3-Methacryloxypropyltrimethoxysilane 2530-85-0 wiki

1. Names and Identifiers

1.1 Name: 3-Methacryloxypropyltrimethoxysilane
1.2 Synonyms: [Γ-(Methacryloyloxy)propyl]trimethoxysilane 2-methyl-6-trimethoxysilyl-1-hexen-3-one 2-Propenoic acid, 2-methyl-, 3- (trimethoxysilyl)propyl ester 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester 3-(Methacryloyloxy)propyltrimethoxysilane 3-(TrimethoxysiL 3-(trimethoxysilyl)propyl 2-methylprop-2-enoate 3-(Trimethoxysilyl)propyl methacrylate 3-(trimethoxysilyl)propyl methacrylate- 3-Methacryloxypropyltrimethoxysilane 3-(Trimethoxysilyl)propyl Methacrylate A 174 A-174, Z6003, KBM-503 CFS-850 CM8550 Co-Formula CFS-850 EINECS 219-785-8 kbm503 kdm503 kh570 m8550 MAPTMS MEMO Methacrylic Acid 3-(Trimethoxysilyl)propyl Ester Methacrylic acid, 3- (trimethoxysilyl)propyl ester Methacrylic acid, 3-(trimethoxysilyl)propyl ester (8CI) methacrylic acid-3-trimethoxysilylpropyl ester MFCD00008593 mops-m Silane A174 Silquest*A-174 trimethoxy-3-hydroxypropylsilane methacrylate γ-methacryloxy propyl trimethoxyl silane Γ-methacryloxypropyltrimethoxysilane

1.3 CAS No.: 2530-85-0

1.4 CID: 17318

1.5 EINECS(EC#): 219-785-8

1.6 Molecular Formula: C10H20O5Si (isomer)

1.7 Inchi: InChI=1S/C10H20O5Si/c1-9(2)10(11)15-7-6-8-16(12-3,13-4)14-5/h1,6-8H2,2-5H3

1.8 InChkey: XDLMVUHYZWKMMD-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(=C)C(=O)OCCC[Si](OC)(OC)OC

1.10 Isomers Smiles: CC(=C)C(=O)OCCC[Si](OC)(OC)OC

2. Properties

2.1 Density: 1.045

2.1 Melting point: <-50 °C

2.1 Boiling point: 190℃

2.1 Refractive index: 1.43-1.432

2.1 Flash Point: 92℃

2.1 Precise Quality: 248.10800

2.1 PSA: 53.99000

2.1 logP: 1.37390

2.1 Appearance: Liquid

2.2 Storage: Moisture Sensitive. Ambient temperatures.

2.3 Autoignition Temperature: 265 °C ( 509 °F)

2.4 Chemical Properties: Colorless transparent liquid 3-Methacryloxypropyltrimethoxysilane Preparation Products And Raw materials Raw materials

2.5 Color/Form: Liquid

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

2.7 Water Solubility: Miscible with water.

2.8 Spectral Properties: Index of refraction: 1.4285 at 25 deg C

2.9 Stability: Stable under normal temperatures and pressures.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Methods of Manufacturing: ... 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.

3.2 Polymerization: ... 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/

3.3 Usage: Srp: in dental materials, prepn of organosiloxane copolymers, preparation of prosthetics, and contact lenses.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Octanol/Water Partition Coefficient: log Kow = 0.75 (est)

4.2 Other Preventative Measures: ... 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.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

4.3 Hazard Declaration: H315

4.3 Cleanup Methods: 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.

4.4 DisposalMethods: 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.

4.5 RIDADR: 3082

4.5 Fire Fighting Procedures: 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.

4.6 FirePotential: Combustible; moderate fire risk
Will burn if involved in a fire ... Combustible liquid and vapor.

4.7 Caution Statement: P260, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.7 Formulations/Preparations: Grade: 97% min purity

4.8 WGK Germany: 1

4.8 RTECS: UC0230000

4.8 Protective Equipment and Clothing: 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.
Eye protection: Safety glasses with side-shields conforming to EN166.
Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.

4.9 Reactivities and Incompatibilities: Incompatibilities with other materials: Strong oxidizing agents, strong acids, strong bases.
Materials to avoid: Strong oxidizing agents, strong acids, strong bases.

4.10 Report: Reported in EPA TSCA Inventory.

4.11 Skin, Eye, and Respiratory Irritations: 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.

4.12 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-28-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S28:After contact with skin, wash immediately with plenty of soap-suds.?
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: 3082
WGK Germany: 1
RTECS: UC0230000
F: 4.4-8-21
TSCA: Yes
A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.

4.13 Sensitive: Moisture Sensitive

4.14 Specification: ?3-Methacryloxypropyltrimethoxysilane (CAS NO.2530-85-0) is also named as (3-(Methacryloxy)propyl)trimethoxysilane ; 1-Propanol, 3-(trimethoxysilyl)-, methacrylate ; 2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester ; 3-(Trimethoxysilyl)-1-propanol methacrylate ; 3-(Trimethoxysilyl)propyl methacrylate ; 3-Methacryloyloxypropyl-trimethoxysilane ; A 174 ; BRN 1952435 ; Dynasylan MEMO ; HSDB 5468 ; KBM 503 ; KDM 503 ; KH 570 ; M 8550 ; Methacrylic acid, 3-(trimethoxysilyl)propyl ester ; Methacryloyloxypropyltrimethoxysilane ; Mops-M ; NSC 93591 ; NUCA 174 ; Q 174 ; Silane adduct, allyl methacrylate trimethoxy- ; Silane, (3-hydroxypropyl)trimethoxy-, methacrylate ; Silane, 3-methacryloxypropyltrimethoxy- ; Silicone A-174 ; Silicone a-174 ; Trimethoxysilyl-3-propylester kyseliny methakrylove ; Trimethoxysilyl-3-propylester kyseliny methakrylove [Czech] ; Trimethoxysilylpropyl methacrylate ; Union carbide A-174 ; Union carbide a-174 ; Z 6030 ; alpha-Methylacryloxypropyltrimethoxysilane .?3-Methacryloxypropyltrimethoxysilane (CAS NO.2530-85-0) is colorless transparent liquid.

4.15 Toxicity: LD50 oral in rat: 22600uL/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

2530-85-0Total: 9 Synthesis Route

67-56-1 386 Suppliers

96-05-9 55 Suppliers

2530-85-0 277 Suppliers

Literatures:
Sakai, Takashi; Hayashi, Kyoko; Yano, Fumika; Takami, Mie; Ino, Megumi; Korenaga, Toshinobu; Ema, Tadashi Bulletin of the Chemical Society of Japan, 2003 , vol. 76, # 7 p. 1441 - 1446
Yield: ~36%

79-41-4 50 Suppliers

80-62-6 4 Suppliers

2530-85-0 277 Suppliers

Literatures:
US5489625 A1, ;
Yield: null

2487-90-3 129 Suppliers

96-05-9 55 Suppliers

2530-85-0 277 Suppliers

Literatures:
US2010/179340 A1, ; Page/Page column 6-7 ;
Yield: null

View all

8. Precursor and Product

precursor:

5536-61-8

1634-04-4

79-41-4

80-62-6

2530-87-2

10025-78-2

96-05-9

6900-35-2

7351-61-3

2487-90-3

67-56-1

product :

63620-14-4

17096-07-0

994-49-0

307531-94-8

9. Other Information

9.0 Storage Conditions: ... 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.

9.1 Henrys Law Constant: Henry's Law constant = 3.0X10-7 atm-cu m/mole at 25 °C (est)

9.2 Experimental Properties: Hydroxyl radical reaction rate constant = 2.5X10-11 cu cm/molecule-sec at 25 °C (est)|Ozone reaction rate constant = 1.1X10-17 cu cm/molecule-sec at 25 °C (est)

9.3 Autoignition Temperature: 265 °C ( 509 °F)

9.4 Disposal Methods: 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.

9.5 Personal Protective Equipment: 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.

9.6 Fire Potential: Combustible; moderate fire risk|Will burn if involved in a fire ... Combustible liquid and vapor.

9.7 Fire Fighting Procedures: 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.

9.8 Cleanup Methods: 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.

9.9 Preventive Measures: ... 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.

9.10 Environmental Concentrations: 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)

9.11 Pollution Sources: Trimethoxysilylpropyl methacrylate's production and use as an adhesion(1) or coupling agent to dental porcelain, ceramic, or glass(2) surfaces may result in its release to the environment through various waste streams(SRC).

9.12 Environmental Fate: 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).

9.13 Abiotic Degradation: 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).

9.14 Bioconcentration: 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).

9.15 Mobility: 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.

9.16 Volatilization: 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).

9.17 Mesh: Materials used in the production of dental bases, restorations, impressions, prostheses, etc. (See all compounds classified as Dental Materials.)

9.18 Metabolism: Small quantities of methacrylates may readily be metabolized by saponification into the alcohol and methacrylic acid. The latter may form an acetyl-coenzyme derivative, which then enters the normal lipid metabolism. /Methacrylates/

9.19 Antidote: /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 as 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. /Silane, Chlorosilane, and Related Compounds/|/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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . Monitor for shock 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. Administer activated charcoal (refer to ingestion protocol in Section Three ... . Cover skin burns with sterile dressings after decontamination ... . /Silane, Chlorosilane, and Related Compounds/|/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. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Silane, Chlorosilane, and related compounds/|/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 as 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. /Esters and related compounds/|For more Antidote and Emergency Treatment (Complete) data for Trimethoxysilylpropyl methacrylate (6 total), please visit the HSDB record page.

9.20 Human Toxicity Excerpts: /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/

9.21 Mesh Entry Terms: 3-methacryloyloxypropyl-trimethoxysilane

9.22 Production: 1,000,000 - 10,000,000 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#5411]|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.

9.23 Formulations: Grade: 97% min purity

9.24 Manufacturing Info: Adhesive manufacturing|2-Propenoic acid, 2-methyl-, 3-(trimethoxysilyl)propyl ester: ACTIVE

9.25 Usage: 3-(Methacryloyloxy)propyltrimethoxysilane (MPS) acts as a functional comonomer, which is used to prepare polystyrene latex having silanol by emulsion polymerization. It is used in the preparation of polymers in association with other monomers like vinyl acetate, acrylic acid and methyl acrylic acid used in coating, adhesive and sealing agents, which provides excellent adhesion and durability. The composite materials made from unsaturated polyester by using MPS improve mechanical property.

9.26 BRN: 1952435

9.27 Introduction

3-Methacryloxypropyltrimethoxysilane is a methacryl-functional silane, it is a clear, light and heat sensitive liquid with a faintly sweet odour.
3-Methacryloxypropyltrimethoxysilane is used as adhesion promoter at organic/inorgainc interfaces, as surface modifier (e.g. imparting water repellency, organophilic surface adjustment) or as crosslinking of polymers). It is used as a coupling agent to improve the physical and electrical properties of glass-reinforced and mineral-filled thermosetting resins under exposure to heat and/or moisture. It is typically employed as a blend additive in resin systems that cure via a free radical mechanism (e.g. polyester, acrylic) and in filled or reinforced thermoplastic polymers, including polyolefins and polyurethanes. It is also used to functionalize resins via radical initiated processes - copolymerization or grafting - and to modify surfaces.
Applications:

3-Methacryloxypropyltrimethoxysilane can improve strength as glass fiber size composite in reinforced polyester composites.
Enhance initial and wet strength of reinforced polyester resin composites.
Enhance the wet electrical properties of many mineral-filled and reinforced composites.
Crosslinked acrylic type resins can improve adhesion and durability of adhesives and coatings.

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9.28 Chemical Properties: Colorless transparent liquid

9.29 General Description: 3-(Trimethoxysilyl)propyl methacrylate (TMSPMA) is a hydrophobic monomer. The presence of an additional functional group of acrylate facilitates TMSPMA for grafting polymerization on plastic surfaces. 3-(Trimethoxysilyl)propyl methacrylate undergoes first-order kinetic polymerization to form polyTMSPMA, which is a moisture stable polymer.

10. Computational chemical data

Molecular Weight: 248.3483g/mol
Molecular Formula: C₁₀H₂₀O₅Si
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 248.10800027
Monoisotopic Mass: 248.10800027
Complexity: 229
Rotatable Bond Count: 9
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 54
Heavy Atom Count: 16
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwOAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGhAAAEAADACgoAJCCAAABACIAgDSCAAAAAAAAAAAAAEAAEAABAAAIQACAAAAAAAAIIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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