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.)

Flash point:

>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

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)

Safety Information

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

MSDS

• Language:English Provider:Ethane-1,2-diylbis(oxyethane-2,1-diyl) bis(2-methylacrylate)
• Language:English Provider:SigmaAldrich

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

Triethyleneglycol dimethacrylate is a methacrylic monomer for use as cross-linking agent for adhesives and dental restorative materials.

Uses

TEGDMA is a monomer typically used in dental resin materials that can cause specific stress responses in eukaryotic cells.

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.

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 160??C 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 160??C for 6 hours, the target resin was obtained by cooling to 100??C under a vacuum of 0.09-0.095 MPa.

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