Effect of multi-purpose primers on the bond durability between tri-n-butylborane initiated resin and gold alloy

Hiraba, Haruto; Nogawa, Hiroshi; Koizumi, Hiroyasu; Kodaira, Akihisa; Akahane, Shunsuke

doi:10.1016/j.jpor.2018.09.002

Cited by 11 publications

(18 citation statements)

References 17 publications

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“…Adhesive functional monomers, e.g., carboxylic acids, phosphates, or organic sulfur compounds, are used for greater bonding to dental metals. Carboxylic acids and phosphates of acidic functional monomers act on the oxide film formed on non-noble metals, and therefore produce no effect on bonding to noble metals that do not easily form the oxide film [4][5][6][7]. Tanaka et al focused on the oxidation of copper in order to solve this problem, and reported that the effects of carboxylic acids included in acrylic resin were improved by oxidation treatment for a noble metal alloy [8,9].…”

Section: Ofmentioning

confidence: 99%

Influence of Oxidation of Copper on Shear Bond Strength to an Acrylic Resin Using an Organic Sulfur Compound

et al. 2020

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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 °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.

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Section: Ofmentioning

confidence: 99%

Influence of Oxidation of Copper on Shear Bond Strength to an Acrylic Resin Using an Organic Sulfur Compound

et al. 2020

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“…Therefore, it is believed that suitable primers for noble metal must be used to create a strong chemical bond with the alloy. Commercial primers for noble metals are generally contained functional monomers such as 6-(4-vinylbenzyl-n-propyl) amino-1,3,5triazine-2,4-dithione (VTD) [1][2][3][4][5][6][7] or 6-methacryloxyhexyl 2-thiouracil-5-carboxylate (MTU-6) [8][9][10][11][12] . On the other hand, commercial primers for base metal alloy include a carboxylic acid monomer or phosphate monomer, e.g.…”

Section: Introductionmentioning

confidence: 99%

Adhesive bonding of alumina air-abraded Ag-Pd-Cu-Au alloy with 10-methacryloyloxydecyl dihydrogen phosphate

et al. 2020

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The aim of this paper is to study changes in the Ag-Pd-Cu-Au alloy surfaces by alumina air-abrasion process and effect of those changes on the adhesive bonding characteristic. Surface roughness, surface composition and chemical state of the alumina airabraded alloys were analyzed by a confocal laser scanning microscope, an energy dispersive X-ray spectroscopy and an X-ray photoelectron spectroscopy. The results showed that the alumina air-abrasion changed the alloy surface by mechanical roughening, alumina remain and copper oxidation. Effect of the changes in the alloy surface on the adhesive bonding characteristic was examined by using a methyl methacrylate/tri-n-butylborane derivative (MMA/TBB) resin cement with the 10-methacryloyloxydecyl dihydrogen phosphate (MDP) contained primer. The shear bond strength test results indicated that the surface oxidation by the abrasion is the main contributor that improved the adhesive bonding rather than other effects such as mechanical roughening or alumina remain.

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“…Based on the findings, organic sulfur compounds with methacryloyl groups have been synthesized. Among them, MTU-6 and MDDT have effectively enhanced the bonding performance of noble metals and alloys [4,[7][8][9][10][11][12].…”

Section: Discussionmentioning

confidence: 99%

“…A thiophosphate, 10-methacryloyloxydecyl dihydrogen thiophosphate (M10PS, MDTP) (Kojima et al, J J Dent Mater 6 Spec 10, 112, 1987) [2]; a disulfide, methacryloyloxydecyl 6,8-dithiooctanoate (MDDT) [3,4]; and a thiouracil, 6-methacryloyloxyhexyl 2-thiouracil-5-carboxylate (MTU-6) [5], have been reported as functional methacrylates. These monomers are dissolved in solvents and are being used as single liquid priming agents capable of bonding dental noble metal alloys [6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a methacrylate monomer with a thiohydantoin structure

Matsumura

Kojima²,

Mio

et al. 2020

J Oral Sci

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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. Keywords; adhesive, bonding, noble metal alloy, thiol, thione Solubility of monomersThe solubility of the synthesized monomer in the current project and VBATDT [1] was evaluated. The solvents used were acetone, isopropanol, and MMA. Monomers were separately added to the three solvents and magnetically stirred for 30 min. The resultant transparent solution was judged as a solution within the soluble wt% concentration of each monomer.

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Effect of multi-purpose primers on the bond durability between tri-n-butylborane initiated resin and gold alloy

Cited by 11 publications

References 17 publications

Influence of Oxidation of Copper on Shear Bond Strength to an Acrylic Resin Using an Organic Sulfur Compound

Influence of Oxidation of Copper on Shear Bond Strength to an Acrylic Resin Using an Organic Sulfur Compound

Adhesive bonding of alumina air-abraded Ag-Pd-Cu-Au alloy with 10-methacryloyloxydecyl dihydrogen phosphate

Synthesis and characterization of a methacrylate monomer with a thiohydantoin structure

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