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Sigma-Aldrich

Triethylene glycol dimethacrylate

99%, cross-linking reagent polymerization reactions, 200 ppm monomethyl ether hydroquinone as inhibitor

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About This Item

Linear Formula:
CH2=C(CH3)COO(CH2CH2O)3COC(CH3)=CH2
CAS Number:
109-16-0
Molecular Weight:
286.32
Beilstein/REAXYS Number:
1797351
EC Number:
203-652-6
MDL number:
MFCD00008591
UNSPSC Code:
12162002
PubChem Substance ID:
329766782
NACRES:
NA.23

product name

Triethylene glycol dimethacrylate, contains 200 ppm monomethyl ether hydroquinone as inhibitor, 99%

Quality Level

100

assay

99%

form

liquid

contains

200 ppm monomethyl ether hydroquinone as inhibitor

reaction suitability

reagent type: cross-linking reagent
reaction type: Polymerization Reactions

refractive index

n20/D 1.461 (lit.)
n/D 1.4613

bp

170-172 °C/5 mmHg (lit.)

density

1.092 g/mL at 25 °C (lit.)
1.074 g/mL

polymer architecture

shape: linear
functionality: homobifunctional

storage temp.

2-8°C

SMILES string

CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C

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

InChI key

HWSSEYVMGDIFMH-UHFFFAOYSA-N

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General 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 a divinylic methacrylic monomer which are widely used to form copolymers with divinylbenzene (DVB) and glycidyl methacrylate (GMA) or hydroxyethyl methacrylate (HEMA) comonomers.

Application

  • Used as a diluent comonomer in dimethacrylate based dental composites.
  • Used as a branching agent in the atom transfer radical polymerization (ATRP) of styrene.

Features and Benefits

Lower viscosity compared to other dimethacrylate monomers enabling higher amounts of filler to be incorporated in dental composites. Non-toxic and can be rapidly polymerized in the presence of oxygen and water.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

332.6 °F - closed cup

flash_point_c

167 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000234211
0000224127
MKCD5684
MKBK2405

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I Sideridou et al.
Biomaterials, 23(8), 1819-1829 (2002-04-13)
In this work the room-temperature photopolymerization of Bis-GMA, Bis-EMA, urethane dimethacrylate (UDMA) and triethylene glycol dimethacrylate (TEGDMA) induced by camphoroquinone/N,N-dimethylaminoethyl methacrylate, as photo-initiator system, was followed by FT-IR. The results obtained were then fitted by a non-linear least square method
Mono-or narrow disperse poly (methacrylate-co-divinylbenzene) microspheres by precipitation polymerization
Li, W. H., & Stover, H. D.
Journal of Polymer Science Part A: Polymer Chemistry, 37(15), 2899-2907 (1999)
Controlled release by using poly (methacrylic acid-g-ethylene glycol) hydrogels
Peppas, N. A., & Klier, J.
Journal of Controlled Release : Official Journal of the Controlled Release Society, 16(1), 203-214 (1991)
Development of branching in atom transfer radical copolymerization of styrene with triethylene glycol dimethacrylate
Yang, H. J., Jiang, B. B., Huang, W. Y., Zhang, D. L., Kong, L. Z., Chen, J. H., & Yang, Y.
Macromolecules, 42(16), 5976-5982 (2009)
Geum-Jun Han et al.
The journal of adhesive dentistry, 14(5), 461-469 (2012-06-23)
To evaluate the effect of applied power on dental ceramic bonding of composite resin using nonthermal atmospheric pressure plasma (APP). A pencil-type APP torch was used to modify the surface chemical composition and hydrophilicity of dental ceramic and to improve
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