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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
ChemSpider
ECHA InfoCard
100.021.930
EC Number
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
Properties
C 10 H 18 O 5
Molar mass
218.249 g·mol−1
Hazards
GHS labelling :
[1]
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).
Chemical compound
Diethylene glycol diglycidyl ether (DEGDGE ) is an
organic chemical in the glycidyl
ether family with the formula C10 H18 O5. . 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
References
^
"Diethylene glycol diglycidyl ether" . pubchem.ncbi.nlm.nih.gov . Retrieved 27 May 2022 .
^ 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.
^ 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 .
^ Zarnitz, Charles.
"Flexibilizing modifiers" (PDF) . CVC Thermosets .
^ 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 2015095994 , Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published 2015-07-02, assigned to
Dow Global Technologies LLC
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^
"Current intelligence bulletin 29 - glycidyl ethers" . 2020-09-24.
doi :
10.26616/NIOSHPUB79104 .
External websites
Mono-epoxy Di-epoxy Tri-epoxy