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1,3-Bis[3-(dimethylamino)propyl]urea [1]
Glycerol triglycidyl ether (triglycidyl glycerol) is an aliphatic organic chemical in the glycidyl ether family.[2] It has the formula C12H20O6.[3] The CAS number is 13236-02-7. The IUPAC name is 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane. A key use is as a modifier for epoxy resins as a reactive diluent.[4]
Alternative names
[edit]There are a variety of names.[5][6]
- TRIGLYCIDYLGLYCEROL
- 1,2,3-Tris(2,3-epoxypropoxy)propane
- Glycerine triglycidyl ether
- Glycerol tris(2,3-epoxypropyl) ether
- 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane
- Propane, 1,2,3-tris(2,3-epoxypropoxy)-
- Glycerol 1,2,3-triglycidyl ether
Manufacture
[edit]Glycerine 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.[7][8]
Uses
[edit]As the molecule has 3 oxirane functionalities, it is a reactive modifier and viscosity reduction agent of epoxy resins.[9] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings, Adhesives, Sealants, and Elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.
References
[edit]- ^ PubChem. "1,3-Bis[3-(dimethylamino)propyl]urea". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-01-02.
- ^ PubChem. "Triglycidylglycerol". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-12-17.
- ^ "Glycerol triglycidyl ether | 13236-02-7". ChemicalBook. Retrieved 2024-12-17.
- ^ Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
- ^ "Glycerol triglycidyl ether | 13236-02-7 | FG173064". www.biosynth.com. Retrieved 2024-12-17.
- ^ "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.
- ^ 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. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN 0887-624X.
- ^ US 5162547, Roth, Martin; Wolleb, Heinz & Truffer, Marc-Andre, "Process for the preparation of glycidyl ethers", published 1992-11-10, assigned to Ciba-Geigy Corp.
- ^ Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", 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, archived from the original on 2022-04-11, retrieved 2022-03-29
Further reading
[edit]- 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).