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1.
New bactericidal polyamides with quaternary ammonium or phosphonium salts were prepared, and their antimicrobial activities were explored. The polyamides were synthesized by the polycondensation of diethyl‐l‐tartrate or chloromethylated diethyl‐l‐tartrate with ethylenediamine in dry absolute ethanol. The polyamides were modified to yield polymers with either quaternary ammonium or phosphonium salts. The polymers were characterized with elemental microanalysis and 1H‐NMR and IR spectra. The antimicrobial activity of the polymers bearing onium salts was studied against Gram‐negative bacteria (Escherichia coli, Pseudomones aeruginosa, Shigella sp., and Salmonella typhae), Gram‐positive bacteria (Bacillus subtilis and Bacillus cereus), and a fungus (Trichophytum rubrum) by the cut‐plug and viable‐cell‐count methods. Although all the polymers showed high antibacterial activity, some had no antifungal activity. The tributyl phosphonium salt of the polyamide was more effective against both Gram‐negative and Gram‐positive bacteria than the triethyl ammonium and triphenyl phosphonium salts of the polyamide. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 4780–4790, 2006  相似文献   

2.
This study describes the effect of antibacterial activity of newly reported five different novel insoluble bead‐shaped polymer‐supported multiquaternary ammonium salts (PM quats) viz., bis‐quat, tris‐quat (2 Nos.), tetrakis‐quat, hexakis‐quat containing two, three, four, and six quaternary ammonium groups, respectively. The presence of number of quaternary ammonium groups in each salt was established already through Fourier‐transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, and chloride ion analyzes. The antibacterial activities of these five different PM quats against three different bacteria viz., Staphylococcus aureus, Klebsiella pneumoniae, and Pseudomonas aeruginosa were investigated by serial dilution and spread plate method and compared the same with a monoquat containing single quaternary ammonium group. The extent of antibacterial activity has been measured in terms of colony forming units (CFU) at different time intervals. The observed results show that all the PM quats exhibited excellent‐antibacterial activity against each bacterium. On the basis of the CFU values, the antibacterial activity was found to increase from bis‐quat to hexakis‐quat, which reveals that the activity of PM quats increases with increase in the number of quaternary ammonium groups. The mechanism of interaction of quats with bacterial cytoplasmic membrane has been explained as an adsorption‐like phenomenon. The reusability of highly active hexakis‐quat against Staphylococcus aureus was studied and the activity was found to reduce after first cycle. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010  相似文献   

3.
Diethyl-benzyl-[3-methyldimethoxyl)]silpropyl ammonium chloride (DEBSAC) was synthesized from N,N-diethyl-aminopropyl-methyldimethoxysilane (DEAPMDES) and benzyl chloride. Diethyl-2,3-epoxypropyl-[3-methyldimethoxyl)] silpropyl ammonium chloride (DEEPSAC) was synthesized from DEAPMDES and epoxy chloropropane. Trimethyl-[3-methyldimethoxyl)] silpropyl ammonium chloride (TMSAC) was synthesized from trimethylamine and γ-chloropropylmethyldimethoxysilane (CPMDMS). The products were characterized by 1H NMR, 13C NMR, and IR. The surface tension measurements showed that the organosilicon quaternary salts exhibit a lower surface tension and a lower critical micelle concentration (CMC) than the hydrocarbon counterparts. The plate count method experiments illustrated that DEEPSAC has a better degree of antibacterial activity against Escherichia coli than DEBSAC. The solubilizing effects of the organosilicon quaternary salts on organosilicone were studied by pseudo-ternary phase diagrams of synthesized products/cosurfactant(n-butanol)/water/octamethylcyclotetrasiloxane. The solubilizing activities decreased in the order of TMSAC > DEBSAC > DEEPSAC.  相似文献   

4.
Four cationic surfactants of quaternary hexammonium silane chloride based on hexamethylenetetramine and alkyl chloride were synthesized. The chemical structures of the prepared cationic surfactants were elucidated using Fourier transform infrared (FT‐IR) spectroscopy and mass spectrometry analysis. The surface and thermodynamic properties of the prepared surfactants were also studied. The performance of these cationic surfactants as microfouling agents against two strains of Gram‐negative bacteria, namely, Pseudomonas aeruginosa and Escherichia coli, and two strains of Gram‐positive bacteria, namely, Staphylococcus aureus and Bacillus subtilis, were evaluated as antimicrobial agents. The results showed that the maximum antimicrobial activity was detected for N‐hexamethylenetetramine‐N‐ethyl silane ammonium trichloride (Ah). The maximum and minimum antimicrobial activities were 73 and 60 % against S. aureus and E. coli, respectively, at a concentration of 5 mg/l, pH 7, and 37 °C.  相似文献   

5.
Oligomeric poly(styrene‐co‐acrylonitrile) quaternary ammonium salts were prepared through reactions of trimethylamine with corresponding poly(styrene–acrylonitrile–vinyl benzyl chloride)s, which were synthesized by the free‐radical polymerization of a mixture of styrene, acrylonitrile, and vinyl benzyl chloride. Then, oligomeric poly(styrene‐co‐acrylonitrile)‐modified clays were prepared through the cation exchange of the sodium ions in the clay with the corresponding poly(styrene‐co‐acrylonitrile) quaternary ammonium salts. The poly(styrene–acrylonitrile–vinyl benzyl chloride)s, poly(styrene‐co‐acrylonitrile) quaternary ammonium salts, and their clay complexes were characterized with infrared spectroscopy, gel permeation chromatography, thermogravimetric analysis, proton nuclear magnetic resonance, X‐ray diffraction, and transmission electron microscopy. X‐ray diffraction and transmission electron microscopy studies showed that these novel clay complexes were well intercalated. Furthermore, thermogravimetric analysis data indicated that this series of polymerically modified clays had high enough thermal stability for nanocomposites by melt blending. The thermal treatment of one of these novel clays at 250°C under nitrogen was also conducted. Solubility and infrared studies of this thermally treated clay complex revealed that a novel polyimine/enamine structure clay complex had been formed in the gallery of the clay. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009  相似文献   

6.
Quaternary ammonium salts Quats‐C8, Quats‐C12, and Quats‐C18 with different alkyl chain lengths have been successfully synthesized, and used for modifying silk fabrics. The optimum reaction conditions of initiator concentration, curing temperature, curing time, and monomer concentration have been studied. The modified fabrics of silk‐g‐C8, silk‐g‐C12, and silk‐g‐C18 were characterized by FTIR spectra. Antibacterial test showed that the modified silk fabrics possessed potent antibacterial activity against both Gram‐positive Staphylococcus aureus and Gram‐negative Escherichia coli. The carbon number in the alkyl chain of monomers Quats‐C8, Quats‐C12, and Quats‐C18 can affect the antibacterial efficacy. With longer alkyl chain, the antibacterial efficacy increased. The quaternary ammonium salts‐modified silk fabrics have small change on the tensile strength and wrinkle recovery angle, and have shown potential practical application. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133, 43450.  相似文献   

7.
Bi‐functional antibacterial material was prepared by co‐grafting N‐halamine and quaternary ammonium salt monomers from cellulose fiber. The grafted fiber was characterized by Fourier transform infrared spectra, and X‐ray photoelectron spectra. The N‐halamine derived from the precursor 4‐[(acryloxy)methyl]‐4‐ethyl‐2‐oxazolidinone via chlorination treatment and the oxidative chlorine (Cl+) leaching behavior were investigated. The antibacterial activities of singly (only QAs‐functionalized or only Cl+‐releasing) and dual (QAs‐functionalized and Cl+‐releasing) functional cellulose fibers were tested against Gram‐negative Escherichia coli and Gram‐positive Staphylococcus aureus. Compared to singly functionalized formulations, the bi‐functional cellulose fiber exhibited excellent and rapid bactericidal performance against both E. coli and S. aureus. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014 , 131, 40070.  相似文献   

8.
Electrospinning from a capillary is one of the methods for the production of nanofibers. The specific properties of such fibers result first of all from their large specific surface and the high porosity of the fiber mat. This article presents a process for producing functional nanofibers with antimicrobiological properties by electrospinning from polyacrylonitrile/dimethyl sulphoxide solution containing a bioactive agent based on quaternary ammonium salts (N, N, n, n,‐didecyl‐N,N‐dimethylammonium chloride, Bis‐(3‐aminopropyl)‐dodecylamine) and 2‐propanol. The structure of the nanofibers obtained and their antimicrobial activity are investigated. A 5 wt % addition of bioactive preparation to the polymer solution (concentration of active substance in solution about 1.5 wt %) makes it possible to obtain fibers showing good bactericidal properties. After 6 h in contact with these fibers, Escherichia coli are eliminated to a level of 99.84% and Staphylococcus aureus to 99.99%. The IR spectrophotometric measurements do not indicate a residue of solvent in the bioactive nanofibers and show an increase in content of CH and CH2 groups in relation to the pure nanofibers, which is connected with the presence of the biocide. Their degree of crystallinity determined by the X‐ray scattering method is 44.4%. The nanofibers obtained can be designed for medical and filtration applications. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013  相似文献   

9.
Thermally‐induced self‐crosslinking behaviour has been found in copolymers containing N‐methyl‐N‐vinylbenzylpyrrolidinium chloride (MVBPC) and methyl methacrylate (MMA). NMR, IR and low molecular weight model reactions demonstrate that this crosslinking reaction occurs between the methyl ester groups of the MMA units and the quaternary ammonium salts, with the resulting benzyl esters forming chemical links between the MVBPC and MMA units with the formation of N,N‐dimethylpyrrolidinium chloride. Similar crosslinking behaviour has also been found when the Cl anion is replaced by Br and I, but not in the case of BF as counter anion. © 2000 Society of Chemical Industry  相似文献   

10.
Amphoteric polymer hydrogels were prepared by the copolymerization of three kinds of N,N′‐dimethyl‐N‐alkylmethacryloxylethyl ammoniumbromide (DMAEA) with different lengths of alkyl chains (DMAEA‐RB) (R‐ehtyl/hexyl/dodecyl), acrylic acid (AA), and acrylamide (AM). The water content of the AA‐AM‐(DMAEA‐RB) terpolymers decreased with the increasing length of alkyl chains in quaternary ammonium group in the terpolymers and increased with the increasing molar ratio of DMAEA‐RB to 2 mol % and then decreased. Their antibacterial activities against Escherichia coli and Staphylococcus hyicus were investigated by a colony count method. It was found that the copolymer exhibited higher antibacterial activity with increasing chain length of alkyl groups in ammonium groups. For P[AA‐AM‐(DMAEA‐DB)], the DMAEA‐DB content is higher and contact time is longer, its antibacterial activity is better. However, when the contact time and quaternary ammonium content were above 30 min and 2%, respectively, the amount of live cells N(t) in a cell suspension increased in the presence of P[AA‐AM‐(DMAEA‐EB)] or P[AA‐AM‐(DMAEA‐HB)]. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011  相似文献   

11.
Currently studies on antibacterial macromolecules, i. e., bactericidal and bacteriostatic ones, have been made to develop a new utilization field of polymeric materials. In these studies, there are immobilizations of iodine to quaternary ammonium salts, antibiotics, antibacterial groups to macromolecular substances, as well as syntheses of polymers with quaternary ammonium salts, biguanide groups, quaternary pyridinium salts, sulphonium salts, phosphonium salts, and other antibacterial groups. On the other hand, studies have been made of bacterium adsorbing macromolecules, which can remove by adsorbing bacterial cells in water. The macromolecules are the ones based on poly(4‐vinylpyridine‐co‐divinylbenzene), crosslinked poly(3‐ and 4‐chloromethylated styrene‐g‐amine), and poly(glycidyl methacrylate‐g‐amine), as well as filters and microporous membranes are covered with a macromolecule based on quaternized poly(4‐vinylpyridine‐co‐styrene). Here, a review is made of the syntheses and preparation of the respective macromolecules, as well as of their antibacterial activities and the bacterium adsorbing activities.  相似文献   

12.
A cationic poly(methyl iodide quaternized styrene–N,N‐dimethylaminopropylmaleamidic acid) copolymer was synthesized through amidoacidification reaction of styrene‐maleic anhydride copolymer with N,N‐dimethylaminopropylamine (ring‐opening reaction). Its properties in various aqueous salt solutions and pH solutions were studied by measurements of reduced viscosity and intrinsic viscosity. The results indicated that the reduced viscosity and intrinsic viscosity of this cationic polyelectrolyte were related to the type and concentration of the added salts and the results also showed a contrary tendency in some salts with monovalent acid groups to polyelectrolyte. At the same time, some salt ions were observed to strongly attract the quaternary ammonium group of the cationic polymeric side chain and resulted in agglomeration of the polymers. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 1619–1626, 2001  相似文献   

13.
A viable method for coating of cellulose fiber with quaternarized N‐halamine is reported in this article. The use of quaternary ammonium salt group in combination with N‐halamine group can reinforce the antibacterial activity. The chemical structure of as‐synthesized N‐halamine precursor 4‐(Bromo‐acetic acid methylester)‐4‐ethyl‐2‐ oxazolidinone (BEO) was characterized by 1H‐NMR. The cellulose fibers were characterized by Fourier transform infrared spectra and X‐ray photoelectron spectra. The spectra data confirmed that the quaternarized N‐halamine‐grafted cellulose fibers were successfully obtained. The antibacterial properties of functional fibers were challenged with both Gram positive and Gram negative bacteria. The antibacterial tests and showed that the as‐prepared antibacterial cellulose fibers exhibited powerful and rapid bactericidal performance against both Gram negative E. coli and Gram positive S. aureus. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015 , 132, 42702.  相似文献   

14.
Quaternary ammonium salts were immobilized on hydrophilic gels based on sucrose methacrylates (SM) and tested for their antibacterial properties. The cross-linked polymers were prepared by copolymerization of monomer–SM mixtures with 4-vinylpyridine and subsequent quaternization with 1-bromoctane and 1-bromoctadecan and by esterification of SM gels with 3-pyridine carboxylic acid chloride and quaternization. In addition, immobilized quaternary salts bonded by hydrophobic as well as by hydrophilic spacers were synthesized by esterification of SM gels with 11-bromundecanoic acid chloride and the tetraethylene glycol-based acid chloride 13c , respectively, and subsequent reaction of the halogen-substituted gels with tertiary amines. Suspension tests for antibacterial properties of the immobilized bactericides against Escherichia coli, Staphylococcus aureus, and Micrococcus luteus demonstrated high activity of the quaternary salts bonded by the hydrophobic spacer. Advantageously, these insoluble bactericides can be applicated without contamination of the substrate; they can be removed easily and used repeatedly. © 1994 John Wiley & Sons, Inc.  相似文献   

15.
The colonization of medical devices such as catheters, topical wound dressings, and surgical implants by micro‐organisms is an ongoing problem, particularly as many strains of bacteria are becoming resistant to antibiotics. Such a problem may be addressed by a material surface that is able to provide a slow release of a disinfectant during its period of usage. To achieve this objective, a novel material was prepared in which a quaternary ammonium salt was covalently bound onto a polyethylene backbone via a hydrolyzable ester linkage, which provided a slow release of the disinfecting agent. A low‐density polyethylene film was treated with glow discharge followed by the graft polymerization of acrylic acid. A tertiary amine function was introduced onto the film by the esterification of the carboxylic acid groups, via an acid chloride intermediate, with 4‐hydroxy‐N‐methyl piperidine. The tertiary amine on the piperidine was then quaternized with a series of alkyl bromides of various chain lengths. The quaternary ammonium salt was released slowly by the hydrolysis of the ester bond over a 4‐h period. To test the efficacy of the quaternary ammonium function itself, soluble compounds were prepared as follows. 4‐Hydroxy‐N‐methyl piperidine was esterified with acetic anhydride and a corresponding series of quaternary ammonium salts prepared again by a reaction with alkyl bromides of various chain lengths. A preliminary microbiological survey of the materials included an investigation of the effect of the chain length as well as the efficacy of the soluble quaternary salts themselves. As expected, only the longer alkyl chains provided quaternary ammonium salts with bactericidal properties, chain lengths of less than 10 carbon atoms proving ineffective. Both the polymer‐bound and soluble long‐chain quaternary ammonium salts were effective against suspensions of Staphylococcus aureus and Escherichia coli. The results therefore indicate that such a system may well be useful in the development of biomedical materials such as surgical implants or dressings in which a slow release of a disinfectant or other physiologically active agent such as an anti‐inflammatory drug may be required. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 100: 538–545, 2006  相似文献   

16.
Novel biodegradable polylactide (PLA) copolymers bearing pendant antimicrobial agent groups were successfully fabricated with a combination of ring‐opening copolymerization and copper(I)‐catalysed azide–alkyne cycloaddition click reaction in a two‐step reaction procedure. First, biodegradable PLA copolymers bearing azido groups were synthesized by the ring‐opening copolymerization of l ‐lactide and 2,2‐ bis(azidomethyl)trimethylene carbonate in the presence of 1‐dodecanol as protic co‐initiator and tin(II) 2‐ethylhexanoate (Sn(Oct)2) as the catalyst. Then, alkyne functionalized quaternary ammonium salts were attached onto the azido groups of the copolymers via a Huisgen 1,3‐dipolar cycloaddition reaction to give PLA imparting antimicrobial activity. The chemical structure and composition of the copolymers were clearly confirmed using 1H NMR and Fourier transform infrared spectroscopies and gel permeation chromatography. Thermal phase transition temperatures (Tm and Tg) and the thermal stability of the polymers were investigated by DSC and TGA experiments, respectively. The antimicrobial activity tests were carried out against Gram‐negative (Escherichia coli) and Gram‐positive (Staphylococcus aureus) bacteria by the drop plate method. It was observed that antimicrobial agents are more active in the polymeric form than in the monomeric form. Also, the activity depends on the compositional ratio and the length of the alkyl group on the ammonium salts. © 2018 Society of Chemical Industry  相似文献   

17.
N,O‐(2‐carboxyethyl)chitosan (N,O‐2‐CEC) was prepared from chitosan with 3‐chloropropionic acid as modifying agent and NaOH as binding‐acid agent. 2‐Hydroxypropyl dimethylbenzylammonium N,O‐(2‐carboxyethyl) chitosan chloride (HPDMBA‐CEC) was obtained by the reaction of N,O‐2‐CEC with glycidyl dimethyl benzyl ammonium chloride (GDMBA) using NaOH as catalyst. The structures of chitosan derivatives were characterized by FTIR, 1H NMR, and gel permeation chromatography. The antimicrobial activity of HPDMBA‐CEC was evaluated against a Gram‐negative bacterium Escherichia coli (E.coli) and a Gram‐positive bacterium Staphylococcus aureus (S. aureus). Compared with CTS, N,O‐2‐CEC, and HPDMBA‐CTS, HPDMBA‐CEC had much stronger antimicrobial activity, and this activity increased with increasing substitution degree of quaternary ammonium group (DQ). When the substitution degree of carboxyethylation (DS of CE) was 0.72 and DQ was 0.60, the minimum inhibitory concentrations (MICs) of HPDMBA‐CEC were 3.1 and 6.3 μg/mL against S. aureus and E. coli, respectively. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009  相似文献   

18.
N‐Phenylmaleimide–N‐(p‐hydroxy)phenylmaleimide–styrene terpolymer (HPMS), carrying reactive p‐hydroxyphenyl groups, was prepared and used to improve the toughness of cyanate ester resins. Hybrid modifiers composed of N‐phenylmaleimide–styrene copolymer (PMS) and HPMS were also examined for further improvement in toughness. Balanced properties of the modified resins were obtained by using the hybrid modifiers. The morphology of the modified resins depends on HPMS structure, molecular weight and content, and hybrid modifier compositions. The most effective modification of the cyanate ester resin was attained because of the co‐continuous phase structure of the modified resin. Inclusion of the modifier composed of 10 wt% PMS (Mw 136 000 g mol?1) and 2.5 wt% HPMS (hydroxyphenyl unit 3 mol%, Mw 15 500 g mol?1) led to 135% increase in the fracture toughness (KIC) for the modified resin with a slight loss of flexural strength and retention of flexural modulus and glass transition temperature, compared with the values for the unmodified resin. Furthermore, the effect of the curing conditions on the mechanical and thermal properties of the modified resins was examined. The toughening mechanism is discussed in terms of the morphological and dynamic viscoelastic behaviour of the modified cyanate ester resin system. © 2001 Society of Chemical Industry  相似文献   

19.
Vinylester resin‐clay hybrids were prepared by the mixing different types of organically‐modified montmorillonite (OMMT) with vinylester resin (VER) prepolymer, followed by thermal polymerization. VER prepolymer was synthesized from the reaction of diglycidylether of bisphenol‐A (DGEBA) with acrylic acid. Various types of organic ammonium salts have been used as intercalating agents for montmorillonite, including N,N‐dimethyl‐N‐(4‐vinylbenzyl)stearyl ammonium chloride (VSA), N‐allyl‐N,N‐dimethyl‐stearyl ammonium chloride (ASA) and N,N‐dimethyl‐stearyl ammonium chloride (SA). The dispersion of OMMT into VER matrix was studied by XRD, which indicates the dependence of the morphology mainly on the OMMT content. UV–vis spectra of the hybrids were used to give a quantitative value of the effect of OMMT content on the transparency of VER/OMMT hybrid films. Also, the Vickers test has been performed to study the effect of OMMT content on the surface hardness of the hybrid films. In addition, the thermal properties of the hybrids have been characterized by measuring the softening points and thermogravimetric analyses of the hybrids in comparison with the pure resin. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010  相似文献   

20.
The poor mechanical properties of electrospun materials remain one of the major hindrances toward their practical application. In this study, we report the synthesis of core‐sheath nanofibrous mats to enhance the mechanical properties of an antimicrobial polymer nanofiber for application in filter media. This objective was achieved via coaxial electrospinning of poly[styrene‐coN‐(N′,N′‐dimethyl‐3‐aminopropyl)maleimide] as the sheath which is an antimicrobial polymer and nylon 6 polymer for the core which is well reported for exceptional mechanical properties. Extensive characterization of these fibers was performed using scanning electron microscopy, scanning transmission electron microscopy, confocal fluorescence microscopy as well as attenuated total reflectance Fourier transform spectroscopy to provide evidence of the core‐sheath morphology. Antimicrobial evaluation was also carried out on the fabricated fibers via the live/dead fluorescence technique. This was done to determine if the poly[styrene‐coN‐(N′,N′‐dimethyl‐3‐aminopropyl)maleimide] retained its antimicrobial activity. The fibers were found to be effective against the Gram‐positive Staphylococcus aureus (ATCC25925) and Gram‐negative Pseudomonas aeruginosa (ATCC27853). Subsequent tensile testing and filtration experiments provided evidence that the incorporation of the nylon core improved mechanical properties of the nanofiber mats. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135, 46303.  相似文献   

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