The synthesis of fluorinated silane coupling agents having methoxy, ethoxy, or isocyanate groups was conducted in the present study and their applications to surface modification of glass and dental material (bovine tooth) are discussed.
Methoxy-type silane coupling agents were prepared by hydrosilylation of trichlorosilane with fluoroalkylated olefins, followed by reaction with sodium methoxide. Isocyanate-type coupling agents were obtained by reactions of chloro-type coupling agents with silver cyanate in benzene. Glasses modified with fluorinated coupling agents showed high repellency toward water and oleic acid. Fluorinated silane coupling agents possessing three methoxy or isocyanate groups formed fluorocarbon layers having high stability in acid and oxidant on glass surfaces. In vivo and in vitro experiments indicated very little plaque to accumulate on bovine tooth surfaces modified with the isocyanate-type coupling agent. Fluorinated silane coupling agents should thus prove useful as surface modifiers for the promotion of oral health.