Neopentyl glycol diglycidyl ether

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.[2] It has two oxirane groups per molecule.[3] Its principle use is in modifying epoxy resins.[4]

Neopentyl glycol diglycidyl ether
Names
IUPAC name
2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane
Other names
Neopentyl glycol diglycidyl ether; 1,3-Bis(2,3-epoxypropoxy)-2,2-dimethylpropane; 2,2'-((2,2-Dimethyl-1,3-propanediyl)bis(oxymethylene))bis(oxirane); CCRIS 2640; Diglycidyl ether of neopentyl gylcol; EINECS 241-536-7; Heloxy WC68; UNII-9288EM7AOW; Oxirane, 2,2'-((2,2-dimethyl-1,3-propanediyl)bis(oxymethylene))bis-; Propane, 1,3-bis(2,3-epoxypropoxy)-2,2-dimethyl-
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.037.745
EC Number
  • 241-536-7
  • InChI=1S/C11H20O4/c1-11(2,7-12-3-9-5-14-9)8-13-4-10-6-15-10/h9-10H,3-8H2,1-2H3
    Key: KUAUJXBLDYVELT-UHFFFAOYSA-N
  • CC(C)(COCC1CO1)COCC2CO2
Properties
C11H20O4
Molar mass 216.275 g/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H317
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is REACH registered.[5] The IUPAC name is 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane.[6]

Synthesis

Neopentyl glycol and epichlorohydrin are reacted in the presence of a Lewis acid catalyst to form a halohydrin. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms Neopentyl glycol diglycidyl ether.[7] 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

A key use is modifying the viscosity and properties of epoxy resins. As an Epoxy modifier it is classed as an epoxy reactive diluent.[8] which may then be formulated into CASE applications: Coatings,[9] Adhesives,[10] Sealants and Elastomers and composite materials. These uses include cationic polymerization reactions.[11][12] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[13][14] It is also used to synthesize other molecules.[15][16][17]

Toxicity

NPGDGE toxicity is fairly well understood.[18] It is classed as a skin irritant and skin sensitizer.[19][20]

See also

References
  1. "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 30 March 2022.
  2. "System of Registries | US EPA". sor.epa.gov. Retrieved 2022-03-25.
  3. PubChem. "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-25.
  4. 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.
  5. "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-03-25.
  6. PubChem. "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-29.
  7. 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.
  8. Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, Dordrecht: Springer Netherlands, vol. 1, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, retrieved 2022-03-29
  9. 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
  10. Luo, Jing; Luo, Jianlin; Zhang, Jizhi; Bai, Yuanyuan; Gao, Qiang; Li, Jianzhang; Li, Li (September 2016). "A New Flexible Soy-Based Adhesive Enhanced with Neopentyl Glycol Diglycidyl Ether: Properties and Application". Polymers. 8 (9): 346. doi:10.3390/polym8090346. ISSN 2073-4360. PMC 6432166. PMID 30974622.
  11. Crivello, James V (March 2006). "Cationic photopolymerization of alkyl glycidyl ethers". Journal of Polymer Science Part A: Polymer Chemistry. 44 (9): 3036–3052. Bibcode:2006JPoSA..44.3036C. doi:10.1002/pola.21419.
  12. Bulut, Umut; Crivello, James V. (2005-04-02). "Investigation of the Reactivity of Epoxide Monomers in Photoinitiated Cationic Polymerization". Macromolecules. 38 (9): 3584–3595. Bibcode:2005MaMol..38.3584B. doi:10.1021/ma050106k. ISSN 0024-9297.
  13. 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.
  14. 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.
  15. Simokaitiene, Jurate; Lazauskaite, Ruta; Grazulevicius, Juozas V (2002-02-28). "Photopolymerization of neopentyl glycol diglycidylether and its compositions with 9-(2-oxiranylmethyl) carbazole". Journal of Photochemistry and Photobiology A: Chemistry. 147 (1): 55–61. doi:10.1016/S1010-6030(01)00622-0. ISSN 1010-6030.
  16. "Polyepoxy Compound Fixation / Yasuharu Noishiki, Teruo Miyata", Encyclopedia of Biomaterials and Biomedical Engineering (2 ed.), CRC Press, 2008, pp. 2263–2272, doi:10.1201/9780429154065-213, ISBN 978-0-429-15406-5, retrieved 2022-03-29
  17. Huang, Bi-wu; Huang, Bo-fen; Chen, Wei-qing; Ouyang, Zhi-qiang (2009-10-11). "Synthesis of a novel UV-curable prepolymer neopentyl glycol diglycidyl ether diacrylate and its cured film tensile property". Journal of Shanghai University (English Edition). 13 (5): 396. doi:10.1007/s11741-009-0511-3. ISSN 1863-236X. S2CID 124976924.
  18. 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
  19. US EPA, OCSPP (2013-03-01). "Chemical Data Reporting under the Toxic Substances Control Act". www.epa.gov. Retrieved 2022-03-29.
  20. Jolanki, R.; Sysilampi, M.-L.; Kanerva, L.; Estlander, T. (1989). "Contact Allergy to Cycloaliphatic Epoxy Resins". In Frosch, Peter; Dooms-Goossens, A.; Lachapelle, J.-M.; Rycroft, R. J. G.; Scheper, R. J. (eds.). Current Topics in Contact Dermatitis. Berlin, Heidelberg: Springer. pp. 360–367. doi:10.1007/978-3-642-74299-6_75. ISBN 978-3-642-74299-6.

Further reading
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