1,6-Hexanediol diglycidyl ether

Last updated
1,6-Hexanediol diglycidyl ether
1,6-Hexanediol diglycidyl ether.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 240-260-4
PubChem CID
  • 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]
GHS-pictogram-exclam.svg
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]

Contents

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]

See also

Related Research Articles

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">Cyclohexanedimethanol</span> Chemical compound

Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

<span class="mw-page-title-main">Reactive diluent</span>

Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer.

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2 an industrial chemical used to reduce the viscosity of epoxy resins. These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6. It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.

<i>o</i>-Cresyl glycidyl ether Chemical compound

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C10H12O2 and the CAS Registry Number 2210-79-9. 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.

Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C11H20O4 and the CAS registry number of 17557-23-2. It has two oxirane groups per molecule. Its principle use is in modifying epoxy resins.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. It has the formula C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane, and the CAS number 14228-73-0. It is It is REACH registered in Europe. It is an industrial chemical and a key use is in the reduction of viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">C12–C14 alcohol glycidyl ether</span> Chemical compound

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family. It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane. Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Castor oil glycidyl ether</span> Chemical compound

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12 and the CAS number 14228-73-0. The IUPAC name is 2,3-bis[12-(oxiran-2-ylmethoxy)octadec-9-enoyloxy]propyl 12-(oxiran-2-ylmethoxy)octadec-9-enoate. A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

<span class="mw-page-title-main">Trimethylolethane triglycidyl ether</span> Chemical compound

Trimethylolethane triglycidyl ether (TMETGE) is an organic chemical in the glycidyl ether family. It has the formula C14H24O6 and the IUPAC name is 2-({2-methyl-3-[(oxiran-2-yl)methoxy]-2-{[(oxiran-2-yl)methoxy]methyl}propoxy}methyl)oxirane. The CAS number is 68460-21-9. A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Poly(propylene glycol) diglycidyl ether</span> Chemical compound

Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. They have the formula (C3H6O)n.C6H10O3 and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer. It is REACH registered.

<span class="mw-page-title-main">Diethylene glycol diglycidyl ether</span> Chemical compound

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C10H18O5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

References

  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. 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.
  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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