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

24 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

Fingerprint

Cationic surfactants
Carbonates
linkages
carbonates
surfactants
chemistry
synthesis
biodegradability
Biodegradability
biochemical oxygen demand
Critical micelle concentration
Biochemical oxygen demand
Lipases
activity (biology)
Bioactivity
Lipase
Ammonium Compounds
micelles

Keywords

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

ASJC Scopus subject areas

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

Cite this

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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).",
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author = "Taisuke Banno and Kazunobu Toshima and Kazuo Kawada and Shuichi Matsumura",
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AU - Banno, Taisuke

AU - Toshima, Kazunobu

AU - Kawada, Kazuo

AU - Matsumura, Shuichi

PY - 2009/8

Y1 - 2009/8

N2 - 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).

AB - 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).

KW - Antimicrobial activity

KW - Biodegradability

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KW - Chemical recycling

KW - Gemini-type cationic surfactant

KW - Lipase

KW - Surface activity

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