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Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive
Novel hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties were synthesized by a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using...
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2010
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2956567/ https://www.ncbi.nlm.nih.gov/pubmed/20978624 http://dx.doi.org/10.3762/bjoc.6.95 |
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author | Klee, Joachim E Lehmann, Uwe |
author_facet | Klee, Joachim E Lehmann, Uwe |
author_sort | Klee, Joachim E |
collection | PubMed |
description | Novel hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties were synthesized by a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl(3). The polymerization enthalpy of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3 as measured by DSC ranges from −29 to −53 kJ·mol(−1). The shear bond strength of adhesive compositions 4, comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin. |
format | Text |
id | pubmed-2956567 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-29565672010-10-26 Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive Klee, Joachim E Lehmann, Uwe Beilstein J Org Chem Full Research Paper Novel hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties were synthesized by a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl(3). The polymerization enthalpy of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3 as measured by DSC ranges from −29 to −53 kJ·mol(−1). The shear bond strength of adhesive compositions 4, comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin. Beilstein-Institut 2010-09-07 /pmc/articles/PMC2956567/ /pubmed/20978624 http://dx.doi.org/10.3762/bjoc.6.95 Text en Copyright © 2010, Klee and Lehmann 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 Klee, Joachim E Lehmann, Uwe Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title | Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title_full | Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title_fullStr | Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title_full_unstemmed | Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title_short | Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
title_sort | novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2956567/ https://www.ncbi.nlm.nih.gov/pubmed/20978624 http://dx.doi.org/10.3762/bjoc.6.95 |
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