Design of a new dental adhesive — Effect of a water-soluble sodium acylphosphine oxide with crown ether on adhesion to dental hard tissues

The behavior of water-soluble photoinitiators with crown ethers in dental adhesives is unknown. This study investigated the effect of sodium acylphosphine oxide (APO-Na) with crown ether in a hydrophobic adhesive on adhesion to teeth. Sodium 2,4,6-trimethylbenzoyl-phenylphosphine oxide (TMPO-Na = APO-Na) was synthesized in 67.1% yield and identified by 1H NMR. APO-Na was dissolved in hydrophobic resins in the presence of a crown ether (ionophore effect). Thirty kinds of experimental single-step adhesives comprising APO-Na, CE, Bis-GMA, 6-methacryloyloxyhexyl phosphonoacetate (6-MHPA), and 4-methacryloyloxyethyl trimellitic acid (4-MET) were thereby prepared. Shear bond strength to unetched ground teeth was measured at a crosshead speed of 1.0 mm/min, and the data were analyzed by ANOVA. The shear bond strength results of bonding resins containing APO-Na with 18-crown-6-ether (CE-6) were significantly higher than that without CE-6 (control) (p