Acrylamides and methacrylamides as alternative monomers for dental adhesives
| Autor: | Vicente Castelo Branco Leitune, Stéfani Becker Rodrigues, Douglas Gamba, Fabrício Mezzomo Collares, Cesar Liberato Petzhold |
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| Rok vydání: | 2018 |
| Předmět: |
Glycidyl methacrylate
Materials science Chemical Phenomena Methacrylic anhydride Dental Cements 02 engineering and technology Methacrylate Polymerization 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Elastic Modulus Materials Testing Methacrylamide General Materials Science General Dentistry Acrylamides Calorimetry Differential Scanning Bond strength 030206 dentistry 021001 nanoscience & nanotechnology Monomer chemistry Mechanics of Materials Methacrylates Adhesive 0210 nano-technology Nuclear chemistry |
| Zdroj: | Dental materials : official publication of the Academy of Dental Materials. 34(11) |
| ISSN: | 1879-0097 |
| Popis: | Objective Synthesize and characterize a methacrylamide monomer for adhesive system and evaluate the physicochemical properties of the adhesive resin. Methods The liquid methacrylamide monomer N,N′,N″-(nitrilotris(ethane-2,1-dyil)tris(2-methylacrylamide) (TMA) was prepared by reaction of methacrylic anhydride and tris(2-aminoethyl)amine with 60% yields. The TMA structure was analyzed by 1H NMR, 13C NMR, ATR-FTIR and UHPLC-QTOF-MS. Experimental adhesive resin containing bisphenol-A glycidyl methacrylate (BISGMA), 2-hydroxyethylacrylamide (HEAA), 2-hydroxyethylmethacrylate (HEMA) and TMA were formulated. Polymerization kinetics of neat TMA and experimental adhesive resin (TMA33%/HEAA66%, TMA50%/HEAA50%, TMA66%/HEAA33%, TMA50%/HEMA50%, BisGMA/HEAA/TMA and BisGMA/HEMA) were evaluated using Differential Scanning Calorimetry. Physiochemical properties for BisGMA/HEAA/TMA and BisGMA/HEMA adhesives were evaluated by cytotoxicity, ultimate tensile strength (UTS), softening in solvent (ΔKHN), contact angle (θ), microtensile bond strength (μTBS) and failure analysis. A primer was also formulated with H2O/HEAA/AMPS (2-acrylamido-2-methylpropane sulfonic acid) and the pH value was verified and compared to commercial primer. Results Adhesive resin with only HEAA and TMA (TMA33%/HEAA66%, TMA50%/HEAA50%, TMA66%/HEAA33%) showed lower conversion and polymerization rate after 40 s of light activation. Conversion up to 60% was found for BisGMA/HEAA/TMA and BisGMA/HEMA adhesive resin without significant difference between groups, p > 0.05. Cytotoxicity, UTS, μTBS, ΔKHN and θ showed no statistical difference, p > 0.05, between BisGMA/HEAA/TMA and BisGMA/HEMA adhesive resin. Significance In this study, the proposed synthetic route resulted in a tris(methacrylamide). A new primer composed without acrylates or methacrylates was formulated for 3-step etch-and-rinse adhesive system without the presence of HEMA monomer. Physicochemical properties and cell viability of BisGMA/HEAA/TMA adhesive resin represents an alternative adhesive resin without HEMA monomer. |
| Databáze: | OpenAIRE |
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