Synthesis and polymerization kinetics of acrylamide phosphonic acids and esters as new dentine adhesives
Identifieur interne : 004947 ( Main/Exploration ); précédent : 004946; suivant : 004948Synthesis and polymerization kinetics of acrylamide phosphonic acids and esters as new dentine adhesives
Auteurs : V. Besse [France] ; L. Le Pluart [France] ; W. D. Cook [Australie] ; T. Pham [France] ; P. Madec [France]Source :
- Journal of Polymer Science Part A: Polymer Chemistry [ 0887-624X ] ; 2013-01-01.
Descripteurs français
- Pascal (Inist)
- Acrylamide dérivé copolymère, Acrylamide dérivé polymère, Acrylamide(N,N-diéthyl) polymère, Adhésif, Copolymère phosphore, Dentisterie restauratrice, Etude expérimentale, Monomère, Méthacrylate copolymère, Phosphonate organique, Phosphonique acide dérivé, Polymère linéaire, Polymère réticulé, Polymérisation photochimique, Réactivité chimique.
- Wicri :
English descriptors
- KwdEn :
- 2jcp, 3jcp, 3jhh, Acrylamide, Acrylamide derivative copolymer, Acrylamide derivative polymer, Acrylamide function, Acrylamide monomers, Acrylamide phosphonic acid, Adhesive, Anhydrous, Anhydrous dichloromethane, Cdcl3, Chem, Chemical reactivity, Column chromatography, Copolymerization, Crosslinked polymer, Crosslinking, Crosslinking process, Crude product, Debaap, Dental adhesives, Dental restoration, Dichloromethane, Diethyl, Double bonds, Enhancement, Ester, Ethyl acetate, Experimental study, Fractional, Fractional conversion, Fractional conversion rate, Hexylphosphonic acid, Homopolymerization, Hrms, Hrms calcd, Irradiation time, Jansen, Kinetics, Linear polymer, Macromolecule, Magnesium sulfate, Maximum polymerization rate, Medium polarity, Methacrylate, Methacrylate copolymer, Methacrylate monomer, Methacrylate monomers, Mmol, Moiety, Monoacrylamide monomer, Monofunctional, Monomer, Nitrogen atmosphere, Organic phosphonate, Phosphonate, Phosphonate ester, Phosphonate ester group, Phosphonic, Phosphonic acid, Phosphonic acid derivatives, Phosphonic acid group, Phosphonic acid groups, Phosphonic acid moiety, Phosphonic acid monomer, Phosphorus copolymer, Photopolymerization, Photopolymerization kinetics, Polym, Polymer, Polymer chemistry, Polymer science part, Polymerization, Polymerization kinetics, Polymerization rate, Polymerizing medium, Previous studies, Radical concentration, Radical polymerization, Rate enhancement, Rate enhancement effect, Room temperature.
- Teeft :
- 2jcp, 3jcp, 3jhh, Acrylamide, Acrylamide function, Acrylamide monomers, Acrylamide phosphonic acid, Anhydrous, Anhydrous dichloromethane, Cdcl3, Chem, Column chromatography, Copolymerization, Crosslinking, Crosslinking process, Crude product, Debaap, Dental adhesives, Dichloromethane, Diethyl, Double bonds, Enhancement, Ester, Ethyl acetate, Fractional, Fractional conversion, Fractional conversion rate, Hexylphosphonic acid, Homopolymerization, Hrms, Hrms calcd, Irradiation time, Jansen, Kinetics, Macromolecule, Magnesium sulfate, Maximum polymerization rate, Medium polarity, Methacrylate, Methacrylate monomer, Methacrylate monomers, Mmol, Moiety, Monoacrylamide monomer, Monofunctional, Monomer, Nitrogen atmosphere, Phosphonate, Phosphonate ester, Phosphonate ester group, Phosphonic, Phosphonic acid, Phosphonic acid group, Phosphonic acid groups, Phosphonic acid moiety, Phosphonic acid monomer, Photopolymerization, Photopolymerization kinetics, Polym, Polymer, Polymer chemistry, Polymer science part, Polymerization, Polymerization kinetics, Polymerization rate, Polymerizing medium, Previous studies, Radical concentration, Radical polymerization, Rate enhancement, Rate enhancement effect, Room temperature.
Abstract
In restorative dentistry, acrylamide monomers bearing phosphonic acid moieties have proved to be useful species for the formulation of dental self‐etch adhesives since they provide enhanced adhesion to hydroxyapatite and are not subject to hydrolysis, thus potentially improving their adhesive durability. Previous studies have demonstrated that phosphonic acid acrylamides increase the rate of photopolymerization of diacrylamide monomers. To understand whether this rate acceleration is specific to the acrylamide function of the monomer, or due to the phosphonic acid group per se, or is applicable only with a crosslinking reaction, we have synthesized several acrylamide and methacrylate monomers bearing phosphonic acid or phosphonate moieties and studied their photopolymerization kinetics. The acrylamide phosphonic acid was found to accelerate the polymerization rate but similar monomers bearing a phosphonate ester group had a much smaller effect. A similar accelerating effect was observed when the phosphonic acid‐based monomers were copolymerized with a monofunctional acrylamide monomer, excluding the possibility that the rate acceleration might be related to the crosslinking process. This rate effect is also observed when a nonpolymerizable organic phosphonic acid is present in the polymerizing medium. We suggest that the increase of the medium polarity is responsible for this rate enhancement effect. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013
Url:
DOI: 10.1002/pola.26339
Affiliations:
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when="2013-01-01">2013-01-01</date></imprint><idno type="ISSN">0887-624X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0887-624X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>2jcp</term><term>3jcp</term><term>3jhh</term><term>Acrylamide</term><term>Acrylamide derivative copolymer</term><term>Acrylamide derivative polymer</term><term>Acrylamide function</term><term>Acrylamide monomers</term><term>Acrylamide phosphonic acid</term><term>Adhesive</term><term>Anhydrous</term><term>Anhydrous dichloromethane</term><term>Cdcl3</term><term>Chem</term><term>Chemical reactivity</term><term>Column chromatography</term><term>Copolymerization</term><term>Crosslinked polymer</term><term>Crosslinking</term><term>Crosslinking process</term><term>Crude product</term><term>Debaap</term><term>Dental adhesives</term><term>Dental restoration</term><term>Dichloromethane</term><term>Diethyl</term><term>Double bonds</term><term>Enhancement</term><term>Ester</term><term>Ethyl acetate</term><term>Experimental study</term><term>Fractional</term><term>Fractional conversion</term><term>Fractional conversion rate</term><term>Hexylphosphonic acid</term><term>Homopolymerization</term><term>Hrms</term><term>Hrms calcd</term><term>Irradiation time</term><term>Jansen</term><term>Kinetics</term><term>Linear polymer</term><term>Macromolecule</term><term>Magnesium sulfate</term><term>Maximum polymerization rate</term><term>Medium polarity</term><term>Methacrylate</term><term>Methacrylate copolymer</term><term>Methacrylate monomer</term><term>Methacrylate monomers</term><term>Mmol</term><term>Moiety</term><term>Monoacrylamide monomer</term><term>Monofunctional</term><term>Monomer</term><term>Nitrogen atmosphere</term><term>Organic phosphonate</term><term>Phosphonate</term><term>Phosphonate ester</term><term>Phosphonate ester group</term><term>Phosphonic</term><term>Phosphonic acid</term><term>Phosphonic acid derivatives</term><term>Phosphonic acid group</term><term>Phosphonic acid groups</term><term>Phosphonic acid moiety</term><term>Phosphonic acid monomer</term><term>Phosphorus copolymer</term><term>Photopolymerization</term><term>Photopolymerization kinetics</term><term>Polym</term><term>Polymer</term><term>Polymer chemistry</term><term>Polymer science part</term><term>Polymerization</term><term>Polymerization kinetics</term><term>Polymerization rate</term><term>Polymerizing medium</term><term>Previous studies</term><term>Radical concentration</term><term>Radical polymerization</term><term>Rate enhancement</term><term>Rate enhancement effect</term><term>Room temperature</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Acrylamide dérivé copolymère</term><term>Acrylamide dérivé polymère</term><term>Acrylamide(N,N-diéthyl) polymère</term><term>Adhésif</term><term>Copolymère phosphore</term><term>Dentisterie restauratrice</term><term>Etude expérimentale</term><term>Monomère</term><term>Méthacrylate copolymère</term><term>Phosphonate organique</term><term>Phosphonique acide dérivé</term><term>Polymère linéaire</term><term>Polymère réticulé</term><term>Polymérisation photochimique</term><term>Réactivité chimique</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>2jcp</term><term>3jcp</term><term>3jhh</term><term>Acrylamide</term><term>Acrylamide function</term><term>Acrylamide monomers</term><term>Acrylamide phosphonic acid</term><term>Anhydrous</term><term>Anhydrous dichloromethane</term><term>Cdcl3</term><term>Chem</term><term>Column chromatography</term><term>Copolymerization</term><term>Crosslinking</term><term>Crosslinking process</term><term>Crude product</term><term>Debaap</term><term>Dental adhesives</term><term>Dichloromethane</term><term>Diethyl</term><term>Double bonds</term><term>Enhancement</term><term>Ester</term><term>Ethyl acetate</term><term>Fractional</term><term>Fractional conversion</term><term>Fractional conversion rate</term><term>Hexylphosphonic acid</term><term>Homopolymerization</term><term>Hrms</term><term>Hrms calcd</term><term>Irradiation time</term><term>Jansen</term><term>Kinetics</term><term>Macromolecule</term><term>Magnesium sulfate</term><term>Maximum polymerization rate</term><term>Medium polarity</term><term>Methacrylate</term><term>Methacrylate monomer</term><term>Methacrylate monomers</term><term>Mmol</term><term>Moiety</term><term>Monoacrylamide monomer</term><term>Monofunctional</term><term>Monomer</term><term>Nitrogen atmosphere</term><term>Phosphonate</term><term>Phosphonate ester</term><term>Phosphonate ester group</term><term>Phosphonic</term><term>Phosphonic acid</term><term>Phosphonic acid group</term><term>Phosphonic acid groups</term><term>Phosphonic acid moiety</term><term>Phosphonic acid monomer</term><term>Photopolymerization</term><term>Photopolymerization kinetics</term><term>Polym</term><term>Polymer</term><term>Polymer chemistry</term><term>Polymer science part</term><term>Polymerization</term><term>Polymerization kinetics</term><term>Polymerization rate</term><term>Polymerizing medium</term><term>Previous studies</term><term>Radical concentration</term><term>Radical polymerization</term><term>Rate enhancement</term><term>Rate enhancement effect</term><term>Room temperature</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Adhésif</term><term>Polymère</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In restorative dentistry, acrylamide monomers bearing phosphonic acid moieties have proved to be useful species for the formulation of dental self‐etch adhesives since they provide enhanced adhesion to hydroxyapatite and are not subject to hydrolysis, thus potentially improving their adhesive durability. Previous studies have demonstrated that phosphonic acid acrylamides increase the rate of photopolymerization of diacrylamide monomers. To understand whether this rate acceleration is specific to the acrylamide function of the monomer, or due to the phosphonic acid group per se, or is applicable only with a crosslinking reaction, we have synthesized several acrylamide and methacrylate monomers bearing phosphonic acid or phosphonate moieties and studied their photopolymerization kinetics. The acrylamide phosphonic acid was found to accelerate the polymerization rate but similar monomers bearing a phosphonate ester group had a much smaller effect. A similar accelerating effect was observed when the phosphonic acid‐based monomers were copolymerized with a monofunctional acrylamide monomer, excluding the possibility that the rate acceleration might be related to the crosslinking process. This rate effect is also observed when a nonpolymerizable organic phosphonic acid is present in the polymerizing medium. We suggest that the increase of the medium polarity is responsible for this rate enhancement effect. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013</div></front></TEI><affiliations><list><country><li>Australie</li><li>France</li></country><region><li>Basse-Normandie</li><li>Région Normandie</li></region><settlement><li>Caen</li></settlement></list><tree><country name="France"><region name="Région Normandie"><name sortKey="Besse, V" sort="Besse, V" uniqKey="Besse V" first="V." last="Besse">V. Besse</name></region><name sortKey="Le Pluart, L" sort="Le Pluart, L" uniqKey="Le Pluart L" first="L." last="Le Pluart">L. Le Pluart</name><name sortKey="Le Pluart, L" sort="Le Pluart, L" uniqKey="Le Pluart L" first="L." last="Le Pluart">L. Le Pluart</name><name sortKey="Le Pluart, L" sort="Le Pluart, L" uniqKey="Le Pluart L" first="L." last="Le Pluart">L. Le Pluart</name><name sortKey="Madec, P" sort="Madec, P" uniqKey="Madec P" first="P." last="Madec">P. Madec</name><name sortKey="Pham, T" sort="Pham, T" uniqKey="Pham T" first="T." last="Pham">T. Pham</name></country><country name="Australie"><noRegion><name sortKey="Cook, W D" sort="Cook, W D" uniqKey="Cook W" first="W. D." last="Cook">W. D. Cook</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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