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 .
Response to Amendment
This is a final Office action in response to Applicant’s remarks and amendments filed on 06/02/2026. Claims 1, 7, and 17 are amended. Claims 2, 9, and 19 are cancelled. Claims 5 – 6 and 14 remain withdrawn. Claims 1, 3 – 4, 7 – 8, 10 – 13, 15 – 18, and 20 are pending in the current Office action.
The 35 U.S.C. 103 rejections set forth in the previous Office action are withdrawn. A new grounds of rejection, necessitated by applicant’s amendment, is established below.
Response to Arguments
Applicant’s arguments with respect to claim(s) 1 and the previously cited prior art: Burkhardt, Kim, and Deng have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant's arguments filed 06/02/2026 regarding the unexpected and synergistic effects of combination of a fluorinated acrylic ester and fluorinated cyclic carbonate have been fully considered but they are not persuasive. Specifically, applicant argues, based on the data in Table 1 and the Declaration filed 09/11/2025, that the claimed combination of a fluorinated acrylic ester and fluorinated cyclic carbonate provides a synergistic effect on the high temperature performances on an electrochemical cell with silicon containing anodes and provides less swelling without deteriorating other performance parameters ,such as the resistance/DC-IR, of the electrolyte formulations (See pg. 13 of arguments).
Examiner acknowledges that based on the data {i.e. EL1-EL2 vs. EL3-6} in Table 1 of the instant specification and the Declaration that, the combination of both a fluorinated acrylic ester and fluorinated cyclic carbonate provides superior capacity retention at both 25°C and 45°C in addition to less swelling without deteriorating other performance parameters, such as the resistance/DC-IR, of the example batteries; however, the examiner notes that the combination of the fluorinated acrylic ester and fluorinated cyclic carbonate only appears critical/the alleged synergistic effects of the combination are achieved when the fluorinated acrylic ester is DFEA; the DFEA is included in an amount of 2.3 wt% - 70 wt% of the electrolyte composition; the fluorinated cyclic carbonate is FEC; and the FEC is included in the amount of 2.9 wt% or 5 wt%, and as claim 1 allows for a broader selection of fluorinated acrylic ester and fluorinated cyclic carbonate as well as a broader amount of fluorinated acrylic ester and fluorinated cyclic carbonate, it is unclear if the combination would be critical for achieving applicant’s alleged unexpected results across the broader selection and amount of fluorinated acrylic ester and fluorinated cyclic carbonate {i.e. the claimed invention appears incommensurate in scope with the invention argued to provide the unexpected results} and applicant’s arguments regarding the unexpected results and synergistic effects of the claimed combination is rendered unpersuasive.
Claim Objections
Claims 1 is objected to because of the following informalities:
In lines 6 and 10, a space should be included between the numbers and the “wt%” units in the claimed wt% ranges.
In line 13, the letter “a” in “SiOa/C” and “Si/SiOa/C” should be a subscript.
The use of parenthesis around 45°C should be avoided as it may be unclear as to whether terminology within parenthesis is actually positively recited. For the purpose of this Office action, Examiner is interpreting the subject matter within the parenthesis as further limiting the claimed invention and therefore the subject matter within the parenthesis is interpreted as having patentable weight on the claimed invention. Instead of “high temperature (at 45°C) cycling performance..” the examiner recommends changing to – cycling performance at 45 °C- (This also incorporates a space between 45 and the °C).
Appropriate correction is required.
Claims 7 and 17 are objected to because of the following informalities: A space should be included between the numbers and the “wt%” units in the claimed wt% ranges . Appropriate correction is required.
Claims 20 is objected to because of the following informalities: The use of units in claim 20 is inconsistent with other claims {i.e. claims 1, 7, and 17}. Specifically, “ vol%” should be included after “8” and after “10” for consistency. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 1 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. {Examiner Note: For citations of the instant specification the examiner utilizes the US PG Pub. version of the instant application: US 2023/0006255 A1}.
Specifically, the limitation “wherein the addition of the fluorinated acyclic carboxylic acid ester compound and the fluorinated cyclic carbonate compound to the electrolyte composition improves high temperature (at 45°C) cycling performance and stability of the electrochemical cell compared to when an electrochemical cell does not comprise both in the same amount” renders the claim indefinite for the following reasons:
The recitation “the addition” makes it unclear if the limitation is referring the previously recited fluorinated acyclic carboxylic acid ester compound and fluorinated cyclic carbonate compound or if the limitation is referring to adding an additional fluorinated acyclic carboxylic acid ester compound and fluorinated cyclic carbonate to the electrolyte composition. That is, in previous limitations of claim 1, the fluorinated acyclic carboxylic acid ester compound and the fluorinated cyclic carbonate compound is already established to be included within the electrolyte composition.
The use of parenthesis in the recitation “high temperature (at 45°C) cycling performance” makes it unclear whether the subject matter contained within the parenthesis is part of the claimed invention [See MPEP 2173.05(d)].
The recitation “compared to when an electrochemical cell does not comprise both in the same amount” renders the claimed indefinite because the use of the negative limitation “does not comprise both in the same amount” to further limit the claimed “an electrochemical cell” makes it unclear as to what the “an electrochemical cell” includes/does not include in comparison to the claimed electrochemical cell {i.e. there is no clear basis of comparison established by the claim}. For instance, “ an electrochemical cell that does not comprise both in the same amount” includes within its scope (1) an electrochemical cell that has amounts of fluorinated acyclic carboxylic acid ester compound and fluorinated cyclic carbonate compound that are different from each other; (2) an electrochemical cell that has amounts of fluorinated acyclic carboxylic acid ester compound and fluorinated cyclic carbonate compound that outside of the ranges recited in instant claim 1; (3) an electrochemical cell that does not include any fluorinated acyclic carboxylic acid ester compound and/or fluorinated cyclic carbonate compound; etc. Furthermore, such a limitation further encompasses within its scope electrochemical cells that also differ in, for example, anode active material type which one with ordinary skill in the art would appreciate/recognize would necessarily perform differently than an electrochemical cell including a silicon and carbon containing composite active material as claimed in instant claim 1.
Therefore, for the purpose of this Office action, the examiner is interpreting the instant limitation as – wherein the electrochemical cell has improved cycling performance at 45 °C and stability compared to an electrochemical cell that is the same as the electrochemical cell except for: based on a total weight of the electrolyte, the amount of fluorinated acyclic carboxylic acid is ester compound is outside of the range of from 0.5 wt% to 70 wt%, and, based on a total weight of the electrolyte, the amount of fluorinated cyclic carbonate compound is outside of the range 0.5 wt% to 10 wt% --. This interpretation appears to be supported by Table 1 and [0120];[0137 – 0140] of the instant specification.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1, 3 – 4, 7, 10 – 13, 15 – 16, 19, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Uehara (US 2014/0017572 A1 – cited in 06/01/2022 IDS) in view of Miyazaki (US PG Pub. 2015/0263334 A1).
Regarding Claim 1, 3 – 4, 7 – 8, and 17 – 18, Uehara discloses an electrochemical cell (Fig. 1; [0026];[0118 – 0119]) comprising an anode (negative electrode; Fig. 1, a; [0079];[[0018 – 0019]), a cathode (positive electrode; Fig. 1, c; [0094];[0118 – 0119]) and an electrolyte composition ([0041];[0115];[0118]), wherein said anode comprises an anode active material ([0079]).
In examples 27 – 52, Uehara explicitly teaches lithium secondary battery embodiments where the anode active material is Si/SiO/C (See Table 2; [0086 – 0087];[0136 – 0137]), as such, Uehara further discloses an electrochemical cell embodiment where the anode active material is a combination of as least a carbon material and a silicon material and further within the claimed selection of a composite material selected from Si/C, SiOa/C, and Si/SiOa/C with o < a < 2.
Uehara further discloses an embodiment of the electrochemical cell with the Si/SiO/C composite anode active material, i.e. example 30, where the electrolyte comprises:
A non-fluorinated solvent, that is Uehara explicitly teaches the example electrolyte having a solvent of EC/PC/DMC/EMC/DEC which are non-fluorinated carbonates (Refer to Example 30 in Table 2; [0070];[0125];[0135];[0137]).
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Chemical structure of the corresponding fluorinated acyclic carboxylic acid of ester in Example 30 of Uehara.
A fluorinated acyclic carboxylic acid of ester of within the claimed general formula, that is Uehara explicitly teaches the example electrolyte including a chain-type fluorinated ether represented by chemical formula (1) where R1 is -CH3 and R2 is -CH2CHF2 (Refer to Example 30 in Table 2; [0044 – 0045]) that, as shown by the chemical structures above, is 2,2-difluoroethylacetate, which is within the scope of claimed formula 1 and the claimed selection of fluorinated acyclic carboxylic acid of esters of claim 3 and further is the fluorinated acyclic carboxylic acid of ester of claim 4.
And an electrolyte salt, that is Uehara explicitly teaches the example electrolyte including LiPF6 (Refer to Example 30 in Table 2; [0078];[0125];[0135];[0137]).
As shown in Example 30 of Table 2, Uehara teaches including 10 vol% of 2,2-difluoroethylacetate {i.e. the content of the fluorinated acyclic carboxylic acid of ester}; therefore, Uehara does not particularly disclose, based on a total weight of the electrolyte, a content of the fluorinated acyclic carboxylic acid being 0.5 – 70 wt%; 0.5 – 10 wt% (Claim 7), or further 2 – 5 wt% (Claim 17).
Generally, however, Uehara teaches the content of the chain-type fluorinated ester being most preferably 1 – 15 mass% of the electrolyte ([0053]). As such Uehara at least suggest including a content of 2,2-difluoroethylacetate that is within the range of claim 1, overlaps the range of claim 7 and further encompasses range of claim 17.
Uehara teaches that a content of 0.1 mass% or more of the chain-type fluorinated ester allows for more effective reduction in the decomposition of the electrolyte liquid, and that a content of 30 mass% or less reduces the internal resistance of the battery due to excess generation caused by the SEI film formed by the chain-type fluorinated ester ([0053]). Uehara further teaches generally that when the content of fluorinated electrolyte solvents is increased, LiPF6 may have more difficulty dissolving and that the carbonate-based, non-fluorinated solvent of the electrolyte improves ion dissociation of the electrolyte liquid, increases electrolyte viscosity, and improves ion mobility ([0071 – 0072]).
Therefore, selection of an amount of 2,2-difluoroethylacetate within overlapping portion of the claimed ranges and the range taught by Uehara for the example electrolyte embodiment would have been obvious to one with ordinary skill in the art, before the effective filing date of the claimed invention, in order to optimize/balance the effects of the 2,2-difluoroethylacetate component {i.e. effective reduction in the decomposition of the electrolyte liquid vs. increases in internal resistance} in the electrolyte in addition to optimizing the effects of the carbonate solvents {i.e. solvents affects the ion dissociation of the electrolyte liquid, electrolyte viscosity, and ion mobility}, with a reasonable expectation of success and without undue experimentation [See MPEP 2144.05(II)].
Uehara also teaches including a chain-type fluorinated ether compound within the electrolyte (Table 2; [0054];[0069]). Uehara further teaches using the electrolyte liquid containing a chain-type fluorinated ester compound and a chain-type fluorinated ether compound with negative electrodes containing silicon because the electrolyte reduces volume change due to charge and discharge as well as improves cycle properties and the resistance change ratio of the battery ([0082];[0086]). As the positive electrode active material of the example embodiment, Uehara teaches using a lithium nickelate ([0123]).
Uehara does not explicitly disclose the electrolyte embodiment further comprising 0.5 wt% to 10 wt%, based on a total weight of the electrolyte, a fluorinated cyclic carbonate compound.
Miyazaki teaches, with respect to a nonaqueous secondary battery, teaches a battery comprising a lithium composite oxide positive electrode and a nonaqueous electrolyte that contains 40% or less by volume of ethylene carbonate to the non-aqueous solvent and 0.5 to 10% by mass of fluoroethylene carbonate to the non-aqueous electrolyte ([0015];[0030 – 0032]). Miyazaki further teaches that the fluoroethylene carbonate enhances storage characteristics and cycle characteristics of the battery ([0033]).
Since, as established above Uehara is concerned with achieving improved cycle properties and teaches an example electrolyte composition including 40% or less by volume of ethylene carbonate {i.e. 20 vol%} ([0125]), it would have been obvious to one with ordinary skill in the art, before the effective filing date of the claimed invention, to modify the electrolyte embodiment of Uehara by adding fluoroethylene carbonate, as taught by Miyazaki, in the interest of enhancing the storage characteristics and further enhancing the cycle characteristics of Uehara’s battery with a reasonable expectation of success.
By including fluoroethylene carbonate as taught by Miyazaki, modified Uehara electrolyte further includes a fluorinated cyclic carbonate compound within the claimed selection of claim 8 and claim 18. Furthermore, modified Uehara includes a content of fluorinated cyclic carbonate of 0.5 to 10% by mass of the electrolyte, which is within the claimed range of 0.5 wt% - 10 wt% and encompasses the claimed ranges of 1 wt% to 9 wt% (Claim 7) and 2 wt% to 5 wt% (Claim 17) based on a total weight of the electrolyte.
Miyazaki further teaches including 0.5% or more by mass of fluoroethylene carbonate to achieve enhanced storage characteristics and cycle characteristics and including 10% or less by mass of fluoroethylene carbonate, because fluoroethylene carbonate can react with the lithium transition-metal composite oxide of the positive electrode active material to generate gas and cause swelling during high temperature storage when its content is large ([0015];[0033]).
Uehara, as established above, further teaches generally that when the content of fluorinated electrolyte solvents is increased, LiPF6 may have more difficulty dissolving and that the carbonate, non-fluorinated solvent of the electrolyte improves ion dissociation of the electrolyte liquid, increases electrolyte viscosity, and improved ion mobility ([0071 – 0072]). Uehara further teaches using the electrolyte liquid containing a chain-type fluorinated ester compound and a chain-type fluorinated ether compound with negative electrodes containing silicon because the electrolyte reduces volume change due to charge and discharge as well as improves cycle properties and the resistance change ratio of the battery ([0082];[0086]). As the positive electrode active material of the example embodiment, Uehara teaches using a lithium nickelate ([0123]).
Therefore, as Uehara is concerned with controlling volume change of the battery {i.e. swelling}, improving cycle properties, and, in the example embodiment, teaches a battery with a lithium nickel-based positive electrode material, selection of an amount of fluoroethylene carbonate within the overlapping portion of the claimed ranges and range taught by Miyazaki when modifying the electrolyte of Uehara to include fluoroethylene carbonate would have been obvious to one with ordinary skill in the art, before the effective filing date of the claimed invention, in order to optimize the beneficial effects of the fluoroethylene carbonate {i.e. enhanced storage characteristics and cycle characteristics} while ensuring that the swelling the battery is minimized and the amount of fluorinated electrolyte components is low within the electrolyte, with a reasonable expectation of success and without undue experimentation [See MPEP 2144.05(II)].
Modified Uehara does not explicitly disclose wherein the electrochemical cell has improved cycling performance at 45°C and stability compared to an electrochemical cell that is the same as the electrochemical cell except for, based on a total weight of the electrolyte, the amount of fluorinated acyclic carboxylic acid is ester compound is outside of the range of from 0.5 wt% to 70 wt%, and, based on a total weight of the electrolyte, the amount of fluorinated cyclic carbonate compound is outside of the range 0.5 wt% to 10 wt%; however, one with ordinary skill in the art would reasonably expect modified Uehara to provide/possess the claimed high temperature (at 45°C) cycling performance improvement and electrochemical cell stability, because, as established above, modified Uehara includes a combination of fluorinated acyclic carboxylic acid ester compound {i.e. 2,2-difluoroethylacetate} and fluorinated cyclic carbonate compound {i.e. fluoroethylene carbonate} in amounts taught by the applicant to be capable of achieving the improved cycling performance 45°C and electrochemical cell stability (Refer to instant specification: Table 1 and [0120]), as well as battery structure similar to the applicant {i.e. nonfluorinated carbonate-based solvent for the electrolyte (Instant Specification: [0074 – 0075]), Si/SiO/C anode (Instant specification: [0043]), and lithium transition metal composite oxide cathode (Instant Specification: [0048 – 0056])}; and further because Uehara already suggests achieving reduced battery expansion and/or improved cycling performance at high temperature through the use of a fluorinated acyclic carboxylic acid ester compound {i.e. 2,2-difluoroethylacetate} (Refer to results of Example 30 in Table 2 of Uehara and Uehara: [0127 – 130]) and Miyazaki suggests achieving improved cycling characteristics as well as reduced swelling at high temperature via the use of fluoroethylene carbonate (Refer to Table 6 in Miyazaki and Miyazaki: [0032 – 0033]). Furthermore, regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Regarding Claim 10 and 15, modified Uehara discloses all limitations as set forth above. As established above, Uehara exemplifies an electrolyte having a solvent of EC/PC/DMC/EMC/DEC which are non-fluorinated carbonates (Refer to Example 30 in Table 2; [0070];[0125];[0135];[0137]). EC and PC are both non-fluorinated cyclic carbonates ([0073]) (Claim 10) and further are within the claimed selection of ethylene carbonate, propylene carbonate, and mixtures thereof (Claim 15).
Regarding Claim 11 and 16, modified Uehara discloses all limitations as set forth above. As established above, Uehara exemplifies an electrolyte having a solvent of EC/PC/DMC/EMC/DEC which are non-fluorinated carbonates (Refer to Example 30 in Table 2; [0070];[0125];[0135];[0137]). DMC, EMC and DEC are all non-fluorinated acyclic carbonates ([0073]) (Claim 11) and further are within the claimed selection of ethyl methyl carbonate, dimethyl carbonate, diethyl carbonate; and mixtures thereof (Claim 16).
Regarding Claim 13, modified Uehara discloses all limitations as set forth above. Uehara further discloses an electronic device, transportation device or telecommunications device comprising the battery ([0190]).
Regarding Claim 20, modified Uehara discloses all limitations set forth above. As established above, Uehara exemplifies an electrolyte having a solvent of EC/PC/DMC/EMC/DEC which are non-fluorinated carbonates in a volume ratio of 20/20/20/20/20 (Refer to Example 30 in Table 2; [0070];[0125];[0135];[0137]). DMC, EMC and DEC are all non-fluorinated acyclic carbonates ([0073]). Therefore, Uehara discloses a non-fluorinated solvent comprising 60 vol% of non-fluorinated acyclic carbonate which is within the claimed range of 10 – 85 vol% and further is a solvent composition within the claimed scope of wherein the non-fluorinated solvent comprises from 8 to 30 vol% of a non-fluorinated cyclic carbonate and/or from 10 to vol% to 85 vol% of a non-fluorinated acyclic carbonate, based on a total volume of the solvent..
Claim(s) 12 is rejected under 35 U.S.C. 103 as being unpatentable over Uehara (US 2014/0017572 A1) in view of Miyazaki (US PG Pub. 2015/0263334 A1) as applied to claim 1 above, and further in view of Burkhardt (WO2018011062A2 – cited in previous Office action mailed 03/03/2026).
Regarding Claim 12, modified Uehara discloses all limitations as set forth above. Uehara further teaches that the non-aqueous solvent can also include compounds other than carbonate compounds like γ-lactones such as γ-butyrolactone; chain-type ethers such as 1,2-ethoxyethane (DEE) and ethoxy methoxy ethane (EME); cyclic-type ethers such as tetrahydrofuran and 2-methyl tetrahydrofuran; aprotic organic solvents such as dimethylsulfoxide, 1,3-dioxolan, formamide, acetamide, dimethylformamide, dioxolane, acetonitrile, propylnitrile, nitromethane, ethyl monoglyme, phosphoric acid triesters, trimethoxy methane, dioxolane derivatives, sulfolane, methyl sulfolane, 1,3-dimethyl-2-imidazolidinone, 3-methyl-2-oxazolidinone, propylene carbonate derivatives, tetrahydrofuran derivatives, ethyl ether, 1,3-propane sultone, anisole, N-methylpyrrolidone, and fluorinated carboxylates. ([0074]).
Uehara does not explicitly disclose an embodiment wherein the electrolyte composition further comprises an additive selected from a lithium boron compound, a cyclic sultone, a cyclic sulfate, a cyclic carboxylic acid anhydride, or a combination thereof.
Burkhardt, also directed to nonaqueous electrolyte compositions for lithium-ion batteries, teaches electrolyte compositions comprising at least one at least one electrolyte component selected from i) a fluorinated acyclic carboxylic acid ester, ii) a fluorinated acyclic carbonate, iii) a fluorinated acyclic ether, or iv) a mixture thereof (Pg. 1, lines 5 – 12). Burkhardt further teaches have the electrolyte further include additives useful for lithium-ion battery electrolyte compositions (Pg. 22, lines 30 – 31; Pg. 23, lines 1 – 4). Burkhardt particularly exemplifies using gas-reduction additives and the list of gas-reduction additives taught by Burkhardt overlaps in scope with Uehara’s taught additional solvents (Pg. 24, lines 10 – 31; Pg. 25, lines 1 – 10). For example, 1,3-propane sultone is a gas-reduction additive that is taught to be used by both Burkardt and Uehara, and further is a cyclic sultone which is included within the claimed scope of additives.
Since Uehara is concerned with reducing gas generation ([0072]), it would have been obvious to one with ordinary skill in the art, before the effective filing date of the claimed invention, to further modify the electrolyte embodiment of Uehara to include an additive such as 1,3-propane sultone, which is within the claimed scope of additives, because such a selection of additive would be from a finite list of additional electrolyte material and thus would have a reasonable expectation of success in being a suitable additive for the electrolyte composition exemplified in Uehara [See MPEP 2133(I)(E)] and further, as taught by Burkhardt, would have a reasonable expectation of success in furthering Uehara’s goal of reducing gas generation within the battery.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ARYANA Y ORTIZ whose telephone number is (571)270-5986. The examiner can normally be reached M-F 7:00 AM - 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jonathan Leong can be reached at (571) 270-1292. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.Y.O./Examiner, Art Unit 1751
/JONATHAN G LEONG/Supervisory Patent Examiner, Art Unit 1751 8/21/2026
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