Hydrolytically stable acidic monomers used in two steps self-etch adhesives
This study deals with the stability of new phosphonic monomers bearing an acrylamide moiety designed to increase the adhesion durability. Synthesis of monomers bearing acrylamide and methacrylate moieties, as well as their use in Self-Etch Adhesives is reported. The adhesion of a degraded methacryla...
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| Veröffentlicht in: | Polymer degradation and stability 2013-09, Vol.98 (9), p.1688-1698 |
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| container_issue | 9 |
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| container_title | Polymer degradation and stability |
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| creator | Derbanne, Mathieu A. Besse, Vincent Le Goff, Stéphane Sadoun, Michaël Pham, Thi-Nhàn |
| description | This study deals with the stability of new phosphonic monomers bearing an acrylamide moiety designed to increase the adhesion durability. Synthesis of monomers bearing acrylamide and methacrylate moieties, as well as their use in Self-Etch Adhesives is reported. The adhesion of a degraded methacrylate based adhesive has been evaluated. Homologous self-etching primers containing monomers bearing acrylamide or methacrylate were formulated and used either immediately after formulation or after 18 months. Their adhesive performances were assessed by shear bond strength testing and their degradation measured by NMR, HPLC-MS. While no differences were found in terms of adhesion between fresh and aged acrylamide based adhesive, the instability of methacrylate based ones was demonstrated. Nevertheless, methacrylate based SEAs still have good adhesion abilities. The co-monomer used, N,N′-diethyl-1,3-bis(acrylamido)propane is expected to be responsible for good mechanical properties even for degraded SEAs. Lastly, the stability of acrylamide monomer seems to be of interest in the prospect of developing SEA with longer shelf life. |
| doi_str_mv | 10.1016/j.polymdegradstab.2013.06.006 |
| format | Article |
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Synthesis of monomers bearing acrylamide and methacrylate moieties, as well as their use in Self-Etch Adhesives is reported. The adhesion of a degraded methacrylate based adhesive has been evaluated. Homologous self-etching primers containing monomers bearing acrylamide or methacrylate were formulated and used either immediately after formulation or after 18 months. Their adhesive performances were assessed by shear bond strength testing and their degradation measured by NMR, HPLC-MS. While no differences were found in terms of adhesion between fresh and aged acrylamide based adhesive, the instability of methacrylate based ones was demonstrated. Nevertheless, methacrylate based SEAs still have good adhesion abilities. The co-monomer used, N,N′-diethyl-1,3-bis(acrylamido)propane is expected to be responsible for good mechanical properties even for degraded SEAs. Lastly, the stability of acrylamide monomer seems to be of interest in the prospect of developing SEA with longer shelf life.</description><identifier>ISSN: 0141-3910</identifier><identifier>EISSN: 1873-2321</identifier><identifier>DOI: 10.1016/j.polymdegradstab.2013.06.006</identifier><identifier>CODEN: PDSTDW</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Acrylamide ; Acrylamide phosphonic acids ; acrylamides ; adhesion ; Adhesive bonding ; Adhesives ; Applied sciences ; Bearing ; Biological and medical sciences ; Degradation ; Dental materials ; Dentin ; durability ; Exact sciences and technology ; Head and neck surgery. Maxillofacial surgery. Dental surgery. Orthodontics ; high performance liquid chromatography ; mass spectrometry ; Maxillofacial surgery. Dental surgery. Orthodontics ; mechanical properties ; Medical sciences ; Methacrylate phosphonic acids ; Model compounds ; Monomers ; nuclear magnetic resonance spectroscopy ; Organic polymers ; Physicochemistry of polymers ; propane ; Seas ; shelf life ; Stability ; Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases</subject><ispartof>Polymer degradation and stability, 2013-09, Vol.98 (9), p.1688-1698</ispartof><rights>2013 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c453t-e4732e078a7ffcf451251f762c218ca42ba3ec042a760eff4f8c15db18776b923</citedby><cites>FETCH-LOGICAL-c453t-e4732e078a7ffcf451251f762c218ca42ba3ec042a760eff4f8c15db18776b923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0141391013001778$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27643703$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Derbanne, Mathieu A.</creatorcontrib><creatorcontrib>Besse, Vincent</creatorcontrib><creatorcontrib>Le Goff, Stéphane</creatorcontrib><creatorcontrib>Sadoun, Michaël</creatorcontrib><creatorcontrib>Pham, Thi-Nhàn</creatorcontrib><title>Hydrolytically stable acidic monomers used in two steps self-etch adhesives</title><title>Polymer degradation and stability</title><description>This study deals with the stability of new phosphonic monomers bearing an acrylamide moiety designed to increase the adhesion durability. Synthesis of monomers bearing acrylamide and methacrylate moieties, as well as their use in Self-Etch Adhesives is reported. The adhesion of a degraded methacrylate based adhesive has been evaluated. Homologous self-etching primers containing monomers bearing acrylamide or methacrylate were formulated and used either immediately after formulation or after 18 months. Their adhesive performances were assessed by shear bond strength testing and their degradation measured by NMR, HPLC-MS. While no differences were found in terms of adhesion between fresh and aged acrylamide based adhesive, the instability of methacrylate based ones was demonstrated. Nevertheless, methacrylate based SEAs still have good adhesion abilities. The co-monomer used, N,N′-diethyl-1,3-bis(acrylamido)propane is expected to be responsible for good mechanical properties even for degraded SEAs. Lastly, the stability of acrylamide monomer seems to be of interest in the prospect of developing SEA with longer shelf life.</description><subject>Acrylamide</subject><subject>Acrylamide phosphonic acids</subject><subject>acrylamides</subject><subject>adhesion</subject><subject>Adhesive bonding</subject><subject>Adhesives</subject><subject>Applied sciences</subject><subject>Bearing</subject><subject>Biological and medical sciences</subject><subject>Degradation</subject><subject>Dental materials</subject><subject>Dentin</subject><subject>durability</subject><subject>Exact sciences and technology</subject><subject>Head and neck surgery. Maxillofacial surgery. Dental surgery. Orthodontics</subject><subject>high performance liquid chromatography</subject><subject>mass spectrometry</subject><subject>Maxillofacial surgery. Dental surgery. Orthodontics</subject><subject>mechanical properties</subject><subject>Medical sciences</subject><subject>Methacrylate phosphonic acids</subject><subject>Model compounds</subject><subject>Monomers</subject><subject>nuclear magnetic resonance spectroscopy</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>propane</subject><subject>Seas</subject><subject>shelf life</subject><subject>Stability</subject><subject>Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases</subject><issn>0141-3910</issn><issn>1873-2321</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqNkT1vFDEQQC1EJI4kv4FtItHsZvyx9l1BgSJIUCJRkNSWzx4nPu2uD89eovv3-LiIggbcuHl6M35m7IJDx4Hry023zcN-DPhYXKDZrTsBXHagOwD9hi340shWSMHfsgVwxVu54vCOvSfaQD2q5wt2e7MPpVrm5N0w7JuDZsDG-RSSb8Y85RELNTvC0KSpmV9yRXBLDeEQW5z9U-PCE1J6RjpjJ9ENhOev9yl7-Prl_uqmvft-_e3q813rVS_nFpWRAsEsnYnRx7qG6Hk0WnjBl94psXYSPSjhjAaMUcWl531Y1-cYvV4Jeco-Hr3bkn_ukGY7JvI4DG7CvCPLteE9iBXof6M9l0pyaVRFPx1RXzJRwWi3JY2u7C0He-htN_av3vbQ24K28HvUxesoR7VlLG7yif5IhNFKGpCV-3DkosvWPZbKPPyoIl2_xMherypxfSSwRnxOWCz5hJPHkAr62Yac_nOnXypOqO8</recordid><startdate>20130901</startdate><enddate>20130901</enddate><creator>Derbanne, Mathieu A.</creator><creator>Besse, Vincent</creator><creator>Le Goff, Stéphane</creator><creator>Sadoun, Michaël</creator><creator>Pham, Thi-Nhàn</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130901</creationdate><title>Hydrolytically stable acidic monomers used in two steps self-etch adhesives</title><author>Derbanne, Mathieu A. ; Besse, Vincent ; Le Goff, Stéphane ; Sadoun, Michaël ; Pham, Thi-Nhàn</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c453t-e4732e078a7ffcf451251f762c218ca42ba3ec042a760eff4f8c15db18776b923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Acrylamide</topic><topic>Acrylamide phosphonic acids</topic><topic>acrylamides</topic><topic>adhesion</topic><topic>Adhesive bonding</topic><topic>Adhesives</topic><topic>Applied sciences</topic><topic>Bearing</topic><topic>Biological and medical sciences</topic><topic>Degradation</topic><topic>Dental materials</topic><topic>Dentin</topic><topic>durability</topic><topic>Exact sciences and technology</topic><topic>Head and neck surgery. Maxillofacial surgery. Dental surgery. Orthodontics</topic><topic>high performance liquid chromatography</topic><topic>mass spectrometry</topic><topic>Maxillofacial surgery. Dental surgery. Orthodontics</topic><topic>mechanical properties</topic><topic>Medical sciences</topic><topic>Methacrylate phosphonic acids</topic><topic>Model compounds</topic><topic>Monomers</topic><topic>nuclear magnetic resonance spectroscopy</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>propane</topic><topic>Seas</topic><topic>shelf life</topic><topic>Stability</topic><topic>Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Derbanne, Mathieu A.</creatorcontrib><creatorcontrib>Besse, Vincent</creatorcontrib><creatorcontrib>Le Goff, Stéphane</creatorcontrib><creatorcontrib>Sadoun, Michaël</creatorcontrib><creatorcontrib>Pham, Thi-Nhàn</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Polymer degradation and stability</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Derbanne, Mathieu A.</au><au>Besse, Vincent</au><au>Le Goff, Stéphane</au><au>Sadoun, Michaël</au><au>Pham, Thi-Nhàn</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrolytically stable acidic monomers used in two steps self-etch adhesives</atitle><jtitle>Polymer degradation and stability</jtitle><date>2013-09-01</date><risdate>2013</risdate><volume>98</volume><issue>9</issue><spage>1688</spage><epage>1698</epage><pages>1688-1698</pages><issn>0141-3910</issn><eissn>1873-2321</eissn><coden>PDSTDW</coden><abstract>This study deals with the stability of new phosphonic monomers bearing an acrylamide moiety designed to increase the adhesion durability. Synthesis of monomers bearing acrylamide and methacrylate moieties, as well as their use in Self-Etch Adhesives is reported. The adhesion of a degraded methacrylate based adhesive has been evaluated. Homologous self-etching primers containing monomers bearing acrylamide or methacrylate were formulated and used either immediately after formulation or after 18 months. Their adhesive performances were assessed by shear bond strength testing and their degradation measured by NMR, HPLC-MS. While no differences were found in terms of adhesion between fresh and aged acrylamide based adhesive, the instability of methacrylate based ones was demonstrated. Nevertheless, methacrylate based SEAs still have good adhesion abilities. The co-monomer used, N,N′-diethyl-1,3-bis(acrylamido)propane is expected to be responsible for good mechanical properties even for degraded SEAs. Lastly, the stability of acrylamide monomer seems to be of interest in the prospect of developing SEA with longer shelf life.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.polymdegradstab.2013.06.006</doi><tpages>11</tpages></addata></record> |
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| ispartof | Polymer degradation and stability, 2013-09, Vol.98 (9), p.1688-1698 |
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| source | Elsevier ScienceDirect Journals |
| subjects | Acrylamide Acrylamide phosphonic acids acrylamides adhesion Adhesive bonding Adhesives Applied sciences Bearing Biological and medical sciences Degradation Dental materials Dentin durability Exact sciences and technology Head and neck surgery. Maxillofacial surgery. Dental surgery. Orthodontics high performance liquid chromatography mass spectrometry Maxillofacial surgery. Dental surgery. Orthodontics mechanical properties Medical sciences Methacrylate phosphonic acids Model compounds Monomers nuclear magnetic resonance spectroscopy Organic polymers Physicochemistry of polymers propane Seas shelf life Stability Surgery (general aspects). Transplantations, organ and tissue grafts. Graft diseases |
| title | Hydrolytically stable acidic monomers used in two steps self-etch adhesives |
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