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Trimethylolpropane triglycidyl ether

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Trimethylolpropane triglycidyl ether
Names
IUPAC name 2-oxirane
Other names 1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 222-384-0
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H26O6/c1-2-15(9-16-3-12-6-19-12,10-17-4-13-7-20-13)11-18-5-14-8-21-14/h12-14H,2-11H2,1H3Key: QECCQGLIYMMHCR-UHFFFAOYSA-N
SMILES
  • CCC(COCC1CO1)(COCC2CO2)COCC3CO3
Properties
Chemical formula C15H26O6
Molar mass 302.364 g/mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H315, H317, H318, H319, H334, H335, H412
Precautionary statements P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P313, P337+P317, P342+P316, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

Alternative names

  • Oxirane, 2,2′--1,3-propanediyl]bis(oxymethylene)]bis-
  • Butane, 1-(2,3-epoxypropoxy)-2,2-bis-
  • Oxirane, 2,2′--1,3-propanediyl]bis(oxymethylene)]bis-
  • 2,2′--1,3-propanediyl]bis(oxymethylene)]bis
  • 1,1,1-Trimethylolpropane triglycidyl ether

Manufacture

Trimethylolpropane and epichlorohydrin are reacted with a Lewis acid catalyst to form a halohydrin. The next step is dehydrochlorination with sodium hydroxide. This forms the triglycidyl ether.

Uses

As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins. These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings, Adhesives, Sealants, Elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins. It produces epoxy coatings with high impact resistance Polymer systems with shape memory may also be produced with this particular molecule. Fluoropolymers have also been produced with the material via a photoinitiated mechanism. Production of biocompatible materials is also possible.

See also

References

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Further reading

External websites

Ethers of glycidol
Mono-epoxy
Di-epoxy
Tri-epoxy
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