CN116655859A - Amphiphilic polymer with comb-shaped structure and preparation method and application thereof - Google Patents
Amphiphilic polymer with comb-shaped structure and preparation method and application thereof Download PDFInfo
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- CN116655859A CN116655859A CN202310628881.0A CN202310628881A CN116655859A CN 116655859 A CN116655859 A CN 116655859A CN 202310628881 A CN202310628881 A CN 202310628881A CN 116655859 A CN116655859 A CN 116655859A
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- Prior art keywords
- vinyl
- monomer
- amphiphilic polymer
- solution
- initiator
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000178 monomer Substances 0.000 claims abstract description 49
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 36
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 36
- 229920000570 polyether Polymers 0.000 claims abstract description 18
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- DVATZODUVBMYHN-UHFFFAOYSA-K lithium;iron(2+);manganese(2+);phosphate Chemical compound [Li+].[Mn+2].[Fe+2].[O-]P([O-])([O-])=O DVATZODUVBMYHN-UHFFFAOYSA-K 0.000 claims abstract description 12
- 239000002270 dispersing agent Substances 0.000 claims abstract description 10
- 150000003254 radicals Chemical class 0.000 claims abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 230000009471 action Effects 0.000 claims abstract description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- -1 pyrrolidinonyl Chemical group 0.000 claims description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-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
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- PABGQABTFFNYFH-UHFFFAOYSA-N 2-methyl-n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C(C)=C PABGQABTFFNYFH-UHFFFAOYSA-N 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000007774 positive electrode material Substances 0.000 claims description 3
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 claims description 2
- WDFFWUVELIFAOP-UHFFFAOYSA-N 2,6-difluoro-4-nitroaniline Chemical compound NC1=C(F)C=C([N+]([O-])=O)C=C1F WDFFWUVELIFAOP-UHFFFAOYSA-N 0.000 claims description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- 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 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- HOZLHJIPBBRFGM-UHFFFAOYSA-N n-dodecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C(C)=C HOZLHJIPBBRFGM-UHFFFAOYSA-N 0.000 claims description 2
- XQPVIMDDIXCFFS-UHFFFAOYSA-N n-dodecylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C=C XQPVIMDDIXCFFS-UHFFFAOYSA-N 0.000 claims description 2
- YRGCLADHMAKURN-UHFFFAOYSA-N n-hexadecyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)C(C)=C YRGCLADHMAKURN-UHFFFAOYSA-N 0.000 claims description 2
- BKWMQCLROIZNLX-UHFFFAOYSA-N n-hexadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCNC(=O)C=C BKWMQCLROIZNLX-UHFFFAOYSA-N 0.000 claims description 2
- CNWVYEGPPMQTKA-UHFFFAOYSA-N n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C=C CNWVYEGPPMQTKA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006053 organic reaction Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
- FFIUNPRXUCRYFU-UHFFFAOYSA-N tert-butyl pentaneperoxoate Chemical compound CCCCC(=O)OOC(C)(C)C FFIUNPRXUCRYFU-UHFFFAOYSA-N 0.000 claims description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 2
- 239000010405 anode material Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 5
- 238000000265 homogenisation Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000004134 energy conservation Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000009467 reduction Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 description 20
- 239000002002 slurry Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 9
- 230000002776 aggregation Effects 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000005054 agglomeration Methods 0.000 description 5
- 239000002033 PVDF binder Substances 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- 239000002041 carbon nanotube Substances 0.000 description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 description 3
- 239000006258 conductive agent Substances 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- 239000006230 acetylene black Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000005653 Brownian motion process Effects 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- PFYQFCKUASLJLL-UHFFFAOYSA-N [Co].[Ni].[Li] Chemical compound [Co].[Ni].[Li] PFYQFCKUASLJLL-UHFFFAOYSA-N 0.000 description 1
- HFCVPDYCRZVZDF-UHFFFAOYSA-N [Li+].[Co+2].[Ni+2].[O-][Mn]([O-])(=O)=O Chemical compound [Li+].[Co+2].[Ni+2].[O-][Mn]([O-])(=O)=O HFCVPDYCRZVZDF-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000006256 anode slurry Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005537 brownian motion Methods 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000006257 cathode slurry Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- QHGJSLXSVXVKHZ-UHFFFAOYSA-N dilithium;dioxido(dioxo)manganese Chemical compound [Li+].[Li+].[O-][Mn]([O-])(=O)=O QHGJSLXSVXVKHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention relates to the technical field of chemical industry, in particular to an amphiphilic polymer with a comb structure, which is prepared by random free radical solution copolymerization of a single-ended vinyl polyether monomer, a vinyl monomer with an acid group, other vinyl monomers and a (methyl) acrylamide monomer with a long-chain alkyl structure under the action of an initiator. Compared with the prior art, the invention has the beneficial effects that: the amphiphilic polymer developed by the invention is used as a dispersing agent, has the effects of good viscosity reduction and high dispersing efficiency in the homogenization of the anode material of the lithium iron (manganese) phosphate battery, and can effectively maintain the stability of the dispersing liquid, thereby greatly reducing the production cost and achieving the purposes of energy conservation and environmental protection.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to an amphiphilic polymer with a comb-shaped structure, and a preparation method and application thereof.
Background
The lithium ion battery mainly comprises a positive electrode, a negative electrode, a diaphragm and electrolyte. The positive electrode and the negative electrode are formed by mixing an active material, a conductive agent, a binder, and the like into a slurry, and then coating the slurry on a current collector. The negative electrode active material is usually a carbon material. The positive electrode active material is usually a lithium-containing compound, and the positive electrode active materials which are commercially applied on a large scale at present mainly comprise several types of lithium iron phosphate, lithium manganese iron phosphate, lithium manganate, ternary materials of lithium nickel cobalt manganate and lithium nickel cobalt aluminate. The lithium iron phosphate as the positive electrode has the characteristics of low cost, high safety and long cycle life, and is increasingly valued and applied on a large scale; lithium iron phosphate has been regarded as having a higher voltage plateau and energy density than lithium iron phosphate.
The lithium iron phosphate (LFP) and lithium manganese iron phosphate (LMFP) which are commercially used at present are basically obtained by jet milling spherical LFP and LMFP, the particle size of the nano-structure material is about 100-500 nm, and compared with the bulk and micron-sized electrode materials, the nano-structure material has the advantages of short transmission distance, large specific surface area, high reversible capacity, stable cycle performance, higher electron transmission speed and the like. Although nanoscale particles have a stronger electrolyte adsorption capacity than micron-sized particles, their surface energy due to their large specific surface area also makes them very susceptible to agglomeration. Meanwhile, the conductive agent also has larger specific surface area, is difficult to be completely dispersed in the glue solution, and brings inconvenience to processing. In the pulping process, the agglomeration and agglomeration cause uneven slurry dispersion, and the conductive agent cannot uniformly cover the active material, so that the conductivity of the positive electrode is reduced, and the capacity, the cycle performance and the consistency of the lithium ion battery are directly reduced. The agglomeration causes the adhesion of the slurry to be reduced during the coating process, increases the internal resistance of the battery, and the protruding portion is easily pressed to pierce the separator during the assembly process, thereby reducing the safety of the battery.
The solid content of the lithium iron (manganese) phosphate anode slurry used in the anode preparation process is usually 50-55wt%, when the solid content of the slurry is continuously improved, the viscosity of the slurry is greatly increased, the viscosity change in the storage process is large, the fluidity of the slurry is reduced, the construction difficulty is increased, and the electrical performance is reduced. The surfactant (dispersing agent comprising anionic surfactant and nonionic surfactant) is added into the lithium iron (manganese) phosphate slurry to disperse the small particles, so that the performance of the slurry is improved, and the small particles are prevented from agglomerating. However, the addition of the conventional dispersing agent generally has adverse effects on the performance of the battery, for example, the addition of the anionic surfactant only can generate salting-out effect, so that the peeling strength of the electrode is obviously reduced, and the stability of the slurry is poor; only adding nonionic surfactant can form micelle, which affects mobility of electrons and has poor conductivity of positive electrode.
At present, high molecular weight polyvinylpyrrolidone is generally used as a dispersing agent in industry to prepare corresponding dispersing liquid, but the dispersing efficiency of the dispersing agent is low, and the viscosity of a dispersing liquid product is high, so that the conductivity is poor. In order to reduce the viscosity of the anode material of the lithium iron (manganese) phosphate battery in the homogenization process, the solid content of the slurry has to be reduced by increasing the solvent consumption to meet the quality requirement of the product. Therefore, how to increase the solid content of the lithium (manganese) iron phosphate cathode slurry, reduce the viscosity of the slurry and maintain the fluidity and stability of the slurry is a great problem at present, and therefore, there is room for improvement.
Disclosure of Invention
In order to solve the problems mentioned in the background art, the present invention provides an amphiphilic polymer with a comb structure, which is prepared by copolymerizing a single-end vinyl polyether monomer, a vinyl monomer with an acid group, other vinyl monomers and a (meth) acrylamide monomer with a long-chain alkyl structure in a random free radical solution under the action of an initiator, wherein the corresponding structural formula is as follows:
wherein a, b, c, d is natural positive integer, R 1 is-H or-COOH, R 2 is-H or-CH 3 ，R 3 Is single-end amino polyether radical, R 4 Is phenyl, pyridyl or pyrrolidinonyl, R 5 Is long chain alkyl amino.
Preferably, the single-ended vinyl polyether monomer is synthesized by organic reaction of single-ended amine polyether and vinyl-containing anhydride in the presence of a polymerization inhibitor, wherein the vinyl-containing anhydride is selected from any one of methacrylic anhydride, acrylic anhydride and maleic anhydride.
Preferably, the vinyl monomer of the acidic group is selected from any one of acrylic acid, methacrylic acid, itaconic acid, vinyl phosphonic acid, 2-hydroxyethyl methacrylate phosphate.
Preferably, the other vinyl monomer is selected from any one of styrene, vinyl pyridine and N-vinyl pyrrolidone.
Preferably, the (meth) acrylamide monomer having a long chain alkyl structure is selected from any one of N-dodecyl acrylamide, N-hexadecyl acrylamide, N-octadecyl acrylamide, N-dodecyl methacrylamide, N-hexadecyl methacrylamide and N-octadecyl methacrylamide.
Preferably, the solvent used in the random radical solution copolymerization is selected from any one of methanol, ethanol, isopropanol, N-methylpyrrolidone, ethylene glycol butyl ether, diethylene glycol butyl ether, ethylene glycol methyl ether, diethylene glycol methyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol butyl ether, dipropylene glycol butyl ether, PPG200, PEG200, N-dimethylformamide and dimethyl sulfoxide.
Preferably, the initiator is azo initiator or peroxy compound initiator;
the azo initiator is selected from any one of azodiisobutyronitrile and azodiisoheptonitrile;
the peroxide compound initiator is selected from any one of benzoyl peroxide, lauroyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyvalerate, cumene hydroperoxide, tert-butyl hydroperoxide, dicumyl peroxide, di-tert-butyl peroxide and di-tert-amyl peroxide.
Preferably, if the total mass of the polymerized monomers is 100 parts, the amount of the single-ended vinyl polyether monomer is 1 to 30 parts, the amount of the vinyl monomer having an acidic group is 1 to 20 parts, the amount of the other vinyl monomer is 1 to 70 parts, and the amount of the (meth) acrylamide monomer having a long chain alkyl structure is 1 to 50 parts.
The invention also provides a preparation method of the amphiphilic polymer, which comprises the following steps:
s1, preparing materials dropwise added in batches
The materials comprise a solution A and a solution B;
the solution A consists of all monomers, part of initiator and part of solvent;
the solution B consists of the rest of the initiator and the rest of the solvent;
s2, carrying out polymerization reaction
Adding part of solvent into a reaction bottle, heating and refluxing for 30-60min, dripping solution A for 1-3h, refluxing for 2-3h after dripping, dripping half of solution B for 1-2h after dripping, continuously dripping the rest of solution B, refluxing for 2-5h after dripping, and removing the low boiling point solvent to obtain the amphiphilic polymer solution.
The invention also provides application of the amphiphilic polymer serving as a dispersing agent in the anode material of the lithium iron phosphate (manganese) battery.
Compared with the prior art, the invention has the beneficial effects that:
1. the macromolecular main chain of the amphiphilic polymer synthesized by the invention has strong polar groups carboxyl or phosphate (phosphonic) groups which can be adsorbed on the surfaces of carbon nano-tube particles, lithium iron phosphate particles and acetylene black particles, and the side chains are long-chain alkyl groups and polyether groups which have good compatibility with methyl pyrrolidone solvent, so that the inorganic particles with the corresponding particles adsorbed with the dispersing agent on the surfaces can be well dispersed in the methyl pyrrolidone solvent through the steric hindrance effect, and the mutual collision among the particles caused by Brownian motion is prevented, and the aggregation and agglomeration among the particles are caused. Therefore, the dispersing agent of the amphiphilic comb polymer can achieve the purposes that particles are easy to disperse and the formed dispersing liquid has good dispersion stability.
2. The amphiphilic polymer developed by the invention is used as a dispersing agent, has the effects of good viscosity reduction and high dispersing efficiency in the homogenization of the anode material of the lithium iron (manganese) phosphate battery, and can effectively maintain the stability of the dispersing liquid, thereby greatly reducing the production cost and achieving the purposes of energy conservation and environmental protection.
Drawings
FIG. 1 is an infrared plot of the polymer obtained in example 1;
FIG. 2 is an infrared plot of the polymer obtained in example 2;
FIG. 3 is an infrared plot of the polymer obtained in example 3.
Detailed Description
Raw materials are commercially available for use in the present invention unless otherwise specified.
Preparation example 1
Synthesis of monomer mixtures with single-ended vinyl polyethers and methacrylic acid
200g of single-ended amine polyether M2070 and 0.07 g of polymerization inhibitor para-hydroxyanisole are added into a reaction bottle, and after being stirred uniformly, 15.4g of methacrylic anhydride is added dropwise under stirring at room temperature, the temperature is kept to be not more than 100 ℃, after the dropwise addition is completed, the reaction is continued for 1h at 100 ℃, and a mixture of single-ended vinyl polyether monomer and methacrylic acid monomer is obtained, and the mixture is refrigerated and stored at 4 ℃.
Preparation example 2
Synthesis of (meth) acrylamide monomer and methacrylic acid monomer mixture having long-chain alkyl structure
269.5g of octadecylamine, 0.16g of polymerization inhibitor p-hydroxyanisole and 106g of solvent N-methylpyrrolidone are added into a reaction bottle, after stirring and dissolving, 154g of methacrylic anhydride is dropwise added at room temperature under stirring, the temperature is kept at not more than 100 ℃, after the dropwise adding is completed, the reaction is continued for 1h at 100 ℃, and a mixture of (methyl) acrylamide monomer and methacrylic acid monomer with long-chain alkyl structure is obtained, and the mixture is refrigerated and stored at 4 ℃.
Example 1
S1, preparing materials dropwise added in batches
The materials comprise a solution A and a solution B;
the solution A consisted of 21.4g of the mixture of single-ended vinyl polyether monomer and methacrylic monomer obtained in preparation example 1, 11.2g of other vinyl monomers, 52.6g of the mixture of (meth) acrylamide monomer and methacrylic monomer having a long-chain alkyl structure obtained in preparation example 2, 90g of PEG200 and 0.3g of AIBN;
the solution B consists of 10g of isopropanol and 0.08g of AIBN;
s2, carrying out polymerization reaction
Adding 30g of isopropanol into a reaction bottle, heating and refluxing for 45 min, dropwise adding the solution A for 2h, carrying out reflux reaction for 2.5h after the completion of dropwise adding, then dropwise adding half of the solution B, carrying out reflux reaction for 1.5h after the completion of dropwise adding, continuing dropwise adding the rest of the solution B, carrying out reflux reaction for 3.5h after the completion of dropwise adding, and removing the low-boiling point solvent to obtain a solution consisting of the amphiphilic polymer and the PEG 200.
In this example, the vinyl monomer having an acidic group is methacrylic acid, and the other vinyl monomer is styrene.
Example 2
This embodiment differs from embodiment 1 in that: the other vinyl monomer was vinylpyridine and the amount added was 11.2g.
Example 3
S1, preparing materials dropwise added in batches
The materials comprise a solution A and a solution B;
the solution A consists of 21.4g of the mixture of single-ended vinyl polyether monomer and methacrylic acid monomer obtained in preparation example 1, 11.2g of other vinyl monomers, 52.6g of the mixture of (meth) acrylamide monomer with long-chain alkyl structure obtained in preparation example 2 and methacrylic acid monomer, 25g of ethylene glycol butyl ether, 25g of propylene glycol methyl ether and 1g of di-tert-amyl peroxide;
the solution B consists of 5g of ethylene glycol butyl ether, 5g of propylene glycol butyl ether and 0.4g of di-tert-amyl peroxide;
s2, carrying out polymerization reaction
Adding 15g of ethylene glycol butyl ether and 15g of propylene glycol methyl ether into a reaction bottle, heating and refluxing for 45 min, dripping solution A for 2h, refluxing for 2.5h after dripping, dripping half of solution B, refluxing for 1.5h after dripping, continuously dripping the rest of solution B, and refluxing for 3.5h after dripping to obtain a solution consisting of the amphiphilic polymer, the ethylene glycol butyl ether and the propylene glycol butyl ether.
In this example, the vinyl monomer having an acidic group is methacrylic acid, and the other vinyl monomer is N-vinylpyrrolidone.
In FIGS. 1-3, the wave number is 3410cm -1 To 3460cm -1 The range is the telescopic vibration absorption peak of carboxyl hydroxyl and the wave number is 1300cm -1 Is carboxyl hydroxyl deformation vibration absorption peak with wave number of 1665-1670 cm -1 Are carbonyl absorption peaks in carboxylic acids with hydrogen bond interactions, which indicate that carboxyl groups, which are acidic groups introduced by methacrylic monomer mer units through copolymerization, are present on the three macromolecular backbones. In the spectrogram, the wave number is 2922cm -1 The nearby strong absorption peaks are methyl and methine telescopic vibration absorption peaks with wave number of 1464cm -1 The absorption peaks are methyl and methine deformation vibration absorption peaks, and the wave number is 652cm -1 The left and right absorption peaks are long-chain alkyl- (CH) 2 ) n Typical backbone vibration absorption peak. These data indicate that long chain alkyl groups have been introduced into the polymer chain by copolymerization of N-octadecyl methacrylamide monomer with other monomers. In the three infrared spectrograms, the wave number is 1113-1117cm -1 The range has a strong absorption peak, which is typical of C-O-C bonds, indicating that polyether molecules have also been incorporated into the macromolecular chains of the present invention. The wavenumber present in FIG. 1 is 3036cm -1 A weak absorption peak, 1504cm -1 These are typical phenyl absorption peaks formed by the introduction of styrene monomer into the macromolecular chain at a strong absorption peak. Two typical absorption peaks are shown in FIG. 2 for the presence of pyridine ring groups in the molecular chain. One is that the CH stretching vibration absorption peak 3150cm in the five-membered ring is shown -1 ～3130cm -1 This is a weak shoulder and the other is at wave number 1464cm -1 Is a strong absorption peak of the five-membered ring. FIG. 3 shows that the typical infrared absorption peak showing the presence of pyrrolidone groups in the molecular chain has a wave number of 2954cm -1 CH telescopic vibration absorption peak in pyrrolidone ring of 1666cm -1 C=o stretching vibration absorption peak in pyrrolidone ring and 1300cm -1 C-N stretching vibration absorption peak of (C-N).
Lithium iron phosphate anode material battery homogenizing result and detection
Firstly, dispersing 2.3 parts by mass of PVDF and 60 parts by mass of NMP to prepare PVDF solution, then adding 0.22 part by mass of polymer samples obtained in examples 1-3 or polyvinylpyrrolidone (average molecular weight 58000) serving as a comparative example to uniformly disperse, continuously adding 95.9 parts by mass of lithium iron phosphate and 1 part by mass of acetylene black, using zirconium beads of 2-3mm, vibrating and grinding for 1h according to the weight ratio of the dispersion liquid to the zirconium beads of 1:1, adding 0.8 part by mass of carbon nano tube slurry to uniformly disperse, and testing fineness by a fineness meter and viscosity by a rotational viscosimeter. The dispersion was knife coated onto a PET film using a 100 μm bar, dried in an oven at 110 ℃ for 40 minutes to form a film, and the resistance of the film was measured using a four-probe tester. The results are shown in Table 1.
TABLE 1
Lithium manganese iron phosphate anode material battery homogenizing result and detection
Firstly, preparing PVDF solution by dispersing 2.35 parts by mass of PVDF and 34.5 parts by mass of NMP at high speed; then, 0.53 parts by mass of the polymer sample obtained in example 1-3 or comparative polyvinylpyrrolidone (average molecular weight 58000) was added to 6.49 parts by mass of NMP and dispersed uniformly, then 55 parts by mass of lithium iron manganese phosphate and 0.63 parts by mass of SP conductive carbon black were added together, zirconium beads of 2-3mm were used, and after shaking and grinding for 1 hour in a weight ratio of 1:1 of dispersion to zirconium beads, 0.5 parts by mass of carbon nanotube slurry was added and dispersed uniformly, and the fineness and rotational viscosimeter were used to test the viscosity, respectively. The dispersion was knife coated onto a PET film using a 100 μm bar, dried in an oven at 110 ℃ for 40 minutes to form a film, and the resistance of the film was measured using a four-probe tester. The results are shown in Table 1.
TABLE 2
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.
Claims (10)
1. The amphiphilic polymer with comb structure is characterized in that the polymer is prepared by random free radical solution copolymerization of single-ended vinyl polyether monomer, vinyl monomer with acid group, other vinyl monomer and (methyl) acrylamide monomer with long-chain alkyl structure under the action of initiator, and the corresponding structural formula is shown as follows:
wherein a, b, c, d is natural positive integer, R 1 is-H or-COOH, R 2 is-H or-CH 3 ，R 3 Is single-end amino polyether radical, R 4 Is phenyl, pyridyl or pyrrolidinonyl, R 5 Is long chain alkyl amino.
2. The amphiphilic polymer with comb structure according to claim 1, wherein the single-ended vinyl polyether monomer is synthesized by organic reaction of single-ended amine polyether and vinyl-containing anhydride in the presence of polymerization inhibitor, wherein the vinyl-containing anhydride is selected from any one of methacrylic anhydride, acrylic anhydride and maleic anhydride.
3. An amphiphilic polymer having a comb structure according to claim 1, wherein the vinyl monomer of the acidic group is selected from any one of acrylic acid, methacrylic acid, itaconic acid, vinyl phosphonic acid, 2-hydroxyethyl methacrylate phosphate.
4. An amphiphilic polymer having a comb structure according to claim 1, wherein the other vinyl monomer is selected from any one of styrene, vinyl pyridine, N-vinyl pyrrolidone.
5. An amphiphilic polymer having a comb structure according to claim 1, wherein the (meth) acrylamide monomer of long chain alkyl structure is selected from any one of N-dodecyl acrylamide, N-hexadecyl acrylamide, N-octadecyl acrylamide, N-dodecyl methacrylamide, N-hexadecyl methacrylamide, N-octadecyl methacrylamide.
6. The comb-structured amphiphilic polymer according to claim 1, wherein the solvent used in the random radical solution copolymerization is selected from any one of methanol, ethanol, isopropanol, N-methylpyrrolidone, ethylene glycol butyl ether, diethylene glycol butyl ether, ethylene glycol methyl ether, diethylene glycol methyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol butyl ether, dipropylene glycol butyl ether, PPG200, PEG200, N-dimethylformamide, and dimethyl sulfoxide.
7. An amphiphilic polymer having a comb structure according to claim 1, wherein the initiator is an azo-type initiator or a peroxy compound initiator;
the azo initiator is selected from any one of azodiisobutyronitrile and azodiisoheptonitrile;
the peroxide compound initiator is selected from any one of benzoyl peroxide, lauroyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyvalerate, cumene hydroperoxide, tert-butyl hydroperoxide, dicumyl peroxide, di-tert-butyl peroxide and di-tert-amyl peroxide.
8. The amphiphilic polymer with comb structure according to claim 1, wherein the amount of single-ended vinyl polyether monomer is 1-30 parts, the amount of vinyl monomer with acid group is 1-20 parts, the amount of other vinyl monomer is 1-70 parts, and the amount of (meth) acrylamide monomer with long chain alkyl structure is 1-50 parts, if the total mass of the polymerized monomers is 100 parts.
9. A process for the preparation of an amphiphilic polymer according to any one of claims 1 to 8, comprising the steps of:
s1, preparing materials dropwise added in batches
The materials comprise a solution A and a solution B;
the solution A consists of all monomers, part of initiator and part of solvent;
the solution B consists of the rest of the initiator and the rest of the solvent;
s2, carrying out polymerization reaction
Adding part of solvent into a reaction bottle, heating and refluxing for 30-60min, dripping solution A for 1-3h, refluxing for 2-3h after dripping, dripping half of solution B for 1-2h after dripping, continuously dripping the rest of solution B for 2-5h after dripping, and removing the low boiling point solvent to obtain the amphiphilic polymer solution.
10. Use of an amphiphilic polymer according to any one of claims 1-8 as a dispersant in a (manganese) iron lithium phosphate battery positive electrode material in a homogenate.
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