Urethane dimethacrylate
[CAS# 72869-86-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: Urethane dimethacrylate
• Synonyms: 7,7,9-Trimethyl-4,13-dioxo-3,14-dioxa-5,12-diaza-hexadecan-1,16-diol dimethacrylate; UDMA
• Molecular Formula: C₂₃H₃₈N₂O₈
• Molecular Weight: 470.56
• CAS Registry Number: 72869-86-4 (934705-15-4)
• EC Number: 276-957-5
• SMILES: CC(CCNC(=O)OCCOC(=O)C(=C)C)CC(C)(C)CNC(=O)OCCOC(=O)C(=C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.479, Calc.^*
• Boiling Point: 594.3±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 313.2±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H317-H411
• Safety Statements: P261-P272-P273-P280-P302+P352-P321-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Urethane dimethacrylate is a chemical compound with a significant impact on various industrial applications due to its versatile properties and unique structure. This compound, characterized by its urethane linkage and two methacrylate groups, has found widespread use in polymer chemistry and materials science.

The discovery of urethane dimethacrylate can be traced back to the ongoing search for improved resins and monomers with enhanced performance characteristics. The incorporation of methacrylate groups provides the compound with excellent polymerization properties, making it a valuable component in the production of advanced materials. The urethane linkage, on the other hand, contributes to the compound’s mechanical strength, flexibility, and durability.

In practical applications, urethane dimethacrylate is primarily used in the formulation of high-performance coatings and adhesives. Its ability to undergo free-radical polymerization enables the creation of strong, durable films with excellent adhesion properties. This makes it particularly useful in the automotive and aerospace industries, where coatings must withstand harsh environmental conditions and mechanical stresses. The compound’s versatility also extends to the field of dental materials, where it is employed in the production of dental composites and sealants. Its properties contribute to the development of materials that offer excellent wear resistance, bonding strength, and aesthetic appeal.

Another significant application of urethane dimethacrylate is in the manufacture of various types of inks and paints. Its inclusion in formulations enhances the durability and adhesion of the final products, making them suitable for use on a wide range of surfaces. The compound’s ability to form high-quality films contributes to the longevity and effectiveness of these products, which are essential for both industrial and consumer applications.

Research continues to explore new ways to utilize urethane dimethacrylate in advanced materials and technologies. Innovations in polymer chemistry aim to optimize the compound’s properties and discover new applications, expanding its role in various industries. As technology progresses, urethane dimethacrylate’s unique characteristics and performance capabilities will likely drive further advancements in material science and engineering.

References

2009. Synthesis of dye functionalized xerogels via nucleophilic aromatic substitution of fluoro aromatic compounds with aminosilanes. Journal of Sol-Gel Science and Technology, 52(2).
DOI: 10.1007/s10971-009-2096-x