1,6-Hexanediol diglycidyl ether

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
CAS Number	16096-31-4;
3D model (JSmol)	Interactive image;
ChemSpider	77541;
ECHA InfoCard	100.036.585
EC Number	240-260-4;
PubChem CID	85960;
CompTox Dashboard (EPA)	DTXSID50275827 DTXSID60864660, DTXSID50275827 ;
	InChI 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;
	SMILES C1C(O1)COCCCCCCOCC2CO2;
Properties
Chemical formula	C12H22O4
Molar mass	230.304 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H412
Precautionary statements	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). Infobox references

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

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

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

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

References

^ "1,6-Hexanediol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 9 April 2022.
^ 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.
^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-04-09.
^ 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.
^ 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.
^ 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.
^ 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
^ 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.
^ 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.
^ 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
^ 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.
^ 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

[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.

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