Search Results (18)

Bacteria pose significant threats to human health, industrial production, and daily life, with widespread microbial contamination remaining a critical challenge for global public health. Conventional porous materials often suffer from insufficient antibacterial efficacy, necessitating the development of advanced antimicrobial systems. Herein, we report a synthetic strategy for fabricating chloride-regenerable porous tubular polymers (HCP-DMH-Cl) via a combination of Friedel–Crafts alkylation and nucleophilic substitution reactions. HCP was initially prepared through a crosslinking reaction via Friedel–Crafts alkylation using FeCl₃ as the catalyst and benzyl alcohol as the monomer. SEM characterization was performed to validate the tubular architectural morphology of HCP. The polymeric N-halamine precursor, HCP-DMH, was subsequently obtained through stepwise bromomethylation and nucleophilic substitution modifications. Upon chlorination, HCP-DMH-Cl exhibited good antibacterial efficacy against both E. coli and S. aureus, coupled with favorable regenerability of its oxidative chlorine content. This approach paves the way for designing next-generation porous media with tailored antibacterial functionality and sustainable chlorine-release capabilities. Full article

Nowadays, there has been an increasing research interest into N-halamine compounds due to their wide antimicrobial properties and no drug resistance. Most of the research mainly focuses on small molecular N-halamines, while few studies are on macromolecule N-halamines. In this work, antibacterial N-halamine polymer materials based on proteins (GS-Cl) were synthesized with an antibacterial component of oxidative chlorine, a support component of a gelatin sponge. After carrying out systematic characterization, the GS-Cls exhibited well-defined porous morphology and had a high efficiency in the killing of Gram-positive bacteria (E. coli) and Gram-negative bacteria (S. aureus). The loading of oxidative chlorine (Cl⁺%) could be controlled by changing the NaClO concentrations and chlorination times. The biocompatibility was confirmed as well. In vivo experiments suggested that the GS-Cl sample could effectively promote the healing of skin wounds in mice E. coli and S. aureus infection models. These studies show that proteins can be chlorinated and endowed with antimicrobial properties, which has great application potential in the treatment of bacteria-infected wounds. Full article

Microbial contamination has profoundly impacted human health, and the effective eradication of widespread microbial issues is essential for addressing serious hygiene concerns. Taking polystyrene (PS) membrane as an example, we herein developed report a robust strategy for the in situ preparation of chlorine-regenerable antimicrobial polymer molecular sieve membranes through combining post-crosslinking and nucleophilic substitution reaction. The cross-linking PS membranes underwent a reaction with 5,5-dimethylhydantoin (DMH), leading to the formation of polymeric N-halamine precursors (PS-DMH). These hydantoinyl groups within PS-DMH were then efficiently converted into biocidal N-halamine structures (PS-DMH-Cl) via a simple chlorination process. ATR-FTIR and XPS spectra were recorded to confirm the chemical composition of the as-prepared PS-DMH-Cl membranes. SEM analyses revealed that the chlorinated PS-DMH-Cl membranes displayed a rough surface with a multitude of humps. The effect of chlorination temperature and time on the oxidative chlorine content in the PS-DMH-Cl membranes was systematically studied. The antimicrobial assays demonstrated that the PS-DMH-Cl membranes could achieve a 6-log inactivation of E. coli and S. aureus within just 4 min of contact time. Additionally, the resulting PS-DMH-Cl membranes exhibited excellent stability and regenerability of the oxidative chlorine content. Full article

Polypropylene melt-blown nonwoven fabric (PP MNF) masks can effectively block pathogens in the environment from entering the human body. However, the adhesion of surviving pathogens to masks poses a risk of human infection. Thus, embedding safe and efficient antibacterial materials is the key to solving pathogen infection. In this study, stable chlorinated poly(methacrylamide-N,N′-methylenebisacrylamide) polypropylene melt-blown nonwoven fabrics (PP-P(MAA-MBAA)-Cl MNFs) have been fabricated by a simple UV cross-link and chlorination process, and the active chlorine content can reach 3500 ppm. The PP-P(MAA-MBAA)-Cl MNFs show excellent hydrophilic and antibacterial properties. The PP-P(MAA-MBAA)-Cl MNFs could kill all bacteria (both Escherichia coli and Staphylococcus aureus) with only 5 min of contact. Therefore, incorporating PP-P(MAA-MBAA)-Cl MNF as a hydrophilic antimicrobial layer into a four-layer PP-based mask holds great potential for enhancing protection and comfort. Full article

In March 2020, the World Health Organization announced a pandemic attributed to SARS-CoV-2, a novel beta-coronavirus, which spread widely from China. As a result, the need for antiviral surfaces has increased significantly. Here, the preparation and characterization of new antiviral coatings on polycarbonate (PC) for controlled release of activated chlorine (Cl⁺) and thymol separately and combined are described. Thin coatings were prepared by polymerization of 1-[3-(trimethoxysilyl)propyl] urea (TMSPU) in ethanol/water basic solution by modified Stöber polymerization, followed by spreading the formed dispersion onto surface-oxidized PC film using a Mayer rod with appropriate thickness. Activated Cl-releasing coating was prepared by chlorination of the PC/SiO₂-urea film with NaOCl through the urea amide groups to form a Cl-amine derivatized coating. Thymol releasing coating was prepared by linking thymol to TMSPU or its polymer via hydrogen bonds between thymol hydroxyl and urea amide groups. The activity towards T4 bacteriophage and canine coronavirus (CCV) was measured. PC/SiO₂-urea-thymol enhanced bacteriophage persistence, while PC/SiO₂-urea-Cl reduced its amount by 84%. Temperature-dependent release is presented. Surprisingly, the combination of thymol and chlorine had an improved antiviral activity, reducing the amount of both viruses by four orders of magnitude, indicating synergistic activity. For CCV, coating with only thymol was inactive, while SiO₂-urea-Cl reduced it below a detectable level. Full article

Many synthetic compounds have been applied to impart antimicrobial properties to fabrics. In this review, the types of bacteria are described. Furthermore, synthetic antimicrobial agents, namely quaternary ammonium compounds (QACs), polyhexamethylene biguanide (PHMB), triclosan, and nitrogen-halamines (N-halamines), are discussed along with their properties, their advantages and disadvantages. Although synthetic antimicrobial agents neutralise microorganisms, some adversely affect the environment, safety and health. These problems led to a novel generation of antimicrobial coating treatments on textiles, such as copper nanoparticles (CNPs) and silver nanoparticles (AgNPs) formed on plant extracts, chitosan and green synthesis, with a lower environmental impact but unaltered premium antimicrobial performance and improved durability. Full article

Cyclic N-halamines are highly antimicrobial, very stable, and not susceptible to bacterial resistance. A polysiloxane delivery vehicle was synthesized to deliver cyclic imide N-halamine onto cellulose via a benign and universal procedure that does not require a harmful solvent or chemical bonding. In brief, Knoevenagel condensation between barbituric acid and 4-hydroxybenzaldehyde furnished 5-(4-hydroxybenzylidene)pyrimidine-2,4,6-trione, whose phenolic O−H was subsequently reacted with the Si−H of poly(methylhydrosiloxane) (PMHS) via silane alcoholysis. The product of silane alcoholysis was interpenetrated into cellulose in supercritical CO₂ (scCO₂) at 50 °C, to form a continuous modification layer. The thickness of the modification layer positively correlated with interpenetration pressure in the experimental range of 10 to 28 MPa and reached a maximum value of 76.5 nm, which demonstrates the ability for tunable delivery, to control the loading of the imide N−H bond originating from barbituric acid unit. The imide N−H bonds on cellulose with the thickest modifier were then chlorinated into N−Cl counterparts using tert-butyl hypochlorite, to exert a powerful biocidability, providing ~7 log reductions of both S. aureus and E. coli in 20 min. The stability and rechargeability of the biocidability were both very promising, suggesting that the polysiloxane modifier has a satisfactory chemical structure and interlocks firmly with cellulose via scCO₂ interpenetration. Full article

Due to the ability of microorganisms to first adhere to a material surface and then to lead to the formation of a biofilm, it is essential to develop surfaces that have antimicrobial properties. It is well known that N-halamine coatings allow us to prevent or minimize such phenomena. In the present work, various polydopamine (PDA) coatings containing chloramine functions were studied. In fact, three PDA-based films were formed by the simple immersion of a gold substrate in a dopamine solution, either at pH 8 in the presence or not of polyethyleneimine (PEI), or at pH 5 in the presence of periodate as an oxidant. These films were characterized by polarization modulation reflection absorption infrared spectroscopy and X-ray photoelectron spectroscopy analyses, and by scanning electron microscopy observations. The chlorination of these PDA films was performed by their immersion in a sodium hypochlorite aqueous solution, in order to immobilize Cl(+I) into the (co)polymers (PDA or PDA–PEI). Finally, antibacterial assays towards the Gram-negative bacteria Escherichia coli (E. coli) and the Gram-positive bacteria Staphylococcus epidermidis (S. epidermidis) were conducted to compare the bactericidal properties of these three N-halamine coatings. Regardless of the bacteria tested, the PDA coating with the best antibacterial properties is the coating obtained using periodate. Full article

The emergence of antibiotic-resistant “superbugs” in recent decades has led to widespread illness and death and is a major ongoing public health issue. Since traditional antimicrobials and antibiotics are in many cases showing limited or no effectiveness in fighting some emerging pathogens, there is an urgent need to develop and explore novel antibacterial agents that are both powerful and reliable. Combining two or more antibiotics or antimicrobials has become a hot topic in antibacterial research. In this contribution, we report on using a simple electrospinning technique to create an N-halamine/graphene oxide-modified polymer membrane with excellent antibacterial activity. With the assistance of advanced techniques, the as-obtained membrane was characterized in terms of its chemical composition, morphology, size, and the presence of active chlorine. Its antibacterial properties were tested with Escherichia coli (E. coli) as the model bacteria, using the colony-counting method. Interestingly, the final N-halamine/graphene oxide-based antibacterial fibrous membrane inactivated E. coli both on contact and by releasing active chlorine. We believe that the synergistic antimicrobial action of our as-fabricated fibrous membrane should have great potential for utilization in water disinfection, air purification, medical and healthcare products, textile products, and other antibacterial-associated fields. Full article

Reducing microbial infections associated with biomedical devices or articles/furniture noted in a hospital or outpatient clinic remains a great challenge to researchers. Due to its stability and low toxicity, the N-halamine compound has been proposed as a potential antimicrobial agent. It can be incorporated into or blended with the FDA-approved biomaterials. Surface grafting or coating of N-halamine was also reported. Nevertheless, the hydrophobic nature associated with its chemical configuration may affect the microbial interactions with the chlorinated N-halamine-containing substrate. In this study, a polymerizable N-halamine compound was synthesized and grafted onto a polyurethane surface via a surface-initiated atom transfer radical polymerization (SI-ATRP) scheme. Further, using the sequential SI-ATRP reaction method, different hydrophilic monomers, namely poly (ethylene glycol) methacrylate (PEGMA), hydroxyethyl methacrylate (HEMA), and [2-(methacryloyloxy) ethyl] dimethyl-(3-sulfopropyl) ammonium hydroxide (SBMA), were also grafted onto the polyurethane (PU) substrate before the N-halamine grafting reaction to change the surface properties of the N-halamine-modified substrate. It was noted that the chains containing the hydrophilic monomer and the polymerizable N-halamine compound were successfully grafted onto the PU substrate. The degree of chlorination was improved with the introduction of a hydrophilic monomer, except the HEMA. All of these hydrophilic monomer-containing N-halamine-modified PU substrates demonstrated a more than 2 log CFU reduction after microbial incubation. In contrast, the surface modified with N-halamine only exhibited significantly less antimicrobial efficacy instead. This is likely due to the synergistic effects caused by the reduced chlorine content, as well as the reduced surface interactions with the microbes. Full article

Microbial contamination is a significant issue in various areas, especially in the food industry. In this study, to overcome microbial contamination, cross-linked polymer brushes containing N-halamine were synthesized, characterized, and investigated for antibacterial properties. The cross-linked polymer brushes with different N-halamine ratios were synthesized by in-situ cross-linking methods with reversible addition−fragmentation chain transfer (RAFT) polymerization using a bifunctional cross-linker. The RAFT agent was immobilized on an amine-terminated silicon wafer surface and utilized in the surface-initiated RAFT polymerization of [N-(2-methyl-1-(4-methyl-2,5-dioxoimidazolidin-4-yl)propane-2-yl)acrylamide] (hydantoin acrylamide, HA), and N-(2-hydroxypropyl)methacrylamide) (HPMA) monomers. Measurement of film thickness, contact angle, and surface morphology of the resulting surfaces were used to confirm the structural characteristics of cross-linked polymer brushes. The chlorine content of the three different surfaces was determined to be approximately 8–31 × 10¹³ atoms/cm². At the same time, it was also observed that the activation–deactivation efficiency decreased during the recharge–discharge cycles. However, it was determined that the prepared N-halamine-containing cross-linked polymer brushes inactivated approximately 96% of Escherichia coli and 91% of Staphylococcus aureus. In conclusion, in the framework of this study, high-performance brush gels were produced that can be used on antibacterial surfaces. Full article

Coating a cationic antibacterial layer on the surface of cotton fabric is an effective strategy to provide it with excellent antibacterial properties and to protect humans from bacterial cross-infection. However, washing with anionic detergent will inactivate the cationic antibacterial coating. Although this problem can be solved by increasing the amount of cationic antibacterial coating, excessive cationic antibacterial coating reduces the drapability of cotton fabric and affects the comfort of wearing it. In this study, a coordinated antibacterial coating strategy based on quaternary ammonium salt and a halogenated amine compound was designed. The results show that the antibacterial effect of the modified cotton fabric was significantly improved. In addition, after mechanically washing the fabric 50 times in the presence of anionic detergent, the antibacterial effect against Staphylococcus aureus and Escherichia coli was still more than 95%. Furthermore, the softness of the obtained cotton fabric showed little change compared with the untreated cotton fabric. This easy-to-implement and cost-effective approach, combined with the cationic contact and the release effect of antibacterial agents, can endow cotton textiles with durable antibacterial properties and excellent wearability. Full article

Current demand for new protective materials ensuring sterility is systematically growing. The purpose of this work was the synthesis of the biocidal N-halamine hydantoin-containing chitosan (CS-CMH-Cl) and characterization of its properties. The functionalization of the chitosan by 5-hydantoinacetic acid substitution leads to obtaining the CS-CMH polymer, which was chlorinated in next step to transform N-H into N-Cl bonds. In this study, the possibility of forming two biocidal N-Cl bonds in hydantoin ring, grafted onto chitosan chains, was proved. The structure and stability of the prepared material was confirmed by spectroscopic (FTIR, NMR, colorimetric test) and microscopic analyses (SEM, AFM). Surface properties were investigated based on contact-angle measurements. In addition, the thermal and photochemical stability of the obtained samples were determined as functional features, determining the range of potential use. It was found that both modified chitosan polymers (CS-CMH and CS-CMH-Cl) were characterized by the smaller thermal stability and more hydrophilic and rougher surface than unmodified CS. Photooxidative degradation of the obtained materials was observed mainly on the sample surface. After irradiation, the surfaces became more hydrophilic—especially in the case of the CS-CMH-Cl—which is advantageous from the point of view of the antibacterial properties. Antibacterial tests against S. aureus and E. coli confirmed the antibacterial activities of received CS-CMH-Cl material. Full article

Microorganism pollution induced by pathogens has become a serious concern in recent years. In response, research on antibacterial N-halamines has made impressive progress in developing ways to combat this pollution. While synthetic polymer-based N-halamines have been widely developed and in some cases even commercialized, N-halamines based on naturally occurring polymers remain underexplored. In this contribution, we report for the first time on a strategy for developing sesbania gum (SG)-based polymeric N-halamines by a four-step approach Using SG as the initial polymer, we obtained SG-based polymeric N-halamines (abbreviated as cSG-PAN nanofibers) via a step-by-step controllable synthesis process. With the assistance of advanced techniques, the as-synthesized cSG-PAN nanofibers were systematically characterized in terms of their chemical composition and morphology. In a series of antibacterial and cytotoxicity evaluations, the as-obtained cSG-PAN nanofibers displayed good antibacterial activity against Escherichia coli and Staphylococcus aureus, as well as low cytotoxicity towards A549 cells. We believe this study offers a guide for developing naturally occurring polymer-based antibacterial N-halamines that have great potential for antibacterial applications. Full article