Quick Search
Description
Tris(2-hydroxyethyl)-1,3,5-triazinetrione (THEIC) is a multifunctional trihydric alcohol and an isocyanurate derivative widely used as a reactive intermediate, crosslinking agent, polyester resin modifier, polyurethane component, and heat-resistant monomer in advanced polymer systems. It contains three hydroxyethyl groups attached to a highly stable triazinetrione (isocyanurate) ring, providing excellent thermal stability, hydrolytic resistance, and outstanding crosslinking capability.
THEIC is extensively employed in the manufacture of saturated polyester resins for powder coatings, high-performance alkyd resins, polyurethane systems, electrical insulation varnishes, engineering plastics, and specialty coatings. Its trifunctional hydroxyl structure enables the formation of densely crosslinked polymer networks that exhibit superior hardness, weather resistance, chemical resistance, mechanical strength, and long-term durability.
Because of its excellent balance of reactivity, thermal performance, and environmental resistance, THEIC is considered one of the most important multifunctional polyols used in high-performance polymer chemistry.
________________________________________
CAS Number
CAS Number: 839-90-7
________________________________________
Synonyms
• Tris(2-hydroxyethyl)-1,3,5-triazinetrione
• Tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione
• Tris(2-hydroxyethyl) Isocyanurate
• Tri(2-hydroxyethyl) Isocyanurate
• THEIC
• Hydroxyethyl Isocyanurate
• Isocyanuric Acid Tris(2-hydroxyethyl) Ester
• THEIC Polyol
________________________________________
Physical Properties
Tris(2-hydroxyethyl)-1,3,5-triazinetrione is supplied as a white crystalline powder or granular solid with excellent thermal stability and long storage life. It is nearly odorless and exhibits low volatility.
Typical characteristics include:
• Appearance: White crystalline powder or granules
• Physical state: Solid
• Odor: Odorless or faint characteristic odor
• Molecular formula: C₉H₁₅N₃O₆
• Molecular weight: 261.23 g/mol
• Melting point: Approximately 132–138°C
• Density: Approximately 1.45–1.50 g/cm³
• Water solubility: Slightly soluble
• Hygroscopicity: Low
Its high melting point and rigid molecular structure contribute to excellent thermal performance during polymer processing.
________________________________________
Chemical Properties
THEIC contains three primary hydroxyl groups capable of reacting with isocyanates, carboxylic acids, acid anhydrides, and other reactive functional groups to form durable thermosetting polymers.
Important chemical characteristics include:
• Trifunctional polyol
• Three reactive hydroxyl groups
• Excellent thermal stability
• High hydrolytic stability
• Superior chemical resistance
• High crosslink density
• Low volatility
• Excellent weatherability
The triazinetrione ring significantly improves heat resistance and dimensional stability in cured polymer systems.
________________________________________
Manufacturing Process
Commercial THEIC is generally produced through the hydroxyethylation of isocyanuric acid using ethylene oxide or related hydroxyethylating agents under controlled reaction conditions.
Typical manufacturing stages include:
• Preparation of isocyanuric acid
• Hydroxyethylation reaction
• Reaction control
• Neutralization (if required)
• Purification
• Crystallization
• Filtration
• Drying
• Quality control testing
• Packaging
Strict manufacturing control ensures high purity and complete substitution of all reactive sites.
________________________________________
Mechanism of Action
THEIC functions as a multifunctional crosslinking building block during polymer synthesis.
Its hydroxyl groups react with carboxyl, isocyanate, or anhydride groups to form ester or urethane bonds, generating highly crosslinked three-dimensional polymer networks. The rigid triazinetrione core contributes additional thermal stability, chemical resistance, and mechanical strength.
Its principal functions include:
• Crosslinking
• Polyester resin synthesis
• Polyurethane formation
• Heat resistance enhancement
• Chemical resistance improvement
• Mechanical reinforcement
• Weatherability enhancement
Its trifunctional nature allows the production of highly durable thermosetting materials.
________________________________________
Applications
THEIC is widely used in various industrial sectors.
Powder Coatings
• Polyester powder coatings
• TGIC-cured powder coatings
• Architectural coatings
• Industrial coatings
• Outdoor durable finishes
Polyester Resin Industry
• Saturated polyester resins
• Coil coating resins
• Appliance coatings
• Heat-resistant polymers
Polyurethane Industry
• Specialty polyurethane systems
• High-temperature elastomers
• Thermosetting polymers
Electrical Industry
• Wire enamels
• Electrical insulation varnishes
• Motor winding insulation
• Electrical encapsulation materials
Composite Materials
• Engineering composites
• High-temperature laminates
• Specialty polymer composites
