Trimethylolethane triglycidyl ether
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Names | |
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IUPAC name
2-({2-Methyl-3-(2-oxiranylmethoxy)-2-[(2-oxiranylmethoxy)methyl]propoxy}methyl)oxirane
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Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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Properties | |
C14H24O6 | |
Molar mass | 288.340 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trimethylolethane triglycidyl ether (TMETGE) is an organic chemical in the glycidyl ether family. It has the formula C14H24O6 and the IUPAC name is 2-({2-methyl-3-[(oxiran-2-yl)methoxy]-2-{[(oxiran-2-yl)methoxy]methyl}propoxy}methyl)oxirane. The CAS number is 68460-21-9.[dubious ][1] A key use is as a modifier for epoxy resins as a reactive diluent.[2][3]
Alternative names
- Trimethylolethane,chloromethyloxirane polymer
- Trimethylolethane triglycidyl ether
- 1,3-Propanediol,2-(hydroxymethyl)-2-methyl-,polymer with (chloromethyl)oxirane
- 1,3-Propanediol,2-(hydroxymethyl)-2-methyl-,polymer with 2-(chloromethyl)oxirane
- 2-(hydroxymethyl)-2-methylpropane-1,3-diol-2-(chloromethyl)oxirane (1:1)
Manufacture
Trimethylolethane 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. Waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine).[5][6]
Uses
As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins but giving higher functionality.[7] 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.[8] It produces epoxy coatings with high impact resistance[9] The molecule has been used to synthesize other molecules.[10][11]
See also
References
- ^ "Trimethylolethane triglycidyl ether | C14H24O6 | ChemSpider". www.chemspider.com. Retrieved 2022-05-17.
- ^ 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, Dordrecht: Springer Netherlands, vol. 1, 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
- ^ 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.
- ^ "68460-21-9". www.chemsrc.com. Retrieved 2022-05-17.
- ^ 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.
- ^ Crivello, James V. (2006-11-01). "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.
- ^ 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. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449.
- ^ US 8062468, Finter, Jürgen; Kramer, Andreas & Schulenburg, Jan Olaf et al., "Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins", published 2011-11-22, assigned to Sika Technology AG
- ^ Bednarczyk, Paulina; Irska, Izabela; Gziut, Konrad; Ossowicz-Rupniewska, Paula (2021-05-24). "Novel Multifunctional Epoxy (Meth)Acrylate Resins and Coatings Preparation via Cationic and Free-Radical Photopolymerization". Polymers. 13 (11): 1718. doi:10.3390/polym13111718. ISSN 2073-4360. PMC 8197387. PMID 34074023.
- ^ Huajaikaew, Eakkapap; Piroonpan, Thananchai; Booncharoen, Kasidit; Pasanphan, Wanvimol (2022-02-01). "Comb-like poly(dodecyl methacrylate) modified SiO2 nanoparticles as nanohybrid coatings: Electron beam grafting and tuning superhydrophobic/water-repellent surface studies". Progress in Organic Coatings. 163: 106658. doi:10.1016/j.porgcoat.2021.106658. ISSN 0300-9440. S2CID 245043074.
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.
- 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).
- Ash, Michael (2007). Handbook of Fillers, Extenders, and Diluents. Synapse Info Resources. p. 64. ISBN 978-1-890595-96-8.</ref>
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- Glycidyl ethers
- Reactive diluents