Kinetics of radical polymerization-XIX. study of the reactivities of phenols towards polyvinyl acetate radicals

M. Simonyi, F. Tüds, J. Pospiŝil

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21 Citations (Scopus)

Abstract

The reactions of substituted phenols with polyvinyl acetate radicals have been investigated. The stoichiometric coefficient of the reaction is independent of the substituents. Electron-repelling substituents in the phenols increase the rate of reaction. The reactivities of the investigated compounds satisfy the following Hammett equation logcβ=0·34-1·52σθ+. The steric hindrance existing in cases of tert. butyl substituents in both ortho positions is discussed on the basis of these experiments and on other data available in the literature. Possible reasons for anomalous behaviour of halogen substituents are considered. After discussing several possible explanations, the electrophilic substituent constants of fluorine, chlorine and bromine are corrected for the case of reaction with polyvinyl acetate radicals. The features of peroxy and carbon radicals in phenolic reactions are compared. The case of chain transfer is distinguished from inhibition.

Original languageEnglish
Pages (from-to)101-115
Number of pages15
JournalEuropean Polymer Journal
Volume3
Issue number1
DOIs
Publication statusPublished - Feb 1967

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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