Biobased cycloolefin polymers: Carvone-derived cyclic conjugated diene with reactive exo-methylene group for regioselective and stereospecific living cationic polymerization

Takenori Nishida, Kotaro Satoh, Shusaku Nagano, Takahiro Seki, Masazumi Tamura, Yingai Li, Keiichi Tomishige, Masami Kamigaito

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1 Citation (Scopus)

Abstract

Carvone, a naturally abundant chiral cyclic α,β-unsaturated carbonyl compound, was chemically transformed into cyclic exo-methylene conjugated dienes. The exo-methylene group had high reactivity in cationic polymerization and was efficiently polymerized in a controlled manner via regioselective 1,4-conjugated additions using initiating systems effective for living cationic polymerization of vinyl ethers. The obtained polymers with 1,3-cyclohexenyl units and tetra-substituted olefins in the main chain showed high glass transition temperatures over 110 °C. The chiral monomer underwent stereospecific polymerization to result in polymers with low solubility and weak packing of the rigid main chain in the lamellar layers. The racemic mixture resulted in soluble amorphous polymers, which were subsequently hydrogenated into cycloolefin polymers with enhanced thermal properties.

Original languageEnglish
Pages (from-to)1178-1183
Number of pages6
JournalACS Macro Letters
Volume9
Issue number8
DOIs
Publication statusPublished - 2020 Aug 18

ASJC Scopus subject areas

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

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