Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide - a tailor-made photoinitiator for dental adhesives

Because of the poor solubility of the commercially available bisacylphosphine oxides in dental acidic aqueous primer formulations, bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide (WBAPO) was synthesized starting from 3-(chloromethyl)-2,4,6-trimethylbenzoic acid by the dichlorophosphine route. The substituent was introduced by etherification with 2-(allyloxy)ethanol. In the second step, 3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoic acid was chlorinated. The formed acid chloride showed an unexpected low thermal stability. Its thermal rearrangement at 180 ° C resulted in a fast formation of 3-(chloromethyl)-2,4,6-trimethylbenzoic acid 2-(allyloxy)ethyl ester. In the third step, the acid chloride was reacted with phenylphosphine dilithium with the formation of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine, which was oxidized to WBAPO. The structure of WBAPO was confirmed by ¹H NMR, ¹³C NMR, ³¹P NMR, and IR spectroscopy, as well as elemental analysis. WBAPO, a yellow liquid, possesses improved solubility in polar solvents and shows UV-vis absorption, and a high photoreactivity comparable with the commercially available bisacylphosphine oxides. A sufficient storage stability was found in dental acidic aqueous primer formulations.

Microtensile vs Microshear Bond Strength of All-in-One Adhesives to Unground Enamel

Purpose To determine the bond strength to unground enamel of all in one adhesives in comparison with an etch and rinse system and to compare the reliability of microtensile and microshear methods in providing such measurements Materials and Methods The bonding procedure was performed on enamel of 64 extracted molars The tested all in one adhesives were Bond Force (Tokuyama), AdheSE One (Ivoclar Vivadent) and Xeno V (Dentsply) Prime&Bond NT (Dentsply) served as control Microtensile specimens were obtained from 4 teeth per group Twelve teeth per group were used for microshear testing Microtensile specimens that failed prior to testing were included in statistical calculations, they were assigned the lowest value measured in the respective group Failure modes were observed under light microscope and classified (cohesive within substrates, adhesive mixed) Statistically significant differences in bond strength were assessed among the adhesives within each testing method and between microshear and microtensile data for each adhesive Failure mode distributions were compared using the chi square test Results All in-one adhesives had similar microshear and microtensile bond strengths In both testing methods, the etch and rinse system achieved the strongest bond For all adhesives significantly higher bond strengths were measured with the microshear test In microtensile testing specimens bonded with the etch and rinse adhesive exhibited a significantly different distribution of failure modes The coefficients of variation were extremely high for microtensile bond strength data, particularly of all in one adhesives Conclusion The adhesive potential to intact enamel of recently introduced all in-one adhesives was inferior to that of an etch and rinse system When testing bond strength to enamel of all in one adhesives, microshear testing may be a more accurate method than microtensile

Effect of water contamination on the shear bond strength of five orthodontic adhesives

Objectives: To evaluate the shear bond strength and site of failure of brackets bonded to dry and wet enamel. Study design: 50 teeth were divided into ten groups of 5 teeth each (10 surfaces). In half the groups enamel was kept dry before bonding, and in the other half distilled water was applied to wet the surface after etching. The following groups were established: 1)Acid/Transbond-XT (dry/wet) XT; 2) Transbond Plus Self Etching Primer (TSEP)/Transbond-XT paste (dry/wet); 3) Concise (dry), Transbond MIP/Concise (wet), 4) FujiOrtho-LC (dry/wet); 5) SmartBond (dry/wet). Brackets were bonded to both buccal and lingual surfaces. Specimens were stored in distilled water (24 hours at 37ºC) and thermocycled. Brackets were debonded using a Universal testing machine (cross-head speed 1 mm/min). Failure sites were classified using a stereomicroscope. Results: No significant differences in bond strength were detected between the adhesives under wet and dry conditions except for Smart- Bond, whose bond strength was significantly lower under dry conditions. For all the adhesives most bond failures were of mixed site location except for Smartbond, which failed at the adhesive-bracket interface. Conclusions: Under wet conditions the bonding capacity of the adhesives tested was similar than under dry conditions, with the exception of SmartBond which improved under wet conditions

Polymerization kinetics and reactivity of alternative initiators systems for use in light-activated dental resins

Objectives. The purpose of this study was to evaluate the reactivity and polymerization kinetics behavior of a model dental adhesive resin with water-soluble initiator systems. Methods. A monomer blend based on Bis-GMA, TEGDMA and HEMA was used as a model dental adhesive resin, which was polymerized using a thioxanthone type (QTX) as a photoinitiator. Binary and ternary photoinitiator systems were formulated using 1 mol% of each initiator. The co-initiators used in this study were ethyl 4-dimethylaminobenzoate (EDAB), diphenyliodonium hexafluorophosphate (DPIHFP), 1,3-diethyl-2-thiobarbituric acid (BARB), p-toluenesulfinic acid and sodium salt hydrate (SULF). Absorption spectra of the initiators were measured using a UV-Vis spectrophotometer, and the photon absorption energy (PAE) was calculated. The binary system camphorquinone (CQ)/amine was used as a reference group (control). Twelve groups were tested in triplicate. Fourier-transform infrared spectroscopy (FTIR) was used to investigate the polymerization reaction during the photoactivation period to obtain the degree of conversion (DC) and maximum polymerization rate (R-p(max)) profile of the model resin. Results. In the analyzed absorption profiles, the absorption spectrum of QTX is almost entirely localized in the UV region, whereas that of CQ is in the visible range. With respect to binary systems, CQ + EDAB exhibited higher DC and R-p(max) values. In formulations that contained ternary initiator systems, the group CQ + QTX + EDAB was the only one of the investigated experimental groups that exhibited an R-p(max) value greater than that of CQ + EDAB. The groups QTX + EDAB + DPIHFP and QTX + DPIHFP + SULF exhibited values similar to those of CQ + EDAB with respect to the final DC; however, they also exhibited lower reactivity. Significance. Water-soluble initiator systems should be considered as alternatives to the widely used CQ/amine system in dentin adhesive formulations. (C) 2012 Academy of Dental Materials. Published by Elsevier Ltd. All rights reserved.

Osteo-odonto-keratoprosthesis (OOKP) and the testing of three different adhesives for bonding bovine teeth with optical poly-(methyl methacrylate) (PMMA) cylinder.

AIM Preparation of the lamina during osteo-odonto-keratoprosthesis (OOKP) design is complex, and its longevity and watertightness important. To date, only acrylic bone cements have been used for bonding the optical cylinder to the tooth dentine. Our aim was to evaluate different dental adhesives for OOKP preparation. METHODS Specimens of bovine teeth were produced by preparing 1.5-mm thick dentine slices with holes having a diameter of 3.5 mm. Each group (n=10 per group) was luted with either classic poly-(methyl methacrylate) (PMMA) bone cement, universal resin cement or glass ionomer cement. All specimens underwent force measurement using a uniaxial traction machine. RESULTS The highest mean force required to break the bond was measured for PMMA bone cement (128.2 N) followed by universal resin cement (127.9 N), with no statistically significant difference. Glass ionomer cement showed significantly lower force resistance (78.1 N). CONCLUSIONS Excellent bonding strength combined with easy application was found for universal resin cement, and thus, it is a potential alternative to acrylic bone cement in OOKP preparation.

Antimicrobial and bond strength properties of a dental adhesive containing zinc oxide nanoparticles

Aim: To assess the effect of adding zinc oxide nanoparticles to dental adhesives on their anti-microbial and bond strength properties. Methods: 45 human premolars were cut at the cement enamel junction (CEJ) and the crowns were sliced into buccal and lingual halves. The specimens were classified into three groups, etched with 37% phosphoric acid for 15 s and rinsed for 30 s. Single Bond, Single Bond+5% zinc oxide and Single Bond+10% zinc oxide were used in the first, second and third groups. A cylinder of Z250 composite was bonded and cured for 40 s. For anti-bacterial testing, 10 samples of each group were assessed by direct contact test; 10 μL of bacterial suspension was transferred into tubes containing adhesives and incubated for one hour; 300 μL of brain heart infusion (BHI) broth was added to each tube and after 12 h, 50 μL of bacteria and broth were spread on blood agar plates and incubated for 24 h. Results: The colony count decreased significantly in the second and third groups compared to the first. Conclusions: Incorporation of zinc oxide nanoparticles into dental adhesives increases their anti-microbial properties without affecting their bond strength.

Amalgamas adhesivas. Un estudio sobre 128 dientes tratados con esta técnica

El propósito de este trabajo es el de presentar la amalgama adherida como un muy válido tratamiento conservador a tener en cuenta a la hora de ofertar soluciones a nuestros pacientes. Es un tratamiento conservador mucho más económico que otros muchos y ante pacientes con no demasiados recursos económicos nos puede ser de gran ayuda. Asimismo, es quizá el tipo de tratamiento más recomendable para una parte de los llamados 'pacientes especiales'. Nos referimos a los pacientes que presentan deficiencias físicas y psíquicas y que por su particularidad nos limitan casi siempre las opciones terapéuticas clásicas. Se presenta un estudio 'in vivo' sobre 128 piezas dentarias, 49 de las cuales habían necesitado tratamiento endodóncico previo y que posteriormente fueron restauradas con amalgama adherida.

Restauraciones fototermocuradas en dentición temporal

La restauración de lesiones proximales en molares deciduos es problemática, no existe un material ideal para reparar este tipo de lesiones. Por otra parte en dientes temporales debilitados tras una pulpotomía, la restauración de elección es la corona metálica preformada. Con la introducción de los nuevos sistemas de adhesión una posible alternativa en el tratamiento de estas situaciones en dentición temporal, serian las incrustaciones para molares y las coronas para incisivos confeccionadas con material composite fototennocurado. En este arüculo se analiza la técnica de preparación de estas restauraciones, sus indicaciones, ventajas e inconvenientes.

Influencia de diferentes sistemas de profilaxis en la adhesión de un sellador de fisuras al esmalte

Introducción: La adhesión de las resinas dentales al esmalte no depende solamente del grabado ácido del esmalte. Otros factores, como el pulido de la superficie del esmalte pueden influir en la fuerza de adhesión de las resinas. El objetivo de este estudio es evaluar la adhesión de un sellador de fisuras fotopolimerizable tras la utilización previa de distintos métodos de profilaxis y dos diferentes tiempos de grabado. Material y método: Ochenta terceros molares extraídos quirúrgicamente se seccionaron en dos mitades (vestibular y lingual). Los dientes se dividieron en ocho grupos de 20 muestras cada uno, de acuerdo con los métodos de profilaxis: polvo de piedra pómez, pasta fluorada, espray de bicarbonato y control (sin profilaxis); y dos tiempos de grabado: 15 y 30 segundos. Se midió la fuerza de adhesión mediante una prueba de tracción en una máquina de ensayos universal INSTRON. Resultados y conclusión: Se utilizó el test estadístico ANOVA, detectándose diferencias significativas en la resistencia a la tracción; el posterior test de Dunnett encontró estas diferencias entre los grupos control y de profilaxis con piedra pómez para 15 y 30 segundos de grabado respecto de los grupos tratados con pasta fluorada y espray de bicarbonato, para los mismos tiempos de grabado (p<0,05), siendo esta diferencia mayor en el grupo de espray con bicarbonato.

Bacterial adhesion efficiency on implant abutments: a comparative study

The attachment of Escherichia coli ATCC 25922 and Staphylococcus aureus ATCC 28213 onto six different materials used to manufacture dental implant abutments was quantitatively determined after 2 and 24 h of contact between the materials and the bacterial cultures. The materials were topographically characterized and their wettability determined, with both parameters subsequently related to bacterial adhesion. Atomic force microscopy, interferometry, and contact angle measurement were used to characterize the materials" surfaces. The results showed that neither roughness nor nano-roughness greatly influenced bacterial attachment whereas wettability strongly correlated with adhesion. After 2 h the degree of E. coli attachment markedly differed depending on the material whereas similar differences were not observed for S. aureus, which yielded consistently higher counts of adhered cells. Nevertheless, after 24 h the adhesion of the two species to the different test materials no longer significantly differed, although on all surfaces the numbers of finally adhered E. coli were higher than those of S. aureus

Effect of adhesive system type and tooth region on the bond strength to dentin

Purpose: This study evaluated the bond strength of two etch-and-rinse adhesive systems (two- and three-step) and a self-etching system to Coronal and root canal dentin.Materials and Methods: The root canals of 30 human incisors and canines were instrumented and prepared with burs. The posts used for luting were duplicated with dual resin cement (Duo-link) inside Aestheti Plus #2 molds. Thus, three groups were formed (n = 10) according to the adhesive system employed: All-Bond 2 (TE3) + resin cement post (rcp) + Duo-link (DI); One-Step Plus (TE2) + rcp + DI; Tyrian/One-Step Plus (SE) + rcp + DI. Afterwards, 8 transverse sections (1.5 mm) were cut from 4 mm above the CEJ up to 4 mm short of the root canal apex, comprising coronal and root canal dentin. The sections were submitted to push-out testing in a universal testing machine EMIC (1 mm/min). Bond strength data were analyzed with two-way repeated measures ANOVA and Tukey's test (p < 0.05).Results: The relationship between the adhesives was not the same in the different regions (p < 0.05). Comparison of the means achieved with the adhesives in each region (Tukey; p < 0.05) revealed that TE3 (mean standard deviation: 5.22 +/- 1.70) was higher than TE2 (2.60 +/- 1.74) and SE (1.68 +/- 1.85).Conclusion: Under the experimental conditions, better bonding to dentin was achieved using the three-step etch-and-rinse system, especially in the coronal region. Therefore, the traditional etch-and-rinse three-step adhesive system seems to be the best choice for teeth needing adhesive endodontic restorations.

Use of one-bottle adhesive as an intermediate bonding layer to reduce sealant microleakage on saliva-contaminated enamel

Purpose: To evaluate the influence of three different adhesives, each used as an intermediary layer, on microleakage of sealants applied under condition of salivary contamination. Materials and Methods: Six different experimental conditions were compared, 3 with adhesives and 3 without. After prophylaxis and acid etching of enamel, salivary contamination was placed for 10 s. In Group SC the sealant was applied after saliva without bonding agent and then light-cured. In Group SCA, after saliva, the surface was air dried, and then the sealant was applied and cured. In Groups ScB, SB and PB, a bonding agent (Scotchbond Dual Cure/3M, Single Bond/3M and Prime & Bond 2.1/Dentsply, respectively) was applied after the saliva and prior to the sealant application and curing. After storage in distilled water at 37°C for 24 hrs, the teeth were submitted to 500 thermal cycles (5°C and 55°C), and silver nitrate was used as a leakage tracer. Leakage data were collected on cross sections as percentage of total enamel-sealant interface length. Representative samples were evaluated under SEM. Results: Sealants placed on contaminated enamel with no bonding agent showed extensive microleakage (94.27% in SC; 42.65% in SCA). The SEM revealed gaps as wide as 20 μm in areas where silver nitrate leakage could be visualized. In contrast, all bonding agent groups showed leakage less than 6.9%. Placement of sealant with a dentin-bonding agent on contaminated enamel significantly reduced microleakage (P< 0.0001). The use of a bonding agent as an intermediary layer between enamel and sealant significantly reduced saliva's effect on sealant microleakage.

Effect of dentinal surface preparation on bond strength of self-etching adhesive systems

The aim of this study was to evaluate the effects of dentin surface treatments on the tensile bond strength (TBS) of the self-etching primer Clearfil SE Bond (CSE) and the one-step self-etching One-Up Bond F (OUB). The exposed flat dentin surfaces of twenty-four sound third molars were prepared with diamond bur at high-speed, carbide bur at low-speed or wet ground with #600 grit SiC paper. The adhesive systems were applied to the dentin surfaces and light-cured according to the manufacturers' instructions. A 6-mm high composite crown was incrementally built-up and each increment was light-cured for 40 seconds. After being stored in water (37°C/24 h), the samples were serially sectioned parallel to the long axis, forming beams (n = 20) with a cross-sectional area of approximately 0.8 mm 2. The specimens were tested in a Universal Testing Machine at 0.5 mm/min. The cross-sectional area was measured and the results (MPa) were analyzed by two-way ANOVA and Tukey Test (p < 0.05). Overall, the groups treated with CSE exhibited the highest TBS for all surface treatments. Dentin surfaces prepared with carbide bur at low speed reduced TBS in the CSE group; however, OUB was not affected by surface treatments. The effect of surface abrasive methods on TBS was material-dependent.

Tensile bond strength: Evaluation of four current adhesive systems in abraded enamel and deep dentin

This study aimed to evaluate the tensile bond strength of adhesive systems in abraded enamel and deep dentin of the occlusal surface of forty human molar teeth. Enamel surfaces as well as the rest of the teeth were coated with epoxy resin and regularized and polished with silicon carbide sandpapers. The 40 teeth were randomized into eight groups of five teeth per group. Four groups were assigned to have deep dentin as the dental substrate and the other four had abraded enamel as the substrate for the adhesives to be tested. The adhesives being tested were the total etching Single Bond: SB, the self-etching Clearfil SE bond: CSEB, self-etching One Up Bond F: OUBF and the self-etching Self-Etch Bond: SEB adhesives. The samples (teeth) were restored with composite resin and subjected to a traction assay. The results were statistically analyzed using the ANOVA and TUKEY tests. The total etching SB adhesive system had the greatest bonding strength of all the adhesives tested, on both dental substrates (20.1 MegaPascals (MPa) on abraded enamel and 19.4 MPa on deep dentin). Of the self-etching dental adhesives tested, CSEB had the greatest bonding strength on both substrates (14.6 MPa on abraded enamel and 15.4 MPa on deep dentin). Both OUBF (11.0 MPa for enamel, 13.1 MPa for dentin) and SEB (10.2 MPa for enamel, 12.6 MPa for dentin) showed comparable bonding strengths without any significant differences for either substrate Thus, the total etching SB adhesive system had better bonding strength than the other self-etching adhesives used, regardless of the dental substrate to which the adhesives had been bonded.