1,4-Butanediol diglycidyl ether

1,4-bis(2,3-epoxypropoxy)butane.svg 2,2′-[Butane-1,4-diylbis(oxymethylene)]bis(oxirane) 1,4-Bis(2,3-epoxypropoxy)butane (Tetramethylenebis(oxymethylene))dioxirane 1,4-Bis(2,3-epoxypropyloxy)butane 1,4-Bis(glycidyloxy)butane 1,4-Bis(oxiranylmethyloxy)butane 1,4-Butane diglycidyl ether 1,4-Butanediol diglycidyl ether 1,4-Diglycidyloxybutane Butane-1:4-diol diglycidyl ether Butanediol diglycidyl ether Tetramethylene glycol diglycidyl ether 2,2'-(1,4-Butanediylbis(oxymethylene)bisoxirane) 2425-79-8 correct FDA E9MU425FIB 1450123 16147 219-371-7 1S/C10H18O4/c1(3-11-5-9-7-13-9)2-4-12-6-10-8-14-10/h9-10H,1-8H2 SHKUUQIDMUMQQK-UHFFFAOYSA-N D88722 17046 C1C(O1)COCCCCOCC2CO2 10 18 4 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.PubChem 1,4-Butanediol diglycidyl ether https://pubchem.ncbi.nlm.nih.gov/compound/17046 2022-04-02 pubchem.ncbi.nlm.nih.gov en Its main use is in modifying epoxy resins especially viscosity reduction.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 It is REACH registered.Substance Information - ECHA https://echa.europa.eu/substance-information/-/substanceinfo/100.017.611 2022-04-02 echa.europa.eu en-GB The IUPAC name is 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane. Synthesis 1,4-Butanediol 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 dehydrochlorination reaction.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 One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight. Uses A key use is modifying the viscosity and properties of epoxy resinsMonte Salvatore J. Diluents and viscosity modifiers for epoxy resins 1998 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 which may then be formulated into CASE applications: Coatings,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 Adhesives, Sealants, Elastomers, composite materials, fillers, putties, plasters, modelling clay and semiconductors. It also has a number of medical applications.Ji Gyu Yeul Oh Chang Hyun Moon Byung Gwan Yi Seong Han In Bo Heo Dong Hwa Kim Ki-Tack Shin Dong Ah Kim Keung Nyun June 2015 Efficacy and Safety of Sodium Hyaluronate with 1,4-Butanediol Diglycidyl Ether Compared to Sodium Carboxymethylcellulose in Preventing Adhesion Formation after Lumbar Discectomy Korean Journal of Spine 12 2 41–47 10.14245/kjs.2015.12.2.41 1738-2262 4513167 26217381Nicoletti A. Fiorini M. Paolillo J. Dolcini L. Sandri M. Pressato D. 2013-01-01 Effects of different crosslinking conditions on the chemical–physical properties of a novel bio-inspired composite scaffold stabilised with 1,4-butanediol diglycidyl ether (BDDGE) Journal of Materials Science: Materials in Medicine en 24 1 17–35 10.1007/s10856-012-4782-4 23053811 22093094 1573-4838 Fiorani Andrea Gualandi Chiara Panseri Silvia Montesi Monica Marcacci Maurilio Focarete Maria Letizia Bigi Adriana 2014-10-01 Comparative performance of collagen nanofibers electrospun from different solvents and stabilized by different crosslinkers Journal of Materials Science: Materials in Medicine en 25 10 2313–2321 10.1007/s10856-014-5196-2 24664673 5270837 1573-4838 The molecule is also used to synthesize other molecules.Wu Chi Zuo Ju Chu Benjamin February 1989 Molecular weight distribution of a branched epoxy polymer: 1,4-butanediol diglycidyl ether with cis-1,2-cyclohexanedicarboxylic anhydride Macromolecules 22 2 633–639 10.1021/ma00192a021 1989MaMol..22..633W 0024-9297 Xue Yu Chen Hongyue Xu Chao Yu Dinghua Xu Huajin Hu Yi 2020 Synthesis of hyaluronic acid hydrogels by crosslinking the mixture of high-molecular-weight hyaluronic acid and low-molecular-weight hyaluronic acid with 1,4-butanediol diglycidyl ether RSC Advances en 10 12 7206–7213 10.1039/C9RA09271D 35493875 9049836 2020RSCAd..10.7206X 214083413 free As an Epoxy modifier it is classed as an epoxy reactive diluent. The use of the diluent does effect 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 Polymer Bulletin en 76 8 3905–3927 10.1007/s00289-018-2577-6 105389177 1436-2449 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 Toxicity The toxicity is fairly well known and understood and is rated as a severe skin and eye irritant. Contact dermatitis is also possible.1,4-Butanediol diglycidyl ether - Hazardous Agents Haz-Map https://haz-map.com/Agents/4025 2022-04-02 haz-map.comJolanki Riitta Estlander Tuula Kanerva Lasse February 1987 Contact allergy to an epoxy reactive diluent: 1,4-butanediol diglycidyl ether Contact Dermatitis 16 2 87–92 10.1111/j.1600-0536.1987.tb01385.x 2952443 36846087 Wiley online Berdasco Nancy Anne M. Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds 2012-08-17 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 Waechter John M. Cohrssen Barbara Powell Charles H. 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 websites 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 Category:Glycidyl ethers Category:Reactive diluents