2,2'-[(1-Methylethyliden)bis(4,1-phenylenoxymethylen)]bisoxiran

Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

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.

Safety cans should be used for storing flammable solvents. /Epoxy resins/

Seperated from strong oxidants.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.

Mixing of volatile materials should always be done in a well ventilated area and precautions should be taken to avoid splashing of materials on hands and face. /Epoxy compounds/

Adequate ventilation should be supplied to work area. In some operations, exhaust ventilation may be necessary to remove excessive concentrations of vapors of curing agent or diluent. /Epoxy resins/

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.

Because of the persistence of dermatitis and the possibility of sensitization, preventive measures are ... important /and/ requires ... provision of adequate facilities for removing the material periodically, together with a designated cleanup period prior to "break" and "quitting" times ... When possible, only persons with no history of allergic conditions or eczematous eruptions should be selected for epoxy resins applications ... Bench and floor areas should be protected with disposable paper. /Epoxy resins/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1800(SRC), determined from a structure estimation method(2), indicates that bisphenol A diglycidyl ether is expected to have low mobility in soil(SRC). Volatilization of bisphenol A diglycidyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.4X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(4) through neutral, acid, or base-mediated reactions(5). Bisphenol A diglycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-7 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,800(SRC), determined from a structure estimation method(2), indicates that bisphenol A diglycidyl ether is not 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 4.4X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 180(SRC), from an estimated log Kow of 3.8(6) suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(7) through neutral, acid, or base-mediated reactions(8). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(8). While data specific to bisphenol A diglycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(7). Biodegradation data were not available(SRC, 2006).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bisphenol A diglycidyl ether, which has an estimated vapor pressure of 1.1X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bisphenol A diglycidyl ether 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 5.8 hrs(SRC), calculated from its rate constant of 6.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase bisphenol A diglycidyl ether may be removed from the air by wet or dry deposition(SRC).

Dry skin. Redness.

Redness. Pain.

Dizziness. Drowsiness.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of bisphenol A diglycidyl ether can be estimated to be 1800(SRC). According to a classification scheme(2), this estimated Koc value suggests that bisphenol A diglycidyl ether is expected to have low mobility in soil(SRC).

The frequency of chromosomal aberrations was determined in rat liver cells exposed in vitro to bisphenol A diglycidyl ether (DGEBA). Slide cultures were exposed to culture medium containing test article at 3.75, 7.5 or 15 ug/ml for 24 hours. An increase in the percentage of cells with chromatid gaps, an increase in chromatid exchange figures, and a single cell with multiple chromatid aberrations was observed at a concentration of 15 ug/ml. In a preliminary cytotoxicity test, exposure to DGEBA at 30 ug/ml resulted in 50% inhibition of cell growth.

The frequency of micronuclei formation was determined in the bone marrow cells of groups of ten B6D2F1 female mice administered 1000 mg/kg bisphenol A diglycidyl ether (in corn oil) by oral gavage 1x daily for 5 days. The test article did not significantly increase (Dunnett's t-test, p > 0.1) micronuclei formation compared to controls under these conditions. The toxic effects of bisphenol A diglycidyl ether in mice at this dose level were not reported.

The mutagenicity of 2,2-bis(p-(2,3-epoxypropyloxy)phenyl)propane (EPOPP) was evaluated in the bacteria Salmonella tester strains TA1535 and TA1538, and E.coli WP2 and WP2uvrA, and the yeast Saccharomyces cerevisiae tester strain JD1, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, EPOPP was tested for mutagenicity at concentrations up to 200 ug/plate using the plate incorporation assay. EPOPP caused a reproducible positive response (>2.5 frequency of mutations for controls) with activation in bacterial tester strain TA1535 at 2, 20, 200, and 2000 and 2000 ug/plate and in TA1537 at 200 and 2000 ug/plate. EPOPP did not cause a reproducible positive response in any of the other bacterial or yeast tester strains, either with or without metabolic activation.

The mutagenicity of 2,2-bis(p-(2,3-epoxypropyloxy)phenyl)propane (EPOPP) was evaluated in Salmonella tester strains TA1535 and TA1538, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, EPOPP was tested for mutagenicity at concentrations up to 2000 ug/plate using the plate incorporation assay. EPOPP caused a reproducible positive response with activation in bacterial tester strain TA1535 at 20, 500 and 2000 ug/plate and in TA1538 at 2000 ug/plate.

For more TSCA Test Submissions (Complete) data for BISPHENOL A DIGLYCIDYL ETHER (12 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ Twenty-three ... individuals patch tested with resins of average mol wt 624 and mol wt 908 did not experience sensitization, and 7 of these individuals patch tested with a resin of average mol wt 1192 did not react ... 8 patients tested with commercial mixtures of epoxy resins with average mol wt 1280 and mol wt 1850 reacted to these mixtures, which contained the mol wt 340 oligomer as determined by gel permeation chromatography. /It was/ concluded that the mol wt 340 oligomer is the component responsible for contact allergy to epoxy resins in humans. These results in humans are consistent with the absence of skin sensitization in guinea pigs for higher-molecular-weight resins.

/SIGNS AND SYMPTOMS/ Diglycidyl ether of bisphenol A, an oligomeric resin, is moderately toxic. Medium mol wt cmpd (liquids) cause CNS depression from large doses. High skin irritancy. Sensitization. Precipitation of asthmatic attacks. /Oligomeric resin; From Table/

/SIGNS AND SYMPTOMS/ Sensitization may follow the initial contact, resulting in the development of a papular, vesicular eczema. This is accompanied by considerable itching, and extension into areas beyond the point of original contact. Only occasionally, areas other than the backs of the hands, the forearms, the face, and the neck are involved ... The lesion usually subsides in 10-14 days. However, it may recur on further contact. If the worker is not withdrawn from contact, the dermatitis usually persists for longer periods, but usually does not become more intense. The lesions may assume a brownish color, and scaling is frequently noted.

/CASE REPORTS/ In most cases, it is not possible to separate effects of uncured epoxy resin from that of curing agent (particularly amines). ... 43% of all workers in epoxy resin industries studied had dermatitis ... There are no reports of dermatitis or sensitization from cured epoxy resins. /Epoxy resins/

For more Human Toxicity Excerpts (Complete) data for BISPHENOL A DIGLYCIDYL ETHER (7 total), please visit the HSDB record page.

Bisphenol A diglycidyl ether's production and use as a major component in epoxy resin(1), a sealer or binder(2), and in the lacquer coating for food and beverage cans(3) may result in its release to the environment through various waste streams(SRC). It is used in the manufacture of lacquers for coating inside of food and beverage cans(2).

Bisphenol A diglycidyl ether (Araldite)

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 47: (1989) Some Organic Solvents, Resin Monomers and Related Compounds, Pigments and Occupational Exposures in Paint Manufacture and Painting

1999

1998

An estimated BCF of 180 was calculated for bisphenol A diglycidyl ether(SRC), using an estimated log Kow of 3.8(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

The Henry's Law constant for bisphenol A diglycidyl ether is estimated as 4.4X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bisphenol A diglycidyl ether is expected to be essentially nonvolatile from water surfaces(2). Bisphenol A diglycidyl ether's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Bisphenol A diglycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-7 mm Hg(SRC), determined from a fragment constant method(3).

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. Oxirane, 2,2'-((1-methylethylidene)bis(4,1-phenyleneoxymethylene))bis- is included on this list.

Bisphenol A glycidyl ether (BADGE) has a molecular weight of 340 g/mole. It is the basic building block of most epoxy resins. The dimer has less potential for skin sensitization. [Kanerva, p. 1759] Used to make epoxy resins and polycarbonates for food packaging; [Merck Index] An epoxy resin used in adhesives and fiberglassing; [REPROTOX] Used to make castings and pottings, in light weight foams, and as binders in making laminates of paper, polyester cloth, fiberglass cloth, and wood sheets; [NTP]

Molding and Core Making [Category: Foundry]

.. sealing, encapsulating, making castings and pottings, and formulating lightweight foams. Castings may be used for patterns, molds, and finished products. These resins are used as binders in the preparation of laminates of paper, polyester cloth, fiberglass cloth, and wood sheets. The epoxy resins have outstanding adhesive properties. /Diglycidyl ethers of bisphenol A/

Major component of liquid epoxy resins

...In the manufacture of lacquers for coating inside of food and beverage cans.

2023: 25,000,000 - <40,000,000 lb

This chemical is listed as a High Production Volume (HPV) (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).

(1986) >1 million-10 million pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane, 2,2'-

(1990) >1 million-10 million pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane, 2,2'-

(1994) >50 million-100 million pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Oxirane, 2,2'-

For more U.S. Production (Complete) data for BISPHENOL A DIGLYCIDYL ETHER (6 total), please visit the HSDB record page.

Reaction of epichlorohydrin and bisphenol A in presence of sodium hydroxide

Produced as an unisolated component of liquid epoxy resins

The synthesis of the basic epoxy resin molecule involves the reaction of epichlorohydrin with bisphenol A, the latter requiring two basic intermediates for synthesis, acetone and phenol. Theoretically, the production of the bisphenol A diglycidyl ether (BADGE) requires 2 mol of epichlorohydrin for each mole of the phenol.

A major component of Aradite GY 250, an epoxy resin

A mixture of monomer, dimer, trimer, and tetramer.

Trade Names: Various trademarks of epoxy resins based on bisphenol A diglycidyl ether are EPON resin series, DER series, Epotuff series, Araldite series, EPI-Rez series and the ERL Bakelite epoxy series.

The resins are usually mixtures and may contain homologues of higher weight, isomers, branched-chain homologues, and occasionally, monoglycidyl ethers.

Paint and Coating Manufacturing

Oxirane, 2,2'-[(1-methylethylidene)bis(4,1-phenyleneoxymethylene)]bis-: ACTIVE

... component of BOWEN, a dental composite.

Epoxy resins of higher molecular weight are obtained by reducing the epichlorohydrin/bisphenol A ratio. This reaction involves consumption of the initial epoxy groups in the epichlorohydrin and of some of the groups formed by dehydrohalogenation.