Aminimides: II. Antimicrobial effect of short chain fatty acid derivatives

A new family of surfactants, aminimides, has been screened forin vitro antimicrobial activity. These compounds are active against both bacteria and yeast, activity being a function of chain length. Maximum activity for acetimide and acrylimide amine derivatives was extablished with chain lengths of C₁₄–C₁₆. Homologous compounds with lower or higher chain lengths were less active. While showing low antimicrobial activity against gram negative bacteria, mixtures containing C₁₂ and C₁₆ gave good activity against gram negative strains without losing gram positive activity. Aminimides gave low acute LD₅₀’s (200–400 mg/kg) when tested in mice by intraperitoneal injection.     

Aminimides: I. Antimicrobial effect of some long chain fatty acid derivatives

Aminimides are a new class of surface active agents which have antimicrobial activity. These bipolar compounds have activity against both gran-positive and yeast organisms. Their activity against gram-negative organisms is low or absent. The acyl derivatives tested showed maximum activity at chain lengths of C₁₄ and C₁₆. Fatty acid derivatives, shorter (14) or longer (>C₁₆), were less active. Unsaturation was an important factor contributing to aminimide activity. Their low toxicity and wide spectrum of antimicrobial activity make aminimides ideal candidates for further investigation.     

Structure and antimicrobial activity relationship of quaternary N‐alkyl chitosan derivatives against some plant pathogens

In the present work, quaternary chitosans as water‐soluble compounds were prepared based on three‐step process. Schiff bases were firstly synthesized by the reaction between the amino groups of chitosan with aliphatic aldehydes followed by a reduction with sodium borohydride (NaBH₄) to form N‐(alkyl) chitosans. N,N,N‐(dimethyl alkyl) chitosans were then obtained by a reaction of chitosan containing N‐butyl, N‐pentyl, N‐hexyl, N‐heptyl, and N‐octyl substituents with methyl iodide. The compounds were characterized using IR and NMR spectroscopy. Subsequent experiments were conducted to test their antimicrobial activities against the most economic plant pathogenic bacteria of crown gall disease Agrobacterium tumefaciens, soft mold disease Erwinia carotovora, fungi of grey mold Botrytis cinerea, root rot disease Fusarium oxysporum, and damping off disease Pythium debaryanum. Quaternary chitosans enhanced the antibacterial activity and N,N,N‐(dimethyl pentyl) chitosan was the most active one with Minimum Inhibitory Concentration (MIC) of 750 and 1225 mg/L against A. tumefaciens and E. carotovora, respectively. All quaternized chitosans gave stronger antifungal activities than chitosan where N,N,N‐(dimethyl pentyl) chitosan and N,N,N‐(dimethyl octyl) chitosan were significantly the highest in mycelial growth inhibiation against B. cinerea (EC₅₀ = 908 and 383 mg/L, respectively), F. oxysporum (EC₅₀ = 871 and 812 mg/L, respectively), and P. debaryanum (EC₅₀ = 624 and 440 mg/L, respectively). In addition, spore germination of B. cinerea and F. oxysporum was significantly affected with the compounds at the tested concentrations and the inhibition activity was increased with an increase in the chain length of the alkyl substituent. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Diels-alder reaction: New antimicrobial pyrazolo-chroman derivatives

Pyrazolo-[2,3-d]-chroman dione derivatives were obtained via Diels-Alder reaction of pyrazolone arylidenes and 1,4-benzoquinone. The reaction rate and its yield have been found to be solvent and time dependent. The evaluation of the bactericidal and fungicidal screening showed significant inhibition effects against some thermophilic organisms grown and incubated at 55°C.     

Durable antimicrobial nylon 66 fabrics: Ionic interactions with quaternary ammonium salts

Acidic or basic dyeing of fibers involves ionic interactions between reactive groups on the polymers and dye molecules. Such interactions can be utilized in the functional finishing of fabrics. This article discusses a new approach of employing the ionic interactions between anionic carboxylic end groups of polyamides and cationic quaternary ammonium salts in the chemical finishing of nylon fabrics to achieve desired durable antimicrobial functions. The finishing conditions such as pH, finishing temperature, and time were studied, and the pH of the finishing bath was very critical in affecting the ionic interactions and thus exhaustion of the salts on the fabrics. The finishing process should be carried out at a temperature above the glass transition temperature of nylon 66. The finished products demonstrated excellent durability of antimicrobial functions. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 2194–2199, 2003     

聚硅氧烷季铵盐抗菌整理剂的合成及应用

介绍了聚硅氧烷季铵盐抗菌整理剂的合成方法及其应用性能。指出了现存的问题和今后的研究方向。聚硅氧烷季铵盐的合成主要以DC-5700型季铵盐和氨基硅油、含氢硅油等聚合物为原料,经过平衡聚合、缩聚、季铵化等反应制得。可用于织物材料的抗菌、除垢、防静电处理,并且能大大降低界面的界面张力。由于其与被处理材料的表面以化学键结合,因而不易脱落,是一种安全高效的新型阳离子表面活性剂,具有广阔的应用前景。     

季铵化聚乙烯亚胺的缓蚀与杀菌性能研究

制备了季铵化的聚乙烯亚胺(QPEI),采用静态挂片失重法研究了在0.5mol/L硫酸溶液中QPEI对低碳钢的缓蚀性能;以大肠杆菌(E.coli)为致病菌体,采用平板活菌记数法研究了QPEI的抗菌活性,并使用TTC-脱氢酶活性测定法,研究了QPEI的抗菌机理。结果表明,QPEI对低碳钢具有十分优良的缓蚀作用,同时具有很强的抗菌性能,其缓蚀作用抗菌作用基于杀菌过程,而不只是抑菌过程。     

Assay of quaternary ammonium antimicrobial compounds by aqueous potentiometric titration

An automatic potentiometric titration method for the determination of quaternary ammonium antimicrobial compounds at the macro level is described. The procedure involves the use of standard sodium lauryl sulfate as the titrant and a nitrate ion-selective or surfactant electrode to detect the end point. The method, which includes a new, simpler means of titrant standardization, avoids the use of hazardous solvents such as chloroform, which are employed in two-phase titration methods currently in common use. In this study, four frequently produced antimicrobial quats were titrated potentiometrically and by a two-phase titration using bromphenol blue as the indicator. Comparison of results shows the automatic potentiometric method to be accurate, more precise, easier, faster, and generally better suited for use in a production laboratory than the two-phase approach. The nitrate and the surfactant electrodes appear to be equal in performance.     

高分子季铵盐型抗菌材料的制备

通过γ-氯丙基三甲氧基硅烷的偶联,将水溶性聚乙烯亚胺(PEI)接枝在纳米SiO2表面,随后分别用1-溴己烷和碘甲烷对接枝的PEI进行N-烷基化修饰,使PEI中的部分氨基转变成季铵盐,得到水不溶性QPEI/SiO2微粒。通过测定PEI/SiO2上PEI的接枝量,考察了各种反应条件对QPEI/SiO2微粒制备的影响规律。研究结果表明,纳米SiO2表面接枝PEI的适宜条件为:反应溶剂为DMF,反应温度90~100℃,反应时间8 h,氯丙基化SiO2与PEI质量比为4∶1,在此条件下制备的QPEI/SiO2微粒中PEI接枝量为14.8%。QPEI/SiO2微粒经甲基化修饰后,季铵盐含量由0.96%增加到3.37%,其抗菌性能显著增强。     

有机硅季铵盐抗菌剂的研究进展

综述了有机硅季铵盐抗菌剂的抗菌机理、合成方法及应用性能,并对其今后的发展作了展望。有机硅季铵盐主要通过季铵化、硅氢化加成和平衡或缩聚等反应制得。由于该产品具有抗菌、抗静电、柔软及滑爽等特点,因此可厂泛用作织物抗菌整理剂、柔软整理剂、防腐剂及头发调理剂等。由于其与被处理材料的表面以化学键结合,因而不易脱落,是一种安全高效的新型阳离子表面活性剂,具有广阔的应用前景。     

Preparation and characterization of quaternary bacterial cellulose composites for antimicrobial oil-absorbing materials

The treatment of various types of oily wastewater is paramount for environmental protection. Bacterial cellulose (BC) stands out as a highly promising material for oil/water separation, owing to its exceptional mechanical properties and three-dimensional porous structures. However, excessive hydroxyl groups on BC make it highly hydrophilic, reducing oil absorption and promoting bacterial growth, affecting its stability. To address these challenges, we developed a straightforward in situ polymerization method for the preparation of BC-DMC composites. The innovation lies in the concurrent enhancement of BC's hydrophobicity and antimicrobial properties only through the addition of 2-(Methacryloyloxy)ethyltrimethylammonium chloride (DMC), considerably simplifying the synthesis of materials possessing oil-absorbing and antimicrobial properties. Morphological and structural characterization results confirmed the successful combination of DMC onto BC while maintaining its porous structure. After process parameter optimization, the BC-DMC composites exhibited a remarkable increase in contact angle (117.7° compared with pure BC's 19.5°). It also demonstrated excellent oil absorption performance, with maximum capacities exceeding 30 g/g for different oils, maintaining values above 20 g/g even after eight cycles. In addition, the BC-DMC composites exhibited strong antibacterial activity, with rates of 82.4% against Escherichia coli and 97.5% against Staphylococcus aureus. The antibacterial mechanism of the BC-DMC composites was also discussed. Our novel BC-DMC composites provides excellent oil absorption and antibacterial properties, making it highly applicable in the field of oily wastewater treatment and serving as a valuable reference for other researchers.     

Preparation and antimicrobial activity of Konjac Glucomannan modified with quaternary ammonium compound

Seven kind of graft copolymerization Konjac Glucomannan with quaternary ammonium group have been prepared, using Konjac Glucomannan (KGM) and methacryloxylethyl alkyl dimethyl ammonium bromide with c₈–c₁₈ alkyl and benzyl in water, ceric ammonium nitrate as initiator, the reaction temperature of 348 K, and the reaction period of 3 h. The structures were confirmed by FTIR. The 15 min inhibitory rates of all the graft copolymerization KGM against Escherichia coli and Staphylococcus aureus reached 99.99%, against Candida albicans somewhat lower, but 30 min inhibitory rate still reached 99.02% for graft copolymerization KGM with quaternary ammonium group having 14 alkyl. The antibacterial mechanism of the graft copolymerization KGM has been investigated by adsorption ability to E. coli, measure of 260 nm absorbing materials and SEM micrographs. Firstly, the bacteria were fastly adsorbed by graft copolymerization KGM. Interactions between bacterial membranes and antibacterial product cause fundamental changes in both membrane structure and function, induced leakage of cytoplasmic contents is a classic indication of damage to the bacterial cytoplasmic membrane. The loss of the connection between the outer membrane and the underlying peptidoglycan induces the abnormality of nodular structures and bleb formation of the cell envelope of E. coli. The antibacterial mechanism is in accordance with microbiologic findings identifying surface blebbing as the first morphologic change occurring in the permeability barrier of gram‐negative bacteria under mild heat stress and laser irradiation, etc. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

甲基碳酸酯季铵盐及其衍生物的研究进展

以碳酸二甲酯作为季铵化试剂替代传统的卤甲烷、硫酸二甲酯等有毒物质进行季铵化反应。主要介绍了各类叔胺与碳酸二甲酯进行季铵化反应的研究进展,同时对所制备的新型季铵盐类阳离子表面活性剂在制备不同阴离子季铵盐和高纯度季铵碱方面的应用进行了介绍,最后对过量的碳酸二甲酯和甲醇的回收与循环利用情况进行了说明,提出了今后研究工作的发展方向。     

Synthesis,characterization, and antimicrobial properties of novel quaternary amine methacrylate copolymers

A novel amine methacrylate monomer trimethylolpropane trimethacrylate–piperazine–ethyleneglycol dimethacrylate (TMPTMA‐PPZ‐EGDMA) was synthesized by amination of trimethylolpropane trimethacrylate (TMPTMA) with excess of piperazine (PPZ) followed by reaction with ethyleneglycol dimethacrylate (EGDMA). Copolymerization of TMPTMA‐PPZ‐EGDMA with 2‐hydroxyethyl methacrylate (HEMA) was carried out by free radical polymerization using ammonium persulfate (APS) and N,N,N′,N′‐tetramethyl ethylenediamine (TEMED) as a redox initiator. The copolymers obtained were then quaternized with 1‐iodooctane. The monomers were characterized by FTIR and ¹H NMR spectral studies. The molecular weights and polydispersity values of the monomers were determined with gel permeation chromatography. Quaternized copolymers containing more than 20% amine methacrylate monomer showed microporosity in the range of 9.9–10.4 μm. The antibacterial activity of the quaternized copolymers against Escherichia coli and Staphylococcus aureus was studied using UV–vis spectrophotometer and scanning electron microscopy. Quaternized copolymers showed broad‐spectrum contact‐killing antibacterial properties without releasing any active agent as checked by iodide selective ion meter. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Synthesis and antimicrobial activities of polysiloxane-containing quaternary ammonium salts on bacteria and phytopathogenic fungi

A series of dimethylaminopropyl benzyl chloride grafted polysiloxanes (PDMS-g-BCs) with tunable molecular weights and cationic content were synthesized, and the effect of polymer structure on the antimicrobial activities against bacteria (Escherichia coli (E. coli) and Staphylococcus albus (S. albus)) and phytopathogenic fungi (Rhizoctonia solani (R. solani) and Fusarium oxysporum f. sp. cubense race 4 (Foc4)) were systematically assessed. The antibacterial activity was evaluated by determining the minimum inhibitory concentration (MIC) against E. coli and S. albus by the broth dilution method, and the antifungal activity was measured by mycelia growth inhibition as well as by the MIC and minimum fungicidal concentration (MFC) values. The molecular weight and cationic content were major determinants of the activities of PDMS-g-BCs; when the molecular weight was approximately 2500 g/mol and the cationic content was approximately 20 mol% of the total siloxane units, PDMS-g-BCs gained strong antimicrobial activities toward both E. coli and Foc4, comparable to those of a commonly used broad-spectrum microbicide benzalkonium chloride, making PDMS-g-BCs promising fungicidal agents for plant disease control.     

降冰片烯类季铵型阴离子交换膜的制备

通过环状烯烃双键打开, 首尾相接形成聚合物的方法, 设计合成了含有季铵阳离子作为功能化基的降冰片烯衍生物单体QRPhNB, 通过开环异位聚合(ROMP)制备得到阴离子交换膜材料, 流延成膜后的分析结果表明:当单体与降冰片二烯1:2投料时所得到的阴离子交换膜的IEC值为1.26 mequiv·g^-1, 其最高离子传导率为20.05 mS·cm^-1;吸水率为14.3%。     

Preparation and application of antimicrobial man-made fibres and of fibrous materials containing quaternary ammonium compounds

Conclusions Biologically active fibres and textile materials based on them, containing salts of quaternary ammonium bases, in particular Katamin AB, have been prepared.It is proposed to used antimicrobial textile materials for biological protection of book and archival materials, purification of air in food industry plants, and in medical practice.Translated from Khimicheskie Volokna, No. 3, pp. 42–44, May–June, 1984.     

Preparation and antimicrobial activity of terpene-based polyurethane coatings with carbamate group-containing quaternary ammonium salts

A series of novel carbamate group-containing quaternary ammonium salts (QASs) have been synthesized, which were subsequently used as antimicrobial agent and incorporated into polyurethane coatings through crosslinking with terpene-based polyol and polyisocyanate. The chemical structures of QASs were characterized by FT-IR, ¹H NMR, and ¹³C NMR. The effects of QASs on the properties of coatings were investigated. The results showed that the resulting coatings exhibited significant antimicrobial activity against both Staphylococcus aureus and Escherichia coli by introducing QASs into the polyurethane networks. Furthermore, with the increasing of QAS content, the antimicrobial activity and adhesion of the coatings were enhanced, while the pencil hardness, water resistance and thermal stability of the coatings were decreased.     

Preparation of iodine containing quaternary amine methacrylate copolymers and their contact killing antimicrobial properties

A novel quaternary amine methacrylate monomer (QAMA) was synthesized by amination of dimethacrylate with piperazine followed by its quaternization using an alkyl iodide. Copolymerization of QAMA with 2‐hydroxyethyl methacrylate was carried out by free radical bulk polymerization technique at room temperature using ammonium persulfate and N,N,N′,N′‐tetramethyl ethylenediamine as a redox initiator. The monomer as well as copolymers was characterized by FTIR and ¹H NMR spectral studies. Thermal and physical characteristics of copolymers of varying compositions of QAMA were evaluated by thermogravimetric analysis, differential calorimetry, contact angle and scanning electron microscopy. The antibacterial activity of the synthesized quaternary amine dimethacrylate copolymers against Escherichia coli and Staphylococcus aureus was studied by zone of inhibition and colony count method. QAMA copolymers showed broad‐spectrum contact killing antibacterial properties without releasing any active agent as checked by iodide‐selective ion meter. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 1038–1044, 2006