Charged porous membranes

Abstract

Porous polymeric membranes are provided herein. A membrane comprises a polymer comprising a repeating unit of the formula: (I), where Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof; Q' comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and n is at least 1. Related copolymers synthesis, membranes, and methods are also provided herein.

Description

CHARGED POROUS MEMBRANESFIELD

[0001] The present disclosure relates to charged porous membranes.BACKGROUND

[0002] Porous polymeric membranes are useful for removing contaminants from a variety of fluids.SUMMARY

[0003] Some embodiments relate to a membrane. In some embodiments, the membrane comprises a polymer. In some embodiments, the polymer comprises a repeating unit of the formula:CF3

[0004] where:

[0005] Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;

[0006] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and

[0007] n is at least 1.

[0008] Some embodiments relate to a membrane. In some embodiments, the membrane comprises a copolymer. In some embodiments, the copolymer comprises repeating units of the formula:CF3CF3O' _"7'n mQ Z

[0009] where:

[0010] Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;

[0011] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0012] n is at least 1 ;

[0013] Z’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0014] Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and

[0015] m is at least 1.

[0016] Some embodiments relate to a method. In some embodiments, the method comprises contacting at least a first monomer, a second monomer, and a solvent to form a polymeric component. In some embodiments, the polymer component comprises a repeating unit of the formula:Q

[0017] where:

[0018] Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;

[0019] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and

[0020] n is at least 1 .DRAWINGS

[0021] FIG. 1 is a flowchart of a method for making a copolymer, according to some embodiments.

[0022] FIG. 2 is a1H-NMR spectra of the polymeric component, according to some embodiments.

[0023] FIG. 3 is a19F-NMR spectra of the polymeric component, according to some embodiments.

[0024] FIG. 4 is a13C-NMR spectra of the polymeric component, according to some embodiments.

[0025] FIG. 5 is a1H-NMR spectra of the copolymer, according to some embodiments.

[0026] FIG. 6 is a19F-NMR spectra of the copolymer, according to some embodiments.DETAILED DESCRIPTION

[0027] As used herein, the term “contacting” refers to bringing two or more components into immediate or close proximity, or into direct contact.

[0028] As used herein, the term “alkyl” refers to a hydrocarbyl having from 1 to 30 carbon atoms. The alkyl may be attached via a single bond. An alkyl having n carbon atoms may be designated as a “Cnalkyl.” For example, a “C3 alkyl” may include n-propyl and isopropyl. An alkyl having a range of carbon atoms, such as 1 to 30 carbon atoms, may be designated as a C1-C30 alkyl. In some embodiments, the alkyl is linear. In some embodiments, the alkyl is branched. In some embodiments, the alkyl is substituted. In some embodiments, the alkyl is unsubstituted. In some embodiments, the alkyl comprises or is selected from the group consisting of at least one of a C1-C30 alkyl, C1-C29 alkyl, Ci-C28 alkyl, C1-C27 alkyl, C1-C26 alkyl, C1-C25 alkyl, C1-C24 alkyl, C1-C23 alkyl, C1-C22 alkyl, C1-C21 alkyl, C1-C20 alkyl, C1-C19 alkyl, C1-C18 alkyl, C1-C17 alkyl, C1-C16 alkyl, C1-C15 alkyl, C1-C14 alkyl, C1-C13 alkyl, C1-C12 alkyl, C1-C11 alkyl, C1-C10 alkyl, a C1-C9 alkyl, a Ci-Csalkyl, a C1-C7 alkyl, a C1-C6 alkyl, a C1-C5 alkyl, a C1-C4 alkyl, a C1-C3 alkyl, a C1-C2 alkyl, a C2-C30 alkyl, a C3-C30 alkyl, a C4-C30 alkyl, a C5-C30 alkyl, a C6-C30 alkyl, a C7-C30 alkyl, a Cs-Cso alkyl, a C9-C30 alkyl, a C10-C30 alkyl, a C11-C30 alkyl, a C12-C30 alkyl, a C13-C30 alkyl, a C14-C30 alkyl, a C15-C30 alkyl, a C16-C30 alkyl, a C17-C30 alkyl, a C18-C30 alkyl, a C19-C30 alkyl, a C20-C30 alkyl, a C21-C30 alkyl, a C22-C30 alkyl, a C23-C30 alkyl, a C24-C30 alkyl, a C25-C30 alkyl, a C26-C30 alkyl, a C27-C30 alkyl, a C28-C30 alkyl, a C29-C30 alkyl, a C2-C10 alkyl, a C3-C10 alkyl, a C4-C10 alkyl, a C5-C10 alkyl, a Ce-C alkyl, a C7-C10 alkyl, a Cs-C10 alkyl, a C2-C9 alkyl, a C2-C8 alkyl, a C2-C7 alkyl, a C2-C6 alkyl, a C2-C5 alkyl, a C3-C5 alkyl, or any combination thereof. In some embodiments, the alkyl comprises or is selected from the group consisting of at least one of methyl, ethyl, n-propyl, 1 -methylethyl (iso-propyl), n-butyl, iso-butyl, sec-butyl, n-pentyl, 1 ,1 -dimethylethyl (t-butyl), n-pentyl, iso-pentyl, n-hexyl, isohexyl, 3-methylhexyl, 2-methylhexyl, heptyl, octyl, nonyl, decyl, dodecyl, octadecyl, or any combination thereof.

[0029] As used herein, the term "aryl" refers to a monocyclic or polycyclic aromatic hydrocarbon. The number of carbon atoms of the aryl may be in a range of 5 carbon atoms to 100 carbon atoms. In some embodiments, the aryl has 5 to 20 carbon atoms. For example, in some embodiments, the aryl has 6 to 8 carbon atoms, 6 to 10 carbon atoms, 6 to 12 carbon atoms, 6 to 15 carbon atoms, or 6 to 20 carbon atoms. The term "monocyclic," when used as a modifier, refers to an aryl having a single aromatic ring structure. The term "polycyclic," when used as a modifier, refers to an aryl having more than one aromatic ring structure, which may be fused, bridged, spiro, or otherwise bonded ring structures. In some embodiments, the aryl is — CeHs.

[0030] Non-limiting examples of aryls include, without limitation, at least one of phenyl, tolyl, xylyl (e.g., o-xylyl, m-xylyl, p-xylyl), t-butyltolyl, (e.g., o-t-butyltolyl, m-t-butyltolyl, p-t-butyltolyl), ethylmethylphenyl (e.g., 1-ethyl-4-methylphenyl, 1-ethyl-3-methylphenyl), 1-isopropyl-4-methylphenyl, 1-t-butyl-4-methylphenyl, mesitylene, pseudocumene, durene, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl (e.g., 1 ,4-diethylphenyl), triethylphenyl, propylphenyl, butylphenyl, isobutylphenyl, sec-butylphenyl, t-butylphenyl, hexylphenyl, styrene, naphthyl, anthracenyl, phenanthrene, biphenyl, terphenyl, methylnaphthyl, biphenylene, dimethylnaphthyl,methylanthracenyl, 4,4'-dimethylbiphenyl, diphenylmethane, any isomer thereof, or any combination thereof, and the like.

[0031] As used herein, the term “amine” refers to a functional group of formula — N(RaRb), wherein Raand Rbare independently a hydrogen or an alkyl (as defined herein, or Raand Rbare bonded to each other to form a C3-C20 N-heterocycle.

[0032] Porous polymeric membranes are useful for removing contaminants from a variety of fluids. Porous polymeric membranes can be formed by polymer phase separation membrane formation processes like non-solvent induced phase separation (NIPS) and vapor-induced phase separation (VIPS). Membrane surfaces can be modified to include charged groups which improves the filtration properties of the membranes by increasing the surface energy and introducing non-sieving retention properties. However, surface modification causes pore plugging which increase the amount of time to flow a fluid through the membrane. Surface modification can also cause potential shedding of monomers, crosslinkers, e.g., unreacted crosslinkers, and initiators which would contamination the fluid. Accordingly, high molecular weight functional polymers are provided herein for producing inherently charged membranes through polymer phase separation processes like NIPS and VIPS, thus eliminating the need to modify the surface of the membrane.

[0033] Some embodiments relate to a membrane. In some embodiments, the membrane is a porous polymeric membrane. In some embodiments, the membrane comprises a polymer comprising a repeating unit of the formula:CF3

[0034] where:

[0035] Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;

[0036] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and

[0037] n is at least 1.

[0038] In some embodiments, Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof. In some embodiments, Q comprises a positively charged functional group. For example, in some embodiments, the positively charged functional group comprises at least one of an ammonium group, an imidazolium group, a pyridinium group, a phosphonium group, a sulfonium group, or any combination thereof. In some embodiments, Q comprises a negatively charged functional group. For example, in some embodiments, the negatively charged functional group comprises at least one of a carboxylate group, a phosphate group, a sulfate group, a sulfonate group, or any combination thereof.

[0039] In some embodiments, Q has the chemical formula:J

[0040] where:

[0041] Ft independently comprises at least one of an alkyl, a haloalkyl, or any combination thereof. In some embodiments, each Ft is the same. In some embodiments, each Ft is different.

[0042] In some embodiments, Q has the chemical formula:

[0043] In some embodiments, Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof. In some embodiments, Q’ has the chemical formula:

[0044] where:

[0045] R’ independently comprises at least one of a hydrogen, an alkyl, a haloalkyl, an amine, or any combination thereof. In some embodiments, each R’ is the same. In some embodiments, each R’ is different. In some embodiments, at least one R’ is the same as at least one R. In some embodiments, at least one R’ is different from at least one R. Although two R’ are shown, it will be appreciated that Q’ can have additional or fewer R’s, without departing from the scope of this disclosure.

[0046] In some embodiments, Q’ has the chemical formula:

[0047] In some embodiments, the polymer comprises a repeating unit of the formula:

[0048] where: n is at least 1.

[0049] In some embodiments, the polymer has a number average molecular weight of 25 kDa to 1000 kDa, or any range or subrange between 25 kDa to 1000 kDa. For example, in some embodiments, the polymer has a number average molecular weight of 25 kDa to 975 kDa, 25 kDa to 950 kDa, 25 kDa to 925 kDa, 25 kDa to 900 kDa, 25 kDa to 875 kDa, 25 kDa to 850 kDa, 25 kDa to 825 kDa, 25 kDa to 800 kDa, 25 kDa to 775 kDa, 25 kDa to 750 kDa, 25 kDa to 725 kDa, 25 kDa to 700 kDa, 25 kDa to 675 kDa, 25 kDa to 650 kDa, 25 kDa to 625 kDa, 25 kDa to 600 kDa, 25 kDa to 575 kDa, 25 kDa to 550 kDa, 25 kDa to 525 kDa, 25 kDa to 500 kDa, 25 kDa to 475 kDa, 25 kDa to 450 kDa, 25 kDa to 425 kDa, 25 kDa to 400 kDa, 25 kDa to 375 kDa, 25 kDa to 350 kDa, 25 kDa to 325 kDa, 25 kDa to 300 kDa, 25 kDa to 275 kDa, 25 kDa to 250 kDa, 25 kDa to 225 kDa, 25 kDa to 200 kDa, 25 kDa to 175 kDa, 25 kDa to 150 kDa, 25 kDa to 125 kDa, 25 kDa to 100 kDa, 25 kDa to 75 kDa, or 25 kDa to 50 kDa.

[0050] In some embodiments, the polymer has a number average molecularweight of 50 kDa to 1000 kDa, 75 kDa to 1000 kDa, 100 kDa to 1000 kDa, 125 kDa to 1000 kDa, 150 kDa to 1000 kDa, 175 kDa to 1000 kDa, 200 kDa to 1000 kDa, 225 kDa to 1000 kDa, 250 kDa to 1000 kDa, 275 kDa to 1000 kDa, 300 kDa to 1000 kDa, 325 kDa to 1000 kDa, 350 kDa to 1000 kDa, 375 kDa to 1000 kDa, 400 kDa to 1000 kDa, 425 kDa to 1000 kDa, 450 kDa to 1000 kDa, 475 kDa to 1000 kDa, 500 kDa to 1000 kDa, 525 kDa to 1000 kDa, 550 kDa to 1000 kDa, 575 kDa to 1000 kDa, 600 kDa to 1000 kDa, 625 kDa to 1000 kDa, 650 kDa to 1000 kDa, 675 kDa to 1000 kDa, 700 kDa to 1000 kDa, 725 kDa to 1000 kDa,750 kDa to 1000 kDa, 775 kDa to 1000 kDa, 800 kDa to 1000 kDa, 825 kDa to 1000 kDa, 850 kDa to 1000 kDa, 875 kDa to 1000 kDa, 900 kDa to 1000 kDa, 925 kDa to 1000 kDa, 950 kDa to 1000 kDa, or 975 kDa to 1000 kDa.

[0051] In some embodiments, the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2, or any range or subrange between 1 pg / cm2to 100 pg / cm2. For example, in some embodiments, the membrane exhibits a dye binding capacity of 1 pg / cm2to 95 pg / cm2, 1 pg / cm2to 90 pg / cm2, 1 pg / cm2to 85 pg / cm2, 1 pg / cm2to 80 pg / cm2, 1 pg / cm2to 75 pg / cm2, 1 pg / cm2to 70 pg / cm2, 1 pg / cm2to 65 pg / cm2, 1 pg / cm2to 60 pg / cm2, 1 pg / cm2to 55 pg / cm2, 1 pg / cm2to 50 pg / cm2, 1 pg / cm2to 45 pg / cm2, 1 pg / cm2to 40 pg / cm2, 1 pg / cm2to 35 pg / cm2, 1 pg / cm2to 30 pg / cm2, 1 pg / cm2to 25 pg / cm2, 1 pg / cm2to 20 pg / cm2, 1 pg / cm2to 15 pg / cm2, 1 pg / cm2to 10 pg / cm2, or 1 pg / cm2to 5 pg / cm2. In some embodiments, the membrane exhibits a dye binding capacity of 5 pg / cm2to 100 pg / cm2, 10 pg / cm2to 100 pg / cm2, 15 pg / cm2to 100 pg / cm2, 20 pg / cm2to 100 pg / cm2, 25 pg / cm2to 100 pg / cm2, 30 pg / cm2to 100 pg / cm2, 35 pg / cm2to 100 pg / cm2, 40 pg / cm2to 100 pg / cm2, 45 pg / cm2to 100 pg / cm2, 50 pg / cm2to 100 pg / cm2, 55 pg / cm2to 100 pg / cm2, 60 pg / cm2to 100 pg / cm2, 65 pg / cm2to 100 pg / cm2, 70 pg / cm2to 100 pg / cm2, 75 pg / cm2to 100 pg / cm2, 80 pg / cm2to 100 pg / cm2, 85 pg / cm2to 100 pg / cm2, 90 pg / cm2to 100 pg / cm2, or 95 pg / cm2to 100 pg / cm2.

[0052] In some embodiments, the membrane has a bubble point of 25 psi to 200 psi, or any range or subrange between 25 psi to 200 psi, when measured using an ethoxynonafluorobutane hydrofluoroether at a temperature of 22 °C. In some embodiments, the membrane has a bubble point of 25 psi to 195 psi, 25 psi to 190 psi, 25 psi to 185 psi, 25 psi to 180 psi, 25 psi to 175 psi, 25 psi to 170 psi, 25 psi to 165 psi, 25 psi to 160 psi, 25 psi to 155 psi, 25 psi to 150 psi, 25 psi to 145 psi, 25 psi to 140 psi, 25 psi to 135 psi, 25 psi to 130 psi, 25 psi to 125 psi, 25 psi to 120 psi, 25 psi to 115 psi, 25 psi to 110 psi, 25 psi to 105 psi, 25 psi to 100 psi, 25 psi to 95 psi, 25 psi to 90 psi, 25 psi to 85 psi, 25 psi to 80 psi, 25 psi to 75 psi, 25 psi to 70 psi, 25 psi to 65 psi, 25 psi to 60 psi, 25 psi to 55 psi, 25 psi to 50 psi, 25 psi to 45 psi, 25 psi to 40 psi, 25 psi to 35 psi, or 25 psi to 30 psi, when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C. In some embodiments, the membrane has a bubble point of 30 psi to 200 psi, 35 psi to 200 psi, 40 psi to 200 psi, 45 psi to 200 psi, 50 psi to 200 psi, 55 psi to 200 psi, 60psi to 200 psi, 65 psi to 200 psi, 70 psi to 200 psi, 75 psi to 200 psi, 80 psi to 200 psi, 85 psi to 200 psi, 90 psi to 200 psi, 95 psi to 200 psi, 100 psi to 200 psi, 105 psi to 200 psi, 110 psi to 200 psi, 115 psi to 200 psi, 120 psi to 200 psi, 125 psi to 200 psi, 130 psi to 200 psi, 135 psi to 200 psi, 140 psi to 200 psi, 145 psi to 200 psi, 150 psi to 200 psi, 155 psi to 200 psi, 160 psi to 200 psi, 165 psi to 200 psi, 170 psi to 200 psi, 175 psi to 200 psi, 180 psi to 200 psi, 185 psi to 200 psi, 190 psi to 200 psi, or 195 psi to 200 psi when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C.

[0053] In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane. In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100%, at least 110%, at least 120%, at least 130%, at least 140%, at least 150%, at least 160%, at least 170%, at least 180%, at least 190%, at least 200%, at least 210%, at least 220%, at least 230%, at least 240%, at least 250%, at least 260%, at least 270%, at least 280%, at least 290%, or at least 300% faster than a flow time of a surface-modified membrane.

[0054] In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is 100% to 300%, or any range or subrange between 100% to 300%, faster than a flow time of a surface-modified membrane. For example, in some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is 100% to 290%, 100% to 280%, 100% to 270%, 100% to 260%, 100% to 250%, 100% to 240%, 100% to 230%, 100% to 220%, 100% to 210%, 100% to 200%, 100% to 190%, 100% to 180%, 100% to 170%, 100% to 160%, 100% to 150%, 100% to 140%, 100% to 130%, 100% to 120%, 100% to 110%, 110% to 300%, 120% to 300%, 130% to 300%, 140% to 300%, 150% to 300%, 160% to 300%, 170% to 300%, 180% to 300%, 190% to 300%, 200% to 300%, 210% to 300%, 220% to 300%, 230% to 300%, 240% to 300%, 250% to 300%, 260% to 300%, 270% to 300%, 280% to 300%, or 290% to 300% faster than a flow time of a surface-modified membrane.

[0055] In some embodiments, the membrane comprises 1 % to 100%, or any range or subrange between 1% to 100%, by weight of the polymer based on a total weight of the membrane. For example, in some embodiments, the membrane comprises 1% to 95%, 1% to 90%, 1% to 85%, 1% to 80%, 1% to 75%, 1% to 70%, 1% to 65%, 1% to 60%, 1% to 55%, 1% to 50%, 1% to 45%, 1% to 40%, 1% to 35%, 1% to 30%, 1% to 25%, 1 % to 20%, 1 % to 15%, 1 % to 10%, 1 % to 5%, 5% to 100%, 10% to 100%, 15% to 100%, 20% to 100%, 25% to 100%, 30% to 100%, 35% to 100%, 40% to 100%, 45% to 100%, 50% to 100%, 55% to 100%, 60% to 100%, 65% to 100%, 70% to 100%, 75% to 100%, 80% to 100%, 85% to 100%, 90% to 100%, or 95% to 100% by weight of the polymer based on the total weight of the membrane.

[0056] In some embodiments, the membrane comprises a second polymer. In some embodiments, the second polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.

[0057] In some embodiments, the membrane comprises 1 % to 99%, or any range or subrange between 1% to 99%, by weight of the second polymer based on the total weight of the membrane. For example, in some embodiments, the membrane comprises 1 % to 95%, 1 % to 90%, 1 % to 85%, 1 % to 80%, 1 % to 75%, 1 % to 70%, 1 % to 65%, 1 % to 60%, 1 % to 55%, 1 % to 50%, 1 % to 45%, 1 % to 40%, 1 % to 35%, 1 % to 30%, 1 % to 25%, 1% to 20%, 1% to 15%, 1% to 10%, 1% to 5%, 5% to 99%, 10% to 99%, 15% to 99%, 20% to 99%, 25% to 99%, 30% to 99%, 35% to 99%, 40% to 99%, 45% to 99%, 50% to 99%, 55% to 99%, 60% to 99%, 65% to 99%, 70% to 99%, 75% to 99%, 80% to 99%, 85% to 99%, 90% to 99%, or 95% to 99% by weight of the second polymer based on the total weight of the membrane.

[0058] In some embodiments, the membrane has a thickness of 1 pm to 1000 pm, or any range or subrange to 1 pm to 1000 pm. In some embodiments, the membrane has a thickness of 1 pm to 900 pm, 1 pm to 800 pm, 1 pm to 700 pm, 1 pm to 600 pm, 1 pm to 500 pm, 1 pm to 400 pm, 1 pm to 300 pm, 1 pm to 200 pm, 1 pm to 100 pm, 1 pm to 90 pm, 1 pm to 80 pm, 1 pm to 70 pm, 1 pm to 60 pm, 1 pm to 50 pm, 1 pm to 40 pm, 1 pm to 30 pm, 1 pm to 20 pm, 1 pm to 10 pm, 1 pm to 5 pm, 5 pm to 1000 pm, 10 pm to 1000 pm, 20 pm to 1000 pm, 30 pm to 1000 pm, 40 pm to 1000 pm, 50 pm to 1000 pm, 60 pm to 1000 pm, 70 pm to 1000 pm, 80 pm to 1000 pm, 90 pm to 1000 pm, 100pm to 1000 pm, 200 pm to 1000 pm, 300 pm to 1000 pm, 400 m to 1000 pm, 500 pm to 1000 pm, 600 pm to 1000 pm, 700 pm to 1000 pm, 800 pm to 1000 pm, or 900 pm to 1000 pm.

[0059] In some embodiments, any variety of characterization techniques known in the art may be used to measure membrane thickness, for example, scanning electron microscopy (SEM), atomic force microscopy (AFM), among others.

[0060] In some embodiments, membranes from the polymers disclosed herein can be formed into a number of different structure or morphologies. In some embodiments, the membranes can be formed into symmetric morphologies where the pore size is very close to the same throughout the cross-section or thickness. In some embodiments, the membranes can be formed into asymmetric (anisotropic) morphologies where the pore size can change across the membrane thickness.

[0061] In some embodiments, the membranes are inherently charged membranes and do not require surface modification to achieve such charge.

[0062] Some embodiments relate to a membrane. In some embodiments, the membrane is a porous polymeric membrane. In some embodiments, the membrane

[0063] where:

[0064] Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;

[0065] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0066] n is at least 1 ;

[0067] Z’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0068] Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0069] m is at least 1.

[0070] In some embodiments, Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof. In some embodiments, Q comprises a positively charged functional group. For example, in some embodiments, the positively charged functional group comprises at least one of an ammonium group, an imidazolium group, a pyridinium group, a phosphonium group, a sulfonium group, or any combination thereof. In some embodiments, Q comprises a negatively charged functional group. For example, in some embodiments, the negatively charged functional group comprises at least one of a carboxylate group, a phosphate group, a sulfate group, a sulfonate group, or any combination thereof.

[0071] In some embodiments, Q has the chemical formula:

[0072] where:

[0073] R independently comprises at least one of an alkyl, a haloalkyl, or any combination thereof. In some embodiments, each R is the same. In some embodiments, each R is different.

[0074] In some embodiments, Q has the chemical formula:

[0075] In some embodiments, Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof. In some embodiments, Q’ has the chemical formula:

[0076] where:

[0077] R’ independently comprises at least one of a hydrogen, an alkyl, a haloalkyl, an amine, or any combination thereof. In some embodiments, each R’ is the same. In some embodiments, each R’ is different. In some embodiments, at least one R’ is the same as at least one R. In some embodiments, at least one R’ is different from at least one R.

[0078] In some embodiments, Q’ has the chemical formula:

[0079] In some embodiment, Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof. In some embodiments, Z comprises an alkyl. In some embodiments, Z comprises a substituted alkyl. In someembodiments, Z comprises an aryl. In some embodiments, Z comprises a substituted aryl.

[0080] In some embodiments, Z’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof. In some embodiments, Z’ has the chemical formula:

[0081] where:

[0082] R’ independently comprises at least one of a hydrogen, an alkyl, a haloalkyl, an amine, or any combination thereof. In some embodiments, each R’ is the same. In some embodiments, each R’ is different.

[0083] In some embodiments, Z’ has the chemical formula:

[0084] In some embodiments, the copolymer comprises repeating units of the formula: / N\

[0085] where: n is at least 1 and m is at least 1.

[0086] In some embodiments, the copolymer has a number average molecular weight of 25 kDa to 1000 kDa, or any range or subrange between 25 kDa to 1000 kDa. For example, in some embodiments, the copolymer has a number average molecularweight of 25 kDa to 975 kDa, 25 kDa to 950 kDa, 25 kDa to 925 kDa, 25 kDa to 900 kDa, 25 kDa to 875 kDa, 25 kDa to 850 kDa, 25 kDa to 825 kDa, 25 kDa to 800 kDa, 25 kDa to 775 kDa, 25 kDa to 750 kDa, 25 kDa to 725 kDa, 25 kDa to 700 kDa, 25 kDa to 675 kDa, 25 kDa to 650 kDa, 25 kDa to 625 kDa, 25 kDa to 600 kDa, 25 kDa to 575 kDa, 25 kDa to 550 kDa, 25 kDa to 525 kDa, 25 kDa to 500 kDa, 25 kDa to 475 kDa, 25 kDa to 450 kDa, 25 kDa to 425 kDa, 25 kDa to 400 kDa, 25 kDa to 375 kDa, 25 kDa to 350 kDa, 25 kDa to 325 kDa, 25 kDa to 300 kDa, 25 kDa to 275 kDa, 25 kDa to 250 kDa, 25 kDa to 225 kDa, 25 kDa to 200 kDa, 25 kDa to 175 kDa, 25 kDa to 150 kDa, 25 kDa to 125 kDa, 25 kDa to 100 kDa, 25 kDa to 75 kDa, or 25 kDa to 50 kDa.

[0087] In some embodiments, the copolymer has a number average molecular weight of 50 kDa to 1000 kDa, 75 kDa to 1000 kDa, 100 kDa to 1000 kDa, 125 kDa to 1000 kDa, 150 kDa to 1000 kDa, 175 kDa to 1000 kDa, 200 kDa to 1000 kDa, 225 kDa to 1000 kDa, 250 kDa to 1000 kDa, 275 kDa to 1000 kDa, 300 kDa to 1000 kDa, 325 kDa to 1000 kDa, 350 kDa to 1000 kDa, 375 kDa to 1000 kDa, 400 kDa to 1000 kDa, 425 kDa to 1000 kDa, 450 kDa to 1000 kDa, 475 kDa to 1000 kDa, 500 kDa to 1000 kDa, 525 kDa to 1000 kDa, 550 kDa to 1000 kDa, 575 kDa to 1000 kDa, 600 kDa to 1000 kDa, 625 kDa to 1000 kDa, 650 kDa to 1000 kDa, 675 kDa to 1000 kDa, 700 kDa to 1000 kDa, 725 kDa to 1000 kDa, 750 kDa to 1000 kDa, 775 kDa to 1000 kDa, 800 kDa to 1000 kDa, 825 kDa to 1000 kDa, 850 kDa to 1000 kDa, 875 kDa to 1000 kDa, 900 kDa to 1000 kDa, 925 kDa to 1000 kDa, 950 kDa to 1000 kDa, or 975 kDa to 1000 kDa.

[0088] In some embodiments, the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2, or any range or subrange between 1 pg / cm2to 100 pg / cm2. For example, in some embodiments, the membrane exhibits a dye binding capacity of 1 pg / cm2to 95 pg / cm2, 1 pg / cm2to 90 pg / cm2, 1 pg / cm2to 85 pg / cm2, 1 pg / cm2to 80 pg / cm2, 1 pg / cm2to 75 pg / cm2, 1 pg / cm2to 70 pg / cm2, 1 pg / cm2to 65 pg / cm2, 1 pg / cm2to 60 pg / cm2, 1 pg / cm2to 55 pg / cm2, 1 pg / cm2to 50 pg / cm2, 1 pg / cm2to 45 pg / cm2, 1 pg / cm2to 40 pg / cm2, 1 pg / cm2to 35 pg / cm2, 1 pg / cm2to 30 pg / cm2, 1 pg / cm2to 25 pg / cm2, 1 pg / cm2to 20 pg / cm2, 1 pg / cm2to 15 pg / cm2, 1 pg / cm2to 10 pg / cm2, or 1 pg / cm2to 5 pg / cm2. In some embodiments, the membrane exhibits a dye binding capacity of 5 pg / cm2to 100 pg / cm2, 10 pg / cm2to 100 pg / cm2, 15 pg / cm2to 100 pg / cm2, 20 pg / cm2to 100 pg / cm2, 25 pg / cm2to 100 pg / cm2, 30 pg / cm2to 100 pg / cm2, 35 pg / cm2to 100 pg / cm2,40 pg / cm2to 100 pg / cm2, 45 pg / cm2to 100 pg / cm2, 50 pg / cm2to 100 pg / cm2, 55 pg / cm2to 100 pg / cm2, 60 pg / cm2to 100 pg / cm2, 65 pg / cm2to 100 pg / cm2, 70 pg / cm2to 100 pg / cm2, 75 pg / cm2to 100 pg / cm2, 80 pg / cm2to 100 pg / cm2, 85 pg / cm2to 100 pg / cm2, 90 pg / cm2to 100 pg / cm2, or 95 pg / cm2to 100 pg / cm2.

[0089] In some embodiments, the membrane has a bubble point of 25 psi to 200 psi, or any range or subrange between 25 psi to 200 psi, when measured using an ethoxynonafluorobutane hydrofluoroether at a temperature of 22 °C. In some embodiments, the membrane has a bubble point of 25 psi to 195 psi, 25 psi to 190 psi, 25 psi to 185 psi, 25 psi to 180 psi, 25 psi to 175 psi, 25 psi to 170 psi, 25 psi to 165 psi, 25 psi to 160 psi, 25 psi to 155 psi, 25 psi to 150 psi, 25 psi to 145 psi, 25 psi to 140 psi, 25 psi to 135 psi, 25 psi to 130 psi, 25 psi to 125 psi, 25 psi to 120 psi, 25 psi to 115 psi, 25 psi to 110 psi, 25 psi to 105 psi, 25 psi to 100 psi, 25 psi to 95 psi, 25 psi to 90 psi, 25 psi to 85 psi, 25 psi to 80 psi, 25 psi to 75 psi, 25 psi to 70 psi, 25 psi to 65 psi, 25 psi to 60 psi, 25 psi to 55 psi, 25 psi to 50 psi, 25 psi to 45 psi, 25 psi to 40 psi, 25 psi to 35 psi, or 25 psi to 30 psi, when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C. In some embodiments, the membrane has a bubble point of 30 psi to 200 psi, 35 psi to 200 psi, 40 psi to 200 psi, 45 psi to 200 psi, 50 psi to 200 psi, 55 psi to 200 psi, 60 psi to 200 psi, 65 psi to 200 psi, 70 psi to 200 psi, 75 psi to 200 psi, 80 psi to 200 psi, 85 psi to 200 psi, 90 psi to 200 psi, 95 psi to 200 psi, 100 psi to 200 psi, 105 psi to 200 psi, 110 psi to 200 psi, 115 psi to 200 psi, 120 psi to 200 psi, 125 psi to 200 psi, 130 psi to 200 psi, 135 psi to 200 psi, 140 psi to 200 psi, 145 psi to 200 psi, 150 psi to 200 psi, 155 psi to 200 psi, 160 psi to 200 psi, 165 psi to 200 psi, 170 psi to 200 psi, 175 psi to 200 psi, 180 psi to 200 psi, 185 psi to 200 psi, 190 psi to 200 psi, or 195 psi to 200 psi when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C.

[0090] In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane. In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100%, at least 110%, at least 120%, at least 130%, at least 140%, at least 150%, at least 160%, at least 170%,at least 180%, at least 190%, at least 200%, at least 210%, at least 220%, at least 230%, at least 240%, at least 250%, at least 260%, at least 270%, at least 280%, at least 290%, or at least 300% faster than a flow time of a surface-modified membrane.

[0091] In some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is 100% to 300%, or any range or subrange between 100% to 300%, faster than a flow time of a surface-modified membrane. For example, in some embodiments, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is 100% to 290%, 100% to 280%, 100% to 270%, 100% to 260%, 100% to 250%, 100% to 240%, 100% to 230%, 100% to 220%, 100% to 210%, 100% to 200%, 100% to 190%, 100% to 180%, 100% to 170%, 100% to 160%, 100% to 150%, 100% to 140%, 100% to 130%, 100% to 120%, 100% to 110%, 110% to 300%, 120% to 300%, 130% to 300%, 140% to 300%, 150% to 300%, 160% to 300%, 170% to 300%, 180% to 300%, 190% to 300%, 200% to 300%, 210% to 300%, 220% to 300%, 230% to 300%, 240% to 300%, 250% to 300%, 260% to 300%, 270% to 300%, 280% to 300%, or 290% to 300% faster than a flow time of a surface-modified membrane.

[0092] In some embodiments, the membrane comprises 1 % to 100%, or any range or subrange between 1 % to 100%, by weight of the copolymer based on a total weight of the membrane. For example, in some embodiments, the membrane comprises 1% to 95%, 1% to 90%, 1% to 85%, 1% to 80%, 1% to 75%, 1% to 70%, 1% to 65%, 1% to 60%, 1% to 55%, 1% to 50%, 1% to 45%, 1% to 40%, 1% to 35%, 1% to 30%, 1% to 25%, 1 % to 20%, 1 % to 15%, 1 % to 10%, 1 % to 5%, 5% to 100%, 10% to 100%, 15% to 100%, 20% to 100%, 25% to 100%, 30% to 100%, 35% to 100%, 40% to 100%, 45% to 100%, 50% to 100%, 55% to 100%, 60% to 100%, 65% to 100%, 70% to 100%, 75% to 100%, 80% to 100%, 85% to 100%, 90% to 100%, or 95% to 100% by weight of the copolymer based on the total weight of the membrane.

[0093] In some embodiments, the membrane comprises a polymer. In some embodiments, the polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.

[0094] In some embodiments, the membrane comprises 1 % to 99%, or any range or subrange between 1% to 99%, by weight of the polymer based on the total weight of the membrane. For example, in some embodiments, the membrane comprises 1% to 95%, 1% to 90%, 1% to 85%, 1% to 80%, 1% to 75%, 1% to 70%, 1% to 65%, 1% to 60%, 1% to 55%, 1% to 50%, 1% to 45%, 1% to 40%, 1% to 35%, 1% to 30%, 1% to 25%, 1% to 20%, 1% to 15%, 1% to 10%, 1% to 5%, 5% to 99%, 10% to 99%, 15% to 99%, 20% to 99%, 25% to 99%, 30% to 99%, 35% to 99%, 40% to 99%, 45% to 99%, 50% to 99%, 55% to 99%, 60% to 99%, 65% to 99%, 70% to 99%, 75% to 99%, 80% to 99%, 85% to 99%, 90% to 99%, or 95% to 99% by weight of the polymer based on the total weight of the membrane.

[0095] In some embodiments, the membrane has a thickness of 1 pm to 1000 pm, or any range or subrange to 1 pm to 1000 pm. In some embodiments, the membrane has a thickness of 1 pm to 900 pm, 1 pm to 800 pm, 1 pm to 700 pm, 1 pm to 600 pm, 1 pm to 500 pm, 1 pm to 400 pm, 1 pm to 300 pm, 1 pm to 200 pm, 1 pm to 100 pm, 1 pm to 90 pm, 1 pm to 80 pm, 1 pm to 70 pm, 1 pm to 60 pm, 1 pm to 50 pm, 1 pm to 40 pm, 1 pm to 30 pm, 1 pm to 20 pm, 1 pm to 10 pm, 1 pm to 5 pm, 5 pm to 1000 pm, 10 pm to 1000 pm, 20 pm to 1000 pm, 30 pm to 1000 pm, 40 pm to 1000 pm, 50 pm to 1000 pm, 60 pm to 1000 pm, 70 pm to 1000 pm, 80 pm to 1000 pm, 90 pm to 1000 pm, 100 pm to 1000 pm, 200 pm to 1000 pm, 300 pm to 1000 pm, 400 pm to 1000 pm, 500 pm to 1000 pm, 600 pm to 1000 pm, 700 pm to 1000 pm, 800 pm to 1000 pm, or 900 pm to 1000 pm.

[0096] In some embodiments, any variety of characterization techniques known in the art may be used to measure membrane thickness, for example scanning electron microscopy (SEM), atomic force microscopy (AFM), among others.

[0097] In some embodiments, the membranes are inherently charged membranes and do not require surface modification to achieve such charge.

[0098] Some embodiments relate to a method. FIG. 1 is a flowchart of a method for making a copolymer 100, according to some embodiments. As shown in FIG. 1, the method for making a copolymer 100 may comprise one or more of the following steps: contacting 102 at least a first monomer, a second monomer, and a solvent to form apolymeric component, contacting 104 a trifluoroacetone component with the polymeric component to form a copolymer.

[0099] At step 102, in some embodiments, the method comprises contacting at least a first monomer, a second monomer, and a solvent to form a polymeric component.

[0100] In some embodiments, the contacting comprises mixing the first monomer, the second monomer, and the solvent. In some embodiments, the contacting comprises agitating the first monomer, the second monomer, and the solvent. In some embodiments, the contacting comprises mixing the first monomer and the solvent in a vessel and then adding the second monomer to the vessel. In some embodiments, the contacting comprises mixing the first monomer and the solvent in a first vessel, separating mixing the second monomer and the solvent in a second vessel, and then adding the mixture in the second vessel to the mixture in the first vessel.

[0101] In some embodiments, the first monomer comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof.

[0102] In some embodiments, the first monomer comprises a monomer of the formula:

[0103] In some embodiments, the second monomer comprises a functional group capable of being charged. In some embodiments, the second monomer comprises a monomer of the formula:

[0104] where:

[0105] Q° comprises a functional group capable of being charged.

[0106] In some embodiments, the second monomer comprises a monomer of the formula:oCF3

[0107] In some embodiments, the polymeric component comprises any one or more of the polymers disclosed herein. For example, in some embodiments, the polymeric component comprises a polymer comprising a repeating unit of the formula:n

[0108] where:

[0109] Q comprises at least one of a positively chargeable functional group, a negatively chargeable functional group, or any combination thereof;

[0110] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and

[0111] n is at least 1.

[0112] In some embodiments, the solvent comprises at least one of dichloromethane, N-methyl pyrrolidone, dimethyl sulfoxide, ethyl acetate, isopropyl alcohol, tetrahydrofuran, acetone, hexane, ethanol, toluene, chloroform, or any combination thereof.

[0113] At step 104, in some embodiments, the method comprises contacting a trifluoroacetone component with the polymeric component to form a copolymer.

[0114] In some embodiments, the contacting comprises mixing the trifluoroacetone component and the polymeric component. In some embodiments, the contacting comprises agitating the trifluoroacetone component and the polymeric component. In some embodiments, the contacting comprises mixing the trifluoroacetone component with a solvent and then adding the polymeric component. In some embodiments, thecontacting comprises mixing the polymeric component and a solvent and then adding the trifluoroacetone component. In some embodiments, the contacting comprises adding the trifluoroacetone component to the solution obtained in step 102.

[0115] In some embodiments, the solvent comprises at least one of dichloromethane, ethyl acetate, isopropyl alcohol, tetrahydrofuran, acetone, hexane, ethanol, toluene, chloroform, or any combination thereof.

[0116] In some embodiments, the copolymer comprises any one or more of the copolymers disclosed herein. For example, in some embodiments, the copolymer comprises repeating units of the formula:

[0117] where:

[0118] Q comprises at least one of a positively chargeable functional group, a negatively chargeable functional group, or any combination thereof;

[0119] Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0120] n is at least 1 ;

[0121] Z’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0122] Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;

[0123] m is at least 1.

[0124] EXAMPLE 1 : Synthesis of Homo-polymer (Trifluoroacetophenone, TFAA)

[0125] TFAA polymer was synthesized according to the following procedure. Biphenyl (2.00 g, 13 mmol) and 4'-(Dimethylamino)-2,2,2-trifluoroacetophenone (4.23 g, 19 mmol) were dissolved in dichloromethane (13 g, 154 mmol) at room temperature. After the solids dissolved, the solution was cooled to 0 °C. Then, trifluoromethanesulfonic acid (TFSA) (19.46 g, 130 mmol) was added in one portion to the solution. The temperature was gradually raised to room temperature over 2 hours. The reaction mixture was stirred at this temperature for 7 days. The solution increased in viscosity until a gum-like solution was obtained. Dichloromethane (18.8 g, 221 mmol) was then added, followed by a dropwise addition of ammonium hydroxide (29% in water, 56.6 g, 468 mmol) to neutralize the acid. The solid precipitate was collected with a spatula, and the liquid was drained from the reactor. The solid was dissolved in N-Methyl-2-pyrrolidone (NMP) (80 g, 807 mmol) at room temperature. The liquid was precipitated in 300 mL of deionized water to isolate the polymer. A purple polymer solid was obtained (3.949 g, yield 86%). The polymer was dried at 40 °C overnight and characterized by GPC in THF solvents using PS standards. The molecular weight was Mw = 89.4 kDa, Mn = 42.57 kDa with a PDI of ~2.1.

[0126] The polymer was characterized by1H-NMR,19F-NMR, and13C-NMR. The1H-NMR of the homopolymer showed a peak at 2.97 ppm integrating for the 6 protons, along with other aromatic protons between 6.50 ppm to 7.66 ppm. The19F-NMR confirmed the structure, as indicated by the change in the chemical shift of fluorine from -68 ppm to -56 ppm. The1H-NMR,19F-NMR, and13C-NMR spectra are shown in FIG. 2, FIG. 3, and FIG. 4, respectively.

[0127] EXAMPLE 2: Synthesis of Copolymer

[0128] The copolymer was synthesized according to the following procedure. The polymerization was completed in two steps but in one pot. In the first step, biphenyl (2.00 g, 13 mmol) was dissolved in dichloromethane (10 g, 118 mmol) at room temperature under stirring. After the solids dissolved, 4'-(Dimethylamino)-2,2,2-trifluoroacetophenone (0.28 g, 1 mmol) was added at room temperature. The solution was then cooled to 0 °C. Trifluoromethanesulfonic acid (TFSA) (3.89 g, 26 mmol) was added in one portion to the solution. The temperature was gradually raised to room temperature over 2 hours. The reaction mixture was stirred at this temperature for 12 hours. The reaction was then cooled to 0 °C in an ice bath, and trifluoroacetone (2.62 g, 23 mmol) was added in one portion to the solution. The reaction was stirred for 48 hours at room temperature. The acid was quenched with a solution of ammonium hydroxide (29% in water, 10.2 g, 84.6 mmol). The solid precipitate was obtained by pouring the suspension into 100 g of isopropyl alcohol (IPA). The solid was filtered and dried in an oven at 60 °C for 8 hours. The solid copolymer collected (3.4 g, 90.6% yield) had a bimodal molecular weight distribution: Mw = 44.2 kDa, PDI = 2.5; Mn = 32.862 kDa, PDI = 1.0. The copolymer structure was characterized by1H-NMR and19F-NMR. The peaks for1H-NMR and19F-NMR are assigned in FIG. 5 and FIG. 6, respectively.

[0129] EXAMPLE 3: Preparation of membranes from the copolymer

[0130] The copolymer from Example 2 was dried overnight at 60 °C to remove any residual solvent and water before membrane preparation. 1.20 g of polymer from Example 2 was dissolved in 10.50 g of N-methyl-2-pyrrolidone (NMP). Once all the polymer was dissolved, isopropyl alcohol (3.30 g) was added, and the mixture was stirred for 4-6 hours until the solution was clear. The casting mixture was then metered through a controlled slot between the casting knife on the glass surface of the TQC Automatic Film Applicator at a speed of 1 inch / second. The porous membrane sheets were made by immersing them into a water bath held at room temperature. The membranes were washed in water for an hour and then air-dried. The membrane properties, such as flow time, bubble point, and thickness, were tested, and the results are shown in Table 1.

[0131] Table 1 :Thickness (pm) HFE Bubble point I PA Flowtime Charge density (psi) (sec / 500mL) (ug / cmA2)75 48 790 43

[0132] Any one or more of the embodiments disclosed herein shall be understood to be combinable without departing from the scope or spirit of the disclosure.

[0133] ASPECTS

[0134] Various Aspects are described below. It is to be understood that any one or more of the features recited in the following Aspect(s) can be combined with any one or more other Aspect(s).Aspect 1. A membrane comprising:a polymer comprising a repeating unit of the formula:CF3- Q' - JnQ Jwhere:Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and n is at least 1.Aspect 2. The membrane according to Aspect 1 , wherein the polymer has a number average molecular weight of 25 kDa to 1000 kDa.Aspect 3. The membrane according to any one of Aspects 1-2, wherein Q’ has the chemical formula:where:R’ independently comprises at least one of a hydrogen, an alkyl, a haloalkyl, an amine, or any combination thereof.Aspect 4. The membrane according to any one of Aspects 1-3, wherein Q’ has the chemical formula:Aspect 5. The membrane according to any one of Aspects 1-4, wherein Q has the chemical formula:where:R independently comprises at least one of an alkyl, a haloalkyl, or any combination thereof.Aspect 6. The membrane according to any one of Aspects 1-5, wherein Q has the chemical formula:Aspect 7. The membrane according to any one of Aspects 1-6, wherein the polymer comprises a repeating unit of the formula:Aspect s. The membrane according to any one of Aspects 1-7, wherein the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2.Aspect 9. The membrane according to any one of Aspects 1-8, wherein the membrane has a bubble point of 25 psi to 200 psi when measured using an ethoxynonafluorobutane hydrofluoroether at a temperature of 22 °C.Aspect 10. The membrane according to any one of Aspects 1-9, wherein, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane.Aspect 11. The membrane according to any one of Aspects 1 -10, further comprising:a second polymer,wherein the second polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.Aspect 12. A membrane comprising:a copolymer comprising repeating units of the formula:CF3CF3O' _"7'n mQ Zwhere:Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;n is at least 1 ;Z’ comprises at least one of an alkyl, a substitute alkyl, an aryl, a substituted aryl, or any combination thereof;Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and m is at least 1.Aspect 13. The membrane according to Aspect 12, wherein the copolymer has a number average molecular weight of 25 kDa to 1000 kDa.Aspect 14. The membrane according to any one of Aspects 12-13, wherein the copolymer comprises repeating units of the formula: / N\Aspect 15. The membrane according to any one of Aspects 12-14, wherein the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2.Aspect 16. The membrane according to any one of Aspects 12-15, wherein the membrane has a bubble point of 25 psi to 200 psi when measured using an ethoxynonafluorobutane hydrofluoroether at a temperature of 22 °C.Aspect 17. The membrane according to any one of Aspects 12-16, wherein, when 500 ml of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane.Aspect 18. The membrane according to any one of Aspects 12-17, further comprising:a polymer,wherein the polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.Aspect 19. A method comprising:contacting at least a first monomer, a second monomer, and a solvent to form a polymeric component,wherein the polymeric component comprises a repeating unit of the formula:CF3nwhere:Q comprises at least one functional group capable of being charged;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and n is at least 1.Aspect 20. The method according to Aspect 19, further comprising:contacting a trifluoroacetone component with the polymeric component to form a copolymer,wherein the copolymer comprises repeating units of the formula:where:Q comprises at least one functional group capable of being charged;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;n is at least 1 ;Z’ comprises at least one of an alkyl, a substitute alkyl, an aryl, a substituted aryl, or any combination thereof; Z comprises at least one of an alkyl, a substituted alky, an aryl, a substituted aryl, or any combination thereof; andm is at least 1.

Claims

CLAIMSWHAT IS CLAIMED IS:

1. A membrane comprising:a polymer comprising a repeating unit of the formula:CF3- Q' - JnQwhere:Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and n is at least 1.

2. The membrane of claim 1 , wherein the polymer has a number average molecular weight of 25 kDa to 1000 kDa.

3. The membrane of claim 1 , wherein Q’ has the chemical formula:where:FT independently comprises at least one of a hydrogen, an alkyl, a haloalkyl, an amine, or any combination thereof.

4. The membrane of claim 1 , wherein Q’ has the chemical formula:

5. The membrane of claim 1 , wherein Q has the chemical formula:where:R independently comprises at least one of an alkyl, a haloalkyl, or any combination thereof.

6. The membrane of claim 1 , wherein Q has the chemical formula:

7. The membrane of claim 1 , wherein the polymer comprises a repeating unit of the formula:

8. The membrane of claim 1 , wherein the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2.

9. The membrane of claim 1 , wherein the membrane has a bubble point of 25 psi to 200 psi when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C.

10. The membrane of claim 1 , wherein, when 500 mL of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane.

11. The membrane of claim 1 , further comprising:a second polymer,wherein the second polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.

12. A membrane comprising:a copolymer comprising repeating units of the formula:CF3CF3O' _"7'n mQ Zwhere:Q comprises at least one of a positively charged functional group, a negatively charged functional group, or any combination thereof;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;n is at least 1 ;Z’ comprises at least one of an alkyl, a substitute alkyl, an aryl, a substituted aryl, or any combination thereof;Z comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and m is at least 1.

13. The membrane of claim 12, wherein the copolymer has a number average molecular weight of 25 kDa to 1000 kDa.

14. The membrane of claim 12, wherein the copolymer comprises repeating units of the formula: / N\15. The membrane of claim 12, wherein the membrane exhibits a dye binding capacity of 1 pg / cm2to 100 pg / cm2.

16. The membrane of claim 12, wherein the membrane has a bubble point of 25 psi to 200 psi when measured using an ethoxy-nonafluorobutane hydrofluoroether at a temperature of 22 °C.

17. The membrane of claim 12, wherein, when 500 ml of a deionized water is flowed through the membrane having a diameter of 47 mm at a pressure of 1 kPa and a temperature of 22 °C, a flow time of the membrane is at least 100% faster than a flow time of a surface-modified membrane.

18. The membrane of claim 12, further comprising:a polymer,wherein the polymer comprises at least one of an aromatic fluoropolymer, a polyphenylsulfone, or any combination thereof.

19. A method comprising:contacting at least a first monomer, a second monomer, and a solvent to form a polymeric component,wherein the polymeric component comprises a repeating unit of the formula:CF3nwhere:Q comprises at least one functional group capable of being charged;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof; and n is at least 1.

20. The method of claim 19, further comprising:contacting a trifluoroacetone component with the polymeric component to form a copolymer,wherein the copolymer comprises repeating units of the formula:where:Q comprises at least one functional group capable of being charged;Q’ comprises at least one of an alkyl, a substituted alkyl, an aryl, a substituted aryl, or any combination thereof;n is at least 1 ;Z’ comprises at least one of an alkyl, a substitute alkyl, an aryl, a substituted aryl, or any combination thereof; Z comprises at least one of an alkyl, a substituted alky, an aryl, a substituted aryl, or any combination thereof; andm is at least 1.

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