Posts Tagged ‘bisEMA’

Optimal Diluent and Base Methacrylate Combinations

Thursday, September 15th, 2011
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Influence of the base and diluent methacrylate monomers on the polymerization stress and its determinants

N. R. G. Fróes-Salgado, L. C. Boaro, B. Pick, C. S. Pfeifer, C. E. Francci, M. M. Méier, R. R. Braga.  Journal of Applied Polymer Science.

Overview:

The correct pairing of methacrylate diluents and resins can optimize properties like polymerization stress, volumetric shrinkage, degree of conversion, maximum rate of polymerization, and elastic modulus in composite formulations.

Abstract:

The aim of this study was to evaluate the effect of the association between bisphenol-A diglycidyl dimethacrylate (BisGMA) or its ethoxylated version (BisEMA) with diluents derived from the ethylene glycol dimethacrylate (EGDMA), with increasing number of ethylene glycol units (1: EGDMA, 2: DEGDMA, 3: TEGDMA, or 4: TETGDMA), or trimethylol propane trimethacrylate (TMPTMA) or 1,10-decanediol dimethacrylate (D3MA) on polymerization stress, volumetric shrinkage, degree of conversion, maximum rate of polymerization (Rpmax), and elastic modulus of experimental composites. BisGMA containing formulations presented lower shrinkage and stress but higher modulus and Rpmax than those containing BisEMA. TMPTMA presented the lowest stress among all diluents, as a result of lower conversion. EGDMA, DEGDMA, TEGDMA, and TETGDMA presented similar polymerization stress which was higher than the stress presented by D3MA and TMPTMA. D3MA presented similar conversion when copolymerized with both base monomers. The other diluents presented higher conversion when associated with BisEMA. EGDMA showed similar shrinkage compared with DEGDMA and higher than the other diluents. The lower conversion achieved by TMPTMA did not jeopardize its elastic modulus, similar to the other diluents. Despite the similar conversion presented by D3MA in comparison with EGDMA and DEGDMA, its lower elastic modulus may limit its use. Rather than proposing new materials, this study provides a systematic evaluation of off the shelf monomers and their effects on stress development, as highlighted by the analysis of conversion, shrinkage and modulus, to aid the optimization of commercially available materials. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011


LINK:  http://onlinelibrary.wiley.com/doi/10.1002/app.34947/full

Article first published online: 1 SEP 2011.  DOI: 10.1002/app.34947


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Esstech Resins in Antibacterial Nanocomposite

Monday, July 11th, 2011
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Development of an antimicrobial resin—A pilot study

Catherine Fan, Lianrui Chu, H. Ralph Rawls, Barry K. Norling, Hector L. Cardenas, Kyumin Whang

Dental Materials.  Volume 27, Issue 4, Pages 322-328 (April 2011)

Summary

To demonstrate that silver nanoparticles (AgNPs) could be synthesized in situ in acrylic dental resins.

Methods: Light-cure (LC; bisphenol A glycidyl methacrylate, tetraethyleneglycol dimethacrylate, bisphenol A ethoxylate dimethacrylate blend) and chemical-cure systems (CC; orthodontic denture resin) were used to synthesize AgNPs using different concentrations of Ag benzoate (AgBz).

Results: Rockwell hardness for LC resins showed that resins could be cured with up to 0.15% AgBz, while the hardness of CC resins were unaffected in the concentrations tested. UV–Vis spectroscopy and transmission electron microscopy confirmed the presence of AgNPs in both LC and CC resins. Generally, CC resins had better distribution of and much smaller AgNPs as compared to LC resins overall. In some samples, especially in LC resins, nanoclusters were visible. An in vitro release study over four-weeks showed that CC resins released the most Ag+ ions, with release detected in all samples. However, LC resins only released Ag+ ions when AgBz concentration was greater than 0.1% (w/w). AgNP-loaded CC resins made with 0.2 and 0.5% (w/w) AgBz were tested for antibacterial activity in vitro against Streptococcus mutans, and results showed 52.4% and a 97.5% bacterial inhibition, respectively. Further work is now warranted to test mechanical properties and to optimize the initiator system to produce commercially useful dental and medical resins.

Significance:  Success in this work could lead to a series of antimicrobial medical and dental biomaterials that can prevent secondary caries and infection of implants.


LINK:  http://www.demajournal.com/article/S0109-5641%2810%2900475-6/abstract


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X-726-0000, Suitable HEMA Replacement

Tuesday, July 5th, 2011
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A new approach in self-etching adhesive formulations: Replacing HEMA for surfactant dimethacrylate monomers

Cesar Henrique Zanchi,, Eliseu Aldrighi Münchow, Fabricio Aulo Ogliari, Rodrigo Varella de Carvalho, Stefano Chersoni, Carlo Prati, Flávio Fernando Demarco, Evandro Piva

Article first published online: 28 JUN 2011.  DOI: 10.1002/jbm.b.31871. © 2011 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 2011.

Abstract

This study evaluated the influence of surfactant dimethacrylates (SD) on the resin-to-dentin microtensile bond strength (μTBS) and characterized the interfacial micromorphology of the hybrid layer of the experimental HEMA-free self-etching systems. Five experimental HEMA-free two-step self-etching systems containing different SD (Bis-EMA 10, Bis-EMA 30, PEG 400, PEG 1000, and PEG 400 UDMA [Esstech Code X-726-0000]) and a HEMA-containing system (control) were compared. Each experimental adhesive system was applied and resin composite restorations were incrementally built up in bovine incisors. After 24 h, restored teeth were sectioned to obtain 24 sticks per group. Thereafter, the specimens were subjected to the μTBS test. Data (MPa) were analyzed by One-way ANOVA and Tukey’s test. Adhesive-dentin interfaces were analyzed through Scanning Electron Microscopy (SEM). The adhesive system formulated with PEG 400 UDMA produced μTBS similar to the HEMA-containing group and statistically higher than the HEMA-free groups. Similar failure percentages were observed in the PEG 400 UDMA and the control group. In the SEM analysis, all the adhesive systems presented similar partially demineralized hybrid layer (1.5–3.0 μm thickness) with well-formed resin tags. All SD presented reasonable initial μTBS, with the PEG 400 UDMA being a promising monomer to be considered as a HEMA substitute in adhesive systems compositions.


Link:  http://onlinelibrary.wiley.com/doi/10.1002/jbm.b.31871/full

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PMGDM / UDMA Used in Remineralization Applications

Friday, September 10th, 2010
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Effects of adhesive, base and diluent monomers on water sorption and conversion of experimental resins

Sabine H. Dickens, Glenn M. Flaim, Cynthia J.E. Floyd

Dental Materials Volume 26, Issue 7, Pages 675-681 (July 2010)

Objectives: To establish the relationship of resin composition and resin hydrophilicity (indicated by solubility parameters and logP) to water sorption (WS), solubility, and degree of double bond conversion (DC) of resin mixtures designed for adhesive restoratives by varying the concentration of pyromellitic glycerol dimethacrylate (PMGDM) and various co-monomers.

Methods: Sixteen resin mixtures were prepared with (30–70) mass fraction % PMGDM. At given PMGDM concentrations there were up to five compositions with increasing logP. Polymer disks (13mm×0.7mm) were exposed to 96% relative humidity (RH) to determine water sorption in humid atmosphere (WSH) and subsequently immersed in water for immersion water sorption (WSI) and solubility. DC was assessed by near infrared spectroscopy.

Results: WSI was somewhat higher than WSH, which ranged from (2.1 to 5.3) mass fraction %. Both data were positively correlated to PMGDM concentrations [Pearson correlation, p<0.02; R2=0.74, 0.73 (WSI)] and solubility (R2=0.64), but not to logP. When grouped by structural similarities, i.e., base resins with bisphenol A core (Group B), Group O containing diluent monomers, or Group U containing urethane dimethacrylate, WS within each group was inversely correlated to logP with R2=0.98, 0.81, 0.95, and WS/solubility correlation improved with R2=0.88, 0.92 and 0.75, respectively. Solubility ranging from 0.3% to 2.3% was inversely related to DC (r=−0.872). Conversion ranging from 41% to 81% was lower for resins with high base monomer concentrations and highest in mixtures with UDMA.

Significance: LogP was a good predictor of WS after grouping the resins according to functional, compositional and structural similarities. WS and conversion were reasonably well predicted from Hoy’s solubility parameters and other physical resin properties.

Link:  http://www.demajournal.com/article/S0109-5641%2810%2900066-7/abstract


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Alternative Photoinitiator Assists in Camphorquinone Cure

Tuesday, July 27th, 2010
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Degree of conversion and color stability of the light curing resin with new photoinitiator systems

Dong-Hoon Shin, H. Ralph Rawls

Dental Materials, August 2009 (Vol. 25, Issue 8, Pages 1030-1038)

Objectives: This study investigated p-octyloxy-phenyl-phenyl iodonium hexafluoroantimonate (OPPI) as a photoinitiator, in combination with camphorquinone/amine photoinitiation systems, for use with di(meth)acrylate-based composite resins. The investigation determined if the inclusion of OPPI improved degree and rate of conversion, initial color and color stability of a representative composite resin dental material.

Methods: Camphorquinone (CQ) and OPPI were combined in various proportions with the amine co-initiator 2-dimethylaminoethyl methacrylate (DMAEMA) and used at two levels in which CQ+OPPI+DMAEMA=1wt.% or 3wt.% to photoinitiate a BisGMA/BisEMA/TEGDMA (37.5:37.5:25wt.%) monomer blend. Monomer mixture (GTE) was made by mixing 37.5wt.% BISGMA (lot # 568-21-07, ESSTECH, Essington, PA), 37.5wt.% BISEMA (lot # 474-32-02, ESSTECH), and 25wt.% TEGDMA (lot # 597-23-02, ESSTECH). A total of eight groups (four groups for each level of total photoinitiator, 1% and 3%) were tested according to the following proportion of components in the photoinitiator system: Each monomer was polymerized using a quartz-halogen curing unit (Demetron 400, Demetron Research Corp., Danbury, CT) with an intensity of 400mW/cm2 for 5s, 20s, 40s, 60s, 300s and their conversion levels (DC) were determined at each exposure time using a Fourier transform infrared spectrophotometer (FTIR). To examine color stability, experimental composite resins were made by mixing 3.2% silanated barium glass (78wt.%, average filler size; 1μm) with each monomer system, except both CQ only group and 1% CO group, which were found to cure insufficiently to be able to prepare useful specimens. Disk-shaped samples (10mm in diameter and 1.5mm in thickness) were made and stored under the conditions of dry or saline solution at room temperature (25°C) or 60°C water bath. Each CIELAB scale was determined with a colorimeter (CHROMA METER CR-400) at the time of baseline (day after curing), 1 week, 2 weeks, and 4 weeks later.

Results: The high level (3%) photoinitiated groups exhibited greater DC than the low level (1%) groups. In the 3% group, the COA group showed the fastest and the highest DC, while in the 1% group the CA and COA groups showed the greatest DC. In the color stability test, both CA groups were darker and more yellow than the CO and COA groups. Color was more stable in composite resins containing OPPI than those containing only the CQ and amine components. The least color change (greatest color stability) was found using 25°C saline solution aging, and the most change (least color stability) occurred using 60°C dry air aging.

Significance: This study suggests that OPPI can be used to replace the amine in a given CQ/amine photoinitiator system to accelerate cure rate, increase conversion, reduce initial color and increase color stability.

Link: http://www.demajournal.com/article/S0109-5641%2809%2900139-0/abstract


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BisGMA:TEGDMA:UDMA Composites Present Optimal Conversion and Mechanical Properties.

Friday, May 21st, 2010
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Bis-GMA  co-polymerizations: Influence on conversion, flexural properties, fracture toughness and susceptibility to ethanol degradation of experimental composites

Carmem S. Pfeifer, Laura R. Silva, Yoshio Kawano, Roberto R. Braga

Dental Materials Volume 25, Issue 9, Pages 1136-1141 (September 2009)

Objectives

The aim of this study was to evaluate the influence of monomer content on fracture toughness (KIc) before and after ethanol solution storage, flexural properties and degree of conversion (DC) of bisphenol A glycidyl methacrylate (Bis-GMA) co-polymers.

Methods

Five formulations were tested, containing Bis-GMA (B) combined with TEGDMA (T), UDMA (U) or Bis-EMA (E), as follows (in mol%): 30B:70T; 30B:35T:35U; 30B:70U; 30B:35T:35E; 30B:70E. Bimodal filler was introduced at 80wt%. Single-edge notched beams for fracture toughness (FT, 25mm×5mm×2.5mm, a/w=0.5, n=20) and 10mm×2mm×1mm beams for flexural strength (FS) and modulus (FM) determination (10mm×2mm×1mm, n=10) were built and then stored in distilled water for 24h at 37°C. All FS/FM beams and half of the FT specimens were immediately submitted to three-point bending test. The remaining FT specimens were stored in a 75%ethanol/25%water (v/v) solution for 3 months prior to testing. DC was determined with FT-Raman spectroscopy in fragments of both FT and FS/FM specimens at 24h. Data were submitted to one-way ANOVA/Tukey test (α=5%).

Results

The 30B:70T composite presented the highest KIc value (in MPam1/2) at 24h (1.3±0.4), statistically similar to 30B:35T:35U and 30B:70U, while 30B:70E presented the lowest value (0.5±0.1). After ethanol storage, reductions in KIc ranged from 33 to 72%. The 30B:70E material presented the lowest reduction in FT and 30B:70U, the highest. DC was similar among groups (69–73%), except for 30B:70U (52±4%, p<0.001). 30B:70U and 30B:35T:35U presented the highest FS (125±21 and 122±14MPa, respectively), statistically different from 30B:70T or 30B:70E (92±20 and 94±16MPa, respectively). Composites containing UDMA or Bis-EMA associated with Bis-GMA presented similar FM, statistically lower than 30B:35T:35U.

Significance

Composites formulated with Bis-GMA:TEGDMA:UDMA presented the best compromise between conversion and mechanical properties.

This version was accepted March 23, 2009.

Link, http://www.demajournal.com/article/S0109-5641%2809%2900162-6/abstract


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Camphorquinone Decomposition Rates Vary Among UDMA and BisGMA/TEGDMA Formulations

Thursday, March 18th, 2010
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Photobleaching of camphorquinone during polymerization of dimethacrylate-based resins

Silvana Asmusen, Gustavo Arenas, Wayne D. Cook, Claudia Vallo

Dental Materials, December 2009 (Vol. 25, Issue 12, Pages 1603-1611)

Abstract: Objective: The aim of this study was to compare the photobleaching rate of CQ in different dental resins. Methods: The photodecomposition rate of CQ/amine system in bis-GMA/TEGDMA, bis-EMA and UDMA polymerizing monomers was evaluated at different light intensities. The photobleaching of the CQ was studied by monitoring the decrease in light absorption as a function of continuous irradiation time. The absorption changes were assessed by recording the transmitted light that passed through samples of monomers containing CQ/amine. Results: Complete photobleaching of CQ was observed in all the monomer tested and the rate constant for the photobleaching was proportional to the radiation intensity. Hydrogen abstraction from amines by the excited CQ state via electron transfer and direct hydrogen abstraction from monomer structures were involved in the CQ photoreduction. CQ was photobleached in the absence of coinitiator in a dimethacrylate monomer containing a carbamate functional group (UDMA). This behavior was attributed to the presence of labile hydrogen atoms in the UDMA monomer. The CQ photobleaching rate constant in UDMA containing CQ/amine was similar to that in UDMA in the absence of amine. Moreover, the efficiency of CQ to photoinitiate the polymerization of UDMA in the absence of amine demonstrated that the radicals derived from the UDMA monomer via hydrogen abstraction are highly reactive toward double bonds.

Significance: CQ photoinitiates the polymerization of the UDMA monomer in the absence of amine and the efficiency of this process is comparable to that of traditional bis-GMA and bis-EMA monomers activated with CQ/amine.

Link:  http://www.demajournal.com/article/S0109-5641(09)00285-1/abstract


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