o-Cresyl glycidyl ether

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.[2] It has the formula C10H12O2 and the CAS Registry Number 2210-79-9.[3] 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.[4]

o-Cresyl glycidyl ether
Names
IUPAC name
2-[(2-Methylphenoxy)methyl]oxirane
Other names
ortho-Cresyl glycidyl ether; o-CGE; Glycidyl 2-methylphenyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.016.951
EC Number
  • 218-645-3
RTECS number
  • TZ3700000
UN number 3334
  • InChI=1S/C10H12O2/c1-8-4-2-3-5-10(8)12-7-9-6-11-9/h2-5,9H,6-7H2,1H3
    Key: KFUSXMDYOPXKKT-UHFFFAOYSA-N
  • CC1=CC=CC=C1OCC2CO2
Properties
C10H12O2
Molar mass 164.204 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H315, H317, H341, H411
P201, P202, P261, P264, P272, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P333+P313, P362, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

The main use of o-CGE is to reduce the viscosity of epoxy resins.[5][6] These reduced viscosity resins may then be used to formulate coatings including UV cured versions.[7] It is a monofunctional diluent and so in polymer science terms is a chain terminator. Chain extenders (f = 2) and cross linkers (f ≥ 3) are low molecular weight di or tri-functional epoxy diluents. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[8][9] As it has glycidyl functionality, it is classed as a Reactive diluent.

Other names

o-CGE is known by a number of other names.[10][11] These include:

  • Oxirane, 2-[(2-methylphenoxy)methyl]-
  • Propane, 1,2-epoxy-3-(o-tolyloxy)-
  • Oxirane, [(2-methylphenoxy)methyl]-[12]
  • 2-[(2-Methylphenoxy)methyl]oxirane
  • 1-(o-Methylphenoxy)-2,3-epoxypropane

Toxicology

The material is a skin irritant and skin sensitizer. The toxicology has been reasonably well studied.[13][14][15][16] It is REACH registered and produced or imported into the European Union in quantities greater than one thousand tonnes per annum.[17]

See also

References
  1. "O-Cresyl glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 4 April 2022.
  2. "o-cresyl glycidyl ether". www.wikidata.org. Retrieved 2022-03-25.
  3. PubChem. "O-Cresyl glycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-25.
  4. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 23,24,39 Master of Science Thesis April 1997 Imperial College London
  5. 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, retrieved 2022-03-29
  6. US 6987144, Anderson, Lawrence G.; De Saw, Shawn A. & Hartman, Marvis E. et al., "Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto", published 2006-01-17, assigned to PPG Industries, Ohio Inc.
  7. WO application 2003076544, Jung, Ki Sung; Kim, Dae Kyu & Kim, Jung Wook et al., "UV-curable epoxy resin composition comprising lactone monomer", published 2003-09-18, assigned to Luvantix Co. Ltd., application discontinued outside South Korea.
  8. 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.
  9. 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.
  10. "System of Registries | US EPA". sor.epa.gov. Retrieved 2022-03-25.
  11. "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2022-03-25.
  12. "Oxirane, [(2-methylphenoxy)methyl]- - MS - Spectrum - SpectraBase". spectrabase.com. Retrieved 2022-03-25.
  13. Kanerva, L.; Jolanki, R.; Alanko, K.; Estlander, T. (July 1999). "Patch-test reactions to plastic and glue allergens". Acta Dermato-Venereologica. 79 (4): 296–300. doi:10.1080/000155599750010706. ISSN 0001-5555. PMID 10429988.
  14. "ICSC 0135 - o-CRESYL GLYCIDYL ETHER". inchem.org. Retrieved 2022-03-25.
  15. "O-cresyl glycidyl ether | Allergic Contact Dermatitis Database". www.contactdermatitisinstitute.com. Retrieved 2022-03-25.
  16. "O-CRESYL GLYCIDYL ETHER | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2022-03-25.
  17. "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-03-25.

Further reading

External Websites
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