Triethylene glycol dimethacrylate
[CAS# 109-16-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Triethylene glycol dimethacrylate
• Synonyms: 2,2'-Ethylenedioxydiethyl dimethacrylate; Ethane-1,2-diylbis(oxyethane-2,1-diyl) bis(2-methylacrylate)
• Molecular Formula: C₁₄H₂₂O₆
• Molecular Weight: 286.32
• CAS Registry Number: 109-16-0
• EC Number: 203-652-6
• SMILES: CC(=C)C(=O)OCCOCCOCCOC(=O)C(=C)C

Properties

• Density: 1.092
• Boiling point: 170-172 ºC (5 mmHg)
• Refractive index: 1.461
• Flash point: >110 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H317-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1B	H317
Respiratory sensitization	Resp. Sens.	1	H334

Discovory and Applicatios

Triethylene glycol dimethacrylate (TEGDMA), with the chemical formula C₁₀H₁₂O₄, is a prominent compound in the field of polymer chemistry, known for its role as a cross-linking agent and monomer in various polymerization processes. The discovery and application of TEGDMA have significantly impacted the development of high-performance materials in both industrial and biomedical fields.

The development of triethylene glycol dimethacrylate began with efforts to modify and enhance the properties of standard methacrylate compounds. TEGDMA is derived from triethylene glycol, which has been functionalized with two methacrylate groups. This structure provides TEGDMA with unique reactivity and utility in polymer chemistry. Its synthesis typically involves the reaction of triethylene glycol with methacrylic acid or its derivatives under controlled conditions to introduce the methacrylate groups.

One of the primary applications of TEGDMA is as a cross-linking agent in the production of dental resins and composites. In the dental industry, TEGDMA is used in combination with other methacrylate monomers to create composite resins with improved mechanical properties and durability. The cross-linking capability of TEGDMA helps to enhance the strength and resistance of dental materials to wear and degradation. These properties make TEGDMA-based composites suitable for use in restorative dentistry, where strong and long-lasting materials are required for fillings, crowns, and other dental applications.

TEGDMA is also widely utilized in the formulation of various adhesives and coatings. Its role as a cross-linker helps to improve the adhesion and performance of these materials. In adhesives, TEGDMA contributes to the formation of strong bonds between surfaces, enhancing the overall effectiveness of the adhesive. In coatings, it helps to create films with excellent mechanical properties, chemical resistance, and durability. These properties are particularly important in protective coatings used in automotive, aerospace, and industrial applications.

In addition to its use in dental materials and coatings, TEGDMA is employed in the production of hydrogels and biomedical materials. The ability of TEGDMA to form cross-linked networks makes it suitable for creating hydrogels with controlled swelling and release properties. These hydrogels are used in various biomedical applications, including wound dressings, tissue engineering scaffolds, and drug delivery systems. The biocompatibility and mechanical strength of TEGDMA-based hydrogels contribute to their effectiveness in these applications.

Handling triethylene glycol dimethacrylate requires proper safety measures, as it can cause irritation to the skin, eyes, and respiratory tract. It is essential to use appropriate protective equipment and follow safety protocols when working with TEGDMA to minimize exposure and potential health risks.

Overall, the discovery and application of triethylene glycol dimethacrylate have had a significant impact on the development of advanced materials in both industrial and biomedical fields. Its versatility as a cross-linking agent and monomer underscores its importance in creating high-performance materials with a wide range of applications.

References

2012. Influence of curing time, overlay material and thickness on three light-curing composites used for luting indirect composite restorations. The Journal of Adhesive Dentistry.
DOI: 10.3290/j.jad.a22765

2009. Excretion of dental resin monomers and metabolic intermediates via urine in guinea pigs. Dental Materials.
DOI: 10.1016/j.dental.2008.08.013

1993. Determination of the degree of cure of dental resins using Raman and FT-Raman spectroscopy. Dental Materials.
DOI: 10.1016/0109-5641(93)90050-z