Trimethylolpropane triglycidyl ether

Trimethylolpropane triglycidyl ether

Names
IUPAC name 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane
Other names 1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
Identifiers
CAS Number	3454-29-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:189372
ChemSpider	93067
EC Number	222-384-0
PubChem CID	103015
CompTox Dashboard (EPA)	DTXSID90873907
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,2-11H2,1H3 Key: QECCQGLIYMMHCR-UHFFFAOYSA-N
SMILES CCC(COCC1CO1)(COCC2CO2)COCC3CO3
Properties
Chemical formula	C15H26O6
Molar mass	302.364 g/mol
Hazards
GHS labelling: [1]
Pictograms
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 [77 °F], 100 kPa). Infobox references

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]

Alternative names

• 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

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. ^{[9] [10]}

Uses

As 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

• Epoxide
• Glycidol
• Glycerol triglycidyl ether

References

1. "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 13 April 2022.
2. PubChem. "1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-11.
3. "2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider". www.chemspider.com. Retrieved 2022-04-12.
4. "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2022-04-12.
5. "Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3". www.chemindustry.com. Retrieved 2022-04-12.
6. "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-12.
7. "Trimethylolpropane triglycidyl ether". www.carbosynth.com. Retrieved 2022-04-12.
8. 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.
9. 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.
10. 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.  
11. 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
12. WOapplication 2019238867,Bevinakatti, Hanamanthsa&Islam, Mojahedul,"Herbicidal formulations comprising glyphosate and cote-based adjuvants",published 2019-12-19, assigned to Nouryon Chemicals International BV  
13. 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.
14. "14228-73-0 | CAS DataBase". www.chemicalbook.com. Archived from the original on 2022-04-11. Retrieved 2022-04-11.
15. 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.
16. 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.
17. US 8062468,Finter, Jürgen; Kramer, Andreas& Schulenburg, Jan Olafet al.,"Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins",published 2011-11-22, assigned to Sika Technology AG  
18. 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.
19. 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.
20. "Journal of Electrochemical Science and Technology". www.jecst.org. Retrieved 2022-04-12.

Further reading

• Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. 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.
• 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).

External websites

• Hexion Poly-functional Modifiers
• Denacol epoxy diluent range
• Cargill Reactive diluents