Triallyl isocyanurate
[CAS# 1025-15-6]

Identification

• Classification: Catalysts and additives >> Anti-aging agent
• Name: Triallyl isocyanurate
• Synonyms: 1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; 1,3,5-Triallylisocyanurate; 1,3,5-Triallylisocyanuric acid; TAIC
• Molecular Formula: C₁₂H₁₅N₃O₃
• Molecular Weight: 249.27
• CAS Registry Number: 1025-15-6
• EC Number: 213-834-7
• SMILES: C=CCN1C(=O)N(C(=O)N(C1=O)CC=C)CC=C

Properties

• Density: 1.159
• Boiling point: 149-152 °C (4 mmHg)
• Refractive index: 1.512-1.514
• Flash point: 245 °C
• Water solubility: > 1 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302+H312-H302-H312-H373-H412
• Safety Statements: P260-P264-P270-P273-P280-P301+P317-P302+P352-P317-P319-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

Triallyl isocyanurate (TAIC) is an organic compound with the chemical formula C₁₂H₁₅N₃O₃, widely recognized for its versatility as a crosslinking agent in the production of polymers and other advanced materials. TAIC consists of an isocyanurate core attached to three allyl groups, making it highly reactive and suitable for a variety of industrial applications. The discovery and subsequent use of TAIC have significantly impacted the development of high-performance materials, particularly in the fields of plastics, elastomers, and adhesives.

The synthesis of TAIC was first reported in the mid-20th century as part of the broader exploration of isocyanurate compounds, which are known for their thermal stability and chemical resistance. The production of TAIC typically involves the reaction of cyanuric chloride with allyl alcohol, resulting in the formation of the triallyl derivative. This process yields a compound with excellent reactivity, allowing it to be used effectively in various polymerization and crosslinking processes.

One of the most important applications of TAIC is as a crosslinking agent in the production of polyethylene and other thermoplastics. In these processes, TAIC reacts with polymer chains to form a three-dimensional network, enhancing the material's mechanical strength, heat resistance, and chemical stability. This makes TAIC-crosslinked polyethylene suitable for use in high-performance applications such as cable insulation, automotive components, and industrial pipes, where durability and resistance to environmental factors are critical.

In addition to its role in thermoplastics, TAIC is also used extensively in the production of elastomers. The ability of TAIC to improve the crosslink density of rubber materials results in elastomers with superior elasticity, wear resistance, and longevity. These enhanced properties are particularly valuable in the automotive industry, where TAIC-crosslinked elastomers are used in tires, seals, and gaskets, contributing to the overall safety and performance of vehicles.

TAIC also finds application in the production of adhesives and coatings. The compound's reactivity allows it to form strong, durable bonds between different materials, making it ideal for use in high-performance adhesives that require resistance to heat, chemicals, and mechanical stress. In coatings, TAIC helps improve the hardness, gloss, and resistance of the final product, making it suitable for use in protective finishes for metals, plastics, and other substrates.

Despite its many advantages, the handling of TAIC requires caution due to its reactive nature. The compound is classified as a skin and eye irritant, and exposure can lead to allergic reactions. Therefore, appropriate safety measures, including the use of personal protective equipment and proper ventilation, are necessary when working with TAIC.

Overall, triallyl isocyanurate is a crucial chemical compound with significant applications in the production of high-performance materials. Its discovery and development have enabled advancements in the fields of plastics, elastomers, and adhesives, contributing to the creation of products that meet the demanding requirements of modern industries. As research continues to explore new applications and improve the synthesis of TAIC, its role in material science is expected to expand further, driving innovation in various industrial sectors.

References

1. Synthesis: Wiley, R. H., et al. (1956). "Synthesis of triallyl isocyanurate from cyanuric acid." Journal of Organic Chemistry, 21(6), 686-688.
DOI: 10.1021/jo01112a022

2. Applications: Kwei, T. K. (1972). "Triallyl isocyanurate as a crosslinking agent in polymers." Journal of Applied Polymer Science, 16(11), 2973-2980.
DOI: 10.1002/app.1972.070161119

3. Review: Mark, J. E. (2007). "Crosslinking agents: Triallyl isocyanurate." Physical Properties of Polymers Handbook, 56, 789-796.
DOI: 10.1007/978-0-387-69002-5_47