Bisphenol A diglycidyl ether

Source: Wikipedia, the free encyclopedia.
Bisphenol A diglycidyl ether
Chemical structure of bisphenol A diglycidyl ether
Names
Preferred IUPAC name
5,5-Dimethyl-3,7-dioxa-1,9(2)-bis(oxirana)-4,6(2,4)-dibenzenanonaphane
Other names
Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
Identifiers
3D model (
JSmol
)
Abbreviations BADGE; DGEBA
ChemSpider
ECHA InfoCard
 100.015.294 Edit this at Wikidata
EC Number
  • 216-823-5
KEGG
MeSH C019273
UNII
  • 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
  • CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
Properties
C21H24O4
Molar mass 340.419 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Bisphenol A diglycidyl ether (commonly abbreviated BADGE or DGEBA) is an

epoxy resin.[1][2][3][4][5] The compound is a colorless viscous liquid (commercial samples can appear pale straw-coloured).[6][7] It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.[8]

Structure of bisphenol-A diglycidyl ether epoxy resin: n denotes the number of polymerized subunits and is typically in the range from 0 to 25

Preparation and reactions

It is prepared by O-

stereoisomers
, although these are not separated.

Bisphenol A diglycidyl ether slowly hydrolyzes to 2,2-bis[4(2,3-dihydroxypropoxy)phenyl)propane (bis-HPPP).

Similarly, DGEBA reacts with acrylic acid to give vinyl ester resins. The reaction results in opening of the epoxide ring, generating unsaturated esters at each terminus of the molecule. Such materials are often diluted with styrene and converted to resin.

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.[10]

Safety

BADGE is highly reactive and forms a number of species upon exposure to water or HCl and many of these compounds (including BADGE) are suspected endocrine disruptors[11] Hydrolysis of the ether bonds liberates bisphenol A, which is also strongly suspected of being an endocrine disruptor.[12][13] From the 1990s onward, concern has been raised over the use of BADGE-based epoxy resins in the lining of some cans for foodstuffs, with the chemical being found to leach into foods.[12][14] Bisphenol A Diglycidyl ether-based epoxy coatings are extensively used for coating the inside of cans which come into contact with food and are thus food contact materials. The materials and analogues and conjugates have been extensively tested for and analytical methods developed.[15][16]

See also

References

  1. OCLC 851368739
    .
  2. ^ "Bisphenol A Liquid Epoxy Resins | Business & Products". DIC Corporation. Retrieved 2023-01-11.
  3. ^ "Epoxy: A Complete Guide". Copps Industries. Retrieved 2023-01-11.
  4. ^ PubChem. "Bisphenol A diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-11.
  5. ^ "2,2-Bis(4-glycidyloxyphenyl)propane 1675-54-3 | TCI AMERICA". www.tcichemicals.com. Retrieved 2023-01-11.
  6. ^ Hofer, Arnold; Schneider, Hildegard, and Siegenthaler, Nikolaus (1996) "Epoxy resin mixtures containing advancement catalysts", U.S. patent 5,521,261.
  7. ISBN 978-3527306732
    .
  8. ISBN 978-94-010-5302-0
    , retrieved 2023-01-11
  9. ISBN 9780470073698
    .
  10. ^ Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8
  11. PMID 34146765
    .
  12. ^ a b 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
  13. ^ "Leitlinie zur hygienischen Beurteilung von organischen Beschichtungen im Kontakt mit Trinkwasser (Beschichtungsleitlinie)" [Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline)] (PDF). www.umweltbundesamt.de (in German). 16 March 2016. Archived from the original (PDF) on 9 January 2017. Retrieved 6 October 2019.
  14. ISBN 978-0-471-12547-1
    , retrieved 2022-07-28
  15. S2CID 251912604
    .
  16. S2CID 252213795
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Bisphenol_A_diglycidyl_ether&oldid=1193762106"