Wettability alteration of organo-vermiculites induced by layer charge and tailored bis-N-heterocyclic quaternary ammonium salts

Wettability is an important surface property that deserves to further explore the factors on its alteration.Series of bis-N-heterocyclic quaternary ammonium salts with different spacer length and N-heterocyclic headgroups(morpholinium(BMMB,BMMD and BMMH),piperidinium(BPMH)and piperazinium(BMPMH))have been synthesized and employed for altering the wettability of vermiculite and its derivates(Vts)treated by Li^(+)-saturated heating method.The results of X-ray diffraction(XRD),Fourier transform infrared spectroscopy(FT-IR),thermogravimetric analysis(TG-DTG),scanning electron microscopy(SEM)and N_(2)adsorption/desorption isotherms indicate that all of the bis-N-heterocyclic quaternary ammonium salts have been successfully inserted into the vermiculite layers,leading to the organic monolayer.The results of capillary rise tests combined with Lipophilic to Hydrophilic Ratio(LHR)values unveil the wettability alteration of the organo-Vts.As the layer charge decreases,the hydrophilicity of the organo-Vts gradually increases,which is probably caused by the decline in binding sites.As the result of the change in spacer length of modifier,the wetting properties of morpholinium-based organo-Vts change in order of BMMD-Vts>BMMH-Vts>BMMB-Vts,and difference in N-heterocyclic headgroups leads to the sequence of wettability:BMPMH-Vts>BPMH-Vts>BMMH-Vts.Layer charge of Vt,spacer length and the type of the N-heterocyclic headgroup of modifier have the synergistic effect on the regulation of the wettability.

Effects of quaternary ammonium chain length on the antibacterial and remineralizing effects of a calcium phosphate nanocomposite

Composites containing nanoparticles of amorphous calcium phosphate （NACP） remineralize tooth lesions and inhibit caries. A recent study synthesized quaternary ammonium methacrylates （QAMs） with chain lengths （CLs） of 3-18 and determined their effects on a bonding agent. This study aimed to incorporate these QAMs into NACP nanocomposites for the first time to simultaneously endow the material with antibacterial and remineralizing capabilities and to investigate the effects of the CL on the mechanical and biofilm properties. Five QAMs were synthesized： DMAPM （CL3）, DMAHM （CL6）, DMADDM （CL12）, DMAHDM （CL16）, and DMAODM （CL18）. Each QAM was incorporated into a composite containing 20% NACP and 50% glass fillers. A dental plaque microcosm biofilm model was used to evaluate the antibacterial activity. The flexural strength and elastic modulus of nanocomposites with QAMs matched those of a commercial control composite （n = 6; P 〉 0.1）. Increasing the CL from 3 to 16 greatly enhanced the antibacterial activity of the NACP nanocomposite （P 〈 0.05）; further increasing the CL to 18 decreased the antibacterial potency. The NACP nanocomposite with a CL of 16 exhibited biofilm metabolic activity and acid production that were 10-fold lesser than those of the control composite. The NACP nanocomposite with a CL of 16 produced 2-log decreases in the colony-forming units （CFU） of total microorganisms, total streptococci, and mutans streptococci. In conclusion, QAMs with CLs of 3-18 were synthesized and incorporated into an NACP nanocomposite for the first time to simultaneously endow the material with antibacterial and remineralization capabilities. Increasing the C/reduced the metabolic activity and acid production of biofilms and caused a 2-log decrease in CFU without compromising the mechanical properties. Nanocomposites exhibiting strong anti-biofilm activity, remineralization effects, and mechanical properties are promising materials for tooth restorations that inhibit caries.

Studies on a Cationically Modified Quaternary Ammonium Salt of Lignin

A new quaternary ammonium salt monomer was synthesized and a quaternary amination of lignin（ noted as QL）, with the monomer was carried out by grafting copolymerization. The products were characterized by Fourier Transform Infrared spectroscopy（ FTIR）. The experimental results indicate that the yield of the monomer was 99.06%, and the conversion of the monomer and the grafting yield of QL were 93.69% and 185.78%, respectively. The feasibility of QL as the flocculant to be applied in color removal of five artificial dyes, erioehrome black T（dye A）, gongo red（dye B ）, direct fast black G （dye C ）, cuprofix blue green B （dye D ）, and acid black ATT （dye E ） was examined. Results show that OL exhihits the favorable flocculation nerformance and high stability.

Superoxide Anion Radical Scavenging Ability of Quaternary Ammonium Salt of Chitosan

A series of N-alkyl or N-aryl chitosan quaternary ammonium salt were prepared using 96% deacetylated chitosan. Their scavenging activities against superoxide anion radical were investigated by chemiluminescence. The IC50 values of these compounds range from 280 to 880 μg/mL, which should be attributed to their different substitutes.

Quaternary ammonium-induced multidrug tolerant Streptococcus mutans persisters elevate cariogenic virulence in vitro

Dental caries are the most prevalent chronic infections in the oral cavity, and Streptococcus mutans acts as the main cariogenic bacterial species. Antibacterial quaternary ammonium compounds （QAs） have been developed to preveFnt or treat dental caries. However, there is no report on the tolerance of S. mutans to QAs. In this study, we investigated the development of S. mutans persistence induced by a novel dental caries defensive agent, dimethylaminododecyl methacrylate （DMADDM）, for the first time. Typical biphasic killing kinetics for persisters were observed in both S. mutans planktonic and biofilm cultures challenged by DMADDM at concentrations of 20 and 200 pg.mL- z respectively. The persisters tolerated six other antibiotics with different antibacterial mechanisms, while only daptomycin and vancomycin could slightly reduce the persister numbers in planktonic cultures. The distribution of persisters in DMADDM-treated biofilms was similar to that in the untreated control, except that the total biomass and biofilm height were significantly reduced. A higher exopolysaccharides （EPS）：bacteria ratio was observed in DMADDM-treated biofilms. Persisters in biofilms significantly upregulated gtf gene expression, indicating an increase in the bacteria＇s ability to produce EPS and an elevated capability of cariogenic virulence. Carbon source metabolism was significantly reduced, as related metabolic genes were all downregulated in persisters. Concentrations of 0.1 mM, 1 mM and 10 mM of extra glucose significantly reduced the number of persisters both in planktonic and biofilm conditions. The formation of non- inheritable and multidrug tolerant persisters induced by DMADDM suggested that drug tolerance and new persistent eradication strategies should be considered for oral antibacterial agents.

PREPARATION AND PHOTOSENSITIVITY OF WATER SOLUBLE PHENOLIC RESINS CONTAINING ACRYLOYL AND QUATERNARY AMMONIUM CHLORIDE GROUPS

New water soluble and photocrosslinkable prepolymers containing acrylate and quaternary ammonium salt groups were synthesized from epoxy phenolic resin via ring-opening reaction with acrylic acid and with aqueous solution of triethylamine hydrochloride successively. The second reaction needs no phase transfer catalyst to accelerate, since the product formed can act as a phase transfer catalyst. The prepolymer obtained contains both photocrosslinkable acrylate groups and hydrophilic quaternary ammonium salt groups. Optimum conditions for these reactions were studied. The photosensitivity of the prepolymer was also investigated. The effects of different photoinitiators, different crosslinkable diluent monomers and amine accelerator on the photosensitivity of the prepolymer were compared. The photoinitiator of hydrogen abstraction type is still effective without using amine or alcohol as accelerator, because the prepolymer contains a H beside the OH groups formed in the ring-opening reactions.

Flotation and adsorption of quaternary ammonium salts collectors on kaolinite of different particle size

The flotation behaviors of decyltrimethylammonium (103C), dodecyltrimethylammonium chloride (DTAC), tetradecyltrimethylammonium chloride (TTAC) and cetyltrimethylammonium chloride (CTAC) on kaolinite of different particle size fraction were studied. The adsorbed amount and adsorption isotherms of collectors on kaolinite were determined for painstaking investigation into the adsorption of quaternary amines at kaolinite-water interface by ultraviolet spectrophotometer methods. The flotation results show that the flotation recovery of kaolinite of different particle fraction increases with an increase in pH when 103C, DTAC, TTAC and CTAC are used as collectors. As the concentration of collectors increases, the flotation recovery increases. Particle size of kaolinite has a strong effect on flotation. The flotation recovery of fine kaolinite decreases with the carbon chain of quaternary ammonium salts collectors increasing, while coarse kaolinite is on the contrary. The adsorbed amount tests and adsorption isotherms show that adsorbed amount increases when the particle size of kaolinite increases or when the carbon chain length of quaternary ammonium salts increases. Within the range of flotation collector concentration, the longer the hydrocarbon chain, the more probable to be absolutely adsorbed by fine kaolinite particles and then the lower the collector concentration in the bulk, which leds to lower flotation recovery.

Direct synthesis of propylene carbonate from propylene and carbon dioxide catalyzed by quaternary ammonium heteropolyphosphatotungstate–TBAB system

In this paper,we have developed a highly efficient method for the direct preparation of propylene carbonate from propylene and carbon dioxide（CO2） using quaternary ammonium heteropolyphosphatotungstate–quaternary ammonium halide catalytic system with anhydrous hydrogen peroxide as an oxidant through one-pot two-step process.The effects of the amount of tetrabutylammonium bromide（TBAB）,the concentration of hydrogen peroxide and other reaction conditions were investigated.The catalyst system gave an optimum propylene oxide yield（91%） at75°C in oxidation step and the highest propylene carbonate yield（99%） at 140°C and 3.0 MPa in cycloaddition step.Based on the results,a reaction mechanism has been proposed.

QSAR Modeling of Toxicity of Quaternary Ammonium Compounds to Chlorella pyrenoidosa Using 2D and 3D Descriptors

To investigate the relationships between structures and toxicities of 13 quaternary ammonium compounds （QACs） to Chlorella pyrenoidosa, 2D- and 3D-QSAR models were built. The 2D-QSAR model included two parameters： averaged polarizability （a） and total connectivity （Tcon）. Furthermore, 3D-QSAR models were proposed by using comparative molecular field analysis （CoMFA） and molecular similarity index analysis （CoMSIA）. All these models were robust and predictive. To our interest, 3D-QSAR model suggested that the hydrophobieity of substituents was the dominating factor for the toxicities, electrostatic effect was the secondly important, and steric field gave the least contribution. Comparatively, the predictive ability of 3D-QSAR model is slightly more advantageous than that of 2D-QSAR. They can be used complementally in the toxicity description of this kind of compounds.

Synthesis and Structure of Ag(I)- Containing Coordination Polymers Based on Quaternary Ammonium Template Reagent

A novel coordination polymer [(C8H20N)(Ag2I3)]n ([C8H20N]+ = tetraethyl ammo- nium (TEA)) was synthesized by the reaction of AgI and C8H20NI at room temperature with pH = 6.5, and structurally characterized by means of X-ray single-crystal diffraction. It crystallizes in orthorhombic, space group Pna21 with a = 7.3323(9), b = 18.250(2), c =12.5294(15) ?, C6.33H16.16NAg2I3, Mr = 702.76, V = 1676.6(4) ?3, Z = 4, Dc = 2.784 g/cm3, F(000) = 1256.6, μ(MoKα) = 7.828 mm-1, the final R = 0.0529 and wR = 0.1586 for 1189 observed reflections with I > 2σ(I). X-ray analysis shows that the [Ag2I3]n- chain is built up by AgI4 tetrahedron and in combination with quaternary ammonium cations ([C8H20N]+) by static attractive forces to form the so-called organic-inorganic hybrid material.

Preparation and Properties of Poly(amidoamine) Dendrimer/Quaternary Ammonium Chitosan Hydrogels

A novel quaternary ammonium chitosan hydrogel modified by poly（amidoamine）（PAMAM） dendrimer was prepared by using glutaraldehyde as a cross-linker. The hydrogel was characterized by Fourier transform infrared spectroscopy（FTIR） and scanning electron microscopy（SEM）. The results confirmed its highly porous three-dimensional network structure. The swelling test of hydrogel proved that it had excellent swelling and p H-sensitive properties. The increasing PAMAM content or quaternization degree led to the increase in swelling properties. And the hydrogel with lower cross-linking agent concentration or quaternary ammonium chitosan concentration exhibited better swelling properties. The antibacterial results indicated that with the increase in the PAMAM content, quaternary ammonium chitosan concentration or cross-linking agent concentration, the hydrogels showed better antibacterial activities against both Staphylococcus aureus（S. aureus） and Escherichia coli（E. coli）. Thus, the hydrogel could serve as a promising antibacterial material in the future.

Current State and Development of Quaternary Ammonium Compounds Disinfectants in China

Quaternary ammonium compound are a class of broad-spectrum,high-efficiency and low-toxicity bactericide,which are widely used in daily life and industrial sterilization.Herein,the current state of domestic quaternary ammonium disinfectant products was summarized,as well as those new products developed and studied,and the development trend was also predicted.

Synthesis and Characterization of a Novel Liquid Crystalline Chitin Quaternary Ammonium Chitosan Salt

N -Butyl chitosan(NBCS) derivatives were prepared by introducing butyl groups into the amine groups of chitosan via Schiff base intermediates. The quaternization of NBCS was carried out by using ethyl iodide to produce water-soluble cationic polyelectrolytes. The degree of the substitution of the products was measured by means of the electron spectroscopy for a successful chemical analysis. The quaternary ammonium chitosan salt(QACS) was proved to be a novel cholesteric liquid crystalline chitin, by means of the polarized optical microscopy and the circular dichroism spectropolarimetry. The critical mass fraction of the QACS/formic acid solution forming a lyotropic liquid crystal phase was 50%, which was almost the same as that of the NBCS/formic acid solution, but much higher than that of the chitosan in the same solvent.

Synthesis of Chitosan Quaternary Ammonium Salts

A series of N-alkyl or N-aryl chitosan quaternary ammonium salts were prepared via Schiffs base intermediates. Quaternization of N-substituted chitosan derivatives was carried out using methyl iodide to produce water-soluble cationic chitosan quaternary ammonium salt. The products were characterized by IR, (HNMR)-H-1 and elemental analysis. The degree of substitution of chitosan quaternary ammonium salt was calculated by elemental analysis.

Synthesis of Polymer-Bonded Quaternary Ammonium Type Metal Porphyrins

The reaction of pyrrole with 4-hydroxybenzaldehyde and 4-pyridinecarboxaldehyde afforded new porphyrin ligand 1. Treatment of 1 with copper( II ) acetate, cobalt ( II ) acetate gave complexes 2-3 respectively. 2 and 3 reacted with Merrifield's peptide resin produced 4 and 5. Complexes 4 and 5 reacted with methyl iodide respectively gave 6-7. The new compounds 1-7 have been identified by H-1 NMR, IR, MS and UV-visible spectra, elemental analysis and AES.

Synthesis, Crystal Structure, Two-photon Absorption and Biological Imaging Application of a Water Soluble Carbazole Quaternary Ammonium Compound

A novel carbazole quaternary ammonium compound（abbreviated as T_2） had been synthesized and characterized by ~1H NMR, ^（13）C NMR and Mass spectrometry. The single-crystal structure has been determined by X-ray single-crystal diffraction. The electrochemical and two-photon absorption properties of T_2 were systematically studied by cyclic voltammetry and Z-scan determination methods, respectively. The results suggested that T_2 had a good oxidation-reduction and excellent nonlinear optical property. The two-photon absorption（TPA） value has a maximum corresponding to cross section σ = 7963.3 GM（Goeppert-Mayer units） at 700 nm, indicating potential applications in nonlinear optical materials. Furthermore, attributing to the excellent water solubility and low cytotoxicity, the compound was explored on its primary application in biological imaging.

Facile Bromination of Aromatic Ethers with Quaternary Ammonium Bromide and Iodosylbenzene

Aromatic ethers were conveniently brominated with quaternary ammonium bromide and iodosylbenzene in glacial acetic acid under mild conditions to give the corresponding monobromo-aromatic ethers in nearly quantitative yields.

Azobenzene quaternary ammonium salt for photo-controlled and reusable disinfection without drug resistance

The abuse of antibiotics causes severe bacterial resistance, and the shortage of antibiotics has created a global public health crisis. This situation has prompted people to develop new antibacterial agents independent of traditional antibiotics. Here, we created a series of photosensitive azobenzene-quaternary ammonium salt smart antibacterial agents by connecting azobenzene with amines with different chain lengths to improve the antibacterial selectivity of quaternary ammonium salt(QAS) and prevent the accumulation of active QAS in the environment. After trans-cis isomerization, the solubility of the title compound(compound 4) increased and the antibacterial property enhanced. The experimental results suggested that the antibacterial effect of compound 4 was significantly enhanced after 365 nm light irradiation, and it had photosensitive intelligent antibacterial activity and could be reused. Notably, we did not obtain any mutants of Staphylococcus aureus or Escherichia coli resistant to compound 4. In general,compound 4 has the advantages of high yield, photo-controllable antibacterial properties, reusability, and does not induce bacterial resistance. This photosensitive antibacterial compound provides a new idea for the construction of intelligent disinfectants and is expected to be a candidate for disinfectants in public facilities and medical architecture.

Facile Fabrication of Hyperbranched Polyacetal Quaternary Ammonium with pH-Responsive Curcumin Release for Synergistic Antibacterial Activity

In the current global crisis of antibiotic resistance,persuit of an effective multi-pathway collaborative approach to enhance antibacterial activity is urgently needed.Here,a kind of hyperbranched polyacetal quaternary ammonium(Hyper-ace-QA)with efficiently antibacterial function were synthesized by a succession of efficient click strategies.The high molecular weights can be obtained just after UV irradiation for 3 h,and the grafting ratio can be easily adjusted through controlling solvent system,molar ratio,and temperature.Cytotoxicity studies indicated that Hyper-ace-QA had good biocompatibility and can be used as a potential antibacterial dressing.More importantly,after in situ encapsulation of bioactive curcumin drugs into the hyperbranched intramolecular cavities,the acid-liable acetal linkers within the hyperbranched backbone made the loading antibacterial drugs rapidly release with pH-or bacterial-responsive behaviors since many bacteria can produce acids at the infection site by the combined actions of immune response and bacterial metabolism.Therefore,the integration of quaternary ammonium characteristics and pH-triggered curcumin release could facilitate the antibacterial activity against gram-positive Staphylococcus aureus.This work represents a synergistic strategy on offering important guidance to rational design of multifunctional antimicrobial vehicles,which would be promising therapeutic alternatives for first aid treatment of wound infection in critical situations.