Monomer composition having antibacterial properties

Abstract

The present invention provides a technology relating to an ionene composition having antibacterial properties. For example, one or more embodiments may include a monomer comprising a single ionene unit. The single ionene unit may include a cation disposed along a molecular backbone. Additionally, a hydrophobic functional group may be covalently bonded to the molecular backbone, and the single ionene unit may have antimicrobial functionality.

Description

TECHNICAL FIELD

[0001] The present disclosure relates to one or more monomers having antibacterial functions, and more specifically, relates to one or more monomers containing one or more cationic or hydrophobic functional groups, or both. BACKGROUND ART

[0002] The discovery and improvement of antibiotics was one of the greatest achievements of the 20th century that revolutionized medical care. For example, antibiotics such as penicillin, ciprofloxacin, and doxycycline can achieve microbial selectivity by targeting and disrupting the metabolism of specific prokaryotes, while remaining benign to eukaryotic cells to provide high selectivity. When administered appropriately, infections can be eradicated. Unfortunately, this therapeutic specificity of antibiotics also leads to countereffects, as underdosing (incomplete killing) allows slight genetic mutations, which reduces the effect of the antibiotic and results in the development of resistance. Consequently, nosocomial infections caused by drug-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), multidrug-resistant Pseudomonas aeruginosa, and vancomycin-resistant Enterococci (VRE), are becoming even more prevalent. Further complicating the situation is the widespread use of antibacterial agents in self-care products, disinfectants, hospital detergents and the like, including anilides, bis-phenols, biguanides and quaternary ammonium compounds, in which the main concern is the development of cross-resistance and co-resistance with clinically used antibiotics, particularly in hospitals. Another unfortunate feature is, for example, the cumulative and persistent effect of triclosan on the skin. Furthermore, biofilms are associated with numerous nosocomial infections and transplant failures, and the eradication of biofilms remains an unachieved challenge to date. There is an additional complexity that leads to the development of drug resistance, as antibiotics cannot penetrate the extracellular polymeric substances that encapsulate bacteria in biofilms.

[0003] However, polymers with cationic charges can lead to electrostatic disruption of bacterial membrane interactions. Furthermore, cationic polymers can be easily made amphiphilic by adding hydrophobic regions that allow for both membrane bonding and integration or dissolution. The balance of amphiphilicity has been shown to play a crucial role not only in antimicrobial properties but also in hemolytic activity. Many of these antimicrobial polymers exhibit relatively low selectivity, defined as relative toxicity to mammalian cells or hemolysis associated with pathogens. [Overview of the project]

[0004] The following outline provides a basic understanding of one or more embodiments of the present invention. This outline is not intended to identify key or important elements or to describe any scope of any particular embodiment or any scope of any claim. Its sole purpose is to present the concepts in a simplified form as a prelude to the more detailed descriptions that will follow. One or more embodiments described herein describe methods or compositions relating to antimicrobial ions, or both.

[0005] In this embodiment, a monomer is provided. The monomer may comprise a single ionene unit. The single ionene unit may comprise a cation arranged along the molecular skeleton. Furthermore, a hydrophobic functional group may be covalently bonded to this molecular skeleton, and the single ionene unit may have antimicrobial properties.

[0006] In another embodiment, a monomer is provided. The monomer may comprise a single ionene unit. The single ionene unit may comprise a cation arranged along a degradable molecular skeleton, which may comprise a terephthalamide structure. Furthermore, the single ionene unit may have antimicrobial properties.

[0007] In another embodiment, a method is provided. The method may include dissolving an amine monomer and an electrophile in a solvent. The electrophile may be an alkyl halide. The method may also include forming a monomer from the amine monomer and the electrophile. The monomer may comprise a single ionene unit. The single ionene unit may comprise a cation arranged along the molecular skeleton, and the single ionene unit may have antimicrobial properties.

[0008] In another embodiment, a method is provided. The method may include dissolving an amine monomer and an electrophile in a solvent. The amine monomer may include a degradable molecular skeleton that may include a terephthalamide structure. The method may also include forming a monomer from the amine monomer and the electrophile. The monomer may include a single ionene unit. The single ionene unit may include a cation arranged along the degradable molecular skeleton and may have antimicrobial properties.

[0009] Another embodiment provides a method which may involve contacting a pathogen with a monomer. The monomer may comprise a single ionene unit which may comprise a cation arranged along a molecular skeleton. Hydrophobic functional groups may also be covalently bonded to this molecular skeleton. Furthermore, the single ionene unit may have antimicrobial properties. In addition, this contact may electrostatically disrupt the pathogen's membrane. [Brief explanation of the drawing]

[0010] [Figure 1] This figure shows, as an example, a non-limiting ionene unit according to one or more embodiments described herein. [Figure 2] This figure illustrates, as an example, a non-limiting dissolution process that can be carried out by one or more ionene units according to one or more embodiments described herein. [Figure 3] This flowchart illustrates, as an example, a non-limiting method that can facilitate the production of one or more ionene compositions according to one or more embodiments described herein. [Figure 4]This figure illustrates, as an example, a non-limiting compound formation scheme that can facilitate the production of one or more ionene compositions according to one or more embodiments described herein. [Figure 5] This figure illustrates, as an example, a non-limiting ionene composition according to one or more embodiments described herein. [Figure 6] Another figure illustrating, as an example, a non-limiting ionene composition according to one or more embodiments described herein. [Figure 7] This figure shows, as an example, a non-limiting chemical structural formula that may characterize one or more ionene units according to one or more embodiments described herein. [Figure 8] This flowchart illustrates, as an example, a non-limiting method that can facilitate the generation of one or more ionene units according to one or more embodiments described herein. [Figure 9] This figure illustrates, as an example, a non-limiting compound formation scheme that can facilitate the production of one or more ionene compositions according to one or more embodiments described herein. [Figure 10] This figure illustrates, as an example, a non-limiting compound formation scheme that can facilitate the production of one or more ionene compositions according to one or more embodiments described herein. [Figure 11] This figure shows, as an example, a non-limiting table that may represent the antimicrobial functions of various ionene compositions according to one or more embodiments described herein. [Figure 12] Another figure, as an example, is a non-limiting table that may represent the antimicrobial properties of various ionene compositions according to one or more embodiments described herein. [Figure 13] Another figure, as an example, is a non-limiting table that may represent the antimicrobial properties of various ionene compositions according to one or more embodiments described herein. [Figure 14] This figure shows, as an example, a non-limiting graph that may represent the hemolytic activity of various ionene compositions according to one or more embodiments described herein. [Figure 15] Another figure, as an example, is a non-limiting graph that may represent the hemolytic activity of various ionene compositions according to one or more embodiments described herein. [Figure 16] Another figure, as an example, is a non-limiting graph that may represent the hemolytic activity of various ionene compositions according to one or more embodiments described herein. [Figure 17] This flowchart illustrates, as an example, a non-limiting method that facilitates the killing of pathogens by one or more ionene units according to one or more embodiments described herein. [Modes for carrying out the invention]

[0011] The following detailed description is not merely illustrative, nor is it intended to limit the embodiments, or the application or use of the embodiments, or both. Furthermore, it is not intended to be bound by any expression or meaning of any information presented in the preceding sections on background art or the summary of the invention, or in the sections on modes for carrying out the invention.

[0012] Here, one or more embodiments are described with reference to the drawings, in which similar figures are used to refer to similar elements throughout. The following description provides numerous specific details for illustrative purposes to give a more thorough understanding of one or more embodiments. However, it will be apparent that in various cases one or more embodiments may be carried out without such specific details.

[0013] The discovery and improvement of antibiotics were one of the greatest achievements of the 20th century, revolutionizing medicine. For example, antibiotics like penicillin, ciprofloxacin, and doxycycline achieve microbial selectivity by targeting and disrupting the metabolism of specific prokaryotes, while simultaneously maintaining benignity and high selectivity for eukaryotic cells. When administered appropriately, they can eradicate infections. Unfortunately, this therapeutic specificity of antibiotics is also counteracted, as underdosing (incomplete killing) allows for slight genetic mutations, thereby reducing the antibiotic's effect and leading to resistance. Consequently, hospital-acquired infections caused by drug-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), multidrug-resistant Pseudomonas aeruginosa, and vancomycin-resistant Enterococci (VRE), are becoming increasingly prevalent. Further complicating matters is the widespread use of antimicrobial agents in self-care products, disinfectants, and hospital cleaning agents, including anilides, bisphenols, biguanides, and quaternary ammonium compounds. In this case, the main concern is the development of cross-resistance and co-resistance with clinically used antibiotics, particularly in hospitals. Another unfortunate characteristic is the cumulative and persistent effects on the skin, such as triclosan. Moreover, biofilms are associated with numerous hospital-acquired infections and transplant failures, and furthermore, the eradication of biofilms remains an unfulfilled challenge to this day. A further complexity exists in that antibiotics cannot penetrate the extracellular polymer material that encapsulates bacteria in biofilms, leading to the development of drug resistance.

[0014] However, polymers bearing cationic charges can lead to electrostatic disruption of bacterial membrane interactions. Furthermore, cationic polymers can be readily made amphiphilic by the addition of hydrophobic regions, which enables both membrane binding and integration or lysis. The amphiphilic balance has been shown to play an important role not only in antibacterial properties but also in hemolytic activity. Many such antibacterial polymers exhibit relatively low selectivity when defined by their relative toxicity to mammalian cells or hemolysis associated with pathogens.

[0015] As used herein, the term "ionene" may refer to a polymer unit, copolymer unit, or monomer unit, or a combination thereof, which contains nitrogen cations, phosphorus cations, or both, that are arranged along, located within, or both along and within the molecular backbone, thereby capable of imparting a positive charge. Examples of nitrogen cations include, but are not limited to, quaternary ammonium cations, protonated secondary amine cations, protonated tertiary amine cations, or imidazolium cations, or combinations thereof. Examples of phosphorus cations include, but are not limited to, quaternary phosphonium cations, protonated secondary phosphine cations, and protonated tertiary phosphine cations. As used herein, the term "molecular backbone" may refer to the central chain of covalently bonded atoms that forms the primary structure of a molecule. In various embodiments described herein, side chains may be formed by attaching one or more functional groups to the molecular backbone. As used herein, the term "polyionene" may refer to a polymer that can contain a plurality of ionenes. For example, a polyionene may comprise repeating ionene units.

[0016] Figure 1 shows an exemplary, non-limiting diagram of an ionene unit 100 according to one or more embodiments described herein. The ionene unit 100 can include a molecular backbone 102, one or more cations 104, or one or more hydrophobic functional groups 106, or a combination thereof. In various embodiments, the ionenes or polyionenes, or both, described herein can include the ionene unit 100. For example, the polyionenes described herein may comprise a plurality of ionenes bonded together, in which case the bonded ionenes may have a composition exemplified by the ionene unit 100.

[0017] The molecular backbone 102 can include a plurality of covalently bonded atoms (shown as circles in Figures 1 and 2). The atoms are bonded in any desired structure, which can include, but is not limited to, a chain structure, or a ring structure, or a combination thereof. The molecular backbone 102 includes one or more chemical structures, which can include, but are not limited to, alkyl structures, aryl structures, alkenyl structures, aldehyde structures, ester structures, carboxy structures, carbonyl structures, amine structures, amide structures, phosphide structures, phosphine structures, or combinations thereof, or others. Those skilled in the art will recognize that the number of atoms that can constitute the molecular backbone can vary depending on the desired function of the ionene unit 100. For example, while 19 atoms are shown in Figure 1, molecular backbones 102 that can include tens, hundreds, or thousands, or a combination thereof, of atoms are also contemplated.

[0018] One or more cations 104 are located within the molecular skeleton 102. As described above, one or more cations 104 may include nitrogen cations, phosphorus cations, or both. The cations 104 may be arranged along the molecular skeleton 102, covalently bonding with other atoms in the molecular skeleton 102. In various embodiments, one or more cations 104 may include at least a portion of the molecular skeleton 102. Those skilled in the art will recognize that the number of cations 104 that can constitute an ionene unit 100 may vary depending on the desired function of the ionene unit 100. For example, while Figure 1 shows two cations 104, ionene units 100 may also be conceivable that contain tens, hundreds, or thousands, or combinations thereof, of cations 104. Furthermore, while Figure 1 shows multiple cations 104 arranged at equal intervals, other stereoconfigurations in which the cations 104 are not arranged at equal intervals are also conceivable. Furthermore, one or more cations 104 may be located at each end of the molecular skeleton 102, or in the intermediate part of the molecular skeleton 102 between two or more ends, or both. One or more cations 104 may contribute a positive charge to one or more positions of the ionene unit 100.

[0019] One or more hydrophobic functional groups 106 may bond to the molecular skeleton 102 to form a side chain. One or more hydrophobic functional groups 106 may bond to the molecular skeleton 102 via bonding with cations 104. In addition, one or more hydrophobic functional groups 106 may bond to electrically neutral atoms of the molecular skeleton 102. The ionene unit 100 may include one or more hydrophobic functional groups 106 bonded to one or more ends of the molecular skeleton 102, all ends of the molecular skeleton 102, or an intermediate portion of the molecular skeleton 102 (e.g., the portion between two ends), or a combination thereof.

[0020] In Figure 1, a biphenyl group is shown as the hydrophobic functional group 106, but other hydrophobic functional groups are also conceivable. Examples of hydrophobic functional groups 106 may include, but are not limited to, alkyl structures, aryl structures, alkenyl structures, ester structures, carboxyl structures, carbonyl structures, carbonate structures, alcohol structures, or combinations thereof, or others. In various embodiments, one or more hydrophobic functional groups 106 may include the same structure. In other embodiments, one or more hydrophobic functional groups 106 may include the first structure, and one or more other hydrophobic functional groups 106 may include different structures.

[0021] Figure 2 shows an example of a non-limiting lysis process 108 that may be facilitated by the ionene unit 100 according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted for brevity. The lysis process 108 may comprise multiple steps, which may collectively comprise an attack mechanism that can be carried out against pathogen cells by the ionene unit 100. Examples of pathogen cells may include, but are not limited to, Gram-positive bacterial cells, Gram-negative bacterial cells, fungal cells, or yeast cells, or combinations thereof.

[0022] The target pathogen cell may contain a membrane having a phospholipid bilayer 110. In various embodiments, the membrane may be an extracellular matrix. The phospholipid bilayer 110 may contain a plurality of membrane molecules 112 covalently bonded together, and each membrane molecule 112 may contain a hydrophilic head 114 and one or more hydrophobic tails 116. Furthermore, one or more of the plurality of membrane molecules 112 may be negatively charged (indicated by the "-" symbol in Figure 2).

[0023] At 118, an electrostatic interaction may occur between the positively charged cation 104 of the ionene unit 100 and one or more negatively charged membrane molecules 112. For example, the negative charge of one or more membrane molecules 112 may attract the ionene unit 100 to the membrane (e.g., the phospholipid bilayer 110). Furthermore, the electrostatic interaction may electrostatically disrupt the integrity of the membrane (e.g., the phospholipid bilayer 110). Once the ionene unit 100 is attracted to the membrane (e.g., the phospholipid bilayer 110), integration into the hydrophobic membrane may occur at 120. For example, at 120, one or more hydrophobic functional groups 106 of the ionene unit 100 may initiate integration into the phospholipid bilayer 110. The positively charged portion of the ionene unit 100 is attracted, electrostatically destroying one or more negatively charged film molecules 112 (e.g., one or more hydrophilic heads 114), and at the same time, one or more hydrophobic functional groups 106 can penetrate between the hydrophilic heads 114 and enter the hydrophobic region formed by the multiple hydrophobic tails 116.

[0024] As a result of the mechanisms occurring in 118 or 120 or both, destabilization of the membrane (e.g., the phospholipid bilayer 110) may occur in 122. For example, one or more hydrophobic functional groups 106 may act to cleave one or more negatively charged membrane molecules 112 from adjacent membrane molecules 112, and positively charged ionene units 100 may move the cleaved membrane segment (e.g., which may include one or more negatively charged membrane molecules 112, or one or more neutral membrane molecules 112, or both, constituting a layer of the phospholipid bilayer 110) away from adjacent segments of the membrane (e.g., adjacent segments of the phospholipid bilayer 110). As the cleaved segments of the membrane (e.g., the phospholipid bilayer 110) are pulled apart, they become completely separated from other membrane molecules 112 in 124, thereby potentially forming a gap in the membrane (e.g., the phospholipid bilayer 110). The formed gap may contribute to the lysis of target pathogen cells. In various embodiments, multiple ionene units 100 can simultaneously carry out the lysis process 108 on the cell. Furthermore, the ionene units 100 involved in the lysis process 108 do not need to carry out the same stage of the attack mechanism simultaneously.

[0025] Figure 3 shows a flowchart illustrating an example of a non-limiting method 200 that can facilitate the production of one or more ionene units 100 (for example, which may be characterized by Figure 1 or 2 or both) according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted for brevity. Method 200 can be carried out using commercially available amine monomers or commercially available electrophiles or both to produce one or more ionene units 100. The ionene units 100 formed by Method 200 may comprise one or more monomers.

[0026] Method 200 may include dissolving one or more amine monomers and one or more electrophiles in a solvent in 202. One or more amine monomers may contain one or more amino groups. Examples of amino groups that may constitute one or more amine monomers may include, but are not limited to, primary amino groups, secondary amino groups, tertiary amino groups, heterocyclic groups (e.g., imidazole groups or pyridine groups or both), or combinations thereof, or others. For example, one or more amine monomers may contain tertiary amino groups. Furthermore, if one or more amine monomers contain multiple amino groups, the first amino group of the amine monomer may have the same or a different structure as the second amino group of the amine monomer. For example, one or more amine monomers may contain two or more tertiary amino groups. In addition, one or more amine monomers may contain an alkyl structure or an aryl structure or both. Moreover, one or more amine monomers may contain one or more functional groups (e.g., hydroxyl groups). Examples of amine monomers may include, but are not limited to, 1-butylimidazole, N-methyldiethanolamine, bis[2-(N,N-dimethylamino)ethyl] ether, N,N,N',N'-tetramethyl-p-phenylenediamine, N,N-dimethylbenzylamine, diethanolamine derivatives, or combinations thereof, or others.

[0027] One or more electrophiles may include alkyl halides (e.g., dialkyl halides). For example, one or more electrophiles may include bromides, chlorides, or both. Examples of electrophiles may include, but are not limited to, p-xylylenedichloride, 4,4'-bis(chloromethyl)biphenyl, 1,4-bis(bromomethyl)benzene, 4,4'-bis(bromomethyl)biphenyl, 1,4-bis(iodomethyl)benzene, 1,6-dibromohexane, 1,8-dibromooctane, 1,12-dibromododecane, 1,6-dichlorohexane, 1,8-dichlorooctane, benzyl bromide, 3-chloro-1-propanol, 1-bromohexane, 2-(2-chloroethoxy)ethanol, 3-chloro-1,2-propanediol, 1-bromooctane, 1-bromododecane, benzyl chloride, or combinations thereof, or others.

[0028] The solvent may be an organic solvent. In addition, the solvent may be a protic or aprotic solvent, or both, or an alcohol, or a combination thereof. Examples of solvents may include, but are not limited to, dimethylformamide (DMF), methanol, tetrahydrofuran (THF), dichloromethane (DCM), or combinations thereof, or others. To facilitate dissolution, method 200 may further include stirring one or more amine monomers, one or more electrophiles, or a solvent, or a combination thereof, at a temperature between 15 degrees Celsius and 150 degrees Celsius for a period of 8 to 72 hours (e.g., 12 to 24 hours).

[0029] Method 200 comprises forming one or more monomers in 204 from one or more amine monomers or one or more electrophiles or both, where each monomer may contain a single ionene unit 100. One or more electrophiles may be covalently bonded to one or more amino groups of one or more amine monomers. For example, the formation in 204 may involve subjecting one or more amino groups of one or more amine monomers to alkylation or quaternization or both using one or more electrophiles, thereby ionizing one or more amino groups. Thus, the formation in 204 can simultaneously induce a polymer formation reaction (e.g., formation of ionene unit 100) and charging (e.g., formation of cation 104).

[0030] One or more single ionene units 100 constituting one or more monomers may contain one or more cations 104 (e.g., formed by the ionization of one or more amino groups in 204) arranged along the molecular skeleton 102. One or more cations 104 may include a protonated secondary amine cation, a protonated tertiary amine cation, a quaternary ammonium cation, or an imidazolium cation, or a combination thereof. In addition, one or more single ionene units 100 constituting one or more monomers may contain one or more hydrophobic functional groups 106 covalently bonded to the molecular skeleton 102 (e.g., via one or more cations 104). For example, one or more hydrophobic functional groups 106 may originate from one or more electrophiles in 204, or be formed by alkylation, quaternization, or both, or both. One or more single ionene units 100 formed in 204, and one or more monomers therefrom, may have antimicrobial properties.

[0031] Figure 4 shows an example of a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions (which may be characterized by Figures 1 and 2, or produced according to Method 200, or both) by one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. The compound formation scheme shown in Figure 4 may be carried out using commercially available amine monomers or commercially available electrophiles or both, and may produce one or more ionene units 100. The ionene units 100 formed and produced by the compound formation scheme of Figure 4 may constitute one or more monomers. Also, "n" in Figure 4 may represent an integer between 1 and 1,000 (for example, an integer between 1 and 100), which may represent one or more specific amine monomers or electrophiles or both. Further embodiments of the compound formation scheme shown in Figure 4 are also conceivable. For example, the main mechanism of the compound formation scheme shown in Figure 4 can be applied to any amine monomer or electrophile, or both, with respect to the various features described herein (see, for example, Figures 1-2 or Method 200, or both).

[0032] As shown in Figure 4, scheme 300 may represent the formation of an ionene composition (e.g., a first ionene composition 302) from a dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) and a plurality of amine monomers (e.g., a first amine monomer 306). For example, a dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) can be dissolved in a solvent (e.g., DMF) together with a plurality of amine monomers (e.g., a first amine monomer 306). The dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl), the plurality of amine monomers (e.g., a first amine monomer 306), and the solvent can be stirred at a temperature of 15°C to 150°C (e.g., room temperature ("RT")) for 8 to 72 hours (e.g., 12 to 24 hours).

[0033] In scheme 300, multiple amine monomers (e.g., a first amine monomer 306) can be covalently bonded with an electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) by one or more amino groups (e.g., tertiary amino groups) of the multiple amine monomers (e.g., a first amine monomer 306). For example, scheme 300 may include alkylating one or more amino groups (e.g., tertiary amino groups) using an electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) to form an ionene composition (e.g., a first ionene composition 302) containing multiple cations 104 (e.g., quaternary ammonium cations). Furthermore, the ionene composition (e.g., the first ionene composition 302) may contain one or more hydrophobic functional groups 106 derived from the electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) as a result of the alkylation. Therefore, the ionene compositions that can be produced by scheme 300 (e.g., the first ionene composition 302) may include the various features described in relation to Figures 1-2, or may be produced according to the various features of method 200, or both.

[0034] As shown in Figure 4, scheme 308 may represent the formation of an ionene composition (e.g., a second ionene composition 310) from an alkyl halide (e.g., 4-(chloromethyl)biphenyl) and an amine monomer (e.g., a first amine monomer 306). For example, the alkyl halide (e.g., 4-(chloromethyl)biphenyl) may be dissolved together with the amine monomer (e.g., a first amine monomer 306) in a solvent (e.g., DMF). The alkyl halide (e.g., 4-(chloromethyl)biphenyl), the amine monomer (e.g., a first amine monomer 306), and the solvent may be stirred at a temperature of 15°C to 150°C (e.g., room temperature ("RT")) for 8 to 72 hours (e.g., 12 to 24 hours).

[0035] In scheme 308, an amine monomer (e.g., a first amine monomer 306) can be covalently bonded with an electrophile (e.g., 4-(chloromethyl)biphenyl) to one or more amino groups (e.g., tertiary amino groups) of the amine monomer (e.g., a first amine monomer 306). For example, scheme 308 may include alkylating one or more amino groups (e.g., tertiary amino groups) using an electrophile (e.g., 4-(chloromethyl)biphenyl) to form an ionene composition (e.g., a second ionene composition 310) containing cation 104 (e.g., a quaternary ammonium cation). Furthermore, the ionene composition (e.g., the second ionene composition 310) may contain one or more hydrophobic functional groups 106 derived from the electrophile (e.g., 4-(chloromethyl)biphenyl) as a result of the alkylation. Therefore, the ionene composition that can be produced by scheme 308 (e.g., the second ionene composition 310) may include the various features described in relation to Figures 1-2, or may be produced according to the various features of method 200, or both.

[0036] As shown in Figure 4, scheme 314 may represent the formation of an ionene composition (e.g., a third ionene composition 316) from multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) and a diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine). For example, multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) can be dissolved together with a diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine) in a solvent (e.g., DMF). Multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl), a diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine) and a solvent can be stirred at a temperature of 15°C to 150°C (e.g., room temperature ("RT")) for 8 to 72 hours (e.g., 12 to 24 hours).

[0037] In Scheme 314, multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) can be covalently bonded to a diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine) by one or more amino groups (e.g., tertiary amino groups) of the diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine). For example, Scheme 314 may include alkylating one or more amino groups (e.g., tertiary amino groups) using multiple electrophiles (e.g., 4-(chloromethyl)biphenyl) to form an ionene composition (e.g., a third ionene composition 316) containing multiple cations 104 (e.g., quaternary ammonium cations). Furthermore, the ionene composition (e.g., the third ionene composition 316) may, as a result of alkylation, contain one or more hydrophobic functional groups 106 derived from the multiple electrophiles (e.g., 4-(chloromethyl)biphenyl). Therefore, the ionene composition that can be produced by scheme 314 (e.g., the third ionene composition 316) may include the various features described in relation to Figures 1-2, or may be produced according to the various features of method 200, or both.

[0038] Figure 5 shows an example of a non-limiting ionene composition that may contain a single ionene unit 100, which may include various features described in Figures 1-2, or may be produced according to various features of Method 200 or the compound formation scheme shown in Figure 4, or both. For brevity, similar elements used in other embodiments described herein are omitted for brevity. The ionene composition shown in Figure 5 may be a monomer and may have antimicrobial properties.

[0039] For example, Figure 5 may show the fourth ionene composition 402, the fifth ionene composition 404, the sixth ionene composition 406, the seventh ionene composition 408, the eighth ionene composition 410, the ninth ionene composition 412, the tenth ionene composition 414, the twelfth ionene composition 418, the thirteenth ionene composition 420, or the fourteenth ionene composition 422, or combinations thereof. Each of the ionene compositions shown in Figure 5 may be produced according to various features of Method 200. Furthermore, each of the ionene compositions shown in Figure 5 may be produced according to the main mechanisms shown in the multiple compound formation schemes of Figure 4.

[0040] Figure 6 shows another diagram illustrating an example of a non-limiting ionene composition that may contain a single ionene unit 100, which may include various features described in Figures 1-2, or may be produced according to various features of Method 200 or the compound formation scheme shown in Figure 4, or both. For the sake of brevity, similar elements used in other embodiments described herein are omitted for brevity. The ionene composition shown in Figure 6 may be a monomer and may have antimicrobial properties.

[0041] For example, Figure 6 may show the 15th ionene composition 502, the 16th ionene composition 504, the 17th ionene composition 506, the 18th ionene composition 508, the 19th ionene composition 510, the 20th ionene composition 512, the 21st ionene composition 514, the 22nd ionene composition 516, the 23rd ionene composition 518, the 24th ionene composition 520, or the 25th ionene composition 522, or combinations thereof. Each of the ionene compositions shown in Figure 6 may be produced according to various features of Method 200. Furthermore, each of the ionene compositions shown in Figure 6 may be produced according to the main mechanisms shown in the multiple compound formation schemes of Figure 4.

[0042] Figure 7 shows an example of a non-limiting chemical structural formula 600 that may characterize the structure of an ionene unit 100 according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted for brevity. In various embodiments, one or more ionene units 100 characterized by chemical structural formula 600 may comprise a monomer composition.

[0043] As shown in Figure 7, one or more ionene units 100 characterized by chemical structural formula 600 may include a degradable molecular skeleton 102. Furthermore, the degradable molecular skeleton 102 may include one or more terephthalamide structures. In various embodiments, one or more ionene units 100 characterized by chemical structural formula 600 may be derived from polyethylene terephthalate (PET), in which case one or more terephthalamide structures may be derived from this PET. However, one or more embodiments of chemical structural formula 600 may include terephthalamide structures derived from one or more molecules other than PET.

[0044] In Figure 7, "X" may represent one or more cations 104. For example, "X" may represent one or more cations 104 selected from the group which may include, but are not limited to, one or more nitrogen cations, one or more phosphorus cations, and / or combinations thereof. For example, "X" may represent one or more nitrogen cations selected from the group which may include, but are not limited to, one or more protonated secondary amine cations, one or more protonated tertiary amine cations, one or more quaternary ammonium cations, or one or more imidazolium cations, or combinations thereof. In another case, "X" may represent one or more phosphorus cations selected from the group which may include, but are not limited to, one or more protonated secondary phosphine cations, one or more protonated tertiary phosphine cations, or one or more quaternary phosphonium cations, or combinations thereof.

[0045] One or more cations 104 (represented, for example, by "X" in chemical structural formula 600) may covalently bond with one or more linking groups to form at least a portion of the degradable molecular skeleton 102. One or more linking groups may link one or more cations 104 to one or more terephthalamide structures, thereby comprising the molecular skeleton 102. "Y" in Figure 7 may represent one or more linking groups. One or more linking groups may include any structure depending on the various characteristics of the molecular skeleton 102 described herein. For example, one or more linking groups may have any desirable structure, including, but not limited to, a chain structure, a ring structure, or a combination thereof. One or more linking groups may include, but not limited to, one or more chemical structures, including alkyl structures, aryl structures, alkenyl structures, aldehyde structures, ester structures, carboxyl structures, carbonyl structures, or combinations thereof, or others. For example, "Y" may represent one or more linking groups that may include an alkyl chain having 2 to 15 carbon atoms.

[0046] As shown in Figure 7, in various embodiments, one or more ionene units 100 characterized by chemical structural formula 600 may contain cations 104 (e.g., represented by "X") at multiple positions along the molecular skeleton 102. For example, the cations 104 may be located at any end of the molecular skeleton 102 (e.g., as shown in Figure 7). However, in one or more embodiments of chemical structural formula 600, the molecular skeleton 102 may contain fewer than or more than two cations 104 as shown in Figure 7.

[0047] Furthermore, “R” in Figure 7 may represent one or more hydrophobic functional groups 106 according to the various embodiments described herein. For example, one or more hydrophobic functional groups 106 may include one or more alkyl groups, one or more aryl groups, or both. For example, the hydrophobic functional group 106 may be derived from an alkyl halide. One or more hydrophobic functional groups 106 (e.g., represented as “R” in Figure 7) can be covalently bonded to one or more cations 104 (e.g., represented as “X” in Figure 7) or molecular skeletons 102 or both, which may include one or more cations 104 (e.g., represented as “X” in Figure 7), one or more linking groups (e.g., represented as “Y” in Figure 7), or one or more terephthalamide structures, or a combination thereof.

[0048] Figure 8 shows another flowchart illustrating an example of a non-limiting method 700 that can facilitate the production of one or more ionene units 100 characterized by chemical structural formula 600. For the sake of brevity, similar elements used in other embodiments described herein are omitted for brevity. One or more ionene units 100 produced by method 700 may comprise a monomer composition, have antimicrobial properties, or both.

[0049] Method 700 may include dissolving one or more amine monomers in a solvent using one or more electrophiles in 702. The one or more amine monomers may include a degradable molecular skeleton 102 which may include one or more terephthalamide structures. In addition, the amine monomers may include one or more amino groups. For example, the one or more amine monomers may be tetraamines. Examples of amino groups that may constitute one or more amine monomers may include, but are not limited to, primary amino groups, secondary amino groups, tertiary amino groups, heterocyclic groups (e.g., imidazole groups or pyridine groups or both), or combinations thereof, or others. Furthermore, if one or more amine monomers contain multiple amino groups, the first amino group of the amine monomer may have the same or a different structure as the second amino group of the amine monomer.

[0050] One or more electrophiles may include, for example, one or more alkyl halides (e.g., dialkyl halides). For example, one or more electrophiles may include chlorides or bromides or both. Examples of electrophiles may include, but are not limited to, benzyl chloride, 3-chloro-1-propanol, 1-bromohexane, 2-(2-chloroethoxy)ethanol, 3-chloro-1,2-propanediol, 1-bromooctane, 1-bromododecane, 4-(chloromethyl)biphenyl, 1-bromodecane, or combinations thereof, or others.

[0051] The solvent may be an organic solvent. In addition, the solvent may be a protic or aprotic solvent, or both, or an alcohol, or a combination thereof. Examples of solvents may include, but are not limited to, dimethylformamide (DMF), methanol, tetrahydrofuran (THF), dichloromethane (DCM), or combinations thereof, or others. To facilitate dissolution, method 200 may further include stirring one or more amine monomers, one or more electrophiles, or a solvent, or a combination thereof, at a temperature of 15°C to 150°C for 8 to 72 hours (e.g., 12 to 24 hours).

[0052] In one or more embodiments, one or more amine monomers can be prepared by aminolysis of PET. For example, PET can be depolymerized with one or more aminolysis reagents. One or more aminolysis reagents may be diamines. The first amino group of the diamine may include, but is not limited to, a primary amino group and a secondary amino group. The second amino group of the diamine may include, but is not limited to, a primary amino group, a secondary amino group, a tertiary amino group, or an imidazole group, or a combination thereof. For example, in one or more embodiments, the secondary amino group is a tertiary amino group or an imidazole group or both.

[0053] Scheme 1, presented below, demonstrates three examples of non-limiting degradable amine monomers that can be prepared by PET aminolysis.

[0054] [ka]

[0055] The preparation of multiple degradable amine monomers (e.g., according to Scheme 1) can be carried out without the need for a catalyst, a solvent, or both. Furthermore, the aminolysis of PET can be carried out using an excess amount of aminolysis reagent (e.g., a four-fold excess of aminolysis reagent). Moreover, aminolysis can depolymerize PET by heating. Upon cooling, the targeted degradable amine monomer can be crystallized with an excess amount of reagent and an alcohol byproduct (e.g., ethylene glycol). The degradable amine monomer can then be filtered and rinsed (e.g., with ethyl acetate) and used without further purification.

[0056] Scheme 1 shows three examples of degradable amine monomers derived from PET, but other degradable amine monomers that may be derived from PET are also conceivable. For example, PET may be depolymerized using aminolysis reagents other than the three shown in Scheme 1. For example, any aminolysis reagent having a primary amino group or a secondary amino group or both, which can donate a hydrogen atom to facilitate bonding to a terephthalamide structure, and a second amino group or an imidazole group or both, which can later become cation 104, may be polymerized using PET to prepare degradable amine monomers for use in 402. Furthermore, the prepared degradable amine monomers derived from PET described herein may comprise one or more amine monomers that can be used in Method 700.

[0057] In addition, in one or more embodiments, one or more amine monomers used with Method 700 may be derived from molecules other than PET. Those skilled in the art will readily recognize that excess amounts of other starting molecules can be polymerized, depolymerized, or both to prepare one or more amine monomers (for example, they may have a degradable skeleton, contain a terephthalamide structure, be tetraamines, or be a combination thereof), and these can be utilized with Method 700.

[0058] Method 700 may optionally include stirring one or more amine monomers, one or more electrophiles, and a solvent at a temperature of 15°C to 150°C for a period of 8 to 72 hours (for example, 12 to 24 hours).

[0059] Method 700 may include forming one or more monomers from one or more amine monomers and one or more electrophiles in 704. The monomer may include a single ionene unit 100 (e.g., characterized by chemical structural formula 600) which may include a cation 104 arranged along a degradable molecular skeleton 102. The molecular skeleton 102 may include a terephthalamide structure (e.g., shown in chemical structural formula 600). Furthermore, the single ionene unit 100 formed in 704 may have antimicrobial properties. In one or more embodiments, the formation in 704 may be carried out under nitrogen gas filling. In addition, the formation in 704 may generate a cation by alkylation, quaternization, or both, using one or more electrophiles. In various embodiments, the terephthalamide structure including the precipitate may be derived from PET obtained by depolymerization to prepare one or more amine monomers.

[0060] During the formation at 704, a nitrogen atom or a phosphorus atom, or both, located at the degradable amine monomer may be subjected to alkylation or quaternization, or both, using one or more electrophiles, thereby enabling the formation at 704 to simultaneously induce a polymer formation reaction (e.g., formation of repeating ionene units 100) and charging (e.g., formation of cation 104, including a nitrogen cation or a phosphorus cation, or both) without the need for a catalyst. Furthermore, one or more hydrophobic functional groups 106 may originate from one or more electrophiles as a result of the alkylation or quaternization, or both, or may be bonded to the degradable molecular skeleton 102 (e.g., via one or more cations 104), or both.

[0061] For example, the single ionene formed in 704 may include one or more embodiments of the ionene unit 100 and may be characterized by one or more embodiments of the chemical structural formula 600. For example, the single ionene unit 100 formed in 704 may include a degradable molecular skeleton 102, which may include one or more cations 104 (e.g., represented by "X" in chemical structural formula 600), one or more linking groups (e.g., represented by "Y" in chemical structural formula 600), one or more terephthalamide structures (e.g., shown in Figure 7), or one or more hydrophobic functional groups 106 (e.g., represented by "R" in chemical structural formula 600), or a combination thereof. The one or more cations 104 may be nitrogen cations (e.g., quaternary ammonium cations, or imidazolium cations, or a combination thereof) or phosphorus cations (e.g., quaternary phosphonium cations), or a combination thereof. Cation 104 can be linked to one or more terephthalamide structures via one or more linking groups (e.g., alkyl groups, aryl groups, or both). Furthermore, one or more cations 104 can be linked to one or more hydrophobic functional groups 106.

[0062] The antimicrobial activity of the repeating ionene units 100 produced by Method 700 may be molecular weight independent. Therefore, Method 700 can target conditions that allow the molecular weight reached by a diffusion-limited mechanism (e.g., polymer precipitation) to disappear down to a moderate molecular weight (e.g., less than 10,000 grams per mole (g / mol)), which may aid in the solubility of one or more ionene units 100 in an aqueous medium.

[0063] Figure 9 shows an example of a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions (which may be characterized by chemical structure formula 600, or produced according to method 700, or both) by one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted for brevity. The ionene unit 100 formed and produced by the compound formation scheme of Figure 9 may constitute one or more monomers, representing one or more specific amine monomers or electrophiles, or both. Further embodiments of the compound formation scheme shown in Figure 9 are also conceivable, while they may represent one or more specific amine monomers or electrophiles, or both. For example, the main mechanism of the compound formation scheme shown in Figure 9 may be applied to any amine monomer or electrophile, or both, with various features described herein (for example, with reference to chemical structure formula 600 or method 700, or both).

[0064] As shown in Figure 9, the compound formation scheme may represent the generation of ionene compositions (e.g., 26th ionene composition 802, 27th ionene composition 806, 28th ionene composition 808, or 29th ionene composition 810, or combinations thereof) from one or more alkyl halides (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or combinations thereof) and amine monomers (e.g., 4th amine monomer 804). For example, one or more alkyl halides (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or combinations thereof) may be dissolved in a solvent (e.g., DMF) together with the amine monomer (e.g., 4th amine monomer 804). One or more alkyl halides (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or a combination thereof), an amine monomer (e.g., a fourth amine monomer 804), and a solvent may be stirred at a temperature of 15°C to 150°C (e.g., room temperature ("RT")) for a period of 8 to 72 hours (e.g., 12 to 24 hours).

[0065] In the compound formation scheme of Figure 9, one or more alkyl halides (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or a combination thereof) can be covalently bonded to an amine monomer (e.g., a fourth amine monomer 804) by one or more amino groups (e.g., imidazole groups) of the amine monomer (e.g., a fourth amine monomer 804). For example, the compound formation scheme in Figure 9 may involve alkylating one or more amino groups (e.g., imidazole groups) using an electrophile (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or a combination thereof) to form an ionene composition (e.g., the 26th ionene composition 802, the 27th ionene composition 806, the 28th ionene composition 808, or the 29th ionene composition 810, or a combination thereof) containing a plurality of cations 104 (e.g., imidazolium cations). Furthermore, the ionene composition (e.g., the 26th ionene composition 802, the 27th ionene composition 806, the 28th ionene composition 808, or the 29th ionene composition 810, or a combination thereof) may, as a result of alkylation, contain one or more hydrophobic functional groups 106 derived from one or more electrophiles (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or a combination thereof). Therefore, the ionene compositions that can be produced by the compound formation scheme of Figure 9 (e.g., the 26th ionene composition 802, the 27th ionene composition 806, the 28th ionene composition 808, or the 29th ionene composition 810, or combinations thereof) may include various features described in relation to Figures 1-2 or chemical structural formula 600 or combinations thereof, or may be produced according to various features of method 700, or both.

[0066] Figure 10 shows an example of a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions (which may be characterized by, for example, chemical structural formula 600, or produced according to method 700, or both) by one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted for brevity. The ionene unit 100 formed and produced by the compound formation scheme of Figure 10 may constitute one or more monomers, while representing one or more specific amine monomers or electrophiles or both. Further embodiments of the compound formation scheme shown in Figure 10 are also conceivable, while representing one or more specific amine monomers or electrophiles or both. For example, the main mechanism of the compound formation scheme shown in Figure 10 may be applied to any amine monomer or electrophile or both (for example, by referring to chemical structural formula 600 or method 700 or both) with various features described herein.

[0067] As shown in Figure 10, the compound formation scheme may represent the generation of ionene compositions (e.g., the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 33rd ionene composition 916, the 34th ionene composition 920, or the 35th ionene composition 924, or a combination thereof) from one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof) and amine monomers (e.g., the 5th amine monomer 904). For example, one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof) can be dissolved in a solvent (e.g., DMF) together with an amine monomer (e.g., fifth amine monomer 904). One or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof), an amine monomer (e.g., fifth amine monomer 904), or a solvent, or a combination thereof, can be stirred at a temperature of 15°C to 150°C (e.g., room temperature ("RT")) for a period of 8 to 72 hours (e.g., 12 to 24 hours).

[0068] In the compound formation scheme of Figure 10, one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof) can be covalently bonded to an amine monomer (e.g., a fifth amine monomer 904) by one or more amino groups (e.g., tertiary groups) of the amine monomer (e.g., a fifth amine monomer 904). For example, the compound formation scheme in Figure 10 may involve quaternizing one or more amino groups (e.g., tertiary groups) using an electrophile (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof) to form an ionene composition (e.g., the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 33rd ionene composition 916, the 34th ionene composition 920, or the 35th ionene composition 924, or a combination thereof) containing multiple cations 104 (e.g., quaternary ammonium cations). Furthermore, the ionene compositions (e.g., the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 33rd ionene composition 916, the 34th ionene composition 920, or the 35th ionene composition 924, or a combination thereof) may, as a result of quaternization, contain one or more hydrophobic functional groups 106 derived from one or more electrophiles (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or a combination thereof).Therefore, the ionene compositions that can be produced by the compound formation scheme of Figure 10 (e.g., the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 33rd ionene composition 916, the 34th ionene composition 920, or the 35th ionene composition 924, or combinations thereof) may include various features described in relation to Figures 1-2 or chemical structural formula 600 or combinations thereof, or may be produced according to various features of method 700, or both.

[0069] Figure 11 illustrates a non-limiting Table 1000 that may represent the antimicrobial effects of one or more ionene compositions according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. To demonstrate the antimicrobial activity of the ionenes described herein (for example, ionene units 100, e.g., ionene compositions shown in Figures 5-6, which may include various features described in relation to Figures 1-2, or may be produced according to one or more features relating to Method 200 or the compound formation scheme of Figure 4 or both, or both), several ionene compositions were evaluated against a wide range of pathogens.

[0070] The first column 1002 of Table 1000 may represent the ionene composition being evaluated. The second column 1004 of Table 1000 shows the minimum inhibitory concentration (MIC) of the ionene composition for Staphylococcus aureus ("SA") in micrograms per milliliter (μg / mL). The third column 1006 of Table 1000 shows the MIC of the ionene composition for Escherichia coli ("EC") in μg / mL. The fourth column 1008 of Table 1000 shows the MIC of the ionene composition for Pseudomonas aeruginosa ("PA") in μg / mL. The fifth column 1010 of Table 1000 shows the MIC of the ionene composition for Candida albicans ("CA") in μg / mL. In column 6, 1012 of Table 1000, the hemolytic activity of the target ionene composition in relation to rat red blood cells ("HC50 The concentration is shown in μg / mL.

[0071] Figure 12 illustrates a non-limiting Table 1100 that may represent the antimicrobial effects of one or more ionene compositions according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. To demonstrate the antimicrobial activity of the ionenes described herein (for example, ionene units 100, e.g., ionene compositions shown in Figure 6, which may include various features described in relation to Figures 1-2, or may be produced according to one or more features relating to Method 200 or the compound formation scheme of Figure 4 or both, or both), several ionene compositions were evaluated against a wide range of pathogens.

[0072] Table 1100's first column 1102 shows the ionene compositions to be evaluated. Table 1100's second column 1104 shows the minimum inhibitory concentration (MIC) of the ionene compositions for Staphylococcus aureus ("SA") in micrograms per milliliter (μg / mL). Table 1100's third column 1106 shows the MIC of the ionene compositions for Escherichia coli ("EC") in μg / mL. Table 1100's fourth column 1108 shows the MIC of the ionene compositions for Pseudomonas aeruginosa (PA) in μg / mL. Table 1100's fifth column 1110 shows the MIC of the ionene compositions for Candida albicans ("CA") in μg / mL. Table 1100's sixth column 1112 shows the hemolytic activity ("HC") of the ionene compositions for rat erythrocytes. 50 The concentration is shown in μg / mL.

[0073] Figure 13 illustrates a non-limiting Table 1200 that may represent the antimicrobial effects of one or more ionene compositions according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. To demonstrate the antimicrobial activity of the ionenes described herein (e.g., ionene unit 100, which may include various features of chemical structural formula 600, or otherwise be produced according to method 700, or the compound formation scheme of Figure 9 or 10 or both, or either one or more features relating to both), several ionene compositions were evaluated against a wide range of pathogens.

[0074] Table 1200's first column, 1202, shows the ionene compositions being evaluated. Table 1200's second column, 1204, shows the minimum inhibitory concentration (MIC) of the ionene compositions for Staphylococcus aureus ("SA") in micrograms per milliliter (μg / mL). Table 1200's third column, 1206, shows the MIC of the ionene compositions for Escherichia coli ("EC") in μg / mL. Table 1200's fourth column, 1208, shows the MIC of the ionene compositions for Pseudomonas aeruginosa ("PA") in μg / mL. Table 1200's fifth column, 1210, shows the MIC of the ionene compositions for Candida albicans ("CA") in μg / mL. Table 1200's sixth column, 1212, shows the hemolytic activity ("HC") of the ionene compositions for rat erythrocytes. 50 The concentration is shown in μg / mL.

[0075] Figure 14 illustrates a non-limiting graph 1300 that may represent the hemolytic activity of various ionene compositions at various concentrations according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. For example, Figure 14 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity shown in graph 1300 may be in relation to rat red blood cells.

[0076] The first line 1302 in Graph 1300 may represent the 25th ionene composition 522. The second line 1304 in Graph 1300 may represent the 24th ionene composition 520. The third line 1306 may represent the third ionene composition 316. The fourth line 1308 in Graph 1300 may represent the 18th ionene composition 508. The fifth line 1310 in Graph 1300 may represent the 22nd ionene composition 516. The sixth line 1312 in Graph 1300 may represent the 23rd ionene composition 518. The seventh line 1314 in Graph 1300 may represent the 17th ionene composition 506. The seventh line 1316 in Graph 1300 may represent the 20th ionene composition 512. The eighth line 1318 in Graph 1300 may represent the 21st ionene composition 514, the 19th ionene composition 510, or the 16th ionene composition 504, or a combination thereof.

[0077] Figure 15 illustrates a non-limiting graph 1320 that may represent the hemolytic activity of various ionene compositions at various concentrations according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. For example, Figure 15 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity shown in graph 1320 is for rat red blood cells.

[0078] The first line 1324 in Graph 1320 may represent the 14th ionene composition 422. The second line 1326 in Graph 1320 may represent the 4th ionene composition 402, the 5th ionene composition 404, the 6th ionene composition 406, the 7th ionene composition 408, the 8th ionene composition 410, the 9th ionene composition 412, the 10th ionene composition 414, the 12th ionene composition 418, or the 13th ionene composition 420, or a combination thereof.

[0079] Figure 16 illustrates a non-limiting graph 1400 that may represent the hemolytic activity of various ionene compositions at various concentrations according to one or more embodiments described herein. For brevity, similar elements used in other embodiments described herein are omitted. For example, Figure 16 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity shown in graph 1400 may be in relation to rat red blood cells.

[0080] The first line 1402 in Graph 1400 may represent the 33rd ionene composition 916. The second line 1404 in Graph 1400 may represent the 26th ionene composition 802, the 27th ionene composition 806, the 28th ionene composition 808, the 29th ionene composition 810, the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 34th ionene composition 920, or the 35th ionene composition 924, or a combination thereof.

[0081] Figure 17 shows another flowchart illustrating an example of 1500 non-limiting methods for killing pathogens, preventing pathogen growth, preventing contamination by pathogens, or a combination thereof. For brevity, similar elements used in other embodiments described herein are omitted for brevity. Examples of pathogens include, but are not limited to, Gram-negative bacteria, Gram-positive bacteria, fungi, yeasts, or combinations thereof, or others.

[0082] Method 1500 may include contacting a pathogen with one or more monomers that may contain a single ionene unit 100 in 1502. One or more single ionene units 100 may contain one or more cations 104 arranged along a molecular skeleton 102. One or more single ionene units 100 may also contain one or more hydrophobic functional groups 106 covalently bonded to the molecular skeleton 102 (e.g., via one or more cations 104). One or more cations 104 may be nitrogen cations or phosphorus cations or both. Examples of nitrogen cations may include, but are not limited to, protonated secondary amine cations, protonated tertiary amine cations, quaternary ammonium cations, or imidazolium cations, or combinations thereof. In one or more embodiments, the molecular skeleton 102 may contain one or more terephthalamide structures. One or more monomers may comprise ionene compositions according to various embodiments described herein (e.g., various features described with respect to Figures 1-10).

[0083] Method 1500 may include electrostatically disrupting the pathogen membrane when the pathogen is brought into contact with a monomer in 1504. The membrane may include a phospholipid bilayer 110. One or more cations 104 constituting a single ionene unit 100 may target, disrupt, or both of the pathogen membrane according to the dissolution process 108. In addition, Method 1500 may include destabilizing the pathogen membrane by integrating one or more hydrophobic functional groups 106 of the ionene unit 100 into the membrane.

[0084] The various structures (e.g., those described in relation to Figures 1, 2, or 7, or combinations thereof), compositions (e.g., those described in relation to Figures 4-6, 9-16), or methods (e.g., those described in relation to Figures 3, 8, or 17, or combinations thereof), or combinations thereof, described herein may be incorporated into various applications. For example, these applications may include, but are not limited to, various items such as food packaging, medical devices, floors, furniture surfaces, wound healing devices (e.g., bandages or gauze or both), building surfaces, plants (e.g., agricultural crops), ground, farming machinery, beds, sheets, clothing, blankets, shoes, doors, door frames, walls, ceilings, mattresses, lighting fixtures, small surfaces, switches, washbasins, handrails, remote controls, dressing tables, computer equipment, carts, trolleys, large baskets, large containers, or combinations thereof, or other cleaning, disinfection, sterilization, or other treatments, or combinations thereof. In another example, this application may include pharmaceuticals, pharmaceutical salts, hygiene products (e.g., soap or shampoo or both), or combinations thereof, or others. In yet another example, this application may include agricultural sprays or aqueous solutions or both that can facilitate the treatment of edible crops.

[0085] In addition, the term “or” is intended to mean an inclusive “or” rather than an exclusive “or.” That is, unless otherwise explicitly stated or evident from the context, “X utilizes A or B” is intended to mean either a natural inclusive substitution. That is, if X utilizes A, or X utilizes B, or X utilizes both A and B, “X utilizes A or B” is satisfied according to one of the aforementioned cases. Furthermore, the terms “a” and “an” as used in the subject specification and accompanying drawings should generally be interpreted as meaning “one or more” and referring to the singular, unless otherwise explicitly stated or evident from the context. As used herein, the terms “example” or “an example” or both are used to mean an example, case, or illustrative action. To avoid misunderstanding, the subject matter disclosed herein is not limited by such examples. In addition, no embodiment or design described herein as an "example" or "exemplary" or both shall necessarily be construed as superior or more advantageous than any other embodiment or design, nor shall it preclude exemplary equivalent structures and techniques known to those skilled in the art.

[0086] The above descriptions include only examples of systems, compositions, and methods. Needless to say, it is impossible to describe every conceivable combination of reagents, products, solvents, or items for the purpose of illustrating this disclosure, but those skilled in the art will recognize that many further combinations and substitutions of this disclosure are possible. Furthermore, to the extent that the terms “contains,” “has,” “possesses,” and others are used in the detailed description, claims, appendices, and drawings, such terms are intended to be comprehensive, as is the term “contains” when used as a substitute in the claims. The descriptions of various embodiments are presented for illustrative purposes only and are not intended to be exhaustive or limiting to the embodiments disclosed. Many variations and modifications will be apparent to those skilled in the art without departing from the scope of the embodiments described. The terms used herein have been chosen to best describe the principles, practical applications, or technological advancements beyond the art found in the market of the embodiments, or to enable others skilled in the art to understand the embodiments disclosed herein.

Claims

1. The following structural formula: 【Chemistry 1】 In the formula, R is C ６ H ５ CH ２ - group, HOCH ２ CH ２ CH ２ - group, HOCH ２ CH ２ OCH ２ CH 2- group, CH ３ CH ２ CH ２ CH ２ CH ２ CH ２ - group, HOCH ２ CH(OH)CH ２ - group, CH ３ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ - group, CH ３ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ - group, C ６ H ５ -C ６ H 4-CH ２ - group and CH ３ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ CH ２ - group, X is selected from the second group consisting of protonated secondary amine cations, protonated tertiary amine cations, quaternary ammonium cations, and imidazolium cations, Y represents a linking group selected from a third group consisting of alkylene groups and arylene groups, where, when X is a quaternary ammonium cation, R is C ６ H ５ CH ２ - group, HOCH ２ CH ２ CH ２ - group and HOCH ２ CH(OH)CH ２ - Selected from a group consisting of, A compound that possesses antibacterial properties.

2. The compound according to claim 1, wherein the functional group represented by R is covalently bonded to the cation.

3. The compound according to claim 1, having a structure selected from 802, 806, 808, 810, 902, 920, and 924 below.

4. Dissolving amine monomers containing a terephthalamide structure and electrophiles in a solvent, and The compound described in claim 1 is formed from the amine monomer and the electrophile. A method that includes this.

5. The method according to claim 4, comprising a process for forming a cation, the formation of which is selected from the group consisting of alkylation and quaternization.

6. The amine monomer, the electrophile, and the solvent are stirred at a temperature of 15 degrees Celsius or higher and 150 degrees Celsius or lower for a predetermined time of 12 hours or more and 24 hours or less. The method according to claim 4 or 5, further comprising:

7. The method according to claim 4, wherein the electrophile is selected from benzyl chloride, benzyl bromide, 3-chloro-1-propanol, 1-bromohexane, 2-(2-chloroethoxy)ethanol, 3-chloro-1,2-propanediol, 1-bromooctane, 1-bromododecane, 4-(chloromethyl)biphenyl, 1-bromodecane, or a combination thereof.

8. The method according to claim 4, wherein the amine monomer has a primary amino group, a secondary amino group, a tertiary amino group, and an imidazole group.

9. The method according to claim 4, wherein the compound has a structure selected from 802, 806, 808, 810, 902, 920, and 924 below.

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