• Polymer(Korea)
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• v.28 no.4
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• pp.321-327
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• 2004

The applications of dental restorative composite resins containing 2,2-bis [4-(2-hydroxy-3-me-thacryloyloxy propoxy) phenyl] propane as a base resin, and triethylene glycol dimethacrylate, as a diluent, were often limited in dentistry due to the relatively large amount of volumetric shrinkage that occurs during the curing reaction. In this study, in order to reduce volumetric shrinkage of the current dental restorative composite resin, asymmetric spiro orthocarbonates were synthesized and then the characteristics of resin composites containing them were explored. The volumetric shrinkage of the dental composites containing spiro orthocarbonates was decreased approximately 45%. However, the curing characteristics and mechanical properties of the new dental composites were slightly poor than those of the commercially available dental composite.

• Bulletin of the Korean Chemical Society
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• v.24 no.9
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• pp.1371-1373
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• 2003

• Bulletin of the Korean Chemical Society
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• v.9 no.4
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• pp.252-253
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• 1988

• Bulletin of the Korean Chemical Society
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• v.13 no.4
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• pp.375-381
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• 1992

In this study we have synthesized two spiro orthocarbonates, which can be polymerized with volume expansion, and determined their crystal structures. The crystal data are as follows; 3,4,10,11-Di(9,10-dihydro-9,10-ethanoanthracenyl)- 1,6,8,13-tetraoxa-6.6-tridecane 5: a = 16.898 (1), b = 9.299 (1), c = 24.359 (2) ${\AA}$, $\beta$ = 123.73 $(7)^{\circ}$, space group P21/c and R = 0.073 for 2954 reflections; compound 8: a = 15.244 (4), b = 15.293 (3), c = 10.772 (3) $\AA$, ${\beta}$ = 99.45 $(2)^{\circ}$, space group P21/c and R = 0.082 for 2346 reflections. The seven-membered rings of compound 5 are chair forms and all the six-membered rings are boat shaped. For a six-membered spiro orthocarbonate, 3,9-Di(9-fluorenylidenyl)-1,4,6,9-tetraoxa-5,5-und ecane 8, fluorene groups [C(1) atom through C(13) atom] are planar within ${\pm}0.09{\AA}$ and the six-membered rings have chair conformations. The whole molecule has pseudo-C2 symmetry. The water molecules in the crystal are linked with each other through the hydrogen bond with distance of 2.790 (20) ${\AA}$.

• 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.