Diethylene glycol dimethacrylate

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/

Liquid

Colorless liquid, with an ester-like odor; [HSDB]

This chemical does not meet GHS hazard criteria for 7% (19 of 273) of reports.

Warning

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

P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 273 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: 2-Propenoic acid, 2-methyl-, oxydi-2,1-ethanediyl ester

2-Propenoic acid, 2-methyl-, 1,1'-(oxydi-2,1-ethanediyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 2-methyl-, 1,1'-(oxydi-2,1-ethanediyl) 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: 04-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32757

2-Propenoic acid, 2-methyl-, oxydi-2,1-ethanediyl ester: Does not have an individual approval but may be used under an appropriate group standard

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/

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

... 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/

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.

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.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 65(SRC), determined from an measured log Kow(2) and a recommended regression-derived equation(3), indicates that diethylene glycol bis(methacrylate) will have high mobility in soil(SRC). Volatilization of diethylene glycol bis(methacrylate) is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 7.9X10-10 atm-cu m/mole(SRC), using a recommended regression equation(4) nor from dry soil surfaces(SRC) based on an estimated vapor pressure of 0.01 mm Hg(SRC), determined from a fragment constant method(5).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 65(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that diethylene glycol bis(methacrylate) is not expected to adsorb to suspended solids and sediment in water(SRC). Diethylene glycol bis(methacrylate) should not volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 7.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF value of 2(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol bis(methacrylate), which has an estimated vapor pressure of 0.01 mm Hg at 25 °C(2,SRC), may exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol bis(methacrylate) is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone radicals(SRC); the half-lives for these reactions in air are estimated to be about 7 and 12 hours, respectively(3,SRC).

Effluent from a municipal waste treatment plant in Philadelphia, collected in 1977, contained diethylene glycol bis(methacrylate) at concentrations from trace quantities to 10 ppb; this compound was not detected in the influent to the plant suggesting that a polymer entering the treatment plant may be degraded into smaller units(1).

The Koc of diethylene glycol bis(methacrylate) is estimated as approximately 65(SRC), using a measured log Kow of 0.81(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that diethylene glycol bis(methacrylate) has high mobility in soil(SRC).

IN A PHOTOPREPOLYMER PRINTING PLATEMAKING PROCEDURE, CONTACT SENSITIZATION TO DIETHYLENE GLYCOL DIMETHACRYLATE WAS FOUND.

2-Hydroxy-ethyl methacrylate and di- and tetra-ethylene glycol dimethacrylates have produced contact sensitization in workers in the printing industry.

Diethylene glycol bis(methacrylate)'s production and use as a crosslinked acrylic/vinyl resin comonomer(1) and as a comonomer ingredient in the synthesis of dental restoratives(2) may result in its release to the environment through various waste streams(SRC).

An estimated BCF value of 2 was calculated for diethylene glycol bis(methacrylate)(SRC), using a measured log Kow of 0.81(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for diethylene glycol bis(methacrylate) is estimated as 7.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that diethylene glycol bis(methacrylate) will be essentially nonvolatile from water surfaces(2,SRC). Diethylene glycol bis(methacrylate)/s estimated value for vapor pressure, 0.01 mm Hg(3,SRC), indicates that volatilization from dry soil surfaces should not be significant(SRC). Volatilization from moist soil surfaces is not expected based on the Henry's Law constant estimated for this compound(1,SRC).

The rate constant for the vapor-phase reaction of diethylene glycol bis(methacrylate) with photochemically-produced hydroxyl radicals has been estimated as 5.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor-phase reaction of diethylene glycol bis(methacrylate) with ozone has been estimated as 2.3X10-17 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 7X10-11 ozone radicals per cu cm(1,SRC). A base-catalyzed second-order rate constant of 1.4X10-2 l/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 16 and 1.5 years at pH values of 7 and 8, respectively(2,SRC).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 2618 workers (6 of these are female) are potentially exposed to diethylene glycol bis(methacrylate) in the USA(1). Occupational and general exposure may be through inhalation and dermal contact with diethylene glycol bis(methacrylate)(SRC).

Diethylene glycol bis(methacrylate)'s production and use as a crosslinked resin comonomer and as an ingredient in the synthesis of dental restoratives may result in its release to the environment through various waste streams. If released to the atmosphere, diethylene glycol bis(methacrylate) may exist solely in the vapor phase in the ambient atmosphere, based on an estimated vapor pressure of 0.01 mm Hg at 25 °C. Vapor-phase diethylene glycol bis(methacrylate) is degraded in the atmosphere by reaction with both photochemically-produced hydroxyl radicals and ozone radicals with estimated half-lives of 7 and 12 hours, respectively. An estimated Koc value of 65 suggests that diethylene glycol bis(methacrylate will have high mobility in soil. Volatilization from dry soil surfaces is not expected to be important based on the vapor pressure of this compound nor from moist soil surfaces given an estimated Henry's Law constant of 7.9X10-10 atm-cu m/mole. In water, diethylene glycol bis(methacrylate) should not adsorb to sediment or particulate matter based on its Koc value. This compound is not expected to volatilize from water surfaces given its estimated Henry's Law constant. Bioconcentration in aquatic organisms should be low based on an estimated BCF value of 2. The major routes of occupational and general exposure to diethylene glycol bis(methacrylate) should be thorugh oral, respiratory, and dermal contact. (SRC)

Used in dental plastic composites; [HSDB] Used in acrylic resins to make artificial nails; [Adams, p. 443]

Plastic Composites Manufacturing [Category: Industry]

Crosslinked acrylic/vinyl resin comonomer

Used as a comonomer ingredient in the synthesis of dental restoratives.

2023: 75,000 - <500,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 G

(1981) PROBABLY GREATER THAN 2.27X10+6 G

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/

Diethylene glycol + methyl methacrylate (transesterification)

Custom Compounding of Purchased Resins

2-Propenoic acid, 2-methyl-, 1,1'-(oxydi-2,1-ethanediyl) ester: ACTIVE

METHYL METHACRYLATE, AND IN GENERAL THE METHACRYLIC ESTERS, POLYMERIZE MUCH LESS READILY THAN THE CORRESPONDING ORDINARY ACRYLATES. NONE THE LESS, THEY ARE STABILIZED BY ADDING HYDROQUINONE OR PYROGALLOL, PARTICULARLY IN THE PRESENCE OF METALLIC COPPER. /METHACRYLATES/