Synthesis and properties of gemini-type cationic surfactants containing carbonate linkages in the linker moiety directed toward green and sustainable chemistry

Taisuke Banno, Kazunobu Toshima, Kazuo Kawada, Shuichi Matsumura

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Gemini-type cationic surfactants containing carbonate linkages as biodegradable and chemically recyclable segments, consisting of two long-chain alkyl groups, two quaternary ammonium groups and a linker moiety, were designed and synthesized as novel green and sustainable cationics with improved physicochemical and biological activities. The gemini-type cationics containing a carbonate linkage showed lower critical micelle concentration values compared to the corresponding single-type cationics. Also, the gemini-type cationics containing a carbonate linkage in the linker moiety showed strong antimicrobial activities. The biodegradability of the gemini-type cationics was significantly improved when a carbonate linkage was introduced into the linker moiety. The maximum biochemical oxygen demand-biodegradability of the gemini-type cationics containing a carbonate linkage in the linker moiety exceeded 70% after a 28-day incubation. Furthermore, the gemini-type cationics containing both a carbonate linkage and an n-dodecyl group showed a chemical recyclability using a lipase (E.C. 3.1.1.3).

Original languageEnglish
Pages (from-to)249-259
Number of pages11
JournalJournal of Surfactants and Detergents
Volume12
Issue number3
DOIs
Publication statusPublished - 2009 Aug 1

Keywords

  • Antimicrobial activity
  • Biodegradability
  • Carbonate linkage
  • Chemical recycling
  • Gemini-type cationic surfactant
  • Lipase
  • Surface activity

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

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