Stéfani Becker Rodrigues1, Cesar Liberato Petzhold2, Douglas Gamba2, Vicente Castelo Branco Leitune1, Fabrício Mezzomo Collares3. 1. Dental Materials Laboratory, School of Dentistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil. 2. Organic Chemistry Department, Chemistry Institute, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil. 3. Dental Materials Laboratory, School of Dentistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil. Electronic address: fabricio.collares@ufrgs.br.
Abstract
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 40s 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.
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 40s 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.
Authors: Ana P Fugolin; Adam Dobson; Wilbes Mbiya; Oscar Navarro; Jack L Ferracane; Carmem S Pfeifer Journal: Dent Mater Date: 2019-02-28 Impact factor: 5.304
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Authors: Ana P Fugolin; Matthew G Logan; Alexander J Kendall; Jack L Ferracane; Carmem S Pfeifer Journal: Dent Mater Date: 2021-03-02 Impact factor: 5.304