1,3,5-TRIGLYCIDYL ISOCYANURATE

1,3,5-Triglycidyl isocyanurate is a trifunctional epoxy compound containing a thermally stable isocyanurate ring.

1,3,5-Triglycidyl isocyanurate functions as a curing agent, crosslinker, reactive monomer, and network-forming intermediate.

1,3,5-Triglycidyl isocyanurate is used primarily in carboxyl-functional polyester powder coatings, solder-mask inks, electronic coatings, adhesives, composites, and specialty thermosetting resins.

CAS Number: 2451-62-9

EC Number: 219-514-3

Molecular Formula: C₁₂H₁₅N₃O₆

Molecular Weight: 297.26 g/mol

SYNONYMS

1,3,5-Triglycidyl isocyanurate, Triglycidyl Isocyanurate, Triglycidylisocyanurate, TGIC, TGI, TGT, Glycidyl Isocyanurate, Triglycidyl Cyanurate, Tris(glycidyl) Isocyanurate, Tris(2,3-epoxypropyl) Isocyanurate, Tris(2,3-epoxypropyl)isocyanurate, Tris(epoxypropyl) Isocyanurate, 1,3,5-Tris(2,3-epoxypropyl) Isocyanurate, 1,3,5-Tris(oxiranylmethyl) Isocyanurate, 1,3,5-Tris(oxiran-2-ylmethyl) Isocyanurate, 1,3,5-Tris(oxiranylmethyl)-1,3,5-triazine-2,4,6-trione, 1,3,5-Tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione, 1,3,5-Triglycidyl-s-triazinetrione, 1,3,5-Triglycidyl-s-triazine-2,4,6-trione, 1,3,5-Triazine-2,4,6-trione, 1,3,5-tris(oxiranylmethyl)-, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2-oxiranylmethyl)-, Isocyanuric Acid Triglycidyl Ester, Isocyanuric Acid Trisglycidyl Ester, Triglycidyl Isocyanuric Acid Ester, Isocyanurate Triepoxide, Isocyanurate-Based Triepoxide, Trifunctional Epoxy Isocyanurate, Trifunctional Epoxy Crosslinker, Triepoxy Isocyanurate, Triglycidyl Triazine Trione, Glycidyl Triazine Trione, Epoxy-Functional Isocyanurate, Three-Functional Epoxy Compound, Carboxyl-Polyester Crosslinker, Polyester Powder-Coating Hardener, Powder-Coating Epoxy Curing Agent, Outdoor Powder-Coating Crosslinker, Solder-Mask Ink Hardener, Printed-Circuit-Board Ink Crosslinker, Heat-Resistant Epoxy Monomer, Thermosetting-Resin Crosslinker, Reactive Epoxy Intermediate, High-Functionality Epoxy Compound, Alpha-TGIC, Beta-TGIC, Technical-Grade TGIC, High-Purity TGIC, CAS 2451-62-9, EC 219-514-3, EINECS 219-514-3, PubChem CID 17142, C₁₂H₁₅N₃O₆

APPLICATIONS

1,3,5-Triglycidyl isocyanurate serves as a trifunctional curing agent for carboxyl-functional polyester powder coatings.
1,3,5-Triglycidyl isocyanurate reacts through its three epoxy groups to form a tightly crosslinked thermoset network during thermal curing.

1,3,5-Triglycidyl isocyanurate supports exterior polyester powder coatings requiring durable gloss, color retention, and resistance to weathering.
1,3,5-Triglycidyl isocyanurate allows the cured coating to combine polyester weatherability with high network density when formulation stoichiometry is controlled.

1,3,5-Triglycidyl isocyanurate functions in powder coatings for aluminum window frames, doors, façades, profiles, and architectural components.
1,3,5-Triglycidyl isocyanurate must be combined with suitable pretreatment, pigments, catalysts, flow agents, and curing conditions.

1,3,5-Triglycidyl isocyanurate contributes to coatings for steel structures, fabricated sections, railings, gates, and exterior metal fixtures.
1,3,5-Triglycidyl isocyanurate supports hardness, adhesion, and chemical resistance after adequate melting, flow, and crosslinking.

1,3,5-Triglycidyl isocyanurate supports powder coatings for household appliances, metal cabinets, shelving, and durable equipment housings.
1,3,5-Triglycidyl isocyanurate helps produce hard and continuous films that tolerate routine handling, cleaning, and abrasion.

1,3,5-Triglycidyl isocyanurate functions in coatings for selected automotive, agricultural, and transportation components.
1,3,5-Triglycidyl isocyanurate suitability depends on impact resistance, flexibility, corrosion protection, chemical exposure, and thermal cycling.

1,3,5-Triglycidyl isocyanurate contributes to powder coatings for outdoor furniture, playground equipment, lighting fixtures, and street furniture.
1,3,5-Triglycidyl isocyanurate supports durable surface performance while pigment stability and substrate pretreatment remain critical.

1,3,5-Triglycidyl isocyanurate supports coatings for electrical cabinets, telecommunications enclosures, HVAC housings, and control panels.
1,3,5-Triglycidyl isocyanurate helps create an electrically insulating and chemically resistant organic film when properly formulated.

1,3,5-Triglycidyl isocyanurate functions in high-gloss polyester powder coatings requiring smooth film formation.
1,3,5-Triglycidyl isocyanurate dosage and catalyst concentration must be optimized to avoid premature gelation, poor leveling, or incomplete curing.

1,3,5-Triglycidyl isocyanurate contributes to matte, textured, structured, and low-gloss powder-coating formulations.
1,3,5-Triglycidyl isocyanurate can be combined with compatible matting agents, fillers, pigments, and texture-forming additives.

1,3,5-Triglycidyl isocyanurate supports clear polyester coatings requiring hardness and chemical resistance.
1,3,5-Triglycidyl isocyanurate must be evaluated for clarity, yellowing, gloss, surface defects, and residual epoxy functionality.

1,3,5-Triglycidyl isocyanurate functions in coatings exposed to oils, cleaning solutions, solvents, and selected industrial chemicals.
1,3,5-Triglycidyl isocyanurate chemical resistance must be validated against the exact substance, concentration, temperature, and contact duration.

1,3,5-Triglycidyl isocyanurate contributes to relatively thin powder-coating films requiring efficient crosslinking.
1,3,5-Triglycidyl isocyanurate provides substantial network formation because each molecule contains three reactive epoxide groups.

1,3,5-Triglycidyl isocyanurate supports low-temperature-cure powder-coating research when used with appropriate catalysts and reactive polyester resins.
1,3,5-Triglycidyl isocyanurate lower-temperature curing must be validated for conversion, adhesion, hardness, chemical resistance, and storage stability.

1,3,5-Triglycidyl isocyanurate functions in overbake-resistant polyester systems intended for variable industrial oven conditions.
1,3,5-Triglycidyl isocyanurate performance under prolonged heating depends on resin structure, pigment stability, catalyst type, and film thickness.

1,3,5-Triglycidyl isocyanurate contributes to powder-coating systems applied electrostatically to grounded metal components.
1,3,5-Triglycidyl isocyanurate-containing powder must be controlled through enclosure, extraction, housekeeping, and suitable respiratory protection.

1,3,5-Triglycidyl isocyanurate serves as a hardener in solder-mask and solder-resistant inks for printed circuit boards.
1,3,5-Triglycidyl isocyanurate promotes thermal crosslinking of the protective ink layer over selected conductive tracks and board surfaces.

1,3,5-Triglycidyl isocyanurate supports screen-printable and photoimageable electronic coating systems requiring post-application thermal cure.
1,3,5-Triglycidyl isocyanurate must be evaluated for dielectric properties, solder resistance, adhesion, thermal cycling, and chemical-processing compatibility.

1,3,5-Triglycidyl isocyanurate functions as a multifunctional epoxy monomer in specialty thermosetting resin systems.
1,3,5-Triglycidyl isocyanurate can react with carboxylic acids, anhydrides, amines, phenols, alcohols, and thiols under suitable conditions.

1,3,5-Triglycidyl isocyanurate contributes to heat-curable adhesives requiring high crosslink density and chemical resistance.
1,3,5-Triglycidyl isocyanurate may increase hardness and thermal performance while reducing flexibility when used at excessive functionality.

1,3,5-Triglycidyl isocyanurate supports reactive adhesive films and bonding compositions for compatible metals, ceramics, and composite substrates.
1,3,5-Triglycidyl isocyanurate suitability depends on substrate wetting, curing temperature, bond-line thickness, catalyst, toughness, and service conditions.

1,3,5-Triglycidyl isocyanurate can be evaluated in encapsulation and potting compounds requiring a rigid thermosetting network.
1,3,5-Triglycidyl isocyanurate must be balanced with flexible segments or toughening agents where impact resistance and thermal-stress tolerance are required.

1,3,5-Triglycidyl isocyanurate functions in fiber-reinforced composite and laminate research requiring a high-functionality epoxy component.
1,3,5-Triglycidyl isocyanurate can improve glass-transition behavior, dimensional stability, solvent resistance, and network rigidity after complete cure.

1,3,5-Triglycidyl isocyanurate contributes to electrical-insulation and electronic-protection resin development.
1,3,5-Triglycidyl isocyanurate performance depends on cure completeness, moisture uptake, ionic purity, dielectric behavior, and thermal aging.

1,3,5-Triglycidyl isocyanurate serves as a laboratory reagent for epoxy-reaction, polymerization, stereochemistry, and coating-cure studies.
1,3,5-Triglycidyl isocyanurate can be characterized through epoxy-equivalent measurement, chromatography, spectroscopy, thermal analysis, gel-time testing, and mechanical evaluation.

DESCRIPTION

1,3,5-Triglycidyl isocyanurate is the substance commonly abbreviated as TGIC.
1,3,5-Triglycidyl isocyanurate is identified by CAS Number 2451-62-9 and EC Number 219-514-3.

1,3,5-Triglycidyl isocyanurate has the molecular formula C₁₂H₁₅N₃O₆ and a molecular weight of approximately 297.26 g/mol.
1,3,5-Triglycidyl isocyanurate has the systematic structure of an isocyanurate ring bearing three oxiranylmethyl substituents.

1,3,5-Triglycidyl isocyanurate contains a six-membered isocyanurate core with three carbonyl groups and three ring nitrogen atoms.
1,3,5-Triglycidyl isocyanurate carries one glycidyl group on each ring nitrogen atom.

1,3,5-Triglycidyl isocyanurate contains three strained epoxide rings and therefore behaves as a trifunctional epoxy compound.
1,3,5-Triglycidyl isocyanurate can form highly crosslinked networks by reacting each epoxide ring with a compatible functional group.

1,3,5-Triglycidyl isocyanurate is an isocyanurate derivative rather than a conventional free-isocyanate compound.
1,3,5-Triglycidyl isocyanurate does not contain the reactive free NCO groups associated with monomeric diisocyanates.

1,3,5-Triglycidyl isocyanurate exists as alpha and beta stereoisomeric forms.
1,3,5-Triglycidyl isocyanurate technical material commonly contains a mixture of stereoisomers with different melting and solubility behavior.

1,3,5-Triglycidyl isocyanurate normally appears as a white crystalline powder, granule, or solid.
1,3,5-Triglycidyl isocyanurate is generally considered essentially odorless at ordinary room temperature.

1,3,5-Triglycidyl isocyanurate technical grades commonly melt within a range near 90–125°C.
1,3,5-Triglycidyl isocyanurate melting behavior varies with purity, stereoisomer ratio, crystal form, and grade specification.

1,3,5-Triglycidyl isocyanurate has a solid density commonly reported near 1.5 g/cm³.
1,3,5-Triglycidyl isocyanurate technical-grade water solubility is reported near 9 g/L at 25°C, although individual stereoisomers differ.

1,3,5-Triglycidyl isocyanurate can be manufactured through reaction of cyanuric acid with excess epichlorohydrin followed by ring closure and purification.
1,3,5-Triglycidyl isocyanurate manufacturing quality control must address residual epichlorohydrin, hydrolysable chlorine, color, epoxy content, and isomer distribution.

1,3,5-Triglycidyl isocyanurate cures carboxyl-functional polyester resins through epoxide-ring opening and ester-bond formation.
1,3,5-Triglycidyl isocyanurate produces an insoluble thermoset matrix when the epoxy-to-carboxyl equivalent ratio and curing schedule are suitable.

1,3,5-Triglycidyl isocyanurate provides high crosslink density, hardness, chemical resistance, adhesion, and thermal-network stability.
1,3,5-Triglycidyl isocyanurate can reduce impact resistance or flexibility when the cured system becomes excessively rigid.

1,3,5-Triglycidyl isocyanurate may polymerize or react vigorously when exposed to excessive heat, active catalysts, or incompatible reactive substances.
1,3,5-Triglycidyl isocyanurate should be separated from strong acids, bases, oxidizing agents, amines, anhydrides, and uncontrolled curing chemicals.

1,3,5-Triglycidyl isocyanurate presents significant occupational hazards in uncured powder form, including acute oral and inhalation toxicity, serious eye injury, skin sensitization, and mutagenicity concerns.
1,3,5-Triglycidyl isocyanurate is included in the European Union Candidate List grouping on the basis of mutagenic properties.

1,3,5-Triglycidyl isocyanurate exposure during powder spraying requires strong engineering controls because respirable or inhalable coating dust can contain unreacted TGIC.
1,3,5-Triglycidyl isocyanurate workplace control should prioritize substitution assessment, enclosure, local extraction, exposure monitoring, protective clothing, and effective respiratory protection.

PROPERTIES

Chemical Name: 1,3,5-Tris(oxiranylmethyl)-1,3,5-triazine-2,4,6-trione

Chemical Class: Trifunctional Epoxy Isocyanurate

CAS Number: 2451-62-9

EC Number: 219-514-3

Molecular Formula: C₁₂H₁₅N₃O₆

Molecular Weight: 297.26 g/mol

Physical Form: Crystalline Powder, Granules, or Solid

Appearance: White

Odor: Essentially Odorless

Melting Range: Commonly Approximately 90–125°C, Grade Dependent

Density: Approximately 1.5 g/cm³

Water Solubility: Approximately 9 g/L at 25°C for Technical Material

Epoxy Functionality: Three Epoxide Groups

Primary Function: Polyester Curing Agent and Thermosetting Crosslinker

Main Uses: Powder Coatings, Solder-Mask Inks, Electronic Coatings, Adhesives, and Specialty Epoxy Resins

Major Handling Concerns: Toxicity, Serious Eye Damage, Skin Sensitization, Mutagenicity, and Airborne Powder Exposure

Storage: Cool, Dry, Tightly Closed, and Separated from Heat and Reactive Chemicals

FIRST AID

Inhalation

1,3,5-Triglycidyl isocyanurate inhalation exposure requires immediate movement to fresh air and rest in a position comfortable for breathing.
1,3,5-Triglycidyl isocyanurate inhalation requires urgent medical assessment because powder or aerosol exposure can be toxic.

Skin Contact

1,3,5-Triglycidyl isocyanurate contamination requires immediate removal of affected clothing and thorough washing of the skin with soap and water.
1,3,5-Triglycidyl isocyanurate skin exposure requires medical attention if redness, itching, swelling, rash, or sensitization symptoms develop.

Eye Contact

1,3,5-Triglycidyl isocyanurate eye exposure requires immediate and continuous rinsing with clean water for at least 15 minutes.
1,3,5-Triglycidyl isocyanurate eye exposure requires urgent ophthalmic attention because serious and potentially persistent eye injury can occur.

Ingestion

1,3,5-Triglycidyl isocyanurate ingestion requires immediate rinsing of the mouth without inducing vomiting unless directed by medical personnel.
1,3,5-Triglycidyl isocyanurate ingestion requires immediate contact with a physician or poison information center because the substance is acutely toxic.

Note to Physicians

1,3,5-Triglycidyl isocyanurate exposure should be treated symptomatically with close observation and appropriate supportive care.
1,3,5-Triglycidyl isocyanurate assessment should consider respiratory effects, eye injury, systemic toxicity, sensitization, exposure amount, route, and duration.

HANDLING AND STORAGE

Handling

1,3,5-Triglycidyl isocyanurate should be handled in enclosed systems wherever practical and occupational exposure should be minimized.
1,3,5-Triglycidyl isocyanurate should not contact the eyes, skin, clothing, food, drink, catalysts, acids, bases, amines, anhydrides, or other reactive substances.

Ventilation

1,3,5-Triglycidyl isocyanurate powder-handling and spraying areas require effective local exhaust ventilation and controlled dust collection.
1,3,5-Triglycidyl isocyanurate respiratory protection must be used when enclosure and engineering controls cannot adequately prevent inhalation exposure.

Storage

1,3,5-Triglycidyl isocyanurate should be stored in tightly closed containers within a cool, dry, well-ventilated, and access-controlled area.
1,3,5-Triglycidyl isocyanurate should be protected from moisture, excessive heat, direct sunlight, catalysts, oxidizing agents, and incompatible reactive chemicals.

Spill and Leak Procedures

1,3,5-Triglycidyl isocyanurate spills should be isolated and collected with suitable filtered vacuum equipment while avoiding airborne dust.
1,3,5-Triglycidyl isocyanurate should not enter drains, soil, groundwater, or surface water, and recovered waste should be placed in sealed labeled containers.

Handling Precautions

1,3,5-Triglycidyl isocyanurate handling requires chemical-resistant gloves, protective clothing, tightly fitting goggles, and suitable face and respiratory protection.
1,3,5-Triglycidyl isocyanurate operations require emergency eyewash facilities, safety showers, exposure monitoring, dust controls, and review of the current grade-specific Safety Data Sheet.