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Dibromo neopentyl glycol diglycidyl ether

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Dibromo neopentyl glycol diglycidyl ether
Identifiers
3D model (JSmol)
  • InChI=1S/C11H18Br2O4/c12-5-11(6-13,7-14-1-9-3-16-9)8-15-2-10-4-17-10/h9-10H,1-8H2
    Key: NLXKDKQYAADKMT-UHFFFAOYSA-N
  • BrCC(COCC1CO1)(COCC2CO2)CBr
Properties
C11H18Br2O4
Molar mass 374.069 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dibromo neopentyl glycol diglycidyl ether is a brominated version of neopentyl glycol diglycidyl ether. It is an aliphatic organic chemical in the glycidyl ether family that is used in epoxy resin formulations. It has the molecular formula C11H18Br2O4

Synthesis

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The usual method of synthesis is to take brominated neopentyl glycol and react with epichlorohydrin using Lewis acid catalysis to form the halohydrin. This species is then reacted with sodium hydroxide to form the diglycidyl ether.[1]

Uses

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A key use of the material is reducing the viscosity of epoxy resins. As an epoxy modifier it is classed as a reactive diluent, which may then be formulated into CASE applications (coatings, adhesives, sealants, and elastomers and composite materials).[2] As it is an organobromine compound it is used to improve the Flame retardant properties of materials.[3] Flame retardant coatings[4] including powder coatings maybe produced.[5]

Toxicity

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There is a trend to try and formulate away from brominated species in general because of the toxicity of the smoke produced when heated.[6]

Further reading

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  • Bruins, Paul F. (1968). Epoxy resin technology. New York: Interscience Publishers. ISBN 0-470-11390-1. OCLC 182890.
  • 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.

References

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  1. ^ Li, Botao. "Synthesis of the Diglycidyl Ether of Brominated Neopentyl Glycol and Properties of the Resulting Cured Material". SSRN 4710385.
  2. ^ Monte, Salvatore J. (1998). "Diluents and viscosity modifiers for epoxy resins". In Pritchard, Geoffrey (ed.). Plastics Additives: An A-Z reference. Polymer Science and Technology Series. Vol. 1. Dordrecht: Springer Netherlands. pp. 211–216. doi:10.1007/978-94-011-5862-6_24. ISBN 978-94-011-5862-6.
  3. ^ YUN YONG-JU. "NONFLAMMABLE ADHESIVE COMPOSITION". Korean Patent KR930023435 (A).
  4. ^ "Epoxy Resins and curatives". dl.asminternational.org. Retrieved 2024-11-14.
  5. ^ Straley, Christian (1983-07-01). "A brominated epoxy embedding system". Powder Technology. 35 (2): 259–261. doi:10.1016/0032-5910(83)87016-8. ISSN 0032-5910.
  6. ^ Glodek, Terese E.; Boyd, Steven E.; McAninch, Ian M.; LaScala, John J. (2008-11-01). "Properties and performance of fire resistant eco-composites using polyhedral oligomeric silsesquioxane (POSS) fire retardants". Composites Science and Technology. Nanocomposites - Processing, Characterization, Properties, Applications and Modelling, selected papers from Nanocomposite Special Symposium of ACCM-5, with regular papers. 68 (14): 2994–3001. doi:10.1016/j.compscitech.2008.06.019. ISSN 0266-3538.
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