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HCID 27423생성일: 2026년 10월 27일

트리메티올프로판 트리아크릴레이트

트라이메틸올프로페인트라이아크릴레이트 · 트라이메틸올프로판트라이아크릴산 · 트라이메틸올프로페인트라이아크릴산 · 트리메티올프로판트리아크릴레이트 · 트리메틸롤프로판트리아크릴산염 · 트라이메틸올프로판트라이아크릴레이트 · 트라이메틸롤프로판트라이아크릴레이트 · 트라이메틸올프로페인트라이아크릴산(TRIMETHYLOLPROPANETRIACRYLATE)

https://huagongshe.com/ko/chemical/27423

트리메티올프로판 트리아크릴레이트 분자 구조식

식별자 및 물리적 특성

CAS No.15625-89-5
분자식C15H20O6
평균 분자량296.31 g/mol
단동위원소 질량296.12598836 g/mol
SMILESC=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C
InChIKeyDAKWPKUUDNSNPN-UHFFFAOYSA-N
PubChem CID27423
ChEMBLCHEMBL1886556
ChEBICHEBI:35028
EC No.239-701-3
DTXSIDDTXSID0027773
현지명트리메티올프로판 트리아크릴레이트

화학 및 물리적 성질

XLogP2.7
극성 표면적78.9
수소 결합 공여자 수0
수소 결합 수용자 수6
회전 가능 결합 수13
무거운 원자 수21
형식 전하0
복잡도364
PolymersPlastics & Rubber -> (Meth)acrylates
화장품Cosmetics ingredient -> Other (Specify)
LogP(분배 계수)log Kow = 2.75
냄새Acrylic or pungent odor
밀도1.11 g/cu cm at 20 °C1.1 g/mL at 25 °C (lit.)
Color/FormViscous, colorless to tan liquid
용해도Insoluble in water
끓는 점BP: >200 °C at 1 mm Hg>200°C
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
굴절률Index of refraction = 1.4735 at 20 °Cn20/D 1.474(lit.)
Physical DescriptionLiquidDry PowderCBI[IUCLID] Colorless liquid with a pungent odorHygroscopicTan or amber in color if impure[NTP] Clear or yellow liquid with a pungent odor[Alfa Aesar MSDS]
Collision Cross Section165.9 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID0027773]
녹는점-66°C
증기 밀도>1 (vs air)
증기압<0.01 mm Hg ( 20 °C)
인화점>230 °F
저장 조건Refrigerator
물리적 상태액체
pKa(산도 계수)0[at 20 ℃]
비중1.1
색상Colorless to Light yellow to Light orange
용해도물과 섞일 수 있습니다.
헨리 상수1.6×104 mol/(m3Pa) at 25℃, HSDB (2015)
화장품 원료 기능필름 형성제헤어 컨디셔닝헤어 스타일링
InChI1S/C15H20O6/c1-5-12(16)19-9-15(8-4,10-20-13(17)6-2)11-21-14(18)7-3/h5-7H,1-3,8-11H2,4H3
InChIKeyDAKWPKUUDNSNPN-UHFFFAOYSA-N
SMILESCCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C
LogP(분배 계수)4.35 at 20℃
NISTTMPTA (Trimethylol propane triacrylate)(15625-89-5)
EPATrimethylolpropane triacrylate (15625-89-5)

화학적 성질

Colorless viscid liquid

안전 및 규제

GHS 분류WarningH315: Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.1% (4 of 3852) of reports.H315 (99.9%): Causes skin irritation [Warning Skin corrosion/irritation]
규제 정보Chemical: 2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl esterHazard Traits - Carcinogenicity2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 1,1'-[2-ethyl-2-[[(1-oxo-2-propen-1-yl)oxy]methyl]-1,3-propanediyl] ester 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)Status: Active Update: 04-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15232Trimethylolpropane triacrylate: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보IMAP assessments - 2-Propenoic acid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester: Human health tier II assessment
유해성 요약Allergic contact dermatitis reported in workers exposed to UV-cured coatings and textile inks[Kanerva, p. 1745] Labeled in the EU as causing skin and eye irritation with the potential to cause skin sensitization[IUCLID] May spontaneously polymerize on exposure to heat or light (stabilized with monomethyl ester of hydroquinone)[NTP] Occupational asthma confirmed in a worker exposed for 20 years in a kiosk to a tint containing trimethylolpropane triacrylate from a thermal printer[Reference #1]
Hazard Classes and CategoriesSkin Irrit. 2 (99.9%)Eye irritation - category 2Skin corrosion/irritation - Category 2Serious eye damage/eye irritation - Category 2ACarc. 2
처리 방법

용도

개요

Trimethylolpropane triacrylate (TMPTA) is a multifunctional acrylie monomer. It reacts with propyleneimine to form polyfunctional aziridine. Sensitization was observed in a textile fabric printer. Patch tests were positive with the polyfunctional aziridine hardener, but were negative to TMPTA. TMPTA caused contact dermatitis in an optic-fiber manufacturing worker and was reported as a sensitizer in a floor top coat or in photopolymerizable inks.

용도

Trimethylolpropane triacrylate has important properties like low volatility, resistance against weather, chemical, water and abrasion, and immediate curing property. The above mentioned properties prompted its use in the production of adhesives, plastics, sealant chemicals, paint additives, photosensitive chemicals, ink and toner. It finds application in alkyd coatings, dental polymers, compact discs, hardwood floors, concrete polymers, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry.

제조 및 합성 방법

제조 방법

Synthesis of trimethylolpropane triacrylate: 2.44 kg of trimethylolpropane, 3.93 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 of BAYER AG), 9 g of hydroquinone and 1.5 liters of petroleum ether (boiling range 60° to 70° C) were heated under a water separator, whilst stirring, in a 10 liter three-necked flask equipped with a stirrer, water separator and gas inlet tube. At the same time, a constant stream of air saturated with allyl alcohol was passed through the flask at a rate of 2 liters/hour. In total, 16 ml of allyl alcohol were introduced into the esterification mixture in this way. After 80 hours, the reaction mixture had an acid number of 32 and the boiling point had risen to 72° C. The petroleum ether was distilled off, remnants being removed by applying a vacuum of 0.2 mm Hg at a product temperature of 40° C. The esterification catalyst was separated off by filtration and was kept for further use. The trimethylolpropane triacrylate obtained in practically quantitative yield was pale yellowish and clear. The viscosity corresponded to a time of outflow of 20 seconds measured in a DIN cup 4 at 20° C. The product showed no change even on storage for 4 months at 60° C. When used in a UV light-curing printing ink which contained a photoinitiator, the product polymerised at high speed.Literature source US04059721

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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.
Other Standards Regulations and GuidelinesWorkplace Environmental Exposure Level (WEEL): 8-hr Time-weighted Average (TWA) 1 mg/cu m, skin.
환경 거동TERRESTRIAL 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).
유해 작용Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of June 21, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=15625-89-5]
Soil Adsorption/MobilityUsing 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.
Human Toxicity Excerpts/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 dermatitisone 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.
Artificial Pollution SourcesTrimethylolpropane 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).
Environmental BiodegradationAEROBIC: Trimethylolpropane triacrylate, present at 100 mg/L, reached 19% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1)however, total degradation of trimethylolpropane triacrylate was 87% over the 4-week period with the formation of the diacrylate and monoacrylate esters plus trimethylolpropane(1).
Carcinogen ClassificationTrimethylolpropane triacrylate, technical gradeGroup 2B: Possibly carcinogenic to humansVolume 122: (2019) Isobutyl Nitrite, β-Picoline, and Some Acrylates2018Trimethylolpropane Triacrylate
Environmental BioconcentrationAn 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).
Volatilization from Water/SoilThe 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).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Eye irritation was scored 9 on a 10-grade scale 24 hours after application of trimethylolpropane triacrylate. By a Draize test, instillation of trimethylolpropane triacrylate into rabbit eyes induced irritation and reversible corneal opacity for 7 days./LABORATORY ANIMALS: Acute Exposure/ The NTP conducted a contact hypersensitivity study in conjunction with a subchronic study of technical grade trimethylolpropane triacrylate. It was not shown to be a skin sensitizer in female BALB/c mice. Although there was a significant trend toward increased responses at doses of 0.05%, 0.1%, and 0.25% in the murine local lymph node assay (LLNA), no individual dose was significantly different from the vehicle control and the highest response did not reach the threefold stimulation index suggested for a positive in the LLNA. Trimethylolpropane triacrylate was negative in a mouse ear swelling test. In the same study, trimethylolpropane triacrylate was positive in the murine irritancy assay at concentrations of 0.05%, 0.25%, and 0.5% when applied directly to the skin./LABORATORY ANIMALS: Acute Exposure/ /Investigators/ immunized outbred male and female Hartley guinea pigs (number not specified) with subcutaneous injection into the footpad and the nape of the neck with 0.1 mL of an emulsion containing trimethylolpropane triacrylate in ethanol:saline (1:4) in FCA. The total trimethylolpropane triacrylate dose was 11.5 umol. Skin tests of 0.02 mL of 0.25% or 0.5% trimethylolpropane triacrylate in acetone:olive oil (4:1) were then applied to the shaved flank of the guinea pig, and reactions were recorded at 24, 48, 72, and 96 hours. Skin reactions were graded on a scale of 0 (no reaction) to 3 (severe reaction). On day 7, the reactions for both concentrations were mild at 24 hours and moderate at 48 hoursthe 24- and 48-hour reactions on day 14 were moderate./LABORATORY ANIMALS: Acute Exposure/ In a maximization test of acrylates and methacrylate esters, outbred female SSc:AL guinea pigs were induced with three 2 x 50 uL intradermal injections, including one of FCA in sterile water and one each of a test compound (methyl methacrylate, ethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, or trimethylolpropane trimethylacrylate) in soybean oil and in a mixture of emulsified FCA and water. On day 7, approximately 250 mg of 10% sodium lauryl sulfate in petrolatum was applied to the neck and left uncovered for 24 hours. On day 8, the test compound or petrolatum (400 uL) was applied to a filter paper patch that was applied to the flank and left in place for 48 hours. On day 21, the guinea pigs were challenged with up to six patches containing 25 uL of the sensitizing compound: 2-hydroxy-methacrylate, 1,6-hexane diolodiacrylate, pentaerythritol triacrylate, or trimethylolpropane triacrylate. Sensitization determinations were made at 48 and 72 hours. The treatment was repeated on the opposite flank of each animal after 35 days. Positive skin sensitization reactions occurred in 14 of 19 guinea pigs induced with trimethylolpropane trimethylacrylate and challenged with 2% trimethylolpropane triacrylateanimals induced with the other test chemicals did not have cross reactions with trimethylolpropane triacrylate.For more Non-Human Toxicity Excerpts (Complete) data for Trimethylolpropane triacrylate (22 total), please visit the HSDB record page.
Environmental Abiotic DegradationThe 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).
수질 위해 등급(WGK)1
TSCA 등재 상태TSCA listed
RTECS 번호AT4810000
독성LD50 oral in rat: 5190uL/kg
관세 코드29161290
위험 문구(R)36/38-43
위험 표시Xi
안전 문구(S)39
기존화학 물질KE-29547
위험 등급Aquatic Acute 1Aquatic Chronic 1Carc. 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
저장 분류10 - Combustible liquids
유해 물질 데이터15625-89-5(Hazardous Substances Data)