EP4081335A2 - A novel composite membrane in nanofiber form for selectively separating anionic and cationic organic compounds, and a preparation method thereof - Google Patents
A novel composite membrane in nanofiber form for selectively separating anionic and cationic organic compounds, and a preparation method thereofInfo
- Publication number
- EP4081335A2 EP4081335A2 EP20906256.1A EP20906256A EP4081335A2 EP 4081335 A2 EP4081335 A2 EP 4081335A2 EP 20906256 A EP20906256 A EP 20906256A EP 4081335 A2 EP4081335 A2 EP 4081335A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- poly
- composite membrane
- acid
- cross
- range
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000012528 membrane Substances 0.000 title claims abstract description 151
- 239000002131 composite material Substances 0.000 title claims abstract description 130
- -1 cationic organic compounds Chemical class 0.000 title claims abstract description 95
- 239000002121 nanofiber Substances 0.000 title claims abstract description 40
- 125000000129 anionic group Chemical group 0.000 title description 12
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000002091 cationic group Chemical group 0.000 claims abstract description 32
- 238000001179 sorption measurement Methods 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000835 fiber Substances 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 12
- 239000011976 maleic acid Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
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- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 239000011877 solvent mixture Substances 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
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- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 2
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- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 claims description 2
- 235000010420 locust bean gum Nutrition 0.000 claims description 2
- 239000000711 locust bean gum Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001814 pectin Substances 0.000 claims description 2
- 229920001277 pectin Polymers 0.000 claims description 2
- 235000010987 pectin Nutrition 0.000 claims description 2
- 229920001504 poly(N-isopropylacrylamide-co-acrylic acid) Polymers 0.000 claims description 2
- 229920001501 poly(N-isopropylacrylamide-co-methacrylic acid) Polymers 0.000 claims description 2
- 229920001446 poly(acrylic acid-co-maleic acid) Polymers 0.000 claims description 2
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- 229920002502 poly(methyl methacrylate-co-methacrylic acid) Polymers 0.000 claims description 2
- 229920006002 poly(vinyl butyral-co-vinyl alcohol-co-vinyl acetate) Polymers 0.000 claims description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 235000019423 pullulan Nutrition 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 235000019832 sodium triphosphate Nutrition 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- 239000000230 xanthan gum Substances 0.000 claims description 2
- 235000010493 xanthan gum Nutrition 0.000 claims description 2
- 229940082509 xanthan gum Drugs 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000005019 zein Substances 0.000 claims description 2
- 229940093612 zein Drugs 0.000 claims description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 description 41
- 239000000975 dye Substances 0.000 description 37
- 239000000463 material Substances 0.000 description 29
- KSCQDDRPFHTIRL-UHFFFAOYSA-N auramine O Chemical compound [H+].[Cl-].C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 KSCQDDRPFHTIRL-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 21
- 238000001914 filtration Methods 0.000 description 17
- KHLVKKOJDHCJMG-QDBORUFSSA-L indigo carmine Chemical compound [Na+].[Na+].N/1C2=CC=C(S([O-])(=O)=O)C=C2C(=O)C\1=C1/NC2=CC=C(S(=O)(=O)[O-])C=C2C1=O KHLVKKOJDHCJMG-QDBORUFSSA-L 0.000 description 16
- 230000008569 process Effects 0.000 description 11
- 238000003556 assay Methods 0.000 description 10
- 150000002894 organic compounds Chemical class 0.000 description 7
- 230000007423 decrease Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- 239000013543 active substance Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- MFUVDXOKPBAHMC-UHFFFAOYSA-N magnesium;dinitrate;hexahydrate Chemical class O.O.O.O.O.O.[Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MFUVDXOKPBAHMC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005211 surface analysis Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D39/00—Filtering material for liquid or gaseous fluids
- B01D39/14—Other self-supporting filtering material ; Other filtering material
- B01D39/16—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres
- B01D39/1607—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres the material being fibrous
- B01D39/1623—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres the material being fibrous of synthetic origin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D39/00—Filtering material for liquid or gaseous fluids
- B01D39/14—Other self-supporting filtering material ; Other filtering material
- B01D39/16—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres
- B01D39/18—Other self-supporting filtering material ; Other filtering material of organic material, e.g. synthetic fibres the material being cellulose or derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/02—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor characterised by their properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
- B01D2239/02—Types of fibres, filaments or particles, self-supporting or supported materials
- B01D2239/025—Types of fibres, filaments or particles, self-supporting or supported materials comprising nanofibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
- B01D2239/06—Filter cloth, e.g. knitted, woven non-woven; self-supported material
- B01D2239/0604—Arrangement of the fibres in the filtering material
- B01D2239/0631—Electro-spun
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
- B01D2239/10—Filtering material manufacturing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
- B01D2239/12—Special parameters characterising the filtering material
- B01D2239/1233—Fibre diameter
Definitions
- FIGURE 6 illustrates the change of the BY2 concentration as a function of time for the adsorption of the cationic organic compound (of BY2) on the cross- linked composite membrane material at 25 °C.
- FIGURE 7 illustrates the change of the AB74 concentration as a function of time for the adsorption of the anionic organic compound (of AB74) on the cross-linked composite membrane material at 25 °C.
- the concentration of cationic BY2 dyestuff remaining in the aqueous solution decreases over time during the adsorption process.
- the initial decrease amount is significantly higher.
- the concentration of anionic AB74 dyestuff in an aqueous solution did not decrease during the adsorption process of 1440 minutes.
- anionic AB74 dyestuff is not adsorbed by the cross-linked composite membrane. Therefore, while the cross-linked composite membrane shows a high affinity towards the cationic organic compound, its affinity towards the anionic organic compound is significantly lower.
- Vacuum filtration method was employed in order to determine that which one of the dyestuffs is adsorbed better by the cross-linked composite membrane and which one of the dyestuffs is allowed to pass through the cross-linked composite membrane from an aqueous dyestuff mixture solution containing both the cationic BY2 dyestuff and the anionic AB74 dyestuff.
- a piece of cross-linked composite membrane was cut suitable in size for the vacuum filtration apparatus and placed onto the filtration apparatus.
- Nanofiltration composite membrane used for selective ion separation, and preparation method thereof Patent: CN108421422 (A). 6) Ratto, T.V. (2011) Membranes with embedded nanotubes for selective permeability, Patent: MX2011000140A.
- Patent W02016129801 (Al).
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TR2019/21099A TR201921099A2 (en) | 2019-12-23 | 2019-12-23 | A NEW COMPOSITE MEMBRANE IN THE FORM OF NANOFIBER TO SELECT ORGANIC COMPOUNDS OF ANIONIC AND CATIONIC STRUCTURE AND A METHOD FOR PREPARING THIS MEMBRANE |
PCT/TR2020/051320 WO2021133332A2 (en) | 2019-12-23 | 2020-12-18 | A novel composite membrane in nanofiber form for selectively separating anionic and cationic organic compounds, and a preparation method thereof |
Publications (2)
Publication Number | Publication Date |
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EP4081335A2 true EP4081335A2 (en) | 2022-11-02 |
EP4081335A4 EP4081335A4 (en) | 2023-10-25 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP20906256.1A Pending EP4081335A4 (en) | 2019-12-23 | 2020-12-18 | A novel composite membrane in nanofiber form for selectively separating anionic and cationic organic compounds, and a preparation method thereof |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP4081335A4 (en) |
TR (1) | TR201921099A2 (en) |
WO (1) | WO2021133332A2 (en) |
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CN113731179B (en) * | 2021-09-02 | 2024-03-12 | 东南大学 | Pervaporation membrane doped with core-shell structured filler and preparation method thereof |
CN117000045B (en) * | 2023-06-01 | 2024-02-20 | 贵州省材料产业技术研究院 | Loose nanofiltration membrane for removing heavy metals and preparation method thereof |
Family Cites Families (2)
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US11192098B2 (en) * | 2015-09-15 | 2021-12-07 | Amogreentech Co., Ltd. | Ion exchange membrane and method for manufacturing same |
CN107983163A (en) * | 2017-11-27 | 2018-05-04 | 桐乡佳车科技有限公司 | A kind of field controllable cation exchange membrane preparation method |
-
2019
- 2019-12-23 TR TR2019/21099A patent/TR201921099A2/en unknown
-
2020
- 2020-12-18 WO PCT/TR2020/051320 patent/WO2021133332A2/en unknown
- 2020-12-18 EP EP20906256.1A patent/EP4081335A4/en active Pending
Also Published As
Publication number | Publication date |
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WO2021133332A3 (en) | 2021-08-26 |
TR201921099A2 (en) | 2021-07-26 |
EP4081335A4 (en) | 2023-10-25 |
WO2021133332A2 (en) | 2021-07-01 |
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