メタクリル酸ブチル

Cosmetic ingredients (Butyl Methacrylate) -> CIR (Cosmetic Ingredient Review)

Viscosity controlling

log Kow = 2.88

2.26-3.01

2.6

0.8975 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8936 g/cu cm at 20 °C

Liquid heat capacity: 0.460 BTU/lb-F at 70 °F; Liquid thermal conductivity: 1.048 BTU-in/hr-sq ft-F at 70 °F; Saturated vapor density: 0.00203 lb/cu ft at 70 °F

Relative density (water = 1): 0.9

0.8836 @ 20°C

3.116 cP at 70 °F

1.02 mm²/s at 24 °C

Insoluble (NTP, 1992)

Very soluble in ethyl ether, ethanol

In water, 800 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 0.08 (very poor)

126 °F (NTP, 1992)

54 °C

126 °F (52 °C) (open cup)

50 °C c.c.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1075) of reports.

Warning

H226 (99.8%): Flammable liquid and vapor [Warning Flammable liquids]

Chemical: 2-Propenoic acid, 2-methyl-, butyl ester

Hazard Traits - Carcinogenicity

Directive (EC) No 2/1995 (Repealed by Reg. EC No 1333/2008 (amended))

2-Propenoic acid, 2-methyl-, butyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, butyl 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: 15-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15151

2-Propenoic acid, 2-methyl-, butyl ester: HSNO Approval: HSR001103 Approved with controls

Flammable Liquid

Flammable Liquid

Behavior in Fire: Containers may explode. (USCG, 1999)

Behavior in Fire: Containers may explode due to polymerization. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 50 °C explosive vapour/air mixtures may be formed.

Inhalation may cause nausea because of offensive odor. Contact with liquid causes irritation of skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

Inhalation may cause nausea because of offensive odor. Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

A skin, eye, and respiratory tract irritant; May cause skin sensitization; [ICSC] An irritant; May cause skin sensitization; [MSDSonline] Danger of skin sensitization; [MAK] n-Butyl methacrylate, stabilized (UN2227) has warning of explosive polymerization; [ERG 2016] See ACRYLIC RESINS (MONOMERS).

Acrylates and Acrylic Acids

Acrylates and Acrylic Acids

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:

Use foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

INHALATION: Remove to fresh air, give oxygen or artificial respiration as required.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Foam, dry chemical, carbon dioxide.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Butyl methacrylate, combustible liquid, N.O.S.,and n-butyl methacrylate, stabilized/

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/

Protect against physical damage. Before entering confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. Outside or detached storage is preferred ... Store in tightly closed containers in a cool, well ventilated area away from incompatible materials ..., light, and heat. Butyl methacrylate should be kept refrigerated and inhibited with 10 ppm hydroquinone monomethylether. Metal containers involving the transfer of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard.

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.

Spill Handling: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Ventilate area of spill or leak after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious); polymerization hazard]:

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.

Options for disposal of waste or spilled material: large quantities can be returned to the manufacturer for recycle. Small quantities may be incinerated under controlled conditions in incinerators suitable for methacrylates. Combustion products include carbon monoxide, carbon dioxide, and water. The product must be disposed of as special waste in accordance with regulations for special waste.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

LC50; Species: Oryzias latipes (Medaka); Conditions: semi-static; Concentration: 5.57 mg/L for 24 hr

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: flow-through; Concentration: 11 mg/L for 96 hr

LC50; Species: Carassius auratus (goldfish); Conditions: static; Concentration: 112 mg/L for 72 hr

EC50; Species: Brachionus calyciflorus (Rotifer, age <2 hr); Conditions: freshwater, static, 25 °C, pH 7.5; Concentration: 128 mg/L for 48 hr (95% confidence interval: 640-193 mg/L); Effect: decreased reproduction, progeny counts/numbers />99.5% purity/

For more Ecotoxicity Values (Complete) data for n-Butyl methacrylate (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that n-butyl methacrylate is expected to have high mobility in soil(SRC). Volatilization of n-butyl methacrylate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 2.12 mm Hg(3), and water solubility, 800 mg/L(4). n-Butyl methacrylate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 88% of the theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 55(SRC), determined from a structure estimation method(2), indicates that n-butyl methacrylate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.0X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 2.12 mm Hg(4), and water solubility, 800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.6 hours and 5.4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 37(SRC), from its log Kow of 2.88(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 80 and 8 years at pHs 7 and 8, respectively(9). Utilizing the Japanese MITI test, 88% of the theoretical BOD was reached in 4 weeks(10) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyl methacrylate, which has a vapor pressure of 2.12 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyl 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 17 hours(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase n-butyl methacrylate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Butyl 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).

Based on available data, the CIR Expert Panel concluded that ... Butyl Methacrylate is safe as used in nail enhancement products when skin contact is avoided. Products containing these ingredients should be accompanied with directions to avoid skin contact, because of the sensitizing potential of Methacrylates.

Safe for use in cosmetics, with qualifications

Sore throat. Cough. Shortness of breath.

Redness.

Watering of the eyes. Redness. Pain.

Cough. Sore throat. Abdominal cramps. Nausea.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of n-butyl methacrylate can be estimated to be 55(SRC). According to a classification scheme(2), this estimated Koc value suggests that n-butyl acrylate is expected to have high mobility in soil.

/HUMAN EXPOSURE STUDIES/ ... In 542 dermatitis patients given covered patch tests with 1% EMA or 1% nBMA in petrolatum, one individual responded to EMA and another to both EMA and nBMA ... No reactions were seen in 22 contact dermatitis patients given 24-hr covered patch tests with esters within the category at a concentration of 1% in petrolatum ... The contact dermatitis of many of the tested individuals was attributed to (meth)acrylate exposure ... The prevalence of positive clinical challenge responses /was reported/ in dental clinicians that had been referred with dermatitis and suspected of having allergy to (meth)acrylates as 1.2% (51/4221) for MMA, 0.7% (16/2323) for EMA and 0.3% (1/347) for BMA ... The prevalence in a similar, pre-selected clinical cohort /was reported/ as 0.8% (9/1161) for MMA and 0.3% (2/625) for EMA ... The prevalence of positive clinical challenge tests in patients referred with dermatitis with previous contact with (meth)acrylates was reported as 4.8% (17/352) for MMA, 4.4% (11/246) for EMA and 0.6% (2/331) for BMA ... Cross-reactivity with common acrylates (i.e. between methacrylates and acrylates) has not been observed ... and methacrylic acid, the common hydrolysis product for these methacrylate esters, is not a contact allergen ... /Short chain alkyl-methacrylate esters/

/HUMAN EXPOSURE STUDIES/ ... In 542 dermatitis patients given covered patch tests with 1% EMA or 1% nBMA in petrolatum, one individual responded to EMA and another to both EMA and nBMA ... No reactions were seen in 22 contact dermatitis patients given 24-hr covered patch tests with esters within the category at a concentration of 1% in petrolatum ... The contact dermatitis of many of the tested individuals was attributed to (meth)acrylate exposure ... The prevalence of positive clinical challenge responses /was reported/ in dental clinicians that had been referred with dermatitis and suspected of having allergy to (meth)acrylates as 1.2% (51/4221) for MMA, 0.7% (16/2323) for EMA and 0.3% (1/347) for BMA ... The prevalence in a similar, pre-selected clinical cohort /was reported/ as 0.8% (9/1161) for MMA and 0.3% (2/625) for EMA ... The prevalence of positive clinical challenge tests in patients referred with dermatitis with previous contact with (meth)acrylates was reported as 4.8% (17/352) for MMA, 4.4% (11/246) for EMA and 0.6% (2/331) for BMA ... Cross-reactivity with common acrylates (i.e. between methacrylates and acrylates) has not been observed ... and methacrylic acid, the common hydrolysis product for these methacrylate esters, is not a contact allergen ... /Short chain alkyl-methacrylate esters/

/SIGNS AND SYMPTOMS/ Short Term Exposure: Contact can irritate the eyes and skin. Inhalation can irritate the respiratory tract with coughing, wheezing, and/or shortness of breath. Higher exposures can cause pulmonary edema, a medical emergency that can be delayed for several hours. This can cause death. Long Term Exposure: Butyl methacrylate may cause skin allergy.

/SIGNS AND SYMPTOMS/ Although there are notable exceptions to the rule, esters of organic acids are generally of low toxicity. Nonspecific irritative effects are commonly associated with the presence of a double bond in these esters which, if saturated, would be essentially harmless. Conjunctivitis and upper airway symptoms may occur and pulmonary edema is possible in case of massive over-exposure. These irritating unsaturated esters include the acrylates, methacrylates ... /Esters/

For more Human Toxicity Excerpts (Complete) data for n-Butyl methacrylate (10 total), please visit the HSDB record page.

n-Butyl methacrylate's production and use in dental technology, acrylic surface coatings(1), as a monomer for resins, solvent coatings, adhesives, oil additives, in emulsions for textiles, and in leather and paper finishing(2) may result in its release to the environment through various waste streams(SRC).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Butyl methacrylate is included on this list. Effective date 4/13/89; Sunset date: 12/19/95.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

The cause of the lacrimatory action of esters containing unsaturated acids is undoubtedly the result of some mechanism ... in which the neighboring keto group has a polarizing effect on double bond, making it capable of adding /to/ nucleophilic agents such as SH groups /from certain enzymes/. /Unsaturated aliphatic esters/

n-BMA, like MMA, is rapidly metabolized by body carboxylesterases ... Hydrolysis of n-BMA yields methacrylic acid and n-butanol which are further metabolized by physiological pathways, methacroyl CoA being a physiological substrate of the valine pathway.

Butyl methacrylate interacts with cytochrome P450 to form type 1 spectral complex.

In vitro hydrolysis of n-BMA was studied using a porcine liver esterase preparation. The Michaelis Menten constant, Km, and Vmax were on the order of 30 uM and 1.49 nmol/min, indicating that n-BMA is readily hydrolyzed by liver esterases. When compared to other methacrylic acid esters, increased chain length of the ester increased substrate affinity but decreased the turnover of the enzymatic hydrolysis.

Acrylates and methacrylates are detoxified predominantly via conjugation with glutathione via the Michael addition reaction or glutathione-S-transferase. They are also likely to be hydrolyzed via carboxylesterases. The lower molecular weight esters are rapidly metabolized and eliminated, therefore, will not likely cause cumulative toxicity.

For more Metabolism/Metabolites (Complete) data for n-Butyl methacrylate (7 total), please visit the HSDB record page.

Recent studies have confirmed that alkyl-methacrylate esters are rapidly hydrolyzed by ubiquitous carboxylesterases ... First pass (local) hydrolysis of the parent ester has been shown to be significant for all routes of exposure. For example, no parent ester can be measured systemically following skin exposure to EMA and larger esters, as the lower rate of absorption for these esters is within the metabolic capacity of the skin ... Parent ester will also be effectively hydrolyzed within the G.I. tract and within the tissues of the upper respiratory tract (particularly the olfactory tissue). Systemically absorbed parent ester will be effectively removed during the first pass through the liver ... resulting in their relatively rapid elimination from the body ... /Short chain alkyl-methacrylate esters/

CIR ingredient: Butyl Methacrylate

Used as a monomer for resins, and in coatings, adhesives, and oil additives; Also used in emulsions for textiles, for leather and paper finishing, and to make contact lenses; [HSDB]

Pulp and Paper Processing [Category: Industry]

Monomer for resins, solvent coatings, adhesives, oil additives; emulsions for textiles; leather and paper finishing.

Butyl methacrylate monomer & polymer are used in dental technology, as components in oil dispersible pesticides & as copolymers, for example, in paraffin embedding media; monomer also used for the manufacture of contact lenses and for acrylic surface coatings.

2023: 10,000,000 - <50,000,000 lb

(1972) > 4.54 X 10+5 g

(1975) > 4.54 X 10+5 g

(1993) 2.61 X 10+7 kg (2.61 X 10+10 g)

2-Propenoic acid, 2-methyl-, butyl 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).

For more U.S. Production (Complete) data for n-Butyl methacrylate (6 total), please visit the HSDB record page.

Reaction of methacrylic acid or methyl methacrylate with butanol.

The methacrylates can be synthesized by catalytic oxidation of isobutylene and subsequent esterification with the appropriate alcohol, or by reacting acetone with hydrocyanic acid and subsequent esterification in sulfuric acid with the appropriate alcohol. /Methacrylic esters/

Technical grade (inhibited)

Inhibitor of polymerization: 9-15 ppm monomethyl ether or 90-120 ppm hydroquinone.

Fragrance Ingredients

Cosmetics -> Viscosity controlling

Wholesale and Retail Trade

2-Propenoic acid, 2-methyl-, butyl ester: ACTIVE

Alkyl mercury compounds have been used as seed disinfectants and for fungicides. They have also been used in organic synthesis. /Mercury alkyl compounds/

Methyl methacrylate, and 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/