CN115322293B - Dispersing agent, preparation method and application thereof in preparation of carbon nanotube dispersion liquid - Google Patents
Dispersing agent, preparation method and application thereof in preparation of carbon nanotube dispersion liquid Download PDFInfo
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- CN115322293B CN115322293B CN202210579863.3A CN202210579863A CN115322293B CN 115322293 B CN115322293 B CN 115322293B CN 202210579863 A CN202210579863 A CN 202210579863A CN 115322293 B CN115322293 B CN 115322293B
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- maleic anhydride
- dispersing agent
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 78
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 239000002041 carbon nanotube Substances 0.000 title claims abstract description 58
- 229910021393 carbon nanotube Inorganic materials 0.000 title claims abstract description 58
- 239000006185 dispersion Substances 0.000 title claims abstract description 24
- 239000007788 liquid Substances 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 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 28
- 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 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 229920000570 polyether Polymers 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 10
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 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 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
- -1 diethyl hexyl peroxydicarbonate Chemical compound 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
- 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 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 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
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 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
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 16
- 239000012074 organic phase Substances 0.000 abstract description 8
- 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 15
- 239000000463 material Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000007599 discharging Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 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
- 238000004321 preservation Methods 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 2
- ULWDYECGHQQXMV-UHFFFAOYSA-N 3-ethyl-3-(3-ethyloctan-3-ylperoxy)octane Chemical compound C(C)C(CCCCC)(CC)OOC(CCCCC)(CC)CC ULWDYECGHQQXMV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000002245 particle Substances 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
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 239000008096 xylene Substances 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
- 230000009286 beneficial effect Effects 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
- 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
- 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
- 230000002349 favourable effect Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 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
- 238000011056 performance test Methods 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 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
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- Y02E60/10—Energy storage using batteries
Abstract
The invention discloses a dispersing agent, a preparation method and application thereof in preparation of carbon nano tube dispersion liquid. The preparation method of the dispersing agent comprises the following steps: under the conditions of a solvent, a chain transfer agent and an initiator, carrying out copolymerization reaction on maleic anhydride and a comonomer to obtain a maleic anhydride copolymer; wherein the comonomer comprises one or more of styrene, 4-vinyl pyridine 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 and a preparation method thereof, and application of the dispersing agent in preparation of carbon nano tube dispersion liquid.
Background
In recent years, with the gradual realization of the environment-friendly and sustainable development concept, electric vehicles are rapidly developed, and as a core component of the electric vehicles, the performance of rechargeable batteries thereof is attracting attention. The carbon nano tube is used as a novel conductive material with excellent electrical conductivity, thermal conductivity and mechanical property, and can be used as a positive electrode material or a negative electrode material or a conductive liquid in a lithium battery, so that the performance of the battery, including battery capacity, power, cycle life, heat dissipation performance and the like, can be greatly improved.
However, since the carbon nanotubes are nano materials, the specific surface area is large, and the carbon nanotubes are easy to aggregate, if the carbon nanotubes cannot be effectively dispersed in the material, the reinforcing effect of the carbon nanotubes on the material is greatly reduced. An important issue in the current carbon nanotube research is to solve the dispersion performance of carbon nanotubes in different media, such as aqueous phase and different organic phases.
In the dispersion of carbon nanotubes, an important ring is to select a proper dispersant, and the excellent dispersant can effectively improve the stability of the dispersion liquid and the concentration of the carbon nanotubes in the dispersion liquid. There are a number of documents and patents currently reporting a number of different types of dispersants of different structures. 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 in the molecule that can form pi-pi intermolecular interactions with carbon nanotubes. Chinese patent CN108017049a reports a carbon nanotube dispersing agent based on a carbazolyl conjugated polymer, wherein the main chain of the dispersing agent is a polycarbazole structure, which can form a stronger pi-pi conjugation with carbon nanotubes, but the side chain is a long-chain alkyl structure, so that the dispersing agent can only be applied to the dispersion of carbon nanotubes in an organic phase, and the preparation method is complex. Chinese patent CN109867776a reports a carbon nanotube dispersing agent with a double hydrophobic and hydrophilic structure containing aromatic groups, which uses an aromatic dianhydride compound to perform a ring-opening reaction with long-chain fatty alcohol, and then performs an amidation reaction on the ring-opening reaction product and polyetheramine, thereby finally obtaining the carbon nanotube dispersing agent. However, the dispersant can only be used for dispersing carbon nanotubes in an aqueous slurry. Chinese patent CN103582660B reports a hyperbranched polymer with acidic groups such as sulfonic acid groups, prepared by condensing triarylamines with aldehydes or ketones under acidic conditions; the research shows that pi-pi interaction of aromatic ring containing triarylamine structure has high affinity to conjugated structure of carbon nanotube, and the existence of branched structure makes the dispersant possess high solubility and excellent heat stability; but the synthesis procedure is complicated and expensive.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a dispersing agent and a preparation method thereof, and application of the dispersing agent in preparing carbon nano tube dispersion liquid. 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 the technical effect, the invention is realized by the following technical scheme:
a dispersant having a structure represented by the general formula (I):
(I)
in the general formula (I), b is an integer of 1-100, a, c and d are integers greater than or equal to 0, and a+c+d is an integer of 1-100;
R 1 is of the structure shown in the formula (II) or the 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 dispersing agent, which comprises the following steps:
(1) Under the conditions of a solvent, a chain transfer agent and an initiator, carrying out copolymerization reaction on maleic anhydride and a comonomer to obtain a maleic anhydride copolymer; wherein the comonomer comprises one or a combination of two or more of styrene, 4-vinyl pyridine and N-vinyl pyrrolidone;
(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 selected from one or more of water, alcohol solvents, ester solvents, ketone solvents, aromatic hydrocarbon solvents, 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.
Further, the chain transfer agent is one or a mixture of more than two of tertiary butanol, tertiary dodecyl mercaptan, mercaptoethanol, mercaptoacetic acid, isooctyl 3-mercaptopropionate and 2, 4-diphenyl-4-methyl-1-pentene; the use amount of the chain transfer agent is 1-10% of the total mass of the maleic anhydride and the comonomer.
Further, the initiator is one or a mixture of more than two of azodiisobutyronitrile, dibenzoyl peroxide, diethyl hexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite and potassium persulfate-sodium bisulfate; the usage amount of the initiator is 1-10% 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 1-10% of the total mass of maleic anhydride and comonomer.
Further, the alkylamine is selected from one of dodecylamine, hexadecylamine and octadecylamine; the polyetheramine is selected from one of ethylene oxide polyetheramine, propylene oxide polyetheramine and ethylene oxide-propylene oxide copolymerized polyetheramine with different molecular weights; the amount of the substance of the alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of the 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 to 5 hours, and the reaction temperature is 80 to 150 ℃.
The invention further provides application of the dispersing agent in preparing a carbon nanotube dispersing liquid, wherein the carbon nanotube dispersing liquid comprises carbon nanotubes, a dispersing solvent and the dispersing agent.
The beneficial effects of the invention are as follows:
the dispersant of the invention is a comb polymer, the main chain of which is a copolymer formed by copolymerization of maleic anhydride and one or more of styrene, 4-vinyl pyridine and N-vinyl pyrrolidone, and then alkyl amine 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-vinyl pyridine both contain large conjugated structures, can be used as anchoring groups through pi-pi intermolecular interaction formed by the carbon nano tubes, and have good affinity with the carbon nano tubes; the structure of polyvinylpyrrolidone obtained by polymerizing N-methyl pyrrolidone is similar to that of N-methyl pyrrolidone which is a common solvent for carbon nanotubes, which is favorable for improving the dispersing effect of carbon nanotubes in the prepared carbon nanotube dispersion liquid, and polyvinylpyrrolidone (PVP) is a dispersing agent with better performance and can cooperate with other groups or side chains in the dispersing agent synthesized by the invention to improve the dispersing effect; wherein the alkyl amine or the alkoxy polyether amine can provide steric hindrance for hydrophobic or hydrophilic side chains 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, alkylamine opens a ring to maleic anhydride to form a hydrophobic side chain, so that the dispersing agent can be used for efficiently dispersing carbon nanotubes in an organic phase; the alkoxy polyether amine is used for opening the maleic anhydride to form a hydrophilic side chain, so that the dispersing agent can be used for efficiently dispersing the carbon nano tube in the water phase.
Therefore, the dispersing agent can be used as a carbon nano tube dispersing agent, has ideal dispersing effect on carbon nano tubes, and the carbon nano tube dispersing liquid prepared by the dispersing agent has good dispersing stability and good dispersing effect on the carbon nano tubes in an aqueous medium and an organic solvent medium.
The preparation method of the dispersing agent is simple, the production cost is low, the structure in the preparation process is controllable, and the large-scale production can be carried out.
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 the 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 following description of the embodiments of the present invention will be made more apparent and fully by reference to the accompanying drawings, in which it is shown, by way of illustration, only some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a dispersing agent, which has a structure shown in a general formula (I):
(I)
in the general formula (I), b is an integer of 1-100, a, c and d are integers greater than or equal to 0, and a+c+d is an integer of 1-100;
R 1 is of the structure shown in the formula (II) or the 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 dispersing agent comprises the following steps:
(1) Adding a bottoming solvent into a reaction container provided with a mechanical stirrer and a condenser tube, and introducing nitrogen to deoxidize for 20 minutes; then, after 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, and after dropwise adding, carrying out heat preservation reaction, and detecting the reaction progress by infrared spectrum;
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 condenser pipe, and introducing nitrogen to deoxidize for 20 minutes; then, after stirring and heating to a certain temperature, slowly dripping a solution in which maleic anhydride and comonomer are dissolved by using one constant-pressure dropping funnel, slowly dripping an initiator by using the other constant-pressure dropping funnel, and after dripping, carrying out heat preservation reaction, and detecting the reaction progress by infrared spectrum;
in the step (1), the dropwise adding time is 1-5 hours, the heat preservation reaction time is 1-3 hours, and the reaction temperature is 40-150 ℃; obtaining maleic anhydride copolymer after reaction;
(2) Adding metered alkylamine or alkoxy polyether amine and a catalyst into the maleic anhydride copolymer obtained in the step (1), regulating to a proper temperature, continuing to react, monitoring the reaction progress through infrared spectrum, and removing the solvent in vacuum after the reaction is finished to obtain a yellowish product, namely the obtained dispersant product;
the reaction time of the step (2) is 3-5 hours, and the reaction temperature is 80-150 ℃.
Wherein the solvent in the step (1) is selected from one or more of water, alcohol solvents, ester solvents, ketone solvents, aromatic hydrocarbon solvents, 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 more than two of tertiary butanol, tertiary dodecyl mercaptan, mercaptoethanol, mercaptoacetic acid, isooctyl 3-mercaptopropionate and 2, 4-diphenyl-4-methyl-1-pentene; the use amount of the chain transfer agent is 1-10% of the total mass of the maleic anhydride and the comonomer.
Wherein the initiator is one or more than two of azodiisobutyronitrile, dibenzoyl peroxide, diethyl hexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite and potassium persulfate-sodium bisulfate; the usage amount of the initiator is 1-10% 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 1-10% of the total mass of maleic anhydride and comonomer.
Wherein the alkylamine is selected from one of dodecylamine, hexadecylamine and octadecylamine; the polyetheramine is selected from one of ethylene oxide polyetheramine, propylene oxide polyetheramine and ethylene oxide-propylene oxide copolymerized polyetheramine; the amount of the substance of the alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of the maleic anhydride.
The dispersing agent can be used as a carbon nano tube dispersing agent for preparing carbon nano tube dispersion liquid. The carbon nanotube dispersion liquid comprises carbon nanotubes, a dispersion solvent and the dispersing agent.
The invention is further illustrated by the following specific examples.
Example 1
200mL of dry butanone was added to a 1000mL three-necked round bottom flask, a mechanical stirrer and a reflux condenser were mounted, and nitrogen was purged for 20 minutes, then 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 initiator azobisisobutyronitrile and 1 g of chain transfer agent mercaptoethanol are dissolved in 200mL of anhydrous butanone, then transferred into a constant pressure dropping funnel, slowly added dropwise into a three-neck round bottom flask for reaction (about 2 hours after the dropwise addition), and the reaction is carried out for 2 hours after the dropwise addition.
After the polymerization was completed, 18.5 g of ethylenediamine and 1 g of triethylamine as a catalyst were added to the three-necked round-bottomed flask, and the temperature was raised to 100℃for reaction for 5 hours. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 1. The infrared spectrum of the dispersant 1 is shown in FIG. 1.
Example 2
200mL of xylene was added to a 1000mL three-necked round bottom flask, equipped with a mechanical stirrer and reflux condenser, deoxygenated by introducing nitrogen for 20 minutes, and then 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 benzoyl peroxide as an initiator and 1 g of mercaptoethanol as a chain transfer agent are dissolved in 200mL of xylene, then transferred into a constant pressure dropping funnel, slowly added into a three-neck round bottom flask in a dropwise manner for reaction (about 1 hour after the dropwise addition is completed), and the reaction is carried out for 2 hours after the dropwise addition is completed.
After the polymerization was completed, 48.2 g of hexadecylamine, 1 g of triethylamine as a catalyst was added to the three-necked round bottom flask, and the temperature was raised to 130℃for reaction for 5 hours. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 2. The infrared spectrum of the dispersant 2 is shown in FIG. 2.
Example 3
200mL of anhydrous toluene was added to a 1000mL three-necked round bottom flask, a mechanical stirrer and a reflux condenser were mounted, and nitrogen was purged for 20 minutes, then the mechanical stirrer was turned on and heated to 100 ℃. 9.8 g of maleic anhydride, 21.1 g of 4-vinylpyridine, 11.1 g of N-vinylpyrrolidone, 2 g of diethyl hexyl peroxide serving as an initiator and 1 g of mercaptoethanol serving as a chain transfer agent are dissolved in 200mL of anhydrous butanone, and then the mixture is slowly added dropwise into a three-necked round bottom flask through a constant pressure dropping funnel to carry out reaction (about 2 hours after the dropwise addition is completed), and the reaction is carried out for 2 hours after the dropwise addition is completed.
After the polymerization was completed, 26.9 g of octadecylamine, 1 g of 4-dimethylaminopyridine as a catalyst was added to the three-necked round bottom flask, and the temperature was raised to 120℃for reaction for 5 hours. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 3. The infrared spectrum of this dispersant 3 is shown in FIG. 3.
Example 4
200mL of dry butanone was added to a 1000mL three-necked round bottom flask, a mechanical stirrer and a reflux condenser were mounted, and nitrogen was purged for 20 minutes, then 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 diethyl hexyl peroxydicarbonate serving as an initiator and 1 g of tert-dodecyl mercaptan serving as a chain transfer agent are dissolved in 150mL of anhydrous butanone, and then transferred into a constant pressure dropping funnel, slowly dropped into a three-necked round bottom flask for reaction (about 2 hours after the dropping is completed), and the reaction is carried out for 2 hours after the dropping is completed.
After the polymerization was completed, 200 g of ethylene oxide polyether amine (mn=2000), 1 g of triethylamine as a catalyst was added to the three-necked round bottom flask, and the temperature was raised to 100 ℃ for reaction for 5 hours. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 4. The infrared spectrum of the dispersant 4 is shown in FIG. 4.
Example 5
200mL of dry butanone was added to a 1000mL three-necked round bottom flask, a mechanical stirrer and a reflux condenser were mounted, and nitrogen was purged for 20 minutes, then 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 diethyl hexyl peroxydicarbonate as an initiator and 1 g of tert-dodecyl mercaptan as a chain transfer agent are dissolved in 200mL of anhydrous butanone, and then transferred into a constant pressure dropping funnel, slowly dropped into a three-necked round bottom flask for reaction (about 2 hours after the dropping), and the reaction is carried out for 2 hours after the dropping is completed by heat preservation.
After the polymerization was completed, 300 g of propylene oxide polyether amine (mn=3000), 1 g of triethylamine as a catalyst, and the temperature was raised to 100 ℃ to react for 5 hours were added to the three-necked round bottom flask. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 5. The infrared spectrum of this dispersant 5 is shown in FIG. 5.
Example 6
200mL of dry butanone was added to a 1000mL three-necked round bottom flask, a mechanical stirrer and a reflux condenser were mounted, and nitrogen was purged 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 diethyl hexyl peroxide serving as an initiator and 1 g of tert-dodecyl mercaptan serving as a chain transfer agent are dissolved in 200mL of anhydrous butanone, and then transferred into a constant pressure dropping funnel, slowly dropped into a three-necked flask for reaction (about 2 hours after the completion of the dropping), and the reaction is carried out for 2 hours after the completion of the dropping.
After the polymerization was completed, 300 g of ethylene oxide-propylene oxide copolyetheramine (mn=3000), 1 g of triethylamine as a catalyst, and the temperature was raised to 100 ℃ to react for 5 hours were added to a three-necked flask. And after the reaction is finished, removing the solvent in vacuum, and discharging the material when the material is hot to obtain the dispersing agent 6. The infrared spectrum of this dispersant 6 is shown in FIG. 6.
Application Performance test
The dispersing agent of the embodiment of the invention and the common dispersing agent on the market as a comparison example are adopted to disperse the carbon nano tube in an aqueous phase or an organic phase, after the dispersing, the viscosity of the slurry and the particle size of the carbon nano tube are tested, and the stability of the slurry after standing for a period of time is observed.
The dispersing 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 grinding is carried out for 4 hours at 25 ℃ and 2000 revolutions per minute, and finally the zirconium beads are filtered, so as to obtain carbon nano tube dispersion liquid.
The properties of the carbon nanotube dispersion were measured, and the measurement results are shown in table 1. As can be seen from table 1, the carbon nanotubes of the examples of the present invention have particle size values and slurry viscosity values lower than those of the comparative examples, both in the aqueous phase and the organic phase. After standing for 72 hours, the carbon nanotube dispersion liquid corresponding to each embodiment of the invention is a uniform solution, but the bottom of the carbon nanotube dispersion liquid corresponding to the comparative example is provided with a sediment, so that the dispersing agent of the embodiment of the invention has better dispersing effect on carbon nanotubes and excellent performance.
TABLE 1
The foregoing description is only illustrative of the present invention and is not intended to limit the scope of the invention, and all equivalent structures or equivalent processes or direct or indirect application in other related arts are included in the scope of the present invention.
Claims (10)
1. A dispersant, characterized in that: has a structure shown in a general formula (I):
in the general formula (I), b is an integer of 1 to 100, a=0, c and d are integers greater than 0, and a+c+d is an integer of 1 to 100;
R 1 is of the structure shown in the formula (II) or the 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 of preparing the dispersant of claim 1, comprising the steps of:
(1) Under the conditions of a solvent, a chain transfer agent and an initiator, carrying out copolymerization reaction on maleic anhydride and a comonomer to obtain a maleic anhydride copolymer; wherein the comonomer comprises 4-vinyl pyridine, N-vinyl pyrrolidone;
(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 producing a dispersant according to claim 2, wherein the solvent in the step (1) is selected from 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, 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 producing a dispersant according to claim 2, wherein the chain transfer agent is one or a mixture of two or more of t-butanol, t-dodecyl mercaptan, mercaptoethanol, mercaptoacetic acid, isooctyl 3-mercaptopropionate, 2, 4-diphenyl-4-methyl-1-pentene; the use amount of the chain transfer agent is 1-10% 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 azobisisobutyronitrile, dibenzoyl peroxide, diethyl hexyl peroxydicarbonate, potassium persulfate, ammonium persulfate, potassium persulfate-sodium hypophosphite, and potassium persulfate-sodium bisulfate; the usage amount of the initiator is 1-10% of the total mass of the maleic anhydride and the comonomer.
6. The method for preparing the dispersing agent 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 1-10% of the total mass of maleic anhydride and comonomer.
7. The method for preparing the dispersing agent according to claim 2, wherein the alkylamine is one selected from dodecylamine, hexadecylamine and octadecylamine; the polyetheramine is selected from one of ethylene oxide polyetheramine, propylene oxide polyetheramine and ethylene oxide-propylene oxide copolymerized polyetheramine; the amount of the substance of the alkylamine or polyetheramine is 0.5 to 1.5 times the amount of the substance of the maleic anhydride.
8. The method for preparing a dispersant according to claim 2, wherein the reaction time in the 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 in the step (2) is 3 to 5 hours and the reaction temperature is 80 to 150 ℃.
10. The use of the dispersant of claim 1 for preparing a carbon nanotube dispersion, wherein the carbon nanotube dispersion comprises carbon nanotubes, a dispersing solvent, and the dispersant of claim 1.
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