(Dicyclopentadienyloxy)ethyl methacrylate
[CAS# 68169-03-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: (Dicyclopentadienyloxy)ethyl methacrylate
• Synonyms: 3a,4,5,6,7,7a-Hexahydro-5(or 6)-(2-hydroxyethoxy)-4,7-methanoindene methacrylate; 512M; Dicyclopentenyloxyethyl methacrylate; Ethylene glycol dicyclopentenyl ether methacrylate; FA 512M; FA 512MT; Fancryl 512M; Fancryl FA 512M; Fancryl FA 512MT; QM 57T; QM 652; Rocryl QM 57; Rocryl QM 57T
• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.34
• CAS Registry Number: 68169-03-9 (68586-19-6)
• SMILES: CC(=C)C(=O)OCCOC1CC2CC1C3C2CC=C3

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.528, Calc.^*
• Boiling Point: 358.9±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 149.7±17.8 ºC, Calc.^*

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

Discovory and Applicatios

(Dicyclopentadienyloxy)ethyl methacrylate is a distinctive chemical compound within the realm of polymer chemistry, known for its unique structural features and versatile applications. As an ester derivative of methacrylic acid, this substance combines the reactive methacrylate group with a dicyclopentadienyloxy moiety, creating opportunities for advanced polymer synthesis and material design.

The discovery of (dicyclopentadienyloxy)ethyl methacrylate can be attributed to the ongoing exploration of functional monomers in polymer chemistry. Researchers aimed to develop new monomers with unique properties that could enhance polymer performance in various applications. The incorporation of the dicyclopentadienyloxy group into the methacrylate structure was particularly appealing due to the unique electronic and steric effects of the dicyclopentadienyl unit. This structure was expected to impart special characteristics to the resulting polymers, such as increased thermal stability and altered solubility.

The synthesis of (dicyclopentadienyloxy)ethyl methacrylate typically involves the reaction of dicyclopentadienyl alcohol with methacrylic acid or its derivatives. The process is designed to ensure the formation of the ester linkage, which is crucial for the polymerization process. The resulting monomer exhibits the ability to undergo polymerization through its methacrylate group, forming polymers with the dicyclopentadienyloxy moiety integrated into the polymer backbone.

One of the primary applications of (dicyclopentadienyloxy)ethyl methacrylate is in the development of specialty polymers with enhanced properties. The unique structure of this monomer allows for the creation of polymers with improved thermal stability, mechanical strength, and chemical resistance. These properties are particularly valuable in applications where durability and performance are critical, such as in high-temperature coatings, advanced composites, and industrial adhesives.

In the field of material science, the use of (dicyclopentadienyloxy)ethyl methacrylate has led to the development of polymers with tailored properties for specific applications. For example, the incorporation of the dicyclopentadienyl unit can enhance the polymer's compatibility with various fillers and additives, leading to improved performance in composite materials. Additionally, the increased thermal stability of the resulting polymers makes them suitable for use in high-temperature environments, such as in aerospace and automotive applications.

Another significant application of (dicyclopentadienyloxy)ethyl methacrylate is in the field of coatings and adhesives. The monomer's ability to form cross-linked polymers contributes to the development of coatings with excellent abrasion resistance and adhesion properties. These characteristics are valuable in protective coatings for metals, plastics, and other substrates, where long-term durability and resistance to environmental factors are essential.

The monomer is also explored in the design of functionalized materials for electronic and optical applications. The dicyclopentadienyl unit can introduce unique electronic properties into the polymer matrix, making it suitable for applications in electronic devices and optical materials. The ability to tailor the electronic and optical properties of the resulting polymers opens up opportunities for innovation in areas such as sensors, display technologies, and optoelectronic devices.

In summary, (dicyclopentadienyloxy)ethyl methacrylate is a valuable monomer in polymer chemistry, offering unique properties and applications. Its discovery has led to the development of advanced polymers with enhanced thermal stability, mechanical strength, and functional properties, benefiting a wide range of industries including aerospace, automotive, coatings, and electronics.