Properties of methacrylate-thiol-ene formulations as dental restorative materials. 2010

Neil B Cramer, and Charles L Couch, and Kathleen M Schreck, and Jordan E Boulden, and Robert Wydra, and Jeffrey W Stansbury, and Christopher N Bowman
Department of Chemical & Biological Engineering, University of Colorado, Boulder, CO 80309, United States. neil.cramer@colorado.edu

OBJECTIVE The objective of this study was to evaluate ternary methacrylate-thiol-ene systems, with varying thiol-ene content and thiol:ene stoichiometry, as dental restorative resin materials. It was hypothesized that an off-stoichiometric thiol-ene component would enhance interactions between the methacrylate and thiol-ene processes to reduce shrinkage stress while maintaining equivalent mechanical properties. METHODS Polymerization kinetics and functional group conversions were determined by Fourier transform infrared spectroscopy (FTIR). Cured resin mechanical properties were evaluated using a three-point flexural test, carried out with a hydraulic universal test system. Polymerization shrinkage stress was measured with a tensometer coupled with simultaneous real-time conversion monitoring. RESULTS The incorporation of thiol-ene mixtures as reactive diluents into conventional dimethacrylate resins previously was shown to combine synergistically advantageous methacrylate mechanical properties with the improved polymerization kinetics and reduced shrinkage stress of thiol-ene systems. In these systems, due to thiol consumption resultant from both the thiol-ene reaction and chain transfer involving the methacrylate polymerization, the optimum thiol:ene stoichiometry deviates from the traditional 1:1 ratio. Increasing the thiol:ene stoichiometry up to 3:1 results in systems with equivalent flexural modulus, 6-20% reduced flexural strength, and 5-33% reduced shrinkage stress relative to 1:1 stoichiometric thiol:ene systems. CONCLUSIONS Due to their improved overall functional group conversion, and shrinkage stress reduction while maintaining equivalent flexural modulus, methacrylate-thiol-ene resins, particularly those with excess thiol, beyond the conventional 1:1 thiol:ene molar ratio, yield superior dental restorative materials compared with purely dimethacrylate resins.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008422 Materials Testing The testing of materials and devices, especially those used for PROSTHESES AND IMPLANTS; SUTURES; TISSUE ADHESIVES; etc., for hardness, strength, durability, safety, efficacy, and biocompatibility. Biocompatibility Testing,Biocompatible Materials Testing,Hemocompatibility Testing,Testing, Biocompatible Materials,Testing, Hemocompatible Materials,Hemocompatibility Testings,Hemocompatible Materials Testing,Materials Testing, Biocompatible,Materials Testing, Hemocompatible,Testing, Biocompatibility,Testing, Hemocompatibility,Testing, Materials,Testings, Biocompatibility
D008689 Methacrylates Acrylic acids or acrylates which are substituted in the C-2 position with a methyl group. Methacrylate
D009636 Norbornanes Compounds that include or are derivatives of norbornane(bicyclo[2.2.1]heptane). Norbornane Derivatives,Norbornene Derivatives,Norbornenes,Norcamphanes,Derivatives, Norbornane,Derivatives, Norbornene
D003188 Composite Resins Synthetic resins, containing an inert filler, that are widely used in dentistry. Composite Resin,Resin, Composite,Resins, Composite
D003793 Dental Restoration, Permanent A restoration designed to remain in service for not less than 20 to 30 years, usually made of gold casting, cohesive gold, or amalgam. (Jablonski, Dictionary of Dentistry, 1992) Dental Fillings, Permanent,Dental Filling, Permanent,Dental Permanent Filling,Dental Permanent Fillings,Dental Restorations, Permanent,Filling, Dental Permanent,Filling, Permanent Dental,Fillings, Dental Permanent,Fillings, Permanent Dental,Permanent Dental Filling,Permanent Dental Fillings,Permanent Dental Restoration,Permanent Dental Restorations,Permanent Filling, Dental,Permanent Fillings, Dental,Restoration, Permanent Dental,Restorations, Permanent Dental
D003799 Dental Stress Analysis The description and measurement of the various factors that produce physical stress upon dental restorations, prostheses, or appliances, materials associated with them, or the natural oral structures. Analyses, Dental Stress,Analysis, Dental Stress,Stress Analyses, Dental,Stress Analysis, Dental,Dental Stress Analyses
D000498 Allyl Compounds Alkenes with the general formula H2C Compounds, Allyl
D000704 Analysis of Variance A statistical technique that isolates and assesses the contributions of categorical independent variables to variation in the mean of a continuous dependent variable. ANOVA,Analysis, Variance,Variance Analysis,Analyses, Variance,Variance Analyses
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines

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