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Comparative Study on Adhesive Performance of Functional Monomers

¹ Department of Biomaterials, Okayama University Graduate School of Medicine and Dentistry, 2-5-1 Shikata-cho, Okayama 700-8525, Japan;
² Research Center for Biomedical Engineering, Okayama University, 2-5-1 Shikata-cho, Okayama 700-8525, Japan;
³ Department of Biomaterials Science, Hiroshima University Graduate School of Biomaterials Science, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8553, Japan;
⁴ Department of Operative Dentistry and Dental Materials, Hiroshima University Graduate School of Biomaterials Science, 1-2-3 Kasumi, Minami-Ku, Hiroshima 734-8553, Japan;
⁵ Research Planning Department, Toray Research Center, Inc., Sonoyama 3-3-7, Otsu, Shiga 520-8567, Japan;
⁶ Division for General Dentistry, Hokkaido University Dental Hospital, Kita 13 Nishi 7, Kita-ku, Sapporo 060-8586, Japan;
⁷ Institute of Experimental Animals, Shinshu University School of Medicine, 3-1-1 Asahi, Matsumoto, Nagano 390-8621, Japan; and
⁸ Leuven BIOMAT Research Cluster, Department of Conservative Dentistry, School of Dentistry, Oral Pathology and Maxillo-Facial Surgery, Catholic University of Leuven, Kapucijnenvoer 7, B-3000 Leuven, Belgium;

View larger version (15K): [in a new window]   Figure 1. XPS wide-scan spectra of untreated hydroxyapatite (a), of hydroxyapatite treated with 15% (w/w) 4-MET for 30 sec (b), of hydroxyapatite treated with 15% (w/w) 10-MDP for 30 sec (c), of hydroxyapatite treated with 15% (w/w) 4-MET for 30 min (d), of hydroxyapatite treated with phenyl-P for 30 min (e), and of hydroxyapatite treated with 10-MDP for 30 min (f).

View larger version (17K): [in a new window]   Figure 2. (a) XPS narrow-scan spectra of the C 1s region of 4-META (4-methacryloxyethyl trimellitate anhydride) powder (top spectrum) and of hydroxyapatite treated with 15% (w/w) 4-MET for 30 min (bottom spectrum). Peak deconvolution revealed that almost all carbon originated from 4-MET, with a peak at 284.6 eV representing C-C, C-H, and C=C bindings, a peak at 286.1 eV representing C-O bindings, and a peak representing ester and carboxyl groups. As compared with 4-META powder (288.6 eV), the carboxyl peak had shifted to a lower binding energy (288.3 eV). Deconvolution of the shifted peak disclosed a peak at 288.6 eV, representing the ester function and unreacted carboxyl groups, and a peak at 288.2 eV that represents carboxyl groups that reacted with the Ca of hydroxyapatite. It should be mentioned that the peak position and intensity of the C-O component (top spectrum) for 4-META powder are slightly different from what theoretically would be expected, and from the C-O subpeak in the bottom spectrum. This must be attributed to impurities within the 4-META powder sample that were readily removed during the adhesive treatment. (b) XPS narrow-scan spectra of the C 1s region of untreated phenyl-P (top spectrum) and of hydroxyapatite treated with 15% (w/w) phenyl-P (bottom spectrum). (c) XPS narrow-scan spectra of the C1s region of untreated 10-MDP (top spectrum) and of hydroxyapatite treated with 15% (w/w) 10-MDP (bottom spectrum). Peak deconvolution revealed that almost all carbon originated from 10-MDP on hydroxyapatite, with a peak at 284.6 eV representing C-C, C-H, and C=C bindings, a peak at 286.1 eV representing C-O bindings, and a peak representing ester at 288.6eV. In high-resolution XPS C 1s spectra, aliphatic carbon shows a large asymmetry due to vibrational effect, while aromatic carbon is symmetrical (Beamson and Briggs, 1992). Therefore, the peak at 284.6 eV representing C-C, C-H, and C=C bindings of 10-MDP is expressed with an asymmetrical shape.

View larger version (90K): [in a new window]   Figure 3. TEM photomicrographs illustrating the resin-dentin interfaces produced by Unifil Bond (GC) (a,b), Clearfil Liner Bond 2 (Kuraray) (c), and Clearfil SE (Kuraray) (d,e). The photomicrographs in (a) and (d) represent unstained, non-demineralized sections, those in (b) and (e) stained, demineralized sections, and that in (c) a stained, non-demineralized section. A = adhesive resin; H = hybrid layer; L = lab-demineralized unaffected dentin; R = resin-impregnated smear plug; U = unaffected dentin.