Diethylene glycol diglycidyl ether

Last updated
Diethylene glycol diglycidyl ether
Diethyleenglycoldiglycidylether t.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 224-122-0
PubChem CID
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]
GHS-pictogram-exclam.svg
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]

Contents

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

Related Research Articles

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">Cyclohexanedimethanol</span> Chemical compound

Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

<span class="mw-page-title-main">Reactive diluent</span>

Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer.

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2 an industrial chemical used to reduce the viscosity of epoxy resins. These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6. It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.

<i>o</i>-Cresyl glycidyl ether Chemical compound

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C10H12O2 and the CAS Registry Number 2210-79-9. It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins. These are then further used in coatings, sealants, adhesives and elastomers.

Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C11H20O4 and the CAS registry number of 17557-23-2. It has two oxirane groups per molecule. Its principle use is in modifying epoxy resins.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. It has the formula C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane, and the CAS number 14228-73-0. It is It is REACH registered in Europe. It is an industrial chemical and a key use is in the reduction of viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">C12–C14 alcohol glycidyl ether</span> Chemical compound

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family. It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane. Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. 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. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Castor oil glycidyl ether</span> Chemical compound

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12 and the CAS number 14228-73-0. The IUPAC name is 2,3-bis[12-(oxiran-2-ylmethoxy)octadec-9-enoyloxy]propyl 12-(oxiran-2-ylmethoxy)octadec-9-enoate. A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

<span class="mw-page-title-main">Trimethylolethane triglycidyl ether</span> Chemical compound

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. A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Poly(propylene glycol) diglycidyl ether</span> Chemical compound

Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. They have the formula (C3H6O)n.C6H10O3 and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer. It is REACH registered.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

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, 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
  8. ↑ WOapplication 2015095994,Shen, Yue; Zhan, Fu& Wu, Yanet 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.
  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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