Creation of Novel Green and Sustainable Gemini‐Type Cationics Containing Carbonate Linkages

Abstract

Novel gemini-type cationics containing carbonate linkages as biodegradable and chemically recyclable segments were designed and synthesized by a green process. The carbonate linkages were introduced into only the hydrophobic moiety or in both the hydrophobic and linker moieties of gemini-type cationics. They showed higher surface activities, such as a low critical micelle concentration value, a surface tension lowering, and a high adsorption efficiency, when compared to the corresponding single-type cationics. Also, the gemini-type cationics containing carbonate linkages in both the hydrophobic and the linker moieties showed stronger antimicrobial activities when compared to those only in the hydrophobic moiety. It was found that some gemini-type cationics containing carbonate linkages showed higher biodegradability compared to the conventional gemini-type cationics. The biodegradability of the gemini-type cationics decreased when a carbonate linkage was introduced into the hydrophobic moiety rather than the linker moiety. However, some gemini-type cationics containing carbonate linkages both in the hydrophobic and linker moieties showed ready biodegradability. The gemini-type cationics containing carbonate linkages in the hydrophobic moiety showed chemical recyclability by a lipase (E.C. 3.1.1.3).

Urea-based gemini surfactants: Synthesis, aggregation behaviour and biological activity

“…They appeared to be good stabilisers of polymer latex particles [30], separation agents in capillary chromatography [31], gelators of organic solvents [32], and reactants in the synthesis of silica mesophases [33]. A positive environmental impact of gemini surfactants is, apart from their low quantities used for a given application, to relate to the presence of biodegradable groups in their molecular structure such as carbon-carbon double bond [34] or carbonate linkages [35].…”

Gemini Alkyldeoxy-D-Glucitolammonium Salts as Modern Surfactants and Microbiocides: Synthesis, Antimicrobial and Surface Activity, Biodegradation

“…The biodegradability of the primary biodegradation intermediates: 1-dodecanol and trimethylene-1,3-bis( N -3-hydroxypropyl- N , N -dimethylammonium iodide) were about 70% and 10% respectively. Based on these results, one can state that the low biodegradability of studied gemini surfactant are due to the low biodegradability of the intermediate having two ammonium groups [36], [37]. Introduction of the carbonate linkage into the linker moiety between the two single-type cationics, or in both the hydrophobic and linker moieties, significantly improved the biodegrability of those surfactants.…”

Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages

“…We have also reported that carbonate linkages of gemini-type cationics are effective as biodegradable and chemically recyclable segments 9,10 .…”