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Home > Encyclopedia > Triglycidyl isocyanurate

Triglycidyl isocyanurate

Triglycidyl isocyanurate structure

Triglycidyl isocyanurate 

structure
  • CAS No:

    2451-62-9

  • Formula:

    C12H15N3O6

  • Chemical Name:

    Triglycidyl isocyanurate

  • Synonyms:

    1,3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(2-oxiranylmethyl)-;s-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(2,3-epoxypropyl)-;1,3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(oxiranylmethyl)-;s-Triazine-2,4,6(1H,3H,5H)-trione,tris(2,3-epoxypropyl)-;1,3,5-Tris(2-oxiranylmethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione;Tris(epoxypropyl) isocyanurate;1,3,5-Triglycidyl isocyanurate;Triglycidyl isocyanurate;1,3,5-Triglycidylisocyanuric acid;Tris(2,3-epoxypropyl) isocyanurate;1,3,5-Triglycidylhexahydro-1,3,5-triazine-2,4,6-trione;1,3,5-Triglycidyl-s-triazine-2,4,6-trione;Glycidyl isocyanurate;N,N′,N′′-Triglycidyl isocyanurate;TGT;NSC 269934;1,3,5-Tris(oxiranylmethyl)-1,3,5-triazine-2,4,6-trione;1,3,5-Tris(2,3-epoxypropyl) isocyanurate;PTGIC;1,3,5-Tris(oxiran-2-ylmethyl)-1,3,5-triazine-2,4,6-trione;HT 702;1,3,5-Tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione;HT 708;414867-60-0

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

White powder or chunks


Tris(2,3-epoxypropyl)isocyanurate is a white crystalline solid. (NTP, 1992)|DryPowder; PelletsLargeCrystals|WHITE POWDER OR GRANULES|White crystalline solid.


Tris(2,3-epoxypropyl)isocyanurate is a white crystalline solid. (NTP, 1992)

Triglycidyl isocyanurate Basic Attributes

297.26400

297.26

423-400-0

1274

296964|296934

DTXSID4026262

White crystalline solid

2933699090

Characteristics

103.59000

-2.63190

White crystalline powder

1.33 g/cm3

95 °C

210 °C @ Press: 0.2 Torr

170ºC

1.635

H2O: <0.1 g/100 mL at 20 ºC;95% EtOH < 1 (mg/mL)

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition so

3.56E-10mmHg at 25°C

LD50 oral in rat: 188mg/kg

No odor at room temperature

Henry's Law constant = <2.16X10-9 atm-cu m/mol at 25 °C (est)

MP range: 94-95 °C at 758-773 mm Hg. log P: approx 0.8 at 95 °C. Solubility in water: about 9 g/L at 25 °C. VP: <0.000072 hPa (0.000054 mm Hg at approx 20 °C|log Kow = -1.07 (OECD Guideline 107 shake-flask method)|Crystals from methanol. MP: 156-157.5 °C. Also reported as methanol-insoluble crystals. MP: 149-154 °C. Index of refraction: 1.532 at 21 °C/D. Enthalpy of fusion: 142,5 J/g /beta-thioglycidyl isocyanurate/|Hydroxyl radical reaction rate constant = 1.86X10-11 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Amides and Imides

Polymerizable

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.

>200 °C (technical grade)

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

6.1(b)

UN 2811 6.1/PG 3

3

R23/25; R41; R43; R48/22; R52/53

S45-S53-S61

XZ1994900

T

Well closed.

Bulk: After heating at 60 °C for 30 days in the dark, the sample purity dropped from > 99% to 93 ± 1 %. (HPLC) Solution: A solution in water decomposed 29% in 72 hours. Aqueous solutions are most stable at pH 6. When acetonitrile was substituted for water as the storage solvent, < 1% decomposition was observed through 72 hours (HPLC).

P201-P261-P273-P280-P301 + P310-P305 + P351 + P338

H301 + H331-H317-H318-H340-H373-H412

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.

Incompatible materials: Strong oxidizing agents.|Triglycidyl isocyanurate reacts rapidly with primary and secondary amines, carboxylic acids and anhydrides, thiols, phenols, and alcohols.

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.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P314, P321, P330, P333+P313, P363, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 786 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P270, P271, P272, P280, P281, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P308+P313, P311, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501

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. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

A combustible liquid.

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.

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.

... Irritant, skin sensitizer.|Triglycidyl isocyanurate is a skin sensitizer ... . It may also cause serious eye damage.

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.

Well closed.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.

The substance is severely irritating to the eyes. The substance may cause effects on the central nervous system, kidneys, liver, lungs and gastrointestinal tract. This may result in tissue lesions.

Repeated or prolonged contact may cause skin sensitization. May cause heritable genetic damage to human germ cells.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST! AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

Toxicity

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.

LD50 Rat oral 188-715 mg/kg bw|LD50 Rat dermal >2000 mg/kg bw

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).

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).

The rate constant for the vapor-phase reaction of triglycidyl isocyanurate with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 21 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis may be an environmental fate process due to the presence of epoxide rings(2). Epoxides hydrolyze rapidly at 298 K and pH7; conjugated and aromatic epoxides have half-lives of a few minutes(3). By analogy, carbonyl urea compounds have estimated neutral hydrolysis half-lives ranging from 30-500 days at pH5-pH7, using a structure estimation method(1). Triglycidyl isocyanurate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(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).

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).

The Henry's Law constant for triglycidyl isocyanurate is estimated as 2.2X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 5.25X10-5 mm Hg(1), and water solubility, 9500 mg/L(1). This Henry's Law constant indicates that triglycidyl isocyanurate is expected to be essentially nonvolatile from water and moist soil surfaces(2). Triglycidyl isocyanurate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

According to the 2016 TSCA Inventory Update Reporting data, 12 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of trigylcidyl isocyanurate in the United States may be as low as 10 workers and as high as 10,000 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|Occupational exposure to triglycidyl isocyanurate may occur through inhalation and dermal contact with this compound at workplaces where triglycidyl isocyanurate is produced or used. The general public is not likely to be exposed to triglycidyl isocyanurate unless by direct medical treatment. (SRC)

Drug Information

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

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.

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 ... 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 ... .

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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.

1,3,5-triglycidyl isocyanurate

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Redness. Pain.

Triglycidyl isocyanurate Use and Manufacturing

Methods of Manufacturing

... 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.

Uses

1. 1,3,5-triglycidyl isocyanurate be used for curing agent of polyester and acrylic resin carboxyl-containing powder coating, manufacturing an electrical insulating laminates, adhesives, plastics stabilizers.
2. TGIC is widely used as a cross-linking agent or curing agent in powder coating industry, It is used also in the printed circuit board industry, electrical insulation and as a stabilizer in plastic industry. Typical applications of polyester TGIC powder coatings are where sharp edges and corners exist such as on automotive wheels, air conditioners, lawn furniture, and air conditioner cabinets.


Adhesives and sealant chemicals


Electrical and electronic products

Production

1,000,000 - 10,000,000 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:

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.

A method for the determination of triglycidyl isocyanurate (TGIC) from powder coatings using gas chromatography with mass spectrometric (GC/MS) detection is presented. The new method is considerably easier to use than the existing methods and has superior performance. It has been novelly applied to the determination of TGIC in a variety of occupational hygiene samples (cotton swabs, gloves and whole suits). Using the GC/MS method, the following percentage recoveries were found: gloves 114 +/- 1.9; swabs 73 +/- 6.5; whole suit 125 +/- 16.3 and 108 +/- 6.8 (two powder coatings); filter 79 +/- 8. The estimated limit of detection was 0.002 micro g/mL.

Computed Properties

Molecular Weight:297.26
XLogP3:-1.5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:297.09608521
Monoisotopic Mass:297.09608521
Topological Polar Surface Area:98.5
Heavy Atom Count:21
Complexity:416
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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