Bis(3,4-epoxycyclohexylmethyl) adipate
[CAS# 3130-19-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Epoxide
• Name: Bis(3,4-epoxycyclohexylmethyl) adipate
• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.45
• CAS Registry Number: 3130-19-6
• EC Number: 221-518-5
• SMILES: C1CC2C(O2)CC1COC(=O)CCCCC(=O)OCC3CCC4C(C3)O4

Properties

• Density: 1.149
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H317-H319
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Bis(3,4-epoxycyclohexylmethyl) adipate, also known as bis(3,4-epoxycyclohexylmethyl)hexanedioate, is an important compound in the realm of epoxy resin technology. With the chemical formula C₁₈H₂₀O₄, this substance is characterized by its two epoxy groups and an adipate ester linkage, making it a valuable component in the synthesis and application of epoxy-based materials.

The discovery of bis(3,4-epoxycyclohexylmethyl) adipate emerged from the need for advanced epoxy resins with improved properties. Early research into epoxy resins focused on developing materials that could offer better performance in terms of heat resistance, mechanical strength, and chemical stability. The introduction of this compound was a significant step forward, as its chemical structure provided enhanced performance characteristics compared to traditional epoxy resins.

Bis(3,4-epoxycyclohexylmethyl) adipate is primarily used as a cross-linking agent or hardener in epoxy resin formulations. Its two epoxy groups allow it to react with various hardeners, forming a three-dimensional network that imparts strength and durability to the final material. This cross-linking capability is crucial in producing high-performance coatings, adhesives, and composite materials. The presence of the adipate ester linkage in the structure contributes to the flexibility and processability of the epoxy resin, making it suitable for applications requiring both rigidity and some degree of flexibility.

In addition to its role as a cross-linking agent, bis(3,4-epoxycyclohexylmethyl) adipate is used in the formulation of specialty coatings. These coatings benefit from the compound's ability to cure at moderate temperatures, resulting in films that exhibit excellent resistance to chemicals, moisture, and thermal degradation. This property makes it ideal for protective coatings in industrial and automotive applications, where resistance to harsh environments is essential.

The compound also finds application in the production of epoxy-based composites. These composites are used in a variety of industries, including aerospace, automotive, and construction, where their high strength-to-weight ratio and durability are advantageous. Bis(3,4-epoxycyclohexylmethyl) adipate enhances the mechanical properties and thermal stability of these composites, contributing to their performance in demanding environments.

Research continues to explore new applications and enhancements for bis(3,4-epoxycyclohexylmethyl) adipate. Innovations in epoxy resin technology aim to improve its performance further and expand its utility in emerging fields. The compound's versatility and effectiveness in forming durable and high-performance materials underscore its importance in advancing both industrial processes and consumer products.

In summary, bis(3,4-epoxycyclohexylmethyl) adipate is a significant compound in the epoxy resin industry, valued for its role as a cross-linking agent and its contributions to the development of specialty coatings and composites. Its chemical structure and properties make it a key player in producing high-performance materials with enhanced durability and stability.

References

2006. High performance holographic polymer dispersed liquid crystal systems using multi-functional acrylates and siloxane-containing epoxides as matrix components. Applied Physics A, 83(1).
DOI: 10.1007/s00339-006-3495-2

2010. Photopolymerization Processes. Additive Manufacturing Technologies.
DOI: 10.1007/978-1-4419-1120-9_4

2015. Vat Photopolymerization Processes. Additive Manufacturing Technologies.
DOI: 10.1007/978-1-4939-2113-3_4