3-(메타크릴옥시프로필)트리메톡시실란

1.045 at 25 °C

1.045 @25 °C

190 °C

Boiling point = 80 °C at 1 mm Hg

190 °C @760 [mm Hg]

When heated to decomposition it emits acrid smoke and irrtating fumes.

Hazardous decomposition products: carbon monoxide, carbon monoxide, carbon dioxide, silicon dioxide.

... In general the methacrylic esters, polymerize much less readily than the corresponding ordinary acrylates. Nonetheless, they are stabilized by adding hydroquinone or pyrogallol, particularly in the presence of metallic copper. /Methacrylates/

Dry Powder; Liquid

Liquid; [HSDB] Colorless liquid; [MSDSonline]

This chemical does not meet GHS hazard criteria for 83.6% (534 of 639) of all reports.

Warning

H315 (15%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 639 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester

Regulation (EC) No 1935/2004 (amended)

2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl 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: 16-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15277

3-(Trimethoxysilyl)propyl methacrylate: Does not have an individual approval but may be used under an appropriate group standard

Combustible; moderate fire risk

Will burn if involved in a fire ... Combustible liquid and vapor.

Lower 0.9 vol%; upper 5.4 vol%

Containers may explode in the heat of a fire.

A skin and eye irritant.

Causes respiratory tract irritation. May be harmful if inhaled.

May be harmful if inhaled. Causes respiratory tract irritation. May be harmful if absorbed through skin. Causes skin irritation. Causes eye irritation.

Incompatibilities with other materials: Strong oxidizing agents, strong acids, strong bases.

Materials to avoid: Strong oxidizing agents, strong acids, strong bases.

Use water spray to cool fire-exposed containers. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.

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

Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Store protected from moisture. Store under nitrogen.

Use explosion-proof ventilation equipment. Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 °C are recommended for the polyfunctional methacrylates. ... The methacrylate monomers should not be stored for longer than one year. Shorter storage times are recommended for the aminomethacrylates, ie, three months, and the polyfunctional methacrylates, ie, six months. Many of these cmpd are sensitive to UV light and should, therefore, be stored in the dark. The methacrylic esters may be stored in mild steel, stainless steel, or aluminum. /Methacrylic acid & derivatives/

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C Moisture sensitive. Handle and store under inert gas. Heat sensitive.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition. Use a spark-proof tool. Do not let this chemical enter the environment.

Methods for cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.

Environmental precautions: Do not let product enter drains.

This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.

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.

... Hazard is the generation of considerable exothermic heat in some of the reactions, so that high pressures & temp may develop. This danger ... should be borne in mind when designing plant. Awareness of the dangers and of good engineering design are essential to safety. Employees should be instructed about the necessity of cleansing the skin if it is contaminated by materials which are irritants or skin-absorbed. With careful design, however, and complete enclosure of those processes where toxic chemicals or intermediates occur, dangerous exposures can be avoided. /Acrylic acid & derivatives/

In case of skin contact: Wash off with soap and plenty of water. Consult a physician.

In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.

Hygiene measures: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

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

71 [mg/m3]

780 [mg/m3]

4700 [mg/m3]

Personal Protective Equipment. Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.

A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) 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).

Hand protection: The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Handle with gloves.

For more Personal Protective Equipment (PPE) (Complete) data for Trimethoxysilylpropyl methacrylate (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,700(SRC), determined from a structure estimation method(2), indicates that trimethoxysilylpropyl methacrylate is expected to have low mobility in soil(SRC). Volatilization of trimethoxysilylpropyl methacrylate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-7 atm-cu m/mole(SRC), by using a fragment constant estimation method(3). Trimethoxysilylpropyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.44 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,700(SRC), determined from a structure estimation method(2), indicates that trimethoxysilylpropyl methacrylate 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 3.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.75(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis of 3-methacryloxypropyl-trimethodxysilane proceeds within a few minutes in a low pH environment as a result of the catalytic action of H+ ions(8). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethoxysilylpropyl methacrylate, which has an estimated vapor pressure of 0.44 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the vapor phase in the ambient atmosphere. Vapor-phase trimethoxysilylpropyl methacrylate 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 15 hours(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The atmospheric half-life for the vapor-phase reaction of trimethoxysilylpropyl methacrylate with ozone has been estimated as 24 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Trimethoxysilylpropyl methacrylate does not contain chromophores that absorb at wavelengths >290 nm(5) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trimethoxysilylpropyl methacrylate can be estimated to be 1,700(SRC). According to a classification scheme(2), this estimated Koc value suggests that trimethoxysilylpropyl methacrylate is expected to have low mobility in soil.

2-Propionic acid, 2-methyl, 3-(trimethoxysilyl)propyl ester (silane A-174) was evaluated for the ability to increase the incidence of micronucleated polychromatic erythrocytes in peripheral blood samples of male and female Swiss-Webster mice treated by I.P. injection. Groups of 10 mice (5 male and 5 female) received a single dose of 2500, 4000, 5000 mg/kg body weight of test article in corn oil; blood samples were drawn 30, 48 and 72 hours after injection. A statistically significant increase in the incidence of micronucleated polychromatic erythrocytes was not observed (Fischer exact test, p > 0.001) at any dose level or time of sampling. A statistically significant (linear regression analysis, r = -0.97) dose related decrease in the PCE/NCE ratio was observed at the 72 hour sampling time (all doses), reflecting the toxic effect of the test article. Additionally, in a preliminary toxicity test, administration of 5000 mg/kg test article (maximum testable dose) induced a 25% decrease in the polychromatic to normochromatic erythrocyte (PCE/NCE) ratio, while mortality was not observed at doses up to and including this level.

The frequency of chromosomal aberrations was determined in Chinese Hamster Ovary (CHO) cells exposed to 2-propionic acid, 2-methyl, 3-(trimethoxysilyl)propyl ester (silane A-174) with and without metabolic activation provided by Aroclor-induced rat liver S9 fraction. CHO-K1-BH4 cells were exposed to test article at concentrations ranging from 0.1 to 0.6 mg/ml in the presence and absence of activation, and samples were withdrawn at 8 and 12 hours for evaluation. In activated tests, statistically significant (Fischer's exact test, p < 0.05) increases in the incidences of aberrations were observed in samples withdrawn at 8 hours from cultures exposed to 0.3, 0.4, and 0.6 mg/ml, and in samples withdrawn at 12 hours from cultures exposed to 0.2 and 0.3 mg/ml. Additionally, it was reported that the frequency of sister chromatid exchange was increased in the 12 hour samples . A statistically significant (p < 0.01) increase in the incidence of aberrations was observed in samples withdrawn at 8 hours from nonactivated cultures exposed to 0.4 mg/ml. In preliminary range finding tests, exposure of cells to test article at a concentration of 0.5 mg/ml with activation reduced the percentage of mitotic cells by 62.1%, while exposure to 0.6 mg/ml without activation resulted in a 44.4% decrease.

The ability of methacryloxypropyltrimethoxysilane (MPTS) to induce mutations at the HGPRT gene locus in Chinese Hamster Ovary (CHO) cells in vitro was evaluated in the presence and absence of Aroclor-induced rat liver S9 metabolic activation. Based on preliminary toxicity determinations, MPTS was tested for mutagenicity at concentrations of 0.2, 0.4, 0.6, 0.7 or 0.8 mg/ml without activation and at concentrations of 0.1, 0.2, 0.4, 0.6, 0.7 or 0.8 mg/ml with activation. Cell survival ranged from 108 - 156% without activation and from 42 - 105% with activation. There were no significant differences between treated and control (methanol solvent vehicle) cultures with respect to mutation frequencies at any of the concentrations tested, either with or without activation.

The mutagenicity of methacryloxypropyltrimethoxysilane (MPTS) was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, MPTS was tested for mutagenicity at concentrations up to 500 ug/plate using the overlay plate assay methods. MPTS did not cause a positive response in any of the bacterial tester strains, either with or without metabolic activation. MPTS was also tested using the spot test, and the results were negative.

For more TSCA Test Submissions (Complete) data for Trimethoxysilylpropyl methacrylate (6 total), please visit the HSDB record page.

/OTHER TOXICITY INFORMATION/ Biologically, methacrylates resemble acrylates, except for lower reactivity and thus decr toxicity. This is probably due to steric hindrance by its methyl group and in turn decr rates of membrane transport and systemic translocation. /Methacrylic esters/

An estimated BCF of 3.2 was calculated for trimethoxysilylpropyl methacrylate(SRC), using an estimated log Kow of 0.75(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).

The Henry's Law constant for trimethoxysilylpropyl methacrylate is estimated as 3.0X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trimethoxysilylpropyl methacrylate is expected to be essentially nonvolatile from water surfaces(2). The Henry's Law constant for trimethoxysilylpropyl methacrylate indicates that volatilization from moist soil surfaces will not occur(SRC). Trimethoxysilylpropyl methacrylate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.44 mm Hg(SRC), determined from a fragment constant method(3).

The rate constant for the vapor-phase reaction of trimethoxysilylpropyl methacrylate with photochemically-produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 15 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of trimethoxysilylpropyl methacrylate with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 2.7X10-3 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 81 and 8.1 years at pH values of 7 and 8, respectively(3). Trimethoxysilylpropyl methacrylate does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The hydrolysis of 3-methacryloxypropyl trimethoxy silane was carried out in an ethanol/water 80/20 (w/w) solution under acidic, alkaline and neutral conditions, and it was found that the kinetic rate of the hydrolysis under neutral conditions was very low; the addition of triethylamine catalyzed both silane hydrolysis and self condensation reactions(1). Acidic conditions enhanced the hydrolysis and the ensuing silanol entities were quite stable; in fact, these conditions slowed down the rate of the self condensation reactions(1). At high and very low pH values, the rate of hydrolysis is higher than at the neutral pH, at which silanes are most stable; the hydrolysis of 3-methacryloxypropyl-trimethoxysilane proceeds within a few minutes in a low pH environment as a result of the catalytic action of H+ ions(2).

Occupational exposure to trimethoxysilylpropyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where trimethoxysilylpropyl methacrylate is produced or used. The most likely pathway by which the general public is exposed to trimethoxysilylpropyl methacrylate is by ingestion or dermal contact during porcelain dental repair work. (SRC)

Trimethoxysilylpropyl methacrylate's production and use as an adhesion or coupling agent to dental porcelain, ceramic, or glass surfaces may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.44 mm Hg at 25 °C indicates trimethoxysilylpropyl methacrylate will exist solely as a vapor in the atmosphere. Vapor-phase trimethoxysilylpropyl methacrylate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 15 hours. The atmospheric half-life for the vapor-phase reaction of trimethoxysilylpropyl methacrylate with ozone has been estimated as 24 hours. Trimethoxysilylpropyl methacrylate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, trimethoxysilylpropyl methacrylate is expected to have low mobility based upon an estimated Koc of 1,700. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 3.0X10-7 atm-cu m/mole. Trimethoxysilylpropyl methacrylate is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, trimethoxysilylpropyl methacrylate is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. The hydrolysis of 3-methacryloxypropyl-trimethodxysilane proceeds within a few minutes in a low pH environment as a result of the catalytic action of H+ ions. A base-catalyzed second-order hydrolysis rate constant of 2.7X10-3 L/mole-sec was estimated using a structure estimation method; this corresponds to half-lives of 81 and 8.1 years at pH values of 7 and 8, respectively. Occupational exposure to trimethoxysilylpropyl methacrylate may occur through inhalation and dermal contact with this compound at workplaces where trimethoxysilylpropyl methacrylate is produced or used. Monitoring data indicate that the general population may be exposed to trimethoxysilylpropyl methacrylate by ingestion or dermal contact during porcelain dental repair work. (SRC)

Used in dental materials and adhesives and adhesives with primer systems; Used to make organosiloxane copolymers, prosthetics, and contact lenses; Also used as coupling agent (room temperature-cured polymers, resin-glass, resin-metal, and resin-resin bonds) and silylating agent for plastic surfaces; [HSDB]

Working with Glues and Adhesives [Category: Other]

Commercial silane coupling agent with applications in unsaturated polymers

Adhesion to dental porcelain or ceramic surface is achieved through the organofunctional silane, 3-methacryloxypropyltrimethoxysilane

Used in dentistry as a porcelain repair system. The system uses a primer containing a 4% solution of trimethoxysilylpropyl methacrylate in methacrylate and ethanol.

Coupling agent for promotion of resin-glass, resin-metal, and resin-resin bonds, for formulation of adhesives having "built in" primer systems.

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

2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5406]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester. Aggreated National Production Volume: 1 to < 10 million lbs.

... Methacrylic-functional silanes were introduced as particularly effective modifiers for organic polymers containing carboxyl groups. These are produced almost exclusively by hydrosilylation of allyl methacrylate. ... This reaction leads to the desired 3-methacryloxypropyl group with good selectivity because of the considerably higher reactivity of the allyl group. The most important of these compounds, the trimethoxy compound ... is produced industrially either by direct addition of trimethoxysilane or preferably via the corresponding trichlorosilyl precursor in the presence of radical scavengers.

By the reaction of 3-chloropropyltrimethoxysilane with methacrylic acid.

Synthetic Rubber Manufacturing

2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester: ACTIVE