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1,6-Hexanediol diglycidyl ether

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1,6-Hexanediol diglycidyl ether
Names
IUPAC name
2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane
Other names
    • 1,6-Hexanediol diglycidyl ether
    • 1,6-Bis(2,3-epoxypropoxy)hexane;
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.036.585 Edit this at Wikidata
EC Number
  • 240-260-4
  • InChI=1S/C12H22O4/c1(3-5-13-7-11-9-15-11)2-4-6-14-8-12-10-16-12/h11-12H,1-10H2
    Key: WTYYGFLRBWMFRY-UHFFFAOYSA-N
  • C1C(O1)COCCCCCCOCC2CO2
Properties
C12H22O4
Molar mass 230.304 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317, H319, H412
P261, P264, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P313, P337+P317, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[2] It is REACH registered.[3]

Manufacture

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1,6-Hexanediol and epichlorohydrin are reacted in the presence of a Lewis acid as catalyst to form a halohydrin: each hydroxyl group of the diol reacts with an epoxide on epichlorohydrin. This process is followed by washing with sodium hydroxide to re-form the epoxide rings in a dehydrochlorination reaction.[4][5] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

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Its main use is for reduction of viscosity in epoxy resin systems - it is thus an epoxy reactive diluent. The chain length helps give some degree of flexibility as an epoxy resin has rigid aromatic rings which are planar.[6] These systems may then be formulated into CASE applications: Coatings,[7] Adhesives, Sealants, Elastomers, and composite materials. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[8][9]

Toxicity

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The toxicity is fairly well understood.[10] It is classed as a skin irritant, skin sensitizer, allergen and has caused contact dermatitis.[11][12]

See also

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References

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  1. ^ "1,6-Hexanediol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 9 April 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. ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-09.
  4. ^ Yi, Wen-Jing; Feng, Zhi-Hua; Zhang, Qin-Fang; Zhang, Ji; Li, Ling-Dong; Zhu, Wen; Yu, Xiao-Qi (2011-03-16). "Diol glycidyl ether-bridged cyclens: preparation and their applications in gene delivery". Organic & Biomolecular Chemistry. 9 (7): 2413–2421. doi:10.1039/C0OB00879F. ISSN 1477-0539. PMID 21340090.
  5. ^ 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.
  6. ^ Monte, Salvatore J. (1998). "Diluents and viscosity modifiers for epoxy resins". In Pritchard, Geoffrey (ed.). Plastics Additives. 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.
  7. ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" page 23 Master of Science Thesis April 1997 Imperial College London
  8. ^ 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.
  9. ^ 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.
  10. ^ Berdasco, Nancy Anne M.; Waechter, John M. (2012-08-17), Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. (eds.), "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds", Patty's Toxicology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 491–528, doi:10.1002/0471435139.tox083.pub2, ISBN 978-0-471-12547-1, retrieved 2022-07-28
  11. ^ Angelini, G.; Rigano, L.; Foti, C.; Grandolfo, M.; Veña, G. A.; Bonamonte, D.; Soleo, L.; Scorpiniti, A. A. (July 1996). "Occupational sensitization to epoxy resin and reactive diluents in marble workers". Contact Dermatitis. 35 (1): 11–16. doi:10.1111/j.1600-0536.1996.tb02259.x. ISSN 0105-1873. PMID 8896948. S2CID 7144917.
  12. ^ Geier, Johannes; Lessmann, Holger; Hillen, Uwe; Skudlik, Christoph; Jappe, Uta (February 2016). "Sensitization to reactive diluents and hardeners in epoxy resin systems. IVDK data 2002-2011. Part I: reaction frequencies". Contact Dermatitis. 74 (2): 83–93. doi:10.1111/cod.12491. ISSN 1600-0536. PMID 26538018. S2CID 22297749.

External websites

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