Triethylene glycol dimethacrylate

Base Information

• Chemical Name: Triethylene glycol dimethacrylate
• CAS No.: 109-16-0
• Deprecated CAS: 102770-39-8,107869-00-1,113723-03-8,116117-65-8,120415-48-7,121150-61-6,121484-13-7,143083-95-8,184845-37-2,202134-79-0,212247-03-5,37291-80-8,52325-89-0,64641-52-7,72145-92-7,76611-53-5,77302-65-9,476300-64-8,544700-08-5,664995-57-7,950837-40-8,2237225-55-5,107869-00-1,113723-03-8,116117-65-8,120415-48-7,121150-61-6,121484-13-7,143083-95-8,184845-37-2,202134-79-0,212247-03-5,37291-80-8,476300-64-8,52325-89-0,544700-08-5,64641-52-7,664995-57-7,72145-92-7,76611-53-5,77302-65-9
• Molecular Formula: C14H22O6
• Molecular Weight: 286.325
• Hs Code.: 29161900
• European Community (EC) Number: 203-652-6
• NSC Number: 84260
• UNII: 14I47YJ5EY
• DSSTox Substance ID: DTXSID3029607
• Nikkaji Number: J77.220H
• Wikidata: Q27251632
• ChEMBL ID: CHEMBL3187544
• Mol file: 109-16-0.mol

Synonyms:TEGDMA;TEGMA;triethylene glycol dimethacrylate;triethylene glycoldimethacrylate;triethyleneglycol dimethacrylate;trioxyethylene dimethacrylate

Chemical Property of Triethylene glycol dimethacrylate

Chemical Property:

• Vapor Pressure: 0.000119mmHg at 25°C
• Melting Point: -52 °C
• Refractive Index: n20/D 1.461(lit.)
• Boiling Point: 335.5 °C at 760 mmHg
• Flash Point: 159.1 °C
• PSA: 71.06000
• Density: 1.063 g/cm³
• LogP: 1.25820
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: 3.6g/L at 20℃
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 286.14163842
• Heavy Atom Count: 20
• Complexity: 314

Purity/Quality:

99.5% (Total Esters) ^*data from raw suppliers

TGM3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-28-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> (Meth)acrylates
• Canonical SMILES: CC(=C)C(=O)OCCOCCOCCOC(=O)C(=C)C
• General Description: Triethylene glycol dimethacrylate (TEGDMA) is a commonly used diluent monomer in dental resin composites, often combined with base monomers like BisGMA to improve handling properties and reduce viscosity. In this study, TEGDMA was incorporated into light-curing dental composites alongside novel liquid crystalline urethane methacrylates and zirconium silicate nanopowder filler. The resulting composites exhibited favorable properties, including controlled volumetric shrinkage, water sorption, and solubility, while maintaining adequate hydrophobicity and potential bacteriostatic effects against *Streptococcus mutans*. Its role as a reactive diluent highlights its importance in optimizing the performance of dental restorative materials.

Technology Process of Triethylene glycol dimethacrylate

There total 10 articles about Triethylene glycol dimethacrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

dimethyltin dichloride (753-73-1) + 4-methoxy-phenol (150-76-5) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → triethyleneglycol dimethacrylate (109-16-0)

Guidance literature:

With sodium methylate; hydroquinone; In n-heptane; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol;

Reference yield: 81.0%

Methacryloyl chloride (920-46-7,26937-45-1) + 2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol (201037-95-8) → triethyleneglycol dimethacrylate (109-16-0) + 2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate (495417-68-0)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃;

DOI:10.1021/ma021257f

Reference yield:

Methacryloyl chloride (920-46-7,26937-45-1) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethyleneglycol dimethacrylate (109-16-0) + 2-(2-(2-hydroxyethoxy)ethoxy)ethyl methacrylate (2351-42-0,25736-86-1)

Guidance literature:

2,2'-[1,2-ethanediylbis(oxy)]bisethanol; With pyridine; In dichloromethane; at 18 - 28 ℃; for 0.5h; Inert atmosphere;

Methacryloyl chloride; In dichloromethane; at 18 - 28 ℃; for 4h; Cooling with ice; Inert atmosphere;

upstream raw materials:

Methacryloyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

poly(methacrylic acid)

methacrylic acid methyl ester

Refernces

Synthesis and properties of liquid crystalline urethane methacrylates for dental composite applications

10.1002/pola.24693

The research focuses on the development and evaluation of novel liquid crystalline urethane methacrylates for use in dental composite materials. The study investigates three newly synthesized liquid crystalline methacrylates—UMA-Q1, UMA-Q2, and UMA-Chol—which are designed to be used as comonomers in light-curing dental resin-based composites. These compounds are combined with BisGMA (bisphenol A diglycidyl methacrylate) or its derivative modified with urethane methacrylate groups, and further diluted with TEGDMA (triethyleneglycol dimethacrylate). The composites are reinforced with 70% filler, specifically zirconium silicate nanopowder that has been silanized. The research explores the relationship between the structure of the liquid crystalline monomers, their photopolymerization rates, and the specific properties of the dental resin composites, such as volumetric shrinkage, water sorption, water solubility, and hydrophobicity. The study also examines the potential bacteriostatic activity of the composites against Streptococcus mutans, a common bacterium in the dental field. The results indicate that the incorporation of these liquid crystalline monomers can enhance the properties of dental composites, making them more suitable for restorative dental applications.

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