WO2024048308A1 - Procédé de production de dispersion de structure organométallique, dispersion de structure organométallique et composition de structure organométallique comprenant une dispersion de structure organométallique - Google Patents
Procédé de production de dispersion de structure organométallique, dispersion de structure organométallique et composition de structure organométallique comprenant une dispersion de structure organométallique Download PDFInfo
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- WO2024048308A1 WO2024048308A1 PCT/JP2023/029742 JP2023029742W WO2024048308A1 WO 2024048308 A1 WO2024048308 A1 WO 2024048308A1 JP 2023029742 W JP2023029742 W JP 2023029742W WO 2024048308 A1 WO2024048308 A1 WO 2024048308A1
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- Prior art keywords
- metal
- dispersion
- organic
- component
- organic framework
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- 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
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
Definitions
- the present invention relates to a method for producing a metal-organic framework (MOF) dispersion having excellent dispersion stability, a metal-organic framework dispersion, and a metal-organic framework composition containing the metal-organic framework dispersion.
- MOF metal-organic framework
- a metal-organic framework is a porous coordination compound obtained by self-assembly of a metal ion and an organic ligand having a site that coordinates with the metal ion. They are bonded by positional bonds and have both inorganic and organic parts. Metal-organic frameworks have excellent porosity and excellent ability to adsorb and desorb molecules into pores, and are therefore being considered for a variety of applications such as gas separation membranes, gas storage, liquid adsorption, and catalysts.
- metal-organic structures examples include tablets formed from powder, and the range of practical applications is limited. The reason for this is that the metal-organic structure has a crystal size on the order of ⁇ m due to crystal growth due to rapid self-organization, and also has the property of easily agglomerating.
- Patent Document 1 For example, in gas separation applications, when a polymer and gas molecules are combined, non-selective pores are created between the polymers due to agglomeration of the metal-organic framework, resulting in a decrease in gas selectivity (Patent Document 1) ).
- Patent Document 1 if the dispersion stability is poor, during the composition preparation process or film formation process, formation of coarse particles due to agglomeration of the metal-organic framework or deterioration of the degree of dispersion of the metal-organic framework may result in film defects or property deterioration. Variations occur.
- Patent Document 1 and Patent Document 2 when synthesizing a metal-organic structure by the solvothermal method, for the purpose of suppressing crystal growth, a large amount of a chemical regulator or surfactant is added to the nanometer level by adding a large amount of chemical regulator or surfactant that is about the same amount as the raw material.
- a large amount of a chemical regulator or surfactant is added to the nanometer level by adding a large amount of chemical regulator or surfactant that is about the same amount as the raw material.
- Patent Document 3 reports that a composite composition can be obtained by coexisting a polymer that serves as a matrix when producing a metal-organic structure by solid-phase synthesis, but there are no specific details regarding dispersion stability. Not shown.
- metal-organic structure powder is mixed with a resin or solvent, and the metal-organic structure is agglomerated by mixing using an ultrasonic homogenizer, a rotational stirring degassing device, etc.
- There are methods to obtain a dispersion liquid by relaxing the state and methods to obtain a dispersion liquid by relaxing the agglomerated state using a mechanical grinding method such as a ball mill or a bead mill.
- mechanical crushing methods such as ball mills and bead mills create conditions that generate strong physical force and shear stress, which causes the problem that the crystal structure of the metal-organic structure is broken (Patent Document 4).
- An object of the present invention is to obtain a metal-organic structure dispersion having good dispersion stability and a metal-organic structure composition containing the metal-organic structure dispersion.
- a solid powder of a metal-organic structure is reduced in crystal size by mechanical pulverization to produce a dispersion, it is necessary to maintain the crystal structure of the metal-organic structure in terms of properties.
- mechanical crushing changes the crystal structure of the metal-organic framework.
- the inventor focused on the crystal size of the metal-organic structure and attempted to increase the crystal size from ⁇ m to nm.
- mechanical crushing methods with weak shear stress do not reduce the crystal size
- mechanical crushing methods with strong shear stress such as ball mills and bead mills, reduce the crystal size but change the crystal structure.
- the inventor discovered that the crystal size of the metal-organic structure can be reduced without changing the crystal structure of the metal-organic structure by adding a suitable dispersant in a ball mill or bead mill.
- the metal-organic structure can be aggregated by appropriately selecting and combining the metal ions and organic ligands that make up the metal-organic structure, as well as the dispersant and dispersion medium. I discovered that it is possible to avoid this. That is, the inventor found an appropriate mechanical crushing method, metal-organic structure, dispersant, and dispersion medium, and completed the invention.
- the present invention is a method for producing a metal-organic structure dispersion, comprising: (a) Component: a metal-organic structure containing a metal ion and an organic ligand coordinated to the metal ion, where the metal ion is at least one selected from the group consisting of Zr ions, Al ions, and Zn ions. a solid powder of (b) Component: As a dispersant, it is a primary amine, secondary amine, or tertiary amine having one amino group represented by the following formula (1) in the molecule, and (c1) a dispersion medium.
- step (1) of mixing with a dispersion medium, and step (2) of preparing a dispersion liquid by a mechanical pulverization method using the resulting mixture (however, the mechanical pulverization method A method for producing a dispersion of a metal-organic structure, provided that the crystal structure of the metal-organic structure does not change and maintains the crystal structure of a solid powder.
- the metal-organic structure dispersion liquid is such that the Z-average particle size of the solid powder of the metal-organic structure in the dispersion liquid is 10 nm or more and less than 1000 nm, and the metal-organic structure is A method for producing a metal-organic structure dispersion, wherein the sedimentation rate of solid powder particles is 100 ⁇ m/s or less.
- organic ligand is at least one selected from the group consisting of fumaric acid, terephthalic acid, isophthalic acid, 2-aminoterephthalic acid, 2-methylimidazole, and dicarboxypyrazole.
- a method for producing a metal-organic structure dispersion wherein the metal-organic structure is MIL-53, CAU-10, ZIF-8, MOF-801, MOF-303, UiO-66, or UiO-NH2-66.
- the method for producing a metal-organic structure dispersion wherein the mechanical pulverization method is a pulverization method using a ball mill or a bead mill.
- the ball mill or bead mill has a ball or bead diameter of 0.01 mm or more and 10 mm or less, and the material of the balls or beads is at least one selected from the group consisting of metal and glass, for producing a metal-organic structure dispersion. Method.
- Component a metal-organic structure containing a metal ion and an organic ligand coordinated to the metal ion, where the metal ion is at least one selected from the group consisting of Zr ions, Al ions, and Zn ions.
- R 1 and R 2 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, and * represents a bond with a carbon atom.
- Component A dispersion liquid containing a dispersion medium, The Z-average particle size of the solid powder of the metal-organic structure in the dispersion is 10 nm or more and less than 1000 nm, and the sedimentation rate of the solid powder particles of the metal-organic structure in an environment with a centrifugal force of 470 G or less is 100 ⁇ m/ s or less.
- a dispersion of a metal-organic structure wherein the organic ligand is at least one selected from the group consisting of fumaric acid, terephthalic acid, isophthalic acid, 2-aminoterephthalic acid, 2-methylimidazole, and dicarboxypyrazole.
- a metal-organic framework dispersion wherein the metal-organic framework is MIL-53, CAU-10, ZIF-8, MOF-801, MOF-303, UiO-66, or UiO-NH2-66.
- a metal-organic structure composition comprising at least one of the metal-organic structure dispersion liquid, a dispersion medium (c2) component different from the dispersion medium (c1) component in the dispersion liquid, and an additive (d) component.
- the method for producing a metal-organic structure dispersion of the present invention it is possible to provide a method for producing a metal-organic structure dispersion with excellent dispersion stability without changing the crystal structure of the metal-organic structure.
- the metal-organic structure dispersion and the metal-organic structure composition containing the metal-organic structure dispersion have the effect of exhibiting excellent dispersion stability without changing the crystal structure of the metal-organic structure. .
- the metal-organic structure dispersion liquid has a Z-average particle size of the solid powder of the metal-organic structure of 10 nm or more and less than 1000 nm, and a solid powder of the metal-organic structure in an environment with a centrifugal force of 470 G or less. It has the effect of exhibiting excellent dispersion stability with a sedimentation rate of powder particles of 100 ⁇ m/s or less.
- FIG. 1 is an X-ray diffraction pattern showing the crystal structure analysis results of the powder of Production Example 1, the powder obtained from the dispersion of Example 1, and the powder obtained from the dispersion of Comparative Example 1.
- FIG. 2 is a photograph of the SEM-EDX analysis results of the powder of Production Example 1, the powder obtained from the dispersion of Example 1, and the powder obtained from the dispersion of Comparative Example 1.
- FIG. 3 is an X-ray diffraction pattern showing the crystal structure analysis results of the powder of Production Example 2, the powder of Production Example 3, the powder obtained from the dispersion of Example 11, and the powder obtained from the dispersion of Example 15. It is.
- a metal-organic framework is a crystalline porous material consisting of metal ions and organic ligands coordinated to the metal ions.
- the metal ion is at least one selected from the group consisting of Mg, V, Cr, Nb, Mo, Zr, Hf, Mn, Fe, Co, Cu, Ni, Zn, Cd, Ru, Al, Ti, V, and Ga. It is an ion of two metals.
- Component (a) of the present invention is a solid powder of a metal-organic framework.
- the organic ligand is a compound having two or more functional groups (coordination functional groups) capable of coordinating with metal ions.
- coordinating functional groups include carboxyl groups, pyridinyl groups, cyano groups, amino groups, sulfonyl groups, porphyrinyl groups, acetylacetonate groups, hydroxyl groups, Schiff bases, amino acid residues, and the like.
- the coordination functional group is preferably one that can form a strong coordination bond with a metal ion.
- the organic ligand can preferably have two or more coordinating functional groups at any position on the organic ligand.
- Organic ligand having a coordinating functional group at the end of the organic ligand is preferable from the viewpoint of easily controlling the structure of the metal-organic structure and obtaining a metal-organic structure having relatively large pores.
- Organic ligands include oxalic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, citric acid, trimesic acid, squaric acid, imidazole, pyrazole, diazole, triazole, tetrazole, and azole. and mixtures thereof.
- fumaric acid, terephthalic acid, isophthalic acid, -At least one selected from the group consisting of aminoterephthalic acid, 2-methylimidazole, and dicarboxypyrazole is preferable.
- Dispersant examples include aliphatic amine compounds such as primary amines, secondary amines, or tertiary amines having one amino group in the molecule. Note that the aliphatic amine compound shown in the present invention has solubility in component (c1) and component (c2). Aliphatic amines include primary amines, secondary amines, and tertiary amines.
- Examples of primary amines include propylamine, butylamine, hexylamine, pentylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine (aminundecane), dodecylamine, tridecylamine, tetradecylamine, and pentadecylamine.
- Examples include saturated aliphatic monoamines having a linear aliphatic hydrocarbon group such as decylamine, hexadecylamine, heptadecylamine, and octadecylamine.
- saturated aliphatic amines include, in addition to the above-mentioned straight-chain aliphatic amines, branched aliphatic amines such as isohexylamine, 2-ethylhexylamine, and tert-octylamine. Further examples include unsaturated aliphatic amines such as cyclohexylamine and oleylamine. Furthermore, in addition to these aliphatic amines, primary amines also include those in which hydrogen atoms are replaced with hydroxyl groups, such as propanolamine.
- secondary amines include linear ones such as dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, octylamine, dinonylamine, didecylamine, diundecylamine, didodecylamine, ethylmethylamine, Examples include dialkyl monoamines such as methylpropylamine, ethylpropylamine, and propylbutylamine. Examples of branched secondary amines include diisohexylamine and di(2-ethylhexyl)amine.
- secondary amines include those in which hydrogen atoms are replaced with hydroxyl groups, such as methylaminoethanol.
- examples of the tertiary amine include tributylamine, tripentylamine, trihexylamine, and the like.
- Examples of branched tertiary amines include triisohexylamine, tri(2-ethylhexyl)amine, and tridodecylamine.
- tertiary amines also include those in which hydrogen atoms are replaced with hydroxyl groups.
- the number of nitrogen atoms in the aliphatic amine (compound) is 1, and the group bonded to the nitrogen atom is a straight chain aliphatic amine having 1 to 15 carbon atoms. It is a hydrocarbon group, and a hydroxyl group is preferable as a substituent for the aliphatic hydrocarbon group.
- (c1) component The aliphatic amines including the primary amines, secondary amines, and tertiary amines have solubility in component (c1) of the dispersion medium of the present invention.
- Component types include solvents, crosslinkable monomers, and polymers. These can be used alone or in combination of two or more. Specific examples of the component (c1) of the present invention are listed below, but the invention is not limited to these examples as long as the effects of the present invention are not lost.
- the solvent include methanol, ethanol, isopropyl alcohol, 1-butanol, 2-butanol, isobutyl alcohol, tert-butyl alcohol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl- 1-butanol, isopentyl alcohol, tert-pentyl alcohol, 3-methyl-2-butanol, neopentyl alcohol, 1-hexanol, 2-methyl-1-pentanol, 2-methyl-2-pentanol, 2-ethyl -1-butanol, 1-heptanol, 2-heptanol, 3-heptanol, 1-octanol, 2-octanol, 2-ethyl-1-hexanol, cyclohexanol, 1-methylcyclohexanol, 2-methylcyclohexanol, 3- Methylcyclohexanol, 1,2-ethanediol,
- a (meth)acrylate compound is mentioned as a specific example of a crosslinkable monomer.
- examples of (meth)acrylate compounds include glycol-based compounds such as polyethylene glycol diacrylate, neopentyl glycol diacrylate, tripropylene glycol diacrylate, polypropylene glycol diacrylate, polyethylene glycol dimethacrylate, and neopentyl glycol dimethacrylate. , tripropylene glycol dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, and mixtures thereof.
- other (meth)acrylate compounds include, for example, 1,4-butanediol dimethacrylate, 1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate, 1,10-decanediol dimethacrylate, Glycerin dimethacrylate, 2-hydroxy-3-acryloyloxypropyl methacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, dimethylol-tricyclodecane diacrylate, 2-hydroxy-3-acryloyloxy Bifunctional (meth)acrylates such as propyl methacrylate, trifunctional (meth)acrylates such as pentaerythritol triacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol hexamethylene diisocyanate urethane prepolymer
- Component (c2) of the present invention may be any compound as long as it dissolves aliphatic amines, and may be a compound different from component (c1).
- Component types include solvents, crosslinking monomers, and polymers, and are used when adjusting the solid content concentration, viscosity, coating properties, etc. of the resulting dispersion, and when forming a film from the dispersion. Can be added to adjust strength.
- Specific examples of component (c2) of the present invention include those described as specific examples of component (c1), but are not limited to these examples as long as the effects of the present invention are not lost.
- the aliphatic amines including the primary amines, secondary amines, and tertiary amines have solubility in the components (c1) and (c2) of the dispersion medium of the present invention. Therefore, regarding this solubility, the present inventor confirmed that the solubility parameter SP value of the (c1) component and (c2) component of the dispersion medium serves as an index.
- the SP value of the dispersion medium used in the examples of the present invention is shown in the column of component (c1) in the examples.
- the dispersion medium used in the examples of the present invention for example, methanol (MeOH) has an SP value of 30, and propylene glycol monomethyl ether acetate (PGMEA) has an SP value of 18.
- the SP value of the dispersion medium it is not particularly limited as long as the effect of the present invention is not lost, but from the viewpoint of dispersion stability, the SP value should be in the range of 5 to 50, and preferably the SP value is 10. 40, more preferably an SP value of 15 to 35.
- Component (d) of the present invention includes additives that are generally added as necessary, such as inorganic fillers, leveling agents, polymerization initiators, polymerization inhibitors, photosensitizers, adhesion agents, and plasticizers. , ultraviolet absorbers, conductive agents, and pigments. As long as the effects of the present invention are not impaired, they may be used alone or in combination of two or more.
- Step (1) is a step of mixing component (a), component (b), and component (c1).
- step (2) the mixture mixed in step (1) is subjected to the condition that the crystal structure (crystalline state) of the metal-organic structure of component (a) does not change and maintains its crystal structure (crystalline state).
- Step (3) is a step of mixing the metal-organic structure dispersion prepared in step (2) with at least one of the components (c2) and (d) to produce a metal-organic structure composition.
- ⁇ Mechanical crushing method> In order to obtain a dispersion liquid in which the metal-organic structure in the dispersion medium is mechanically pulverized and the crystal size of the metal-organic structure is reduced from ⁇ m size to nm size, stirring blades, ultrasonic stirring, homogenizer, ultra Techniques such as sonic homogenizers, hammer mills, vibrating mills, high speed rotary mills, etc. can be used.
- stirring methods that generate strong physical force or shearing force may change the crystals of the metal-organic structure, resulting in unfavorable results.
- one of the objects of the present invention is to obtain a nanometer-sized metal-organic structure while maintaining the crystal structure without changing the crystal of the metal-organic structure. Therefore, in the present invention, it is possible to control the material, size, and number of media to be placed in the container, as well as the rotation speed and rotation time of the container, and it is possible to suppress changes in the crystals of the metal-organic structure.
- a ball mill and a bead mill were used.
- changes in the crystals of the metal-organic structure were suppressed by selecting an appropriate dispersant in addition to the metal-organic structure to be placed in the containers of the ball mill and bead mill.
- One of the mechanical grinding techniques used in the present invention is a ball mill and a bead mill.
- the difference between a ball mill and a bead mill is the mechanism of rotational movement: in a ball mill, the container rotates, whereas in a bead mill, a mixer inside the container rotates.
- the media placed in both containers is the same, and the rotation speed and rotation time can be adjusted. Therefore, similar effects can be expected no matter which method is used.
- Media materials for ball mills and bead mills include (high) alumina, natural silica, silicon carbide, silicon nitride, glass, iron-cored nylon, zirconia, stainless steel, steel, carbon steel, and chrome steel.
- a media having a diameter of 0.01 mm or more and 10 mm or less can be used. From the above point of view, preferred sizes include diameters of 0.03 mm to 5.0 mm, more preferably diameters of 0.1 mm to 2.0 mm.
- Ultrasonic generator Ultrasonic cleaner (US CLEANER) manufactured by As One Co., Ltd. Frequency: 40kHz
- the Z-average particle diameter of the solid powder of the metal-organic framework can be calculated, for example, by a dynamic light scattering method.
- the metal-organic structure dispersion can be placed in a measurement cell, irradiated with light, and the Z average particle diameter can be calculated from the solution viscosity and temperature based on the principle of Brownian motion.
- the Z average particle diameter is preferably less than 1000 nm, more preferably 800 nm or less, and more preferably 600 nm or less.
- the apparatus used in the present invention, measurement conditions, etc. are shown. Equipment: Spectris Co., Ltd.
- the sedimentation velocity of the solid powder particles of the metal-organic framework was measured using a centrifugal sedimentation type device.
- the sedimentation velocity of the particles was calculated by forcibly causing the particles to sediment using the centrifugal force of the device, and by optically capturing and analyzing the changes.
- the sedimentation rate was calculated using the time change of the cell position at which the transmittance was 50%.
- the apparatus used in the present invention, measurement conditions, etc. are shown.
- Dispersion stability indicates that the lower the sedimentation rate, the better the dispersibility. From the viewpoint of handling properties and quality stabilization, it can be said that dispersion stability is good if the sedimentation velocity is 100 ⁇ m/s or less in an environment with a centrifugal force of 470 G or less.
- the sedimentation rate is preferably 90 ⁇ m/s or less, preferably 80 ⁇ m/s or less, and more preferably 70 ⁇ m/s or less.
- X-ray diffraction device X-ray diffraction device
- the measurement principle of an X-ray diffractometer is to analyze the diffraction that occurs as a result of X-rays scattering and interfering with electrons around atoms when a sample is irradiated with X-rays.
- XRD X-ray diffraction device
- the apparatus used in the present invention is shown.
- SEM scanning electron microscopy
- SEM/EDX energy dispersive X-ray spectroscopy
- the apparatus used in the present invention is a high-performance field emission scanning electron microscope that can obtain high resolution at an extremely low accelerating voltage of 1 kV or less in order to observe information on the surface of a sample.
- the apparatus used in the present invention, measurement conditions, etc. are shown.
- the reaction solution was heated to 130°C using an oil bath, and reacted at 130°C for 24 hours.
- a white powder formed and precipitated in the reaction solution was collected on a filter paper by Kiriyama filtration, and after washing with 300 ml of DMF and 300 ml of MeOH, the obtained metal-organic framework powder was vacuum-dried at 150° C. for 5 hours.
- the obtained powder was observed using a SEM, it was found to have a polyhedral shape close to a sphere with a primary particle size of about 1 ⁇ m, and secondary agglomeration to a size of about 5 to 50 ⁇ m.
- the reaction solution was heated to 120°C using an oil bath and reacted at 120°C for 6 hours.
- a yellowish white powder formed and precipitated in the reaction solution was collected on a filter paper by Kiriyama filtration, and after washing with 300 ml of MeOH and 300 ml of acetone, the obtained metal organic framework powder was vacuum dried at 120° C. for 5 hours.
- the obtained powder was observed using a SEM, it was found to be spherical with a primary particle size of about 0.6 to 1.0 ⁇ m, and secondary agglomeration to a size of about 20 to 50 ⁇ m.
- ⁇ MIL-53 Basolite (registered trademark) A100 (metal species: Al, organic ligand: terephthalic acid) [Sigma-Aldrich] From SEM observation, the primary particle size is approximately 1.0 to 1.5 ⁇ m in length and approximately 1.5 ⁇ m in width. It is acicular with a size of 15 to 30 nm, and the secondary aggregate is spherical with a size of about 20 to 40 ⁇ m.
- CAU-10 Aluminum isophthalic acid hydroxide MOF (metal species: Al, organic ligand: isophthalic acid) [Fujifilm Wa Hikari Pure Chemical Industries, Ltd.] From SEM observation, the primary particle size was cubic with a side of approximately 3.0 to 7.0 ⁇ m.
- ZIF-8 Zinc 2-methylimidazole MOF (metal species: Zn, organic ligand: 2- Methylimidazole) [Fujifilm Wako Pure Chemical Industries, Ltd.] From SEM observation, the primary particle size is spherical with a size of about 0.2 to 0.3 ⁇ m, and the secondary aggregate is elliptical with a size of about 10 ⁇ m.
- UiO-66 Zirconium 1,4-dicarboxybenzene MOF (metal type: Zr, organic ligand: 1,4-dicarboxybenzene) [Fujifilm Wako Pure Chemical Industries, Ltd.]
- ⁇ Dispersant, component (b)> The dispersants used in the present invention are shown together with abbreviations.
- ⁇ AM-2: Propanolamine [Tokyo Kasei Kogyo Co., Ltd.]
- ⁇ AM-4 1-Aminoundecane [Tokyo Kasei Kogyo Co., Ltd.]
- ⁇ AM-6: Trimethylstearylammonium chloride [Tokyo Kasei Kogyo Co., Ltd.]
- ⁇ AM-7: N,N-bis(3-aminopropyl)ethylenediamine [Tokyo Kasei Kogyo Co., Ltd
- ⁇ (c1) component> The component (c1) used in the present invention is shown together with abbreviations.
- ⁇ Homogeneity> The appearance of the prepared dispersion liquid was visually confirmed and evaluated according to the criteria shown below. It is preferable to use "A" as the dispersion liquid. A: No aggregated particles can be visually confirmed in the solution, and a colloidal color is observed. C: Agglomerated particles are visible, but no colloidal color is observed.
- the metal species constituting the metal-organic structure was Zr, and the dispersant was a polymer having one amino group in the molecule. It includes aliphatic amine compounds that are primary amines, secondary amines, or tertiary amines.
- the metal-organic framework is dispersed in a small size on the order of nm. , and a dispersion liquid exhibiting excellent dispersion stability was obtained.
- the metal species constituting the metal-organic structure was Zr, and the dispersant was a quaternary aliphatic amine compound having one amino group in the molecule. It includes. As shown in Table 2, compared to Examples 1 to 9, the metal-organic structures were aggregated in a large size on the ⁇ m order, and the dispersion stability was inferior.
- the metal species constituting the metal-organic structure was Zr, and the dispersant was a primary amine having a plurality of amino groups in the molecule, It includes an aliphatic amine compound that is a secondary amine or a tertiary amine.
- the metal-organic structures were aggregated in a large size on the ⁇ m order, and the dispersion stability was inferior.
- the metal species constituting the metal-organic structure was Zr, and the dispersant was a primary amine having one amino group in the molecule; It contains aromatic amine compounds that are secondary amines or tertiary amines.
- the metal-organic structures were aggregated in a large size on the ⁇ m order, and the dispersion stability was inferior.
- the metal species constituting the metal-organic structure was Zr, and the dispersant contained monocarboxylic acid or phosphonic acid.
- the metal-organic structures were aggregated in a large size on the ⁇ m order, and the dispersion stability was inferior.
- the metal species constituting the metal-organic framework was Al, and the dispersant contained one amino acid in the molecule. It contains an aliphatic amine compound which is a tertiary amine having a group.
- the metal-organic framework is on the order of nm. A dispersion liquid was obtained which was dispersed in a small size and showed excellent dispersion stability.
- the metal species constituting the metal-organic structure was Zn, and the dispersant was an aliphatic amine, which was a tertiary amine having one amino group in the molecule. It contains compounds.
- a dispersion liquid was obtained in which the metal-organic framework was dispersed in a small size on the nanometer order and had excellent dispersion stability.
- the metal species constituting the metal-organic framework was Zr, and the dispersant had one nitrogen atom in the molecule. It contains an aliphatic amine compound which is a tertiary amine.
- dispersions were obtained in which the metal-organic structures were dispersed in small sizes on the order of nanometers, and showed excellent dispersion stability, although the media types and sizes were different. .
- the metal species constituting the metal-organic structure was Zr, and the dispersant was an aliphatic amine, which was a tertiary amine having one amino group in the molecule.
- the processing method was ultrasonic treatment, and compared to the one that was mechanically pulverized in a ball mill in Example 1, the metal organic structure was aggregated in a large size on the ⁇ m order, It also showed that the dispersion stability was poor.
- the metal species constituting the metal-organic framework was Zr
- the dispersant was a tertiary amine having one nitrogen atom in the molecule. It contains a certain aliphatic amine compound, and the dispersion medium is crosslinking monomers D-1 and D-2.
- Examples 19 and 20 compared to Comparative Example 1 which does not contain a dispersant, Examples 19 and 20 have metal-organic structures dispersed in a small size on the order of nm, and have excellent A dispersion exhibiting dispersion stability was obtained.
- the metal species constituting the metal-organic structure was Al, and the dispersant was an aliphatic amine, which was a tertiary amine having one nitrogen atom in the molecule. It contains a compound, and the solid content concentration is higher than that of Examples 1 to 20 (15% by mass).
- a dispersion liquid was obtained in which the metal-organic framework was dispersed in a small size on the nanometer order and had excellent dispersion stability.
- the crystal structure of the white powder obtained by the above treatment and the powder obtained in Production Example 1 before the ball milling treatment was analyzed using XRD.
- the diffraction peak of the powder obtained from Comparative Example 1 which did not contain a dispersant and was subjected to ball milling, is different from the diffraction peak of the powder obtained from Production Example 1 and Example 1. It was suggested that the crystal structure had changed. From this result, in order to form a dispersion liquid while maintaining the crystal structure through mechanical pulverization, it is necessary to use a primary amine, secondary amine, or tertiary amine that has one amino group in the molecule as a dispersant. It was suggested that inclusion of aliphatic amine compounds is important.
- the white powder obtained by the above treatment and the powder obtained in Production Example 1 before the ball mill treatment were analyzed by SEM-EDX.
- the elemental composition of the powder obtained from Comparative Example 1 which did not contain a dispersant and was subjected to ball milling, was different from the elemental composition of the powder obtained from Production Example 1 and Example 1. It was suggested that the structure had changed. From this result, in order to form a dispersion liquid while maintaining the crystal structure through mechanical pulverization, it is necessary to use a primary amine, secondary amine, or tertiary amine that has one amino group in the molecule as a dispersant. It was suggested that it is important to include aliphatic amine compounds.
- the precipitated metal-organic framework white powder was collected on a filter paper by Kiriyama filtration, and DMF and MeOH were collected. After washing, the obtained metal-organic structure powder was vacuum-dried at 150° C. for 5 hours to obtain a powder.
- the crystal structures of the obtained powder and the powders obtained in Production Example 2 and Production Example 3 before ball milling were analyzed using XRD. As shown in FIG. 3, it was suggested that the crystal structure was maintained before and after the ball milling treatment.
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- Manufacture Of Metal Powder And Suspensions Thereof (AREA)
Abstract
[Problème] Fournir un procédé d'utilisation d'une technique de pulvérisation mécanique pour produire une dispersion comprenant une structure organométallique de taille nm qui présente une bonne stabilité de dispersion tout en conservant une structure cristalline. [Solution] Un procédé de production de dispersion de structure organométallique comprenant : une étape (1) consistant à mélanger un composant (a), qui représente une poudre solide d'une structure organométallique qui contient des ions métalliques et des ligands organiques coordonnés aux ions métalliques, lesdits ions métalliques étant au moins un type choisi dans le groupe constitué par des ions Zr, des ions Al, et des ions Zn, un composant (b), qui représente un dispersant et qui représente un composé amine aliphatique qui est une amine primaire, une amine secondaire, ou une amine tertiaire ayant un groupe amino dans une molécule de celle-ci, et qui est soluble dans un milieu de dispersion (c1), et un composant (c1), qui représente ledit milieu de dispersion ; et une étape (2) consistant à utiliser le mélange obtenu pour produire une dispersion par l'intermédiaire d'une technique de pulvérisation mécanique (dans laquelle, dans la technique de pulvérisation mécanique, la structure cristalline de la structure organométallique (a) ne change pas, et la structure cristalline de la poudre solide est conservée).
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