Aliphatic long-chain C 20 polyesters from Olefin metathesis

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2011
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Macromolecular Rapid Communications. 2011, 32(17), pp. 1352-1356. ISSN 1022-1336. eISSN 1521-3927. Available under: doi: 10.1002/marc.201100319
Zusammenfassung

Self-metathesis of undecenoic acid with [(PCy3)2Cl2Ru=CHPh] (2), followed by exhaustive hydrogenation yielded pure 1,20-eicosanedioic acid (5) (>99%) free of side-products from isomerization. Polycondensation with eicosane-1,20-diol (6), formed by reduction of the diol, yielded polyester 20,20 (Tm = 108 °C). By comparison, the known ADMET polymerization of undec-10-enyl undec-10-enoate (7), and subsequent exhaustive polymer-analogous hydrogenation yielded a polyester (poly-8) with irregular structure of the ester groups in the polymer chain (-O(C=O)[BOND] vs. -C(=O)O-) (Tm = 103 °C). Hydrogenation of secondary dispersions of poly-7 yielded aqueous dispersions of the long-chain aliphatic polyester poly-8.

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540 Chemie
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Dispersions, metathesis, polyesters, thermal properties, thermoplastics
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ISO 690TRZASKOWSKI, Justyna, Dorothee QUINZLER, Christian BÄHRLE, Stefan MECKING, 2011. Aliphatic long-chain C 20 polyesters from Olefin metathesis. In: Macromolecular Rapid Communications. 2011, 32(17), pp. 1352-1356. ISSN 1022-1336. eISSN 1521-3927. Available under: doi: 10.1002/marc.201100319
BibTex
@article{Trzaskowski2011-09-01Aliph-17555,
  year={2011},
  doi={10.1002/marc.201100319},
  title={Aliphatic long-chain C 20 polyesters from Olefin metathesis},
  number={17},
  volume={32},
  issn={1022-1336},
  journal={Macromolecular Rapid Communications},
  pages={1352--1356},
  author={Trzaskowski, Justyna and Quinzler, Dorothee and Bährle, Christian and Mecking, Stefan}
}
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    <dcterms:abstract xml:lang="eng">Self-metathesis of undecenoic acid with [(PCy3)2Cl2Ru=CHPh] (2), followed by exhaustive hydrogenation yielded pure 1,20-eicosanedioic acid (5) (&gt;99%) free of side-products from isomerization. Polycondensation with eicosane-1,20-diol (6), formed by reduction of the diol, yielded polyester 20,20 (Tm = 108 °C). By comparison, the known ADMET polymerization of undec-10-enyl undec-10-enoate (7), and subsequent exhaustive polymer-analogous hydrogenation yielded a polyester (poly-8) with irregular structure of the ester groups in the polymer chain (-O(C=O)[BOND] vs. -C(=O)O-) (Tm = 103 °C). Hydrogenation of secondary dispersions of poly-7 yielded aqueous dispersions of the long-chain aliphatic polyester poly-8.</dcterms:abstract>
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