Incorporating Carbamate Functionalities in Multifunctional Monomer System Enhances Mechanical Properties of Methacrylate Dental Adhesives

Although resin-based composite is the most popular direct restoration material in the U.S., composite restorations can fail shortly after placement. The leading cause of failure is recurrent marginal decay. The adhesive that bonds the composite to the tooth is intended to seal the margin, but the degradation of the adhesive seal to dentin leads to gaps that are infiltrated by cariogenic bacteria. The development of strategies to mitigate adhesive degradation is an area of intense interest. Recent studies focus on exploiting hydrogen–bond interactions to enhance polymer network stability. This paper presents the preparation and characterization of model adhesives that capitalize on carbamate-functionalized long-chain silane monomers to enhance polymer stability and mechanical properties in wet environments. The adhesive composition is HEMA/BisGMA, 3-component photoinitiator system, carbamate-functionalized long-chain silane monomers, e.g., commercial SHEtMA (Cb1) and newly synthesized SHEMA (Cb2). Polymerization behavior, water sorption, leachates, and dynamic mechanical properties were investigated. The properties of Cb1 and Cb2 were compared to previously studied middle- (SC4) and short-chain (SC5) silane monomers. Cb1- and Cb2-formulations exhibit greater resilience under wet conditions as compared to middle-chain silane monomers. Dental adhesives containing the carbamate-functionalized long-chain silane monomers exhibit reduced flexibility in water-submersed conditions and enhanced stability as a result of increased hydrogen–bond interactions. The results emphasize the critical role of hydrogen bonding in maintaining structural integrity of dental adhesive formulations under conditions that simulate the wet, oral environment.