New Families of Photocurable Oligomeric Fluoromonomers for Use in Dental Composites

Choi, Kyung; Stansbury, Jeffrey W.

doi:10.1021/cm9603260

Cited by 22 publications

(8 citation statements)

References 18 publications

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“…It is generally considered that polymerization of monomers with large molecular volume and low double bond content will result in the lower polymerization shrinkage [12,13] and polymerization of monomers with low viscosity will result in the higher double bond conversion [14][15][16][17]. It has been reported that the branchedpolymers have both a large molecular volume and low viscosity [18].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of New Tri-methacrylates as a Reactive Diluent in Root Canal Sealant

Liu

Liao

et al. 2011

Journal of Biomaterials Science, Polymer Edition

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In this work, a novel tri-methacrylate oligomer, GPTEMA, with three long-branched chain structures was synthesized through the reaction of glycerol propoxylate triglycidyl ether (GPTE) and methacrylic acid. The structure of GPTEMA was confirmed by FT-IR, (1)H-NMR, gel-permeation chromatography (GPC) and element analysis. The GPTEMA was used to partially or completely replace TEGDMA as reactive diluent and applied in a root canal sealant system containing Bis-GMA. The effects of GPTEMA on the polymerization behavior of Bis-GMA/TEGDMA/GPTEMA co-polymer and properties of its polymerizing product were investigated. Polymerization shrinkage, double bond conversion, glass transition temperature, flexural strength, flexural modulus, water sorption and diffusion coefficient of the Bis-GMA/TEGDMA/GPTEMA co-polymer were measured. The results illustrated that the Bis-GMA/TEGDMA/GPTEMA co-polymer attained lower polymerization shrinkage and higher double bond conversion. However, its T g, flexural strength and flexural modulus decreased with increasing content of GPTEMA, water sorption and diffusion coefficient increased with increasing content of GPTEMA.

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Section: Introductionmentioning

confidence: 99%

Evaluation of New Tri-methacrylates as a Reactive Diluent in Root Canal Sealant

Liu

Liao

et al. 2011

Journal of Biomaterials Science, Polymer Edition

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“…Polymerization‐induced phase separation can also occur between reactive species. Fluorinated methacrylate monomers exhibit phase separation of growing polymer from unreacted monomer upon polymerization 41. The polymerization of a fluorinated acrylate produces a phase‐separated homopolymer when the fluorocarbon side chains selectively associate to minimize interactions with the hydrocarbon polymer backbone chains formed during polymerization 42.…”

Section: Introductionmentioning

confidence: 99%

(Meth)acrylate vinyl ester hybrid polymerizations

Lee¹,

Cramer²,

Hoyle³

et al. 2009

J. Polym. Sci. A Polym. Chem.

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In this study vinyl ester monomers were synthesized by an amine catalyzed Michael addition reaction between a multifunctional thiol and the acrylate double bond of vinyl acrylate. The copolymerization behavior of both methacrylate/vinyl ester and acrylate/vinyl ester systems was studied with near-infrared spectroscopy. In acrylate/vinyl ester systems, the acrylate groups polymerize faster than the vinyl ester groups resulting in an overall conversion of 80% for acrylate double bonds in the acrylate/vinyl ester system relative to only 50% in the bulk acrylate system. In the methacrylate/vinyl ester systems, the difference in reactivity is even more pronounced resulting in two distinguishable polymerization regimes, one dominated by methacrylate polymerization and a second dominated by vinyl ester polymerization. A faster polymerization rate and higher overall conversion of the methacrylate double bonds is thus achieved relative to polymerization of the pure methacrylate system. The methacrylate conversion in the methacrylate/ vinyl ester system is near 100% compared to only ~60% in the pure methacrylate system. Utilizing hydrophilic vinyl ester and hydrophobic methacrylate monomers, polymerization-induced phase separation is observed. The phase separated domain size is on the order of ~1 μm under the polymerization conditions. The phase separated domains become larger and more distinct with slower polymerization and correspondingly increased time for diffusion.

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“…In practice, a visible light photoinitiator consisting of CQ and ethyl p-(N,N-dimethylamino)benzoate (EDMAB) as the tert-amine is used in commercial dental resin formulations. [4,[15][16][17] Upon exposure, CQ is transferred to a triplet excited state, which combines with the DMA group of EDMAB to form an exciplex. Then the resulting exciplex generates the reactive free radical at the a-carbon of a DMA group; this is considered to be the effective initiating species for the polymerization.…”

Section: Introductionmentioning

confidence: 99%

“…There have been furious research efforts to modify the Bis-GMA type methacrylates by incorporating suitable functional groups. [1,[15][16][17][21][22][23] The authors have reported some unique results obtained with modified Bis-GMAs, which have additional methacrylate groups, to improve the water uptake and viscosity problems in light-curable dental polymers. [24,25] In this paper, we report a new type of polymerizable, aromatic tert-amines, similar to the modified Bis-GMAs, with EDMAB analogues for enhancing photosensitivity as well as improving compatibility.…”

Section: Introductionmentioning

confidence: 99%

New Aromatic tert‐Amines for Application as Photoinitiator Components in Photocurable Dental Materials

Ahn

Han

Lee

et al. 2003

Macro Chemistry & Physics

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A new type of aromatic tert‐amine with a bisphenol A (BPA) skeleton has been prepared and applied as a photoinitiator (PI) component for enhancing photosensitivity in formulations of visible light curable dental polymers. Two N,N‐dimethylamino (DMA) groups were incorporated into BPA diglycidyl ether to make 2,2‐bis[4‐(2‐hydroxy‐3‐(p‐N,N‐dimethylaminobenzoyloxy)propyloxy)phenyl]propane (DMABPA). One or two (meth)acryloyl groups were reacted with the hydroxyl groups of DMABPA to obtain the polymerizable, BPA‐based tert‐amines DMABPA‐1M (one methacrylate), DMABPA‐2M (two methacrylates), and DMABPA‐1A (one acrylate). The aromatic tert‐amines and ethyl p‐(N,N‐dimethylamino)benzoate (EDMAB) were combined with a camphorquinone sensitizer to form a photoinitiating system, which was applied in photopolymerizations of dental resin formulations, based on Bis‐GMA as a matrix prepolymer, by visible light exposure. The photoconversion of the formulations using the new aromatic tert‐amines as PIs was determined by the spectral changes in FTIR absorption intensities of methacrylate groups in cast films. High conversion (over 70%) resulted from photopolymerizations with (meth)acrylated DMABPA‐(1M, 2M, and 1A).magnified image

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New Families of Photocurable Oligomeric Fluoromonomers for Use in Dental Composites

Cited by 22 publications

References 18 publications

Evaluation of New Tri-methacrylates as a Reactive Diluent in Root Canal Sealant

Evaluation of New Tri-methacrylates as a Reactive Diluent in Root Canal Sealant

(Meth)acrylate vinyl ester hybrid polymerizations

New Aromatic tert‐Amines for Application as Photoinitiator Components in Photocurable Dental Materials

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