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  • C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
  • C09D181/02—Polythioethers; Polythioether-ethers
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  • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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  • H01M10/054—Accumulators with insertion or intercalation of metals other than lithium, e.g. with magnesium or aluminium
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  • H01M10/05—Accumulators with non-aqueous electrolyte
  • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
  • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
  • H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
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  • H01M4/04—Processes of manufacture in general
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  • H01M4/00—Electrodes
  • H01M4/02—Electrodes composed of, or comprising, active material
  • H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
  • H01M4/139—Processes of manufacture
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  • H01M4/00—Electrodes
  • H01M4/02—Electrodes composed of, or comprising, active material
  • H01M4/36—Selection of substances as active materials, active masses, active liquids
  • H01M4/38—Selection of substances as active materials, active masses, active liquids of elements or alloys
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  • H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
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  • H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
  • H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
  • H01M50/403—Manufacturing processes of separators, membranes or diaphragms
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  • H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
  • H01M50/409—Separators, membranes or diaphragms characterised by the material
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  • H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
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  • H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
  • H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
  • H01M50/46—Separators, membranes or diaphragms characterised by their combination with electrodes
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  • C08J2381/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen, or carbon only; Polysulfones; Derivatives of such polymers
  • C08J2381/02—Polythioethers; Polythioether-ethers
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  • H01M2300/00—Electrolytes
  • H01M2300/0017—Non-aqueous electrolytes
  • H01M2300/0065—Solid electrolytes
  • H01M2300/0082—Organic polymers
• • 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

• compositions comprising a polymer and inorganic particles, the polymer being the product of the reaction of at least one monomer comprising at least one polymerizable or crosslinkable function and of an organic compound comprising one or more group(s). ) SH.
• the liquid electrolytes used in lithium-ion batteries are flammable and slowly degrade to form a passivation layer on the surface of the lithium film or solid electrolyte interface (SEI for "solid electrolyte interface” or “solid electrolyte interphase” in English) irreversibly consuming lithium, which decreases the coulombic efficiency of the battery.
• SEI solid electrolyte interface
• solid electrolyte interphase solid electrolyte interphase
• solid electrolytes comprising a polymer, either as a solid polymer electrolyte or in a ceramic-polymer composite, generally require the presence of a polymerization initiator or initiator and polymerization conditions by heating or irradiation, which often requires additional equipment and longer manufacturing times.
• this initiator or initiator of polymerization will remain trapped inside the film, being able for example, thus to interfere with the electrochemical reaction during the cycling.
• the present technology relates to a composition
• a composition comprising a polymer and inorganic particles, the polymer being the product of the reaction of at least one monomer comprising at least one polymerizable or crosslinkable function and of an organic compound comprising one or SH group(s).
• the monomer is a compound of formula R 2 (X) m , where R 2 is an organic group, X is a polymerizable or crosslinkable group, and m is a number included in the range from 1 to 8 ; or the monomer is a macromonomer comprising at least one crosslinkable segment comprising units of formula R 2 (X) m and optionally a non-crosslinkable polymer segment.
• the non-crosslinkable polymer segment is present and is of Formula I:
• R is a hydrogen atom, a C 1 -C 10 alkyl group, or a -(CH2-OR a -R b ) group;
• R a is (CH 2 -CH 2 -O)j or (CH(CH 3 )-CH 2 -O)j;
• R b is a hydrogen atom or a C 1 -C 10 alkyl group; i is an integer selected from the range of 2 to 200,000; and j is an integer selected from the range of 0 to 100.
• X is a polymerizable or crosslinkable group comprising a double bond.
• the units of the polymer originating from the monomer comprise units of at least one of the formulas: in which R 2 , R 3 , R 4 and m are as previously defined, and in which — when attached to C(R 3 R 4 ) or CH 2 represents a bond with a hydrogen or sulfur atom of the organic compound , a terminal group, or another unit of the polymer, and represents a macromonomer when adjacent to R 2 .
• R 2 or the macromonomer comprising R 2 is chosen from C 2-12 linear or branched alkyl, alkylene oxide or poly(alkylene oxide), alkylene sulphide or poly(sulphide alkylene), siloxane or polysiloxane, and mono or polyaromatic, for example R 2 is chosen from C 2-12 linear or branched alkyl, alkylene oxide or poly(alkylene oxide), and phenyl groups.
• m is a number in the range 2 to 4.
• the monomer is chosen from branched poly(ethylene glycol) comprising acrylate groups at the end of the main and/or side chain and/or on the chains, poly(ethylene glycol) diacrylate, tetraacrylate of pentaerythritol, triethylene glycol divinyl ether, ethylene glycol dimethacrylate, and divinylbenzene.
• the units of the polymer originating from the monomer comprise units of at least one of the formulas:
• R 4 and — are as defined above, and p is a number other than zero.
• R 4 is H or C 1 -C 6 alkyl, preferably H or C 1 -C 3 alkyl, preferably H or methyl.
• the monomer content (before reaction) in the composition is in the range of about 1 wt% to about 95 wt%, or about 2 wt% to about 90 wt%. by weight, or from about 3% by weight to about 80% by weight, or from about 4% by weight to about 50% by weight, or from about 10% by weight to about 70% by weight, or d from about 20% by weight to about 65% by weight.
• the organic compound is of formula R 1 (SH) n , where R 1 is an organic group linking the SH group(s), and where n is a number in the range of 1 to 10, or the compound is a macromonomer comprising at least one segment comprising units of the formula R 1 (SH) n .
• the units of the polymer originating from the organic compound comprise units of at least one of the formulas: wherein R 1 and n are as previously defined and where — when attached to a sulfur atom represents a bond with another unit of the polymer, such as a unit from the monomer, and represents a macromonomer when adjacent to R 1 .
• R 1 or the segment comprising R 1 is chosen from linear or branched C 2-12 alkyl, linear or branched C 2-12 alkyl polyol ether or ester, alkylene oxide or poly(oxide alkylene) optionally comprising one or more sulfur atom(s) in a chain, alkylene sulfide or poly(alkylene sulfide), siloxane or polysiloxane, mono or poly-cycloalkyl or heterocycloalkyl, mono or poly-aromatic or fused or unfused heteroaromatics optionally comprising a linking atom, or a combination thereof.
• n is a number in the range of 1 to 4.
• the organic compound is chosen from 1-(2-mercaptoethoxy-2-ethoxyethyl-2-thioethyl)-2-pyrrolidone, 2,2'-
• polymer units from the organic compound include units of at least one of the formulas:
• the organic compound content in the composition (before reaction) is in the range of about 0.01% by weight to about 60% by weight, or about 0.05% by weight to about 50 wt%, or about 10 wt% to about 30 wt%, or about 15 wt% to about 40 wt%.
• the polymer of the composition is a polymer of random, block, or alternating configuration.
• the inorganic particles comprise an inorganic compound of the amorphous, ceramic or glass-ceramic type, for example, based on oxide, sulphide or oxysulphide, the inorganic compound being natural or synthetic.
• the inorganic particles comprise a natural or synthetic ceramic chosen from inorganic compounds of formulas MLZO (for example, M 7 La 3 Zr 2 O 12 , M (7-a) La 3 Zr 2 AlbO 12 , M (7-a) La 3 Zr 2 Ga b O 12 , M(7- a ) La 3 Zr (2-b) Ta b O 12 , and M(7- a ) La 3 Zr (2-b) NbbO 12 ); MLTaO (e.g., M 7 La 3 Ta 2 O 12 , MsLa 3 Ta 2 O 12 , and M6La 3 Ta1.5Y0.5O 12 ); MLSnO (e.g., M 7 LasSn2O 12 ); MAGP (for example, M 1+a Al a Ge 2-a (PO 4 )3); MATP (for example, M 1+a Al a Ti 2-a (PO 4 )3,); MLTiO (e.g., M 3a La (2/3-a )Ti
• M a GebP c S d O e MSiPS (for example, M a Si b P c S d such as M 10 SiP 2 S 12 ); MSiPSO (e.g., M a Si b P c S d O e ); MSnPS (for example, M a Sn b P c S d such as M 10 SnP 2 S 12 ); MSnPSO (eg, M a Sn b P c S d O e ); MPS (for example, M a P b S c such as M 7 P3S11); MPSO (e.g., M a P b S c Od); MZPS (e.g., M a Zn b P c S d ); MZPSO (for example, M a ZribP c S d O e ); xM 2S -yP 2S 5 ; xM 2S -yP 2S 5 -zMX; xM
• M is an alkali metal, an alkaline earth metal, or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
• X is selected from F, Cl, Br, I or a combination thereof; a, b, c, d, e and f are numbers other than zero and are independently in each formula selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are independently in each formula selected to yield a stable compound.
• the inorganic particles comprise a natural or synthetic ceramic chosen from among Al2O 3 , Mg2B2O 5 , Na2O 2B2O 3 , xMgO yB2O 3 zH2O, TiO 2 , ZrO 2 , ZnO, Ti2O 3 , SiO 2 , Cr2O 3 , CeO 2 , B2O 3 , B2O, SrBi 4 Ti 4 0is, LLTO, LLZO, LAGP, LATP, Fe2O 3 , BaTiO 3 y-LiAIO 2 , molecular sieves and zeolites (e.g.
• aluminosilicate mesoporous silica
• ceramics sulphides such as LiePS 5 CI, U7P3S11
• glass-ceramics such as LIPON, etc.
• other ceramics as well as combinations thereof.
• the ceramic has the formula Li7-bLa 3 Zr 2 M'bO 12 , where b is such that 0 ⁇ b ⁇ 1 and M' is Al, Ga, Ta, Fe or Nb or is absent, for example, b is 0 and M' is absent.
• the ceramic is an aluminosilicate compound.
• the ceramic is a sulfide or oxysulfide ceramic.
• the inorganic particles are in the form of spherical particles, in rods, in needles, in nanotubes, or one of their combinations.
• the content of inorganic particles in the composition is in the range from about 5% by weight to about 99% by weight, or from about 5% by weight to about 90% by weight, or from about 10% by weight to about 80% by weight, or from about 15% by weight to about 40% by weight.
• the composition is solid. According to another preferred embodiment, the composition is free of polymerization initiator or crosslinking agent.
• the present technology relates to a method for preparing a composition as defined above, the method comprising a step of mixing inorganic particles, at least one monomer comprising at least one polymerizable or crosslinkable function and of an organic compound comprising one or more SH group(s).
• the mixing step is carried out at a temperature situated in the range of 15°C to 50°C, or in the range of 20°C to 35°C, or in the range from 20°C to 30°C.
• the mixing step is carried out in the presence of oxygen (eg under air).
• the mixing step is carried out under an inert atmosphere.
• the process excludes the addition of a polymerization initiator or a crosslinking agent.
• the method further comprises spreading the mixture obtained on a support.
• the support is an inert film and the method optionally includes removing the film.
• the support is an electrode film.
• the support is a current collector or an electrolyte film.
• the present technology relates to an electrolyte comprising the composition as defined here, or obtained according to the present process.
• the electrolyte is in the form of a solid electrolyte film.
• the present technology relates to an electrode comprising the composition as defined here or as obtained according to the present process, and an electrochemically active material.
• the electrode further comprises a current collector.
• the electrode further comprises an electronically conductive material
• the present technology relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, in which the electrolyte is as defined above.
• the positive electrode comprises an electrochemically active positive electrode material and optionally on a current collector.
• the positive electrode electrochemically active material is selected from metal phosphates, lithiated metal phosphates, metal oxides, and lithiated metal oxides.
• M'PO 4 where M' is Fe, Ni, Mn, Co, or a combination thereof, LiVa
• the positive electrode material further comprises an electronically conductive material, a binder, a salt, and/or inorganic particles.
• the electrolyte is in direct contact with the positive electrode and/or the negative electrode, preferably with the positive electrode.
• the present technology relates to an electrochemical cell comprising a negative electrode, a positive electrode and an electrolyte, wherein the positive electrode is as herein defined (and includes the composition).
• the electrolyte and the positive electrode are as defined above.
• the negative electrode comprises an electrochemically active negative electrode material and optionally a current collector.
• the negative electrode electrochemically active material comprises a metallic film comprising an alkali or alkaline earth metal or an alloy comprising an alkali or alkaline earth metal.
• the alkali metal is chosen from lithium and sodium or an alloy comprising one of these.
• the electrochemically active negative electrode material comprises an intermetallic compound (eg, SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2 and CoSn2), a metal oxide, a metal nitride, a phosphide metal, metal phosphate (e.g. LiTi2(PO 4 )3), metal halide (e.g. metal fluoride), metal sulfide, metal oxysulfide, carbon (e.g.
• an intermetallic compound eg, SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2 and CoSn2
• a metal oxide e.g. LiTi2(PO 4 )3
• metal halide e.g. metal fluoride
• metal sulfide metal oxysulfide
• carbon e.g.
• the metal oxide is chosen from compounds of formula M”” g Oh (where M”” is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof; and g and h are numbers such that the h:g ratio is in the range of 2 to 3) (for example, MoO 3 MOO 2 , MoS2, V2O5, and TiNb2O 7 ) , spinel oxides (for example, NiCo2O 4 , ZnCo2O 4 , MnCo2O 4 , CUCO2O 4 , and CoFe2O 4 ) and LiM'””O (where M'”” is Ti, Mo, Mn, Ni, Co, Cu, V , Fe, Zn, Nb, or a combination thereof) (for example, a lithium titanate (such as Li4TisO 12 ) or a lithium molybdenum oxide (such as U2MO4O13)).
• the negative electrode material further comprises an
• the present technology also relates to a battery comprising at least one electrochemical cell as defined here.
• the battery is chosen from among a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a potassium battery, a potassium-ion battery, a magnesium battery, and a magnesium-ion battery.
• the battery is a lithium battery.
• the battery is a lithium-ion battery.
• Figure 1 shows the (a) 6 Li NMR spectra of LLZO and of the TBT/LLZO mixture and (b) 13 C of TBT and of the TBT/LLZO mixture.
• Figure 2 shows the results of impedance measurements for electrolytes comprising a sulfide ceramic, an ionic pastic salt, and a macromonomer with 0.5 wt% UV crosslinker (•), with 2 wt% TBT (A ) and with 4% by weight of TBT ( ⁇ ).
• Figure 3 shows the results of impedance measurements for electrolytes comprising a sulfide ceramic, an ionic pastic salt, and a macromonomer with 2 wt% TBT (A), with an O:Li ratio of 30:1 LiFSI and 2 wt% TBT ( ⁇ ), and with a 20:1 O:Li ratio of LiFSI and 2 wt% TBT ( ⁇ ).
• alkyl refers to optionally substituted saturated hydrocarbon groups having 1 to 20 carbon atoms (unless otherwise indicated), including linear or branched alkyl groups.
• alkyls can include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, tert-butyl, sec-butyl, isobutyl and the like.
• an "alkylene” group denotes an alkyl group located between groups, for example, methylene, ethylene, propylene, butylene, etc.
• cycloalkyl here designates a group comprising a saturated or partially unsaturated carbon cycle comprising from 3 to 15 members, this being able to be in the form of a monocycle or a polycyclic system, including spiro, fused or bridged carbocycles. and may optionally be substituted.
• heterocycloalkyl designates here a monocyclic group having from 3 to 7 members or a bicyclic group having from 7 to 15 members and being chemically stable, being saturated or partially unsaturated, and having carbon atoms and 1 to 4 heteroatoms selected from oxygen, nitrogen and sulfur. It is understood that when a nitrogen atom as a ring atom in a heterocycloalkyl, the nitrogen may also include a hydrogen atom or a substituent.
• the heterocycloalkyl group can be attached to the rest of the molecule through a carbon atom or a ring nitrogen atom.
• aromatic refers to an aromatic moiety having 4n+2 conjugated Tr(pi) electrons where n is a number from 1 to 3, in a monocyclic group, or a fused bicyclic or tricyclic system or not having a total of six to 15 ring members, wherein at least one of the rings of a system is aromatic.
• heteroaryl denotes an aromatic group possessing 4n+2 conjugated electrons Tr(pi) in which n is a number from 1 to 3, for example having from 5 to 18 ring atoms, preferably 5, 6, or 9 ring atoms; and possessing, in addition to the carbon atoms, from 1 to 5 heteroatoms chosen from oxygen, nitrogen and sulphur. It is understood that when a nitrogen atom as a ring atom in a heteroaryl, the nitrogen may also include a hydrogen atom or a substituent.
• the heteroaryl group can be attached to the rest of the molecule through a carbon atom or a ring nitrogen atom.
• a monomer refers to a molecule which can undergo polymerization.
• a monomer can include a macromonomer, i.e. a macromolecule which can itself undergo polymerization.
• a "macromonomer” as used refers more particularly to a macromolecule comprising a polymeric chain.
• the polymer chain of the macromonomer can itself comprise a homopolymer or a copolymer and can comprise branches to form multi-branched macromonomers of the star, comb, etc. type.
• compositions preferably solid, comprising polymer and inorganic particles, the polymer being the product of the reaction of at least one monomer comprising at least one polymerizable or crosslinkable function and of an organic compound comprising one or more SH group(s).
• the combination of monomer, of the SH group(s) of the organic compound and of the inorganic particles makes it possible to obtain polymerization and/or crosslinking and solidification without the addition of polymerization initiator or crosslinking agent (for example, a activated by heat or irradiation).
• Non-limiting examples of the monomer include a compound of formula R 2 (X) m , where R 2 is an organic group, X is a polymerizable or crosslinkable group, and m is a number in the range 1 to 8; or the monomer is a macromonomer comprising at least one crosslinkable segment comprising units of formula R 2 (X) m and optionally a non-crosslinkable polymer segment.
• non-crosslinkable polymer segment is present and is of Formula I:
• R is a hydrogen atom, a C 1 -C 10 alkyl group, or a -(CH 2 -OR a - R b ) group;
• R a is (CH 2 -CH 2 -O)j or (CH(CH 3 )-CH 2 -O)j;
• R b is a hydrogen atom or a C 1 -C 10 alkyl group; i is an integer selected from the range of 2 to 200,000; and j is an integer selected from the range of 0 to 100.
• R 2 or the macromonomer comprising R 2 can be chosen from the groups C 2-12 linear or branched alkyl, alkylene oxide or poly(alkylene oxide), alkylene sulfide or poly(alkylene sulfide), siloxane or polysiloxane, and mono or polyaromatic, preferably R 2 is chosen from C 2-12 linear or branched alkyl, alkylene oxide or poly(alkylene oxide), and phenyl groups. According to some examples, m is a number in the range 2 to 4.
• the polymer units from the monomer include units of at least one of the formulas: in which R 2 , R 3 , R 4 and m are as defined previously, and in which — when attached to C(R 3 R 4 ) or CH2 represents a bond with a hydrogen or sulfur atom of the organic compound, a terminal group, or another unit of the polymer, and represents a macromonomer when adjacent to R 2 .
• Examples of monomers include branched poly(ethylene glycol) comprising acrylate groups at the end of the main and/or side chain and/or on the chains, poly(ethylene glycol) diacrylate, pentaerythritol tetraacrylate, divinyl ether of triethylene glycol, ethylene glycol dimethacrylate, and divinylbenzene.
• Other examples include macromonomers consisting of polyether chains and comprising crosslinkable groups (such as acrylates or methacrylates), the polyether chains optionally being branched (multi-branched).
• the polymer units from the monomer include units of at least one of the formulas:
• R 4 and — are as defined in the preceding formulas, and p is a number other than zero.
• R 4 is H or C 1 -C 6 alkyl, for example H or C 1 -C 3 alkyl, or even H or methyl.
• R 4 when R 4 is attached to a carbon adjacent to a carbonyl, R 4 may be hydrogen or a C 1 -C 6 alkyl (such as C 1 -C 3 alkyl, or such as methyl) , and when R 4 is not attached to a carbon adjacent to a carbonyl (for example resulting from the polymerization of a vinyl group), R 4 can be a hydrogen atom.
• the monomer content in the composition can be in the range of about 1 wt% to about 95 wt%, or about 2 wt% to about 90 wt%, or about 3 wt%. weight to about 80% by weight, or from about 4% by weight to about 50% by weight, or from about 10% by weight to about 70% by weight, or from about 20% by weight to about 65% in weight.
• the organic compound comprising one or more SH group(s) generally comprises an organic group serving as a carrier group for the SH group(s). This may be a linear or branched alkyl, alkenyl or alkynyl, optionally comprising heteroatoms (such as O, N, S, etc.) and/or being optionally substituted.
• the organic group can also be a monocyclic or polycyclic group optionally comprising heteroatoms (such as O, N, S, etc.) and/or being optionally substituted.
• the organic group can comprise an oligomeric or polymeric chain.
• the organic group can also comprise a combination of the preceding elements.
• the organic compound has the formula R 1 (SH) n , where R 1 is an organic group linking the SH group(s), and where n is a number in the range from 1 to 10 (or 1 to 4), or the compound is a macromonomer comprising at least one segment comprising units of formula R 1 (SH) n .
• R 1 or the segment comprising R 1 can be chosen from linear or branched C 2-12 alkyl, linear or branched C 2-12 alkyl polyol ether or ester groups, alkylene oxide or poly(carbon oxide) alkylene) optionally comprising one or more sulfur atom(s) in a chain, alkylene sulfide or poly(alkylene sulfide), siloxane or polysiloxane, mono or polycycloalkyl or heterocycloalkyl, mono or polyaromatic or heteroaromatic fused or unfused optionally comprising a linking atom, or a combination thereof.
• Non-limiting examples of organic compounds include 1-(2-mercaptoethoxy-2-ethoxyethyl-2-thioethyl)-2-pyrrolidone, 2,2'-(ethylenedioxy)diethanethiol, pentaerythritol tetrakis(3-mercaptopropionate) , and 4,4'-thiobisbenzenethiol.
• the units of the polymer originating from the organic compound comprise units of at least one of the formulas: wherein R 1 and n are as previously defined and where — when attached to a sulfur atom represents a bond with another unit of the polymer, such as a unit from the monomer, and represents a macromonomer when adjacent to R 1 .
• the polymer units from the organic compound include units of at least one of the formulas:
• the organic compound content in the composition is in the range of about 0.01 wt% to about 60 wt%, or about 0.05 wt% to about 50 wt%, or about 10 wt% to about 30 wt%, or about 15 wt% to about 40 wt%.
• the polymer resulting from the reaction of the monomer and the organic compound can be polymer of random, block, or alternating configuration.
• the inorganic particles can comprise an inorganic compound of the amorphous, ceramic or glass-ceramic type, for example, based on oxide, sulphide or oxysulphide, the inorganic compound being natural or synthetic.
• inorganic compounds include a natural or synthetic ceramic selected from inorganic compounds of formulas MLZO (for example, M 7 La 3 Zr 2 O 12 , M ⁇ 7- a )La 3 Zr 2 AlbO 12 , M (7-a ) La 3 Zr 2 Ga b O 12 , M(7- a )La 3 Zr (2-b) Ta b O 12 , and M(7- a )La 3 Zr (2-b) NbbO 12 ); MLTaO (e.g., M 7 La 3 Ta 2 O 12 , MsLa 3 Ta 2 O 12 , and M6La 3 Ta1.5Y0.5O 12 ); MLSnO (e.g., M 7 LasSn2O 12 ); MAGP (for example, M 1+a
• M a GebP c S d O e MSiPS (for example, M a Si b P c S d such as M 10 SiP 2 S 12 ); MSiPSO (e.g., M a Si b P c S d O e ); MSnPS (for example, M a Sn b P c S d such as M 10 SnP 2 S 12 ); MSnPSO (eg, M a Sn b P c S d O e ); MPS (for example, M a P b S c such as M 7 P3S11); MPSO (e.g., M a P b S c Od); MZPS (e.g., M a Zn b P c S d ); MZPSO (e.g., M a Zn b P c S d O e ); xM 2S -yP 2S 5 ; xM 2S -yP 2S 5 -zM
• M is an alkali metal, an alkaline earth metal, or a combination thereof, and wherein when M comprises an alkaline earth metal ion, then the number of M is adjusted to achieve electroneutrality;
• X is selected from F, Cl, Br, I or a combination thereof; a, b, c, d, e and f are numbers other than zero and are independently in each formula selected to achieve electroneutrality; and v, w, x, y and z are non-zero numbers and are independently in each formula selected to yield a stable compound.
• the inorganic particles comprise a natural or synthetic ceramic chosen from among Al2O 3 , Mg2B2O 5 , Na2O 2B2O 3 , xMgO yB2O 3 zH2O, TiO 2 , ZrO 2 , ZnO, Ti2O 3 , SiO 2 , Cr2O 3 , CeO 2 , B2O 3 , B2O, SrBi 4 Ti 4 O15, LLTO, LLZO, LAGP, LATP, Fe2O 3 , BaTiO 3 y-LiAIO 2 , molecular sieves and zeolites (e.g.
• aluminosilicate mesoporous silica
• sulfide ceramics such as Li6PS 5 CI, Li7P3S11
• glass ceramics such as LIPON, etc.
• other ceramics as well as combinations thereof.
• the ceramic has the formula Li7-bLa-Zr 2 M'bO 12 , where b is such that 0 ⁇ x ⁇ 1 and M' is Al, Ga, Ta, Fe or Nb or is absent, for example, b is 0 and M is absent.
• the ceramic is an aluminosilicate compound.
• the ceramic is a sulfide or oxysulfide ceramic.
• the inorganic particles can be in any form, for example, as spherical particles, rods, needles, nanotubes, or a combination thereof.
• the inorganic particle content in the composition is preferably in the range of about 5 wt% to about 99 wt%, or about 5 wt% to about 90 wt%, or about 10% by weight to about 80% by weight, or from about 15% by weight to about 40% by weight.
• composition after reaction of the monomer with the organic compound, is generally solid.
• the composition is also generally free of polymerization initiator or crosslinking agent, the polymerization and/or crosslinking taking place in situ, and mainly in the presence of the inorganic particles.
• This document also describes a process for the preparation of a composition as defined here, the process comprising a step of mixing inorganic particles, at least one monomer comprising at least one polymerizable or crosslinkable function and a compound organic comprising one or more SH group(s).
• the mixing step can be carried out at a temperature in the range of 15°C to 50°C, or in the range of 20°C to 35°C, or in the range of 20°C to 30°C.
• the temperature of the reaction mixture may be higher although the reaction may occur at lower temperature or generally without heating (at room temperature).
• the mixing step can be carried out in the presence of oxygen (e.g. under air) or under an inert atmosphere (e.g. argon, nitrogen).
• oxygen e.g. under air
• inert atmosphere e.g. argon, nitrogen
• the choice of the type of atmosphere may depend on the sensitivity to air of the elements included in the composition or on the type of process recommended. For example, a process carried out in the assembly line and being followed by a contacting step (spreading of the mixture or application of a solid film) directly or indirectly with a film of lithium could be carried out in an anhydrous chamber or under an inert atmosphere. .
• An inorganic compound used in the composition could also be more sensitive to air.
• the method may also comprise the spreading of the composition on a support before the complete polymerization of the latter.
• the support may be a film which will optionally be removed after the polymerization and/or the hardening of the composition.
• the support can also be a film intended to remain in contact with the composition.
• the composition when used for the manufacture of an electrolyte, it can be spread directly on one or the other of the electrodes. Alternately, when the composition is included in an electrode material, the latter can be applied to another element of the cell such as a current collector or an electrolyte film.
• the present composition can be used in the manufacture of electrolyte films.
• This document therefore also relates to an electrolyte comprising the composition as defined here, or obtained according to the present process.
• the electrolyte is in the form of a solid electrolyte film.
• the composition as described here could also be used in the manufacture of electrode material, by being mixed with an electrochemically active material and possibly applied to a current collector.
• the electrode material may also optionally include an electronically conductive material, a binder, a salt, or a combination of two or more of these.
• LiM'PCL where M' is Fe, Ni, M
• This document also relates to electrochemical cells comprising a negative electrode, a positive electrode and an electrolyte, in which the electrolyte is as defined herein.
• the positive electrode can then comprise an electrochemically active material of positive electrode and possibly on a current collector.
• the positive electrode electrochemically active material can be chosen from metal phosphates, lithiated metal phosphates, metal oxides, and lithiated metal oxides. Alternatively, the positive electrode electrochemically active material can be chosen from those described above.
• the positive electrode may also comprise optionally an electronic conductive material, a binder, a salt, and/or inorganic particles.
• the electrolyte as defined here or the composition intended to form this electrolyte can be deposited directly on the film of the positive or negative electrode during the formation of the cell.
• the electrolyte film thus formed is then in direct contact with the positive electrode and/or the negative electrode, preferably with the positive electrode.
• the electrochemical cell comprises a negative electrode, a positive electrode and an electrolyte, wherein the positive electrode is as defined above and comprises the composition, or the positive electrode and the electrolyte both comprise the present composition.
• the negative electrode of electrochemical cells as described herein typically includes a negative electrode electrochemically active material and optionally a current collector.
• the electrochemically active negative electrode material comprises a metal film comprising an alkali or alkaline-earth metal or an alloy comprising an alkali or alkaline-earth metal, preferably chosen from lithium or sodium or a alloy comprising one of these.
• the metallic film can therefore also be an alloy of lithium and of an element chosen from alkali metals other than lithium (such as Na, K, Rb, and Cs), alkaline-earth metals (such as Mg, Ca, Sr, and Ba), rare earth metals (such as Sc , Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu), zirconium, copper, silver, bismuth, cobalt, manganese, zinc, aluminum, silicon, tin, antimony, cadmium, mercury, lead, molybdenum, iron, boron, indium, thallium, nickel and germanium (eg Zr, Cu, Ag, Bi, Co, Zn , Al, Si, Sn, Sb, Cd, Hg, P b , Mn, B, In, Tl, Ni, or Ge), preferably the lithium alloy comprising at least 50%, or at least 75%, or at least 90%, or at
• the negative electrode electrochemically active material comprises an intermetallic compound (eg, SnSb, TiSnSb, Cu2Sb, AlSb, FeSb2, FeSn2 and CoSn2), a metal oxide, a metal nitride, a metal phosphide , a metal phosphate (for example, LiTi 2 (PO 4 )3), a metal halide (for example, a metal fluoride), metal sulfide, metal oxysulfide, carbon (e.g., graphite, graphene, reduced graphene oxide, hard carbon, soft carbon, exfoliated graphite, and amorphous carbon) , silicon (Si), a silicon-carbon composite (Si-C), a silicon oxide (SiO x ), a silicon oxide-carbon composite (SiO x -C), tin (Sn), a tin-carbon composite (Sn-C), a tin oxide (SnO x x
• the metal oxide can be selected from compounds of formula M”” g Oh (where M”” is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination of these; and g and h are numbers such that the h:g ratio is in the range from 2 to 3) (for example, MoO 3 MOO 2 , M0S2, V2O5, and TiNb 2 O7), spinel oxides (for example, NiCo 2 O 4 , ZnCo 2 O 4 , MnCo 2 O 4 , CuCo 2 O 4 , and CoFe 2 O 4 ) and LiM'””O (where M'”” is Ti, Mo, Mn, Ni, Co, Cu, V, Fe, Zn, Nb, or a combination thereof) (for example, a lithium titanate (such as Li4TisOi 2 ) or a lithium molybdenum oxide (such as Li 2 Mo4Oi3)).
• M is Ti, Mo, Mn, Ni, Co, Cu,
• the negative electrode material may also optionally comprise an electronically conductive material, a binder, a salt, inorganic particles or a combination of two or more of these.
• the battery can be selected from a lithium battery, a lithium-ion battery, a sodium battery, a sodium-ion battery, a potassium battery, a potassium-ion, a magnesium battery, and a magnesium-ion battery, preferably a lithium or lithium-ion battery.
• electrochemical batteries and accumulators described here are intended, for example, for use in mobile devices, such as mobile phones, cameras, tablets or laptops, in electric or hybrid vehicles, or in the storage of 'renewable energy.
• compositions 1, 2, and 4 (comparative) and the present compositions 3 and 5 to 19 are prepared with the elements and proportions indicated in Table 1, where the following abbreviations are used:
• US’674 a multibranched polyether (macromonomer) comprising crosslinkable acrylate units at the chain ends, as described in US Patent No. 7,897,674;
• PEGDA poly(ethylene glycol) diacrylate
• PETA pentaerythritol tetraacrylate
• TEGDVE tri(ethylene glycol) divinyl ether
• EGDMA ethylene glycol dimethacrylate
• DVB divinylbenzene (about 80% 1,4-divinylbenzene, 20% 1,2-divinylbenzene);
• HNT a natural ceramic of the aluminosilicate type (Halloysite nanotube);
• LLZO lithium lanthanum zirconium oxide (Li7La 3 Zr 2 O 12 );
• EDDET 2,2'-(ethylenedioxy)diethanethiol
• PTM P pentaerythritol tetrakis(3-mercaptopropionate); and TBT: 4,4'-thiobisbenzenethiol.
• compositions 1 to 19 of Table 1 are prepared according to the following procedures.
• Layout 6 1.5 g of US'674, 0.76 g of HNT and 0.36 g of MT are well mixed in a flask at room temperature under air, the solution is stirred with a magnetic bar. After 3 hours, the solution became solid, indicating polymer formation.
• Layout 12 1.4 g of PETA, 0.7 g of HNT and 0.7 g of MT are well mixed in a flask at room temperature under air, the solution is stirred with a magnetic bar. After 15 minutes, the solution became solid, indicating polymer formation.
• Layout 18 1.2 g of US'674 and 0.3 g of TBT are mixed well in a flask at room temperature under air overnight. When the solution is homogeneous, 0.5 g of HNT is added with stirring. After 15 minutes, the solution became solid, indicating polymer formation.
• the solid-state NMR analyzes of TBT, LLZO and the TBT/LLZO mixture were carried out on a 500 MHz NMR spectrometer equipped with a 4 mm triple resonance probe with MAS (“ magic angle spinning”), up to 15 kHz.
• the TBT/LLZO mixture was prepared by grinding in a mortar.
• the 6 Li NMR spectra of LLZO and of the TBT/LLZO mixture and 13 C of TBT and of the TBT/LLZO mixture are shown in FIGS. 1(a) and (b).
• Figure 1(a) shows that the signal intensity of LLZO in the mixture becomes weaker than that of LLZO, suggesting an interaction between LLZO and TBT that changes the chemical environment of Li ions in LLZO.
• Figure 1(b) a displacement of the peak corresponding to the carbons next to the SH group in the TBT/LLZO mixture indicates the formation of -S' anion, which will be able to initiate the polymerization anionically.
• the binder is formed by a 40/60 mixture by weight respectively of (a) US'674 polymer with 0.5% by weight of UV crosslinker, or (b) of US'674 polymer with 2% by weight of TBT, or (c) US'674 polymer with 4 wt% TBT; and ionic plastic salt (bis(trifluoromethanesulfonyl)imide of 1,T-hexamethylene bis(1-methylpyrrolidinium)) dissolved in dichloromethane (DCM).
• DCM dichloromethane
• the ratio by weight between sulphide and binder is 90/10 by mass.
• the quantity of DCM is adjusted in order to achieve a good viscosity of the mixture.
• the mixture thus obtained is coated on a previously degreased aluminum foil. After drying in a glove box, UV crosslinking is carried out for the film comprising UV crosslinking agent. ii. Impedance measurements:
• the films are prepared as in Example 3(a)(i), where the binder is a 40/60 by weight mixture respectively of (a) US'674 polymer with 2% by weight of TBT, or (b) of US'674 polymer with a 30:1 O:Li ratio of LiFSI and 2 wt% TBT, or (c) US'674 polymer with a 20:1 O:Li ratio of LiFSI and 2 wt% of TBT, and of ionic plastic salt (bis(trifluoromethanesulfonyl)imide of 1,T-hexamethylene bis(1-methylpyrrolidinium)) dissolved in DCM.
• ionic plastic salt bis(trifluoromethanesulfonyl)imide of 1,T-hexamethylene bis(1-methylpyrrolidinium
• the ionic conductivity of the films decreases with the addition and increase of LiFSI salt.
• the addition of LiFSI salt increases the ionic conductivity of the US'674 polymer as described in US Patent No. 7,897,674.
• the opposite is seen here.
• the TBT by placing itself between the chains of the polymer US'674 horn monomer, makes it possible to inhibit its ionic conductive character.
• the product of the reaction of the US’674 polymer and the TBT then serves as a support for the film by bringing a flexible character to this film.
• the added LiFSI salt does not participate in conduction and therefore blocks this conduction as dead matter because it does not react with the other constituents of the film.

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