Diethylene glycol diglycidyl ether

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C₁₀H₁₈O_5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.^[2]

Diethylene glycol diglycidyl ether

Names
IUPAC name 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane
Other names Diethylene glycol diglycidyl ether; 2,2'-(Oxybis(2,1-ethanediyloxymethylene))bisoxirane; 4,7,10-Trioxatridecane, 1,2:12,13-diepoxy-; BRN 1308085; Diethylene glycol bis-glycidyl ether; Diglycidyl diethyleneglycol ether; EINECS 224-122-0; NSC 517936; UNII-DU5YP0O31R; 2,2'-(Oxybis(ethyleneoxymethylene))bisoxirane; Ether, bis(2-(2,3-epoxypropoxy)ethyl); Oxirane, 2,2'-(oxybis(2,1-ethanediyloxymethylene))bis-; Oxirane, 2,2'-(oxybis(2,1-ethanediyloxymethylene))bis- (9CI)
Identifiers
CAS Number	4206-61-5
3D model (JSmol)	Interactive image
ChemSpider	311676
ECHA InfoCard	100.021.930
EC Number	224-122-0
PubChem CID	351024
UNII	DU5YP0O31R
CompTox Dashboard (EPA)	DTXSID70960086
InChI InChI=1S/C10H18O5/c1(3-12-5-9-7-14-9)11-2-4-13-6-10-8-15-10/h9-10H,1-8H2 Key: SEFYJVFBMNOLBK-UHFFFAOYSA-N
SMILES C1C(O1)COCCOCCOCC2CO2
Properties
Chemical formula	C10H18O5
Molar mass	218.249 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Manufacture

The product is manufactured by adding diethylene glycol and a Lewis acid catalyst into a reactor and streaming in epichlorohydrin slowly to control the exothermic reaction. This forms the halohydrin, which is dehydrochlorinated with sodium hydroxide. This forms the diglycidyl ether. The waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine).^[3][4] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Uses

A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer.^[5] The molecule has 2 oxirane functionalities, and thus does not at as a chain terminator but it modifies and reduces the viscosity of epoxy resins.^[6][7] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,^[8] (including antimicrobial versions^[9]) adhesives,^[10] sealants, and elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[11][12]

The species has also been used to synthesize other chemical compounds.^[13][14][15]

The toxicology has been studied.^[16][17]

See also

• Epoxide
• Glycidol

Further reading

• Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.{{cite book}}: CS1 maint: others (link)
• Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.{{cite book}}: CS1 maint: location missing publisher (link)
• Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.
• "Dow Epoxy Resins" (PDF).