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N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters
Isosorbide was esterified with acryloyl chloride and crotonic acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Po...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077400/ https://www.ncbi.nlm.nih.gov/pubmed/24991239 http://dx.doi.org/10.3762/bjoc.10.88 |
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author | Goerz, Oliver Ritter, Helmut |
author_facet | Goerz, Oliver Ritter, Helmut |
author_sort | Goerz, Oliver |
collection | PubMed |
description | Isosorbide was esterified with acryloyl chloride and crotonic acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Poly(isosorbide itaconite -co- succinate) 13 as a bio-based unsaturated polyester was cross-linked by a 1,3-dipolar cycloaddition with the received dinitrones 10a/b. The 1,3-dipolar cycloaddition led to a strong change of the mechanical properties which were investigated by rheological measurements. Nitrones derived from methyl acrylate (3a) and methyl crotonate (3b) were used as model systems and reacted with dimethyl itaconate to further characterize the 1,3-dipolaric cycloaddition. |
format | Online Article Text |
id | pubmed-4077400 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-40774002014-07-02 N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters Goerz, Oliver Ritter, Helmut Beilstein J Org Chem Full Research Paper Isosorbide was esterified with acryloyl chloride and crotonic acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Poly(isosorbide itaconite -co- succinate) 13 as a bio-based unsaturated polyester was cross-linked by a 1,3-dipolar cycloaddition with the received dinitrones 10a/b. The 1,3-dipolar cycloaddition led to a strong change of the mechanical properties which were investigated by rheological measurements. Nitrones derived from methyl acrylate (3a) and methyl crotonate (3b) were used as model systems and reacted with dimethyl itaconate to further characterize the 1,3-dipolaric cycloaddition. Beilstein-Institut 2014-04-22 /pmc/articles/PMC4077400/ /pubmed/24991239 http://dx.doi.org/10.3762/bjoc.10.88 Text en Copyright © 2014, Goerz and Ritter https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Goerz, Oliver Ritter, Helmut N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title | N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title_full | N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title_fullStr | N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title_full_unstemmed | N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title_short | N-Alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
title_sort | n-alkylated dinitrones from isosorbide as cross-linkers for unsaturated bio-based polyesters |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077400/ https://www.ncbi.nlm.nih.gov/pubmed/24991239 http://dx.doi.org/10.3762/bjoc.10.88 |
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