The preparation of hyperbranched aromatic and aliphatic polyether epoxies by chloride-catalyzed proton transfer polymerization from ABn and A2 + B3 monomers

Todd Emrick, Han Ting Chang, Jean M.J. Fréchet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

112 Scopus citations

Abstract

Hyperbranched polymers consisting of aromatic or aliphatic polyether cores and epoxide chain-end peripheries were prepared by proton transfer polymerization. AB2 diepoxyphenol monomer 1 proved to be well suited for the preparation of hyperbranched aromatic polymer 2 by this proton transfer polymerization. The use of chloride-ion catalysis, rather than conventional base catalysis, for the preparation of polymers from diepoxyphenol 1 offered a unique method to control the ultimate molecular weight of the polymer product through variations of the initial concentration of monomer 1 in tetrahydrofuran. An alternative route to hyperbranched polyether epoxies made use of commercially available or easily prepared aliphatic monomers of the types AB2, AB3, and A2 + B3. Although these aliphatic polymerizations can be initiated with a base, chloride-ion catalysis proved most effective for controlling the polymerization. The hyperbranched epoxies were characterized by NMR spectroscopy, gel permeation chromatography, and multi-angle laser light scattering. Chemical modification of the polymers after polymerization was carried out via nucleophilic addition on the epoxide groups or derivatization of the hydroxy substituents within the hyperbranched polymer structure. Spectroscopic measurements suggested that some such ring-opened materials may adopt reverse unimolecular micellar structures in appropriate solution environments.

Original languageEnglish (US)
Pages (from-to)4850-4869
Number of pages20
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume38
Issue numberSUPPL.
DOIs
StatePublished - Nov 27 2000

Keywords

  • Epoxy polymer
  • Hyperbranched polymer
  • Proton transfer polymerization

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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