Tricyclodecanedimethanol diacrylate
[CAS# 42594-17-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Tricyclodecanedimethanol diacrylate
• Synonyms: [8-(prop-2-enoyloxymethyl)-3-tricyclo[5.2.1.02,6]decanyl]methyl prop-2-enoate
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.38
• CAS Registry Number: 42594-17-2
• EC Number: 255-901-3
• SMILES: C=CC(=O)OCC1CCC2C1C3CC(C2C3)COC(=O)C=C

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 396.5±15.0 ºC 760 mmHg (Calc.)^*
• Flash point: 192.2±18.8 ºC (Calc.)^*
• Index of refraction: 1.505 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H315-H317-H319-H335-H411
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
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
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovory and Applicatios

Tricyclodecanedimethanol diacrylate is a multifunctional acrylate monomer known for its rigid, tricyclic hydrocarbon backbone and two pendant acrylate groups. The structure features a tricyclodecane core—specifically, tricyclo\[5.2.1.0^2,6]decane—substituted with two hydroxymethyl groups that are further esterified with acrylic acid to yield the diacrylate ester. This unique molecular architecture imparts a combination of high rigidity, thermal stability, and crosslinking ability, making the compound suitable for advanced polymer and coating applications.

The development of tricyclodecanedimethanol diacrylate can be traced to efforts to synthesize monomers that improve the mechanical and thermal properties of crosslinked polymer networks. Conventional diacrylates, such as ethylene glycol diacrylate or hexanediol diacrylate, often impart flexibility and lower glass transition temperatures. In contrast, the incorporation of a tricyclic hydrocarbon scaffold offers increased rigidity and results in materials with higher hardness and better dimensional stability. The compound was developed through esterification reactions involving tricyclodecanedimethanol—a commercially available diol derived from dicyclopentadiene—and acrylic acid or its derivatives under acid catalysis.

This diacrylate monomer is primarily used in the formulation of UV-curable resins and coatings. Its two acrylate functionalities allow it to participate in free-radical polymerization, leading to highly crosslinked, thermoset networks when exposed to UV light in the presence of photoinitiators. The rigid tricyclic core contributes to excellent scratch resistance, low shrinkage upon curing, and improved thermal performance. As a result, it is employed in protective coatings for wood, plastics, and electronics where durability and surface hardness are critical.

In the field of photopolymerization, tricyclodecanedimethanol diacrylate is widely used in 3D printing, especially in digital light processing (DLP) and stereolithography (SLA) technologies. It enhances the dimensional accuracy of printed parts and improves mechanical properties such as tensile strength and modulus. Its low viscosity also facilitates easy handling and formulation with other monomers and oligomers.

Adhesives and sealants also benefit from the incorporation of this monomer. The high crosslink density achievable upon curing results in adhesives with superior bond strength and resistance to solvents and thermal degradation. These properties are valuable in both structural and optical bonding applications, particularly in electronics assembly.

In dental materials, tricyclodecanedimethanol diacrylate has been explored as a component of resin-based composites. Its low polymerization shrinkage helps reduce the formation of marginal gaps and improves the longevity of dental restorations. The high stiffness of the cured network contributes to enhanced wear resistance, an essential feature for materials used in load-bearing regions of the mouth.

The monomer has also been investigated in the development of high-performance composite materials. Its compatibility with fillers and reinforcing agents enables the design of materials that combine rigidity with tailored thermal and chemical resistance. The low water absorption and high hydrophobicity imparted by the tricyclic structure further support its use in outdoor and moisture-sensitive environments.

Tricyclodecanedimethanol diacrylate is commercially available and is often used as a reactive diluent in acrylate formulations. It serves to reduce viscosity while simultaneously enhancing the final properties of the cured product. It is generally considered to have a low tendency for skin irritation compared to some other acrylates, though appropriate handling precautions are necessary due to its reactivity.

Overall, tricyclodecanedimethanol diacrylate represents a well-characterized and widely utilized monomer in high-performance polymer systems. Its structural features provide a valuable combination of low shrinkage, high mechanical strength, and thermal stability, making it an essential ingredient in advanced coatings, 3D printing resins, adhesives, and dental materials.

References

2018. The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products. Scientific Data, 5, 180125.
DOI: 10.1038/sdata.2018.125