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Home > Encyclopedia > Diethylene glycol, dimethacrylate

Diethylene glycol, dimethacrylate

Diethylene glycol, dimethacrylate structure

Diethylene glycol, dimethacrylate 

structure
  • CAS No:

    2358-84-1

  • Formula:

    C12H18O5

  • Chemical Name:

    Diethylene glycol, dimethacrylate

  • Synonyms:

    2-Propenoic acid,2-methyl-,1,1′-(oxydi-2,1-ethanediyl) ester;Methacrylic acid,oxydiethylene ester;2-Propenoic acid,2-methyl-,oxydi-2,1-ethanediyl ester;Methacrylic acid,diester with diethylene glycol;Diethylene glycol,dimethacrylate;Diethylene glycol bis(methacrylate);Oxydiethylene methacrylate;DGM 2;TGM 2;NK Ester 2G;Blemmer PDE 100;2,2′-Oxybisethanol dimethacrylate;2,2′-Oxydiethyl dimethacrylate;SR 231;2G;Light Ester 2EG;PDE 100;SR 231E;Sartomer SR 231;EM 329;Bisomer DEGDMA HI;2-[2-(2-Methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate;67957-99-7;76611-52-4;77302-64-8;129011-76-3;171428-77-6;1081804-95-6;1565841-57-7

  • Categories:

    Cosmetic Ingredient  >  Film Forming

Description

Clear Colourless Oil


Liquid

Diethylene glycol, dimethacrylate Basic Attributes

242.268

242.27

219-099-9

R42PUI926F

DTXSID8044882

Colorless liquid

2916190090

Characteristics

61.83000

2.17

Liquid

1.056 g/cm3 @ Temp: 20 °C

<25 °C

120-125 °C @ Press: 2.0 Torr

138.7±21.0 °C

1.453

Temp during storage must be kept low to minimize formation of peroxides and other oxidation products. ... Storage temp below 30 deg 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 me

Ester-like odor

Safety Information

UN 3082 9/PG 3

1

R36/37/38

S26-S36

Xi

P261-P305 + P351 + P338

H315-H319-H335

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.

|Warning|H315 (17.94%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 243 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SUITABLE PROTECTIVE CLOTHING & SELF-CONTAINED RESP PROTECTIVE APPARATUS SHOULD BE AVAILABLE FOR USE OF THOSE WHO MAY HAVE TO RESCUE PERSONS OVERCOME BY FUMES. /ACRYLIC ACID & DERIVATIVES/

... 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.

Methacrylates ... produce slight to moderate skin and eye irritation ... depending upon volatility, these materials also may be sensory irritants. /Methacrylic acid & derivatives/

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).

Toxicity

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).

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).

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).

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 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).

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).

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).

Drug Information

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.

DGM 2

Diethylene glycol, dimethacrylate Use and Manufacturing

Methods of Manufacturing

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)

Uses

Esters of acrylic acid and methacrylic acid, more commonly known as acrylates and methacrylates are key raw materials in the coatings and printing industry, and in food packaging.


Intermediates


Adhesives and sealants

Production

(1979) PROBABLY GREATER THAN 4.54X10+6 G|(1981) PROBABLY GREATER THAN 2.27X10+6 G

Adhesive manufacturing|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/

Thin-layer chromatography (TLC), polarography, and spectrometry are used for soln measurements. Methacrylates in air have been analyzed by TLC, polarography, and colorimetry. Polarography has been used for determination of any residual monomer in the polymer. A variety of spectroscopic techniques, eg, NMR, IR, and Raman spectroscopy also have been used, particularly for analysis of surgical cements and dental restorative resins. /Methacrylic acid & derivatives/|THE ELECTRON-IMPACT AND METHANE CHEM-IONIZATION MASS SPECTRA OF SELECTED ACRYLATE AND METHACRYLATE MONOMERS, INCLUDING DIETHYLENE GLYCOL DIMETHYACRYLATE, COMMONLY USED IN DENTAL MATERIALS ARE REPORTED AND DISCUSSED. THE TWO IONIZATION MODES COMPLEMENT EACH OTHER, AND TOGETHER THE MASS SPECTRA OFFER ADEQUATE INFORMATION FOR IDENTIFICATION PURPOSES. THE APPLICATION OF THE MASS SPECTRAL METHOD IS DEMONSTRATED ON RESIN-BASED DENTAL MATERIALS WITH IDENTIFICATION OF THE MONOMER CONTENT.

Computed Properties

Molecular Weight:242.27
XLogP3:1.8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:242.11542367
Monoisotopic Mass:242.11542367
Topological Polar Surface Area:61.8
Heavy Atom Count:17
Complexity:276
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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