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This study assessed the effect of a primer containing 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl)propionate (MDTHP) on the bonding of noble metal alloys to an acrylic resin. Three noble metal alloys were selected as adherends, and V-Primer containing 6-(4-vinylbenzyl-n-propyl)amino-1,3,5-triazine-2,4-dithione was used as a comparative control. The disk specimens of each noble metal alloy were wet-ground and divided into three conditions: specimens primed with MDTHP primer or V-Primer, and specimens without priming. An acrylic resin was bonded to each specimen, and the specimens were performed the shear bond test. The MDTHP primer showed higher shear bond strength than the V-Primer for all specimens. X-ray photoelectron spectroscopic analysis showed that MDTHP was adsorbed on the Au-Pt-Pd alloy surface even after acetone cleaning. MDTHP binds not only with Cu but also with Au and Ag, promoting the bond strength of noble metal alloys. The effectiveness of MDTHP on dental noble metal alloys was suggested.

Recently in Japan, due to the increased prices of palladium and gold, cast titanium restorations have been included in the Japanese national health insurance system. The purpose of this review was to survey the available literature on titanium bonding systems, focusing on the adhesive monomer in the luting agent in order to expand the application of resin-bonded fixed prostheses made of titanium or titanium alloys. It was found that adhesive monomers are effective for bonding to titanium, and provide results equal to the procedures of silanization and tribochemical silica coating. A primer or a luting agent, including 10-methacryloyloxydecyl dihydrogen phosphate (MDP), methacryloyloxyalkyl thiophosphate derivative (MEPS), 6-methacryloxyhexyl phosphonoacetate (6-MHPA), and 4-methacryloyloxyethl trimellitate anhydride (4-META) promotes bonding characteristics between titanium and the resin material.

Objective The purpose of this study was to assess the effects of an experimental primer containing acetone solution and a sulfur-containing functional monomer, 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl)propionate (MDTHP), on the bonds between noble metals and acrylic resin. Methods The experimental primer used as the control for comparison consisted of 6-(4-vinylbenzyl-n-propyl)amino-1,3,5-triazine-2,4-dithione (VBATDT) in acetone. These primers were prepared as equimolar functional monomers (0.1 mol%). A self-polymerizing acrylic resin initiated with tri-n-butylborane (TBB) was used as the luting agent. Four elemental metal disks (silver, copper, palladium, and gold) were used as adherend specimens. All the disks were wet-ground with silicon carbide paper (#1500). Bonding reactions were performed on 12 combinations of the four metals, and the disks were either primed with MDTHP or VBATDT or were unprimed (control). Shear bond strengths were determined pre- and post-thermocycling (5–55 °C, dwell time 60 s, 20,000 cycles). The results were statistically analyzed via a non-parametric test (α = 0.05). Results The post-thermocycling shear bond strengths of the MDTHP primer were as follows (median, n = 11): 13.2 MPa on silver, 25.9 MPa on copper, 4.1 MPa on palladium, and 11.3 MPa on gold. The MDTHP primer showed higher post-thermocycling shear bond strength on all the four metals. Additionally, on silver and copper, the MDTHP bond strengths were higher than on the other metals. Significance Within the limitation of current of experimental setting, the MDTHP compound may be applicable as a functional monomer for bonding noble metal alloys.

The purpose of this study is to investigate the combined effect of two-liquid silane-phosphate primer and single-liquid sodium sulfite primer on bonding between self-polymerizing resins and feldspathic ceramics, and to promote the polymerization behavior of self-polymerizing resins at the bonding interface. The silane-phosphate primer (Super-Bond PZ Primer; PZ) and the sodium sulfite primer (Teeth Primer; TP) were used as the surface treatment agents for bonding the feldspathic ceramics and the self-polymerizing resins (MMA-TBB resin and 4-META/MMA-TBB resin). Combined PZ and TP showed high shear bond strengths. The peak of the differential scanning calorimetry curve was shown to occur early through the addition of TP. These results indicated that additional TP promoted the conversion in the initial polymerization of resin, and the firmly bond was obtained at the interface. PZ+TP treatment can be regarded as an effective treatment for a temporary splint used in teeth restoration.

This study aimed to clarify the degree of difference in radiopacity between sixteen CAD/CAM composite resin blocks, one ceramic block, and teeth of the same thickness on radiographs. The radiographic density of CAD/CAM composite resin blocks was measured and the results were compared with the corresponding values for enamel and dentin. Additionally, the study analyzed the constituent elements of each type of CAD/CAM composite resin block and conducted an examination to identify those elements exerting an influence on radiopacity. Compared to the enamel, there were five blocks with significantly higher radiopacity, two blocks with the same level in radiopacity, and ten blocks with notably lower radiopacity. Compared to the dentin, there were ten blocks with significantly higher radiopacity, one block with the same level in radiopacity, and six blocks with notably lower radiopacity. All of the CAD/CAM composite resin blocks for molars contained barium and strontium. This result suggests that the addition of heavy metals, for example, barium, strontium, and zirconium, would be effective in providing CAD/CAM composite resin blocks with radiopacity.

To clarify the effect of a multi-purpose primer combining several functional monomers on two prosthodontic materials (cast titanium and a gold alloy) after airborne-particle abrasion.Disk-shaped adherends were prepared from cast titanium (CP Titanium JIS2) and a gold alloy (Casting Gold M.C. Type IV). A silane-containing two-liquid primer (MC primer (MC)) and two silane-free single-liquid primers (Alloy Primer (AP) and V-Primer (VP)) were used as surface-treatment agents. The shear bond strengths were determined before and after thermocycling to evaluate the adhesive durability, and the results were compared using a non-parametric statistical analysis. The effect of airborne-particle abrasion with alumina on the titanium surface was analyzed by X-ray photoelectron spectroscopy (XPS).There was no significant difference in bond strength between the MC and AP before and after thermocycling, whereas VP showed significantly lower values. XPS revealed that the titanium acquired hydrophilic properties after the airborne-particle abrasion.The novelty of this study is that it shows that the presence/absence of the silane had no effect on the bonding of cast titanium with an acrylic resin. The study also showed that the multi-purpose primer can be used without any problems with both cast titanium and gold alloy, in combination with airborne-particle abrasion with alumina.

This study assessed the gloss and surface roughness of computer-aided design/computer-aided manufacturing (CAD/CAM) resin composites corroded with acidulated phosphate fluoride (APF) application. One ceramic block, ten CAD/CAM resin composites for premolars, and four CAD/CAM resin composites for molars were assessed. The surface topography of the materials before and after APF application was observed using an electron microscope. The results were analyzed by Wilcoxon signed-rank test and Dunnett's many to one test (p

The purpose of the current study was to evaluate the effect of etching with potassium hydrogen difluoride (KHF2) and ammonium hydrogen difluoride (NH4HF2) on the bond strength of a self-polymerizing methyl methacrylate resin (MMA-TBB) bonded to zirconia. Zirconia disks were prepared using the following surface treatment: no treatment, alumina blasting, and etching with KHF2 or NH4HF2. The specimens were bonded with the MMA-TBB. The shear bond (O=5 mm) strength was measured. The surface free energies of the specimens were determined by measuring contact angles. The KHF2 and NH4HF2 groups exhibited higher shear bond strength and surface free energy than did the alumina blasting and no treatment groups. Compared with alumina blasting, etching with KHF2 and NH4HF2 exhibited superior bonding ability of mechanical retention to zirconia.

This study was conducted to clarify the influence of the copper surface oxidation and reduction on the shear-bond strength with functional monomers. Unheated copper specimens (UH, n = 88) were wet-ground. Three-quarters of the UH were then heated (HT). Two-thirds of the HT was then immersed in a hydrochloric acid solution (AC). Half of the AC was then reheated (RH). Each group was further divided into two groups (n = 11), which were primed by either 6-methacryloyloxyhexyl 2-thiouracil-5-carboxylate (MTU-6) or 10-methacryloyloxydecyl dihydrogen phosphate (MDP). The shear-bond strength tests were used for bonding with an acrylic resin. The surface roughness values and chemical states of the four groups were analyzed using a confocal scanning laser microscope and X-ray photoelectron spectroscopy (XPS). The shear-bond strengths of HT and RH were the lowest in the MTU-6-primed groups. The result of AC was significantly lower than others in the MDP-primed groups. The XPS results showed that the surfaces of UH and AC consisted of Cu2O and Cu. The surface changed to CuO upon heating. The presence or absence of copper-oxide films showed the opposite trends in the effectiveness of MTU-6 and MDP to improve bond strength. The results could elucidate the effects of functional monomers on copper-oxide films.

Purpose: This study evaluated the effect of an aromatic silane compound and acidic functional monomer on the bond strength of fused quartz. Materials and Methods: A total of 264 disk specimens were fabricated from fused quartz for shear bond testing. Two silane compounds were used: 3-(trimethoxysilyl)propyl methacrylate (3-TMSPMA) and 3-(4-methacryloyloxyphenyl) propyltrimethoxysilane (3-MPPTS). As acidic functional monomers, 4-methacryloyloxyethyl trimellitate (4-MET) and 10-methacryloyloxydecyl dihydrogen phosphate (10-MDP) were used. The disks were primed with one of each silane compound with or without the acidic functional monomer of the same molarity. The specimens were bonded with a tri-n-butylborane (TBB) initiated luting material. The shear bond strength was determined before and after 10,000 thermocycles. Bond strength was statistically evaluated with Kruskal-Wallis, Mann-Whitney U-, and Steel- Dwass tests. To test dye penetration, the specimens were immersed in 0.5 wt% fuchsin solution for 24 h after priming with each condition, bonding, and 10,000 thermocycles. The dye penetration area was determined by observing the backside of the bonded specimen with an optical microscope. The relationship between the shear bond strength and dye penetration ratio was analyzed with Spearman’s rank correlation test. Results: The highest post-thermocycling bond strengths in the 1 mol% and 2 mol% groups were 3-TMSPMA + 10- MDP and 3-MPPTS + 10-MDP. Spearman’s rank correlation coefficient between shear bond strength and dye penetration area was γ = -0.7519, indicating a strong negative correlation. Conclusion: The surface treatments of 3-TMSPMA and 3-MPPTS combined with 10-MDP yielded higher bond strength after 10,000 thermocycles than those combined with 4-MET, despite the similarity in molarity. The shear bond strength was negatively correlated with the dye penetration area.

Purpose To evaluate the influence of polymerization methods and a metal priming agent on the bond strength between gold alloy for metal ceramic restorations and dual-cure-type resin luting agents, and on the strength and hardness of the luting agents. Methods A total of 154 disks cast by a gold alloy were treated with or without a metal priming agent. One of the three luting agents was applied on the disk. The luting agent was either chemically or dual-polymerized. The shear bond strength was measured both before and after thermocycling. In addition, scanning electron microscope (SEM) observation, flexural strength test, and Knoop hardness test were performed. Results Significant differences among the luting agents were observed in terms of bond strength and flexural strength. Significant differences between chemically and dual-polymerized luting agents were observed regarding shear bond strength, flexural strength, and Knoop hardness before thermocycling. The application of the priming agent was effective only for a luting agent. Conclusion Both bond strength and flexural strength differed among three luting agents. The effect of the priming agent on bond strength differed among the luting agents. Both the bond and flexural strength of a chemically polymerized luting agent differed before or after thermocycling.

The aim of this study was to clarify the influence of the copper surfaces changed from Cu or Cu2O to CuO on the bonding strength of resin with organic sulfur compounds. The disk-shaped specimens (n = 44) of copper were wet-ground. Half of the specimens were heated at 400 &deg, C for 4 min in an electric furnace (HT: heated). Half of the specimens were not heated (UH: unheated). The specimens were further divided into two groups. Each group was primed by 6-methacryloyloxyhexyl 2-thiouracil-5-carboxylate (MTU-6) or unprimed (n = 11). A statistical analysis of the results of shear bond strength testing was performed, and the failure mode of the bonded areas was classified with an optical microscope. Two types of specimen surface (UH or HT) were analyzed chemically using X-ray photoelectron spectroscopy (XPS). When primed with MTU-6, unheated Cu (28.3 MPa) showed greater bond strength than heated (19.1 MPa). When unprimed, heated Cu (4.1 MPa) showed greater bond strength than unheated (2.3 MPa). The results of the debonded surfaces observation showed that only the UH-MTU-6 group demonstrated a combination of adhesive and cohesive failures in all specimens. The XPS results showed that the surface of copper changed from Cu or Cu2O to CuO when HT. These results confirmed that it is necessary to take care of the copper oxide contained in noble metal alloys when using organic sulfur compounds for adhesion.

The purpose of this study was to evaluate the surface properties and gloss of CAD/CAM composites after toothbrush abrasion testing. Four CAD/CAM composites for molars (Cerasmart 300, Estelite P block, Katana Avencia P block, and KZR-CAD HR3 Gammatheta), one CAD/CAM composite for premolars (Shofu Block HC Hard), and one feldspathic ceramics (Vitablocs Mark II) were assessed. Knoop hardness number, gloss, and surface roughness (Ra, Rz, and Sa) were measured before and after toothbrush abrasion testing. Knoop hardness number values were in the order Vitablocs Mark II > Katana Avencia P block > Estelite P Block > Shofu Block HC Hard > Cerasmart 300 > KZR-CAD HR3 Gammatheta. After testing, the gloss of Estelite P block and KZR-CAD HR3 Gammatheta was greatly decreased and surface roughness was greatly increased. Periodic recall and re-polishing may thus be necessary when these products are used clinically.

Purpose This study investigated the influence of an interaction between sulfur-containing monomers and other monomers in multipurpose primers on the bond durability of a tri-n-butylborane (TBB)-initiated acrylic resin to a gold alloy. Methods The disk-shaped adherend materials were prepared from a gold alloy (Casting Gold M.C. Type IV). Two multipurpose-primers (Universal Primer, Monobond Plus), four metal primers containing an organic sulfur compound (M.L. Primer, Alloy Primer, Metaltite, and V-Primer), and three acidic primers (Estenia Opaque Primer, Acryl Bond, and Super-Bond Liquid) were used. The shear bond strengths were determined pre- and post-thermocycling to evaluate the bond durability. A statistical analysis of the results was performed using a non-parametric procedure, and the cohesive failure ratios of the debonded surfaces were compared. Results Among the pre-thermocycling groups, M.L. Primer, Metaltite, Monobond Plus, Universal Primer, and Alloy Primer showed the greatest bond strengths. Among the post-thermocycling groups, M.L. Primer, Metaltite, Monobond Plus, and Universal Primer showed the greatest bond strengths, whereas Acryl Bond, Super-Bond Liquid, Estenia Opaque Primer, and the unprimed control showed the lowest. Similarly, the primers that did not contain either a sulfur compound showed an obvious reduction in the cohesive failure ratio. Conclusions Multi-purpose primers containing a sulfur-containing monomer increased the bond strength of a TBB-initiated acrylic resin to a gold alloy. The proportion of the area of cohesive failure to the bonded area showed an interrelationship with the shear bond strength testing results.

The purpose of the current study was to synthesize a methacrylate monomer with a thiohydantoin structure. In a flask, (2-thiohydantoin-4-yl) propionic acid, 10-hyroxydecyl methacrylate, 4-dimethylaminopyridine, and tetrahydrofuran (THF) were placed in a nitrogen atmosphere. A THF solution of N,N'-dicyclohexylcarbodiimide was added and stirred at room temperature. Ethyl acetate and n-hexane were then added to the reaction mixture. The reacted slurry was purified by chromatography with silica gel and hexane-ethyl acetate gradient elution solvent. The structure of the compound was assigned with proton nuclear magnetic resonance spectrum analysis, infrared spectroscopy, and high-resolution mass spectral analysis. The colorless viscous liquid obtained in yield of 49% was characterized as 10-methacryloyloxydecyl-(2-thiohydantoin-4-yl)propionate (MDTHP) or 10-((3-(5-oxo-2-thioxysoimidazolidin-4-yl)propanoyl)oxy)decyl methacrylate (2-THPDM). The MDTHP was soluble to acetone, isopropanol, and methyl methacrylate up to 2.6% or more. This compound could be potentially applicable as a functional monomer for bonding metals and alloys.

This study aimed to investigate how different compositions of experimental silane-based primers in a methyl methacrylate solution containing 3-(trimethoxysilyl)propyl methacrylate (3-TMSPMA) or 3-(4-methacryloyloxyphenyl)propyl trimethoxysilane (3-MPPTS) might act as silicon dioxide bonding agents. With or without post-silanization heat treatment, primer-treated quartz discs were bonded using the MMA-TBB resin and their bond strengths were evaluated. The disks were primed with one of the following materials: 1 mol% 3-TMSPMA, 2 mol% 3-TMSPMA, 1 mol% 3-MPPTS, and 2 mol% 3-MPPTS. Shear bond strength was determined both before and after thermocycling. Statistical analyses were performed with non-parametric procedure (Kruskal-Wallis, Mann-Whitney U, and Steel-Dwass tests). Both primers were effective with heat treatment to enhance bonding between quartz and the MMA-TBB, and the bonding durability of the 1 and 2 mol% 3-MPPTS (16.8 and 24.9 MPa) with heat groups was significantly higher than in the 1 and 2 mol% 3-TMSPMA (5.4 and 9.8 MPa) with heat groups.

This study evaluated the light intensity of light-emitting diode (LED) units and the effects of five laboratory polymerization units on hardness and flexural strength. Two indirect composite materials (Cesead N and Solidex Hardura) were polymerized with five units (α-Light II, Hyper LII, LED Cure Master, Twinkle LED, and α-Light V). The light intensity of the devices was measured with a spectroradiometer. After light exposure, Knoop hardness number, flexural strength, and elastic modulus were determined. Evaluation of light intensity, using a wavelength range of 400 to 500 nm, revealed that the α-Light V and Hyper LII units had the highest light intensity. For the top surface of the two composites, the Knoop hardness number was significantly higher for the α-Light V and Hyper LII. For the two composite materials, flexural strength did not differ among the five polymerizing units. The present results indicate that the Cesead N and Solidex Hardura composites can be adequately polymerized with laboratory LED units.

This study aimed to evaluate the effect of surface preparation on bond strength of a tri-n-butylborane initiated resin (MMA-TBB) bonded to zirconia. Zirconia disks were either airborne-particle abraded with alumina or silica-coated. The disks were thereafter primed with one of the following materials: phosphate-silane (Clearfil Ceramic Primer), phosphate (Alloy Primer), or silane (ESPE Sil). The specimens were bonded with the MMA-TBB. Shear bond strength was determined both before and after thermocycling. Bond strength of unprimed zirconia (control) was not affected by the surface roughness of each adherend. Priming with phosphate was effective for bonding alumina-blasted zirconia. Priming with silane was effective for bonding silica-coated zirconia. Priming effect of the phosphate-silane was superior to that of silane alone for bonding silica-coated zirconia. Bond strength to zirconia of the MMATBB is significantly influenced by a combination of the specific functional monomer and the surface modification performed rather than the material surface roughness.

Purpose The aim of this study was to evaluate the shear bond strength and durability of MMA-TBB resin to human enamel applied a self-etching primer with phosphoric acid etching. Methods A self-etching primer (Teeth primer, TP) containing 4-methacryloyloxyethyl trimellitate anhydride (4-META) and sodium sulfite and two etchants having different phosphoric acid concentrations (K-etchant gel, KE, 35–45%: Red gel, RG, 20–25%) were used as treatment agent, and MMA-TBB resin was used as luting agent. Enamel surfaces were treated with six methods which were as follow: KE, RG, TP, KE + TP, and RG + TP. After enamel specimens were bonded with MMA-TBB resin and stored in distilled water for 24 h, the shear bond strength test was done at 0 thermocycling or 20,000 thermocycling. These results were statistically verified with Steel-Dwass multiple comparisons and Man–Whitney U test. Results The shear bond strength of TP group, KE + TP group, and RG + TP group were significantly higher than KE group and RG group in pre-thermocycling. KE + TP group and RG + TP group were significantly higher than other groups in post-thermocycling. Conclusions Applying TP with phosphoric acid etching can increased shear bond durability despite difference of phosphoric acid concentrations (35–45% or 20–25%).

This study aimed to investigate how different compositions of experimental silane-based primers in a methyl methacrylate solution containing 3-(trimethoxysilyl)propyl methacrylate (3-TMSPMA) or 3-(4-methacryloyloxyphenyl)propyl trimethoxysilane (3-MPPTS) might act as silicon dioxide bonding agents. With or without post-silanization heat treatment, primer-treated quartz discs were bonded using the MMA-TBB resin and their bond strengths were evaluated. The disks were primed with one of the following materials: 1 mol% 3-TMSPMA, 2 mol% 3-TMSPMA, 1 mol% 3-MPPTS, and 2 mol% 3-MPPTS. Shear bond strength was determined both before and after thermocycling. Statistical analyses were performed with non-parametric procedure (Kruskal-Wallis, Mann-Whitney U, and Steel-Dwass tests). Both primers were effective with heat treatment to enhance bonding between quartz and the MMA-TBB, and the bonding durability of the 1 and 2 mol% 3-MPPTS (16.8 and 24.9 MPa) with heat groups was significantly higher than in the 1 and 2 mol% 3-TMSPMA (5.4 and 9.8 MPa) with heat groups.

The purpose of the current study was to evaluate the bonding performance of two single-liquid primers, which contained 6-(4-vinylbenzyl-n-propyl) amino-1,3,5-triazine-2,4-dithione (VTD) or 6-methacryloyloxyhexyl 2-thiouracil 5-carboxylate (MTU-6), used for bonding between metals and an acrylic resin. A gold alloy and high-purity titanium were used as adherend materials, and a transparent acrylic resin initiated with tri-n-butylborane derivative was selected as the luting material. Both adherends were treated with one of the primers and bonded with the luting material, after which shear bond strength was determined. Fourier transform infrared spectroscopy was used to analyze debonded resin specimens. Shear bond strength to gold alloy was significantly greater than that to titanium for both the VTD and MTU-6 primers. A trace of thiol structure, probably derived from VTD and MTU-6, was detected on resin surfaces debonded from gold alloy. These results indicate that the two organic sulfur compounds, which are stable in an atmospheric environment, are tautomerized into a thiol structure, thus allowing adsorption onto noble metals. In addition, the adsorbed thiol compounds contribute to chemical bonding between the acrylic resin and noble metal alloy, as polymerizable adhesive functional monomers.

This study aimed to evaluate the effect of surface preparation on bond strength of a tri-n-butylborane initiated resin (MMA-TBB) bonded to zirconia. Zirconia disks were either airborne-particle abraded with alumina or silica-coated. The disks were thereafter primed with one of the following materials: phosphate-silane (Clearfil Ceramic Primer), phosphate (Alloy Primer), or silane (ESPE Sil). The specimens were bonded with the MMA-TBB. Shear bond strength was determined both before and after thermocycling. Bond strength of unprimed zirconia (control) was not affected by the surface roughness of each adherend. Priming with phosphate was effective for bonding alumina-blasted zirconia. Priming with silane was effective for bonding silica-coated zirconia. Priming effect of the phosphate-silane was superior to that of silane alone for bonding silica-coated zirconia. Bond strength to zirconia of the MMATBB is significantly influenced by a combination of the specific functional monomer and the surface modification performed rather than the material surface roughness.

This study compared the wear characteristics of a heat-pressed lithium disilicate ceramic material opposed to feldspathic porcelain, a lithium disilicate glass ceramic, and zirconia materials. Ceramic plate specimens were prepared from feldspathic porcelain (EX-3 nA1B), lithium disilicate glass ceramics (e.max CAD MO1/C14), and zirconia (Katana KT 10) and then ground or polished. Rounded rod specimens were fabricated from heat-pressed lithium disilicate glass ceramic (e.max press LT A3) and then glazed or polished. A sliding wear testing apparatus was used for wear testing. Wear of glazed rods was greater than that of polished rods when they were abraded with ground zirconia, ground porcelain, polished porcelain, or polished lithium disilicate ceramics. For both glazed and polished rods, wear was greater when the rods were abraded with ground plates. The findings indicate that application of a polished surface rather than a glazed surface is recommended for single restorations made of heat-pressed lithium disilicate material. In addition, care must be taken when polishing opposing materials, especially those used in occlusal contact areas. (J Oral Sci 58, 117-123, 2016).