Diglycidyl ether of bisphenol A

Bisphenol A diglycidyl ether

Names
IUPAC name 2-[[4-[2-[4-(Oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane
Other names Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
Identifiers
CAS Number	1675-54-3 Y
3D model (JSmol)	Interactive image
Abbreviations	BADGE; DGEBA
ChemSpider	2199 N
ECHA InfoCard	100.015.294
EC Number	216-823-5
KEGG	C14348 N
MeSH	C019273
PubChem CID	2286
InChI InChI=1S/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3 N Key: LCFVJGUPQDGYKZ-UHFFFAOYSA-N N InChI=1/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3 Key: LCFVJGUPQDGYKZ-UHFFFAOYAQ
SMILES CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
Properties
Chemical formula	C21H24O4
Molar mass	340.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is an organic compound used as constituent of epoxy resins. The compound is a colorless solid (commercial samples can appear yellow) that melts slightly above room temperature.

It is prepared by O-alkylation of bisphenol A with epichlorohydrin. This reaction mainly affords bisphenol A diglycidyl ether, as well as some oligomer. The degree of polymerization may be as low as 0.1. The epoxide content of such epoxy resins is of interest. This parameter is commonly expressed as the epoxide number, which is the number of epoxide equivalents in 1 kg of resin (Eq./kg), or as the equivalent weight, which is the weight in grams of resin containing 1 mole equivalent of epoxide (g/mol). Since unsymmetrical epoxides are chiral, the bis epoxide consists of three stereoisomers, although these are not separated.

Epoxy resins are thermosetting polymers, which are crosslinked using hardeners (curing agents). The most common curing agents for epoxy resins are polyamines, aminoamides, and phenolic compounds.

DGEBA react with acrylic acid to give so-called vinyl esters. The reaction results in opening of the epoxide ring, generating unsaturated esters at each terminus of the chain. Such materials are diluted with styrene and converted to resin.

Bisphenol A has attracted much attention as a potential endocrine disruptor. It has antiandrogen and PPARγ-modulating properties.

BADGE is listed as an IARC Group 3 carcinogen, meaning it is "not classifiable as to its carcinogenicity to humans". From the 1990s onward, concern has been raised over this possible carcinogenicity because BADGE is also used in epoxy resins in the lining of some tin cans for foodstuffs, and unreacted BADGE may end up in the contents of those cans.