Diethylene glycol diglycidyl ether

Diethylene glycol diglycidyl ether
Names
IUPAC name
2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane
Other names
Diethylene glycol diglycidyl ether; 2,2'-(Oxybis(2,1-ethanediyloxymethylene))bisoxirane; 4,7,10-Trioxatridecane, 1,2:12,13-diepoxy-; BRN 1308085; Diethylene glycol bis-glycidyl ether; Diglycidyl diethyleneglycol ether; EINECS 224-122-0; NSC 517936; UNII-DU5YP0O31R; 2,2'-(Oxybis(ethyleneoxymethylene))bisoxirane; Ether, bis(2-(2,3-epoxypropoxy)ethyl); Oxirane, 2,2'-(oxybis(2,1-ethanediyloxymethylene))bis-; Oxirane, 2,2'-(oxybis(2,1-ethanediyloxymethylene))bis- (9CI)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.930 Edit this at Wikidata
EC Number
  • 224-122-0
UNII
  • InChI=1S/C10H18O5/c1(3-12-5-9-7-14-9)11-2-4-13-6-10-8-15-10/h9-10H,1-8H2
    Key: SEFYJVFBMNOLBK-UHFFFAOYSA-N
  • C1C(O1)COCCOCCOCC2CO2
Properties
C10H18O5
Molar mass 218.249 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P333+P313, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C10H18O5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.[2]

Manufacture

The product is manufactured by adding diethylene glycol and a Lewis acid catalyst into a reactor and streaming in epichlorohydrin slowly to control the exothermic reaction. This forms the halohydrin, which is dehydrochlorinated with sodium hydroxide. This forms the diglycidyl ether. The waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine).[3][4] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Uses

A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer.[5] The molecule has 2 oxirane functionalities, and thus does not at as a chain terminator but it modifies and reduces the viscosity of epoxy resins.[6][7] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,[8] (including antimicrobial versions[9]) adhesives,[10] sealants, and elastomers. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[11][12]

The species has also been used to synthesize other chemical compounds.[13][14][15]

The toxicology has been studied.[16][17]

See also

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.{{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).

References

  1. ^ "Diethylene glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 27 May 2022.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. 
  5. ^ Liu, Fengdan; Guo, Kunkun; Yuan, Jianmin (December 2013). "Preparation of the modified epoxy resins with flexible diglycidyl ether of diethylene glycol". High Performance Polymers. 26 (3): 326–334. doi:10.1177/0954008313514083. ISSN 0954-0083. S2CID 96247006.
  6. ^ Zarnitz, Charles. "Flexibilizing modifiers" (PDF). CVC Thermosets.
  7. ^ 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
  8. ^ WO application 2015095994, Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published 2015-07-02, assigned to Dow Global Technologies LLC 
  9. ^ Mao, Shihua; Zhang, Dong; He, Xiaomin; Yang, Yuting; Protsak, Iryna; Li, Yuting; Wang, Jiawen; Ma, Chunxin; Tan, Jun; Yang, Jintao (2021-01-20). "Mussel-Inspired Polymeric Coatings to Realize Functions from Single and Dual to Multiple Antimicrobial Mechanisms". ACS Applied Materials & Interfaces. 13 (2): 3089–3097. doi:10.1021/acsami.0c16510. ISSN 1944-8244. PMID 33400490. S2CID 230783212.
  10. ^ Yuan, Cheng; Luo, Jing; Luo, Jianlin; Gao, Qiang; Li, Jianzhang (2016). "A soybean meal-based wood adhesive improved by a diethylene glycol diglycidyl ether: properties and performance". RSC Advances. 6 (78): 74186–74194. Bibcode:2016RSCAd...674186Y. doi:10.1039/C6RA07844C. ISSN 2046-2069.
  11. ^ 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.
  12. ^ 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.
  13. ^ Nakatsuji, Yohji; Tsuji, Yuichi; Ikeda, Isao; Okahara, Mitsuo (January 1986). "Reactions of oligoethylene glycol diglycidyl ethers with hydroxy compounds". The Journal of Organic Chemistry. 51 (1): 78–81. doi:10.1021/jo00351a016. ISSN 0022-3263.
  14. ^ Moini, Nasrin; Kabiri, Kourosh; Zohuriaan-Mehr, Mohammad J. (2016-02-11). "Practical Improvement of SAP Hydrogel Properties via Facile Tunable Cross-linking of the Particles Surface". Polymer-Plastics Technology and Engineering. 55 (3): 278–290. doi:10.1080/03602559.2015.1070873. ISSN 0360-2559. S2CID 101375643.
  15. ^ Ikeda, Isao; Tsuji, Yuichi; Nakatsuji, Yohji; Okahara, Mitsuo (April 1986). "Synthesis of dihydroxy thia crown ethers and derivatization to bicyclic crown compounds". The Journal of Organic Chemistry. 51 (7): 1128–1130. doi:10.1021/jo00357a037. ISSN 0022-3263.
  16. ^ Jolanki, R.; Takwinun, K.; Tatar, T.; Estlander, T.; Henriks-Eckerman, M.-L.; Mustakallio, K. K.; Kanerva, L. (June 1996). "Occupational dermatoses from exposure to epoxy resin compounds in a ski factory". Contact Dermatitis. 34 (6): 390–396. doi:10.1111/j.1600-0536.1996.tb02239.x. PMID 8879923. S2CID 8996324.
  17. ^ "Current intelligence bulletin 29 - glycidyl ethers". 2020-09-24. doi:10.26616/NIOSHPUB79104. {{cite journal}}: Cite journal requires |journal= (help)

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