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ALPHA-TRIGLYCIDYL ISOCYANURATE

Alpha-triglycidyl isocyanurate is a trifunctional epoxy compound structurally based on an isocyanurate (triazine) ring bearing three reactive glycidyl (epoxy) groups.
Alpha-triglycidyl isocyanurate typically appears as a white crystalline solid and is used primarily in powder coating formulations, polyester resins, adhesives, and high-performance composite materials.
Alpha-triglycidyl isocyanurate is widely applied in exterior architectural coatings for aluminum profiles, window frames, metal panels, and construction components where high weather and UV resistance are required.

CAS Number: 2451-62-9
EC Number: 219-514-3
Molecular Formula: C12H15N3O6
Molecular Weight: 297.27 g/mol

Synonyms: alpha-TGT, GATGI, 456V4159SL, DTXSID301318560, RefChem:203362, DTXCID901748367, alpha-1,3,5-triglycidyl-s-triazinetrione, NSC296934, 24N3OU2YDR, Triglycidyl isocyanurate, (R,R,S)-, UNII-24N3OU2YDR, (RS,RS,SR)-1,3,5-Tris(2,3-epoxypropyl)-s-triazine-2,4,6(1H,3H,5H)-trione, Teroxirone (USAN), TEROXIRONE [USAN], BRN 0765833, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3-bis((2R)-2-oxiranylmethyl)-5-((2S)-2-oxiranylmethyl)-, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3-bis((2R)-oxiranylmethyl)-5-((2S)-oxiranylmethyl)-, 1,5-bis[[(2R)-oxiran-2-yl]methyl]-3-[[(2S)-oxiran-2-yl]methyl]-1,3,5-triazinane-2,4,6-trione, 240408-79-1, Teroxirone [USAN:INN], Teroxironum [INN-Latin], Teroxirona [INN-Spanish], .alpha.-triglycidyl isocyanurate, UNII-456V4159SL, TEROXIRONE [INN], |A-Triglycidyl isocyanurate, alpha-1,3,5-Tris(2,3-epoxypropyl)-s-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-Triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(oxiranylmethyl)-, (alpha)-, orb1740442, s-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2,3-epoxypropyl)-, alpha-, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(oxiranylmethyl)-, (1(R*),3(R*),5(S*))-(+-)-

Alpha-triglycidyl isocyanurate is a trifunctional epoxy compound structurally based on an isocyanurate (triazine) ring bearing three reactive glycidyl (epoxy) groups.
Due to its three epoxide functionalities, Alpha-triglycidyl isocyanurate acts as a highly efficient crosslinking agent in thermosetting resin systems.

During curing, Alpha-triglycidyl isocyanurate reacts with carboxyl-functional polyesters, amines, or other suitable curing agents to form dense, three-dimensional polymer networks.
This high crosslink density results in coatings and polymer materials with excellent hardness, chemical resistance, thermal stability, and weather durability.

Alpha-triglycidyl isocyanurate consists of an isocyanurate ring core substituted with three glycidyl (epoxy) groups, providing high reactivity toward carboxyl, hydroxyl, and amine functional groups.
The presence of three epoxy functionalities enables Alpha-triglycidyl isocyanurate to form densely crosslinked polymer networks with enhanced mechanical strength and chemical resistance.

Alpha-triglycidyl isocyanurate typically appears as a white crystalline solid and is used primarily in powder coating formulations, polyester resins, adhesives, and high-performance composite materials.
Alpha-triglycidyl isocyanurate contributes to improved thermal stability, corrosion resistance, and durability in cured systems.

Alpha-triglycidyl isocyanurate is a highly functional epoxy compound derived from an isocyanurate (triazinetrione) core structure substituted with three glycidyl (epoxy) groups.
This trifunctional configuration gives the molecule a high level of reactivity and enables it to form tightly crosslinked, three-dimensional thermoset polymer networks when reacted with suitable curing partners such as carboxyl-functional polyester resins or amine-based hardeners.
The presence of three epoxide groups significantly increases crosslink density compared to difunctional epoxy resins, resulting in enhanced hardness, chemical resistance, thermal stability, and mechanical strength in the cured material.

In industrial applications, Alpha-triglycidyl isocyanurate is most commonly used as a crosslinking agent in polyester powder coating systems designed for exterior durability.
Coatings formulated with this compound exhibit excellent weatherability, UV resistance, corrosion protection, and long-term performance in demanding environmental conditions.

Alpha-triglycidyl isocyanurate is widely applied in architectural aluminum profiles, metal facades, automotive components, appliances, and industrial equipment.
Alpha-triglycidyl isocyanurate's stable heterocyclic ring structure contributes to consistent curing behavior and reliable performance in high-temperature processing systems.

Applications of Alpha-Triglycidyl Isocyanurate:
Alpha-triglycidyl isocyanurate is primarily used as a crosslinking agent in carboxyl-functional polyester powder coating systems.
Alpha-triglycidyl isocyanurate is widely applied in exterior architectural coatings for aluminum profiles, window frames, metal panels, and construction components where high weather and UV resistance are required.

Alpha-triglycidyl isocyanurate is also used in automotive parts, agricultural machinery, household appliances, industrial equipment, and metal furniture coatings that demand high hardness, chemical resistance, and long-term durability.
Additionally, Alpha-triglycidyl isocyanurate is applied in hybrid epoxy-polyester powder coatings and specialty thermosetting formulations requiring high crosslink density and superior mechanical performance.

Advantages of Alpha-Triglycidyl Isocyanurate:
Alpha-triglycidyl isocyanurate provides high crosslink density due to its three reactive epoxy groups, resulting in superior network formation.
Alpha-triglycidyl isocyanurate delivers excellent weather resistance and strong UV stability, making it highly suitable for exterior powder coatings.

Alpha-triglycidyl isocyanurate enhances chemical resistance against solvents, acids, alkalis, and environmental pollutants.
Alpha-triglycidyl isocyanurate improves mechanical performance, including hardness, abrasion resistance, and impact strength.

Alpha-triglycidyl isocyanurate offers good thermal stability and maintains coating integrity at elevated temperatures.
Alpha-triglycidyl isocyanurate supports long-term durability and corrosion resistance in demanding industrial and architectural environments.

Structure of Alpha-Triglycidyl Isocyanurate:
Alpha-triglycidyl isocyanurate consists of a central isocyanurate ring (1,3,5-triazine-2,4,6-trione core) to which three glycidyl (epoxy) groups are attached via nitrogen atoms.

Core structure:
Six-membered heterocyclic ring containing three nitrogen atoms and three carbonyl (C=O) groups arranged alternately (isocyanurate ring).

Functional groups:
Three epoxide (oxirane) rings attached through methylene (–CH₂–) linkages to the nitrogen atoms of the ring.

Functional functionality:
Trifunctional (three reactive epoxy groups).

Simplified structural description:
Isocyanurate core → N–CH₂–CH–CH₂ (epoxide) ×3

Each epoxide ring provides a highly reactive site for crosslinking reactions with carboxyl, amine, or hydroxyl-containing polymers, enabling the formation of dense three-dimensional thermoset networks.

Stability and Reactivity of Alpha-Triglycidyl Isocyanurate:

Chemical stability:
Stable under recommended dry storage conditions.

Reactivity:
Reacts with amines, acids, bases, and carboxyl-functional polyesters during curing.

Conditions to avoid:
Heat, moisture, dust formation, and contamination.

Incompatible materials:
Strong oxidizing agents, strong acids, strong bases.

Hazardous decomposition products:
Carbon oxides (CO, CO₂) and nitrogen oxides (NOx) under fire or high-temperature decomposition.

Handling and Storage of Alpha-Triglycidyl Isocyanurate:

Handling:
Avoid inhalation of dust.
Avoid skin and eye contact.
Use adequate ventilation and minimize dust generation.

Storage:
Store tightly closed in a cool, dry, well-ventilated area.

Storage conditions:
Protect from moisture and direct sunlight.
Keep away from incompatible materials.

First Aid Measures of Alpha-Triglycidyl Isocyanurate:

Inhalation:
Move to fresh air.
Seek medical attention if symptoms persist.

Skin contact:
Wash thoroughly with soap and water.
Remove contaminated clothing.

Eye contact:
Rinse cautiously with water for at least 15 minutes.
Seek medical attention if irritation continues.

Ingestion:
Rinse mouth.
Do not induce vomiting.
Seek medical advice.

Most important symptoms:
May cause irritation and possible skin sensitization with repeated exposure.

Firefighting Measures of Alpha-Triglycidyl Isocyanurate:

Suitable extinguishing media:
Foam, dry chemical powder, carbon dioxide, or water spray.

Specific hazards:
Combustible solid.
Dust may form explosive mixtures in air.
Toxic fumes possible in fire.

Protective equipment for firefighters:
Self-contained breathing apparatus and full protective clothing.

Special precautions:
Avoid creating dust clouds.
Cool exposed containers with water spray.

Accidental Release Measures of Alpha-Triglycidyl Isocyanurate:

Personal precautions:
Avoid dust inhalation and contact.
Ensure ventilation.
Wear appropriate personal protective equipment.

Environmental precautions:
Prevent large releases from entering drains and waterways.

Methods for cleanup:
Sweep or vacuum using dust-minimizing methods.
Collect in suitable containers for disposal according to regulations.

Exposure Controls / Personal Protection of Alpha-Triglycidyl Isocyanurate:

Occupational exposure limits:
Not specifically established.
Control dust exposure.

Engineering controls:
Local exhaust ventilation recommended where dust may form.

Respiratory protection:
Use particulate respirator if dust is generated.

Hand protection:
Chemical-resistant gloves such as nitrile.

Eye protection:
Safety goggles.

Skin protection:
Protective clothing to avoid repeated contact.

Hygiene measures:
Wash hands after handling.
Avoid eating or drinking in work areas.

Identifiers of Alpha-Triglycidyl Isocyanurate:
IUPAC Name: 1,3,5-Tris(2,3-epoxypropyl)-1,3,5-triazine-2,4,6-trione
Chemical Family: Trifunctional epoxy compound
Physical State: Solid

CAS Number: 2451-62-9
EC Number: 219-514-3
Molecular Formula: C₁₂H₁₅N₃O₆
Molecular Weight: 297.27 g/mol
Chemical Class: Multifunctional epoxy compound
Structure Type: Isocyanurate ring substituted with three glycidyl (epoxy) groups

Properties of Alpha-Triglycidyl Isocyanurate:
Catalogue number: PA 27 03870
Chemical name: α-Triglycidyl Isocyanurate
CAS Number: 59653-73-5
Category: miscellaneous compounds
Synonyms: rel-1,3-Bis[(2R)-2-oxiranylmethyl]-5-[(2S)-2-oxiranylmethyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; rel-1,3-Bis[(2R)-oxiranylmethyl]-5-[(2S)-oxiranylmethyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; Henkel’s Compound; Teroxirone; αTGI
Molecular form: C12H15N3O6
Appearance: NA
Mol. Weight: 297.26
Storage: 2-8°C Refrigerator
Shipping Conditions: Ambient
Applications: NA

Physical state: Solid (crystalline)
Appearance: White to off-white powder or flakes
Odor: Mild or nearly odorless
Melting point: Approx. 90–110 °C
Epoxy equivalent weight (EEW): Approx. 100–110 g/eq
Density (25 °C): Approx. 1.30–1.35 g/cm³

Molecular Weight: 297.26 g/mol
XLogP3-AA: -1.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 6
Exact Mass: 297.09608521 Da
Monoisotopic Mass: 297.09608521 Da
Topological Polar Surface Area: 98.5 Å²
Heavy Atom Count: 21
Complexity: 416
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes