Bis-(acrylamide)s as new cross-linkers for resin-based composite restoratives

OBJECTIVES: The objective of this study was to investigate the use of three new bis-(acrylamide)s as cross-linker in resin-based composite restoratives. Selected mechanical properties such as flexural strength and flexural modulus of model composites containing bis-(acrylamide)s were investigated and compared to the properties of composites that are based on only conventional dimethacrylates. In addition, the hydrolytic stability of composites containing an acidic monomer was examined. METHODS: The flexural strength and flexural modulus of elasticity were determined according to ISO 4049:2000. For this purpose, test specimens (2 mm x 2 mm x 25 mm) of the composites investigated were prepared in stainless steel moulds and light-cured (150 mW/cm2, 2 x 180 s). The flexural strength and flexural modulus were measured after the samples had been stored in dry conditions or in water for 24 h at 37 degrees C as well as after they had been stored in water for 7 days at 37 degrees C, and in certain cases, after they had been boiled for 24 h in water. RESULTS: Visible light cured mixtures of dimethacrylates with bis-(acrylamide)s and composites based on these mixtures show a similar reactivity, flexural strength and flexural modulus of elasticity compared to materials that contain only dimethacrylate. The composites did not show any deterioration of the mechanical properties after water storage. Only when strongly acidic monomers were added to the composites containing dimethacrylates or bis-(acrylamide)s did the flexural strength and flexural modulus of the samples decrease after they were stored in water. SIGNIFICANCE: Bis-(acrylamide)s were similarly reactive than dimethacrylates and therefore can be used as diluents to substitute dimethacrylate diluents in composites. Although the bis-(acrylamide)s are entirely soluble in water, non-ionic materials based on bis-(acrylamide)s did not strongly change their mechanical properties during storage in water.     

Sol-gel materials 2. Light-curing dental composites based on ormocers of cross-linking alkoxysilane methacrylates and further nano-components.

OBJECTIVES: The objective of this study was to investigate the use of ormocers, which were synthesized from amine or amide dimethacrylate trialkoxysilanes. Ormocers showed improved biocompatibility in dimethacrylate-diluent-free composite restoratives. Selected mechanical properties, such as flexural strength and flexural modulus of experimental composites containing ormocers were investigated. In addition, the influence of methacrylate-substituted ZrO2 clusters and SiO2 organosols on the mechanical properties of composites was studied. METHODS: The flexural strength and flexural modulus of elasticity were determined according to ISO 4049: 2000. For this purpose, test specimens (2mmx2mmx25mm) of the composites investigated were prepared in stainless steel moulds and light-cured (150mW/cm2, 2x180s). The flexural strength and flexural modulus of elasticity were measured after the samples had been stored in water for 24h at 37 degrees C. RESULTS: While visible light-cured dimethacrylate-diluent-free composite restoratives based on the investigated ormocers showed a similar flexural strength and flexural modulus of elasticity compared to composites that contain only dimethacrylates, their double bond conversion was considerable lower. The simultaneous addition of methacrylate-substituted ZrO2 clusters and SiO2 organosols to the ormocer composite improved the mechanical properties of the composites. SIGNIFICANCE: Ormocers of amine or amide dimethacrylate trialkoxysilanes enabled the preparation of dimethacrylate-diluent-free composite restoratives. Based on the lower cytotoxicity of the ormocers, the prepared restorative composites should show improved biocompatibility. With the addition of nanoparticles, such as methacrylate-substituted ZrO2 clusters or SiO2 organosols, the mechanical properties of composites can be improved.     

Development of new diacrylate monomers as substitutes for Bis-GMA and UDMA

ObjectiveBisphenol A-glycidyl methacrylate (Bis-GMA) and urethane dimethacrylate (UDMA) are widely used as the primary components of (meth)acrylic monomers. However, the use of Bis-GMA, which is a bisphenol A derivative, in dentistry is being questioned after bisphenol A was found to exhibit estrogenic activity. Although UDMA is being considered as a substitute for bis-GMA, the mechanical properties of cured resin composites containing UDMA are less than desirable. Therefore, in this study, we developed new alternative (meth)acrylic monomers to enhance the mechanical strength of cured composite resins.MethodsFive urethane acrylic monomers were synthesized in this study as (meth)acrylic monomer substituents to replace Bis-GMA and UDMA. The elastic modulus, strength, and breaking energy values of cured resins consisting of mixtures of the urethane acrylates and diluting monomers were determined using the three-point flexural test. The data obtained were analyzed using one-way ANOVA and the post-hoc Tukey HSD tests (p < 0.05). Viscosities of the urethane acrylic monomers were measured with a cone-plate viscometer. Refractive indices of the urethane acrylic monomers were determined with an Abbe refractometer.ResultsThe results of the three-point flexural tests revealed that the cured urethane acrylic monomer-based resin exhibited higher elastic modulus (up to 40%) and strength (up to 21%) compared to the cured UDMA-based resin. Viscosity and refractive index of the urethane acrylic monomers were between those of UDMA and Bis-GMA.SignificanceThe developed urethane diacrylates prepared from diisocyanates which have an aromatic or aliphatic ring, 1,3-bis(1-isocyanato-1-methylethyl)benzene (TMXDI), 1,3-bis(isocyanatomethyl)benzene (XDI), or norbornane diisocyanate (NBDI) are worth considering as alternative options of Bis-GMA and UDMA for restorative resin composites.     

Properties of eight methacrylated beta-cyclodextrin composite formulations.

OBJECTIVES: Methacrylated beta-cyclodextrins (MCDs) are novel candidate dental monomers if all or some of the hydroxyl groups of beta-cyclodextrin are substituted with methacrylate groups. The main objective of this study was to evaluate mechanical properties of a number of composite formulations having MCDs as novel dental comonomers. The properties determined were flexural strength (FS), volumetric shrinkage (VS), and degree of conversion (DC). METHODS: A mass fraction of 50% of MCD monomers was mixed with a mass fraction of 50% each of a series of dimethacrylate or monomethacrylate diluent comonomers to produce consistent formulations of a workable viscosity. For comparison a resin mixture of a mass fraction of 50% Bis-GMA and a mass fraction of 50% triethyleneglycol dimethacrylate (a typical dental resin mixture) was also studied. The mixtures were activated with camphorquinone and ethyl 4-dimethylamino benzoate. One part by mass of each activated resin formulation was mixed with three parts by mass of glass filler. Samples for the FS tests were prepared in (2 x 2 x 25) mm3 molds by light-curing the composites for 2 min on each side. The cured samples were immersed in 37 degrees C water for 24 h, and FS was measured with an Instron machine at a crosshead speed of 0.5 mm/min. VS was measured by a computer-controlled mercury dilatometer. DC was measured by near-infrared spectroscopy. RESULTS: The properties of the MCD-based composites depended on the kind of diluent used. With these MCD monomers, diluents of triethyleneglycol dimethacrylate, 1,10-decamethylenediol dimethacrylate, or benzyl methacrylate yielded the best composite properties. SIGNIFICANCE: Although not yet fully optimized, MCD-based composite formulations containing triethyleneglycol dimethacrylate, 1,10-decamethylenediol dimethacrylate, or benzyl methacrylate yielded flexural strength and volumetric shrinkage values were comparable to those of the Bis-GMA/triethyleneglycol dimethacrylate controls. These findings lend support for further development and evaluations of polymerizable cyclodextrin derivatives for use in dental materials.     

Physical and mechanical properties of an experimental dental composite based on a new monomer.

OBJECTIVE: The purpose of this study was to investigate the physical and mechanical properties of a dental composite based on BTDMA, a new dimethacrylate monomer based on BTDA (3,3',4,4'-benzophenone tetracarboxylic dianhydride), and to compare these with the properties of a composite based on commonly used Bis-GMA monomer. METHODS: Experimental composites were prepared by mixing the silane-treated filler with the monomers. The prepared pastes were inserted into the test molds and heat-cured. Light-cured composites were also prepared using camphorquinone and amine as photoinitiator system. Degree of conversion of the light-cured and heat-cured composites was measured using FTIR spectroscopy. The flexural strength, flexural modulus, diametral tensile strength (DTS), water sorption, water contact angle, microhardness and thermal expansion coefficient of the prepared composites were measured and compared. Water uptake of the monomers was also measured. RESULTS: The results showed that the mechanical properties of the new composite are comparable with the properties of the Bis-GMA-based composite but its water sorption is higher. BTDMA as a monomer containing aromatic rings and carboxylic acid groups in its structure gives a composite with good mechanical properties. There is a close relation between the contact angle, water sorption of the cured composite and water uptake of their monomers. SIGNIFICANCE: Finding new monomers as alternatives for Bis-GMA have been a challenge in the field of dental materials and any investigation into the properties of new composites would be beneficial in the development of dental materials.     

Evaluation of dental restorative composites containing polyhedral oligomeric silsesquioxane methacrylate.

OBJECTIVES: The aim of this study was to explore novel polymeric dental restorative composites, in which polyhedral oligomeric silsesquioxane methacrylate monomer (POSS-MA) was used to partially (or completely) replace the commonly used base monomer 2,2'-bis-[4-(methacryloxypropoxy)-phenyl]-propane (Bis-GMA). METHODS: The composites were cured (hardened) by photo-initiated free radical polymerization. Mechanical properties (i.e. flexural strength, Young's modulus and diametral tensile strength) of the composites were tested by a universal mechanical testing machine; photopolymerization induced volumetric shrinkage was measured using a mercury dilatometer; and near infrared (NIR) technique was used to study the degree of methacrylate double bond conversion and photopolymerization rate. RESULTS: Small percentage POSS-MA substitution of Bis-GMA (i.e. mass fraction of 10% or less) in the resin system improved the mechanical properties of the composites; while large amount substitution led to less desirable mechanical properties, lower methacrylate double bond conversion, and slower photopolymerization rate. Statistical examinations showed the maximum flexural strength of the composites occurred when 10% (mass fraction) of Bis-GMA was replaced by POSS-MA, while the highest modulus occurred when the mass fraction of POSS-MA was 2%. SIGNIFICANCE: Polymeric dental restorative composites with improved mechanical properties may be designed by judicious choice of monomer (POSS-MA, Bis-GMA and TEGDMA) compositions.     

Physical properties of current dental nanohybrid and nanofill light-cured resin composites

Objectives

The purpose of this work was the detailed study of sorption characteristics of water or artificial saliva, the determination of flexural strength and the flexural modulus, and the study of the thermal stability of some current commercial dental light-cured nanocomposites containing nano-sized filler particles.

Methods

Three nanohydrid dental composites (Tetric EvoCeram (TEC), Grandio (GR) and Protofill-nano (PR)) and two nanofill composites (Filtek Supreme Body (FSB) and the Filtek Supreme Translucent (FST)) were used in this work. The volumetric shrinkage due to polymerization was first determined. Also the sorption, solubility and volumetric increase were measured after storage of composites in water or artificial saliva for 30 days. The flexural strength and flexural modulus were measured using a three-point bending set-up according to the ISO-4049 specification, after immersion of samples in water or artificial saliva for 1 day or 30 days. Thermal analysis technique TGA method was used to investigate the thermal stability of composites.

Results

GR and TEC composites showed statistically no difference in volumetric shrinkage (%) which is lower than the other composites, which follow the order PR < FSB < FST. The amount of sorbed water and solubility is not statistically different than those in artificial saliva. In all the composites studied the amount of water, which is sorbed (% on composite) is not statistically different than the amount of water, which is desorbed and follows the order: GR < TEC < PR < FSB < FST. After immersion in water for 1 day the highest flexural strength showed the FSB and the lowest TEC. GR, PR and FST showed no statistically different flexural strength. The flexural modulus of composites after immersion for one day follows the order TEC < PR≤FST < FSB < GR.

Significance

Among the composites studied, Grandio had the lowest polymer matrix content, consisting mainly of Bis-GMA. It showed the lowest polymerization shrinkage and water sorption and the highest flexural strength and flexural modulus after immersion in water or artificial saliva for 30 days. The water and artificial saliva generally showed the same effect on physical properties of the studied composites. Thermogravimetric analysis gave good information about the structure and the amount of organic polymer matrix of composites.     

Network structure of Bis-GMA- and UDMA-based resin systems

OBJECTIVES: The commonly used dental base monomers 2,2-bis[p-(2'-hydroxy-3'-methacryloxypropoxy)phenylene]propane (Bis-GMA) and 1,6-bis(methacryloxy-2-ethoxycarbonylamino)-2,4,4-trimethylhexane (UDMA) require the use of a diluent monomer, such as triethylene glycol dimethacrylate (TEGDMA). The aim of this study was to measure double bond conversion of UDMA/TEGDMA and Bis-GMA/TEGDMA polymeric systems, determine the leachable portion, and analyze network formation by evaluating crosslinking and pendant double bonds. METHODS: UDMA or Bis-GMA was combined with TEGDMA in systematic increments and irradiated to form light cured polymers. Fourier transform infrared spectroscopy in the near-infrared region was used to measure double bond conversion. The leachable sol fraction was analyzed by 1H NMR. Resin composites were formulated. Flexural strength was measured by three-point bending and volumetric shrinkage was determined with a mercury dilatometer. RESULTS: The amount of base monomer greatly influenced double bond conversion, sol fraction, and crosslinking. Increasing base monomer concentration decreased double bond conversion, increased the leachable fraction, and decreased crosslinking and network formation. At mole fractions higher than 0.125, the UDMA polymers had significantly higher conversion than the Bis-GMA polymers. Bis-GMA polymers had higher leachable amounts of unreacted monomer, while UDMA mixtures had more crosslinking than the Bis-GMA mixtures. In regards to the physical properties of resin composites, increasing the base monomer improved flexural strength and decreased volumetric shrinkage. SIGNIFICANCE: This systematic study for the evaluation of conversion, leachability, crosslinking, and network structure along with physical properties, like volumetric shrinkage and flexural strength, are required for the optimization of competing desirable properties for the development of durable materials.     

Polymerization characteristics of light- and auto-curing resins for individual splints.

OBJECTIVES: The aim of this in vitro study was to assess different resins for occlusal splints regarding a number of polymerization characteristics. METHODS: One autopolymerizing resin (Palapress) and four light-curing resins (Acrylight, Primosplint, Triad TranSheet Colorless and Pink) were tested for flexural strength, modulus of elasticity, water sorption, volumetric shrinkage, and conversion of double bonds. These resins were polymerized for 10 and 15 min in a light oven at frequencies between 320 and 400 nm or 400 and 500 nm, respectively. Data were treated statistically by ANOVA and by Scheffé test. RESULTS: Concerning flexural strength and modulus of elasticity, Triad TranSheet Colorless showed significantly greater values than Primosplint and Palapress (p<0.05). The light curing resins Acrylight and Primosplint featured significantly higher water sorption when cured for 10 min compared to all other resins (p<0.05). Acrylight displayed significantly higher volumetric shrinkage and a higher quantity of remaining double bonds compared to all other light-curing resins (p<0.05). Primosplint, Triad TranSheet Colorless and Pink showed significantly lower shrinkage values than autopolymerizing Palapress (p<0.05). For all light curing resins, polishing of the samples resulted in a significantly lower quantity of remaining double bonds (p<0.05) compared to unpolished samples. SIGNIFICANCE: With respect to the polymerization properties evaluated, the light-curing resins reached similar material properties to the autopolymerizing resin or even surpassed them. Light-curing resins seem to be suitable for the fabrication of occlusal splints and can been seen as an alternative to autopolymerizing polymethylmethacrylates.     

Synthesis and evaluation of modified urethane dimethacrylate resins with reduced water sorption and solubility

ObjectivesNew aliphatic and aromatic urethane dimethacrylate monomers containing pendant phenyl methoxy or ethyl substituents were synthesized in order to reduce the water sorption and solubility of urethane dimethacrylate systems. Selected properties including flexural strength, flexural modulus, water sorption and solubility, and water contact angle were evaluated. Hoy's solubility parameters were also calculated to rank copolymer hydrophilicity.MethodsFilled (20%) composite resins were formulated with each of the newly synthesized dimethacrylates as well as the commercially available urethane dimethacrylate monomer, UDMA. Flexural strength, flexural modulus, water sorption and solubility of the urethane composites were evaluated after light-cured specimens were immersed in water for seven days. Water contact angles were measured on the surface of each material. Data were analyzed using ANOVA and Ryan–Einot–Gabriel–Welsch multiple range tests (α = 0.05).ResultsA significant reduction of nearly 30% and 40% in water uptake was observed with composite polymers containing pendant ethyl and phenyl methoxy groups, respectively, compared to UDMA (p < 0.05). Urethane copolymers containing pendant ethyl groups also showed a significant reduction in water solubility (p < 0.05). A positive correlation was found between contact angle and water sorption as well as Hoy's δ_h for hydrogen bonding forces.SignificanceThe results of this study indicate that the incorporation of pendant hydrophobic substituents within the monomer backbone may be an effective method in reducing the water sorption and water solubility of urethane based dimethacrylate systems. The use of Hoy's solubility parameters to determine the relative hydrophilicity of a polymer may be limited by its three-dimensional chemical structure.     

Thiol-ene-methacrylate composites as dental restorative materials

Objectives

The objective of this study was to evaluate composite methacrylate-thiol-ene formulations with varying thiol:ene stoichiometry relative to composite dimethacrylate control formulations. It was hypothesized that the methacrylate-thiol-ene systems would exhibit superior properties relative to the dimethacrylate control resins and that excess thiol relative to ene would further enhance shrinkage and conversion associated properties.

Methods

Polymerization kinetics and functional group conversions were determined by Fourier transform infrared spectroscopy (FTIR). Volume shrinkage was measured with a linometer and shrinkage stress was measured with a tensometer. Flexural modulus and strength, depth of cure, water sorption and solubility tests were all performed according to ISO 4049.

Results

All of the methacrylate-thiol-ene systems exhibited improvements in methacrylate conversion, flexural strength, shrinkage stress, depth of cure, and water solubility, while maintaining equivalent flexural modulus and water sorption relative to the dimethacrylate control systems. Increasing the thiol to ene stoichiometry resulted in further increased methacrylate functional group conversion and decreased volume shrinkage. Flexural modulus and strength, shrinkage stress, depth of cure, water sorption and solubility did not exhibit statistically significant changes with excess thiol.

Significance

Due to their improved overall functional group conversion and reduced water sorption, the methacrylate-thiol-ene formulations are expected to exhibit improved biocompatibility relative to the dimethacrylate control systems. Improvements in flexural strength and reduced shrinkage stress may be expected to result in composite restorations with superior longevity and performance.     

Benzoyl germanium derivatives as novel visible light photoinitiators for dental materials.

OBJECTIVES: The objective of this study was to investigate the use of benzoyl germanium derivatives as a novel visible light photoinitiator of resin-based dental composites. Selected mechanical properties, such as flexural strength and flexural modulus, setting time, storage stability, and UV light stability, of the composites based on the novel photoinitiators benzoyltrimethylgermane (BTMGe) or dibenzoyldiethylgermane (DBDEGe) were investigated and compared to the properties of materials that are cured with a mixture of camphorquinone (CQ) and ethyl 4-(N,N-dimethylamino)benzoate (EMBO). METHODS: The flexural strength and flexural modulus of elasticity were determined according to ISO 4049. For this purpose, test specimens (2 mm x 2 mm x 25 mm) of the composites investigated were prepared in stainless steel moulds and light-cured (150 mW/cm2, 2 s x 180 s). The flexural strength and flexural modulus of elasticity were measured after immersing the cured specimens in water for 24h at 37 degrees C and in certain cases, after they had been boiled for 24h in water. In addition, the setting time, curing depth, storage and UV stability of selected composites were determined. RESULTS: The novel photoinitiators BTMGe or DBDEGe can be used to substitute the binary photoinitiator CQ/EMBO in visible light-cured restorative composites. Especially, DBDEGe showed a significantly higher photocuring activity in composites with a filler load of about 60 wt. % in comparison to that of CQ/EMBO. In addition, composites based on BTMGe or DBDEGe showed an improved UV stability and a storage stability comparable to that of CQ/EMBO-based composites.     

Properties of a dental resin composite with a spherical inorganic filler

This study compared the mechanical properties, generalized wear resistance and polymerization shrinkage of a resin composite filled with spherical inorganic filler to other commercial resin composites. Six dental resin composites were tested, including a submicron filled composite (Estelite sigma, Estelite), 1 nano-composite (Filtek Supreme, Supreme), 2 microfilled composites (Heliomolar; Renamel Microfill, Renamel) and 2 microhybrid composites (Esthet X Improved; Tetric Ceram). Compressive strength (CS), diametral tensile strength (DTS), flexural strength (FS), flexural modulus (FM), generalized wear resistance (WV) and polymerization shrinkage (PS) were evaluated for the 6 materials. The specimens were cured according to the manufacturers' instructions in appropriate molds, stored (37 degrees C water, 24 hours), then tested on an Instron testing machine (0.5 mm/minute). PS was tested according to the Archimedes method at 1, 24 and 48 hours continually after polymerization. Data were analyzed by analysis of variance. The results showed that CS values ranged from 252 to 298 MPa, DTS ranged from 35 to 54 MPa, FS from 73 to 140 MPa, FM from 4.8 to 11.1 GPa, WV from 0.037 to 0.086 mm(3) and PS at 24 hours from 2.17 to 3.96 vol%. Composite had statistically significant influence on the in vitro properties tested. Estelite performed similarly to nano-composite and microhybrid composites in mechanical properties and generalized wear resistance, while Estelite and Supreme had the lowest PS among the materials tested. The 2 microhybrid materials had similar properties, while the 2 microfilled composites were different for most properties tested. Overall, the microfilled composites had lower strength than the other composites except Renamel for CS. All the materials had a similar shrinkage pattern in that about 99% of shrinkage occurred in less than 24 hours.     

Degree of cure and fracture properties of experimental acid-resin modified composites under wet and dry conditions.

OBJECTIVE: Evaluate the effects of core structure and storage conditions on the mechanical properties of acid-resin modified composites and a control material by three point bending and conversion measurements 15min and 24h after curing. METHODS: The monomers pyromellitic dimethacrylate (PMDM), biphenyldicarboxylic-acid dimethacrylate (BPDM), (isopropylidene-diphenoxy)bis(phthalic-acid) dimethacrylate (IPDM), oxydiphthalic-acid dimethacrylate (ODPDM), and Bis-GMA were mixed with triethyleneglycol dimethacrylate (TEGDMA) in a 40/60 molar ratio, and photo-activated. Composite bars (Barium-oxide-glass/resin=3/1 mass ratio, (2mmx2mmx25mm), n=5) were light-cured for 1min per side. Flexural strength (FS), elastic modulus (E), and work-of-fracture (WoF) were determined in three-point bending after 15min (stored dry); and after 24h under dry and wet storage conditions at 37 degrees C. Corresponding degrees of conversion (DC) were evaluated by Fourier transform infrared spectroscopy. Data was statistically analyzed (2-way analysis of variance, ANOVA, Holm-Sidak, p<0.05). RESULTS: Post-curing significantly increased FS, E and DC in nearly all cases. WoF did not change, or even decreased with time. For all properties ANOVA found significant differences and interactions of time and material. Wet storage reduced the moduli and the other properties measured with the exception of FS and WoF of ODPDM; DC only decreased in BPDM and IPDM composites. SIGNIFICANCE: Differences in core structure resulted in significantly different physical properties of the composites studied with two phenyl rings connected by one ether linkage as in ODPDM having superior FS, WoF and DC especially after 24h under wet conditions. As expected, post-curing significantly contributed to the final mechanical properties of the composites, while wet storage generally reduced the mechanical properties.     

Synthesis, characterization and evaluation of urethane derivatives of Bis-GMA.

OBJECTIVES: The aims of the study were to synthesize derivatives of Bis-GMA having pendant n-alkyl urethane substituents and to characterize and evaluate their physicochemical properties. METHODS: Stoichiometric amounts of Bis-GMA and n-alkyl isocyanates were reacted in dichloromethane with dibutyltin dilaurate as a catalyst. Volumetric shrinkage, water uptake, degree of vinyl conversion, refractive index and viscosity of resulting urethane monomers and those of Bis-GMA were measured. The flexural strengths of their corresponding homopolymers and that of Bis-GMA were also measured. RESULTS: These types of urethane derivatives of Bis-GMA exhibited lower viscosities and were more hydrophobic than Bis-GMA. Generally, the viscosity of these experimental monomers decreased with increasing chain length of the alkyl urethane substituent. Photopolymerization of the new monomers gave high degrees of vinyl conversion compared to Bis-GMA. The experimental monomers also yielded polymers with lower polymerization shrinkages at equivalent degrees of vinyl conversion, than Bis-GMA. The refractive indices of these urethane derivatives were similar to Bis-GMA, but the flexural strengths of their polymers were lower than that of the Bis-GMA homopolymer, decreasing with increasing chain length of the alkyl urethane substituent. SIGNIFICANCE: Because of their excellent overall properties, these new derivatives of Bis-GMA have potential as dental monomers that can improve many properties of resin based dental materials that utilize methacrylate monomer systems.     

Characterization of urethane-dimethacrylate derivatives as alternative monomers for the restorative composite matrix

ObjectiveThe aim was accomplished by a comparative analysis of the physicochemical properties of urethane-dimethacrylate (UDMA) monomers and their homopolymers with regard to the properties of basic dimethacrylates used presently in dentistry. The homologous series of UDMA were obtained from four oligoethylene glycols monomethacrylates (HEMA, DEGMMA, TEGMMA and TTEGMMA) and six diisocyanates (HMDI, TMDI, IPDI, CHMDI, TDI and MDI).MethodsPhotopolymerization was light-initiated with the camphorquinone/tertiary amine system. Monomers were tested for viscosity and density. Flexural strength, flexural modulus, hardness, water sorption and polymerization shrinkage of the polymers were studied. The glass transition temperature and the degree of conversion were also discussed.ResultsHEMA/IPDI appeared to be the most promising alternative monomer. The monomer exhibited a lower viscosity and achieved higher degree of conversion, the polymer had lower water sorption as well as higher modulus, glass temperature and hardness than Bis-GMA. The polymer of DEGMMA/CHMDI exhibited lower polymerization shrinkage, lower water sorption and higher hardness, however it exhibited lower modulus when compared to HEMA/TMDI. The remaining monomers obtained from HEMA were solids. Monomers with longer TEGMMA and TTEGMMA units polymerized to rubbery networks with high water sorption. The viscosity of all studied UDMA monomers was too high to be used as reactive diluents.SignificanceThe systematic, comparative analysis of the homologous UDMA monomers and corresponding homopolymers along with their physico-mechanical properties are essential for optimizing the design process of new components desirable in dental formulations. Some of the studied UDMA monomers may be simple and effective alternative dimethacrylate comonomers.     

Dimethacrylate based on cycloaliphatic epoxide for dental composite.

OBJECTIVES: The aim of this study was to investigate the kinetics and mechanical properties of dimethacrylate monomer based on cycloaliphatic epoxide for dental restorative composite. METHODS: Dimethacrylate based on cycloaliphatic epoxide (EPCDMA) was copolymeirzed with TEGDMA by varying the curing conditions: monomer composition and light intensity. A real-time near FTIR technique was employed to monitor the double bond conversion and the rate of polymerization. Dynamic mechanical analysis was performed on a dynamic mechanical analyzer, and volume shrinkage of the cured samples was determined by pycnometric method. RESULTS: The results of kinetics showed that, two peaks of maximum rate of polymerization (Rpmax) occurred when the amount of TEGDMA was more than 30wt%. Increasing the amount of TEGDMA, the final double bond conversion and polymerization shrinkage both increased, while the glass transition temperature (Tg) decreased. All EPCDMA/TEGDMA mixtures had slightly higher storage modulus at body temperature (37 degrees C). When compared with Bis-GMA/TEGDMA (70/30), the EPCDMA/TEGDMA (70/30) system assumed similar reactivity and volume shrinkage but higher Tg. SIGNIFICANCE: EPCDMA had comparable mechanical properties to those of Bis-GMA.     

High performance dental resin composites with hydrolytically stable monomers

Objective

The objectives of this project were to: 1) develop strong and durable dental resin composites by employing new monomers that are hydrolytically stable, and 2) demonstrate that resin composites based on these monomers perform superiorly to the traditional bisphenol A glycidyl dimethacrylate/triethylene glycol dimethacrylate (Bis-GMA/TEGDMA) composites under testing conditions relevant to clinical applications.

Evaluation of two Bis-GMA analogues as potential monomer diluents to improve the mechanical properties of light-cured composite resins.

OBJECTIVES: The aim of this study was to investigate the influence of new diluent agents, diluent ratio and filler content, on relevant mechanical properties of several novel composite resins containing Bis-GMA as resin matrices, and to compare these with the properties of composites based on TEGDMA, a conventionally used diluent. METHODS: Two Bis-GMA analogues were synthesized and 20 experimental composite resins were prepared combining three monomer mixtures (Bis-GMA/TEGDMA, Bis-GMA/CH3 Bis-GMA and Bis-GMA/CF3 Bis-GMA), at three dilution rates (85/15, 10/90, 0/100) and three levels of hybrid filler content (barium aluminosilicate glass): 0, 10 and 35%. Flexural strength (FS), modulus of elasticity (ME) and microhardness (VHN) of the composites were evaluated. Five specimens of each material were prepared for each mechanical test, light-cured over 120 s and stored in water at 37 degrees C for 1 week. Three-point bending test was used for FS measurement and VHN was quantified by using a Vickers microindentor. Data were analyzed by ANOVA and Student-Newman-Keuls tests (P<0.05). RESULTS: Materials with CH3 Bis-GMA showed an enhanced VHN. Mean FS was higher for matrices containing TEGDMA. Overall, dilution favored FS and VHN but not ME. Filler loading specially improved ME and VHN. SIGNIFICANCE: Results correlate with an increase in the extent of polymerization due to the higher flexibility of the less viscous comonomer starting system and the hydrophobic character of the Bis-GMA analogues.     

Synthesis and characterization of acetyloxypropylene dimethacrylate as a new dental monomer

Objective

In this study acetyloxypropylene dimethacrylate was synthesized and proposed as an alternative monomer for triethyleneglycol dimethacrylate (TEGDMA) in dental mixtures.

Methods

The monomer was prepared by the reaction of glycerol dimethacrylate with acetic anhydride. The exchange reaction was carried out in the presence of catalytic amounts of sulfuric acid. After purification the monomer was mixed with 2,2-dimethoxy-2-phenyloacetophenone and photo-irradiated. Unfilled homopolymer was evaluated for photopolymerization conversion and volumetric curing shrinkage. Water sorption, water solubility, flexural strength and hardness were measured. Also, dynamic mechanical studies were performed. For comparison TEGDMA was homopolymerized and its properties were evaluated.

Results

The proposed dimethacrylate has viscosity comparable to TEGDMA, lower curing shrinkage and lower degree of double bond conversion. After homopolymerization, its water sorption is much lower than that of homopolymerized TEGDMA. Concerning the mechanical properties, the homopolymerized acetyloxypropylene dimethacrylate has higher modulus and hardness than analogically cured TEGDMA.

Significance

New dimethacrylate is a promising photocurable dental diluent owing to its low viscosity, good mechanical and water uptake properties.