o-Cresyl glycidyl ether

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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 Edit this at Wikidata
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).

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]

Uses[edit]

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[edit]

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[edit]

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[edit]

References[edit]

  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. ^ 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[edit]

External Websites[edit]

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