TRIAZENE TRIEPOXIDE (TRIGLYCIDYL ISOCYANURATE)

Introduction

Triazene triepoxide is the common name for the chemical compound Triglycidyl Isocyanurate (TGIC) , also known by the drug name Teroxirone. It is a heterocyclic compound containing a triazine ring and three epoxide (oxirane) functional groups. It is classified as a triazene triepoxide due to its triazene-like structure and three epoxide groups.

Importantly, TGIC is not a food additive nor a food contact substance. It has been used in industrial applications, primarily as a crosslinking agent for polyester-based powder coatings, which are used to coat metal surfaces. Its presence in a food chemistry context is likely due to its biological activity as a chemotherapeutic agent, as it has been investigated for its antineoplastic (anti-cancer) and antiangiogenic properties.

CAS Number

2451-62-9

Synonyms

• Triglycidyl Isocyanurate (TGIC)
• Teroxirone
• Tris(2,3-epoxypropyl) isocyanurate
• α-triglycidyl isocyanurate
• Teroxine

Topic Headings

1. Primary Applications (List Form)

• Industrial crosslinking agent — The primary industrial use of TGIC is as a hardener for durable polyester powder coatings used on cars, appliances, and outdoor furniture.
• Antineoplastic agent (investigational) — Has been studied as a potential chemotherapy drg; it is an alkylating agent that crosslinks DNA, inhibiting cancer cell replication.
• Research chemical — Used in biochemical research to study DNA alkylation and the p53 signaling pathway.
• Plastic stabilizer — In some industrial formulations, it acts as a heat stabilizer.

2. Mechanism as a Crosslinking Agent (paragraph form)

In industrial powder coatings, TGIC functions as a crosslinking agent due to its three highly reactive epoxide groups. When heated (thermoset process), these epoxide groups react with the carboxyl (-COOH) groups on a polyester resin. This reaction forms a dense, three-dimensional polymer network, creating a coating that is very hard, durable, and resistant to chemicals, heat, and UV degradation. Without crosslinkers like TGIC, the polyester would remain a low-molecular-weight, soft, and ineffective film.

3. Physical and chemical properties (list form)

• Appearance — White to off-white crystalline solid.
• Molecular weight — 297.26 g/mol.
• Epoxide equivalent weight — Typically around 110 g/eq.
• Melting point — 95-115°C.
• Solubility — Practically insoluble in water but soluble in many organic solvents.
• Stability — Stable under normal storage conditions but highly reactive with nucleophiles (e.g., water, alcohols, amines) when activated.

4. Safety and Regulatory Status (paragraph form)

This substance is not approved for use as a food additive. It is classified as a hazardous substance in most jurisdictions. It is toxic if swallowed, causes skin and eye irritation, and is a known skin and respiratory sensitizer (may cause an allergic reaction upon contact). The International Agency for Research on Cancer (IARC) has classified TGIC as a Group 3 agent (not classifiable as to its carcinogenicity to humans), but it is considered a potential occupational carcinogen and is regulated as a hazardous chemical. Due to these toxicity concerns, the industrial use of TGIC has been restricted in some jurisdictions (e.g., it is classified as a SVHC under EU REACH).