Diglycidyl resorcinol ether explained

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.[1] [2]

The formula is C12H14O4[3] and the CAS Registry Number 101-90-6.[4] It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins.[5] These are then further used in coatings, sealants, adhesives and elastomers.[6] It has the CAS Registry Number 101-90-6.[7] It has the IUPAC name 2-3-(oxiran-2-ylmethoxy)phenoxymethyl]oxirane and is registered on TSCA (Toxic Substances Control Act of 1976) as Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-.[8] It is REACH registered and on EINECS.[9]

Synonyms

Synthesis

Resorcinol and epichlorohydrin are reacted in the presence of a base and not a Lewis acid catalyst as normal with glycidyl ethers. A halohydrin is formed. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms Resorcinol diglycidyl ether.[12] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

The material has two oxirane groups and is thus used mainly in epoxy resins systems as a reactive diluent and modifier.[13] [14] [15] It has found use as an additive for bonding resin systems[16] and also as a modifier for phenolic resins[17] Despite the toxicity it generally gives excellent properties and so there are military applications.[18] The use of the diluent does effect mechanical properties and microstructure of epoxy resins. However, this diluent is one of the best for not reducing properties too much.[19] [20]

Toxicology

It is classed as IARC group 2B by the International Agency for Research on Cancer. The toxicology has been studied for a long time and is fairly well understood.[21]

See also

Further reading

External Websites

Notes and References

  1. Web site: Resorcinol diglycidyl ether C12H14O4 ChemSpider . 2022-05-25 . www.chemspider.com.
  2. Web site: NCI Thesaurus . 2022-05-25 . ncithesaurus.nci.nih.gov.
  3. Web site: Resorcinol diglycidyl ether . 2022-05-25 . www.chemsrc.com . en.
  4. Web site: Inc . Abt Associates . Toxics Release Inventory (TRI) GuideME . 2022-05-25 . ordspub.epa.gov . en.
  5. Web site: Resorcinol diglycidyl ether CAS 101-90-6 . 2022-05-25 . www.scbt.com . en.
  6. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 23,24,39 Master of Science Thesis April 1997 Imperial College London
  7. Web site: PubChem . Diglycidyl resorcinol ether . 2022-05-27 . pubchem.ncbi.nlm.nih.gov . en.
  8. Web site: New Jersey Resorcinol Diglycidyl Ether Hazardous Substance Sheet. New Jersey government.
  9. Web site: Substance Information - ECHA . 2022-05-27 . echa.europa.eu . en-GB.
  10. Web site: Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis- ]. 2022-05-25 . webbook.nist.gov . en.
  11. Web site: PubChem . Hazardous Substances Data Bank (HSDB) : 4166 . 2022-05-25 . pubchem.ncbi.nlm.nih.gov . en.
  12. Crivello . James V. . 2006 . Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization . Journal of Polymer Science Part A: Polymer Chemistry . 44 . 21 . 6435–6448 . 10.1002/pola.21761 . 2006JPoSA..44.6435C . 0887-624X.
  13. Jagtap . Ameya Rajendra . More . Aarti . 2022-08-01 . Developments in reactive diluents: a review . Polymer Bulletin . en . 79 . 8 . 5667–5708 . 10.1007/s00289-021-03808-5 . 235678040 . 1436-2449.
  14. Sorokin . V. P. . Bobylev . V. A. . Eselev . A. D. . 2007-09-01 . Epoxy resins based on resorcinol and its derivatives . Polymer Science Series C . en . 49 . 3 . 272–275 . 10.1134/S1811238207030149 . 94228644 . 1555-614X.
  15. Web site: Diglycidyl Resorcinol Ether - an overview ScienceDirect Topics . 2022-05-25 . www.sciencedirect.com.
  16. WO. 2021124125. application. 2021-06-24. Stora Enso Oyj. Process for the preparation of a bonding resin.
  17. US. 11161976. 2021-11-02. Hexion Vad LLC. Phenolic epoxy system. Goodwin. Kimberly. Viswanathan. Ganapathy S.. Peace. Scott. Anthony Maiorana;Vishal Patil.
  18. Booth . Hubert J. . 1973-07-26 . Synthesis of Epoxy Resins for Property-Structure Studies . https://web.archive.org/web/20210514172550/https://apps.dtic.mil/sti/citations/AD0765694 . live . May 14, 2021 . en.
  19. Pastarnokienė . Liepa . Jonikaitė-Švėgždienė . Jūratė . Lapinskaitė . Neringa . Kulbokaitė . Rūta . Bočkuvienė . Alma . Kochanė . Tatjana . Makuška . Ričardas . 2023-07-01 . The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings . Journal of Coatings Technology and Research . en . 20 . 4 . 1207–1221 . 10.1007/s11998-022-00737-4 . 256749849 . 1935-3804.
  20. Khalina . Morteza . Beheshty . Mohammad Hosain . Salimi . Ali . 2019-08-01 . The effect of reactive diluent on mechanical properties and microstructure of epoxy resins . Polymer Bulletin . en . 76 . 8 . 3905–3927 . 10.1007/s00289-018-2577-6 . 105389177 . 1436-2449.
  21. National Toxicology Program . 2011 . Diglycidyl resorcinol ether . Report on Carcinogens: Carcinogen Profiles . 12 . 163–164 . 1551-8280 . 21852825.

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