EP3749705A1 - Copolymers of ester and ether units, processes for producing same and uses thereof - Google Patents
Copolymers of ester and ether units, processes for producing same and uses thereofInfo
- Publication number
- EP3749705A1 EP3749705A1 EP19747279.8A EP19747279A EP3749705A1 EP 3749705 A1 EP3749705 A1 EP 3749705A1 EP 19747279 A EP19747279 A EP 19747279A EP 3749705 A1 EP3749705 A1 EP 3749705A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polymer
- lithium
- electrolyte
- mol
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 14
- 125000001033 ether group Chemical group 0.000 title claims description 5
- 229920001577 copolymer Polymers 0.000 title description 11
- 238000000034 method Methods 0.000 title description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 161
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 34
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011230 binding agent Substances 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 11
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 9
- 239000005518 polymer electrolyte Substances 0.000 claims abstract description 7
- 239000011245 gel electrolyte Substances 0.000 claims abstract description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 239000011591 potassium Substances 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 239000011734 sodium Substances 0.000 claims abstract description 4
- 239000003792 electrolyte Substances 0.000 claims description 35
- -1 lithium hexafluorophosphate Chemical compound 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 238000004132 cross linking Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000011244 liquid electrolyte Substances 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002134 carbon nanofiber Substances 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 8
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000002608 ionic liquid Substances 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- 239000004020 conductor Substances 0.000 claims description 7
- 239000007772 electrode material Substances 0.000 claims description 7
- 229910003002 lithium salt Inorganic materials 0.000 claims description 7
- 159000000002 lithium salts Chemical group 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000006230 acetylene black Substances 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 239000011262 electrochemically active material Substances 0.000 claims description 6
- 239000010954 inorganic particle Substances 0.000 claims description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 claims description 6
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 claims description 6
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 claims description 6
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 6
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 5
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical group C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004917 carbon fiber Substances 0.000 claims description 5
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims description 5
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 claims description 5
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007774 positive electrode material Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000004634 thermosetting polymer Substances 0.000 claims description 5
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 4
- IPOHWNJLUUURGY-UHFFFAOYSA-N (2,2,2-trifluoroacetyl)peroxyboronic acid Chemical compound OB(O)OOC(=O)C(F)(F)F IPOHWNJLUUURGY-UHFFFAOYSA-N 0.000 claims description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 3
- VFRGATWKSPNXLT-UHFFFAOYSA-N 1,2-dimethoxybutane Chemical compound CCC(OC)COC VFRGATWKSPNXLT-UHFFFAOYSA-N 0.000 claims description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- PPDFQRAASCRJAH-UHFFFAOYSA-N 2-methylthiolane 1,1-dioxide Chemical compound CC1CCCS1(=O)=O PPDFQRAASCRJAH-UHFFFAOYSA-N 0.000 claims description 3
- 206010006580 Bundle branch block left Diseases 0.000 claims description 3
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- 229910015040 LiAsFe Inorganic materials 0.000 claims description 3
- 229910012223 LiPFe Inorganic materials 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 239000002253 acid Chemical group 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000002041 carbon nanotube Substances 0.000 claims description 3
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000006352 cycloaddition reaction Methods 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010894 electron beam technology Methods 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000002240 furans Chemical class 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910021389 graphene Inorganic materials 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- BSFLBLPKMFBUKI-UHFFFAOYSA-M lithium 4,5-dicyanotriazole-4-carboxylate Chemical compound C(#N)C1(N=NN=C1C#N)C(=O)[O-].[Li+] BSFLBLPKMFBUKI-UHFFFAOYSA-M 0.000 claims description 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 150000003141 primary amines Chemical class 0.000 claims description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
- 238000007142 ring opening reaction Methods 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004073 vulcanization Methods 0.000 claims description 3
- 150000004862 dioxolanes Chemical class 0.000 claims description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 2
- CVVIFWCYVZRQIY-UHFFFAOYSA-N lithium;2-(trifluoromethyl)imidazol-3-ide-4,5-dicarbonitrile Chemical compound [Li+].FC(F)(F)C1=NC(C#N)=C(C#N)[N-]1 CVVIFWCYVZRQIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910010941 LiFSI Inorganic materials 0.000 claims 1
- 229920000451 Polycaprolactone-block-polytetrahydrofuran-block-polycaprolactone Polymers 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 5
- 125000004386 diacrylate group Chemical group 0.000 abstract description 2
- 239000011159 matrix material Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 20
- 230000001351 cycling effect Effects 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- 230000032258 transport Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 210000001787 dendrite Anatomy 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 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 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002105 nanoparticle Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910052748 manganese Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 3
- 238000012549 training 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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 229910010689 LiFePC Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 230000037427 ion transport Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007784 solid electrolyte Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0088—Composites
- H01M2300/0091—Composites in the form of mixtures
-
- 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
- H01M4/624—Electric conductive fillers
- H01M4/625—Carbon or graphite
-
- 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
Definitions
- the present application relates to the field of polymers and their uses in electrochemical applications, especially in lithium batteries. More particularly, the technology relates to the field of polymers for use as a solid polymer electrolyte (SPE), as a matrix for forming gel electrolytes or as a binder in electrode materials.
- SPE solid polymer electrolyte
- liquid electrolytes such as ethylene carbonate, propylene carbonate and diethyl carbonate, capable of effectively solubilizing and ionizing ionic salts such as LIPF6, LiTFSI and the like. LiFSI.
- these liquid electrolytes present significant safety and toxicity problems.
- alkaline metals such as lithium
- these metals can react with the liquid electrolytes, leading to the degradation of these electrolytes and, as a result, to a gradual decrease in the performance of the battery throughout its use.
- one of the major problems related to the use of these metals is the formation of dendritic structures that can lead to a violent short circuit between the electrodes when they manage to pierce the separator. This reaction may lead to ignition of the electrolyte, even to the point of battery explosion (see Guo, Y. et al., Advanced Materials, 29.29 (2017): 1-25).
- the degradation of the electrolyte can also generate reactive and toxic byproducts that, in the long term, expose the user to additional hazards, and in addition greatly reduce the capabilities of the electrochemical system.
- polymer structures capable of efficiently solvating Li + cations and which can be used as EPS.
- ethers such as tetrahydrofuran (THF), oxetane, 1,3-dioxolane, propylene oxide), esters (for example, caprolactone) and carbonates (e.g. ethylene carbonate, trimethylene carbonate and propylene carbonate).
- Polycaprolactone for example, has good ionic conductivity (see Lin, CK et al., Polymer 52.18 (201 1): 4106-4113). However, like polyethylene oxide, this polymer is semi-crystalline and crystallizes around 60 ° C, thus limiting its use at higher temperatures. By modifying its architecture and, mainly, introducing units other than caprolactone, it is possible to reduce the crystallinity of this polymer (see Mindemark, J. et al., Journal of Power Sources 298 (2015): 166-170) . In addition to having conductivities of more than 4.1 x 10 5 cm -1 , these copolymers based on of caprolactone units have high transport numbers (> 0.6).
- the SPEs may be in thermoplastic or thermosetting form.
- the crosslink density is high, they generally see their increased high voltage stability.
- thermosetting base examples include polyethers (other than polyethylene oxide), polyesters and polycarbonates.
- low molecular weight caprolactone oligomers are used for hybrid silicone ionic conductive electrolytes for applications in electrochromic systems (see Pereira, RFP et al., Electrochimica Acta 211 (2016): 804-813; Leones, R et al., Solar Energy Materials and Solar Cells 169 (2017): 98-106 and Fernandes, M. et al., ACS Applied Materials & Interfaces 3.8 (2011): 2953-2965).
- thermosetting polymers based on the tetrahydrofuran repeating unit are less good ionic conductors than their counterparts based on ethylene oxide units (see Alloin, F. et al., Electrochimica acta 43.10 (1998)). : 1199-1204).
- the present disclosure relates to a polymer comprising at least one ester repeating unit and an ether repeating unit, the polymer being of Formula I:
- x, y and z are natural numbers each independently selected such that the average molecular weight of the polymer is between 200 g / mol and 5,000,000 g / mol, where x> 1 and y + z>1;
- R1 and R2 are linear or branched substituents each independently selected from hydrogen, C1-2alkyl, C2-22alkenyl, C1-10alkoxyallyl, C1-10alkyl- (acrylate) and C1-10alkyl- (methacrylate);
- n, m, o and p are natural integers, where o is 1 to 10 and n, m and p are 0 to 10; and
- a and B are substituted or unsubstituted groups, each independently selected from alkyls, alkenyls, alkynyls, acetyls, alkoxyls, groups comprising epoxies, groups comprising furans, groups comprising primary amines, groups comprising maleimides, groups
- the polymer as defined herein is a thermoplastic polymer or a thermosetting polymer.
- At least one of the groups A, B, R 1 and R 2 comprises functionalities permitting the crosslinking of said polymer.
- the crosslinking is carried out by a reaction chosen from a radical-type reaction, a Diels-Alder reaction, a click chemistry, a reaction alkene hydrothiolization, ring opening reaction, vulcanization, cyclo addition, esterification and amidation.
- the crosslinking is carried out by UV irradiation, by heat treatment, by microwaves, under an electron beam, by gamma irradiation, or by X-ray irradiation.
- the crosslinking is carried out in the presence of a crosslinking agent, a thermal initiator, a catalyst, a plasticizer, or a combination of at least two thereof.
- compositions comprising at least one polymer as defined herein, and one or more liquid electrolytes, ionic salts, ionic liquids, polymers, inorganic particles, aprotic polar solvents, or additives.
- the present description relates to an electrolyte comprising a polymer as defined herein.
- the electrolyte is a solid polymer electrolyte (SPE) or a gel electrolyte.
- the electrolyte further comprises an ionic salt, an ionic liquid, a separator, an aprotic polar solvent, an additive or a combination of at least two thereof.
- the ionic salt is a lithium salt chosen from lithium hexafluorophosphate (LiPFe), lithium bis (trifluoromethanesulfonyl) imide (LiTFSI), lithium bis (fluorosulfonyl) imide (LiFSI), 2- lithium trifluoromethyl-4,5-dicyanoimidazolate (LiTDI), lithium 4,5-dicyano-1,2,3-triazolate (LiDCTA), lithium bis (pentafluoroethylsulfonyl) imide (LiBETI), tetrafluoroborate of lithium Lithium (L1BF4), lithium bis (oxalato) borate (LiBOB), lithium nitrate (UNO3), lithium chloride (LiCl), lithium bromide (LiBr), lithium fluoride (LiF), lithium lithium perchlorate (UCIO4), lithium hexafluoroarsenate (LiAsFe),
- the polar aprotic solvent is selected from ethylene carbonate (EC), diethyl carbonate (DEC), propylene carbonate (PC), dimethyl carbonate (DMC), methyl carbonate and ethyl (EMC), ⁇ -butyrolactone (g-BL), vinylene carbonate (VC), methyl butyrate (MB), g-valerolactone (g-VL), 1,2-dimethoxyethane ( DME), 1,2-diethoxyethane (DEE), 2-methyltetrahydrofuran, dimethylsulfoxide, formamide, acetamide, dimethylformamide, dioxolane, acetonitrile, propylnitrile, nitromethane, ethylmonoglyme, trimethoxymethane , dioxolane derivatives, sulfolane, methylsulfolane, propylene carbonate derivatives, tetrahydrofuran and mixtures thereof.
- EC ethylene carbonate
- the present disclosure relates to an electrode material comprising an electrochemically active material and a polymer as defined herein.
- the polymer is a binder.
- the present disclosure relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein at least one of the negative electrode, the positive electrode and the electrolyte comprises a polymer such as 'here defined.
- the positive electrode comprises an electrochemically active electrode positive material and a binder, optionally an electronically conductive material, or a combination thereof.
- the binder comprises a polymer as defined herein.
- the conductive material is selected from carbon black, Ketjen TM carbon, acetylene black, graphite, graphene, carbon nanotubes, and carbon fibers (such as carbon nanofibers, or VGCF formed in the gas phase), or a combination of at least two thereof.
- the present description refers to an electrochemical accumulator comprising at least one electrochemical cell as defined herein.
- the electrochemical accumulator is selected from a lithium battery, a sodium battery, a potassium battery and a lithium-ion battery.
- Figure 1 shows the stability cycling results of a battery, according to one embodiment, where the discharge capacity and the efficiency were recorded: (A) at a charge / discharge rate of C / 24 for First 5 cycles then C / 2 at a temperature of 50 ° C; and (B) at a charge / discharge rate of C / 5 at a temperature of 50 ° C, as described in Example 4 (a).
- Figure 2 shows the discharge capacity results as described in Example 4 (a), and at different charge / discharge rates and at different battery temperatures according to one embodiment.
- Figure 3 shows the stability cycling results as described in Example 4 (a) of a battery according to one embodiment.
- Figure 4 shows the results of cyclic voltammetry as described in Example 4 (b) of a symmetrical stack according to one embodiment.
- alkyl refers to saturated hydrocarbon groups having 1 to 21 carbon atoms, including linear or branched alkyl groups. Non-limiting examples of alkyls may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, tert-butyl, sec-butyl, isobutyl and the like.
- C 1 -C alkyl refers to an alkyl group ranging from the number 1 to the indicated number "n" of carbon atom (s).
- alkenyl refers to unsaturated hydrocarbons including at least one double bond between two carbon atoms.
- alkenyl groups include vinyl, allyl, 1-propen-2-yl, 1-buten-3-yl, 1-buten-4-yl, 2-buten-4-yl, 1 -pentene, 5-yl, 1, 3-pentadien-5-yl, and other similar groups.
- C2-C n alkenyl refers to an alkenyl group having from 2 to the indicated "n" number of carbon atom (s).
- alkynyl refers to unsaturated hydrocarbons including at least one triple bond between two carbon atoms.
- alkynyl groups include ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 2-butyn-4-yl, 1-pentyn-5-yl, 1,3-pentadiyl, and the like. 5-yl, and other similar groups.
- C2-C n alkynyl refers to an alkynyl group having from 2 to the indicated "n" number of carbon atom (s).
- alkoxy refers to an alkyl group to which an oxygen atom is attached, the latter being between two carbon atoms.
- alkoxy includes both substituted and unsubstituted alkoxy groups.
- Representative alkoxy groups include groups having 1 to about 10 carbon atoms, for example, methoxy, ethoxy, isopropyloxy, propoxy, butoxy, pentoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, and the like.
- substituted when included in combination with a moiety, refers to a moiety where at least one hydrogen atom has been replaced by a suitable substituent. These substituents may also be substituted if permissible, for example, if it contains an alkyl, alkoxy, alkenyl, alkynyl, etc. group.
- copolymers including both ethers and esters repeating units introducing defects in the repeating structure of the copolymer and thus leading to a decrease in crystallinity as compared to the homopolymers used alone.
- These copolymers make it possible to obtain functional SPEs at room temperature, by combining the good electrochemical and physicochemical properties of the ether and ester repeating units. These properties are also useful when the copolymers described here are used in the composition of electrolyte gel matrices, composites based on the addition of nanoparticles or as binders in electrodes.
- the polymers of the present application possess high numbers of transport in comparison with the polyethylene oxide generally used in the intended applications.
- the present application therefore describes copolymers possessing low crystallization temperatures, very low glass transitions (TV) and high numbers of transport, which is desirable for the efficient operation of SPEs at room temperature.
- the copolymers described herein may be crosslinked by different stimuli to form, for example, thermosetting polymers having high mechanical properties, being resistant and preventing the formation of dendrites.
- This mechanical strength can also be enhanced by the addition of nanoparticles such as S1O2, Al2O3, PO2 or any other appropriate nanoparticles.
- These crosslinked polymers can also be used as a "hard" polymer gel base when their three-dimensional network is impregnated with liquid electrolytes and / or ionic liquids in order to increase the ionic conductivity of the polymer while retaining superior mechanical properties that can prevent the formation of dendrites.
- the present application thus describes how it is possible to replace the gels conventionally used in lithium-ion batteries, whose weak mechanical properties can not prevent the formation of such dendrites and whose main non-ionic conductive structure involves the use of a large amount of liquid electrolyte.
- the present disclosure relates to a polymer comprising at least one ester repeating unit and an ether repeating unit.
- the polymer is represented by Formula I:
- Formula I in which: x, y and z are natural numbers each independently selected so that the average molecular weight of the polymer is between 200 g / mol and 5,000,000 g / mol; x>1; y + z>1;
- R1 and R2 are linear or branched substituents each independently selected from hydrogen, C1-2alkyl, C2-22alkenyl, C1-10alkoxyallyl,
- n, m, o and p are natural whole numbers representing the average number of units in the polymer; o is from 1 to 10; n, m and p are from 0 to 10; and A and B are substituted or unsubstituted groups each independently selected from alkyls, alkenyls, alkynyls, acetyls, alkoxyls, groups comprising epoxies, groups comprising furans, groups comprising primary amines, groups comprising maleimides, groups comprising acrylates and acid groups.
- the monomers before polymerization used to form the ether units may be, for example, ethylene oxide, propylene oxide, tetrahydrofuran, oxymethylene, trimethylene oxide, trioxymethylene allyl ether and glycidyl ether, and 3,4-epoxy-1-butene.
- R 1 is hydrogen and n is 3.
- the monomers before polymerization used to form the ester units may be, for example, 1,4-butylene adipate, 1,3-propylene succinate, ethylene adipate, glutarate or 1,3-propylene, and ethylene succinate.
- the ester units can be obtained via the opening of lactones such as ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone and ⁇ -caprolactone.
- they can be obtained by opening a lactide or a glycolide.
- o is between 2 and 4 and p between 2 and 4.
- m is between 0 and 4, and R2 is chosen from hydrogen and methyl.
- F3 ⁇ 4 is hydrogen and m is 4.
- A is an acrylate group.
- B is an acrylate group.
- a and B are acrylate groups.
- R 1 is hydrogen, n is 3, R 2 is hydrogen, m is 4, and A and B are acrylate groups.
- R 1 is hydrogen, n is 3, R 2 is hydrogen, m is 4, z is 0, and A and B are acrylate groups.
- the polymer is represented by Formula
- the polymer of Formula II can be prepared by a polymerization process as illustrated in Scheme 1:
- the average molecular weight of the polymer of formula I is between 200 g / mol and 5,000,000 g / mol, particularly between 200 g / mol and 1,000,000 g / mol, more particularly between 200 g / mol and mol and 500 000 g / mol, more particularly between 400 g / mol and 100 000 g / mol and ideally between 400 g / mol and 20 000 g / mol, upper and lower limits included.
- the average molecular weight of the polymer of Formula II is between 200 g / mol and 5,000,000 g / mol, particularly between 200 g / mol and 1,000,000 g / mol, more particularly between 200 g and 500,000 g / mol, more particularly between 400 g / mol and 100,000 g / mol and ideally between 400 g / mol and 20,000 g / mol, upper and lower limits included.
- the ester and ether repeating units can be chained alternately, randomly or blockwise.
- the ester and ether repeating units are each attached to a polymer in a configuration selected from linear, star and branched configurations.
- the polymer is a branched or hyperbranched polymer including comb polymers and dendritic polymers.
- the polymer is a star polymer and the linear chains of said star polymer are of length and homogeneous structure, alternatively they are of heterogeneous length and structure.
- the polymer of the present description can both have in its structure, one or more ionic conducting segment (s) and one or more function (s) that can lead to the controlled crosslinking of the polymer.
- the polymer further comprises functionalities allowing its controlled crosslinking under different external stimuli.
- at least one of the groups A, B, R 1 and R 2 includes functionalities for crosslinking said polymer.
- the crosslinking makes it possible, for example, to obtain a three-dimensional structure that is very resistant to high voltages, also making it possible to prevent the formation of dendrites.
- the selected repeating units can give the polymer a high transport number.
- the crosslinking can be carried out by a reaction chosen from a radical-type reaction, a Diels-Alder reaction, a click chemistry, an alkene hydrothiolization reaction, a ring opening reaction, a vulcanization, a cyclo addition. , esterification and amidation.
- the crosslinking is carried out by UV irradiation, by heat treatment, by microwaves, under an electron beam, by gamma irradiation, or by X-ray irradiation.
- Crosslinking can also be carried out in the presence, in the presence of in addition, a crosslinking agent, a thermal initiator, a UV initiator, a catalyst, a plasticizer such as tetraethylene glycol dimethyl ether (or tetraglyme), poly (ethylene glycol) dimethyl ether (PEGDME and such as conventional liquid electrolytes, molten salt electrolytes (ionic liquid) or a combination of at least two thereof.
- the UV crosslinking agent is 2,2-dimethoxy-2-phenylacetophenone (Irgacure 651).
- said polymer is a thermoplastic polymer or a thermosetting polymer.
- said polymer may be included in a composition comprising at least one polymer as defined herein, and one or more electrolytes liquids, ionic salts, ionic liquids, polymers, inorganic particles, aprotic polar solvents, or additives.
- said polymer may be included in an electrolyte such as a solid electrolyte or gel.
- an electrolyte such as a solid electrolyte or gel.
- the polymer described herein may further comprise a liquid electrolyte, an ionic salt, an ionic liquid, another polymer, a separator, a single-ion polymer, inorganic particles, a polar aprotic solvent, an additive or a combination of at least two thereof.
- a liquid electrolyte such as a solid electrolyte or gel
- the polymer described herein may further comprise a liquid electrolyte, an ionic salt, an ionic liquid, another polymer, a separator, a single-ion polymer, inorganic particles, a polar aprotic solvent, an additive or a combination of at least two thereof.
- the electrolyte is a solid polymer electrolyte (SPE) that can be used in an electrochemical cell or an electrochemical accumulator, for example, an "all solid" type electrochemical accumulator.
- the electrolyte is a gel electrolyte.
- the polymer of the present description may further have in its structure one or more function (s) that can lead to its grafting on the surface of one or more element (s) of the positive electrode or the negative electrode or on the surface of solid elements contained in the SPE.
- Non-limiting examples of separators may include polyethylene (PE), polypropylene (PP), cellulose, polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF) and polypropylene-polyethylene-polypropylene membranes (PP / PE / PE).
- PE polyethylene
- PP polypropylene
- cellulose cellulose
- PTFE polytetrafluoroethylene
- PVdF polyvinylidene fluoride
- PP / PE / PE polypropylene-polyethylene-polypropylene membranes
- the ionic salt may be a lithium salt.
- lithium salts include lithium hexafluorophosphate (LiPFe), lithium bis (trifluoromethanesulfonyl) imide (LiTFSI), lithium lithium bis (fluorosulfonyl) imide (LiFSI), lithium 2-trifluoromethyl-4,5-dicyanoimidazolate (LiTDI), lithium 4,5-dicyano-1,2,3-triazolate (LiDCTA), lithium lithium bis (pentafluoroethylsulfonyl) imide (LiBETI), lithium tetrafluoroborate (L1BF4), lithium bis (oxalato) borate (LiBOB), lithium nitrate (UNO3), lithium chloride (LiCl), lithium bromide, lithium (LiBr), lithium fluoride (LiF), lithium perchlorate (UCIO4), lithium hexafluoroarsenate (L
- LiPFe
- Non-limiting examples of aprotic polar solvents include ethylene carbonate (EC), diethyl carbonate (DEC), propylene carbonate (PC), dimethyl carbonate (DMC), methyl and ethyl carbonate (EMC), vinylene carbonate (VC), methyl butyrate (MB), ⁇ -butyrolactone (g-BL), g-valerolactone (g-VL), 1,2-dimethoxyethane (DME), 1,2-diethoxyethane (DEE), 2-methyltetrahydrofuran, dimethylsulfoxide, formamide, acetamide, dimethylformamide, dioxolane, acetonitrile, propylnitrile, nitromethane, ethylmonoglyme, trimethoxymethane, derivatives thereof of dioxolane, sulfolane, methylsulfolane, propylene carbonate derivatives, tetrahydrofuran and mixtures thereof.
- EC
- the concentration of the polymer in the electrolyte composition is between 5% and 100% by weight, between 10% and 100% by weight, between 20% and 100% by weight, between 30% and 100% by weight. by weight, between 40% and 100% by weight, between 50% and 100% by weight, between 60% and 100% by weight, between 75% and 100% by weight, and between 90% and 100% by weight, upper and lower included.
- the present application also provides an electrode material comprising an electrochemically active material and a polymer as defined herein.
- the binder comprises a polymer as described herein.
- the polymer as described herein is present in the electrode material as a coating of particles of electrochemically active material.
- the present application also provides an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein at least one of the negative electrode, the positive electrode and the electrolyte comprises a polymer of the present application.
- the polymer is present in the electrolyte, or in one of the positive and negative electrodes, or in one of the electrodes and in the electrolyte.
- the electrochemical cell comprises the electrolyte of the present application.
- the negative electrode is lithium.
- the polymer of the present disclosure may be combined with various inorganic materials to form composites.
- the inorganic particles may be inactive such as titanium dioxide (T1O2), silicon dioxide (S102) and aluminum oxide (Al2O3).
- the inorganic particles may be active, such as, for example, Lio.33Lao.557TiO3 (LLTO) lithium and lanthanum titanate, L7La3Zr20i2 (LLZO) lanthanum and lithium zirconate, and Li6.75La3Zn.75Tao.25O12 ( LLZTO).
- the functional properties of the polymer of the present description make it possible to graft it onto electrochemically active or inactive micro or nanoparticles to increase the ionic conductivity / polymer transport number and / or to increase the mechanical properties of the final composite.
- the positive electrode comprises a positive electrode material, which comprises an electrochemically active material, for example, in the form of a particle.
- electrochemically active positive electrode materials include lithium metal phosphates, complex oxides, such as LiM'PO4 where M 'is Fe, Ni, Mn, Co, or a combination thereof, UV3O8, V2O5, LiMn2O4, LiM2O, where M "is Mn, Co, Ni, or a combination thereof, Li (NiM "') O 2, where M""is Mn, Co, Al, Fe, Cr, Ti, or Zr, and combinations thereof.
- the positive electrode material may also further comprise an electronically conductive material, a binder, or a combination of both.
- the binder comprises a polymer as described herein.
- the polymer as described herein is present in the electrode material as a coating of particles of electrochemically active material.
- the electronically conductive material is selected from carbon black, Ketjen MC carbon, acetylene black, graphite, graphene, carbon nanotubes, and carbon fibers (such as carbon nanofibers). carbon or VGCF formed in the gas phase), or a combination of at least two thereof.
- the conductive material is a combination of acetylene black (such as Denka carbon HS100) and VGCF.
- the positive electrode material may be applied to a current collector (eg, aluminum or copper) to form the positive electrode.
- the positive electrode may be self-supporting.
- the current collector is made of aluminum coated with carbon.
- SPES membranes and / or electrodes comprising the polymer of the present disclosure can be continuously formed on roll-to-roll roll processing systems for large scale production.
- an electrochemical cell of the present application is included in an electrochemical accumulator.
- the electrochemical accumulator is selected from a lithium battery, a sodium battery, a potassium battery and a lithium-ion battery.
- the electrochemical accumulator is a lithium-ion battery.
- the electrochemical accumulators of the present application are used in mobile devices, for example mobile phones, cameras, tablets or laptops, in electric or hybrid vehicles, or in energy storage. renewable.
- the synthesis of the polymer was carried out in a 500 mL flask equipped with a magnetic bar by solubilizing 72 g of polycaprolactone-block-polytetrahydrofuran-block-polycaprolactone commercial molecular weight of 2,000 g / mol in 160 g of toluene.
- Acrylic acid (12.8 g), hydroquinone (0.4 g) and para-toluenesulfonic acid (1.6 g) were then added.
- the solution was stirred at 80 ° C under partial vacuum for 24 hours to extract the water by azeotropic distillation.
- the solvent was then evaporated using a rotary evaporator under vacuum at a temperature of 60 ° C for 2 hours.
- 200 g of a saturated aqueous solution of sodium bicarbonate and 100 ml of water were then added to the flask containing the polymer.
- the solvent was then evaporated on a rotary evaporator under vacuum at a temperature of 60 ° C for 2 hours. Subsequently, 200 g of a saturated aqueous solution of sodium bicarbonate and 100 ml of water were added to the flask containing the polymer. The solution was then vigorously stirred until the polymer was neutralized. Once the agitation stopped, the polymer was deposited at the bottom of the flask and the supernatant was decanted. Subsequently, the polymer was washed six times with nanopure water with vigorous stirring and was separated by centrifugation. The isolated polymer was dried using a rotary evaporator and then analyzed by FTIR, DSC and NMR.
- Example 2 Preparation of symmetrical batteries
- Polymer P1 (3 g) and Polymer P2 (3 g) were solubilized in a flask with 6 g of ethanol, 1.06 g of LiTFSI and 0.015 g of MC 651 Irgacide using a vortex . Subsequently, the solution was spread by the "Doctor blade" method on a stainless steel collector and then oven dried at a temperature of 75 ° C for 5 minutes before being inserted into a UV oven under inert nitrogen atmosphere with continuous flow. An intensity of 300 WPI was applied for 5 minutes, in order to induce the crosslinking of the polymer. Subsequently, the coating was left in the oven at a temperature of 75 ° C overnight prior to use.
- Polymer P1 (3 g) and 0.53 g of LiTFSI were solubilized in a determined amount (see Table 1) of a 1 M solution of LiTFSI in the previously prepared PC and 0.015 g of MC 651 a vortex. Subsequently, the solution was spread by the "Doctor blade" method on a stainless steel collector and then inserted in a UV oven under a continuous flow nitrogen atmosphere. An intensity of 300 WPI was applied for 5 minutes, in order to induce crosslinking. The coating was then used as it is without preheating to prevent evaporation of the PC. Table 1. Ion conductivity versus% by weight of propylene carbonate
- the SPE was prepared as described in Example 2 (a) by replacing the stainless steel current collector with a polypropylene film.
- the 80 ⁇ m thick SPE was then stripped off the polypropylene film with hexane, transferred to a PTFE sheet and covered with another sheet of PTFE.
- the PE sandwiched between two sheets of PTFE was then punched in order to obtain an SPE separator and assemble a lithium / SPE / lithium battery. The assembly was carried out in a glove box.
- the transport number of the polymer P1 was measured between two lithium electrodes. An average value of 0.71 on 4 batteries was obtained at a temperature of 50 ° C.
- Example 3 Preparation of LiFePO4 / SPE / Lithium Batteries a) Preparation of LiFePC> 4 / SPE / Lithium Batteries Comprising Polymer P1 Only The preparation is entirely carried out in an anhydrous chamber. 6 g of Polymer P1 were solubilized with 7.53 g of ethanol, 1.5 g of LiTFSI and 0.03 g of MC 651 Irgacide in a vortex bottle. 7.53 g of this solution was then transferred to a planetary centrifugal mixer container (THINKY TM type).
- a planetary centrifugal mixer container TINKY TM type
- the stock solution containing the polymer, the lithium salt and the UV initiator was spread by the "Doctor blade" method on the positive electrode.
- the positive electrode with the SPE coating thus obtained was oven dried at a temperature of 75 ° C for 5 minutes before being inserted into a UV oven under a continuous stream of nitrogen inert atmosphere. An intensity of 300 WPI has then applied for 5 minutes to induce crosslinking. The coating was then left in the oven at a temperature of 75 ° C overnight prior to use.
- the batteries were assembled with a metal lithium anode with a thickness of 45 ⁇ m.
- Two different formats of batteries were used: the button cell format and the bag stack format.
- the stock solution containing the polymer, the lithium salt and the UV initiator was spread by the "Doctor blade" method on the positive electrode.
- the positive electrode thus obtained with the SPE coating was oven dried at a temperature of 75 ° C for 5 minutes before being inserted into a UV oven under a continuous stream nitrogen atmosphere. An intensity of 300 WPI was then applied for 10 minutes to induce crosslinking. The coating was then left in the oven at a temperature of 75 ° C overnight prior to use.
- the batteries were assembled as described in Example 3 (a).
- Example 3 (a) Training and stability cycling Training cycling and battery stability tests prepared in Example 3 (a) were performed at different rates of charge and discharge as well as at different temperatures. The results are presented for a battery comprising a total charge of 4.39 mg / cm 2 , a SPE with a thickness of 20 ⁇ m and a positive electrode with a thickness of 25 ⁇ m.
- Figure 1A shows the cycling of a battery obtained in Example 3 (a).
- a stable capacity of 149 mAh / g was obtained with an efficiency close to 100%.
- the battery was then started in stability at C / 2 (charge / discharge) still at 50 ° C.
- a rapid decrease in capacity during the first 40 cycles was observed and then stabilized at around 100 mAh / g.
- the capacity was about 80 mAh / g while keeping a high efficiency of about 100%.
- Figure 1B shows the cycling of a battery obtained in Example 3 (a), at a rate of C / 5 (charge / discharge) and at 50 ° C. At this rate and this cycling temperature, a very high stability with an initial capacity of 137 mAh / g in the first cycle, a capacity of 123 mAh / g after the 257 th cycle and an efficiency of 99.9% were observed.
- Figure 2 shows the cycling at different charge / discharge rates and at different temperatures of a battery obtained in Example 3 (a).
- the box on the left and right respectively show the results of cycling at a temperature of 50 ° C and 25 ° C.
- a temperature of 50 ° C it was observed that the battery can be cycled to C / 5 while maintaining a high capacity of about 150 mAh / g. It has been observed that at speeds of C / 2 and 1 C, the capacity drops more strongly and becomes respectively less than 120 mAh / g and 40 mAh / g after 5 cycles.
- the battery For use at 25 ° C., it has been observed that the battery has a good capacity of about 145 mAh / g at C / 24, but falls below 40 mAh / g at a rate of C / 5. The battery was then tested for stability at a C / 10 speed and it was possible to observe that after more than 90 cycles the battery still held a capacity of about 100 mAh / g and tended to stabilize.
- Example 3 (b) Training cycling and battery stability tests prepared in Example 3 (b) were performed at different charge and discharge rates as well as at different temperatures. The results are presented for a battery comprising a total charge of 5.72 mg / cm 2 , a SPE with a thickness of 20 ⁇ m and a positive electrode with a thickness of 32 ⁇ m.
- Figure 3 shows the cycling of a battery obtained in Example 3 (b).
- a stable capacity of approximately 141 mAh / g was obtained with an efficiency close to 100%.
- the battery was then started in stability at C / 5 (charge / discharge) still at 50 ° C.
- C / 5 charge / discharge
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CA2994005A CA2994005A1 (en) | 2018-02-05 | 2018-02-05 | Ester and ether copolymer units, their fabrication process and their uses |
PCT/CA2019/050145 WO2019148299A1 (en) | 2018-02-05 | 2019-02-05 | Copolymers of ester and ether units, processes for producing same and uses thereof |
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JP2024514218A (en) * | 2021-07-29 | 2024-03-28 | エルジー エナジー ソリューション リミテッド | Gel polymer electrolyte and lithium secondary battery containing it |
CN114853621B (en) * | 2022-05-05 | 2023-08-01 | 华中科技大学 | Method for catalyzing primary amine-acrylic ester double-addition reaction and application thereof |
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