Description
Most epoxy resins result from polymerization of
bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity
is caused by the low-molecular-weight
monomer BADGE (MW 340 g/mol), the dimer having
a much lower sensitization power. This allergen caused
contact dermatitis in six workers in a plant producing
printed circuits boards made of copper sheets and
fiberglass fabric impregnated with a brominated epoxy
resin. It can also be contained in adhesives.
Description
PPARγ is a ligand-activated transcription factor involved in the regulation of lipid homeostasis and may function as a master regulator of adipogenesis. Ligands for PPARγ include antidiabetic drugs of the thiazolidinedione structural class, 15-deoxy-Δ
12,14-prostaglandin J
2 , and NSAIDS. BADGE is a synthetic compound used in the production of polycarbonate and industrial plastics. This compound was recently identified as an antagonist of PPARγ. BADGE binds to PPARγ with an apparent K
d of 100 μM and interferes with the ability of 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation.
Chemical Properties
Diglycidyl ether of bisphenol A is a colorless to light amber liquid. Slight epoxy odor.
Uses
Bisphenol A derivative. A PPARγ antagonist; exhibits estrogenic activity; An inhibitor of PPARγ and suppressor of TNFα.
Uses
The uniqueness of D.E.R. 332 epoxy resin is reflected in its maximum epoxide equivalent weight of 178. Because of its high purity and lack of polymer factions, samples embedded using D.E.R. 322 have uniform performance, exceptionally low viscosity and color; and improved elevated temperature properties.
Uses
In the manufacture of epoxy resins and polycarbonates for food packaging.
Definition
ChEBI: Bisphenol A diglycidyl ether is a diarylmethane.
Production Methods
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 requires 2 mol of epichlorohydrin for each
mole of the phenol.
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.
General Description
Odorless yellowish brown liquid. Sinks in water.
Air & Water Reactions
Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. Insoluble in water.
Reactivity Profile
Epoxides, such as BISPHENOL A DIGLYCIDYL ETHER RESIN, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.
Health Hazard
Contact with liquid irritates eyes. Prolonged or repeated contact with skin causes irritation and dermatitis.
Fire Hazard
BISPHENOL A DIGLYCIDYL ETHER RESIN is probably combustible.
Biological Activity
PPAR γ pure antagonist with micromolar affinity in 3T3-L1 and 3T3-F442A preadipocyte cells; selective over PPAR δ and PPAR α . Antagonizes the ability of rosiglitazone to stimulate transcriptional activity of PPAR γ . Acts as a PPAR γ agonist in an ECV304 cell line. Also produces PPARg-independent apoptosis of tumor cells via several mechanisms. Active in vivo .
Contact allergens
Most epoxy resins result from polymerization of bisphenol
A diglycidyl ether (BADGE). Delayed hypersensitivity
is caused by the low-molecular-weight
monomer BADGE (Molecular Weight 340 g/mol),
the dimer having much a lower sensitization power.
This allergen caused contact dermatitis in six workers
in a plant producing printed circuits boards made
of copper sheets and fiber glass fabric impregnated
with a brominated epoxy resin. It can be contained in
adhesives.
Biochem/physiol Actions
PPARγ inhibitor that blocks rosiglitazone- and insulin-induced adipogenesis.
Potential Exposure
Diglycidyl ether of bisphenol A is used as a basic active ingredient of epoxy resins.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Carcinogenicity
In summary, a number of carcinogenicity studies involving
the topical application of pure BADGE as well as EPON
Resin 828 and other commercial BADGE-based resins have
been carried out in experimental animals.Viewing the studies
as a whole, the weight of evidence does not show that
BADGE or BADGE-based epoxy resins are carcinogenic.
storage
Color Code—Blue: Health Hazard (skin sensitization): Store in a secure location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a dark, cool,well-ventilated area away from strong oxidizers, acids, and heat. Recommended storage (and pumping)temperature=45-50℃.
Shipping
This material is not covered in DOT’sPerformance-Oriented Packaging Standards. It may,however, be classified as a Combustible Liquid, n.o.s. Thisclass requires no shipping label. It falls in Hazard Class 3[each reference to a Class 3 material is modified to read“COMBUSTIBLE LIQUID” when that material is reclassified in accordance with y173.150 (e) or (f) of this subchapter or has a flash point above 60.5℃/141°F but below93℃/200°F], and Packing Group III. The symbol “D” identifies proper shipping names which are appropriate fordescribing materials for domestic transportation but may beinappropriate for international transportation under the provisions of international regulations (e.g., IMO, ICAO). Analternate proper shipping name may be selected when eitherdomestic or international transportation is involved.
Incompatibilities
Easily oxidized in air; presumed to form unstable and explosive peroxides in storage. Incompatible with strong acids; strong oxidizers.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
References
1) Cuzzocrea?et al. (2004),?Rosiglitazone , a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation; Eur. J. Pharmacol.,?483?79
2) Fehlberg?et al. (2003),?Bisphenol A diglycidyl ether-induced apoptosis involves Bax/Bid-dependent mitochondrial release of apoptosis-inducing factor (AIF), cytochrome c and Smac/DIABLO; Br. J. Pharmacol.,?139?495
3) Chamorro-Garcia?et al.?(2012),?Bisphenol A diglycidyl ether induces adipogenic differentiation of multipotent stromal stem cells through a peroxisome proliferator-activated receptor gamma-independent mechanism; Environ. Health Perspect.,?120?984
4) Duque?et al. (2013),?Pharmacological inhibition of PPARgamma increases osteoblastogenesis and bone mass in male C57BL/6 mice; J. Bone Miner. Res.,?28?639
