1,4-Cyclohexanedimethanol diglycidyl ether

The material is known under various names which include:{{Cite web |title=14228-73-0 {{!}} 1,4-Cyclohexanedimethanol Diglycidyl Ether {{!}} 2,2'-[1,4-Cyclohexanediylbis(methyleneoxymethylene)]bis[oxirane]; 1,4-Bis(glycidoxymethyl)cyclohexane; 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether; 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane; 1,4-Bis[(glycidyloxy)methyl]cyclohexane; 1,4-Cyclohexanedimethanol diglycidyl Ether {{!}} {{chem|C|14|H|24|O|4}} {{!}} TRC |url=https://www.trc-canada.com/product-detail/?C997973 |access-date=2022-04-11 |website=www.trc-canada.com |archive-date=2022-04-11 |archive-url=https://web.archive.org/web/20220411203505/https://www.trc-canada.com/product-detail/?C997973 |url-status=live }}

• 2,2'-[1,4-Cyclohexanediylbis(methyleneoxymethylene)]bis[oxirane]
• 1,4-Bis(glycidoxymethyl)cyclohexane
• 1,4-Bis(hydroxymethyl)cyclohexane diglycidyl Ether
• 1,4-Bis[(2,3-epoxypropoxy)methyl]cyclohexane
• 1,4-Bis[(glycidyloxy)methyl]cyclohexane
• 1,4-Cyclohexanedimethanol diglycidyl Ether

The manufacturing process involves reacting cyclohexanedimethanol with epichlorohydrin, using a Lewis acid as catalyst, to form a halohydrin. This is followed by washing with sodium hydroxide in a dehydrochlorination step to form the epoxide rings.{{Cite journal |last=Crivello |first=James V. |date=2006 |title=Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization |url=https://doi.org/10.1002/pola.21761 |journal=Journal of Polymer Science Part A: Polymer Chemistry |volume=44 |issue=21 |pages=6435–6448 |doi=10.1002/pola.21761 |bibcode=2006JPoSA..44.6435C |issn=0887-624X|url-access=subscription }} The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

As the molecule has oxirane functionality, a key use is reducing the viscosity of epoxy resins.{{Citation |last=Monte |first=Salvatore J. |title=Diluents and viscosity modifiers for epoxy resins |date=1998 |url=https://doi.org/10.1007/978-94-011-5862-6_24 |work=Plastics Additives: An A-Z reference |series=Polymer Science and Technology Series |volume=1 |pages=211–216 |editor-last=Pritchard |editor-first=Geoffrey |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-94-011-5862-6_24 |isbn=978-94-011-5862-6 |access-date=2022-03-29 |archive-date=2022-04-11 |archive-url=https://web.archive.org/web/20220411203514/https://link.springer.com/chapter/10.1007/978-94-011-5862-6_24 |url-status=live |url-access=subscription }} These reactive diluent modified epoxy resins may then be further formulated into which may then be formulated into CASE applications: Coatings,{{Cite patent|country=WO|number=2015095994|pubdate=2015-07-02|title=Epoxy resin composition|assign1=Dow Global Technologies LLC|inventor1-last=Shen|inventor1-first=Yue|inventor2-last=Zhan|inventor2-first=Fu|inventor3-last=Wu|inventor3-first=Yan|inventor4-last=Drumright|inventor4-first=Ray E.|status=application}} Adhesives, Sealants,{{Cite web |title=14228-73-0 {{!}} CAS DataBase |url=https://www.chemicalbook.com/CASEN_14228-73-0.htm |access-date=2022-04-11 |website=www.chemicalbook.com |archive-date=2022-04-11 |archive-url=https://web.archive.org/web/20220411203519/https://www.chemicalbook.com/CASEN_14228-73-0.htm |url-status=live }} Elastomers, and electronic encapsulant.{{Cite patent|country=JP|number=4965715|pubdate=2012-07-04|title=Epoxy resin composition and semiconductor sealing material using the same|assign1=Namics Corp.|inventor1-first=Yohei|inventor1-last=Hosono|inventor2-first=Hiroki|inventor2-last=Homma}} The use of the diluent does affect mechanical properties and microstructure of epoxy resins.{{Cite journal |last1=Khalina |first1=Morteza |last2=Beheshty |first2=Mohammad Hosain |last3=Salimi |first3=Ali |date=2019-08-01 |title=The effect of reactive diluent on mechanical properties and microstructure of epoxy resins |url=https://doi.org/10.1007/s00289-018-2577-6 |journal=Polymer Bulletin |language=en |volume=76 |issue=8 |pages=3905–3927 |doi=10.1007/s00289-018-2577-6 |s2cid=105389177 |issn=1436-2449|url-access=subscription }}{{Cite journal |last1=Pastarnokienė |first1=Liepa |last2=Jonikaitė-Švėgždienė |first2=Jūratė |last3=Lapinskaitė |first3=Neringa |last4=Kulbokaitė |first4=Rūta |last5=Bočkuvienė |first5=Alma |last6=Kochanė |first6=Tatjana |last7=Makuška |first7=Ričardas |date=2023-07-01 |title=The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings |url=https://doi.org/10.1007/s11998-022-00737-4 |journal=Journal of Coatings Technology and Research |language=en |volume=20 |issue=4 |pages=1207–1221 |doi=10.1007/s11998-022-00737-4 |s2cid=256749849 |issn=1935-3804|url-access=subscription }}

It is also used as a monomer in UV curing systems.{{Cite journal |last1=Sangermano |first1=M. |last2=Bongiovanni |first2=R. |last3=Malucelli |first3=G. |last4=Priola |first4=A. |last5=Pollicino |first5=A. |last6=Recca |first6=A. |date=2003-08-08 |title=Fluorinated epoxides as surface modifying agents of UV-curable systems |url=https://onlinelibrary.wiley.com/doi/10.1002/app.12244 |journal=Journal of Applied Polymer Science |language=en |volume=89 |issue=6 |pages=1524–1529 |doi=10.1002/app.12244 |issn=0021-8995|url-access=subscription }} In addition it is used to synthesize other molecules such as the acrylated version.{{Cite journal |last1=Huang |first1=Biwu |last2=Deng |first2=Chong |last3=Xu |first3=Qinchang |last4=Chen |first4=Weiqing |last5=Zou |first5=Huaihua |date=2014-12-01 |title=Synthesis of a novel UV-curable {{sic|nolink=y|reason=error in source|oligmer}} 1,4-cyclohexanedimethanol glycidyl ether acrylate and study on its UV-curing properties |url=https://doi.org/10.1007/s11595-014-1082-5 |journal=Journal of Wuhan University of Technology-Mater. Sci. Ed. |language=en |volume=29 |issue=6 |pages=1283–1289 |doi=10.1007/s11595-014-1082-5 |s2cid=94880993 |issn=1993-0437 |access-date=2022-04-11 |archive-date=2022-04-11 |archive-url=https://web.archive.org/web/20220411203532/https://link.springer.com/article/10.1007/s11595-014-1082-5 |url-status=live |url-access=subscription }}

The material is classed as a skin irritant.{{Cite web |title=An assessment of skin sensitisation by the use of epoxy resin in the construction industry |url=https://www.hse.gov.uk/research/rrpdf/rr079.pdf |date=April 2022 |website=UK Health and Safety Executive |access-date=2022-04-11 |archive-date=2021-10-09 |archive-url=https://web.archive.org/web/20211009155956/https://www.hse.gov.uk/research/rrpdf/rr079.pdf |url-status=live }}{{Citation |last1=Berdasco |first1=Nancy Anne M. |title=Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds |date=2012-08-17 |url=https://onlinelibrary.wiley.com/doi/10.1002/0471435139.tox083.pub2 |work=Patty's Toxicology |pages=491–528 |editor-last=Bingham |editor-first=Eula |place=Hoboken, NJ, USA |publisher=John Wiley & Sons, Inc. |language=en |doi=10.1002/0471435139.tox083.pub2 |isbn=978-0-471-12547-1 |access-date=2022-07-28 |last2=Waechter |first2=John M. |editor2-last=Cohrssen |editor2-first=Barbara |editor3-last=Powell |editor3-first=Charles H. |archive-date=2022-07-28 |archive-url=https://web.archive.org/web/20220728141821/https://onlinelibrary.wiley.com/doi/10.1002/0471435139.tox083.pub2 |url-status=live |url-access=subscription }}

• Glycidol

{{Reflist}}

• {{Cite book|url=https://www.worldcat.org/oclc/182890|title=Epoxy resin technology.|date=1968|publisher=Interscience Publishers|others=Paul F. Bruins, Polytechnic Institute of Brooklyn|isbn=0-470-11390-1|location=New York|oclc=182890}}
• {{Cite book|last=Flick|first=Ernest W.|url=https://www.worldcat.org/oclc/915134542|title=Epoxy resins, curing agents, compounds, and modifiers : an industrial guide|date=1993|isbn=978-0-8155-1708-5|location=Park Ridge, NJ|oclc=915134542}}
• {{Cite book|last=Lee|first=Henry|url=https://www.worldcat.org/oclc/311631322|title=Handbook of epoxy resins|date=1967|publisher=McGraw-Hill|others=Kris Neville|isbn=0-07-036997-6|edition=[2nd, expanded work]|location=New York|oclc=311631322}}
• {{Cite web|url=http://nmt.edu/academics/mtls/faculty/mccoy/docs2/chemistry/DowEpoxyResins.pdf|title=Dow Epoxy Resins}}

• [https://www.hexion.com/en-us/chemistry/epoxy-resins-curing-agents-modifiers/functional-modifiers/di-functional Hexion difunctional epoxy diluents]
• [https://nagaseamerica.com/product/denacol-aliphatic-epoxies-5/ Denacol epoxy diluent range]
• [https://www.cargill.com/bioindustrial/chemmod-reactive-diluents Cargill Reactive diluents]
• [https://www.aalchem.com/en/product/category/diluent-dilu AALChem DE 204 CHDMDGE]

{{Glycidyl ethers}}

{{DEFAULTSORT:Cyclohexanedimethanol diglycidyl ether, 1,4-}}

Category:Glycidyl ethers

Category:Reactive diluents

Category:Cyclohexanes