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Triethylene glycol dimethacrylate

Basic information Description Application Reference Safety Related Supplier

Triethylene glycol dimethacrylate Basic information

Product Name:
Triethylene glycol dimethacrylate
CAS:
109-16-0
MF:
C14H22O6
MW:
286.32
EINECS:
203-652-6
Mol File:
109-16-0.mol
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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.)
refractive index 
n20/D 1.461(lit.)
Flash point:
>230 °F
storage temp. 
2-8°C
Specific Gravity
1.092
BRN 
1797351
InChIKey
HWSSEYVMGDIFMH-UHFFFAOYSA-N
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)
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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
8-19
HS Code 
29161900
Hazardous Substances Data
109-16-0(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 10837mg/kg

MSDS

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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.

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.

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Triethylene glycol dimethacrylateSupplierMore

Liyang Ruipu New Materials Co., Ltd. Gold
Tel:
+86-0519-82038123/18951201333
Email:
sales@ruipuchem.net
Qingdao RENAS Polymer Material Co.,Ltd. Gold
Tel:
86-0532-86867058
Email:
sales@qdrenas.com
Qingdao ZKHT Chemical Co., Ltd. Gold
Tel:
532-86898076
Email:
zkhtchem@163.com
Aikon International Limited Gold
Tel:
025-66113011
Email:
hywu@aikonchem.com
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Basic information Description Application Reference Safety Related Supplier