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Long‐Chain Alkyl Epoxides and Glycidyl Ethers: An Underrated Class of Monomers
Author(s) -
Verkoyen Patrick,
Frey Holger
Publication year - 2020
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.202000225
Subject(s) - amphiphile , polymerization , monomer , polymer chemistry , alkyl , copolymer , ethylene oxide , chemistry , self healing hydrogels , ethylene glycol , micelle , polymer , cationic polymerization , ring opening polymerization , materials science , aqueous solution , organic chemistry
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.