Bogumił Brycki

The biodegradation of monomeric and dimeric alkylammonium surfactants

Quaternary ammonium compounds (QACs) are salts known for having antiseptic and disinfectant properties. These compounds are toxic to aquatic organisms and should thus be removed from wastewater before its discharge into surface waters. The biodegradation of QACs takes place in the presence of microorganisms under aerobic conditions. The susceptibility of these compounds to degradation depends on numerous parameters. A number of them, such as the structure-adsorption on solids, and concentration of the QACs, as well as the presence of additional substances, have been reviewed in this article. Moreover, the biodegradability of new dimeric alkylammonium salts, i.e., cationic gemini surfactants, has been discussed and compared with that of anionic and nonionic geminis. The biodegradation study of monomeric and dimeric alkylammonium surfactants show that they are not easily degraded. The degradation process is very complex and strongly depends on the structure of the compound, adsorption-desorption processes on sludge, type of microorganism consortia and the presence of anions. Alkylammonium surfactants with biological motifs, like amide, peptides or carbohydrates, are much better degraded.

Synthesis, Molecular Structure, Spectral Properties and Antifungal Activity of Polymethylene-α,ω-bis(N,N-dimethyl-N- dodecyloammonium bromides)

Hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) (1), pentamethylene-1,5-bis(N,N-dimethyl-N-dodecylammonium bromide) (2), tetramethylene-1,4-bis(N,N-dimethyl-N-dodecylammonium bromide) (3), trimethylene-1,3-bis(N,N-dimethyl-N-dodecylammonium bromide) (4) and ethylene-1,2-bis(N,N-dimethyl-N-dodecylammonium bromide) (5) have been obtained and characterized by FTIR and NMR spectroscopy. DFT calculations have also been carried out. The optimized bond lengths, bond angles and torsion angles calculated by Hartree-Fock/3-21G(d,p) approach have been presented. MIC values for A. niger, P. chrysogenum, C. albicans have been determined and the relationship between MIC and spacer length has been discussed.

Synthesis and antimicrobial activities of new quats

Summary (Alkoxymethyl)dodecyldimethylammonium, (cycloalkoxymethyl)dodecyldimethylammonium, (alkylthiomethyl)dodecyldimethylarnmonium, (alkoxymethyl)dimethyloctylammonium, (cycloalkoxymethyl)dimethyloctylammonium and (alkylthiomethyl)dimethyloctylammonium chlorides were prepared in high yield. All the chlorides studied showed antimicrobial activity. The relationship between the chemical structure and antimicrobial activity was analyzed using the rough sets method.

FTIR and 13C NMR studies of hydrogen bonds and proton transfer in complexes of N-dodecyl-N,N-dimethylamine oxide with 26 phenols, carboxylic and mineral acids in solution.

Abstract Carbon-13 NMR spectra of N-dodecyl-N,N-dimethylamine oxide (DDAO) and its 26 hydrogen bonded complexes in deuteriated chloroform have been studied in relation to the variation of their aqueous pKa (AH) values ranging from −10 to 15. Correlation of the chemical shifts with pKa(AH) yields typical titration curves fitted by the equation: y = (Amax + Amin 10(C ± DX))/ (1 + 10(C ± DX)) where Amax and Amin are maximum (due to a molecular complex, B…HA) and minimum (due to a polar complex, B+H..A−) values of chemical shifts,and C and D are constants. The pKa values at the inflection point vary modestly with the carbon atom used in the calculation (from pKa = 4.55 to 4.87). A single carbonyl band in the second-derivative FTIR spectra of equimolar mixtures DDAO with four acetic acids in dichloromethane implies that hydrogen bonds are described by a strongly asymmetrical quasi-single minimum potential and that the tautomeric equilibrium, B…HA ⇌ B+H…A−, is excluded in the investigated complexes. Some equimolar complexes interact with a second molecule of DDAO to form homoconjugated complex, RCOO−(B.H.B)+. This interaction is controlled by pKa(AH). The equimolar complexes interact also with a second molecule of acid, and the second hydrogen bond causes only a minor effect on the first hydrogen bond. Relation between the acid-base titration curves and shape of potential energy function is discussed.

Preparation and NMR characterisation of hydrogen bonding in 2- and 2,6-bis- (N,N-diethylaminomethyl) - 4R-phenols

Abstract A series of Mannich mono- and di-bases derived from 4-substituted phenols were prepared and investigated by 1H and 13C NMR spectroscopy in chloroform-d1 solution. The chemical shifts of intramolecular hydrogen-bonded protons in Mannich bases depend on the pKa of the parent phenols. A correlation between Hammetts constants, σp, and 13C NMR chemical shifts of para carbon atoms has been found. All the results obtained from 1H and 13C NMR spectra show that in the case of the di-bases the OH proton symmetrically bridges the two nitrogen atoms. Earlier infrared studies showed that the proton oscillated between the two oxygen atoms in each of the respective di-N-oxide molecules. On average the structure is, however, symmetrical.

New Filtering Antimicrobial Nonwovens With Various Carriers for Biocides as Respiratory Protective Materials Against Bioaerosol

Abstract This study evaluated the bioactivity of polypropylene melt-blown filtering nonwovens used in respiratory protective devices (RPD) with a biocidal agent (alkylammonium microbiocides) on 2 mineral carriers. Two types of carriers were tested: a bentonite, with an aluminosilicate base, and a perlite, volcanic glass. High biostatic and biocidal effects of modified nonwovens with biocides were tested against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) bacteria. Nonwovens modified with a biocide on a bentonite carrier showed an opposite reaction to a biocide on a perlite. The research also showed that 10% concentration of a biocidal agent on a perlite carrier was sufficient to inhibit the growth of bacteria (100% reduction) placed in the structure of a filtering material during normal use of RPD. A comparison of the biological activity of 2 filtering materials, each containing 10% of a perlite and produced in a laboratory and industrial conditions, showed no statistically significant differences.

Monomeric and gemini surfactants as antimicrobial agents - influence on environmental and reference strains.

Quaternary ammonium salts (QAS) belong to surfactant commonly used both, in the household and in different branches of industry, primarily in the process of cleaning and disinfection. They have several positive features inter alia effectively limiting the development of microorganisms on many surfaces. In the present work, two compounds were used as biocides: hexamethylene-1,6-bis-(N,N-dimethyl-N-dodecylammonium bromide) that belongs to the gemini surfactant (GS), and its single analogue - dodecyl(trimethyl)ammonium bromide (DTAB). Two fold dilution method was used to determine the minimum concentration of compounds (MIC) which inhibit the growth of bacteria: Staphylococcus aureus (ATCC 6538 and an environmental strain), Pseudomonas aeruginosa (ATCC 85327 and an environmental strain), and yeast Candida albicans (ATCC 11509 and an environmental strain). The viability of cells in liquid cultures with addition of these substances at ¼ MIC, ½ MIC and MIC concentrations were also determined. The obtained results show that DTAB inhibits the growth of bacteria at the concentration of 0.126-1.010 µM/ml, and gemini surfactant is active at 0.036-0.029 µM/ml. Therefore, GS is active at more than 17-70-fold lower concentrations than its monomeric analogue. Strains isolated from natural environment are less sensitive upon testing biocides than the references strains. Both compounds at the MIC value reduced the number of cells of all strains. The use of too low concentration of biocides can limit the growth of microorganisms, but often only for a short period of time in case of special environmental strains. Later on, they can adapt to adverse environmental conditions and begin to evolve defence mechanisms.

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

Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-α,ω-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides), a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and 1H and 13C NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.

Quaternary ammonium biocides as antimicrobial agents protecting historical wood and brick

Quaternary ammonium compounds (QACs) are widely used in disinfection of water, surfaces and instruments as well as in textile, leather and food industries because of their relatively low toxicity, broad antimicrobial spectrum, non-volatility and chemical stability. Due to these advantages, QACs are also used in restoration and can be applied on historical material. The aim of this study was to determine the usefulness of biocides based on quaternary ammonium salts and containing various excipients in the protection of historical materials against microbial growth. The study determined the antimicrobial activity of three biocides against bacteria: Pseudomonas fluorescens, Staphylococcus equorum, Bacillus cereus, Bacillus muralis, Sporosarcina aquimarina and Rhodococcus fascians, and moulds: Chaetomium globosum, Penicillium citreonigrum, Cladosporium cladosporioides I, Acremonium strictum, Aspergillus fumigatus and Cladosporium cladosporioides II, all isolated from historical wood and brick. Staphylococcus equorum, Bacillus cereus, Sporosarcina aquimarina and Rhodococcus fascians bacteria, and Cladosporium cladosporioides I and Acremonium strictum moulds showed high sensitivity to quaternary ammonium biocides. Historical wood can be effectively disinfected by three applications of biocide A (30% v/v) containing dodecyl dimethyl ammonium chloride (DDAC), citric acid, propiconazole and propanol. Disinfection of historical brick can be carried out by three applications of 6% v/v solutions of biocide B (based on DDAC and ethylenediaminetetraacetic acid - EDTA) or biocide C (containing a non-ionic surfactant, DDAC and EDTA). Effective protection of historical building materials against microbial growth for a period of seven days can be achieved by the application of biocide A (30% v/v) on the wood surface and biocide B (6% v/v) on the brick surface.

Synthesis, Spectroscopic and Theoretical Studies of New Quasi-Podands from Bile Acid Derivatives Linked by 1,2,3-Triazole Rings

A novel method for the synthesis of bile acid derivatives has been developed using “click chemistry”. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester of bile acids and azide groups of 1,3,5-tris(azidomethyl)benzene gave a new quasi-podands with 1,2,3-triazole rings. The structures of the products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).