Prosecution Insights
Last updated: September 17, 2026
Application No. 18/539,576

ELECTROLYTES INCLUDING OXALATE-BASED ADDITIVES FOR BATTERIES THAT CYCLE LITHIUM IONS AND BATTERIES INCLUDING THE SAME

Non-Final OA §103
Filed
Dec 14, 2023
Examiner
LEONARD, MICHELLE TURNER
Art Unit
Tech Center
Assignee
GM Global Technology Operatins LLC
OA Round
1 (Non-Final)
70%
Grant Probability
Favorable
1-2
OA Rounds
8m
Est. Remaining
82%
With Interview

Examiner Intelligence

Grants 70% — above average
70%
Career Allowance Rate
79 granted / 113 resolved
+9.9% vs TC avg
Moderate +12% lift
Without
With
+12.0%
Interview Lift
resolved cases with interview
Typical timeline
3y 5m
Avg Prosecution
22 currently pending
Career history
143
Total Applications
across all art units

Statute-Specific Performance

§101
0.5%
-39.5% vs TC avg
§103
58.7%
+18.7% vs TC avg
§102
20.5%
-19.5% vs TC avg
§112
17.1%
-22.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 113 resolved cases

Office Action

§103
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 § 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) 1-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. [US20160329599A1] as provided on the IDS dated 11/5/2024 and the German Office Action cited on the IDS, hereinafter Kim, in further view of Xiao et al. [US20190363345A1], hereinafter Xiao. Regarding Claim 1, Kim discloses a battery that cycles lithium ions [Kim title, abstract, claim 13 and throughout], the battery comprising: a positive electrode comprising an electroactive material comprising a lithium- and manganese-containing oxide [Kim 0065-0067 and throughout]; and an electrolyte comprising [Kim abstract and throughout]: an organic solvent [Kim abstract, 0022-0023, 0055-0057, and throughout]; a lithium salt in the organic solvent [Kim abstract, 0022-0026, 0033, 0058-0059, 0077, 0087, and throughout]; and an oxalate-based additive in the organic solvent [Kim abstract 0037-0040, 0044, 0079-0087, and throughout], the oxalate-based additive comprising at least one oxalate compound selected from the group consisting of bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout] tert-butyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, fourth structure], methyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, first structure], ethyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, second structure], bis(2-chloroethyl) oxalate [Kim 0012-0016, 0033-0040, and throughout, formula 1 where R2 may be (C1-C5)alkyl substituted with halogen reads on the oxalate]. Kim does not explicitly teach the electrolyte infiltrating the positive electrode. Xiao teaches lithium-ion batteries [Xiao 0001-0004 and throughout] where an electrolyte infiltrates the positive electrode [Xiao 0022, 0068, and throughout]. It would have been obvious to one of ordinary skill in the art before the effective filing date to combine Xiao’s teaching with Kim’s lithium-ion battery for the predictable result of a lithium-ion battery reversibly transporting lithium ions [Xiao 0002-0005, 0087, 0091, and throughout]. MPEP2143 (A) Combining prior art elements according to known methods to yield predictable results. Regarding Claim 2, modified Kim discloses the battery of claim 1, wherein the oxalate-based additive comprises at least one fluorinated oxalate compound selected from the group consisting of bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout] tert-butyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, fourth structure], methyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, first structure], and ethyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, second structure]. Regarding Claim 3, modified Kim discloses the battery of claim 1, wherein the oxalate-based additive constitutes, by weight, greater than or equal to 0.001% and less than or equal to 10% of the electrolyte [Kim 0018, 0021, 0044, 0078-0079, 0097 and throughout, Kim teaches an example with 1 wt % bis(2,2,2-trifluoroethyl) oxalate [Kim 0078-0079, 0097] which anticipates the claimed range. Further, Kim teaches 0.1 to 5.0 % [0018, 0021, 0044], which overlaps and obviates the claimed range. Per MPEP 2144.05, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.]. Regarding Claim 4, modified Kim discloses the battery of claim 1, wherein the oxalate-based additive comprises bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout]. Regarding Claim 5, modified Kim discloses the battery of claim 4, wherein the bis(2,2,2-trifluoroethyl) oxalate constitutes, by weight, greater than or equal to 0.1% and less than or equal to 2% of the electrolyte [Kim 0018, 0021, 0044, 0078-0079, 0097 and throughout, Kim teaches an example with 1 wt % bis(2,2,2-trifluoroethyl) oxalate [Kim 0078-0079, 0097] which anticipates the claimed range. Further, Kim teaches 0.1 to 5.0 % [0018, 0021, 0044] and preferably 1 wt % to 3 wt %, which overlaps and obviates the claimed range. Per MPEP 2144.05, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.]. Regarding Claim 6, modified Kim discloses the battery of claim 1, wherein the oxalate-based additive further comprises at least one other compound selected from the group consisting of lithium oxalate, lithium difluorophosphate, lithium bis(oxalato)borate [Kim 0020 and throughout], lithium difluoro(oxalato)borate [Kim 0020 and throughout], and lithium bis(trifluoromethanesulfonyl)imide [Kim 0024, Kim teaches bis(trifluoromethanesulfonyl)imide as a salt; however, since one or more salts may be added, the limitation is met by Kim.]. Regarding Claim 7, modified Kim discloses the battery of claim 1, wherein the electroactive material of the positive electrode comprises a lithium manganese-based oxide represented by the formula LiMeO2 [Kim 0066], LiMe2O4[Kim 0065-0067] and/or Li1+xMe1-xO2 [Kim 0066], where Me comprises a transition metal selected from the group consisting of Co, Ni, Mn, Fe, Al, and V [Kim 0065-0067], where Me comprises, by weight, greater than or equal to 50% manganese (Mn) [Kim 0065-0067, since A, B, E, G, Q, and J can be Mn in the formulas in 0066, Mn equal to or greater than 50% is met by Kim.], and where 0<x≤0.33 [Kim 0066, x is in the claimed range when a in Kim’s formulas of 0066 is in the range of greater 1 or less than or equal to 1.33]. Regarding Claim 8, modified Kim discloses the battery of claim 1, wherein the lithium salt comprises lithium hexafluorophosphate (LiPF6) [Kim 0024, 0058, 0077 and throughout]. Regarding Claim 9, modified Kim discloses the battery of claim 1, wherein the organic solvent comprises a linear carbonate and a cyclic carbonate [Kim 0022-0023]. Regarding Claim 10, modified Kim discloses the battery of claim 1, wherein the organic solvent comprises fluoroethylene carbonate (FEC) [Kim 0022-0023] and diethyl carbonate (DEC) [Kim 0022-0023, 0056, Kim teaches the FEC as a cyclic carbonate and DEC as a linear carbonate, and further teaches the linear and cyclic carbonates are mixed.]. Regarding Claim 11, Kim discloses a battery that cycles lithium ions [Kim title, abstract, claim 13 and throughout], the battery comprising: a negative electrode comprising an electroactive negative electrode material [Kim 0068-0074]; a positive electrode comprising an electroactive positive electrode material [Kim 0065-0067 and throughout] comprising a lithium manganese-based oxide represented by the formula LiMeO2 [Kim 0066], LiMe2O4[Kim 0065-0067] and/or Li1+xMe1-xO2 [Kim 0066], where Me comprises a transition metal selected from the group consisting of Co, Ni, Mn, Fe, Al, and V [Kim 0065-0067], where Me comprises, by weight, greater than or equal to 50% manganese (Mn) [Kim 0065-0067, since A, B, E, G, Q, and J can be Mn in the formulas in 0066, Mn equal to or greater than 50% is met by Kim.], and where 0<x≤0.33 [Kim 0066, x is in the claimed range when a in Kim’s formulas of 0066 is in the range of greater 1 or less than or equal to 1.33]. an electrolyte comprising [Kim abstract and throughout]: an organic solvent [Kim abstract, 0022-0023, 0055-0057, and throughout]; a lithium salt in the organic solvent [Kim abstract, 0022-0026, 0033, 0058-0059, 0077, 0087, and throughout]; and an oxalate-based additive in the organic solvent [Kim abstract 0037-0040, 0044, 0079-0087, and throughout], the oxalate-based additive comprising at least one oxalate compound selected from the group consisting of bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout] tert-butyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, fourth structure], methyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, first structure], ethyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, second structure], bis(2-chloroethyl) oxalate [Kim 0012-0016, 0033-0040, and throughout, formula 1 where R2 may be (C1-C5)alkyl substituted with halogen reads on the oxalate]. Kim does not explicitly teach the electrolyte infiltrating the positive electrode. Xiao teaches lithium-ion batteries [Xiao 0001-0004 and throughout] where an electrolyte infiltrates the positive electrode [Xiao 0022, 0068, and throughout]. It would have been obvious to one of ordinary skill in the art before the effective filing date to combine Xiao’s teaching with Kim’s lithium-ion battery for the predictable result of a lithium-ion battery reversibly transporting lithium ions [Xiao 0002-0005, 0087, 0091, and throughout]. MPEP2143 (A) Combining prior art elements according to known methods to yield predictable results. Regarding Claim 12, modified Kim discloses the battery of claim 11, wherein the oxalate-based additive comprises at least one fluorinated oxalate compound selected from the group consisting of bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout] tert-butyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, fourth structure], methyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, first structure], and ethyl 2,2,2-trifluoroethyl oxalate [Kim 0012-0017, 0033-0040, and throughout, second structure]. Regarding Claim 13, modified Kim discloses the battery of claim 11, wherein the oxalate-based additive constitutes, by weight, greater than or equal to 0.001% and less than or equal to 10% of the electrolyte [Kim 0018, 0021, 0044, 0078-0079, 0097 and throughout, Kim teaches an example with 1 wt % bis(2,2,2-trifluoroethyl) oxalate [Kim 0078-0079, 0097] which anticipates the claimed range. Further, Kim teaches 0.1 to 5.0 % [0018, 0021, 0044], which overlaps and obviates the claimed range. Per MPEP 2144.05, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.]. Regarding Claim 14, modified Kim discloses the battery of claim 11, wherein the oxalate-based additive comprises bis(2,2,2-trifluoroethyl) oxalate [Kim 0012-0017, 0033-0040, 0078-0079, 0097 (PEA46), and throughout]. Regarding Claim 15, modified Kim discloses the battery of claim 14, wherein the bis(2,2,2-trifluoroethyl) oxalate constitutes, by weight, greater than or equal to 0.1% and less than or equal to 2% of the electrolyte [Kim 0018, 0021, 0044, 0078-0079, 0097 and throughout, Kim teaches an example with 1 wt % bis(2,2,2-trifluoroethyl) oxalate [Kim 0078-0079, 0097] which anticipates the claimed range. Further, Kim teaches 0.1 to 5.0 % [0018, 0021, 0044] and preferably 1 wt % to 3 wt %, which overlaps and obviates the claimed range. Per MPEP 2144.05, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.]. Regarding Claim 16, modified Kim discloses the battery of claim 11, wherein the oxalate-based additive further comprises at least one other compound selected from the group consisting of lithium oxalate, lithium difluorophosphate, lithium bis(oxalato)borate [Kim 0020 and throughout], lithium difluoro(oxalato)borate [Kim 0020 and throughout], and lithium bis(trifluoromethanesulfonyl)imide [Kim 0024, Kim teaches bis(trifluoromethanesulfonyl)imide as a salt; however, since one or more salts may be added, the limitation is met by Kim.]. Regarding Claim 17, modified Kim discloses the battery of claim 11, wherein the lithium salt comprises lithium hexafluorophosphate (LiPF6) [Kim 0024, 0058, 0077 and throughout]. Regarding Claim 18, modified Kim discloses the battery of claim 11, wherein the organic solvent comprises fluoroethylene carbonate (FEC) [Kim 0022-0023] and diethyl carbonate (DEC) [Kim 0022-0023, 0056, Kim teaches the FEC as a cyclic carbonate and DEC as a linear carbonate, and further teaches the linear and cyclic carbonates are mixed.]. Regarding Claim 19, modified Kim discloses the battery of claim 11, wherein the electroactive negative electrode material comprises at least one of a silicon oxide-based material and a carbon-based material [Kim 0068, 0089, Kim discloses the anode may be a carbon-based material [Kim 0068] and provides an example with artificial graphite [Kim 0089]. Kim does not teach a silicon oxide-based material but the claim only requires one of a silicon based-material or a carbon-based material, thus, the limitation is met by Kim]. Claim(s)20 is/are rejected under 35 U.S.C. 103 as being unpatentable over modified Kim as provided in claim 11 above, and in further view of Tsujita et al. [US20230207784A1], hereinafter Tsujita. Regarding Claim 20, modified Kim discloses the battery of claim 11. Kim teaches where the anode active material can be lithium metal [Kim 0068] but does not explicitly teach wherein the electroactive negative electrode material comprises, by weight, greater than 97% lithium. Tsujita discloses a battery where electroactive negative electrode material comprises, by weight, greater than 97% lithium [Tsujita 0098, Tsujita teaches when the negative active material is metallic Li, the content of the negative active material in the negative active material layer may be 99% by mass or more, and may be 100% by mass.]. Tsujita’s range overlaps and obviates the claimed range. Per MPEP 2144.05, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. It would have been obvious to one of ordinary skill in the art before the effective filing date to combine Tsujita’s teaching of the lithium composition of the negative electrode active material as described above with Kim’s lithium negative electrode active material [Kim 0068] for the predictable result of a negative electrode with sufficient energy density [Tsujita 0098] for Kim’s lithium-ion battery [Kim 0003 and throughout]. MPEP2143 (A) Combining prior art elements according to known methods to yield predictable results. Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to M. T. LEONARD whose telephone number is (571)270-1681. The examiner can normally be reached Monday, Wednesday, Thursday 9:00-5:00 EST. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Miriam Stagg can be reached at (571)270-5256. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /M. T. LEONARD/Examiner, Art Unit 1724 /STEWART A FRASER/Primary Examiner, Art Unit 1724
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Prosecution Timeline

Dec 14, 2023
Application Filed
Aug 31, 2026
Non-Final Rejection mailed — §103 (current)

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Prosecution Projections

1-2
Expected OA Rounds
70%
Grant Probability
82%
With Interview (+12.0%)
3y 5m (~8m remaining)
Median Time to Grant
Low
PTA Risk
Based on 113 resolved cases by this examiner. Grant probability derived from career allowance rate.

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