Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family.[2][3] It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3.[4][5] It also has another CAS number of 30499-70-8[6][7] A key use is as a modifier for epoxy resins as a reactive diluent.[8]
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| Names | |
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| IUPAC name
2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane
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| Other names
1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C15H26O6 | |
| Molar mass | 302.364 g/mol |
| Hazards | |
| GHS labelling:[1] | |
  
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| Danger | |
| H315, H317, H318, H319, H334, H335, H412 | |
| 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 [77 °F], 100 kPa).
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Alternative names
edit- Oxirane, 2,2′-[[2-ethyl-2-[(2-oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis-
- Butane, 1-(2,3-epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]-
- Oxirane, 2,2′-[[2-ethyl-2-[(oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis-
- 2,2′-[[2-Ethyl-2-[(2-oxiranylmethoxy)methyl]-1,3-propanediyl]bis(oxymethylene)]bis[oxirane]
- 1,1,1-Trimethylolpropane triglycidyl ether
Manufacture
editTrimethylolpropane 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.[9][10]
Uses
editAs the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins.[11] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: Coatings,[12] Adhesives,[13] Sealants,[14] Elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[15][16] It produces epoxy coatings with high impact resistance[17] Polymer systems with shape memory may also be produced with this particular molecule.[18] Fluoropolymers have also been produced with the material via a photoinitiated mechanism.[19] Production of biocompatible materials is also possible.[20]
See also
editReferences
edit- ^ "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 13 April 2022.
- ^ PubChem. "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-11.
- ^ "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.
- ^ "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2022-04-12.
- ^ "Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3". www.chemindustry.com. Retrieved 2022-04-12.
- ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-12.
- ^ "Trimethylolpropane triglycidyl ether". www.carbosynth.com. Retrieved 2022-04-12.
- ^ 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.
- ^ 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
- ^ WO application 2019238867, Bevinakatti, Hanamanthsa & Islam, Mojahedul, "Herbicidal formulations comprising glyphosate and cote-based adjuvants", published 2019-12-19, assigned to Nouryon Chemicals International BV
- ^ Hao, Xiu; Fan, Dong-Bin (2018-12-17). "Preparation and characterization of epoxy-crosslinked soy protein adhesive". Journal of Adhesion Science and Technology. 32 (24): 2682–2692. doi:10.1080/01694243.2018.1517488. ISSN 0169-4243. S2CID 105550538.
- ^ "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
- ^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
- ^ 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. S2CID 105389177.
- ^ 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
- ^ Santiago, David; Guzmán, Dailyn; Ferrando, Francesc; Serra, Àngels; De la Flor, Silvia (March 2020). "Bio-Based Epoxy Shape-Memory Thermosets from Triglycidyl Phloroglucinol". Polymers. 12 (3): 542. doi:10.3390/polym12030542. ISSN 2073-4360. PMC 7182903. PMID 32131508.
- ^ Trusiano, Giuseppe; Vitale, Alessandra; Bonneaud, Céline; Pugliese, Diego; Dalle Vacche, Sara; Joly-Duhamel, Christine; Friesen, Chadron M.; Bongiovanni, Roberta (2021-03-01). "Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers". Colloid and Polymer Science. 299 (3): 509–521. doi:10.1007/s00396-020-04723-3. ISSN 1435-1536. PMC 7952294. PMID 33785978.
- ^ "Journal of Electrochemical Science and Technology". www.jecst.org. Retrieved 2022-04-12.
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).