1,3,5-Tris(oxiranylmethyl)-1,3,5-triazin-2,4,6 (1H,3H,5H)-trion

less than 1 mg/mL at 68 °F (NTP, 1992)

Exists as a mixture of 2 pairs of diastereomer racemates, designated alpha and beta, that are separable on the basis of their solubility properties

log Kow: -0.8. Solubility in water: 0.9 g/100 mL at 25 °C /Triglycidyl isocyanurate technical grade/

In water, 9-10.5 g/L at 25 °C, pH 5-8

In water, <1 mg/mL at 68 °F

Soluble in water

170 °C /Open cup vs. closed cup not specified/

>170 °C c.c. (technical grade)

> 240 °C, decomposition

BP: 210 °C at 0.2 mm Hg

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx).

When heated to decomposition it emits toxic vapors of /nitrogen oxides and cyanide/.

203 to 208 °F (NTP, 1992)

95 °C

MP: 203 to 208 °F

Crystals from methanol. MP: 103-104.5 °C. Also reported as crystals from frational crystalization from methanol. MP: 95-103 °C. Enthalpy of fusion: 77.0 J/g /alpha-thioglycidyl isocyanurate/

95 °C

203-208 °F

Hazardous autopolymerization occurs following heating to >120 °C for more than 12 hours.

Triglycidyl isocyanurate ... can be polymerized by catalysts and may undergo violent autopolymerization.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2-oxiranylmethyl)-

Hazard Traits - Genotoxicity

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2-oxiranylmethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2-oxiranylmethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: 1,3,5-tris(oxiranylmethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (EC: 219-514-3)

Substance: 1,3,5-Tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione (TGIC)

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(oxiranylmethyl)-, (triglycidalisocyanurate): HSNO Approval: HSR001553 Approved with controls

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

A nonsmoking spray painter, after using a polyester powder paint containing 4% TGIC for four years, developed allergic contact dermatitis and work-related asthma. The painter had negative skin tests for common allergens and negative challenge test with lactose powder. A challenge test with 4% TGIC induced a dual response with a late 23% fall in FEV1. [Piirila P, et al. Occupational Asthma Caused by Triglycidyl Isocyanurate (TGIC). Clin Exp Allergy 1997 May;27(5):510-4] TGIC causes male reproductive damage in high-dose animal studies. [ACGIH] A severe eye irritant; May cause skin sensitization; [ICSC] Danger of skin and airway sensitization; [MAK]

Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

The substance may polymerize due to heating to more than 120 °C for more than 12 hours, or under the influence of catalysts. Decomposes on burning. This produces toxic fumes including nitrogen oxides. The molten form reacts rapidly with primary and secondary amines, carboxylic acids and anhydrides, thiols, phenols and alcohols.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use foam, powder, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

For more Preventive Measures (Complete) data for Triglycidyl isocyanurate (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triglycidyl isocyanurate is expected to have very high mobility in soil(SRC). Volatilization of triglycidyl isocyanurate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.25X10-5 mm Hg(3), and water solubility, 9500 mg/L(3). Triglycidyl isocyanurate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(4) indicating that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triglycidyl isocyanurate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 5.25X10-5 mm Hg(4), and water solubility, 9500 mg/L(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 1.21(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis may be an environmental fate process due to the presence of epoxide rings(6). Epoxides hydrolyze rapidly at 298 K and pH7; conjugated and aromatic epoxides have half-lives of a few minutes(7). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(8) indicating that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triglycidyl isocyanurate, which has a vapor pressure of 5.25X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase triglycidyl isocyanurate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 hrs(SRC), calculated from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase triglycidyl isocyanurate may be removed from the air by wet and dry deposition(SRC). Triglycidyl isocyanurate contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

IDENTIFICATION AND USE: Triglycidyl isocyanurate (TGT) is a white solid. TGT is used as a crosslinking agent in polymer synthesis, additive in plastic, rubber, and adhesives, hardener in polyester powder coatings, in protective coatings of electronic devices, in top-coated and solder-resistant inks. HUMAN STUDIES: The reported health effects in humans are contact dermatitis and respiratory sensitization. It may also cause serious eye damage. TGT did not induce chromosomal aberrations in human lymphocytes at concentrations up to 2500 ng/mL. Only one aberration was reported at each of the two higher concentrations of 5000 and 10,000 ng/mL. Human trials were performed during clinical development of alpha-TGT as an antitumor agent. In these studies, alpha-TGT was administered iv to cancer patients at doses up to 900 mg/kg bw using a variety of dosing regimes. Toxic signs included myelosuppression, nausea and vomiting, and, rarely, alopecia and leucopenia at high doses (>600 mg/kg bw). Owing to its severe local toxicity (thrombophlebitis) at the site of injection, the use of alpha-TGT as an antitumor agent was not pursued. ANIMAL STUDIES: Acute animal toxicity studies reveal that TGT is toxic by oral and inhalation routes of exposure but has low acute dermal toxicity. TGT produces serious eye irritation. It is a skin sensitizer but not a skin irritant. Short-term repeated dose studies revealed renal, lung, gastric/duodenal, and sperm cell damage. In a subchronic toxicity/fertility study conducted in rats, a dose-dependent reduction in the number of spermatozoa was the only effect observed at concentrations of up to 100 ppm TGT in the diet. The chemical has produced positive results in a range of in vitro genotoxicity studies (gene mutation in bacterial and mammalian cells, unscheduled DNA synthesis, sister chromatid exchanges, and chromosomal aberration assays). Genotoxic effects have also been observed in vivo in somatic (bone marrow) cells and germ cells in the testes. Genotoxicity studies have revealed that the inhalation of TGT produces cytotoxicity and chromosomal aberrations in mouse spermatogonia. A 13-week dietary study in rats has indicated no effects on male fertility.

The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for triglycidyl isocyanurate is available.[Available from, as of February 1, 2019: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of February 4, 2019: http://actor.epa.gov/dashboard/]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of triglycidyl isocyanurate can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triglycidyl isocyanurate is expected to have very high mobility in soil(SRC).

/HUMAN EXPOSURE STUDIES/ Allergic contact dermatitis has been reported in several case-studies of exposure to triglycidyl isocyanurate and powder coatings containing triglycidyl isocyanurate. ... Symptoms included dermatitis, itchy rashes, and swelling on the face, hands, arms, neck, and thighs. All subjects tested positive to patch testing with triglycidyl isocyanurate.

/HUMAN EXPOSURE STUDIES/ Human trials were performed during clinical development of alpha-triglycidyl isocyanurate as an antitumor agent. In these studies, alpha-triglycidyl isocyanurate was administered iv to cancer patients at doses up to 900 mg/kg bw using a variety of dosing regimes. Toxic signs included myelosuppression, nausea and vomiting, and, rarely, alopecia and leucopenia at high doses (>600 mg/kg bw). Owing to its severe local toxicity (thrombophlebitis) at the site of injection, the use of alpha-triglycidyl isocyanurate as an antitumor agent was not pursued.

/HUMAN EXPOSURE STUDIES/ Two schedules of teroxirone, a triazine triepoxide, were evaluated in a phase I study. Twenty-six patients were treated on 1 day every 5 weeks at doses of 36-2250 mg/sq m. At doses greater than or equal to 1500 mg/sq m, severe thrombophlebitis was seen without cytotoxic effect, and this schedule was closed. Twenty-seven patients were treated on 5 days every 5 weeks at daily doses of 16-450 mg/sq m. Mild thrombophlebitis and moderate leukopenia were encountered.

/HUMAN EXPOSURE STUDIES/ alpha-1,3,5-Triglycidyl-s-triazinetrione (TGT) is a triepoxide derivative with alkylating properties discovered by random screening. TGT has been found to be active against a wide variety of murine tumors, including a P388 subline resistant to cyclophosphamide. The starting dose in this phase-I study was 30 mg/sq m as a single dose IV, repeated every 3-4 weeks, increasing up to 2,700 mg/sq m. Severe dose-limiting toxicity took the form of phlebitis becoming apparent a few days after treatment. This was initially seen at the 480 mg/sq m dose level, and was observed with increasing frequency and intensity at higher dose levels. Leukopenia occurred regularly at dose levels above 1,800 mg/sq m and resulted in life-threatening leukopenia in one patient, and in a toxic death at 2,700 mg/sq m in another patient. Other toxic side-effects included moderate reversible thrombocytopenia, nausea, and vomiting. ...

For more Human Toxicity Excerpts (Complete) data for Triglycidyl isocyanurate (13 total), please visit the HSDB record page.

Triglycidyl isocyanurate's production and use as a crosslinking agent in polymer synthesis, additive in plastic, rubber and adhesives, a hardener in polyester powder coatings, in protective coatings of electronic devices, in top-coated and solder-resistant inks(1), as a non-BPA epoxy coating(2) and a component in surgical dressings and tapes(3) may result in its release to the environment through various waste streams(SRC).

An estimated BCF of 3 was calculated in fish for triglycidyl isocyanurate(SRC), using an estimated log Kow of 1.21(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

In ... intravenous studies with [(14)C]alpha-triglycidyl isocyanurate in rabbits, ... the half-life of triglycidyl isocyanurate in the blood was <5 min.

The only available human data are from clinical trials with alpha-triglycidyl isocyanurate (intravenous administration), which indicate that alpha-triglycidyl isocyanurate has a mean half-life in the blood of approximately 1 min ... .

In an oral (gavage) study in mice, ... blood plasma analysis indicated that triglycidyl isocyanurate was metabolized by hydrolysis to the diol diepoxide, the bis-diol epoxide, and the fully hydrolysed tris-diol, with no free triglycidyl isocyanurate detected 8 hr after treatment.

In in vitro studies, rapid hydrolysis of triglycidyl isocyanurate involving the enzyme epoxide hydrolase was observed in mouse liver preparations. Hydrolysis was also observed in rat liver preparations but not in rat lung preparations. Microsomal epoxide hydrolase activity with triglycidyl isocyanurate as substrate measured in two human livers obtained from kidney donors was found to be greater than the activity in rat liver.

... Metabolism of TGIC involves hydrolysis of the epoxy functions, leading to the formation of the trisdiol derivative, and is promoted by hepatic but not pulmonary epoxide hydrolase. Non-enzymatic hydrolysis of the epoxy functions occurs under conditions of low pH. Further mechanisms for the metabolism of TGIC have not been investigated. Excretion of TGIC and/or its metabolites is largely via the urine. Urinary metabolites of TGIC have not been identified.

In an oral (gavage) study in mice, at least 17% of the administered dose was absorbed within 24 hr, with blood analysis indicating that the absorption of triglycidyl isocyanurate administered in aqueous solution was twice that of triglycidyl isocyanurate in sesame oil. Triglycidyl isocyanurate was distributed to the liver, stomach, and testes (the only tissues studied).

The only available human data are from clinical trials with alpha-triglycidyl isocyanurate (intravenous administration), which indicate that alpha-triglycidyl isocyanurate has ... total body clearance of 5.7 L/min. Less than 1% of the administered dose was recovered unchanged in urine within 24 hr.

In oral (gavage) and intravenous studies with [14C]alpha-triglycidyl isocyanurate in rabbits, the radioactivity recovered in urine within 24 hr was approximately 30% and 60-70%, respectively.

Used in powder coatings containing less than 5% TGIC; [ACGIH] Occupational asthma and allergic contact dermatitis reported in workers manufacturing thermosetting paints; [Reference #1] Causes allergic contact dermatitis in screen-printing workers handling UV-cured inks; [Adams, p. 467]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

Crosslinking agent in polymer synthesis; additive in plastic, rubber, and adhesives; hardener in polyester powder coatings; in protective coatings of electronic devices; in top-coated and solder-resistant inks.

The main use of triglycidyl isocyanurate is as a three-dimensional cross-linking or curing agent in polyester powder coatings (paints). ...Triglycidyl isocyanurate is also used in solder "mask" inks in the printed circuit board industry.

2023: 2,500,000 - <4,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Triglycidyl isocyanurate:

... obtained by reacting cyanuric acid with epichlorohydrin.

Improved process for the preparation and separation of the alpha and beta-forms by crystallization: M. Budnowski, United States of America patent 3300490 (1967 to Henkel & Cie.). Preparation of the (R,R,R) and (S,S,S) isomers: H. Ikeda et al., United States of America patent 6605717 (2003 to Nissan Chem. Ind.).

Reaction of CA /cyanuric acid/ with epichlorohydrin in alkaline dioxane solution gives tris(3-chloro-2-hydroxypropyl)isocyanurate. This material can be converted into the commercial product, tris(2,3-epoxypropyl)isocyanurate ... by dehydrohalogenation with alkali.

Exists as a mixture of two pairs of diastereomer racemates, designated alpha and beta, that are separable on the basis of their solubility properties.

... Manufactured and supplied as the technical grades TEPIC and Araldite PT810. Technical-grade triglycidyl isocyanurate is a mixture of two diastereomers, alpha and beta.

Electrical Equipment, Appliance, and Component Manufacturing

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2-oxiranylmethyl)-: ACTIVE

... In the manufacture of powder coatings, triglycidyl isocyanurate granules are mixed with other ingredients; the mix is then melted and extruded as a brittle sheet, chipped, and packaged. Generally, the particle size of 90-95% of the powder coating is >10 um. Powder coatings usually contain 4-10% triglycidyl isocyanurate and are sprayed onto metal objects by an electrostatic process. The coated metal objects are then treated in an oven to a temperature of about 200 °C. This heating causes the powder coatings to melt, flow, and chemically cross-link. The coatings are durable and resist ultraviolet damage; as a result, they are typically used in outdoor applications. Triglycidyl isocyanurate is also used in solder "mask" inks in the printed circuit board industry. The two-part inks contain approximately 60% triglycidyl isocyanurate in the hardener component. The inks are applied by curtain coating, electrostatic spraying, or screen printing. The coated circuit board is finally passed through an oven at 150 °C to complete the curing.