Synthesis and Antibacterial Activity of Polymerizable Acryloyloxyalkyltriethyl Ammonium Salts

Abstract

This study reports an efficient and practical synthetic approach for the synthesis of a particularly important class of polymerizable quaternary ammonium salts (PQASs), that is, acryloxyalkyltriethylammonium bromides (AATEABs), which may find application as antimicrobial coatings for commercial membranes with antifouling and anti‐biofouling properties, to be used for wastewater treatment. The synthetic method is based on a simple two‐step procedure from commercially available substrates, entirely carried out under air and without any need for chromatographic purification. All the newly synthesized AATEABs were tested for their antimicrobial activity, and the results showed that AATEABs bearing an alkyl chain of 11 and particularly 12 carbon atoms possessed significant activity against Gram positive bacteria and yeast strains.

Preparation and properties of antibacterial ABS plastics based on polymeric quaternary phosphonium salts antibacterial agents

“…The results of MIC and MBC of every monomer were shown in Table . It could be seen from Table that the values decreased when the alkyl chain length increased from 3 to 11, implying a stronger antibacterial activity could be achieved by increasing alky chain length of antibacterial monomer, just as results of other researches . This phenomenon could be explained by the antibacterial mechanism of quaternary phosphonium salts.…”

“…It could be seen from Table 4 that the values decreased when the alkyl chain length increased from 3 to 11, implying a stronger antibacterial activity could be achieved by increasing alky chain length of antibacterial monomer, just as results of other researches. 32,33 This phenomenon could be explained by the antibacterial mechanism of quaternary phosphonium salts. Firstly, the antibacterial molecules absorb onto the membrane of bacteria through the cationic groups, and then the hydrophobic alkyl chain inserts into the membrane of bacteria and disrupt it, leading the death of bacteria.…”

Viscosity Modification of Polymerizable Bicontinuous Microemulsion by Controlled Radical Polymerization for Membrane Coating Applications

“…The method for the PBM preparation reported by Galiano et al [1] was used with the mass fraction of each component shown in Table 1. The antimicrobial [11] and polymerizable AUTEAB surfactant was chemically bound to the solid PBM matrix upon co-polymerization. Other components used were the cross-linking agent ethylene glycol dimethacrylate (EGDMA) and the co-surfactant 2-hydroxyethylmethacrylate (HEMA).…”

New Polymeric Films with Antibacterial Activity Obtained by UV-induced Copolymerization of Acryloyloxyalkyltriethylammonium Salts with 2-Hydroxyethyl Methacrylate

“…In this field, we recently reported a novel and practical synthetic approach to a particularly interesting class of polymerizable quaternary ammonium salts (PQASs), which are ω-(acryloyloxy)- N , N , N -triethylalcan-1-aminium bromides (or acryloyloxyalkyltriethylammonium bromides, AATEABs), as shown in Scheme 1 [46].…”

“…We previously assessed the antimicrobial activity of the newly synthetized AATEABs against several Gram-positive and Gram-negative bacteria and yeast strains [46]. The results obtained showed that the AATEABs bearing a C-11 and a C-12 alkyl chain linker (11-(acryloyloxy)- N , N , N -triethylundecan-1-aminium bromide or acryloyloxyundecyltriethylammonium bromide, AUTEAB, and 12-(acryloyloxy)- N , N , N -triethyldodecan-1-aminium bromide (or acryloyloxydodecyltriethylammonium bromide, ADTEB, respectively) were the most active, in particular, against Gram-positive bacteria Staphylococcus aureus and Streptococcus pyogenes [46]. The higher bioactivity of AUTEAB and ADTEAB with respect to the other derivatives with shorter alkyl chain linkers was also recently theoretically interpreted by ab initio modeling calculations [50].…”