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TRİS(2,3-EPOXYPROPYL) ISOCYANURATE

Description

Tris(2,3-epoxypropyl) Isocyanurate (TEPIC) is a highly functional trifunctional epoxy compound widely used as a crosslinking agent, reactive intermediate, adhesion promoter, and high-performance resin modifier in coatings, electronics, adhesives, composites, powder coatings, and specialty polymer systems. The molecule consists of an isocyanurate ring substituted with three glycidyl (epoxy) groups, providing exceptionally high crosslinking capability and outstanding thermal, chemical, and mechanical performance after curing.

TEPIC is particularly valued for producing highly crosslinked polymer networks that exhibit superior hardness, corrosion resistance, chemical resistance, electrical insulation, weatherability, and thermal stability. It is commonly incorporated into epoxy resins, polyester systems, acrylic resins, hybrid coatings, electrical encapsulation materials, and advanced composite formulations.

Because of its three reactive epoxy groups, TEPIC offers significantly higher crosslink density than difunctional epoxy compounds, making it an essential component in high-performance industrial coatings and engineering materials.


CAS Number

CAS Number: 2451-62-9


Synonyms

  • Tris(2,3-epoxypropyl) Isocyanurate
  • TEPIC
  • Triglycidyl Isocyanurate
  • TGIC
  • Isocyanuric Acid Triglycidyl Ester
  • Tris(Glycidyl) Isocyanurate
  • 1,3,5-Tris(2,3-epoxypropyl)-1,3,5-triazinane-2,4,6-trione
  • Epoxy Isocyanurate Crosslinker

Physical Properties

Tris(2,3-epoxypropyl) Isocyanurate is supplied as a white crystalline powder or fine granules with excellent storage stability under dry conditions.

Typical characteristics include:

  • Appearance: White crystalline powder or granules
  • Physical state: Solid
  • Odor: Nearly odorless
  • Molecular formula: C₁₂H₁₅N₃O₆
  • Molecular weight: 297.27 g/mol
  • Melting point: Approximately 90–110°C
  • Density: Approximately 1.30–1.35 g/cm³
  • Water solubility: Slightly soluble
  • Solubility in organic solvents: Good

Its crystalline nature allows easy storage and handling before incorporation into resin systems.


Chemical Properties

TEPIC contains three highly reactive epoxy rings attached to a thermally stable isocyanurate core. During curing, these epoxy groups react with curing agents such as amines, anhydrides, phenolic resins, or carboxyl-functional polyesters to form densely crosslinked thermoset networks.

Important chemical characteristics include:

  • Trifunctional epoxy compound
  • High epoxy equivalent functionality
  • Excellent thermal stability
  • Outstanding chemical resistance
  • High crosslink density
  • Excellent electrical insulation
  • Low volatility
  • Good hydrolytic stability

The rigid isocyanurate ring contributes significantly to heat resistance and long-term durability.


Manufacturing Process

Commercial TEPIC is typically produced through the glycidylation of isocyanuric acid using epichlorohydrin under alkaline conditions.

Typical manufacturing stages include:

  • Preparation of isocyanuric acid
  • Reaction with epichlorohydrin
  • Alkaline ring closure
  • Removal of inorganic salts
  • Washing
  • Vacuum purification
  • Crystallization
  • Drying
  • Quality control testing
  • Packaging

Careful purification ensures high epoxy functionality and low residual chlorides.


Mechanism of Action

TEPIC functions through epoxy ring-opening reactions.

During thermal curing, each epoxy group reacts with suitable curing agents, producing an extensively crosslinked three-dimensional polymer network. Because each molecule contains three reactive epoxy groups, the resulting materials exhibit superior mechanical strength and thermal resistance.

Its primary functions include:

  • Crosslinking
  • Network formation
  • Hardness enhancement
  • Adhesion improvement
  • Corrosion protection
  • Chemical resistance enhancement
  • Electrical insulation

High crosslink density significantly improves coating durability and dimensional stability.


Applications

TEPIC is used in numerous advanced industrial applications.

Powder Coatings

  • Polyester powder coatings
  • Hybrid powder coatings
  • Industrial finishes
  • Architectural coatings

Epoxy Systems

  • Epoxy adhesives
  • Protective coatings
  • Composite resins
  • Structural laminates

Electronics Industry

  • Electrical encapsulation
  • Printed circuit boards
  • Insulating materials
  • Semiconductor packaging

Composite Industry

  • Fiber-reinforced composites
  • Aerospace materials
  • High-performance laminates
  • Structural composites

Specialty Polymers

  • High-temperature polymers
  • Corrosion-resistant coatings
  • Functional resin modifiers

 

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