Antibacterial activity of copolymers of trialkyl(4‐vinylbenzyl)ammonium chlorides with acrylonitrile

Abstract

Homopolymers of cetyldimethyl(4-viny1benzyl)ammonium chloride (VB 16), lauryldimethyl(4-vinylbenzyl)ammonium chloride (VB 12), and trimethyl (4-vinylbenzy1)ammonium chloride (VBI), and copolymers of these compounds with acrylonitrile were examined for antibacterial activity using B. subtilis, S. aureus, E. coli, and P. aeruginosa. All homopolymers and copolymers showed germicidal action to the bacterias, especially strong action to gram-positive B. subtilis and S. aureus. The strength of the germicidal action of the quaternary ammonium branches was in the order: VB16 > VB12 % VB1. ZUSAMMENFASSUNG:Die antibakterielle Wirkung von Homopolymeren von Cetyldimethyl(4-vinyl-benzy1)ammoniumchlorid (VB16), huryldimethyl(4-vinylbenzyl)ammoniumchlorid (VB 12) und Trimethyl(4-vinylbenzyl)ammoniumchlorid (VB 1) und deren Copolymeren mit Acrylnitril wurde untersucht. Alle Homo-und Copolymeren wirkten bei den getesteten Bakterienarten -B. subtilis, S. aureus, E. coli und P. aeruginosakeimtotend. Besonders starke Effekte zeigten sich bei gram-positiven B.-subtilis-und S.-aureus-Kulturen. Die keimtotende Wirkung nahm in der Reihe VB16 > VB12 % VBl ab.

Antibacterial and Bacterium Adsorbing Macromolecules

“…Senuma et al [36,37] synthesized poly[{dimethylhexadecyl-3-(and 4-)vinylbenzylammonium chloride}-co-acrylonitril]s, examining their antibacterial activities against E.coli, B.subtilies, and S.aureus. The activities have been found to be larger in Gram-positive bacteria than in gram-negative ones, and to increase with an increase in the QAS concentration in the copolymers.…”

“…Incorporation scheme of phosphonium biocides onto filter surfaces and the structures of the immobilized biocides(37).…”

Biocidal Activity of Polystyrenes That Are Cationic by Virtue of Protonation

“…Poly(1) is somewhat less active than is the magainin derivative, particularly toward the pathogenic S. aureus and E. faecium strains; however, this variation seems relatively modest in light of the profound difference in molecular structure between the peptide and poly(1) and the difference in effort required for chemical synthesis of the peptide vs the homopolymer. We compared poly(1) with poly(3) (synthesized from monomer 3 via reported methods 13,21 ) in order to evaluate the difference between N-protonation and N-quaternization as a source of positive charge. Poly(3) was reported to display antimicrobial activity in an agar-plate assay, 13,21 but in our liquid-medium assay, this material showed little or no Host-defense peptides, such as the magainins, are much more effective at disrupting bacterial cell membranes than at disrupting eukaryotic cell membranes.…”

Covalent attachment of quaternary ammonium compounds to a polyethylene surface via a hydrolyzable ester linkage: Basis for a controlled‐release system of antiseptics from an inert surface

“…A cell count of 10 8 cfu/mL was higher than that expected normally. For this reason, further experiments were carried out with a lower cell count of 10 5 or 10 6 cfu/mL, values consistent with those used by other workers 28, 30, 31. In addition, the immobilized quaternary ammonium salt samples (films) were investigated only with long alkyl chain lengths of 12 and 18 carbon atoms (as discussed later).…”

“…The reason for this sharp cutoff in activity is not clear at this stage. However, as mentioned previously, the initial cell count in these experiments was greater than that used by some researchers,28, 30, 31 and to investigate fully the activity of the quaternary ammonium compounds, further experiments were carried out with a lower initial cell concentration. Furthermore, the concentration of the quaternary ammonium salt, which had been immobilized, was expected to be lower than 1 × 10 −5 ; in all further experiments, it was reduced to 1 × 10 −6 M .…”