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<0.05). Higher bond strength values [for enamel: BR24 at 19.3 (3.2) MPa; for dentin: BR29 at 20.2 (4.7) MPa] were achieved with the adhesives containing APO-Na, CE-6, 6-MHPA, and 4-MET. Therefore, it was found that APO-Na with CE-6 contributed to the efficient bonding performance of single-step adhesive to teeth. However, in view of the biosafety hazard posed by crown ethers, the search is still on for reagents that are biologically safer than crown ethers--but with ionophor effects--to be used in dental adhesives.
Ikemura
Kunio
K
Department of Research and Development, Shofu Inc., 11 Kamitakamatsu-cho, Fukuine, Higashiyama-ku, Kyoto 605-0983, Japan. k-ikemura@shofu.co.jp
Ichizawa
Kensuke
K
Fuchigami
Kiyomi
K
Ito
So
S
Endo
Takeshi
T
D000215:Acylation; D000818:Animals; D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry; D002417:Cattle; D003188:Composite Resins / Q000737:chemistry; D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D055117:Curing Lights, Dental; D001840:Dental Bonding; D003738:Dental Cements / Q000138:chemical synthesis* / Q000737:chemistry; D003743:Dental Enamel / Q000648:ultrastructure*; D003799:Dental Stress Analysis / Q000295:instrumentation; D003804:Dentin / Q000648:ultrastructure*; D057927:Hydrophobic and Hydrophilic Interactions; D007476:Ionophores / Q000737:chemistry; D008689:Methacrylates / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D010721:Phosphinic Acids / Q000737:chemistry; D010746:Phosphonoacetic Acid / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D011109:Polymethacrylic Acids / Q000737:chemistry; D019279:Resin Cements / Q000138:chemical synthesis / Q000737:chemistry; D033081:Shear Strength; D012995:Solubility; D014233:Tricarboxylic Acids / Q000737:chemistry; D014867:Water / Q000737:chemistry
C470433:Beautifil composite resin; D003188:Composite Resins; D043844:Crown Ethers; D003738:Dental Cements; D007476:Ionophores; D008689:Methacrylates; D010720:Phosphines; D010721:Phosphinic Acids; D011109:Polymethacrylic Acids; D019279:Resin Cements; D014233:Tricarboxylic Acids; D014867:Water; C020946:triethylene glycol dimethacrylate; C480970:phenylphosphinic acid; D011092:Polyethylene Glycols; D017438:Bisphenol A-Glycidyl Methacrylate; C098756:4-methacryloxyethyltrimellitic acid; D010746:Phosphonoacetic Acid