Synthesis of Permethacrylated Beta-Cyclodextrin for Potential Uses in Dental Resins

Published

October 16, 2008

Author(s)

Rafael L. Bowen

Abstract

Literature searches to date have not revealed reports of methacrylated cyclodextrins in dental resins. The purpose of this study was to determine the feasibility of synthesizing methacrylated cyclodextrins, and to test the hypothesis that beta-cyclodextrin would become soluble in low-viscosity dental monomers if an adequate proportion of its hydroxyl groups were converted to methacrylate ester moieties. An excess of methacrylic anhydride, relative to all of the hydroxyl groups of the beta-cyclodextrin, was added with stirring to dried beta-cyclodextrin dissolved in pyridine. When the solution became clear, an aliquot portion was added to distilled water with stirring. A semisolid product remained after decanting off the aqueous supernatant. On drying, an amorphous solid remained. The product was practically insoluble in water but was soluble (miscible) in hydroxyethyl methacrylate, various other methacrylate monomers, and organic solvents; it polymerized in methanol when free-radical initiators were added. The methacrylated beta-cyclodextrin described here, and other varieties of polymerizable cyclodextrin derivatives, appear likely to have potential characteristics that would clearly justify further investigations regarding their value for uses in preventive and restorative dental materials.

Citation

Journal of Dental Research

Pub Type

Journals

Keywords

cyclodextrins, dental monomers, methacrylates, polymerization, shrinkage, synthesis

Citation

Bowen, R. (2008), Synthesis of Permethacrylated Beta-Cyclodextrin for Potential Uses in Dental Resins, Journal of Dental Research (Accessed July 26, 2024)