1,4-Cyclohexanedimethanol diglycidyl ether

1,4-Cyclohexanedimethanol diglycidyl ether.svg skin-invert-image 2,2′-[Cyclohexane-1,4-diylbis(methyleneoxymethylene)]bis(oxirane) 1,4-Bis(glycidyloxymethyl)cyclohexane 1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane 2,2'-(1,4-Cyclohexanediylbis(methyleneoxymethylene))bis-oxirane 14228-73-0 3184513 55618 DTXSID1044805 238-098-4 61718 1S/C14H24O4/c1-2-12(6-16-8-14-10-18-14)4-3-11(1)5-15-7-13-9-17-13/h11-14H,1-10H2 VQMQXWYQIIUJIT-UHFFFAOYSA-N C1CC(CCC1COCC2CO2)COCC3CO3 14 24 4 1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane https://pubchem.ncbi.nlm.nih.gov/compound/61718#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 12 April 2022 en 10 April 2022 https://web.archive.org/web/20220410225727/https://pubchem.ncbi.nlm.nih.gov/compound/61718#section=Safety-and-Hazards live 07 Warning 315 317 319 412 261 264 264+265 272 273 280 302+352 305+351+338 321 332+317 333+313 337+317 362+364 501 1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family.https://www.carbosynth.com/carbosynth/website.nsf/(w-productdisplay)/AF1D41E1109A11E780257FBD0036A789 1,4-Cyclohexanedimethanol diglycidyl ether 2022-04-10 www.carbosynth.com 2022-04-11 https://web.archive.org/web/20220411203516/https://www.carbosynth.com/carbosynth/website.nsf/%28w-productdisplay%29/AF1D41E1109A11E780257FBD0036A789 live Its formula is C14H24O4 and the IUPAC name is 2-4-(oxiran-2-ylmethoxymethyl)cyclohexylmethoxymethyloxirane. It has the CAS number of 14228-73-0PubChem 1,4-Bis((2,3-epoxypropoxy)methyl)cyclohexane https://pubchem.ncbi.nlm.nih.gov/compound/61718 2022-04-10 pubchem.ncbi.nlm.nih.gov en 2022-04-10 https://web.archive.org/web/20220410225727/https://pubchem.ncbi.nlm.nih.gov/compound/61718 live and is REACH registered in Europe.Substance Information – ECHA https://echa.europa.eu/substance-information/-/substanceinfo/100.034.620 2022-04-11 echa.europa.eu en-GB 2022-04-11 https://web.archive.org/web/20220411203503/https://echa.europa.eu/substance-information/-/substanceinfo/100.034.620 live An industrial chemical, a key use is in the reduction of the viscosity of epoxy resin systems functioning as a reactive diluent.EP 2013-08-07 Dow Global Technologies LLC 2621994 Epoxy resin compositions Hefner Robert E.Jagtap Ameya Rajendra More Aarti 2022-08-01 Developments in reactive diluents: a review https://doi.org/10.1007/s00289-021-03808-5 Polymer Bulletin en 79 8 5667–5708 10.1007/s00289-021-03808-5 235678040 1436-2449 subscription Synonyms The material is known under various names which include: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 C 14 H 24 O 4 TRC https://www.trc-canada.com/product-detail/?C997973 2022-04-11 www.trc-canada.com 2022-04-11 https://web.archive.org/web/20220411203505/https://www.trc-canada.com/product-detail/?C997973 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 Manufacture 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.Crivello James V. 2006 Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization https://doi.org/10.1002/pola.21761 Journal of Polymer Science Part A: Polymer Chemistry 44 21 6435–6448 10.1002/pola.21761 2006JPoSA..44.6435C 0887-624X 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. Uses As the molecule has oxirane functionality, a key use is reducing the viscosity of epoxy resins.Monte Salvatore J. Diluents and viscosity modifiers for epoxy resins 1998 https://doi.org/10.1007/978-94-011-5862-6_24 Plastics Additives: An A-Z reference Polymer Science and Technology Series 1 211–216 Pritchard Geoffrey Dordrecht Springer Netherlands en 10.1007/978-94-011-5862-6_24 978-94-011-5862-6 2022-03-29 2022-04-11 https://web.archive.org/web/20220411203514/https://link.springer.com/chapter/10.1007/978-94-011-5862-6_24 live subscription These reactive diluent modified epoxy resins may then be further formulated into which may then be formulated into CASE applications: Coatings,WO 2015095994 2015-07-02 Epoxy resin composition Dow Global Technologies LLC Shen Yue Zhan Fu Wu Yan Drumright Ray E. application Adhesives, Sealants,14228-73-0 CAS DataBase https://www.chemicalbook.com/CASEN_14228-73-0.htm 2022-04-11 www.chemicalbook.com 2022-04-11 https://web.archive.org/web/20220411203519/https://www.chemicalbook.com/CASEN_14228-73-0.htm live Elastomers, and electronic encapsulant.JP 4965715 2012-07-04 Epoxy resin composition and semiconductor sealing material using the same Namics Corp. Yohei Hosono Hiroki Homma The use of the diluent does affect mechanical properties and microstructure of epoxy resins.Khalina Morteza Beheshty Mohammad Hosain Salimi Ali 2019-08-01 The effect of reactive diluent on mechanical properties and microstructure of epoxy resins https://doi.org/10.1007/s00289-018-2577-6 Polymer Bulletin en 76 8 3905–3927 10.1007/s00289-018-2577-6 105389177 1436-2449 subscription 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 https://doi.org/10.1007/s11998-022-00737-4 Journal of Coatings Technology and Research en 20 4 1207–1221 10.1007/s11998-022-00737-4 256749849 1935-3804 subscription It is also used as a monomer in UV curing systems.Sangermano M. Bongiovanni R. Malucelli G. Priola A. Pollicino A. Recca A. 2003-08-08 Fluorinated epoxides as surface modifying agents of UV-curable systems https://onlinelibrary.wiley.com/doi/10.1002/app.12244 Journal of Applied Polymer Science en 89 6 1524–1529 10.1002/app.12244 0021-8995 subscription In addition it is used to synthesize other molecules such as the acrylated version.Huang Biwu Deng Chong Xu Qinchang Chen Weiqing Zou Huaihua 2014-12-01 Synthesis of a novel UV-curable y error in source oligmer 1,4-cyclohexanedimethanol glycidyl ether acrylate and study on its UV-curing properties https://doi.org/10.1007/s11595-014-1082-5 Journal of Wuhan University of Technology-Mater. Sci. Ed. en 29 6 1283–1289 10.1007/s11595-014-1082-5 94880993 1993-0437 2022-04-11 2022-04-11 https://web.archive.org/web/20220411203532/https://link.springer.com/article/10.1007/s11595-014-1082-5 live subscription Toxicology The material is classed as a skin irritant.An assessment of skin sensitisation by the use of epoxy resin in the construction industry https://www.hse.gov.uk/research/rrpdf/rr079.pdf April 2022 UK Health and Safety Executive 2022-04-11 2021-10-09 https://web.archive.org/web/20211009155956/https://www.hse.gov.uk/research/rrpdf/rr079.pdf live Berdasco Nancy Anne M. Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds 2012-08-17 https://onlinelibrary.wiley.com/doi/10.1002/0471435139.tox083.pub2 Patty's Toxicology 491–528 Bingham Eula Hoboken, NJ, USA John Wiley & Sons, Inc. en 10.1002/0471435139.tox083.pub2 978-0-471-12547-1 2022-07-28 Waechter John M. Cohrssen Barbara Powell Charles H. 2022-07-28 https://web.archive.org/web/20220728141821/https://onlinelibrary.wiley.com/doi/10.1002/0471435139.tox083.pub2 live subscription See also Glycidol References Further reading Epoxy resin technology. 1968 Interscience Publishers Paul F. Bruins, Polytechnic Institute of Brooklyn 0-470-11390-1 New York 182890 Flick Ernest W. Epoxy resins, curing agents, compounds, and modifiers : an industrial guide 1993 978-0-8155-1708-5 Park Ridge, NJ 915134542 Lee Henry Handbook of epoxy resins 1967 McGraw-Hill Kris Neville 0-07-036997-6 [2nd, expanded work] New York 311631322 http://nmt.edu/academics/mtls/faculty/mccoy/docs2/chemistry/DowEpoxyResins.pdf Dow Epoxy Resins External links Hexion difunctional epoxy diluents https://web.archive.org/web/20220127104433/https://www.hexion.com/en-us/chemistry/epoxy-resins-curing-agents-modifiers/functional-modifiers/di-functional 2022-01-27 Denacol epoxy diluent range Cargill Reactive diluents AALChem DE 204 CHDMDGE Category:Glycidyl ethers Category:Reactive diluents Category:Cyclohexanes