WO2000070012A1 - Filtres a chelateurs de metaux et filtres a chelates de metaux - Google Patents
Filtres a chelateurs de metaux et filtres a chelates de metaux Download PDFInfo
- Publication number
- WO2000070012A1 WO2000070012A1 PCT/AU2000/000477 AU0000477W WO0070012A1 WO 2000070012 A1 WO2000070012 A1 WO 2000070012A1 AU 0000477 W AU0000477 W AU 0000477W WO 0070012 A1 WO0070012 A1 WO 0070012A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- filter
- metal
- linker
- species
- groups
- 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.)
- Ceased
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
-
- 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
- B01D69/14—Dynamic membranes
- B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J45/00—Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties
Definitions
- the present invention relates generally to the separation and analysis of molecules.
- the invention relates to the isolation of these molecules from a mixture in a fluid phase on a porous membrane comprising a metal chelating filter or metal chelate filter
- porous membrane is in a microplate format, tube, vial
- bioaffinity molecules may then be analysed using a wide variety of methodologies including the employment of specific bioaffinity molecules, specific
- the molecules may be released
- affinity separation is very broad and include antibodies, antigens, enzymes, peptides, oligonucleotides, isolated receptors, carbohydrates,
- Microporous membranes as support matrices have also
- Ligand immobilised membranes provide a compact
- Ligands have been immobilised on support materials in the
- membranes have been initially coated with a water-insoluble protein such as Zein,
- Porous membrane materials used for non-covalent ligand immobilisation in affinity chromatography have included materials such
- PVDF polyvinylidene fluoride
- Non-covalent binding results in random orientation of the ligand and can
- peptides and the oligonucleotides are not only covalently bound to the
- peptides may be coupled to a solid support via
- biomolecules as ligands onto activated membranes are:-
- N ⁇ 2+ and Zn 2+ are the most widely.
- Suitable donor ligands include ammo acids histidine, cysteine and tryptophan Since natural proteins rarely contain suitably arranged donor
- ligands recombinant proteins are engineered with a metal chelate
- binding tag at either the C- or N- terminal ends of the protein for
- microporous filter materials such as Sepharose (IDA-sepharose, Pharmacia), magnetic beads (Ni-NTA Magnetic Agarose Beads, Qiagen) and microtitre plates (Ni-NTA HisSorb, Qiagen).
- Iminodiacetic acid (IDA) has also been covalently attached to a stable IDA
- MPS microporous plastic sheet
- the MPS matrix is an inert polymeric microporous sheet that contains
- silica that can either be fu ⁇ ctionalised with ion exchange groups or affinity ligands solely for the purpose of protein purification.
- metal chelate filter or metal chelating species filter when processed in accordance with the invention to provide a metal chelate filter or metal chelating species filter may provide a number of
- the invention provides a ligand immobilisation
- the invention provides for the capture and
- the invention has particularity in the diagnostics, high-throughput screening, and biotechnology industries.
- the invention has particularity in the diagnostics, high-throughput screening, and biotechnology industries.
- the invention has particularity in the diagnostics, high-throughput screening, and biotechnology industries.
- the invention has particularity in the diagnostics, high-throughput screening, and biotechnology industries.
- the invention has particularity in the diagnostics, high-throughput screening, and biotechnology industries.
- the process of the invention includes the following variants:-
- the invention includes within its scope products produced
- filter means a porous material
- filter media having an average pore size in the region of 0.01 to 1000 microns and more preferably 0.1-5 microns.
- the filter may be formed from either fully or partly from
- accessible functional groups such as -Si-OH groups or which may be treated with a reagent to provide accessible functional groups including -OH, -Si-OH, -NH 2 and other amine
- groups including alkylamino, thiols, cyanobromides, aldehydes, carboxylates, sulfonylchlorides, ketones, halogens,
- haloacetyl inclusive of chloroacetyl, iodoacetyl or bromoacetyl and
- epoxy groups may be attached directly to the filter or by an appropriate spacer arm or linker.
- porous filter materials comprising
- polyamides inclusive of nylon, cellulose acetate, nitrocellulose,
- polyvinylidene fluoride or other fluoropolymers, polysulfone, paper, or
- linkers and/or a metal chelating species or a metal chelate may also be suitable media for the attachment of linkers and/or a metal chelating species or a metal chelate.
- linker as used herein means any spacer group
- the linker prior to use has an appropriate functional group as
- linker can be utilised which may include substituted or
- unsubstituted alkyl groups having from one to twenty, or more preferably one to six carbons, and wherein the alkyl groups may be linear or
- branched Linkers may also comprise substituted or unsubstituted aryl or aryl alkyl groups
- the linking group may be variable comprising a single methylene or a plurality of methylene groups
- linking group may also comprise peptides or branched peptides inclusive
- linkers include, for example, both linear,
- polyamides polyethyleneimines, polyarylene sulfides, polysiloxanes,
- polyimides polyacetates, dend ⁇ mers and dendrime ⁇ c-like molecules or
- linker as used
- cross-linking species or reagents used to couple the metal chelate or metal chelating species to accessible functional
- cross-linking species either on the filter or which have been produced by de ⁇ vatisation
- Such cross-linking species are referred to by way of example to the
- microfibre In a preferred embodiment of the invention, microfibre
- glass filters made from silica are especially adapted for use in the
- Such filters have silanol (Si-OH) functional groups as part of
- the filter matrix may be derivatised using a suitable reagent to
- such reagents may have an in-built linker or the linker may be pre-attached to the metal
- the metal chelating species may be any metal chelating species.
- the metal chelating species includes a functional group capable of reacting with Si-OH groups such as triethoxysilane or trimethoxysilane.
- silanisation reagents which may be used for the
- filters comprise accessible amine groups on the surface of the filter.
- linker or metal chelating species with linker attached may
- peptides as linkers.
- filters may be treated with a reagent such as ethylenediamine which may be
- a short linker in a suitable solvent such as acetonitrile and usually in the presence of a catalyst such as triethylamine.
- Suitable reactive groups may need to be
- Such hydroxyl groups can be directly used for the attachment of a filter
- hydroxyl groups may be further derivatised with silanisation reagents
- Such reagents for example may include cyanogen bromide, tosyl chloride, N-hydroxy succinamide, diamines, hydrazine and its
- dialdehydes such as glutaraldehyde, carbodiimides, and
- MCS metal chelating species
- metal chelating species include iminodiacetic acid, nitrilotriacetic acid, diethylenetriamine
- metal chelate means the metal chelating species having a metal coordinated thereto. Chelation type associations make use of metal ions such as but not limited to, the
- metal chelate filters of the invention which include the
- metal can be used for immobilisation of ligands that coordinate with the
- species may be attached to the filter by a covalent bond, charge
- metal chelating species may be attached to the filter via a linker by either of the
- the linker may be pre-attached to the metal chelating species followed by attachment of
- suitable protecting groups include Fmoc, Boc, trityl groups and any other protecting groups.
- branched species such as lysine or branched polymeric species such as dendrimers may increase
- FIG. 1 shows a derivatised glass fibre filter
- imidodiacetic acid metal chelate attached to the filter with a linker.
- FIG. 2 shows a polyacrylamide gel with a low range
- dendrimer-HRP conjugate at about 73 kDa is readily apparent in the
- FIG. 3 shows results of an experiment using Zn 2+ immobilised on the filter in which HRP, HRP-antibody conjugate and HRP-dendrimer conjugate were passed through metal chelate filter discs
- FIG. 4 shows free HRP, HRP-antibody and E5 dendrimer-
- metal chelate glass fibre filters (Whatman GF/B, GF/C and GF/F).
- metal ion used was Zn 2+ .
- FIG. 5 shows results of an experiment in which E5-
- dendrimer conjugate, diluent only, E5 dend ⁇ mer only and E5 dendrimer- antibody conjugate were passed through Zn 2+ metal chelate filter discs
- FIG 6 of a polyacrylamide gel shows that metal chelate filter discs efficiently capture a 6 x histidine tagged protein from a
- the concentration of the tagged protein was found to be approximately five times higher in material eluted from the discs than material that flowed through the discs
- TNBS trmitrobenzynesulfonic acid
- HBTU Benzotriazole-N,N,N',N',-Tetramethyl-Uronium-Hexafluorophosphate
- HOBt N-Hydroxybenzothazole
- DIPEA diisopropylethylamine
- the Fmoc group was then tested with a TNBS test.
- the deprotected filters were treated with nitrilotriacetic acid
- Nitrilotriacetic acid derivatised filter discs were each placed on a sintered glass funnel connected to a vacuum pump. The discs were
- FIG. 1 shows an example of a molecular structure showing the derivatised filter, linker(s) and the metal chelate.
- FIG. 2 shows examples of different molar ratios of E5 dendrimer-HRP conjugations.
- FIG. 3 shows results of an experiment using Zn 2+
- HRP-dendrimer conjugate were passed through metal chelate filter discs
- FIG. 4 shows free HRP, HRP-antibody and E5 dendrimer-
- metal chelate glass fibre filters (Whatman GF/B, GF/C and GF/F).
- E5-dendrimer conjugate, diluent only, E5 dendrimer only and E5 dendrimer-antibody conjugate were passed through Zn 2+ metal
- TMB substrate was applied and washed as described above.
- FIG. 5 shows the results. It can be seen that the presence
- FIG 6 of a polyacrylamide gel shows that metal chelate filter discs efficiently captured a hexahistidme tagged protein from a
- MC and MCS filters may be incorporated into an immunoassay filter plate, column, syringe filter housing or tube for a wide
- the MC and MCS filters may also be embodied with a second type filter such as an FTATM Gene Guard
- the MC and MCS filters may further embodied with a second filter such as to restrict
- the bound genetic material such as human genomic DNA can be ultimately removed by use of reagents such as restriction endonucleases
- the fragments of the restriction digest can be incubated in the presence of a MC filter harbouring
- probes could be derivatised at their 5' or 3' ends with a metal chelate tail such as a hexahistidme tag or dendrimer e g PAMAM
- genomic DNA E g traditional methodology (other than FTA) of purification yields genomic DNA as a soluble fraction After restriction digest, or in vitro
- template nucleic acid can be produced that is in a position to be captured by such
- oligonucleotide probes may be mixed with the genomic DNA whereby the
- DNA/probe hybrids formed can be captured on MC
- a second probe conjugated to a detector label e g
- Oligonucleotides, mRNA and cDNA coupled to dendrimers or other species capable of acting as a ligand, for example a hexahistidine tag, can be
- dendrimers or a hexahistidine may be added directly to a MC filter sheet to form a microarray suitable for analysis without the need for a multi-well plate format.
- proteins including a hexahistidine tail may be immobilised on a metal chelate filter. This will
- Unstable recombinant protein may be immobilized on MC filters quickly and at room temperature
- incorporating an MC filter would enable the user to rapidly immobilize potential drugs or target
- the method could also be combined with a FTA filter for simultaneous
- MCF-captured proteins may then be tested for function in bioassays.
- An indicator of cellular events is the change in kinase activity. Interaction at the cell surface is
- a synthetic kinase substrate is incubated with the kinase sample of
- the substrate was engineered to contain a 6xHis
- a MC filter will have greater specificity than Promega's streptavidin filter that is commonly used together with biotin tagged peptides.
- the isolated library compound may then be further interrogated to
- target molecule may be conjugated to a dendrimer or hexahistidine tag either of which
- dendrimer or hexahistidine may then be further
- Overlapping peptide sequences may be tagged with a hexahistidme tail or dendrimers and immobilised onto metal chelate filters for subsequent screening
- metal chelate filter bottoms could be used to capture hexahistidine or dendrimer tagged or target molecules
- product may be engineered to bear a hexahistidme sequence This product may then readily be captured onto a metal chelate filter
- a deep well multiwell plate encapsulating a MC filter at the bottom of each well may be constructed
- each well may be carried out mammalian, yeast or bacterial culture without fluid dripping through the filter bottoms Protein
- FTA and MC filter materials within the same device may be constructed.
- the cells will lyse, the cells
- episomal and/or genomic DNA will bind to the FTA, and the recombinant protein containing an
- the recombinant protein can be harvested and assayed. If the protein collected is of interest
- Metalloproteases are implicated with the onset of
- metastasis being part of the mechanism utilised by
- Recombinant proteins and enzymes expressing a tag such as a hexahistidine tail may be assayed directly from culture to determine a) levels of
- each tube, column or well will amplify the capacity
- microorganisms or parts of microorganisms such as antigens or nucleic acids
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Dispersion Chemistry (AREA)
- Organic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00926556A EP1183327A1 (fr) | 1999-05-14 | 2000-05-15 | Filtres a chelateurs de metaux et filtres a chelates de metaux |
| AU45258/00A AU4525800A (en) | 1999-05-14 | 2000-05-15 | Metal chelating filters and metal chelate filters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPQ0343 | 1999-05-14 | ||
| AUPQ0343A AUPQ034399A0 (en) | 1999-05-14 | 1999-05-14 | Metal chelating filters and metal chelate filters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000070012A1 true WO2000070012A1 (fr) | 2000-11-23 |
Family
ID=3814547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/AU2000/000477 Ceased WO2000070012A1 (fr) | 1999-05-14 | 2000-05-15 | Filtres a chelateurs de metaux et filtres a chelates de metaux |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1183327A1 (fr) |
| AU (1) | AUPQ034399A0 (fr) |
| WO (1) | WO2000070012A1 (fr) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006502857A (ja) * | 2002-10-18 | 2006-01-26 | プロメガ コーポレイション | 分子を分離するための方法 |
| US8114197B2 (en) | 2009-12-22 | 2012-02-14 | Hollingsworth & Vose Company | Filter media and articles including dendrimers and/or other components |
| US9610546B2 (en) | 2014-03-12 | 2017-04-04 | Lockheed Martin Corporation | Separation membranes formed from perforated graphene and methods for use thereof |
| US9744617B2 (en) | 2014-01-31 | 2017-08-29 | Lockheed Martin Corporation | Methods for perforating multi-layer graphene through ion bombardment |
| US9833748B2 (en) | 2010-08-25 | 2017-12-05 | Lockheed Martin Corporation | Perforated graphene deionization or desalination |
| US9834809B2 (en) | 2014-02-28 | 2017-12-05 | Lockheed Martin Corporation | Syringe for obtaining nano-sized materials for selective assays and related methods of use |
| US9844757B2 (en) | 2014-03-12 | 2017-12-19 | Lockheed Martin Corporation | Separation membranes formed from perforated graphene and methods for use thereof |
| US9870895B2 (en) | 2014-01-31 | 2018-01-16 | Lockheed Martin Corporation | Methods for perforating two-dimensional materials using a broad ion field |
| US10005038B2 (en) | 2014-09-02 | 2018-06-26 | Lockheed Martin Corporation | Hemodialysis and hemofiltration membranes based upon a two-dimensional membrane material and methods employing same |
| US10017852B2 (en) | 2016-04-14 | 2018-07-10 | Lockheed Martin Corporation | Method for treating graphene sheets for large-scale transfer using free-float method |
| US10118130B2 (en) | 2016-04-14 | 2018-11-06 | Lockheed Martin Corporation | Two-dimensional membrane structures having flow passages |
| US10203295B2 (en) | 2016-04-14 | 2019-02-12 | Lockheed Martin Corporation | Methods for in situ monitoring and control of defect formation or healing |
| US10201784B2 (en) | 2013-03-12 | 2019-02-12 | Lockheed Martin Corporation | Method for forming perforated graphene with uniform aperture size |
| US10213746B2 (en) | 2016-04-14 | 2019-02-26 | Lockheed Martin Corporation | Selective interfacial mitigation of graphene defects |
| US10376845B2 (en) | 2016-04-14 | 2019-08-13 | Lockheed Martin Corporation | Membranes with tunable selectivity |
| US10418143B2 (en) | 2015-08-05 | 2019-09-17 | Lockheed Martin Corporation | Perforatable sheets of graphene-based material |
| US10471199B2 (en) | 2013-06-21 | 2019-11-12 | Lockheed Martin Corporation | Graphene-based filter for isolating a substance from blood |
| US10500546B2 (en) | 2014-01-31 | 2019-12-10 | Lockheed Martin Corporation | Processes for forming composite structures with a two-dimensional material using a porous, non-sacrificial supporting layer |
| US10653824B2 (en) | 2012-05-25 | 2020-05-19 | Lockheed Martin Corporation | Two-dimensional materials and uses thereof |
| US10696554B2 (en) | 2015-08-06 | 2020-06-30 | Lockheed Martin Corporation | Nanoparticle modification and perforation of graphene |
| US10980919B2 (en) | 2016-04-14 | 2021-04-20 | Lockheed Martin Corporation | Methods for in vivo and in vitro use of graphene and other two-dimensional materials |
| KR102357806B1 (ko) | 2021-08-10 | 2022-02-09 | 주식회사 에이치이공일 | 친환경 금속 킬레이트 겔필터, 이의 제조방법 및 이를 이용한 연수 샤워 헤드 |
| CN115583710A (zh) * | 2022-07-19 | 2023-01-10 | 江苏驰佳环保科技有限公司 | 一种螯合剂及其制备方法 |
| WO2024002382A1 (fr) * | 2022-06-28 | 2024-01-04 | 江苏久膜高科技股份有限公司 | Procédé de préparation d'une membrane de chélation pour purifier des produits chimiques électroniques humides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5914780A (ja) * | 1982-07-19 | 1984-01-25 | 電気化学工業株式会社 | タバコフイルタ |
| EP0984095A1 (fr) * | 1997-04-22 | 2000-03-08 | Chelest Corporation | Fibres formant chelate metallique, leur procede de fabrication, procede de sequestration par ces fibres, et filtre en fibres de ce type |
-
1999
- 1999-05-14 AU AUPQ0343A patent/AUPQ034399A0/en not_active Abandoned
-
2000
- 2000-05-15 EP EP00926556A patent/EP1183327A1/fr not_active Withdrawn
- 2000-05-15 WO PCT/AU2000/000477 patent/WO2000070012A1/fr not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5914780A (ja) * | 1982-07-19 | 1984-01-25 | 電気化学工業株式会社 | タバコフイルタ |
| EP0984095A1 (fr) * | 1997-04-22 | 2000-03-08 | Chelest Corporation | Fibres formant chelate metallique, leur procede de fabrication, procede de sequestration par ces fibres, et filtre en fibres de ce type |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Derwent World Patents Index; Class P15, AN 1984-058401 * |
| SERAFICA G.C. ET AL.: "Protein fractionation using fast flow immobilized metal chelate affinity membranes", BIOTECHNOLOGY AND BIOENGINEERING, vol. 43, 1994, pages 21 - 36 * |
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1581337A4 (fr) * | 2002-10-18 | 2008-05-07 | Promega Corp | Composition permettant de separer des molecules |
| EP1585970A4 (fr) * | 2002-10-18 | 2008-08-06 | Promega Corp | Procedes destines a separer des molecules |
| JP2006502857A (ja) * | 2002-10-18 | 2006-01-26 | プロメガ コーポレイション | 分子を分離するための方法 |
| US8114197B2 (en) | 2009-12-22 | 2012-02-14 | Hollingsworth & Vose Company | Filter media and articles including dendrimers and/or other components |
| US8956437B2 (en) | 2009-12-22 | 2015-02-17 | Hollingsworth & Vose Company | Filter media and articles including dendrimers and/or other components |
| US9833748B2 (en) | 2010-08-25 | 2017-12-05 | Lockheed Martin Corporation | Perforated graphene deionization or desalination |
| US10653824B2 (en) | 2012-05-25 | 2020-05-19 | Lockheed Martin Corporation | Two-dimensional materials and uses thereof |
| US10201784B2 (en) | 2013-03-12 | 2019-02-12 | Lockheed Martin Corporation | Method for forming perforated graphene with uniform aperture size |
| US10471199B2 (en) | 2013-06-21 | 2019-11-12 | Lockheed Martin Corporation | Graphene-based filter for isolating a substance from blood |
| US9870895B2 (en) | 2014-01-31 | 2018-01-16 | Lockheed Martin Corporation | Methods for perforating two-dimensional materials using a broad ion field |
| US9744617B2 (en) | 2014-01-31 | 2017-08-29 | Lockheed Martin Corporation | Methods for perforating multi-layer graphene through ion bombardment |
| US10500546B2 (en) | 2014-01-31 | 2019-12-10 | Lockheed Martin Corporation | Processes for forming composite structures with a two-dimensional material using a porous, non-sacrificial supporting layer |
| US9834809B2 (en) | 2014-02-28 | 2017-12-05 | Lockheed Martin Corporation | Syringe for obtaining nano-sized materials for selective assays and related methods of use |
| US9844757B2 (en) | 2014-03-12 | 2017-12-19 | Lockheed Martin Corporation | Separation membranes formed from perforated graphene and methods for use thereof |
| US9610546B2 (en) | 2014-03-12 | 2017-04-04 | Lockheed Martin Corporation | Separation membranes formed from perforated graphene and methods for use thereof |
| US10005038B2 (en) | 2014-09-02 | 2018-06-26 | Lockheed Martin Corporation | Hemodialysis and hemofiltration membranes based upon a two-dimensional membrane material and methods employing same |
| US10418143B2 (en) | 2015-08-05 | 2019-09-17 | Lockheed Martin Corporation | Perforatable sheets of graphene-based material |
| US10696554B2 (en) | 2015-08-06 | 2020-06-30 | Lockheed Martin Corporation | Nanoparticle modification and perforation of graphene |
| US10017852B2 (en) | 2016-04-14 | 2018-07-10 | Lockheed Martin Corporation | Method for treating graphene sheets for large-scale transfer using free-float method |
| US10376845B2 (en) | 2016-04-14 | 2019-08-13 | Lockheed Martin Corporation | Membranes with tunable selectivity |
| US10213746B2 (en) | 2016-04-14 | 2019-02-26 | Lockheed Martin Corporation | Selective interfacial mitigation of graphene defects |
| US10203295B2 (en) | 2016-04-14 | 2019-02-12 | Lockheed Martin Corporation | Methods for in situ monitoring and control of defect formation or healing |
| US10118130B2 (en) | 2016-04-14 | 2018-11-06 | Lockheed Martin Corporation | Two-dimensional membrane structures having flow passages |
| US10980919B2 (en) | 2016-04-14 | 2021-04-20 | Lockheed Martin Corporation | Methods for in vivo and in vitro use of graphene and other two-dimensional materials |
| US10981120B2 (en) | 2016-04-14 | 2021-04-20 | Lockheed Martin Corporation | Selective interfacial mitigation of graphene defects |
| KR102357806B1 (ko) | 2021-08-10 | 2022-02-09 | 주식회사 에이치이공일 | 친환경 금속 킬레이트 겔필터, 이의 제조방법 및 이를 이용한 연수 샤워 헤드 |
| WO2024002382A1 (fr) * | 2022-06-28 | 2024-01-04 | 江苏久膜高科技股份有限公司 | Procédé de préparation d'une membrane de chélation pour purifier des produits chimiques électroniques humides |
| US12330122B2 (en) | 2022-06-28 | 2025-06-17 | Jiangsu Jiumo Hi-Tech Co., Ltd. | Preparation method for chelating membrane for purifying wet electronic chemicals |
| CN115583710A (zh) * | 2022-07-19 | 2023-01-10 | 江苏驰佳环保科技有限公司 | 一种螯合剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1183327A1 (fr) | 2002-03-06 |
| AUPQ034399A0 (en) | 1999-06-03 |
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