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

Abstract

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.

Recent Developments of New Components for Dental Adhesives and Composites

“…Furthermore, a number of novel trimethacrylates were synthesised and evaluated for improved dental restoratives. [95][96][97][98] (Figure 25). TMPE (molecular weight: 643 g Á mol À1 ) and TMMPE with a similar molecular weight, respectively, showed a lower viscosity of 11.5 and 13.1 Pa Á s, compared to the 800 Pa Á s of Bis-GMA (512 g Á mol À1 ).…”

“…VL-cured composite formulations of TMPE mixtures with TEGDMA exhibited a similar flexural strength as filled Bis-GMA/-TEGDMA mixtures, whereas the linear polymerisation shrinkage was reduced in TMPE resins or filled materials compared with the Bis-GMA control. [96] The trimethacrylate TTEMA (719 g Á mol À1 ) was synthesised as a pale yellow oil. The polymerisation shrinkage of this monomer was only 2.09 vol.-% after 60 s of irradiation using a camphorquinone (CQ)/2-(dimethylamino)ethyl methacrylate (DMAEMA) photoinitiator system.…”

Preparation and properties of novel dentin adhesives with esterase resistance

“…[19][20][21][22] To a three-neck flask containing TMPE (10 g, 0.057 mol), TEA (20.1 mL, 0.143 mol), and dry ethyl acetate (72 mL) under N 2 atmosphere, a solution of methacryloyl chloride (14 mL, 0.143 mol) in dry ethyl acetate was added dropwise with stirring at 08C. An ice bath was used to maintain 08C during the addition of the methacryloyl chloride solution.…”

2,3-Branching benzyl ether dendrimers for the enhancement of dental composites

“…This modified resin was then mixed with 3 parts by weight of silanated filler (Schott Glass GM27884, UF1.0, 3.2% silane) to yield samples containing 0.5%, 2.5%, 7.5%, and 12.5% dendritic additive by weight. The composite mixtures were stored at 0°C in the dark subsequent to formulation [20,44].…”

“…The samples were dried at ambient temperature for 8 hours before testing. The peak and break loads of the bar samples were determined using the Instron 4204 screw-drive apparatus (Instron Corp., Canton, MA; three-point break, 1 kN load cell, 1.0 mm/min crosshead speed) and collected using the Testworks software package [20,44].…”