• Journal of the Korean Chemical Society
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• v.38 no.10
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• pp.753-762
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• 1994

Dephosphorylation of diphenyl- or isopropylphenyl-4-nitrophenylphosphinate (DPNPIN or IPNPIN) mediated by $OH^-$ or o-iodosobenzoate ion ($IB^-$) are relatively slow in aqueous solution. The reactions in CTAX micellar solutions are, however, very accelerated, because CTAX micelles can accommodate both reactants in their Stern layer in which they can easily react, while hydrophilic $OH^-$(or $IB^-$) and hydrophobic phosphinates are not mixed in water. Even though the concentrations (> $10^{-3}$ M) of $OH^-$(or $IB^-$) in CTAX solutions are much larger amounts than those ($6{\times}10^{-6}$ M) of phosphinates, the rate constants of the dephosphorylations are largely influenced by change of the concentration of the ions, which means that the reactions are not followed by the pseudo first order kinetics. In comparison to effect of the counter ions of CTAX in the reactions, CTACl is more effective on the dephosphorylation of DPNPIN (or IPNPIN) than CTABr due to easier expelling of $Cl^-$ ion by $OH^-$(or $IB^-$) ion from the micelle, because of easier solvation $Cl^-$ ion by water molecules. The reactivity of IPNPIN with $OH^-$(or $IB^-$) is lower than that of DPNPIN. The reason seems that the 'bulky' isopropyl group of IPNPIN hinders the attack of the nucleophiles. The mechanism of reaction of IPNPIN with IB- ion concluded as 'nucleophilic' instead of 'general basic' by a trapping experiment and a measured kinetic isotope effect.

• Restorative Dentistry and Endodontics
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• v.36 no.4
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• pp.280-289
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• 2011

Objectives: The purpose of this study was to evaluate ${\mu}TBS$ (microtensile bond strength) of current dentin bonding adhesives which have different hydrophobicity with low-shrinkage silorane resin. Materials and Methods: Thirty-six human third molars were used. Middle dentin was exposed. The teeth were randomly assigned to nine experimental groups: Silorane self-etch adhesives (SS), SS + phosphoric acid etching (SS + pa), Adper easy bond (AE), AE + Silorane system bonding (AE + SSb), Clearfil SE bond (CSE), CSE + SSb, All-Bond 2 (AB2), AB2 + SSb, All-Bond 3 (AB3). After adhesive's were applied, the clinical crowns were restored with Filtek LS (3M ESPE). The 0.8 mm ${\times}$ 0.8 mm sticks were submitted to a tensile load using a Micro Tensile Tester (Bisco Inc.). Water sorption was measured to estimate hydrophobicity adhesives. Results: ${\mu}TBS$ of silorane resin to 5 adhesives: SS, 23.2 MPa; CSE, 19.4 MPa; AB3, 30.3 MPa; AB2 and AE, no bond. Additional layering of SSb: CSE + SSb, 26.2 MPa; AB2 + SSb, 33.9 MPa; AE + SSb, no bond. High value of ${\mu}TBS$ was related to cohesive failure. SS showed the lowest water sorption. AE showed the highest solubility. Conclusions: The hydrophobicity of adhesive increased, and silorane resin bond-strength was also increased. Additional hydrophobic adhesive layer did not increase the bond-strength to silorane resin except AB2 + SSb. All-Bond 3 showed similar ${\mu}TBS$ & water sorption with SS. By these facts, we could reach a conclusion that All-Bond 3 is a competitive adhesive which can replace the Silorane adhesive system.