Synthesis of Poly(p-hydroxy-α-methylstyrene) by Cationic Polymerization and Chemical Modification

Hiroshi Ito*, C. Grant Willson, Jean Frechet, M. Jean Farrall, Eva Eichler

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

92 Scopus citations

Abstract

High molecular weight, soluble poly(p-hydroxy-α-methylstyrene) has been synthesized for the first time by cationic polymerization of p-[(tert-butoxycarbonyl)oxy]-'-methylstyrene with boron trifluoride etherate as an initiator in liquid sulfur dioxide followed by thermolytic deprotection. Cationic polymerization of p-acetoxy-α-methylstyrene in dichloromethane followed by hydrazinolysis afforded the title compound, but the polymerization was accompanied by partial cleavage of the protecting group. Conventional cationic polymerization of p-[(tert-butoxycarbonyl)oxy]-α-methylstyrene in dichloromethane resulted in formation of low molecular weight polymer accompanied by partial cleavage of the protecting group. Ether monomers, such as p-methoxy- and p-(ethoxymethoxy)-α-methylstyrenes, readily underwent cationic polymerization, while the p-(2-methoxyethoxy)methyl derivative suffered from partial deprotection and cross-linking. Removal of the ether protecting group was, in all cases, accompanied by chain degradation and/or cross-linking. Chemical modification of poly(α-methylstyrene) and poly(p-bromo-α-methylstyrene) by lithiation followed by hydroxylation produced cross-linked materials.

Original languageEnglish (US)
Pages (from-to)510-517
Number of pages8
JournalMacromolecules
Volume16
Issue number4
DOIs
StatePublished - Jan 1 1983

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of Poly(p-hydroxy-α-methylstyrene) by Cationic Polymerization and Chemical Modification'. Together they form a unique fingerprint.

Cite this