Bisphenol A diglycidyl ether

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
Abbreviations	BADGE; DGEBA
CAS Registry Number	1675-54-3 Y
ChemSpider	2199 N
EC number	216-823-5
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
Jmol-3D images	Image
KEGG	C14348 N
MeSH	C019273
PubChem	2286
SMILES CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
Properties
Molecular formula	C21H24O4
Molar mass	340.41 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is a chemical compound used as constituent of epoxy resins. It is a derivative of bisphenol A and glycidol that is used in epoxy resins for its cross-linking properties.^[1]

Many standard epoxies are based on a formula containing diglycidyl ethers, including BADGE.^[2] Epoxy resins are crosslinked using hardeners (curing agents). The most common curing agents for epoxy resins are polyamines, aminoamides and phenolic compounds.^[3]

BADGE is listed as an IARC Group 3 carcinogen, meaning it is "not classifiable as to its carcinogenicity to humans".^[4] 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.^[1]

See also

• Bisphenol A (BPA)
• Bisphenol AF (BPAF)
• Bisphenol S (BPS)

References

1. ↑ 1.0 1.1 Walfried Rauter, Gerald Dickinger, Rudolf Zihlarz and Josef Lintschinger, “Determination of Bisphenol A diglycidyl ether (BADGE) and its hydrolysis products in canned oily foods from the Austrian market”, Z. Lebensm. Unters. Forsch. A 208 (1999) 208–211
2. ↑ Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline) http://www.umweltbundesamt.de/wasser/themen/downloads/trinkwasser/beschichtungsleitlinie.pdf
3. ↑ Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8
4. ↑ Group 3: Not classifiable as to carcinogenicity to humans, International Agency for Research on Cancer