• Polymer(Korea)
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• v.31 no.6
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• pp.491-496
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• 2007

In the polymeric dental restorative composites, the resin matrix mainly contains 70 wt% 2,2-bis[4-(2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane (Bis-GMA), as a base resin and 30 wt% triethylene glycol dimethacrylate (TEGDMA) as a diluent. Even though the viscosity of the resin matrix is rapidly decreased by adding TEGDMA, addition of TEGDMA to the Bis-GMA results in reduction in the mechanical properties and increase in the curing shrinkage of the dental composite. In order to fabricate dental composite exhibiting excellent properties by reducing TEGDMA content in the resin matrix, in this study, Bis-GMA derivatives, which do not contain hydroxyl groups, were used instead of Bis-GMA. The curing characteristics of Bis-GMA derivatives were similar with those of Bis-GMA, while the former exhibited lower viscosity and water absorption than the latter. Comparing the curing shrinkage of the dental composite containing Bis-GMA derivative with that prepared from Bis-GMA, the reduction in curing shrinkage was about 25%. Dental composites prepared from new resin matrices also exhibited low water uptake and better properties in mechanical strength.

• Restorative Dentistry and Endodontics
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• v.36 no.2
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• pp.139-148
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• 2011

Objectives: This study investigated the effect of the strength and wetting characteristics of adhesives on the bond strength to dentin. The experimental adhesives containing various ratios of hydrophobic, low-viscosity Bis-M-GMA, with Bis-GMA and TEGDMA, were made and evaluated on the mechanical properties and bond strength to dentin. Materials and Methods: Five experimental adhesives formulated with various Bis-GMA/Bis-MGMA/TEGDMA ratios were evaluated on their viscosity, degree of conversion (DC), flexural strength (FS), and microtensile bond strength (MTBS). The bonded interfaces were evaluated with SEM and the solubility parameter was calculated to understand the wetting characteristics of the adhesives. Results: Although there were no significant differences in the DC between the experimental adhesives at 48 hr after curing (p > 0.05), the experimental adhesives that did not contain Bis-GMA exhibited a lower FS than did those containing Bis-GMA (p < 0.05). The experimental adhesives that had very little to no TEGDMA showed significantly lower MTBS than did those containing a higher content of TEGDMA (p < 0.05). The formers exhibited gaps at the interface between the adhesive layer and the hybrid layer. The solubility parameter of TEGDMA approximated those of the components of the primed dentin, rather than Bis-GMA and Bis-M-GMA. Conclusions: To achieve a good dentin bond, a strong base monomer, such as Bis-GMA, cannot be completely replaced by Bis-M-GMA for maintaining mechanical strength. For compatible copolymerization between the adhesive and the primed dentin as well as dense cross-linking of the adhesive layer, at least 30% fraction of TEGDMA is also needed.

• Polymer(Korea)
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• v.34 no.6
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• pp.517-521
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• 2010

Microprous polyethylene (PE) membranes are widely used as lithium-ion battery separators. A separator having higher meltdown temperature than PE separator is still required for useful safety feature at a high temperature. To enhance meltdown temperature of PE separator, it was coated with polymers synthesized from bis-GMA derivatives by radical polymerization. Polymer was not formed when bis-GMA monomer having a high viscosity was used, while polymers were formed when bis-GMA derivatives having a low viscosity were used. When the separator was coated with polymer synthesized from reaction mixture containing proper amount of bis-GMA derivative, its meltdown temperature were increased up to $160^{\circ}C$ without reduction in the air permeability.

• Polymer(Korea)
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• v.28 no.5
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• pp.426-432
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• 2004

To reduce volumetric shrinkage of the commercially available polymeric dental composite during curing reaction, (2,2-bis [4-(2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane) (bis -GMA) derivatives, i.e., (2,2-bis[3-methyl, 4-(2-hydroxy-3-methacryloyloxy propoxy) phenyl] propan) (DMBis-GMA) and (2,2-his [3,5-dimethyl ,4- (2-hydroxy-3-methacryloyloxy propoxy) phenyl] propane) (TMBis-GMA) were synthesized and then new dental composite resin composed of Bis-GMA derivatives, diluent, spiro orthocarbonate (SOC), and inorganic filler was produced. Among the Bis-GMA derivative/Bis-GMA derivative/diluent mixtures, Bis-GMA/ TMBis-GMA/TEGDMA mixture exhibited the lowest volumetric shrinkage. Volumetric shrinkage of this mixture was further reduced by adding SOC. Volumtric shrinkage of dental composite prepared from commercially available resin monomer mixture was $2.5\%$, while that prepared from resin monomer mixture having minimum volumetric shrinkage was reduced to $0.7\%$. Mechanical strength of this dental composite was nearly the same with that of commercial products but the time required for the curing reaction was retarded.

• Journal of Industrial Technology
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• v.35
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• pp.31-34
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• 2015

The purpose of the study was to investigate the mechanical properties (diametral tensile strength, flexural strength, compressive strength, Vickers hardness) of 4 kinds of composit resins; Bis-GMA based composit, Bis-EMA based composit, Bis-GMA/UDMA based composit, and Bis-EMA/UDMA based composit, The composit resin based Bis-GMA showed stronger mechanical properties than Bis-EMA. It was found that the addition of UDMA to both Bis-GMA based composit and Bis-EMA based composit highly improved mechanical properties. However, the mechanical properties of the composit resins prepared in this study were lower than those of the commercialized products in market(Charmfil flow(Denkist), Quadrant flow(CAVEX)), since the composit resins prepared in this study has much lower inorganic filler content of 43wt% comparing with 50~70wt% inorganic filler content of the commercialized products.

• Polymer(Korea)
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• v.30 no.6
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• pp.538-544
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• 2006

Two kinds of novel bifunctional methacrylated prepolymers (170-2MA and 631-2MA) which have similar structure with 2,2-bis[4- (2'-hynroxy-3'-methacryloyloxypropoxy)phenyl] propane (Bis-GMA) was synthesized for dental applications as an alternative to Bis-GMA containing bisphenol A that is doubtful as an endocrine disrupter. The organic matrices were prepared by mixing a diluent and/or a monomer with the synthesized methacrylated prepolymers. The yield, viscosity, and chemical structures of the prepolymers and the physical and methanical properties of the organic matrices were evaluated. The yields of the prepolymers synthesized through a ring-opening reaction of epoxy compound and methacrylic acid were above 90% and the viscosities of the prepolymers were much lower than that of the Bis-GMA control. From the results of $^1H-NMR$ and FTIR analyses, the chemical structures of the prepolymers were similar to that of Bis-GMA. In addition, the curing time, poly-merization shrinkage, photoconversion, polymerization depth, and compressive strength of the organic matrices formulated with 170-2MA and 631-2MA prepolymers exhibited comparable to or better than those of the existing Bis-GMA-based one. These results suggest that the novel methacrylated prepolymers which have no endocrine disrupter can be an alternative to Bis-GMA and be applicable to dental polymer materials.

• Restorative Dentistry and Endodontics
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• v.24 no.1
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• pp.26-39
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• 1999

Bis-GMA, the representative monomer of bonding resin, contributes to the rigidity of bonding layer. Hydrophilic monomer contributes to the permeability into dentin substrates while weaken the bonding layer due to its small molecular weight. The degree of conversion also contributes to the ultimate strength of the bonding layer. This study was performed for the correlation analysis of monomer ratio and dentin bonding strength via degree of conversion. 7 experimental bonding resins were prepared with Bis-GMA, ratio from 20% to 80% by 10% increment, and hydrophilic HEMA monomer. Their degree of conversion and shear bond strength to dentin were compared with Scotchbond Multi-Purpose adhesive, and the fractured surfaces were examined microscopically. The results were as follows; 1. The degree of conversion increased when, the ratio of Bis-GMA increased from 20% to 70%, whereas it decreased when the ratio of Bis-GMA was 80%. 2. Shear bond strengths of the experimental bonding resins of 80%, 70%, 60% ratio of Bis-GMA were significantly higher than those of the experimental bonding resin of 50% ratio of Bis-GMA and Scotchbond Multi-Purpose adhesive. Lower shear bond strengths were obtained with the experimental bonding resins of 40%, 30%, 20% ratio of Bis-GMA (p<0.05). 3. Adhesive fractures were associated with the bonding resins of the lower bond strength, while cohesive fractures within the bonding resin layer were associated with the bonding resins of higher bond strength. Bonding resins with shear bond strength higher than 18MPa showed some cohesive fractures within the composite resin or within the dentin. 4. Correlations between Bis-GMA ratio and the degree of conversion (r=0.826), between Bis-GMA ratio and shear bond strength (r=0.853), and between the degree of conversion and shear bond strength (r=0.786) were significant (p<0.05).

• Proceedings of the KOSOMBE Conference
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• v.1996 no.11
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• pp.140-141
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• 1996

Bis-GMA is an important component in commercial dental restorative composites, but its hydroxy groups are considered to promote water absorption of the cured composite in a mouth. In this work, multifunctional methacrylates were prepared by blocking the hydroxy groups in bis-GMA with methacryloyl groups. Comparing to bis-GMA, new prepolymers having three methacryloyl groups (BPA-3M) and four methacryloyl groups (BPA-4M) showed much lower viscosities. Photopolymerization conversion of BPA-3M was slightly higher than that of bis-GMA. Water absorption of the photo-cured composite containing BPA-3M was measured for one month and found to be much lower than that of bis-GMA.

• Restorative Dentistry and Endodontics
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• v.32 no.5
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• pp.469-475
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• 2007

The purpose of this study was to evaluate the effect of a new resin monomer on the microleakage of composite resin restorations. By adding new methoxylated Bis-GMA (Bis-M-GMA, 2,2-bis[4-(2-methoxy-3-methacryloyloxy propoxy) phenyl] propane) having low viscosity, the content of TEGDMA which has adverse effects on polymerization shrinkage might be decreased. As a result, microleakage might be improved. $2\;mm\;{\times}\;2\;mm\;{\times}\;2\;mm$ cavities with occlusal margins in enamel and gingival margins in dentin were prepared on buccal and lingual surfaces of 40 extracted human premolars. Prepared teeth were randomly divided into four groups and restored with Clearfil SE bond (Kuraray, Japan) and one of experimental composite resins; EX1, Experimental composite resin1 (Bis-M-GMA/TEGDMA = 95/5 wt%, 40 mm nanofillers); EX2, Experimental composite resin2 (Bis-M-GMA/TEGDMA = 95/5 wt%, 20 mm nanofillers); EX3, Experimental composite resin3 (Bis-GMA/TEGDMA = 70/30 wt%, 40 nm nanofillers); and Filtek Z250 (3M ESPE, USA) was filed as a control group. The restored teeth were thermocycled, and immersed in 2% methylene blue solution for 24 hours. The teeth were sectioned buccolingually with a low speed diamond saw and evaluated for microleakage under stereomicroscope. The data were statistically analyzed by Pearson Chi-Square test and Fisher Exact test (p = 0.05). The microleakage scores seen at the enamel margin were significantly lower than those of dentin margin (p = 0.007). There were no significant differences among the composite resins in the microleakage scores within each margin (p > 0.05). Bis-M-GMA, a new resin monomer having low viscosity, might in part replace high viscous Bis-CMA and might improve the quality of composite resin.

• Restorative Dentistry and Endodontics
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• v.33 no.1
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• pp.1-8
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• 2008

The purpose of this study was to evaluate the effect of a new resin monomer, filler size and polishing technique on the surface roughness of composite resin restorations using confocal laser scanning microscopy. By adding new methoxylated Bis-GMA (Bis-M-GMA, 2,2-bis[4-(2-methoxy-3-methacryloyloxy propoxy) phenyl] propane) having low viscosity, the content of TEGDMA might be decreased. Three experimental composite resins were made: EX1 (Bis-M-GMA/TEGDMA = 95/5 wt%, 40 nm nanofillers); EX2 (Bis-M-GMA/TEGDMA = 95/5 wt%, 20 nm nanofillers); EX3 (Bis-GMA/TEGDMA = 70/30 wt%, 40 nm nanofillers). Filtek Z250 was used as a reference. Nine specimens (6 mm in diameter and 2 mm in thickness) for each experimental composite resin and Filtek Z250 were fabricated in a teflon mold and assigned to three groups. In Mylar strip group, specimens were left undisturbed. In Sof-lex group, specimens were ground with #1000 SiC paper and polished with Sof-lex discs. In DiaPolisher group, specimens were ground with #1000 SiC paper and polished with DiaPolisher polishing points. The Ra (Average roughness), Rq (Root mean square roughness), Rv (Valley roughness), Rp (Peak roughness), Rc (2D roughness) and Sc (3D roughness) values were determined using confocal laser scanning microscopy. The data were statistically analyzed by Two-way ANOVA and Tukey multiple comparisons test (p = 0.05). The type of composite resin and polishing technique significantly affected the surface roughness of the composite resin restorations (p < 0.001). EX3 showed the smoothest surface compared to the other composite resins (p < 0.05). Mylar strip resulted in smoother surface than other polishing techniques (p < 0.05). Bis-M-GMA. a new resin monomer having low viscosity, might reduce the amount of diluent, but showed adverse effect on the surface roughness of composite resin restorations.