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 .
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 4, 6-8, and 11-12 is rejected under 35 U.S.C. 102 (a)(1) as being unpatentable over Yamaguchi, et. al. (JP2012109089A).
Regarding Claim 1, Yamaguchi recites a nonaqueous electrolytic solution (electrolytic solution 90), comprising: a solute (a solute is a substance dissolved a solvent to create a solution; because this is not defined, this includes the “[p.3-4] supporting salt (supporting electrolyte)” which includes LiPF6) and a nonaqueous organic solvent (“[p.3.] As the non-aqueous solvent in the non-aqueous electrolyte disclosed herein . . . examples include ethylene carbonate (EC), propylene carbonate (PC), diethyl carbonate (DEC), dimethyl carbonate (DMC), ethyl methyl carbonate (EMC)”). Yamaguchi at [p.3-4].
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General Formula (1) of Claim 1.
Claim 1 requires a compound represented by the following General Formula (1) in the General Formula (1), R1's each independently represent PO(Rf)2 or SO2Rf, Rf's each independently represent a fluorine atom, a linear alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 4 carbon atoms, an oxygen atom may be included between a carbon atom-carbon atom bond in the alkyl group, and any hydrogen atom of the alkyl group may be substituted with a fluorine atom,R2's each independently represent a hydrogen atom, a lithium ion, a sodium ion, a potassium ion, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms, an oxygen atom may be included between a carbon atom-carbon atom bond in the alkyl group, any hydrogen atom of the alkyl group may be substituted with a fluorine atom, the alkyl group may contain an unsaturated bond, and when R2 represents a lithium ion, a sodium ion, or a potassium ion, a bond between a nitrogen atom and R2 in the General Formula (1) represents an ionic bond, and n represents an integer of 0 to 3.
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Yamaguchi at line 10, page 16, showing the synthesis of compound 6.
Notably, n may equal 0, meaning the amides may be directly linked to one another. Yamaguchi teaches a compound 6 (also referred to as additive B-4), wherein a diamide type molecule comprises R2 groups which are lithium ions, and R1 groups which are SO2Rf, wherein Rf is “a linear alkyl group having . . . 4 carbon atoms . . . and any hydrogen atom of the alkyl group may be substituted with a fluorine atom [in this case, all of the hydrogen atoms are replaced].” Yamaguchi at [p. 10-11, 16]. This meets the limitations of Claim 1’s general formula 1.
Claim 1 is recited by Yamaguchi.
Regarding Claim 4, Claim 4 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
Yamaguchi teaches additive B-4, wherein R2s in the General Formula (1) each independently represent a lithium ion. This meets “wherein R2's in the General Formula (1) each independently represent a hydrogen atom, a lithium ion, a sodium ion, a linear alkyl group having I to 4 carbon atoms, or a branched alkyl group having 3 to 4 carbon atoms.”
Claim 4 is recited by Yamaguchi.
Regarding Claim 6, Claim 6 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi. Yamaguchi recites a nonaqueous organic solvent (”[p.3] As the non-aqueous solvent in the non-aqueous electrolyte disclosed herein . . . examples include ethylene carbonate (EC), propylene carbonate (PC), diethyl carbonate (DEC), dimethyl carbonate (DMC), ethyl methyl carbonate (EMC)”). Yamaguchi at [p.3]. This solvent meets “wherein the nonaqueous organic solvent contains at least one selected from the group consisting of cyclic carbonate and chain carbonate.”
Claim 6 is recited by Yamaguchi.
Regarding Claim 7, Claim 7 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi. Yamaguchi recites a nonaqueous organic solvent (”[p.3] As the non-aqueous solvent in the non-aqueous electrolyte disclosed herein . . . examples include ethylene carbonate (EC), propylene carbonate (PC), diethyl carbonate (DEC), dimethyl carbonate (DMC), ethyl methyl carbonate (EMC)”). Yamaguchi at [p.3]. This solvent meets “wherein the cyclic carbonate is at least one selected from the group consisting of ethylene carbonate, propylene carbonate, and fluoroethylene carbonate, and the chain carbonate is at least one selected from the group consisting of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate, and methyl propyl carbonate.”
Claim 7 is recited by Yamaguchi.
Regarding Claim 8, Claim 8 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi. Yamaguchi recites “In view of solubility in a non-aqueous solvent (for example, a carbonate-based solvent), the content of the additive with respect to an electrolyte constituent other than the additive is usually 5% by mass or less (that is, other than the additive). A nonaqueous electrolyte is preferable in which the content of the additive is 5 g or less with respect to 100 g of the electrolyte constituent component. In a preferred embodiment, the content of the additive is 0.05 to 5% by mass (typically 0.1 to 5% by mass, for example 0.5 to 3% by mass). If the content of the additive is too small, a sufficient additive effect tends to be hardly exhibited. If the content of the additive is too large, it may be difficult to prepare the non-aqueous electrolyte, or the additive may be easily deposited in the battery container depending on the time, use environment, or the like.” Yamaguchi at [p.4]. This is within the range, “a content of the compound represented by the General Formula (1) with respect to a total amount of the compound represented by the General Formula (1), the solute, and the nonaqueous organic solvent is 0.001% by mass to 10.0% by mass.” This is anticipated because Yamaguchi teaches “[p.11] According to electrolyte sample 5 containing 0.1 to 5% by mass (here 0.1% by mass) of additive B-4,” and a specific example in the prior art which is within a claimed range anticipates the range. MPEP 2131.03.
Claim 8 is recited by Yamaguchi.
Regarding Claim 11, Claim 11 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi. Yamaguchi recites “[p.11] Such a nonaqueous secondary battery includes, for example, a positive electrode, a negative electrode, and a nonaqueous electrolyte, and the negative electrode includes a negative electrode active material layer mainly composed of a negative electrode active material, and the negative electrode active material layer has a bivalent or higher valence.” Yamaguchi at [p.11]. Yamaguchi as noted in the Claim 1 analysis teaches the solution of Claim 1. This meets, “a nonaqueous electrolytic solution battery, comprising: a positive electrode; a negative electrode; and the nonaqueous electrolytic solution according to claim 1.”
Claim 11 is recited by Yamaguchi.
Regarding Claim 12, Claim 12 requires a compound represented by the following General Formula (l),
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General Formula (1) of Claim 12.
wherein in the General Formula (1), R1's each independently represent POF2 or SO2F,R2's each independently represent a hydrogen atom, a lithium ion, a sodium ion, a potassium ion, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms, and an oxygen atom may be included between a carbon atom- carbon atom bond in the alkyl group, any hydrogen atom of the alkyl group may be substituted with a fluorine atom, the alkyl group may contain an unsaturated bond, and when R2 represents a lithium ion, a sodium ion, or a potassium ion, a bond between a nitrogen atom and R2 in the General Formula (1) represents an ionic bond, and n represents an integer of 0 to 3.
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Yamaguchi at line 10, page 16, showing the synthesis of compound 6.
Notably, n may equal 0, meaning the amides may be directly linked to one another. Yamaguchi teaches a compound 6 (also referred to as additive B-4), wherein a diamide type molecule comprises R2 groups which are lithium ions, and R1 groups which are SO2Rf, wherein Rf is “a linear alkyl group having . . . 4 carbon atoms . . . and any hydrogen atom of the alkyl group may be substituted with a fluorine atom [in this case, all of the hydrogen atoms are replaced].” Yamaguchi at [p.16]. This meets the limitations of Claim 12’s general formula 1.
Claim 12 is anticipated by Yamaguchi.
Claim Rejections - 35 USC § 103
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.
Claims 2 – 3, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Yamaguchi, in view of Zhamu, et. al. (US20200028205 A1).
Regarding Claim 2, Claim 2 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
Yamaguchi teaches “[p.11] Such a nonaqueous secondary battery includes, for example, a positive electrode, a negative electrode, and a nonaqueous electrolyte, and the negative electrode includes a negative electrode active material layer mainly composed of a negative electrode active material, and the negative electrode active material layer has a bivalent or higher valence. It may be a derivative of an oxocarbonic acid or a divalent or higher carboxylic acid containing an amidolithium salt having at least one N-fluorinated alkanesulfonyl group,” and “[p.2] The amidolithium salt in the technology disclosed herein has at least one, typically two or more (preferably two) N-alkanesulfonyl fluoride groups in one molecule. The N-alkanesulfonyl fluoride group is a group in which an alkanesulfonyl group is bonded to the nitrogen atom of the amide group, and can be represented by the general formula: N—SO 2 Rf.” This Rf group constitutes the alkanesulfonyl group. However Claim 3 requires effectively no Rf group.
Zhamu teaches a rechargeable lithium ion battery, wherein the electrolyte may comprise “[0011] lithium-capturing groups” which contribute to providing “[0010] a simple, cost-effective, and easy-to-implement approach to preventing potential Li metal dendrite-induced internal short circuit and thermal runaway problems in various fast-charging Li-ion batteries.” Zhamu at [0010 – 11]. [0021] The lithium ion-capturing groups may contain ionic liquids, which are low melting temperature salts that are in a molten or liquid state when above a desired temperature . . . [0022] A typical and well-known ionic liquid is formed by the combination of a 1-ethyl-3-methylimidazolium (EMI) cation and an N,N-bis(trifluoromethane)sulphonamide (TFSI) anion. This combination gives a fluid with an ionic conductivity comparable to many organic electrolyte solutions and a low decomposition propensity and low vapor pressure up to ˜300-400° C. This implies a generally low volatility and non-flammability and, hence, a much safer electrolyte for batteries. [0023] Ionic liquids are basically composed of organic ions that come in an essentially unlimited number of structural variations owing to the preparation ease of a large variety of their components. Thus, various kinds of salts can be used to design the ionic liquid that has the desired properties for a given application. These include, among others, imidazolium, pyrrolidinium and quaternary ammonium salts as cations and bis(trifluoromethanesulphonyl) imide, bis(fluorosulphonyl)imide, and hexafluorophosphate as anions. Based on their compositions, ionic liquids come in different classes that basically include aprotic, protic and zwitterionic types, each one suitable for a specific application . . . [0024] Relatively speaking, the combination of imidazolium- or sulfonium-based cations and complex halide anions such as . . . N(SO2 F)2 − . . . results in RTILs with good working conductivities.” Id. at [0022 – 24]. In other words, Zhamu teaches that additives found within an electrolyte may reduce dendrite formation and improve conductivity, and that ionic liquids comprising N—SO2F2- as an anionic component of a larger salt show this improvement. Further, these benefits may also apply to a side group of a larger molecule. Id. at [0016 -17].
Regarding “each independently,” this indicates each R1 receives separate treatment, meaning this includes an embodiment wherein both R1s are SO2F.
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolytic solution of Yamaguchi, such that the additive of Yamaguchi comprises N—SO2F instead of N—SO2Rf groups, because Zhamu teaches additives within an electrolyte comprising complex halide anions like N—SO2F improve conductivity and contribute to lithium capture, which in turn reduce dendrite formation.
Claim 2 is obvious over Yamaguchi, in view of Zhamu.
Regarding Claim 3, Claim 3 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
As previously described above, Zhamu teaches a rechargeable lithium ion battery, wherein the electrolyte may comprise “[0011] lithium-capturing groups” which contribute to providing “[0010] a simple, cost-effective, and easy-to-implement approach to preventing potential Li metal dendrite-induced internal short circuit and thermal runaway problems in various fast-charging Li-ion batteries.” Zhamu at [0010 – 11]. To summarize the Claim 2 analysis, Zhamu teaches that additives found within an electrolyte may reduce dendrite formation and improve conductivity, and that ionic liquids comprising N—SO2F2- as an anionic component of a larger salt show this improvement. Further, these benefits may also apply to a side group of a larger molecule. Id. at [0016 -17].
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolytic solution of Yamaguchi, such that the additive of Yamaguchi comprises two N—SO2F instead of N—SO2Rf groups, because Zhamu teaches additives within an electrolyte comprising complex halide anions like N—SO2F improve conductivity and contribute to lithium capture, which in turn reduce dendrite formation.
Claim 3 is obvious over Yamaguchi, in view of Zhamu.
Regarding Claim 9, Claim 9 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
Zhamu teaches the electrolyte may comprise a solvent, comprising vinylene carbonate, and teaches a “combination” solvent which may comprise multiple organic solvent components. Zhamu at [0046].
Yamaguchi teaches “in a preferred embodiment, the content of the additive is 0.05 to 5% by mass (typically 0.1 to 5% by mass, for example 0.5 to 3% by mass). If the content of the additive is too small, a sufficient additive effect tends to be hardly exhibited. If the content of the additive is too large, it may be difficult to prepare the non-aqueous electrolyte, or the additive may be easily deposited in the battery container depending on the time, use environment, or the like.” This lower bound is of interest because it demonstrates a lower threshold for secondary components of an electrolytic mixture to show measurable effects.
One of ordinary skill in the art before the effective filing rate of the claimed invention would find it obvious to further modify the solution of modified Yamaguchi such that it comprises vinylene carbonate in an amount of 0.01% by mass to 5.0% by mass with respect to a total amount of the nonaqueous electrolytic solution because below this threshold, effects are minimal, and above this threshold deposits of excess material may become an issue.
Claim 9 is obvious over Yamaguchi, in view of Zhamu.
Claims 10 is rejected under 35 U.S.C. 103 as being unpatentable over Yamaguchi, in view of Chapples, et. al. (EP2226627A1).
Regarding Claim 10, Claim 10 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
Yamaguchi is silent as to at least one compound selected from the group consisting of compounds represented by the following General Formulas (2) to (3); however, Yamaguchi teaches a supporting electrolyte which acts as a lithium salt, and specifies these may be one kind or two or more kinds. Yamaguchi at [p.3-4]. Yamaguchi teaches a benefit to utilizing an additive content of 0.05 to 5% by mass, because if the amount is too small effects are minimum, and above this range deposition of excess material may be an issue.
Chapples teaches an electrochemical device (an electrochemical gas sensor) comprising an anode and a cathode separated by an electrolyte, having a supporting / second component, which comprises methanesulfonylacetone. Chapples at [0035]. This second component meets General Formula (3) of Claim 10, described below:
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General Formula (3) of Claim 10.
in the General Formula (3), X represents a sulfonyl group or a ketone group, and R4and RS are each independently selected from aliphatic hydrocarbon groups having I to t0 carbon atoms, at least one selected from the group consisting of a fluorine atom, an oxygen atom, an unsaturated bond, and an ester bond may be present in the aliphatic hydrocarbon group. Here, methanesulfonylacetone comprises an R4 group which is methane, i.e. an aliphatic hydrocarbon having 1 carbon atom, an R5 group which is also methane, and an X group which is a ketone.
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A generic diagram of methanesulfonylacetone, as taught in Chapples; note: this image was generated via ChemSpider.
Chapples teaches the use of methanesulfonylacetone improves ease of handling and compatibility with other materials in the primary material (in the case of Chapples, this includes a fluorinated bis-sulfonimide, indicating some compatibility with the material of Yamaguchi.
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolyte solution of modified Yamaguchi, such that it also comprises the methanesulfonylacetone in an amount of 0.01% by mass to 5.0% by mass with respect to a total amount of the nonaqueous electrolytic solution, because Chapples teaches a benefit to ease of handling and compatibility, and because Yamaguchi teaches a benefit to preventing additional deposition of additive material.
Claim 10 is obvious over Yamaguchi, in view of Chapples.
Claims 5 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Yamaguchi, in view of Zhamu, and further in view of Kinoshita, et. al. (CN 111433964 A).
Regarding Claim 5, Claim 5 relies upon Claim 1. Claim 1 is anticipated by Yamaguchi.
Zhamu teaches a rechargeable lithium ion battery, wherein the electrolyte may comprise “[0011] lithium-capturing groups” which contribute to providing “[0010] a simple, cost-effective, and easy-to-implement approach to preventing potential Li metal dendrite-induced internal short circuit and thermal runaway problems in various fast-charging Li-ion batteries.” Zhamu at [0010 – 11]. Zhamu teaches “[0021] The lithium ion-capturing groups may contain ionic liquids, which are low melting temperature salts that are in a molten or liquid state when above a desired temperature . . . [0022] A typical and well-known ionic liquid is formed by the combination of a 1-ethyl-3-methylimidazolium (EMI) cation and an N,N-bis(trifluoromethane)sulphonamide (TFSI) anion. This combination gives a fluid with an ionic conductivity comparable to many organic electrolyte solutions and a low decomposition propensity and low vapor pressure up to ˜300-400° C. This implies a generally low volatility and non-flammability and, hence, a much safer electrolyte for batteries.” In other words, Zhamu teaches that additives found within an electrolyte may reduce dendrite formation and improve conductivity, and that ionic liquids comprising N—SO2F2- as an anionic component of a larger salt show this improvement. Further, these benefits may also apply to a side group of a larger molecule. Id. at [0016 -17].
Kinoshita teaches an electrolytic solution which comprises an auxiliary agent, wherein N,N-diethylmethanesulfonamide may be the auxiliary agent, as well as “nitrogen contain compounds such as . . . methylsuccinimide, and . . . dimethyl succinate,” as well as fluorinated compounds. Kinoshita at [p.42 - 43]. Further, Kinoshita teaches “[b]y adding these additives, the capacity retention characteristics and cycle characteristics after high-temperature storage can be improved.” Id. These materials may be utilized alone or in combination (“[p.43] These may be used individually by 1 type, and may be used in combination of 2 or more types”); the presence of similar succinates, malonamides, and oxalates, alongside the methylated methanesulfonamide, indicates or at least implies, for example, a sulfonamide would provide similar improvements to capacity retention characterizations if it included an additional methyl group, as in the case of “N,N-dimethylmethanesulfonamide, [and] N,N-diethylmethanesulfonamide.” Id.
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolytic solution of Yamaguchi, such that the compound represented by the General Formula (1) is a compound represented by the following Formula (1a), because Kinoshita teaches a benefit to capacity retention.
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Formula 1(a) of Claim 5, differing from the material of Claim 2 primarily by the inclusion of the additional methyl groups.
Claim 5 is obvious over Yamaguchi, in view of Zhamu, and further in view of Kinoshita.
Regarding Claim 13, Yamaguchi teaches a compound 6 (also referred to as additive B-4), wherein a diamide type molecule comprises R2 groups which are lithium ions, and R1 groups which are SO2Rf, wherein Rf is “a linear alkyl group having . . . 4 carbon atoms . . . and any hydrogen atom of the alkyl group may be substituted with a fluorine atom [in this case, all of the hydrogen atoms are replaced].” Yamaguchi at [p.16].
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Yamaguchi at line 10, page 16, showing the synthesis of compound 6.
Zhamu teaches a rechargeable lithium ion battery, wherein the electrolyte may comprise “[0011] lithium-capturing groups” which contribute to providing “[0010] a simple, cost-effective, and easy-to-implement approach to preventing potential Li metal dendrite-induced internal short circuit and thermal runaway problems in various fast-charging Li-ion batteries.” Zhamu at [0010 – 11]. Zhamu teaches “[0021] The lithium ion-capturing groups may contain ionic liquids, which are low melting temperature salts that are in a molten or liquid state when above a desired temperature . . . [0022] A typical and well-known ionic liquid is formed by the combination of a 1-ethyl-3-methylimidazolium (EMI) cation and an N,N-bis(trifluoromethane)sulphonamide (TFSI) anion. This combination gives a fluid with an ionic conductivity comparable to many organic electrolyte solutions and a low decomposition propensity and low vapor pressure up to ˜300-400° C. This implies a generally low volatility and non-flammability and, hence, a much safer electrolyte for batteries.” In other words, Zhamu teaches that additives found within an electrolyte may reduce dendrite formation and improve conductivity, and that ionic liquids comprising N—SO2F2- as an anionic component of a larger salt show this improvement. Further, these benefits may also apply to a side group of a larger molecule. Id. at [0016 -17].
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolytic solution of Yamaguchi, such that the additive of Yamaguchi comprises N—SO2F instead of N—SO2Rf groups, because Zhamu teaches additives within an electrolyte comprising complex halide anions like N—SO2F improve conductivity and contribute to lithium capture, which in turn reduce dendrite formation.
Kinoshita teaches an electrolytic solution which comprises an auxiliary agent, wherein N,N-diethylmethanesulfonamide may be the auxiliary agent, as well as “nitrogen contain compounds such as . . . methyl succinimide, and . . . dimethyl succinate,” as well as fluorinated compounds. Kinoshita at [p.43]. These materials may be utilized alone or in combination; the presence of similar succinates and oxalates, alongside the methylated methanesulfonamide, indicates or at least implies, for example, a sulfonamide would provide similar improvements to capacity retention characterizations if it included an additional methyl group, as in the case of “N,N-dimethylmethanesulfonamide, [and] N,N-diethylmethanesulfonamide.”
One of ordinary skill in the art before the effective filing date of the claimed invention would find it obvious to modify the electrolytic solution of Yamaguchi, such that the compound represented by the General Formula (1) is a compound represented by the following Formula (1a), because Kinoshita teaches a benefit to capacity retention.
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Formula 1(a) of Claim 13, differing from the material of Claim 2 primarily by the inclusion of the additional methyl groups.
Claim 13 is obvious over Yamaguchi, in view of Zhamu, and further in view of Kinoshita.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KRISHNA RAJAN HAMMOND whose telephone number is (571)272-9997. The examiner can normally be reached 9:00 - 6:30 PM M-F.
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/K.R.H./Examiner , Art Unit 1725
/NICOLE M. BUIE-HATCHER/Supervisory Patent Examiner, Art Unit 1725
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