DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement/
The information disclosure statements (IDSs) submitted on 04/08/2024, 07/01/2024, 10/07/2025, and 07/02/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Specification
The specification filed on 04/08/2024 was reviewed and is acceptable.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nakazawa et al. (US 20160013517 A1, hereinafter Nakazawa), as cited in IDS filed 04/08/2024, in view of Yagupolskii et al. (“The immense acidifying effect of the supersubstituent =NSO2CF3 on the acidity of amides and amidines of benzoic acids in acetonitrile, hereinafter Yagupolskii), as cited in IDS filed 04/08/2024.
Regarding Claim 1, Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract). Nakazawa discloses that the nonaqueous electrolyte solution contains at least one compound selected from the group consisting of a compound having a fluorosulfonyl structure (—SO2F) (Nakazawa, Abstract), and the compound having a fluorosulfonyl structure (—SO2F) has a high degree of polarization because of having a fluorine atom bonded to the SO2 group, and the elimination property of the fluorine atom is high. which reacts with the Si surface to suppress a lowering of the surface activity or a change in properties of the active material (Nakazawa, [0039]).
Nakazawa is silent regarding at least one selected from the group consisting of a compound represented by the following Formula (1),
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where, M1m+ represents a proton, and m represents a valence of the cation,
R1 and R2 each independently represent a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydrocarbon group having 1 to 10 carbon atoms (the hydrocarbon group may have a hetero atom or a halogen atom, and may have a branched chain or a cyclic structure if the number of carbon atoms is 3 or more),
R3 represents a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, a perfluoroalkenyl group having 2 to 4 carbon atoms, a perfluoroalkynyl group having 2 to 4 carbon atoms, a cyano group, an amino group, an aminocarbonyl group, a perfluoroalkylcarbonyl group having 2 to 4 carbon atoms, a hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or a cyclic structure if the number of carbon atoms is 3 or more, -C(=O)-R', where R' represents a hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or cyclic structure if the number of carbon atoms is 3 or more, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, where the alkoxy group, alkenyloxy group, and alkynyloxy group described above may further have a hetero atom or a halogen atom and may have a branched chain or cyclic structure if the number of carbon atoms is 3 or more, an aryloxy group having 6 to 10 carbon atoms, or -O-(Map+)q, where Map+ represents a proton, a metal cation, or an onium cation, p represents a valence of the cation and q represents a number to satisfy p x q = 1, -Ra-S(=O)2(Rb), or -Rc-P(=O)(Rd)(Rc).
Ra and RC each independently represent a perfluoroalkylene group having 1 to 4 carbon atoms or a hydrocarbon group having 1 to 10 carbon atoms, where the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or cyclic structure if the number of carbon atoms is 3 or more,
Rb represents a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 10 carbon atoms, where the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or cyclic structure if the number of carbon atoms is 3 or more, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or -O-(M2r+)s, where M2r+ represents a proton, a metal cation, or an onium cation, r represents a valence of the cation, and s represents a number to satisfy r x s = 1,
Rd and Re each independently represent a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms, a hydrocarbon group having 1 to 10 carbon atoms, where the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or cyclic structure if the number of carbon atoms is 3 or more, an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, an alkynyloxy group having 2 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, a cycloalkenyloxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, or -O-(M3t+)u, where M3t+ represents a proton, a metal cation, or an onium cation, t represents a valence of the cation and u represents a number to satisfy t x u = 1.
Yagupolskii discloses the limitations regarding a compound comprising:
(I) at least one selected from the group consisting of a compound represented by the following Formula (1),
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where, M1m+ represents a proton, and m represents a valence of the cation,
R1 and R2 each independently represent a hydrocarbon group having 1 carbon atom (the hydrocarbon group may have a halogen atom),
R3 represents a hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or a cyclic structure if the number of carbon atoms is 3 or more (Yagupolskii, N,N’-bis(trifluoromethylsulfonyl)benzamidines 4a-f, Page 1951, paragraph starting with “The N,N’-bis(trifluoromethylsulfonyl)benzamidines…”, Chemical Structure below; The Examiner notes that N,N’-bis(trifluoromethylsulfonyl)benzamidines compound comprises a proton, a hydrocarbon group having 1 carbon atom (the hydrocarbon group may have a halogen atom) (Yagupolskii, the introduction of electron-acceptor supersubstitutents like =NSO2CF3 and =NSO2F into acidic systems is indeed predicted to lead to very significant increase in their acidity, Page 1950, paragraph starting with “The introduction of…”).
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Yagupolskii teaches that the introduction of electron-acceptor supersubstitutents like =NSO2CF3 and =NSO2F into acidic systems is indeed predicted to lead to very significant increase in their acidity (Yagupolskii, Page 1950, paragraph starting with “The introduction of…”)
Nakazawa and Yagupolskii are analogous to the current invention as they are all directed towards a compound having a fluorosulfonyl structure.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to include the N,N’-bis(trifluoromethylsulfonyl)benzamidine of Yagupolskii in the nonaqueous electrolyte solution of Nakazawa, in order to increase acidity of the system.
Regarding Claim 2, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein at least one of Rl and R2 in the Formula (1) represents a fluorine atom (Yagupolskii, the introduction of electron-acceptor supersubstitutents like =NSO2CF3 and =NSO2F into acidic systems is indeed predicted to lead to very significant increase in their acidity, Page 1950, paragraph starting with “The introduction of…”).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to use =NSO2F instead of =NSO2CF3 as an obvious substitute as they are both known to be an electron-acceptor supersubstitutent.
Regarding Claim 3, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract). Modified Nakazawa is silent regarding at least one of R4 and R5 in the Formula (2) represents a fluorine atom.
However, since Formula 1 has been selected, as noted above, Claim 3, which requires Formula 2, is rendered moot.
Regarding Claim 4, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract). Modified Nakazawa is silent regarding at least one of R9 and R10 in the Formula (3) represents a fluorine atom.
However, since Formula 1 has been selected, as noted above, Claim 4, which requires Formula 3, is rendered moot.
Regarding Claim 5, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), further comprising:(II) a solute (Nakazawa, inorganic lithium salts such as LiPF6, [0151]).
Regarding Claim 6, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), further comprising:(III) a nonaqueous organic solvent (Nakazawa, nonaqueous organic solvent, [0166]).
Regarding Claim 7, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the (II) solute is at least one selected from the group consisting of LiPF6, LiBF4, LiSbF6, LiAsF6, LiClO4, LiCF3SO3, LiC4F9SO3, LiN(SO2F)2 (Nakazawa, inorganic lithium salts such as LiPF6, LiBF4, LiClO4, LiSbF6, LiC(SO2CF)3, LiN(FSO2)2, [0149-0162]).
Regarding Claim 8, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the (III) nonaqueous organic solvent comprises at least one selected from the group consisting of a cyclic ester, a chain ester, a chain ether, and a sulfone compound (Nakazawa, cyclic carbonate, a linear carbonate, a cyclic or linear carboxylate, an ether compound, and a sulfone compound, [0166]).
Regarding Claim 9, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the nonaqueous organic solvent comprises a cyclic ester, and the cyclic ester comprises cyclic carbonate (Nakazawa, organic solvents include a cyclic carbonate, [0166]).
Regarding Claim 10, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the cyclic carbonate comprises at least one selected from the group consisting of ethylene carbonate, propylene carbonate, and fluoroethylene carbonate (Nakazawa, the cyclic carbonates include ethylene carbonate, propylene carbonate, and fluoroethylene carbonate, [0119, 0169]).
Regarding Claim 11, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the nonaqueous organic solvent comprises a chain ester, and the chain ester comprises chain carbonate (Nakazawa, linear carbonates, [0173]).
Regarding Claim 12, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein the chain carbonate comprises at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate (Nakazawa, the linear carbonates include ethylmethyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl-n-propyl carbonate, [0174]).
Regarding Claim 13, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein a content of the (I) is 0.01% by mass to 5.0% by mass with respect to the total amount of the nonaqueous electrolyte solution (Nakazawa, the content of the at least one compound selected from the group consisting of a compound having a fluorosulfonyl structure (—SO2F) is 0.01% by mass to 10.0% by mass, based on the total amount of the nonaqueous electrolyte solution, [0032]; the disclosed range of 0.01% by mass to 10.0% by mass overlaps the claimed range of 0.01% by mass to 5.0% by mass).
Modified Nakazawa teaches that a battery comprising a fluorosulfonyl structure had improved high-temperature storage characteristics, cycle gas suppression, cycle characteristics, rate characteristics, and battery expansion (Nakazawa, [0040]).
It would have been obvious to one having ordinary skill in the art before the time of the effective filing date of the current invention to select the overlapping portions of the disclosed because it would improve high-temperature storage characteristics, cycle gas suppression, cycle characteristics, rate characteristics, and battery expansion and selection of overlapping portions of ranges has been held to be a prima facie case of obviousness (see MPEP 2144.05 (I)).
Regarding Claim 14, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), further comprising: at least one selected from fluorobenzene (Nakazawa, other assistants include fluorobenzene, [0275-0283]).
Regarding Claim 15, modified Nakazawa discloses all of the claim limitations as set forth above. Modified Nakazawa discloses the limitations regarding a nonaqueous electrolyte solution battery (Nakazawa, nonaqueous electrolyte secondary battery, [0458]), at least comprising:
a positive electrode (Nakazawa, positive electrode, [0458]);
a negative electrode (Nakazawa, negative electrode, [0458]);
a separator (Nakazawa, separator, [0458]); and the nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, [0458])
Claim(s) 16-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yagupolskii et al. (“The immense acidifying effect of the supersubstituent =NSO2CF3 on the acidity of amides and amidines of benzoic acids in acetonitrile, hereinafter Yagupolskii), as cited in IDS filed 04/08/2024.
Regarding Claim 16, Yagupolskii discloses the limitations regarding a compound represented by the following Formula (I)
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where, M1m+ represents a proton, and m represents a valence of the cation,
R1 and R2 each independently represent a hydrocarbon group having 1 carbon atom (the hydrocarbon group may have a halogen atom),
R3 represents a hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group may have a hetero atom or a halogen atom and may have a branched chain or a cyclic structure if the number of carbon atoms is 3 or more (Yagupolskii, N,N’-bis(trifluoromethylsulfonyl)benzamidines 4a-f, Page 1951, paragraph starting with “The N,N’-bis(trifluoromethylsulfonyl)benzamidines…”, Chemical Structure below; The Examiner notes that N,N’-bis(trifluoromethylsulfonyl)benzamidines compound comprises a proton, a hydrocarbon group having 1 carbon atom (the hydrocarbon group may have a halogen atom)
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Regarding Claim 17, Yagupolskii discloses all of the claim limitations as set forth above. Yagupolskii discloses the limitations regarding a nonaqueous electrolyte solution (Nakazawa, nonaqueous electrolyte solution, Abstract), wherein at least one of Rl and R2 in the Formula (1) represents a fluorine atom (Yagupolskii, the introduction of electron-acceptor supersubstitutents like =NSO2CF3 and =NSO2F into acidic systems is indeed predicted to lead to very significant increase in their acidity, Page 1950, paragraph starting with “The introduction of…”).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to use =NSO2F instead of =NSO2CF3 as an obvious substitute as they are both known to be an electron-acceptor supersubstitutent.
Regarding Claim 18, Yagupolskii discloses all of the claim limitations as set forth above. Yagupolskii discloses the limitations regarding a compound (Yagupolskii, N,N’-bis(trifluoromethylsulfonyl)benzamidines 4a-f, Page 1951, paragraph starting with “The N,N’-bis(trifluoromethylsulfonyl)benzamidines…”, Chemical Structure above). Yagupolskii is silent regarding at least one of R4 and R5 in the Formula (2) represents a fluorine atom.
However, since Formula 1 has been selected, as noted above, Claim 3, which requires Formula 2, is rendered moot.
Regarding Claim 19, Yagupolskii discloses all of the claim limitations as set forth above. Yagupolskii discloses the limitations regarding a compound (Yagupolskii, N,N’-bis(trifluoromethylsulfonyl)benzamidines 4a-f, Page 1951, paragraph starting with “The N,N’-bis(trifluoromethylsulfonyl)benzamidines…”, Chemical Structure above). Yagupolskii is silent regarding at least one of R9 and R10 in the Formula (3) represents a fluorine atom.
However, since Formula 1 has been selected, as noted above, Claim 4, which requires Formula 3, is rendered moot.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
US 20190292054 A1 discloses a method the enables easy production of bis(fluorosulfonyl)imide suitable for a non-aqueous electrolytic solution for a lithium ion secondary battery (Title).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KEVIN NGUYEN whose telephone number is (703)756-1745. The examiner can normally be reached Monday-Thursday 9:50 - 7:50 ET.
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/K.N./Examiner, Art Unit 1752
/OSEI K AMPONSAH/Primary Examiner, Art Unit 1752
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