Wound dressings and preparations, and methods for using them.

Abstract

This specification describes wound dressings, compositions, and formulations for wound healing. These dressings, compositions, and formulations contain at least one quaternary ammonium polymer, quaternary ammonium copolymer, quaternary ammonium interpenetrating polymer network, quaternary ammonium polyelectrolyte complex, quaternary ammonium blend, or quaternary ammonium complex having broad-spectrum antimicrobial properties.

Description

[Technical Field]

[0001] Cross-reference of related applications This application claims priority to U.S. Provisional Patent Application No. 63 / 460399, filed on 19 April 2023, which is incorporated herein by reference in its entirety.

[0002] field Embodiments of this disclosure relate to wound dressings and formulations comprising a composition of a quaternary ammonium polymer structure having broad-spectrum antimicrobial properties, as well as methods for using the same. [Background technology]

[0003] Wound healing is a natural physiological response to tissue damage. Wounds typically heal within 4 to 6 weeks. Chronic wounds are those that do not heal within this timeframe. One factor that can lead to impaired healing is bacterial colonization. Wound dressings and / or topical formulations with antimicrobial properties can control, reduce, or prevent infection, thereby promoting wound healing. [Overview of the Initiative]

[0004] In one embodiment, the following is described herein: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A wound dressing containing a polymer component selected from the group consisting of the following.

[0005] In some embodiments, (i) a first adduct and (ii) a polyethyleneimine intermediate or a second adduct are prepared separately and then mixed to form a polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite. In some embodiments, the polymer component is antibacterial against one or both of Gram-negative and Gram-positive bacterial strains. In some embodiments, the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:1. In some embodiments, the outer layer of the wound dressing contains the polymer component. In some embodiments, the polymer component is impregnated into the wound dressing. In some embodiments, the wound dressing is selected from the group consisting of wraps, covers, barriers, layers, packings, gauze, plasters, bandages, lints, sutures, films, foam products, hydrogels, hydrocolloids, alginate products, bioactive products, tissue manipulation skin substitutes, medicinal products, liquid bandages, smart dressings, and composites, or any combination thereof. In some embodiments, the wound dressing is configured to provide indication of one or more parameters related to the condition of the wound site.

[0006] In another embodiment, what is described herein is: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A topical preparation containing, The polyethyleneimine intermediate is a topical formulation having a total quaternary amine to total hydroxyl group ratio of at least 1:1.

[0007] In some embodiments, the topical formulation may be in the form of a cream, gel, paste, foam, spray, powder, emulsion, liquid, or ointment. In some embodiments, the polymer component is antibacterial against one or both of Gram-negative and Gram-positive bacterial strains.

[0008] In another aspect, the foregoing describes a method for preventing or reducing bacterial growth or reducing infection in a wound, surgical site, or implant, wherein the method involves applying the following to the wound, surgical site, or implant: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method involves applying or coating a composition containing the following.

[0009] In another aspect, the Specified herein describes a method for treating a wound or surgical site in a person in need, wherein the wound or surgical site is (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method involves applying a composition containing [the specified substance].

[0010] In another embodiment, the foregoing describes a method for promoting the healing of a wound or surgical site in a person who needs to do so, wherein the wound or surgical site is (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method involves applying a composition containing [the specified substance].

[0011] In some embodiments, the wound is an external wound. In some embodiments, the wound is an internal wound. In some embodiments, the method is part of an acute wound care regimen. In some embodiments, the method is part of a chronic wound care regimen. In some embodiments, the wound is infected. In some embodiments, the wound is not infected.

[0012] In another embodiment, the method described herein is for protecting a wound site in an area where such protection is needed, comprising covering at least a portion of the wound site with a covering material, and protecting the wound site (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method involves contacting a composition containing the substance.

[0013] In another embodiment, what is described herein is a method for preventing or reducing infection in a subject where such prevention or reduction is necessary, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprises administering a composition containing [a certain substance].

[0014] In another embodiment, the foregoing describes a method for treating an infection in a subject in need, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprises administering a composition containing [a certain substance].

[0015] In some embodiments, the infection is localized. In some embodiments, the infection is systemic.

[0016] In another embodiment, the foregoing describes a method for treating sepsis in a subject in need, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprises administering a composition containing [a certain substance].

[0017] In another embodiment, the foregoing describes a method for preventing or reducing necrosis in an object in need, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites comprising a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent, (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprises administering a composition containing [a certain substance].

[0018] In some embodiments, the subject is human or animal. In some embodiments, the composition is antibacterial against one or both of Gram-negative and Gram-positive bacterial strains. In some embodiments, the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:1.

[0019] In some embodiments, the polyethyleneimine intermediate comprises a reaction product of a reagent comprising polyethyleneimine and an alkylating agent. In some embodiments, the reagent further comprises a monoepoxide or a lactone. In some embodiments, the monoepoxide or lactone is -(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with hydroxy, C1-C6 alkoxy, C6-C 10 aryl optionally substituted with a substituent selected from carboxy, and C1-C6 alkyl optionally substituted with a substituent selected from carboxy. In some embodiments, the monoepoxide is a C1-C6 alkyloxirane. In some embodiments, the C1-C6 alkyl epoxide is selected from the group consisting of methyloxirane, ethyloxirane, propyloxirane, and butyloxirane. In some embodiments, the polyethyleneimine intermediate comprises a reaction product of a reagent comprising polyethyleneimine, a monoepoxide, and optionally, an alkylating agent, the monoepoxide being substituted with -(C1-C6 alkylene)-N + (R 20 )3X - , each R 20 being independently selected from the group consisting of C1-C 18 alkyl; C1-C 18 heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N; and C6-C 10 aryl optionally substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl), each X - being independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organic substituted derivatives thereof. In some embodiments, the alkylating agent is one or more R 21-Includes LG, in the formula, each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 The alkylating agent is selected from C1-C6 alkyl groups that may be substituted with substituents selected from aryl groups and -OH-(C1-C6 alkoxy), where each LG is a leaving group. In some embodiments, the alkylating agent is phenacyl halogenate, benzyl halogenate, or hexyl halogenate.

[0020] In some embodiments, the reagent for the reaction product contained in the polyethyleneimine intermediate further comprises a monoisocyanate. In some embodiments, the monoisocyanate comprises one or more R 30 -Includes NCO, in the formula, each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a These are independently C1-C6 alkyl groups, and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3. In some embodiments, the monoisocyanate includes octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0021] In some embodiments, polyethyleneimine has a molecular weight of about 300 to about 270,000 daltons. In some embodiments, polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons. In some embodiments, polyethyleneimine has a molecular weight of about 25,000 to about 120,000 daltons. In some embodiments, polyethyleneimine is branched. In some embodiments, polyethyleneimine is hyperbranched. In some embodiments, polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:2:1 to about 1:1:1. In some embodiments, polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:1:0.7. In some embodiments, polyethyleneimine intermediates are TIFF2026514865000002.tif131130, and one or more copolymers or blends of any two or more of them, in the formula, Each Y 3 These are independently H or -OY 2 And, Each Y 2 These are independently H or -C(O)-NHR 30 And, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 Independently, hydrogen;-N + (R 20 )3X - ,-(C6-C 10 C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl 10 Selected from aryl, and carboxyl, each R 20 It is independently, C1-C 18Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, each X -These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. however, R 10 However, -(C6-C 10 -(C1-C6 alkoxy), -(C1-C6 alkoxy), -(C1-C6 alkyl), which may be substituted with -(aryl) and -OH. 10 If the polyethyleneimine intermediate is a C1-C6 alkyl group which may be substituted with substituents selected from aryl and carboxyl groups, then independently, Selected from TIFF2026514865000003.tif90128. In some embodiments, the polyethyleneimine intermediate is The filename is TIFF2026514865000004.tif36128. In the formula, each R 60 These are independently -OH and -N + (R 20 )3X - ,-(C1-C6 alkoxy),carboxy,-(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 It may be substituted with 1 to 3 substituents selected from aryl and -OH-(C1-C6 alkoxy) groups. 4 -(C1-C 18 Selected from alkyl groups, with at least one R 60 However, although it is substituted with -OH, all R 60 Less than 50% of it is substituted with -OH, Y 4 It either does not exist or is -C(O)-, Each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18Heteroalkyl; and - (C1-C6 alkyl), - (C1-C6 alkoxy), -C (O) O- (C1-C6 alkyl), -C (O) NH (C1-C6 alkyl), -C (O) N (C1-C6 alkyl) 2, or -OC (O)- (C1-C6 alkyl) may be substituted C6-C 10 Selected from the group consisting of aryl, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000, Each X - Is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and organic substitution derivatives thereof. In some embodiments, the polyethyleneimine intermediate is, TIFF2026514865000005.tif36128, Wherein each R 60 Is independently -OH, -N + (R 20 ) 3X - , - (C6-C 10 Aryl), -C (O) O (C1-C6 alkyl), and -C (O)-(C6-C 10 Aryl) may be substituted with 1 to 3 substituents selected from -Y 4 - (C1-C 18 Alkyl), at least one R 60 Is substituted with -OH, but less than 50% of all R 60 Is substituted with -OH, Y 4 Is absent or -C (O)-, Each R 20 Is independently selected from the group consisting of C1-C6 alkyl, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000, Each X -These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. Several embodiments, each R 60 It may be independently substituted with -OH -(C1-C 18 Selected from alkyl groups, with at least one R 60 However, although it is substituted with -OH, all R 60 Less than 50% of it is substituted with -OH.

[0022] In some embodiments, the polyethyleneimine intermediate is selected from the group consisting of: TIFF2026514865000006.tif218166* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000007.tif36128, and B is, TIFF2026514865000008.tif34128, where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100. In some embodiments, one or more bromide anions are X independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. - It has been replaced with.

[0023] In some embodiments, the polyethyleneimine intermediate is selected from the group consisting of: TIFF2026514865000009.tif218150* indicates the molecular weight of the polyethyleneimine precursor. Unless otherwise indicated, based on the stoichiometric ratio of theoretical chemistry (based on the amounts of reactants used in the synthesis protocol) In the table, A is TIFF2026514865000010.tif35128, and B is TIFF2026514865000011.tif34128, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100, and each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and their organic substituted derivatives.

[0024] In some embodiments, at least 20% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized.

[0025] In some embodiments, the polymer component is a polyethyleneimine intermediate.

[0026] In some embodiments, the first quaternary ammonium salt has the chemical structure of TIFF2026514865000012.tif17128, wherein R 1 is -(C8-C 30 alkyl), -(C8-C 30 heteroalkyl), -(C8-C 30 heteroalkyl)-(C6-C 10 aryl), -(C6-C 10 aryl), -(C6-C 10 aryl)-(C8-C 30 alkyl), -(C6-C 10 aryl)-(C8-C 30 heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q )y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 Selected from the group consisting of H-, -(C8-C 30 Heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C8-C 30 A heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. R 2 -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel), -(C6-C 10 Aryl)-(C1-C4 alkyl),-(C6-C 10 Aryl)-(C1-C4 heteroalkyl);-(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -Selected from the group consisting of H, -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The aryl)-(C1-C4 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si. R 3 is, -(C1-C 30 Alkyl), -(C1-C 30 Heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10Ariel), -(C6-C 10 Ariel), -(C6-C 10 Ariel)-(C1-C 30 Alkyl), -(C6-C 10 Ariel)-(C1-C 30 Heteroalkyl), -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m R n ) x31 -W 31 -(CR p R q ) y31 -Selected from the group consisting of H, -(C1-C 30 Heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C1-C 30 A heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. A is -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m R n ) x40 -W 40 -(CR p R q ) y40 -, and -(CR m R n ) x41 -W 41 -(CR p R q ) y41 - is a linking group selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m , R n , R p , and R q These are independently selected from H and C1-C4 alkyl groups. W 10 , W 20 , W 30 , and W 40 These are independently selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 11 , W 21 , W 31 , and W 41 These are independently 5-6 member cycloalkyl, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x10 is an integer between 1 and 30, y10 is an integer between 0 and 29, and 8 ≤ (x10 + y10) ≤ 30. x11 is an integer between 1 and 30, y11 is an integer between 0 and 29, and 8 ≤ (x11 + y11) ≤ 30. x² is an integer between 1 and 4, y² is an integer between 0 and 3, and x² + y² ≤ 4. x²⁻¹ is an integer between 1 and 4, y²⁻¹ is an integer between 0 and 3, and x²⁻¹ + y²⁻¹ ≤ 4. x30 is an integer between 1 and 30, y30 is an integer between 0 and 29, and x30 + y30 ≤ 30. x31 is an integer between 1 and 30, y31 is an integer between 0 and 29, and x31 + y31 ≤ 30. x40 is an integer between 1 and 19, y40 is an integer between 1 and 19, and 3 ≤ (x40 + y40) ≤ 20. x41 is an integer between 1 and 20, y41 is an integer between 0 and 19, and 3 ≤ (x41 + y41) ≤ 20. Y is -OH, -NHR 4 -SH, -CO2H, -C(O)NHR 4 -C(S)NHR 4 , Selected from the group consisting of TIFF2026514865000013.tif23128, Each R 4 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives.

[0027] In some embodiments, R 1 is, -(C 12 -C 30 Alkyl), -(C 12 -C30 Heteroalkyl), -(C 12 -C 30 Alkyl)-(C6-C 10 Ariel), -(C 12 -C 30 Heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel)-(C 12 -C 30 Alkyl), and -(C6-C 10 Ariel)-(C 12 -C 30 Selected from the group consisting of heteroalkyls, -(C 12 -C 30 Heteroalkyl), -(C 12 -C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C 12 -C 30 The heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 These are -(C1-C4 alkyl), -(C1-C4 heteroalkyl), and -(C1-C4 alkyl)-(C6-C 10 (aryl), -(C1-C4 heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Aryl)-(C1-C4 alkyl), and -(C6-C 10 Selected from the group consisting of aryl)-(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The aryl)-(C1-C4 heteroalkyl) has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 and R 3 At least one of them is -(C1-C4 alkyl). In some embodiments, R 2 and R 3 is methyl. In some embodiments, A is -(CH2)m -or-(CH2CHR 5 -O-) n -CH2CHR 5 - is an integer between 2 and 20, where m is an integer between 0, 1, 2, 3, 4, or 5, and each R 5 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, in the formula -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 5 is H or methyl. In some embodiments, the first quaternary ammonium salt is TIFF2026514865000014.tif53128, or a combination of two or more of these. In some embodiments, the first quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 1% to about 50% by weight.

[0028] In some embodiments, the first polyfunctional crosslinking agent is a bifunctional crosslinking agent. In some embodiments, the bifunctional crosslinking agent is a diisocyanate. In some embodiments, the diisocyanate is selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the second polyfunctional crosslinking agent, if present, is a second polyisocyanate, and the third polyfunctional crosslinking agent, if present, is a third polyisocyanate, and the second and third polyisocyanates are different. In some embodiments, the second polyfunctional crosslinking agent, if present, is the second polyisocyanate, and the third polyfunctional crosslinking agent, if present, is the third polyisocyanate, and the second and third polyisocyanates are the same. In some embodiments, the first polyfunctional crosslinking agent is the first polyisocyanate, the second polyfunctional crosslinking agent, if present, is the second polyisocyanate, and the third polyfunctional crosslinking agent, if present, is the third polyisocyanate, and the first, second, and third polyisocyanates are different. In some embodiments, the first polyfunctional crosslinking agent is the first polyisocyanate, the second polyfunctional crosslinking agent, if present, is the second polyisocyanate, and the third polyfunctional crosslinking agent, if present, is the third polyisocyanate, and the first, second, and third polyisocyanates are the same. In some embodiments, each of the first, second, and third polyisocyanates has an average isocyanate functional value of 2 to 5. In some embodiments, each of the first, second, and third polyisocyanates has an average isocyanate functional value of 3 to 4.In some embodiments, each of the first, second, and third polyisocyanates is prepared from a diisocyanate independently selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates. In some embodiments, the first adduct has an average isocyanate functional value of 2 to 3. In some embodiments, the first adduct has an average isocyanate functional value of about 2.05 to about 2.3. In some embodiments, the first polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 2% to about 25% by weight. In some embodiments, the second polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or polymer component (4) in an amount of about 0.1% to about 10% by weight. In some embodiments, the third polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 0.1% to about 20% by weight.

[0029] In some embodiments, the polyol is selected from the group consisting of polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, any two or more copolymers thereof, and any two or more combinations thereof. In some embodiments, the polyol is selected from the group consisting of poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol). In some embodiments, the polyol has a weight-average molecular weight of about 300 to about 3000. In some embodiments, the polyol has a weight-average molecular weight of about 400 to about 2000. In some embodiments, the polyol has a weight-average molecular weight of about 600 to about 1500. In some embodiments, the polyol is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 1% to about 40% by weight.

[0030] In some embodiments, polymer component (1) comprises (vi) a first polyfunctional crosslinking agent and a second quaternary ammonium salt. Further including a third adduct of TIFF2026514865000015.tif17128, in the formula, R 1a , R 2a , and R 3a These are, independently, -(C1-C 20 Alkyl), -(C1-C 20 Alkyl)-(C6-C 10 (aryl), or -(C6-C) 10 Ariel)-(C1-C 20 It is alkyl, A 1 is, -(C3-C 20 Alkylene)-,-(C3-C 20Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 , and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 - is a linking group selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m1 , R n1 , R p1 , and R q1 These are independently selected from H and C1-C4 alkyl groups. W 42 It is selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 43 These are 5-6 member cycloalkyl groups, C6-C 10Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x42 is an integer between 1 and 19, y42 is an integer between 1 and 19, and 3 ≤ (x42 + y42) ≤ 20. x43 is an integer between 1 and 20, y43 is an integer between 0 and 19, and 3 ≤ (x43 + y43) ≤ 20. Y 1 -OH, -NHR 4a -SH, -CO2H, -C(O)NHR 4a -C(S)NHR 4a , Selected from the group consisting of TIFF2026514865000016.tif23128, Each R 4a These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives. In some embodiments, R 1a , R 2a , and R 3aAt least one of them is -(C1-C4 alkyl). In some embodiments, R 1a , R 2a , and R 3a Two of them are -(C1-C4 alkyl).

[0031] In some embodiments, polymer component (1) is (vi) a fourth polyfunctional crosslinking agent and a second quaternary ammonium salt Further including a third adduct of TIFF2026514865000017.tif17128, in the formula, R 1a , R 2a , and R 3a These are, independently, -(C1-C 20 Alkyl), -(C1-C 20 Alkyl)-(C6-C 10 (aryl), or -(C6-C) 10 Ariel)-(C1-C 20 It is alkyl, A 1 is, -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 , and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 - is a linking group selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m1 , R n1 , R p1 , and R q1 These are independently selected from H and C1-C4 alkyl groups. W 42 It is selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 43 These are 5-6 member cycloalkyl groups, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x42 is an integer between 1 and 19, y42 is an integer between 1 and 19, and 3 ≤ (x42 + y42) ≤ 20. x43 is an integer between 1 and 20, y43 is an integer between 0 and 19, and 3 ≤ (x43 + y43) ≤ 20. Y 1 -OH, -NHR 4a -SH, -CO2H, -C(O)NHR 4a -C(S)NHR 4a , Selected from the group consisting of TIFF2026514865000018.tif23128, Each R 4a These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives. In some embodiments, R 1a , R 2a , and R 3a At least one of them is -(C1-C4 alkyl). In some embodiments, R 1a , R 2a , and R 3a Two of them are -(C1-C4 alkyl).

[0032] In some embodiments, the fourth polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 0.1% to about 15% by weight. In some embodiments, the fourth polyfunctional crosslinking agent is different from the first polyfunctional crosslinking agent, and if present, the second polyfunctional crosslinking agent, and if present, the third polyfunctional crosslinking agent. In some embodiments, the fourth polyfunctional crosslinking agent is a fourth polyisocyanate. In some embodiments, the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0033] In some embodiments, the second quaternary ammonium salt is The reference is TIFF2026514865000019.tif26128. In some embodiments, the second quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 1% to about 15% by weight. In some embodiments, the third adduct has an average isocyanate functional value of 2 to 3. In some embodiments, the third adduct has an average isocyanate functional value of about 2.05 to about 2.3. In some embodiments, the third adduct is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 2% to about 30% by weight.

[0034] In some embodiments, the polyethyleneimine intermediate is present in the polymer, copolymer, or interpermeable polymer network of polymer component (1), (3), or (4) in an amount of about 0.1% to about 50% by weight. In some embodiments, the second adduct is present in the polymer, copolymer, or interpermeable polymer network of polymer component (1) or (4) in an amount of about 1% to about 30% by weight.

[0035] In some embodiments, the water-soluble polymer is crosslinked with (a) a first polyfunctional crosslinking agent incorporated into a first adduct, (b) a second polyfunctional crosslinking agent incorporated into a second adduct, if present, (c) a third polyfunctional crosslinking agent, if present, or (d) any combination of two or more of these. In some embodiments, the water-soluble polymer is selected from the group consisting of hydroxyethylcellulose (HEC), hydroxypropylcellulose, polyvinyl alcohol, poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), polyacrylamide, polyethyleneimine intermediates, copolymers of two or more of these, copolymers of one or more of these with polyvinylpyrrolidone poly(glycidyl acrylate) or poly(glycidyl methacrylate), and combinations or blends of two or more of these. In some embodiments, the water-soluble polymer is hydroxyethylcellulose or a hydrophobic modified derivative thereof. In some embodiments, the water-soluble polymer is another polyethyleneimine intermediate. In some embodiments, the water-soluble polymer is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 0.5% to about 15% by weight. In some embodiments, polymer components (1) and (2) are HO-(C n H 2n )-OH and HO-(C n H2n-2 The formula further comprises a chain extender selected from the group consisting of )-OH or combinations thereof, where n is an integer from 2 to 8. In some embodiments, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more of these. In some embodiments, the chain extender is present in the polymer component in an amount of about 0.5% to about 10% by weight.

[0036] In some embodiments, the polymer component is a third quaternary ammonium salt Further including TIFF2026514865000020.tif17128, in the formula, R 1a , R 2a , and R 3a These are independently methyl or ethyl, A 2 is, -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 , and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -Selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m1 , R n1 , R p1 , and R q1 These are independently selected from H and C1-C4 alkyl groups. W 42 It is selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 43 These are 5-6 member cycloalkyl groups, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x42 is an integer between 1 and 19, y42 is an integer between 1 and 19, and 3 ≤ (x42 + y42) ≤ 20. x43 is an integer between 1 and 20, y43 is an integer between 0 and 19, and 3 ≤ (x43 + y43) ≤ 20. Y 1a H is, Each R 4a These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives.

[0037] In another aspect, this specification describes a method for preparing a wound dressing as described herein, wherein a composition comprising a polymer component is used. (i) spraying the composition onto a fibrous material, (ii) Immersing a fibrous material in a fluid containing the composition, (iii) Impregnating the fibers of a fibrous material with a fluid containing the composition, (iv) Applying a coating layer containing the composition to the surface of a fibrous material, (v) Adhering a backing material containing the composition to a fibrous material, (vi) Applying microneedles containing the composition to a fibrous material, (vii) embedding a layer containing the composition within a fibrous material, (viii) constructing fibers of a fibrous material containing a composition by electrospinning, (ix) Interleaving fibers containing the composition with fibers of a fibrous material. The method involves integrating into a fibrous material by one of the following means.

[0038] In another embodiment, the foregoing provides a method for producing a polyurethane foam wound dressing, comprising integrating a composition containing polymer components into a polyurethane foam wound dressing by mixing the composition with polyurethane before curing.

[0039] In another embodiment, the polymers described herein are those having wound-healing properties, comprising a polyethyleneimine intermediate, wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:1. In some embodiments, the polymers are selected from the group consisting of: TIFF2026514865000021.tif218166* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000022.tif36128, and B is, TIFF2026514865000023.tif34128, where each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100. In some embodiments, one or more bromide anions are X independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. - It is replaced by: In some embodiments, the polymer is selected from the group consisting of: TIFF2026514865000024.tif218150* indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) ***Actual stoichiometric ratio determined by NMR analysis In the table, A is, The filename is TIFF2026514865000025.tif35128, and B is, The file is TIFF2026514865000026.tif34128, where each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100, and each X -These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. [Brief explanation of the drawing]

[0040] [Figure 1A] SEM images of a control S. aureus biofilm are shown. [Figure 1B] As discussed in Example 4, SEM images of S. aureus biofilms treated with the compounds disclosed herein (100 μM) are shown. [Figure 2A] Figures 2A and 2B show the quantitative analysis of the activity of the compounds disclosed herein (25 μM) over time on S. aureus biofilms using SYTO 9 staining or propidium iodide staining, respectively. All time points were compared to the control (0 hour) using one-way ANOVA followed by Bonferroni's multiple comparison test. *p=0.01, **p=0.001, ***p=0.0001, ****p=<0.0001. Mean (±SEM) of the data shown, n=3. [Figure 2B] See the explanation in Figure 2A. [Figure 3A] Figures 3A and 3B show the quantitative analysis of the activity of the compounds disclosed herein at various concentrations (6.25, 12.5, 25, 50, and 100 μM) on S. aureus biofilms using SYTO 9 staining or propidium iodide staining, respectively. All concentrations were compared to the control (0 μM) using one-way ANOVA followed by Bonferroni's multiple comparison test. *p=0.01, **p=0.001, ***p=0.0001, ****p=<0.0001. Mean (±SEM) of the data shown, n=3. [Figure 3B] See the explanation in Figure 3B. [Figure 4A] Figures 4A and 4B show non-specific examples of adhesive bandages. [Figure 4B]See the explanation in Figure 4A. [Figure 4C] This shows a non-limiting example of a foam product in the form of a pad. [Figure 5] This paper presents a study design for efficacy research in a mouse model of Staphylococcus aureus-induced wound infection. [Figure 6A] Figures 6A and 6B show the in vivo antimicrobial efficacy of the two compounds disclosed herein in a mouse wound infection model at 72 and 96 hours, respectively, after seeding. S. aureus NRS384 was seeded at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL. The concentration used is shown on the x-axis. Total bacteria from the wound were counted on a TSA plate. Individual symbols represent biological replication (mouse, n=3). Bar plots represent the mean ± SEM for each group. Limit of detection (LOD) of CFU set to 1 Log CFU (1, Log) on ​​a spread plate. For statistical comparison, all treatment groups were compared to the control bacteria or antibiotic control (vancomycin) group using standard one-way ANOVA followed by Dunnett's multiple comparison test. ****p<0.0001. [Figure 6B] See the explanation in Figure 6A. [Figure 7A] Figures 7A and 7B show the in vivo antimicrobial efficacy of the two compounds disclosed herein in a mouse wound infection model 24 and 72 hours after seeding, respectively. S. aureus NRS384 was seeded at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL, and the concentration used is shown on the x axis. Total bacteria from wounds on TSA plates were counted at (A) 24 hours and (B) 72 hours after treatment. Individual symbols represent biological replication (mouse, n=5). Bar plots and lines represent the mean ± sem for each group. Limit of detection (LOD) of CFU set to 1 Log CFU (1, Log) on ​​spread plates. For statistical comparison, all treatment groups were compared to the control bacterial group using standard one-way ANOVA followed by Dunnett's multiple comparison test. **p<0.005, ***p<0.001, ****p<0.0001. [Figure 7B]See the explanation in Figure 7A. [Figure 8A] Figures 8A and 8B show the in vivo antimicrobial efficacy of the two compounds disclosed herein in a mouse wound infection model 72 hours after seeding. S. aureus NRS384 was seeded at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL, and the concentration used is shown on the x axis. At 72 hours post-treatment, the total bacteria from the wounds on TSA plates were counted. Individual symbols represent biological replication (mouse, n=5). Bar plots and lines represent the mean ± sem for each group. Limit of detection (LOD) of CFU set to 1 Log CFU (1, Log) on ​​spread plates. For statistical comparison, all treatment groups were compared to the control bacterial group using standard one-way ANOVA followed by Dunnett's multiple comparison test. ns = not significant. *p<0.01, **p<0.005, ***p<0.001, ****p<0.0001. [Figure 8B] See the explanation in Figure 8A. [Figure 9] This study demonstrates the in vivo antimicrobial efficacy of two compounds disclosed herein in a mouse wound infection model 7 days post-treatment. S. aureus NRS384 was seeded at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL, with the concentration used shown on the x-axis. Total bacteria from wounds on TSA plates were counted 7 days post-treatment. Individual symbols represent biological replication (mouse, n=5). Bar plots and lines represent the mean ± sem for each group. Limit of detection (LOD) of CFU set to 1 Log CFU (1, Log) on ​​spread plates. For statistical comparison, all treatment groups were compared to the control bacterial group using standard one-way ANOVA followed by Dunnett's multiple comparison test. ****p<0.0001. ns=not significant. [Figure 10]This document demonstrates the in vivo antimicrobial efficacy of the two compounds disclosed herein in a mouse wound infection model 24 hours after inoculation and treatment. S. aureus NRS384 was inoculated at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL, with the concentration used shown on the x-axis. Total bacteria from wounds on TSA plates were counted 24 hours post-treatment. Individual symbols represent biological replication (mouse, n=3). Bar plots and lines represent the mean ± sem for each group. The dotted line indicates the limit of detection (LOD) of CFU, set to 1 Log CFU (1, Log) on ​​a spread plate. The efficacy of the same test compounds was compared with that of male BALB / c mice using female BALB / c mice from the same group from the pilot study shown in Figure 7A. For statistical comparison, both groups were compared across all groups using two-way ANOVA followed by Tukey's multiple comparison test. ns = not significant. ****p<0.0001. There was no statistically significant difference in the antibacterial efficacy of either compound between male BALB / c mice and female BALB / c mice. [Figure 11A] Figures 11A and 11B show the antimicrobial efficacy of the compounds disclosed herein in a dressing loaded with HYDROFIBER®. S. aureus NRS384 was seeded at 1 × 10⁵ CFU / wound. Treatment was applied in a total volume of 10 μL, and the concentration used is shown on the x-axis. (A) Total bacteria counted on TSA and (B) CHROMagar® Staph aureus (CHROMO). Individual symbols represent biological replication (n=3 mice). Mean ± SEM for each group. Limit of detection (LOD) of CFU set at 10 CFU (1, Log) for TSA and 100 CFU (2, Log) for CHROMO, as shown by the red dotted line. Control group = no bacteria. For statistical comparison, all treatment groups were compared to the "bacteria only" group using standard one-way ANOVA followed by Dunnett's multiple comparison test. *p<0.01, **p<0.005, ****p<0.0001. [Figure 11B] See the explanation in Figure 11A. [Figure 12]This indicates the percentage of wound area remaining up to 9 days after wound treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 13] This indicates the percentage of wound area remaining up to 9 days after wound treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 14] The percentage of wound closure by shrinkage up to 9 days post-wound treatment is shown after treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 15] This shows the percentage of wound closure by re-epithelialization up to 9 days post-wound treatment after treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 16] The percentage of wound closure by shrinkage up to 9 days post-wound treatment is shown after treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 17] This shows the percentage of wound closure by re-epithelialization up to 9 days post-wound after treatment with various concentrations of the compounds disclosed herein or with the vehicle. [Figure 18] The MICs of the selective compounds disclosed herein against a range of wound bacteria (Gram-positive or Gram-negative) are shown. For each trio of bars, compound 32-1 is represented by the left bar, compound 32-1A by the middle bar, and compound 32-1B by the right bar. *p<0.01, **p<0.005, ***p<0.001, ****p<0.0001. [Figure 19A] Figures 19A and 19B show the MICs of the selective compounds disclosed herein against a range of wound bacteria (Gram-positive or Gram-negative). For each set of bars, A = compound 32-2, B = compound 32-2A, C = compound 32-2B, D = compound 32-2C, E = compound 32-2D, F = compound 32-2E. *p<0.01, **p<0.005, ***p<0.001, ****p<0.0001. [Figure 19B] See the explanation in Figure 19A. [Figure 20]This shows the dose-dependent inhibition zone against methicillin-resistant Gram+VE (NRS384 / MRSA) bacteria using compound-impregnated wound dressings. ****p<0.0001. [Figure 21] This shows the dose-dependent inhibition zone against methicillin-resistant Gram+VE (NRS384 / MRSA) bacteria using compound-impregnated wound dressings. ****p<0.0001. [Modes for carrying out the invention]

[0041] Detailed explanation In the following description, many specific details are provided for illustrative purposes to ensure a thorough understanding of the technology. However, it may be apparent that the technology can be implemented without these specific details. To provide a substantial understanding of the technology, please understand that specific aspects, modes, embodiments, variations, and features of the technology are described below at varying levels of detail.

[0042] definition For convenience, the meanings of some terms and phrases used in this specification, the examples, and the appended claims are provided below. Unless otherwise stated or implied by the context, the following terms and phrases have the meanings provided below. The definitions are provided to aid in describing specific embodiments and are not intended to limit the subject matter claimed. Unless otherwise expressly stated, all technical and scientific terms used herein have the same meanings as commonly understood by those skilled in the art. In the event of any apparent conflict between the use of a term in the art and its definition provided herein, the definition provided herein shall prevail.

[0043] As used herein and in the appended claims, the singular forms "a," "an," and "the" include multiple references unless otherwise explicitly indicated by their content. For example, a reference to "a cell" includes a combination of two or more cells, etc.

[0044] Where used herein, the terms “approximately” or “about” with respect to a value or parameter are generally interpreted to include a number that falls within the range of 5%, 10%, 15%, or 20% (greater than or less than) of the possible value, unless otherwise stated or the context makes clear (except when such a number is less than 0% or greater than 100%). A reference to “approximately” or “about” a value or parameter includes (and describes) embodiments relating to that value or parameter. For example, a reference to “about X” includes a description of “X.”

[0045] As used herein, the term "or" means "and / or". In phrases such as "A and / or B" as used herein, the term "and / or" is intended to include both A and B, A or B, A (alone), and B (alone). Similarly, the term "and / or" in phrases such as "A, B and / or C" is intended to encompass each of the following embodiments: A, B, and C; A, B, or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone).

[0046] As used herein, the term “includes” means that, in addition to the defined elements presented, other elements may also be present. The use of “includes” indicates inclusion, not limitation.

[0047] The term "consisting of" refers to the compositions, methods, and their respective components described herein, excluding any elements not listed in the description of the embodiments.

[0048] As used herein, the term “essentially derived from” refers to elements necessary for a given embodiment. The term permits the presence of additional elements that do not substantially affect the basic and novel or functional features of that embodiment of the Art.

[0049] As used herein, “aryl” refers to a fully aromatic carbocyclic (all-carbon) ring. An “aryl” group may consist of two or more fused rings (rings sharing two adjacent carbon atoms). If the aryl group is a fused ring system, the ring connected to the rest of the molecule is fully aromatic. Other rings in the fused ring system may or may not be fully aromatic. Examples of aryl groups include, but are not limited to, the radicals of benzene, naphthalene, and azulene.

[0050] As used herein, “alkyl” refers to a hydrocarbon group that is fully saturated (without double or triple bonds) in a linear or branched chain. The alkyl groups of the compounds disclosed herein may contain 1 to 15 carbon atoms. The alkyl groups herein may have 1 to 4 carbon atoms, 1 to 5 carbon atoms, 1 to 6 carbon atoms, 1 to 7 carbon atoms, 1 to 8 carbon atoms, 1 to 9 carbon atoms, 1 to 10 carbon atoms, 1 to 11 carbon atoms, 1 to 12 carbon atoms, 1 to 13 carbon atoms, 1 to 14 carbon atoms, or 1 to 15 carbon atoms. As used herein, for example, C1-C6 alkyl represents an alkyl group having 1 to 6 carbon atoms, C1-C4 alkyl represents an alkyl group having 1 to 4 carbon atoms, and C1-C3 alkyl represents an alkyl group having 1 to 3 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, amyl, t-amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0051] As used herein, “alkoxy” refers to the alkyl group as defined above, which is attached to the parent molecule via an oxy group (-O-). As used herein, C1-C6 alkoxy refers to an alkoxy group containing 1 to 6 carbon atoms, and C1-C3 alkoxy refers to an alkoxy group containing 1 to 3 carbon atoms. Typical examples of alkoxys include, but are not limited to, methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy.

[0052] As used herein, "cycloalkyl" means, in some embodiments, a group of 3 to 14 carbon atoms (e.g., C3-C3-C3). 14 Cycloalkyl groups, or groups of 3 to 10 carbon atoms (e.g., C3-C 10 This refers to monocyclic, bicyclic, or polycyclic hydrocarbon ring systems having 3 to 8 carbon atoms (e.g., C3-C8 cycloalkyl), 3 to 6 carbon atoms (e.g., C3-C6 cycloalkyl), or 5 to 6 carbon atoms (e.g., C5-C6 cycloalkyl). Cycloalkyl groups may be saturated or characterized by one or more unsaturated points (i.e., carbon-carbon double and / or triple bonds), provided that the unsaturated points do not result in an aromatic system. Examples of monocyclic cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexeneyl, cyclohexylyl, cycloheptyl, cyclohepteneyl, cycloheptadieneyl, cyclooctyl, cycloocteneyl, and cyclooctadieneyl. The rings of bicyclic and polycyclic cycloalkyl groups can be condensed, crosslinked, or spirocyclic.

[0053] As used herein, unless otherwise specified, “heteroalkyl” refers to an alkyl group as defined herein in which one or more of its constituent carbon atoms are replaced by nitrogen, oxygen, sulfur, or silicon. Typical examples of heteroalkyl groups are alkoxys. Heteroalkylenes are divalent heteroalkyl groups.

[0054] As used herein, unless otherwise specified, the term “heteroaryl” means, in some embodiments, a monocyclic or fused bicyclic aromatic group (or ring) having 5 to 14 (i.e., 5 to 14-membered heteroaryl), 5 to 10 (i.e., 5 to 10-membered heteroaryl), or 5 to 6 (i.e., 5 to 6-membered heteroaryl) members (i.e., ring vertices) and containing 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1 heteroatom selected from nitrogen (N), oxygen (O), and sulfur (S). Heteroaryl groups can be attached to the rest of a molecule through the carbon atoms or heteroatoms of the heteroaryl group, if chemically permissible. Non-exclusive examples of heteroaryl groups include pyridyl, pyridadinyl, pyrazinyl, pyrimindinyl, triazinyl, purinyl, thienopyridinyl, thienopyrimidinyl, pyrazolopyrimidinyl, pyrazolopyridinyl, imidazopyridine, isothiazolyl, pyrazolyl, indazolyl, pteridinyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiadiazolyl, pyrrolyl, thiazolyl, furyl, and thienyl.

[0055] The term "heterocycloalkyl" refers, in some embodiments, to a non-aromatic monocyclic, bicyclic, or polycyclic cycloalkyl ring having 3 to 14 members (e.g., a 3 to 14-membered heterocycle), or 3 to 10 members (e.g., a 3 to 10-membered heterocycle), or 3 to 8 members (e.g., a 3 to 8-membered heterocycle), or 3 to 6 members (e.g., a 3 to 6-membered heterocycle), or 5 to 6 members (e.g., a 5 to 6-membered heterocycle), and having 1 to 5, 1 to 4, 1 to 3, 1 to 2, or 1 heteroatom selected from nitrogen (N), oxygen (O), sulfur (S), and silicon (Si). A heterocycloalkyl group is saturated or characterized by one or more unsaturated points (e.g., one or more carbon-carbon double bonds, carbon-carbon triple bonds, carbon-nitrogen double bonds, and / or nitrogen-nitrogen double bonds), provided that the unsaturated points do not result in an aromatic system. The rings of bicyclic and polycyclic heterocycloalkyl groups can be condensed, crosslinked, or spirocyclic. Non-limiting examples of heterocycloalkyl groups include aziridine, oxirane, thiirane, pyrrolidine, imidazolidine, pyrazolidine, dioxolane, phthalimide, piperidine, 1,4-dioxane, morpholine, thiomorpholine, thiomorpholine-S-oxide, thiomorpholine-S,S-oxide, piperazine, 3,4,5,6-tetrahydropyridazine, tetrahydropyran, pyran, decahydroisoquinoline, 3-pyrroline, thiopyran, tetrahydrofuran, tetrahydrothiophene, and quinuclidine. Heterocycloalkyl groups can be attached to the rest of the molecule through ring carbon atoms or ring heteroatoms, if chemically acceptable.

[0056] Where used herein, unless otherwise specified, “independently selected” means that each of the specified bases is independently selected from the list of subsequent species.

[0057] The terms "statistically significant" or "significantly significant" refer to statistical significance, which generally means a difference of two standard deviations (2SD) or more.

[0058] The terms “reduce,” “reduced,” “decrease,” and “inhibit” are all used herein to mean a reduction of a statistically significant amount. In some embodiments, “reduce,” “decrease,” or “decrease,” or “inhibit” typically mean a reduction of at least 10% compared to a reference level (e.g., the absence of a given treatment or drug), and may include reductions of, for example, at least about 10%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 65%, at least about 70%, at least about 75%, at least about 80%, at least about 85%, at least about 90%, at least about 95%, at least about 98%, at least about 99%, or greater. As used herein, “decrease” or “inhibit” does not include complete inhibition or reduction compared to a reference level. “Complete inhibition” is 100% inhibition compared to a baseline level. The reduction may preferably be reduced to a level that is acceptable as being within the normal range for a given non-disabled individual.

[0059] The terms “increased,” “enhance,” “strengthen,” or “activate” are all used herein to mean an increase of a statically significant amount. In some embodiments, the terms “increased,” “enhance,” or “activate” may mean an increase of at least 10% compared to a reference level, e.g., at least about 20%, or at least about 30%, or at least about 40%, or at least about 50%, or at least about 60%, or at least about 70%, or at least about 80%, or at least about 90%, or up to 100%, including 100%, or any increase between 10% and 100% compared to a reference level, or an increase of at least about 2 times, or at least about 3 times, or at least about 4 times, or at least about 5 times, or at least about 10 times compared to a reference level, or any increase between 2 times and 10 times or more. In the context of markers or symptoms, “increase” is a statistically significant increase of such a level.

[0060] As used herein, the term "polyisocyanate" generally refers to a family of polyisocyanates containing two or more isocyanate-reactive groups, including, but not limited to, DESMODUR® N3300 and N100 (produced by Covestro Deutschland AG in Leverkusen, Germany), which are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimers; DESMODUR® Z4470SN (produced by Covestro Deutschland AG in Leverkusen, Germany), which is a polyfunctional polyisocyanate based on IPDI (isophorone diisocyanate); WANNATE® T-series polyisocyanates, which are toluene diisocyanate (TDI)-based aromatic polyisocyanates; and LUPRANATE® M-series polyisocyanates, which are 4,4-diphenylmethane diisocyanate (MDI)-based aromatic polyisocyanates.

[0061] As used herein, the term “antimicrobial” is generally used to indicate that a composition or coating of a portion of a surface (e.g., a wound) kills at least a certain level of pathogenic bacteria. For example, antimicrobial may be used to indicate biosuppressive efficacy, a reduction in the bactericidal level (3-log, or 99.9%) in at least one organism, or a reduction in the disinfectant level (5-log, or 99.999%) in at least one organism, or sterilization (no detectable organisms). Pathogens, or microorganisms, may include any species of bacteria, viruses, fungi including molds and yeasts, or spores. Thus, antimicrobial as used herein includes antiviral, antibacterial, and antifungal properties.

[0062] The term "polymer" as used herein includes random polymers, alternating polymers, block polymers, and graft polymers. The term "copolymer" as used herein includes random copolymers, block copolymers, graft copolymers, interpolymer composites, interpenetrating networks, and blends thereof.

[0063] Where used herein, and unless otherwise specified, the term “weight %” has the usual meaning of the weight percentage (%) of a component in a chemical composition based on the total weight of the “as prepared” composition. For example, an aqueous composition containing 1 weight % of an amine “based on the total weight of the composition” is equivalent to a composition containing 99.0 grams of water and 1.0 gram of amine. Weight % in a composition indicates the weight % of the active substance unless otherwise specified. “As prepared” means that the written composition refers to what it is as added to a mixing vessel and does not refer to what the mixture may ultimately become after certain components react, such as through hydrolysis or polymerization.

[0064] As used herein, “subject” refers to an animal, such as a mammal (including a human), that has been or will be the object of treatment, observation, or experimentation. “Subject” and “patient” may be used interchangeably unless otherwise indicated. Mammals include, but are not limited to, mice, rodents, rats, monkeys, humans, farm animals, dogs, cats, sport animals, and pets. The methods described herein may be useful in human therapeutic and / or veterinary applications. In some embodiments, the subject is a mammal. In some embodiments, the subject is a human.

[0065] The term "therapeutically effective dose" refers to an amount of the compound sufficient to deliver a therapeutic effect when administered in one or more doses to a patient (e.g., a human) requiring such treatment as defined below. The therapeutically effective dose will vary depending on the patient, the disease being treated, the patient's weight and / or age, the severity of the disease or disability, or the method of administration as determined by a qualified prescriber or caregiver.

[0066] The terms “treatment (or processing)” or “to treat (or process)” mean administering any of the formulations disclosed herein for the following purposes: (i) delaying the onset of a disease / disorder, i.e., preventing the onset of the clinical symptoms of the disease / disorder or delaying the onset of the disease / disorder; (ii) inhibiting the disease / disorder, i.e., preventing the onset of the clinical symptoms; and / or (iii) alleviating the disease / disorder, i.e., causing regression of the clinical symptoms or their severity.

[0067] As used herein, the terms “dressing” or “wound dressing” include any type of wrap, cover, barrier, layer, packing, gauze, plaster, bandage, lint, suture, film, foam product, hydrogel, hydrocolloid, alginate product, bioactive product, tissue manipulation skin substitute, medicinal product, liquid bandage, or composite product (which may include two or more of the aforementioned products or substitute products). For example, such dressings may be used on or near the stratum corneum or other parts of the skin, or for internal wound healing. In some embodiments, dressings may be provided as an over-skin bandage (Figure 1A) or a foam pad (Figure 1B).

[0068] Unless otherwise defined herein, scientific and technical terms used in connection with this application shall have the meanings generally understood by those skilled in the art to which this disclosure belongs. It should be understood that the Art is not limited to the specific methodologies, protocols, and reagents described herein, and that these are subject to change. The technical terms used herein are for the sole purpose of describing specific embodiments and are not intended to limit the scope of the Art as defined solely by the claims. Definitions of common terms in immunology and molecular biology can be found below: The Merck Manual of Diagnosis and Therapy (2011), 19 thEdition, Published by: Merck Sharp & Dohme Corp. (ISBN 978 - 0 - 911910 - 19 - 3), The Encyclopedia of Molecular Cell Biology and Molecular Medicine, Robert S. Porter et al. (eds.), Published by: Blackwell Science Ltd., 1999 - 2012 (ISBN 9783527600908), Molecular Biology and Biotechnology: a Comprehensive Desk Reference (1995). Robert A. Meyers (ed.), Published by: VCH Publishers, Inc. (ISBN 1 - 56081 - 569 - 8), Immunology (2006). Werner Luttmann, Published by: Elsevier; Janeway’s Immunobiology (2014). Kenneth Murphy, Allan Mowat, Casey Weaver (eds.), Taylor & Francis Limited, (ISBN 0815345305, 9780815345305), Lewin’s Genes XI, (2014). Published by: Jones & Bartlett Publishers (ISBN - 1449659055); Molecular Cloning: A Laboratory Manual., 4 thed.,2012,Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY,USA(ISBN 1936113414),Basic Methods in Molecular Biology,2012,Elsevier Science Publishing,Inc.,New York,USA(ISBN 044460149X);Laboratory Methods in Enzymology:DNA,(2013).Jon Lorsch(ed.) Elsevier(ISBN 0124199542), Current Protocols in Molecular Biology(CPMB)(2014).Frederick M.Ausubel(ed.),John Wiley and Sons(ISBN 047150338X,9780471503385), Current Protocols in Protein Science(CPPS)(2005).John E.Coligan(ed.), John Wiley and Sons, Inc., and Current Protocols in Immunology (CPI) (2003).Coligan, JE, et al., (eds.) John Wiley and Sons, Inc. (ISBN 0471142735,9780471142737).

[0069] Other terms are defined herein within the descriptions of various aspects of this technology.

[0070] Polymer components of wound dressings, compositions, and formulations of this technology The polymer components described herein are antiinfective. In some embodiments, the polymer components are antibacterial against one or both of Gram-negative and Gram-positive bacterial strains.

[0071] In one embodiment, the following is described herein: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them It is a polymer component selected from the group consisting of the following:

[0072] When used in this example, "a combination of two or more of them" encompasses a blend of two or more polymer components. For example, the polymer component could be a blend of the polymer of polymer component (1) and the polymer of polymer component (2). In another example, the polymer component could be a blend of the interpenetrating polymer network of polymer component (1) and the interpenetrating polymer network of polymer component (2). The term "blend" refers to a physical mixture in which there are no further chemical reactions between the components within the blend.

[0073] In some embodiments, the polymer component is a polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite, and the polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, and composite are (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) optionally, a third polyfunctional crosslinking agent, comprising, essentially consisting of, or comprising.

[0074] In some embodiments, the polymer component is a polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite, which comprises, essentially consists of, or comprises a first adduct, polyol, water-soluble polymer, and optionally a third polyfunctional crosslinking agent.

[0075] In some embodiments, the polymer component is a polyethyleneimine intermediate.

[0076] In some embodiments, the polymer component is a second adduct.

[0077] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, and (iii) a water-soluble polymer, or comprises or comprises random polymerization / crosslinking products of a reagent comprising them. In some embodiments, the polymer comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, and (iii) a water-soluble polymer, or comprises or comprises random polymerization / crosslinking products of a reagent comprising them.

[0078] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, and (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, or comprises or comprises a random polymerization / crosslinking product of a reagent consisting of these. In some embodiments, the polymer comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, and (ii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, or comprises a random polymerization / crosslinking product of a reagent consisting of these.

[0079] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) optionally a polyol, (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, (iv) optionally a third polyfunctional crosslinking agent, and (v) a random polymerization / crosslinking product of a reagent comprising, essentially comprising, or consisting of a water-soluble polymer. In some embodiments, the polymer comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) optionally a polyol, (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, (iv) optionally a third polyfunctional crosslinking agent, and (v) random polymerization / crosslinking products of reagents comprising, essentially comprising, or consisting of a water-soluble polymer.

[0080] In some embodiments, (i) a first adduct and (ii) a polyethyleneimine intermediate or a second adduct are prepared separately and then mixed to form a polymer, copolymer, interpenetrating polymer network, polyelectrolyte composite, blend, or complex.

[0081] The water-soluble polymers include, essentially, or consist of, hydroxyethylcellulose, hydroxypropylcellulose, methylcellulose, hydrophobic modified cellulose, polyvinyl alcohol poly(hydroxyethyl methacrylate-co-alkyl methacrylate), poly(hydroxyethyl methacrylate-co-alkyl acrylate), poly(hydroxyethyl acrylate-co-alkyl methacrylate), poly(hydroxyethyl acrylate-co-alkyl acrylate), polyethyleneimine, polyacrylamide, or modified polymers or copolymers thereof on the side chain or main chain (e.g., modifications(possibly) that provide reactive functional groups, hydrophobicity, and / or surface activity), or combinations or blends of two or more of these, or copolymers of two or more of these, or one or more copolymers of polyvinylpyrrolidone, poly(glycidyl acrylate), or poly(glycidyl methacrylate).

[0082] The water-soluble polymer may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts ranging from about 0.5% to about 15% by weight. This includes amounts ranging from about 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, or 15% by weight, or any value in between. In some embodiments, the water-soluble polymer may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts ranging from about 0.5% to about 15% by weight, from about 3% to about 12% by weight, or from about 5% to about 10% by weight.

[0083] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) optionally a polyol, (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, and (iv) optionally a third polyfunctional crosslinking agent, comprising, essentially comprising, a random polymerization / crosslinking product of a reagent comprising, or consisting thereof.

[0084] The first quaternary ammonium salt has the following chemical structure: TIFF2026514865000027.tif16128 may exist, in the formula, R 1 is, -(C8-C 30 Alkyl), -(C8-C 30 Heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel), -(C6-C 10 Ariel)-(C8-C 30 Alkyl), -(C6-C 10 Ariel)-(C8-C 30 Heteroalkyl), -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H and -(CR m R n ) x11 -W 11 -(CR p R q ) y11 Selected from the group consisting of H-, -(C8-C 30 Heteroalkyl), -(C8-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C8-C 30A heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. R 2 -(C1-C4 alkyl), -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel), -(C6-C 10 Aryl)-(C1-C4 alkyl),-(C6-C 10 Aryl)-(C1-C4 heteroalkyl);-(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H and -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -Selected from the group consisting of H, -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The aryl)-(C1-C4 heteroalkyl) has 1-2 heteroatoms independently selected from O, S, and Si. R 3 is, -(C1-C 30 Alkyl), -(C1-C 30 Heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel), -(C6-C 10 Ariel)-(C1-C 30 Alkyl), -(C6-C 10 Ariel)-(C1-C 30 Heteroalkyl), -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H and -(CR m Rn ) x31 -W 31 -(CR p R q ) y31 -Selected from the group consisting of H, -(C1-C 30 Heteroalkyl), -(C1-C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C1-C 30 A heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. A is -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m R n ) x40 -W 40 -(CR p R q ) y40 -, and -(CR m R n ) x41 -W 41 -(CR p R q ) y41 - is a linking group selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m , Rn , R p , and R q These are independently selected from H and C1-C4 alkyl groups. W 10 , W 20 , W 30 , and W 40 These are independently selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 11 , W 21 , W 31 , and W 41 These are independently 5-6 member cycloalkyl, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x10 is an integer between 1 and 30, y10 is an integer between 0 and 29, and 8 ≤ (x10 + y10) ≤ 30. x11 is an integer between 1 and 30, y11 is an integer between 0 and 29, and 8 ≤ (x11 + y11) ≤ 30. x² is an integer between 1 and 4, y² is an integer between 0 and 3, and x² + y² ≤ 4. x²⁻¹ is an integer between 1 and 4, y²⁻¹ is an integer between 0 and 3, and x²⁻¹ + y²⁻¹ ≤ 4. x30 is an integer between 1 and 30, y30 is an integer between 0 and 29, and x30 + y30 ≤ 30. x31 is an integer between 1 and 30, y31 is an integer between 0 and 29, and x31 + y31 ≤ 30. x40 is an integer between 1 and 19, y40 is an integer between 1 and 19, and 3 ≤ (x40 + y40) ≤ 20. x41 is an integer between 1 and 20, y41 is an integer between 0 and 19, and 3 ≤ (x41 + y41) ≤ 20. Y is -OH, -NHR 4 -SH, -CO2H, -C(O)NHR 4-C(S)NHR 4 , Selected from the group consisting of TIFF2026514865000028.tif23128, Each R 4 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives.

[0085] In some embodiments, R 1 is, -(C 12 -C 30 Alkyl), -(C 12 -C 30 Heteroalkyl), -(C 12 -C 30 Alkyl)-(C6-C 10 Ariel), -(C 12 -C 30 Heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Ariel)-(C 12 -C 30 Alkyl), and -(C6-C 10 Ariel)-(C 12 -C 30 Selected from the group consisting of heteroalkyls, -(C 12-C 30 Heteroalkyl), -(C 12 -C 30 Heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Ariel)-(C 12 -C 30 The heteroalkyl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 1 is, -(C 12 -C 30 It is alkyl. In some embodiments, R 1 It has 1 to 4 heteroatoms independently selected from O, S, and Si - (C8-C 30 It is a heteroalkyl group. In some embodiments, R 1 is, -(C6-C 10 Ariel)-(C 12 -C 30 It is alkyl. In some embodiments, R 1 is, -(C 12 -C 30 Alkyl)-(C6-C 10 It is R. In some embodiments, 1 It has 1 to 4 heteroatoms independently selected from O, S, and Si - (C6-C 10 Ariel)-(C 12 -C 30 It is a heteroalkyl group. In some embodiments, R 1 It has 1 to 4 heteroatoms independently selected from O, S, and Si - (C 12 -C 30 Heteroalkyl)-(C6-C 10 It is R. In some embodiments, 1 is, -(CR m R n ) x10 -W 10 -(CR p R q ) y10 -H is the case in some embodiments. 1 is, -(CR m R n )x11 -W 11 -(CR p R q ) y11 -H

[0086] In some embodiments, R 2 is -(C1-C4 alkyl). In some embodiments, R 2 R is a (C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 2 is, -(C6-C 10 It is aryl)-(C1-C4 alkyl). In some embodiments, R 2 is -(C1-C4 alkyl)-(C6-C 10 It is R. In some embodiments, 2 is, -(C6-C 10 It is R. In some embodiments, 2 It has 1 to 4 heteroatoms independently selected from O, S, and Si - (C6-C 10 It is an aryl)-(C1-C4 heteroalkyl) group. In some embodiments, R 2 This is a -(C1-C4 heteroalkyl)-(C6-C) molecule having 1 to 4 heteroatoms independently selected from O, S, and Si. 10 It is R. In some embodiments, 2 is, -(CR m R n ) x20 -W 20 -(CR p R q ) y20 -H is the case in some embodiments. 2 is, -(CR m R n ) x21 -W 21 -(CR p R q ) y21 -H

[0087] In some embodiments, R 3These are -(C1-C4 alkyl), -(C1-C4 heteroalkyl), and -(C1-C4 alkyl)-(C6-C 10 (aryl), -(C1-C4 heteroalkyl)-(C6-C 10 Ariel), -(C6-C 10 Aryl)-(C1-C4 alkyl), and -(C6-C 10 Selected from the group consisting of aryl)-(C1-C4 heteroalkyl), where in the formula -(C1-C4 heteroalkyl), -(C1-C4 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 The aryl)-(C1-C4 heteroalkyl) independently has 1 to 4 heteroatoms selected from O, S, and Si. In some embodiments, R 3 is -(C1-C4 alkyl). In some embodiments, R 3 R is a (C1-C4 heteroalkyl) having 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 3 is, -(C6-C 10 It is aryl)-(C1-C4 alkyl). In some embodiments, R 3 is -(C1-C4 alkyl)-(C6-C 10 It is R. In some embodiments, 3 It has 1 to 4 heteroatoms independently selected from O, S, and Si - (C6-C 10 It is an aryl)-(C1-C4 heteroalkyl) group. In some embodiments, R 3 This is a -(C1-C4 heteroalkyl)-(C6-C) molecule having 1 to 4 heteroatoms independently selected from O, S, and Si. 10 It is R. In some embodiments, 3 is, -(CR m R n ) x30 -W 30 -(CR p R q ) y30 -H is the case in some embodiments. 3 is, -(CR m Rn ) x31 -W 31 -(CR p R q ) y31 -H

[0088] In some embodiments, R 2 and R 3 At least one of them is -(C1-C4 alkyl). In some embodiments, R 2 and R 3 is methyl. In some embodiments, R 1 C 12 -C 30 It is alkyl, R 2 and R 3 It is methyl.

[0089] In some embodiments, A is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 (aryl) may be substituted with 1 to 6 substituents independently selected from -(C3-C 20 A is an alkylene. In some embodiments, A has 1 to 4 heteroatoms independently selected from O, S, and Si -(C3-C 20 Heteroalkylene)- and -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 A may be substituted with 1 to 6 substituents independently selected from aryl. In some embodiments, A is -(C6-C 10 Arrene)-(C3C20 Alkylene)-. In some embodiments, A is -(C3-C 20 Alkylene)-(C6-C 10 (Arirene) - is

[0090] In some embodiments, A is -(CR m R n ) x40 -W 40 -(CR p R q ) y40 -. In some embodiments, A is -(CR m R n ) x41 -W 41 -(CR p R q ) y41 - is

[0091] In some embodiments, A is -(CH2) m -or-(CH2CHR 5 -O-) n CH2CHR 5 - is an integer between 2 and 20, where m is an integer between 0, 1, 2, 3, 4, or 5, and each R 5 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the alphabet, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, R 5 It is either H or methyl.

[0092] In some embodiments, Y is -OH. In some embodiments, Y is -NHR. 4 In some embodiments, Y is -SH. In some embodiments, Y is -CO2H. In some embodiments, Y is -C(O)NHR. 4 And in the formula, R 4 H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is -C(S)NHR 4 And in the formula, R 4 H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is The file is TIFF2026514865000029.tif14128, and in the formula, each R 4 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. In some embodiments, Y is The file is TIFF2026514865000030.tif22128, and in the formula, each R 4 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0093] X -The organically substituted derivatives of the following can be independently selected: acetates, halides (e.g., chlorides, bromides, or iodides), sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. As used herein, and unless otherwise specified, “organically substituted derivatives” refers to anions in which a sulfur atom, phosphorus atom, boron atom, silicon atom, or carbonyl group is substituted with either an alkyl group or an aryl group. Non-limiting examples include methyl sulfate, methanesulfonate, p-toluenesulfonate, trifluoromethylsulfonate, and trifluoroacetate.

[0094] In some embodiments, the first quaternary ammonium salt is TIFF2026514865000031.tif40128, or a combination of two or more of these.

[0095] The first quaternary ammonium salt may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts ranging from about 1% to about 50% by weight. This includes about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, or 50% by weight, or any value in between. In some embodiments, the first quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 5% to about 25% by weight. More precisely, the amount of the quaternary ammonium salt may be expressed in millin / g (mN / g) instead of weight % based on the total weight of the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2). The first quaternary ammonium salt may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 0.1 mN / g to about 1.0 mN / g. This includes any values ​​between 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, or 1.0 mN / g. In some embodiments, the first quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 0.4 mN / g to about 0.9 mN / g. In some embodiments, the first quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 0.5 mN / g to about 0.8 mN / g.

[0096] The first polyfunctional crosslinking agent may be a bifunctional crosslinking agent. In some embodiments, the bifunctional crosslinking agent is a diisocyanate. In some embodiments, the diisocyanate is selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0097] The first polyfunctional crosslinking agent may be a first polyisocyanate. In some embodiments, the first polyisocyanate has an average isocyanate functional value of 2 to 5. This includes average isocyanate functional values ​​of 2, 3, 4, or 5. In some embodiments, the first polyisocyanate has an average isocyanate functional value of 3 to 4.

[0098] The second polyfunctional crosslinking agent may be a second polyisocyanate. In some embodiments, the second polyisocyanate has an average isocyanate functional value of 2 to 5. This includes average isocyanate functional values ​​of 2, 3, 4, or 5. In some embodiments, the second polyisocyanate has an average isocyanate functional value of 3 to 4.

[0099] The third polyfunctional crosslinking agent may be a third polyisocyanate. In some embodiments, the third polyisocyanate has an average isocyanate functional value of 2 to 5. This includes average isocyanate functional values ​​of 2, 3, 4, or 5. In some embodiments, the third polyisocyanate has an average isocyanate functional value of 3 to 4.

[0100] In some embodiments, the first polyfunctional crosslinking agent is a first polyisocyanate, the second polyfunctional crosslinking agent is a second polyisocyanate if present, and the third polyfunctional crosslinking agent is a third polyisocyanate if present, and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are different. In some embodiments, the first polyfunctional crosslinking agent is a first polyisocyanate, the second polyfunctional crosslinking agent is a second polyisocyanate if present, and the third polyfunctional crosslinking agent is a third polyisocyanate if present, and the first polyisocyanate, the second polyisocyanate, and the third polyisocyanate are the same.

[0101] Each of the first, second, and third polyisocyanates may be prepared from a diisocyanate independently selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI).

[0102] In some embodiments, each of the first, second, and third polyisocyanates is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates. DESMODUR® N-3300 and DESMODUR® N-100 are aliphatic polyisocyanates based on HDI (hexamethylene diisocyanate) trimers. DESMODUR® Z4470SN is a polyfunctional polyisocyanate based on IPDI (isophorone diisocyanate). WANNATE® T-series polyisocyanates are toluene diisocyanate (TDI)-based aromatic polyisocyanates. LUPRANATE® M-series polyisocyanates are aromatic polyisocyanates based on 4,4-diphenylmethane diisocyanate (MDI).

[0103] The first polyfunctional crosslinking agent may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 2% to about 25% by weight. This includes 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25% by weight, or any value in between. In some embodiments, the first polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 7% to about 15% by weight or about 5% to about 20% by weight.

[0104] The second polyfunctional crosslinking agent may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or polymer component (4) in an amount of about 0.1% to about 10% by weight. This includes 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, or 10% by weight, or any value in between. In some embodiments, the second polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or polymer component (4) in an amount of about 1% to about 10% by weight, about 2% to about 8% by weight, or about 3% to about 6% by weight.

[0105] A third polyfunctional crosslinking agent may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of approximately 0.1% to approximately 20% by weight. This includes 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 17.5, 18, 18.5, 19, 19.5, or 20% by weight, or any value in between. In some embodiments, the third polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of about 1% to about 20% by weight or about 2% to about 15% by weight.

[0106] In some embodiments, the first adduct has an average isocyanate functional value of 2 to 3. In some embodiments, the first adduct has an average isocyanate functional value of about 2.05 to about 2.3.

[0107] The first adduct may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in an amount of approximately 5% to 70% by weight. This includes approximately 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, or 70% by weight, or any value in between. In some embodiments, the first adduct is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts of about 10% to about 50% by weight, about 15% to about 65% by weight, about 15% to about 60% by weight, about 15% to about 50% by weight, about 20% to about 70% by weight, about 20% to about 60% by weight, or about 20% to about 50% by weight.

[0108] The polyol may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts ranging from about 1% by weight to about 40% by weight. This includes 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40% by weight, or any value in between. In some embodiments, the polyol may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) or (2) in amounts ranging from about 5% by weight to about 25% by weight.

[0109] The polyol can be selected from the group consisting of polyether polyols, polyester polyols, polyacrylic polyols, polymethacrylic polyols, polycaprolactone polyols, polybutadiene polyols, poly(acrylonitrile-co-butadiene) polyols, polysiloxane polyols, copolymers of any two or more of these, and any combination of any two or more of these.

[0110] In some embodiments, the polyol comprises, essentially consists of, or comprises one or more copolymers of polytetramethylene glycol (PTMG), polyethylene glycol (PEG), polypropylene glycol (PPG), or two or more combinations thereof, or polyester, polycaprolactone, polybutadiene, poly(acrylonitrile-butadiene), polysiloxane, or polyacrylate. In some embodiments, the polyol is selected from the group consisting of poly(tetramethylene glycol), polyethylene glycol, polypropylene glycol, poly(ethylene glycol-b-propylene glycol-b-ethylene glycol), and poly(propylene glycol-b-polyethylene glycol-b-propylene glycol).

[0111] In some embodiments, the polyol includes, is essentially, or consists of a polyether polyol, a polyester polyol, or a combination thereof.

[0112] Polyols can have an average molecular weight of about 300 to about 3000 daltons. This includes about 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, 1200, 1250, 1300, 1350, 1400, 1450, 1500, 1550, 1600, 1650, 1700, 1750, 1800, 1850, 1900, 1950, or 2000 daltons, or any value in between. In some embodiments, polyols have an average molecular weight of about 400 to about 2000, or about 600 to about 1500 daltons.

[0113] In some embodiments, the polyol is pre-reacted with a first polyisocyanate to form an isocyanate end-cap prepolymer. In some embodiments, the polyol is pre-reacted with a third polyisocyanate to form an isocyanate end-cap prepolymer.

[0114] In some embodiments, the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:1. This includes 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1, 1.9:1, 2:1, 2.2:1, 2.4:1, 2.6:1, 2.8:1, 3:1, 3.2:1, 3.4:1, 3.6:1, 3.8:1, 4:1, 4.2:1, 4.4:1, 4.6:1, 4.8:1, 5:1, 5.2:1, 5.4:1, 5.6:1, 5.8:1, 6:1, 6.2:1, 6.4:1, 6.6:1, 6.8:1, and 7:1. This includes ratios of 7.2:1, 7.4:1, 7.6:1, 7.8:1, 8:1, 8.2:1, 8.4:1, 8.6:1, 8.8:1, 9:1, 9.2:1, 9.4:1, 9.6:1, 9.8:1, 10:1, 15:1, 20:1, 25:1, 30:1, 35:1, 40:1, 45:1, 50:1, 55:1, 60:1, 65:1, 70:1, 75:1, 80:1, 85:1, 90:1, 95:1, 99:1, or any ratio of any value between them.

[0115] In some embodiments, the polyethyleneimine intermediate comprises a first adduct and, if present, a second polyfunctional crosslinking agent, and an optionally substituted hydroxyalkylene functional group that reacts with the second polyfunctional crosslinking agent. In some embodiments, the polyethyleneimine intermediate comprises a first adduct and, if present, a second polyfunctional crosslinking agent, and, if present, a third polyfunctional crosslinking agent, and an optionally substituted hydroxyalkylene functional group that reacts with the second polyfunctional crosslinking agent.

[0116] In some embodiments, the hydroxyalkylene functional group is -N + (R 20 )3X - ,-(C6-C 10 -(C1-C6 alkoxy), -(C1-C6 alkoxy), -(C1-C6 alkyl), which may be substituted with -(aryl) and -OH. 10 Each R may be substituted with a C1-C6 alkyl group which may be substituted with a substituent selected from aryl and carboxyl groups, 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, each X - However, these are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. In some embodiments, the hydroxyalkylene functional group is -N + (R 20 )3X - It is substituted with C1-C6 alkyl groups, and each R20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, each X - The functional group is independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. In some embodiments, the hydroxyalkylene functional group is -(CH2)-N + (Me)3Cl - It is substituted with. In some embodiments, the hydroxyalkylene functional group is hydroxyethylene, hydroxypropylene, hydroxybutylene, or an oligomer thereof.

[0117] In some embodiments, the polyethyleneimine intermediate comprises a reaction product of a reagent containing polyethyleneimine and an alkylating agent. In some embodiments, the reagent further comprises a monoepoxide or lactone. In some embodiments, the monoepoxide or lactone is -(C6-C 10 C1-C6 alkoxy, C1-C6 alkoxy, and C1-C6 alkyl may be substituted with aryl, C1-C6 alkyl, and C1-C6 alkyl. 10 It may be substituted with a C1-C6 alkyl group, which may be substituted with a substituent selected from aryl and carboxyl groups.

[0118] In some embodiments, the polyethyleneimine intermediate comprises a reaction product of a reagent containing polyethyleneimine, a monoepoxide, and an alkylating agent, wherein the monoepoxide is -(C6-C 10 C1-C6 alkoxy, C1-C6 alkoxy, and C1-C6 alkyl may be substituted with aryl, C1-C6 alkyl, and C1-C6 alkyl. 10 It may be substituted with a C1-C6 alkyl group, which may be substituted with a substituent selected from aryl and carboxyl groups.

[0119] In some embodiments, the monoepoxide is a C1-C6 alkyloxirane. In some embodiments, the C1-C6 alkyloxirane is selected from the group consisting of methyloxirane (propylene oxide), ethyloxirane (1-butylene oxide or 1,2-epoxybutane), propyloxirane (1-pentene oxide), butyloxirane (1-hexene oxide), and hexyloxirane (1-octenoxide). In some embodiments, the C1-C6 alkyloxirane is methyloxirane or propylene oxide. In some embodiments, the C1-C6 alkyloxirane is butyloxirane or 1-hexene oxide. In some embodiments, the C1-C6 alkyloxirane is hexyloxirane or octenoxide.

[0120] In some embodiments, the polyethyleneimine intermediate comprises a reaction product of polyethyleneimine, a monoepoxide, and optionally, a reagent containing an alkylating agent, wherein the monoepoxide is -(C1-C6 alkylene)-N + (R 20 )3X - It is replaced by each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0121] In some embodiments, the polyethyleneimine intermediate comprises a reaction product of a reagent containing polyethyleneimine and a monoepoxide, wherein the monoepoxide is -(C1-C6 alkylene)-N + (R 20 )3X - It is replaced by each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0122] In some embodiments, the alkylating agent is one or more R 21 -Includes LG, in the formula, each R 21These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 The alkylating agent is selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-(C1-C6 alkoxy), and each LG is a leaving group. As used herein and unless otherwise specified, the leaving group may be a halide, sulfonate, etc. In some embodiments, the alkylating agent is phenacyl halogenate, benzyl halogenate, or hexyl halogenate.

[0123] In some embodiments, the reagent for the reaction product contained in the polyethyleneimine intermediate further comprises a monoisocyanate. In some embodiments, the monoisocyanate comprises one or more R 30 -Includes NCO, in the formula, each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a These are independently C1-C6 alkyl groups, and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3. In some embodiments, the monoisocyanate includes octyl isocyanate, octadecyl isocyanate, or a combination thereof.

[0124] Polyethyleneimine intermediates may be present in amounts ranging from approximately 0.1% to approximately 50% by weight in the polymer, copolymer, or interpenetrating polymer network of polymer components (1), (3), or (4). These amounts are 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 12.5, 13, 13.5, 14, 14.5, 15, 15.5, 16, 16.5, 17, 1 The amounts include 7.5, 18, 18.5, 19, 19.5, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, or 50% by weight, or any value in between. In some embodiments, the polyethyleneimine intermediate is present in the polymer, copolymer, or interpermeable polymer network of polymer component (1), (3), or (4) in an amount of about 3% to about 30% by weight.

[0125] In some embodiments, at least 20% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized. In some embodiments, at least 30% of the nitrogen atoms in the polyethyleneimine intermediate are quaternized.

[0126] Polyethyleneimines can have molecular weights ranging from about 300 to about 270,000 daltons. This includes about 300, 400, 500, 600, 700, 800, 900, 1000, 2500, 5000, 10,000, 25,000, 50,000, 75,000, 100,000, 125,000, 150,000, 175,000, 200,000, 225,000, 250,000, or 270,000 daltons, or any value in between. In some embodiments, polyethyleneimines have molecular weights ranging from about 10,000 to about 200,000 daltons, or about 25,000 to about 120,000 daltons.

[0127] In some embodiments, the polyethyleneimine is branched. In some embodiments, the polyethyleneimine is polybranched.

[0128] In some embodiments, polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:2:1 to about 1:1:1. In some embodiments, polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:1:0.7.

[0129] In some embodiments, the polyethyleneimine intermediate is TIFF2026514865000032.tif88136, and any two or more copolymers or blends thereof selected, in the formula, Each Y 3 These are independently H or -OY 2 And, Each Y 2 These are independently H or -C(O)-NHR 30 And, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 Independently, hydrogen;-N(R 20 )3, -(C6-C 10 C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl 10 Selected from aryl, and carboxyl, each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. however, R 10 However, -(C6-C10 aryl), and -(C1-C6 alkoxy), -(C1-C6 alkoxy), -(C1-C6 alkyl) which may be substituted with -OH and may be substituted with a substituent selected from - (C6-C 10 aryl), and when it is C1-C6 alkyl which may be substituted with a substituent selected from carboxy, the polyethyleneimine intermediate is independently selected from TIFF2026514865000033.tif88128.

[0130] In some embodiments, the polyethyleneimine intermediate is TIFF2026514865000034.tif36128, wherein each R 60 is independently -OH, -N + (R 20 )3X - -, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 aryl), and a substituent selected from 1 to 3 substituents which may be substituted with -OH and may be substituted with -(C1-C6 alkoxy) -Y 4 -(C1-C 18 alkyl) is selected, at least one R 60 is substituted with -OH, but less than 50% of all R 60 is substituted with -OH, Y 4 is absent or -C(O)-, each R 20 is independently C1-C 18 alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 heteroalkyl; and -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl) which may be substituted C6-C 10Selected from the group consisting of aryl, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000, each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and their organic substituted derivatives.

[0131] In some embodiments, the polyethyleneimine intermediate is TIFF2026514865000035.tif37128, wherein each R 60 is independently optionally substituted with one to three substituents selected from -OH, -N + (R 20 )3X - ,-(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), and -C(O)-(C6-C 10 aryl), and is selected from -Y 4 -(C1-C 18 alkyl), at least one R 60 is substituted with -OH, but less than 50% of all R 60 are substituted with -OH, Y 4 is absent or -C(O)-, each R 20 is independently selected from the group consisting of C1-C6 alkyl, each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000, each X -These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0132] Several embodiments, each R 60 It may be independently substituted with -OH -(C1-C 18 Selected from alkyl groups, with at least one R 60 It is substituted with -OH, but all R 60 Less than 50% of it is substituted with -OH.

[0133] Several embodiments, each R 60 These are independently -CH3, -C4H9, and -C6H 13 -C8H 17 , -C 18 H 37 , -CH2Ph, -CH2C(O)OCH2CH3, -CH2C(O)Ph, -(CH2)3OH, -CH2CH(CH3)OH, -CH2CH(OH)CH2N + Selected from the group consisting of (CH3)3 and -C(O)(CH2)5OH. In some embodiments, each R 60 These are independently -CH3, -C4H9, and -C6H 13 -C8H 17 , -C 18 H 37 , -CH2Ph, -CH2C(O)OCH2CH3, -CH2C(O)Ph, -(CH2)3OH, -CH2CH(CH3)OH, -CH2CH(OH)CH2N + Selected from the group consisting of (CH3)3 and -C(O)(CH2)5OH, and at least one R 60 However, although it is substituted with -OH, all R 60 Less than 50% of it is substituted with -OH.

[0134] In some embodiments, at least one R 60 However, although it is substituted with -OH, all R60 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, or 49% of are substituted with -OH. In some embodiments, all R 60 Approximately 1% to 49% of the molecule is substituted with -OH groups. This includes approximately 1% to 40%, 1% to 30%, 1% to 20%, 1% to 18%, 1% to 15%, 1% to 10%, 5% to 40%, 5% to 30%, 5% to 20%, 5% to 18%, 5% to 15%, 5% to 10%, and any range in between.

[0135] In some embodiments, the polyethyleneimine intermediate is selected from the group consisting of: TIFF2026514865000036.tif223165* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000037.tif36128, and B is, TIFF2026514865000038.tif34128, where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100. In some embodiments, one or more bromide anions are X independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. - It has been replaced with.

[0136] In some embodiments, the polyethyleneimine intermediate is selected from the group consisting of: TIFF2026514865000039.tif218155* indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) ***Actual stoichiometric ratio determined by NMR analysis In the table, A is, The filename is TIFF2026514865000040.tif35128, and B is, The file is TIFF2026514865000041.tif34128, where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100, and each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0137] In some embodiments, the second appendage is of formula (I), TIFF2026514865000042.tif43128 formula, Each A is independent, TIFF2026514865000043.tif136132, or any two or more copolymers or blends thereof, wherein the attachment of each A forms a carbamate linkage, Each Y 3 These are independently H or -OY 2 And all Y 3 However, it cannot be H, Each Y 2 These are independently H or -C(O)-NHR 30 And all Y 2 However, -C(O)-NHR 30 It cannot be, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 Independently, hydrogen;-N(R 20 )3, -(C6-C 10 C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl 10 Selected from aryl, and carboxyl, each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, (2)halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10Aryl, and (3) Selected from TIFF2026514865000044.tif42128, where each R a is independently -(C1-C6 alkyl), and each R b and each R c is independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, each R 40 is independently phenyl or -(C1-C 10 alkylene)- optionally substituted with a 3- to 8-membered cycloalkyl ring, each X - is independently selected from the group consisting of acetate, halide, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and their organic substituted derivatives, provided that R 10 is -(C6-C 10 aryl), and -(C1-C6 alkoxy) optionally substituted with -OH, -(C1-C6 alkoxy), -(C1-C6 alkyl) optionally substituted with -(C6-C 10 aryl), and C1-C6 alkyl optionally substituted with a substituent selected from carboxy, each A is independently Selected from TIFF2026514865000045.tif44145.

[0138] In some embodiments, the second adduct is of formula (II), TIFF2026514865000046.tif43128 where each A is independently TIFF2026514865000047.tif134132, or selected from any two or more of their copolymers or blends, and the attachment of each A forms a carbamate linkage, each Y 3 is independently H or -O-Y 2And all Y 3 However, it cannot be H, Each Y 2 These are independently H or -C(O)-NHR 30 And all Y 2 However, -C(O)-NHR 30 It cannot be, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 Independently, hydrogen;-N(R 20 )3, -(C6-C 10 C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkyl 10 Selected from aryl, and carboxyl, each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (ORb )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, (2)halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Ariel, and (3) Selected from TIFF2026514865000048.tif42128, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, Each R 40 These may be independently substituted with phenyl or a 3- to 8-membered cycloalkyl ring - (C1-C 10 Alkilen)- each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives. however, R 10 However, -(C6-C 10 -(C1-C6 alkoxy), -(C1-C6 alkoxy), -(C1-C6 alkyl), which may be substituted with -(aryl) and -OH. 10 If A is a C1-C6 alkyl group which may be substituted with substituents selected from aryl and carboxyl groups, then each A is independently, Selected from TIFF2026514865000049.tif44146.

[0139] In some embodiments, the second adduct is present in the polymer, copolymer, or interpermeable polymer network of polymer component (1) or (4) in an amount of about 1% to about 30% by weight. This includes about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30% by weight, or any value in between. In some embodiments, the second adduct is present in the polymer, copolymer, or interpermeable polymer network of polymer component (1) or (4) in an amount of about 3% to about 15% by weight.

[0140] The reagents for random polymerization / crosslinking products are (i) a first or fourth polyfunctional crosslinking agent and (ii) a second quaternary ammonium salt. It may further include a third adduct of TIFF2026514865000050.tif16128, in the formula, R 1a , R 2a , and R 3a These are, independently, -(C1-C 20 Alkyl), -(C1-C 20 Alkyl)-(C6-C 10 (aryl), or -(C6-C) 10 Ariel)-(C1-C 20 It is alkyl, A 1 is, -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 , and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43- is a linking group selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20 Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m1 , R n1 , R p1 , and R q1 These are independently selected from H and C1-C4 alkyl groups. W 42 It is selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 43 These are 5-6 member cycloalkyl groups, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x42 is an integer between 1 and 19, y42 is an integer between 1 and 19, and 3 ≤ (x42 + y42) ≤ 20. x43 is an integer between 1 and 20, y43 is an integer between 0 and 19, and 3 ≤ (x43 + y43) ≤ 20. Y 1 -OH, -NHR 4a -SH, -CO2H, -C(O)NHR 4a -C(S)NHR 4a , Selected from the group consisting of TIFF2026514865000051.tif23128, Each R 4a These are independently H, (C-(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives.

[0141] The fourth polyfunctional crosslinking agent may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 0.1% to about 15% by weight. This includes 0.1, 0.25, 0.5, 0.75, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 11, 12, 13, 14, or 15% by weight, or any value in between. In some embodiments, the fourth polyfunctional crosslinking agent is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 2% to about 8% by weight.

[0142] The fourth polyfunctional crosslinking agent may differ from the first polyfunctional crosslinking agent, and, if present, the second polyfunctional crosslinking agent, and, if present, the third polyfunctional crosslinking agent.

[0143] In some embodiments, the fourth polyfunctional crosslinking agent is a fourth polyisocyanate. In some embodiments, the fourth polyisocyanate is prepared from a diisocyanate selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the fourth polyisocyanate is selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0144] In some embodiments of the second quaternary ammonium salt, R 1a , R 2a , and R 3a At least one of them is -(C1-C4 alkyl). In some embodiments of the second quaternary ammonium salt, R 1a , R 2a , and R 3a Two of them are -(C1-C4 alkyl). In some embodiments, the second quaternary ammonium salt is The filename is TIFF2026514865000052.tif26152.

[0145] The second quaternary ammonium salt may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 1% to about 15% by weight. This includes about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15% by weight, or any value in between. In some embodiments, the second quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 3% to about 10% by weight.

[0146] In some embodiments, the third adduct has an average isocyanate functional value of 2 to 3. In some embodiments, the third adduct has an average isocyanate functional value of 2.05 to about 2.3.

[0147] The third adduct may be present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 2% to about 30% by weight. This includes about 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30% by weight, or any value in between. In some embodiments, the second quaternary ammonium salt is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1) in an amount of about 3% to about 20% by weight.

[0148] The reagent for random polymerization / crosslinking products is HO-(C n H 2n )-OH and HO-(C n H 2n-2The formula may further include a chain extender selected from the group consisting of )-OH or combinations thereof, where n is an integer from 2 to 8. In some embodiments, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more of these. The chain extender may be present in the polymer, copolymer, or interpenetrating polymer network of polymer components (1) and (2) in an amount of about 0.5% to about 10% by weight. This includes about 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10% by weight, or any value in between. In some embodiments, the chain extender may be present in the polymer, copolymer, or interpenetrating polymer network of polymer components (1) and (2) in an amount of about 1% to about 5% by weight.

[0149] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which comprises (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) optionally a polyol, (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, (iv) optionally a third polyfunctional crosslinking agent, (v) optionally a third adduct of (a) a first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent and (b) a second quaternary ammonium salt, (vi) optionally a chain extender, and (vii) a random polymerization / crosslinking product of a reagent comprising, essentially comprising, a water-soluble polymer, or comprising thereof.

[0150] In some embodiments, the polymer component is a polymer, an interpenetrating polymer network, a polyelectrolyte complex, a blend, or a composite, each of which (i) a first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, (ii) optionally a polyol, (iii) a polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, (iv) optionally a third polyfunctional crosslinking agent, (v) optionally a third adduct of (a) a first polyfunctional crosslinking agent or a fourth polyfunctional crosslinking agent and (b) a second quaternary ammonium salt, and (vi) optionally a random polymerization / crosslinking product of a reagent comprising, essentially comprising, or consisting of a chain extender.

[0151] In some embodiments, the polymer component is a third quaternary ammonium salt Further including TIFF2026514865000053.tif17128, in the formula, R 1a , R 2a , and R 3a These are independently methyl or ethyl, A 2 is, -(C3-C 20 Alkylene)-,-(C3-C 20 Heteroalkylene)-,-(C6-C 10 Arrene)-(C3C 20 Alkilen)-,-(CR m1 R n1 ) x42 -W 42 -(CR p1 R q1 ) y42 , and -(CR m1 R n1 ) x43 -W 43 -(CR p1 R q1 ) y43 -Selected from the group consisting of -(C3-C 20 Heteroalkylenes have 1 to 4 heteroatoms independently selected from O, S, and Si, and -(C3-C 20Alkylene)- and -(C3-C 20 Heteroalkylene)- is -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 Aryl)-, and-(C6-C 10 It may be substituted with 1 to 6 substituents independently selected from the aryl group. Each R m1 , R n1 , R p1 , and R q1 These are independently selected from H and C1-C4 alkyl groups. W 42 It is selected from -C(O)-, -C(O)O-, -OC(O)-, -C(O)NH-, and -NHC(O)-, W 43 These are 5-6 member cycloalkyl groups, C6-C 10 Selected from aryl, 5-6 membered heterocycloalkyl, and 5-6 membered heteroaryl, where heterocycloalkyl contains 1-2 ring heteroatoms selected from O, N, S, and Si, and heteroaryl contains 1-3 ring heteroatoms selected from O, N, S, and Si. x42 is an integer between 1 and 19, y42 is an integer between 1 and 19, and 3 ≤ (x42 + y42) ≤ 20. x43 is an integer between 1 and 20, y43 is an integer between 0 and 19, and 3 ≤ (x43 + y43) ≤ 20. Y 1a H is, Each R 4a These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si. X - These are independently acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, borates, or any of the aforementioned organically substituted derivatives.

[0152] In some embodiments, a first quaternary ammonium salt reacts with a first polyisocyanate to form a first adduct, which retains unreacted isocyanate functional groups from the first polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to about 33%, of the isocyanate functional groups on the first polyisocyanate are converted to, for example, urethane or urea by reaction with the first quaternary ammonium salt. The unreacted isocyanate functional groups then react with one or more of the following: a polyol (if present), a chain extender (if present), a polyethyleneimine intermediate or a second adduct, water, and a water-soluble polymer (if reactive). Similarly, in some embodiments, a second quaternary ammonium salt reacts with a first or fourth polyisocyanate to form a third adduct, which retains unreacted isocyanate functional groups from the first or fourth polyisocyanate. In some embodiments, about 10% to about 40%, preferably about 25% to 33%, of the isocyanate functional groups on the first or fourth polyisocyanate are converted to, for example, urethane or urea by reaction with a second quaternary ammonium salt. If present, a third polyfunctional crosslinking agent and / or third adduct may also react with one or more of the following: polyol (if present), chain extender (if present), polyethyleneimine intermediate or second adduct, water, and water-soluble polymer (if reactive). The first and third adducts are pre-formed before interacting with the polyol (if present), chain extender (if present), polyethyleneimine intermediate or second adduct, and water-soluble polymer (if reactive).

[0153] In another embodiment, the polymer or interpenetrating polymer network is (a) Reacting a first polyfunctional crosslinking agent with a first quaternary ammonium salt to form a first adduct, (b) Optionally reacting the polyethyleneimine intermediate with a second polyfunctional crosslinking agent to form a second adduct, (c) optionally reacting the first polyfunctional crosslinking agent or the fourth polyfunctional crosslinking agent with the second quaternary ammonium salt to form a third adduct, (d) (i) the first adduct, (ii) the polyethyleneimine intermediate or the second adduct, and (iii) the third adduct, if present, optionally combined with a polyol and optionally a third polyfunctional crosslinking agent to form an oil phase. (e) Dissolving a water-soluble polymer in water to form an aqueous phase, (f) Combining the oil phase and the aqueous phase to form an oil-in-water emulsion, and (g) Prepared by applying the emulsion to a surface, drying and curing the emulsion on the surface to form the polymer or interpenetrating polymer network on the surface.

[0154] In some embodiments, the blocking agent is added to the oil phase after step (d) but before step (f).

[0155] In some embodiments, step (d) further comprises forming an oil phase in an organic solvent or diluent by combining (i) a first adduct, (ii) a polyethyleneimine intermediate or a second adduct, and (iii) a third adduct, if present, optionally with a polyol and optionally a second polyfunctional crosslinking agent.

[0156] In some embodiments, step (d) further includes adding a chain extender to the oil phase. In some embodiments, step (d) further includes adding a chain extender to the aqueous phase.

[0157] In some embodiments, step I further includes adding a surfactant to the aqueous phase. In some embodiments, step I further includes adding an antifoaming agent or defoaming agent to the aqueous phase. In some embodiments, step I further includes adding a surfactant and either an antifoaming agent or defoaming agent to the aqueous phase.

[0158] In some embodiments, step (f) further includes carrying out a direct emulsification process in which the emulsion is formed by vigorous shearing and mixing. In some embodiments, step (f) further includes carrying out a direct emulsification process in which the emulsion is formed by sonication.

[0159] In some embodiments, step (f) further includes carrying out a phase inversion emulsification process in which a water-in-oil emulsion is first prepared, followed by a phase inversion to form an oil-in-water emulsion. Phase inversion can be carried out, for example, by changing the phase ratio, temperature, surfactant, solvent, or any combination of two or more of these.

[0160] In some embodiments, the multiphase water-in-oil-in-water emulsion is formed before the conversion to an oil-in-water emulsion in step (f).

[0161] In some embodiments, combining the oil phase and the aqueous phase in step (f) forms a combination of an oil-in-water emulsion and a multiphase water-in-oil emulsion.

[0162] In another embodiment, reagents for preparing the polymers or interpenetrating polymer networks described herein are included in the composition.

[0163] Therefore, in another embodiment, a composition comprising an oil-in-water emulsion, wherein the oil-in-water emulsion is (i) an oil phase, A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, Optionally, polyols, Polyethyleneimine intermediate, or a second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, and Optionally, an oil phase containing a third polyfunctional crosslinking agent, (ii) An antimicrobial composition comprising an aqueous phase containing a water-soluble polymer is provided herein. This composition can be applied to a surface, dried, and cured to form the polymer or interpenetrating polymer network of the present technology.

[0164] The reactive linking groups of the first quaternary ammonium salt are -OH, -NHR 4 -SH, -CO2H, -C(O)NHR 4 -C(S)NHR 4 , Selected from the group consisting of TIFF2026514865000054.tif23128, in the formula, each R 4 These are independently H, -(C6-C 10 Aryl)-(C1-C3 alkyl),-(C6-C 10 Aryl)-(C1-C3 heteroalkyl),-(C1-C3 alkyl)-(C6-C 10 Aryl),-(C1-C3 heteroalkyl)-(C6-C 10 aryl), and -(C6-C 10 Selected from the group consisting of aryls, -(C6-C 10 Aryl)-(C1-C3 heteroalkyl) and -(C1-C3 heteroalkyl)-(C6-C 10 The aryl group has 1 to 4 heteroatoms independently selected from O, S, and Si.

[0165] The first quaternary ammonium salt described herein and incorporated into the first adduct may be present in the oil phase in an amount of about 1% to about 50% by weight based on the dry weight of the oil phase. Where used herein, and unless otherwise specified, “dry weight of oil phase” refers to the weight of the oil phase in the absence of any organic solvents and any water. This includes approximately 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, or 50%, or any value in between. In some embodiments, the first quaternary ammonium salt incorporated into the first adduct is present in the oil phase in an amount of about 1% to about 25% by weight, or about 5% to about 25% by weight, based on the dry weight of the oil phase.

[0166] The first polyfunctional crosslinking agent (e.g., the first polyisocyanate) described herein and incorporated into the first adduct may be present in the oil phase in an amount of about 2% to about 25% by weight based on the dry weight of the oil phase. This includes any value in between, such as about 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, or 25%. In some embodiments, the first polyfunctional crosslinking agent (e.g., the first polyisocyanate) incorporated into the first adduct may be present in the oil phase in an amount of about 5% to about 20% by weight based on the dry weight of the oil phase.

[0167] The first adducts described herein may be present in the oil phase in amounts of about 5% to about 70% by weight based on the dry weight of the oil phase. This can range from about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, about 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40% %, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, 50%, 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 61%, 62%, 63%, 64%, 65%, 66%, 67%, 68%, 69%, or 70%, or any value in between. In some embodiments, the first adduct is present in amounts of about 10% to about 50% by weight, about 15% to about 65% by weight, about 15% to about 60% by weight, about 15% to about 50% by weight, about 20% to about 70% by weight, about 20% to about 60% by weight, or about 20% to about 50% by weight based on the dry weight of the oil phase.

[0168] The polyethyleneimine intermediates described herein may be present in the oil phase in amounts ranging from about 0.1% to about 50% by weight, based on the dry weight of the oil phase. This corresponds to 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, 10.5%, 11%, 11.5%, 12%, 12.5%, 13%, 13.5%, 14%, 14.5%, about 15%, 15.5%, 16%, 16.5%, and 17%. , 17.5%, 18%, 18.5%, 19%, 19.5%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, 40%, 41%, 42%, 43%, 44%, 45%, 46%, 47%, 48%, 49%, or 50%, or any value in between. In some embodiments, the polyethyleneimine intermediate is present in the oil phase in an amount of about 3% to about 30% by weight based on the dry weight of the oil phase.

[0169] The second polyfunctional crosslinking agent (e.g., a second polyisocyanate) described herein and incorporated into the second adduct may be present in the oil phase in an amount of about 0.1% to about 10% by weight based on the dry weight of the oil phase. This includes about 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, or 10%, or any value in between. In some embodiments, the second polyfunctional crosslinking agent (e.g., a second polyisocyanate) is present in the oil phase in an amount of about 2% to about 8% by weight, or about 3% to about 6% by weight, based on the dry weight of the oil phase.

[0170] The second adduct described herein may be present in the oil phase in an amount of about 1% to about 30% by weight based on the dry weight of the oil phase. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, or 30%, or any value in between. In some embodiments, the second adduct is present in the oil phase in an amount of about 3% to about 15% by weight based on the dry weight of the oil phase.

[0171] In some embodiments, the oil phase further comprises a third polyfunctional crosslinking agent as described herein. The third polyfunctional crosslinking agent (e.g., a third polyisocyanate) may be present in the oil phase in an amount of about 5% to about 25% by weight based on the dry weight of the oil phase. This includes any value in between, such as about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, or 25%. In some embodiments, the third polyfunctional crosslinking agent (e.g., a third polyisocyanate) may be present in the oil phase in an amount of about 5% to about 20% by weight based on the dry weight of the oil phase.

[0172] In some embodiments, the oil phase further comprises a third adduct described herein. The third adduct may be present in the oil phase in an amount of about 2% to about 30% by weight based on the dry weight of the oil phase. This includes any value in between, or about 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, or 30%. In some embodiments, the third adduct is present in the oil phase in an amount of about 3% to about 20% by weight based on the dry weight of the oil phase.

[0173] In some embodiments, the second quaternary ammonium salt described herein and incorporated into the third adduct is present in the oil phase in an amount of about 1% to about 15% by weight based on the dry weight of the oil phase. This includes about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, or 15%, or any value in between. In some embodiments, the second quaternary ammonium salt described herein and incorporated into the third adduct is present in the oil phase in an amount of about 3% to about 10% by weight based on the dry weight of the oil phase.

[0174] A fourth polyfunctional crosslinking agent (e.g., a fourth polyisocyanate) described herein and incorporated into a third adduct may be present in the oil phase in an amount of about 0.1% to about 15% by weight based on the dry weight of the oil phase. This includes about 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 4.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, 10%, 11%, 12%, 13%, 14%, or 15%, or any value in between. In some embodiments, a fourth polyfunctional crosslinking agent (e.g., a fourth polyisocyanate) described herein and incorporated into the third adduct is present in the oil phase in an amount of about 2% to about 8% by weight based on the dry weight of the oil phase.

[0175] In some embodiments, the reactive isocyanate functional groups on the first and / or third adducts are protected with a blocking agent. The reaction with the blocking agent converts the reactive isocyanate functional groups into blocked isocyanates (i.e., the isocyanate groups are reversibly protected from immediate reaction with nucleophiles). This reduces the rate of the polyisocyanate reaction with water in the subsequent emulsification step, as well as / or the crosslinking reaction with any polyol(s) in the oil phase and / or water-soluble polymers (such as hydroxyethylcellulose) in the aqueous phase. In some embodiments, there is a significant improvement in the rheological properties, particle size, and distribution reproducibility of the resulting emulsion. In some embodiments, the coatability and process window of the coating process are also significantly improved. In some embodiments, the defect rate of the resulting surface coating is reduced, and the yield of the coated product is also improved. In some embodiments, no blocking agent is used to provide a coating that cures more rapidly.

[0176] In some embodiments, the blocking agent is selected from the group consisting of oximes, phenols, malonates, alcohols, lactams, dicarbonyl compounds, hydroxamates, bisulfite adducts, hydroxylamines, esters of p-hydroxybenzoic acid and salicylic acid. In some embodiments, the blocking agent is selected from the group consisting of acetone oxime, methyl ethyl ketone oxime, sodium bisulfite, diethyl malonate, and 3,5-dimethylpyrazole.

[0177] In some embodiments, the composition further comprises a deblocking agent. Examples of deblocking agents include, but are not limited to, organotin, organobismuth, and tert-amines. Non-limiting examples include triethanolamine, N,N,N'N'-tetrakis(2-hydroxyethyl)ethylenediamine, and K-KAT XK-651 (bismuth carboxylate catalyst).

[0178] In some embodiments, the oil phase is HO-(C) n H 2n )-OH and HO-(C n H 2n-2 The formula further comprises a chain extender selected from the group consisting of )-OH or combinations thereof, where n is an integer from 2 to 8. In some embodiments, the chain extender is propanediol, 1,4-butanediol, neopentyl glycol, hexanediol, cyclohexanedimethanol, or a combination of two or more of these. The chain extender may be present in the oil phase in an amount of up to about 10% by weight based on the dry weight of the oil phase. This includes any value in between about 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%. In some embodiments, the chain extender is present in the oil phase in an amount of about 0.5% to about 10% by weight, or about 1% to about 5% by weight, based on the dry weight of the oil phase.

[0179] In some embodiments, the oil phase further comprises an organic solvent or diluent. In some embodiments, the organic solvent or diluent in the oil phase is water-miscible. In some embodiments, the organic solvent or diluent is acetone. In some embodiments, the organic solvent or diluent is present in the oil phase in an amount of about 5% to about 35% by weight based on the weight of the oil phase. This includes about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, or 35%, or any value in between. In some embodiments, the organic solvent or diluent is present in the oil phase in an amount of about 10% to about 30% by weight based on the weight of the oil phase.

[0180] Polyols may be present in the oil phase in amounts ranging from about 1% to about 40% by weight, based on the dry weight of the oil phase. This includes amounts ranging from about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, 26%, 27%, 28%, 29%, 30%, 31%, 32%, 33%, 34%, 35%, 36%, 37%, 38%, 39%, or 40%, or any value in between. In some embodiments, polyols are present in the oil phase in amounts ranging from about 5% to about 25% by weight, based on the dry weight of the oil phase.

[0181] The weight percentage of the water-soluble polymer in the aqueous phase is calculated by the amount present in the oil phase due to interactions with the oil phase itself and / or oil phase components (e.g., a first adduct, an optional second polyfunctional crosslinking agent). The water-soluble polymers described herein may be present in the aqueous phase in amounts of about 0.5% to about 15% by weight of the dry weight of the oil phase. This includes about 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, or 15%, or any value in between. In some embodiments, the water-soluble polymers described herein are present in the aqueous phase in amounts of about 3% to about 12% by weight, or about 5% to about 10% by weight, of the dry weight of the oil phase.

[0182] The water-soluble polymer may be a reactive water-soluble polymer that crosslinks with one or more of the first adduct and the third polyfunctional crosslinking agent (if present). In some embodiments, the water-soluble polymer is a reactive water-soluble polymer that crosslinks with the first adduct, the third polyfunctional crosslinking agent (if present), the third adduct (if present), or any combination of two or more of them.

[0183] In some embodiments, the water-soluble polymer is a non-reactive water-soluble polymer and does not covalently bond to any components in the oil or aqueous phase (e.g., a first adduct, a third polyfunctional crosslinking agent (if present), a third adduct (if present), or any combination of two or more of these).

[0184] In some embodiments, the aqueous phase further comprises a water-soluble low molecular weight chain extender or crosslinking agent. The inclusion of a water-soluble low molecular weight chain extender or crosslinking agent can increase the degree of crosslinking of the random polymerization product. Examples of water-soluble low molecular weight chain extenders or crosslinking agents include, but are not limited to, polyfunctional amines such as ethylenediamine, diethylenetriamine, and triethylenetetraamine.

[0185] In some embodiments, the aqueous phase further comprises a surfactant. In some embodiments, the surfactant is a nonionic surfactant. In some embodiments, the nonionic surfactant preferably has an average HLB (hydrophilic-lipophilic balance) value of about 12 to about 15. Examples of nonionic surfactants include, but are not limited to, TRITON® X-114 ((1,1,3,3-tetramethylbutyl)phenyl polyethylene glycol), SILWET® L-7604 (siloxane polyalkylene oxide copolymer), and combinations thereof.

[0186] The weight percentage of surfactant in the aqueous phase is calculated by the amount present in the oil phase for interaction with or adsorption to the oil phase. The surfactant may be present in the aqueous phase in amounts ranging from about 0.01% to about 2% by weight, based on the dry weight of the oil phase. This includes amounts ranging from about 0.05%, 0.075%, 0.1%, 0.25%, 0.5%, 0.75%, 1%, 1.25%, 1.5%, 1.75%, or 2%, or any value in between. In some embodiments, the surfactant is present in the aqueous phase in amounts ranging from about 0.05% to about 2% by weight, or from about 0.1% to about 1% by weight, based on the dry weight of the oil phase.

[0187] In some embodiments, the aqueous phase further comprises an antifoaming agent or foam inhibitor. In some embodiments, the antifoaming agent is FOAMSTAR® ST 2410 (a star-shaped polymer-based antifoaming agent).

[0188] Polyethyleneimine intermediates can be used as antimicrobial compounds. In some embodiments, quaternization occurs on pendant substitution rather than on the polyethyleneimine skeleton. Therefore, in another embodiment, Antimicrobial compounds selected from TIFF2026514865000055.tif86136, or any two or more copolymers or blends thereof, are provided herein, in the formula, Each Y 3 These are independently H or -OY 2 And, Each Y 2 These are independently H or -C(O)-NHR 30 And, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 is, -N + (R 20 )3X - It is a C1-C6 alkyl substituted with, and each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0189] In some embodiments, each Y 2 H is H.

[0190] In some embodiments, the compound is selected from the following: TIFF2026514865000056.tif223165* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000057.tif36128, and B is, TIFF2026514865000058.tif34128, where each n is an integer independently selected from 1 to 3000 or 2 to 3000, preferably an integer independently selected from 10 to 100. In some embodiments, one or more bromide anions are X independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. - It has been replaced with.

[0191] In some embodiments, the compound is selected from the following: TIFF2026514865000059.tif218150* indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) ***Actual stoichiometric ratio determined by NMR analysis In the table, A is, The filename is TIFF2026514865000060.tif35128, and B is, The file is TIFF2026514865000061.tif34128, where each n is an integer independently selected from 1 to 3000 or 2 to 3000, preferably an integer independently selected from 10 to 100, and each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0192] A second adduct, which is a random polymerization product of the polyethyleneimine intermediate and a (polyfunctional) crosslinking agent disclosed herein, may be used as an antimicrobial compound. Thus, in another embodiment, a random polymerization product of a polyethyleneimine intermediate and a crosslinking agent is provided herein, wherein the polyethyleneimine intermediate is TIFF2026514865000062.tif86136, or any two or more copolymers or blends thereof, selected from the formula, Each Y 3 These are independently H or -OY 2 And all Y 3 However, it cannot be H, Each Y 2 These are independently H or -C(O)-NHR 30 And all Y 2 However, -C(O)-NHR 30 It cannot be, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 is, -N + (R 20 )3X - It is a C1-C6 alkyl substituted with, and each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, as well as (2) halogens, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Selected from the aryl group, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0193] In some embodiments, the crosslinking agent is a polyisocyanate. In some embodiments, the polyisocyanate is prepared from a diisocyanate independently selected from the group consisting of hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), toluene diisocyanate (TDI), methylenediphenyl diisocyanate (MDI), xylene diisocyanate (XDI), methylene-bis-(4-cyclohexyl isocyanate) (H12MDI), meta-tetramethylxylene diisocyanate (TMXDI), and trimethylhexamethylene diisocyanate (TMDI). In some embodiments, the polyisocyanate is independently selected from the group consisting of DESMODUR® N-3300, DESMODUR® N-100, DESMODUR® Z4470SN, WANNATE® T-series polyisocyanates, and LUPRANATE® M-series polyisocyanates.

[0194] In some embodiments, the random polymerization product is of formula (I), TIFF2026514865000063.tif43128 formula, Each A is independent, TIFF2026514865000064.tif132132, or any two or more copolymers or blends thereof, wherein each attachment of A forms a carbamate linkage, Each Y 3 These are independently H or -OY 2 And all Y 3 However, it cannot be H, Each Y 2 These are independently H or -C(O)-NHR 30 And all Y 2 However, -C(O)-NHR 30 It cannot be, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 is, -N + (R 20 )3X - It is a C1-C6 alkyl substituted with, and each R 20 It is independently, C1-C 18 Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, (2)halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Ariel, and (3) Selected from TIFF2026514865000065.tif42128, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R cThese are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, Each R 40 These may be independently substituted with phenyl or a 3- to 8-membered cycloalkyl ring - (C1-C 10 Alkilen)- each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0195] In some embodiments, the random polymerization product is of formula (II), TIFF2026514865000066.tif43128In formula, Each A is independent, TIFF2026514865000067.tif131132, or any two or more copolymers or blends thereof, wherein the attachment of each A forms a carbamate linkage, Each Y 3 These are independently H or -OY 2 And all Y 3 However, it cannot be H, Each Y 2 These are independently H or -C(O)-NHR 30 And all Y 2 However, -C(O)-NHR 30 It cannot be, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C2-C6 alkylene)-, Each R 10 is, -N + (R 20 )3X - It is a C1-C6 alkyl substituted with, and each R 20 It is independently, C1-C 18Alkyl; C1-C having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N 18 Heteroalkyl; as well as C6-C6 alkyl; may be substituted with -(C1-C6 alkyl), -(C1-C6 alkoxy), -C(O)O-(C1-C6 alkyl), -C(O)NH(C1-C6 alkyl), -C(O)N(C1-C6 alkyl)2, or -OC(O)-(C1-C6 alkyl). 10 Selected from the group consisting of aryls, Each R 21 These are independently -OH, -(C1-C6 alkoxy), carboxy, -(C6-C 10 aryl), -C(O)O(C1-C6 alkyl), -C(O)-(C6-C 10 Selected from C1-C6 alkyl groups, which may be substituted with substituents selected from aryl groups and -OH-substituted C1-C6 alkyl groups, Each R 30 These are independently (1) halogen, -SiR a (OR b )(OR c ), and -(C6-C 10 C6-C may be substituted with 1 to 3 substituents independently selected from the aryl group. 20 Alkyl, (2)halogen, -(C1-C6 alkyl), and -SiR a (OR b )(OR c C6-C may be substituted with 1 to 3 substituents independently selected from ) 10 Ariel, and (3) Selected from TIFF2026514865000068.tif42128, in the formula, each R a Each R is independently -(C1-C6 alkyl), and each R b and each R c These are independently selected from -(C1-C6 alkyl) and -Si(C1-C6 alkyl)3, Each R 40 These may be independently substituted with phenyl or a 3- to 8-membered cycloalkyl ring - (C1-C 10 Alkilen)- each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0196] Provided herein, in another embodiment, are polymers having wound-healing properties comprising, essentially comprising, or consisting of a polyethyleneimine intermediate, wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:1.

[0197] In some embodiments, the polymer is selected from the group consisting of: TIFF2026514865000069.tif223165* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000070.tif36128, and B is, The filename is TIFF2026514865000071.tif34128, where each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100.

[0198] In some embodiments, the polymer is selected from the group consisting of: TIFF2026514865000072.tif156165* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** In the table, A is, The filename is TIFF2026514865000073.tif36128, and B is, TIFF2026514865000074.tif34128, where each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100. In some embodiments, one or more bromide anions are X independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. - It has been replaced with.

[0199] In some embodiments, the polymer is selected from the group consisting of: TIFF2026514865000075.tif218150* indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) ***Actual stoichiometric ratio determined by NMR analysis In the table, A is, The filename is TIFF2026514865000076.tif35128, and B is, The file is TIFF2026514865000077.tif34128, where each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100, and each X - These are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, as well as their organically substituted derivatives.

[0200] It will be understood that the polymers described herein and the general methods for preparing them offer considerable versatility for tuning and fine-tuning their physical and chemical properties, as well as their antimicrobial properties, for a wide range of different surfaces, substrates, and applications. Examples of variables available for this fine-tuning include, but are not limited to, the structure and amount of a first quaternary ammonium salt, an optional polyol, an optional chain extender, a water-soluble polymer, a first polyfunctional crosslinker (e.g., a first polyisocyanate), a polyethyleneimine intermediate or a second adduct (including its second polyfunctional crosslinker, e.g., a second polyisocyanate), an optional third polyfunctional crosslinker (e.g., a third polyisocyanate), an optional second quaternary ammonium salt, an optional fourth polyfunctional crosslinker (e.g., a fourth polyisocyanate), and the degree of crosslinking. Furthermore, it should be understood that polyfunctional crosslinking agents other than polyisocyanates may be used, including but not limited to polyfunctional epoxides, imines, carbodiimides, and aldehydes.

[0201] Compositions and formulations In another embodiment, what is provided herein is a composition comprising, essentially comprising, or consisting of a polymer component described herein.

[0202] In another embodiment, what is provided herein is, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A composition containing, essentially being, or consisting of.

[0203] In some embodiments, the composition comprises, essentially consists of, or consists of polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites, and the polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites are (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) optionally, a third polyfunctional crosslinking agent, comprising, essentially consisting of, or comprising.

[0204] In some embodiments, the composition comprises, essentially consists of, or comprises polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites, wherein the polymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprise, essentially consist of, or comprise a first adduct, a polyol, a water-soluble polymer, and optionally a third polyfunctional crosslinking agent.

[0205] In some embodiments, the composition comprises, is essentially, or consists of the polyethyleneimine intermediates described herein.

[0206] In some embodiments, the composition includes, is essentially, or consists of the second adduct described herein.

[0207] In some embodiments, the polymer component includes, is essentially, or consists of polymers or interpenetrating polymer networks described in U.S. Provisional Application No. 63 / 410,714 or U.S. Provisional Application No. 63 / 410,722 (the contents of both of which are incorporated herein by reference).

[0208] In some embodiments, the polymer component is present in the composition upon administration to the subject or to the wound site of the subject. In some embodiments, precursors of the polymer component are present in the composition upon administration to the subject or to the wound site of the subject, and the precursors react with each other to provide the polymer component. In non-limiting examples, the composition comprises, is essentially derived from, or consists of an oil-in-water emulsion described herein. In some embodiments, the oil-in-water emulsion is as described in U.S. Provisional Application No. 63 / 410,714 or U.S. Provisional Application No. 63 / 410,722.

[0209] The compositions described herein may contain at least one pharmaceutically acceptable excipient.

[0210] The compositions described herein may be formulated for topical administration. Topical formulations include, but are not limited to, creams, gels, pastes, foams, sprays, powders, emulsions, liquids, or ointments. In some embodiments, the liquid is a solution. In some embodiments, the liquid is a suspension. In some embodiments, the liquid is an oil.

[0211] Examples of pharmaceutically acceptable excipients include solvents, thickeners, preservatives, emulsifiers and / or surfactants, pH adjusters and buffers, penetration enhancers, antioxidants, chelating agents, solubilizers, viscosity enhancers, and emollients. “Pharmaceutically acceptable” means a non-biological or otherwise undesirable material that, for example, can be incorporated into a pharmaceutical composition administered to a patient without causing any undesirable biological effects or interacting in a harmful manner with any other components of the composition in which it is contained. When the term “pharmaceutically acceptable” is used to refer to a pharmaceutical carrier or excipient, it means that the carrier or excipient meets the required standards for toxicity and manufacturing testing, or is included in the inactive ingredient guide provided by the U.S. Food and Drug Administration.

[0212] Examples of solvents include, but are not limited to, sterile water, glycerin, medium-chain triglycerides, isopropyl myristate, diisopropyl adipate, isopropyl palmitate, propylene glycol, olive oil, castor oil, coconut oil, light mineral oil, diethylene glycol monoethyl ether (TRANSCUTOL® P), diethyl sebacate, benzyl alcohol, cyclomethicone, PEG400, dehydrated alcohol, and dimethyl isosorbide.

[0213] Thickening agents may be selected from cross-linked polyacrylic acid polymers (e.g., carbomers), cellulose derivatives (e.g., hydroxyethylcellulose, ethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose), xanthan gum, locust bean gum, guar gum or their derivatives, alginic acid, inorganic polymers (such as Weegum, aluminum and magnesium silicates), PEMULEN® (a copolymer of acrylic acid and C10-C30 alkyl acrylates cross-linked with allyl pentaerythritol), or any combination thereof. Examples of thickening agents include, but are not limited to, xanthan gum, cetearyl alcohol, PROMULGEN® D, CARBOPOL® 974P NF polymer, PEMULEN® TR-2, PEMULEN® TR-1, KLUCEL® HG Pharm, CARBOPOL® 980NF polymer, and SEPINEO® P600. Commercially available carbomers include, but are not limited to, CARBOPOL® Ultrez 10 NF, CARBOPOL® Ultrez 20, CARBOPOL® ETD 2020 NF, CARBOPOL® 71G NF, CARBOPOL® 971P NF, CARBOPOL® 974P NF, CARBOPOL® 980 NF, CARBOPOL® 981 NF, and CARBOPOL® 5984 EP. CARBOPOL® Ultrez 10 NF and CARBOPOL® ETD 2020 NF are carbomer homopolymers or copolymers containing a block copolymer of polyethylene glycol and a long-chain alkylate ester.

[0214] Examples of preservatives include, but are not limited to, phenoxyethanol, urea derivatives (diazolidinyl urea and imidazolidinyl urea), ethylhexylglycerin, hydantoin, benzoic acid, sorbic acid, anisic acid, methylparaben, and propylparaben.

[0215] Examples of emulsifiers include, but are not limited to, BRIJ® L4, ARLACEL® 165, TWEEN® 20, BRIJ® S721, BRIJ® S2, PROMULGEN® D, stearalkonium chloride, PEMULEN® TR-2, PEMULEN® TR-1, sodium monostearate, SEPINEO® P600, laureth-4, polysorbate 20, sorbitan monostearate, and PEG-35 castor oil. Examples of nonionic emulsifiers include, but are not limited to, BRIJ® L4, ARLACEL® 165, sodium monostearate, laureth-4, polysorbate 20, and PEG-35 castor oil. Examples of cationic surfactants include, but are not limited to, stearalkonium chloride.

[0216] Examples of pH adjusters and buffers include, but are not limited to, triethanolamine, hydrogen chloride, sodium hydroxide, potassium hydroxide, and cocoamide diethylamine.

[0217] Examples of penetration enhancers include dimethyl sulfoxide (DMSO) and decylmethyl sulfoxide (C 10Examples of substances that may be found include, but are not limited to, sulfoxides such as MSO; ethers such as diethylene glycol monoethyl ether (commercially available as TRANSCUTOL® P) and diethylene glycol monomethyl ether; 1-substituted azacycloheptan-2-ones such as 1-n-dodecyl-cycloazaicycloheptan-2-one; alcohols such as propanol, octanol, and benzyl alcohol; fatty acids such as lauric acid, oleic acid, and valeric acid; fatty acid esters such as isopropyl myristate, isopropyl palmitate, methylpropionate, and ethyl oleate; polyol esters and amides such as butanediol and polyethylene glycol monolaurate; as well as urea, N,N-dimethylacetylamide (DMA), N,N-dimethylformamide (DMF), 2-pyrrolidone, 1-methyl-2-pyrrolidone, ethanolamine, diethanolamine, and triethanolamine; terpenes and terpinoids; alkanones; organic acids such as salicylic acid and salicylates, citric acid, and succinic acid; and any mixtures thereof. Suitable penetration enhancers include, but are not limited to, medium-chain triglycerides, isopropyl myristate, diisopropyl adipate, isopropyl palmitate, propylene glycol, diethylene glycol monoethyl ether (TRANSCUTOL® P), oleyl alcohol, dehydrated alcohol, benzyl alcohol, laureth-4, diethyl sebacate, and dimethyl isosorbide.

[0218] Examples of antioxidants include, but are not limited to, citric acid, butylated hydroxytoluene, ascorbic acid, glutathione, retinol, α-tocopherol, β-carotene, α-carotene, ubiquinone, butylated hydroxyanisole, ethylenediaminetetraacetic acid, selenium, zinc, lignans, uric acid, lipoic acid, and N-acetylcysteine.

[0219] Examples of chelating agents include, but are not limited to, EDTA, its salts and / or solvates; citric acid; and tartaric acid.

[0220] Examples of solubilizing agents include, but are not limited to, laureth-4.

[0221] Examples of viscosity enhancers include, but are not limited to, PEG3350.

[0222] Examples of softening agents include, but are not limited to, olive oil, medium-chain triglycerides, isopropyl myristate, diisopropyl adipate, isopropyl palmitate, castor oil, light mineral oil, cyclomethicone, diethyl sebanate, benzyl alcohol, PEG-35 castor oil, and coconut oil.

[0223] wound dressing In another embodiment, what is provided herein is a wound dressing comprising the polymer component described herein.

[0224] In another embodiment, what is provided herein is, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A wound dressing containing a polymer component selected from the group consisting of the following.

[0225] In some embodiments, the outer layer of the wound dressing contains a polymer component. In some embodiments, the polymer component is impregnated into the wound dressing.

[0226] The dressings described herein include or comprise coatings, coating fluids, or spray fluids comprising, essentially, or consisting of the compositions described herein. The dressings are configured to beneficially absorb exudate, maintain moisture, facilitate gas exchange, provide thermal separation, act as anti-infective (e.g., between the wound site and the environment), be easily removable, and be biocompatible. In some embodiments, the dressings are configured to be disposable and / or sterilizable. In some embodiments, the dressings are configured for use in topical negative pressure therapy.

[0227] For example, such dressings may include wraps, covers, barriers, layers, packings, gauze, plaster, bandages, lint, sutures, films, foam products, hydrogels, hydrocolloids, alginate products, bioactive products, tissue manipulation skin substitutes, medicinal products, liquid bandages, smart dressings, or composite products (which may include two or more of the aforementioned or substitutes), or any combination of any of the aforementioned.

[0228] In particular, dressings may be constructed from one or more natural polymers, one or more synthetic polymers, or blends thereof. Natural polymers include (a) cellulose and its compounds which can be used for ulcer dressings, for example, including pain relief and improved recovery time; (ii) alginates composed of polysaccharide chains which contribute to coagulation during wound healing and drug release; (ii) complex branched glucans including extra polysaccharides composed of dextran and glucose molecules; (iii) polysaccharides including chitosan, linear polysaccharides, and chitin, glucose amide derivatives, and (iv) hyaluronic acid, for example glycosaminoglycans which can be injected in gel form; (b) polysaccharide sulfates including (i) heparin which has a blood coagulation effect and (ii) chondroitin; and (c) proteins including (i) collagen and (ii) fibrin which is a blood coagulant. Examples of synthetic polymers include (a) polycaprolactone, (b) polyglycolic acid, which is a biodegradable polystyrene, (c) polylactic acid, which is also a biodegradable polystyrene, (c) polylactic acid co-glyolic acid, which is a polymer of polylactic acid and glycolic acid, (d) polyvinyl alcohol, (i) polyurethane, (f) polyorthoester, and (g) polytetrafluoroethylene.

[0229] In another embodiment, an antibacterial barrier can be applied to a wound site by providing the above-mentioned covering material with one of the compositions described herein (e.g., in the form of a coating, coating fluid, or spray fluid), thereby enabling control of bacteriostatic activity while promoting cell and tissue proliferation and regeneration. Furthermore, by preventing or reducing the likelihood of infection, the compositions according to the techniques of this disclosure prevent functional damage and / or loss that may result from infection. The compositions disclosed herein are antibacterial against both Gram-negative and Gram-positive bacterial strains, including, for example, methicillin-resistant Staphylococcus aureus (MRSA), without causing bacterial resistance. In some embodiments, the compositions described herein may be used alone or in combination with one or more drugs and / or one or more medical devices for use in both humans and animals for multiple indications, including, for example, acute wound care, chronic wound care, burn care, local infection, systemic infection, sepsis, and necrosis.

[0230] In some embodiments, a dressing comprising the composition described herein further comprises at least one indicator. The at least one indicator may be, for example, an internal indicator or an external indicator. The at least one indicator is configured to provide an indication of one or more parameters, such as temperature, pH, humidity, or oxygenation. For example, in some embodiments, the dressing may undergo a color change in response to contact with a microenvironment of bacterial infection. The selection of a particular type of dressing, composition, and optionally an indicator allows for the personalization of treatment. Furthermore, by providing indicators, the level of effectiveness, such as wound condition and / or healing condition, can be communicated to the care provider by such a “smart dressing.”

[0231] In some embodiments, a coating comprising the compositions described herein is a medicinal product. When used herein, the “medicinal product” coating contains at least one additional pharmaceutical agent. Suitable additional pharmaceutical agents include, but are not limited to, anti-inflammatory agents, anesthetic agents, additional anti-infective agents, or combinations thereof.

[0232] In some embodiments, the coating consists of, includes, or substantially consists of, the compositions according to embodiments of the present disclosure. In some embodiments, the coating is prepared by modifying an existing coating, for example, by combining or adding the compositions according to embodiments of the present disclosure.

[0233] In another embodiment, a method for producing an antimicrobial coating includes providing a coating containing one or more of the natural polymers or synthetic polymers discussed above, and applying a coating, coating fluid, or spray fluid to a coating, coating, or coating fluid which is essentially made from or composed of the compositions described herein. For example, the method may include, for instance, (i) spraying a spray fluid onto a coating material, (ii) immersing the coating material in a fluid, thereby immersing the coating material in the fluid, (iii) impregnating the fibers of the coating material with the fluid, (iv) applying a layer of coating to the surface of the coating material, (v) adhering a backing material containing the coating to the coating material, (vi) applying microneedles containing the composition to the natural or synthetic polymer of the coating material, or (vii) constructing the fibers of the coating material with polymer components within the coating material, for example, using electrospinning to produce nanofibers containing the polymer(s), copolymer(s), or interpenetrating polymer network(s) described herein, or by alternative techniques, contacting natural and / or synthetic polymers with a coating, coating fluid, or spray fluid.

[0234] Therefore, in another embodiment, what is provided herein is a method for preparing a wound dressing as described herein, wherein a composition comprising a polymer component is used. (i) spraying the composition onto a fibrous material, (ii) Immersing a fibrous material in a fluid containing the composition, (iii) Impregnating the fibers of a fibrous material with a fluid containing the composition, (iv) Applying a coating layer containing the composition to the surface of a fibrous material, (v) Adhering a backing material containing the composition to a fibrous material, (vi) Applying microneedles containing the composition to a fibrous material, (vii) embedding a layer containing the composition within a fibrous material, (viii) constructing fibers of a fibrous material containing a composition by electrospinning, (ix) Interleaving fibers containing the composition with fibers of a fibrous material. The method involves integrating into a fibrous material by one of the following means.

[0235] In another embodiment, the foregoing provides a method for producing a polyurethane foam wound dressing, comprising integrating a composition containing polymer components into a polyurethane foam wound dressing by mixing the composition with polyurethane before curing.

[0236] How to use In another aspect, provided herein are methods for preventing or reducing bacterial growth or reducing infection in a wound, surgical site, or implant, wherein the method involves applying the following to the wound, surgical site, or implant: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising applying or coating a composition containing, essentially consisting of, or comprising the following.

[0237] In another embodiment, provided herein is a method for treating a wound or surgical site in a person in need thereof, wherein the wound or surgical site is (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially being, or consisting of applying a composition containing.

[0238] In another embodiment, provided herein is a method for promoting the healing of a wound or surgical site in a person in need thereof, wherein the wound or surgical site is (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially being, or consisting of applying a composition containing.

[0239] In some embodiments, the wound is infected. In some embodiments, the wound is not infected.

[0240] In another embodiment, provided herein is a method for protecting a wound site in an area where such protection is needed, comprising covering at least a portion of the wound site with a dressing, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising contacting a composition containing, or comprising, essentially consisting of, or comprising.

[0241] In some embodiments, the composition is positioned on the dressing before contact with the wound site. In some embodiments, the composition is applied to the wound site before the wound site comes into contact with the dressing.

[0242] In another embodiment, provided herein is a method for preventing or reducing infection in a subject where such prevention or reduction is needed, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially, or consisting of administering a composition containing.

[0243] In another embodiment, provided herein is a method for treating an infection in a subject in need, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially, or consisting of administering a composition containing.

[0244] In some embodiments, the infection is localized. In some embodiments, the infection is systemic.

[0245] In another aspect, provided herein is a method for treating sepsis in a subject in need, (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially, or consisting of administering a composition containing.

[0246] In another embodiment, provided herein is a method for preventing or reducing necrosis in an object in need, wherein the object (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising, essentially, or consisting of administering a composition containing.

[0247] In another aspect, provided herein are methods for preventing or reducing bacterial growth or reducing infection in a wound, surgical site, or implant, wherein the method involves applying the following to the wound, surgical site, or implant: (1)(i) A first adduct comprising a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) A polyethyleneimine intermediate, or a second adduct of a polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites that include, essentially consist of, or comprise them. (2) Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, and composites comprising, essentially, or consisting of, a first adduct, polyol, water-soluble polymer, and optionally, a third polyfunctional crosslinking agent. (3) Polyethyleneimine intermediate, (4) Second appendage, and (5) A combination of two or more of them A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A method comprising applying or coating a composition containing, essentially consisting of, or comprising the following.

[0248] In some embodiments, the subject is either a human or an animal.

[0249] In some embodiments, the wound is an external wound. External wounds include, but are not limited to, abrasions, lacerations, punctures, delaminations, skin lacerations, and burns. In some embodiments, the wound is an internal wound. In some embodiments, the wound is a complication of a disease or disorder. Non-limiting examples include diabetic ulcers, venous ulcers, and arterial ulcers.

[0250] The compositions disclosed herein are administered to a subject in an effective or therapeutically effective amount. “Effective amount” means an amount of the compound sufficient to produce the desired effect, e.g., to prevent bacterial growth, necrosis, and / or infection.

[0251] The description of embodiments of this disclosure is not intended to be exhaustive or to limit the disclosure to the exact form disclosed. Specific embodiments and examples of the disclosure are described herein for illustrative purposes, but various equivalent modifications are possible within the scope of the disclosure, as will be recognized by those skilled in the art. For example, while method steps or functions are presented in a given order, alternative embodiments may perform the functions in a different order, or the functions may be performed substantially simultaneously. The teachings of the disclosure provided herein may be applied to other procedures or methods where appropriate. Further embodiments may be provided by combining the various embodiments described herein. Aspects of the disclosure may be modified, as needed, to adopt compositions, functions, and concepts of the above-mentioned references and uses to provide further embodiments of the disclosure. Furthermore, several modifications may be made to the protein structure without affecting the type or amount of biological or chemical action, taking into consideration biological functional equivalence. These and other modifications may be made to the disclosure in light of the detailed description. All such modifications are intended to be included within the scope of the appended claims.

[0252] Any particular element of any of the embodiments described above may be combined with or substituted for an element of another embodiment. Furthermore, while the advantages associated with specific embodiments of this disclosure are described in the context of those embodiments, other embodiments may also demonstrate such advantages, and not all embodiments are required to demonstrate advantages that fall within the scope of the Art.

[0253] The techniques described herein are further illustrated by the following examples, which should not be construed as further limitations. Methods and materials similar to or equivalent to those described herein may be used in the practice or testing of this disclosure, but preferred methods and materials are described below. [Examples]

[0254] Although the technology has been generally described herein, it will be more readily understood by referring to the following examples. These are included solely for illustrative purposes of specific aspects and embodiments of the technology and are not intended to limit the technology.

[0255] Synthesis example Examples 1-4. Aqueous compositions containing or not containing a water-soluble polyethyleneimine intermediate. TIFF2026514865000078.tif61162

[0256] Preparation of the aqueous phase: 3.1 parts of HEC 380K (Aldrich, 2-hydroxyethylcellulose, average Mw=380,000) were completely dissolved in 96.9 parts of DI water. The pH of the solution was adjusted to 4.5 with a 5% H3PO4 solution.

[0257] Example 1: Preparation of a polymer free of polyethyleneimine intermediates Preparation of the oil phase: 5.0 g (10.7 mmol) of well-dried C18DMDEG was added to a solution of 7.67 g (16.03 mmol, 48 mmol reactive NCO) of DESMODUR® N100 in 5 g of dry toluene at 90°C under nitrogen, and the mixture was reacted for 15 hours. After removing the toluene under reduced pressure, a clear viscous liquid (first adduct) was obtained.

[0258] 4.144 parts of the first adduct (N100-C18DMDEG(Br-)), 0.356 parts of PTMG 1000 (Aldrich poly(tetramethylene glycol), average Mn=1000), and 1.5 parts of MEK (methyl ethyl ketone) were pre-reacted at 70°C for 1 hour. The mixture was cooled to room temperature and dried under vacuum until the solids content reached approximately 90% by weight. To the solution, 0.828 parts of polyisocyanate N100 (Convestro DESMODUR N100) and 1.276 parts of dry acetone were added and mixed homogeneously.

[0259] Preparation of oil-in-water emulsions The aqueous solution prepared above was added to the oil phase at room temperature and emulsified five times by sonication (100 watts) for 10 seconds each, with a 10-second pulse between each sonication treatment. The total emulsification time was approximately 90-120 seconds. After heating at 60°C for 15 hours, a polymer product was obtained.

[0260] Examples 2-4 Preparation of QPEI 37169 TIFF2026514865000079.tif40135QPEI 37169 was prepared as shown in the reaction scheme above.

[0261] For the purposes of the chemicals described herein, the ratio of primary, secondary, and tertiary amines in branched PEI is assumed to be 1:2:1, as reported in the literature. See, for example, Klibanov, A., et al., (2006). “One-Step Painting-Like Coating Procedures to make Surfaces Highly and Permanently Bactericidal.” Biotechnol. Prog., 22(2):584-589, and Gao, B., et al., (2007). “Studies on the Preparation and Antibacterial Properties of Quaternized Polyethyleneimine.” J. Biomaterials Science, Polymer Edition, 18(5):531-544.

[0262] The procedure used is essentially as described in Gao et al. (2007). The structure of QPEI 37169 is intended to be an approximation showing that most primary and secondary amines react with epoxides, and most tertiary amines are quaternized by alkylation with benzyl chloride.

[0263] 3.33 g of 70 kDa PEI solution (assuming 30% PEI / 1 g in water, mw = 43.1 g / mol, 23.2 mmol) was added to a 25 mL two-necked flask under nitrogen and cooled to 0°C. 5.4 g (92.8 mmol) of propylene oxide was added dropwise to this mixture at 0–3°C. After the addition was complete, the reaction mixture was stirred at 0–3°C for 7 hours. The temperature of the reaction mixture was then raised to 35°C, and the unreacted propylene oxide was distilled (approximately 3.60 mL). 11.75 g (10.6 mL, 92.8 mmol) of benzyl chloride was added to the resulting solution, and the reaction mixture was heated at 50°C for 30 hours. The reaction mixture was extracted with diethyl ether (3 × 20 mL) to remove unreacted benzyl chloride, residual propylene oxide, and any oleophilic by-products or impurities. The aqueous phase was separated, vaporized under vacuum, and dried by freeze-drying to leave QPEI 37169 as a clear solid (2.85 g). The product was characterized by proton NMR and infrared (IR) spectroscopy. QPEI 37169 contains nitrogen functionalization with benzyl chloride versus propylene oxide in a ratio of approximately 1:1 (i.e., the number of benzyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atoms).

[0264] Preparation of QPEI HB37169 The same reaction used for preparing QPEI HB37169 was used for preparing QPEI HB37169, except that a branched polyethyleneimine of the same molecular weight was used.

[0265] Preparation of QPEI HB37478 The same reaction used in the preparation of QPEI 37169 was applied to the preparation of QPEI HB37478, except that the quaternizing agent benzyl bromide was replaced with hexyl bromide and a branched polyethyleneimine of the same molecular weight was used.

[0266] Examples 5-9. QPEI 37169 as a polyethyleneimine intermediate in the aqueous phase

[0267] [Table 3]

[0268] The compositions of Examples 5-9 were prepared using the same procedures as those in Examples 1-4, except that the compositions were modified as shown in Table 3.

[0269] Examples 10-20 illustrate examples of the addition of polyethyleneimine intermediates or second adducts that may be used in this technology.

[0270] Example 10. Synthesis of polyethyleneimine intermediate 40840 A thermometer, condenser, and magnetic stirrer were attached to a 500 mL three-necked round-bottom flask. The reaction flask was rinsed with nitrogen gas, and the reaction was carried out under a flow of nitrogen gas.

[0271] 10 g of PEI (70 kDa branched, 30 wt% aqueous solution, amine content 18 mmol / gram solid polymer, primary, secondary, and tertiary amine ratio = 1:2:1), potassium carbonate (37.07 g, 0.232 mol), and 150 mL of t-amyl alcohol were added to a round-bottom flask. The mixture was stirred under nitrogen for 30 minutes, and then 3-bromo-1-propanol (64.5 g, 0.464 mol, 1.3 equivalents for complete quaternization) was added dropwise at room temperature. The resulting mixture was heated and stirred at 95°C for 96 hours.

[0272] After 96 hours, the mixture was cooled to room temperature and filtered to remove insoluble solids. The filtered solid was washed with 150 mL of methanol. The combined filtrate was treated with 250 mL of diethyl ether, and a white precipitate was formed. The organic phase was decanted, the white solid was dissolved in 200 mL of methanol, and precipitated with 200 mL of diethyl ether. This dissolution / precipitation process was repeated two more times, and the resulting white paste-like solid was dried in a rotary evaporator and then further dried under high vacuum for 5 hours. The yield of the dried product was then 17.4 g. The product was then processed, 1The compounds were characterized by 1H NMR, and the degree of quaternization was analyzed using Mohr silver titration to measure the amount of bromide.

[0273] Example 11. Synthesis of polyethyleneimine intermediate 40660 A dropping funnel, condenser, and magnetic stirrer were attached to a 2L three-necked round-bottom flask (TIFF2026514865000082.tif481642). The reaction flask was rinsed with nitrogen gas, and the reaction was carried out under a flow of nitrogen gas.

[0274] 10 g of PEI (70 kDa branched, 30 wt% aqueous solution, amine content 18 mmol / gram solid polymer, primary, secondary, and tertiary amine ratio = 1:2:1) was added to a reaction flask, and 835 mL of water was added thereto. 114.3 g of glycidyltrimethylammonium chloride (0.754 mol, approximately 4 equivalents for theoretical complete conversion) was dissolved in 130 mL of water and added dropwise to the reaction mixture. 153 g (210 mL, 1.5 mol) of triethylamine was added dropwise to the reaction mixture at room temperature. The resulting two-phase reaction mixture was vigorously stirred at room temperature for 4 days, after which the reaction mixture was a single clear phase. All solvent was removed by rotary evaporator at 55°C. The paste-like liquid residue was dissolved in 200 mL of methanol, and the polymer product was precipitated with 400 mL of diethyl ether. This methanol / diethyl ether dissolution and precipitation was repeated 6 times. The final precipitate was dried in a rotary evaporator, and then dried under high vacuum to obtain 46.5 g of the final product. 1 The compounds were characterized by 1H NMR, and the degree of quaternization was analyzed using Mohr silver titration to determine the amount of chloride.

[0275] Example 12. Synthesis of polyethyleneimine intermediate 40818 A condenser, heating cup, and magnetic stirrer were attached to a 100 mL single-neck round-bottom flask. The reaction flask was rinsed with nitrogen gas, and the reaction was carried out under a flow of nitrogen gas.

[0276] 2 g of glycidyl-functionalized PEI (3.3 mmol, 13.3 mmol, reactive N), bromohexane (7 g, 40 mmol, 3 equivalents), and 4.4 mL of t-amyl alcohol were added to a flask, and the reaction mixture was heated at 96°C for 96 hours. The reaction mixture changed from colorless to pale orange. The reaction mixture was cooled to room temperature, and the resulting solution was poured into tertiary butyl methyl ether (TBME) with vigorous stirring to form a precipitate. The liquid was decanted from the precipitated solid, the solid was dissolved in methanol, and reprecipitation was performed with TBME. This process was repeated three times, and after drying in a rotary evaporator and then under high vacuum, 4.06 g of product was obtained. The product was then... 1 The compounds were characterized by 1H NMR, and the degree of quaternization was analyzed using Mohr silver titration to measure the amount of halides.

[0277] Example 13. Synthesis of a monoisocyanate-capped polyethyleneimine intermediate (approximately 85% of free OH groups) As shown below, the structure of the polymer product is intended to be an approximation indicating that the majority of the hydroxyl groups (approximately 85% molar equivalent) react with the monoisocyanate blend to form a urethane, while some hydroxyl groups remain unreacted. TIFF2026514865000084.tif54128

[0278] The concentration of reactive hydroxyl groups (mmol / gram of dry polymer) was determined by titrating a known amount (grams) of dry hydroxylalkyl quaternary polyethyleneimine (HA-Q-PEI) with a known excess amount (grams, mmol) of octadecyl isocyanate. The proportion of monoisocyanate consumed in the reactant was monitored using infrared (IR) spectroscopy at 2263 cm⁻¹. -1This was determined by monitoring the decrease in the isocyanate peak. From the percentage decrease in this peak, the number of millimoles of isocyanate consumed was estimated. This value corresponded to the number of millimoles of polymer hydroxyl groups that reacted with the isocyanate. In this way, the hydroxyl group concentration of the polymer (mmol reactive hydroxyl groups / g dry polymer) was calculated and then used in subsequent reactions to determine the amount of monoisocyanate(s) required to functionalize a specific percentage of reactive hydroxyl groups in the polymer, thereby fine-tuning the hydrophilic / hydrophobic properties of the polymer.

[0279] Using the procedure described in Example 2, 2.0 g (2.27 mmol, assuming a molecular weight of 881 g / mol per polymer unit cell) of hydroxypropyl quaternary ammonium PEI, QPEI 37169 was prepared, then dried under vacuum at 60°C for 2 hours, followed by storage overnight in a drying oven at room temperature. To the dried polymer, 13.8 g of t-butyl alcohol and 9.2 g of dimethylacetamide were added. The resulting mixture was stirred under nitrogen until the polymer was completely dissolved. Both of these solvents were thoroughly dried using a molecular sieve of 4 Å before use. A mixture of 1.6 g (5.41 mmol) of octadecyl isocyanate and 0.36 g (2.32 mmol) of octyl isocyanate was added dropwise to the polymer solution. This mixture totaled 7.73 mmol of monoisocyanate, corresponding to approximately 85% of the available hydroxyl groups. The reaction mixture became slightly cloudy. The resulting reaction mixture was stirred under nitrogen at room temperature for 12 hours. The resulting reaction mixture was filtered through a PTFE filter (pore size 1 μm) to obtain 20.83 grams of QPEI 37169 caps as a 12.19% solid solution. IR spectroscopy showed a novel peak expected to correspond to the urethane carbonyl, and no residual isocyanate peak was observed.

[0280] In some embodiments, after the reaction with monoisocyanate(s) was complete, the reaction mixture was added to water to precipitate the cap product. This product was isolated, washed with water to remove any water-soluble impurities, and then dried for use in the next step. This water precipitation step was useful in removing any water-soluble impurities that could contribute to toxicity.

[0281] Example 14. Process for crosslinking reaction of octadecyl / octylurethane quaternary ammonium PEI (Example of second adduct formation) As shown below, the structure of polymer compound (A) is intended to be an approximation indicating that some of the unreacted hydroxyl groups in the QPEI 37169 cap reacted with the polyisocyanate to form a urethane crosslink. TIFF2026514865000085.tif212118

[0282] Using the procedure described in Example 13, 20 g of octadecyl / octylurethane quaternary ammonium PEI was prepared, to which 1.25 g of Desmodur N3300 (50% solution in anhydrous acetone) and 0.18 g of a 1% solution of dibutyltin dilaurate in dry toluene were added. The resulting mixture was thoroughly mixed, and the reaction to form compound (A) was carried out at 60°C for 30 minutes to obtain the second adduct.

[0283] It should be noted that the above crosslinking procedure has also been carried out without the dibutyltin dilaurate catalyst.

[0284] Example 15. Aqueous solutions of HA-Q-PEI polymers having various PEI molecular weights, quaternary nitrogen groups, and anion counterions. The following formula: Various HA-Q-PEI (hydroxyalkyl quaternary PEI) from TIFF2026514865000086.tif39128 were prepared using a procedure similar to that described in Example 2 (Preparation of QPEI 37169). See Table 5 (R1 = methyl for each polymer).

[0285] [Table 5]

[0286] Example 16. Aqueous solutions of HA-Q-PEI polymers having various PEI molecular weights. The following formulas have various molecular weights: Additional HA-Q-PEI polymers (R1=methyl, R2=hexyl, X=bromide) from TIFF2026514865000088.tif39128 were prepared using a procedure similar to that described in Example 2 (preparation of QPEI 37169). See Table 6.

[0287] [Table 6]

[0288] Example 17. Preparation of the second adduct The following formula: The second adduct of TIFF2026514865000090.tif41128 was prepared by replacing octadecyl / octylurethane quaternary ammonium PEI with HA-Q-PEI (PEI: molecular weight = 70,000 (branched), R1 = methyl, R2 = hexyl, X = bromide) using a procedure similar to that described in Example 14, and crosslinking agent Z (DESMODUR® N100): The solution was prepared by varying the amount of TIFF2026514865000091.tif46128 (see Table 7).

[0289] [Table 7] *Weight percentage of the second appendage

[0290] Example 18. Polyethyleneimine intermediates with or without monoisocyanate substitution The following formula: Polyethyleneimine intermediate having monoisocyanate substitution (MUA-Q-PEI-A polymer, where R3=C) of TIFF2026514865000093.tif53128 18 Alkyl or C8 alkyl groups were prepared from HA-Q-PEI (PEI: molecular weight = 70,000 (branched), R1 = methyl, R2 = benzyl) and a monoisocyanate mixture (octadecyl isocyanate to octyl isocyanate in a 7:3 ratio), where approximately 90% of the HA-Q-PEI hydroxyl groups reacted with the monoisocyanate mixture (see a similar protocol in Example 13). The MUA-Q-PEI-A100 polymer was prepared similarly, where approximately 100% of the HA-Q-PEI hydroxyl groups reacted with the monoisocyanate mixture. See Table 8.

[0291] [Table 8]

[0292] Example 19. Second adduct using N3300 polyisocyanate crosslinking agent The following formula: The second adduct of TIFF2026514865000095.tif52128 (PUA-Q-PEI-B polymer, where R3=C) 18 Alkyl or C8 alkyl groups were prepared using a procedure similar to that described in Example 14. In particular, HA-Q-PEI (prepared from PEI: molecular weight = 25,000 (multibranched), R1 = methyl, R2 = hexyl, X = bromide) was reacted with a monoisocyanate mixture (7:3 ratio of octadecyl isocyanate to octyl isocyanate), where approximately 90% of the hydroxyl groups of HA-Q-PEI reacted with the monoisocyanate mixture, and the remaining hydroxyl groups were then reacted with various amounts of crosslinking agent Z (DESMODUR® N3300): I responded with TIFF2026514865000096.tif41128.

[0293] [Table 9] *Weight percentage of crosslinking agent relative to PUA-Q-PEI-B polymer product

[0294] Example 20. Compound 20-1 Compound 20-1 was similar to QPEI samples 3-8 and 3-9 of Example 16 and was prepared from PEI with MW = 270 kDa. Compound 20-1 (batch 105159) contains nitrogen functionalization with halogenated hexyl versus nitrogen functionalization with propylene oxide in a ratio greater than 1:1 (i.e., there are more hexyl groups than 2-hydroxypropyl groups on the nitrogen atom). Compound 20-1 (batch 99367) contains nitrogen functionalization with halogenated hexyl versus nitrogen functionalization with propylene oxide in a ratio of approximately 1:1 (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atom).

[0295] Example 21. Compound 21-1 Compound 21-1 is similar to compound HB37478 but is prepared from PEI with MW = 25 kDa. Compound 21-1 contains nitrogen functionalization with hexyl halogens versus nitrogen functionalization with propylene oxide in a ratio of approximately 1:1 (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atoms).

[0296] Example 22. Compound 22-1 Compound 22-1 (batch 109590) is similar to HB37478 of Example 4, but uses branched 70 kDa PEI instead of multi-branched 70 kDa PEI. Compound 22-1 (batch 109590) contains nitrogen functionalization with halogenated hexyl versus nitrogen functionalization with propylene oxide in a ratio of approximately 1:1 (i.e., the number of hexyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atoms).

[0297] Example 23. Compound 23-1 Compound 23-1 (batch 105402 and batch 109634) is similar to QPEI sample 2-9 of Example 15 (prepared from PEI with MW=70 kDa). Compound 23-1 (batch 105402 and batch 109634) contains nitrogen functionalization with phenacyl halogenate versus nitrogen functionalization with propylene oxide in a ratio of approximately 1:1 (i.e., the number of phenacyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atoms).

[0298] Example 24. Compound 24-1 Compound 24-1 (batch 109781) is similar to QPEI 37169 (prepared from PEI with MW=70kDa) in Example 2. Compound 24-1 (batch 109781) contains nitrogen functionalization with benzyl halide versus nitrogen functionalization with propylene oxide in a ratio of approximately 1:1 (i.e., the number of benzyl groups is approximately equal to the number of 2-hydroxypropyl groups on the nitrogen atoms).

[0299] Example 25. Compound 25-1 Compound 25-1 (batch 110417) is similar to compound 23-1, but is prepared from PEI with MW = 750 kDA.

[0300] Example 26. Compound 26-1 Compound 26-1 (batch 109831) is similar to polyethyleneimine intermediate 40660 (prepared from PEI with MW=70kDa) in Example 11.

[0301] Example 27. Compound 27-1 Compound 27-1 (batch 110420) is similar to polyethyleneimine intermediate 40818 (prepared from PEI with MW=70kDa) in Example 12.

[0302] Example 28. Compound 28-1 Compound 28-1 corresponds to the intermediate compound in the synthesis of QPEI 37169 in Example 2, which is obtained from the reaction of PEI (MW=70kDa) with propylene oxide. Therefore, no quaternary amine is present in compound 28-1.

[0303] Example 29. Compound 29-1 A dropping funnel, condenser, water bath, and mechanical stirrer were attached to a three-necked round-bottom flask (TIFF2026514865000098.tif371611L). The flask was rinsed with nitrogen gas, and the reaction was carried out under a flow of nitrogen gas.

[0304] 20 g of a 50% aqueous solution of 70 kDa branched PEI (10 g of PEI polymer, with a primary amine to secondary amine to tertiary amine ratio of approximately 1:2:1 and an amine content of 0.180 moles) was added to a flask and stirred at approximately 200 RPM. It should be noted that, theoretically, the 0.180 mole nitrogen content of primary, secondary, and tertiary amines in this ratio can react with 0.36 moles of alkyl halide, which in this example is defined as "1 equivalent of alkyl halide".

[0305] 150 ml of tert-amyl alcohol was added to the flask at ambient temperature, followed by the addition of K2CO3 (32.1 g, 0.232 mol). A mixture of bromopropanol (1.29 g, 0.0093 mol) and 1-bromohexane (151.86 g, 0.92 mol) (total alkyl halide = 0.93 mol, mol% content of each alkyl halide = 2.6 equivalents of 1% bromopropanol / 99% 1-bromohexane) was added dropwise at ambient temperature over 1 to 2 hours.

[0306] The reaction temperature was raised to 96°C, and the reactants were stirred at 96°C for 98 hours. The reactants were cooled to 25-30°C, filtered, and the filtered material was washed with methanol (50 ml). The filtrate was evaporated to dryness under vacuum while maintaining a temperature below 50°C. Diethyl ether (200 ml) was added to the residue, and the mixture was stirred at room temperature for 30-60 minutes, after which a light brown slurry was formed. This mixture was allowed to settle, and the supernatant was decanted. This grinding and decanting of the diethyl ether was repeated 3-4 times until the residual alkyl halide content in the decant layer was less than 0.5%, as determined by GC analysis.

[0307] After completing the grinding / decantation process, the mixture was evaporated to dryness under reduced pressure while maintaining the temperature below 40°C to obtain an off-white, sticky solid. This solid was dissolved in methyl ethyl ketone (100 mL) at 25–30°C, filtered through Celite, and the filtrate was evaporated to dryness under reduced pressure at 45°C. The resulting solid was oven-dried at below 45°C for 4–6 hours to obtain the product (37.8 g) as an off-white solid. The water content was measured as 0.24% by Karl Fischer analysis. The bromine content was measured as 23.6% by AgNO3 titration. The theoretical molar percentages of the PEI reaction with 1-bromopropanol and 1-bromohexane are 1% and 99%, respectively, assuming similar alkylation rates between the two alkyl halides.

[0308] Example 30. Compound 30-1 A four-necked round-bottom flask (TIFF2026514865000099.tif421531L) was fitted with a dropping funnel, condenser, water bath, and mechanical stirrer. The flask was rinsed with nitrogen gas, and the reaction was carried out under a flow of nitrogen gas.

[0309] Ten g of 25 kDa multibranched PEI (with an amine content of 0.180 moles, having a primary amine to secondary amine to tertiary amine ratio of approximately 1:1:1) was added to a flask with water (10 ml). Note that, theoretically, 0.180 moles of nitrogen content in this ratio of primary, secondary, and tertiary amines can react with 0.36 moles of alkyl halide. This is defined in this example as "one equivalent of alkyl halide".

[0310] 50 ml of tert-amyl alcohol was added to a flask at ambient temperature, and the suspension was stirred at 160–180 RPM. After stirring for 15–30 minutes, the mixture was cooled to 0–5°C, and 3.2 g, 0.023 mol, 0.064 equivalents of bromopropanol were added dropwise over 15–30 minutes at 0–5°C. The reaction mixture was stirred at 0–5°C for 4–5 hours, after which the temperature was raised to ambient temperature. The reactants were stirred at ambient temperature for 14–15 hours, after which the reaction mixture was a cloudy solution.

[0311] The water content of the reactants was reduced by azeotropic distillation of the solvent (approximately 10 mL). This volume of tert-amyl alcohol was added to the reactants, and the distillation process was repeated three times. Tert-amyl alcohol was added to restore the original reactant volume, and the resulting mixture was stirred at 50-60°C for 60-90 minutes, after which a clear solution was obtained.

[0312] A mixture of 1-bromooctadecane (232.1 g, 0.696 mol) and 1-bromooctane (44.8 g, 0.232 mol) (0.928 mol, 2.6 equivalents of alkyl halide) was added at 50-60°C. The temperature was raised to 94-98°C, and the reaction mixture was stirred at this temperature for 48 hours to obtain a clear brown solution. The solvent was removed under reduced pressure at below 60°C, and the resulting residue was cooled to 25-30°C. 500 mL of acetone was added. The resulting suspension was stirred at 25-30°C for 30-60 minutes. Stirring was stopped, and the suspension was allowed to settle for 1 hour. The supernatant was decanted from the solid, and 500 mL of acetone was added to the solid residue. This suspension was stirred at 25–30°C for 30–60 minutes, then the stirring was stopped, and the suspension was allowed to settle for 30–60 minutes. The supernatant was then decanted from the settled solid. This stirring, settling, and decanting process of the suspension was repeated several times until the levels of 1-bromooctadecane and 1-bromooctane in the supernatant were less than 0.5%, as measured by GC analysis.

[0313] The remaining solvent was removed under reduced pressure at a temperature below 35°C. The solid product was further dried at a temperature below 35°C for 8–10 hours to obtain 40.6 g of the QPEI product as a pale brown solid. The bromine content was determined to be approximately 23%, as measured by AgNO3 titration. The theoretical molar percentages of the reaction with 1-bromopropanol, as well as with a 75 / 25 mixture of 1-bromooctadecane and 1-bromooctane, are 6.4% and 93.6%, respectively.

[0314] Example 31. Compound 31-1 A dropping funnel, condenser, water bath, and mechanical stirrer were attached to a 0.5L four-necked round-bottom flask. The flask was rinsed with nitrogen gas, and the reaction was carried out under a nitrogen gas flow.

[0315] Ten g of 25 kDa multibranched PEI (with an amine content of 0.180 moles, having a primary amine to secondary amine to tertiary amine ratio of approximately 1:1:1) was added to a flask and stirred at 160-180 RPM. Note that, theoretically, the 0.180 mole nitrogen content of primary, secondary, and tertiary amines in this ratio can react with 0.120 moles of caprolactone ("one equivalent of caprolactone" in this example) and 0.360 moles of 1-bromohexane ("one equivalent of 1-bromohexane" in this example).

[0316] Water (10g) was added to a flask along with tert-amyl alcohol (50ml), and the resulting solid suspension was cooled to 0-5°C.

[0317] Caprolactone (2.65 g, 0.0238 mol, 0.2 equivalents) was added dropwise over 15-30 minutes at 0-5°C. The resulting mixture was stirred at 0-5°C for 4-5 hours. The temperature was raised to 25-30°C, and the reactants were stirred at this temperature for 14-15 hours to obtain a cloudy solution.

[0318] The tert-amyl alcohol was removed by distillation, and water was removed azeotropically from the reaction mixture. Fresh tert-amyl alcohol was added to replace the removed solvent. The reaction temperature was raised to 50-60°C, and the reactants were stirred for 60-90 minutes to obtain a clear solution. 1-bromohexane (153.2 g, 0.928 mol, 2.6 equivalents) was added. The resulting reaction mixture was stirred at 50-60°C for 15-30 minutes, and then the temperature was raised to 94-98°C. The reactants were stirred at this temperature for 48 hours to obtain a solid suspension.

[0319] The reaction mixture was cooled to 25-30°C. 100 ml of diethyl ether was added dropwise, and the resulting suspension was stirred at 25-30°C for 30-60 minutes. Stirring was stopped, and the suspension was allowed to settle for 1 hour. The supernatant was decanted from the settled solid, and 100 ml of fresh diethyl ether was added. This stirring, settling, and decanting process of the suspension was repeated several times until the 1-bromohexane content in the decanted liquid was less than 0.5%, as measured by GC analysis.

[0320] The remaining solvent was removed under reduced pressure at a temperature below 35°C. The crude solid product was further dried at a temperature below 35°C for 10-12 hours to obtain the QPEI product (32 g) as a beige solid. The water content was determined to be 1200 PPM, as measured by Karl Fischer analysis. The bromine content was determined to be approximately 35%, as measured by AgNO3 titration.

[0321] The theoretical molar percentages of the PEI reaction with caprolactone and 1-bromohexane are approximately 7% and 93%, respectively, assuming that caprolactone primarily reacts with primary amines.

[0322] Example 32. Additional Compounds The following compounds were prepared using a procedure similar to that described in the above examples. A= TIFF2026514865000101.tif36128;B= TIFF2026514865000102.tif34128.

[0323] TIFF2026514865000103.tif195150* indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)**

[0324] Compounds 32-1 and 32-2 were prepared in the same manner as described in Example 29. The general steps for the synthesis of compounds 32-1 and 32-2 were as follows: (1) A mixture of 70 kDa PEI, bromopropanol, bromohexane, and aqueous solutions of K2CO3 and t-amyl alcohol was heated at 96-98°C for 4 days and then cooled to room temperature. (2) The resulting mixture was filtered to remove the inorganic salts, and the filtered solid was washed with t-amyl alcohol. (3) The filtrate was concentrated under reduced pressure. (4) The residue was pulverized 5 to 6 times with diethyl ether. (5) The crude product obtained was dissolved in methyl ethyl ketone, filtered, and evaporated to dryness under reduced pressure.

[0325] R for each of the following compounds (32-1A, 32-1B, and 32-2A~32-2I) 60 The stoichiometric ratios of the groups are theoretical values ​​calculated based on the amounts of reactants used in the synthesis protocol, unless otherwise specified.

[0326] Compound 32-1A [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(10%), -C6H 13 (90%) was synthesized in the same manner as compound 32-1, but the crude product dissolved in methyl ethyl ketone was treated with an aqueous sodium bicarbonate solution, and the pH of the QPEI product was brought close to neutral before filtration, and then evaporated to dryness.

[0327] Compound 32-1B [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(10%), -C6H 13(90%) was synthesized in the same manner as compound 32-1, but the residue from step (3) was dissolved in dichloromethane, washed with an aqueous sodium bicarbonate solution, and then the dichloromethane layer was separated from the aqueous layer and evaporated to dryness under reduced pressure. The crude product was then used in steps (4) and (5).

[0328] Compound 32-2A [General structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13 (95%) was synthesized in the same manner as compound 32-2, but the crude product dissolved in methyl ethyl ketone was treated with an aqueous sodium bicarbonate solution, and the pH of the QPEI product was brought close to neutral before filtration, and then evaporated to dryness.

[0329] Compound 32-2B [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13 (95%) was synthesized in the same manner as compound 32-2, but the residue from step (3) was dissolved in dichloromethane, washed with an aqueous sodium bicarbonate solution, and then the dichloromethane layer was separated from the aqueous layer and evaporated to dryness under reduced pressure. The crude product was then used in steps (4) and (5).

[0330] Compound 32-2C [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(15%), -C6H 13 (85%-NMR analysis) Compound 32-2 was synthesized in the same manner as compound 32-2, but the residue from step (3) was dissolved in an aqueous KOH / ethanol solution, filtered, and concentrated under reduced pressure. The crude product was then used in steps (4) and (5). The crude product from step (5) was dissolved in ethanol for biological testing.

[0331] Compound 32-2D [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13(95%) was synthesized in the same manner as compound 32-2, but with additional water added to the initial reaction mixture in step (1). The crude product from step (5) was dissolved in ethanol for biological testing.

[0332] Compound 32-2E [General structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(12%), -C6H 13 (88%) - Actual measurement by NMR analysis: Compound 32-2C was synthesized in the same manner as compound (32-2C), the residue from step (3) was dissolved in an aqueous KOH / ethanol solution, filtered, and concentrated under reduced pressure. The crude product was then used in steps (4) and (5). The crude product from step (5) was dissolved in ethanol for biological testing.

[0333] Compound 32-2F [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13 (95%) was synthesized in the same manner as compound 32-2, but the mixture from step (1) was heated to 80°C instead of 96-98°C. The crude product from step (5) was dissolved in ethanol for biological testing.

[0334] Compound 32-2G [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13 (95%) was synthesized in the same manner as compound 32-2, except that the mixture in step (1) was heated to 80°C instead of 96-98°C, and the grinding in step (4) was carried out using methyl t-butyl ether (MTBE) instead of diethyl ether. The crude product from step (5) was dissolved in ethanol for biological testing.

[0335] Compound 32-2H [General structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13(95%)) was synthesized in the same manner as compound 32-2, except that the mixture in step (1) contained i-propyl alcohol instead of t-amyl alcohol, the mixture in step (1) was heated to 80°C instead of 96-98°C, and the grinding in step (4) was carried out using methyl t-butyl ether (MTBE) instead of diethyl ether. The crude product from step (5) was dissolved in i-propyl alcohol for biological testing.

[0336] Compound 32-2I [General Structure B; 70kDa PEI (branched); R 60 :-(CH2)3OH(5%), -C6H 13 (95%) was synthesized in the same manner as compound 32-2, but the mixture in step (1) had i-propyl alcohol instead of t-amyl alcohol, and the mixture in step (1) was heated to 80°C instead of 96-98°C. The crude product from step (5) was dissolved in i-propyl alcohol for biological testing.

[0337] Biological examples Example 1. Study of the efficacy of polymers in a mouse Staphylococcus Aureus-induced wound infection model. Grouping This project typically involved five separate efficacy studies, including a wound control group, an infection control group, a vancomycin group, and several test material groups (e.g., polymers of this technology).

[0338] Preparation of the inoculation i. The day of infection was defined as day 0 or hour 0. ii. On day 1, bacteria were streaked onto TSA from a glycerol stock at -80°C. The plates were incubated overnight (20-24 hours) in an incubator at 35±2°C. iii. On day 0, a single colony was taken from the TSA plate, suspended in sterile saline, and the OD600 (Biochrom-ultrospec-10) was monitored. Colonies or saline were added to adjust the bacterial concentration to the required level. (For Biochrom-ultrospec-10, the CFU / OD600 ratio is approximately 2.50E+08 CFU / ml when OD600 = 0.30). This is the inoculum. iv. Count the actual CFU levels of the inoculum, take 200 μL of the inoculum into a 96-well plate, and perform a series of 10-fold dilutions. 0 ~10 -5 Six-fold dilutions were obtained. 10 μL of each dilution was placed on a TSA plate and then incubated overnight at 35±2°C in an incubator. On the second day, the number of CFUs in each dilution was counted, and then the actual CFU level of the inoculum was further calculated. The calculation formula is as follows: TIFF2026514865000104.tif9128

[0339] The inoculation was administered locally. A total of 20 μl of inoculation was used for each mouse.

[0340] Establishment of a wound infection model i. On day 0 of the wound and inoculation, mice were anesthetized with injections of 50 mg / kg of zoletil and 10 mg / kg of xylazine. ii. Hair was clipped from the neck to the mid-lower back, the skin was scrubbed with iodine solution, and then rinsed with ethanol. A full-thickness skin wound was created on the dorsal side of each mouse using a 10.0 mm disposable skin biopsy punch. iii. A 20 μL inoculum containing approximately 5.0E+06NRS384 cells in a saline suspension was pipetteed into the wound and allowed to be absorbed for 3-5 minutes. To avoid cross-infection, a TEGADERM® adhesive bandage was placed over the wound.

[0341] treatment Preparation of vancomycin solution Vancomycin solution: Vancomycin was weighed and added to the corresponding volume of physiological saline to prepare a solution at a concentration of 1 mg / mL or 0.2 mg / mL. The dose volume was 10 μL or 50 μL per wound site.

[0342] Preparation of test substance solutions Compound 20-1 solution: Compound 20-1 (batch 105159) was weighed and added to the corresponding volume of dd water to prepare a solution at a concentration of 300 μM or 30 μM. The dose volume was 10 μL or 50 μL / wound site.

[0343] A solution of compound 21-1 was prepared in the same manner.

[0344] A solution of control compound 39637 was prepared in the same manner. TIFF2026514865000105.tif16128

[0345] Vancomycin treatment Treatment was initiated 5 minutes after infection according to the study design. See Figure 5. Formulation was based on target concentrations. 10 μL / 50 μL of vancomycin was pipetteed to the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, a TEGADERM® bandage was placed over the wound. 12 hours after infection, the TEGADERM® bandage was removed, and the wound was dry at this point. 10 μL / 50 μL of vancomycin was pipetteed to the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, the original TEGADERM® bandage was placed over the wound. 24 hours after infection, the TEGADERM® bandage was removed, and the wound was dry at this point. 10 μL / 50 μL of vancomycin was pipetteed to the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, a new TEGADERM® bandage was placed over the wound. 36 hours after infection, the TEGADERM® bandage was removed. There was some exudate from the wound. A dry swab was used to absorb the exudate around the edges of the wound without touching the surface of the wound. 10 μL / 50 μL of vancomycin was pipetteed onto the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, a TEGADERM® bandage (not a new one) was placed over the wound. The above process was followed for the next few days. The TEGADERM® bandage was changed daily. 72 hours after infection, the TEGADERM® bandage was removed. There was still some exudate from the wound. A dry swab was used to absorb the exudate around the edges of the wound without touching the surface of the wound. Then, the wound site was collected to detect bacterial load.

[0346] Processing of test items Five minutes after infection, treatment was initiated according to the study design. The preparation of the formulation was based on the target concentration. 50 μL of the test material was pipetteed to the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, a TEGADERM® bandage was placed over the wound. 24 hours after infection, the TEGADERM® bandage was removed, and at this point the wound was dry. 50 μL of the test material was pipetteed to the wound site and allowed to absorb for 5 minutes. Then, to avoid cross-infection, a new TEGADERM® bandage was placed over the wound. 48 hours after infection, the TEGADERM® bandage was removed. There was some exudate from the wound. A dry swab was used to absorb the exudate around the edges of the wound without touching the surface of the wound. 50 μL of the test material was pipetteed to the wound site and allowed to absorb for 5 minutes. Next, to avoid cross-infection, a new TEGADERM® bandage was placed over the wound. 72 hours after infection, the TEGADERM® bandage was removed. There was also some exudate from the wound. A dry swab was used to absorb the exudate around the edges of the wound without touching the surface of the wound. The wound site was then collected to detect bacterial load.

[0347] Determining the bacterial load at the wound site At some point after infection, the animals were euthanized with CO2. Each wound sample was excised and collected in 5 ml of sterile saline for homogenization. An IKA T10 homogenizer equipped with an S10N-10G dispersion tool was used at maximum speed. The homogenized tissue was serially diluted 10 times in a 96-well plate, and 10 μL of each dilution was spotted onto a TSA agar plate. The plates were incubated overnight in a 35 ± 2°C incubator, or until the colonies reached countable size. CFUs were counted by visual inspection.

[0348] statistical analysis The data was analyzed using GraphPad Prism7 and expressed as mean ± SEM.

[0349] Summary of results: Study I: At 12 and 24 hours post-infection with Staphylococcus aureus, the bacterial load at the wound site was similar, increasing to 8.59 lg CFU / wound site and 8.78 lg CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159), the bacterial load at 12 and 24 hours post-infection was significantly reduced to 4.07 lg CFU / wound site and 4.06 lg CFU / wound site, respectively, compared to the corresponding infection control group (P<0.05, P<0.05). Simultaneously, in the vancomycin group, a single 10 μg dose at 12 hours post-infection did not show any effect, but after two doses, the bacterial load decreased by only 1.12 lg CFU / wound site at 24 hours compared to the infection control group (P<0.05). See Table 10.

[0350] [Table 10]

[0351] Research II At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site was similar, increasing to 8.59 lg CFU / wound site and 8.86 lg CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159) at a concentration of 300 μM, the bacterial load at 12 and 24 hours was significantly reduced to 3.05 lg CFU / wound site and 4.97 lg CFU / wound site, respectively, compared to the corresponding infection control group (P<0.05, P<0.05).

[0352] At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site was similar, increasing to 8.59 lg CFU / wound site and 8.86 lg CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159) at a concentration of 100 μM, the bacterial load at 12 and 24 hours was significantly reduced to 3.36 lg CFU / wound site and 4.21 lg CFU / wound site, respectively, compared to the corresponding infection control group (P<0.05, P<0.05).

[0353] At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site was similar, increasing to 8.59 lg CFU / wound site and 8.86 lg CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159) at a concentration of 30 μM, the bacterial load at 12 and 24 hours was significantly reduced to 5.69 lg CFU / wound site and 5.70 lg CFU / wound site, respectively, compared to the corresponding infection control group (P<0.05, P<0.05).

[0354] At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site was similar, increasing to 8.59 lg CFU / wound site and 8.86 lg CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159) at a concentration of 10 μM, the bacterial load at 12 and 24 hours was significantly reduced to 5.83 lg CFU / wound site and 6.54 lg CFU / wound site, respectively, compared to the corresponding infection control group (P<0.05, P<0.05).

[0355] Compared to the corresponding infection control group, compound 20-1 (batch 105159) showed clear antibacterial activity at four different test concentrations: 300 μM and 100 μM, and 30 μM and 10 μM. This activity demonstrated a dose-response relationship. Among these, concentrations of 300 μM and 100 μM showed the best efficacy. See Table 11.

[0356] [Table 11]

[0357] Research III At 24, 48, and 72 hours post-infection with Staphylococcus aureus, the bacterial load at the wound site reached 8.77 1g CFU / wound site, 8.57 1g CFU / wound site, and 7.96 1g CFU / wound site, respectively. After intervention with compound 20-1 (batch 105159), the bacterial load was significantly reduced compared to the corresponding infection group. The bacterial load at 24, 48, and 72 hours was significantly reduced to 5.15 1g, 5.39 1g, and 4.22 1g, respectively (P<0.001).

[0358] The effect of compound 20-1 (batch 105159) appears to be more stable with extended treatment duration. See Table 12.

[0359] [Table 12] Note: ** T-test analysis showed P<0.001 for the infected group. * T-test analysis showed P<0.05 for the infected group.

[0360] Research IV At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site reached 8.59 1g CFU / wound site and 8.72 1g CFU / wound site, respectively. After intervention with compound 21-1 at a concentration of 300 μM, the bacterial load at 24 and 48 hours was significantly reduced to 5.21 1g CFU / wound site and 5.58 1g CFU / wound site, respectively (P<0.005).

[0361] At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site reached 8.59 lg CFU / wound site and 8.72 lg CFU / wound site, respectively. After intervention with compound 21-1 at a concentration of 100 μM, the bacterial load at 24 and 48 hours was significantly reduced to 6.37 lg CFU / wound site and 6.80 lg CFU / wound site, respectively (P<0.005).

[0362] At 12 and 24 hours post-Staphylococcus aureus infection, the bacterial load at the wound site reached 8.59 1g CFU / wound site and 8.72 1g CFU / wound site, respectively. After intervention with compound 21-1 at a concentration of 25 μM, the bacterial load at 24 and 48 hours was significantly reduced to 7.81 1g CFU / wound site and 8.01 1g CFU / wound site, respectively (P<0.05).

[0363] Compared to the corresponding infection group, compound 21-1 showed significant antibacterial activity at three different test concentrations, and this activity exhibited a dose-response relationship. See Table 13.

[0364] Research V At 12, 24, and 72 hours post-infection with Staphylococcus aureus, the bacterial load at the wound site was 8.46 lg CFU / wound, 8.54 lg CFU / wound, and 8.26 lg CFU / wound, respectively. A single application of compound 20-1 (batch 105159) reduced the bacterial load by 4.54 lg CFU / wound, 2.88 lg CFU / wound, and 0.43 lg CFU / wound at 24, 48, and 72 hours post-infection, respectively. That is, its effect gradually decreased from 24 hours to 72 hours post-infection. See Table 14.

[0365] With once-daily application at a concentration of 100 μM, compound 20-1 (batch 105159) showed a reduction of 2.56 1 g CFU / wound site in bacterial load compared to the infection control group over 72 hours (p<0.005).

[0366] [Table 13]

[0367] [Table 14]

[0368] Example 2. Study of cytotoxicity of mammalian cells Primary human dermal fibroblasts (HDF) and human keratinocytes (HaCaT) cells were selected for cytotoxicity and proliferation studies. HDF cells were cultured in high-glucose, glutamine-free, phenol red-free Dulbecco's Modified Eagle Medium (DMEM) (GIBCO®). The HDF medium was further supplemented with 10% heat-inactivated fetal bovine serum (GIBCO®), 1% L-glutamine (GIBCO®), and 1% penicillin-streptomycin (GIBCO®). HaCaTs cells were cultured throughout in high-glucose, glutamine-free, calcium-free DMEM (GIBCO®) supplemented with 10% heat-inactivated fetal bovine serum, 1% L-glutamine, and 1% penicillin-streptomycin 1 mM calcium chloride (Sigma).

[0369] Mammalian cell populations were maintained under standard culture conditions of 37°C, 5% CO2, and >95% relative humidity. Upon reaching 80% total confluence, cells were removed from the incubator, the culture medium was aspirated, and the monolayer was washed with Dulbecco's Modified Eagle Medium in saline (DPBS). After washing, 10 mL of 1% trypsin (GIBCO®) was added to the flask and incubated to facilitate cell separation from the culture vessel. After dissociation, 10 mL of culture medium was then added to each flask to neutralize the trypsin enzyme activity. The total flask volume of 20 mL was transferred to a universal tube and centrifuged at 400 rcf for 5 minutes. Upon completion, the cell pellet was resuspended in 10 mL of warmed culture medium, and the cell count per mL was determined using a hemocytometer. The cell suspension was then adjusted to 5 × 10⁴ cells / mL for HDF and 1 × 10⁵ cells / mL for HaCaT. 100 μL of cell suspension was added to each well of a sterile 96-well microtiter plate that had been treated for cell culture. The plate was incubated under standard culture conditions for 16–24 hours to allow cell adhesion to the culture vessel. After adhesion, the stock compounds were thawed, and serial 2-fold dilutions of each compound at concentrations ranging from 100 μM to 0.8 μM were prepared in warmed culture medium in a flat 96-well plate (compounds 20-1 and 25-1: 2.5 μM–0.02 μM). The culture plate was removed from the incubator, the medium was removed, and the monolayer was washed with 100 μL of warmed DPBS. The contents of the test dilution plates were transferred to the culture plate. This was applied to the mean of three biological replicates, each with three technical replicates (n=9) for each dilution in each compound. The plate was returned to the incubator under standard culture conditions for 24 hours.

[0370] Cytotoxicity test Cell damage and cytotoxicity were quantitatively measured using the secretion of the lactate dehydrogenase (LDH) enzyme. When damage to the cell plasma membrane releases LDH into the cell culture medium, the extracellular LDH in the medium can be quantified by a coupling enzyme reaction in which LDH catalyzes the conversion of lactate to pyruvate via the reduction of NAD+NADH. Oxidation of NADH by diaphorase results in the reduction of rezazurin, which forms a highly fluorescent resorphin. Therefore, cytotoxicity is measured using the resorphin level, which is directly proportional to the amount of LDH released into the medium.

[0371] Following incubation with the selected compounds, 50 μL of culture medium from each well was transferred to the corresponding wells of a fresh 96-well culture plate. The presence of lactate dehydrogenase (LDH) was then quantified using the INVITROGEN® CyQUANT® LDH Cytotoxicity Assay, Fluorescence Kit. Total fluorescence was measured by reading the plate on a plate reader at 560 nm excitation and 590 nm emission.

[0372] Cell proliferation test After collecting the culture medium for LDH quantification, the remaining cell culture medium was aspirated, the cell monolayer was washed with 100 μL of warmed DPBS, and fresh culture medium was added. The number of cells present in the remaining culture vessel was then determined using the CELLTITER 96® Aqueous One Solution Cell Proliferation Assay. The assay utilizes a tetrazolium compound (3-(4,5-dimethylthiazole-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, intramolecular salt) which is bioreduced by NADPH or NADH in metabolically active cells to produce a colored formazan product.

[0373] 20 μL of MTS (CELLTITER 96® Aqueous One Solution Cell Proliferation Assay) solution was added to each well, and the plates were returned to the incubator for 4 hours. Cell plates were collected, and colorimetric changes were detected on a plate reader at 490 nm absorbance. The number of viable cells present under each treatment condition was determined using calibration curves.

[0374] Microbiological methods: Bacterial strains and culture media conditions All microbial work was performed in a Class II biosafety hood. Clinically isolated strains of Klebsiella pneumoniae KL1 (isolated from leg wound swabs) and Staphylococcus aureus MR1 ​​(methicillin-resistant Staphylococcus aureus (MRSA) isolated from leg ulcers) were provided from our in-hospital clinical isolate bank. All other strains were obtained from ATCC. Table 15 lists all bacterial strains used in this study. Mueller-Hinton (MH) medium was used as the broth in all subsequent experiments. Overnight cultures (ONCs) were prepared by inoculating bacteria from a single colony maintained on MH agar into 5 mL of MH broth and incubating overnight at 37°C for 14–15 hours with continuous shaking (200 rpm).

[0375] [Table 15]

[0376] Summary of results:

[0377] [Table 16] *Compound 40598 is This corresponds to TIFF2026514865000113.tif13128. **Compound 40597 is, This corresponds to TIFF2026514865000114.tif13128.

[0378] There was a strong agreement between cell viability (MTS) and total cytotoxicity (LDH). Overall cytotoxicity appeared slightly higher in the HDF population. No positive effects on mammalian cell proliferation were observed in response to any of the screened compounds. For most compounds, a negative effect on cell viability was observed at treatment concentrations equivalent to those that could inhibit bacterial growth. Most compounds induced cytotoxicity at higher treatment concentrations (50 μM, 100 μM). A dose-dependent reduction in cytotoxicity and cell death was observed for almost all compounds.

[0379] Compound 20-1 (batch 105159 and 99367) resulted in a dose-dependent increase in LDH secretion at 0.31 μM.

[0380] For compound 39637 (batches 105543 and 109466), LDH secretion in HDF and HaCaT populations rapidly exceeded control levels at 3.12 μM. Batch 105543 appeared to exhibit a slightly higher cytotoxic effect. However, for both batches, near-complete absence of viable cells was observed in each cell population at 6.3 μM.

[0381] The concentrations at which compound 22-1 (batch 109590) and compound 21-1 (batch 109770) exhibited cytotoxicity were very similar, with HDF and HaCaT viable cells almost completely absent at 3.12 μM.

[0382] Compound 24-1 (batch 109781) exhibited slightly reduced cytotoxic effects on mammalian cells, accompanied by a surge in LDH secretion and the absence of viable cells observed at 6.25 μM.

[0383] Compounds 40840 and 40598 showed minimal cytotoxicity against mammalian cells: overall HDF cytotoxicity increased by 13.8% compared to the control.

[0384] Compounds 40840, 40598, 28-1 (batch 109666), and 40597 (batch 10944) exhibited minimal cytotoxicity. These compounds also showed limited antimicrobial activity.

[0385] Compound 20-1 (batch 105159) and Compound 20-1 (batch 99367) exhibited broad-spectrum antimicrobial activity at relatively low concentrations. Compound 20-1 (batch 105159) and Compound 20-1 (batch 99367) also showed high mammalian cytotoxicity in addition to broad-spectrum antimicrobial activity at relatively low concentrations.

[0386] Compounds 26-1 and 27-1 were cytotoxic to mammalian cells at all test concentrations. Compound 26-1 exhibited selective antimicrobial activity against both Staphylococcus aureus strain ATCC 29213 and clinical isolate MR1.

[0387] Compound 25-1 was most active against all Gram+VE species, including one Gram-VE species, Klebsiella pneumoniae KL1, at a relatively low μM concentration (6.25 μM).

[0388] Example 3. Antimicrobial activity study Minimum inhibitory concentration (MIC) The antimicrobial efficacy of the tested compounds was investigated using a standard microdilution method. Serial 2-fold dilutions were prepared for each compound at concentrations ranging from 100 μM to 0.8 μM in sterile MH broth in a flat 96-well plate. The ONC of each bacterial strain was adjusted to standard bacterial concentrations (5 × 10⁻⁶). 5The MIC (CFU / mL) was obtained and added to each dilution to determine the MIC in a total volume of 100 μL of MH broth. All plates were statically incubated at 37°C for 24 hours. Sterile dH2O was used as the vehicle-only control, and each bacterial strain included positive (bacteria only) and negative (MH medium only) controls. MIC breakpoint plates were stained with 10 μL of 0.02% resazurin and incubated at 37°C for 30 minutes. After incubation, all plates were imaged and absorbance was measured at 570 nm (plate reader). MIC is defined as the lowest concentration of a compound that inhibits growth. For all compounds tested, MH medium was used as the negative control and bacteria only as the positive control on each plate. Serial 2-fold dilutions were performed by mixing 50 μL of the highest concentration (x2) into rows A through H, which contained 50 μL of sterile MH broth.

[0389] MIC Data Analysis The data was exported to Microsoft Excel and background-normalized by subtracting the OD570nm values ​​from the medium-only wells (-VE control). MIC values ​​were determined by plotting the OD570nm value (Y) against the logarithmic concentration (X) of each compound. A modified Gompertz model was used to fit the data for more accurate MICs. The average OD570nm for each test compound concentration was fitted to a sigmoid curve using the modified Gompertz function (y=A+Ce-e(B(xM))), and the minimum inhibitory concentration (MIC) was identified from the inflection point of the lower asymptote (GraphPad Prism 9.0). This was applied to the mean of three biological replicates, each with four technical replicates (n=12), for each dilution in each compound.

[0390] Minimum Lethal Concentration (MBC) Procedure To determine the MBC compound concentration, breakpoints were estimated from the MIC curve. For all bacterial strains, the overnight culture was prepared as described above. The following day, the overnight culture was adjusted to 5 × 10⁶ per mL. 5A cell density of was obtained. Briefly, the culture was adjusted to McFarland standards (0.08-0.12) and diluted (1:150). The adjusted culture was inoculated into a 96-well plate containing 50 μL of sterile Muller-Hinton broth (MHB) and two concentrations of each compound. The MBC plate was statically incubated at 37°C for 24 hours. Sterile dH2O was used as a vehicle control, and positive controls (bacteria only) and negative controls (culture medium only) were also included in the assay. The MBC culture was serially diluted in the 96-well plate and quantified by spot plating onto Muller-Hinton agar (MHA). The MHA plate was incubated at 37°C for 24 hours and counted. Results are shown as CFU per mL.

[0391] Summary of results:

[0392] [Table 17]

[0393] [Table 18] -: No activity was observed.

[0394] Compounds 23-1 (batches 105402 and 109634), 39637 (batches 105543 and 109466), 22-1 (batch 109590), 21-1 (batch 109770), and 24-1 (batch 109781) showed strong antibacterial activity against the Gram+ve species Enterococcus faecalis and Staphylococcus aureus.

[0395] In Gram-negative species (Klebsiella pneumonia and Pseudomonas aeruginosa), three compounds, 20-1 (batch 105159), 20-1 (batch 99367), and 22-1 (batch 109590), were able to show inhibitory effects within the investigated concentration range.

[0396] Compounds 39637 (batches 105543 and 109466), 22-1 (batch 109590), and 21-1 (batch 109770) inhibited Staphylococcus Aureus at concentrations ranging from 1.57 μM to 6.25 μM.

[0397] Of all the compounds tested, the most effective MIC and MBC were lower in Gram-positive bacteria, but appeared to exhibit broad-spectrum activity in Gram-negative bacteria at much higher concentrations.

[0398] Compound 20-1 (batch 105159 and 99367) showed the most effective MBC inhibition profile across all bacterial strains. MBC levels clearly indicated inhibition in all strains at relatively low concentrations.

[0399] Of all the compounds tested above, the following showed the lowest antimicrobial activity: compound 40840 (batch 110435), 40598 (batch 109448), 28-1 (batch 109666), 26-1 (batch 109831), and 40597 (batch 109444). Compound 25-1 (batch 110417) showed low antimicrobial efficacy via MIC, but inhibited 5 out of 7 strains in MBC at 6.25 μM.

[0400] Additional compounds were tested to obtain MIC values ​​for the same bacteria shown in Tables 17 and 18 (see Table 19). ****: For all bacteria tested, QPEI MIC ≤ 12.5 μM; ***: QPEI MIC > 12.5 μM and QPEI MIC ≤ 50 μM (for > 50% of tested bacteria); **: QPEI MIC > 12.5 μM and QPEI MIC ≤ 50 μM (for < 50% of tested bacteria); *: For all bacteria tested, QPEI MIC > 100 μM.

[0401] [Table 19]

[0402] Example 4. Efficacy of biofilm inhibition microscopy results General bacterial cell culture All culture techniques were performed using aseptic techniques in a Class II microbiological safety cabinet (Microflow, Bioquell, Hampshire, UK). To contribute to sterile working conditions, all surfaces and items within the Class II hood were sprayed with 70% ethanol. Stock plates were prepared as needed by streaking a single microbank bead onto a Mueller Hinton agar plate (MHA; Oxoid, UK) followed by incubation at 37°C for 24 hours. The stock plates were then wrapped in Parafilm to reduce moisture loss and stored at 4°C for up to 2 months.

[0403] Biofilm preparation Overnight (O / N) bacterial cultures of *S. aureus* were prepared by inoculating a single colony into 10 mL of Mueller Hinton broth (MHB; Oxoid, UK) and then incubating at 37°C for 16 hours using 140 rpm shaking (Labnet 211DS shaking incubator, Labnet International, USA). The O / N cultures in the steady-state growth phase were diluted to obtain a cell density of 107 CFU / mL, which was validated by spot plating and colony count. Biofilms were prepared by inoculating a sterile filter membrane (0.22 μm, GE Healthcare, USA) with 4 μL of a controlled inoculum onto Mueller Hinton agar (MHA; Oxoid, UK). After drying, the plates were incubated upright at 37°C for 4 hours. After incubation, the biofilm was removed from the incubator and treated with 4 μL of a selected compound at various concentrations (100, 50, 25, 12.5, or 6.25 μM) from Table 19. The biofilm was then re-incubated upright at 37°C for the duration of the specific treatment incubation.

[0404] Scanning electron microscopy After treatment with a selected compound, the biofilm-containing filtration membrane was aseptically removed from the agar surface and transferred to a 6-well plate. In each well, 3-4 mL of 1% (v / v) glutaraldehyde (Sigma-Aldrich; Poole, UK) in distilled water was used to cover the biofilm. The glutaraldehyde solution was then left at RT (room temperature) for at least 1 hour. After 1 hour, the 1% glutaraldehyde was removed and replaced with pure water. This step was repeated two or three times to ensure complete removal of the glutaraldehyde solution. In each well, 3-4 mL of 10% (v / v) ethanol in distilled water was added to the biofilm and left for 30 minutes. This process was then repeated with successive solutions of ethanol in 30%, 50%, 70%, and 90% (v / v) distilled water. After incubation with increasing ethanol concentrations, the biofilm was immersed in 100% EtOH for 30 minutes. This process was repeated twice with fresh 100% EtOH. After all ethanol washing, the biofilm was critically dried using an E3100 critical point dryer (Quorum, Houston, US). This process replaces the remaining ethanol in the sample with liquid carbon dioxide to produce a dried sample. After drying, the biofilm was coated with 5 nm of gold using a Polaron T-100 coater / thickness monitor (Ladd, Williston, US). The sample was then imaged using a scanning electron microscope, specifically a Zeiss EVO-60 microscope. Imaging was performed using a LaB6 emitter with a 20 kilovolt (kV) EHT and a 100 pA probe current. Biological triple samples were used for all biofilm processing conditions (n=3).

[0405] SEM images of the control biofilm treated with the selected compound (100 μM) and the biofilm itself are shown in Figures 1A and 1B, respectively.

[0406] Confocal microscopy observation After treatment with a selected compound, the biofilm-containing filter membranes were stained with the FILMTRACER® LIVE / DEAD® biofilm viability kit, prepared according to the manufacturer's instructions. The LIVE / DEAD® biofilm viability stain incorporates SYTO 9 (live cell permeable stain) and propidium iodide (PI) (dead cell impermeable stain). The staining solution (4 μL) was applied directly to the surface of the biofilm and incubated in the dark at room temperature for 20 minutes. The biofilm-containing filter membranes were then inverted onto a clean coverslip.

[0407] Confocal laser microscopy imaging was performed using a Zeiss LSM710 laser scanning confocal microscope. A 488 nm laser was used for SYTO 9 and a 561 nm laser for PI to acquire the signal. For 3D imaging, z-stack series were performed on more than 10 slices at 45 μM for all samples. Representative images were taken from the maximum intensity projection for each sample. To quantify the LIVE / DEAD® signal, the relative intensity of both tracks (SYTO9 and PI) in each sample was measured across the corresponding region. Biological triple samples were used for all biofilm processing conditions (n=3).

[0408] The quantitative analysis of the activity of the selected compound (25 μM) on S. aureus colony biofilms over 3 hours is shown in Figure 2A (SYTO 9) and Figure 2B (Propidium Iodide). The quantitative analysis of the activity of the same compound at different concentrations on S. aureus colony biofilms is shown in Figure 3A (SYTO 9) and Figure 3B (Propidium Iodide). The selected compound rapidly inhibited biofilm viability to a measurable level of dead cells at 15 minutes compared to the untreated control, suggesting that its mode of action is immediate and most likely contact-dependent via membrane disruption and / or membrane permeabilization.

[0409] Example 5. In vitro efficacy of the compound against Gram-positive and Gram-negative bacteria The bacterial strains tested included CLSI and NCTC reference and quality control (QC) strains from the following biological groups: Acinetobacter baumannii, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Staphylococcus aureus. Several strains contained molecularly characterized β-lactamase genes, including the carbapenemase (KPC-2) and extended-spectrum β-lactamase (SHV-18) genes.

[0410] The isolates were tested for antibiotic susceptibility using the broth microdilution method in accordance with CLSI M07 (2018) and M100 (2023) guidelines. 96-well MIC panels were prepared in frozen form. The test medium was cation-modified Mueller-Hinton broth (CAMHB). For each of the nine strains tested, a single MIC value was measured for eight test compounds. For some QC strains, an additional MIC value was generated for levofloxacin (comparative drug).

[0411] Compound stock solutions were prepared and mixed overnight as needed. The pH of each stock solution was checked and adjusted as needed until a minimum pH of 5.0 (pH range 5.0-7.0) was achieved. Some compound stock solutions also required heating to aid in solubilization.

[0412] Current CLSI quality assurance practices were followed when conducting broth microdilution susceptibility testing. MIC values ​​were verified by simultaneously testing a control agent (levofloxacin) against CLSI-recommended QC strains, including S. aureus ATCC 29213 (methicillin-sensitive), E. coli ATCC 25922, Enterococcus faecalis ATCC 29212, and P. aeruginosa ATCC 27853. The initial inoculation density (target, 5 × 10⁵ CFU / mL) during susceptibility testing was monitored by bacterial colony count.

[0413] Table 20 shows the MIC values ​​of the eight test compounds and levofloxacin tested against nine QCs and reference strains.

[0414] [Table 20] (I)=A.baumannii(NCTC 13304), (II)=E.faecalis(ATCC 29212), (III)=E.faecalis(ATCC 51299), (IV)=E.coli(ATCC 25922), (V)=E.coli(ATCC BAA-2452), (VI)=K.pneumoniae(ATCC 700603), (VII)=K.pneumoniae (ATCC BAA 1705), (VIII)=P.aeruginosa (ATCC 27853), (IX)=S.aureus (ATCC 29213). A = Compound 32-10, B = Compound 21-1, C = Compound 29-1, D = Compound 32-2B, E = Compound 32-1B, F = Compound 22-1, G = Compound 32-11, H = Compound 32-3, Levo = Levofloxacin * indicates the highest compound concentration that can be tested for solubility of the compound in CAMHB.

[0415] Compound 32-10 exhibited broad-spectrum antibacterial activity with Gram-positive MIC values ​​ranging from 3.125 μM to 6.25 μM against S. aureus and E. faecalis, respectively, and Gram-negative activity ranging from 12.5 μM to 50 μM against Enterobacterales and non-fermenting bacteria (A. baumannii and P. aeruginosa).

[0416] Gram-positive activity of compound 21-1 was observed against S. aureus and E. faecalis isolates with an MIC value of 0.2 μM. Due to solubility issues in CAMHB, the highest concentration of compound 21-1 at which the MIC value could be determined was 0.8 μM. For Gram-negative bacteria, the MIC value of compound 21-1 ranged from 0.8 μM to >8 μM.

[0417] Compound 29-1 exhibited broad-spectrum activity with a Gram-positive MIC of 0.8 μM against S. aureus and Gram-positive MICs of 1.6 μM to 3.125 μM against E. faecalis. Gram-negative activity ranged from 6.25 μM to 25 μM against the tested Enterobacterales (E. coli and K. pneumoniae) and non-fermenting strains (A. baumannii and P. aeruginosa).

[0418] Gram-positive activity of compound 32-2 was observed against S. aureus and E. faecalis isolates with MIC values ​​of 0.4 μM and 1.6 μM, respectively. Due to solubility issues in CAMHB, the highest concentration of compound 32-2 at which the MIC value could be determined was 6.25 μM. For Gram-negative bacteria, the MIC value of compound 32-2 ranged from 6.25 μM to >6.25 μM.

[0419] Compound 32-1 exhibited broad-spectrum activity with a Gram-positive MIC value of ≤0.1 μM against S. aureus and a Gram-positive MIC value of 0.2 μM against E. faecalis. Due to solubility issues in CAMHB, the highest concentration of compound 32-1 at which the MIC value could be determined was 1.6 μM. Gram-negative activity ranged from 0.8 μM to ≥1.5 μM against the tested Enterobacterales (E. coli and K. pneumoniae) and non-fermenting strains (A. baumannii and P. aeruginosa).

[0420] Compound 22-1 exhibited broad-spectrum activity with a Gram-positive MIC of 1.6 μM against S. aureus and a Gram-positive MIC of 6.25 μM against E. faecalis. Gram-negative activity ranged from 6.25 μM for A. baumannii, 12.5 μM for E. coli, and 50 μM to ≥ 100 μM for K. pneumoniae and P. aeruginosa.

[0421] Compound 32-11 exhibited broad-spectrum activity with a Gram-positive MIC value of 0.4 μM against S. aureus and Gram-positive MIC values ​​of 0.4 μM to 0.8 μM against E. faecalis. Due to solubility issues in CAMHB, the highest concentration of compound 32-11 at which the MIC value could be determined was 0.8 μM. Gram-negative activity ranged from 0.8 μM to >0.8 μM against the tested Enterobacterales (E. coli and K. pneumoniae) and non-fermenting strains (A. baumannii and P. aeruginosa).

[0422] Compound 32-3 exhibited potent Gram-positive activity with MIC values ​​of 0.4 μM against S. aureus and 0.4 μM to >0.4 μM agains...

Claims

1. (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A wound dressing comprising a polymer component selected from the group consisting of the following.

2. The wound dressing according to claim 1, wherein the polymer component is antibacterial against one or both of Gram-negative and Gram-positive bacteria.

3. The wound dressing according to claim 1 or 2, wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:

1.

4. The wound dressing according to any one of claims 1 to 3, wherein the outer layer of the wound dressing contains the polymer component.

5. The wound dressing according to any one of claims 1 to 3, wherein the polymer component is impregnated into the wound dressing.

6. The wound dressing according to any one of claims 1 to 5, wherein the wound dressing is selected from the group consisting of wraps, covers, barriers, layers, packings, gauze, plaster, adhesive bandages, lint, sutures, films, foam products, hydrogels, hydrocolloids, alginate products, bioactive products, tissue manipulation skin substitutes, medicinal products, liquid adhesive bandages, smart dressings, and composites, or any combination thereof.

7. The wound dressing according to any one of claims 1 to 5, wherein the wound dressing is configured to display one or more parameters related to the condition of the wound site.

8. (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and A topical preparation containing, The topical formulation wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:

1.

9. The topical formulation according to claim 8, which is in the form of a cream, gel, paste, foam, spray, powder, emulsion, liquid, or ointment.

10. The topical formulation according to claim 8 or 9, wherein the polymer component is antibacterial against one or both of Gram-negative and Gram-positive bacterial strains.

11. A method for preventing or reducing bacterial growth or reducing infection in a target wound, surgical site, or implant, wherein the wound, surgical site, or implant (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising applying or coating a composition containing the following.

12. A method for treating a wound or surgical site in a person who needs treatment, wherein the wound or surgical site is (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising applying a composition containing the following.

13. A method for promoting the healing of a wound or surgical site in a person who needs it, wherein the wound or surgical site is (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising applying a composition containing the following.

14. The method according to any one of claims 11 to 13, wherein the wound is an external wound.

15. The method according to any one of claims 11 to 13, wherein the wound is an internal wound.

16. The method according to any one of claims 11 to 15, wherein the method is part of a regimen for acute wound care.

17. The method according to any one of claims 11 to 15, wherein the method is part of a chronic wound care regimen.

18. The method according to any one of claims 11 to 17, wherein the wound is infected.

19. The method according to any one of claims 11 to 17, wherein the wound is not infected.

20. A method for protecting a wound site in a person who needs it, comprising: surrounding at least a portion of the wound site with a covering material; and protecting the wound site (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising contacting with a composition containing the following.

21. A method for preventing or reducing infection in a target that needs to be prevented, (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising administering a composition containing the following.

22. A method for treating an infection in a person in need, wherein the person in need (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising administering a composition containing the following.

23. The method according to claim 21 or 22, wherein the infection is a local infection.

24. The method according to claim 21 or 22, wherein the infection is a systemic infection.

25. A method for treating sepsis in a person in need, wherein the person in need (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising administering a composition containing the following.

26. A method for preventing or reducing necrosis in a subject in need, wherein the subject (1) Polyethyleneimine intermediate, (2) (i) A first adduct of a first polyfunctional crosslinking agent and a first quaternary ammonium salt, wherein the first quaternary ammonium salt has a reactive linking group that reacts with the first polyfunctional crosslinking agent, (ii) The polyethyleneimine intermediate, or the second adduct of the polyethyleneimine intermediate and a second polyfunctional crosslinking agent, wherein the polyethyleneimine intermediate contains an optionally substituted hydroxyalkylene functional group that reacts with the first adduct, and the nitrogen atoms present in the polyethyleneimine intermediate are at least partially quaternized, (iii) Optionally, polyol and (iv) Optionally, a water-soluble polymer and (v) Optionally, a third polyfunctional crosslinking agent and Polymers, copolymers, interpenetrating polymer networks, polyelectrolyte complexes, blends, or composites, including, (3) A polymer, copolymer, interpenetrating polymer network, polyelectrolyte complex, blend, or composite comprising the first adduct, the polyol, the water-soluble polymer, and optionally the third polyfunctional crosslinking agent, (4) The second appendage, and (5) Two or more combinations of the above A polymer component selected from the group consisting of, At least one pharmaceutically acceptable excipient and The method comprising administering a composition containing the following.

27. The method according to any one of claims 11 to 26, wherein the subject is a human or an animal.

28. The method according to any one of claims 11 to 27, wherein the composition is antibacterial against one or both of Gram-negative and Gram-positive bacterial strains.

29. The method according to any one of claims 11 to 28, wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:

1.

30. The wound dressing, topical formulation, or method according to any one of claims 1 to 29, wherein the polyethyleneimine intermediate comprises a reaction product of a reagent containing polyethyleneimine and an alkylating agent.

31. The wound dressing, topical formulation, or method according to claim 30, wherein the reagent further comprises a monoepoxide or a lactone.

32. The monoepoxide or the lactone is —(C ６ —C １０ aryl), and —(C １ —C ６ alkoxy) optionally substituted with hydroxy, C １ —C ６ alkoxy, C １ —C ６ aryl optionally substituted with alkyl, and C ６ —C １０ aryl optionally substituted with a substituent selected from carboxy, C １ —C ６ The wound dressing, topical preparation, or method according to claim 31, optionally substituted with alkyl.

33. The aforementioned monoepoxide is C １ -C ６ The wound dressing, topical formulation, or method according to claim 31, wherein the alkyloxirane is used.

34. Said C １ -C ６ The wound dressing, topical formulation, or method according to claim 33, wherein the alkyl epoxide is selected from the group consisting of methyl oxirane, ethyl oxirane, propyl oxirane, and butyl oxirane.

35. The polyethyleneimine intermediate comprises a reaction product of polyethyleneimine, a monoepoxide, and optionally a reagent containing an alkylating agent, wherein the monoepoxide is -(C １ -C ６ Alkylene)-N ＋ (R ２０ ) ３ X － It is replaced by each R ２０ However, independently, C １ -C １８ Alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl; and -(C １ -C ６ Alkyl), -(C １ -C ６ Alkoxy), -C(O)O-(C １ -C ６ Alkyl), -C(O)NH(C １ -C ６ Alkyl), -C(O)N(C １ -C ６ Alkyl) ２ , or -OC(O)-(C １ -C ６ C may be substituted with alkyl. ６ -C １０ Selected from the group consisting of aryls, each X － A wound dressing, topical formulation, or method according to any one of claims 1 to 29, wherein the following are independently selected from the group consisting of acetate, halogenated compounds, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and their organically substituted derivatives.

36. The alkylating agent comprises one or more R ２１ -Includes LG, in the formula, each R ２１ However, independently, -OH, -(C １ -C ６ Alkoxy), carboxy, -(C ６ -C １０ Aryl), -C(O)O(C １ -C ６ Alkyl), -C(O)-(C ６ -C １０ aryl), and possibly substituted with -OH - (C １ -C ６ C may be substituted with substituents selected from alkoxys. １ -C ６ A wound dressing, topical formulation, or method according to any one of claims 30 to 35, wherein each LG is selected from alkyl groups and is a leaving group.

37. The wound dressing, topical formulation, or method according to claim 36, wherein the alkylating agent is phenacyl halogenate, benzyl halogenate, or hexyl halogenate.

38. The wound dressing, topical formulation, or method according to any one of claims 30 to 37, wherein the reagent for the reaction product contained in the polyethyleneimine intermediate further comprises a monoisocyanate.

39. The monoisocyanate comprises one or more R ３０ -Includes NCO, in the formula, each R ３０ However, they became independent, (1) Halogen, -SiR ａ (OR ｂ ) ( OR ｃ ), and -(C ６ -C １０ C may be substituted with 1 to 3 substituents independently selected from aryl. ６ -C ２０ Alkyl, and (2) Halogen, -(C １ -C ６ Alkyl), and -SiR ａ (OR ｂ ) ( OR ｃ C may be substituted with 1 to 3 substituents independently selected from ) ６ -C １０ Ariel Selected from, in the formula, each R ａ However, independently, C １ -C ６ It is alkyl, and each R ｂ and each R ｃ However, independently, -(C １ -C ６ Alkyl) and -Si(C １ -C ６ Alkyl) ３ A wound dressing, topical formulation, or method according to claim 38, selected from the above.

40. The wound dressing, topical formulation, or method according to claim 38 or 39, wherein the monoisocyanate comprises octyl isocyanate, octadecyl isocyanate, or a combination thereof.

41. The wound dressing, topical formulation, or method according to any one of claims 30 to 40, wherein the polyethyleneimine has a molecular weight of about 300 to about 270,000 daltons.

42. The wound dressing, topical formulation, or method according to any one of claims 30 to 41, wherein the polyethyleneimine has a molecular weight of about 10,000 to about 200,000 daltons.

43. The wound dressing, topical formulation, or method according to any one of claims 30 to 42, wherein the polyethyleneimine has a molecular weight of about 25,000 to about 120,000 daltons.

44. The wound dressing, topical preparation, or method according to any one of claims 30 to 43, wherein the polyethyleneimine is branched.

45. The wound dressing, topical preparation, or method according to any one of claims 30 to 43, wherein the polyethyleneimine is hyperbranched.

46. The wound dressing, topical formulation, or method according to any one of claims 30 to 45, wherein the polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:2:1 to about 1:1:

1.

47. The wound dressing, topical formulation, or method according to any one of claims 30 to 45, wherein the polyethyleneimine has a primary amine to secondary amine to tertiary amine ratio of about 1:1:0.

7.

48. The polyethyleneimine intermediate is , and one or more copolymers or blends thereof, in the formula, Each Y ３ However, independently, H or -O-Y ２ And, Each Y ２ However, independently, H or -C(O)-NHR ３０ And, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Z is -(C ２ -C ６ Alkylene) - and Each R １０ is independently hydrogen; -N ＋ (R ２０ ) ３ X － , -(C ６ -C １０ aryl), and -(C １ -C ６ alkoxy) which may be substituted with a substituent selected from the group consisting of -OH, and C １ -C ６ alkyl, -(C １ -C ６ alkoxy), -(C １ -C ６ alkyl) which may be substituted with -(C ６ -C １０ ), and aryl), and carboxy, each R ２０ is independently C １ -C １８ alkyl; C １ -C １８ heteroalkyl having 1 to 4 heteroatoms independently selected from O, S, Si and tertiary substituted N; and -(C １ -C ６ alkyl), -(C １ -C ６ alkoxy), -C(O)O-(C １ -C ６ alkyl), -C(O)NH(C １ -C ６ alkyl), -C(O)N(C １ -C ６ alkyl) ２ , or -OC(O)-(C １ -C ６ alkyl) which may be substituted with C ６ -C １０ aryl, selected from the group consisting of Each R ２１ However, independently, -OH, -(C １ -C ６ Alkoxy), carboxy, -(C ６ -C １０ Aryl), -C(O)O(C １ -C ６ Alkyl), -C(O)-(C ６ -C １０ aryl), and possibly substituted with -OH - (C １ -C ６ C may be substituted with substituents selected from alkoxys. １ -C ６ Selected from alkyl groups, Each R ３０ However, they became independent, (1) Halogen, -SiR ａ (OR ｂ ) ( OR ｃ ), and -(C ６ -C １０ C may be substituted with 1 to 3 substituents independently selected from aryl. ６ -C ２０ Alkyl, and (2) Halogen, -(C １ -C ６ Alkyl), and -SiR ａ (OR ｂ ) ( OR ｃ C may be substituted with 1 to 3 substituents independently selected from ) ６ -C １０ Ariel Selected from, in the formula, each R ａ However, independently, -(C １ -C ６ Alkyl) and each R ｂ and each R ｃ However, independently, -(C １ -C ６ Alkyl) and -Si(C １ -C ６ Alkyl) ３ Selected from, Each X － However, independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives, however, R １０ However, -(C ６ -C １０ aryl), and possibly substituted with -OH - (C １ -C ６ Alkoxy), -(C １ -C ６ Alkoxy), -(C １ -C ６ (C) may be substituted with alkyl. ６ -C １０ C may be substituted with substituents selected from aryl, and carboxyl. １ -C ６ If it is alkyl, the polyethyleneimine intermediate is independently, Selected from, A wound dressing, topical preparation, or method according to any one of claims 1 to 29.

49. The polyethyleneimine intermediate is And, In the formula, each R ６０ However, independently, -OH and -N ＋ (R ２０ ) ３ X － , - (C １ -C ６ Alkoxy), carboxy, -(C ６ -C １０ Aryl), -C(O)O(C １ -C ６ Alkyl), -C(O)-(C ６ -C １０ aryl), and possibly substituted with -OH - (C １ -C ６ It may be substituted with 1 to 3 substituents selected from alkoxys - Y ４ - (C １ -C １８ Selected from alkyl groups, and at least one R ６０ However, although it is substituted with -OH, all R ６０ Less than 50% of it is substituted with -OH. Y ４ However, it does not exist, or it is -C(O)-, Each R ２０ However, independently, C １ -C １８ Alkyl; C having 1 to 4 heteroatoms independently selected from O, S, Si, and tertiary substituted N １ -C １８ Heteroalkyl; and -(C １ -C ６ Alkyl), -(C １ -C ６ Alkoxy), -C(O)O-(C １ -C ６ Alkyl), -C(O)NH(C １ -C ６ Alkyl), -C(O)N(C １ -C ６ Alkyl) ２ , or -OC(O)-(C １ -C ６ C may be substituted with alkyl. ６ -C １０ Selected from the group consisting of aryls, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Each X － However, independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives, A wound dressing, topical preparation, or method according to any one of claims 1 to 29.

50. The polyethyleneimine intermediate is And, In the formula, each R ６０ However, independently, -OH and -N ＋ (R ２０ ) ３ X － , - (C ６ -C １０ Aryl), -C(O)O(C １ -C ６ Alkyl), and -C(O)-(C ６ -C １０ It may be substituted with 1 to 3 substituents selected from aryls - Y ４ - (C １ -C １８ Selected from alkyl groups, and at least one R ６０ However, although it is substituted with -OH, all R ６０ Less than 50% of it is substituted with -OH. Y ４ However, it does not exist, or it is -C(O)-, Each R ２０ However, independently, C １ -C ６ Selected from the group consisting of alkyl groups, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 1000. Each X － However, independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives, A wound dressing, topical preparation, or method according to any one of claims 1 to 29.

51. Each R ６０ However, it may be independently substituted with -OH - (C １ -C １８ Selected from alkyl groups, and at least one R ６０ However, although it is substituted with -OH, all R ６０ The wound dressing, topical formulation, or method according to claim 50, wherein less than 50% of the ions are replaced with -OH groups.

52. The polyethyleneimine intermediate is * indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** Selected from the group consisting of, In the table, A is And B is, The wound dressing, topical formulation, or method according to any one of claims 1 to 29, wherein each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100.

53. X in which one or more bromide anions are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. － A wound dressing, topical preparation, or method according to claim 52, which is replaced by [the specified substance].

54. The polyethyleneimine intermediate is * indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) are used.** ***Actual stoichiometric ratios determined by NMR analysis Selected from the group consisting of, In the table, A is And B is, Each n is an integer independently selected from 1 to 3000, preferably an integer independently selected from 10 to 100, and each X － A wound dressing, topical formulation, or method according to any one of claims 1 to 29, wherein the following are independently selected from the group consisting of acetate, halogenated compounds, sulfate, sulfonate, phosphate, phosphonate, carbonate, silicate, hexafluorophosphate, hexafluoroantimonate, triflate, and borate, and their organically substituted derivatives.

55. A wound dressing, topical formulation, or method according to any one of claims 1 to 54, wherein at least 20% of the nitrogen atoms of the polyethyleneimine intermediate are quaternized.

56. The wound dressing, topical formulation, or method according to any one of claims 1 to 55, wherein the polyethyleneimine intermediate is present in the polymer, copolymer, or interpenetrating polymer network of polymer component (1), (3), or (4) in an amount of about 0.1% to about 50% by weight.

57. The wound dressing, topical formulation, or method according to any one of claims 1 to 56, wherein the polymer component is the polyethyleneimine intermediate.

58. A composition containing the aforementioned polymer component (i) spraying the composition onto a fibrous material, (ii) Immersing a fibrous material in a fluid containing the composition, (iii) Impregnating the fibers of a fibrous material with a fluid containing the composition, (iv) Applying a coating layer containing the composition to the surface of a fibrous material. (v) Adhering a backing material containing the composition to a fibrous material, (vi) Applying microneedles containing the composition to a fibrous material, (vii) embedding a layer containing the composition within a fibrous material, (viiii) constructing fibers of a fibrous material containing the composition by electrospinning, or (ix) Interleaving fibers containing the composition with fibers of a fibrous material. A method for producing a wound dressing according to any one of claims 1 to 8 and 30 to 57, comprising integrating the fibrous material by one of the following.

59. A polymer having wound-healing properties, comprising a polyethyleneimine intermediate, wherein the polyethyleneimine intermediate has a total quaternary amine to total hydroxyl group ratio of at least 1:

1.

60. * indicates the molecular weight of the polyethyleneimine precursor. **Theoretical stoichiometric ratio (based on the amount of reactants used in the synthesis protocol)** Selected from the group consisting of, In the table, A is And B is, The polymer according to claim 59, wherein each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100.

61. X in which one or more bromide anions are independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives. － The polymer according to claim 60, which is substituted with

62. * indicates the molecular weight of the polyethyleneimine precursor. **Unless otherwise specified, theoretical stoichiometric ratios (based on the amounts of reactants used in the synthesis protocol) are used.** Selected from the group consisting of, In the table, A is And B is, Each n is an integer independently selected from 2 to 3000, preferably an integer independently selected from 10 to 100, and each X － The polymer according to claim 59, wherein the polymer is independently selected from the group consisting of acetates, halides, sulfates, sulfonates, phosphates, phosphonates, carbonates, silicates, hexafluorophosphates, hexafluoroantimonates, triflates, and borates, and their organically substituted derivatives.

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