Biodegradation Studies of Novel Fluorinated Di-Vinyl Urethane Monomers and Interaction of Biological Elements with Their Polymerized Films

The monomeric components of resin composites in dental restorative materials are susceptible to hydrolysis in the oral cavity. The main objective of this study was to assess the bio-stability of fluorinated urethane dimethacrylates and determine the nature of fluoro-chemistry interactions with protein and bacterial adhesion (both sources of hydrolytic activity) onto cured resin. Degradation studies were performed in the presence of either albumin (in a mildly alkaline pH) or cholesterol esterase (CE). The surface chemistry of the polymers was assessed by water contact angle measurements, pre- and post- incubation with albumin. Adhesion of Streptococcus mutans to cured resin was investigated. The fluorinated monomers were more stable against degradation when compared to the commercial monomer bisphenol A-diglycidyl methacrylate (BisGMA). While fluorinated monomers showed hydrolytic stability with respect to CE, all fluorinated monomers underwent some degree of degradation with albumin. The fluoro-chemistry did not reduce protein and/or bacterial adhesion onto the surface, however post incubation with albumin, the fluorinated surfaces still presented hydrophobic character as determined by the high contact angle values ranging from 79° to 86°. These monomers could potentially be used to increase the hydrophobicity of polymeric composites and provide a means to moderate esterolytic degradation associated with the monomeric component of the polymers within the oral cavity.