1,6-Hexanediol diglycidyl ether explained

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

Manufacture

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.[3] [4] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

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.[5] These systems may then be formulated into CASE applications: Coatings,[6] Adhesives, Sealants, Elastomers, and composite materials. The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[7] [8]

Toxicity

The toxicity is fairly well understood. It is classed as a skin irritant, skin sensitizer, allergen and has caused contact dermatitis.[9] [10]

See also

External websites

Notes and References

  1. Jagtap . Ameya Rajendra . More . Aarti . 2022-08-01 . Developments in reactive diluents: a review . Polymer Bulletin . en . 79 . 8 . 5667–5708 . 10.1007/s00289-021-03808-5 . 235678040 . 1436-2449.
  2. Web site: Substance Information - ECHA . 2022-04-09 . echa.europa.eu . en-GB.
  3. 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 . en . 9 . 7 . 2413–2421 . 10.1039/C0OB00879F . 21340090 . 1477-0539.
  4. 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 . 10.1002/pola.21761 . 2006JPoSA..44.6435C . 0887-624X.
  5. Book: Monte, Salvatore J. . Plastics Additives . Diluents and viscosity modifiers for epoxy resins . Polymer Science and Technology Series . 1998 . 1 . 211–216 . Pritchard . Geoffrey . Dordrecht . Springer Netherlands . en . 10.1007/978-94-011-5862-6_24 . 978-94-011-5862-6 .
  6. 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
  7. 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 . en . 76 . 8 . 3905–3927 . 10.1007/s00289-018-2577-6 . 105389177 . 1436-2449.
  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 . en . 20 . 4 . 1207–1221 . 10.1007/s11998-022-00737-4 . 256749849 . 1935-3804.
  9. 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 . 10.1111/j.1600-0536.1996.tb02259.x . 0105-1873 . 8896948. 7144917 .
  10. 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 . 10.1111/cod.12491 . 1600-0536 . 26538018. 22297749 .

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "1,6-Hexanediol diglycidyl ether".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.