The methacryloyl fluoride(MF)-methyl methacrylate(MMA) copolymer was prepared and the rates of fluoride ion release from the copolymer and the blended polymer with poly(methylmethacrylate) (PMMA)were determined by the use of a fluoride electrode. The rates were found to be constant over 60 days.Infrared analysis revealed that the fluoride ion was released by the hydrolysis occurred exclusively at the MF-MF configurations, followed by an anhydride formation. The dentins of extracted bovine teeth were treated with 3% of various metal chlorides in a 10% citric acid aqueous solution, and the effect of the formulations of cleaning solution on the adhesive strength of 5%-4-META/MMA/TBB-O resin to the treated dentin surface was examined. The highest adhesive strength was obtained for 3% ferric chloride or 3% cupric chloride. The adhesive strengths of the fluoride-containing resin to human enamel treated with a 65% phosphoric acid aqueous solution and human dentin treated with 3% cupric chloride in a 10% citric acid aqueous solution were 8.3 MPa and 12.2 MPa, respectively.