Thermal degradation of photo-polymerized BisGMA/TEGDMA-based dental resins

Teshima, Wataru; Nomura, Yuji; Ikeda, Atsuharu; Kawahara, Tsuyoshi; Okazaki, Masanori; Nahara, Yukinori

doi:10.1016/j.polymdegradstab.2003.10.007

Cited by 15 publications

(7 citation statements)

References 26 publications

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Section: Introductionmentioning

confidence: 99%

“…Although breakdown of BisGMA to BPA has been postulated, such breakdown appears unlikely based on the results of studies that investigated potential degradation via enzymatic or salivary action, 15 extreme pH values, 13,15 and high temperature. 16 Recently, 2 published studies 17,18 reported that BisGMA produced adverse effects on the fertility and reproductive systems of male and female mice, respectively. In a study of male reproductive toxicity, Al-Hiyasat and Darmani 17 reported that BisGMA, administered in an alcoholic water solution to male mice for 28 days at 25 and 100 mg/kg, caused significant dose-related reductions in body weight, absolute weight of preputial glands, testis weight, and total sperm per epididymis.…”

Section: Introductionmentioning

confidence: 99%

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Reproductive Toxicity Evaluation of the Dental Resin Monomer Bisphenol A Glycidyl Methacrylate (CAS 1565-94-2) in Mice

Moilanen

Dahms²,

Hoberman

2013

Int J Toxicol

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The reproductive toxicity potential of the dental resin monomer bisphenol A glycidyl methacrylate (BisGMA; CASRN 1565-94-2) was investigated in male and female Crl: CD1(ICR) mice, 4 dosage groups, and 25 mice/sex/group. Formulations of BisGMA (0, 0.008, 0.08, or 0.8 mg/kg/d) in 0.8% ethanol in deionized water were intubated once daily beginning 28 days before cohabitation and continuing through mating (males) or through gestation day 17. 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 BisGMA occurred. No significant changes in male and female body weights and body weight gains were recorded at any of the administered dosages of BisGMA. All mating and fertility parameters, and all litter and fetal data, were considered to be unaffected by dosages of BisGMA as high as 0.8 mg/kg/d. Gross or histopathologic tissue changes attributable to the test article were not observed. Reproductive and developmental no observed effect levels (NOAELs) for BisGMA were 0.8 mg/kg/d, the highest dose tested. Comparison of this NOAEL value to published probabilistic estimates of human BisGMA exposure from dental products suggests a margin of safety of at least 280- to nearly 2000-fold. Under the conditions of this study, BisGMA is not a reproductive toxicant.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Reproductive Toxicity Evaluation of the Dental Resin Monomer Bisphenol A Glycidyl Methacrylate (CAS 1565-94-2) in Mice

Moilanen

Dahms²,

Hoberman

2013

Int J Toxicol

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“…The most common dimethacrylate monomer used in current commercial dental composites is bisglycidyl methacrylate (Bis‐GMA), which is the reaction product of bisphenol A and glycidyl ester methacrylate. The advantages of using Bis‐GMA over the first used small dental monomers, such as methyl methacrylate, include less shrinkage, higher modulus, and reduced toxicity due to its lower volatility and diffusivity into tissues 1–4. These desirable properties of Bis‐GMA are partially negated by its relatively high viscosity, which does not permit the use of high amounts of a filler.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the light polymerization efficiency of copolymers used in dental formulations by differential scanning calorimetry

Rigoli¹,

Riga²,

Cavalheiro³

et al. 2007

J of Applied Polymer Sci

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Different compositions of visible‐light‐curable triethylene glycol dimethacrylate/bisglycidyl methacrylate copolymers used in dental resin formulations were prepared through copolymerization photoinitiated by a camphorquinone/ethyl 4‐dimethylaminobenzoate system irradiated with an Ultrablue IS light‐emitting diode. The obtained copolymers were evaluated with differential scanning calorimetry. From the data for the heat of polymerization, before and after light exposure, obtained from exothermic differential scanning calorimetry curves, the light polymerization efficiency or degree of conversion of double bonds was calculated. The glass‐transition temperature also was determined before and after photopolymerization. After the photopolymerization, the glass‐transition temperature was not well defined because of the breadth of the transition region associated with the properties of the photocured dimethacrylate. The glass‐transition temperature after photopolymerization was determined experimentally and compared with the values determined with the Fox equation. In all mixtures, the experimental value was lower than the calculated value. Scanning electron microscopy was used to analyze the morphological differences in the prepared copolymer structures. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008

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“…HEMA is also produced from TEGDMA monomers. It is not observed the presence of MA and HEMA at temperature up to 250°C suggesting that the scission of TEGDMA an BisGMA occurred in the initial phase of the thermal decomposition, and their amounts decreased with increasing degree of conversion of the copolymers 28…”

Section: Resultsmentioning

confidence: 96%

Thermal decomposition of copolymers used in dental resins formulations photocured by ultra blue IS

Rigoli

Cavalheiro

Neumann

et al. 2007

J of Applied Polymer Sci

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Kinetics of thermal decomposition of acrylates copolymers used in dental resins formulations were studied with dynamic thermogravimetric analysis experiments. The kinetic parameters, including activation energy, pre-exponential factor, and 60 min half-life temperature, which were calculated by the Flynn and Wall method, are presented. The results indicate that thermal decomposition of the material occurred in three different stages characterized by different mechanism. These three events were separated and the kinetics parameters were determined. The loss mass was observed in the onset of the thermal decomposition for the all of copolymers studied. When the copolymers were submitted to thermal treatment before of thermal analysis was not observed the loss mass in the beginning of the process. The analysis of intermediates by GC of the condensed material extracted after thermal treatment at TB copolymers showed the presence of the methacrylic acid and 2-hydroxyethyl methacrylate, which are products of decomposition of BisGMA and triethyleneglycol dimethacrylate monomers.

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Thermal degradation of photo-polymerized BisGMA/TEGDMA-based dental resins

Cited by 15 publications

References 26 publications

Reproductive Toxicity Evaluation of the Dental Resin Monomer Bisphenol A Glycidyl Methacrylate (CAS 1565-94-2) in Mice

Reproductive Toxicity Evaluation of the Dental Resin Monomer Bisphenol A Glycidyl Methacrylate (CAS 1565-94-2) in Mice

Evaluation of the light polymerization efficiency of copolymers used in dental formulations by differential scanning calorimetry

Thermal decomposition of copolymers used in dental resins formulations photocured by ultra blue IS

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