O-Cresyl glycidyl ether

Last updated
o-Cresyl glycidyl ether
O-cresyl glycidyl ether.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-645-3
PubChem CID
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]
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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).

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, composites and elastomers. [4]

Contents

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:

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, vol. 1, Dordrecht: Springer Netherlands, 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. ↑ WOapplication 2003076544,Jung, Ki Sung; Kim, Dae Kyu& Kim, Jung Wooket 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

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