Trimethylolpropane triacrylate

296.319

296.32

239-701-3

4B67KGL96S

DTXSID0027773

Viscous, colorless to tan liquid

29161290

78.9

2.75

Liquid

1.11 g/cu cm at 20 deg C

-66°C

>100 °C

>230 °F

n 20/D 1.474(lit.)

Insoluble in water

Refrigerator

<0.01 mm Hg ( 20 °C)

>1 (vs air)

LD50 oral in rat: 5190uL/kg

Acrylic or pungent odor

Henry's Law constant = 6X10-10 atm-cu m/mol at 25 °C (est)

Hygroscopic, light sensitive, and incompatible with strong oxidizing agents, acids, and bases; may undergo spontaneous polymerization when exposed to direct sunlight and heat|Hydroxyl radical reaction rate constant = 3.4X10-11 cu cm/molecule-sec at 25 °C (est)

III

8

UN3265

1

R36/38;R43

39

AT4810000

Xi

P280-P305 + P351 + P338

H315-H317-H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 3802 companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501

LD50 Rabbit skin 5170 mg/kg|LD50 Rat oral 5190 mg/kg

Groups of 65 male and 65 female mice received dermal applications of 0, 0.3, 1.0, or 3.0 mg trimethylolpropane triacrylate/kg body weight in acetone, 5 days per week for 105 to 106 weeks (core study). At 2 weeks, 13 weeks, and 12 months, five animals per sex per dose group were randomly selected for histological examination of skin tissue. Survival and mean body weights of all dosed groups were similar to those of the vehicle control groups. Liver neoplasms in female mice included hepatoblastoma in the 0.3 and 3.0 mg/kg groups and hepatocholangiocarcinoma in the 1.0 and 3.0 mg/kg groups. Based on the rarity of these neoplasms in female mice, and their absence in the concurrent vehicle controls, hepatoblastoma and hepatocholangiocarcinoma were considered to be treatment-related lesions. The incidences of uterine stromal polyp and stromal polyp or stromal sarcoma (combined) in female mice occurred with positive trends, and the incidences were significantly increased in the 3.0 mg/kg group. Compared to the vehicle control incidences, the incidences of epidermal hyperplasia, melanocyte hyperplasia, and chronic inflammation at the site of application were significantly increased in core study males and females administered 3.0 mg/kg; incidences of epidermal hyperplasia in 1.0 mg/kg females and chronic inflammation in 1.0 mg/kg males were also significantly increased. At the interim evaluations, increased incidences of epidermal hyperplasia and inflammation or chronic active inflammation were observed at the site of application in males and females.|Groups of 65 male and 65 female rats received dermal applications of 0, 0.3, 1.0, or 3.0 mg trimethylolpropane triacrylate/kg of body weight in acetone, 5 days per week for 104 to 105 weeks (core study). At 2 weeks, 13 weeks, and 12 months, five animals per sex per dose group were randomly selected for histological examination of skin tissue. Survival and mean body weights of all dosed groups were similar to those of the vehicle control groups. In male rats, there was a positive trend in the incidences of malignant mesothelioma; the incidence in 3.0 mg/kg males was significantly greater than the vehicle control incidence. Nonneoplastic skin lesions at the site of application in core study rats included epidermal hyperplasia and hyperkeratosis. The incidences of these lesions in male rats administered 1.0 or 3.0 mg/kg were significantly increased. In females at the site of application, incidences of epidermal hyperplasia were significantly increased at 1.0 and 3.0 mg/kg and incidences of hyperkeratosis were significantly increased in all dosed groups. At the interim evaluations, increased incidences of epidermal hyperplasia, sebaceous gland hyperplasia, and or hyperkeratosis were observed at the site of application in males and females.|Trimethylolpropane triacrylate (1,500 to 10,000 ug per plate) did not induce gene mutations in S. typhimurium strains TA98 or TA100 or in E. coli strain WP2 uvrA/pKM101, with or without exogenous metabolic activation.

Trimethylolpropane triacrylate's production and use as a multifunctional monomer, cross-linking agent, reactive diluent, and chemical intermediate and use in producing inks, coatings, varnishes, paints and resins(1) 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 1510(SRC), determined from a structure estimation method(2), indicates that trimethylolpropane triacrylate is expected to have low mobility in soil(SRC). Volatilization of trimethylolpropane triacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Trimethylolpropane triacrylate's estimated vapor pressure of 5.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), suggests that volatilization from dry soil surfaces will not be important fate process(SRC); however, trimethylolpropane triacrylate is a liquid with a noticeable acrylic odor(3) suggesting some volatilization may occur(SRC). A 19% of theoretical BOD using activated sludge in the Japanese MITI test(4) suggests that some biodegradation may occur in soil(SRC); in the 4-week biodegradation test, 87% of initial trimethylolpropane triacrylate was degraded yielding the di- and monoacrylate esters plus trimethylolpropane(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1510(SRC), determined from a structure estimation method(2), indicates that trimethylolpropane triacrylate is 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 6X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 30(SRC), from a log Kow of 2.75(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Bioconcentration tests using 6 or 8 week exposures found low bioconcentration(6). A base-catalyzed second-order hydrolysis rate constant of 0.0242 L/mole-sec at 25 °C(SRC) was estimated using a structure estimation method(7); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(SRC). A 19% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that some biodegradation may occur in soil(SRC); in the 4-week biodegradation test, 87% of initial trimethylolpropane triacrylate was degraded yielding the di- and monoacrylate esters plus trimethylolpropane(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethylolpropane triacrylate, which has an estimated vapor pressure of 5.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trimethylolpropane triacrylate 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase trimethylolpropane triacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 5.25X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Trimethylolpropane triacrylate is reported to be light sensitive when exposed to direct sunlight(3); therefore, direct photolysis may have some importance in the environment(SRC).

The rate constant for the vapor-phase reaction of trimethylolpropane triacrylate with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of trimethylolpropane triacrylate with ozone has been estimated as 5.25X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1) which corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.0242 L/mole-sec at 25 °C(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 9 years and 331 days at pH values of 7 and 8, respectively(SRC). Trimethylolpropane triacrylate is reported to be light sensitive and may undergo spontaneous polymerization when exposed to direct sunlight(3); therefore, photodegradation may have some importance in the environment(SRC).

An estimated BCF of 30 was calculated in fish for trimethylolpropane triacrylate(SRC), using a log Kow of 2.75(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on exposure periods of 6 or 8 weeks in flow-through tests, the bioconcentration potential of trimethylolpropane triacrylate in carp has been classified as low (actual BCF values not reported)(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trimethylolpropane triacrylate can be estimated to be 1510(SRC). According to a classification scheme(2), this estimated Koc value suggests that trimethylolpropane triacrylate is expected to have low mobility in soil.

The Henry's Law constant for trimethylolpropane triacrylate is estimated as 6X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trimethylolpropane triacrylate is expected to be essentially nonvolatile from water surfaces(2). Trimethylolpropane triacrylate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Trimethylolpropane triacrylate's estimated vapor pressure of 5.9X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(1), suggests that volatilize from dry soil surfaces will not be important fate process(SRC); however, trimethylolpropane triacrylate is a liquid with a noticeable acrylic odor(3) suggesting some volatilization may occur(SRC).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of trimethylolpropane triacrylate is 1000 or greater; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,274 workers (809 of these were female) were potentially exposed to trimethylolpropane triacrylate in the US(1). Occupational exposure to trimethylolpropane triacrylate may occur through inhalation and dermal contact with this compound at workplaces where trimethylolpropane triacrylate is produced or used(SRC). Workers involved in the manufacturing, processing, product handling, and application of trimethylolpropane triacrylate are at risk of exposure(2). A potential exists for widespread exposure of consumers through the use of trimethylolpropane triacrylate in products such as latex paints and furniture and floor polishes(2).

In male B6C3F1 mice, 75% of the dose was absorbed 72 hours after a single application of 1.2 mg/kg. The percent dose remaining at the dose site was higher in mice (31%) than in rats (9%). Approximately 42% of the applied dose was recovered in urine, feces, and exhaled carbon dioxide 72 hours after application, an amount similar to that excreted by rats (45%) following dermal application of 1.7 mg/kg. The radioactivity associated with tissues at 72 hours was less than 1%. The nonapplication site skin had an elevated tissue:blood ratio.|Metabolism and disposition of (14)C-trimethylolpropane triacrylate was investigated in male F344/N rats and B6C3F1 mice following single intravenous administration and dermal application (protected from oral grooming). In male rats, the percent dose absorbed was 55.7%, 32.7%, or 18.7% at 72 hours following dermal application of 1.7, 15.2, or 130 mg/kg. In mass terms, approximately five times more trimethylolpropane triacrylate was absorbed as the dose concentration increased by one order of magnitude. About 9% of the dose was recovered from the dose site regardless of the applied dose. About 45%, 19%, or 5% of the applied dose was recovered in the excreta 72 hours after dermal application of 1.7, 15.2, or 130 mg/kg, respectively. The radioactivity associated with tissues at 72 hours was less than 1%. The kidney had elevated tissue:blood ratios at each dose. Following intravenous administration of 9.4 mg/kg (14)C-trimethylolpropane triacrylate in male rats, a total of 77.4% of the applied dose was excreted in urine, feces, and exhaled carbon dioxide 72 hours after administration. Among the tissues collected, the highest radiolabeled concentration was associated with blood.|After a single 124 mg/kg dermal application of (14)C-trimethylolpropane triacrylate in male rats followed by tape stripping the application site at 72 hours, most of the radioactivity associated with the dose site was trimethylolpropane triacrylate thereby confirming that the test article was stable on the skin.

Trimethylolpropane triacrylate is manufactured by esterification of trimethylolpropane; acrylic acid is a known impurity in the technical-grade compound.

/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 the 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Skin sensitivity and photo patch testing of 0.2% trimethylolpropane triacrylate in petrolatum was performed on 47 employees of a citrus juice bottling plant who were exposed to ultraviolet-cured printing inks. All 47 workers had positive reactions to one or both tests. Because few workers showed skin sensitization to trimethylolpropane triacrylate, the past skin reactions were considered to be irritant, not allergic, reactions to the inks and their components.|/HUMAN EXPOSURE STUDIES/ Four workers in a plastic floor manufacturing facility developed hand and face dermatitis a year after the introduction of a varnish with an aziridine-based hardener containing 3% to 5% trimethylolpropane triacrylate. The workers had positive reactions to skin patch tests with trimethylolpropane triacrylate in acetone at 0.0001% (1/4), 0.03% (3/4), and 0.1% (4/4), with the most severe reactions occurring in the worker who reacted to the 0.0001% formulation.|/HUMAN EXPOSURE STUDIES/ Seven of 10 workers exposed to ultraviolet-curable printing inks at a plastic food container manufacturing plant developed contact dermatitis; one person had a positive reaction for sensitization to 0.1% trimethylolpropane triacrylate in petrolatum.|/HUMAN EXPOSURE STUDIES/ /Investigators/ reported the development of allergic dermatitis in six people who worked with ultraviolet-curable inks containing trimethylolpropane triacrylate for 3 to 32 weeks. All six had positive reactions to skin patch tests with 0.1% or 0.5% trimethylolpropane triacrylate in acetone.|For more Human Toxicity Excerpts (Complete) data for Trimethylolpropane triacrylate (6 total), please visit the HSDB record page.

TMPTA

Adhesive manufacturing|2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester: ACTIVE|Ethylenimine and propylenimine react with trifunctional acrylates, such as 2-ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate ... to produce trifunctional aziridines.