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Full Paper
Unsaturated PA X,20 from Renewable Resources via Metathesis and Catalytic Amidation
Article first published online: 20 MAY 2009
DOI: 10.1002/macp.200900045
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Mutlu, H. and Meier, M. A. R. (2009), Unsaturated PA X,20 from Renewable Resources via Metathesis and Catalytic Amidation. Macromolecular Chemistry and Physics, 210: 1019–1025. doi: 10.1002/macp.200900045
Publication History
- Issue published online: 19 JUN 2009
- Article first published online: 20 MAY 2009
- Manuscript Accepted: 8 APR 2009
- Manuscript Revised: 7 APR 2009
- Manuscript Received: 29 JAN 2009
Funded by
- German Federal Ministry of Food, Agriculture and Consumer Protection (represented by the Fachagentur Nachwachsende Rohstoffe). Grant Number: FKZ 22026905
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Keywords:
- amidation;
- catalysis;
- fatty acids;
- olefin metathesis;
- plant oil;
- polyamides;
- renewable resources
Graphical Abstract
Renewable polyamides of the type PA X,20 were prepared via metathesis and catalytic amidation revealing good polymer properties. Optimization of the synthetic protocol could reduce the required amount of precious ruthenium metathesis catalyst by a factor of at least 100.
Abstract
The synthesis of unsaturated polyamides that can be obtained from plant oil derivatives via two different approaches is described. First, long chain aliphatic α,ω-dienes with two symmetrically spaced amide segments were polymerized via ADMET polymerization. Secondly, dimethyl(E)-icos-10-enedioate, a bio-based unsaturated monomer that was obtained via metathesis, was polymerized with different aliphatic diamines using strong organic bases, such as TBD, as catalysts. Both reaction pathways led to unsaturated PA X,20 and the two different routes were investigated, optimized and compared. Moreover, the polymers were characterized by 1H NMR analysis and SEC, and the properties of the resulting polyamides were investigated by DSC and TGA.