Bisphenol A Glycerolate Dimethacrylate Research Articles

Validation of a human saliva model for the determination of leachable monomers and other chemicals from dental materials

This study aimed to prove the validity of a mixture of chemicals, including salts, small organic molecules, mucin, and α-amylase, as saliva surrogate (“artificial saliva”) for assessing leakage of methacrylate monomers and other constituents from dental materials. To achieve this, we developed and validated a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the quantification of 2-hydroxyethyl methacrylate (HEMA), triethylene glycol dimethacrylate (TEGDMA), diurethane dimethacrylate (UDMA), bisphenol A glycerolate dimethacrylate (BisGMA), diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), bisphenol A (BPA), and five homologues of ethoxylated bisphenol A dimethacrylate (BisEMA EO2–6) in unstimulated and artificial saliva, and compared their concentrations in the two saliva media following either spiking with a mixture of the compounds or incubation of test specimens of printed biomaterials. Test specimens were immersed in unstimulated/artificial saliva, incubated at 37 °C for 24 h, and saliva aliquots were extracted with methanol and subsequently analyzed by LC-MS/MS. The method was validated with regard to matrix effects, linearity, selectivity, lower limits of quantification (LLOQ), precision, bias and combined measurement uncertainty (u′). The performance characteristics of the method were comparable for unstimulated and artificial saliva samples. The combined u’ for individual chemicals at a concentration of 10 × LLOQ were within the range of 5.3–14 % for unstimulated saliva and 6.9–16 % for artificial saliva, except for the BisEMA homologues. Combined u’ for the latter were 27–74 % in unstimulated saliva, and 27–79 % in artificial saliva. There was no detectable release of BPA from the test specimens, and the TPO concentrations were mainly below the LLOQ. TEGDMA and UDMA were detected in the highest quantities, and at comparable concentrations in the unstimulated and artificial saliva. For all BisEMA homologues, the release was higher in unstimulated saliva than in artificial saliva. The study showed that the artificial saliva model can be a suitable replacement for native saliva, but might underestimate leakage of more lipophilic methacrylates.

Chemical Modification of Dental Dimethacrylate Copolymer with Tetramethylxylylene Diisocyanate-Based Quaternary Ammonium Urethane-Dimethacrylates-Physicochemical, Mechanical, and Antibacterial Properties.

In this study, two novel quaternary ammonium urethane-dimethacrylates (QAUDMAs) were designed for potential use as comonomers in antibacterial dental composite restorative materials. QAUDMAs were synthesized via the reaction of 1,3-bis(1-isocyanato-1-methylethyl)benzene with 2-(methacryloyloxy)ethyl-2-decylhydroxyethylmethylammonium bromide (QA10+TMXDI) and 2-(methacryloyloxy)ethyl-2-dodecylhydroxyethylmethylammonium bromide (QA12+TMXDI). Their compositions with common dental dimethacrylates comprising QAUDMA 20 wt.%, urethane-dimethacrylate monomer (UDMA) 20 wt.%, bisphenol A glycerolate dimethacrylate (Bis-GMA) 40 wt.%, and triethylene glycol dimethacrylate (TEGDMA) 20 wt.%, were photocured. The achieved copolymers were characterized for their physicochemical and mechanical properties, including their degree of conversion (DC), glass transition temperature (Tg), polymerization shrinkage (S), water contact angle (WCA), flexural modulus (E), flexural strength (FS), hardness (HB), water sorption (WS), and water leachability (WL). The antibacterial activity of the copolymers was characterized by the minimum bactericidal concentration (MBC) and minimum inhibitory concentration (MIC) against Staphylococcus aureus and Escherichia coli. The achieved results were compared to the properties of a typical dental copolymer comprising UDMA 40 wt.%, Bis-GMA 40 wt.%, and TEGDMA 20 wt.%. The introduction of QAUDMAs did not deteriorate physicochemical and mechanical properties. The WS and WL increased; however, they were still satisfactory. The copolymer comprising QA10+TMXDI showed a higher antibacterial effect than that comprising QA12+TMXDI and that of the reference copolymer.

A resin adhesive with balanced antibacterial and mineralization properties for improved dental restoration

ObjectiveAiming to develop an adhesive formulation that achieves a harmonious equilibrium between antibacterial efficacy and mineralization potential, 2-methacryloyloxy ethyl phosphorylcholine (MPC), N,N-dodecylvinylimidazole (DCV), and Sr-doped hydroxyapatite (Sr/HAp) nanorods were incorporated as functional constituents into the adhesive matrix, employing carefully optimized proportions. MethodsThe adhesive formulation comprised a blend of bisphenol A glycerolate dimethacrylate (Bis-GMA), 2-hydroxyethyl methacrylate (HEMA), and 1,6-hexanediol dimethacrylate (HDDMA) monomers. The effects of MPC and DCV additions, ranging from 1% to 4% (wt%), on various aspects such as adhesive curing kinetics, bonding strength, water contact angle, mechanical properties, and antibacterial activities against Streptococcus mutans (S. mutans) and Human Saliva Bacterial Flora (HSBF), was investigated both individually and in combination. Following the determination of the optimized MPC/DCV ratio, the effect of Sr/HAp on the mineralization potential of the adhesives was evaluated by soaking the samples in 1.5 times simulated body fluid (SBF) at 37 °C for 3 days followed by examination using scanning electron microscopy (SEM). Additionally, biocompatibility assay was conducted using L929 fibroblasts. ResultsThe introduction of MPC and DCV did not interfere the CC conversion degree of the resin blends in all the preparations. Notably, the incorporation of 3 wt% MPC demonstrated a significantly enhancement in the hydrophilicity of the adhesive, resulting in reduced bacterial adsorption. The addition of 3 wt% DCV exhibited potent antibacterial properties against attached bacteria. Furthermore, the introduction of 8 wt% Sr/HAp displayed a positive effect on mineral deposition on the adhesive surface. Importantly, all adhesive formulations demonstrated negligible cytotoxicity. Although a decrease in bonding strength was observed upon the introduction of MPC/DCV, the supplementation of Sr/HAp exhibited a reinforcing effect, effectively compensating for the decline. This beneficial outcome can be attributed to a substantial improvement in the flexural strength/modulus of the composite adhesive. SignificanceThe adhesive, simultaneously having ability in inhibiting bacteria adsorption, killing bacteria and promoted mineralization, holds great potential in achieving strong bonding strength for dental restoration applications to minimize repair failure.

Novel mechanically strong and antibacterial dimethacrylate copolymers based on quaternary ammonium urethane-dimethacrylate analogues.

This study assumed that the quaternary ammonium urethane-dimethacrylate derivative (QAUDMA-m, where m was 8, 10, 12, 14, 16, 18, and corresponded to the number of carbon atoms in the N-alkyl substituent) can be used to achieve copolymers with high mechanical performance and antibacterial activity. Photocured copolymers of bisphenol A glycerolate dimethacrylate (Bis-GMA) 40wt%, QAUDMA-m 40wt%, and triethylene glycol dimethacrylate (TEGDMA) 20wt% (BG:QAm:TEG) were characterized by the degree of conversion (DC), flexural strength (FS), flexural modulus (E), hardness (HB), and antibacterial properties (the number of bacteria colonies adhered to copolymer surfaces and inhibition zone diameter (IZD)) against Staphylococcus aureus and Escherichia coli. Reference copolymers of Bis-GMA, urethane-dimethacrylate monomer (UDMA), and TEGDMA (BG:TEG and BG:UD:TEG) were also characterized. The DC of BG:QAm:TEGs ranged from 0.59 to 0.68, HB from 83.84 to 153.91MPa, FS from 50.81 to 74.47MPa, and E from 1986.74 to 3716.68MPa. The number of S. aureus and E. coli bacteria adhered to BG:QAm:TEG surfaces was from 0 (no bacteria observed) to 6.47 and 4.99log(CFU/mL), respectively. IZD was from 10 and 5mm (no inhibition zone) to 23 and 21mm, respectively. Three copolymers: BG:QA8:TEG, BG:QA10:TEG, and BG:QA12:TEG had similar or better mechanical properties than the reference copolymers, but unlike them, they showed high antibacterial activity against both bacteria strains. The obtained copolymers can offer a good, mechanically efficient, bioactive alternative to BG:TEG and BG:UD:TEG copolymers. The use of such materials can help to make progress in dental health care.

Fabric phase sorptive extraction of monomers released from dental resins in alcoholic beverages prior to their HPLC-UV determination

Fabric Phase Sorptive Extraction (FPSE) combined with High Pressure Liquid Chromatography coupled to UV (HPLC-UV) was applied for the simultaneous determination of organic monomers bisphenol-A (BPA), bisphenol A glycerolate dimethacrylate (Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), and urethane dimethacrylate (UDMA)]that can be released from dental resins [in alcoholic beverages. The FPSE procedure was optimized with regards to the critical parameters that affect the performance of the method: a) FPSE membrane type and size, b) sample loading volume c) elution solvent, d) volume of elution solvent, e) stirring rate during extraction and elution, f) extraction time, and g) desorption/elution time. The developed FPSE-HPLC-UV method was subsequently validated in terms of linearity, trueness, precision and selectivity, showing satisfactory results. The limits of detection (LOD) and limits of quantification (LOQ) were equal to 0.06 ng/μL and 0.2 ng/μL, respectively. Relative recoveries ranged between 92.0% and 99.2% in white wine samples, and between 85.4% and 95.0% in vodka samples for within-day assay (n = 5). For between-day assay (n = 3 × 4), recoveries ranged between 92.0% and 101.8% in white wine samples, and between 88.4% and 95.2% in vodka samples. The method was successfully implemented in the investigation of monomers released from alcoholic beverages incubated with dental resins for a period of 24 h and 7 days.

Physicochemical Properties of Novel Copolymers of Quaternary Ammonium UDMA Analogues, Bis-GMA, and TEGDMA.

This study aimed to elucidate the physicochemical properties of copolymers comprising 40 wt.% bisphenol A glycerolate dimethacrylate (Bis-GMA), 40 wt.% quaternary ammonium urethane-dimethacrylate analogues (QAUDMA-m, where m corresponds to the number of carbon atoms in the N-alkyl substituent), and 20 wt.% triethylene glycol dimethacrylate (TEGDMA) copolymers (BG:QAm:TEGs). The BG:QAm:TEG liquid monomer compositions and reference compositions (40 wt.% Bis-GMA, 40 wt.% urethane-dimethacrylate (UDMA), 20 wt.% TEGDMA (BG:UD:TEG) and 60 wt.% Bis-GMA, 40 wt.% TEGDMA (BG:TEG)) were characterized in terms of their refractive index (RI) and monomer glass transition temperature (Tgm) and then photocured. The resulting copolymers were characterized in terms of the polymer glass transition temperature (Tgp), experimental polymerization shrinkage (Se), water contact angle (WCA), water sorption (WS), and water solubility (SL). The prepared BG:QAm:TEG liquid monomer compositions had RI in the range 1.4997-1.5129, and Tgm in the range -52.22 to -42.12 °C. The BG:QAm:TEG copolymers had Tgp ranging from 42.21 to 50.81 °C, Se ranging from 5.08 to 6.40%, WCA ranging from 81.41 to 99.53°, WS ranging from 25.94 to 68.27 µg/mm3, and SL ranging from 5.15 to 5.58 µg/mm3. Almost all of the developed BG:QAm:TEGs fulfilled the requirements for dental materials (except BG:QA8:TEG and BG:QA10:TEG, whose WS values exceeded the 40 µg/mm3 limit).

Design of a polymerizable dithioaniline derivative with double functions of reducing volume shrinkage and initiating polymerization for LED photopolymerization

This work reports a photopolymerizable dithioaniline derivative (OMABS), having the double functions of reducing volume shrinkage and initiating polymerization under light emitting diode (LED) irradiation. Its photochemistry and photoinitiation properties were investigated by UV–vis absorption spectroscopy, electron paramagnetic resonance spectroscopy (EPR), real-time infrared spectroscopy (RTIR) and confocal micro-Raman spectroscopy. OMABS shows a weak absorption around 385 nm and 405 nm, but can generate arylthiyl radicals to effectively initiate the polymerization of bisphenol A glycerolate dimethacrylate (Bis-GMA)/triethylene glycol dimethacrylate (TEGDMA) system and itself under 385 and 405 nm LED irradiation, and the double bond conversion reaches up to 83.2 %. Significantly, OMABS can obviously reduce the volume shrinkage of Bis-GMA/TEGDMA system, and the volume shrinkage (4.89 %) of Bis-GMA/TEGDMA with OMABS system declines by almost half compared with that (8.10 %) without OMABS system due to the existence of dynamic reversible SS bond and intermolecular hydrogen bonding interaction. Moreover, OMABS has little influence on the gel yield, thermal stability and frictional resistance of the Bis-GMA/TEGDMA system.

Characterization of the Mechanical Properties, Water Sorption, and Solubility of Antibacterial Copolymers of Quaternary Ammonium Urethane-Dimethacrylates and Triethylene Glycol Dimethacrylate

The use of dental composites based on dimethacrylates that have quaternary ammonium groups is a promising solution in the field of antibacterial restorative materials. This study aimed to investigate the mechanical properties and behaviors in aqueous environments of a series of six copolymers (QA:TEG) comprising 60 wt.% quaternary ammonium urethane-dimethacrylate (QAUDMA) and 40 wt.% triethylene glycol dimethacrylate (TEGDMA); these copolymers are analogous to a common dental copolymer (BG:TEG), which comprises 60 wt.% bisphenol A glycerolate dimethacrylate (Bis-GMA) and 40 wt.% TEGDMA. Hardness (HB), flexural strength (FS), flexural modulus (E), water sorption (WS), and water solubility (SL) were assessed for this purpose. The pilot study of these copolymers showed that they have high antibacterial activity and good physicochemical properties. This paper revealed that QA:TEGs cannot replace BG:TEG due to their insufficient mechanical properties and poor behavior in water. However, the results can help to explain how QAUDMA-based materials work, and how their composition should be manipulated to produce the best performance. It was found that the longer the N-alkyl chain, the lower the HB, WS, and SL. The FS and E increased with the lengthening of the N-alkyl chain from eight to ten carbon atoms. Its further extension, to eighteen carbon atoms, caused a decrease in those parameters.

Synthesis and Characterization of Methacrylate-Functionalized Betulin Derivatives as Antibacterial Comonomer for Dental Restorative Resins.

Secondary caries is the primary cause of composite restoration failures, resulting from marginal leakage and bacterial accumulation in the oral environment. Antibacterial dental composites, especially antibacterial monomers, have emerged as a promising strategy to inhibit secondary caries, which is pivotal to prolonging the lifespan of dental restorations. In this work, monomethacrylate- and dimethacrylate-functionalized betulin derivatives (M1Bet and M2Bet) were synthesized via an esterification reaction and served as antibacterial comonomers to develop novel dental resin formulations, in which M1Bet and M2Bet were incorporated to partially or completely replace bisphenol A glycerolate dimethacrylate (Bis-GMA). The control resin was a mixture based on Bis-GMA and tri(ethyleneglycol) dimethacrylate (TEGDMA) with a weight ratio of 50:50 (5B5T). The effect of the resin compositions and the chemical structures of M1Bet and M2Bet on the rheology behavior, optical property, polymerization kinetics, mechanical performance, cell viability, and antibacterial activity of dental resins were systematically investigated. Among all materials, the 1M2Bet4B5T resin with 10 wt % substitution of Bis-GMA by M2Bet exhibited comparable viscosity, higher light transmittance, improved degree of conversion, and mechanical properties compared with 5B5T. After incubation for 24 h, this optimal resin also possessed the best antibacterial activity against Streptococcus mutans, which had a significantly lower bacterial concentration (1.53 × 109 CFU/mL) than 5B5T (9.03 × 109 CFU/mL). Introducing betulin-based comonomers into dental resins is a potential strategy to develop antibacterial dental materials without sacrificing physical-mechanical properties.

Hydrophobically Modified Isosorbide Dimethacrylates as a Bisphenol-A (BPA)-Free Dental Filling Material.

A series of bio-based hydrophobically modified isosorbide dimethacrylates, with para-, meta-, and ortho- benzoate aromatic spacers (ISBGBMA), are synthesized, characterized, and evaluated as potential dental restorative resins. The new monomers, isosorbide 2,5-bis(4-glyceryloxybenzoate) dimethacrylate (ISB4GBMA), isosorbide 2,5-bis(3-glyceryloxybenzoate) dimethacrylate (ISB3GBMA), and isosorbide 2,5-bis(2-glyceryloxybenzoate) dimethacrylate (ISB2GBMA), are mixed with triethylene glycol dimethacrylate (TEGDMA) and photopolymerized. The resulting polymers are evaluated for the degree of monomeric conversion, polymerization shrinkage, water sorption, glass transition temperature, and flexural strength. Isosorbide glycerolate dimethacrylate (ISDGMA) is synthesized, and Bisphenol A glycerolate dimethacrylate (BisGMA) is prepared, and both are evaluated as a reference. Poly(ISBGBMA/TEGDMA) series shows lower water sorption (39–44 µg/mm3) over Poly(ISDGMA/TEGDMA) (73 µg/mm3) but higher than Poly(BisGMA/TEGDMA) (26 µg/mm3). Flexural strength is higher for Poly(ISBGBMA/TEGDMA) series (37–45 MPa) over Poly(ISDGMA/TEGDMA) (10 MPa) and less than Poly(BisGMA/TEGDMA) (53 MPa) after immersion in phosphate-buffered saline (DPBS) for 24 h. Poly(ISB2GBMA/TEGDMA) has the highest glass transition temperature at 85 °C, and its monomeric mixture has the lowest viscosity at 0.62 Pa·s, among the (ISBGBMA/TEGDMA) polymers and monomer mixtures. Collectively, this data suggests that the ortho ISBGBMA monomer is a potential bio-based, BPA-free replacement for BisGMA, and could be the focus for future study.

Polymer infiltrated ceramic networks with biocompatible adhesive and 3D-printed highly porous scaffolds

Herein, for the first time is described the design of a novel porous zirconia scaffolds manufactured by using polymer-infiltrated ceramic network (PICN) and 3D-printing technologies. Cubic geometry of pieces was obtained by perpendicular layer-by-layer deposition of yttrium-stabilized tetragonal zirconia polycrystal (3Y-TZP) and Pluronic® hydrogel ceramic paste. The specimens were prepared by robocasting assembly with 50% infill and 50% of pores, as feed setup. Bisphenol A glycerolate dimethacrylate (Bis-GMA) and tri(ethylenglycol) dimethacrylate (TEGDMA) copolymer, a well-known biocompatible adhesive, which is widely used in dentistry field, was employed to reinforce the pores of the 3D-printed ceramic structure. The success of the acrylate polymer infiltration above the scaffold surface and among the 3Y-TZP filaments was achieved through previous ceramic functionalization with 3-(trimethoxysilyl)propyl methacrylate (γ-MPS). The well infiltration of the material on pores was evaluated by gravimetry, obtaining a value of 87.5 ± 6.6% of pores covered by the adhesive. Such successful infiltration of methacrylate copolymer had also a positive effect on the mechanical properties of the scaffold material, being the PICN sample that one with the highest elongation resistance. The new system showed reduced bacteria proliferation, over 24 h of incubation with Gram-negative Escherichia coli and Gram-positive Streptococcus salivarius bacteria lines, when compared to the control.

Validation of a Simple HPLC-UV Method for the Determination of Monomers Released from Dental Resin Composites in Artificial Saliva.

Bisphenol-A (BPA), bisphenol A glycerolate dimethacrylate (Bis-GMA), triethylene glycol dimethacrylate (TEGDMA), and urethane dimethacrylate (UDMA) are organic monomers that can be released from dental composites into the oral cavity. Over specific concentrations, they can act as endocrine disruptors or cause toxic effects. The purpose of this work is to develop and validate an analytical method to determine BPA, Bis-GMA, TEGDMA, and UDMA monomers released from synthetic dental resins in artificial saliva. The method was validated before its application to new hybrid ceramic materials used in computer-aided design and computer-aided manufacturing (CAD/CAM) restorations to determine the release of monomers in various time intervals (e.g., 24 h, and 7, 14, 30, and 60 days), both in methanolic solutions, as well as in artificial saliva. Chromatographic analysis was performed isocratically on a Perfect Sil Target ODS-3 analytical column (250 mm × 4.6 mm, 5 µm) with CH3CN/H2O, 58/42% v/v as mobile phase within 23 min. The developed method was validated in terms of selectivity, linearity, accuracy, and precision.

Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials.

In this study, novel urethane-dimethacrylate monomers were synthesized from 1,3-bis(1-isocyanato-1-methylethyl)benzene (MEBDI) and oligoethylene glycols monomethacrylates, containing one to three oxyethylene groups. They can potentially be utilized as matrices in dental restorative materials. The obtained monomers were used to prepare four new formulations. Two of them were solely composed of the MEBDI-based monomers. In a second pair, a monomer based on triethylene glycol monomethacrylate, used in 20 wt.%, was replaced with triethylene glycol dimethacrylate (TEGDMA), a reactive diluent typically used in dental materials. For comparison purposes, two formulations, using typical dental dimethacrylates (bisphenol A glycerolate dimethacrylate (Bis-GMA), urethane-dimethacrylate (UDMA) and TEGDMA) were prepared. The monomers and mixtures were tested for the viscosity and density. The homopolymers and copolymers, obtained via photopolymerization, were tested for the degree of conversion, polymerization shrinkage, water sorption and solubility, hardness, flexural strength and modulus. The newly developed formulations achieved promising physico-chemical and mechanical characteristics so as to be suitable for applications as dental composite matrices. A combination of the MEBDI-based urethane-dimethacrylates with TEGDMA resulted in copolymers with a high degree of conversion, low polymerization shrinkage, low water sorption and water solubility, and good mechanical properties. These parameters showed an improvement in relation to currently used dental formulations.

The synergistic effects of SrF2 nanoparticles, YSZ nanoparticles, and poly-ε-l-lysin on physicomechanical, ion release, and antibacterial-cellular behavior of the flowable dental composites

Resin-based pit-and-fissure sealants (flowable resin composites) were formulated using bisphenol-A-glycerolatedimethacrylate (Bis-GMA)-triethylene glycol dimethacrylate-(TEGDMA)-diurethanedimethacrylate (UDMA) mixed monomers and multiple fillers, including synthetic strontium fluoride (SrF2) nanoparticles as a fluoride-releasing and antibacterial agent, yttria-stabilized zirconia (YSZ) nanoparticles as an auxiliary filler, and poly-ε-l-lysin (ε-PL) as an auxiliary antibacterial agent. Based on the physical, mechanical and initial antibacterial properties, the formulated nano-sealant containing 5wt% SrF2, 5wt% YSZ and 0.5wt% ε-PL was selected as the optimal specimen and examined for ion release and cytotoxicity. The results showed an average release rate of 0.87μg·cm-2·day-1 in the aqueous medium (pH6.9) and 1.58μg·cm-2·day-1 in acidic medium (pH4.0). The maximum cytotoxicity of 20% toward human bone marrow mesenchymal stem cells (hMSCs) was observed according to the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) cytotoxicity assay and acridine orange staining test. A synergy between SrF2 nanoparticles and ε-PL exhibited a better antibacterial activity in terms of colony reduction compared to the other samples. However, the inclusion of SrF2 and ε-PL caused mechanically weakening of the sealants that was partly compensated by incorporation of YSZ nanoparticles (up to 10wt%).

Evaluation of Monomer Leaching from a Resin Cement Through Dentin.

The aim of the study was to evaluate the elution of Triethylene glycol dimethacrylate (TEGDMA), Urethane dimethacrylate (UDMA), Bisphenol A glycerolate dimethacrylate (BisGMA), and Bisphenol A (BPA), from a dual-cured resin cement through human dentin, under constant positive pulpal pressure. Ten human dentin disks were adjusted into a custom made testing device and transparent glass slabs were luted with Variolink II cement, under a steady pressure. The device was filled with Ringer's solution and a pressure of 14.1 cm H₂O was applied. Eluates were retrieved from each one of the ten specimens at 9 time interval. All the samples were analyzed by High Performance Liquid Chromatography (HPLC). TEGDMA was detected from the second and UDMA was detected from the fourth time interval and then. The highest average concentration of TEGDMA and UDMA was detected in the 3 day time interval. Time had a significant effect on their elution. BPA and BisGMA were not detected in any sample of any time interval. The clinical relevance of the present study is that the concentration of the eluted monomers, under the conditions that were chosen, did not reach toxic levels for the pulp.

Studies on the Curing Efficiency and Mechanical Properties of Bis-GMA and TEGDMA Nanocomposites Containing Silver Nanoparticles.

Bioactive dimethacrylate composites filled with silver nanoparticles (AgNP) might be used in medical applications, such as dental restorations and bone cements. The composition of bisphenol A glycerolate dimethacrylate (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) mixed in a 60/40 wt% ratio was filled from 25 to 5000 ppm of AgNP. An exponential increase in resin viscosity was observed with an increase in AgNP concentration. Curing was performed by way of photopolymerization, room temperature polymerization, and thermal polymerization. The results showed that the polymerization mode determines the degree of conversion (DC), which governs the ultimate mechanical properties of nanocomposites. Thermal polymerization resulted in a higher DC than photo- and room temperature polymerizations. The DC always decreased as AgNP content increased. Flexural strength, flexural modulus, hardness, and impact strength initially increased, as AgNP concentration increased, and then decreased at higher AgNP loadings. This turning point usually occurred when the DC dropped below 65% and moved toward higher AgNP concentrations, according to the following order of polymerization methods: photopolymerization < room temperature polymerization < thermal polymerization. Water sorption (WS) was also determined. Nanocomposites revealed an average decrease of 16% in WS with respect to the neat polymer. AgNP concentration did not significantly affect WS.

Effect of trifluoroethyl methacrylate comonomer on physical properties of Bis-GMA based dental composites.

The purpose of this study was to investigate the effect of substituting triethyleneglycol dimethacrylate (TEGDMA) with 2,2,2-trifluoroethyl methacrylate (TFEMA) on water sorption, water solubility, degree of conversion, polymerization shrinkage, fluoride release and flexural strength of bisphenol-A-glycerolate dimethacrylate (Bis-GMA)/TEGDMA/urethane dimethacrylate (UDMA) dental composites. Flexural strength, water sorption and water solubility were measured according to ISO 4049 standard. Degree of conversion was determined by FTIR technique. Fluoride release rate in deionized water at 37°C was determined by using photometric method. One-way ANOVA and Tukey's HSD tests were used for statistical significance analysis (p<0.05). The results demonstrated that TFEMA decreased water solubility and volumetric shrinkage significantly but neither reduced water sorption, enhanced flexural strength nor improved degree of conversion. Partial substitution of TEGDMA with TFEMA in Bis-GMA/TEGDMA/UDMA dental composite had positive effect on its water solubility and volumetric shrinkage quality.

New silyl-functionalized BisGMA provides autonomous strengthening without leaching for dental adhesives

Resin-based composite has overtaken dental amalgam as the most popular material for direct restorative dentistry. In spite of this popularity the clinical lifetime of composite restorations is threatened by recurrent decay. Degradation of the adhesive leads to gaps at the composite/tooth interface–bacteria, bacterial by-products and fluids infiltrate the gaps leading to recurrent decay and composite restoration failure. The durability of resin-dentin bonds is a major problem. We address this problem by synthesizing silyl-functionalized BisGMA (e.g., silyl-BisGMA), formulating dental adhesives with the new monomer and determining the physicochemical properties and leaching characteristics of the silyl-BisGMA adhesives. Silyl-BisGMA was synthesized by stoichiometric amounts of BisGMA and 3-isocyanatopropyl trimethoxysilane (IPTMS). The control adhesive was a mixture based on HEMA/BisGMA (45/55, w/w). In the experimental formulations, BisGMA was partially or completely replaced by silyl-BisGMA. Water miscibility, polymerization behavior (Fourier transform infrared spectroscopy, FTIR), thermal property (modulated differential scanning calorimetry, MDSC), mechanical properties in dry and wet conditions (dynamic mechanical analysis, DMA), and leached species (HPLC) were investigated. Data from all tests were submitted to appropriate statistical analysis (α = 0.05). Silyl-BisGMA-containing adhesives exhibited comparable water miscibility, lower viscosities, and significantly improved degree of conversion of CC bond as compared to the control. After 4 weeks aqueous aging, the glass transition temperature and rubbery moduli of the experimental copolymers were significantly greater than the control (p < 0.05). HPLC results indicated a substantial reduction of leached HEMA (up to 99 wt%) and BisGMA (up to 90 wt%). By introducing silyl-functional group, the new BisGMA derivative exhibited potential as a monomer that can lead to dental adhesives with improved mechanical properties and reduced leaching under conditions relevant to the oral environment. Statement of SignificanceThe low-viscosity adhesive that bonds the composite to the tooth (enamel and dentin) is intended to seal and stabilize the composite/tooth interface, but it degrades leading to a breach at the composite/tooth margin. As the most popular crosslinking monomer in adhesives, Bisphenol A-glycerolate dimethacrylate (BisGMA) has limitations, e.g. susceptible to hydrolysis and concomitant property degradation. A methoxysilyl-functionalized BisGMA derivative (silyl-BisGMA) was introduced in this work to respond to these limitations. Our results indicated that by introducing silyl-BisGMA, higher crosslinked networks were obtained without sacrificing the homogeneity, and the leached amount of HEMA was reduced up to 99%. This novel resin offers potential benefits including prolonging the functional lifetime of dental resin materials.

Modulating pH through lysine integrated dental adhesives

ObjectivesThe objective of this study was to explore the effect of lysine integration to dental adhesives with respect to the polymerization kinetics, neutralization capacities in the acidic microenvironment, dynamic mechanical properties, and thermal properties. Materials and methodLysine was incorporated into liquid resin formulations at 2.5 and 5.0wt % with additional water/ethanol co-solvents. The co-monomer system contained 2-hydroxyethyl-methacrylate (HEMA) and Bisphenol A glycerolate dimethacrylate (BisGMA) with a mass ratio of 45/55. The kinetics of photopolymerization, neutralization capacities, lysine-leaching, dynamic mechanical properties and thermal properties of the control and experimental adhesives were analyzed. ResultsThe degree of conversion of the experimental adhesive was increased substantially at 2.5wt% lysine as compared to the control. The experimental polymers provided acute neutralization of the acidic microenvironment. Approximately half of the lysine was released from the polymer network within one month. Under dry conditions and physiologic temperatures, the incorporation of lysine did not compromise the storage modulus. Comparison of the thermal properties suggests that the more compact structure of the control adhesive inhibits movement of the polymer chains resulting in increased Tg. SignificanceIncorporating lysine in the adhesive formulations led to promising results regarding modulating pH, which may serve as one aspect of a multi-spectrum approach for enhancing the durability of composite restorations. The results provide insight and lay a foundation for incorporating amino acids or peptides into adhesive formulations for pH modulation or desired bioactivity at the interfacial margin between the composite and tooth.

Preparation and Characterization of Novel Dental Material with High Shear Bond Strength.

HPMA (hydroxypropyl methacrylate) and Bis-GMA (bisphenol A glycerolate dimethacrylate), the main ingredients, and styrene, TEGDMA (triethylene glycol dimethacrylate), BPO (benzoyl peroxide) and camphoroquinone, the photo-initiators, and BHT (butylated hydroxytoluene), the photocatalyst were mixed by different ratios and stirred to investigate the compatibility of dental materials with photoinitiators. The degree of polymerization was checked and determination of the most ideal ratio for photopolymerization was followed by establishing the basic combination of styrene, HPMA, Bis-GMA, BHT, TEGDMA and HEMA. The mixture made in accordance to the predetermined ratio was stirred for 24 hours and was polymerized at a wavelength of 440 to 480 nm for 40 secs. The physical properties of each combination were also evaluated to analyze the functionality of the prepared resin cement. And also, the cytotoxicity of the samples was tested, and as a result, the cell lysis rate was 0% in negative control and 100% in positive control and 0% in S-1 combination which indicates that it does not possess cytotoxicity against cultured cells. It is considered suitable for commercializing and will be highly applicable as high quality dental resin cement.