Synthesis and Properties of Cleavable Quaternary Ammonium Compounds

Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel a...

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Bibliographic Details
Published in:Journal of Oleo Science 2021, Vol.70(1), pp.59-65
Main Authors: Gilbert, Elangeni A., Guastavino, Javier F., Nicollier, Rocío A., Lancelle, María Verónica, Russell-White, Karen, Murguía, Marcelo C.
Format: Article
Language:English
Subjects:
Alcohols
Ammonium compounds
Antiinfectives and antibacterials
antimicrobial activity
Antimicrobial agents
Aqueous solutions
Biodegradability
carbonate
cleavable surfactants
Natural products
Properties (attributes)
quaternary ammonium
Quaternary ammonium salts
Reagents
surface activity
Surface properties
Surfactants
Synthesis
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Summary:Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel amphiphilic molecules with similar properties to those already known but more biodegradable. Based on benzalkonium chloride (BAC), novel carbonate cleavable surfactants (CBAC) were synthesized. The breakable carbonate sites make CBAC compounds more degradable and potentially more biodegradable than their non-cleavable BAC analogues. Natural products such as fatty alcohols (C8-C16) and N,N-dimethyl-2-aminoethanol were used as reagents for the synthesis of CBAC8-16. These amphiphilic compounds were characterized in terms of surface properties and antimicrobial activity against Gram-positive and Gram-negative bacteria, yeasts and moulds. The novel surfactants showed similar surface activities in aqueous solutions when compared to BAC. Also, the surface activity/structure relationship revealed that carbonate cleavable surfactants with n-decyl group (CBAC10) showed the same behaviour as non-cleavable BAC. Furthermore, compounds containing n-octyl (CBAC8), n-decyl (CBAC10) and n-dodecyl (CBAC12) group showed strong antimicrobial activities.
ISSN:1345-8957
1347-3352
DOI:10.5650/jos.ess20216