title: Novel fluoro-carbon functional monomer for dental bonding.
abstract: Among several functional monomers, 10-methacryloxydecyl dihydrogen phosphate (10-MDP) bonded most effectively to hydroxyapatite (HAp). However, more hydrolysis-resistant functional monomers are needed to improve bond durability. Here, we investigated the adhesive potential of the novel fluoro-carbon functional monomer 6-methacryloxy-2,2,3,3,4,4,5,5-octafluorohexyl dihydrogen phosphate (MF8P; Kuraray Noritake Dental Inc., Tokyo, Japan) by studying its molecular interaction with powder HAp using solid-state nuclear magnetic resonance ((1)H MAS NMR) and with dentin using x-ray diffraction (XRD) and by characterizing its interface ultrastructure at dentin using transmission electron microscopy (TEM). We further determined the dissolution rate of the MF8P_Ca salt, the hydrophobicity of MF8P, and the bond strength of an experimental MF8P-based adhesive to dentin. NMR confirmed chemical adsorption of MF8P onto HAp. XRD and TEM revealed MF8P_Ca salt formation and nano-layering at dentin. The MF8P_Ca salt was as stable as that of 10-MDP; MF8P was as hydrophobic as 10-MDP; a significantly higher bond strength was recorded for MF8P than for 10-MDP. In conclusion, MF8P chemically bonded to HAp. Despite its shorter size, MF8P possesses characteristics similar to those of 10-MDP, most likely to be associated with the strong chemical bond between fluorine and carbon. Since favorable bond strength to dentin was recorded, MF8P can be considered a good candidate functional monomer for bonding.
authors.affiliation: KU Leuven BIOMAT, Department of Oral Health Sciences, KU Leuven (University of Leuven) & Dentistry, University Hospitals Leuven, Belgium.
authors.forename: K
authors.initials: K
authors.lastname: Yoshihara
authors.forename: Y
authors.initials: Y
authors.lastname: Yoshida
authors.forename: S
authors.initials: S
authors.lastname: Hayakawa
authors.forename: N
authors.initials: N
authors.lastname: Nagaoka
authors.forename: S
authors.initials: S
authors.lastname: Kamenoue
authors.forename: T
authors.initials: T
authors.lastname: Okihara
authors.forename: T
authors.initials: T
authors.lastname: Ogawa
authors.forename: M
authors.initials: M
authors.lastname: Nakamura
authors.forename: A
authors.initials: A
authors.lastname: Osaka
authors.forename: B
authors.initials: B
authors.lastname: Van Meerbeek
mesh_terms: D000268:Adhesiveness; D000327:Adsorption; D002118:Calcium / Q000737:chemistry; D001840:Dental Bonding; D003804:Dentin / Q000648:ultrastructure; D017886:Durapatite / Q000737:chemistry; D005465:Fluorocarbon Polymers / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry*; D046529:Microscopy, Electron, Transmission; D010755:Organophosphates / Q000737:chemistry*; D019279:Resin Cements / Q000737:chemistry*; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013314:Stress, Mechanical; D013499:Surface Properties; D013718:Tensile Strength; D014867:Water / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: C587457:6-methacryloxy-2,2,3,3,4,4,5,5-octafluorohexyl dihydrogen phosphate; C438313:Clearfil SE Bond; D005465:Fluorocarbon Polymers; D005466:Fluorocarbons; D008689:Methacrylates; D010755:Organophosphates; D019279:Resin Cements; D014867:Water; C069749:methacryloyloxydecyl dihydrogen phosphate; D017886:Durapatite; D002118:Calcium
keywords: 10-MDP; MF8P; adhesion; adhesive; dentin; hydroxyapatite