Effect Of Quaternary Ammonium Salts Research Articles

Strong, bacteriostatic and transparent polylactic acid-based composites by incorporating quaternary ammonium cellulose nanocrystals

Renewable natural fibers (e.g., cellulose nanocrystals (CNCs)) are being applied for reinforcing bio-based polylactic acid (PLA). For improvement in the interfacial compatibility between CNCs and PLA and the dispersibility of CNCs, a quaternary ammonium salt-coated CNCs (Q-CNCs) hybrid was prepared in this study based on an esterification self-polymerization method, and such hybrid was further utilized as a new strengthening/toughening nanofiller for producing the Q-CNCs-reinforced PLA composite. The results confirmed that quaternary ammonium salt coatings could efficiently enhance CNCs/PLA interfacial compatibility via mechanical interlocking and semi-interpenetrating networks. Attributing to the synergistic effect of quaternary ammonium salts and CNCs, a considerable enhancement in processing, mechanical, and thermal properties was gained in the obtained Q-CNCs-reinforced PLA composite. With the addition of 0.5 wt% Q-CNCs, the tensile strength, Young's modulus, and elongation at break of the Q-CNCs-reinforced PLA composite was raised by approximately 23 %, 37 % and 18 %, respectively; compared with pure PLA, the obtained composite had excellent bacteriostatic properties and good transparency. This work discusses the development of high-performance, low-cost and sustainable PLA-based composites on a potential application in packaging materials.

Experimental study on the effect of quaternary ammonium salt + monoethylene glycol compound to methane hydrate agglomeration in oil-water system

Natural gas hydrate has been a critical risk to the safety of offshore oil and gas well test and subsea transportation. Herein, the effect of three quaternary ammonium salt (QAS) surfactants with monoethylene glycol (MEG) to methane hydrate agglomeration in water-oil system was experimentally studied by a rocking cell. Based on the hydrate volume fraction and the slider trajectory, a classification method of the gas hydrate anti-agglomerants was established. All the QASs in this work show the capability of reducing hydrate agglomeration, among which N1,N3-didodecyl-N1,N1,N3,N3-tetramethylpropane-1,3-diaminium chloride (AA-2) has the best anti-agglomerating performance, and the slider moved at a large trajectory of 61–174 mm. The three QASs were compounded with 5, 10, and 15 wt% (based on water) MEG, respectively. Experimental results showed that AA-2 compounded with MEG (10 wt%) can effectively prevent hydrate agglomeration. The slider moved in the cell at the full trajectory range, showing the compound of grade A performance. The compound of QAS and MEG shows a synergistic effect. The addition of QAS can significantly reduce the required MEG dosage for the hydrate blockage prevention than the MEG only situation. Considering the economic factors of the filed hydrate management, the combination application of QAS + MEG may provide a promising option.

Synergistic antibacterial effect of quaternary ammonium salt functionalized metal–organic framework

Pseudomonas aeruginosa (P. aeruginosa) can be an important causative factor for severe infections in humans, especially in patients with respiratory infections.

Synthesis, characterization, antifungal properties of quaternary ammonium salts derived from natural rosin

In the paper, five quaternary ammonium salts derived from rosin were synthesized, characterized and their antifungal activities against different molds were studied. Choline quaternary ammonium salt and tetramethylammonium hydroxide were synthesized from dehydroabietic acid and the rosin ethanolamine ester quaternary ammonium salts which are new compounds were synthesized from propylene pimaric acid. Their structures were confirmed by FTIR, 1HNMR, 13CNMR, and high resolution mass spectrometry. The antifungal activities of the synthesized quaternary ammonium salts from rosin acid were tested by Oxford cup method, and their minimum inhibitory concentration was determined. The results show that quaternary ammonium salts derived from rosin acid have inhibitory effects on bamboo slices to some extent. Among them, propylene pimaric acid ethanolamine ester quaternary ammonium salts (A1 and A2) showed obvious antifungal activity in the Oxford cup test. The Oxford cup activity test and anti-mildew effect of quaternary ammonium salts (B1 and B2) synthesized from rosin acid are significant, and there are almost no mould growth on bamboo slices. It can be inferred that A1, A2, B1 and B2 are expected to be used as bamboo mildew inhibitors.Graphical abstractFive quaternary ammonium salts derived from rosin were synthesized and characterized; and their antifungal activities against different molds were studied.

The quaternary ammonium salts as corrosion inhibitors for X65 carbon steel under sour environment in NACE 1D182 solution: Experimental and computational studies

The effect of quaternary ammonium salts (DDPC and DDQC) with different concentrations on the corrosion inhibition of X65 carbon steel in the sour brine solution at different temperatures were investigated by weight loss, electrochemical measurements, surface analysis (SKP, AFM, SEM, EDS, and ATR-FTIR), and theoretical calculations (DFT, Monte Carlo, and molecular dynamics). It was found that the corrosion rate decreased with increasing inhibitor concentration, and the inhibition efficiency was about 98%. The adsorption of inhibitors on the metal surface followed the Langmuir adsorption isotherm. Furthermore, inhibitors showed good performance at elevated temperatures. The computational studies supported the experimental data well.

The effect of quaternary ammonium salts with different chain lengths on copper filling behavior in blind holes of printed circuit board

The rapid and defect free blind hole copper super filling is the key technology to ensure the quality and development of printed circuit boards (PCBs). The linear quaternary ammonium compounds with a low molecular weight are expected to act as a potential suppressor for blind hole copper filling. Here, three quaternary ammonium salts with different molecular chain lengths (the dodecyl trimethyl ammonium chloride, the cetyl trimethyl ammonium chloride and the stearyl trimethyl ammonium chloride) were selected to study the effects of the molecular chain length of quaternary ammonium salt on the copper filling behavior of the PCB blind holes. The electrochemical results show that the three quaternary ammonium salts show greater inhibition ability on copper deposition compared with the traditional additives (polyethylene glycol (PEG) and Cl−) and furthermore, the suppressor effect becomes stronger with the increase of molecular weight. The blind hole copper filling experiment of PCB is also carried out to study the copper filling capacity of three quaternary ammonium salts. The filling experiment reveals that compared with the traditional suppressors (PEG and Cl−), the filling quality of blind hole copper is significantly improved when the three quaternary ammonium salts are used as suppressors. Moreover, under the coordination of accelerator (bis (3-sulfopropyl) disulfide (SPS)), the three quaternary ammonium salts can realize more rapid copper super filling without chloride ion in the electrolyte. Cross-section and surface morphological analysis further illuminates that the quaternary ammonium salt as an suppressor can also more effectively inhibit the deposition of copper on the PCB surface and reduce the roughness of the copper layer. The present results imply that quaternary ammonium salts have greater advantages for copper filling and are expected to replace traditional suppressors as new suppressors.

Effect of Quaternary Ammonium Salts and 1,2,4-Triazole Derivatives on Hydrogen Absorption by Mild Steel in Hydrochloric Acid Solution.

The treatment of low-carbon steel items with hydrochloric acid solutions is used in many industrial technologies. This process is accompanied not only by metal corrosion losses, but also by hydrogen absorption by the metal. In this study, the kinetics of hydrogen cathodic reduction on low-carbon steel in 2 M HCl containing corrosion inhibitors, namely, quaternary ammonium salts and a 3-substituted 1,2,4-triazole, have been studied. Adsorption isotherms of corrosion inhibitors on cathodically polarized steel surface have been obtained. XPS data provide valuable information on the composition and structure of protective layers formed on steel in HCl solutions containing inhibitors. The main rate constants of the stages of gaseous hydrogen evolution and incorporation of hydrogen atoms into the metal have been determined. The addition of quaternary ammonium salts or 3-substituted 1,2,4-triazole inhibits the cathodic reduction of hydrogen and its penetration into steel in the HCl solution. 3-substituted 1,2,4-triazole is the most efficient inhibitor of hydrogen absorption. The inhibitory effect of this compound is caused by a decrease in the ratio of the hydrogen concentration in the metal phase to the degree of surface coverage with hydrogen. The maximum decrease in hydrogen concentration in the metal bulk in the presence of the 3-substituted 1,2,4-triazole is 8.2-fold, which determines the preservation of the plastic properties of steel as it corrodes in HCl solutions. The high efficiency of the 3-substituted 1,2,4-triazole as an inhibitor of hydrogen cathodic reduction and absorption results from strong (chemical) adsorption of this compound on the steel surface and the formation of a polymolecular protective layer.

The Antibacterial Effects of Quaternary Ammonium Salts in the Simulated Presence of Inhibitors in Root Canals: A Preliminary In-Vitro Study

To investigate the antibacterial effects of two newly developed quaternary ammonium salts (QAMs)-dimethylaminododecyl methacrylate (DMADDM) and dimethylaminohexadecyl methacrylate (DMAHDM), in the presence of various root canal inhibitors. Streptococcus gordonii, Enterococcus faecalis, Lactobacillus acidophilus and Actinomyces naeslundii were used. Dentine, dentine matrix and dead bacteria were selected as inhibitors. The antimicrobial efficacy of monomers of DMADDM and DMAHDM was tested against suspensions formed by mixtures of four bacterial species in or without the presence of inhibitors. The inhibition results were compared with chlorhexidine (CHX) and sodium hypochlorite (NaOCl). One-way analyses of variance (ANOVA) followed by Tukey’s multiple comparison test was performed to determine significant differences. The antibacterial effects of DMADDM and DMAHDM were variably inhibited dentine, dentine matrix and dead bacteria. CHX and NaOCl showed substantivity and they inhibited bacteria present in suspension. The concentration of compound decreased in the dentine block due to constant release. Bacterial colonies on the dentine surface and dentine tubules were significantly inhibited by DMADDM and DMAHDM. The antibacterial effects of DMADDM and DMAHDM could be inactivated by dentine, dentine matrix and dead bacteria, while DMADDM and DMAHDM could inhibit bacteria colonization on the dentine surface and kill bacteria present in dentinal tubules. The antibacterial effects of DMADDM and DMAHDM as free monomers in the presence of inhibitors was evaluated for the first time. They could help inhibit the residual bacteria on the dentine surface and in dentinal tubules that may cause persisting infection. Therefore the novel QAMs showed great potentials as root canal medication.

Immobilization of a Pd(II) complex on hydrophilic graphite oxide and its catalytic investigation in the Heck coupling reaction

Tetraamminepalladium(II) chloride monohydrate was heterogenized on hydrophilic graphite oxide (GO), synthesized by Brodie's method. Two samples, with Pd contents of 2% and 5%, referred to as Pd2 and Pd5, respectively, were prepared by a simple and scalable impregnation method and tested as catalysts in the Heck coupling reaction of styrene and bromobenzene. The reactions were carried out at 423 K for 3 hr by applying Na2CO3 as a base and N‐methylpirrolidone or dimethylformamide (DMF) as a solvent. The Pd complexes heterogenized on graphene oxide platelets proved to be highly active and selective catalysts, and Pd2 was more efficient than Pd5. The effect of quaternary ammonium salts (tetrabutylammonium bromide and tetrabutylammonium chloride, TBAC) as modifiers and that of an ionic liquid (1‐butyl‐3‐methylimidazolium bromide, bmim) was studied and the highest conversions were obtained when TBAC was employed. The selectivity for the formation of the main product, E‐stilbene, was in the range 91–96%. Catalyst recycling was investigated and the extent of leaching was found to depend on the solvent. DMF proved to be a highly feasible reaction medium because both catalysts could be recycled five times in this solvent without any significant loss of activity. A hot filtration test was performed and gave evidence that leaching of the active Pd species did not take place under the above reaction conditions. These results substantiate the fact that simple cationic Pd species can be efficiently immobilized on pristine GO surfaces without the requirement of the functionalization of GO with nitrogen‐containing mono or multidentate ligands as binding sites.

Effect of quaternary ammonium salts on spectral properties of zinc octacarboxyphthalocyanine

The paper presents results of the research on the influence of quaternary ammonium salts on UV–vis absorption and emission spectra of zinc octacarboxyphthalocyanine (ZnPcOC). Quaternary ammonium salts which show biological activity play a crucial role. In ZnPcOC solutions with a proper concentration of tetrabutylammonium salts (TBAX), a strong bathochromic shift band (λmax = 760 nm – “R” band) showing red fluorescence appears in time. The presence of tetrabutylammonium salt causes pH increase and, consequently, a gradual dissociation of carboxyl groups in ZnPcOC molecule. It seems that –COO— anions present in the ZnPcOC complex can interact with tetraalkylammonium cations, causing a decrease in symmetry in ZnPcOC complex. As a result, the “R”- band appears in the UV–vis spectrum of ZnPcOC.

The inhibitory effect of quaternary ammonium salt on bacteria in root canal

Persisting apical periodontitis is a primary reason for multiple intervention in root canal. Persisting bacteria in root canal is related with the persisting infection. Despite the advancement in treatment strategies the persisting infection is a major challenge for endodontist. Here we tested two newly developed quaternary ammonium methacrylates (QAMs) against endodontic bacteria and their biofilms. Their antibacterial and antibiofilm efficiency were compared with chlorhexidine (CHX) and sodium hypochlorite (NaOCl). We measured the MIC, MBC and MBIC of DMADDM and DMAHDM respectively. We also detected the ratio of live/dead bacteria and bacterial composition in the biofilms treated by DMADDM and DMAHDM. We found that DMADDM and DMAHDM could inhibit the growth of bacteria and biofilms formation. The result showed that novel QAMs were remarkably efficient than CHX against biofilms. In addition, we found that Streptococcus gordonii (S. gordonii) and Enterococcus faecalis (E. faecalis) were frequent isolates after treatment with antimicrobial compounds.

Light-Induced Production of Reactive Oxygen Species by a Novel Water-Soluble Benzophenone Derivative Containing Quaternary Ammonium Groups and Its Assembly on the Protein Fiber Surface.

Developing an efficient antimicrobial surface has important significance in the field of advanced biomaterials. A novel water-soluble benzophenone tetracarboxylamine derivative containing two quaternary ammonium groups, 3,3'-[4,4'-carbonyl-diphthalimide-]-bis(N-benzyl-N,N-dimethyl-N-propyl-1-aminium)dichloride (BPTCA-N), as a photoactive antibacterial agent was designed and synthesized. The ability of BPTCA-N to generate reactive oxygen species (ROS) in solution was investigated by light-induced activity. Its antibacterial activity in a dark environment or UV exposure was tested on Staphylococcus aureus and Escherichia coli. The influences of different solvents and the pH values on the ability of BPTCA-N to generate ROS were also discussed. BPTCA-N possessed high photoactivity and efficient ROS generation ability. The generation of hydroxyl radicals could be greatly affected by addition of other solvents and H+ or OH-. For the BPTCA-N solution at a concentration of 0.2 mmol/L, the reduction of S. aureus and E. coli could all reach 99.99%. The BPTCA-N compound was assembled onto wool protein fibers. The modified protein fabrics also showed excellent photoactivity and antibacterial property against S. aureus and E. coli. For the wool fabric modified with 30 g/L of BPTCA-N, the reduction of S. aureus could reach 99.91% and that of E. coli was 91.23%. BPTCA-N had the synergistic antibacterial effect of quaternary ammonium salt and benzophenones. It has potential application in the biomedical field as highly effective antimicrobial agent or antimicrobial biomaterial.

Utilizing dextran to improve hemocompatibility of antimicrobial wound dressings with embedded quaternary ammonium salts.

Dextran, a polysaccharide with interfering effects on coagulation hemeostasis was utilized to compensate the hostile effects of quaternary ammonium salts (QAS) embed in the backbone of a wound dressing membrane as an antimicrobial agent. Despite the high antimicrobial efficiency of QAS, their adverse hemolytic effect on red blood cells is a challenging problem for using them as an active antiseptic agent in wound dressings. To this end, wound dressings made through the sol-gel hydrolysis and polycondensation reaction of a methoxysilane-functionalized quaternary ammonium compound (Si-RQ) and a methoxysilane terminated polyurethane prepolymer (Si-PPU), at different compositions, were surface modified with dextran. The final dressings were then subjected to various biological and physico-mechanical assays. The low hemolysis rate and prolonged clot formation on dextran-modified dressings confirmed their excellent hemocompatibility. Meanwhile, the optimized dressings preserved their excellent antimicrobial activity against both Gram-positive and Gram-negative bacteria and a fungal strain up to 100% killing efficiency. In addition, they exhibited very good cytocompatibility since the fibroblast cells could grow and proliferate efficiently on their surface. The recorded results confirmed the effectiveness of surface anchored dextran for regulation of hemocompatibility of QAS containing wound dressings without deterioration of their basic physical and biological properties.

Exploring the conformational space of cobalt(III)–salen catalyst for CO2/epoxide copolymerization: Effect of quaternary ammonium salts on preference of alternative isomers

Model catalysts for CO2 /epoxide copolymerization based on Co(III) complexes were studied, with focus on the preference of their alternative isomers, cisβ vs. trans. The systems range from model structures without the co-catalyst, as derived from crystallographic data, to complex models with two (CH2 )4 N+ R3 co-catalyst chains (R = Me, Bu) grafted onto a Co(III)-salcy core. To explore the conformational space of the latter complexes, a computational protocol was developed, combining a systematic model-building approach with static and molecular dynamics calculations, and multilevel energy assessment (PM7 and DFT). Results demonstrate an influence of the co-catalyst on the relative stability of the isomers. The cisβ isomer is preferred for complexes without N+ -chains and the cisβ ↔ trans isomerization is feasible. Five-coordinate species and open-shell electronic configurations are energetically disfavored. The cisβ preference decreases with the introduction and enlargement of (CH2 )4 N+ R3 : both isomers can be populated for R = Me, while the trans isomer is visibly preferred for R = Bu. © 2018 Wiley Periodicals, Inc.

Effect of Quaternary Ammonium Salts on Phase Equilibrium Condition of Coal Mine Methane Gas Hydrate

Effect of Quaternary Ammonium Salts on Phase Equilibrium Condition of Coal Mine Methane Gas Hydrate

Synthesis, Characterization, and the Antioxidant Activity of Double Quaternized Chitosan Derivatives.

With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts’ quantity, single quaternized chitosan N-phenmethyl-N,N-dimethyl chitosan (PDCS), double quaternized chitosan N-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan (MP2MDCS), N-(1-pyridylmethyl-3-ylmethyl)-N,N-dimethyl chitosan (MP3MDCS), and N-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan (MP4MDCS) were designed and synthesized successfully through chemical modification of chitosan. Besides, three kinds of antioxidant activities, including hydroxyl radicals, superoxide radicals, and 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radicals were tested in vitro. As shown in this paper, the scavenging ability was ranking in order of MP3MDC > MP4MDCS > MP2MDCS > PDCS > chitosan at 1.6 mg/mL in all assays. All double quaternary ammonium salts were better than chitosan or the single quaternary ammonium salt. In addition, MP3MDCS could scavenge hydroxyl radicals totally at 1.6 mg/mL. MP2MDCS and MP4MDCS with more than 90% scavenging indices both had great scavenging ability on hydroxyl radicals or DPPH radicals. Furthermore, these data demonstrated that the increasing number of the positive charge would improve the antioxidant property of chitosan derivatives, and the N-pyridinium position would influence the scavenging radical ability.

Effect of Quaternary Ammonium Salts with Fluorine Atoms on Selected Weed Species

This study investigated the effects of four structurally different quaternary ammonium salts (QASs), i.e., tetrabutylammonium tetrafluoroborate [TBA][BF4], tetrahexylammonium tetrafluoroborate [THA][BF4], tetrabutylammonium hexafluorophosphate [TBA][PF6], and tetrahexylammonium hexafluorophosphate [THA][PF6], on the growth and development of three weed species: gallant soldier (Galinsoga parviflora Cav.), white goosefoot (Chenopodium album L.) and common sorrel (Rumex acetosa L.). The examined compounds were applied in the form of foliar spraying and soil application. Strong herbicidal properties of the examined compounds were demonstrated in case of their soil application. Growth inhibition of plant shoots and roots was greater with soil application than with foliar treatment. The strongest herbicidal activity of compounds was demonstrated with [TBA][BF4] have demonstrated [TBA][BF4] and [TBA][PF6] applied to the soil, while [THA][BF4] demonstrated the weakest herbicidal action. The increased concentration of applied QASs caused a decrease in the assimilation pigments, change in dry weight content and inhibition of length of shoots and roots.

Rapid, Microwave-Assisted Synthesis of Cubic, Three-Dimensional, Highly Porous MOF-205 for Room Temperature CO2 Fixation via Cyclic Carbonate Synthesis

A dual-porous, three-dimensional, metal-organic framework [Zn4O(2,6-NDC)(BTB)4/3] (MOF-205, BET = 4200 m2/g) has been synthesized using microwave power as an alternative energy source for the first time, and its catalytic activity has been exploited for CO2-epoxide coupling reactions to produce five-membered cyclic carbonates under solvent-free conditions. Microwave synthesis was performed at different time intervals to reveal the formation of the crystals. Significant conversion of various epoxides was obtained at room temperature, with excellent selectivity toward the desired five-membered cyclic carbonates. The importance of the dual porosity and the synergistic effect of quaternary ammonium salts on efficiently catalyzed CO2 conversion were investigated using various experimental and physicochemical characterization techniques, and the results were compared with those of the solvothermally synthesized MOF-205 sample. On the basis of literature and experimental inferences, a rationalized mechanism mediated by the zinc center of MOF-205 for the CO2-epoxide cycloaddition reaction has been proposed.

Dyeing polypropylene fiber with disperse dyes using quaternary ammonium salts

The results of studying the effect of quaternary ammonium salts in colorimetric coloration characteristics and thermodynamic parameters of the process of dyeing polypropylene fiber with disperse dyes are presented.

Effect of quaternary ammonium salts in the process of extracting oil filled rubber from latex

Currently, much attention is paid to the improvement of production technology of synthetic rubber. Much attention is given to rubber is produced by emulsion polymerization. This is due to the fact that rubbers produced by emulsion polymerization have a number of positive characteristics, and are widely used in the tire and rubber industry, in composite formulations for various purposes. In recent years, the technology of production of synthetic rubbers are widely used quaternary ammonium salts which are produced on an industrial scale. Application low and high molecular weight quaternary ammonium salts to reduce pollution of environ-mental protection, exclude the use of mineral salts without significant changes in the process flowsheet. It is found that quaternary ammonium salts react with the components of the emulsion system to form insoluble complexes, which are captured produced rubber crumb. However, Applications, quaternary salts in the manufacture of oil-filled rubber in the literature sources have not been given due attention. The study presents the results of research on the effect of the concentration of a coagulating agent, tempera tours and concentration of the dispersed phase in the process of coagulation of latex in the preparation of oil-filled rubber stamps SCS-30 ARKM-15. The concentration of the coagulating agent does not significantly affect the process of separation of the rubber from the latex. The process of isolation rubber latex is advantageously carried out at a reduced temperature. The concentration of the dispersed phase also provides material effect on the coagulation process. The lead researches mouthestablished that produced rubber, rubber compounds and vulcanizates based on these indicators correspond to their requirements.