Poly(propylene glycol) diglycidyl ether

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.[1] They have the formula (C3H6O)n.C6H10O3[2] and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- [3] A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer.[4][5] It is REACH registered.[6]

Poly(propylene glycol) diglycidyl ether
Names
Other names
Polyoxypropylene diglycidyl ether; PPGDGE
Identifiers
ECHA InfoCard 100.130.913
Properties
(C3H6O)n.C6H10O3
Molar mass Variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Manufacturing

The product is made by taking polypropylene glycol and epichlorohydrin and reacting in the presence of a Lewis acid catalyst to form a halohydrin. The next step is dehydrochlorination with sodium hydroxide. This forms the diglycidyl ether. Waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine).[7][8] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Use

The molecule has 2 oxirane functionalities, and so a key use is modifying and reducing the viscosity of epoxy resins.[9][10] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,[11] adhesives, sealants, and elastomers. It produces epoxy coatings with high impact resistance.[12] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[13]

Synthesis of waterborne polymers has been a feature with this substance. As the basic building block is propylene oxide, there are 3 carbons per oxygen on the backbone. This confers some degree of water miscibility though not as good as ethylene oxide based molecules.[14][15]

The material maybe used to produce polymers with shape memory and good thermomechanical properties.[16] In addition, the molecule is used to synthesize other molecules.[17][18][19][20][21]

Toxicology

The toxicology of the material is reasonably well known.[22]

See also

Further reading
  • Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.{{cite book}}: CS1 maint: others (link)
  • Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.{{cite book}}: CS1 maint: location missing publisher (link)
  • Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.
  • "Dow Epoxy Resins" (PDF).

References
  1. "Poly(propylene glycol) (600) diglycidyl ether". www.polysciences.com. Retrieved 2022-05-17.
  2. "Polypropylenglycol diglycidyl ether | 26142-30-3". ChemicalBook. Retrieved 2022-05-17.
  3. "Poly(propylene glycol) diglycidyl ether". Sigma Aldrich.
  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. 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, archived from the original on 2022-04-11, retrieved 2022-03-29
  6. "Substance Information Polypropylene Glycol Diglycidyl Ether- ECHA". echa.europa.eu. Retrieved 2022-05-17.
  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. US 5162547, Roth, Martin; Wolleb, Heinz & Truffer, Marc-Andre, "Process for the preparation of glycidyl ethers", published 1992-11-10, assigned to Ciba-Geigy Corp.
  9. Zarnitz, Charles. "Flexibilizing modifiers" (PDF). CVC Thermosets.
  10. 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, archived from the original on 2022-04-11, retrieved 2022-03-29
  11. WO application 2015095994, Shen, Yue; Zhan, Fu & Wu, Yan et al., "Epoxy resin composition", published 2015-07-02, assigned to Dow Global Technologies LLC
  12. US 8062468, Finter, Jürgen; Kramer, Andreas & Schulenburg, Jan Olaf et al., "Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins", published 2011-11-22, assigned to Sika Technology AG
  13. 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.
  14. "US Patent for Water soluble polymers and polymer adducts along with aqueous solutions thereof Patent (Patent # 10,920,011 issued February 16, 2021) - Justia Patents Search". patents.justia.com. Retrieved 2022-05-17.
  15. Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 36-28, 52-60 Master of Science Thesis April 1997 Imperial College London
  16. Wei, Kun; Zhu, Guangming; Tang, Yusheng; Tian, Guangming; Xie, Jianqiang (2012-05-01). "Thermomechanical properties of shape-memory hydro-epoxy resin". Smart Materials and Structures. 21 (5): 055022. Bibcode:2012SMaS...21e5022W. doi:10.1088/0964-1726/21/5/055022. ISSN 0964-1726. S2CID 136532406.
  17. Castillejos, Sandra; Cerna, Jorge; Meléndez, Francisco; Castro, María Eugenia; Aguilar, Rocío; Márquez-Beltrán, César; González, Maykel (November 2018). "Bulk Modification of Poly(lactide) (PLA) via Copolymerization with Poly(propylene glycol) Diglycidylether (PPGDGE)". Polymers. 10 (11): 1184. doi:10.3390/polym10111184. ISSN 2073-4360. PMC 6290617. PMID 30961109.
  18. Huang, Biwu; Huang, Bofen; Du, Guoping; Chen, Weiqing (2008-08-01). "Synthesis of a novel UV-curable prepolymer polypropyleneglycol diglycidyl ether diacrylate". Journal of Wuhan University of Technology-Mater. Sci. Ed. 23 (4): 495–498. doi:10.1007/s11595-006-4495-y. ISSN 1993-0437. S2CID 136731416.
  19. Li, Yun; You, Yanhong; Huang, Weijia; Yang, Jie (2019-01-01). "Solubilities of CO2 in, densities and kinematic viscosities of poly(propylene glycol) diglycidyl ether and poly(ethylene glycol) monooleate". The Journal of Chemical Thermodynamics. 130: 38–46. doi:10.1016/j.jct.2018.09.031. ISSN 0021-9614. S2CID 105754055.
  20. Ke, Jiexi; Li, Xiaoyun; Wang, Feng; Jiang, Shuai; Kang, Maoqing; Wang, Junwei; Li, Qifeng; Wang, Zhijie (2017). "Non-isocyanate polyurethane/epoxy hybrid materials with different and controlled architectures prepared from a CO 2 -sourced monomer and epoxy via an environmentally-friendly route". RSC Advances. 7 (46): 28841–28852. Bibcode:2017RSCAd...728841K. doi:10.1039/C7RA04215A. ISSN 2046-2069. S2CID 98934685.
  21. 朱, 麒霏; 徐, 璐.; 张, 臣.; 陆, 冲.; 程, 树军 (2017). "Plastification of Polypropylene Glycol Diglycidyl Ether-co-Citric Acid Copolyester on Polylactide". 华东理工大学学报(自然科学版). 43 (1): 42–49. doi:10.14135/j.cnki.1006-3080.2017.01.007. Retrieved 2022-05-17.
  22. 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

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