CN115322293A - Dispersing agent, preparation method and application of dispersing agent in preparation of carbon nano tube dispersion liquid - Google Patents
Dispersing agent, preparation method and application of dispersing agent in preparation of carbon nano tube dispersion liquid Download PDFInfo
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- CN115322293A CN115322293A CN202210579863.3A CN202210579863A CN115322293A CN 115322293 A CN115322293 A CN 115322293A CN 202210579863 A CN202210579863 A CN 202210579863A CN 115322293 A CN115322293 A CN 115322293A
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- maleic anhydride
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 81
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 239000002041 carbon nanotube Substances 0.000 title claims abstract description 57
- 229910021393 carbon nanotube Inorganic materials 0.000 title claims abstract description 57
- 239000006185 dispersion Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000007788 liquid Substances 0.000 title abstract description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229920000570 polyether Polymers 0.000 claims abstract description 20
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 13
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- JLSIEHRMXULWOA-UHFFFAOYSA-N carboxyoxy 3-ethyloctan-3-yl carbonate Chemical compound CCCCCC(CC)(CC)OC(=O)OOC(O)=O JLSIEHRMXULWOA-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 4
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 claims description 3
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 3
- 239000005456 alcohol based solvent Substances 0.000 claims 1
- 239000003759 ester based solvent Substances 0.000 claims 1
- 239000005453 ketone based solvent Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000012071 phase Substances 0.000 abstract description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000004321 preservation Methods 0.000 description 5
- 238000007142 ring opening reaction Methods 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- -1 aromatic dianhydride compound Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- DOMLXBPXLNDFAB-UHFFFAOYSA-N ethoxyethane;methyl prop-2-enoate Chemical compound CCOCC.COC(=O)C=C DOMLXBPXLNDFAB-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/158—Carbon nanotubes
- C01B32/168—After-treatment
- C01B32/174—Derivatisation; Solubilisation; Dispersion in solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
- C08F222/08—Maleic anhydride with vinyl aromatic monomers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
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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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract
The invention discloses a dispersing agent, a preparation method and application thereof in preparation of a carbon nano tube dispersion liquid. The preparation method of the dispersant comprises the following steps: carrying out copolymerization reaction on maleic anhydride and a comonomer under the conditions of a solvent, a chain transfer agent and an initiator to obtain a maleic anhydride copolymer; wherein, the comonomer comprises one or the combination of two or more of styrene, 4-vinylpyridine and N-vinyl pyrrolidone; the maleic anhydride copolymer is reacted with alkylamine or polyether amine under the condition of catalyst to obtain the dispersant. The dispersing agent has controllable structure, simple preparation method and lower production cost, can be used for preparing carbon nano tube dispersion liquid with better dispersion stability, and improves the dispersibility of the carbon nano tube in a water phase or an organic phase.
Description
Technical Field
The invention relates to the technical field of new materials and chemical industry, in particular to a dispersing agent, a preparation method thereof and application of the dispersing agent in preparation of carbon nano tube dispersion liquid.
Background
In recent years, electric vehicles have been rapidly developed with the view of environmental protection and sustainable development, and the performance of rechargeable batteries has been drawing attention as a core component of electric vehicles. The carbon nano tube is used as a novel conductive material with excellent electrical conductivity, thermal conductivity and mechanical property, and can greatly improve the performance of the battery including battery capacity, power, cycle life, heat dispersion and the like when being applied to a lithium battery as a positive and negative electrode material or a conductive liquid.
However, since the carbon nanotubes belong to the nano material, the carbon nanotubes have large specific surface area and are easy to gather, and if the carbon nanotubes cannot be effectively dispersed in the material, the reinforcing effect of the carbon nanotubes on the material can be greatly reduced. Therefore, an important issue in the current research of carbon nanotubes is to solve the dispersion of carbon nanotubes in different media, such as aqueous phase and different organic phase.
In the dispersion of the carbon nanotubes, it is important to select a proper dispersant, and the excellent dispersant can effectively improve the stability of the dispersion and the concentration of the carbon nanotubes in the dispersion. There are a number of different structural types of dispersants reported in the literature and patents. For example, chinese patent CN110437372A reports a carbon nanotube dispersant based on a copolymer of 4-vinylpyridine and poly (ethylene glycol) methyl ether acrylate, but the dispersant has fewer groups capable of forming pi-pi intermolecular interaction with carbon nanotubes. Chinese patent CN108017049A reports a carbazolyl conjugated polymer-based carbon nanotube dispersant, the main chain of the dispersant is a polycarbazole structure, and can form strong pi-pi conjugation with a carbon nanotube, but the side chain is a long-chain alkyl structure, so that the dispersant can only be applied to carbon nanotube dispersion of an organic phase, and the preparation method is complex. Chinese patent CN109867776A reports a carbon nanotube dispersant with aromatic group and double hydrophobic and hydrophilic group structure, which uses aromatic dianhydride compound and long-chain fatty alcohol to perform ring-opening reaction, and then performs amidation reaction on the ring-opening reaction product and polyether amine to obtain the carbon nanotube dispersant. However, the dispersant can only be used for dispersing carbon nanotubes in aqueous slurry. Chinese patent CN103582660B reports a highly branched polymer with acidic groups such as sulfonic acid group, which is prepared by condensing triarylamines and aldehydes or ketones under acidic conditions; researches show that the pi-pi interaction of aromatic rings containing triarylamine structures has high affinity to conjugated structures of carbon nanotubes, and the existence of a branched structure also enables the dispersing agent to have high solubility which a linear chain polymer does not have and excellent thermal stability; however, the synthesis steps are complicated and expensive.
Disclosure of Invention
In order to solve the above technical problems, the present invention aims to provide a dispersant, a preparation method thereof, and an application of the dispersant in preparation of a carbon nanotube dispersion. The dispersing agent has controllable structure, simple preparation method and lower production cost, can be used for preparing carbon nano tube dispersion liquid with better dispersion stability, and improves the dispersibility of the carbon nano tube in a water phase or an organic phase.
In order to achieve the technical purpose and achieve the technical effect, the invention is realized by the following technical scheme:
a dispersant having the structure of formula (I):
(I)
in the general formula (I), b is an integer of 1 to 100, a, c and d are integers of 0 or more, and a + c + d is an integer of 1 to 100;
R 1 is a structure shown in formula (II) or formula (III):
(II)
(III)
in the formula (II), e is an integer of 1 to 30; in the formula (III), f and g are integers of 0 or more, and f + g is an integer of 1 to 100.
The invention further provides a preparation method of the dispersant, which comprises the following steps:
(1) Carrying out copolymerization reaction on maleic anhydride and a comonomer under the conditions of a solvent, a chain transfer agent and an initiator to obtain a maleic anhydride copolymer; wherein the comonomer comprises one or the combination of two or more of styrene, 4-vinylpyridine and N-vinylpyrrolidone;
(2) And (2) reacting the maleic anhydride copolymer obtained in the step (1) with alkylamine or polyether amine under the condition of a catalyst to obtain the dispersing agent.
Further, the solvent in the step (1) is one or a mixture of two or more of water, an alcohol solvent, an ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, N-methylpyrrolidone and N, N-dimethylformamide; the dosage of the solvent is 1 to 10 times of the total mass of the maleic anhydride and the comonomer.
Further, the chain transfer agent is one or a mixture of two or more of tert-butyl alcohol, tert-dodecyl mercaptan, mercaptoethanol, thioglycolic acid, isooctyl 3-mercaptopropionate and 2, 4-diphenyl-4-methyl-1-pentene; the dosage of the chain transfer agent is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Further, the initiator is one or a mixture of two or more of azodiisobutyronitrile, dibenzoyl peroxide, diethylhexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite and potassium persulfate-sodium bisulfite; the dosage of the initiator is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Further, the catalyst is one or a mixture of two or more of triethylamine, 4-dimethylaminopyridine, ethanolamine, ethylenediamine and potassium carbonate; the dosage of the catalyst is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Further, the alkylamine is selected from one of dodecylamine, hexadecylamine and octadecylamine; the polyether amine is selected from one of ethylene oxide polyether amine, propylene oxide polyether amine and ethylene oxide-propylene oxide copolymerization polyether amine with different molecular weights; the amount of the substance of alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of maleic anhydride.
Further, the reaction time of the step (1) is 1 to 3 hours, and the reaction temperature is 40 to 150 ℃.
Further, the reaction time of the step (2) is 3-5 hours, and the reaction temperature is 80-150 ℃.
The invention further provides application of the dispersing agent in preparation of carbon nano tube dispersion liquid, wherein the carbon nano tube dispersion liquid comprises carbon nano tubes, a dispersing solvent and the dispersing agent.
The invention has the beneficial effects that:
the dispersant is a comb polymer, the main chain of the comb polymer is a copolymer formed by copolymerizing maleic anhydride and one or more of styrene, 4-vinylpyridine and N-vinyl pyrrolidone, and then alkylamine or alkoxy polyether amine is used for ring-opening the maleic anhydride to form a hydrophobic or hydrophilic side chain. Wherein, the styrene and the 4-vinylpyridine both contain large conjugated structures, can be used as anchoring groups through the interaction between pi-pi molecules formed by the styrene and the 4-vinylpyridine and have good affinity with the carbon nano tubes; the structure of polyvinylpyrrolidone polymerized by N-methyl pyrrolidone is similar to that of N-methyl pyrrolidone which is a common solvent for carbon nano tubes, which is beneficial to improving the dispersion effect of the carbon nano tubes in the prepared carbon nano tube dispersion liquid, and the polyvinylpyrrolidone (PVP) is a dispersant with better performance and can be cooperated with other groups or side chains in the dispersant synthesized by the invention to improve the dispersion effect; the alkylamine or alkoxy polyether amine can provide steric hindrance for a hydrophobic or hydrophilic side chain formed by ring opening of maleic anhydride, so that the carbon nano tube anchored with the dispersing agent can be effectively dispersed in an aqueous phase or an organic phase. Specifically, the alkylamine opens the ring of the maleic anhydride to form a hydrophobic side chain, so that the dispersing agent can be used for efficiently dispersing the carbon nano tube in the organic phase; the alkoxy polyether amine forms a hydrophilic side chain for maleic anhydride ring opening, so that the dispersant can be used for high-efficiency dispersion of carbon nanotubes in a water phase.
Therefore, the dispersant of the invention can be used as a carbon nano tube dispersant, has ideal dispersion effect on the carbon nano tube, and the carbon nano tube dispersion liquid prepared by the dispersant has good dispersion stability and has good dispersion effect on the carbon nano tube in an aqueous medium and an organic solvent medium.
The preparation method of the dispersant is simple, the production cost is low, the structure in the preparation process is controllable, and the dispersant can be produced in a large scale.
Drawings
FIG. 1 is an infrared spectrum of a dispersant obtained in example 1 of the present invention.
FIG. 2 is an infrared spectrum of the dispersant obtained in example 2 of the present invention.
FIG. 3 is an infrared spectrum of a dispersant obtained in example 3 of the present invention.
FIG. 4 is an infrared spectrum of the dispersant obtained in example 4 of the present invention.
FIG. 5 is an infrared spectrum of the dispersant obtained in example 5 of the present invention.
FIG. 6 is an infrared spectrum of a dispersant obtained in example 6 of the present invention.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to specific embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a dispersant, which has a structure shown in a general formula (I):
(I)
in the general formula (I), b is an integer of 1 to 100, a, c and d are integers of 0 or more, and a + c + d is an integer of 1 to 100;
R 1 is a structure shown in formula (II) or formula (III):
(II)
(III)
in the formula (II), e is an integer of 1 to 30; in the formula (III), f and g are integers of 0 or more, and f + g is an integer of 1 to 100.
The preparation method of the dispersant comprises the following steps:
(1) Adding a bottoming solvent into a reaction container provided with a mechanical stirrer and a condenser pipe, and introducing nitrogen to remove oxygen for 20 minutes; then, stirring and heating to a certain temperature, slowly dropwise adding a solution containing maleic anhydride, a comonomer, an initiator and a chain transfer agent by using a constant-pressure dropping funnel, keeping the temperature for reaction after dropwise adding is finished, and detecting the reaction progress by infrared spectroscopy;
alternatively, this step may be performed as follows:
adding a bottoming solvent and a chain transfer agent into a reaction container provided with a mechanical stirrer and a condensation pipe, and introducing nitrogen to remove oxygen for 20 minutes; then, stirring and heating to a certain temperature, slowly dropwise adding a solution in which maleic anhydride and a comonomer are dissolved by using one constant-pressure dropping funnel, slowly dropwise adding an initiator by using the other constant-pressure dropping funnel, carrying out heat preservation reaction after dropwise adding is finished, and detecting the reaction progress by infrared spectroscopy;
in the step (1), the dripping time is 1 to 5 hours, the heat preservation reaction time is 1 to 3 hours, and the reaction temperature is 40 to 150 ℃; obtaining maleic anhydride copolymer after reaction;
(2) Adding a metered amount of alkylamine or alkoxy polyether amine and a catalyst into the maleic anhydride copolymer obtained in the step (1), adjusting to a proper temperature for continuous reaction, monitoring the reaction progress through infrared spectrum, and removing the solvent in vacuum after the reaction is finished to obtain a light yellow product, namely the obtained dispersing agent product;
the reaction time of the step (2) is 3 to 5 hours, and the reaction temperature is 80 to 150 ℃.
Wherein, the solvent in the step (1) is one or the mixture of two or more of water, an alcohol solvent, an ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, N-methyl pyrrolidone and N, N-dimethylformamide; the dosage of the solvent is 1 to 10 times of the total mass of the maleic anhydride and the comonomer.
Wherein the chain transfer agent is one or a mixture of two or more of tert-butyl alcohol, tert-dodecyl mercaptan, mercaptoethanol, thioglycolic acid, isooctyl 3-mercaptopropionate and 2, 4-diphenyl-4-methyl-1-pentene; the dosage of the chain transfer agent is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Wherein the initiator is one or a mixture of two or more of azodiisobutyronitrile, dibenzoyl peroxide, diethylhexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite and potassium persulfate-sodium bisulfite; the dosage of the initiator is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Wherein the catalyst is one or a mixture of two or more of triethylamine, 4-dimethylaminopyridine, ethanolamine, ethylenediamine and potassium carbonate; the dosage of the catalyst is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
Wherein, the alkylamine is selected from one of dodecylamine, hexadecylamine and octadecylamine; the polyether amine is selected from one of ethylene oxide polyether amine, propylene oxide polyether amine and ethylene oxide-propylene oxide copolymerized polyether amine; the amount of the substance of alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of maleic anhydride.
The dispersant can be used as a carbon nano tube dispersant for preparing carbon nano tube dispersion liquid. The carbon nanotube dispersion liquid includes a carbon nanotube, a dispersion solvent, and the dispersant.
The present invention will be further described with reference to specific examples.
Example 1
A1000 mL three necked round bottom flask was charged with 200mL dry butanone, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, after which the mechanical stirrer was turned on and heated to 80 ℃. 10.4 g of styrene, 9.8 g of maleic anhydride, 10.5 g of 4-vinylpyridine, 11.1 g of N-vinylpyrrolidone, 2 g of azodiisobutyronitrile serving as an initiator and 1 g of mercaptoethanol serving as a chain transfer agent are dissolved in 200mL of anhydrous butanone, then the obtained solution is transferred into a constant-pressure dropping funnel, slowly and dropwise added into a three-neck round-bottom flask for reaction (the dropwise addition is finished for about 2 hours), and the reaction is carried out for 2 hours under heat preservation after the dropwise addition is finished.
After the polymerization reaction is finished, 18.5 g of dodecylamine and 1 g of triethylamine serving as a catalyst are added into a three-neck round-bottom flask, and the temperature is raised to 100 ℃ for reaction for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the reaction is hot, so that the dispersing agent 1 is obtained. The infrared spectrum of the dispersant 1 is shown in FIG. 1.
Example 2
A1000 mL three necked round bottom flask was charged with 200mL xylene, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, after which the mechanical stirrer was turned on and heated to 110 ℃. 10.4 g of styrene, 19.6 g of maleic anhydride, 10.5 g of 4-vinylpyridine, 2 g of initiator benzoyl peroxide and 1 g of chain transfer agent mercaptoethanol are dissolved in 200mL of dimethylbenzene, then transferred into a constant pressure dropping funnel, slowly dropped into a three-neck round-bottom flask for reaction (dropping is finished for about 1 hour), and after the dropping is finished, the reaction is kept for 2 hours.
After the polymerization reaction, 48.2 g of hexadecylamine and 1 g of triethylamine as a catalyst were added into a three-necked round-bottomed flask, and the temperature was raised to 130 ℃ to react for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the reaction is hot, so that the dispersing agent 2 is obtained. The infrared spectrum of the dispersant 2 is shown in FIG. 2.
Example 3
A1000 mL three necked round bottom flask was charged with 200mL of anhydrous toluene, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, then the mechanical stirrer was turned on and heated to 100 ℃. Dissolving 9.8 g of maleic anhydride, 21.1 g of 4-vinylpyridine, 11.1 g of N-vinylpyrrolidone, 2 g of initiator diethylhexyl peroxydicarbonate and 1 g of chain transfer agent mercaptoethanol in 200mL of anhydrous butanone, slowly dropwise adding the mixture into a three-neck round-bottom flask for reaction (after about 2 hours of dropwise addition), and then preserving the temperature for 2 hours after the dropwise addition.
After the polymerization reaction, 26.9 g of octadecylamine and 1 g of 4-dimethylaminopyridine serving as a catalyst are added into a three-neck round-bottom flask, and the temperature is raised to 120 ℃ for reaction for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the reaction is hot, so that the dispersing agent 3 is obtained. The infrared spectrum of the dispersant 3 is shown in FIG. 3.
Example 4
A1000 mL three necked round bottom flask was charged with 200mL dry butanone, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, after which the mechanical stirrer was turned on and heated to 80 ℃. 10.4 g of styrene, 9.8 g of maleic anhydride, 11.1 g of N-vinyl pyrrolidone, 2 g of initiator diethylhexyl peroxydicarbonate and 1 g of chain transfer agent tert-dodecyl mercaptan are dissolved in 150mL of anhydrous butanone, then transferred into a constant-pressure dropping funnel, slowly added into a three-neck round-bottom flask for reaction (after about 2 hours of dropping, the reaction is carried out for 2 hours under heat preservation after the dropping is finished).
After the polymerization reaction was completed, 200 g of ethylene oxide polyetheramine (Mn = 2000) and 1 g of triethylamine as a catalyst were added to a three-necked round-bottomed flask, and the temperature was raised to 100 ℃ to react for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the material is hot, so that the dispersing agent 4 is obtained. The infrared spectrum of the dispersant 4 is shown in FIG. 4.
Example 5
A1000 mL three necked round bottom flask was charged with 200mL dry butanone, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, after which the mechanical stirrer was turned on and heated to 80 ℃. 10.4 g of styrene, 9.8 g of maleic anhydride, 5 g of 4-vinylpyridine, 11.1 g of N-vinylpyrrolidone, 3 g of initiator diethylhexyl peroxydicarbonate and 1 g of chain transfer agent tert-dodecyl mercaptan are dissolved in 200mL of anhydrous butanone, and then transferred into a constant pressure dropping funnel, slowly added dropwise into a three-necked round-bottomed flask for reaction (about 2 hours are completely added dropwise), and after the dropwise addition is completed, the reaction is kept for 2 hours.
After the polymerization reaction, 300 g of propylene oxide polyetheramine (Mn = 3000) and 1 g of triethylamine as a catalyst were added to a three-necked round-bottomed flask, and the temperature was raised to 100 ℃ to react for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the material is hot, so that the dispersing agent 5 is obtained. The infrared spectrum of the dispersant 5 is shown in FIG. 5.
Example 6
A1000 mL three necked round bottom flask was charged with 200mL of dry butanone, equipped with a mechanical stirrer and reflux condenser, and purged with nitrogen to remove oxygen for 20 minutes, then the mechanical stirrer was turned on and heated to 80 ℃. 9.8 g of maleic anhydride, 10.5 g of 4-vinylpyridine, 22.2 g of N-vinylpyrrolidone, 1.5 g of initiator diethylhexyl peroxydicarbonate and 1 g of chain transfer agent tert-dodecyl mercaptan are dissolved in 200mL of anhydrous butanone, and then transferred into a constant-pressure dropping funnel, slowly added into a three-necked flask for reaction (the dropping is finished for about 2 hours), and after the dropping is finished, the reaction is carried out for 2 hours under heat preservation.
After the polymerization reaction was completed, 300 g of ethylene oxide-propylene oxide copolyether amine (Mn = 3000) and 1 g of triethylamine as a catalyst were added to a three-necked flask, and the temperature was raised to 100 ℃ to react for 5 hours. After the reaction is finished, the solvent is removed in vacuum, and the material is discharged when the reaction is hot, so that the dispersing agent 6 is obtained. The infrared spectrum of the dispersant 6 is shown in FIG. 6.
Application performance testing
The dispersant of the embodiment of the present invention and a commercially available dispersant as a comparative example were used to disperse carbon nanotubes in an aqueous phase or an organic phase, and after dispersion, the viscosity of the slurry and the particle size of the carbon nanotubes were measured, and the stability after standing for a certain period of time was observed.
The dispersion method comprises the following steps: 10 g of carbon nano tube, 1 g of dispersing agent, 500 g of dispersing solvent and 400 g of 0.3 mm zirconium beads are added into a vertical grinding cylinder, then the mixture is ground for 4 hours at the temperature of 25 ℃ and the rotating speed of 2000 r/min, and finally the zirconium beads are filtered to obtain the carbon nano tube dispersion liquid.
The performance of the carbon nanotube dispersion was tested, and the test results are shown in table 1. As can be seen from table 1, the particle size values of the carbon nanotubes of the examples of the present invention and the viscosity values of the slurry were lower than those of the comparative examples in terms of the particle size of the carbon nanotubes and the viscosity of the slurry, both in the aqueous phase and in the organic phase. After standing for 72 hours, the carbon nanotube dispersions corresponding to the embodiments of the present invention are all homogeneous solutions, but the bottom of the carbon nanotube dispersion corresponding to the comparative example has a sediment, so it can be seen that the dispersant of the embodiments of the present invention has a good dispersion effect on carbon nanotubes and excellent performance.
TABLE 1
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (10)
1. A dispersant, characterized by: has a structure represented by the general formula (I):
in the general formula (I), b is an integer of 1 to 100, a, c and d are integers of 0 or more, and a + c + d is an integer of 1 to 100;
R 1 is a structure shown in formula (II) or formula (III):
in the formula (II), e is an integer of 1 to 30; in the formula (III), f and g are integers of 0 or more, and f + g is an integer of 1 to 100.
2. A method for preparing the dispersant of claim 1, comprising the steps of:
(1) Carrying out copolymerization reaction on maleic anhydride and a comonomer under the conditions of a solvent, a chain transfer agent and an initiator to obtain a maleic anhydride copolymer; wherein the comonomer comprises one or the combination of two or more of styrene, 4-vinylpyridine and N-vinylpyrrolidone;
(2) And (2) reacting the maleic anhydride copolymer obtained in the step (1) with alkylamine or polyether amine under the condition of a catalyst to obtain the dispersing agent.
3. The method for preparing the dispersant according to claim 2, wherein the solvent in step (1) is one or a mixture of two or more selected from the group consisting of water, alcohol solvents, ester solvents, ketone solvents, aromatic hydrocarbon solvents, N-methylpyrrolidone, and N, N-dimethylformamide; the dosage of the solvent is 1 to 10 times of the total mass of the maleic anhydride and the comonomer.
4. The method for preparing the dispersant according to claim 2, wherein the chain transfer agent is one or a mixture of two or more of tert-butyl alcohol, tert-dodecyl mercaptan, mercaptoethanol, mercaptoacetic acid, isooctyl 3-mercaptopropionate, and 2, 4-diphenyl-4-methyl-1-pentene; the dosage of the chain transfer agent is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
5. The method for preparing the dispersing agent according to claim 2, wherein the initiator is one or a mixture of two or more of azodiisobutyronitrile, dibenzoyl peroxide, diethylhexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite and potassium persulfate-sodium bisulfite; the dosage of the initiator is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
6. The preparation method of the dispersant according to claim 2, wherein the catalyst is one or a mixture of two or more of triethylamine, 4-dimethylaminopyridine, ethanolamine, ethylenediamine and potassium carbonate; the dosage of the catalyst is 1 to 10 percent of the total mass of the maleic anhydride and the comonomer.
7. The method for preparing a dispersant according to claim 2, wherein the alkylamine is selected from one of dodecylamine, hexadecylamine and octadecylamine; the polyether amine is selected from one of ethylene oxide polyether amine, propylene oxide polyether amine and ethylene oxide-propylene oxide copolymer polyether amine; the amount of the substance of alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of maleic anhydride.
8. The method for preparing a dispersant according to claim 2, wherein the reaction time of step (1) is 1 to 3 hours, and the reaction temperature is 40 to 150 ℃.
9. The method for preparing a dispersant according to claim 2, wherein the reaction time of the step (2) is 3 to 5 hours and the reaction temperature is 80 to 150 ℃.
10. Use of the dispersant of claim 1 for the preparation of a carbon nanotube dispersion comprising carbon nanotubes, a dispersing solvent and the dispersant of claim 1.
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