N-acryloxysuccinimide: Synthesis, characterization, and incorporation in dental adhesives

Abstract In an attempt to enrich the world of dentistry through the development of new materials, this study proposes to synthesize and incorporate a monomer containing the N -hydroxysuccinimide (NHS) ester reactive group to a dental adhesive. As such, this study developed a simple method to obtain NHS esters by employing acrylic acid (AA) and NHS in the presence of EDC ( N -ethyl- N ′-(3-dimethylaminopropyl)carbodiimide), from an aprotic medium. The experimental N -acryloxysuccinimide (NSA) monomer was analyzed by infrared spectroscopy (FTIR) and nuclear magnetic resonance of hydrogen ( 1 H NMR). This monomer was then incorporated within a prepared dental adhesive, in a 5% proportion. The modified adhesive, containing NSA, was applied to the dental surface of bovine teeth to obtain an adhesive/dentin interface in vitro . The characterization of this interface by Raman spectroscopy presented the formation of new amide bonds. Moreover, through scanning electron microscopy (SEM), it became possible to observe an intense penetration of this modified adhesive on the dental surface. Considering the outcome, it can be concluded that the synthesized NSA monomer provided a favorable condition for the dental adhesives to interact chemically with the dentin collagen fibers.