WO2019200478A1

WO2019200478A1 - Use of compounds for making products with at least one n-halamine precursor group and at least one cationic center

Info

Publication number: WO2019200478A1
Application number: PCT/CA2019/050479
Authority: WO
Inventors: Ahmed I. Abdelrahman; Gurmeet BINDRA; Marcelo DUBIEL; Zachary WOLFF
Original assignee: Exigence Technologies Inc.
Priority date: 2018-04-20
Filing date: 2019-04-17
Publication date: 2019-10-24

Abstract

The present disclosure relates to using 2,2,6,6-tetramethyl-4-piperidone (TMPD) as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic N-halamine precursor group and at least one cationic center, and optionally a coating incorporation group. The present disclosure also relates to using TMPD as a reactant in at least one chemical reaction for making: (a) an intermediate compound that comprises at least one cyclic N-halamine precursor group and at least one coating incorporation group, (b) an intermediate compound that comprises at least one cyclic N-halamine precursor group and at least one cationic center, or (c) an intermediate compound that comprises at least one cyclic N-halamine precursor group, at least one coating incorporation group, and at least one cationic center. The compounds disclosed herein may have biocidal activity, and/or they may have increased biocidal activity following one or more chemical-modification reactions.

Description

USE OF COMPOUNDS FOR MAKING PRODUCTS WITH AT LEAST ONE N- HALAMINE PRECURSOR GROUP AND AT LEAST ONE CATIONIC CENTER

TECHNICAL FIELD

[0001] This disclosure generally relates to methods of synthesizing intermediate compounds and reaction-product compounds. In particular, the disclosure relates to the use of compounds as reactants to synthesize reaction- product compounds that have at least one /V-halamine precursor group and at least one cationic center.

BACKGROUND [0002] Microorganisms, such as bacteria, archaea, yeast or fungi, can cause disease, spoilage of inventory, process inefficiencies, disruptions of healthy natural environments, and infrastructure degradation. More specifically, healthcare-associated infections (HAIs) are a serious and growing challenge to health care systems around the world. HAIs cause over 100,000 deaths annually and have become the 3^rd leading cause of death in Canada. It is estimated that in any given year, HAIs directly cost the United States healthcare system between about $30B and about $45B. Added to this challenge is the increasing prevalence of microorganisms that are resistant to currently available antimicrobial intervention products and processes, including preventative approaches (disinfectants used to control environmental contamination) and reactive approaches (remedies including the use of antibiotics). Therefore, it is necessary to deploy biocidal technologies in various environments as a strategy for controlling unwanted levels or types of micro-organisms.

[0003] A common approach for disinfecting both hard and soft surfaces is the use of liquid disinfectants. Selection of a suitable disinfectant for any given application is dependent upon the environment where the disinfectant will be applied. Selection criteria include the types of micro-organisms targeted, contact time for the disinfectant, level of toxicity tolerable in each application, cleanliness (or lack thereof) of the surface to be cleaned, sensitivity of the surface materials to oxidization (i.e. , leading to corrosion of the substrate), the presence or absence of biofilms, the amount of organic load present on substrate surfaces, and local regulations that may restrict the use of certain active ingredients within a disinfectant. Select environments are far more challenging to adequately disinfect than others.

[0004] It is known to modify soft surfaces, such as textiles, to provide biocidal properties. For example, the antimicrobial properties of silver have been known since at least the 1960s. Specifically, silver nanoparticles possess broad- spectrum antimicrobial activities and exhibit few toxicological side effects. Currently there are commercially available textiles that incorporate silver. For example, there is a LULULEMON ® (Lululemon is a registered trademark of Lululemon Athletica Canada Inc.), SILVERSCENT ® (Silverscent registered trademark of Lululemon Athletica Inc.) product that incorporates the X-STATIC ® (X-static registered trademark of Noble Fiber Technologies, LLC) silver product. Additionally, UNDER ARMOUR ® (Under Armour registered trademark of Under Armour, Inc.) markets a scent control technology that comprises a blend of at least silver and zinc. The biocidal activity of these silver-incorporated textiles is limited by the amount of silver that is present and available to react with micro- organisms. The amount of silver is finite and may decrease as the textiles are laundered.

[0005] It is also known to modify textiles that incorporate polyethylene terephthalate (PET). These modifications may be achieved by forming a surface network of polyacrylamide (PAM) and PET, and then converting immobilized amides within the surface network to /V-chloramine. Composite fabrics with such surface networks have been termed PAM-PETs. PAM-PETs have been challenged with different strains of multi-drug resistant bacteria including health- care acquired Staphylococcus aureus , an MRSA (isolate #70065); community- acquired S. aureus , also an MRSA (isolate #70527); multi-drug-resistant (MDR) ESBL E. coli (isolate #70094); MDR Pseudomonas aeruginosa (isolate #73104); and S. aureus ATCC 25923. The PAM-PET composite fabric demonstrated close to a 6-log reduction of all the tested bacteria. Furthermore, the /V-chloramine on the PAM-PET was evaluated. After 29 regeneration cycles, the PAM-PET (active chlorine 306 ppm) was still able to provide 6-log reduction of HA-MRSA (isolate #70527) within 20 minutes of contact. [0006] International patent application number PCT/CA2013/000491 teaches forming a semi-interpenetrating network upon a PET surface. The network provides at least one alkynyl group for covalently bonding cyclic amide, azido-5, 5-dimethyl-hydantoin (ADMH). This modified PET sample could bring 7- log reductions of both MDR ESBL #70094 and CA-MRSA #70527. PCT/CA/- 2013/00491 also teaches linking the ADMH functionality with a short-chain quaternary ammonium cation to create A/-(2-azidoethyl)-3-(4, 4-dimethyl-2, 5- dioxoimidazolidin-1 -yl)-N, A/-dimethylpropan-1 -aminium chloride (ADPA) and covalently bonding this molecule onto the PET using the Cu (l)-catalyzed azide- alkyne cyclo addition (CuAAC, usually termed as“click chemistry”). [0007] However, forming the surface semi-interpenetrating network as taught by PCT/CA2013/00491 , as used in the first step of modification as a priming process, cannot be easily scaled up to industrially relevant levels. For example, the process requires multiple processing steps as well as the introduction of environmentally unfriendly additives, such as a methanol bath at elevated temperature. Additionally, the process requires UV irradiation to promote crosslinking in a methanol saturated environment, which may cause safety concerns. Furthermore, the teaching of PCT/CA2013/00491 may have limited applicability for use with hard surfaces.

SUMMARY [0008] Select embodiments of the present disclosure relate to use of

2,2,6,6-tetramethyl-4-piperidone (TMPD) as a reactant in at least one chemical reaction for making a first reaction-product compound that comprises at least one cyclic /V-halamine precursor group and at least one cationic center. The first reaction-product compound may further comprise at least one coating incorporation group.

[0009] Select embodiments of the present disclosure relate to use of TMPD as a reactant in at least one chemical reaction for making a first intermediate compound that comprises at least one cyclic /V-halamine precursor group and at least one coating incorporation group. The first intermediate compound may be prepared from a preliminary intermediate compound. The first intermediate compound may be used to make a second reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

[0010] Select embodiments of the present disclosure relate to use of TMPD as a reactant in at least one chemical reaction for making a second intermediate compound that comprises at least one cyclic /V-halamine precursor group and at least one cationic center. The second intermediate compound may be prepared from a preliminary intermediate compound. The second intermediate compound may be used to make a third reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

[0011] Select embodiments of the present disclosure relate to use of TMPD as a reactant in at least one chemical reaction for making a third intermediate compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. The third intermediate compound may be prepared from a preliminary intermediate compound. The third intermediate compound may be used to make a fourth reaction-product compound that comprises at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center.

[0012] Select embodiments of the present disclosure relate to a coating comprising at least one of the first reaction-product compound, the second reaction-product compound, the third reaction product compound, the fourth reaction product compound, or combinations thereof.

[0013] Select embodiments of the present disclosure relate to a process for making a fifth reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one cationic center, and at least one coating incorporation group, the process comprising reacting TMPD with at least one further reactant, wherein the at least one further reactant comprises the at least one coating incorporation group.

Select embodiments of the present disclosure relate to a process for making a reaction-product compound that comprises at least one cyclic N-halamine precursor group and at least one cationic center, the process comprising reacting TMPD with at least one reactant in at least one chemical reaction, wherein: (a) the at least one reactant comprises the at least one cationic center; (b) the at least one reactant reacts with 2,2,6,6-tetramethylpiperidone to form the at least one cationic center; (c) the at least one reactant reacts with an intermediate compound derived from 2,2,6,6-tetramethylpiperidone to form the at least one cationic center; or (d) any combination of (a) through (c).

BRIEF DESCRIPTION OF THE DRAWINGS

[0014] These and other features of the present disclosure will become more apparent in the following detailed description in which reference is made to the appended drawings:

[0015] FIG. 1 shows one example of a use of 2,2,6,6-tetramethyl-4- piperidone (TMPD) as a reactant in a chemical reaction for making a preliminary intermediate compound;

[0016] FIG. 2 shows an example of a nuclear magnetic resonance (NMR) spectrum obtained for the preliminary intermediate compound prepared in the reaction of FIG. 1 ; [0017] FIG. 3 shows an example of a mass-spectroscopy (MS) spectrum obtained for the preliminary intermediate compound prepared in the reaction of

FIG. 1 ;

[0018] FIG. 4 shows one example of a use of a preliminary intermediate compound derived from TMPD as a reactant in a chemical reaction for making an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group;

[0019] FIG. 5 shows an example of an NMR spectrum obtained for the intermediate compound prepared in the reaction of FIG. 4; [0020] FIG. 6 shows an example of an MS spectrum obtained for the intermediate compound prepared in the reaction of FIG. 4;

[0021] FIG. 7 shows one example of a use of an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making a reaction-product compound that includes at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center;

[0022] FIG. 8 shows an example of an NMR spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 7; [0023] FIG. 9 shows an example of an MS spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 7;

[0024] FIG. 10 shows an example of a use of an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making a reaction-product compound that includes at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center; [0025] FIG. 11 shows an example of an NMR spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 10;

[0026] FIG. 12 shows an example of an MS spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 10; [0027] FIG. 13 shows one example of a use of a preliminary intermediate compound derived from TMPD as a reactant in a chemical reaction for making an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group;

[0028] FIG. 14 shows one example of a larger scale use of an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making the reaction-product compound that includes at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center; [0029] FIG. 15 shows an example of an NMR spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 14;

[0030] FIG. 16 shows an example of an MS spectrum obtained for the reaction-product compound prepared in the reaction of FIG. 14;

[0031] FIG. 17 shows one example of a use of a preliminary intermediate compound derived from TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that includes at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center;

[0032] FIG. 18 shows an example of an NMR spectrum obtained for the reaction-product compound prepared in the at least one chemical reaction of

FIG. 17; [0033] FIG. 19 shows an example of an MS spectrum obtained for the reaction-product compound prepared in the at least one chemical reaction of

FIG. 17;

[0034] FIG. 20 shows one example of a use of TMPD as a reactant in a chemical reaction for making a preliminary intermediate compound;

[0035] FIG. 21 shows an example of an NMR spectrum obtained for the preliminary intermediate compound prepared in the reaction of FIG. 20;

[0036] FIG. 22 shows an example of a MS spectrum obtained for the preliminary intermediate compound prepared in the reaction of FIG. 20; [0037] FIG. 23 shows one example of a use of the preliminary intermediate compound prepared in the reaction of FIG. 20 as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers; [0038] FIG. 24 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, a coating incorporation group, and three cationic centers;

[0039] FIG. 25 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, a coating incorporation group, and a cationic center;

[0040] FIG. 26 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, a coating incorporation group, and three cationic centers; [0041] FIG. 27 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and three cationic centers; [0042] FIG. 28 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers;

[0043] FIG. 29 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, a coating incorporation group, and two cationic centers;

[0044] FIG. 30 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers;

[0045] FIG. 31 shows an example of three intermediate compounds that are each made by a reaction in which TMPD is a reactant, each intermediate compound is part of a reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups and two cationic centers; and

[0046] FIG. 32 shows an example of a general structure for a reaction product and an intermediate compound that may be made using TMPD as a reactant in one more reactions. [0047] The drawings are limited to show three-dimensional chemical compounds in only two dimensions. The present disclosure is not limited to the specific compounds shown in the drawings. The present disclosure also contemplates resonance structures and isomers, such as stereoisomers, diastereomers and enantiomers that have the same functional groups as the compounds shown in the drawings. Furthermore, the present disclosure is not limited to the specific counter ions depicted in the drawings herein. The present disclosure contemplates other suitable counter ions. For example, the Br or Ch ions depicted may also represent other counter ions, such as other halogen ions, phosphate ions or other similar ions.

DETAILED DESCRIPTION

[0048] Select embodiments of the present disclosure relate to use of 2,2,6,6-tetramethyl-4-piperidone (TMPD) as a reactant in at least one chemical reaction for making an intermediate compound and/or at least one reaction- product compound. Each of the intermediate compound and the reaction-product compound may comprise at least one cyclic /V-halamine precursor group and at least one cationic center. Each of the intermediate compound and the reaction- product compound may also comprise at least one coating incorporation group. [0049] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.

[0050] As used herein, the term“about” refers to an approximately +/- 10% variation from a given value. It is to be understood that such a variation is always included in any given value provided herein, whether or not it is specifically referred to.

[0051] As used herein, the term "activity" refers to biocidal activity.

[0052] As used herein, the term "biocide" means a chemical compound or a chemical composition or a chemical formulation that can kill or render harmless one or more microbes.

[0053] As used herein, the term“cationic center” means an atom within a compound that has a positive charge. The positive charge at a cationic center may be balanced by the presence of one or more negatively-charged ionic species, which may also be referred to herein as a counter-ion. Examples of select atoms that form part of cationic centers described here include but are not limited to: nitrogen, phosphorous, and sulfur.

[0054] As used herein, the term“coating incorporation group” refers to a chemical functionality that is linkable or bondable to another component. In select embodiments, a coating incorporation group may be one or more of: a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group or combinations thereof.

[0055] As used herein, the terms "halo" and "halogen" by themselves or as part of another substituent, have the same meaning as commonly understood by one of ordinary skill in the art, and preferably refer to chlorine, bromine, iodine or combinations thereof.

[0056] As used herein, the terms “microbe”, “microbes”, and “micro- organisms” refer to one or more single-celled or multi-cellular microorganisms such as those exemplified by bacteria, archaea, yeast, and fungi.

[0057] The terms“organic load”,“organic loading”, or“organic soil”, which may be used interchangeably, as used herein, refer to matter composed of organic compounds that have come from the waste products or the remains of living organisms (plant and animal) or organic molecules made by chemical reactions. Organic load is used herein in a context-dependent mannerwhich may vary per facility, but organic load can be generalized into the following non- limiting examples: animal feces; blood; debris; soil; milk; fats; oils; greases; manure; plant residue etc. These examples of organic load are mainly high in proteins, nitrogen, lipids and carbohydrates. [0058] As used herein, the terms "/V-halamine",“/V-halamine compound”, and “/V-halamine group” are used interchangeably to refer to a compound containing one or more nitrogen-halogen covalent bonds that is normally formed by the halogenation of imide and/or amide and/or amine groups within the compound. The presence of the halogen may render the compound biocidal. N- halamine compounds, as referred to in the present disclosure, include both cyclic and acyclic /V-halamine compounds.

[0059] As used herein, the terms“/V-halamine precursor” and“/V-halamine precursor group” are used interchangeably to refer to a functional group of a compound that contains an imide, amide or amine that is susceptible to halogenation to form /V-halamines or /V-halamine groups with biocidal activity. When part of a compound, /V-halamine precursors provide the potential for biocidal activity and/or the potential for increased biocidal-activity. Increased or enhanced biocidal-activity is as compared to the biocidal activity of the compound independent of the halogenation of the /V-halamine precursor group.

[0060] As used herein, the terms“textile”, “cloth” and“fabric” may be interchangeable and these terms refer to products made by knitting, weaving or matting of natural fibers, synthetic fibers or combinations thereof.

[0061] In select embodiments of the present disclosure, a cationic center may comprise a positively charged atom, for example a quaternized ammonium group, a quaternized phosphonium group, or a tertiarized sulfonium group.

[0062] In select embodiments of the present disclosure, there is one cationic center in the reaction-product compound. In select embodiments of the present disclosure, there are at least two cationic centers in the reaction-product compound that are separated by a chain of carbon atoms, saturated or unsaturated hydrocarbons. The chain may include cyclic structures and/or branches, or not. In embodiments where there are at least two cationic centers, the at least two cationic centers may be the same or different. [0063] In select embodiments of the present disclosure a coating incorporation group may allow a reaction-product compound to form at least part of or incorporate into at least one of: an acetate polymer; a vinyl ester polymer, including a vinyl acetate polymer; a vinyl acetate homopolymer; an acrylate polymer, including a methacrylate polymer; a polystyrene polymer; a modified polystyrene polymer; a melamine; a modified melamine; a urethane polymer; a polyurethane polymer; an acrylate polyol; a polyester; a self-crosslinking polyester; an epoxide polymer, including an epoxide-ester polymer or a fluoropolymer; a silicone or silicone derivative polymer; a polyethylene; a polypropylene; a polyvinyl chloride; a polyamide; a polybutylene; a poly(buta-1 ,3- diene); a polysulfone; a precursor for any of the components listed above; a copolymer comprising two or more of the components listed above; or any combinations thereof.

[0064] In select embodiments, the coating incorporation group allows the reaction-product compounds to form part of or be incorporated into a polymer as either homopolymers or heteropolymers, which are also referred to herein as copolymers. Forming part of or becoming incorporated into a polymer may occur by forming one or more chemical bonds between monomers that form the polymer. The polymer structure may be organized so that at least select of the /V-halamine precursor groups are positioned external to the polymer structure. This organization allows the polymer to have biocidal activity or the potential for biocidal activity or the potential for enhanced biocidal activity. Furthermore, when the polymer is subjected to a chemical-modification step, the polymer will have greater biocidal activity as compared to prior to the chemical-modification step. The chemical-modification step may be performed once or multiple times so that the biocidal activity of the polymer may be increased once or multiple times.

[0065] In select embodiments of the present disclosure, a reaction- product compound may be used as a component in one or more coating formulations. One or more of these coating formulations may be useful for coating soft surfaces such as textiles, and/or hard-surfaces. One or more of these coating formulations may be useful as epoxy coatings. The coating formulations may further include other components such as one or more of a potentiator compound, a cross-linker, a hardener, a diluent, a surfactant or other chemical additives.

[0066] In select embodiments of the present disclosure, the coating incorporation group may connect to a component that is already linked or bonded to a surface or to another component that can readily link with or bond the surface. When the at least two components of the coating formulation become chemically linked or bonded upon the surface, the surface may then be considered coated. Alternatively, the coating formulation may comprise a reaction-product compound as substantially the only active ingredient and the reaction-product compound may homopolymerize to form a polymer that is coated on the surface. Due to the reaction-product compound being coated on the surface, the coated surface may have biocidal activity or the potential for biocidal activity or the potential for enhanced biocidal activity. [0067] In select embodiments of the present disclosure, a coating incorporation group may include a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof or combinations thereof. Reaction-product compounds containing such coating incorporation groups may be useful as, but not limited to, components of a coating formulation.

[0068] Select embodiments of the present disclosure relate to reaction- product compounds that have one or more vinyl groups as the coating incorporation group. The one or more vinyl terminal-groups may allow the reaction-product compound to chemically link to or bond with another component of a coating formulation.

[0069] Select embodiments of the present disclosure relate to reaction- product compounds that have one or more hydroxyl groups as a coating incorporation group. The one or more hydroxyl linking coating incorporation groups may allow the reaction-product compound to chemically link to or bond with another component of the coating formulation.

[0070] TMPD may also be used as a reactant to synthesize reaction- product compounds that are suitable for use in an epoxy-based coating system. In particular, TMPD may be used as a reactant to synthesize reaction-product compounds that have one or more /V-halamine precursor groups, one or more cationic centers, and one or more coating incorporation groups, where the coating incorporation groups are based on primary amines. These reaction- product compounds may be suitable as components of an epoxy-based coating system, which are suitable for coating hard surfaces.

[0071] TMPD is a cyclic amine compound as shown in formula (I):

[0072] Select embodiments of the present disclosure relate to the use of a TMPD as a reactant in one or more synthesis reactions to make one or more intermediate compounds or one or more reaction-product compounds. The reaction-product compounds may comprise at least one /V-halamine precursor group, at least one cationic center, and at least one coating incorporation group. The at least one cationic center may be incorporated in: a first reaction step in which TMPD is a reactant; a second reaction step that follows the first reaction step; a third reaction step that follows the second reaction step; or a combination thereof. The at least one coating incorporation group may be incorporated in: a first reaction step in which TMPD is a reactant; a second reaction step that follows the first reaction step; a third reaction step that follows the second reaction step; or a combination thereof. [0073] The reaction-product compounds disclosed herein may have biocidal activity or they may have a potential for biocidal activity or they may have a potential for enhanced biocidal activity. Following one or more chemical- modification reactions, the reaction-product compounds may have an increased biocidal activity than prior to the further modification reactions. Furthermore, over time the reaction-product compounds may demonstrate a reduced biocidal activity or no biocidal activity due to various reasons including, but not limited to: exposure to microbes; inhibition caused by organic load; depletion of one or more biocidal components; or combinations thereof. When the reaction-product compounds have a reduced biocidal activity or no biocidal activity, the reaction- product compounds may regain biocidal activity by being exposed to one or more further chemical-modification reactions so that the biocidal activity increases to a greater level than the biocidal activity prior to being exposed to the one or more further chemical-modification reactions. The increase in biocidal activity may also be referred to herein as enhanced biocidal activity. The one or more chemical- modification reactions may be the same as the one or more further chemical- modifications reactions, or not.

[0074] In the reaction-product compounds disclosed herein, the N- halamine precursor group can be chemically modified to change the /V-halamine precursor group to an /V-halamine group. Following the chemical modification, the one or more reaction-production compounds may have biocidal activity or enhanced biocidal activity, as compared to the biocidal activity prior to the chemical modification. The chemical modification may occur once or more than once. The /V-halamine precursor group may be chemically modified by a halogenation reaction, such as a fluorination, bromination, a chlorination, an iodination or combinations thereof. [0075] Embodiments of the present disclosure will now be described by reference to FIG. 1 to FIG. 27 and the following examples.

EXAMPLES

[0076] In the following examples, nuclear magnetic resonance spectroscopy analysis (NMR) and mass spectrometry (MS) were used to verify compound purity. Unless otherwise indicated, the NMR was proton 1 H-NMR performed at 300 MHz and the MS was matrix assisted laser desorption/ionization performed on a tandem mass spectrometer.

[0077] FIG. 1 shows one example of a use of TMPD as a reactant in a chemical reaction for making a preliminary intermediate compound (A). A reaction vessel was charged with 1 equivalent (55 g; 357 mmol) of TMPD, 1 equivalent (66 g; 357 mmol) of 1 -dodecylamine and 8.5 g of sodium borohydride was dissolved in 300 ml_ methanol. The contents of the reaction vessel were mixed at room temperature for 24 hours before the methanol was evaporated to yield a viscous orange product that was dried under vacuum. The viscous orange product was washed with three cycles of deionized water to substantially remove remaining sodium borohydride. The reaction produced 1 10 g of compound (A) (95 % yield). The purity of compound (A) was determined to be > 98 % by NMR in DMSO-D6. FIG. 2 shows an example of the NMR spectrum obtained. The molecular mass of compound (A) was verified through MS. FIG. 3 shows an example of the MS spectrum obtained.

[0078] TMPD can be used to make a preliminary intermediate compound by different synthetic routes. For example, compound (A) can be prepared by catalytic hydrogenation as described in US patent application publication number 2010/00074083.

[0079] FIG. 4 shows one example of a use of a preliminary intermediate compound derived from TMPD as a reactant in a chemical reaction for making an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group. In the reaction of FIG. 4, an intermediate compound (B) is prepared from the preliminary intermediate compound (A). A reaction vessel was charged with 1.0 equivalent (2.9 g; 6.16 mmol) of compound (A), 1.0 equivalent (1.1 g; 6.16 mmol) of 3-chloro-2- hydroxypropyl methacrylate, and 2.0 equivalents (1.7 g; 12.32 mmol) of potassium carbonate were dissolved in 30 mL of acetonitrile. The contents of the reaction vessel were refluxed for 24 hours. The reaction mixture was then filtered to substantially remove potassium carbonate and any chloride salts that may have formed. Acetonitrile was then evaporated out of the filtered solution under vacuum to provide 2.81 g compound (B) as a viscous orange oil (98 % yield). The purity of determined to be > 99 % by NMR in CDCb. FIG. 5 shows an example of the NMR spectrum obtained. The molecular mass of compound (B) was verified through MS. FIG. 6 shows an example of the MS spectrum obtained.

[0080] FIG. 7 shows one example of a use of an intermediate compound derived from TMPD that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making a reaction-product compound that includes at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the reaction of FIG. 7, a reaction product compound (C) is prepared from the intermediate compound (B). In a reaction vessel, 1.0 equivalent (1 .0 g; 2.14 mmol) of compound (B) was added to 1.0 equivalent (1.025 g; 2.14 mmol) of (4-bromobutyl)triphenylphosphonium bromide in 10 mL of methanol. The contents of the reaction vessel were refluxed for 24 hours before the methanol was evaporated to yield a viscous amber-colored product that was dried under vacuum. The reaction produced 2.0 g of compound (C) (99 % yield). The purity of compound (C) was determined to be > 98 % by NMR in DMSO-D6. FIG. 8 shows an example of the NMR spectrum obtained. The molecular mass of compound (C) was verified through MS. FIG. 9 shows an example of the MS spectrum obtained.

[0081] FIG. 10 shows an example of a use of an intermediate compound derived from TMPD that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making a reaction-product compound that includes at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the reaction of FIG. 10, a reaction product compound (D) is prepared from the intermediate compound (B). In a reaction vessel, 1.0 equivalent (1.0 g; 2.14 mmol) of compound (B) was added to 1.0 equivalent (0.99 g; 2.14 mmol) of (4-bromopropyl)triphenylphosphonium bromide in 10 mL of methanol. The contents of the reaction vessel were refluxed for 72 hours before the methanol was evaporated to yield a viscous amber-colored product that was washed with brine and deionized water (to remove any sodium borohydride remaining from an earlier synthetic step) and dried under vacuum. The reaction produced 1 .95 g of compound (D) (99 % yield). The purity of compound (D) was determined to be > 98 % by NMR in DMSO-D6. FIG. 11 shows an example of the NMR spectrum obtained. The molecular mass of compound (D) was verified through MS. FIG. 12 shows an example of the MS spectrum obtained. The spectrum of FIG. 12 suggests that one Br ion may be replaced by a Cl ion in compound (D). Without being bound to any particular theory, the Cl ion may have been introduced by the brine washing.

[0082] FIG. 13 shows one example of a potentially larger-scale use of a preliminary intermediate compound derived from TMPD as a reactant in a chemical reaction for making an intermediate compound that includes at least one cyclic /V-halamine precursor group and at least one coating incorporation group ( e.g . producing greater than about 50 g of the intermediate compound). In the reaction of FIG. 13, the intermediate compound (B) is prepared from the preliminary intermediate compound (A). A reaction vessel was charged with 1 .0 equivalent (40.0 g; 0.123 mol) of compound (A), 1.0 equivalent (22.0 g; 0.123 mol) of 3-chloro-2-hydroxypropyl methacrylate, and 2.0 equivalents (34.0 g; 0.246 mol) of potassium carbonate dissolved in 150 ml_ of acetonitrile. The contents of the reaction vessel were refluxed for 24 hours. The reaction mixture was then filtered to substantially remove potassium carbonate and any chloride salts that may have formed. Acetonitrile was then evaporated out of the filtered solution under vacuum to provide 57.4 g compound (B) as a viscous orange oil (98 % yield). The purity of compound (B) determined to be > 99 % by NMR in CDCb (NMR substantially the same as that shown in FIG. 5). The molecular mass of compound (B) was verified through MS (MS substantially the same as that shown in FIG. 6).

[0083] FIG. 14 shows one example of a larger-scale use of an intermediate compound derived from TMPD that includes at least one cyclic N- halamine precursor group and at least one coating incorporation group as a reactant in a chemical reaction for making the reaction-product compound that includes at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the reaction of FIG. 14, the reaction product compound (C) is prepared from the intermediate compound (B). In a reaction vessel, 1.0 equivalent (24.95 g; 53.5 mmol) of compound (B) was added to 1.0 equivalent (25.62 g; 53.5 mmol) of (4- bromobutyl)triphenylphosphonium bromide in 100 ml_ of methanol. The contents of the reaction vessel were refluxed for 24 hours before the methanol was evaporated to yield a viscous amber-colored product that was washed with brine and deionized water (to remove any sodium borohydride remaining from an earlier synthetic step) and dried under vacuum. The reaction produced 50.1 g of compound (C) (99 % yield). The purity of compound (C) was determined to be > 98 % by NMR in DMSO-D6. FIG. 15 shows an example of the NMR spectrum obtained. The molecular mass of compound (C) was verified through MS. FIG. 16 shows an example of the MS spectrum obtained. The spectrum of FIG. 16 suggests that one Br ion may be replaced by a Cl ion in compound (C). Without being bound to any particular theory, the Cl ion may have been introduced by the brine washing.

[0084] FIG. 17 shows one example of a use of a preliminary intermediate compound derived from TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that includes at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the reaction of FIG. 17a, the intermediate compound (B) is prepared from the preliminary intermediate compound (A) using an alternate reagent. A reaction vessel was charged with 1.0 equivalent (70 g; 210 mmol) of compound (A), 1.0 equivalent (30 g; 210 mmol) of glycidyl methacrylate in methanol. The contents of the reaction vessel were stirred at room temperature for 2 hours before the methanol was evaporated under reduced pressure to provide a crude product. In the reaction of FIG. 17b, the reaction-product compound (C) is prepared from the intermediate compound (C). A second reaction vessel was charged with 47g (100 mmol) of the crude product and 50 g (100 mmol) of (4-bromobutyl)triphenylphosphonium bromide in 70 ml_ of methanol. The reaction mixture was refluxed for 48 hours before the methanol was evaporated under reduced pressure to provide compound (C) as an amber oil that was washed with brine and deionized water (to remove any sodium borohydride remaining from an earlier synthetic step) and dried under vacuum. The yield of the reaction was 99 %. FIG. 18 shows an example of the NMR spectrum obtained from the reaction product, for which the purity was inconclusive. The molecular mass of compound (C) was verified through MS. FIG. 19 shows an example of the MS spectrum obtained. The spectrum of FIG. 19 suggests that one Br ion may be replaced by a Cl ion in compound (C). Without being bound to any particular theory, the Cl ion may have been introduced by the brine washing.

[0085] FIG. 20 shows one example of a use of TMPD as a reactant in a chemical reaction for making a preliminary intermediate compound (E). A reaction vessel was positioned in an ice bath and charged with 1 equivalent (60 g; 386 mmol) of TMPD and 1.5 equivalent (35.4 g; 579 mmol) of 2-aminoethanol dissolved in 150 ml_ methanol. Sodium borohydride (17.5 g, 1.2 equivalents, 463 mmol) was added to the reaction mixture in small batches and the ice bath was removed from the reaction vessel. The contents of the reaction vessel were mixed at room temperature for 24 hours, and then 100 ml_ of deionized water was added to the reaction mixture. The reaction product was extracted three times with 50 ml_ aliquots of chloroform, which were then combined, dried with magnesium sulfate, and filtered. The chloroform was evaporated to yield a viscous orange product that was dried under vacuum. The reaction produced 74 g of compound (E) (95 % yield). The product was characterized by NMR in CDCb. FIG. 21 shows an example of the NMR spectrum obtained. The molecular mass of compound (E) was verified through MS. FIG. 22 shows an example of the MS spectrum obtained.

[0086] FIG. 23 shows one example of a use of the preliminary intermediate compound (E) as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic N- halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 23, a reaction- product compound (G) was prepared in a two-step synthesis including the reaction of FIG. 23A, and the reaction of FIG. 23B. In the reaction of FIG. 23A, the intermediate compound (E) was used as a reactant in a chemical reaction with 2-bromoethan-1-ol to form an intermediate compound (F) that comprises a cyclic /V-halamine precursor group and two coating incorporation groups. In the reaction of FIG. 23B, the intermediate compound (F) was used as a reactant in a chemical reaction with (3-bromopropyl)triphenylphosphonium bromide to form the reaction-product compound (G) which comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers.

[0087] FIG. 24 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 24, a reaction-product compound (I) was prepared in a three- step synthesis including the reaction of FIG. 24A, the reaction of FIG. 24B, and the reaction of FIG. 24C. In the reaction of FIG. 24A, TMPD was used as a reactant in a chemical reaction with dodecylamine to form the preliminary intermediate compound (A) that comprises a cyclic /V-halamine precursor group. In the reaction of FIG. 24B, the preliminary intermediate compound (A) was used as a reactant in a chemical reaction with 4-bromo-/V-(2-(methacryloyloxy)ethyl)- A/,/V-dimethylbutan-1-aminium bromide to form an intermediate compound (H) that comprises a cyclic /V-halamine precursor group, a coating incorporation group, and a cationic center. In the reaction of FIG. 24C, the intermediate compound (H) was used as a reactant in a chemical reaction with (3- bromopropyl)triphenylphosphonium bromide to form the reaction-product compound (I) which comprises a cyclic /V-halamine precursor group, a coating incorporation group, and three cationic centers. [0088] FIG. 25 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 25, a reaction-product compound (J) was prepared in a three- step synthesis including the reaction of FIG. 25A, the reaction of FIG. 25B, and the reaction of FIG. 25C. In the reaction of FIG. 25A, TMPD was used as a reactant in a chemical reaction with dodecylamine to form the preliminary intermediate compound (A) that comprises a cyclic /V-halamine precursor group. In the reaction of FIG. 25B, the preliminary intermediate compound (A) was used as a reactant in a chemical reaction with 3-chloro-2-hydroxypropyl methacrylate to form the intermediate compound (B) which comprises a cyclic /V-halamine precursor group and a coating incorporation group. In the reaction of FIG. 25C, the intermediate compound (B) was used as a reactant in a chemical reaction with 1 -bromobutane to form the reaction-product compound (J) which comprises a cyclic /V-halamine precursor group, a coating incorporation group, and a cationic center.

[0089] FIG. 26 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 26, a reaction-product compound (I) was prepared in a three- step synthesis including the reaction of FIG. 26A, the reaction of FIG. 26B, and the reaction of FIG. 26C. In the reaction of FIG. 26A, TMPD was used as a reactant in a chemical reaction with dodecylamine to form the preliminary intermediate compound (A) that comprises a cyclic /V-halamine precursor group. In the reaction of FIG. 26B, the preliminary intermediate compound (A) was used as a reactant in a chemical reaction with (3-bromopropyl)triphenylphosphonium bromide to form an intermediate compound (K) that comprises a cyclic N- halamine precursor group, and a cationic center. In the reaction of FIG. 26C, the intermediate compound (K) was used as a reactant in a chemical reaction with 4-bromo-/V-(2-(methacryloyloxy)ethyl)-/V,/V-dimethylbutan-1-aminium bromide to form the reaction-product compound (I) which comprises a cyclic /V-halamine precursor group, a coating incorporation group, and three cationic centers.

[0090] FIG. 27 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 27, a reaction-product compound (O) was prepared in a three- step synthesis including the reaction of FIG. 27A, the reaction of FIG. 27B, and the reaction of FIG. 27C. In the reaction of FIG. 27A, TMPD was used as a reactant in a chemical reaction with A/¹,/V¹-dimethylethane-1 ,2-diamine to form an intermediate compound (M) that comprises a cyclic /V-halamine precursor group. In the reaction of FIG. 27B, the intermediate compound (M) was used as a reactant in a chemical reaction with (4-bromobutyl)triphenylphosphonium bromide to form an intermediate compound (N) that comprises a cyclic N- halamine precursor group and two cationic centers. In the reaction of FIG. 27C, the intermediate compound (N) was used as a reactant in a chemical reaction with 4-bromo-/V,/V-bis(2-hydroxyethyl)-/V-methylbutan-1-aminium bromide to form the reaction-product compound (O) which comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and three cationic centers.

[0091] FIG. 28 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 28, a reaction-product compound (P) was prepared in a three- step synthesis including the reaction of FIG. 28A, the reaction of FIG. 28B, and the reaction of FIG. 28C. In the reaction of FIG. 28A, TMPD was used as a reactant in a chemical reaction with A/¹,/V¹-dimethylethane-1 ,2-diamine to form an intermediate compound (M) that comprises a cyclic /V-halamine precursor group. In the reaction of FIG. 28B, the intermediate compound (M) was used as a reactant in a chemical reaction with (4-bromobutyl)triphenylphosphonium bromide to form an intermediate compound (N) that comprises a cyclic N- halamine precursor group and two cationic centers. In the reaction of FIG. 28C, the intermediate compound (N) was used as a reactant in a chemical reaction with 3-chloro-2-hydroxypropyl methacrylate to form the reaction-product compound (P) which comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers.

[0092] FIG. 29 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 29, a reaction-product compound (S) was prepared in a three- step synthesis including the reaction of FIG. 29A, the reaction of FIG. 29B, and the reaction of FIG. 29C. In the reaction of FIG. 29A, TMPD was used as a reactant in a chemical reaction with 2-aminoethyl methacrylate to form an intermediate compound (Q) that comprises a cyclic /V-halamine precursor group and a coating incorporation group. In the reaction of FIG. 29B, the intermediate compound (Q) was used as a reactant in a chemical reaction with (4- bromobutyl)triphenylphosphonium bromide to form an intermediate compound (R) that comprises a cyclic /V-halamine precursor group, a cationic center and a coating incorporation group. In the reaction of FIG. 29C, the intermediate compound (R) was used as a reactant in a chemical reaction with ethyl bromide to form the reaction-product compound (S) which comprises a cyclic /V-halamine precursor group, a coating incorporation group, and two cationic centers.

[0093] FIG. 30 shows one example of a use of TMPD as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center. In the at least one chemical reaction of FIG. 30, a reaction-product compound (V) was prepared in a three- step synthesis including the reaction of FIG. 30A, the reaction of FIG. 30B, and the reaction of FIG. 30C. In the reaction of FIG. 30A, TMPD was used as a reactant in a chemical reaction with 2-aminopropane-1 ,3-diol to form an intermediate compound (T) that comprises a cyclic /V-halamine precursor group and two coating incorporation groups. In the reaction of FIG. 30B, the intermediate compound (T) was used as a reactant in a chemical reaction with (4-bromobutyl)triphenylphosphonium bromide to form an intermediate compound (U) that comprises a cyclic /V-halamine precursor group, a cationic center and two coating incorporation groups. In the reaction of FIG. 30C, the intermediate compound (U) was used as a reactant in a chemical reaction with ethyl bromide to form the reaction-product compound (V) which comprises a cyclic /V-halamine precursor group, two coating incorporation groups, and two cationic centers.

[0094] FIG. 31 shows an example of three intermediate compounds that are each made by a reaction in which TMPD is a reactant, each intermediate compound is part of a reaction for making a reaction-product compound that comprises a cyclic /V-halamine precursor group, two coating incorporation groups and two cationic centers; and

[0095] FIG. 32 shows an example of a general structure for a reaction product and an intermediate compound that may be made using TMPD as a reactant in one more reactions.

Claims

1 . Use of 2,2,6,6-tetramethyl-4-piperidone as a reactant in at least one chemical reaction for making a first reaction-product compound that comprises at least one cyclic /V-halamine precursor group and at least one cationic center.

2. The use of claim 1 , wherein the first reaction-product compound further comprises at least one coating incorporation group.

3. The use of claim 2, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

4. The use of claim 2, wherein the at least one coating incorporation group incorporates the first reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

5. Use of 2,2,6,6-tetramethyl-4-piperidone as a reactant in at least one chemical reaction for making a first intermediate compound that comprises at least one cyclic /V-halamine precursor group and at least one coating incorporation group.

6. The use of claim 5, wherein the first intermediate is prepared from a preliminary intermediate compound.

7. The use of claim 6, wherein the preliminary intermediate is prepared by a chemical reaction involving 2,2,6,6-tetramethyl-4-piperidone and a primary amine.

8. Use of the first intermediate compound of any one of claims 5 through 7 as a reactant in at least one chemical reaction for making a second reaction- product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

9. The use of claim 8, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

10. The use of claim 8, wherein the at least one coating incorporation group incorporates the second reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

1 1. Use of 2,2,6,6-tetramethyl-4-piperidone as a reactant in at least one chemical reaction for making a second intermediate compound that comprises at least one cyclic /V-halamine precursor group and at least one cationic center.

12. The use of claim 1 1 , wherein the second intermediate compound is prepared from a preliminary intermediate compound.

13. The use of claim 12, wherein the preliminary intermediate is prepared by a chemical reaction involving 2,2,6,6-tetramethyl-4-piperidone and a primary amine.

14. Use of the second intermediate compound of any one of claims 1 1 through 13 as a reactant in at least one chemical reaction for making a third reaction- product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

15. The use of claim 14, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

16. The use of claim 14, wherein the at least one coating incorporation group incorporates the third reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

17. Use of 2,2,6,6-tetramethyl-4-piperidone as a reactant in at least one chemical reaction for making a third intermediate compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

18. The use of claim 17, wherein the third intermediate is prepared from a preliminary intermediate compound.

19. The use of claim 18, wherein the preliminary intermediate is synthesized in a chemical reaction involving 2,2,6,6-tetramethyl-4-piperidone and a primary amine.

20. Use of the third intermediate compound of any one of claims 17 through 19 as a reactant in at least one chemical reaction for making a fourth reaction- product compound that comprises at least one cyclic /V-halamine precursor group, at least one coating incorporation group, and at least one cationic center.

21. The use of claim 20, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

22. The use of claim 20, wherein the at least one coating incorporation group incorporates the second reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

23. A coating comprising the first reaction-product compound defined in claim 1 , the second reaction-product compound defined in claim 8, the third reaction- product defined in claim 14, the fourth reaction-product defined in claim 20, or combinations thereof.

24. A process for making a fifth reaction-product compound that comprises at least one cyclic /V-halamine precursor group, at least one cationic center, and at least one coating incorporation group, the process comprising reacting 2, 2, 6, 6- tetramethyl-4-piperidone with at least one further reactant, wherein the at least one further reactant comprises the at least one coating incorporation group.

25. The process of claim 24, wherein the at least one coating incorporation group is a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

26. The process of claim 24, wherein the at least one coating incorporation group incorporates the fourth reaction-product compound into an acetate polymer, a vinyl ester polymer, an acrylate polymer, a polystyrene polymer, a modified polystyrene polymer, a melamine, a modified melamine, a urethane polymer, a polyurethane polymer, an acrylate polyol, a polyester, a self- crosslinking polyester, an epoxide polymer, a fluoropolymer, a silicone polymer, a silicone derivative polymer, a polyethylene, a polypropylene, a polyvinyl chloride, a polyamide, a polybutylene, a poly(buta-1 , 3-diene), a polysulfone, a precursor of any of the polymers listed above, or combinations thereof.

27. The process of claim 26, wherein the vinyl ester polymer is a vinyl acetate polymer.

28. The process of claim 27, wherein the vinyl acetate polymer is a vinyl acetate homopolymer.

29. The process of claim 26, wherein acrylate polymer is a methacrylate polymer.

30. The process of claim 26, wherein the epoxide polymer is an epoxide-ester polymer.

31. Use of 2,2,6,6-tetramethylpiperidone as a reactant in at least one chemical reaction for making a reaction-product compound that comprises at least one cyclic N-halamine precursor group and at least one cationic center.

32. The use of claim 31 , wherein the at least one cationic center is a cationic nitrogen center, a cationic phosphorous center, a cationic sulfur center, or combinations thereof.

33. The use of claim 31 or 32, wherein the reaction-product compound further comprises at least one coating incorporation group.

34. The use of claim 33, wherein the reaction-product compound is prepared from an intermediate compound that comprises the at least one coating incorporation group.

35. The use of claim 33 or 34, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

36. The use of claim 33 or 34, wherein the at least one coating incorporation group incorporates the first reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.

37. The use of any one of claims 34 through 36, wherein the intermediate compound further comprises the at least one cationic center.

38. The use of claim 37, wherein the at least one cationic center is a cationic nitrogen center, a cationic phosphorous center, a cationic sulfur center, or combinations thereof.

39. A coating comprising the reaction-product compound defined in any one of claims 31 through 38.

40. A process for making a reaction-product compound that comprises at least one cyclic N-halamine precursor group and at least one cationic center, the process comprising reacting 2,2,6,6-tetramethylpiperidone with at least one reactant in at least one chemical reaction, wherein:

(a) the at least one reactant comprises the at least one cationic center;

(b) the at least one reactant reacts with 2,2,6,6-tetramethylpiperidone to form the at least one cationic center;

(c) the at least one reactant reacts with an intermediate compound derived from 2,2,6,6-tetramethylpiperidone to form the at least one cationic center; or

(d) any combination of (a) through (c).

41. The process of claim 40, wherein the at least one cationic center is a cationic nitrogen center, a cationic phosphorous center, a cationic sulfur center, or combinations thereof.

42. The process of claim 40 or 41 , wherein the reaction-product compound further comprises at least one coating incorporation group.

43. The process of claim 42, wherein the at least one reactant comprises the at least one coating incorporation group.

44. The process of claim 42 or 43, wherein the intermediate compound derived from 2,2,6,6-tetramethylpiperidone comprises the at least one coating incorporation group.

45. The process of any one of claims 42 through 44, wherein the at least one coating incorporation group is a vinyl group, a hydroxyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an epoxide group, a thioruea group, a cyanate group, an isocyanate group, an amine group or combinations thereof.

46. The process of any one of claims 42 through 44, wherein the at least one coating incorporation group incorporates the second reaction-product compound into an acetate polymer, a vinyl group, a vinyl acetate group, an acrylate group, a methacrylate group, a methyl methacrylate group, an acrylamide group, a styrenic group, a hydroxyl group, an alkyloxy group, an aldehyde group, a ketone group, a carboxy group, an epoxide group, an amine group, an imine group, an imide group, an azide group, an amide group, a cyanate group, an isocyanate group, a carbamide group, a thioruea group, a thiol group, a sulfinic group, a sulfone group, a sulfoxide group, or combinations thereof.