WO2022255596A1 - Surface de particules de polymère de coordination à base de cuivre pour la capture de dioxyde de carbone et l'absorption de composés organiques volatils et procédé de préparation pour celle-ci - Google Patents
Surface de particules de polymère de coordination à base de cuivre pour la capture de dioxyde de carbone et l'absorption de composés organiques volatils et procédé de préparation pour celle-ci Download PDFInfo
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- WO2022255596A1 WO2022255596A1 PCT/KR2022/002753 KR2022002753W WO2022255596A1 WO 2022255596 A1 WO2022255596 A1 WO 2022255596A1 KR 2022002753 W KR2022002753 W KR 2022002753W WO 2022255596 A1 WO2022255596 A1 WO 2022255596A1
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- Prior art keywords
- copper
- cpp
- adsorbent
- polymer particles
- carbon dioxide
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 239000010949 copper Substances 0.000 title claims abstract description 56
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 54
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- SATWKVZGMWCXOJ-UHFFFAOYSA-N 4-[3,5-bis(4-carboxyphenyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(C=2C=CC(=CC=2)C(O)=O)=CC(C=2C=CC(=CC=2)C(O)=O)=C1 SATWKVZGMWCXOJ-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
- B01D53/04—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography with stationary adsorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28028—Particles immobilised within fibres or filaments
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- B01J20/30—Processes for preparing, regenerating, or reactivating
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- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3206—Organic carriers, supports or substrates
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- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3268—Macromolecular compounds
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F3/00—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems
- F24F3/12—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems characterised by the treatment of the air otherwise than by heating and cooling
- F24F3/14—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems characterised by the treatment of the air otherwise than by heating and cooling by humidification; by dehumidification
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F3/00—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems
- F24F3/12—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems characterised by the treatment of the air otherwise than by heating and cooling
- F24F3/14—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems characterised by the treatment of the air otherwise than by heating and cooling by humidification; by dehumidification
- F24F3/1411—Air-conditioning systems in which conditioned primary air is supplied from one or more central stations to distributing units in the rooms or spaces where it may receive secondary treatment; Apparatus specially designed for such systems characterised by the treatment of the air otherwise than by heating and cooling by humidification; by dehumidification by absorbing or adsorbing water, e.g. using an hygroscopic desiccant
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D2257/50—Carbon oxides
- B01D2257/504—Carbon dioxide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
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- B01D2257/708—Volatile organic compounds V.O.C.'s
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
Definitions
- the present invention relates to a surface of copper-based coordination polymer particles for capturing carbon dioxide and absorbing volatile organic compounds and a method for preparing the same, and in particular, to a novel adsorbent comprising a surface of copper-based coordination polymer particles coated on a nonwoven fabric surface, and It relates to a manufacturing method thereof.
- non-woven fibers are widely used as commercial air filtration substrates because the curved channels formed by randomly stacked fibers are advantageous for increasing filtration, but have limitations as a single material, and copper-based coordinating polymer particles Although it can be used as an adsorbent material, it has a problem in that it is difficult to apply to a gas containing pollutants because it is in the form of a powder.
- An object of the present invention is to provide a copper-based coordinated polymer particle surface for stably capturing carbon dioxide and absorbing volatile organic compounds and a method for preparing the same.
- a gas adsorbent including nonwoven fibers coated with copper-based coordination polymer particles is provided.
- the copper-based coordination polymer particle may include a ligand having 1 or 4 aromatic rings.
- the ligand may be any one or more selected from those represented by the following formulas 1 to 2:
- R 1 is -F, -Cl, -Br, -I, -S - , -O - , -NO 2 , -CN, -SO 3 - -COO - or -COCl - ;
- R 2 to R 4 are each independently -H, -CH 3 or -C 2 H 5 ;
- p is 0 to 3;
- the nonwoven fabric may have a melting point of 115 ° C. or higher.
- the nonwoven fabric fiber may be a condensed polymer material.
- the gas may include at least one selected from volatile organic compounds and carbon dioxide.
- immersing non-woven fibers in a solution containing copper-based coordination polymer particles processing at 115° C. to 140° C. for 4 to 12 hours; And it is possible to provide a method for preparing a gas adsorbent, including; washing and drying.
- the copper-based coordination polymer particle may include a ligand having 1 or 4 aromatic rings.
- the gas may include at least one selected from volatile organic compounds and carbon dioxide.
- an adsorbent prepared by the method of the present invention may be provided.
- an air purifier including the adsorbent of the present invention may be provided.
- the present invention can effectively remove carbon dioxide and volatile organic compounds by providing a copper-based coordination polymer particle surface for capturing carbon dioxide and absorbing volatile organic compounds.
- Figure 1 shows the synthesis of a nonwoven fiber (NWF) surface decorated with copper-based coordination polymer particles (Cu-CPP) by an in situ growth method.
- NWF nonwoven fiber
- Cu-CPP copper-based coordination polymer particles
- SEM 2 is a scanning electron microscope (SEM) confirming the surface morphology of the nonwoven fabric fiber before the Cu-CPP coating.
- 3 is a scanning electron microscope to confirm the surface morphology of nonwoven fibers after Cu-CPP coating.
- FIG. 7 is a schematic diagram showing equipment for confirming p-xylene adsorption efficiency of Cu-CPP/NWF.
- FIG. 10 is a schematic diagram showing the p-xylene adsorption mechanism of Cu-CPP.
- FIG. 12 is a schematic diagram showing the carbon dioxide adsorption mechanism of Cu-CPP.
- An object of the present invention is to provide a copper-based coordinated polymer particle surface for stably capturing carbon dioxide and absorbing volatile organic compounds and a method for preparing the same.
- Cu-based coordination polymer particles refers to a compound composed of copper ions or clusters coordinated to organic ligands, and includes copper ions acting as Lewis acids and It can be used as a heterogeneous catalyst showing different substrate selectivity and efficiency depending on the various structures formed between organic compounds acting as Lewis bases.
- VOCs Volatile Organic Compounds
- a gas adsorbent including nonwoven fibers coated with copper-based coordination polymer particles is provided.
- the copper-based coordination polymer particle may include a ligand having 1 or 4 aromatic rings.
- the ligand may be at least one selected from those represented by Formulas 1 and 2 below:
- R 1 may be included without limitation as long as it is an element or ion capable of functioning as a Lewis base, but is preferably -F, -Cl, -Br, -I, -S - , -O - , -NO 2 , -CN, -SO 3 - -COO - or -COCl - ; R 2 to R 4 are each independently -H, -CH 3 or -C 2 H 5 ; p may be 0 to 3.
- the copper-based coordinated polymer particles including Chemical Formulas 1 and 2 are connected to the center of the node, and the cation- ⁇ interaction between the aromatic of the volatile organic compound and the copper metal and the ⁇ - between the aromatic of the volatile organic compound and the Chemical Formulas 1 to 2 A geometric structure capable of adsorbing the volatile organic compound may be provided through the ⁇ interaction.
- the copper-based coordination polymer particles including Formulas 1 to 2 provide an unsaturated copper ion center through a paddle wheel structure to induce a large quadrupole moment of carbon dioxide through an electrostatic interaction with carbon dioxide, and selectively release carbon dioxide. It is possible to form a cavity of a size that can be captured by
- the ligand may be represented by the following Chemical Formulas 3 to 5:
- R 5 is -H or -CH 3 .
- the ligand is trimesic acid (benzene-1,3,5-tricarboxylic acid; Trimesic acid), 1,3,5-tris (bromomethyl) -2,4,6-trimethylbenzene (1, 3,5-Tris(bromomethyl)-2,4,6-trimethylbenzene; C 12 H 15 Br 3 ) and 1,3,5-tris(4-carboxyphenyl)benzene (1,3,5-Tris(4- It may be one or more selected from carboxyphenyl)benzene; H 3 BTB).
- the nonwoven fabric may have a melting point of 115° C. or higher.
- the melting point of the nonwoven fiber is less than 115° C., denaturation may occur while the copper-based coordination polymer particles are coated on the surface of the nonwoven fabric.
- the nonwoven fabric fiber may be a condensed polymer material, preferably at least one selected from polyester and polyamide.
- the condensation polymer prepared by condensation polymerization of monomers has a higher heat resistance effect than the polymer prepared by addition polymerization of monomers, and can stably provide a surface structure of the adsorbent.
- the gas may include at least one selected from volatile organic compounds and carbon dioxide, and preferably, the volatile organic compounds may be aromatic compounds.
- the volatile organic compound may be any one or more selected from benzene, ethylene glycol, formaldehyde, methylene chloride, tetrachloroethylene, toluene, xylene and 1,3-butadiene, more preferably p-xylene (p-Xylene).
- the volatile organic compound and carbon dioxide can be captured or absorbed on the surface of the copper-based coordination polymer particle of the present invention to improve air quality.
- immersing the non-woven fabric fibers in a solution containing copper-based coordination polymer particles; processing at 115° C. to 140° C. for 4 to 12 hours; And washing and drying; containing, an adsorbent manufacturing method may be provided.
- the treatment temperature when the treatment temperature is less than 115 ° C., the reaction may not sufficiently occur, and when the treatment temperature is higher than 140 ° C., the surface area may not be maximized because the copper-based coordination polymer particles are not evenly distributed.
- the treatment time is less than 4 hours, the reaction may not sufficiently occur, and if the treatment time is more than 12 hours, the surface area of the copper-based coordination polymer particles may not be maximized.
- the copper-based coordination polymer particle may include a ligand having 1 or 4 aromatic rings.
- the copper-based coordination polymer particle may be any one selected from Chemical Formulas 1 to 2 described above, preferably any one selected from Chemical Formulas 3 to 5 described above.
- the nonwoven fabric may have a melting point of 115° C. or higher.
- the melting point of the nonwoven fabric is less than 115° C., modification may occur during the treatment so that the copper-based coordination polymer particles are coated on the surface of the nonwoven fabric.
- the gas may include at least one selected from volatile organic compounds and carbon dioxide.
- an adsorbent prepared by the method of the present invention may be provided.
- a filtration membrane, a filter, an air purifier, an air conditioner, an air conditioner, and the like including the adsorbent of the present invention may be provided.
- the surface of nonwoven fibers (NWF) decorated with copper-based coordinating polymer particles (Cu-CPP) was synthesized by an in situ growth method. Specifically, 2.18 g of Cu(NO 3 ) 2 .3H 2 O was dissolved in 60 mL of an aqueous solution, and then 60 mL of an ethanol solution containing 1.05 g of trimesic acid as an organic ligand was poured. The mixed solution was vortexed, shaken, and sonicated for 4 minutes.
- NWF nonwoven fabric
- Cu-CPP copper-based coordination polymer particles
- Cu-CPP copper-based coordination polymer particles
- Cu-CPP copper-based coordination polymer particles
- the normal material growth method of Preparation Example 1 was used, but 1,3,5-tris (bromomethyl) -2,4, Cu-CPP was prepared using 6-trimethylbenzene (1,3,5-Tris(bromomethyl)-2,4,6-trimethylbenzene; C 12 H 15 Br 3 ).
- Cu-CPP copper-based coordination polymer particle
- the normal material growth method of Preparation Example 1 was used, but 1,3,5-tris (4-carboxyphenyl) benzene (1, Cu-CPP was prepared using 3,5-Tris(4-carboxyphenyl)benzene; H 3 BTB).
- Cu-CPP copper-based coordination polymer particles
- the normal material growth method of Preparation Example 1 was used, but 2,5-dihydroxyterephthalic acid (2,5-dihydroxyterephthalic acid) was used as an organic ligand. acid; dhtp) was used to prepare Cu-CPP.
- Cu-CPP copper-based coordination polymer particles
- Comparative Example 8 the normal material growth method of Preparation Example 1 was used, but Cu-CPP was prepared using fumaric acid as an organic ligand.
- Cu-CPP copper-based coordination polymer particles
- Comparative Example 9 the normal material growth method of Preparation Example 1 was used, but Cu-CPP was prepared using propanedioic acid as an organic ligand.
- the BET surface area (SBET) of Preparation Examples 1 to 5 is 1,200 m 2 /g or more and the pore volume (VBJH) is 0.4 cm 2 /g or more, which is comparable to Comparative Examples 1 to 9 and This is a significantly higher value than the BET surface area and pore volume of activated carbon, and the average pore diameter of Preparation Examples 1 to 5 is also 12 ⁇ or more, which is significantly higher than that of Comparative Examples 1 to 9.
- Use of trimesic acid or dhtp organic ligand After manufacturing Cu-CPP, the effect of excellent surface properties was confirmed in the case of the copper surface grown on polyester, polyamide, polycarbonate or polyphenylene oxide nonwoven fiber material at 120 ° C. for 6 hours.
- Example 1 the surface morphology of the nonwoven fabric (NWF) before the Cu-CPP coating was confirmed with a scanning electron microscope (SEM) and shown in FIG. 2, and the surface morphology of the nonwoven fabric (NWF) after the Cu-CPP coating The surface morphology was confirmed with a scanning electron microscope (SEM) and shown in FIG. 3 .
- the nonwoven fabric before Cu-CPP coating showed a clean and smooth surface and a wavy channel
- the result showed Cu- The appearance of CPP microcrystals was clearly detected.
- the Cu-CPP crystals densely covered the non-woven fabric (NWF) and each had a diameter of about 12 ⁇ m using an octahedral topology.
- EDS energy-dispersive spectrum
- the peaks of carbon and oxygen, which are the main elements forming nonwoven fabric fibers, are displayed, and the peak of copper is also displayed, indicating that all elements constituting the Cu-CPP/NWF are uniformly distributed over the entire surface of the filter. Bar, it was confirmed that Cu-CPP was successfully grown on nonwoven fabric fibers.
- the nitrogen gas absorption ability according to the change of the BET surface area was evaluated. Specifically, nitrogen gas absorption isotherms of Cu-CPP/NWF (or Cu-CPP microcrystals) according to Preparation Example 1 and Cu-CPP/NWF according to Comparative Example 3 and non-woven fabric fibers without copper coating were measured, and FIG. 6 shown in
- the amount of p-xylene absorbed by using nonwoven fabric (NWF) was measured by GC/MS and shown in FIGS. 8 and 9 .
- the nonwoven fabric (NWF) used as a control has no absorption capacity, whereas the Cu-CPP/NWF filter absorbs up to 100% p-xylene for 350 minutes, reducing carcinogenic volatility. It was confirmed that organic compounds can be utilized in high-efficiency and eco-friendly processes for decontamination.
- Cu-CPP adsorbs p-xylene. Since Cu-CPP composed of copper cations can be adsorbed through the cation- ⁇ interaction between the aromatics of p-xylene and the metal as the connecting center of the node, the Cu-CPP of the present invention has an adsorption effect of volatile organic compound contaminants. It was possible to confirm that In addition, Cu-CPP has 1,3,5-benzene tricarboxylic acid as an organic linker, which was effective for adsorption due to the ⁇ - ⁇ interaction between the phenyl ring of p-xylene and the Cu-CPP structure. Moreover, the large cavities and rich gas adsorption sites of Cu-CPP together with the very high surface area provided a positive contribution to the adsorption of contaminants.
- the carbon dioxide gas absorbing ability according to the change of the BET surface area was evaluated. Specifically, Cu-CPP/NWF (or Cu-CPP microcrystals) according to Preparation Example 1 and Cu-CPP/NWF and non-copper coated NWF according to Comparative Example 3 respectively absorb carbon dioxide at 0 bar to 1 bar. The ability to do was confirmed and shown in Figure 11.
- the pure nonwoven fabric had no carbon dioxide adsorption activity, whereas the Cu-CPP microcrystals showed excellent adsorption performance with a relatively high adsorption capacity of 34.47 cm 3 /g.
- Cu-CPP microcrystals are in powder form, they can clog pipes and cause large gas resistance in practical applications, so it is preferable to use Cu-CPP/NWF in dynamic processes and practical applications.
- Comparative Example 3 it had an adsorption capacity of 19.81 cm 3 /g, and it was confirmed that it had a higher carbon dioxide adsorption capacity than pure nonwoven fabric fibers.
- FIG. 12 is a schematic diagram showing the carbon dioxide adsorption mechanism of Cu-CPP.
- the carbon dioxide adsorption mechanism was confirmed by the high porosity, large specific surface area and abundant open metal sites of the Cu-CPP deposited on the fibers.
- the two major adsorption sites contributing to the carbon dioxide adsorption mechanism of Cu-CPP are open metal sites and small cage window sites.
- the site was, firstly, that open metal ions could expose equally unsaturated copper ion centers through a paddlewheel structure, which led to the polarization of carbon dioxide through electrostatic interactions and to make carbon dioxide have a large quadrupole moment. induced, contributing to having the strongest binding site.
- An object of the present invention is to provide a copper-based coordinated polymer particle surface for stably capturing carbon dioxide and absorbing volatile organic compounds and a method for preparing the same.
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Abstract
La présente invention concerne une surface de particules de polymère de coordination à base de cuivre pour la capture de dioxyde de carbone et l'absorption de composés organiques volatils et un procédé de préparation pour celle-ci et, spécifiquement, un nouvel adsorbant comprenant une surface de particules de polymère de coordination à base de cuivre revêtues sur une surface d'un tissu non tissé et un procédé de fabrication pour l'adsorbant.
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JP2008161838A (ja) * | 2006-12-28 | 2008-07-17 | Nbc Inc | 触媒担持体 |
US20210154610A1 (en) * | 2020-05-22 | 2021-05-27 | Carlo Kristian Chu Carredo | Copper microbicidal filter |
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KR102050608B1 (ko) | 2011-03-31 | 2019-11-29 | 카운슬 오브 사이언티픽 앤드 인더스트리얼 리서치 | 강화된 기체 흡착 용량을 갖는 활성탄-금속 유기 골격 복합 물질 및 이의 제조 방법 |
JP6242136B2 (ja) * | 2013-09-30 | 2017-12-06 | 株式会社クラレ | 多孔性金属錯体組成物 |
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US20210154610A1 (en) * | 2020-05-22 | 2021-05-27 | Carlo Kristian Chu Carredo | Copper microbicidal filter |
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CHEVALIER V., MARTIN J., PERALTA D., ROUSSEY A., TARDIF F.: "Performance of HKUST-1 Metal-Organic Framework for a VOCs mixture adsorption at realistic concentrations ranging from 0.5 to 2.5 ppmv under different humidity conditions", JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING, ELSEVIER BV, NL, vol. 7, no. 3, 1 June 2019 (2019-06-01), NL , pages 103131, XP093009882, ISSN: 2213-3437, DOI: 10.1016/j.jece.2019.103131 * |
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