Quaternary Ammonium Salts as Germicides. III. Quaternary Ammonium Salts Derived from Cyclic Amines

Abstract

The activity of these compounds against E.typhosa is considerably below that already reported for cetyltriethylammonium bromide and cetyltri-M-butylammonium bromide. Summary N -Carbamylmethyl, N-carbethoxymethyl and Nß-acetoxyethyl derivatives of several quaternary ammonium compounds containing one Ncetyl or N-lauryl group and three low molecular weight N-alkyl radicals were prepared. The germicidal activity of these compounds was studied, and in some, cases the effect on the activity of different anions was tested.In the N-lauryl group of compounds the germicidal activity was improved by the substitution of a carbethoxymethyl or /3-acetoxyethyl group for an original N-methyl radical. In the N-cetyl group the reverse was true. The halide salts and the nitrate all gave about the same activity. Organic anions usually lowered the activity of the compound. Cincinnati, Ohio

Synthesis and micellar properties of surface-active ionic liquids: 1-Alkyl-3-methylimidazolium chlorides

“…The intense interest in studying short-chain ILs has not been matched by effort to study their surface active counterparts, although the latter have very interesting properties, in addition to being surface active: low melting points (32-34 and 86-87 • C, for C 12 MeImCl and C 12 PyCl, respectively) [61], high polarities (situated between those of dipolar aprotic solvents and protic ones) [62], and high chemical and thermal stabilities. Additionally, the presence of two alkyl groups in the imidazolium ring introduces a structural flexibility because its bulk can be tailored to ones need.…”

Oxazoline‐Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2

“…Antimicrobial polymers are suggested to disrupt the cytoplasmic membrane by two main mechanisms after the initial binding step: insertion of the polymer perpendicularly to the membrane with the formation of a either barrel-stave or toroidal transmembrane pores causing permeabilization and depolarization of the membrane or accumulation of the polymer at the membrane surface until a certain threshold concentration is reached causing subsequent disruption in a detergent like manner (carpet mechanism), with the consequent lysis of the bacterial cells. [23] It is possible that the different killing rates of 1b and 4b comparatively to 5 are due to different modes of action of these polymers. The polycation 5 is more effective in attaching to the bacterial cell surface due the higher positive charge per polymer chain, but less efficient in crossing the outer membrane of gram-negative bacteria and the thick peptidoglycan layer of the gram-positive bacteria and thus taking longer time to kill the bacteria.…”

“…[20,21] Most of the studies of polymers with antimicrobial activity are based on compounds and materials possessing quaternary ammonium salts in their structure since its antimicrobial activity has been known for decades. [22][23][24] Waschinski and co-workers reported the synthesis of a series of oxazoline-based polymers, terminated with quaternary ammonium groups (using a series of Nalkyl-N,N-dimethylamines but also pyridine), prepared via standard CROP. Their antimicrobial properties were later evaluated by determining the minimal inhibitory concentration (MIC) against Staphylococcus aureus.…”

Synthesis and characterization of 1-carbalkoxymethyl-4-hydroxy-1-methylpiperidinium chlorides

“…The effects of substituents, structures and anions of quaternary salts on the antimicrobial activity have been extensively studied. 1 The germicidal activity is the greatest in the compounds containing a long alkyl chain from 12 to 16 carbon atoms. 1 To increase solubility of the quaternary salts an ester group is introduced to compounds of a series of N-methylmorpholinium, N,N'-dimethyl-piperazinium, N-methyl-piperidinium salts and they were tested against same bacteria.…”