Trimethylolpropane trimethacrylate
[CAS# 3290-92-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: Trimethylolpropane trimethacrylate
• Synonyms: TMPTMA; 2,2-Bis(methacryloyloxymethyl)butyl methacrylate; 2-Ethyl-1,3-dimethacryloxy-2-(methacryloxymethyl)propane
• Molecular Formula: C₁₈H₂₆O₆
• Molecular Weight: 338.40
• CAS Registry Number: 3290-92-4
• EC Number: 221-950-4
• SMILES: CCC(COC(=O)C(=C)C)(COC(=O)C(=C)C)COC(=O)C(=C)C

Properties

• Density: 1.06
• Melting point: -14 °C
• Refractive index: 1.472
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS09 Warning
• Risk Statements: H411
• Safety Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	1B	H360
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Trimethylolpropane trimethacrylate is a versatile chemical compound widely used in polymer chemistry and material science. As a trimethacrylate ester, it is derived from trimethylolpropane, which is reacted with methacrylic acid to form the corresponding ester. This substance is characterized by its three methacrylate groups attached to a central trimethylolpropane backbone.

The discovery of trimethylolpropane trimethacrylate can be traced back to research focused on developing multifunctional monomers that enhance the properties of polymeric materials. The incorporation of multiple methacrylate groups allows for increased cross-linking density during polymerization, leading to materials with enhanced mechanical properties and chemical resistance. This discovery was instrumental in advancing the field of high-performance polymers and resins.

One of the primary applications of trimethylolpropane trimethacrylate is in the formulation of dental materials. In dental composites and adhesives, this compound acts as a cross-linking agent that improves the strength and durability of the material. The ability of trimethylolpropane trimethacrylate to form a highly cross-linked network enhances the mechanical properties of dental restorations, making them more resistant to wear and degradation.

In addition to its use in dental applications, trimethylolpropane trimethacrylate is employed in the production of various coatings and inks. Its role as a cross-linking agent in these formulations contributes to the development of coatings with superior adhesion, chemical resistance, and hardness. The compound is particularly useful in UV-curable coatings, where it helps to achieve rapid curing and high-performance characteristics.

Another notable application of trimethylolpropane trimethacrylate is in the creation of advanced polymeric materials. Its inclusion in polymer formulations facilitates the development of materials with tailored properties, such as high impact resistance, flexibility, and thermal stability. These properties are crucial for applications in industries ranging from automotive to aerospace, where performance and durability are paramount.

Trimethylolpropane trimethacrylate is also utilized in the manufacture of adhesives and sealants. The compound’s ability to form strong, cross-linked networks enhances the bonding strength and longevity of these products. This makes it valuable in various industrial and consumer applications where reliable adhesion is required.

The compound's utility extends to the field of biomaterials as well. Research into its use in medical and pharmaceutical applications explores its potential for developing materials with specific biological properties, such as controlled release systems or tissue engineering scaffolds.

Overall, trimethylolpropane trimethacrylate is a significant compound in polymer chemistry due to its ability to enhance the properties of various materials through cross-linking. Its diverse applications in dental materials, coatings, adhesives, and advanced polymers underscore its importance in modern material science and industrial applications.

References

1973 Some Fundamental Aspects of the Polymerization of Vinyl Monomers with Electron Beams. Nonpolluting Coatings and Coating Processes.
DOI: 10.1007/978-1-4684-0736-5_12

2024 Bridging the future: unveiling the latest innovations in ethylene vinyl acetate blends and composites through electron beam irradiation-a comprehensive review. Macromolecular Research, 32(9).
DOI: 10.1007/s13233-024-00292-4

2024 PBS melt strength improving for supercritical CO2 foaming molding by physical adsorption and crystallization. Polymer Bulletin, 81(14).
DOI: 10.1007/s00289-024-05251-8