2,
  2. Michael A. R. Meier1,*

Article first published online: 12 JUN 2008

DOI: 10.1002/ejlt.200800028

Issue

European Journal of Lipid Science and Technology

European Journal of Lipid Science and Technology

Volume 110, Issue 9, pages 853–859, No. 9 September 2008

Additional Information

How to Cite

Çayli, G. and Meier, M. A. R. (2008), Polymers from renewable resources: Bulk ATRP of fatty alcohol-derived methacrylates. European Journal of Lipid Science and Technology, 110: 853–859. doi: 10.1002/ejlt.200800028

Author Information

  1. 1

    University of Applied Sciences Oldenburg/Ostfriesland/Wilhelmshaven, Emden, Germany

  2. 2

    Boǧaziçi University, Department of Chemistry, Istanbul, Turkey

*University of Applied Sciences Oldenburg/Ostfriesland/Wilhelmshaven, Constantiaplatz 4, 26723 Emden, Germany. Fax: + 49 4921 807-1593

Publication History

  1. Issue published online: 18 SEP 2008
  2. Article first published online: 12 JUN 2008
  3. Manuscript Accepted: 7 MAR 2008
  4. Manuscript Received: 28 JAN 2008

Funded by

  • German Federal Ministry of Food, Agriculture and Consumer Protection (represented by the Fachagentur Nachwachsende Rohstoffe). Grant Number: FKZ 22026905
  • BASF chemical company

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Keywords:

  • ATRP;
  • Controlled polymerization;
  • Fatty alcohols;
  • Lauryl methacrylate;
  • Renewable resources

Abstract

Copper-mediated atom transfer radical polymerization (ATRP) of lauryl methacrylate (LMA) and other long-chain methacrylates was investigated in bulk at 35 °C by using CuCl/N,N,N′,N′,N′′-pentamethyldiethylenetriamine (PMDETA)/tricaprylylmethylammonium chloride (Aliquat®336) as the catalyst system and ethyl 2-bromoisobutyrate (EBIB) as the initiator. The investigated monomers can be derived from fatty alcohols and are therefore an important renewable resource for a sustainable development of our future. The amounts of ligand, Aliquat®336 and CuCl were optimized and the effect of their concentrations on the control of the polymerization and the observed conversions were investigated. It was found that a molar ratio of EBIB/CuCl/Ligand/Aliquat®336 of 1 : 1 : 3 : 1 provided the highest conversions of LMA and the best controlled polymerizations. These optimized conditions allowed for the synthesis of poly(lauryl methcarylate)s with different targeted DP (25, 50, 75, 100, 120, 240, and 500), including high-molecular-weight polymers with narrow molecular weight distributions. In addition, methacrylate monomers were prepared from fatty alcohols (capric, myristic, palmitic, stearic) and polymerized using the developed procedure to obtain polymers with the same DP and different chain lengths (C10, C12, C14, C16, and C18) of pending alkyl groups. Finally, the thermal properties of these polymers were examined by differential scanning calorimetry and thermogravimetric analysis.

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