Glycidyl (METH)acrylate material and methods of use

Abstract

This invention provides a material comprising glycidyl (meth)acrylate or a salt thereof of formula (I), wherein m is an integer from 1 to 10000, n is an integer from 0 to 10000, each R1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperyl or -NR2-, R2 is hydrogen, aryl, heteroaryl, C1-6 alkylaryl, C1-6 alkyl heteroaryl or C1-6 alkyl, each Y is independently present as desired and is -NR3- or substituted C1-6 alkyl as desired, R3 is hydrogen or C1-6 alkyl, and each Z is independently aryl, heteroaryl or C1-6 alkyl. 2-6 heterocyclic groups, each substituted as required, and each * independently representing a hydrogen, a terminal group, or a bond connected to the remainder of the material, wherein at least one * is a bond connected to the remainder of the material, and wherein the remainder of the material is bonded via sp3-sp3 carbon-carbon bonds.

Description

Glycidyl (meth)acrylate materials and methods of use The present invention relates to a material comprising glycidyl (meth)acrylate of formula (I): Formula (I), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl, heteroaryl or C 2-6 a heterocyclic group, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, provided that at least one * is a bond to the rest of the material and wherein the rest of the material is bonded via an sp3-sp3 carbon-carbon bond. The present invention also relates to a method for making the material, the method comprising: (i) (a) irradiating a polymer support with a radiation source and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on a polymer support in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer support comprises one or more CH aliphatic bonds, to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer support via one or more sp3-sp3 carbon-carbon bonds, and (ii) modifying the grafted glycidyl (meth)acrylate or a polymer thereof with one or more compounds of the formula X'-Y'-Z', wherein X' is HO-, HOOC-, HS-, piperidine or HNR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, Y' is optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, and Z' is aryl, heteroaryl or C 2-6 heterocyclic groups, each of which is optionally substituted. Membrane-based liquid treatment processes have been applied across various industries. For example, direct flow filtration (DFF) and tangential flow filtration (TFF), including microfiltration, ultrafiltration, nanofiltration, and diafiltration, can be used to separate dissolved molecules or suspended particles. However, removing small, soluble particles, such as metal ions, from aqueous and / or organic solutions remains a challenge. Therefore, there remains a need for materials and methods for removing one or more metal ions from solutions. The present invention provides such materials and methods. These and other advantages of the present invention (e.g., simple and clean conjugation, uniform conjugation, rotational migration of ligands, efficient deprotonation, and / or accessible chelation / coordination of ligands), as well as other features of the present invention, will be apparent from the description of the invention provided herein. The present invention provides a material comprising glycidyl (meth)acrylate of formula (I): Formula (I), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl (such as halogenated aryl), heteroaryl or C 2-6heterocyclyl, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, with the proviso that at least one * is a bond to the rest of the material, and wherein the rest of the material is bound via an sp3-sp3 carbon-carbon bond. The present invention further provides a method for making the materials described herein, the method comprising: (i) (a) irradiating (e.g., radiating) a polymer support with an irradiation (e.g., radiation) source and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on a polymer support in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer support comprises one or more CH aliphatic bonds to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer support via one or more sp3-sp3 carbon-carbon bonds, and (ii) modifying the grafted glycidyl (meth)acrylate or a polymer thereof with one or more compounds of the formula X'-Y'-Z', wherein X' is HO-, HOOC-, HS-, piperidine or HNR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, Y' is optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, and Z' is aryl (such as halogenated aryl), heteroaryl or C 2-6 heterocyclic groups, each of which is optionally substituted. The present invention further provides a method of removing one or more metal ions from a solution comprising passing the solution through or contacting the solution with a material described herein. One aspect of the present invention provides a material comprising glycidyl (meth)acrylate of formula (I): Formula (I), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl (such as halogenated aryl), heteroaryl or C 2-6 heterocyclyl, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, with the proviso that at least one * is a bond to the rest of the material, and wherein the rest of the material is bound via an sp3-sp3 carbon-carbon bond. In some embodiments, the material comprises glycidyl (meth)acrylate of formula (Ia): Formula (Ia), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl (such as halogenated aryl), heteroaryl or C 2-6 heterocyclyl, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, with the proviso that at least one * is a bond to the rest of the material, and wherein the rest of the material is bound via an sp3-sp3 carbon-carbon bond. As used herein, the term "(meth)acrylate" refers to acrylate or methacrylate. Thus, in any embodiment of the materials described herein, each R 1 is independently hydrogen or methyl. In some embodiments, each R 1 is methyl. In other specific examples, each R 1 is hydrogen. In any of the material embodiments described herein, m is an integer from 1 to 10,000 (e.g., 1 to 5,000, 1 to 1,000, 1 to 500, 1 to 100, 10 to 50, or 1 to 10). In some embodiments, m is an integer from 1 to 1,000. In certain embodiments, m is 1, meaning that the glycidyl (meth)acrylate monomer is grafted onto the remainder of the material. In other embodiments, m is greater than 1, meaning that the glycidyl (meth)acrylate polymer is grafted onto the remainder of the material. In any of the embodiments of the materials described herein, n is an integer from 0 to 10,000 (e.g., 0 to 5,000, 0 to 1,000, 0 to 500, 0 to 100, 0 to 50, or 0 to 10). In other words, unmodified glycidyl (meth)acrylate monomers, designated by the variable n, are optionally present. In some embodiments, n is an integer from 0 to 1,000. In certain embodiments, unmodified glycidyl (meth)acrylate monomers are present, and thus n is an integer from 1 to 10,000 (e.g., 1 to 5,000, 1 to 1,000, 1 to 500, 1 to 100, 10 to 50, or 1 to 10). In some embodiments, n is an integer from 1 to 1,000. In any of the embodiments of the materials described herein, each X is independently -O-, -COO-, -S-, piperidine, or -NR 2-, where R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 In some embodiments, each X is independently -NR 2-, and R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6Alkyl (e.g., linear or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl). In some embodiments, each X is -S-. In any of the embodiments of the materials described herein, each Y is independently optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl), where R 3 is hydrogen or C 1-6 In some embodiments, each Y is independently -NR 3-, where R 3 is hydrogen or C 1-6 Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl or hexyl). In other embodiments, each Y is independently an optionally substituted C 1-6 Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl). In any of the embodiments of the materials described herein, each Z is independently aryl, heteroaryl, or C 2-6 heterocyclic groups, each of which is optionally substituted. For example, Z can be phenyl, furyl, benzofuranyl, phenylthio, benzophenylthio, pyrrolyl, indolyl, isoindolyl, azaindolyl, pyridinyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, benzoxazolyl, pyrazolyl, imidazolyl, benzimidazolyl, thiazolyl, benzothiazolyl, isothiazolyl, pyrimidinyl, pyrimidinyl, trithiophene, oxazolyl, oxazolyl, quinazolinyl, oxazolidinyl, pyrrolidinone, pyrrolidinyl, piperidinyl, hydantoinyl, valerolactamyl, oxiranyl, oxetane, tetrahydrofuranyl, tetrahydropyranyl, tetrahydropyridinyl, tetrahydropyrimidinyl, tetrahydrophenylthio, tetrahydrothiopyranyl, tetrahydropyrimidinyl, tetrahydrophenylthio, tetrahydrothiopyranyl, piperidinyl or dihydropyrimidinyl, each of which is optionally substituted. In some embodiments, at least one Z is a halogenated aryl (e.g., a fluorinated aryl) or a halogenated heteroaryl (e.g., a fluorinated heteroaryl). Alternatively or additionally, at least one Z is an optionally substituted pyridinyl. In certain embodiments, at least one Z is an optionally substituted pyridinyl. In some embodiments, each Z is independently selected from the following: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and , each of which is replaced as necessary. As used herein, the term "optionally substituted" refers to one or more substituents selected from the group consisting of halo (e.g., fluorine, chlorine, bromine, or iodine), cyano, nitro, trifluoromethyl, sulfonic acid (e.g., sulfate, sulfonate, sulfonyl, etc.), hydroxyl, amino (e.g., primary, secondary, or tertiary amine with 1 to 8 carbon atoms), C 1-8 Alkyl, C 1-8 Alkoxy, C 1-8 aminoalkyl, C 1-8 Alternatively or additionally, when referring to an optionally substituted aryl, heteroaryl or C 2-6 In the case of heterocyclic groups, the term "optionally substituted" may refer to fused or bridged aryl, heteroaryl or C 2-6 Heterocyclic group. In some embodiments, each moiety XYZ is independently selected from the following: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and . In any of the embodiments of the materials described herein, each * independently represents a hydrogen, a terminal group, or a bond to the remainder of the material, provided that at least one * is a bond to the remainder of the material, and wherein the remainder of the material is bonded via an sp3-sp3 carbon-carbon bond. As used herein, the term "terminating group" refers to any chemical moiety that remains as a result of quenching a free radical. Common terminal groups will be readily apparent to one of ordinary skill in the art. In some embodiments of the materials described herein, each * independently represents a hydrogen or a bond to the remainder of the material, provided that at least one * is a bond to the remainder of the material, and wherein the remainder of the material is bonded via an sp3-sp3 carbon-carbon bond. In some embodiments, the material comprising the glycidyl (meth)acrylate of Formula (I) or the glycidyl (meth)acrylate of Formula (Ia) has more than one C-C bond to the remainder of the material. Alternatively or additionally, the material may comprise more than one glycidyl (meth)acrylate of formula (I) or glycidyl (meth)acrylate of formula (Ia). The glycidyl (meth)acrylate of formula (I) or the glycidyl (meth)acrylate of formula (Ia) can be incorporated into any suitable material (e.g., a compound or medium), as long as the glycidyl (meth)acrylate of formula (I) or the glycidyl (meth)acrylate of formula (Ia) is bonded to the remainder of the material via at least one carbon designated by * in formulas (I) and (Ia), wherein the remainder of the material is bonded via an sp3-sp3 carbon-carbon bond. A person skilled in the art will readily understand that the glycidyl (meth)acrylate of formula (I) or the glycidyl (meth)acrylate of formula (Ia) can be incorporated into the material at any number of positions and at any number of times. Thus, the material can be any suitable material (e.g., a compound or medium) that includes aliphatic C-H bonds available for sp3-sp3 carbon-carbon bonding. In some embodiments, the material is porous, thereby allowing liquids or fluids to pass through the material. In some embodiments, the remainder of the material to which the glycidyl (meth)acrylate of formula (I) or the glycidyl (meth)acrylate of formula (Ia) is bound is a macromolecular support selected from a membrane (e.g., a porous membrane or a permeable membrane), a fiber medium, a polymer coating (e.g., a laminate or sealing layer, such as a polyurethane coating, an epoxy coating, an acrylic coating, etc.) or a material (e.g., gelatin, alginate, starch, polyethylene, polypropylene, nylon, polyvinylidene fluoride, polyethylene oxide, polypropylene oxide, polyethylene oxide / polypropylene oxide, polyacrylonitrile, poly(meth)acrylate, poly(meth)acrylamide, polyamide, polyimide, polyester, cellulose, polystyrene, etc.), a metal organic framework, a monolithic support (e.g., a catalyst support), a bead (e.g., a polymer bead), a filter, or a resin (e.g., a chromatography resin). In some embodiments, the macromolecular carrier comprises gelatin, alginate, starch, polyethylene (e.g., high-density polyethylene), polypropylene, nylon, polyvinylidene fluoride, polyethylene oxide, polypropylene oxide, polyethylene oxide / polypropylene oxide, polyacrylonitrile, poly(meth)acrylate, poly(meth)acrylamide, polyamide (e.g., nylon), polyimide, polyester, cellulose, polystyrene, or a combination thereof. In certain embodiments, the macromolecular carrier comprises polyethylene, polypropylene, nylon, polyvinylidene fluoride, polyethylene oxide, polypropylene oxide, polyethylene oxide / polypropylene oxide, polyacrylonitrile, cellulose, or a combination thereof. In preferred embodiments, the macromolecular carrier comprises polyvinylidene fluoride, polyethylene (e.g., high-density polyethylene), polypropylene, nylon, or a combination thereof. Thus, in some embodiments, the material has formula (II): , or formula (IIa): or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl, heteroaryl or C 2-6 heterocyclic group, each of which is optionally substituted, and each Q is independently hydrogen, a terminal group, or MS, with the proviso that at least one Q is MS, and each MS is independently a macromolecular support selected from a membrane, a fiber medium, a polymer coating or material, a metal organic framework, a monolithic support, a bead, a filter, or a resin, and wherein MS is bound via an sp3-sp3 carbon-carbon bond. All other variables m, n, R 1. Definitions and specific examples of X, Y, Z and macromolecular carriers are as described herein with respect to the materials of the present invention. In any of the embodiments of the materials described herein, each Q is independently hydrogen, a terminal group, or MS, with the proviso that at least one Q is MS, wherein MS is bound via an sp3-sp3 carbon-carbon bond. In some embodiments of the materials described herein, each Q is independently hydrogen or MS, with the proviso that at least one Q is MS, wherein MS is bound via an sp3-sp3 carbon-carbon bond. In certain embodiments, the materials of Formula (II) or Formula (IIa) have more than one C-MS bond. In some embodiments, the material comprises glycidyl (meth)acrylate modified with 3-picolylamine, glycidyl (meth)acrylate modified with 4-fluorobenzylamine, glycidyl (meth)acrylate modified with 2-picolylamine, glycidyl (meth)acrylate modified with 1-(3-aminopropyl)imidazole, or a combination thereof. In this regard, the materials disclosed herein may comprise one or more -XYZ moieties as defined herein. For example, the material may comprise glycidyl (meth)acrylate modified with 3-picolylamine, glycidyl (meth)acrylate modified with 4-fluorobenzylamine, glycidyl (meth)acrylate modified with 2-picolylamine, or glycidyl (meth)acrylate modified with 1-(3-aminopropyl)imidazole, or any combination of these modifications. In some embodiments, the material comprises a combination of glycidyl (meth)acrylate modified with 3-picolylamine and glycidyl (meth)acrylate modified with 4-fluorobenzylamine. In some embodiments, the materials described herein are present in the form of a film (e.g., a thin film). The film can have any suitable thickness. For example, the film can have a thickness of about 2 mil to about 20 mil, about 2 mil to about 15 mil, about 2 mil to about 10 mil, about 5 mil to about 20 mil, about 5 mil to about 15 mil, about 5 mil to about 10 mil, about 7 mil to about 20 mil, about 7 mil to about 15 mil, or about 7 mil to about 10 mil. Alternatively or additionally, the materials described herein can comprise multiple films (e.g., thin films) that are stacked to form a composite material (e.g., a composite film). Thus, in some embodiments, the materials described herein are layered (e.g., stacked) to provide a composite material comprising one or more layers of the materials described herein. Thus, each layer of the composite material can comprise a material of Formula (I) or (Ia) or Formula (II) or (IIa) containing one or more XYZ moieties. In some embodiments, the one or more XYZ moieties in each layer are the same. In other embodiments, one or more XYZ portions of each layer are different. The present invention also provides an aspect of a method for making the materials described herein, the method comprising: (i) (a) irradiating (e.g., radiating) a polymer support with an irradiation (e.g., radiation) source and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on the polymer support in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer support comprises one or more CH aliphatic bonds to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer support via one or more sp3-sp3 carbon-carbon bonds, and (ii) modifying the grafted glycidyl (meth)acrylate or a polymer thereof with one or more compounds of the formula X'-Y'-Z', wherein X' is HO-, HOOC-, HS-, piperidine or HNR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, Y' is optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, and Z' is aryl, heteroaryl or C 2-6heterocyclyl, each of which is optionally substituted. All other variables m, n, R 1. Definitions and specific examples of X, Y, Z, and macromolecular carriers are as described herein with respect to the present materials. In some embodiments, step (i) is performed in an oxygen-free environment (e.g., less than 50 ppm O). 2. Less than 40 ppm O 2. Less than 30 ppm O 2. Less than 20 ppm O 2. Less than 10 ppm O 2 or less than 5 ppm O 2). In some embodiments, step (ii) is performed in an oxygen-free environment (e.g., less than 50 ppm O 2. Less than 40 ppm O 2. Less than 30 ppm O 2. Less than 20 ppm O 2. Less than 10 ppm O 2 or less than 5 ppm O 2). In some embodiments, steps (i) and (ii) are performed in an oxygen-free environment (e.g., less than 50 ppm O 2. Less than 40 ppm O 2. Less than 30 ppm O 2. Less than 20 ppm O 2 or less than 10 ppm O 2). In certain embodiments, step (i) and / or step (ii) are carried out in a condition with 0 to 10 ppm O 2. 0 to 5 ppm O 2 to 10 ppm O 2 or 2 to 5 ppm O 2. Carry out in an oxygen-free environment. The method comprises (a) irradiating (e.g., irradiating) a polymer support with an irradiation (e.g., radiation) source and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on the polymer support in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer support comprises one or more C—H aliphatic bonds, to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer support via one or more sp3-sp3 carbon-carbon bonds. Thus, the polymer support can be irradiated or activated (e.g., by generating free radicals) in the presence or absence of glycidyl (meth)acrylate or a polymer thereof. If the polymer support is irradiated or activated (e.g., by generating free radicals) in the absence of glycidyl (meth)acrylate or a polymer thereof, the glycidyl (meth)acrylate or a polymer thereof can then be impregnated onto the polymer support. The polymer support can be irradiated or activated (e.g., by generating free radicals) by any suitable means. For example, the polymer support can be irradiated or activated (e.g., by generating free radicals) by electron beam irradiation, gamma irradiation, X-ray irradiation, ultraviolet light, plasma, corona discharge, chemical initiators, or combinations thereof. In some embodiments, the method comprises irradiating the polymer support with electron beam irradiation, gamma irradiation, X-ray irradiation, or combinations thereof, and then impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof. In other embodiments, the method comprises generating free radicals on the polymer support using ultraviolet light, plasma, corona discharge, chemical initiators, or combinations thereof in the presence of glycidyl (meth)acrylate or a polymer thereof. Glycidyl (meth)acrylate or its polymer can be grafted onto the polymer support using any suitable means at any suitable temperature. For example, the irradiated or activated (e.g., by generating free radicals) polymer support can be immersed in a solution (e.g., a monomer solution) containing glycidyl (meth)acrylate or its polymer, the irradiated or activated (e.g., by generating free radicals) polymer support can be sprayed with a solution (e.g., a monomer solution) containing glycidyl (meth)acrylate or its polymer, or the polymer support can be irradiated or activated (e.g., by generating free radicals) while immersed in a solution (e.g., a monomer solution) containing glycidyl (meth)acrylate or its polymer. Glycidyl (meth)acrylate or its polymer can be grafted onto the polymer support at a temperature of 0°C to 100°C, 0°C to 50°C, 10°C to 30°C, or 20°C to 30°C. Typically, glycidyl (meth)acrylate or its polymer is grafted onto the polymer support at room temperature (e.g., approximately 25°C). In some embodiments, the polymer support or the polymer support that has been irradiated or activated (eg, by generating free radicals) is in the form of a roll that can be wound or unwound during any stage of the process. The solution containing glycidyl (meth)acrylate or its polymer (e.g., monomer solution) can contain any suitable solvent. For example, the solution containing glycidyl (meth)acrylate or its polymer (e.g., monomer solution) can include an organic solvent such as an alcohol (e.g., ethanol or methanol), sulfide, sulfide, acetate, ether, amide, nitrile, or a combination thereof. In some embodiments, the solution containing glycidyl (meth)acrylate or its polymer (e.g., monomer solution) includes an alcohol such as methanol as a solvent. In certain embodiments, the solution containing glycidyl (meth)acrylate or its polymer (e.g., monomer solution) further includes allyl glycidyl ether, 1,2-epoxy-5-hexene, 3,4-epoxy-1-butene, allyl 2,3-epoxypropyl ether, or a combination thereof. The method comprises modifying the grafted glycidyl (meth)acrylate or its polymer with one or more compounds of the formula X'-Y'-Z', wherein X' is HO-, HOOC-, HS-, piperidine or HNR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl (eg, linear or branched methyl, ethyl, propyl, butyl, pentyl or hexyl), Y' is optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl), R 3 is hydrogen or C 1-6 alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl), and Z' is aryl, heteroaryl, or C 2-6 heterocyclic groups, each of which is optionally substituted. In some embodiments of compounds of formula X'-Y'-Z', X' is -NHR 2, and R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl, or hexyl). In some embodiments of the compound of formula X'-Y'-Z', X' is -SH. In some embodiments of compounds of formula X'-Y'-Z', Y' is -NR 3-, where R 3 is hydrogen or C 1-6 Alkyl (e.g., straight-chain or branched methyl, ethyl, propyl, butyl, pentyl or hexyl). In other embodiments of compounds of formula X'-Y'-Z', Y' is optionally C 1-6 The alkyl group is substituted with an alkyl group (e.g., a straight-chain or branched methyl, ethyl, propyl, butyl, pentyl or hexyl group). In some embodiments of compounds of formula X'-Y'-Z', Z' is aryl, heteroaryl or C 2-6 heterocyclic groups, each of which is optionally substituted. For example, Z can be phenyl, furyl, benzofuranyl, phenylthio, benzophenylthio, pyrrolyl, indolyl, isoindolyl, azaindolyl, pyridinyl, quinolyl, isoquinolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyrazolyl, imidazolyl, benzimidazolyl, thiazolyl, benzothiazolyl, isothiazolyl, pyrimidinyl, pyrimidinyl, triazolyl, oxazolyl, pyrimidinyl, pyrimidinyl, triazolyl, pyrimidin ... substituted 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, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 119, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 132, 133, 134, In some embodiments, the compound of formula X'-Y'-Z' is selected from the following compounds: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 and . The grafted glycidyl (meth)acrylate or polymer thereof can be modified with one or more compounds of the formula X'-Y'-Z' by any suitable means at any suitable temperature. For example, the grafted glycidyl (meth)acrylate or polymer thereof can be modified by mixing, contacting, immersing, or similar means. The grafted glycidyl (meth)acrylate or polymer thereof can be modified with a solution containing one or more compounds of the formula X'-Y'-Z' or a plurality of solutions containing compounds of the formula X'-Y'-Z'. The solution containing one or more compounds of the formula X'-Y'-Z' can contain a solvent such as water, an alcohol (e.g., ethanol or methanol), a sulfide, a sulfide, an acetate, an ether, an amide, a nitrile, or a combination thereof. In some embodiments, the solution comprising one or more compounds of formula X'-Y'-Z' comprises dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), and / or dimethylsulfoxide (DMSO), optionally combined with water. The grafted glycidyl (meth)acrylate or polymer thereof can be modified at a temperature of 25°C to 200°C, 25°C to 150°C, 25°C to 100°C, 50°C to 200°C, 50°C to 150°C, or 50°C to 100°C. Typically, the glycidyl (meth)acrylate or polymer thereof is grafted onto the polymer support at a temperature of about 75°C to 100°C. The solution comprising one or more compounds of Formula X'-Y'-Z' can comprise any suitable amount of the one or more compounds of Formula X'-Y'-Z'. For example, the solution comprising one or more compounds of Formula X'-Y'-Z' can comprise from about 0.1 wt.% to about 50 wt.%, from about 0.1 wt.% to about 40 wt.%, from about 0.1 wt.% to about 30 wt.%, from about 0.1 wt.% to about 20 wt.%, from about 1 wt.% to about 50 wt.%, from about 1 wt.% to about 40 wt.%, from about 1 wt.% to about 30 wt.%, from about 1 wt.% to about 20 wt.%, from about 5 wt.% to about 50 wt.%, from about 5 wt.% to about 40 wt.%, from about 5 wt.% to about 30 wt.%, or from about 5 wt.% to about 20 wt.% of the one or more compounds of Formula X'-Y'-Z'. Modification of the grafted glycidyl (meth)acrylate or polymer thereof can be facilitated by an acid (e.g., a Brønsted acid or a Lewis acid) or a base (e.g., a Brønsted base or a Lewis base). In some embodiments, modification of the grafted glycidyl (meth)acrylate or polymer thereof is facilitated by an amine base (e.g., trimethylamine, trimethylamine, diisopropylethylamine, or the like). The modified grafted glycidyl (meth)acrylate or its polymer (i.e., the materials described herein) can be washed with water, an organic solvent (e.g., an alcohol such as ethanol or methanol, sulfone, sulfide, acetate, ether, amide, nitrile, or a combination thereof), an acidic solution (e.g., aqueous hydrochloric acid or aqueous sulfuric acid), an alkaline solution (e.g., aqueous tetramethylammonium hydroxide or aqueous ammonium hydroxide), or a combination thereof. In some embodiments, the modified grafted glycidyl (meth)acrylate or its polymer (i.e., the materials described herein) is washed with an acidic solution (e.g., aqueous hydrochloric acid or aqueous sulfuric acid) followed by an alkaline solution (e.g., aqueous tetramethylammonium hydroxide or aqueous ammonium hydroxide). The modified grafted glycidyl (meth)acrylate or its polymer (i.e., the material described herein) or its intermediate can be dried by any suitable means. For example, the modified grafted glycidyl (meth)acrylate or its polymer (i.e., the material described herein) or its intermediate can be dried by air, high temperature, a desiccant, a screen, or a combination thereof. For any suitable purpose, the materials described herein can be used in any suitable industrial application. For example, the materials described herein can be used in water purification applications, wastewater treatment applications, organic solvent processing applications, mining applications, electronic (e.g., microelectronics) applications, papermaking applications, pharmaceutical applications, biomedical applications, energy applications (e.g., as separators in fuel cells or battery packs), or metallurgical applications. In general, the materials described herein are used to selectively remove one or more metal ions from a fluid (i.e., a solution). The fluid can be any suitable liquid containing a solvent (e.g., water, alcohol, sulfite, sulfide, acetate, ether, ketone, amide, nitrile, or a combination thereof) and one or more metal ions. In some embodiments, the fluid (i.e., solution) is an aqueous solution. In some embodiments, the fluid (i.e., solution) comprises an organic solvent, such as an alcohol (e.g., ethanol or methanol), sulfite, sulfide, acetate, ether, ketone, amide, nitrile, or a combination thereof. In some embodiments, the fluid comprises cyclohexanone (CHN), propylene glycol methyl ether (PGME), propylene glycol methyl ether acetate (PGMEA), ethyl lactate, or a combination thereof. In some embodiments, the materials described herein can be used in a method for removing one or more metal ions from a solution, the solution comprising (i) passing the solution through the material or (ii) contacting the solution with the material. For example, the material can be used as a filter, porous medium, chromatography resin, membrane, or the like, through which the solution is passed or contacted to remove the one or more metal ions. Therefore, the present invention further provides a method for removing one or more metal ions from a solution, the method comprising (i) passing the solution through a material comprising a glycidyl (meth)acrylate of Formula (I), Formula (Ia), Formula (II), or Formula (IIa) or (ii) contacting the solution therewith. In some embodiments, the present invention provides a method for removing one or more metal ions from a solution, the method comprising (i) passing the solution through one or more materials comprising a glycidyl (meth)acrylate of Formula (I), Formula (Ia), Formula (II), or Formula (IIa) or (ii) contacting the solution therewith. The method can be used to remove any suitable ion. Alternatively or additionally, the method can be used to pass any suitable ion through the material. For example, the method can be used to selectively remove one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. Alternatively or additionally, the method can be used to selectively allow one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. In certain embodiments, the method selectively passes lithium through the material and removes one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. The method can remove any suitable amount of one or more metal ions from the solution. For example, the method can remove at least 40% of the one or more metal ions from the solution, remove at least 50% of the one or more metal ions from the solution, remove at least 60% of the one or more metal ions from the solution, remove at least 70% of the one or more metal ions from the solution, remove at least 80% of the one or more metal ions from the solution, or remove at least 90% of the one or more metal ions from the solution. In some embodiments, the method removes at least 50% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. In certain embodiments, the method removes at least 60% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. In a preferred embodiment, the method removes at least 70% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. In some embodiments, the solution that has passed through or been in contact with the material is a desired product of the methods described herein. Thus, in such embodiments, the method may further comprise recovering the solution (e.g., an aqueous or organic solution) that has passed through or been in contact with the material. Without wishing to be bound by any particular theory, it is believed that when smaller metal ions (such as lithium and / or sodium) are desired, the recovered solution will be a desired product because smaller metal ions (such as lithium and / or sodium) are more likely to pass through the materials described herein. In other embodiments, the one or more metal ions removed from the solution are the desired products of the methods described herein. Thus, in these embodiments, the method may further comprise recovering the one or more metal ions removed from the solution. The one or more metal ions may be recovered by any suitable means. For example, the material containing the one or more metal ions may be washed with a recovery solution. Without wishing to be bound by any particular theory, it is believed that when larger metal ions, such as magnesium, aluminum, potassium, calcium, manganese, iron, barium, etc., are desired, these desired metal ions will remain in the material because larger metal ions are less likely to pass through the materials described herein. The aspects of the invention described above (including embodiments) may be beneficial alone or in combination with one or more other aspects or embodiments. Without limiting the foregoing description, certain non-limiting embodiments of the present disclosure, numbered 1-24, are provided below. As will be apparent to one of ordinary skill in the art upon reading this disclosure, each of the individually numbered embodiments may be used or combined with any of the preceding or following individually numbered embodiments. It is intended that support be provided for all such combinations of embodiments and is not limited to the combinations of embodiments explicitly provided below: (1) In embodiment (1), a material is presented, which comprises glycidyl (meth)acrylate of formula (I): Formula (I), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl, heteroaryl or C 2-6 heterocyclyl, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, with the proviso that at least one * is a bond to the rest of the material, and wherein the rest of the material is bound via an sp3-sp3 carbon-carbon bond. (2) In embodiment (2), a material as in embodiment (1) is presented, wherein the material comprises a glycidyl (meth)acrylate of formula (Ia): Formula (Ia), or a salt thereof, wherein m is an integer from 1 to 10,000, n is an integer from 0 to 10,000, and each R 1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperidine or -NR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, each Y is independently present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, each Z is independently aryl, heteroaryl or C 2-6 heterocyclyl, each of which is optionally substituted, and each * independently represents hydrogen, a terminal group, or a bond to the rest of the material, with the proviso that at least one * is a bond to the rest of the material, and wherein the rest of the material is bound via an sp3-sp3 carbon-carbon bond. (3) In embodiment (3), the material of embodiment (1) or embodiment (2) is presented, wherein each R 1 is a methyl group. (4) In embodiment (4), the material of any one of embodiments (1) to (3) is presented, wherein m is an integer from 1 to 1000. (5) In embodiment (5), the material of any one of embodiments (1) to (4) is presented, wherein n is an integer from 1 to 1000. (6) In embodiment (6), the material of any one of embodiments (1) to (5) is presented, wherein each X is independently -NR 2-, and R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 alkyl. (7) In embodiment (7), the material of any one of embodiments (1) to (5) is presented, wherein each X is -S-. (8) In embodiment (8), a material as in any one of embodiments (1) to (7) is presented, wherein each Z is independently phenyl, furyl, benzofuranyl, phenylthio, benzophenylthio, pyrrolyl, indolyl, isoindolyl, azaindolyl, pyridyl, quinolyl, isoquinolyl, oxazolyl, isoxazolyl, benzoxazolyl, pyrazolyl, imidazolyl, benzimidazolyl, thiazolyl, benzothiazolyl, isothiazolyl, pyrimidin ... substituted 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, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 70, 69, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 110 (9) In embodiment (9), a material as in any one of embodiments (1) to (8) is presented, wherein at least one Z is a halogenated aryl or a halogenated heteroaryl. (10) In embodiment (10), a material as in any one of embodiments (1) to (9) is presented, wherein at least one Z is a fluorinated aryl or fluorinated heteroaryl. (11) In embodiment (11) there is presented a material as in any one of embodiments (1) to (10), wherein at least one Z is an optionally substituted pyridyl group. (12) In embodiment (12), a material as in any one of embodiments (1) to (11) is presented, wherein the bond to the remainder of the material is a bond to a macromolecular support selected from the group consisting of a membrane, a fiber medium, a polymer coating or material, a metal organic framework, a monolithic support, a bead, a filter, or a resin, and wherein the macromolecular support is bound via an sp3-sp3 carbon-carbon bond. (13) In embodiment (13), a material as in embodiment (12) is presented, wherein the macromolecular carrier comprises gelatin, alginate, starch, polyethylene, polypropylene, nylon, polyvinylidene fluoride, polyethylene oxide, polypropylene oxide, polyethylene oxide / polypropylene oxide, polyacrylonitrile, poly(meth)acrylate, poly(meth)acrylamide, polyamide, polyimide, polyester, cellulose, polystyrene or a combination thereof. (14) In embodiment (14), a material as in embodiment (12) is presented, wherein the macromolecular carrier comprises polyvinylidene fluoride, polyethylene, polypropylene, nylon, or a combination thereof. (15) In embodiment (15), a method for producing a material as in any one of embodiments (1) to (14) is presented, the method comprising: (i) (a) irradiating (e.g., radiating) a polymer support with an irradiation (e.g., radiation) source and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on the polymer support in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer support comprises one or more CH aliphatic bonds to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer support via one or more sp3-sp3 carbon-carbon bonds, and (ii) modifying the grafted glycidyl (meth)acrylate or a polymer thereof with one or more compounds of the formula X'-Y'-Z', wherein X' is HO-, HOOC-, HS-, piperyl or HNR 2-, R 2 is hydrogen, aryl, heteroaryl, C 1-6 Alkyl aryl, C 1-6 Alkyl heteroaryl or C 1-6 Alkyl, Y' is optionally present and is -NR 3- or C substituted as necessary 1-6 Alkyl, R 3 is hydrogen or C 1-6 alkyl, and Z' is aryl, heteroaryl or C 2-6 heterocyclic groups, each of which is optionally substituted. (16) In embodiment (16), a method as in embodiment (15) is presented, wherein the method comprises irradiating (e.g., radiating) the polymer support with electron beam irradiation, gamma irradiation, X-ray irradiation, or a combination thereof, and subsequently impregnating the polymer support with glycidyl (meth)acrylate or a polymer thereof. (17) In embodiment (17), a method as in embodiment (15) is presented, wherein the method comprises generating free radicals on the polymer support using ultraviolet light, plasma, corona discharge, chemical initiator or a combination thereof in the presence of glycidyl (meth)acrylate or a polymer thereof. (18) In embodiment (18), a method as in any one of embodiments (15) to (17) is presented, wherein steps (i) and / or (ii) are performed in 2. The test should be carried out in an environment with a concentration of 50 ppm or less. (19) In embodiment (19), a method of removing one or more metal ions from a solution is presented, the method comprising (i) passing the solution through the material of any one of embodiments (1) to (14) or (ii) contacting the solution with the material of any one of embodiments (1) to (14). (20) In embodiment (20), a method as in embodiment (19) is presented, wherein the solution is an aqueous solution. (21) In embodiment (21), the method of embodiment (19) or embodiment (20) is presented, wherein the solution comprises an organic solvent. (22) In embodiment (22), a method as in any one of embodiments (19) to (21) is presented, wherein the method removes at least 50% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. (23) In embodiment (23), a method as in any one of embodiments (19) to (21) is presented, wherein the method removes at least 60% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. (24) In embodiment (24), the method of any one of embodiments (19) to (21) is presented, wherein the method removes at least 70% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or a combination thereof. The following examples further illustrate the present invention but should not be construed as limiting its scope in any way. This example provides an exemplary experimental procedure for preparing glycidyl methacrylate grafted coils, which is summarized in Scheme 1. Scheme 1. A high-density polyethylene (HDPE) (1 micron) substrate was fed into an electron beam, irradiated in the electron beam, wound with an interleaf, and dipped in a coating solution containing glycidyl methacrylate, and then wound to form a glycidyl methacrylate grafted roll. The coating solution was prepared by dissolving glycidyl methacrylate (2 kg) in methanol (18 kg) and mixing for 10 minutes to form a 10 wt% solution of glycidyl methacrylate in methanol. The electron beam and grafting conditions are described in Table 1 below. Table 1. Electron beam and grafting conditions As indicated in Table 1, all unwinding, irradiation, monomer dipping and rewinding processes are performed at The results were performed in an environment with a 2 content of <50 ppm. Weight change, critical water surface tension (CWST), and FTIR were used to confirm the grafting of glycidyl methacrylate onto the HDPE substrate. The glycidyl methacrylate grafted rods were washed with methanol for 4 hours using a recirculating trickle wash, followed by a deionized water trickle wash for 6 hours to remove any residual ungrafted monomer, oligomer, and polymer. After drying the glycidyl methacrylate grafted rods, the glycidyl methacrylate uptake was determined to be approximately 100-140 wt % based on the HDPE substrate. Example 2 This example provides an exemplary experimental procedure for preparing the materials of formula (I) described herein, which is summarized in Scheme 2. Scheme 2. 3-Picolylamine (10 g) was dissolved in 90 g of water / DMSO (1:1), and the resulting solution was added to a 12" x 12" strip of glycidyl methacrylate-grafted HDPE. The combination was heated to 85°C for 24 hours. After the glycidyl methacrylate-grafted HDPE was cooled and the remaining solution removed, the resulting medium was washed several times with isopropanol and water. The washed medium was then dried in an oven at 65°C for 2 hours. The absorption of 3-picolylamine was determined to be approximately 10-30% by weight. The washed surface-modified medium was then cleaned by soaking it in methanol for 30 minutes, in 50% isopropanol or methanol for 30 minutes, and in deionized water for 2 hours. Following soaking in various solvents, the surface-modified medium was soaked in 1% hydrochloric acid for 2 hours and then rinsed with deionized water to a pH of 7. The protonated functional groups on the medium were then deprotonated by soaking the medium in 1% tetramethylammonium hydroxide for 2 hours and then rinsed with deionized water to a pH of 7. The resulting material was then drip-washed with deionized water for 1 hour and dried in an oven at 65°C for 2 hours. The 3-picolylamine uptake after cleaning was determined to be approximately 10-30% by weight. The HDPE grafted with glycidyl methacrylate modified with 3-picolylamine was analyzed by scanning electron microscopy (SEM), and the top surface image and cross-sectional image are shown in FIG1A and FIG1B , respectively. This example demonstrates the metal removal efficiency of the material of Example 2 described herein. Metal removal efficiency (MRE) testing was conducted using 47 mm punched discs of the coated HDPE material from Example 2. 20-30 mL of a solution containing 1 ppb of each metal impurity (i.e., titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver) in (a) cyclohexanone (CHN), (b) propylene glycol methyl ether (PGME), or (c) propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) was passed through the disc, and the resulting metal ion concentration was measured by inductively coupled plasma-mass spectrometry (ICP-MS). The metal removal efficiency (i.e., percentage of concentration after removal) was calculated for three separate experiments for each of solvents (a) to (c), and the results are plotted in Figures 2 to 4, respectively. As is apparent from the results shown in Figures 2-4, the coated HDPE material of Example 2 removed over 80% of titanium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver, and in some cases, vanadium, from a variety of solvents. Additionally, the coated HDPE material of Example 2 was particularly effective at removing chromium, manganese, iron, cobalt, nickel, copper, and zinc from all tested solvents, exhibiting MREs greater than 90% in all cases. Example 4 This example provides an exemplary experimental procedure for preparing the materials of formula (I) described herein, which is summarized in Scheme 3. Scheme 3. 4-Fluorobenzylamine (10 g) was dissolved in 90 g of DMSO, and the resulting solution was added to a 12" x 12" strip of glycidyl methacrylate-grafted HDPE. The combination was heated to 85°C for 24 hours. After the glycidyl methacrylate-grafted HDPE was cooled and the remaining solution removed, the resulting medium was washed several times with isopropanol and water. The washed medium was then dried in an oven at 65°C for 2 hours. The absorption of 4-fluorobenzylamine was determined to be approximately 10-30% by weight. The washed surface-modified medium was then cleaned by soaking it in methanol for 30 minutes, in 50% isopropanol or methanol for 30 minutes, and in deionized water for 2 hours. Following soaking in various solvents, the surface-modified medium was soaked in 1% hydrochloric acid for 2 hours and then rinsed with deionized water to a pH of 7. The protonated functional groups on the medium were then deprotonated by soaking the medium in 1% tetramethylammonium hydroxide for 2 hours and then rinsed with deionized water to a pH of 7. The resulting material was then drip-washed with deionized water for 1 hour and dried in an oven at 65°C for 2 hours. The 4-fluorobenzylamine uptake after cleaning was determined to be approximately 10-30% by weight. Scanning electron microscopy (SEM) confirmed that HDPE grafted with glycidyl methacrylate modified with 4-fluorobenzylamine. Example 5 This example demonstrates the metal removal efficiency of the material of Example 4 described herein. Metal removal efficiency (MRE) testing was conducted using 47 mm punched discs of the coated HDPE material from Example 4. 20-30 mL of a solution containing 1 ppb of each metal impurity (i.e., titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver) in (a) cyclohexanone (CHN), (b) propylene glycol methyl ether (PGME), or (c) propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) was passed through the disc, and the resulting metal ion concentration was measured by inductively coupled plasma-mass spectrometry (ICP-MS). The metal removal efficiency (i.e., percentage of concentration after removal) was calculated for three separate experiments for each of solvents (a) to (c), and the results are plotted in Figures 5 to 7, respectively. As is apparent from the results shown in Figures 5-7, the coated HDPE material of Example 4 removed over 80% of titanium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver, and in some cases, vanadium, from a variety of solvents. Additionally, the coated HDPE material of Example 4 was particularly effective at removing chromium, manganese, iron, cobalt, nickel, copper, and zinc from all tested solvents, exhibiting MREs greater than 90% in all cases. Example 6 This example demonstrates the metal removal efficiency of a composite material comprising the material of Example 2 and the material of Example 4 described herein. Metal removal efficiency (MRE) testing was conducted using a 47 mm punched disc with a double layer consisting of one layer of the coated HDPE material from Example 2 and one layer of the coated HDPE material from Example 4. 20-30 mL of a solution containing 1 ppb of each metal impurity (i.e., titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver) in (a) cyclohexanone (CHN), (b) propylene glycol methyl ether (PGME), or (c) propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) was passed through the disc, and the resulting metal ion concentration was measured by inductively coupled plasma-mass spectrometry (ICP-MS). The metal removal efficiency (i.e., percentage of concentration after removal) was calculated for three separate experiments for each of solvents (a) to (c), and the results are plotted in Figures 8 to 10, respectively. Figures 8-10 labeled "A," i.e., Figures 8A, 9A, and 10A, are oriented with a layer of Example 2 coated HDPE material on top and a layer of Example 4 coated HDPE material on the bottom, i.e., the solution first passed through the layer of Example 2 coated HDPE material. Figures 8-10 labeled "B," i.e., Figures 8B, 9B, and 10B, are oriented with a layer of Example 4 coated HDPE material on top and a layer of Example 2 coated HDPE material on the bottom, i.e., the solution first passed through the layer of Example 4 coated HDPE material. As is apparent from the results shown in Figures 8 to 10, the composite material comprising the material of Example 2 and the material of Example 4 provides an MRE that matches the performance of the material of Example 2 and the material of Example 4. Example 7 This example provides an exemplary experimental procedure for preparing the materials of formula (I) described herein, which is summarized in Scheme 4. Scheme 4. 3-Picolylamine (5 g) and 4-fluorobenzylamine (5 g) were dissolved in 90 g of water / DMSO (1:1), and the resulting solution was added to a 12" x 12" strip of glycidyl methacrylate-grafted HDPE. The combination was heated to 85°C for 24 hours. After the glycidyl methacrylate-grafted HDPE was cooled and the remaining solution removed, the resulting medium was washed several times with isopropanol and water. The washed medium was then dried in an oven at 65°C for 2 hours. The absorption of 3-picolylamine and 4-fluorobenzylamine was determined to be approximately 10-30% by weight. The washed surface-modified medium was then cleaned by soaking it in methanol for 30 minutes, in 50% isopropanol or methanol for 30 minutes, and in deionized water for 2 hours. Following soaking in various solvents, the surface-modified medium was soaked in 1% hydrochloric acid for 2 hours and then rinsed with deionized water to a pH of 7. The protonated functional groups on the medium were then deprotonated by soaking the medium in 1% tetramethylammonium hydroxide for 2 hours and then rinsed with deionized water to a pH of 7. The resulting material was then drip-washed with deionized water for 1 hour and dried in an oven at 65°C for 2 hours. The absorption of 3-picolylamine and 4-fluorobenzylamine after cleaning was determined to be approximately 10-30% by weight. Scanning electron microscopy (SEM) confirmed the HDPE grafted with glycidyl methacrylate modified with 3-picolylamine and 4-fluorobenzylamine. Example 8 This example demonstrates the metal removal efficiency of the material of Example 7 described herein. Metal removal efficiency (MRE) testing was conducted using 47 mm punched discs of the coated HDPE material from Example 7. 20-30 mL of a solution containing 1 ppb of each metal impurity (i.e., titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver) in (a) cyclohexanone (CHN), (b) propylene glycol methyl ether (PGME), or (c) propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) was passed through the disc, and the resulting metal ion concentration was measured by inductively coupled plasma-mass spectrometry (ICP-MS). The metal removal efficiency (i.e., percentage of concentration after removal) was calculated for three separate experiments for each of solvents (a) to (c), and the results are plotted in Figures 11 to 13, respectively. As is apparent from the results shown in Figures 11 to 13, the coated HDPE material of Example 7 removed over 80% of titanium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver, and in some cases, vanadium, from a variety of solvents. Furthermore, the coated HDPE material of Example 7 was particularly effective at removing titanium, manganese, iron, cobalt, nickel, copper, zinc, and silver from all tested solvents, exhibiting MREs greater than 90% in all cases. All references, including publications, patent applications, and patents, cited herein are hereby incorporated by reference to the same extent as if each reference were individually and specifically indicated to be incorporated by reference and were set forth in its entirety herein. Unless otherwise indicated herein or clearly contradicted by context, the use of the terms "a," "an," "the," "at least one," and similar referents in the context of describing the present invention, especially in the context of the following claims, should be understood to cover both the singular and the plural. Unless otherwise indicated herein or clearly contradicted by context, the use of the term "at least one" followed by a list of one or more items (e.g., "at least one of A and B") should be understood to mean one item (A or B) or any combination of two or more of the listed items (A and B) selected from the listed items. Unless otherwise noted, the terms "comprising," "having," "including," and "containing" should be understood as open-ended terms (i.e., meaning "including but not limited to") Unless otherwise indicated herein, the recitation of ranges of values ​​herein is merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or clearly contradicted by context. The use of any and all examples or exemplary language (e.g., "such as") provided herein is intended merely to better illustrate the invention and does not limit the scope of the invention unless otherwise claimed. The language in this specification should not be construed as indicating that any unclaimed element is essential to the practice of the invention. Preferred embodiments of the present invention are described herein, including the best modes known to the inventors of this case for implementing the present invention. After reading the foregoing description, variations of those preferred embodiments may become apparent to those with common knowledge in the art. The inventors of this case expect that those with common knowledge in the art will adopt such variations as appropriate, and the inventors of this case intend to practice the present invention in a manner different from that specifically described herein. Therefore, if applicable law permits, the present invention includes all modifications and equivalents of the subject matter described in the claims appended hereto. In addition, unless otherwise indicated herein or otherwise clearly contradictory to the context, the present invention encompasses any combination of the above-mentioned elements in all possible variations thereof. none FIG1A provides a scanning electron microscope (SEM) image of the top surface of the 3-picolylamine-modified glycidyl methacrylate-grafted high-density polyethylene (HDPE) prepared in Example 1. FIG1B provides a scanning electron microscope (SEM) image of a cross-section of the 3-picolylamine-modified glycidyl methacrylate-grafted HDPE prepared in Example 1. FIG2 provides a bar graph showing the percentage of metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a cyclohexanone (CHN) solvent exhibited by the 3-picolylamine-modified glycidyl methacrylate-grafted HDPE prepared in Example 2, as described in Example 3. [Figure 3] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from propylene glycol methyl ether (PGME) solvent, as described in Example 3, exhibited by 3-picolylamine-modified glycidyl methacrylate-grafted HDPE prepared in Example 2. [Figure 4] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) solvent, as described in Example 3, exhibited by 3-picolylamine-modified glycidyl methacrylate-grafted HDPE prepared in Example 2. [Figure 5] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from cyclohexanone (CHN) solvent, as described in Example 5, exhibited by 4-fluorobenzylamine-modified glycidyl (meth)acrylate-grafted HDPE prepared in Example 4. [Figure 6] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from propylene glycol methyl ether (PGME) solvent, as described in Example 5, exhibited by 4-fluorobenzylamine-modified glycidyl (meth)acrylate-grafted HDPE prepared in Example 4. FIG7 provides a bar graph showing the percentage of metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) solvent, as described in Example 5, exhibited by the 4-fluorobenzylamine-modified glycidyl (meth)acrylate-grafted HDPE prepared in Example 4.[ FIG8A ] provides a bar graph showing the percentage metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a cyclohexanone (CHN) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 2 on top and a layer of the coated HDPE material of Example 4 on the bottom, as described in Example 6. [ FIG8B ] provides a bar graph showing the percentage metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a cyclohexanone (CHN) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 4 on top and a layer of the coated HDPE material of Example 2 on the bottom, as described in Example 6. [ FIG. 9A ] provides a bar graph showing the percentage metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a propylene glycol monomethyl ether (PGME) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 2 on top and a layer of the coated HDPE material of Example 4 on the bottom, as described in Example 6. [ FIG. 9B ] provides a bar graph showing the percentage metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a propylene glycol monomethyl ether (PGME) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 4 on top and a layer of the coated HDPE material of Example 2 on the bottom, as described in Example 6. [ FIG. 10A ] provides a bar graph showing the percent metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 2 on top and a layer of the coated HDPE material of Example 4 on the bottom, as described in Example 6. [ FIG. 10B ] provides a bar graph showing the percent metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from a propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) solvent exhibited by a composite material oriented with a layer of the coated HDPE material of Example 4 on top and a layer of the coated HDPE material of Example 2 on the bottom, as described in Example 6. FIG11 provides a bar graph showing the percentage of metal removal efficiency (MRE) for the removal of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from cyclohexanone (CHN) solvent, as described in Example 8, exhibited by glycidyl (meth)acrylate-grafted HDPE modified with 3-picolylamine and 4-fluorobenzylamine prepared in Example 7.[Figure 12] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from propylene glycol methyl ether (PGME) solvent, as described in Example 8, exhibited by glycidyl (meth)acrylate-grafted HDPE modified with 3-picolylamine and 4-fluorobenzylamine prepared in Example 7. [Figure 13] provides a bar graph showing the percentage metal removal efficiency (MRE) of titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, and silver ions from propylene glycol methyl ether acetate (PGMEA) / ethyl lactate (EL) solvent, as described in Example 8, exhibited by glycidyl (meth)acrylate-grafted HDPE modified with 3-picolylamine and 4-fluorobenzylamine prepared in Example 7.

Claims

1. A glycidyl (meth)acrylate material comprising glycidyl (meth)acrylate of formula (I): Formula (I). Or its salts, wherein m is an integer from 1 to 10000, n is an integer from 0 to 10000, each R1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperyl or -NR2-, R2 is hydrogen, aryl, heteroaryl, C1-6 alkylaryl, C1-6 alkyl heteroaryl or C1-6 alkyl, each Y is independently present as desired and is -NR3- or substituted C1-6 alkyl as desired, R3 is hydrogen or C1-6 alkyl, each Z is independently aryl, heteroaryl or C2-6 heterocyclic, each substituted as desired, and each * independently represents hydrogen, a terminal group or a bond connected to the remainder of the glycidyl (meth)acrylate material, wherein at least one * is a bond connected to the remainder of the glycidyl (meth)acrylate material, and wherein the remainder of the glycidyl (meth)acrylate material is bonded via sp3-sp3 carbon-carbon bonds.

2. The glycidyl (meth)acrylate material of claim 1, wherein the glycidyl (meth)acrylate material comprises glycidyl (meth)acrylate of formula (Ia): Formula (Ia). Or its salts, wherein m is an integer from 1 to 10000, n is an integer from 0 to 10000, each R1 is independently hydrogen or methyl, each X is independently -O-, -COO-, -S-, piperyl or -NR2-, R2 is hydrogen, aryl, heteroaryl, C1-6 alkylaryl, C1-6 alkyl heteroaryl or C1-6 alkyl, each Y is independently present as desired and is -NR3- or substituted C1-6 alkyl as desired, R3 is hydrogen or C1-6 alkyl, each Z is independently aryl, heteroaryl or C2-6 heterocyclic, each substituted as desired, and each * independently represents hydrogen, a terminal group or a bond connected to the remainder of the glycidyl (meth)acrylate material, wherein at least one * is a bond connected to the remainder of the glycidyl (meth)acrylate material, and wherein the remainder of the glycidyl (meth)acrylate material is bonded via sp3-sp3 carbon-carbon bonds.

3. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein each R1 is methyl.

4. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein m is an integer from 1 to 1000.

5. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein n is an integer from 1 to 1000.

6. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein each X is independently -NR2- and R2 is hydrogen, aryl, heteroaryl, C1-6 alkylaryl, C1-6 alkyl heteroaryl or C1-6 alkyl.

7. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein each X is -S-.

8. Glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, wherein each Z is independently phenyl, furanyl, benzofuranyl, phenylthio, benzophenylthio, pyrroleyl, indolyl, isoindolyl, azaindolyl, pyridyl, quinolinyl, isoquinolinyl, acezolyl, isoacezolyl, benzoacezolyl, pyrazolyl, imidazoleyl, benzimidazoleyl, thiazolyl, benzothiazolyl, isothiazolyl, dazolyl, Pyrimidinyl, pyridine, triphenyl, phenolinyl, teridine, quinazolinyl, pyrrolidone, pyrrolidinyl, piperidinyl, hydantoinyl, valproic acid, epoxyethyl, oxacyclobutane, tetrahydrofuranyl, tetrahydropiperanyl, tetrahydropyridinyl, tetrahydropyrimidinyl, tetrahydrophenylthio, tetrahydrothiopiperanyl, piperidinyl, or dihydropyrimidinyl, each substituted as required.

9. The glycidyl (meth)acrylate material of claim 1 or claim 2, wherein at least one Z is a halogenated aryl or a halogenated heteroaryl.

10. The glycidyl (meth)acrylate material of claim 1 or claim 2, wherein at least one Z is a fluorinated aryl or a fluorinated heteroaryl.

11. The glycidyl (meth)acrylate material of claim 1 or claim 2, wherein at least one Z is a substituted pyridyl group as desired.

12. The glycidyl (meth)acrylate material of claim 1 or claim 2, wherein the bond attached to the remainder of the glycidyl (meth)acrylate material is a bond attached to a macromolecular carrier selected from: membranes, fibrous media, polymer coatings or materials, metal-organic frameworks, monolithic carriers, beads, filters or resins, and wherein the macromolecular carrier is bonded via sp3-sp3 carbon-carbon bonds.

13. The glycidyl (meth)acrylate material of claim 12, wherein the macromolecular carrier comprises gelatin, alginate, starch, polyethylene, polypropylene, nylon, polyvinylidene fluoride, polyethylene oxide, polypropylene oxide, polyethylene oxide / polypropylene oxide, polyacrylonitrile, poly(meth)acrylate, poly(meth)acrylamide, polyamide, polyimide, polyester, cellulose, polystyrene, or combinations thereof.

14. A method for manufacturing a glycidyl (meth)acrylate material as claimed in claim 1 or claim 2, the method comprising: (i) (a) irradiating a polymer carrier with an irradiation source and subsequently impregnating the polymer carrier with glycidyl (meth)acrylate or a polymer thereof, or (b) generating free radicals on the polymer carrier in the presence of glycidyl (meth)acrylate or a polymer thereof, wherein the polymer carrier comprises one or more CH aliphatic bonds to graft the glycidyl (meth)acrylate or a polymer thereof onto the polymer carrier via one or more sp3-sp3 carbon-carbon bonds, and (ii) using one or more X'-Y' The compound -Z' modifies the grafted glycidyl (meth)acrylate or its polymer, wherein X' is HO-, HOOC-, HS-, piperyl or HNR2-, R2 is hydrogen, aryl, heteroaryl, C1-6 alkylaryl, C1-6 alkyl heteroaryl or C1-6 alkyl, Y' is present as needed and is -NR3- or a substituted C1-6 alkyl as needed, R3 is hydrogen or C1-6 alkyl, and Z' is aryl, heteroaryl or C2-6 heterocyclic, each of which is substituted as needed.

15. The method of claim 14, wherein the method comprises irradiating the polymer carrier with an electron beam, gamma irradiation, X-ray irradiation or a combination thereof, and subsequently impregnating the polymer carrier with glycidyl (meth)acrylate or a polymer thereof.

16. The method of claim 14, wherein the method comprises generating free radicals on the polymer carrier in the presence of glycidyl (meth)acrylate or a polymer thereof using ultraviolet light, plasma, corona discharge, a chemical initiator or a combination thereof.

17. A method for removing one or more metal ions from a solution, comprising (i) passing the solution through a glycidyl (meth)acrylate material as claimed in claim 1, or (ii) contacting the solution with a glycidyl (meth)acrylate material as claimed in claim 1 or claim 2.

18. The method of claim 17, wherein the solution is an aqueous solution.

19. The method of claim 17 or claim 18, wherein the solution contains an organic solvent.

20. The method of claim 17 or claim 18, wherein the method removes at least 50% of one or more metal ions selected from sodium, magnesium, aluminum, potassium, calcium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, arsenic, zirconium, molybdenum, silver, cadmium, tin, barium, tungsten, strontium, lead, or combinations thereof.

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