Poly(propylene glycol) diglycidyl ether explained

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] It is REACH registered.[5]

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).[6] [7] 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.[8] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings,[9] adhesives, sealants, and elastomers. It produces epoxy coatings with high impact resistance.[10] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[11]

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.[12] [13]

The material maybe used to produce polymers with shape memory and good thermomechanical properties.[14] In addition, the molecule is used to synthesize other molecules.[15] [16] [17] [18] [19]

Toxicology

The toxicology of the material is reasonably well known.

See also

Further reading

External websites

Notes and References

  1. Web site: Poly(propylene glycol) (600) diglycidyl ether . 2022-05-17 . www.polysciences.com . en.
  2. Web site: Polypropylenglycol diglycidyl ether 26142-30-3 . 2022-05-17 . ChemicalBook . en.
  3. Web site: Poly(propylene glycol) diglycidyl ether . Sigma Aldrich.
  4. 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.
  5. Web site: Substance Information Polypropylene Glycol Diglycidyl Ether- ECHA . 2022-05-17 . echa.europa.eu . en-GB.
  6. 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.
  7. US. 1992-11-10. Ciba-Geigy Corp.. 5162547. Process for the preparation of glycidyl ethers.
  8. Web site: Zarnitz . Charles . Flexibilizing modifiers . CVC Thermosets.
  9. WO. 2015095994. 2015-07-02. Epoxy resin composition. Dow Global Technologies LLC. Shen. Yue. Zhan. Fu. Wu. Yan. Drumright. Ray E.. application.
  10. US. 8062468. 2011-11-22. Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins. Sika Technology AG. Finter. Jürgen. Kramer. Andreas. Schulenburg. Jan Olaf. Rheinegger. Urs.
  11. 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.
  12. Web site: 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 . 2022-05-17 . patents.justia.com . en.
  13. 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
  14. 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 . 10.1088/0964-1726/21/5/055022 . 2012SMaS...21e5022W . 136532406 . 0964-1726.
  15. 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 . en . 10 . 11 . 1184 . 10.3390/polym10111184 . 2073-4360 . 6290617 . 30961109. free .
  16. 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. . en . 23 . 4 . 495–498 . 10.1007/s11595-006-4495-y . 136731416 . 1993-0437.
  17. 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 . en . 130 . 38–46 . 10.1016/j.jct.2018.09.031 . 105754055 . 0021-9614.
  18. 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 . en . 7 . 46 . 28841–28852 . 10.1039/C7RA04215A . 2017RSCAd...728841K . 98934685 . 2046-2069. free .
  19. Plastification of Polypropylene Glycol Diglycidyl Ether-co-Citric Acid Copolyester on Polylactide . 2022-05-17 . 华东理工大学学报(自然科学版) . 2017 . 43 . 1 . 42–49 . 10.14135/j.cnki.1006-3080.2017.01.007 . 朱 . 麒霏 . 徐 . 璐. . 张 . 臣. . 陆 . 冲. . 程 . 树军 .

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