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Product Safety Assessment: Bisphenol A Diglycidyl Ether

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Product Overview
Manufacture of Product
Product Description
Product Uses
Exposure Potential
Health Information
Environmental Information
Physical Hazard Information
Regulatory Information
Additional Information
References

Names

CAS No. 1675-54-3	BADGE	2,2-bis(4-hydroxyphenyl)propane
PM Ref. No. 13510	bis(2,3-epoxypropyl)ether	2,2-bis(p-2,3-epoxypropoxy) phenyl)propane
Ref. No. 39700	Diglycidyl ether of bisphenol A	4,4'-Isopropylidenediphenol diglycidyl ether
Bisphenol A diglycidyl ether	DGEBPA	D.E.R. * (Dow Epoxy Resins)

Product Overview

• For roughly 40 years, bisphenol A diglycidyl ether (BADGE) has been used commercially as a raw material. BADGE is the primary chemical building block for the broad spectrum of materials referred to generally as epoxy resins. Depending on the end-use application, BADGE is used without additives, or in solutions including various solvents. Epoxy resins sold by Dow vary widely in some physical properties such as molecular weight, solvent type and specific composition, but they rely on the same basic chemistry. See Process.
• Major uses for Dow epoxy resins are adhesives, potting and encapsulating media and coatings.¹ Some BADGE-based materials, when properly formulated and cured, are approved for food contact applications such as can coatings.² See Product Uses.
• Because of the variety of formulations in which epoxy resins are sold, users should consult the Safety Data Sheet for hazard information specific to the product being used. Broadly speaking, direct contact with these materials should be avoided. Although BADGE is not acutely irritating to the skin, it is capable of causing skin sensitization in some individuals.³ See Health Information
• Dow epoxy resins are organic products and will burn when sufficient heat and oxygen are supplied. D.E.R.* solution epoxy resins, in particular, require precautions against fire and explosion hazards because of the presence of flammable solvents. The thermal decomposition products of epoxy resins should be treated as potentially hazardous substances.⁴ See Physical Hazard Information.
• Occupational and consumer exposure is dependent upon the conditions under which BADGE is used. See Exposure Potential.
• BADGE is moderately toxic to aquatic organisms. It also has a moderate bioconcentration potential.⁵ See Environmental Information.

Manufacture of Product

• Capacity – Dow is a leading manufacturer of epoxy products and intermediates, producing and marketing more than 100 epoxy products. Dow has epoxy plants in the U.S., Brazil, Germany (2), Italy, Japan, China and the Republic of Korea. Annual global production of BADGE was estimated to be 2.1 billion pounds (957 thousand metric tons) in 2003.⁶ 
• Process – BADGE is produced by reacting epichlorohydrin with bisphenol A as shown below.

 

The reaction between bisphenol A and epichlorohydrin can be controlled to produce different molecular weights.  Low molecular weight molecules tend to be liquids and higher molecular weight molecules tend to be more viscous liquids or solids. The molecule below shows the structure of higher molecular weight BADGE, designating the bracketed section as the basic chemical structure with epoxide rings at the end. The small ‘n’ indicates that products could have any number of those units placed between the end epoxide rings.

Product Description

BADGE is a colorless liquid with a low flash point that is insoluble in water (0.5 mg/l at 20ºC).  It has a low vapor pressure and mild odor.⁷

Some Dow products are solutions or mixtures of BADGE with diluents, solvents and/or modifiers used to create products for a variety of performance needs. These mixtures will have flash points, solubilities, odors and hazards that are unique to the specific product formulation. Because of the diversity of products that contain BADGE, the information included in this risk profile broadly applies to BADGE and should only be used along with the Safety Data Sheet and Product Information for the specific product of interest. 

Product Uses

Epoxy surface coatings are among the most widely used industrial finishes and provide superior adhesion, flexibility and corrosion resistance when applied to metallic substrates.⁸  Epoxy resins are used with various curing agents, diluents, and modifiers to create products with an almost unlimited range and variety of performance properties.⁹ BADGE products are used in a variety of epoxy markets (see pie chart¹⁰) and applications, some of which are listed below:¹¹ 

• Adhesives
• Civil Engineering
• Composites
• Electrical Laminates
• Electrical Castings / Potting and Encapsulation / Tooling
• Industrial Coatings
  • Automotive
  • Can and coil
  • Marine and protective
  • UV / photocure
  • Powder

Exposure Potential

Because of the potential health and flammability risks associated with some BADGE products, precautions should be taken to minimize potential harm to people, pets and the environment. Such precautions include using appropriate personal protective equipment when handling these materials and following all label instructions and warnings on consumer products. Based on the most common uses for BADGE, the public could be exposed through:

• Workplace exposure – Exposure can occur either in a BADGE manufacturing facility or in the various industrial facilities that use BADGE or epoxy resins. Broadly speaking, direct contact with these materials should be avoided. This is best accomplished through the use of a “closed” system. However, because customer/user needs vary so widely, such systems must be individually designed to meet the specific needs of each plant site.¹² Each manufacturing and industrial facility should have appropriate work processes and safety equipment policies in place to limit BADGE exposure. Good industrial hygiene practices minimize the risk of exposure.
• Consumer exposure to products containing BADGE – Although Dow does not sell BADGE for consumer use, BADGE-based products may be used in consumer and construction products manufactured or sold by distributors, packagers or formulators. For example, adhesives and protective coatings may contain BADGE as an ingredient. It is important to read and follow the instructions for use on the container because these instructions help prevent injury. It is also important to keep all chemical products out of the reach of children. See Health Information.
• Environmental releases¹³ – In the event of a spill, the focus should be on containing the spill to prevent contamination of soil, surface or ground water. If a BADGE-based material does reach soil and/or surface water, it can pose a flammability and health concern. Spills can be cleaned up by applying an absorbent or a high surface-area material such as sand.  The mass can then be shoveled into a suitable container for proper disposal.  The residue on the floor or dock should be removed with steam or hot soapy water. All ignition sources should be removed from the area, proper grounding and bonding techniques used and proper protective equipment worn. See Environmental, Health and Physical Hazard Information.
• Large release – Industrial spills or releases are infrequent and are generally contained. If a large spill does occur, the material is captured, collected and re-processed, or disposed of according to federal, state/provincial or local regulations. Emergency personnel should wear proper protective equipment and follow emergency procedures carefully. All ignition sources should be removed from the area, proper grounding and bonding techniques used. If a fire does occur, the decomposition products should be treated as potentially hazardous substances and appropriate precautions should be taken, including the wearing of full protective clothing. See Environmental, Health and Physical Hazard Information.

Health Information

Because of the diversity of BADGE-based materials, the health effects associated with exposure to BADGE depend on the other components in the mixture, the exposure level and the duration of the exposure.

BADGE-based materials can cause eye irritation and minor skin irritation. Although the potential for skin irritation is slight, all skin contact with Dow epoxy resins should be avoided. Lower molecular weight BADGE-based materials can cause allergic skin reactions after repeated exposures. Some resins were found to be mild sensitizers according to animal tests, but were not found to have sensitizing potential when patch tested in humans. However, susceptibility to skin irritation and sensitization varies from person to person.¹⁴

Inhalation of liquid and solid epoxy resin vapors is unlikely because of their low volatility at room temperature. However, solid resins are prone to create dusts. Although there is no indication that these dusts pose an inhalation hazard, control of dusts through adequate ventilation and good housekeeping practices is recommended.¹⁵

Liquid epoxy resins and some solid epoxy resins have been tested for genetic toxicity (carcinogenic and mutagenic properties). Looking at all the studies together, the weight of evidence does not show that epoxy resins are carcinogenic.  The International Agency for Research on Cancer (IARC) has determined that there is limited evidence for the carcinogenicity of BADGE in experimental animals.¹⁶ IARC has concluded that this chemical is not classifiable as to its carcinogenicity to humans (Group 3).  A 2004 opinion published by the Scientific Panel on Food Additives concluded that BADGE and its chlorohydrins do not raise concern for carcinogenicity and genotoxicity in vivo, respectively.¹⁷

For more information on the health hazards of epoxy resins and recommended protective equipment, please consult the Safety Data Sheet. 

Environmental Information 

Properties of BADGE-based materials vary by product. Please consult the Safety Data Sheet for the product of interest.  Environmental parameters can vary significantly from product to product.

BADGE is poorly soluble in water, has very low vapor pressure, and has a moderately high log K_ow.  These properties dictate that the material has low potential to volatilize from water to air, and moderate potential for adsorption to soil and sediments.  If unintentionally released to water, a significant fraction of the material will adsorb to sediment.  When released to soil, the material will be primarily adsorbed to soil particles.  Slow biodegradation of the material is expected to occur in these environmental compartments.¹⁸

Any circumstances where BADGE might unintentionally enter the environment is considered low in risk. ¹⁹  BADGE exhibits moderate bioconcentration potential.  It is not considered as “readily biodegradable;” however this does not necessarily mean that a specific product is not biodegradable under environmental conditions.²⁰

Physical Hazard Information ²¹

Properties of BADGE-based materials vary by product.  Please consult the Safety Data Sheet for the product of interest.  Physical properties can vary significantly from product to product.  For example, the range of flash points recorded for some Dow epoxy resins range from -4 to 495º F (-20 to 257ºC). 

Materials with lower flash points are more flammable. All D.E.R.* products are organic and will burn when sufficient heat and oxygen are supplied.  D.E.R. solution epoxy resins, in particular, require precautions against fire and explosion hazards because of the presence of flammable solvents. 

When epoxy resins burn, they release toxic by-products.  For this reason, the breathing of fumes, smoke and gas given off during burning must be avoided.  The primary by-products expected during incomplete pyrolysis or combustion of epoxy resins include phenolics, carbon monoxide and water.  The D.E.R. 500 resin series also generates brominated compounds, such as hydrogen bromide.  Thus, the thermal decomposition products of epoxy resins should be treated as potentially hazardous substances and appropriate precautions should be taken, including the wearing of full protective clothing.

D.E.R. liquid epoxy resins have high boiling points and relatively low vapor pressures.  However, under special conditions, explosive mixtures can occur.  Epoxy resins also contain the reactive oxirane ring structure commonly called “epoxy.”  As the molecular weight of the resins increases, another reactive site – the hydroxyl group – is introduced.  Through these two sites, epoxy resins react spontaneously with carboxylic acids, amines, amides, and mercaptans (thiols).  Epoxy resins react slowly with anhydrides, alcohols, phenols and other epoxy resins. All of these materials are used commercially to cure epoxy resins.  Because epoxy reactions generate heat (are exothermic), take care to control the materials that come into contact with BADGE and to avoid excessive exotherms.

Regulatory Information

Regulations may exist that govern the manufacture, sale, transportation, use and/or disposal or BADGE.  These regulations may vary by city, state, country or geographic region.  Information may be found by consulting the relevant Safety Data Sheet or Contact Us.

Additional Information

• Safety Data Sheet
• Dow’s Epoxy Technical Information page
• Society of Plastics Industry information site
• Dow’s Epoxy web site
• Dow Customer Information Group, 1-800-447-4369

 For more business information about BADGE and epoxy resins, visit Dow’s Epoxy web site.

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References

®™* Trademark of The Dow Chemical Company ("Dow") or an affiliated company of Dow

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