Antiviral and antimicrobial coatings and methods thereof

Abstract

The disclosure features a method of inhibiting microorganisms on a surface, the method including applying to the surface a polymer including repeating units, the repeating units including a benzimidazolium-containing moiety; an imidazolium-containing moiety; or any combination thereof.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Patent Application No. 63 / 163,605, filed March 19, 2021, the entire disclosure of which is incorporated herein by reference. [Background technology]

[0002] Antiviral and antimicrobial compounds are chemical compounds that reduce or ameliorate the growth or development of viruses and microorganisms, respectively. The use of antiviral and antimicrobial compounds results in the death or cessation of growth of target microorganisms, including viruses and microorganisms.

[0003] Minimizing infections caused by pathogenic microorganisms is a major concern in many sectors, such as medical devices, hospital surfaces / furniture, dental restorations and surgical instruments, healthcare products and sanitary applications, water purification systems, textiles, food packaging and storage, industrial or household appliances, aviation, etc.

[0004] Infections are caused by touching, eating, drinking, or inhaling pathogen-containing materials. Generally, these infections are combated by drugs that target the pathogen. Of particular concern, however, are microorganisms that can quickly and easily mutate their genes to become resistant to these drugs, making their elimination difficult. For example, Staphylococcus aureus (S. aureus) generally colonizes human skin and mucous membranes without causing serious problems, but once the bacteria enters the body, it can cause a range of mild to life-threatening illnesses, including skin and wound infections, infectious eczema, abscess infections, heart valve infections or endocarditis, pneumonia, and bloodstream infections or bacteremia. Some S. aureus strains are resistant to methicillin and other β-lactam antibiotics - methicillin-resistant S. aureus (MRSA) - and require alternative types of antibiotics to treat them. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2013 / 149328 [Patent Document 2] International Publication No. 2015 / 157848 [Patent Document 3] International Publication No. 2018 / 026743 [Patent Document 4] International Publication No. 2018 / 023097 [Non-patent literature]

[0006] [Non-Patent Document 1] Maity S. and Jana T., Appl. Mater. Interfaces, 2014, 6(9), pp. 6851-6864 Summary of the Invention [Problem to be solved by the invention]

[0007] There is a need for antiviral and antimicrobial materials that exhibit broad spectrum antiviral and / or antimicrobial activity and can be used in a variety of environments (e.g., homes, healthcare facilities, schools), surfaces (e.g., wood, stainless steel, marble, glass, and textiles), and applications (e.g., food packaging, water or air filters). These materials can have high kill rates, be effective for weeks, and be non-toxic. The present disclosure meets these needs and provides additional advantages. [Means for solving the problem]

[0008] This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key features of the claimed subject matter, nor is it intended to be used as an aid in determining the scope of the claimed subject matter.

[0009] In one aspect, the disclosure provides a method of inhibiting microorganisms on a surface, comprising applying to the surface a polymer comprising a repeat unit: (i) A benzimidazolium-containing moiety of formula (I):

[0010] [ka]

[0011] (In the formula, R 1AA is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3AA is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1AA , R 2AA , R 3AA , and R 5AA at least one of which is a polymer; (ii) an imidazolium-containing moiety having formula (II):

[0012] [ka]

[0013] (In the formula, R 1XX is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3XX is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1XX , R 2XX , R 3XX , and R 5XX at least one of which is a polymer; or Any combination of these The present invention is characterized by a method comprising:

[0014] The foregoing aspects and many of the attendant advantages of this invention will become more readily appreciated as the same become better understood by reference to the following detailed description, when taken in conjunction with the accompanying drawings, in which: [Brief description of the drawings]

[0015] [Figure 1A] 1 is a graph showing the antimicrobial effect of embodiments of the polymer coating of the present disclosure against viruses and bacteria. [Figure 1B] 1 is a graph showing the antimicrobial effect of embodiments of the polymer coating of the present disclosure against viruses and bacteria. [Figure 1C] 1 is a graph showing the antimicrobial effect of embodiments of the polymer coating of the present disclosure against viruses and bacteria. [Figure 1D] 1 is a graph showing the antimicrobial effect of embodiments of the polymer coating of the present disclosure against viruses and bacteria. [Diagram 2]1 is a scanning electron micrograph of an embodiment of a polymer coating of the present disclosure. Unlike nanosilver, the polymer coating of the present disclosure provides a smooth surface that enhances antimicrobial activity. Freeze-fracture SEM on high surface area carbon (>3000 m2 / g) shows a penetration depth in the range of 0.3-0.6 μm (300-600 nm). Area loadings equivalent to about 1 μm can provide a coherent coating, but coatings less than 1 μm can be easily formed on less porous surfaces. [Figure 3A] 1 is a graph of % transmission as a function of wavelength for an exemplary polymer coating of the present disclosure. [Figure 3B] FIG. 1 shows a thermogravimetric analysis (TGA) scan of an exemplary polymer coating of the present disclosure. [Figure 4] 1 is a table of embodiments of the polymer coating of the present disclosure. Water uptake can vary depending on the counterion. Chloride + low functionality variants are very hydrophobic, chloride or acetate + high functionality variants are hydrophilic, and nitrate + high functionality variants are in between. Hydrophilicity / hydrophobicity can provide differentiation of antibacterial and / or antiviral properties. For example, changes in hydrophilicity can result in changes in interactions with bacterial cell walls, viral envelopes, and affect polymer mobility. [Figure 5A] Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 5B]Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 5C] Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 5D] Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 5E] Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 5F] Schematic diagram of antimicrobial and / or antiviral testing. The selected ISO / JIS standard is considered the "gold standard" test and is designed to test the antimicrobial properties of non-porous surfaces. The test involves six data points per sample (three replicates + two "platings"), plus an additional blank / uncoated glass slide control. The antiviral tests performed included contamination (5% serum in the virus inoculum solution) and included testing for cytotoxicity as a potential confounding variable (all negative). [Figure 6] 1 is a table of parameters for antimicrobial and / or antiviral testing of polymer coating embodiments of the present disclosure. Staphylococcus aureus (Gram+) and Escherichia coli (E. coli) (Gram-) were represented in the antimicrobial testing of G+ and G- bacteria. Human coronavirus (229E) was used as a model for enveloped viruses such as coronaviruses (e.g., SARS-CoV-2). Feline calicivirus (F-9) was used as a model for non-enveloped viruses such as respiratory viruses (e.g., Calicivirus family). Ultrathin films of approximately 0.75-1.5 μm were tested. [Figure 7] FIG. 1 shows a table of antimicrobial test results for embodiments of the polymeric coating of the present disclosure. [Figure 8] 1 is a table of kinetic analysis of antimicrobial test results for polymer coating embodiments of the present disclosure. Unprecedented activity for surface modifications was observed - half-lives of human coronavirus (229E), G+, and G- bacteria were demonstrated to be only less than 2.1 minutes - 4-5 log reduction to above detection limit within 30 minutes. All variants passed JIS / ISO protocols for antimicrobial activity (>2 log reduction in 24 hours). Acetic acid and 1.5 μm "thick" chloride films had better activity - ultra-thin coatings may increase hydrophobicity. [Figure 9] FIG. 1 is a schematic diagram of a drip flow reactor. [Figure 10] Photograph of the drip flow reactor configuration during continuous flow operation. [Figure 11]FIG. 1 is a schematic side view of a drip flow reactor used to calculate the angle of the drip flow reactor. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] The present disclosure provides a method of inhibiting microorganisms on a surface, comprising applying to the surface a polymer comprising a repeating unit: (i) A benzimidazolium-containing moiety of formula (I):

[0017] [ka]

[0018] (In the formula, R 1AA is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3AA is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1AA , R 2AA , R 3AA , and R 5AA at least one of which is a polymer; (ii) an imidazolium-containing moiety having formula (II):

[0019] [ka]

[0020] (In the formula, R 1XX is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3XX is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1XX , R 2XX , R 3XX , and R 5XX at least one of which is a polymer; or any combination of these The present invention is characterized by a method comprising:

[0021] Exemplary polymers are described, for example, in PCT Publication Nos. WO 2013 / 149328, WO 2015 / 157848, WO 2018 / 026743, and WO 2018 / 023097, each of which is incorporated herein in its entirety.

[0022] The polymer can effectively render the coated surface bactericidal, viricidal, and / or germicidal such that microorganisms (e.g., fungi, viruses, and / or microorganisms (e.g., bacteria or single-cell organisms) on the coated surface are killed and / or inhibited on the coated surface. In some embodiments, the polymer can inhibit the attachment of microorganisms on the surface.

[0023] The polymers of the present disclosure can form clear, transparent, durable ultra-thin films on any surface using a variety of solvents, including non-toxic solvents. The polymer coatings can provide unprecedented antimicrobial activity. In some embodiments, up to 99.995% or more reduction in enveloped viruses, G- bacteria (E. coli), and G+ bacteria (Staphylococcus aureus) is seen within 30 minutes. The half-life of viruses and bacteria can be on the order of less than 10 minutes (e.g., less than 5 minutes, less than 3 minutes). Unlike silver nanoparticles and nanostructured surfaces, the universally applicable and cost-effective polymer coatings of the present disclosure do not lose efficacy under mechanical stress (e.g., through cleaning / disinfecting cycles). The coated surfaces can have increased smoothness, which can enhance the antimicrobial properties of the surface. Furthermore, the coatings can be non-toxic to humans and the environment, and can be chemically (e.g., against contamination, fouling, UV, disinfectants, and bleach) and mechanically stable.

[0024] In some embodiments, when a polymer-coated surface is exposed to microorganisms, the number of microorganisms on the surface may be reduced by more than 99% after a period of 24 hours (e.g., less than 24 hours, less than 20 hours, less than 12 hours, less than 6 hours, less than 3 hours, less than 1 hour, less than 30 minutes, less than 20 minutes, less than 10 minutes, or less than 5 minutes). The microorganisms may include fungi (i.e., one or more species of fungi), bacteria (i.e., one or more species of bacteria), viruses (i.e., one or more species of viruses), or any combination thereof.

[0025] In some embodiments, when a polymer coated surface is exposed to fungi, the number of fungi on the surface may be reduced by more than 99% after a period of 24 hours (e.g., less than 24 hours, less than 20 hours, less than 12 hours, less than 6 hours, less than 3 hours, less than 1 hour, less than 30 minutes, less than 20 minutes, less than 10 minutes, or less than 5 minutes).

[0026] In some embodiments, when the polymer-coated surface is exposed to bacteria, the number of bacteria is reduced by more than 99% after a 24 hour period. The bacteria can be gram-positive and / or gram-negative. The bacteria can be pathogenic.

[0027] In some embodiments, when the polymer coated surface is exposed to a virus, the number of viruses is reduced by more than 99% after a period of 24 hours (e.g., less than 24 hours, less than 20 hours, less than 12 hours, less than 6 hours, less than 3 hours, less than 1 hour, less than 30 minutes, less than 20 minutes, less than 10 minutes, or less than 5 minutes).

[0028] definition At various places in the present specification, substituents of compounds of the present disclosure are disclosed in groups or in ranges. It is specifically intended that the present disclosure include any and all individual subcombinations of the members of such groups and ranges. For example, "C 1~6 The term "alkyl" is specifically intended to individually disclose methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0029] It is further intended that the compounds of the present disclosure are stable. As used herein, "stable" refers to a compound that is sufficiently robust to survive isolation to a useful degree of purity from a reaction mixture.

[0030] It will be further appreciated that certain features of the present disclosure, which are, for clarity, described in the context of separate embodiments, can also be provided in combination in a single embodiment. Conversely, various features of the present disclosure, which are, for brevity, described in the context of a single embodiment, can also be provided separately or in any suitable subcombination.

[0031] An "optionally substituted" group can refer to, for example, a functional group that may be substituted or unsubstituted with an additional functional group. For example, when a group is unsubstituted, the group may be referred to as a group name, such as an alkyl or aryl. When a group is substituted with an additional functional group, the group may be more generally referred to as a substituted alkyl or substituted aryl.

[0032] As used herein, the term "substituted" or "substitution" refers to the replacement of a hydrogen atom with a substituent other than H. For example, "N-substituted piperidin-4-yl" refers to the replacement of the H atom from the NH of piperidinyl with a non-hydrogen substituent such as, for example, alkyl.

[0033] As used herein, the term "alkyl" refers to a straight-chain or branched hydrocarbon group having the indicated number of carbon atoms. Representative alkyl groups include methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, sec-butyl, and tert-butyl), pentyl (e.g., n-pentyl, tert-pentyl, neopentyl, isopentyl, pentan-2-yl, pentan-3-yl), and hexyl (e.g., n-pentyl and isomers).

[0034] As used herein, the term "alkylene" refers to a linking alkyl group.

[0035] As used herein, the term "perfluoroalkyl" refers to a straight or branched fluorocarbon chain. Representative alkyl groups include trifluoromethyl, pentafluoroethyl, and the like.

[0036] As used herein, the term "perfluoroalkylene" refers to a linking perfluoroalkyl group.

[0037] As used herein, the term "heteroalkyl" refers to a straight or branched chain alkyl group having the indicated number of carbon atoms, where one or more of the carbon atoms is replaced with a heteroatom selected from O, N, or S.

[0038] As used herein, the term "heteroalkylene" refers to a linking heteroalkyl group.

[0039] As used herein, the term "alkoxy" refers to an alkyl or cycloalkyl group, as described herein, attached to an oxygen atom. Representative alkoxy groups include methoxy, ethoxy, propoxy, and isopropoxy groups.

[0040] As used herein, the term "perfluoroalkoxy" refers to a perfluoroalkyl or cyclic perfluoroalkyl group, as described herein, attached to an oxygen atom. Representative perfluoroalkoxy groups include trifluoromethoxy, pentafluoroethoxy, and the like.

[0041] As used herein, the term "aryl" refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms. Representative aryl groups include phenyl groups. In some embodiments, the term "aryl" includes monocyclic or polycyclic (e.g., having 2, 3, or 4 fused rings) aromatic hydrocarbons, such as, for example, phenyl, naphthyl, anthracenyl, phenanthrenyl, indanyl, and indenyl.

[0042] As used herein, the term "arylene" refers to a linking aryl group.

[0043] As used herein, the term "aralkyl" refers to an alkyl or cycloalkyl group, as defined herein, having an aryl group, as defined herein, substituted for one of the alkyl hydrogen atoms. A representative aralkyl group is a benzyl group.

[0044] As used herein, the term "aralkylene" refers to a linking aralkyl group.

[0045] As used herein, the term "heteroaryl" refers to a 5-10 membered aromatic monocyclic or bicyclic ring containing 1-4 heteroatoms selected from O, S, and N. Representative 5- or 6-membered aromatic monocyclic ring groups include pyridine, pyrimidine, pyridazine, furan, thiophene, thiazole, oxazole, and isoxazole. Representative 9- or 10-membered aromatic bicyclic ring groups include benzofuran, benzothiophene, indole, pyranopyrrole, benzopyran, quionoline, benzocyclohexyl, and naphthyridine.

[0046] As used herein, the term "heteroarylene" refers to a linking heteroaryl group.

[0047] As used herein, the term "halogen" or "halo" refers to fluoro, chloro, bromo, and iodo groups.

[0048] As used herein, the term "bulky group" refers to a group that provides steric bulk by having a size at least as large as a methyl group.

[0049] As used herein, the term "copolymer" refers to a polymer that is the result of polymerization of two or more different monomers. The number and nature of each constitutional unit can be controlled separately within the copolymer. The constitutional units can be arranged in a purely random configuration, an alternating random configuration, a regular alternating configuration, a regular block configuration, or a random block configuration, unless explicitly stated otherwise. A purely random configuration can be, for example, xxyzxyyzyzzz... or yzxyzyzxx.... An alternating random configuration can be xyxzyxyzyxz... and a regular alternating configuration can be xyzxyzxyz.... A regular block configuration (i.e., a block copolymer) has the following general configuration: ...xxxyyyzzzxxx... and a random block configuration has the general configuration: ...xxxzzxxyyyyzzzxxzzz-....

[0050] As used herein, the term "random copolymer" refers to a copolymer having an uncontrolled mixture of two or more types of constitutional units. The distribution of constitutional units throughout the polymer backbone (or main chain) can be or approach a statistical distribution of constitutional units. In some embodiments, one or more distributions of constitutional units are favored.

[0051] As used herein, the term "building block" of a polymer refers to an atom or group of atoms in the polymer that, if any, constitutes part of a chain together with its pendant atom or group of atoms. A building block can refer to a repeating unit. A building block can also refer to an end group on a polymer chain. For example, a building block of polyethylene glycol can be -CH2CH2O-, which corresponds to the repeating unit, or -CH2CH2OH, which corresponds to the end group.

[0052] As used herein, the term "repeating unit" corresponds to the smallest building block, the repetition of which constitutes a regular polymer (or oligomeric molecule or block).

[0053] As used herein, the term "end group" refers to a unit located at the end of a polymer, having only one bond to the polymer chain. For example, an end group may be derived from a monomer unit at the end of a polymer when the monomer unit is polymerized. As another example, an end group may be part of a chain transfer agent or initiator used to synthesize the polymer.

[0054] As used herein, the term "end" of a polymer refers to a constitutional unit of the polymer that is located at the end of the polymer backbone.

[0055] As used herein, the term "cationic" refers to a moiety that is positively charged or that is capable of ionizing to a positively charged moiety under physiological conditions. Examples of cationic moieties include, for example, amino, ammonium, pyridinium, imino, sulfonium, quaternary phosphonium groups, and the like.

[0056] As used herein, the term "anionic" refers to a functional group that is negatively charged or capable of ionizing to a negatively charged moiety under physiological conditions. Examples of anionic groups include carboxylates, sulfates, sulfonates, phosphates, and the like.

[0057] As used herein, the term "applying" refers to any suitable technique used to transfer the polymer composition to a surface. For example, the technique for applying can be, but is not limited to, brushing, rolling, spraying, wiping, mopping, pouring, painting, absorbing, imbibing, immersing, saturating, permeating, soaking, and combinations of these methods.

[0058] As used herein, the term "bactericidal, virucidal, and / or pathogenic" refers to reducing the presence (e.g., eliminating, killing, or preventing and / or inhibiting the growth of) microorganisms such as bacteria, viruses, and / or pathogens (including fungi such as Aspergillas brasliensis) to any suitable extent. As used herein, the term "any suitable extent" refers to a reduction of 50% or more, including a reduction of 60% or more, a reduction of 70% or more, a reduction of 80% or more, a reduction of 90% or more, a reduction of 92% or more, a reduction of 94% or more, a reduction of 95% or more, a reduction of 97% or more, a reduction of 98% or more, a reduction of 99% or more, or a reduction of 99.5% or more.

[0059] As used herein, the term "microorganism" includes pathogens (e.g., fungi), single-celled organisms (e.g., bacteria, archaea), and / or viruses.

[0060] As used herein, "medical device" includes any device having a surface that contacts tissue, blood, or other bodily fluids in the course of their use or operation, which are found on a mammal (e.g., a human) or are subsequently used within a mammal. Medical devices include, for example, extracorporeal devices for use in surgery, such as blood oxygenators, blood pumps, blood storage bags, blood collection tubes, blood filters containing filtration media, dialysis membranes, tubing used to carry blood, etc., which contact blood that is then returned to the patient or mammal. Medical devices also include endoprostheses implanted in a mammal (e.g., a human), such as artificial blood vessels implanted in a blood vessel or heart, stents, pacemaker leads, surgical artificial conduits, heart valves, etc. Medical devices also include devices for temporary intravascular use, such as catheters, guidewires, amniotic and biopsy needles, cannulas, drains, shunts, sensors, transducers, probes, etc., which are placed in a blood vessel, heart, organ, or tissue for the purpose of monitoring or repair or treatment. Medical devices also include artificial joints, such as hips or knees, and prosthetic organs, such as artificial hearts. Additionally, medical devices include penile implants, condoms, tampons, sanitary napkins, ophthalmic lenses, sling materials, sutures, hemostats used in surgery, surgical meshes, percutaneous patches, and wound dressings / bandages.

[0061] As used herein, a "diagnostic device" includes any equipment or tool used to diagnose or monitor a medical condition. Examples include ultrasound, magnetic resonance imaging (MRI) machines, positron emission tomography (PET) scanners, computed tomography (CT) scanners, ventilators, heart-lung machines, extracorporeal membrane oxygenation (ECMO) machines, dialysis machines, blood pressure monitors, otoscopes, ophthalmoscopes, stethoscopes, sphygmomanometers, blood pressure cuffs, electrocardiographs, thermometers, defibrillators, speculas, sigmoidoscopes, and anoscopes.

[0062] As used herein, a "surgical instrument" includes any tool or instrument used to perform a surgical procedure or operation. Examples include scalpels, lancets, trocars, hemostats, graspers, forceps, clamps, retractors, distractors, positioners, tracheotomes, dilators, staplers, irrigation needles, syringe needles, drills, scopes, endoscopes, probes, rulers, and calipers.

[0063] As used herein, "safety equipment" includes equipment used to protect a person, animal, or object. Examples of "safety equipment" are masks, face shields, visors, goggles, glasses, gloves, shoe covers, foot guards, leg guards, belts, smocks, aprons, coats, vests, rain gear, hats, helmets, chin straps, hair nets, shower caps, hearing protection (earplugs, ear muffins, hearing bands), respirators, gas masks, attached air hoods, collars, lanyards, and first aid kits.

[0064] As used herein, "fabric" includes any type of suitable fabric, such as bedding, curtains, towels, table covers, coverlets, dish towels, and the like.

[0065] As used herein, an "apparel item" includes an item of clothing, footwear, or other item that someone wears on themselves. Examples include uniforms, coats, shirts, pants, waterproof pants, scrubs, socks, shoe or boot liners, insoles, gloves, hats, shoes, boots, and sandals.

[0066] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. Furthermore, the materials, methods, and examples are merely illustrative and are not intended to be limiting.

[0067] It will be readily understood that the aspects of the present disclosure, as generally described herein and illustrated in the Figures, can be arranged, substituted, combined, separated, and designed in a wide variety of different configurations, all of which are expressly contemplated herein.

[0068] Additionally, the particular arrangements shown in the drawings should not be considered limiting. It should be understood that other embodiments may include more or less of each element shown in a given drawing. Additionally, some of the illustrated elements may be combined or omitted. Still further, exemplary embodiments may include elements not illustrated in the drawings. As used herein, with respect to measurements, "about" means ±5%. As used herein, recited ranges include the endpoints, such that 0.5 mole percent to 99.5 mole percent includes both 0.5 mole percent and 99.5 mole percent.

[0069] Goods The polymer may be in the form of a coating on a surface or in the form of a film that may be applied to a surface. In some embodiments, the polymer (e.g., the polymer in the coating or film) is in the form of a fiber, such as a spun fiber, an electrospun fiber, an extruded fiber, a nanofiber, or any combination thereof. In some embodiments, the polymer may be coated onto a surface by any method, such as solution cast coating. In certain embodiments, the polymer may be in the form of a microporous film, a nanoporous film, a nonwoven sheet, a woven sheet, a mat, a fabric, or any combination thereof.

[0070] The polymer may be applied as a pure polymer or as part of a blend with other materials. For example, the polymer may be a blend with one or more other polymers. In certain embodiments, the polymer is a graft copolymer, an interpenetrating network, an aerogel, and / or a hydrogel.

[0071] The surface that the polymer can be applied to can include the surface or part of a medical device.For example, the medical device can be a urinary catheter, a percutaneous catheter, a central venous catheter, a vascular access device, a heart valve, a stent, an artificial blood vessel, a skeletal joint, a dental filling, a dental implant, an oxygen transport membrane, a suture, an intravenous delivery site, a drug delivery catheter, a drain, a gastric feeding tube, a tracheotomy tube, a contact lens, an intraocular lens, an orthopedic implant, a neurostimulation lead, a pacemaker lead, a blood bag, an air filter, and / or a drug diffusion matrix (e.g., a membrane, a film, a rod, a bead, or any combination thereof).In certain embodiments, the medical device is a contact lens, an intraocular lens, or an air filter.

[0072] In some embodiments, the polymer is incorporated into a water treatment device or a medical device. In some embodiments, the polymer is in the form of a separation membrane in the water treatment device. In some embodiments, the polymer can be coated or incorporated into a medical device (e.g., a part of a medical device, a surface of a medical device, a part of a surface of a medical device), and the medical device can include a urinary catheter, a percutaneous catheter, a central venous catheter, a vascular access device, a heart valve, a stent, an artificial blood vessel, a skeletal joint, a dental filling, a dental implant, an oxygen transport membrane, a suture, an intravenous delivery site, a drug delivery catheter, a drain, a gastric feeding tube, a tracheotomy tube, a contact lens, an intraocular lens, an orthopedic implant, a neurostimulation lead, a pacemaker lead, a blood bag, an air filter, and / or a drug diffusion matrix (including a membrane, a film, a rod, or a bead). In certain embodiments, the medical device is a contact lens, an intraocular lens, and / or an air filter. For example, the medical device can be an air filter.

[0073] The polymers of the present disclosure may be applied to or incorporated into a variety of articles where antiviral and / or antimicrobial properties are advantageous. For example, articles may include food or beverage equipment (e.g., tanks, conveyors, floors, drains, coolers, freezers, refrigerators, equipment surfaces, walls, valves, belts, pipes, drains, joints, crevasses, combinations thereof, etc.); building surfaces (e.g., walls, wood framing, floors, windows), kitchens (sinks, drains, countertops, refrigerators, cutting boards), bathrooms (showers, toilets, drains, pipes, bathtubs), (decks, wood, wallboard and other home exterior surfaces, asphalt shingles, patios or stone areas (especially for algae treatment); boats and boat equipment surfaces; airplanes and airplane equipment surfaces; garbage disposals, trash cans and Dumpsters™ or other trash removal equipment and surfaces; non-food equipment related pipes and drains; surfaces in hospitals, operating rooms or outpatient centers or veterinary surfaces (e.g., walls, floors, beds, equipment, clothing worn in hospitals / veterinary or other healthcare settings (including scrubs, shoes, and other hospital or veterinary surfaces)), first responder or other emergency services equipment and clothing; sawmill equipment, surfaces and wood products; bathroom surfaces such as sinks, showers, counters, and toilets; clothing and shoes; toys; school and gym equipment, walls, floors, windows and other surfaces, kitchen surfaces such as sinks, counters, appliances; wooden or composite decks, pool, whirlpool and spa surfaces; carpets; paper; leather; animal carcasses, furs and hides.

[0074] The polymers of the present disclosure may be coated or incorporated onto fibrous substrates, including fibers, yarns, fabrics, textiles, nonwovens, carpets, leather, or paper. The fibrous substrates are made of natural fibers such as wool, cotton, jute, sisal, seaweed, paper, coir, and cellulose, or mixtures thereof; or made of synthetic fibers such as polyamides, polyesters, polyolefins, polyaramids, acrylics, and blends thereof; or made of blends of at least one natural fiber and at least one synthetic fiber. By "fabric" we mean natural or synthetic fabrics, or blends thereof, composed of fibers such as cotton, rayon, silk, wool, polyester, polypropylene, polyolefins, nylon, and aramids such as "NOMEX®" and "KEVLAR®". By "fabric blend" we mean fabrics made of two or more types of fibers. Typically, these blends are a combination of at least one natural fiber and at least one synthetic fiber, but they can also be blends of two or more natural fibers or two or more synthetic fibers. Nonwoven substrates include, for example, spunlaced nonwovens, such as SONTARA, available from EI du Pont de Nemours and Company, Wilmington, Del., USA, and laminate nonwovens, such as spunbond-meltblown-spunbond nonwovens.

[0075] Examples of surface materials onto which polymers may be coated or incorporated include metals (e.g., steel, stainless steel, chromium, titanium, iron, copper, brass, aluminum, and alloys thereof), minerals (e.g., concrete), other polymers and plastics (e.g., polyolefins such as polyethylene, polypropylene, polystyrene, poly(meth)acrylates, polyacrylonitrile, polybutadiene, poly(acrylonitrile, butadiene, styrene), poly(acrylonitrile, butadiene), acrylonitrile butadiene; polyesters such as polyethylene terephthalate; and polyamides such as nylon). Additional surfaces include brick, tile, ceramic, porcelain, wood, vinyl, and linoleum.

[0076] The polymers of the present disclosure can be a component (e.g., a surface, bulk, or part) of a larger structure. For example, the polymers can be used in medical devices, diagnostic devices, implants, gloves, masks, curtains, mattresses, sheets, blankets, gauze, dressings, tissue, surgical drapes, tubing, surgical instruments, safety equipment, fabrics, apparel items, floors, handles, walls, sinks, showers or bathtubs, toilets, furniture, wall switches, toys, athletic equipment, play equipment, shopping carts, countertops, appliances, handrails, doors, air filters, pipes, utensils, dishes, cups, containers, object display containers, food, food display containers, food packaging, food processing equipment, food handling equipment, food transport equipment, food vending machines, food storage equipment, food packaging equipment, plants, phones, cell phones, remote controls, computers, mice, keyboards, touch screens, leather, cosmetics, cosmetics manufacturing equipment, cosmetics storage equipment, cosmetics packaging equipment, pa The present invention may be part of a substrate such as a personal care product, a personal care product manufacturing equipment, a personal care storage equipment, a personal care packaging equipment, an animal care product, an animal care product manufacturing equipment, a veterinary equipment, a powder, a cream, a gel, an ointment, an eye care product, an eye care product manufacturing equipment, a contact lens, an eyeglass, an eye care storage equipment, a contact lens case, jewelry, jewelry manufacturing equipment, jewelry storage equipment, an animal housing, an agricultural equipment, an animal food handling equipment, an animal food storage space, an animal food storage equipment, an animal food container, an aircraft, a land vehicle, an air treatment device, an air filter, a water storage space, a water storage device, a water treatment device, a water storage container, a water filter, a pharmaceutical display container, a pharmaceutical packaging, a pharmaceutical treatment device, a pharmaceutical handling equipment, a pharmaceutical transport equipment, a pharmaceutical sales equipment, a pharmaceutical, a pharmaceutical storage equipment, and / or a pharmaceutical packaging equipment.

[0077] The polymers may be incorporated into or coated onto parts of toys or athletic equipment, including exercise equipment, playground equipment, or pools.

[0078] "Animal care items" and "veterinary equipment" can be any product used in a setting involving animals, such as a home, a boarding house, or a livestock hospital. Of course, veterinary equipment can be used in places other than hospitals. Animals are typically any animal considered to be pets, non-pets, boarding animals, animals treated by a veterinarian, and wild animals. Examples include dogs, cats, reptiles, birds, rabbits, ferrets, guinea pigs, hamsters, rats, mice, fish, turtles, horses, goats, cows, and pigs. Suitable animal care items include personal care items, toys, beds, crates, kennels, carriers, bowls, dishes, leashes, collars, litter boxes, and grooming items (e.g., clippers, scissors, brushes, combs, de-matting tools, and de-shedding tools) described herein. Suitable veterinary equipment includes any of the medical and surgical instruments described herein, as well as other devices such as tables, bathtubs, stretchers, sinks, scales, cages, carriers, and leashes.

[0079] "Animal housing" can be any suitable housing, such as a chicken coop, stable, shelter, grab bag shelter, hutch, pen, shed, drive-in pen, nest box, feeder, divider, cage, carrier, or bed.

[0080] "Agricultural equipment" is any equipment used in an agricultural setting, including a farm or ranch, particularly a farm or ranch that houses animals, processes animals, or both. Animal livestock that can be housed or processed as described herein include, for example, horses, cattle, bison, and small animals such as poultry (e.g., chickens, quail, turkeys, geese, ducks, pigeons, doves, pheasants, swans, ostriches, guinea fowl, Indian peacocks, emus), pigs, sheep, goats, alpacas, llamas, deer, donkeys, rabbits, and fish. Examples of farm equipment include wagons, trailers, carts, barns, sheds, fences, sprinklers, shovels, scrapers, halters, ropes, restrainers, feeders, waterers, troughs, water filters, water treatment equipment, ponds, fountains, buckets, pails, hay racks, scales, poultry flooring, egg treatment equipment, barn curtains, tractors, seeders, planters, plows, rotators, tillers, spreaders, sprayers, agitators, sorters, balers, harvesters, cotton pickers, threshers, lawnmowers, backhoe loaders, squeeze chute, hydraulic chutes, head chutes, head gates, crowding tubs, corral tubs, alleys, weaning stalls, calf tables, and milking machines.

[0081] The article may be part of a vehicle, such as an aircraft, land vehicle, or water vehicle. Suitable vehicles include cars, vans, trucks, buses, ambulances, recreational vehicles, campers, motorcycles, scooters, bicycles, wheelchairs, trains, trams, ships, boats, canoes, submarines, unmanned underwater vehicles (UUVs), personal watercraft, airplanes, jet planes, helicopters, unmanned autonomous vehicles (UAVs), and hot air balloons.

[0082] microorganisms In some embodiments, the microorganisms inhibited or killed by the polymeric coatings of the present disclosure are gram-positive bacteria. In certain embodiments, the microorganisms are gram-negative bacteria. The bacteria can be pathogenic. For example, pathogenic bacteria include Escherichia coli, Staphylococcus aureus, Campylobacter spp., Legionella spp., Salmonella spp., Shigella spp., Tsukamurella spp., Leptospires spp., Mycobacterium spp., Pseudomonas aeruginosa, Aeromonas spp., Vibrio spp., Yersinia spp., Bacillus spp., Enterobacter sakazakii, Burkholderia pseudomallei, and others. The pathogen may be selected from the group consisting of Bacillus subtilis, Bacillus pseudomallei, Acinetobacter spp., Helicobacter pylori, Klebsiella spp., Clostridium spp., and Streptococci. The terms "pathogen" and "pathogenic" are used interchangeably herein and refer to bacteria, fungi, viruses, and other microscopic organisms capable of exerting a pathogenic effect on multicellular organisms. Thus, use of the term "pathogen" contemplates microscopic organisms capable of causing disease in plants, mammals, including humans.

[0083] Further exemplary Gram-positive bacteria that are inhibited or killed by the polymer coating include, but are not limited to, Mycobacterium tuberculosis. tuberculosis, Mycobacterium bovis, Mycobacterium typhimurium, Mycobacterium bovis strain BCG, BCG substrains, Mycobacterium avium, Mycobacterium intracellulare, Mycobacterium africanum, Mycobacterium kansasii, Mycobacterium marinum, Mycobacterium ulcerans, Mycobacterium avium subsp. paratuberculosis, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus equi, Streptococcus pyogenes These include: S. pyogenes, Streptococcus agalactiae, Listeria monocytogenes, L. ivanovii, Bacillus anthracis, B. subtilis, Nocardia asteroids and other Nocardia species, Streptococcus viridans group, Peptococcus species, Peptostreptococcus species, Actinomyces israelii and other Actinomyces species, Propionibacterium acnes, and Enterococcus species. Gram-negative bacteria that are inhibited or killed by the polymer coating include, but are not limited to, Clostridium tetani, C. perfringens, C. botulinum,botulinum, other Clostridium spp., Pseudomonas aeruginosa, other Pseudomonas spp., Campylobacter spp., Vibrio cholerae, Ehrlichia spp., Actinobacillus pleuropneumoniae, Pasteurella haemolytica, P. multocida, other Pasteurella spp., Legionella pneumophila, other Legionella spp., Salmonella typhi typhi, other Salmonella spp., Shigella spp., Brucella abortus, other Brucella spp., Chlamydia trachomatis, C. psittaci, Coxiella burnetti, Escherichia coli, Neiserria meningitidis, N. gonorrhea, Haemophilus influenzae, H. ducreyi, other Haemophilus spp., Yersinia pestis, Y. enterocolitica, other Yersinia spp., Escherichia coli, Enterococcus hiraehirae and other Escherichia species, as well as other Enterobacteriacae, Brucella abortus and other Brucella species, Burkholderia cepacian, Burkholderia pseudomallei, Francisella tularensis, Bacteroides fragilis, Fusobacterium nucleatum, Provetella species, Cowdria ruminantium, Klebsiella species, and Proteus species.

[0084] In some embodiments, the microorganisms inhibited or killed by the polymer coating of the present disclosure are viruses, including alphacoronaviruses, betacoronaviruses (e.g., SARS-CoV-2), deltacoronaviruses, gammacoronaviruses, and toroviruses; influenza virus A, influenza virus B, influenza virus C, influenza virus D, hepatitis A virus, hepatitis B virus, simplex virus, cytomegalovirus, mamastrovirus, mastadenovirus, poxviruses, hepadnaviruses, asfarviridae, flaviviruses, alphaviruses, togaviruses, paramyxoviruses, rhabdoviruses, bunyaviruses, filoviruses, retroviridae, coxsackieviruses (enveloped and non-enveloped), rotaviruses, polioviruses, caliciviruses, orthopoxviruses, polyomaviruses, vegicloviruses, varicelloviruses, phleboviruses, alphatorqueviruses, noroviruses, leukemia virus ... The virus may be selected from a rubulavirus, a spumavirus, a rubulavirus, a hantavirus, a sapovirus, a sarivirus, a rubivirus, a rosavirus, a lyssavirus, an enterovirus, an arenavirus, an orthobunyavirus, a parapoxvirus, a henipavirus, a morsipoxvirus, a polyomavirus, a cardiovirus, a morbillivirus, a Marburgvirus, a deltaretrovirus, an orthopneumovirus, an erythrovirus, a respirovirus, an alphapapillomavirus, a mupapillomavirus, a rhadinovirus, a roseolovirus, a deltavirus, a hepevirus, a hepacivirus, an orthohepadnavirus, a henipavirus, a pegivirus, a lymphocryptovirus, an Ebolavirus, a nairovirus, a thogotovirus, a cosavirus, a ceradornavirus, a kobuvirus, a dependovirus, or any combination thereof. In certain embodiments, the virus is a coronavirus, such as SARS-CoV or SARS-CoV2.

[0085] In some embodiments, the microorganisms inhibited or killed by the polymer coatings of the present disclosure include fungi. For example, fungi include those of the genera Candida spp., Cryptococcus spp., Blastomyces spp., Coccidioides spp., Aspergillus spp., Emmonsia spp., Chrysosporium spp., Fonsecaea spp., Trychophyton spp., Histoplasma spp., Ajellomyces spp., Pneumocystis spp., and the like. The fungus may be Candida species, Microsporum species, Magnaporthe species, Fusarium species, Sporothrix species, Cyberlindnera species, Mucormycetes species, Epidermophyton species, Trichosporon species, Paracoccidioides species, Talaromyces species, Uncinocarpus reesii, and Aphanoascus species. In some embodiments, the fungus is a Candida species or a Cryptococcus species.Other exemplary fungi that may be inhibited or killed by the polymeric coatings of the present disclosure include Alternaria alternata, Aspergillus niger, Aureobasidium pullulans, Cladosporium cladosporioides, Drechslera australiensis, Gliomastix cerealis, Monilia grisea, Penicillium commune, Phoma fimeti, Pithomyces chartarum, Scolecobasidium humicola, or any combination thereof.

[0086] polymer In one aspect, a polymer is provided. The polymer comprises one or more repeat units ("monomeric units"). In one embodiment, at least one of the monomeric units comprises one or more benzimidazolium-containing moieties M1 having formula (I):

[0087] [ka]

[0088] (In the formula, R 1AA is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3AAis independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1AA , R 2AA , R 3AA , and R 5AA at least one of which is a polymer Includes.

[0089] These definitions of "R groups" are consistent for all formulas, figures, and schemes throughout this disclosure. In each instance, every R group is independently selected.

[0090] In another aspect, another polymer is provided. The polymer comprises one or more repeat units. In one embodiment, at least one of the repeat units comprises one or more imidazolium-containing moieties M2 having formula (II):

[0091] [ka]

[0092] (In the formula, R 1XX is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3XX is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1XX, R 2XX , R 3XX , and R 5XX at least one of which is a polymer In each instance, every R group is independently selected.

[0093] As used herein, the term moiety is used to refer to one or both of the moieties of formula (I) and the moieties of formula (II). These may be collectively referred to as moieties. These may also be referred to as imidazolium moieties or benzimidazolium moieties.

[0094] The steric crowding of the provided moieties arises from the interaction of the R3 imidazolium or benzimidazolium group with the relatively "bulky" group at the R1 position on the aryl ring. 1AA Groups and R 1XX The group is at least as large as a methyl group.

[0095] The moiety can be incorporated into the polymer in any manner known to one of skill in the art. In particular, the moiety can be 1AA rank, R 2AA rank, R 3AA rank, R 5AA rank, R 1XX rank, R 2XX rank, R 3XX rank, and R 5XX The moieties can be attached to the polymer chain at any of the R group positions. As used herein, when an R group is defined as a "polymer," that R group position connects one of the moieties to the polymer chain. As discussed further herein, multiple R groups can be "polymers," and the moieties can be incorporated into the polymer in several ways, including as part of the polymer backbone and / or as pendants.

[0096] In one embodiment, the moiety M1 is incorporated into a monomer as part of the polymer backbone, as described in further experimental details below. As used herein, a monomer that is part of the main chain (or backbone) of a polymer is a repeat unit that is connected at least at two ends to a polymer chain. The moiety may be the only moiety in the backbone monomer:

[0097] [ka]

[0098] It will be appreciated that the moiety may alternatively be one of multiple moieties within the backbone of the monomer: [M1] x [A] y [B] z .

[0099] As an example of incorporating the moiety M1 into the backbone of a polymer, the following exemplary structures of formula (IA) are illustrative:

[0100] [ka]

[0101] (In the formula, L 1AA are optional additional groups on either side of the moiety). L 1AA can be any group known to one of ordinary skill in the art (e.g., alkyl, aryl, etc.).

[0102] In one embodiment, the moiety M1 is incorporated as a pendant moiety attached to the backbone of the polymer. As used herein, the term "pendant" refers to a moiety that is attached to the polymer backbone at only one end. The moiety may be directly connected to the polymer backbone, or an additional moiety (e.g., a linker group, L) may be inserted between the moiety and the polymer backbone. 2AA It is recognized that a bond may be present. 1AA rank, R 2AA rank, R 3AA Rank or R 5AA You can come in at any of the following places:

[0103] For example, the bond may be R on an aryl as shown in formula (IB) below: 2AA You can pass the rank. 2AA is the polymer backbone, P 1AA is an optional linker group connecting the moiety to 2AA can be any group known to those of skill in the art.

[0104] [ka]

[0105] Alternatively, the bond may be R on the benzimidazolium as shown in formula (IC) below: 3AA You can pass the rank.

[0106] [ka]

[0107] In one embodiment, the moiety M2 is incorporated as a pendant moiety attached to the backbone of the polymer. The moiety may be directly connected to the polymer backbone, or an additional moiety (e.g., a linker group, L 2AA It is recognized that a bond may be present. 1AA rank, R 2AA rank, R 3AA Rank or R 5AA You can come in at any of the following places:

[0108] For example, the bond may be R on an aryl as shown in formula (II-A) below: 2XX You can pass the rank.

[0109] [ka]

[0110] Similarly, the bond can be R on the imidazolium as shown in formula (II-B) below:3XX You can pass the rank.

[0111] [ka]

[0112] Given multiple available positions on the moiety for attachment to the polymer backbone, the moiety can be attached to multiple polymer chains (e.g., as part of a crosslink). 3XX Two polymer chains, P 1XX and P 2XX An exemplary embodiment showing cross-linking between is shown below in formula (II-C): It will be appreciated that the cross-linking ability of the moieties is not limited to the illustrated embodiment.

[0113] [ka]

[0114] In one embodiment, the moiety M1 is grafted onto an already formed polymer. For example, a monosubstituted R 3AA Using a benzimidazole (formula ID) having the position P 1AA By mixing with and heating, the previously vacant R 3AA A pendant benzimidazolium (formula IC) can be produced, in which the P 1AA Examples include alkyl halide-containing polymers such as chloromethylated polysulfone and poly(chloromethylstyrene), including perfluorinated polymers containing haloalkyl groups. Additionally, perfluorinated sulfonyl halide-containing polymers, or acyl halide-containing polymers can be functionalized using this method.

[0115] [ka]

[0116] Alternatively, the moiety M2 is grafted onto an already formed polymer using an imidazole with a monosubstituted R3 position (formula II-D) to generate a pendant imidazolium (formula II-C).

[0117] [ka]

[0118] In certain embodiments, the disclosed cationic moieties form salts with anions. Any anion sufficient to balance the charge of the moiety-containing polymer can be used. Representative anions include iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate.

[0119] The polymer containing moieties can be of any size known to those of skill in the art.

[0120] In some embodiments, the polymer is a polymer of Formula III:

[0121] [ka]

[0122] It is.

[0123] In one embodiment, in formula (III), R 1AA and R 3AA is a methyl group, and R 2AA is hydrogen.

[0124] In some embodiments, polymers of the present disclosure may include one or more repeat units, where at least one of the repeat units comprises one or more benzimidazolium-containing moieties of formulae (IV)-(VIII):

[0125] [ka]

[0126] (In the formula, R1 is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups, and polymers; R2 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and polymers; R5 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; At least one of R1, R2, R3, and R5 is a polymer; X is independently selected from the group consisting of alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and no group. Includes.

[0127] In some embodiments, the polymer is a salt formed with an anion selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bicarbonate, bisulfate, hydrogen phosphate, and dihydrogen phosphate.

[0128] In some embodiments, the benzimidazolium-containing moiety is included in the main chain (ie, backbone) of the polymer.

[0129] In some embodiments, the benzimidazolium-containing moiety is included in a pendant group of the polymer.

[0130] In some embodiments, the benzimidazolium-containing moiety is part of a crosslink in a polymer.

[0131] In some embodiments, a polymer having at least one of the repeat units comprising one or more benzimidazolium-containing moieties of formulae (IV)-(VIII) further comprises a second repeat unit defined by formula (IV-A):

[0132] [ka]

[0133] (In the formula, R1 is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups, and polymers; R2 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and polymers; R5 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; At least one of R1, R2, R3, and R5 is a polymer; X is independently selected from the group consisting of alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and no group. It may further include.

[0134] The benzimidazolium-containing moieties can be incorporated into the polymer in any manner known to those skilled in the art. In particular, the moieties can be attached to the polymer chain at either the R1, R2, R3, or R5 positions. As used herein, when an R group is defined as a "polymer," that R group position connects one of the benzimidazolium-containing moieties to the polymer chain. As discussed further herein, multiple R groups can be "polymers," and the benzimidazolium-containing moieties can be incorporated into the polymer in several ways, including as part of the polymer backbone and / or as pendants.

[0135] In one embodiment, the benzimidazolium-containing moiety is incorporated into the polymer backbone, as described in further experimental details below. As used herein, a monomer that is part of the main chain (or backbone) of a polymer is a repeat unit that is connected at least at two ends to the polymer chain. The moiety may be the only moiety within the backbone monomer:

[0136] [ka]

[0137] It will be appreciated that the moiety may alternatively be one of multiple moieties within the backbone of the monomer: [benzimidazolium-containing moiety] x [A] y [B] z .

[0138] In one embodiment, the benzimidazolium-containing moiety is incorporated as a pendant moiety attached to the backbone of the polymer. As used herein, the term "pendant" refers to a moiety that is attached to the polymer backbone at only one end. It is recognized that the benzimidazolium-containing moiety may be directly connected to the polymer backbone, or there may be an additional moiety (e.g., a linker group) between the moiety and the polymer backbone. Again, the attachment may be at any of the R1, R2, R3, or R5 positions.

[0139] Given the multiple available positions on the moiety for attachment to the polymer backbone, the moiety can be attached to multiple polymer chains (e.g., as part of a crosslink). An exemplary embodiment showing a crosslink between two polymer chains, P1 and P2, via the R3 position is shown below in formula (IV-B). It is recognized that the crosslinking ability of the moiety is not limited to the illustrated embodiment.

[0140] [ka]

[0141] As described above, the polymers of the present disclosure include one or more repeat units, at least one of which includes one or more of the benzimidazolium-containing moieties of formula (IV)-(VIII) in any combination. In some embodiments, the polymer includes one or more repeat units, at least one of which includes a benzimidazolium-containing moiety of formula (IV). In some embodiments, the polymer includes one or more repeat units, at least one of which includes a benzimidazolium-containing moiety of formula (V). In some embodiments, the polymer includes one or more repeat units, at least one of which includes a benzimidazolium-containing moiety of formula (VI). In some embodiments, the polymer includes one or more repeat units, at least one of which includes a benzimidazolium-containing moiety of formula (VII). In some embodiments, the polymer includes one or more repeat units, at least one of which includes a benzimidazolium-containing moiety of formula (VIII).

[0142] In some embodiments, the polymer comprises one or more repeat units, wherein one or more repeat units comprise a benzimidazolium-containing moiety of Formula (IV) and Formula (V); Formula (IV) and Formula (VI); Formula (IV) and Formula (VII); Formula (IV) and Formula (VIII); Formula (IV) and Formula (IV-A); Formula (V) and Formula (VI); Formula (V) and Formula (VII); Formula (V) and Formula (VIII); Formula (V) and Formula (IV-A); Formula (VI) and Formula (VII); Formula (VI) and Formula (VIII); Formula (VI) and Formula (IV-A); Formula (VII) and Formula (VIII); Formula (VII) and Formula (IV-A); Formula (VII) and Formula (VIII); Formula (VII) and Formula (IV-A); or Formula (VIII and Formula (IV-A).

[0143] In some embodiments, the polymer comprises one or more repeat units, and the one or more repeat units comprises a benzimidazolium-containing moiety of three of Formula (IV), Formula (V), Formula (VI), Formula (VII), Formula (VIII), and Formula (IV-A).

[0144] In some embodiments, the polymer comprises one or more repeat units, and one or more repeat units comprises a benzimidazolium-containing moiety of formula (IV), formula (VIII), and formula (IV-A). In some embodiments, one or more repeat units of the polymer comprises a benzimidazolium-containing moiety of formula (V), formula (VI), formula (VII), formula (VIII), and formula (IV-A). In certain embodiments, one or more repeat units of the polymer comprises a benzimidazolium-containing moiety of formula (V), formula (VIII), and formula (IV-A).

[0145] The above polymers can have the following embodiments and features:

[0146] In some embodiments, R1 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, and heteroaryl.

[0147] In some embodiments, R1 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, and perfluoroalkoxy.

[0148] In some embodiments, R1 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, and heteroalkyl.

[0149] In some embodiments, R1 is independently selected from the group consisting of alkyl, perfluoroalkyl, and heteroalkyl.

[0150] In some embodiments, R1 is alkyl.

[0151] In some embodiments, R1 is methyl.

[0152] In some embodiments, R2 is independently selected from the group consisting of hydrogen and any group.

[0153] In some embodiments, R2 is independently selected from the group consisting of hydrogen and alkyl.

[0154] In some embodiments, R2 is independently selected from the group consisting of hydrogen and methyl.

[0155] In some embodiments, R3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl.

[0156] In some embodiments, R3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, and aryl.

[0157] In some embodiments, R3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, and heteroalkyl.

[0158] In some embodiments, R3 is independently selected from the group consisting of alkyl, perfluoroalkyl, and heteroalkyl.

[0159] In some embodiments, R3 is alkyl.

[0160] In some embodiments, R3 is methyl.

[0161] In some embodiments, R5 is independently selected from the group consisting of hydrogen, alkyl, and a polymer.

[0162] In some embodiments, R5 is independently selected from the group consisting of hydrogen and a polymer.

[0163] In some embodiments, X is independently selected from the group consisting of alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and no group.

[0164] In some embodiments, X is independently selected from the group consisting of alkylene, arylene, and aralkylene.

[0165] In some embodiments, X is independently selected from the group consisting of alkylene and arylene.

[0166] In some embodiments, X is arylene.

[0167] In some embodiments, X is phenylene (eg, 1,4-phenylene).

[0168] The polymer is a copolymer of formula (IX)

[0169] [ka]

[0170] (In the formula, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are H and C, respectively. 1~6Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 13a , R 13b , R 14a , and R 14b Two of them are non-existent, the remaining two are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 23a , R 23b , R 24a , and R 24b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 23a , R 23b , R 24a and R 24b One of them is non-existent, the remaining three are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 Alkyl, C 1~6 Haloalkyl, C1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; X 11 , X 21 , and X 31 are non-existent, C 1~6 Alkylene, C 1~6 independently selected from the group consisting of haloalkylene, arylene, and heteroarylene; a, b, and c are mole percentages; a is 0 mole percent to 45 mole percent; b+c is 55 mole percent to 100 mole percent; b and c are each greater than 0 percent; a+b+c=100%.) It could be.

[0171] In some embodiments, the copolymer of formula (IX) is a copolymer of formula (IXa)

[0172] [ka]

[0173] (In the formula, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 13a , R 13b , R 14a , and R 14b Two of them are non-existent, the remaining two are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 23a , R 23b , R 24a, and R 24b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 23a , R 23b , R 24a and R 24b One of them is non-existent, the remaining three are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; X 11 , X 21 , and X 31 are non-existent, C1~6 Alkylene, C 1~6 independently selected from the group consisting of haloalkylene, arylene, and heteroarylene; a, b, and c are mole percentages; a is 0 mole percent to 45 mole percent; b+c is 55 mole percent to 100 mole percent; b and c are each greater than 0 percent; a+b+c=100%.) It is.

[0174] The copolymers of formula (IX) (and formula (IXa)) above can have the following embodiments and features:

[0175] In some embodiments, the copolymer of Formula (IX) (and Formula (IXa)) is a random copolymer.

[0176] In some embodiments, the copolymer of formula (IX) (and formula (IXa)) is a block copolymer. Block copolymers can be made, for example, as described in Maity S. and Jana T., Appl. Mater. Interfaces, 2014, 6(9), pp. 6851-6864. For example, two separate homopolymers can be synthesized and then reacted together in a separate polymerization to obtain a block copolymer. Post-polymerization functionalization (described in more detail below) can then provide a block copolymer with an ionic amine backbone, with N-substitutions randomly distributed along the polymer chain.

[0177] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 Alkyl, C1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0178] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0179] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 Alkyl and C 1~6 haloalkyl.

[0180] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 alkyl.

[0181] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are each independently selected from methyl and ethyl.

[0182] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are methyl.

[0183] In some embodiments, R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0184] In some embodiments, R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R32c , and R 32d are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0185] In some embodiments, R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are H and C, respectively. 1~6 Alkyl, and C 1~6 haloalkyl.

[0186] In some embodiments, R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are H and C, respectively. 1~6 alkyl.

[0187] In some embodiments, R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are each independently selected from H, methyl, and ethyl.

[0188] In some embodiments, R12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are each independently selected from H and methyl.

[0189] In some embodiments, R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0190] In some embodiments, R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0191] In some embodiments, R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 Alkyl, and C 1~6 haloalkyl.

[0192] In some embodiments, R 12a , R 12c , R 22a , R 22c, R 32a , and R 32c are H and C, respectively. 1~6 alkyl.

[0193] In some embodiments, R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H, methyl, and ethyl.

[0194] In some embodiments, R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H and methyl.

[0195] In some embodiments, R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 haloalkoxy, and halo, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0196] In some embodiments, R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6haloalkoxy, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0197] In some embodiments, R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, and C 1~6 haloalkyl, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 Alkyl and C 1~6 haloalkyl.

[0198] In some embodiments, R 13a , R 13b , R 14a , and R 14b are non-existent and C 1~6 alkyl, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 alkyl.

[0199] In some embodiments, R 13a , R 13b , R 14a , and R 14b are each independently selected from absent, methyl, and ethyl, with the proviso that R 13a , R 13b , R 14a , and R 14bTwo of are absent and the remaining two are present and are independently selected from methyl and ethyl.

[0200] In some embodiments, R 13a , R 13b , R 14a , and R 14b are each independently selected from absent and methyl, with the proviso that R 13a , R 13b , R 14a , and R 14b Two of the are absent and the remaining two are present and are methyl.

[0201] In some embodiments, R 23a , R 23b , R 24a , and R 24b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 haloalkoxy, and halo, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0202] In some embodiments, R 23a , R 23b , R 24a , and R 24b are non-existent, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 Alkyl, C1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0203] In some embodiments, R 23a , R 23b , R 24a , and R 24b are non-existent, C 1~6 Alkyl, and C 1~6 haloalkyl, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 Alkyl and C 1~6 haloalkyl.

[0204] In some embodiments, R 23a , R 23b , R 24a , and R 24b are non-existent and C 1~6 alkyl, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 alkyl.

[0205] In some embodiments, R 23a , R 23b , R 24a , and R 24b are each independently selected from absent, methyl, and ethyl, with the proviso that R 23a , R 23b , R 24a , and R 24b is absent and the remaining three are present and are independently selected from methyl and ethyl.

[0206] In some embodiments, R 23a , R 23b , R 24a , and R24b are each independently selected from absent and methyl, with the proviso that R 23a , R 23b , R 24a , and R 24b One of the is absent and the remaining three are present and are methyl.

[0207] In some embodiments, R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0208] In some embodiments, R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy and C 1~6 haloalkoxy.

[0209] In some embodiments, R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 Alkyl and C 1~6 haloalkyl.

[0210] In some embodiments, R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 alkyl.

[0211] In some embodiments, R 33a , R 33b , R 34a , and R 34bare each independently selected from methyl and ethyl.

[0212] In some embodiments, R 33a , R 33b , R 34a , and R 34b are each independently methyl.

[0213] In some embodiments, R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 Alkyl, C 1~6 Haloalkyl, C 1~6 Alkoxy, C 1~6 Independently selected from haloalkoxy, and halo.

[0214] In some embodiments, R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 Alkyl, and C 1~6 haloalkyl.

[0215] In some embodiments, R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 alkyl.

[0216] In some embodiments, R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H, respectively.

[0217] In some embodiments, X 11 , X 21 , and X 31 are respectively, C 1~6 Alkylene, C 1~6 is independently selected from the group consisting of haloalkylene, arylene, and heteroarylene.

[0218] In some embodiments, X 11 , X 21 , and X 31 are each independently selected from the group consisting of arylene and heteroarylene.

[0219] In some embodiments, X 11 , X 21 , and X 31 are each independently selected from arylene.

[0220] In some embodiments, X 11 , X 21 , and X 31 are each phenylene (eg, 1,4-phenylene).

[0221] In some embodiments, a, b, and c are mole percentages; a is 5 mole percent or more; b+c is 95 mole percent or less; b and c are each greater than 0 percent; a+b+c=100%.

[0222] In some embodiments, a, b, and c are mole percentages; a is 5 mole percent to 45 mole percent; b+c is 55 mole percent to 95 mole percent; b and c are each greater than 0 percent; a+b+c=100%.

[0223] In some embodiments, a, b, and c are mole percentages; a is 2 mole percent to 45 mole percent; b+c is 55 mole percent to 98 mole percent; b and c are each greater than 0 percent; a+b+c=100%.

[0224] In some embodiments, a, b, and c are mole percentages; a is 0 mole percent to 45 mole percent; b+c is 55 mole percent to 100 mole percent; b and c are each greater than 0 percent; a+b+c=100%.

[0225] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 independently selected from alkyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 independently selected from alkyl; R 13a , R 13b , R 14a , and R 14b are non-existent, C 1~6 Alkyl, and C 1~6 haloalkyl, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 Alkyl and C 1~6 haloalkyl; R 23a , R 23b , R 24a , and R 24b are non-existent, C 1~6 Alkyl, and C 1~6 haloalkyl, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 Alkyl and C 1~6 haloalkyl; R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6Alkyl and C 1~6 haloalkyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 X is independently selected from alkyl; 11 , X 21 , and X 31 are each independently selected from arylene; a, b, and c are mole percentages, a is from 2 mole percent to 45 mole percent, b+c is from 55 mole percent to 98 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0226] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are respectively, C 1~6 independently selected from alkyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are H and C, respectively. 1~6 independently selected from alkyl; R 13a , R 13b , R 14a , and R 14b are non-existent and C 1~6alkyl, where R 13a , R 13b , R 14a , and R 14b Two of them are absent and the remaining two are present, and C 1~6 independently selected from alkyl; R 23a , R 23b , R 24a , and R 24b are non-existent and C 1~6 alkyl, where R 23a , R 23b , R 24a , and R 24b One of the three is absent and the remaining three are present, and C 1~6 independently selected from alkyl; R 33a , R 33b , R 34a , and R 34b are respectively, C 1~6 independently selected from alkyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1~6 X is independently selected from alkyl; 11 , X 21 , and X 31 are each independently selected from arylene; a, b, and c are mole percentages, a is from 2 mole percent to 45 mole percent, b+c is from 55 mole percent to 98 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0227] In some embodiments, R 11a , R 11b, R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are each independently selected from methyl and ethyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H, methyl, and ethyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent, methyl, and ethyl, with the proviso that R 13a , R 13b , R 14a , and R 14b two of R are absent and the remaining two are present and are independently selected from methyl and ethyl; 23a , R 23b , R 24a , and R 24b are each independently selected from absent, methyl, and ethyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of R is absent and the remaining three are present and independently selected from methyl and ethyl; 33a , R 33b , R 34a , and R 34b are each independently selected from methyl and ethyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c, R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31 are each independently selected from arylene; a, b, and c are mole percentages, a is from 0 mole percent to 45 mole percent, b+c is from 55 mole percent to 100 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0228] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are each independently selected from methyl and ethyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H, methyl, and ethyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent, methyl, and ethyl, with the proviso that R 13a , R 13b , R 14a , and R 14b two of R are absent and the remaining two are present and are independently selected from methyl and ethyl; 23a , R 23b , R 24a , and R 24b are each independently selected from absent, methyl, and ethyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of R is absent and the remaining three are present and independently selected from methyl and ethyl;33a , R 33b , R 34a , and R 34b are each independently selected from methyl and ethyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31 are each independently selected from arylene; a, b, and c are mole percentages, a is from 2 mole percent to 45 mole percent, b+c is from 55 mole percent to 98 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0229] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are methyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H and methyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent and methyl, with the proviso that R 13a , R13b , R 14a , and R 14b two of the are absent and the remaining two are present and are methyl; R 23a , R 23b , R 24a , and R 24b are each independently selected from absent and methyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of the groups is absent and the remaining three are present and are methyl; R 33a , R 33b , R 34a , and R 34b are each independently methyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31 are each independently selected from arylene; a, b, and c are mole percentages, a is from 2 mole percent to 45 mole percent, b+c is from 55 mole percent to 98 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0230] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R31d are methyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H and methyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent and methyl, with the proviso that R 13a , R 13b , R 14a , and R 14b two of the are absent and the remaining two are present and are methyl; R 23a , R 23b , R 24a , and R 24b are each independently selected from absent and methyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of the groups is absent and the remaining three are present and are methyl; R 33a , R 33b , R 34a , and R 34b are each independently methyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31are each independently selected from arylene; a, b, and c are mole percentages, a is from 0 mole percent to 45 mole percent, b+c is from 55 mole percent to 100 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0231] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are methyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H and methyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent and methyl, with the proviso that R 13a , R 13b , R 14a , and R 14b two of the are absent and the remaining two are present and are methyl; R 23a , R 23b , R 24a , and R 24b are each independently selected from absent and methyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of the groups is absent and the remaining three are present and are methyl; R 33a , R 33b , R 34a , and R 34b are each independently methyl; R 15a , R 15b , R 15c , R 15d , R 15e , R15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31 are each phenylene (e.g., 1,4-phenylene); a, b, and c are mole percentages, a is from 2 mole percent to 45 mole percent, b+c is from 55 mole percent to 98 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0232] In some embodiments, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are methyl; R 12a , R 12c , R 22a , R 22c , R 32a , and R 32c are each independently selected from H and methyl; R 13a , R 13b , R 14a , and R 14b are each independently selected from absent and methyl, with the proviso that R 13a , R 13b , R 14a , and R 14b two of the are absent and the remaining two are present and are methyl; R 23a , R 23b , R 24a , and R 24bare each independently selected from absent and methyl, with the proviso that R 23a , R 23b , R 24a , and R 24b one of the groups is absent and the remaining three are present and are methyl; R 33a , R 33b , R 34a , and R 34b are each independently methyl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and X 11 , X 21 , and X 31 are each phenylene (e.g., 1,4-phenylene); a, b, and c are mole percentages, a is from 0 mole percent to 45 mole percent, b+c is from 55 mole percent to 100 mole percent, b and c are each greater than 0 percent, and a+b+c=100%.

[0233] In some embodiments, the degree of N-substitution (e.g., N-alkylation) in the polymers of the present disclosure is greater than 50 mole percent (e.g., 60 mole percent, 70 mole percent, 80 mole percent, or 90 mole percent) to about 95 mole percent (about 92 mole percent, about 90 mole percent, about 80 mole percent, about 70 mole percent, or about 60 mole percent).

[0234] In certain embodiments, the cationic benzimidazolium-containing moiety or polymer of formula (IX) or (IXa) described forms a salt with an anion. Any anion sufficient to balance the charge of the moiety-containing polymer can be used. Representative anions include iodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, triiodide, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate.

[0235] The polymer containing moieties and the polymers of formula (IX) or (IXa) can be of any size known to those of skill in the art.

[0236] The polymers of the present disclosure are described, for example, in PCT Publication No. WO 2015 / 157848, which is incorporated by reference in its entirety.

[0237] In some embodiments, the present disclosure provides a repeat unit of formula (X):

[0238] [ka]

[0239] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY or R 2XY The imidazolyl group to which R 1XY or R 2XYand (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XY The imidazolyl group to which R 4XY or R 5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XY is selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XY are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl. The present invention relates to a polymer comprising (or consisting essentially of, or consisting of)

[0240] In some embodiments, the polymer comprising (or consisting essentially of, or consisting of) recurring units of formula (x) comprises recurring units of formula (XA):

[0241] [ka]

[0242] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY or R 2XY The imidazolyl group to which R 1XY or R 2XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XY The imidazolyl group to which R 4XY or R 5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XYeach is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XY is selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XY are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl. Includes.

[0243] In some embodiments, a polymer comprising (or consisting essentially of, or consisting of) a repeat unit of formula (X) comprises a repeat unit of formula (XB), or a polymer comprising a repeat unit of formula (XA) further comprises a repeat unit of formula (XB):

[0244] [ka]

[0245] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XYeach is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY or R 2XY The imidazolyl group to which R 1XY or R 2XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XY The imidazolyl group to which R 4XY or R 5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XYis selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XY are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl.

[0246] In some embodiments, a polymer comprising (or consisting essentially of, or consisting of) a recurring unit of formula (X) comprises a recurring unit of formula (XC), or a polymer comprising recurring units of formula (XA) and / or formula (XB) further comprises a recurring unit of formula (XC):

[0247] [ka]

[0248] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY and R 2XYThe imidazolyl group to which R 1XY or R 2XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XY The imidazolyl group to which R 4XY or R 5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XY is selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XYare each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl.

[0249] In some embodiments, a polymer comprising (or consisting essentially of, or consisting of) a recurring unit of formula (X) comprises a recurring unit of formula (XD), or a polymer comprising recurring units of formula (XA), formula (XB), and / or formula (XC) further comprises a recurring unit of formula (XD):

[0250] [ka]

[0251] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY or R 2XY The imidazolyl group to which R 1XY or R 2XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XY The imidazolyl group to which R 4XY or R5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XY is selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XY are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl.

[0252] A polymer of formula (X) may have a mixture of repeat units of formula (XA), formula (XB), formula (XC), and / or formula (XD). For example, the polymer may include repeat units of formula (XA), formula (XB), formula (XC), and formula (XD); formula (XA), formula (XB), and formula (XC); formula (XA), formula (XB), and formula (XD); formula (XA), formula (XC), and formula (XD); formula (XB), formula (XC), formula (XD); formula (XA) and formula (XB); formula (XA) and formula (XC); formula (XA) and formula (XD); formula (XB) and formula (XC); formula (XB) and formula (XD); formula (XC) and formula (XD); formula (XA); formula (XB); formula (XC); or formula (XD).

[0253] In any of the above embodiments of the polymer comprising (or consisting essentially of, or consisting of) repeat units of formula (I); or comprising repeat units of formula (XA), formula (XB), formula (XC), and / or formula (XD), R 1XY , R 2XY , R 4XY , and R 5XY may each be independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, and aryl; 1XY and R 2XY At least one of R is selected from alkyl, perfluoroalkyl, heteroalkyl, and aryl; 4XY and R 5XY At least one of R is selected from alkyl, perfluoroalkyl, heteroalkyl, and aryl. For example, R 1XY , R 2XY , R 4XY , and R 5XY may each be independently selected from absent, alkyl, perfluoroalkyl, and heteroalkyl; 1XY and R 2XY at least one of R is selected from alkyl, perfluoroalkyl, and heteroalkyl; 4XY and R 5XYAt least one of R is selected from alkyl, perfluoroalkyl, and heteroalkyl. 1XY , R 2XY , R 4XY , and R 5XY are each independently selected from absent, methyl, and trifluoromethyl; 1XY and R 2XY At least one of R is selected from methyl and trifluoromethyl; 4XY and R 5XY At least one of is selected from methyl and trifluoromethyl.

[0254] In any of the above embodiments of the polymer comprising (or consisting essentially of, or consisting of) repeat units of formula (X); or comprising repeat units of formula (XA), formula (XB), formula (XC), and / or formula (XD), R 3XY and R 6XY can each independently be aryl. For example, R 3XY and R 6XY may each independently be phenyl. In some embodiments, R 3XY and R 6XY is independently ethyl or methyl. 3XY and R 6XY are each independently methyl.

[0255] In any of the above embodiments of the polymer comprising (or consisting essentially of, or consisting of) repeat units of formula (X); or comprising repeat units of formula (XA), formula (XB), formula (XC), and / or formula (XD), R 15XY and R 16XY Each of R can be independently selected from arylene and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl and halo. For example, R 15XY and R 16XYmay each independently be an arylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl and halo. For example, R 15XY and R 16XY may each be phenylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl and halo. In some embodiments, R 15XY and R 16XY are each phenylene.

[0256] In any of the above embodiments of the polymer comprising (or consisting essentially of, or consisting of) repeat units of formula (X); or comprising repeat units of formula (XA), formula (XB), formula (XC), and / or formula (XD), R 7XY , R 10XY , R 11XXY , and R 14XY can each independently be alkyl. For example, R 7XY , R 10XY , R 11XY , and R 14XY may each independently be methyl or ethyl. For example, R 7XY , R 10XY , R 11XY , and R 14XY may each independently be methyl.

[0257] In any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a recurring unit of Formula (X); or comprising a recurring unit of Formula (XA), Formula (XB), Formula (XC), and / or Formula (XD), the polymer can comprise a counterion selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate. In any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a repeat unit of formula (X); or comprising a repeat unit of formula (XA), formula (XB), formula (XC), and / or formula (XD), the polymer may further comprise one or more anions X selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, cyanide, acetate, nitrate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof. - wherein one or more anions X− counterbalance one or more positive charges in the polymer. In some embodiments, the polymer may comprise one or more anions X selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more anions X selected from iodide, bromide, chloride, fluoride, hydroxide, carbonate, bicarbonate, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more anions X selected from iodide, bromide, chloride, hydroxide, and any combination thereof. - and one or more anions X -compensates for one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more anions X selected from iodide, hydroxide, and any combination thereof. - and one or more anions X - counterbalance one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more hydroxides, and the one or more hydroxides counterbalance one or more positive charges in the polymer.

[0258] The present disclosure also relates to a repeat unit of formula (XI):

[0259] [ka]

[0260] (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of is non-existent, then non-existent R 1XY or R 2XY The imidazolyl group to which R 1XY or R 2XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of is non-existent, then non-existent R 4XY or R 5XYThe imidazolyl group to which R 4XY or R 5XY and (ii) an imidazolyl group having one of the following substituents but not the other is neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY and R 12XY are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl. The present invention provides a polymer comprising (or consisting essentially of, or consisting of)

[0261] In some embodiments, for the above polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XI), R 1XY , R 2XY , R 4XY , and R 5XY are each independently selected from absent, alkyl, perfluoroalkyl, and heteroalkyl; 1XY and R 2XY at least one of R is selected from alkyl, perfluoroalkyl, and heteroalkyl; 4XY and R 5XY At least one of R is selected from alkyl, perfluoroalkyl, and heteroalkyl. For example, R 1XY , R 2XY , R 4XY , and R 5XY are each independently selected from absent, methyl, and trifluoromethyl; 1XY and R 2XY At least one of R is selected from methyl and trifluoromethyl; 4XY and R 5XYAt least one of is selected from methyl and trifluoromethyl.

[0262] In some embodiments, for any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a recurring unit of formula (XI), R 3XY and R 6XY are each independently aryl. For example, R 3XY and R 6XY may each independently be phenyl. In some embodiments, R 3XY and R 6XY is independently methyl or ethyl. 3XY and R 6XY are each independently methyl.

[0263] In some embodiments, for any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a recurring unit of formula (XI), R 7XY , R 8XY , R 10XY , R 11XY , R 12XY , and R 14XY are each independently alkyl. For example, R 7XY , R 8XY , R 10XY , R 11XY , R 12XY , and R 14XY are each independently methyl or ethyl. For example, R 7XY , R 8XY , R 10XY , R 11XY , R 12XY , and R 14XY are each independently methyl.

[0264] In some embodiments, for any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a repeat unit of formula (XI), the polymer comprises one or more counterions selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate. In some embodiments, for any of the above embodiments of a polymer comprising (or consisting essentially of, or consisting of) a repeat unit of formula (XI), the polymer comprises one or more counterions X selected from the group consisting of iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, cyanide, acetate, nitrate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. For example, one or more anions X - may be selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof; and one or more anions X - In some embodiments, the one or more anions X- are selected from iodide, bromide, chloride, fluoride, hydroxide, carbonate, bicarbonate, and any combination thereof, and the one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more anions X selected from iodide, bromide, chloride, hydroxide, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more anions X selected from iodide, hydroxide, and any combination thereof. -and one or more anions X - counterbalance one or more positive charges in the polymer. In some embodiments, the polymer comprises one or more hydroxides, and the one or more hydroxides counterbalance one or more positive charges in the polymer.

[0265] The present disclosure relates to a repeat unit of formula (XII-A):

[0266] [ka]

[0267] The present invention further provides a polymer comprising:

[0268] In some embodiments, the polymer comprising a repeat unit of formula (XII-A) comprises a repeat unit of formula (XII-B):

[0269] [ka]

[0270] Further includes:

[0271] In some embodiments, a polymer comprising a repeat unit of formula (XII-A), or comprising repeat units of formula (XII-A) and formula (XII-B), further comprises a repeat unit of formula (XII-C):

[0272] [ka]

[0273] (In the formula, R 1d and R 4d One of the two is non-existent, and the remaining R 1d or R 4d is methyl; the absent R 1d or R 4d The imidazolyl group to which R 1d or R 4d An imidazolyl group in which one of the groups is absent is neutral. Further includes:

[0274] In some embodiments, for any of the above polymers comprising (or consisting essentially of, or consisting of) repeat units of Formula (XII-A), Formula (XII-B), and / or Formula (XII-C), the polymer comprises one or more counterions selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate. In some embodiments, for any of the above polymers comprising (or consisting essentially of, or consisting of) repeat units of Formula (XII-A), Formula (XII-B), and / or Formula (XII-C), the polymer may further comprise one or more anions X selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, cyanide, acetate, nitrate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, one or more anions X - is selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof; and one or more anions X - compensates for one or more positive charges in the polymer. For example, one or more anions X - may be selected from iodide, bromide, chloride, fluoride, hydroxide, carbonate, bicarbonate, and any combination thereof, and one or more anions X - compensates for one or more positive charges in the polymer. In some embodiments, one or more anions X - is selected from iodide, bromide, chloride, hydroxide, and any combination thereof; and one or more anions X -compensates for one or more positive charges in the polymer. In some embodiments, one or more anions X - is selected from iodide, hydroxide, and any combination thereof, and one or more anions X - counterbalance one or more positive charges in the polymer. For example, for any of the above polymers comprising repeat units of formula (XII-A), formula (XII-B), and / or formula (XII-C), the polymer can comprise one or more hydroxide anions, where the one or more hydroxide anions counterbalance one or more positive charges in the polymer.

[0275] The present disclosure relates to repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C):

[0276] [ka]

[0277] (In the formula, R 1a and R 2a One of the two is non-existent, and the remaining R 1a or R 2a is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4a and R 5a One of the two is non-existent, and the remaining R 4a or R 5a is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1b , R 2b , R 4b , and R 5b One of them is non-existent, and the non-existent R 1b , R 2b , R 4b , or R 5b The imidazolyl group to which R 1b , R 2b , R 4b , or R 5bAn imidazolyl group in which one of R is absent is neutral, 1b , R 2b , R 4b , and R 5b the remaining three of are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1c , R 2c , R 4c , and R 5c are each independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 3a , R 6a , R 3b , R 6b , R 3c , and R 6c each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 7a , R 10a , R 11a , R 14a , R 7b , R 10b , R 11b , R 14b , R 7c , R 10c , R 11c , and R 14c each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8a , R 12a , R 8b , R 12b , R 8c , and R 12c are each independently selected from hydrogen (H), alkyl, perfluoroalkyl, and heteroalkyl. A random polymer comprising (or consisting essentially of, or consisting of) m mole percentage of repeat units of formula (XIII-A), n mole percentage of repeat units of formula (XIII-B), and p mole percentage of repeat units of formula (XIII-C), m is 0 mole percent to 60 mole percent; n+p is between 40 mole percent and 100 mole percent; m+n+p=100%. A random polymer is further provided.

[0278] In some embodiments, for random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C) above, R 1a and R 2a is absent and the remaining R 1a or R 2a is selected from methyl and trifluoromethyl; R 4a and R 5a is absent and the remaining R 4a or R 5a is selected from methyl and trifluoromethyl.

[0279] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), R 1b , R 2b , R 4b , and R 5b is non-existent and one of 1b , R 2b , R 4b , or R 5b The imidazolyl group to which R 1b , R 2b , R 4b , or R 5b one of the imidazolyl groups is absent) is neutral, and R 1b , R 2b , R 4b , and R 5b and the remaining three of R are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl. 1b , R 2b , R 4b , and R 5bis non-existent and one of 1b , R 2b , R 4b , or R 5b The imidazolyl group to which R 1b , R 2b , R 4b , or R 5b one of the imidazolyl groups is absent) is neutral, and R 1b , R 2b , R 4b , and R 5b The remaining three of are each independently selected from methyl and trifluoromethyl.

[0280] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), R 1c , R 2c , R 4c , and R 5c are each independently selected from alkyl, perfluoroalkyl, and heteroalkyl. For example, R 1c , R 2c , R 4c , and R 5c may each be independently selected from methyl and trifluoromethyl. 1c , R 2c , R 4c , and R 5c is independently methyl or ethyl. 1c , R 2c , R 4c , and R 5c are methyl.

[0281] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), R 3a , R 6a , R 3b , R 6b , R 3c, and R 6c are each independently aryl. For example, R 3a , R 6a , R 3b , R 6b , R 3c , and R 6c may each independently be phenyl.

[0282] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), R 7a , R 10a , R 11a , R 14a , R 7b , R 10b , R 11b , R 14b , R 7c , R 10c , R 11c , and R 14c are each independently alkyl. For example, R 7a , R 10a , R 11a , R 14a , R 7b , R 10b , R 11b , R 14b , R 7c , R 10c , R 11c , and R 14c may each independently be methyl or ethyl. For example, R 7a , R 10a , R 11a , R 14a , R 7b , R 10b , R 11b , R 14b , R 7c , R 10c , R 11c , and R 14c may each independently be methyl.

[0283] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), R 8a , R 12a , R 8b , R 12b , R 8c , and R 12c are each independently alkyl. For example, R 8a , R 12a , R 8b , R 12b , R 8c , and R 12c may each independently be methyl or ethyl. For example, R 8a , R 12a , R 8b , R 12b , R 8c , and R 12c may each independently be methyl.

[0284] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), n and p are each greater than 0 percent.

[0285] In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of formula (XIII-A), formula (XIII-B), and formula (XIII-C), the polymer comprises one or more counterions selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate. In some embodiments, for any of the above random polymers comprising (or consisting essentially of, or consisting of) repeat units of Formula (XIII-A), Formula (XIII-B), and Formula (XIII-C), the polymer may further comprise one or more anions X selected from iodide, bromide, chloride, fluoride, triiodide, hydroxide, carbonate, bicarbonate, cyanide, acetate, nitrate, sulfate, phosphate, triflate, tosylate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, bis(trifluoromethane)sulfonamide, and any combination thereof. - and one or more anions X - compensates for one or more positive charges in the polymer. For example, one or more anions X - may be selected from iodide, bromide, chloride, fluoride, hydroxide, carbonate, bicarbonate, and any combination thereof, and one or more anions X - compensates for one or more positive charges in the polymer. For example, one or more anions X - may be selected from iodide, bromide, chloride, hydroxide, and any combination thereof; and one or more anions X - compensates for one or more positive charges in the polymer. - may be selected from iodide, hydroxide, and any combination thereof, and one or more anions X - In some embodiments, for any of the random copolymers described above that include repeat units of formula (IV-A), formula (IV-B), and formula (IV-C), the polymer includes one or more hydroxide anions, and the one or more hydroxide anions compensate for one or more positive charges in the polymer.

[0286] In some embodiments, the polymer comprises a moiety of formula (XIV):

[0287] [ka]

[0288] The repeat unit includes:

[0289] In some embodiments, the polymer comprises a moiety of formula (XV):

[0290] [ka]

[0291] The repeat unit includes:

[0292] In some embodiments, the polymer comprises a moiety of formula (XVI):

[0293] [ka]

[0294] The repeat unit includes:

[0295] Antimicrobial polymeric coatings are described in the examples below. EXAMPLES

[0296] Example 1 Antimicrobial activity evaluation The overall antimicrobial test procedure is shown in Figure 5. This example was carried out on two different lots of polymer with different degrees of methylation (dm). The structures of the polymers are shown in Scheme 1 and Scheme 2 below. These are hereafter referred to as high (91%) dm and low (57%) dm. The iodide form of the polymer was dissolved at 2% by weight in 50:50 (v / v) methanol:acetone by heating at 40°C with stirring, and then precipitated in 1M aqueous solutions of the desired anions: sodium chloride, sodium nitrate and ammonium acetate, respectively. The precipitated anion-exchange polymer was filtered, washed with water and dried (80°C, 12 hours).

[0297] Dissolution for casting was performed by dissolving with stirring at 40°C. High dm polymers were dissolved in pure methanol at 0.7% by weight, and low dm polymers were dissolved in 88:12 (v / v) methanol:acetone. Untreated microscope slides (AmScope BS-50P, clear glass, ground edge, 1'' x 3'') were cleaned before use by sonicating in methanol for 30 min at room temperature. 1 mL aliquots of a given polymer solution were drop cast onto glass slides and allowed to dry overnight at room temperature in a fume hood.

[0298] Referring to Figure 2 (micrograph), Figure 3A (transmission), and Figure 3B (TGA), the polymer coated sample (high dm) was smooth, clear, and transparent. The polymer film properties are also shown in Figure 4.

[0299] [ka]

[0300] Referring to Figure 6 and Table 1 below, Samples 1, 2, 3, 4, and 5 represent polymers with polymer anions of nitrate, acetate, chloride (thin casting), chloride, and chloride (low degree of methylation), respectively. Two controls were also included; Sample C consisted of uncoated glass, and SBSC was an untreated internal control provided by Situ-Bioscience. Samples were provided in replicates of 3.

[0301] [Table 1]

[0302] Antibacterial Testing The ISO-22196 test method is designed to measure the antimicrobial properties of solid or hard surface treatment test samples incubated with selected microorganisms. The basis of the test method is that a bacterial inoculum in contact with the test sample is incubated, without drying, for a period of 24 hours. After this exposure, the inoculated bacteria is recovered and the concentration of the organisms is determined. Antimicrobial performance is determined by comparing the organisms recovered from the untreated material to those recovered from the treated material after the 24 hour incubation.

[0303] Antimicrobial performance is reported as both Log10 and % reduction compared to untreated control samples. Three time points were tested: 30 min, 6 hr, and 24 hr.

[0304] result All samples were tested in triplicate according to JIS Z 2801 and inoculated with Staphylococcus aureus (6538) and Escherichia coli (8739). All samples were plated in duplicate and tested for activity at 0.5 hours, 6 hours and 24 hours.

[0305] Referring to Figures 1B, 1D, and 7, Sample 1 showed a reduction in activity of 75.07% (0.6 Log10 reduction), 98.42% (1.8 Log10 reduction), and 99.80% (2.7 Log10 reduction) against Staphylococcus aureus, and 56.59% (0.4 Log10 reduction), 99.95% (3.3 Log10 reduction), and 99.68% (2.5 Log10 reduction) against Escherichia coli.

[0306] Sample 2 showed a reduction in activity of 99.00% (4.3 Log10 reduction), 99.99% (4.3 Log10 reduction) and 99.99% (2.74.6 Log10 reduction) against Staphylococcus aureus and 82.46% (0.8 Log10 reduction), >99.99% (5 Log10 reduction) and >99.99% (5.5 Log10 reduction) against E. coli.

[0307] Sample 3 showed a reduction in activity of 77.26% (0.6 Log10 reduction), 99.92% (3.1 Log10 reduction) and >99.99% (4.6 Log10 reduction) against Staphylococcus aureus and 40.50% (0.2 Log10 reduction), >99.99% (5.3 Log10 reduction) and >99.99% (5 Log10 reduction) against E. coli.

[0308] Sample 4 showed a reduction in activity of 98.72% (1.9 Log10 reduction), 99.99% (4.5 Log10 reduction), and >99.99% (4.6 Log10 reduction) against Staphylococcus aureus, and >99.99% (4.3 Log10 reduction), >99.99% (5.3 Log10 reduction), and >99.99% (5.5 Log10 reduction) against E. coli.

[0309] Sample 5 showed a 50.53% (0.3 Log10 reduction), 99.83% (2.8 Log10 reduction) and over 99.99% (4.6 Log10 reduction) reduction in activity against Staphylococcus aureus and 23.42% (0.1 Log10 reduction), 97.03% (1.5 Log10 reduction) and 98.93% (2 Log10 reduction) reduction in activity against E. coli.

[0310] Sample C showed a reduction in activity of 25.28% (0.1 Log10 reduction), 46.68% (0.3 Log10 reduction) and 69.24% (0.5 Log10 reduction) against Staphylococcus aureus and 9.58% (0 Log10 reduction), 0% (0 Log10 reduction) and 0% (0 Log10 reduction) against E. coli.

[0311] The internal control sample SBSC untreated control showed bacterial concentrations of 7.1E5 CFU / mL, 1.0E6 CFU / mL at 0 and 0.5 hours, respectively, and 7.7E5 CFU / mL, 1.4E6 CFU / mL, and 2.0E6 CFU / mL at 0, 0.5 and 24 hours, respectively, for Staphylococcus aureus.

[0312] The SBSC untreated control showed bacterial concentrations of 9.3E5 CFU / mL, 1.0E6 CFU / mL at 0 and 0.5 hours, respectively, and 7.0E5 CFU / mL, 1.1E7 CFU / mL, and 1.4E7 CFU / mL at 0, 6, and 24 hours, respectively, for E. coli.

[0313] Antiviral Testing ISO 21702 provides a test method for the quantitative evaluation of virucidal activity on plastics and other non-porous surfaces. The product to be tested is intended to be a treated antiviral product, which is tested against a specific virus. The basis of the test method is to incubate a virus inoculum in contact with the test sample for a period of 24 hours, without allowing it to dry. After this exposure, the inoculated virus is recovered and the concentration of infectious virus is determined. Antiviral performance is determined by comparing the virus recovered from untreated material with that recovered from treated material after 24 hours of incubation.

[0314] Antimicrobial performance is reported as both Log10 and % reduction compared to untreated control samples.

[0315] Tests were performed by contamination with the virus inoculum solution by incorporating 5% serum.

[0316] Results and Discussion Result: Log reduction rounded to one decimal place (e.g. 3.1).

[0317] All samples were tested according to ISO 21702 and inoculated with feline calicivirus (F-9) and human coronavirus (229E). All samples were tested for activity at 0.5 and 24 hours.

[0318] Cytotoxicity optimization was performed on sample 4 only.

[0319] Referring to Figures 1A, 1C, and 7, Sample 4 showed 0% (0 Log10 reduction) and 90% (1 Log10 reduction) reduction in activity against feline calicivirus (F-9) and greater than 99.99% (4.2 log10 reduction) and 99.99% (4 Log10 reduction) reduction in activity against human coronavirus (229E) at 0.5 hours and 24 hours, respectively.

[0320] Sample 5 showed a 78.5% (0.7 Log10 reduction) and 95.4% (1.3 Log10 reduction) reduction in activity against feline calicivirus (F-9) and a 99.7% (2.5 Log10 reduction) and 99% (2 Log10 reduction) reduction in activity against human coronavirus (229E) at 0.5 and 24 hours, respectively.

[0321] Sample C showed 0% (0 Log10 reduction) and 85.3% (0.8 Log10 reduction) reduction in activity against feline calicivirus (F-9) and 93.2% (1.2 Log10 reduction) and 95.4% (1.3 Log10 reduction) reduction in activity against human coronavirus (229E) at 0.5 and 24 hours, respectively.

[0322] The internal control samples, SBSC untreated controls, showed virus concentrations of 2.9E6log10TCID50 / sq cm, 2.9E6log10TCID50 / sq cm, and 6.1E6log10TCID50 / sq cm at 0, 0.5, and 24 hours, respectively, for feline calicivirus (F-9) and 6.1E5log10TCID50 / sq cm, 9.0E5TCID50 / sq cm, and 6.2E5Log10TCID50 / sq cm at 0, 0.5, and 24 hours, respectively, for human coronavirus (229E).

[0323] The ISO21702 intrinsic cytotoxicity optimization for sample 4 was negative.

[0324] Kinetic analysis and half-life data were also obtained and the results are shown in Figure 8.

[0325] Detailed antibacterial and antiviral tests and results. ISO22196: Antibacterial testing (Method for evaluating the antimicrobial activity of antimicrobial-treated plastic products, including intermediate products). It is not intended to be used to evaluate the efficacy and bacterial growth in plastics without antimicrobial treatment. Antimicrobial activity is determined by the following method: R = (Ut-U0) - (At-U0) = Ut-At (In the formula, R is antibacterial activity; U0 is the average common logarithm of the number of viable bacteria recovered from untreated test specimens immediately after inoculation (cells / cm2); Ut is the mean common logarithm of the number of viable bacteria recovered from untreated test specimens after 24 hours (cells / cm2); At is the mean common logarithm of the viable bacterial count recovered from treated test specimens after 24 hours (cells / cm2).

[0326] For general reference, the % reduction is also reported in the notes section for each sample result.

[0327] Legend CFU = colony forming units (typically stated per unit volume or surface area). CFU is determined by plating bacteria on a test sample according to a specified method and subsequently counting the resulting colonies.

[0328] Untreated Control (UTC) - Untreated control sample material used to demonstrate normal test performance, exhibiting robust microorganism growth.

[0329] Interval - represents the point or time at which a result value was determined; TO indicates that the result is from the earliest possible time from inoculation to collection of the inoculated sample (typically less than 5 minutes).

[0330] Result - The result is a measure of change or abundance. Result units often indicate the actual measurement relative to a control value depending on the method or test requirements.

[0331] Notes on changes to published test methods: Some references are made to "count agar plates" for testing method plating following neutralization and recovery of bacteria from the test sample. As a standard practice, counts are performed on appropriate plate media such as nutrient agar, tryptic soy agar, or as required by the particular organism being tested.

[0332] The published standard refers to incubation conditions of 35 ± 1 °C. Standard microbiological practice with other international methods is for incubations to occur at 37 ± 1 °C. Test conditions performed are at 37 ± 1 °C unless other temperature conditions are specified.

[0333] The expanded uncertainty of the test method for k=2 is for 95% confidence of Log10(0.136).

[0334] The uncertainty value for CFU is obtained by converting the CFU count (C1) to a Log10 value (Log10 C1); this result is multiplied by the expanded uncertainty (Log 10 C1 *EU), then subtracted from the Log10 value (Log C1 ± (Log10 C1 * EU)); convert it again by taking the real number (1×10^(Log C1±(Log10 C1 * EU)), upper and lower 95% confidence limits for CFU are obtained.

[0335] Defined method standards For ISO 22196, interlaboratory testing demonstrated results with a standard deviation of Log10(0.45) or approximately 1 / 2 log, which corresponds to a -mean ± 50% reduction.

[0336] Conditions for a valid test A test is considered valid if three conditions are met: If all conditions are not met, the test is not considered valid and the specimens should be retested.

[0337] The logarithm of the viable count recovered from the untreated test specimen immediately after inoculation must meet the following requirements: (L 最大 -L 最小 ) / (L 平均 )≦0.2 (In the formula, L 最大 is the common logarithm (i.e., logarithm to the base 10) of the maximum number of viable bacteria found on a specimen; L 最小 is the base 10 logarithm of the minimum number of viable bacteria found on a specimen; L 平均 is the base 10 logarithm of the average number of viable bacteria found on a specimen).

[0338] overview The ISO-22196 test method is designed to measure the antimicrobial properties of solid or hard surface treatment test samples incubated with selected microorganisms. The basis of the test method is that a bacterial inoculum in contact with the test sample is incubated, without drying, for a period of 24 hours. After this exposure, the inoculated bacteria is recovered and the concentration of the organisms is determined. Antimicrobial performance is determined by comparing the organisms recovered from the untreated material to those recovered from the treated material after the 24 hour incubation.

[0339] Antimicrobial performance is reported as both Log10 and % reduction compared to untreated control samples.

[0340] Three time points were tested: 30 min, 6 h and 24 h.

[0341] Results and Discussion Provide the results in a results data table

[0342] Test sample results Time point of outcome: (typically T0 or other time during the study) Unit of time: typically "hr" (hours) Result: Log reduction rounded to 1 decimal place (e.g. 3.1) Unit: Log decrease Limit of Detection (LOD): The LOD is entered in the results notes for each sample in which no bacteria were recovered.

[0343] JIS Z 2801-Antibacterial products-Testing of antimicrobial activity and effectiveness JIS Z 2801 specifies a method for the evaluation of antimicrobial activity of plastic products. It is a commonly used method to evaluate the antimicrobial properties of many material types, which can range from coated surfaces or those of monolithic composition. The basis of the test method is to incubate a microorganism inoculum in close contact with the test material on a flat horizontal surface for 24 hours. After this exposure, a sample of the inoculum is collected and the concentration of organisms is determined. Antimicrobial performance is determined by comparing the organisms recovered from the untreated inoculum-only test material after selected time points with the organisms recovered from the treated test material after selected time points. It is not intended to be used to evaluate efficacy and bacterial growth on plastics without antimicrobial treatment.

[0344] test Inoculum preparation After overnight incubation of the test bacteria, perform the transfer to the inoculum solution. Using a sterile inoculating loop, transfer one loop of the test bacteria into the prepared small volume of 1 / 500 NB. Make dilutions of this suspension with 1 / 500 NB as needed to establish the estimated bacterial concentration to obtain bacterial concentrations of SES CFU / mL to 2E6 CFU / mL with a target concentration of 1E6 CFU / mL.

[0345] Inoculation of test specimens The surface to be tested is the exposed outer surface of the product. · Pipette 0.2mL of the prepared test inoculum onto the test surface. · Cover the test inoculum with a 40mm x 40mm piece of film and gently press the film down so that the test inoculum spreads to the edges. · Ensure that the test inoculum does not leak past the edge of the film. After inoculating the specimen and applying the cover film, replace the lid of the Petri dish.

[0346] Incubation of inoculated test specimens The standard procedure for incubating the inoculated specimens is to incubate the Petri dishes containing the inoculated test specimens (including half of an untreated test specimen) at a temperature of (37±1)°C and a relative humidity of 90% or greater for (24±1) hours, unless otherwise specified.

[0347] Recovery of bacteria from test specimens. Immediately after inoculation, one-half of the untreated test specimens are treated by adding 5 mL of the appropriate neutralizing agent to the Petri dish containing the test specimen.

[0348] Test specimens after incubation After incubation, the remaining test specimens are processed. Viable bacteria recovered from the test specimens are immediately processed and counted.

[0349] reagent Nutrient Broth 2 (NB2) D / E Neutralizing Broth (D / E) Phosphate-buffered saline (PBS) Tryptic Soy Agar Laboratory RO water, deionized

[0350] Device List Thermo Orbital Shaker Incubator Balance (Mettler H80, Mettler PM-11K, Mettler MS104S / 03) Autoplater Spiral Biotech 4000 National Water Incubator Shimadzu spectrophotometer MarketForge Autoclave Hach pH meter / 02 measurement unit / conductivity meter Dwyer Hygrometer Gilson Pipettor

[0351] Test organism Staphylococcus aureus E. coli

[0352] Sample preparation Each test material was prepared according to the requirements of the analytical method. Each test sample was prepared in replicates of 3 unless otherwise stated. Flat samples were obtained and cut into 50 x 50 mm pieces as available. Sample variability was adjusted when necessary for standard testing, and notes regarding differences in sample characteristics were recorded in the report summary.

[0353] [Table 2A]

[0354] [Table 2B]

[0355] [Table 2C]

[0356] ISO21702: Antiviral testing ISO 21702 provides a test method for the quantitative evaluation of virucidal activity on plastics and other non-porous surfaces. The products tested are intended to be treated antiviral products that are tested against a specific virus. The basis of the test method is to incubate a virus inoculum in contact with the test sample for a period of 24 hours, without allowing it to dry. After this exposure, the inoculated virus is recovered and the concentration of infectious virus is determined. Antiviral performance is determined by comparing the virus recovered from untreated material with that recovered from treated material after 24 hours of incubation.

[0357] Antimicrobial performance is reported as both Log10 and % reduction compared to untreated control samples.

[0358] Results and Discussion Provide the results in a results data table Tests were performed by contamination with the virus inoculum solution by incorporating 5% serum.

[0359] ISO21702 specifies a method for evaluating the virucidal activity of non-porous surfaces. Each product was tested using clean test conditions (no additional contamination). Unless otherwise stated, secondary effects of antimicrobial treatments, measured antimicrobial performance, or durability of measured activity are not covered by this standard. This standard is not intended to be used or referenced as a method for documenting or claiming antimicrobial performance unless indicated in a test report. Determination of product performance within a given environment can vary dramatically and must be specifically documented and then determined within the context of a specific project plan.

[0360] method Project - Special Biological Culture - Virus Cell culture of non-standard viruses used in a given test method. For each virus, employ the necessary media and culture conditions according to the standard requirements established by the laboratory.

[0361] ISO21702 - Determination of antiviral activity on plastic and other non-porous surfaces The ISO 21702 method is used to evaluate the virucidal efficacy of non-porous products. Tests can incorporate various exposure times, contamination, and virus types, as well as other variables, according to the test standard or the specific needs of the product. The most common test conditions employ standard method protocols that require 24 hours of exposure to the test material depending on the intended use of the product. The test virus is prepared prior to testing, followed by viral titer determination. The created inoculum is then utilized as the inoculum for exposing the test material to the virus.

[0362] ISO21702 Intrinsic Cytotoxicity Optimization Antiviral testing requires the use of host cells for growth and counting of virus concentration. The host cells must be viable and biologically intact to allow viral infection. Successful infection by the virus results in replication and eventual lysis and loss of the host cell. This process provides a means to measure the virus. Host cell cytotoxicity as a result of any chemical carryover from the test sample can affect the biological viability of the host cell and interfere with the processes necessary after exposing the cell to the virus. This interference is generally considered the intrinsic cytotoxicity of the test sample.

[0363] The test is performed by incubating the test sample with a neutralized recovery solution for 30 seconds, followed by exposing the host cells to eight concentrations of recovery solution. Intrinsic cytotoxicity is determined by the loss of cell culture viability.

[0364] test Inoculum preparation Prepare a suspension of known virus titer to a concentration of at least 1E6TCID50 / mL. Do not use virus passages greater than 10 passages from the original seed culture.

[0365] Experimental conditions After inoculation, the samples are incubated at 25°C ± 1°C (unless otherwise stated). Incubation is performed to prevent the inoculum from drying out while in contact with the test surface. After the incubation period, the virus is recovered in neutralizing medium and then diluted for culture.

[0366] Recovery of virus from test specimens Two time points are created for each test item, and washout of the inoculated samples is collected immediately after inoculation by placing the sample in a vial and adding 10 mL of the neutralizer solution of choice, followed by vortexing.

[0367] A second withdrawal is made after the intended incubation time (24 hours) after which the sample is placed into a vial containing 10 mL of neutralizing solution and vortexed. After test sample neutralization, aliquots of the sample are withdrawn and used to determine the infectious titer after each incubation period.

[0368] reagent Dulbecco's Modified Eagle Medium (DMEM; EM-1) Soybean casein lecithin polysorbate 80 medium (SCDLP) Phosphate-buffered saline (PBS) Formaldehyde solution (3.7%) Crystal Violet (0.5%) Fetal bovine serum Virus maintenance medium Trypsin Ethylenediaminetetraacetic acid solution (EDTA) Laboratory RO water, deionized

[0369] Device List Thermo Orbital Shaker Incubator Balance (Mettler H80, Mettler PM-11K, Mettler MS104S / 03) Nuaire BSL 2 Cabinet Nuaire Water Jacket Incubator Nikon inverted microscope Vortex Mixer centrifuge Liquid Nitrogen Dewar MarketForge Autoclave Hach pH meter / 02 measurement unit / conductivity meter Dwyer Hygrometer Gilson Pipettor

[0370] ISO21702 - Determination of antiviral activity on plastic and other non-porous surfaces Feline calicivirus (F-9) {CCL-94 Eu cell host) Human coronavirus (229E) Human lung fibroblast MRC-5 (CCL-171)

[0371] Sample preparation Each test material was prepared according to the requirements of the analytical method. Each test sample was prepared in replicates of 3 for each time point. Samples were cut into approximately 50 mm x 50 mm pieces as available. Sample variability was adjusted when necessary for standard testing, and notes regarding differences in sample characteristics were recorded in the report summary.

[0372] Ideally, the test sample is flat and non-hydrophobic to allow layering of the inoculum onto the sample surface.

[0373] calculation Perform end-point dilutions with the recovered virus inoculum using serial log10 dilution factors. Use TCIDSO (Spearman-Karber method; modified by MARamakrishnan) to determine the concentration of virus to be inoculated based on the result of the end-point dilution that results in the CTE of the host cells. This represents the end-point dilution (average) of the host cell monolayer that exhibits a CTE. Log10 50% endpoint dilution = -[(total number of CTE wells / total number of dilution replicates) + 0.5] x log dilution factor R = -[total CTE / number of replicates per dilution) + 0.5] x Log dilution factor R = log50% end point dilution Total CTE - the average logarithm of the number of viable viruses recovered from untreated test specimens immediately after inoculation (cells / cm2) Number of replicates per dilution - number of replicate wells inoculated at each dilution Log Dilution Factor - the dilution factor used for each dilution series (typically 10x or log10(10) = 1)

[0374] Antiviral activity value R = U(t24) - C(t24) R = antiviral activity value C(t24) = logarithmic average of three infectivity values ​​after 24 hours from untreated material U(t24) = the common logarithm mean of the three infectivity values ​​after the contact time (24 hours) with the treated (test) sample

[0375] statistical methods Replicate data are used for Spearman-Karber calculations and no additional statistical analysis is performed.

[0376] [Table 3A]

[0377] [Table 3B]

[0378] Example 2 Antimicrobial activity against Escherichia coli The polymer used was HMT-PMBI having a degree of 89% methylation, as described, for example, in PCT Publication No. WO 2015 / 157848, which is incorporated herein by reference in its entirety.

[0379] [ka]

[0380] The test method was based on JIS Z 2801:2010, the Japanese Industrial Standards Test for Antimicrobial Activity and Effectiveness of Antimicrobial Products. The specific content of the test method applied in this project is described below.

[0381] This test method was primarily designed to evaluate (quantitatively) the antimicrobial effectiveness of agents incorporated or attached in or onto flat (two-dimensional) hydrophobic or polymeric surfaces.

[0382] The test organism was Escherichia coli ATCC number 8739.

[0383] The samples presented were inoculated in triplicate with 0.4 mL of 0.2% nutrient broth inoculated with a standardized culture of the test organism. The inoculated samples were covered with an inert film and incubated in a humidity chamber at 36±2° C. for 24 hours. Viable microorganisms were recovered by elution of the broth inoculum from the test sample into neutralizing broth. The microbial counts of the samples were determined and the percent reduction in microorganisms (treated vs. untreated at the time point) was calculated.

[0384] The 1.2 mil polymeric film demonstrated antimicrobial activity against E. coli with 99.99% reduction and antimicrobial activity value of 4.04 after 24 hours incubation using JIS Z 2801 test method. The percent reduction and antimicrobial activity were calculated relative to the control at the 24 hour time point.

[0385] [Table 4]

[0386] [Table 5]

[0387] [Table 6]

[0388] Example 3 Antimicrobial activity against Staphylococcus aureus The polymer used was HMT-PMBI having a degree of 89% methylation, as described, for example, in PCT Publication No. WO 2015 / 157848, which is incorporated herein by reference in its entirety.

[0389] [ka]

[0390] The test method was based on JIS Z 2801:2010, the Japanese Industrial Standards Test for Antimicrobial Activity and Effectiveness of Antimicrobial Products. The specific content of the test method applied in this project is described below.

[0391] This test method was primarily designed to evaluate (quantitatively) the antimicrobial effectiveness of agents incorporated or attached in or onto flat (two-dimensional) hydrophobic or polymeric surfaces.

[0392] The test organism was Staphylococcus aureus ATCC number 6538.

[0393] Submitted samples were inoculated in triplicate with 0.4 mL of 0.2% nutrient broth inoculated with a standardized culture of the test organism. The inoculated samples were covered with an inert film and incubated in a humidity chamber at 36±2° C. for 24 hours. Viable microorganisms were recovered by elution of the broth inoculum from the test sample into neutralizing broth. The microbial counts of the samples were determined and the percent reduction in microorganisms (treated vs. untreated at time point) was calculated.

[0394] The 1.2 mil polymeric film demonstrated antimicrobial activity against Staphylococcus aureus with greater than 99.94% reduction and antimicrobial activity value of greater than 3.19 after 24 hours incubation using the JIS Z 2801 test method. The percent reduction and antimicrobial activity were calculated relative to the control at the 24 hour time point.

[0395] [Table 7]

[0396] [Table 8]

[0397] [Table 9]

[0398] Example 4 Antifouling test Test polymer coupons are prepared by spraying a 5% by weight solution of the partially demethylated polymeric material of the present disclosure in mixed chloride / iodide form onto a glass slide to obtain a continuous film of a given thickness and a given mass loading. The coupons are then subjected to biofilm growth conditions and cell counts according to ASTM E2647-13, the Standard Test Method for Quantification of Pseudomonas aeruginosa Biofilms Grown Using a Drip Flow Biofilm Reactor with Low Shear and Continuous Flow, which is incorporated herein by reference in its entirety.

[0399] Specifically, ASTM E2647-13 specifies the operating parameters necessary to grow reproducible P. aeruginosa biofilms near the air / liquid interface in a reactor with a continuous flow of nutrients under low fluid shear conditions. The resulting biofilms do not represent one specific environment, but rather the generalized situation in which biofilms exist at the air / liquid interface under low fluid shear.

[0400] The test method uses a drip flow reactor. A drip flow reactor (DFR) is a plug flow reactor with laminar flow resulting in low fluid shear. This reactor is versatile and can also be used to grow and / or characterize biofilms of different species.

[0401] This test method describes how to sample and analyze viable cell biofilms. Biofilm population density is recorded as log colony forming units per surface area.

[0402] This test method is used to grow reproducible P. aeruginosa biofilms in a drip flow reactor. Biofilms are established by operating the reactor in batch mode (no nutrient flow) for 6 hours. Mature biofilms form while the reactor is operated for an additional 48 hours with a continuous flow of nutrients. During the continuous flow, the biofilm experiences very low shear caused by gravity flow of the medium dripping onto a surface set at a 10° angle. At the end of 54 hours, biofilm accumulation is quantified by removing coupons from the reactor channel, rinsing the coupons to remove planktonic cells, scraping the biofilm from the coupon surface to break up clumps, and then diluting and plating for viable cell counts.

[0403] The experimental setup is as shown in FIGS.

[0404] Water Purity - All references to water as a diluent or reagent are intended to mean distilled water or water of equivalent purity.

[0405] Culture medium: Bacterial liquid growth broth - Tryptic soy broth (TSB) 7 is recommended. Two different TSB concentrations are used in the test method: 3000 mg / L for inoculum and batch reactor operation and 270 mg / L for continuous flow reactor operation.

[0406] Bacterial plating medium - R2A agar7 is recommended.

[0407] Buffered Water - 0.0425 g / L KH2PO4 distilled water, filter-sterilized and 0.405 g / L MgCl·6H2O distilled water, filter-sterilized (prepared according to method 9050C.1a).

[0408] Pseudomonas aeruginosa (ATCC700888) is the organism used in this study. Isolated colonies from the R2A plates are aseptically removed and inoculated into 100 mL of sterile bacterial liquid growth broth (3000 mg TSB / L). The bacterial suspension is incubated for 20-24 hours at 35 ± 2 °C in an environmental shaker. The viable bacterial density should be equal to 108 CFU / mL and can be confirmed by serial dilution and plating.

[0409] procedure Batch phase: Place the cooling reactor in a horizontal position on the bench top. Aseptically add 15 mL of sterile 3000 mg TSB / L and 1 mL of inoculum to each channel. Tighten the lid of each channel with the nylon screw. Incubate the reactor system in a horizontal position at room temperature (2162 °C) for 6 hours in batch mode. Remove the foil from the outflow tube and attach the end to a waste carboy. Do not remove the clamp until the continuous flow phase.

[0410] Preparation for the continuous flow phase: Prepare continuous flow nutrient broth by adding sterile bacterial liquid growth medium to 20 L of sterile reagent grade water for a final concentration equal to 270 mg TSB / L (see 7.2.1). That is, dissolve the broth concentrate in a small volume of water and sterilize to prevent caramelization that may occur under the long sterilization times required for large volumes. Aseptically pour the concentrated medium into a carboy of sterile water to make a total of 20 L.

[0411] Adjust the angle of the reactor (Figure 11): Measure the length a (cm) of the reactor bottom. The angle (x) is 10°. Calculate y using the following formula: ya[sin(x)]) (In the formula, a = measured length of the reactor base (cm), x = angle (10°), and y = the difference between the length of b and the length of c (cm).

[0412] Determine the length of b and the length of c to get the required difference (y). Use the following formula: Y=bc (In the formula, b = measured length from the lower corner of the inlet end of the reactor base to the laboratory surface (cm); c = the measured length (cm) from the lower corner of the outlet end of the reactor bottom to the laboratory surface, and y = the difference between the length of b and the length of c (cm).

[0413] Remove the clamp on the outflow tube and attach the legs to the DFR. Adjust the legs of the reactor chamber so that the reactor chamber is tilted downwards at 10° until the required length (b and c) is achieved.

[0414] Continuous flow phase: Aseptically connect the inflow nutrient tube lines to the carboy containing the continuous flow nutrient broth. Feed each line through a pump head and connect a sterile needle to the end of each line. Aseptically attach the inflow tubing by inserting a sterile needle into the Mininert valve in the channel lid.

[0415] Turn on the pump and allow the medium to drip slowly onto the bacterial cells attached to the coupons. Pump a continuous flow of nutrients into the reactor through the pump set at a flow rate equal to 200 mL / hr (50 mL / hr per channel). The medium should flow downward from the inlet port to the outlet port. Regularly check the reactor for proper drainage and leakage. If problems occur, visually inspect the inlets and tubing for bacterial clogging. Run the reactor in CF mode for 48 hours.

[0416] Biofilm Sampling: Prepare sampling materials: vortexer, homogenizer, sterile beakers, sterile centrifuge tubes, culture tubes, pipettes, empty sterile Petri dishes, sterile spatula, and flame-sterilized stainless steel hemostats or forceps.

[0417] Loosen the screw on the channel lid with gloved hands and lift the channel lid. Aseptically remove one of the coupons by slowly lifting it with sterile hemostat. Place the coupon on a sterile Petri dish while carrying it to the sampling area. Hold the coupon with flame-sterilized hemostat, taking care not to disturb the attached biofilm. Rinse the coupon to remove planktonic cells: slowly immerse the coupon in a centrifuge tube containing 45 mL of sterile buffered water with fluid motion until the slide is completely covered. Immediately remove the slide by inverting, taking care not to agitate the liquid and the biofilm.

[0418] Remove biofilm from coupons: Using the flat end of a sterile spatula or scraper, scrape the biofilm-covered coupon surface downwards for approximately 15 seconds and place into a beaker containing 45 mL of sterile dilution buffer. Rinse the spatula or scraper by stirring in the beaker. Repeat the scraping and rinsing process 3-4 times to ensure complete coverage of the coupon surface.

[0419] Hold the coupon at a 60° angle over a sterile beaker and pipette 1 mL of sterile buffered water onto the top surface of the coupon. Repeat for a total of five rinses. The final volume in the beaker is 50 mL.

[0420] Analysis of biofilm samples: The scraped biofilm sample is homogenized in the beaker at 20,500±5000 r / min for 30 seconds. If more than one biofilm sample is taken, rinse the homogenizer probe between each new sample as follows: homogenize the dilution blank at 20,500±5000 r / min for 30 seconds, homogenize the tube containing 70% ethanol for 15 seconds, then remove the probe and leave it in the ethanol tube for 1 minute. Shake off any remaining ethanol from the probe, reattach the probe and homogenize the dilution blank for 30 seconds. Homogenize the third dilution blank and then the next sample beaker. Homogenizing the sample breaks down the biofilm clumps to form a homogenous cell suspension. Inadequate breakup can result in an underestimation of the viable cells present in the sample.

[0421] Using sterile culture tubes, perform serial 10-fold dilutions on the samples. Plate each dilution in duplicate for colony growth using an approved plating technique such as spread plating or spiral plating (Practice D5465). Incubate the plates at 35 ± 2 °C for 17-20 hours.

[0422] Cell counting: Count the appropriate number of colonies according to the plating method used. Calculate the arithmetic mean of the colonies counted on the two replicate plates. Calculate the log density of a coupon as follows; LOG 10 (CFU / cm 2 )=LOG 10 [(X / B)(V / A)(D)] (In the formula, X=average CFU, B = plated volume, V = volume scraped off, A = surface area scraped off, and D=dilution).

[0423] Calculate overall biofilm accumulation by calculating the average log density.

[0424] Example 4 Additional Polymer Performance Another exemplary polymer having the morphology shown in Scheme 3 was tested.

[0425] [ka]

[0426] This "methylbutyl" polymer was tested under similar conditions as the "high dm" polymer from the previous example. In comparison, it showed improved aliphatic properties for improved activity against non-enveloped viruses. Equivalent functionality against gram- bacteria, gram+ bacteria, and enveloped viruses. Equivalent ability to be cast as a film from low boiling and / or non-toxic solvents. Equivalent optical clarity, clarity, and transparency. Improved lot-to-lot charge density consistency. Reduced water uptake (or "water uptake to charge" ratio) for improved durability on surfaces exposed to water or frequently cleaned surfaces.

[0427] While exemplary embodiments have been illustrated and described, it will be recognized that various changes can be made therein without departing from the spirit and scope of the invention.

[0428] The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

Claims

1. 1. A method of inhibiting microorganisms on a surface, comprising applying to the surface a polymer comprising repeating units comprising: (i) A benzimidazolium-containing moiety of formula (I): 【Chemistry 1】 (In the formula, R 1AA is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups, and polymers; R 2AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3AA is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5AA is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1AA , R 2AA , R 3AA , and R 5AA at least one of which is a polymer; (ii) an imidazolium-containing moiety having formula (II): 【Chemistry 2】 (In the formula, R 1XX is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups and polymers; R 2XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3XX is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, polymeric, and no group; R 5XX is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1XX , R 2XX , R 3XX , and R 5XX at least one of which is a polymer; or Any combination of these A method comprising:

2. The method of claim 1, further comprising exposing the surface to the microorganisms and killing the microorganisms present on the surface.

3. The method of claim 1, further comprising inhibiting the attachment of said microorganisms onto said surface.

4. 10. The method of claim 1, wherein when the surface is exposed to the microorganisms, the number of microorganisms on the surface is reduced by greater than 99% after a 24 hour period.

5. The method of claim 1 , wherein the microorganism comprises a fungus, a bacterium, a virus, or any combination thereof.

6. 6. The method of claim 5, wherein when the surface is exposed to a fungus, the number of the fungus is reduced by more than 99% after a 24 hour period.

7. The fungus may be selected from the group consisting of Candida spp., Cryptococcus spp., Blastomyces spp., Coccidioides spp., Aspergillus spp., Emmonsia spp., Chrysosporium spp., Fonsecaea spp., Trychophyton spp., Histoplasma spp., Ajellomyces spp., Pneumocystis spp., and the like.

6. The method of claim 5, wherein the protease is selected from the group consisting of Azotobacter spp., Microsporum spp., Magnaporthe spp., Fusarium spp., Sporothrix spp., Cyberlindnera spp., Mucormycetes spp., Epidermophyton spp., Trichosporon spp., Paracoccidioides spp., Talaromyces spp., Uncinocarpus reesii, and Aphanoascus spp.

8. 6. The method of claim 5, wherein when the surface is exposed to bacteria, the number of bacteria is reduced by more than 99% after a 24 hour period.

9. The method of claim 5, wherein the bacterium is a gram-positive bacterium.

10. The method of claim 5, wherein the bacterium is a gram-negative bacterium.

11. The method of claim 5, wherein the microorganism is a pathogenic bacterium.

12. The pathogenic bacteria are selected from the group consisting of Escherichia coli, Staphylococcus aureus, Campylobacter species, Legionella, Salmonella species, Shigella species, Tsukamurella, Leptospires, Mycobacterium, Pseudomonas aeruginosa, Aeromonas species, Vibrio species, Yersinia, Bacillus species, Enterobacter sakazakii, Burkholderia 12. The method of claim 11, wherein the bacterium is selected from the group consisting of Acinetobacter spp., Helicobacter pylori, Klebsiella spp., Clostridium spp., and Streptococci spp.

13. 6. The method of claim 5, wherein when the surface is exposed to a virus, the number of the virus is reduced by more than 99% after a 24 hour period.

14. The viruses include alphacoronaviruses, betacoronaviruses (e.g., SARS-CoV-2), deltacoronaviruses, gammacoronaviruses, and toroviruses; influenza virus A, influenza virus B, influenza virus C, influenza virus D, hepatitis A virus, hepatitis B virus, simplex virus, cytomegalovirus, mamastrovirus, mastadenovirus, poxvirus, hepadnavirus, asfarviridae, flavivirus, alphavirus, togavirus, paramyxovirus, rhabdovirus, bunyaviridae, filovirus, retroviridae, coxsackievirus (enveloped and non-enveloped), rotavirus, poliovirus, calicivirus, orthopoxvirus, polyomavirus, vegiclovirus, varicellovirus, phlebovirus, alphatorquevirus, norovirus, 6. The method of claim 5, wherein the virus is selected from the group consisting of rubulavirus, spumavirus, rubulavirus, hantavirus, sapovirus, sarivirus, rubivirus, rosavirus, lyssavirus, enterovirus, arenavirus, orthobunyavirus, parapoxvirus, henipavirus, morsipoxvirus, polyomavirus, cardiovirus, morbillivirus, Marburgvirus, deltaretrovirus, orthopneumovirus, erythrovirus, respirovirus, alphapapillomavirus, mupapillomavirus, rhadinovirus, roseolovirus, deltavirus, hepevirus, hepacivirus, orthohepadnavirus, henipavirus, pegivirus, lymphocryptovirus, Ebolavirus, nairovirus, thogotovirus, cosavirus, ceadornavirus, kobuvirus, dependovirus, and any combination thereof.

15. 2. The method of claim 1, wherein the polymer comprises a counterion selected from the group consisting of iodide, triiodide, hydroxide, chloride, bromide, fluoride, cyanide, acetate, carbonate, nitrate, sulfate, phosphate, triflate, tosylate, bisulfate, bicarbonate, hydrogen phosphate, and dihydrogen phosphate.

16. 2. The method of claim 1, wherein the benzimidazolium-containing moiety of formula (I), the imidazolium-containing moiety of formula (II), or both, are each independently in the backbone of the polymer.

17. 2. The method of claim 1, wherein the benzimidazolium-containing moiety of formula (I), the imidazolium-containing moiety of formula (II), or both, are each independently in a pendant group of the polymer.

18. 2. The method of claim 1, wherein the benzimidazolium-containing moiety of formula (I), the imidazolium-containing moiety of formula (II), or both, are each independently part of a crosslink of the polymer.

19. The polymer is a polymer of formula (III): 【Chemistry 3】 (In the formula, R 1AA and R 3AA is a methyl group, and R 2AA is hydrogen) 2. The method of claim 1, comprising:

20. The repeat unit is a benzimidazolium-containing moiety of formulas (IV)-(VIII): 【Chemistry 4】 (In the formula, R 1 is independently selected from the group consisting of H, methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, alkoxy, perfluoroalkoxy, halo, aryl, heteroaryl groups, and polymers; R 2 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 3 is independently selected from the group consisting of methyl, trifluoromethyl, alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and polymers; R 5 is independently selected from the group consisting of hydrogen, an arbitrary group, and a polymer; R 1 , R 2 , R 3 , and R 5 at least one of is a polymer; X is independently selected from the group consisting of alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and no group.

2. The method of claim 1, comprising:

21. The polymer is a polymer of formula (IX): 【Chemistry 5】 (In the formula, R 11a , R 11b , R 11c , R 11d , R 21a , R 21b , R 21c , R 21d , R 31a , R 31b , R 31c , and R 31d are H and C, respectively. 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 12a , R 12b , R 12c , R 12d , R 22a , R 22b , R 22c , R 22d , R 32a , R 32b , R 32c , and R 32d are H and C, respectively. 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 13a , R 13b , R 14a , and R 14b are non-existent, C 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 13a , R 13b , R 14a , and R 14b Two of them are non-existent, the remaining two are present, and C 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 23a , R 23b , R 24a , and R 24b are non-existent, C 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl, where R 23a , R 23b , R 24a and R 24b One of them is non-existent, the remaining three are present, and C 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 33a , R 33b , R 34a , and R 34b are respectively, C 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; R 15a , R 15b , R 15c , R 15d , R 15e , R 15f , R 25a , R 25b , R 25c , R 25d , R 25e , R 25f , R 35a , R 35b , R 35c , R 35d , R 35e , and R 35f are H and C, respectively. 1～6 Alkyl, C 1～6 Haloalkyl, C 1～6 Alkoxy, C 1～6 independently selected from haloalkoxy, halo, aryl, and heteroaryl; X 11 , X 21 , and X 31 are non-existent, C 1～6 Alkylene, C 1～6 independently selected from the group consisting of haloalkylene, arylene, and heteroarylene; a, b, and c are mole percentages; a is from 0 mole percent to 45 mole percent; b+c is 55 mole percent to 100 mole percent; b and c are each greater than 0 percent; a+b+c=100%.) 2. The method of claim 1, comprising:

22. The repeat unit is an imidazolium-containing moiety of formula (X): 【Chemistry 6】 (In the formula, R 1XY , R 2XY , R 4XY , and R 5XY each is independently selected from absent, alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; however, R 1XY and R 2XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 1XY and R 2XY If one of R is absent, then the absent R 1XY or R 2XY is attached to an imidazolyl group that is charge neutral; R 4XY and R 5XY at least one of is selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, and aralkyl; R 4XY and R 5XY If one of R is absent, then the absent R 4XY or R 5XY is attached to an imidazolyl group that is charge neutral; R 3XY and R 6XY each is independently selected from alkyl, perfluoroalkyl, heteroalkyl, aryl, aralkyl, and heteroaryl; R 15XY is selected from alkylene, perfluoroalkylene, heteroalkylene, arylene, aralkylene, and heteroarylene, each of which is optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 16XY is selected from a bond, arylene, and heteroarylene, each of said arylene and heteroarylene optionally substituted with 1, 2, 3, or 4 substituents independently selected from alkyl, perfluoroalkyl, heteroalkyl, and halo; R 7XY , R 10XY , R 11XY , and R 14XY each is independently selected from H, alkyl, perfluoroalkyl, and heteroalkyl; R 8XY , R 9XY , R 12XY , and R 13XY are each independently selected from hydrogen, alkyl, perfluoroalkyl, and heteroalkyl.

2. The method of claim 1, comprising:

23. The repeating unit is a moiety of formula (XI) 【Chemistry 7】 2. The method of claim 1, comprising:

24. The repeating unit is a moiety of formula (XII) 【Chemistry 8】 2. The method of claim 1, comprising:

25. The repeating unit is a moiety of formula (XIII) 【Chemistry 9】 2. The method of claim 1, comprising:

26. 26. The method of any one of claims 1 to 25, wherein the polymer is in the form of a coating or film.

27. 26. The method of any one of claims 1 to 25, wherein the polymer is in the form of a spun fiber, an electrospun fiber, a solution cast coating, an extruded fiber, a nanofiber, or any combination thereof.

28. 26. The method of any one of claims 1 to 25, wherein the polymer is in the form of a microporous film, a nanoporous film, a nonwoven sheet, a woven sheet, a mat, a fabric, or any combination thereof.

29. 26. The method of any one of claims 1 to 25, wherein the polymer is a blend.

30. 30. The method of claim 29, wherein the blend is a polymer blend.

31. 26. The method of any one of claims 1 to 25, wherein the polymer is a graft copolymer, an interpenetrating network, an aerogel, or a hydrogel.

32. 26. The method of any one of claims 1 to 25, wherein the surface comprises a surface or part of a medical device.

33. 33. The method of claim 32, wherein the medical device is selected from a urinary catheter, a percutaneous catheter, a central venous catheter, a vascular access device, a heart valve, a stent, a vascular graft, a skeletal joint, a dental filling, a dental implant, an oxygen transport membrane, a suture, an intravenous delivery site, a drug delivery catheter, a drain, a gastric feeding tube, a tracheotomy tube, a contact lens, an intraocular lens, an orthopedic implant, a neurostimulation lead, a pacemaker lead, a blood bag, an air filter, and a drug diffusion matrix (e.g., a membrane, a film, a rod, a bead, or any combination thereof).

Images