Synthesis, characterization and evaluation of new fluorene-based dimethacrylates for formulating dental composites

Culbertson, B. M.; Tiba, Amer; Sang, Ji‐Long; Liu, Y. N.

doi:10.1002/(sici)1099-1581(199905)10:5<275::aid-pat874>3.0.co;2-v

Cited by 24 publications

(6 citation statements)

References 7 publications

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“…The polymers containing fluorene skeletons, especially those possessing diaryl substituents at the bridge (C‐9) position which are recognized as the cardo structure, have attracted considerable interest owing to their high solubility in addition to high thermal stability. The cardo skeleton consisiting of fluorene moiety is also expected to contribute to a variety of good properties such as high refractive index, low birefringence, and high affinity toward fillers enabling fine dispersion of them in composite materials 9–12. Sakurai et al, introduced a fluorene moiety into aromatic polycarbonates and found drastic decrease in birefringence 13.…”

Section: Introductionmentioning

confidence: 99%

Fluorene‐rich high performance polyesters: Synthesis and characterization of 9,9‐fluorenylidene and 2,7‐fluorenylene‐based polyesters with excellent optical property

Seesukphronrarak¹,

Kawasaki²,

Kobori³

et al. 2008

J. Polym. Sci. A Polym. Chem.

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Polyesters PEs containing high content of fluorene units in their backbones were synthesized from 9,9‐diarene‐substituted fluorene diols (1) and fluorene‐based diacid chlorides (2) by high temperature polycondensation at 185 °C in diphenyl ether. The molecular weights of the polyesters PE1‐PE5 were in a range of Mw 25,000–165,000. The polyesters displayed their high thermostability: the glass transition temperatures (Tg) by differential scanning calorimetry analysis ranged from 109 to 217 °C, while the 10% weight loss temperatures (Td10) measured by thermogravimetric analysis were over 400 °C in nitrogen and 395 °C in air. The polyesters had good solubility in most common organic solvents such as chloroform and toluene and gave tough, transparent and flexible cast films. The transmittance of the films was over 80% in the wavelength range from 450 to 700 nm in any PEs. The PEs exhibited high refractive index values around 1.65, while they had very low degree of birefringence. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2549–2556, 2008

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Section: Introductionmentioning

confidence: 99%

Fluorene‐rich high performance polyesters: Synthesis and characterization of 9,9‐fluorenylidene and 2,7‐fluorenylene‐based polyesters with excellent optical property

Seesukphronrarak¹,

Kawasaki²,

Kobori³

et al. 2008

J. Polym. Sci. A Polym. Chem.

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“…Many experimental dimethacrylates have been explored for the reduction of shrinkage and water sorption in composites, seeking to improve such things as dimensional stability, creep resistance, fracture toughness, and wear resistance (36,(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64)(65). The goal is to formulate a better alternative to the commonly used amalgam.…”

Section: Monomers or Matrix Phase Although Bisgma Is Widely Used In mentioning

confidence: 99%

Dental Applications

Culbertson

Kerby

2010

Encyclopedia of Polymer Science and Technology

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The various types of monomers and polymers and methods of polymerization used in dentistry are discussed, along with brief attention given to new areas of promise for preparing better materials for dental applications. Polymeric materials discussed in this article include impression materials, dentures and denture liners, artificial teeth, crown and bridge materials, mouth protectors, maxillofacial materials, restoratives (filling materials), such as glass‐ionomers or glass polyalkenoates, composites and compomers, adhesives, cements, and sealants. While enormous progress has been made in developing improved materials for meeting oral health needs, it remains clear that there are still many opportunities for development of improved materials for use in dental applications.

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“…Depending on the determination approaches, preparation procedures for the crosslinked polymer network, such as photopolymerization or chemical curing and so on, a varied T g for the cured BisGMA network has been published, i.e., 63 C [10], 72 C [25], 230 C [26] and even a double T g of 64 C and 133 C [6]. Experimentally, differential scanning calorimetry (DSC) and dynamic mechanic analysis (DMA) are the most used methods to determine T g of polymers, with the latter having higher sensitivity than the former usually revealing multi-transitions below T g .…”

Section: Novel Trimethacrylates 261mentioning

confidence: 99%

“…To achieve this goal, two types of polymer based restoratives, i.e., composites and glass-ionomers have become the materials of choice in tooth restorations. Based on the concept of improving BisGMA, many other dimethacrylates have been developed, which can be divided into three categories: a) monomers having lower viscosity, such as replacing the hydroxyl on BisGMA or changing the core structure of the BisGMA [4À7]; b) preparing monomers having decreased water sorption, such as fluorine substituted dimethacrylates [8,9]; c) producing monomers having higher T g with more bulky structural units, such as fluorine-based dimethacrylates [10], and exploring poly(isopropylidenediphenol) resin based oligomeric multimethacrylates [11]. 2,2-Bis[4-(2-hydroxy-3-methacryloyloxy-propoxy) phenyl]propane (BisGMA) was the first dimethacrylate based formulation exhibiting satisfactory clinical performance, especially for anterior restoration [3].…”

Section: Introductionmentioning

confidence: 99%

Novel Trimethacrylates: Synthesis, Characterization, and Evaluation of New Monomers for Improved Dental Restoratives

Gao

Schricker

Tong

et al. 2002

Journal of Macromolecular Science, Part A

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Two novel trimethacrylates, i.e., 1,1,1-tri-[4-(methacryloxyethoxy)phenyl] ethane (TMPE) and 1,1,1-tri-[4-(2-methyl-2-methacryloxyethoxy)phenyl]ethane (TMMPE), have been synthesized by reacting methacryloyl chloride with the corresponding hydroxyl intermediates. Both trimethacrylate monomers, having a low viscosity of 11.5 and 13.1 Pa.S, respectively, were blended with TEGDMA at three different weight ratios, i.e., 90=10, 70=30, and 50=50. The mixtures were made visible light-curable (VLC) by the addition of camphorquinone (0.5 wt%) and N,N-dimethylaminoethyl methacrylate (1.0 wt%). In addition to evaluation as cured neat resins, VLC formulations with 70% by wt. of silanated microfiller were also prepared and evaluated. The control in both cases was a VLC formulation of BisGMA=TEGDMA (70=30 and 50=50 wt=wt). These new, formulated resins have both improved physical properties and higher double bond conversion than the BisGMA control, as well as decreased linear polymerization shrinkage (LPS). The neat resin having 70=30 (wt=wt) ratio of TMPE=TEGDMA (T7T3, Table 2) exhibited a compressive strength (CS) of 496 (AE51) MPa compared to the 70=30 (wt=wt) ratio of BisGMA=-TEGDMA control having 425(AE27) MPa. A filled resin having a 90=10 (wt=wt) ratio of TMPE=TEGDMA exhibited a flexural strength (FS) of 122.6(AE 23) MPa, compared with a similar filled BisGMA=TEGDMA (70=30, wt=wt) resin exhibiting 112.7(AE 19) MPa. These and other results suggest that these new trimethacrylates have potential application in formulating dental composites with improved performance.

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Synthesis, characterization and evaluation of new fluorene-based dimethacrylates for formulating dental composites

Cited by 24 publications

References 7 publications

Fluorene‐rich high performance polyesters: Synthesis and characterization of 9,9‐fluorenylidene and 2,7‐fluorenylene‐based polyesters with excellent optical property

Fluorene‐rich high performance polyesters: Synthesis and characterization of 9,9‐fluorenylidene and 2,7‐fluorenylene‐based polyesters with excellent optical property

Dental Applications

Novel Trimethacrylates: Synthesis, Characterization, and Evaluation of New Monomers for Improved Dental Restoratives

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