scholarly journals A Low-Viscosity BisGMA Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties

Materials ◽  
2021 ◽  
Vol 14 (2) ◽  
pp. 338
Author(s):  
Ali Alrahlah ◽  
Abdel-Basit Al-Odayni ◽  
Haifa Fahad Al-Mutairi ◽  
Bashaer Mousa Almousa ◽  
Faisal S. Alsubaie ◽  
...  
Keyword(s):  
Substantial Reduction ◽  
Triethylene Glycol ◽  
High Viscosity ◽  
Resin Matrix ◽  
Resonance Spectroscopy ◽  
Dental Resin ◽  
Triethylene Glycol Dimethacrylate ◽  
Oh Groups ◽  
Low Viscosity ◽  
13C Nuclear Magnetic Resonance

This study aimed to synthesize new bisphenol A-glycidyl methacrylate (BisGMA) derivatives, targeting a reduction in its viscosity by substituting one of its OH groups, the leading cause of its high viscosity, with a chlorine atom. Hence, this monochloro-BisGMA (mCl-BisGMA) monomer was synthesized by Appel reaction procedure, and its structure was confirmed using Fourier transform infrared spectroscopy, 1H and 13C-nuclear magnetic resonance spectroscopy, and mass spectroscopy. The viscosity of mCl-BisGMA (8.3 Pa·s) was measured under rheometry conditions, and it was found to be more than 65-fold lower than that of BisGMA (566.1 Pa·s) at 25 °C. For the assessment of the viscosity changes of model resins in the presence of mCl-BisGMA, a series of resin matrices, in which, besides BisGMA, 50 wt % was triethylene glycol dimethacrylate, were prepared and evaluated at 20, 25, and 35 °C. Thus, BisGMA was incrementally replaced by 25% mCl-BisGMA to obtain TBC0, TBC25, TBC50, TBC75, and TBC100 blends. The viscosity decreased with temperature, and the mCl-BisGMA content in the resin mixture increased. The substantial reduction in the viscosity value of mCl-BisGMA compared with that of BisGMA may imply its potential use as a dental resin matrix, either alone or in combination with traditional monomers. However, the various properties of mCl-BisGMA-containing matrices should be evaluated.

Simulated Body Fluid Sorption and Solubility of Silica Reinforced Dental Resin Composites

2013 ◽  
Vol 795 ◽  
pp. 626-630 ◽  
Author(s):  
Saad Omar Alsharif ◽  
Md Akil Hazizan ◽  
Nasser Abbas Abd El-Aziz ◽  
Zainal Arifin Ahmad
Keyword(s):  
Simulated Body Fluid ◽  
Body Fluid ◽  
Resin Composite ◽  
Triethylene Glycol ◽  
Filler Loading ◽  
Resin Matrix ◽  
Resin Composites ◽  
Dental Resin ◽  
Triethylene Glycol Dimethacrylate ◽  
Dental Resin Composites

The aim of this study is to investigate the effect of filler loading on the sorption and solubility of Simulated Body Fluid (SBF) of self-prepared micro dental resin composites. The prepared resin composite was based on silica (SiO2) particles and bisphenol-a-glycidyl methacrylate (Bis-GMA) as a base monomer and triethylene glycol dimethacrylate (TEGDMA) as a co-monomer. The filler was mixed with monomers, in proportions of 40, 50 and 60 wt.%. A resin matrix containing 0 wt.% filler was used as the control composition to evaluate the effect of filler loading on the sorption and solubility of SBF. The experimental methods were based on the procedure mentioned in the ISO 4049 (2009) standard for dentistry-Polymer-based restorative Materials. The sorption and solubility of resin matrix/SiO2composite decreased gradually as the filler loading increased. The increase of filler loading showed significant differences in the sorption and solubility as tested by ANOVA (P= 0.000).

Influence of Silica and Zirconia Particles as Filler Loading on the Radiopacity of Dental Resin Composites

2012 ◽  
Vol 620 ◽  
pp. 345-349 ◽  
Author(s):  
Saad Omar Alsharif ◽  
Md Akil Hazizan ◽  
Nasser Abbas Abd El-Aziz ◽  
Zainal Arifin Ahmad
Keyword(s):  
Glycidyl Methacrylate ◽  
Triethylene Glycol ◽  
Filler Loading ◽  
Aluminum Plate ◽  
Resin Matrix ◽  
Resin Composites ◽  
Dental Resin ◽  
Triethylene Glycol Dimethacrylate ◽  
Dental Resin Composites ◽  
Base Resin

The aim of this study is to evaluate the radiopacity of silica (SiO2) and zirconia (ZrO2) particles dispersed in a bisphenol-a-glycidyl methacrylate (Bis-GMA) as a base resin and triethylene glycol dimethacrylate (TEGDMA) as a diluent. The fillers were mixed separately with bis-GMA/TEGDMA monomers, in proportions of 40, 50 and 60 wt.%. A resin matrix containing 0 wt.% filler was used as the control composition to evaluate the effect of filler loading on the radiopacity. Samples of the composites with 2.5 mm thickness were compared their radiopacity with the same thickness of the standard aluminum plate. The radiopacity of both resin matrix/SiO2and resin matrix/ZrO2composites increased gradually as the filler loading increased. The resin matrix/ZrO2composites possessed radiopacity higher than the standard aluminum plate. The increase of filler loading showed highly significant differences in the radiopacity as tested by ANOVA (P= 0.000).

scholarly journals A Novel Organic–Inorganic Hybrid Admixture for Increasing Flowability and Reducing Viscosity of Ultra-High Performance Paste

Materials ◽  
2020 ◽  
Vol 13 (15) ◽  
pp. 3385 ◽  
Author(s):  
Min Wang ◽  
Hao Yao
Keyword(s):  
Steric Hindrance ◽  
High Performance ◽  
High Performance Concrete ◽  
High Viscosity ◽  
Inorganic Hybrid ◽  
Oh Groups ◽  
Low Viscosity ◽  
Binder Ratio ◽  
The One ◽  
Water Binder Ratio

The low flowability and high viscosity of ultra-high performance concrete (UHPC), which is mainly caused by the silica fume (SF) agglomeration and low water–binder ratio, is a severe defect in its engineering applications. Herein, a novel organic–inorganic hybrid (OIH) admixture was synthesized by grafting comb-like polycarboxylate ether (PCE) onto the surface of SF. On the one hand, PCE-grafting could effectively prevent SF agglomeration and improve the dispersion of SF core. The reason being the consumption of polar silicon hydroxyl (Si-OH) groups on the surface of SF and the steric hindrance effect generated from PCE arms. On the other hand, OIH admixture could adsorb onto the surface of cement and SF particles by electrostatic interaction, exhibiting stronger steric hindrance effect than traditional comb-like PCE. As a result, UHPC system with this star-like OIH admixture presented high flowability and low viscosity at low water–binder ratio (0.18).

scholarly journals Correlation between the degree of conversion and the elution of leachable components from dental resin-based cements

2011 ◽  
Vol 76 (9) ◽  
pp. 1307-1323 ◽  
Author(s):  
Kosovka Obradovic-Djuricic ◽  
Vesna Medic ◽  
Marina Radisic ◽  
Mila Lausevic
Keyword(s):  
Triethylene Glycol ◽  
Degree Of Conversion ◽  
Cement Matrix ◽  
Dental Resin ◽  
Resin Cements ◽  
Triethylene Glycol Dimethacrylate ◽  
Urethane Dimethacrylate ◽  
Post Hoc ◽  
Composite Cements ◽  
One Way Anova

This study examined the possible correlation between the degree of conversion (DC) and the amount of substances eluted from three commercial cured resin-based cements. The DC of the various resin-based cements was measured by Raman spectroscopy, while the quantity of unreacted monomers released from the cement matrix (triethylene glycol dimethacrylate, TEGDMA, urethane dimethacrylate, UDMA, 2- hydroxyethyl methacrylate, HEMA and bis phenol A) was determined by high pressure liquid chromatography (HPLC). The obtained results, after multiple statistical evaluation (one way ANOVA, LSD post hoc test), showed no significant differences in the DC values between the resin cements. On the contrary, the results of the HPLC analysis depicted statistically significant differences between the three materials with respect to the amount of leached monomers. In addition, no correlation between the DC and the amount of eluted substances from the tested cured composite cements was found.

scholarly journals Bioenergetic Impairment of Triethylene Glycol Dimethacrylate- (TEGDMA-) Treated Dental Pulp Stem Cells (DPSCs) and Isolated Brain Mitochondria are Amended by Redox Compound Methylene Blue

Materials ◽  
2020 ◽  
Vol 13 (16) ◽  
pp. 3472
Author(s):  
Krisztina Mikulás ◽  
Timea Komlódi ◽  
Anna Földes ◽  
Gergely Sváb ◽  
Gergő Horváth ◽  
...  
Keyword(s):  
Stem Cells ◽  
Methylene Blue ◽  
Membrane Potential ◽  
Dental Pulp ◽  
Triethylene Glycol ◽  
Dental Pulp Stem Cells ◽  
Resin Matrix ◽  
Glycol Dimethacrylate ◽  
Triethylene Glycol Dimethacrylate ◽  
Isolated Mitochondria

Background: Triethylene glycol dimethacrylate (TEGDMA) monomers released from resin matrix are toxic to dental pulp cells, induce apoptosis, oxidative stress and decrease viability. Recently, mitochondrial complex I (CI) was identified as a potential target of TEGDMA. In isolated mitochondria supported by CI, substrates oxidation and ATP synthesis were inhibited, reactive oxygen species production was stimulated. Contrary to that, respiratory Complex II was not impaired by TEGDMA. The beneficial effects of electron carrier compound methylene blue (MB) are proven in many disease models where mitochondrial involvement has been detected. In the present study, the bioenergetic effects of MB on TEGDMA-treated isolated mitochondria and on human dental pulp stem cells (DPSC) were analyzed. Methods: Isolated mitochondria and DPSC were acutely exposed to low millimolar concentrations of TEGDMA and 2 μM concentration of MB. Mitochondrial and cellular respiration and glycolytic flux were measured by high resolution respirometry and by Seahorse XF extracellular analyzer. Mitochondrial membrane potential was measured fluorimetrically. Results: MB partially restored the mitochondrial oxidation, rescued membrane potential in isolated mitochondria and significantly increased the impaired cellular O2 consumption in the presence of TEGDMA. Conclusion: MB is able to protect against TEGDMA-induced CI damage, and might provide protective effects in resin monomer exposed cells.

Synthesis and Characteristics of Dental Composites with Novel Bis-GMA Derivate as a Resin Base

2013 ◽  
Vol 745-746 ◽  
pp. 442-446 ◽  
Author(s):  
Rui Li Wang ◽  
Mo Zhu ◽  
Sheng Liu ◽  
Feng Wei Liu ◽  
Xiao Ze Jiang ◽  
...  
Keyword(s):  
Adverse Effects ◽  
Triethylene Glycol ◽  
High Viscosity ◽  
Dental Composites ◽  
Resin Matrix ◽  
Hydroxyl Groups ◽  
Acetyl Group ◽  
Matrix Differential ◽  
Dental Restorative ◽  
Kinetics Of

2,2-bis [4-(2-hydroxy-3-methacryloyloxypropoxy) pheny propane (Bis-GMA) and triethylene glycol dimethacrylate (TEGDMA) have been commonly used as a viscous monomer and a reactive diluent in the organic phase of dental restorative composites, respectively. The purpose of addition of TEGDMA is mainly to decrease the high viscosity of Bis-GMA caused by hydrogen bonding between hydroxyl groups. However, some adverse effects will accompany with increased amounts of the TEGDMA, such as higher values of polymerization shrinkage, which is not undesirable for the clinical application. Therefore, substituting hydroxyl groups of Bis-GMA might be an appropriate and effective way to reduce the amount of diluents and weaken the accompanied adverse effects. This work focuses on the synthesis of a novel Bis-GMA derivate, substituting acetyl groups for hydroxyl groups in Bis-GMA. The viscosity of Bis-GMA characterized with rotational rheometer was significantly decreased from 820 Pa.s to 11 Pa.s by substitution of acetyl group, leading to the low amount of TEGDMA in resin matrix. Differential Scanning Calorimeter (DSC) was used for investigating the reaction kinetics of this novel monomer with different mass ratios of TEGDMA. The results suggested that the maximum conversion of the Ac-Bis-GMA can reach 88% while the corresponding value for Bis-GMA is 75%. Dental composites were prepared from 2,2-bis [4-(2-acetyl-3-methacryloyloxypropoxy) pheny propane (Ac-Bis-GMA) or Bis-GMA resin mixtures with TEGDMA filled with 70 wt% silica co-fillers. The results presented that dental composites prepared from new resin matrixes exhibited adequate mechanical properties.

Reproductive Toxicity Evaluation of the Dental Resin Monomer Triethylene Glycol Dimethacrylate (CASRN 109-16-0) in Mice

2013 ◽  
Vol 33 (2) ◽  
pp. 106-115 ◽  
Author(s):  
Lori H. Moilanen ◽  
Janell K. Dahms ◽  
Alan M. Hoberman
Keyword(s):  
Reproductive Toxicity ◽  
Sperm Concentration ◽  
Clinical Signs ◽  
Triethylene Glycol ◽  
Glycol Dimethacrylate ◽  
Dental Resin ◽  
Triethylene Glycol Dimethacrylate ◽  
Male And Female ◽  
Body Weights ◽  
Chemical Abstracts Service

The reproductive toxicity potential of the resin monomer triethylene glycol dimethacrylate (TEGDMA; Chemical Abstracts Service Registry Number 109-16-0) was investigated in male and female Crl:CD1(ICR) mice, 4 dosage groups, 25 mice/sex/group. Formulations of TEGDMA (0, 0.01, 0.1, or 1.0 mg/kg/d) in reverse osmosis-processed deionized water were intubated once daily beginning 28 days before cohabitation and continuing through mating (males) or through gestation day 17 (females). The following parameters were evaluated: viability, clinical signs, body weights, estrous cyclicity, necropsy observations, organ weights, sperm concentration/motility/morphology, cesarean-sectioning and litter observations, and histopathological evaluation of select tissues. No deaths or clinical signs related to TEGDMA occurred. No significant changes in male and female body weights and body weight gains were recorded for any of the administered dosages of TEGMDA. All mating and fertility parameters and all litter and fetal data were considered to be unaffected by dosages of TEGMDA as high as 1 mg/kg/d. Gross or histopathologic tissue changes attributable to the test article were not observed. Reproductive and developmental no observed adverse effect levels (NOAELs) for TEGMDA were 1.0 mg/kg/d, the highest dose tested. Comparison of conservatively estimated TEGDMA exposures from dental treatments to the NOAEL of 1.0 mg/kg/d identified in this study indicates margins of exposure of at least 120- to 3000-fold depending on the exposure scenario. The results of this study support the continued safe use of TEGDMA in polymeric dental products applied according to the manufacturers’ instructions.

scholarly journals DEGREE OF POLYMERIZATION OF DUAL CURE RESIN CEMENT MEASURED BY FTIR

2018 ◽  
Vol 9 (1) ◽  
Author(s):  
Aleksandra Maletin ◽  
Dubravka Marković ◽  
Isidora Nešković ◽  
Branislava Petronijević ◽  
Tanja Veljović ◽  
...  
Keyword(s):  
Clinical Success ◽  
Triethylene Glycol ◽  
Mean Value ◽  
Degree Of Polymerization ◽  
Resin Cement ◽  
Polymerization Reaction ◽  
Dental Resin ◽  
Triethylene Glycol Dimethacrylate ◽  
High Degree

Introduction: The degree of polymerization of dental resin cement materi- als is very important for the longevity and quality of the clinical success of the restorative procedure. Insufficiently effective polymerization reaction of dental resin cement materials may result in adverse effects on the mechanical and adhesive performance of the material. It is believed that the proportion of triethylene glycol dimethacrylate (TEGDMA) mono- mers in the chemical structure of the material significantly influences the polymerization reaction. With the increase in TEGDMA, the degree of conversion of monomers into the polymer increases. Aim: The aim of this study has been to determine the degree of polymerization of dual cure dental resin cement. Material and methods: For the analysis of the degree of polymerization, Fourier transform infrared (FTIR) spectroscopy was used. 10 samples of dual cure resin based cement Variolink II were prepared in accordance with the manufacturer's instructions. Analysis was performed 24 hours after polymerization procedure. Results: Degree of polymerization of Variolink II resin based cement ranged from 69.2% to 98.7% with a mean value of 85.81%. Conclusion: Variolink II dual cure resin cement contains a significant percentage of TEGDMA which can be the cause of high degree of polymerization. The minimum accep- table percentage of the degree of polymerization of dental resin cement has not yet been established.

TEGDMA Modulates Glutathione Transferase P1 Activity in Gingival Fibroblasts

2004 ◽  
Vol 83 (12) ◽  
pp. 914-919 ◽  
Author(s):  
M. Lefeuvre ◽  
K. Bourd ◽  
M.-A. Loriot ◽  
M. Goldberg ◽  
P. Beaune ◽  
...  
Keyword(s):  
Biochemical Analysis ◽  
Glutathione Transferase ◽  
Aqueous Media ◽  
Triethylene Glycol ◽  
Gingival Fibroblasts ◽  
Dental Resin ◽  
Competitive Antagonist ◽  
Triethylene Glycol Dimethacrylate ◽  
Low Concentrations

Dental resinous materials can contain large amounts (from 30 to 50%) of triethylene-glycol-dimethacrylate (TEGDMA). This compound leaches into aqueous media and is toxic to dental pulp, as well as to gingival fibroblasts in vitro. To elucidate the mechanism of TEGDMA toxicity, we investigated the effects on glutathione (GSH) level and glutathione transferase P1 (GSTP1) activity in cultured human gingival fibroblasts. TEGDMA cytotoxic concentrations (from 0.5 to 2 mM) induced a depletion of GSH without formation of oxidized GSH (GSSG). In fibroblasts expressing the wild-type GSTP1, TEGDMA both inhibited and potentiated GSTP1 activity at high (IC50 = 1.1 mM) and low concentrations, respectively. In contrast, cells expressing the GSTP1 *A/*B variant showed a weak inhibition of GST activity only, associated with greater sensitivity to drug toxicity. Biochemical analysis of GSTP1 inhibition revealed that TEGDMA is a non-competitive antagonist with respect to GSH and substrate. Thus, TEGDMA interference with GSH and GSTP1 activity may contribute to dental-resin-induced adverse effects.

The applicability of organomodified nanoclays as new fillers for mechanical reinforcement of dental composites

2017 ◽  
Vol 52 (7) ◽  
pp. 963-970 ◽  
Author(s):  
Lívia Rodrigues Menezes ◽  
Emerson Oliveira da Silva ◽  
Anne Caroline da Silva Rocha ◽  
Dayane Carvalho Ramos Salles de Oliveira ◽  
Paulo Ricardo de Barros Campos
Keyword(s):  
Mechanical Test ◽  
Reaction Medium ◽  
Triethylene Glycol ◽  
Resin Matrix ◽  
Aluminum Silicate ◽  
Test Results ◽  
Mechanical Reinforcement ◽  
Triethylene Glycol Dimethacrylate ◽  
Light Curing ◽  
Urethane Dimethacrylate

Objectives This study reports the evaluation of changes in crosslink structure and mechanical properties of dental microhybrid composite reinforced with clays when compared to silica nanofillers, which are already extensively used for this application. Materials and methods A standardized resin matrix with a glycerolate dimethacrylate, triethylene glycol dimethacrylate, and urethane dimethacrylate copolymers associated with a camphorquinone photoinitiator system was blended with 75 wt% filler content. As fillers, two organically modified clays (hydrophilic silica and organomodified silica) and a boron-aluminum-silicate glass with 4 µm were used to obtain nanohybrid nanocomposites. The samples were prepared by light curing and were evaluated by measuring flexural strength, elasticity modulus, hardness, tensile resistance, and crosslinking. Results The mechanical test results indicated that the system with 2.5% clay was better dispersed in the system, while the highest concentrations caused agglomeration of these clays. On the other hand, the silicas showed gradual gain in properties. The increase in concentration of all nanofillers reduced the crosslinking ability of the systems. This behavior can be explained because the clay’s presence makes the reaction medium more viscous or because the fillers act as points of light absorption and scattering.

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