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US 2019/0169416 A1Published application
Fabricating ionic/polyimide membranes
AssigneeThe Board of Regents of the Nevada System of Higher Education on Behalf of the University of Ne
InventorsKwang Jin KIM, Dong-Chan LEE, Jungsoo NAM, Tae Seon HWANG
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Abstract
Disclosed are polyimide blends and methods of making and using same. The disclosed polyimide blends are prepared by first blending an ionic polymer and a poly(amic acid) to form a poly(amic acid) precursor, followed by cyclization. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Claims41
A method of making a polyimide blend, the method comprising:
- a) mixing an ionic polymer selected from a perfluorinated ionomer membrane, a poly(acrylic acid) salt, sulfonated polystyrene, sulfonated poly(arylene ether sulfone), sulfonated poly(arylene thioether sulfone), cross-linked poly(styrene-ran-ethylene), sulfonated poly(styrene-b-ethylene-co-butylene-b-styrene), poly(fluoroalkyl methyacrylate-co-acrylic acid), poly(fluoroalkyl methacrylate-co-2-acylamido-2-methyl-1-propanesulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid-co-2-hydroxyethyl methacrylate), poly(vinylidene-g-sulfonated N-ethylenecarbazole), poly(vinylidene fluoride-co-hexafluoropropylene), poly(ethylene-co-tetrafluoroethylene), and Nafion, and a poly(amic acid) comprising at least one residue having a structure represented by a formula selected from:
- wherein
- comprises a structure represented by a formula selected from:
- wherein n is an integer greater than 1;
- wherein m is 0 or 1;
- wherein A is selected from —Ar1— and a structure represented by a formula:
- wherein Z, when present, is selected from O, NR3, CR4aR4b, CO, and SO2;
- wherein each of R3, R4a, and R4b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl;
- wherein Ar1, when present, is selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein each of Ar2 and Ar3, when present, is independently selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein Q, when present, is selected from O, NR1, SO, SO2, C(O), and CR2aR2b;
- and
- wherein each of R1, R2a, and R2b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl,
- thereby making a poly(amic acid) blend;
- and
- b) cyclizing the poly(amic acid) blend.
13 more elements
A poly(amic acid) blend comprising:
- a) an ionic polymer selected from a perfluorinated ionomer membrane, a poly(acrylic acid) salt, sulfonated polystyrene, sulfonated poly(arylene ether sulfone), sulfonated poly(arylene thioether sulfone), cross-linked poly(styrene-ran-ethylene), sulfonated poly(styrene-b-ethylene-co-butylene-b-styrene), poly(fluoroalkyl methyacrylate-co-acrylic acid), poly(fluoroalkyl methacrylate-co-2-acylamido-2-methyl-1-propanesulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid-co-2-hydroxyethyl methacrylate), poly(vinylidene-g-sulfonated N-ethylenecarbazole), poly(vinylidene fluoride-co-hexafluoropropylene), poly(ethylene-co-tetrafluoroethylene), and Nafion;
- and
- b) a poly(amic acid) comprising at least one residue having a structure represented by a formula selected from:
- wherein
- comprises a structure represented by a formula selected from:
- wherein n is an integer greater than 1;
- wherein m is 0 or 1;
- wherein A is selected from —Ar1— and a structure represented by a formula:
- wherein Z, when present, is selected from O, NR3, CR4aR4b, CO, and SO2;
- wherein each of R3, R4a, and R4b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl;
- wherein Ar1, when present, is selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein each of Ar2 and Ar3, when present, is independently selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein Q, when present, is selected from O, NR1, SO, SO2, C(O), and CR2aR2b;
- and
- wherein each of R1, R2a, and R2b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl.
12 more elements
A polyimide blend comprising:
- a) an ionic polymer selected from a perfluorinated ionomer membrane, a poly(acrylic acid) salt, sulfonated polystyrene, sulfonated poly(arylene ether sulfone), sulfonated poly(arylene thioether sulfone), cross-linked poly(styrene-ran-ethylene), sulfonated poly(styrene-b-ethylene-co-butylene-b-styrene), poly(fluoroalkyl methyacrylate-co-acrylic acid), poly(fluoroalkyl methacrylate-co-2-acylamido-2-methyl-1-propanesulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid), poly(fluoroalkyl methacrylate-co-sulfonic acid-co-2-hydroxyethyl methacrylate), poly(vinylidene-g-sulfonated N-ethylenecarbazole), poly(vinylidene fluoride-co-hexafluoropropylene), poly(ethylene-co-tetrafluoroethylene), and Nafion;
- and
- b) a polyimide comprising at least one residue having a structure represented by a formula:
- wherein
- comprises a structure represented by a formula selected from:
- wherein n is an integer greater than 1;
- wherein m is 0 or 1;
- wherein A is selected from —Ar1— and a structure represented by a formula:
- wherein Z, when present, is selected from O, NR3, CR4aR4b, CO, and SO2;
- wherein each of R3, R4a, and R4b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl;
- wherein Ar1, when present, is selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein each of Ar2 and Ar3, when present, is independently selected from aryl, 5-membered heteroaryl, and 6-membered heteroaryl and substituted with 0, 1, 2, or 3 groups independently selected from halogen, —OH, —CN, —NH2, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
- wherein Q, when present, is selected from O, NR1, SO, SO2, C(O), and CR2aR2b;
- and
- wherein each of R1, R2a, and R2b, when present, is independently selected from hydrogen, C1-C4 alkyl, and C1-C4 haloalkyl.
12 more elements
Dependencies are inferred from the claim text.