Synthesis of a novel monomer "DDTU-IDI" for the development of low-shrinkage dental resin composites.

OBJECTIVE: The current dental resin composites often suffer from polymerization shrinkage, which can lead to microleakage and potentially result in recurring tooth decay. This study presents the synthesis of a novel monomer, (3,9-diethyl-1,5,7,11-tetraoxaspiro[5,5]undecane-3,9-diyl)bis(methylene) bis((2-(3-(prop-1-en-2-yl)phenyl)propan-2-yl)carbamate) (DDTU-IDI), and evaluates its effect in the formulation of low-shrinkage dental resin composites. METHODS: DDTU-IDI was synthesized through a two-step reaction route, with the initial synthesis of the required raw material monomer 3,9-diethyl-3,9-dihydroxymethyl-1,5,7,11-tetraoxaspiro-[5,5] undecane (DDTU). The structures were confirmed using Fourier-transform infrared (FT-IR) spectroscopy and hydrogen nuclear magnetic resonance (1HNMR) spectroscopy. Subsequently, DDTU-IDI was incorporated into Bis-GMA-based composites at varying weight percentages (5, 10, 15, and 20 wt%). The polymerization reaction, degree of conversion, polymerization shrinkage, mechanical properties, physicochemical properties and biocompatibility of the low-shrinkage composites were thoroughly evaluated. Furthermore, the mechanical properties were assessed after a thermal cycling test with 10,000 cycles to determine the stability. RESULTS: The addition of DDTU-IDI at 10, 15, and 20 wt% significantly reduced the polymerization volumetric shrinkage of the experimental resin composites, without compromising the degree of conversion, mechanical and physicochemical properties. Remarkably, at a monomer content of 20 wt%, the polymerization shrinkage was reduced to 1.83 ± 0.53%. Composites containing 10, 15, and 20 wt% DDTU-IDI exhibited lower water sorption and higher contact angle. Following thermal cycling, the composites exhibited no significant decrease in mechanical properties, except for the flexural properties. SIGNIFICANCE: DDTU-IDI has favorable potential as a component which could produce volume expansion and increase rigidity in the development of low-shrinkage dental resin composites. The development of low-shrinkage composites containing DDTU-IDI appears to be a promising strategy for reducing polymerization shrinkage, thereby potentially enhancing the longevity of dental restorations.

Residual Monomer Release after the Polymerization of Different-Colored Flowable Compomer.

BACKGROUND: Compomers are restorative materials commonly used in pediatric dentistry. It is important to investigate the monomer release of materials used especially in pediatric patients. The aim of this study was to evaluate the residual monomer released from different-colored flowable compomers at five polymerization times. MATERIALS AND METHODS: Three experimental groups were formed: Group 1: pink flowable compomer (Twinky Star, VOCO, Germany), Group 2: blue flowable compomer (Twinky Star, VOCO), Group 3: white flowable compomer, A2 color of Dyract XP (Dentslpy DeTrey, Konstanz, Germany). For each group, samples were prepared using standard cylindrical Teflon molds (n = 10), and the compomers were cured using a light-emitting diode (LED) source in accordance with the manufacturer's recommendations. During each time period, the number of residual monomers: bisphenol-A glycidyl methacrylate (bis-GMA), urethane dimethacrylate (UDMA), hydroxyethyl methacrylate (HEMA), and triethylene glycol dimethacrylate (TEGDMA) were determined with high-performance liquid chromatography (HPLC). All data were analyzed statistically. RESULTS: In all groups, the amount of residual monomers increased after 1-h release periods (P < 0.05). For 2 weeks, the total residual monomers released were determined at most in Group 3 and at least in Group 1. However, there was no significant difference between the groups in terms of released amounts of monomers (P > 0.05). CONCLUSIONS: According to the study, when the total amount of residual monomer released from all groups was compared, no difference was found and it was observed that none of them exceeded the toxic dose. Flowable colored compomers can be used as safely as white compomers in pediatric dentistry.

Bond Strength, Microleakage, Microgaps, and Marginal Adaptation of Self-adhesive Resin Composites to Tooth Substrates with and without Preconditioning with Universal Adhesives.

PURPOSE: This study investigated and compared the bond strengths, microleakage, microgaps, and marginal adaptation of self-adhesive resin composites (SAC) to dentin with or without universal adhesives. MATERIALS AND METHODS: Dentin surfaces of 75 molars were prepared for shear and microtensile bond strength testing (SBS and µTBS). Silicon molds were used to build up direct restorations using the following materials to form 5 groups: 1. Surefil One; 2. Prime&Bond active Universal Adhesive + Surefil One; 3. Vertise Flow; 4. OptiBond Universal + Vertise Flow; 5. Scotchbond Universal + Filtek Z500 (control group). Bonded specimens were thermocycled 10,000x before being tested either for SBS or µTBS using a universal testing machine at a crosshead speed of 0.5 mm/min. Direct mesial and distal class-II cavities were created on 100 sound premolars, with the gingival margin of distal cavities placed below CEJ and restored according to the five groups. After thermocycling, microleakage scores were assessed following immersion of restored premolars in 2% methylene blue dye for 24 h, while marginal gaps and adaptation percentages were investigated on epoxy resin replicas under SEM at magnifications of 2000X and 200X, respectively. Results were statistically analyzed with parametric and non-parametric tests as applicable, with a level of significance set at α = 0.05. RESULTS: Bond strengths, microleakage scores, microgaps, and percent marginal adaptation of Surefil One and Vertise Flow were significantly (p < 0.001) inferior to the control group. Dentin preconditioning with universal adhesives significantly increased the study parameter outcomes of Surefil One and Vertise Flow, yet they were still significantly below the performance of the control group. CONCLUSION: Conventional resin composite outperformed the SAC whether applied solely or in conjunction with their corresponding universal adhesives.

Evaluation of the amount of residual monomer released from different flowable composite resins.

Today, resin materials are used in the restoration of permanent and deciduous teeth or as fissure sealants. The materials can contain different types of monomers (Bis-GMA, UDMA, TEGDMA). These monomers can be released into the oral cavity after polymerization. Residual monomers released from resin-containing restorative materials after polymerization have been reported to have negative effects on mechanical properties. The aim of our study is to evaluate the amount of residual monomers released after polymerization of different flowable composite resin materials using two different modes of LED light source. Composite disc samples (8 mm diameter/2 mm depth) prepared for each material group were polymerized using two different modes of the LED light device (Standard mode and extra power mode). HPLC (High Performance Liquid Chromatography) device was used to measure the amount of residual monomer release at 1 h, 1 day, 3 days and 7 days periods. Pairwise comparison of the differences between the materials was performed by Post-hoc test. For each residual monomer, the Kruskal Wallis test was used to analyze the difference between the materials in standard mode and the difference between the materials in extra power mode. According to the results of the study; Grandio flow flowable composite showed the highest release of TEGDMA and Bis-GMA while SDR® Flow flowable composite showed the lowest release of TEGDMA, Bis-GMA and UDMA. For all materials, the extra power mode resulted in more residual monomer release. TEGDMA and Bis-GMA release was detected in all tested flowable composites at all time periods.

Monomer release, cell adhesion, and cell viability of indirect restorative materials manufactured with additive, subtractive, and conventional methods.

PURPOSE: The aim of this study was to measure residual monomer, cell adhesion, and cell viability of 3-dimensional printable permanent resin (PR), hybrid ceramic block (HCB), and indirect composite (IC) produced with additive, subtractive, and conventional techniques. METHODS: Five 8 × 8 × 2 mm3 samples of each material were prepared for each experiment. In a 24-h period, monomer release was analyzed with high-performance liquid chromatography, and cell viability and adhesion were evaluated with the water-soluble tetrazolium salt test. Data were analyzed with IBM SPSS Statistics 26.0 statistical software, and results were regarded as significant at α = 0.05. RESULTS: Monomer release (triethylene glycol dimethacrylate, urethane dimethacrylate, and Bisphenol A glycerolate dimethacrylate) was significantly higher in the IC group. Mean cell viability was significantly lower in the HCB group than in the IC group. CONCLUSION: All monomers in the tested materials were released at rates that were below clinical significance. Cell adhesion rates in the groups were similar. Cytotoxic response was classified as minor in the HCB and PR groups and non-cytotoxic in the IC group.

The impact of chitosan in experimental resin with different photoinitiator systems.

OBJECTIVE: to investigate the effect of different concentrations of chitosan added to experimental resins containing either BAPO or camphorquinone (CQ) as photoinitiators, regarding degree of conversion (DC), flexural strength (FS), flexural elastic modulus (E), Knoop microhardness (KHN), cytotoxicity, genotoxicity and antimicrobial activity. METHODS: Experimental resins with polymeric matrix of BisGMA and TEGDMA was added either 0.5 wt% BAPO or 0.5 wt% camphorquinone/0.2% amine along with and chitosan concentrations of 0.5%; 1.0% or 2.0%. Degree of conversion was measured using Fourier transformed infrared spectroscopy. Flexural strength and elastic modulus were obtained through three-point bending test and Knoop microhardness was measured in a microidenter. Direct cytotoxicity was performed in human keratinocytes and genotoxicity test was done in murine macrophages cells. Antimicrobial activity was acessed against Staphylococcus aureus and Streptococcus mutans through the inhibition halo. Data were analyzed using two-way ANOVA and Tukey teste (α = 0.05). RESULTS: The materials containing photoinitiator BAPO showed higher values of DC, FS, E, and KHN compared to resins with CQ. The addition of chitosan did not affect the properties of these materials. However, in resins containing CQ, the addition of chitosan improve these properties compared to control group. For the groups containing BAPO the chitosan reduced cytotoxicity and genotoxicity compared to materials with camphorquinone. The materials with 1.0% and 2.0% chitosan showed increased antibacterial activity in the materials containing BAPO as photoinitiator for both bacteria. SIGNIFICANCE: The alternative photoinitiator BAPO and chitosan can improve physical and biological properties of photoactivated resins when compared with the materials with photoinitiator camphorquinone.

Transdentinal cytotoxicity of resin luting cements using the bovine and human dentin barrier.

STATEMENT OF PROBLEM: Based upon ethical questions and because of the difficulty of obtaining intact human teeth, researchers have used bovine teeth to assess the physical and mechanical properties of different dental materials. However, data from transdentinal cytotoxicity tests showing that the bovine dentin barrier is similar to the human dentin barrier is lacking. PURPOSE: The purpose of this in vitro study was to evaluate whether the bovine dentin barrier produces similar results to those obtained when the human dentin barrier is used to assess the transdentinal cytotoxicity of resin luting cements. MATERIAL AND METHODS: The number and diameter of dentinal tubules present in the human dentin barrier and bovine dentin barrier were evaluated and assessed with a t test (α=.05). After inserting the standardized dentin barriers into artificial pulp chambers, murine dental papilla-derived cells (MDPC-23) were seeded on the pulpal surface of the specimens, and the luting cements were applied to their occlusal surfaces. Then, the following groups were established for both human and bovine dentin barriers: no treatment (negative control); Single Bond Universal; RelyX Luting 2; RelyX U200; and RelyX Ultimate. After 24 hours, the viability (alamarBlue) and morphology (scanning electron microscopy) of the cells were evaluated with a 2-way analysis of variance and the Tukey honest significance test (α=.05). RESULTS: Dentinal tubules with larger diameters were observed in bovine dentin (P<.05), but the number of tubules was similar (P>.05). A reduction in viability and notable changes in the morphology of MDPC-23 cells occurred in the Single Bond Universal and RelyX Luting 2 groups in comparison with the negative control (P<.05). The RelyX U200 and RelyX Ultimate groups were statistically similar to the negative control (P>.05). No difference was found in cytotoxicity when the same luting cement was applied on human or bovine dentin barriers (P>.05). CONCLUSIONS: For transdentinal cytotoxicity tests of resin luting cements, the bovine dentin barrier proved similar results to the human dentin barrier.

Acylthiourea oligomers as promising reducing agents for dimethacrylate-based two-component dental materials.

OBJECTIVES: Currently used thiourea-based two-component dental materials may release bitter compounds if they are not properly cured. To address this issue, the objective of this study was to evaluate the potential of acylthiourea oligomers as reducing agents for the development of self-cure composites. METHODS: Acylthiourea oligomers ATUO1-3 were synthesized via cotelomerization of the acylthiourea methacrylate ATU1 with butyl methacrylate. They were characterized by 1H NMR spectroscopy and size exclusion chromatography. Self-cure composites based on the redox initiator system cumene hydroperoxide/acylthiourea oligomer/copper(II) acetylacetonate were formulated. The flexural strength and modulus were measured using a three-point bending setup. The double bond conversions were determined using NIR spectroscopy. The working time of each self-cure composite was measured using an oscillating rheometer. Leaching experiments using light-cure composites were performed in DMSO-d6. RESULTS: Acylthiourea oligomers ATUO1-3 were successfully synthesized in good yields. Both the oligomer molecular weight and the amount of thiourea groups were varied. Self-cure composites containing ATUO1 or ATUO2 as reducing agents exhibited excellent mechanical properties and high double-bond conversions. The amounts of reducing agent, cumene hydroperoxide and copper(II) acetylacetonate were shown to have a significant impact on the working time. Moreover, a correlation between flexural modulus and the amount of metal salt was clearly established. Self-cure composites containing the oligomer ATUO1 exhibited a longer working time than materials containing ATU1 or acetylthiourea. Contrary to acetylthiourea, ATUO1 was not able to leach out of light-cured composites. SIGNIFICANCE: Acylthiourea oligomers are promising reducing agents for the formulation of two-component dental materials that do not induce a bitter taste in mouth.

Evaluation of physical/mechanical properties of an experimental dental composite modified with a zirconium-based metal-organic framework (MOF) as an innovative dental filler.

OBJECTIVES: This study aimed to modify an experimental dental composite using a synthesized nano-structured methacrylated zirconium-based MOF to enhance physical/mechanical properties. METHODS: The previously known Uio-66-NH2 MOF was first synthesized and post-modified with Glycidyl Methacrylate (GMA). Fourier Transform Infrared (FTIR) Spectroscopy and CHNS analysis confirmed the post-modification reaction. The prepared filler was investigated by XRD, BET, SEM-EDS, and TEM. The experimental composite was prepared by mixing 60% wt. of resin matrix with 40% wt. of fillers, including silanized silica (SS) or Uio-66-NH-Me (UM). The experimental composites' depth of cure (DPC) was investigated in five groups (G1 =40% SS, G2 =30%SS+10%UM, G3 =20%SS+20%UM, G4 =10%SS+30%UM, G5 =40%UM). Then flexural strength(FS), Elastic Modulus(EM), solubility(S), water sorption(WS), degree of conversion(DC), polymerization shrinkage(PS), and polymerization stress(PSR) of the groups with DPC of more than 1 mm were investigated. Finally, the cytotoxicity of composites was studied. RESULTS: The groups with more than 20% wt. UM, filler (G4, G5) had lesser than 1 mm DPC. Therefore, we investigated three groups' physical and mechanical properties with lower than 20% UM filler (G1-G3). Within these groups, G3 has a higher FS, EM (P < 0.05), and lower WS and S (P < 0.05). DC dropped in G2 and G3 compared to G1 (p < 0.05), but there was no significant difference between G2 and G3 (P = 0.594). SIGNIFICANCE: This new filler is an innovative coupling-agent free filler and can be part of dental filler technology itself. It can also introduce a new group of dental fillers based on MOFs, but it still needs a complete investigation to be widely used.

Degree of conversion and residual monomer elution of 3D-printed, milled and self-cured resin-based composite materials for temporary dental crowns and bridges.

The aim of this work was to investigate the elution of residual monomers as a function of the manufacturing process, which are CAD/CAM manufacturing, self-curing and 3D printing. The experimental materials used consisted of the base monomers TEGDMA, Bis-GMA and Bis-EMA and 50 wt.% fillers. Additionally, a 3D printing resin without fillers was tested. The elution of the base monomers into the different media (water, ethanol and ethanol/water (75/25 vol. %)) at 37 °C over a period of up to 120 d as well as the degree of conversion (DC) by FTIR were investigated. No monomer elution could be detected in water. Most residual monomers in both other media were released from the self-curing material whereas the 3D printing composite released relatively little. The CAD/CAM blanks released hardly any quantitatively detectable amounts of monomers. Relative to the base composition, TEGDMA eluted less than Bis-GMA and Bis-EMA. DC did not correlate with residual monomer release; thus, leaching was determined not only by the amount of residual monomers present but by further factors as possibly network density and structure. The CAD/CAM blanks and the 3D printing composite showed similar high DC but lower residual monomer release from the CAD/CAM blank, likewise the self-curing composite and the 3D printing resin exhibited similar DC but different monomer elution. In terms of residual monomer elution and DC, the 3D printing composite seems promising as a new material class for the use as temporary dental crowns and bridges.

Comparison of residual monomer amounts released from indirect bonding adhesives.

OBJECTIVES: To quantify the amount of residual monomer released from orthodontic adhesives used in the indirect bonding technique and compare it to a direct bonding composite resin. MATERIALS AND METHODS: Five hundred stainless steel orthodontic brackets were bonded on bovine incisors using five groups of bonding resins: Transbond XT (TXT), Transbond Supreme LV (SLV), Sondhi Rapid-Set (SRS), Transbond IDB (IDB), and Custom I.Q. (CIQ). Liquid samples were gathered on the first, seventh, 21st, and 35th days. Residual monomer release was measured from the liquid samples with a liquid chromatography device. In addition, the amount and shape of the adhesive between the tooth surface and the bracket base was evaluated using obtained electron microscopy images. The data were analyzed using analysis of variance, and a Tukey post-hoc test was applied. RESULTS: Hydroxyethylmethacrylate and bisphenol A-glycidyl methacrylate monomers were released by all study groups. Urethane-dimethacrylate was released from the TXT, SLV, IDB, and CIQ groups. Triethylene glycol dimethacrylate was released from TXT, SLV, IDB, and SRS groups. The amount of total monomer release was higher in chemically cured adhesives than in light-cured adhesives. Among the chemically cured adhesives, premix adhesives had the highest amount of total monomer release. The light-cured adhesives had less thickness. CONCLUSIONS: Light-curing adhesives have significantly less monomer release than chemically polymerized adhesives.

Evaluation of a biobased polycarbonate interpenetrated network in a dental resin composite.

Silanization of filler particles in a dental resin composite is achieved by the formation of Si-O-Si bonds, however, these bonds are especially vulnerable to hydrolysis because this covalent bond has a significant ionic character due to the electronegativity differences between the atoms. The objective of this study was to evaluate the use of an interpenetrated network (IPN) as alternative of silanization reaction and to assess its effect in selected properties of experimental photopolymerizable resin composites. The interpenetrate network was obtained during the photopolymerization reaction of organic matrix (BisGMA/TEGDMA) with a biobased polycarbonate. Its characterization was performed via FTIR, flexural strength, flexural modulus, depth of cure, sorption water and solubility. A resin composite formulated with non-silanized filler particles was used as control. The IPN with a biobased polycarbonate was successfully synthesized. The results showed that the IPN based resin composite had higher values of flexural strength, flexural modulus, and degree of double bond conversion than the control (p < 0.05). Polymerization shrinkage, water sorption and solubility were statistically significantly lower than the control resin (p < 0.05). Finally, this study shows there were no statistically significant differences for the biocompatibility outcomes (p > 0.05). The biobased IPN replaces the silanization reaction in resin composites, improving physical and chemical properties. Therefore, IPN with a biobased polycarbonate could be potentially useful in the formulation of dental resin composites.

Low shrinkage bulk-filled dental resin composites with non-estrogenic dimethacrylate.

This study synthesized and characterized different proportions of nonestrogenic di(meth)acrylate 9,9-bis[4-((2-(2-methacryloyloxy)ethyl-carbamate)ethoxy)phenyl] fluorine (Bis-EFMA)-based resin composite systems to study their physical, chemical, optical and biological characteristics, and adhesive properties after bonding to a tooth. The estrogenic activity of raw materials was evaluated and compared with estrogen and commercial bisphenol A. After photopolymerization, all resin composite systems were prepared, and their properties were systematically investigated. Notably, the nonestrogenic di(meth)acrylate Bis-EFMA exhibited a more suitable refractive index, excellent biocompatibility, low marginal microleakage and improved bonding strength. Except for the pure UDMA and Bis-EFMA groups, the depth of cure and Vickers microhardness ratios of all the other groups met the requirements of bulk filling (one-time curing depth of more than 4 mm). Bis-EFMA resin systems exhibited lower volumetric polymerization shrinkage (about 3-5%), higher curing depth (>6 mm in specific proportions), mechanical properties (flexural strength of 120-130 MPa, etc.), and microtensile bonding strength (>27.8 MPa), which were comparable or superior to Bis-GMA or commercial composites. Herein, we believe that the novel nonestrogenic di(meth)acrylate (Bis-EFMA) has a wide application prospect as an alternative to Bis-GMA.

Effect of preheating on mechanical properties of a resin-based composite containing elastomeric urethane monomer.

This study investigated the effect of preheating an elastomeric urethane monomer (Exothane-24) experimental resin composite on its physicochemical properties. Two resin matrices were formulated: (a) 50 wt% Bisphenol-glycidyl methacrylate (Bis-GMA) and 50 wt% triethylene glycol dimethacrylate (TEGDMA); and (b) 20 wt% Exothane-24, 40 wt% Bis-GMA and 40 wt% TEGDMA. A photoinitiator system (0.25 wt% camphorquinone and 0.50 wt% ethyl-4-dimethylamino benzoate) and 65 wt% of the inorganic filler (20 wt% 0.05 µm silica and 80 wt% 0.7 µm BaBSiO2 glass) were added to both matrices. These formulations were then assigned to four groups: Exothane-24 (E); Exothane-24 plus preheating (EH); no Exothane-24 (NE); and no Exothane-24 plus preheating (NEH). NEH and EH were preheated at 69 °C. The dependent variables were as follows: film thickness (FT); polymerization shrinkage stress (PSS); gap width (GW); maximum rate of polymerization (Rpmax); and degree of conversion (DC). Data were statistically analyzed by two-way ANOVA and Tukey's test (α = 0.05). Preheating reduced FT for both composites. PSS and GW were significantly lower for EH, when compared with E. The DC for EH and NEH and the Rpmax for EH increased significantly. Preheating improved most of the physicochemical properties (FT, PSS, GW, and DC) of the experimental resin composite containing Exothane-24.

Lignin-derived new hydrogen donors for photoinitiating systems in dental materials.

OBJECTIVES: The aim of this study is to develop amine free photo-initiating system (PIs) for the photopolymerization of dental methacrylate resins, using seven new hydrogen donors HDA-HDG derived from ß-O-4 lignin model. METHODS: Seven experimental CQ/HD PIs were formulated with Bis-GMA/TEGDMA (70 w%/30 w%). CQ/EDB system was chosen as the comparison group. FTIR-ATR was used to monitor the polymerization kinetics and double bond conversion. Bleaching property and color stability were evaluated using a spectrophotometer. Molecular orbitals calculations were used to demonstrate C-H bond dissociation energies of the novel HDs. Depth of cure of the HD based systems were compared to the EDB based one. Cytotoxicity was also studied by CCK8 assay using tissue of mouse fibroblasts (L929 cells). RESULTS: Compared to CQ/EDB system, the new CQ/HD systems show comparable or better photopolymerization performances (1 mm-thick samples). Comparable or even better bleaching properties were also obtained with the new amine-free systems. Comparing to EDB, all HDs exhibited significantly lower C-H bond dissociation energies by molecular orbitals calculations. Groups with new HD showed higher depth of cure. OD and RGR values were similar to that of the CQ/EDB group, ensuring the feasibility of the new HDs in dental materials. CLINICAL SIGNIFICANCE: The new CQ/HD PI systems could be potentially useful in dental materials, presenting improvements in restorations' esthetic and biocompatibility.

Preparation of a fluorinated dental resin system and its anti-adhesive properties against S. mutans.

OBJECTIVES: The purpose of this study was to characterize physicochemical properties and investigate anti-bacterial adhesion effect of dental resins containing fluorinated monomers. METHOD: Fluorinated dimethacrylate FDMA was mixed with commonly used reactive diluent triethylene- glycol dimethacrylate (TEGDMA) and fluorinated diluent 1 H,1 H-heptafluorobutyl methacrylate (FBMA) separately at a mass ratio of 60 wt./40 wt. to prepare fluorinated resin systems. Double bond conversion (DC), flexural strength (FS) and modulus (FM), water sorption (WS) and solubility (SL), contact angle and surface free energy, surface element concentration, and anti-adhesion effect against Streptococcus mutans (S. mutans) were investigated according to standard or referenced methods. 2,2-bis[4-(2-hydroxy-3-methacryloy-loxypropyl)-phenyl]propane (Bis-GMA)/TEGDMA (60/40, wt./wt.) was used as control. RESULTS: Both fluorinated resin systems had higher DC than Bis-GMA based resin (p < 0.05); compared with Bis-GMA based resin (FS, FDMA/TEGDMA resin system had higher FS (p < 0.05) and comparable FM (p > 0.05), while FDMA/FBMA resins system had lower FS and FM (p < 0.05). Both fluorinated resin systems had lower WS and SL than Bis-GMA based resin (p < 0.05), and FDMA/TEGDMA resin system had the lowest WS (p < 0.05) in all experimental resin systems. Only FDMA/FBMA resin system showed lower surface free energy than Bis-GMA based resin (p < 0.05). When the surface was smooth, FDMA/FBMA resin system had lower amount of adherent S. mutans than Bis-GMA based resin (p < 0.05), while after the surface became roughness, FDMA/FBMA resin system had comparable amount of adherent S. mutans as Bis-GMA based resin (p > 0.05). SIGNIFICANCE: Resin system prepared exclusively with fluorinated methacrylate monomers reduced the S. mutans adhesion due to their increased hydrophobicity and decreased surface energy., while flexural properties of it should be improved.

Release of leachable products from resinous compounds in the saliva of children with anterior open bite treated with spur.

BACKGROUND: To evaluate the release of bisphenol-A glycidyl methacrylate (BisGMA), triethylene glycol dimethacrylate (TEGDMA), bisphenol A (BPA), and phthalates of the composite resin used in the bonding of spurs applied in the treatment of children with anterior open bite and its effects on human keratinocytes. METHODOLOGY: Saliva samples of 22 children were collected before spur attachment (baseline) and 30 minutes (min) and 24 hours (h) after spur bonding. Analysis was performed using high-performance liquid chromatography (HPLC) coupled to tandem mass spectrometry (HPLC-MS/MS) and gas chromatography coupled to mass spectrometry (GC-MS). Standardized resin increments were added to three different dilutions of the cell culture medium. Keratinocytes (HaCaT) were cultivated in the conditioned media and evaluated for cell viability (MTT) and cell scratch assay. RESULTS: The levels of BisGMA (1.74±0.27 µg/mL), TEGDMA (2.29±0.36 µg/mL), and BPA (3.264±0.88 µg/L) in the saliva after 30 min, in comparison to baseline (0±0 µg/mL, 0±0 µg/mL, and 1.15±0.21 µg/L, respectively), presented higher numbers. After 24 h, the levels of the monomers were similar to the baseline. Phthalates showed no significant difference among groups. HaCat cells showed increased viability and reduced cell migration over time after exposure to methacrylate-based resin composites. CONCLUSION: Resin composites, used to attach spurs in children with anterior open bite during orthodontic treatment, release monomers after polymerization and can influence the behavior of human keratinocytes, even at very low concentrations. Orthodontists should be aware of the risks of the resinous compounds release and preventive procedures should be held to reduce patient exposure.

New dimethacrylate monomers based on phenolphthalein and resveratrol for the application of dental materials.

Potential estrogenic effects and changes in fertility are some of the health problems associated with bisphenol A (BPA) derivatives used to produce some polymers, including dental materials that contain Bis-GMA. Those issues drove this study proposing the synthesis of methacrylate resveratrol and phenolphthalein monomers that, combined with diluent monomers, generate copolymers. Their key characteristics were determined and analyzed on the chemical structure-property perspective considering monomer planarity and flexibility based on molecular dynamic simulations. METHODS: Methacrylate resveratrol ((E)-5-(4-(methacryloyloxy)styryl)-1,3-phenylenebis(2-methylacrylate)), EMPM) and methacrylate phenolphthalein ((3-oxo-1,3-dihydroisobenzofuran-1,1-diyl)bis(4,1-phenylene)bis(2-methylacrylate)), DIFPM) were synthesized through the reaction of precursors with methacryloyl chloride. After monomers purification and spectroscopic characterization (FTIR and NMR), the following copolymers were produced: DIFPM/TEGDMA and Bis-GMA/TEGDMA, EMPM/HEMA and Bis-GMA/HEMA. Microhardness, degree of conversion, water sorption and contact angle data were statistically analyzed through one-way ANOVA and Tukey's test (p ≤ 0.05). RESULTS: The DIFPM molecular structure's reduced flexibility proved to be an important factor to inhibit TEGDMA cyclization. In turn, the EMPM molecule's high planarity modified the spatial organization of the HEMA copolymer, altering the water diffusion and, therefore, the water sorption when compared to Bis-GMA copolymers. CONCLUSION: The scientific findings contribute to better understand the effect of monomer chemical structures, molecular geometry, and planarity on some physicochemical properties of copolymers. Knowledge that can contribute to the design of new monomers to replace Bis-GMA.

Impact of different pretreatments and attachment materials on shear bond strength of indirectly bonded brackets using CAD/CAM transfer trays to monolithic zirconia.

OBJECTIVE: Investigating the impact of different pretreatment methods, attachment materials and aging regimens on shear bond strength (SBS) between zirconia and indirectly bonded brackets using CAD/CAM transfer trays. METHODS: Zirconia substrates were conditioned with silica coated alumina (CoJet) and a) Clearfil Ceramic Primer Plus (CF), b) RelyX Ceramic Primer (RXP), c) Futurabond U (FU). Brackets were virtually placed, transfer tray designed (OnyxCeph) and 3D-printed for indirect bonding with a) Transbond LV (TBL), b) Nexus NX3 (NX3), c) Maximum Cure (MC). SBS testing was performed with a universal testing machine after 24 h, 500 thermal cycles, 90 d. Directly bonded brackets to human enamel using Transbond XT Adhesive served as control. The adhesive remnant index (ARI) was evaluated. Data was analyzed with Shapiro-Wilk, Kruskal-Wallis and Dunn's post-hoc test with Bonferroni correction, Chi2 test (p < 0.05), and the Weibull modulus was calculated. RESULTS: SBS ranged from 0.1 to 15.5 MPa and were influenced mostly by the attachment material. NX3 generally showed the highest values (9.5-15.8 MPa). Initially RXP/TBL and FU/TBL presented the lowest values (4.3/4.8 MPa). Aging regimens reduced SBS of MC irrespective of pretreatment, after 90 d values ranged from 0.1 to 0.9 MPa. ARI 1 was predominant in all MC groups and FU/NX3, 2 and 3 in the other groups. Weibull moduli ranged between 0.15 (MC/RXP/500 TC) and 6.24 (NX3/RXP/500 TC). SIGNIFICANCE: MC seems not to be suitable for indirect bonding using CAD/CAM transfer trays to zirconia. NX3 showed similar SBS values compared to the control, TBL lower.

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).