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1.
OBJECTIVES: This study was performed to determine the compositions of commercial temporary restorative resins and to evaluate the leachability of plasticizer and residual monomer from them. METHODS: The chemicals in four commercial temporary restorative resins (Dura Seal, Fit Seal, Plast Seal Quick, and Poly Seal) were detected by GCMS and HPLC. The amounts of plasticizers and residual monomers that leached from cured resin samples immersed in ethanol for 1 h to 14 d were determined by HPLC. RESULTS: Phthalate esters used as plasticizers contained 40-55 wt% either di-n-butyl phthalate (DBP) or butyl phthalyl butyl glycolate. The resin monomer included methyl methacrylate (MMA) or a mixture of MMA and 2-hydroxyethyl methacrylate (HEMA); 1,3-butanediol dimethacrylate was added as a cross-linking agent. Each resin contained 40-60 wt% monomer. The amounts of phthalate esters leached increased with immersion time up to 7 d, reaching 120-190 microg/mg, and did not change subsequently. The residual monomers leached gradually for up to 3d and did not change subsequently. The amount of leached residual monomer (MMA, HEMA) was 20-90 microg/mg after 3d storage. More than 50% of the leachable plasticizers and monomers were eluted from the cured resins within 24 and 3 h, respectively. CONCLUSIONS: The amounts of leached plasticizers and residual monomers were extremely large compared with the concentrations of endocrine disrupters and their potentially genotoxic effects. Therefore, it is very important to evaluate the leachability of these compounds from temporary restorative resins.  相似文献   

2.
目的检测Bis-GMA/TEGDMA树脂片经去离子水浸泡后的水解产物。方法 Bis-GMA/TEGDMA单体加入CQ/DMAEMA后光照聚合制备树脂片,将树脂片经37℃恒温去离子水浸泡24 h,其中在1h、3 h、6 h和24 h四个时间点各取1 mL浸泡液,用乙酸乙酯萃取、旋蒸,通过高效液相色谱质谱法(HPLC/MS)检测分析,确定树脂水解产物。结果树脂片的水解产物为双酚A-二甘油醚(Bis-GMA-2MA)、双酚A-二氧代丙基醚(Bis-GMA-2MA-2H2O)、单甲基丙烯酸二缩三乙二醇酯(TEGDMA-MA)和二缩三乙二醇(TEGDMA-2MA)。结论 Bis-GMA/TEGDMA树脂片经去离子水浸泡后树脂可发生水解,水解产物及残余Bis-GMA/TEGDMA树脂单体可析出并释放到去离子水中。  相似文献   

3.
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.  相似文献   

4.
New experimental acrylic resins were prepared by polymerization of MMA in the presence of vinylidene fluoride/hexafluoropropylene copolymer. The amount of residual monomer in the resins prepared by visible light curing, cold curing, and heat curing, at various polymer/monomer ratios, was measured and compared with the usual MMA/PMMA resin. In the visible light cured resins containing 60 or 70 wt% of the fluoropolymer, the amount of residual monomer was less than 0.1%. In the cold cured resins, the amount of residual monomer was very low: 0.2% and 0.7% for the resins containing 70 and 60 wt% of the polymer, respectively. These values were comparable to the usual heat cured MMA/PMMA resins. In the heat cured resins, the amount of residual monomer was the lowest; less than 0.1%, even in the resin consisting of 50 wt% polymer. Thus, we prepared new acrylic resins with much less residual monomer than the usual MMA/PMMA resins.  相似文献   

5.
Residual monomer contents and surface hardness are important factors in determining the serviceability of provisional restorations. The intent of this study was to systemically evaluate the effects of curing conditions on provisional polymethyl methacrylate (PMMA) resins which utilize a free-radical polymerization reaction. Combinations of the three curing factors of temperature, pressure, curing environment (water/air) were adjusted during the fabrication of autopolymerized specimen disks. The initial hardness of tested materials was measured with a microhardness tester 1 h after disc fabrication, and the amounts of residual methyl methacrylate (MMA) released into water were analyzed by reverse-phase HPLC after 7 d of water immersion. Results from multiple regressions showed that curing temperature was the dominant factor in improving resin surface hardness, whereas curing in water was the key factor for reducing the quantity of residual monomer. The pressure factor, which was thought to be critical for managing autopolymerized resins, showed no significant influences on the properties tested. ANOVA results showed that provisional PMMA resins cured in hot water, with or without pressure, significantly reduced the amount of residual MMA elution (up to 80%) and increased the microhardness values (up to 50%).  相似文献   

6.
The purpose of this study was to examine the quality of commercially available Bis-GMA because concerns about Bis-GMA and Bis-GMA-based resins have been recently expressed in dentistry. Four major components and bisphenol A, which is a compound of recent controversy, were quantitatively analyzed using high performance liquid chromatography (HPLC) in three commercial Bis-GMA and six Bis-GMA-based composite resins. The contents of genuine Bis-GMA, Iso-bis-GMA, Bis-GMA-H, and Bis-GMA-M as well as the total content of the four monomers were 45.7-57.5%, 19.9-26.2%, 1.8-5.0%, 0.6-15.0% and 83.7-85.6% in the commercial Bis-GMAs, or 3.8-9.1%, 1.7-4.3%, 0.1-0.5%, 0.1-2.0% and 5.8-14.0% in composite resins, respectively. There were some differences in the composition of the major components between domestic and foreign materials. Bisphenol A contents in the unpolymerized composite resins were 1.5-10.2 micrograms/g resin.  相似文献   

7.
Studies were done to decrease both the water sorption and solubility of visible light cured resin. As monomer, three kinds of cyclophosphazene monomers and three kinds of commercial monomers were prepared to the visible light cured unfilled resins. When these set products were immersed in water, MeOH and THF, water sorption and solubility in water, MeOH sorption and solubility in MeOH, THF sorption, and mechanical properties were examined. Water sorption was increased by degrees for all the monomers. In the cases of 4 PN-(EMA)8, 4 PN-(TF)1-(EMA)7, 4 PN-(TF)2-(EMA)6, Tri-EDMA, BMPEPP and Bis-GMA + Tri-EDMA, the value of solubility in water after 30 days, was 0.16, 0.20, 0.51, 0.65, 0.17 and 0.81% respectively. MeOH sorption showed a tendency to increase, except for Bis-GMA + Tri-EDMA and 4 PN-(TF)2-(EMA)6. Solubility in MeOH after 30 days, for cyclophosphazene monomers and commercial monomers, was 0.09-0.36% and 1.36-5.40%. THF sorption after 30 days, for cyclophosphazene monomers, was small in comparison with that of commercial monomers. Compressive strength was 230-275 MPa in all cases. But, transverse strength, for all the cyclophosphazene monomers, was 45 MPa or below. In the cases of commercial monomers, the value of transverse strength was 55-90 MPa.  相似文献   

8.
The durability of visible light-cured composite resin was examined. Five kinds of commercial redox type composite resin and 7 kinds of visible light-cured composite resin were used and their base monomers were analyzed by HPLC. After the set products were immersed in MeOH, transverse strength and transverse elastic modulus were measured. Furthermore, the MeOH sorption, solubility in MeOH and main soluble component were examined. The main component of the base monomer in all 5 kinds of redox type was Bis-GMA. Seven kinds of visible light-cured composite resin consisted of 4 kinds of Bis-GMA (including BMPEPP) and 3 kinds of UDMA. Both cases of redox type and visible light-cured type of composite resin, when they were immersed in MeOH, transverse strength and transverse elastic modulus decreased. In the case of redox type (Clearfil posterior new bond), the decrease of transverse strength and transverse elastic modulus was small, that is, its base monomer was Bis-GMA, and large quantities of hybrid type filler were mixed. In the case of redox type, transverse strength and transverse elastic modulus showed a tendency to decrease with the increase of MeOH sorption. Solubility of 12 kinds of these composite resins was 0.25-4.78% and its main component in Pyrofil light bond A was BMPEPP, the residual were coincident with the main component of base monomer.  相似文献   

9.
The purpose of this study was to establish a method using FTIR to evaluate the polymerization characteristics of UDMA-based resins. Three kinds of experimental UDMA-based resins were prepared with various molar fractions. IR spectra of the cured film specimens were measured with FTIR before and after extracting residual monomer from each specimen by MeOH. From the IR spectra, the changes in the number of double bonds were measured, with the NH absorbance peak as an internal standard, and the amounts of residual monomers (RM) were calculated. The MeOH-immersed specimens were analyzed by HPLC. The RM measured by FTIR were compared with those measured by HPLC. The RM measured by HPLC were more than those by FTIR. Since these differences could be due to the difference in the area measured, this FTIR estimation method of residual monomers in cured resins using the NH absorbance peak as an internal standard could be an appropriate method when the resin monomer does not contain aromatic compounds.  相似文献   

10.
Water sorption and solubility of six proprietary composite resin materials were assessed, and monomers eluted from the organic matrix during water storage identified. Water sorption and solubility tests were carried out with the following storage times: 4 h, 24 h and 7, 60 and 180 days. After storage, water sorption and solubility were determined. Eluted monomers were analysed by high performance liquid chromatography (HPLC). Correlation between the retention time of the registered peak and the reference peak was observed, and UV-spectra confirmed the identity. The results showed an increase in water sorption until equilibrium for all materials with one exception. The solubility behaviour of the composite resin materials tested revealed variations, with both mass decrease and increase. The resin composition influences the water sorption and solubility behaviour of composite resin materials. The HPLC analysis of eluted components revealed that triethyleneglycol dimethacrylate (TEGDMA) was the main monomer released. Maximal monomer concentration in the eluate was observed after 7 days. During the test period, quantifiable quantities of urethanedimethacrylate (UEDMA) monomer were observed, whereas 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)-phenyl]propane (Bis-GMA) was only found in detectable quantities. No detectable quantities of bisphenol-A were observed during the test period.  相似文献   

11.
Monomer composition was examined to improve durability of matrix resin of visible light cured composite resin. As a monomer, five kinds of cyclophosphazene monomers, two kinds of commercial monomers and a mixture of commercial monomers were prepared to the visible light cured resins. The mechanical properties of these set products were examined with time after immersion in MeOH, an aging accelerating solvent. Compressive strength of the resins using cyclophosphazene monomers tended to decrease with time, but it increased in accordance with the increase of the number of polymerization group. Compressive strength of the resins using commercial monomers tended to decrease, but that using the BMPEPP monomer tended to increase with time. Yield point of the resins with the cyclophosphazene monomer 4 PN-(EMA)8 tended to increase with the time but that of the resins with other cases monomers decreased. The yield point of all three resins made using commercial monomers tended to decrease with time, but the rate of decrease was small for BMPEPP monomer. Compressive elastic modulus of the resins using cyclophosphazene monomers tended to increase with time when the number of polymerization group was 6-8, while it decreased when the number was 4-5. When commercial monomers were used, it tended to decrease with time, but the rate of decrease was small for the BMPEPP monomer. Transverse strength of the resins using cyclophosphazene monomers showed a tendency to decrease with time. When a commercial monomer was used, cracks appeared in the Bis-GMA+Tri-EDMA monomer after 7 days, and with the other two monomers, the transverse strength tended to decrease with time, though the rate of decrease was small for the BMPEPP monomer. Transverse elastic modulus tended to decrease with time, but the rate of decrease was small for the BMPEPP monomer.  相似文献   

12.
Hashimoto M, Nagano F, Endo K, Ohno H. Measurements of volatile compound contents in resins using a moisture analyzer. Eur J Oral Sci 2010; 118: 94–99. © 2010 The Authors. Journal compilation © 2010 Eur J Oral Sci
The contents of volatile adhesive compounds, such as water, solvents, and residual unpolymerized monomers, affect the integrity and durability of adhesive bonding. However, there is no method available that can be used to rapidly assess the residual solvent or water contents of adhesive resins. This study examined the effectiveness of a digital moisture analyzer to measure the volatile compound contents of resins. Five self-etching adhesives and seven experimental light-cured resins prepared with different contents (0, 10, and 20% by weight) of water or solvents (acetone and ethanol) were examined in this study. The resins were prepared using different methods (with and without air blast or light-curing) to simulate the clinical conditions of adhesive application. Resin weight changes (% of weight loss) were determined as the residual volatile compound contents, using the moisture analyzer. After the measurements, the resin films were examined using a scanning electron microscope. The weight changes of the resins were found to depend on the amount of water or solvents evaporating from the resin. Water and solvents were evaporated by air blast or light-curing, but some of the water and solvents remained in the cured resin. The moisture analyzer is easy to operate and is a useful instrument for using to measure the residual volatile compound contents of adhesive resin.  相似文献   

13.
Rods of a visible-light-cured dental composite resin were photo-polymerized and immersed in water at 37 degrees C for 7 days. The residual monomers (TEGDMA and Bis-GMA) trapped in the set composite and those eluted into water were analysed by gas-liquid chromatography. It became evident that minor amounts of the residual monomers dissolved in water, but that most residual monomers remained in the set composite. Extension of the irradiation period contributed to the significant reduction in the residual monomer level and its elution into water.  相似文献   

14.
Light-cured opaque resins with excellent physical properties were prepared using five types of monomer liquid and titanium dioxide as the powder. The five opaque resin monomer liquid had the following monomer compositions. Methyl methacrylate (MMA)/di(methacryloxyethyl) trimethylhexamethylene diurethane (UDMA) = 70/30 (M-U), MMA/neopenthylglycol dimethacrylate (NPG)/UDMA = 45/45/10 (M-N-U), UDMA/MMA = 70/30 (U-M), 2,2-bis (4-methacryloxypolyethoxy phenyl) propane (2.6 E)/2,2-bis [4-(3-methacryloxy-2-hydroxy propoxy) phenyl] propane (Bis-GMA)/triethyleneglycol dimethacrylate (3 G) = 60/35/5(2.6-B-3) and 3 G/UDMA = 70/30 (3-U) by weight. The bond strength, photo-curability and handling properties of the opaque resin were improved. Three MMA-based opaque resins showed nearly the same values in Knoop hardness number, diametral tensile strength and shear bond strength. The depth of cure increased with the decrease in MMA content of monomer composition, while the amount of residual monomer decreased. The 2.6-B-3 opaque resin had nearly the same properties in depth of cure and Knoop hardness number as the 3-U opaque resin. However, the 2.6-B-3 and 3-U opaque resins had a diametral tensile strength more than twice as high as that of the U-M opaque resin. The bond strength of three MMA-based opaque resins showed 0MPa after 5,000 thermocycles, while the 2.6-B-3 opaque resin, about 16 MPa, and the 3-U opaque resin, about 25 MPa. Therefore, the bond strength of the opaque resin was influenced by monomer composition. 3G-UDMA opaque resin showed excellent physical properties and may be clinically acceptable to bond fixed prosthodontic composite.  相似文献   

15.
OBJECTIVE: To study the aging of neat resins, prepared from bis-GMA, UDMA, D(3)MA or a mixture of bis-GMA/UDMA/D(3)MA (65/20/15 w/w/w), in water or 75% (v/v) ethanol/water 37 degrees C. Also the study of aging of Heliomolar RO, which is a radiopaque, microfilled, light cured composite, the resin matrix of which is the copolymer of bis-GMA/UDMA/D(3)MA (65/20/15 w/w/w). METHODS: Samples of neat resins and Heliomolar RO prepared by light curing were immersed in water or 75% (v/v) ethanol/water 37 degrees C, for 1, 7 or 30 days. Then the flexural and tensile strength were determined. The fractured surface of samples after the flexural tests was observed by scanning electron microscopy. RESULTS: Bis-GMA and copolymer resin did not showed any significant change in mechanical properties after immersion in water or 75% (v/v) ethanol/water 37 degrees C, for 30 days. On the contrary UDMA, D(3)MA and the composite Heliomolar RO showed a significant decrease. SIGNIFICANCE: The results obtained showed that the effect of aging in water or ethanol/water solution on mechanical properties of a light cured dimethacrylate resin depends on the chemical structure of resin. In the case of resin composite this effect depends on the filler-matrix bond strength.  相似文献   

16.
alpha-Methylene-gamma-butyrolactone (MBL), which can be described as the cyclic analog of methyl methacrylate, exhibits greater reactivity in free radical polymerizations than conventional methacrylate monomers. Unfilled resin formulations composed of Bis-GMA/MBL or Bis-GMA/TEGDMA/MBL were light-cured. The effect of the more reactive methylene lactone monomer on mechanical properties and the degree of conversion of the polymers was examined. The infrared absorption bands for the carbon-carbon double bonds of MBL and the methacrylate monomers are well resolved and allow the conversion of each component to be calculated individually. The incorporation of a small amount of MBL (5 w/o) to Bis-GMA significantly increased the conversion; however, additional MBL (10 to 30 w/o) did not further increase the Bis-GMA conversion level. This appears to indicate an incompatibility between MBL and the bulky Bis-GMA monomer. Addition of 10 w/o MBL to Bis-GMA/TEGDMA (7:3) resulted in a cured resin with 71% methacrylate and 75% overall conversion efficiencies compared with the 57% conversion of the control formulation. The diametral tensile and the transverse strengths were approximately 10% greater for the MBL resin compared with the Bis-GMA/TEGDMA control; however, these differences were not statistically significant. The synthesis and polymerization of several substituted methylene lactones was also studied.  相似文献   

17.
Bisphenol-A content of resin monomers and related degradation products   总被引:1,自引:1,他引:0  
Recently, it was reported that Bisphenol-A (BPA) was released from one fissure sealant (Delton) into saliva causing estrogenic activity in vitro. The aim of this study was to chemically analyze the BPA content of different fissure sealant resin monomers and their release of BPA under hydrolytic conditions. BPA content was first measured in commercially available monomers of bisphenol-A glycidyldimethacrylate (Bis-GMA), bisphenol-A dimethacrylate (Bis-DMA) and bisphenol-A diglycidylether (BADGE). Then, Bis-GMA-monomer and Bis-DMA-monomer in methanol were subjected to pH values of 0 to 11 for 30 minutes at 50°C, to porcine liver esterase, and to pooled saliva for up to 24 hours. The BPA-content was determined by high-performance liquid chromatography (HPLC). Bis-GMA-monomer and BADGE-monomer from one manufacturer did not contain any detectable amounts of BPA (≤2 ppm); Bis-DMA and BADGE-monomer from a second manufacturer contained BPA quantities of 4–155 ppm. For Bis-GMA-monomer, no BPA could be detected under any hydrolytic conditions chosen (detection limit: ≤1%). For Bis-DMA-monomer an increase of BPA was observed at pH 11, resulting in a conversion of approx. 100% Bis-DMA to BPA. When Bis-DMA was subjected to esterase, a conversion of 82.5 % resulted after 24 h; saliva led to an 81.4 % conversion of Bis-DMA after 24 h. Hence, we conclude that the results reported in the literature may be attributed to the Bis-DMA-content of the fissure sealant tested (Delton). No BPA-release is expected under physiologic conditions from fissure sealants based on Bis-GMA if pure base monomers are used. Received: 16 June 1999 / Accepted: 19 July 1999  相似文献   

18.
In order to ascertain whether an estrogenic bisphenol A is produced from bisphenol A-related monomers by chemical-induced hydrolysis and to clarify their hydrolytic mechanisms, bisphenol A dimethacrylate (Bis-DMA) and bisphenol A bis(glycidyl methacrylate) (Bis-GMA) were reacted with phosphoric acid, hydrochloric acid, and sodium hydroxide in methanol or methanol/water mixed media at 37 degrees C. Amounts of monomethacrylate intermediates as well as bisphenol A (BPA) were determined by the use of high-performance liquid chromatography (HPLC), and time-conversion curves of hydrolytic products were prepared. BPA and bisphenol A monomethacrylate were produced by acid-catalyzed hydrolysis of Bis-DMA. Bis-GMA was partly converted into monomethacrylate by phosphoric acid and into monomethacrylate and 2,2-bis[4-(2,3-dihydroxypropoxy) phenyl]propane (BHP) by hydrochloric acid. Hydrolytic reactions by sodium hydroxide were completed almost within 1 day, resulting in the production of BPA from Bis-DMA, and BHP from Bis-GMA. No BPA was formed from Bis-GMA by chemical-induced hydrolysis. The hydrolytic behaviors of these monomers were discussed.  相似文献   

19.
目的:研究纳米义齿基托树脂在使用有机蒙脱土(OMMT)增强义齿基托的机械性能后,材料中OMMT的含量对固化后材料中残留甲基丙烯酸甲酯(MMA)含量的影响,并确定合适的OMMT的混合比例,使固化后材料的机械性能得到较好提高的同时残留MMA含量也在可接受的范围内。同时对该固化材料在水中MMA的释放量进行测定。方法:材料中残留的MMA用丙酮进行抽提,材料在水中释放的MMA用氯仿萃取。抽提液和萃取液用气相色谱测定其中MMA的浓度。结果:OMMT的量对固化材料中残留MMA的量有显著性影响(P<0.05),随着固化材料中OMMT的量的增加,残留MMA的量也逐渐增加。当OMMT的混合比例为1wt%时,不仅材料的机械性能的到了较好提升,材料中的残留MMA的量也在YY0270-2003标准(最大2.2wt%)范围内。放置于37℃水中7d后,MMA的释放量随时间的增加趋于稳定;观察3周,MMA水中释放量小于用丙酮抽提时所测得的残留MMA量。结论:固化材料中MMA的含量随着OMMT含量的增加而增加。材料在水中的MMA释放量小于用丙酮抽提时所测得的MMA量。  相似文献   

20.
Plasma arc light units for curing resin composites have been introduced with the claim of relatively short curing times. The purpose of the present study was to measure and compare elution of monomers from an experimental BisGMA-TEGDMA resin and a commercial resin composite when cured with a halogen unit and when cured with a plasma arc unit. Specimens of the materials were immersed in methanol, and the amounts of monomers released with time were analyzed by HPLC. By use of Fick's laws of diffusion, the amount of eluted monomers from the specimen at infinity was estimated. The elution from resin specimens and from resin composite specimens cured with the plasma arc light unit was 7 and 4 times higher, respectively, compared to the elution from specimens cured with the halogen unit. It was concluded that the plasma arc light curing unit did not provide optimal cure when used as recommended by the manufacturer.  相似文献   

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