TY - JOUR A1 - Kreye, Oliver A1 - Toth, Tommy A1 - Meier, Michael A. R. T1 - Copolymers derived from rapeseed derivatives via ADMET and thiol-ene addition JF - European polymer journal N2 - Novel (co)polymers were synthesized from substances obtained from rapeseed via ADMET and thiol-ene additions. alpha,omega-Dienes derived from oleic and erucic acid were copolymerized with a ferulic acid derivative, a representative phenolic acid (p-hydroxycinnamic acid) present, for instance, in rapeseed cake. Copolymers with different ratios of these monomers were prepared via two different routes (ADMET and thiol-ene) and studied in detail. Both monomer and polymer synthesis were optimized in order to achieve high yielding synthetic procedures that meet the requirements of green chemistry. Some thermal properties of the resulting copolymer series were then studied and correlated to the co-monomer composition. KW - Rapeseed oil KW - Rapeseed cake KW - p-Hydroxycinnamic acids KW - alpha,omega-Dienes KW - ADMET polymerization KW - Thiol-ene addition Y1 - 2011 U6 - https://doi.org/10.1016/j.eurpolymj.2011.06.012 SN - 0014-3057 VL - 47 IS - 9 SP - 1804 EP - 1816 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Kreye, Oliver A1 - Toth, Tommy A1 - Meier, Michael A. R. T1 - Introducing multicomponent reactions to polymer science passerini reactions of renewable monomers JF - Journal of the American Chemical Society N2 - Combination of the Passerini three component-reaction (3CR) and olefin metathesis led to the formation of poly[1-(alkyl carbamoyl)alkyl alkanoates], a new class of polyesters with amide moieties in their side chain, from renewable resources. Two different approaches were studied and compared to each other. First, monomers were synthesized by the Passerini-3CR and then polymerized via acyclic diene metathesis. Alternatively, bifunctional monomers were synthesized by self-metathesis and then polymerized by Passerini-3CR. Both approaches led to the formation of high-molecular-weight polymers. Moreover, Passerini-3CRs were shown to be a versatile grafting-onto method. The results clearly demonstrate that the Passerini-3CR offers an interesting new access to monomers and polymers and thus broadens the synthetic portfolio of polymer science. Y1 - 2011 U6 - https://doi.org/10.1021/ja1113003 SN - 0002-7863 VL - 133 IS - 6 SP - 1790 EP - 1792 PB - American Chemical Society CY - Washington ER - TY - JOUR A1 - Kreye, Oliver A1 - Toth, Tommy A1 - Meier, Michael A. R. T1 - Poly-alpha,beta-unsaturated aldehydes derived from castor oil via ADMET polymerization JF - European journal of lipid science and technology N2 - 10-Undecenal, derived by pyrolysis and reduction from castor oil, was almost quantitatively transformed into the corresponding aldol condensation product under basic conditions. This alpha,omega-diene monomer was polymerized using acyclic diene metathesis (ADMET) polymerization. In a catalyst screening, four of nine different ruthenium-based metathesis catalysts showed good reactivity under neat conditions at 80 degrees C in the presence of 1,4-benzoquinone and polymers with molecular weights up to 11 kDa were formed. Furthermore, the (1)H NMR spectra showed that the metathesis catalysts tolerate the alpha,beta-unsaturated aldehyde function and due to the addition of benzoquinone, the degree of double bond isomerization was low. Further experiments investigating reduced catalyst amounts (down to 0.2 mol%) and the temperature dependence of these ADMET polymerizations gave also satisfying results for the formation of poly-alpha,beta-unsaturated aldehydes. Moreover, ADMET polymerizations with different amounts of methyl 10-undecenoate as chain-stopper were performed and the integrals of the corresponding (1)H NMR spectra allowed the determination of an absolute degree of polymerization. Finally, a reduction of a poly-alpha,beta-unsaturated aldehyde with sodium borohydride was accomplished. The resulting poly-(allyl alcohol) could be a useful compound in the generation of polymer networks like polyesters, polyurethanes, and polycarbonates and thus be of high interest in materials research. KW - ADMET KW - Aldol condensation KW - Castor oil KW - Poly(allyl alcohol)s KW - Poly-alpha,beta-unsaturated aldehydes Y1 - 2011 U6 - https://doi.org/10.1002/ejlt.201000108 SN - 1438-7697 VL - 113 IS - 1 SP - 31 EP - 38 PB - Wiley-VCH CY - Weinheim ER -