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| | Triethylene glycol dimethacrylate Chemical Properties |
| Melting point | -52°C | | Boiling point | 170-172 °C5 mm Hg(lit.) | | density | 1.092 g/mL at 25 °C(lit.) | | vapor pressure | 0.077Pa at 20℃ | | refractive index | n20/D 1.461(lit.) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | Chloroform, Methanol | | form | Oil | | color | Colourless to Pale Yellow | | Specific Gravity | 1.092 | | Water Solubility | 3.6g/L at 20℃ | | α-end | methacrylate | | Ω-end | methacrylate | | BRN | 1797351 | | Henry's Law Constant | 5.8×106 mol/(m3Pa) at 25℃, HSDB (2015) | | Stability: | Light Sensitive | | Cosmetics Ingredients Functions | NAIL CONDITIONING | | InChI | 1S/C14H22O6/c1-11(2)13(15)19-9-7-17-5-6-18-8-10-20-14(16)12(3)4/h1,3,5-10H2,2,4H3 | | InChIKey | HWSSEYVMGDIFMH-UHFFFAOYSA-N | | SMILES | CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C | | LogP | 2.3 at 20℃ | | CAS DataBase Reference | 109-16-0(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Propenoic acid, 2-methyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester(109-16-0) | | EPA Substance Registry System | Triethylene glycol dimethacrylate (109-16-0) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38-43 | | Safety Statements | 26-28-36/37 | | RIDADR | UN 3334 | | WGK Germany | 1 | | RTECS | OZ4100000 | | F | 8-19 | | TSCA | TSCA listed | | HS Code | 29161900 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Skin Sens. 1 | | Hazardous Substances Data | 109-16-0(Hazardous Substances Data) | | Toxicity | LD50 oral in rat: 10837mg/kg |
| | Triethylene glycol dimethacrylate Usage And Synthesis |
| Description | Triethylene glycol dimethacrylate is used as a cross-linking agent in the synthesis of poly (methacrylic acid-g-ethylene glycol) hydrogels which shows large changes in swelling due to changes in pH, temperature and solvent composition. They are also used as divinylic methacrylic monomers which are widely used to form copolymers with divinylbenzene (DVB) and glycidyl methacrylate (GMA) or hydroxyethyl methacrylate (HEMA) comonomers. As a monomer, it is typically used in dental resin materials that can cause specific stress responses in eukaryotic cells. It commonly used to aesthetically restore the structure and function of teeth impaired by caries, erosion, or fracture.
It is cytotoxic via apoptosis, induce genotoxic effects, and delay the cell cycle. It also influences the response of cells of the innate immune system, inhibit specific odontoblast cell functions, or delay the odontogenic differentiation and mineralization processes in pulp-derived cells including stem cells. It is also used as a diluent co-monomer in dimethacrylate based dental composites as well as being used as a branching agent in the atom transfer radical polymerization (ATRP) of styrene.
| | Application | Triethylene glycol dimethacrylate (TEGDMA) is a resin monomer widely used in the composition of dentin bonding agents and composite resins to restore teeth structures impaired by caries and/or fractures. However, resin monomers can be released into the oral environment and can trigger hazardous biological effects on oral tissues. The release of the resin monomers due to degradation and incomplete polymerization can occur hours or days after the treatment. Due to its hydrophilic nature, hydrolysis plays an important role in the degradation processe of TEGDMA. Chemical interactions with oral fluids and mechanical influences may also cause the degradation of resin monomers. Direct contact or diffusion of resin monomers through the dentinal tubules creates ways of interaction between dental pulp tissue and resin monomers. Dentin thickness and the severity of caries lesions are important factors in determining the amount of resin monomers interacting with dental pulp tissue. TEGDMA has been reported to cause cytotoxicity, impaired cellular functions, pulpal inflammatory responses, and changes in the immune system. In addition, TEGDMA may reduce the mineralization capacity of dental pulp cells by decreasing the expression of the mineralization related genes pathways and causing adverse effects.
| | Reference | Krifka, S, et al. "A review of adaptive mechanisms in cell responses towards oxidative stress caused by dental resin monomers. " Biomaterials 34.19(2013):4555-4563.
| | Description | Triethylene glycol dimethacrylate was employed to
optimize the dilution of high-viscosity monomers and
to link together the macromolecules constituting the
polymer, to make their three-dimentional structure
more rigid. It is also a crosslinking agent of acrylic
resins, used in sealents or in dental bonding resins.
These are mainly used in dentistry, by dental technicians
and dentists. | | Chemical Properties | Colorless liquid
 | | Uses | Esters of acrylic acid and methacrylic acid, more commonly known as acrylates and methacrylates are key raw materials in the coatings and printing industry, and in food packaging. | | Uses | TEGDMA is a monomer typically used in dental resin materials that can cause specific stress responses in eukaryotic cells. | | Uses | Triethyleneglycol dimethacrylate is a methacrylic monomer for use as cross-linking agent for adhesives and dental restorative materials. | | General Description | Triethylene glycol dimethacrylate (TEGDMA) is a hydrophilic, low viscosity, difunctional methacrylic monomer employed as a crosslinking agent. | | reaction suitability | reagent type: cross-linking reagent
reaction type: Polymerization Reactions | | Synthesis | Biomass dibasic acid-based unsaturated polyester resins: Dai et al. synthesized a series of biobased unsaturated polyesters (UPRs) derived from 2,5-furandicarboxylic acid (FDCA), itaconic acid (IA), succinic acid (SA), and 1,3-propanediol (PD) by direct polycondensation and cured them with a biobased, non-volatile reactive diluent, guaiacol methacrylate. The results showed that the thermal properties, flexural strength and modulus of the cured UPRs improved considerably after the introduction of FDCA; heat loss of 5 wt% was achieved up to a temperature of 330 C, and flexural strength and modulus reached 122.8 MPa and 3521 MPa, respectively.Rorrer et al. combined muconic acid from biomass with poly(ethylene glycol succinate), poly(propylene glycol butanedioate), poly(succinic acid) butylene glycol) and poly(butylene glycol adipate) into polyesters by polycondensation.Dai et al. introduced a molar ratio of 1.2:1 of itaconic acid (20 g, 154 mmol) and ethylene glycol (7.76 g, 0.125 mol), p-toluenesulfonic acid-hydrate (0.146 g, 0.5 mol% (based on itaconic acid)) as catalyst for prepolymerization, and 4-methoxybenzene (0.146 g, 0.5 mol% (based on itaconic acid)) as a free-radical polymerization blocker 4-methoxyphenol (0.139 g, 0.5 wt% (based on the total amount of itaconic acid and diol)) were added to a four-necked round-bottomed flask fitted with a mechanical stirrer, a thermometer, a reflux condenser and a nitrogen inlet. The mixture was pre-polymerized by reacting at 160C for 2 hours to form oligomers. Then 0.028 g of dibutyltin dilaurate (1 wt% relative to the total weight of the reactants) was added as a polycondensation catalyst. After reacting the oligomer at 160C for 6 hours, the target resin was obtained by cooling to 100C under a vacuum of 0.09-0.095 MPa. |
| | Triethylene glycol dimethacrylate Preparation Products And Raw materials |
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