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Bis-GMA
DENTAL MATERIALS · 2021 · IF 5.304

Preparation and evaluation of novel bio-based Bis-GMA-free dental composites with low estrogenic activity

Yinan Sun,Zeying Zhou,Hao Jiang,Yuting Duan,Jialin Li,Xiaoqiu Liu,Lihua Hong,Chengji Zhao

Objective Although bisphenol Aglycidyl methacrylate (Bis-GMA) are widely used in the dental composite , its raw materials include the petroleum-based product bisphenol A (BPA) with high estrogenic activity (EA). In this study, two new BPA-free dimethacrylate monomers from bio-based material creosol were synthesized and evaluated. Methods The renewable bisphenol monomer 5, 5'-methylenedicreosol (BCF) was prepared from bio-based material creosol. By the human breast cancer cells (MCF-7 cells) proliferation assay, a risk assessment of BCF was performed to determine if BCF possessed reduced EA in comparison to BPA. Then, the novel monomers 5, 5'-methylenedicreosol diglycidyl ether diacrylate (BCF-EA) and 5, 5'-methylenedicreosol diglycidyl ether dimethacrylate (BCF-GMA) were synthesized from BCF with epichlorohydrin and (meth)acrylate. All products were investigated by 1 H NMR and FT-IR spectra. The control resin was a mixture based on Bis-GMA and tri(ethyleneglycol) dimethacrylate (TEGDMA) with a weight ratio of 5:5 (5B5T). Similarly, experimental resin matrix was a mixture based on BCF-EA/TEGDMA (5E5T) and BCF-GMA/TEGDMA (5G5T). And their corresponding composites were then prepared with corresponding resin matrices and hybrid SiO 2 (5E5TC, 5G5TC and 5B5TC). The properties of these composites were investigated according to the standard or referenced methods. Each sample was evaluated for double bond conversion (DC), shrinkage stress (SS) and volumetric polymerization shrinkage (VS). Water sorption (WS), water solubility (SL), mechanical properties and cytotoxicity were also measured. Results 1 H NMR and FT-IR spectra confirmed the chemical structure of each monomer. EA test revealed that bio-based bisphenol monomer BCF as the precursor of BCF-EA and BCF-GMA showed lower EA than BPA. Cured resin matrix: Both 5E5T and 5G5T had nearly the same DC (p < 0.05), which was higher than 5B5T (p < 0.05); 5E5T and 5G5T had lower VS, SL and cytotoxicity than 5B5T (p < 0.05); mechanical properties of 5E5T and 5G5T were all better than those of 5B5T (p < 0.05). Cured composite: There was no significant difference in conversion (p < 0.05); 5E5TC and 5G5TC had significantly lower VS (p < 0.05); WS of 5E5TC and 5G5TC were similar (p < 0.05), but higher compared to 5B5TC (p < 0.05); 5E5TC and 5G5TC had the deeper depth of cure (p > 0.05); before water immersion, there was no significant difference in flexural strength between 5E5TC and 5G5TC (p > 0.05), and higher than 5B5TC (p < 0.05); 5E5TC and 5G5TC showed less cytotoxicity than 5B5TC (p < 0.05). Significance The new BPA-free di(meth)acrylates are promising photocurable dental monomers owning to bio-based raw material, high degree of conversion coupled with low curing shrinkage and good mechanical properties. Therefore, BCF-EA and BCF-GMA has a potential to be used as the substitution for Bis-GMA to prepare Bis-GMA-free dental composite.

研究领域: 材料科学 · 口腔医学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Omega · 2020 · IF 2.87

Effect of APTES- or MPTS-Conditioned Nanozirconia Fillers on Mechanical Properties of Bis-GMA-Based Resin Composites

Jiaxue Yang,Mengyuan Liao,Gaoying Hong,Shiqi Dai,Jiadi Shen,Haifeng Xie,Chen Chen

To investigate the effects of 3-aminopropyltriethoxysilane (APTES)- or (3-mercaptopropyl)trimethoxysilane (MPTS)-conditioned nanozirconia fillers on the mechanical properties of Bis-GMA-based resin composites. The conditioned fillers were characterized by Fourier transform infrared (FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS), and thermodynamic calculations. They were then used to prepare Bis-GMA-based resin composites, whose flexural strength and elastic modulus were evaluated. The Cell Counting Kit-8 (CCK-8) assessed the composites’ cytotoxicity. The FTIR spectra of the conditioned fillers showed new absorption bands at 1569 and 1100 cm–1, indicating successful grafting of APTES or MPTS onto nanozirconia. XPS confirmed the Zr–O–Si bonds in the APTES- or MPTS-conditioned fillers at contents of 2.02 and 6.98%, respectively. Thermodynamic calculations reaffirmed the chemical binding between the two silanes and nanozirconia fillers. Composites containing the conditioned nanozirconia fillers had significantly greater flexural strengths (APTES, 121.02 ± 8.31 MPa; MPTS, 132.80 ± 15.80 MPa; control, 94.84 ± 9.28 MPa) and elastic moduli (8.76 ± 0.52, 9.24 ± 0.60, and 7.44 ± 0.83 GPa, respectively) than a control with untreated fillers. The cytotoxicity assay identified no significant cytotoxicity by composites containing the conditioned fillers. Silanes were previously considered to be unable to chemically condition zirconia to bond with resin. Inclusion of APTES- or MPTS-conditioned nanozirconia fillers can improve the mechanical properties of Bis-GMA-based resin composites without obvious cytotoxicity in this study.

CAS / MDL: 109-16-0
研究领域: 材料科学 · 牙科材料 · 高分子科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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DENTAL MATERIALS JOURNAL · 2020 ·Vol. 39 ·期 5 ·900-908 · IF 1.359

Effect of resin composition on performance of polymer-infiltrated feldspar-network composites for dental restoration

Longzhao KANG,Yan ZHOU,Jinle LAN,Yunhua YU,Qing CAI,Xiaoping YANG

This study intends to obtain a kind of polymer-infiltrated ceramic-network (PICN) composite with improved performance for dental restoration. Porous ceramic network was prepared via compressing feldspar powders, followed by resin infiltration using Bis-GMA/TEGDMA or UDMA/TEGDMA mixtures to obtain PICN composites after thermocuring. The sintering parameters (temperature, duration) for the formation of feldspathic network with proper porosity were investigated. The ratios of resin mixtures were adjusted to optimize the infiltration. Comprehensive characterizations were conducted on the porosity and the shrinkage of preformed ceramic-networks, the viscosity of resin mixtures and their infiltration into the ceramic networks, as well as, flexural properties, Vickers hardness and wear resistance of the final PICN composites. It turned out that the PICN composite prepared from Bis-GMA/TEGDMA (6:4) achieved the best performance among all the samples, which is expected to be a suitable material for computer-aided design/computer-aided manufacturing (CAD/CAM) dental restorative applications.

研究领域: 材料科学 · 牙医学
✓ 已验证 DOI PubMed 高影响因子
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DENTAL MATERIALS · 2019 · IF 4.44

Composite resin reinforced with fluorescent europium-doped hydroxyapatite nanowires for in-situ characterization

Lei Li,Dan Li,Wenwen Zhao,Qing Cai,Gang Li,Yunhua Yu,Xiaoping Yang

Objective The object is to find an easy but efficient way to illustrate the in-situ dispersion of nano-scaled one-dimensional fillers in composite resins, and to correlate their dispersion status with the properties of composite resins. Methods Fluorescent europium-doped hydroxyapatite nanowires (HANW:Eu) were synthesized via the hydrothermal method . The HANW:Eu was mixed into Bis-GMA/TEGDMA (60/40, w/w) at different contents (1–5   wt.%), and different processing methods (kneading, grinding, stirring) were tested to achieve good dispersion of HANW:Eu with the aid of fluorescent imaging system. Then, the mixtures of HANW:Eu and barium glass powder (BaGP) were kneaded into resin at a fixed content (70   wt.%) while at different mixing ratios. In addition to the 3D fluorescent imaging, characterizations were carried out on mechanical properties , fractured surface, wear resistance and polymerization shrinkage, to correlate the composite properties of with the dispersion status of the incorporated HANW:Eu. Results By doping calcium with 5   mol.% of europium , the obtained HANW:Eu displayed strong fluorescence, which made the illustration of its in-situ dispersion status within composites being possible. And this helped to judge that kneading was more efficient to homogeneously disperse HANW:Eu than grinding and stirring. However, it was illustrated vividly that HANW:Eu aggregated severely when it was co-incorporated with BaGP into composites at the total content of 70   wt.%, which had not been previously revealed by other microscope observations. In comparison with composites containing 70   wt.% of BaGP, improvements in the mechanical properties of resulting composites were identified for the cases containing 3   wt.% of HANW and 67   wt.% of BaGP, however, their wear volume loss and the polymerization shrinkage did not decrease as expected due to the HANW aggregations. Significance The fluorescent filler prepared in this study provides a feasible strategy to illustrate the in-situ dispersion status of inorganic fillers, which provides guidance for the processing of composite resins.

CAS / MDL: 112-80-1
研究领域: 材料科学 · 纳米技术 · 牙科材料 · 高分子科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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INTERNATIONAL JOURNAL OF ADHESION AND ADHESIVES · 2024 · IF 3.2

Effect of silica nanospheres silanized by functional silanes on the physicochemical and mechanical properties of Bis-GMA/TEGDMA dental composite resin by photocuring synthesis

Song Guo,Shao-hua Luo,Xiaolong Li,Zihan Wang,Xian Zhang,Xuefei Lei,Sheng-xue Yan

This investigation focused on the contribution of various silane blends, used as coupling agents, to the ultimate performance of dental nanocomposite dimethacrylate photocurable resins . Initially, the surface of silica nanospheres was silanized with three different silane coupling agents : γ-MPS, APTES , and OTMS, with the grafting rate serving as the index. Fourier Transform infrared (FTIR) spectroscopy and thermogravimetric analysis (TGA) verified the modification of nanosilica . Through orthogonal test experiments on the three silane coupling agents, the optimal modifier concentration, temperature, and time were determined. Subsequently, 15 wt% organomodified SiO 2 nanospheres were incorporated into Bis-GMA/TEGDMA (70/30 by wt%) based resins via a photocuring process. Scanning electron microscopy (SEM) findings revealed a relatively vague interface between inorganic fillers and resins in the polymer composite , especially when reactive silanes like γ-MPS and their corresponding blends were used. The combination of SiO 2 and γ-MPS functional silane blend provided the highest flexural properties and the lowest solubility after storing the nanocomposite in water for 1 week at 37 °C. With these methods, composite resins containing 15 wt% MPS-SiO 2 nanospheres in a Bis-GMA/TEGDMA (70/30 by wt%) mixture exhibited the best comprehensive properties, making them a promising choice for achieving long-term durable restorations in clinical therapies.

CAS / MDL: 1565-94-2 75980-60-8
研究领域: 材料科学 · 牙科医学
✓ 已验证 产品关联 DOI 高影响因子
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JOURNAL OF DENTISTRY · 2020 · IF 3.242

Effects of nano-zirconia fillers conditioned with phosphate ester monomers on the conversion and mechanical properties of Bis-GMA- and UDMA-based resin composites

Jiaxue Yang,Jiadi Shen,Xinyi Wu,Feng He,Haifeng Xie,Chen Chen

Objectives This study investigated the effects of the surface conditioning of nano-zirconia fillers with 10-methacryloyloxydecyl dihydrogen phosphate (MDP) and dipentaerythritol penta-acrylate phosphate (PENTA) on the degree of conversion and mechanical properties of Bis-GMA- and UDMA-based resin composites containing the fillers. Methods MDP or PENTA conditioned nano-zirconia fillers were characterized by Fourier transform infrared spectroscopy (FTIR) and X-ray photoelectron spectroscopy (XPS). The conditioned nano-zirconia fillers were then used to prepare Bis-GMA- and UDMA-based resin composites. The bending strength and elastic modulus of the prepared composites were evaluated, and Weibull analysis was adopted to evaluate the reliability of the bending tests. Degree of conversion (DC) was measured by FTIR. Results FTIR and XPS analysis confirmed formation of Zr O P bonds in the MDP-conditioned and PENTA-conditioned zirconia fillers. MDP-conditioning and PENTA-conditioning increased bending strength of Bis-GMA-based composites (100.70 ± 7.15 MPa, 98.65 ± 4.76 Mpa) and UDMA-based composites (99.02 ± 4.45 MPa, 99.92 ± 5.78 MPa) compared to the groups with untreated nano-zirconia fillers (Bis-GMA-based, 84.98 ± 5.13 MPa; UDMA-based, 88.24 ± 4.61 MPa). The same trend was observed for the Weibull modulus ( m ) and elastic modulus. The MDP/PENTA conditioning did not affect the DC of the composites. Conclusion MDP or PENTA conditioning of nano-zirconia fillers improved the mechanical properties of the composite compared to the composites containing untreated nano-zirconia fillers; however, it did not affect DC. Clinical significance Mixing MDP- or PENTA-conditioned nano-zirconia fillers directly with gamma-MPS-conditioned silica to the resin composite has the potential to improve the composite’s mechanical properties.

研究领域: 牙科材料学 · 高分子化学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF DENTISTRY · 2024 · IF 4.8

Light-curable urushiol enhanced bisphenol A glycidyl dimethacrylate dentin bonding agent

Fei Wei,Tingting Bai,Huan Chen,Guangdi Sun,Xue Chen,Song Zhu

Objectives The low durability of composite resin restorations can be attributed to the degradation of the resin dentin bonding interface. Owing to the presence of hydrophilic components in the adhesive, the integrity of the resin dentin bonding interface is easily compromised, which, in turn, leads to a reduction in bond strength. The hydrophilic nature of the adhesive leads to water sorption, phase separation, and leaching of the resin component. Therefore, hydrophobic adhesives could effectively be used to stabilize the integrity and durability of the resin dentin bonding interface. Methods We synthesized a novel hydrophobic dentin adhesive by partially replacing bisphenol A glycidyl dimethacrylate (Bis-GMA) with a light-curable urushiol monomer. The properties of the produced adhesive, including the degree of conversion, viscosity, contact angle, water sorption/solubility, and mechanical strength, were comprehensively examined and compared to those of the commercially adhesive Adper Single Bond 2 as a positive control. The adhesive properties were determined using microtensile bond strength measurements, laser confocal microscopy, scanning electron microscopy observations, and nanoleakage tests. Finally, the novel adhesive was subjected to biocompatibility testing to determine its potential cytotoxicity. Results At a light-curable urushiol content of 20 %, the synthesized adhesive exhibited high degrees of conversion and hydrophobicity, low cytotoxicity, good mechanical properties, and outstanding adhesive strength. Conclusions The introduction of the light-curable urushiol into dentin adhesives can significantly enhance their hydrophobic, mechanical, and bonding properties, demonstrating potential to significantly improve restoration longevity. Clinical significance The integration of light-curable urushiol has endowed the experimental adhesives with several enhanced functionalities. These notable benefits underscore the suitability of this monomer for expanded applications in clinical practice.

研究领域: 牙科材料 · 粘接牙科学 · 高分子科学 · 生物相容性
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PROGRESS IN ORGANIC COATINGS · 2024 · IF 6.5

Photopolymerization initiated by p-diethylene glycol monomethyl ether cinnamyl formamide-based disulfide under 455 nm LED with minimized volume shrinkage

Yuhan Zhang,Nan Xiao,Yanjing Gao,Fang Sun

This study introduces a novel p -diethylene glycol monomethyl ether cinnamyl formamide-based disulfide monomer , N,N′ -(disulfanediylbis(2,1-phenylene)) bis(4-(4-(2-(2-methoxyethoxy)ethoxy) phenyl)-2-oxobut-3-enamide) (Mp-BSCF), designed to reduce the volume shrinkage of photosensitive resins and initiate monomer polymerization under 455 nm LED light irradiation. The photochemical properties and photoinitiation efficiency of Mp-BSCF are systematically investigated using UV–vis absorption spectroscopy , electron paramagnetic resonance (EPR) and real-time infrared spectroscopy . Although its weak absorption around 455 nm, Mp-BSCF can generate arylthiyl radicals under 455 nm LED irradiation, and then effectively initiate the polymerization of triethylene glycol dimethacrylate (TEGDMA)/A glycerolate dimethacrylate (Bis-GMA) system. Increasing Mp-BSCF addition enhances the final double bond conversion and maximum polymerization rate of the TEGDMA/Bis-GMA system, reaching up to 82.0 % and 2.02 % s −1 , respectively. Notably, Mp-BSCF significantly reduces the volume shrinkage of the photopolymerization system, with the addition of 10 % Mp-BSCF resulting in a 50 % reduction compared to the control system. This reduction is attributed to the dynamic reversible nature of the S S bond “breaking-recovery” and the intermolecular hydrogen bond interaction. Additionally, Mp-BSCF improves the thermal stability, friction resistance, and hardness of the TEGDMA/Bis-GMA photopolymerization system.

研究领域: 材料科学 · 高分子化学 · 光化学
✓ 已验证 DOI 高影响因子
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