Ethyl 4 dimethylaminobenzoate

Manufactured by Merck Group

Sourced in United States, Germany

Ethyl 4-dimethylaminobenzoate is a chemical compound used in laboratory settings. It is a crystalline solid with a specific molecular structure and chemical properties. The core function of this product is to serve as a reagent or intermediate in various scientific experiments and analyses, though its precise applications may vary depending on the specific research or testing requirements.

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Lab products found in correlation

30 protocols using ethyl 4 dimethylaminobenzoate

Hydrophilic Adhesive for Peptide Functionalization

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The model hydrophilic adhesive consisted of 2-hydroxyethylmethacrylate (HEMA), triethylene glycol dimethacrylate (TEGDMA) and (trimethoxysilyl) propyl methacrylate (MPS) with a mass ratio of 8/1/1 (HEMA/TEGDMA/MPS). This model hydrophilic adhesive system has been developed and optimized for peptide engineering in our previous investigations (Ye et al., 2011 (link); Abedin et al., 2014 (link); Xie et al., 2020 (link)). The following photoinitiators (all from Aldrich, Milwaukee, WI, United States) were used: camphoroquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB) and diphenyliodonium hexafluorophosphate (DPIHP). The amounts of photosensitizer, coinitiator amine and iodonium salt were fixed at 0.5 mass% with respect to the total amount of monomer (Guo et al., 2008 (link); Ye et al., 2009 (link); Song et al., 2014 (link)). The resin mixtures were prepared in a brown glass vial under amber light. Continuous shaking and sonication for 48 h were required to yield well-mixed homogenous resin solutions (Song et al., 2016 (link)). The hydrophilic adhesive formulation was mixed with 10 mass per-cent co-polymerizable hydroxyapatite-binding peptide, e.g., MMES- KGGG_HABP, and diluted with ethanol in a weight ratio of 80/20.

Spencer P., Ye Q., Kamathewatta N.J., Woolfolk S.K., Bohaty B.S., Misra A, & Tamerler C. (2021). Chemometrics-Assisted Raman Spectroscopy Characterization of Tunable Polymer-Peptide Hybrids for Dental Tissue Repair. Frontiers in materials, 8, 681415.

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Adhesive Resin Formulation and Characterization

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2,2-Bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]-propane (BisGMA, Polysciences, Warrington, PA) and 2-hydroxyethylmethacrylate (HEMA, Acros Organics, NJ) were used as received without further purification, as monomers in dentin adhesives. Two siloxane methacrylate monomers (SM1 and SM2) were synthesized in our lab. The control adhesive resin consisted of HEMA and BisGMA with a mass ratio of 45/55. This control was used to compare with the experimental adhesive resins with HEMA / BisGMA / SM = 45/55-x/x (w/w) ratio. The control and experimental adhesives were also formulated with 12 wt % water to simulate bonding in the mouth. The concentration of water was based on the total final weight of the adhesive resin. Camphorquinone (CQ, 0.5 wt %), ethyl-4-(dimethylamino) benzoate (EDMAB, 0.5 wt %) and diphenyliodonium hexafluorophosphate (DPIHP,1.0 wt %) were obtained from Aldrich (Milwaukee, WI, USA) and used as a three-component-photoinitiator system without further purification. 2,4,6,8-Tetramethyl-2,4,6,8-tetrakis (propyl glycidyl ether) cyclotetrasiloxane (TPGTS), Glycerol dimethacrylate (GDMA, assay 85%, mixture of isomers), ethyl acetate, boron trifluoride diethyl etherate (BF₃O(C₂H₅)₂), anhydrous magnesium sulfate (MgSO₄), and all other chemicals were purchased from Sigma-Aldrich at reagent grade and used without further purification.

Ge X., Ye Q., Song L., Misra A, & Spencer P. (2014). Synthesis and evaluation of novel siloxane-methacrylate monomers used as dentin adhesives. Dental materials : official publication of the Academy of Dental Materials, 30(9), 1073-1087.

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Hydrophilic Adhesive for Peptide Functionalization

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Adhesive System Formulation with MMP Inhibitor

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The experimental adhesive system (EXP) was formulated as in previous study,^{14 (link)} using the following monomers (wt.%): HEMA (25%), 4-META (30%), TEGDMA (25%) (Essthec, Inc. Essington, PA, USA). Acetone (15%) and water (4%) were used as solvents and Camphorquinone (0.5%) and EDMAB (0.5%) (Ethyl 4-(dimethylamino)benzoate – Aldrich Chemical Company, Inc., Milwaukee, WI, USA) were incorporated as photosensitizer and reducing agents, respectively. The components of the adhesive were weighed using an analytical balance (AUW 220D, Shimadzu, Tokyo, Japan), mixed and homogenized in a dual centrifuge (150.1 FVZ SpeedMixer DAC, FlackTek Inc., Herrliberg, Germany) at 1300 rpm for 2 minutes.
The MMP inhibitor GM1489 (EMD Chemicals, Inc. San Diego, CA, USA) was incorporated in this formulation in different concentrations 0, 1 µM, 5 µM and 10 µM, obtaining four different experimental adhesives. The adhesive system Adper Single Bond 2 (SB) (3M ESPE, Sumaré, SP, Brazil) was used as a commercial reference and also received different concentration of GM1489. After incorporation of GM1489 in each adhesive system, they were homogenized at 2400 rpm for 2 min.^{14 (link)}Figure 1 shows the tested groups.
Figure 1Experimental groups and adhesive systems used in this study

MIRANDA M.E., da SILVA E.M., de OLIVEIRA M.F., SIMMER F.S., dos SANTOS G.B, & AMARAL C.M. (2020). Resin-dentin bond stability of etch-and-rinse adhesive systems with different concentrations of MMP inhibitor GM1489. Journal of Applied Oral Science, 28, e20190499.

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Formulation and Preparation of Cu-MBGN Glass-Reinforced Dental Resin Composites

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Cu-MBGN glass particles were prepared as mentioned previously in Zheng et al. [31 (link)]. The dental resin matrix was prepared by mixing Bisphenol A–glycidyl methacrylate (BisGMA; Merck, Darmstadt, Germany) and triethylene glycol dimethacrylate (TEGDMA; Merck, Darmstadt, Germany) in a 60/40 ratio and made photoactive by adding 0.2 wt% camphorquinone and 0.8 wt% ethyl-4-dimethylamino benzoate (Merck, Darmstadt, Germany). The resin was mixed with fillers to obtain eight experimental resin composites, the detailed composition of which is described in Table 1, while the composition of the fillers, as provided by the manufacturers, is listed in Table 2. The resin was preheated to 100 °C and fillers were gradually added under the orange illumination. Resin and fillers were mixed with an asymmetric centrifugal mixer (Speed Mixer 150 FVZ, Hauschild & Co. KG, Hamm, Germany) at 27,000 rpm for 5 min to obtain the composite materials.

Munir A., Marovic D., Nogueira L.P., Simm R., Naemi A.O., Landrø S.M., Helgerud M., Zheng K., Par M., Tauböck T.T., Attin T., Tarle Z., Boccaccini A.R, & Haugen H.J. (2022). Using Copper-Doped Mesoporous Bioactive Glass Nanospheres to Impart Anti-Bacterial Properties to Dental Composites. Pharmaceutics, 14(10), 2241.

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Interfacial Tension Measurement of Multiphase Microfluidic System

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Fluorinated oil (HFE, Novec 7500 3 M, Merck, Darmstadt, Germany) was used as the core dispersed phase, whose density and dynamic viscosity are 1.61 g/mL and 1.31 mPa·s, respectively [8 (link)]. The shell dispersed phase was a polymer consisting of 0.06 g ethyl-4(dimethylamino) benzoate (Merck, Darmstadt, Germany), 0.05 g camphorquinone (Merck), and 10 g trimethylolpropane trimethacrylate (TMPTMA, Merck). The corresponding density and dynamic viscosity are 1.07 g/mL and 42 mPa·s, respectively [35 (link)]. The continuous phase was 80% glycerol dissolved in 20% DI water, with 0.1% Tween 20, and its density and dynamic viscosity are 1.21 g/mL and 75.42 mPa·s, respectively [36 (link)]. The laboratory temperature was maintained at 23 °C.
The interfacial tension

σ_{i j}

between each pair of two liquid phases were measured using the reverse pendant drop method with an optical tensiometer (Theta Flex from Biolin Scientific, Gothenburg, Sweden). Figure 2A reports the mean contact angles of each pair of two phases, while Figure 2B,C show the images of the pendant drops. The interfacial tensions of the inner and outer interfaces were measured for 10 s for each case with 33 frames per second, and the measured time-averaged mean interfacial coefficients are 3.45 and 8.48 mN/m, respectively.

Dai Y., Cha H., Nguyen N.K., Ouyang L., Galogahi F., Yadav A.S., An H., Zhang J., Ooi C.H, & Nguyen N.T. (2022). Dynamic Behaviours of Monodisperse Double Emulsion Formation in a Tri-Axial Capillary Device. Micromachines, 13(11), 1877.

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Synthesis and Characterization of Bioactive Dental Composites

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Bisphenol A–glycidyl methacrylate (BisGMA) and triethylene glycol dimethacrylate (TEGDMA) were purchased from Merck, Darmstadt, Germany. An identical resin matrix containing 60:40 weight ratio of BisGMA: TEGDMA with a photoinitiator system (camphorquinone (0.2 wt %; Merck) and ethyl-4-dimethylamino benzoate (0.8 wt %; Merck)) was used for all materials. Resin was heated to 60 °C prior to admixture of fillers.
Four types of fillers were used in this study, as shown in Table 1.
The materials were mixed in the absence of blue light using an asymmetrical centrifugal mixer (Speed Mixer TM DAC 150 FVZ, Hauschild & Co KG, Hamm, Germany) at gradually increasing speed up to 2700 rpm.
Eight experimental resin composites were prepared, divided into two groups:

Group testing the bimodal approach with 65 wt % total filler load and

Group testing the trimodal approach with 70 wt % total filler load used for investigating 1, 5, and 10 wt % Cu-MBGN composites with silica fillers.

Each group contained both inert control (silica and microfillers; 10-Si and 15-Si) and bioactive control (45S5 BG and microfillers, 10-BG and 15-BG) in adequate amounts corresponding to the total filler load (Table 2).

Marovic D., Haugen H.J., Negovetic Mandic V., Par M., Zheng K., Tarle Z, & Boccaccini A.R. (2021). Incorporation of Copper-Doped Mesoporous Bioactive Glass Nanospheres in Experimental Dental Composites: Chemical and Mechanical Characterization. Materials, 14(10), 2611.

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Synthesis and Formulation of Cu-MBGN Composite

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We synthesised Cu-MBGN according to a protocol described elsewhere [22 (link)]. The fillers used in this study are presented in Table 2. We admixed fillers to form a photoreactive resin mixture composed of bisphenol-A-glycidyldimethacrylate (BisGMA; Merck, Darmstadt, Germany) and triethylene glycol dimethacrylate (TEGDMA, Merck) at a 60/40 ratio, with 0.2 wt.% of camphorquinone (Merck) and 0.8 wt.% of ethyl-4-(dimethylamino) benzoate (Merck). The compositions of the composites are presented in Table 3. The total filler load was kept constant at 65 wt.%.

Marovic D., Par M., Tauböck T.T., Haugen H.J., Negovetic Mandic V., Wüthrich D., Burrer P., Zheng K., Attin T., Tarle Z, & Boccaccini A.R. (2022). Impact of Copper-Doped Mesoporous Bioactive Glass Nanospheres on the Polymerisation Kinetics and Shrinkage Stress of Dental Resin Composites. International Journal of Molecular Sciences, 23(15), 8195.

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Dental Resin Monomer Formulation

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The primary monomers Bis-GMA (B) (BOC Sciences Inc., USA) and/or UDMA (U) (ESSTECH Inc., USA) were combined with TEGDMA (T) (BOC Sciences Inc., USA) using various mass ratios. Among them, the binary dental resins were abbreviated according to the mass ratios of Bis-GMA or UDMA, i.e., B20 for B/T resins with 20 wt% Bis-GMA and U20 for U/T resins with 20 wt% UDMA. The photoinitiator system was composed of CQ (camphorquinone) and EDAB (ethyl 4-dimethylaminobenzoate) (both from Sigma-Aldrich, Milwaukee, WI) with 0.2 wt% and 0.8 wt%, respectively [20 (link), 21 ]. The resin monomers and photoinitiator system were blended in a centrifugal mixer (DAC 150FVZ, FlackTek Inc., Landrum, SC), and stirred for about 30 min (2000r/s) to ensure the dental resin compounds were well-mixed. The monomers were stored under refrigeration and the photoinitiators were kept in the dark before used.

Li W., Wang K., Wang Z, & Li B. (2022). Optimal resin monomer ratios for light-cured dental resins. Heliyon, 8(9), e10554.

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Silicone-Based Photocurable Dental Composite

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A silicone containing di-cycloaliphatic epoxy resin (bis[2-(3,4-epoxycyclohexyl)ethyl] tetramethyldisiloxane, UV30) was purchased from ABCR (Karlsruhe, Germany). Iodonium salt photoinitiator [4(1-methylethyl)phenyl][4-methylphenyl] iodonium tetrakis (pentafluorophenyl) borate, Rhodorsil 2074, was given by Rhodia (Lyon, France). Camphoquinone and ethyl 4-(dimethylamino)benzoate (EMBO) were purchased by Sigma-Aldrich (St. Louis, MO, USA). The chemical structures of the monomer and the photoinitiators are reported in Figure 1. Very low refractive dental glass filler, G018-163 (Schott), Sr-(15%) and F-(2%)-containing, with a mean particle size of 1.5 μm were used.

Vitale A., Sangermano M., Bongiovanni R., Burtscher P, & Moszner N. (2014). Visible Light Curable Restorative Composites for Dental Applications Based on Epoxy Monomer. Materials, 7(1), 554-562.

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