Effect of phenol and derivatives on atom transfer radical polymerization in the presence of air

Yves Gnanou, Gürkan Hizal*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

87 Scopus citations

Abstract

The various phenolic compounds in conjunction with Cu(II) or Cu(I)-N,N,N′,N″,N″-pentamethyl diethylenetriamine (PMDETA) complexes are used to initiate atom transfer radical polymerization (ATRP) of methyl methacrylate, styrene, and methyl acrylate in the presence of a limited amount of air at temperatures in the range of 80-110°C. Meanwhile, an effort is directed toward the elucidation of the role of phenol and derivatives in ATRP catalyzed by Cu(II)/PMDETA. The catalytic sequence involves the formation of Cu(I) by electron transfer from phenol to Cu(II); Cu(I) so formed can then react in two distinctly different ways: with organic halide to form a propagating radical or with oxygen to form copper salt in its higher oxidation state; and regeneration of Cu(I) by excess phenol. Such regeneration of Cu(I) would be expected to lead to polymerization as a result of the consumption of oxygen and phenol as well. The phenols with electron releasing groups tended to increase the conversion of the polymerization. In this respect, sodium phenoxide, a more effective additive was found, whereas p-nitro phenol was the least effective. The obtained polymers displayed the common features of a controlled polymerization such as molecular weight control and low polydispersity index value (Mw/Mn > 1.5).

Original languageEnglish (US)
Pages (from-to)351-359
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume42
Issue number2
DOIs
StatePublished - Jan 15 2004

Keywords

  • Atom transfer radical polymerization
  • Methyl acrylate
  • Methyl methacrylate
  • Phenol derivatives
  • Styrene

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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