Long-Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers

Macromol Rapid Commun. 2020 Aug;41(15):e2000225. doi: 10.1002/marc.202000225. Epub 2020 Jun 22.

Abstract

Long-chain epoxides and specifically alkyl glycidyl ethers represent a class of highly hydrophobic monomers for anionic ring-opening polymerization (AROP), resulting in apolar aliphatic polyethers. In contrast, poly(ethylene glycol) is known for its high solubility in water. The combination of hydrophobic and hydrophilic monomers in block and statistical copolymerization reactions enables the synthesis of amphiphilic polyethers for a wide range of purposes, utilizing micellar interactions in aqueous solutions, e.g., viscosity enhancement of aqueous solutions, formation of supramolecular hydrogels, or for polymeric surfactants. Controlled polymerization of these highly hydrophobic long-chain epoxide monomers via different synthesis strategies, AROP, monomer-activated anionic ring-opening polymerization, catalytic polymerization, or via postmodification, enables precise control of the hydrophilic/lipophilic balance. This renders amphiphilic polymers highly interesting candidates for specialized applications, e.g., as co-surfactants in microemulsion systems. Amphiphilic polyethers based on propylene oxide and ethylene oxide, such as poloxamers are already utilized in many established applications due to the high biocompatibility of the polyether backbone. Long alkyl chain epoxides add an interesting perspective to this area and permit structural tailoring. This review gives an overview of the recent developments regarding the synthesis of amphiphilic polyethers bearing long alkyl chains and their applications.

Keywords: amphiphilic polyethers; epoxide monomers; ethylene glycol; pluronics; poly(ethylene glycol).

Publication types

  • Review

MeSH terms

  • Epoxy Compounds / chemical synthesis
  • Epoxy Compounds / chemistry*
  • Ethylene Oxide / chemical synthesis
  • Ethylene Oxide / chemistry
  • Hydrophobic and Hydrophilic Interactions
  • Micelles
  • Poloxamer / chemical synthesis
  • Poloxamer / chemistry*
  • Polymerization
  • Polymers / chemical synthesis
  • Polymers / chemistry
  • Surface-Active Agents / chemistry

Substances

  • Epoxy Compounds
  • Micelles
  • Polymers
  • Surface-Active Agents
  • glycidyl ethers
  • Poloxamer
  • Ethylene Oxide