Prosecution Insights
Last updated: August 01, 2026
Application No. 17/835,758

CYANO-CONTAINING ORGANOTRIFLUOROBORATE ADDITIVES FOR LITHIUM ION BATTERIES

Final Rejection §103
Filed
Jun 08, 2022
Priority
Jun 17, 2021 — provisional 63/211,825 +2 more
Examiner
BLACKWELL-RUDASIL, RYAN KENZIE
Art Unit
1722
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Apple Inc.
OA Round
2 (Final)
71%
Grant Probability
Favorable
3-4
OA Rounds
0m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 71% — above average
71%
Career Allowance Rate
12 granted / 17 resolved
+5.6% vs TC avg
Strong +42% interview lift
Without
With
+41.7%
Interview Lift
resolved cases with interview
Typical timeline
3y 4m
Avg Prosecution
30 currently pending
Career history
53
Total Applications
across all art units

Statute-Specific Performance

§103
88.3%
+48.3% vs TC avg
§102
10.4%
-29.6% vs TC avg
§112
0.7%
-39.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 17 resolved cases

Office Action

§103
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 . Status of Claims Claims 1-20 are pending. Claim 21 is cancelled. Claims 5-11 are withdrawn. Status of Amendment The amendment filed on July 14th, 2025 has been fully considered but does not place the application in condition for allowance. Status of Objections and Rejections Pending Since the Office Action of April 14th, 2025 The 112(b) rejection has been withdrawn in view of the Applicant's amendment. The 102 rejections over Zhao (Dual-functionalized ionic liquids: synthesis and characterization of imidazolium salts with a nitrile-functionalized anion”) has been withdrawn in view of the Applicant's amendment. The 103 rejections over Giroud (US 2011/0151317 A1) in view of Zhao, Ignatyen (US 2014/0155566 A1), Abe (US 2009/0136838), and/or Su (US 2020/0044285) are withdrawn in view of the Applicant's amendment. Claim Objections Claims 18-20 are objected to because the limitation of “a second additive selected from (LiDFOB)” should be changed to “a second additive selected from LiDFOB” such that “LiDFOB” is no longer in parentheses. Claims 19 and 20 are objected to because of their dependence on claim 18. 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. 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. Claims 1-3, 12-14, and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Giroud (US 2011/0151317 A1) and further in view of Zhao (Dual-functionalized ionic liquids: synthesis and characterization of imidazolium salts with a nitrile-functionalized anion”). Regarding claims 1-3, Giroud teaches ionic liquid electrolytes with an imidazolium ion and a quaternary ammonium ion [0065] with an anion containing a halogenic element, but is silent with respect to the organotrifluoroborate claimed in Formula I and the wt. % of the additive. Zhao is analogous art to Giroud because both teach ionic liquids. Zhao teaches the ionic liquids that contain the imidazolium ion taught by Giroud and the anion depicted below (the organotrifluoroborate of interest). PNG media_image1.png 224 352 media_image1.png Greyscale Zhao continues to teach that ionic liquids with this structure have low viscosities and melting points (Zhao, right column, page 2500), and Giroud indicates that a low viscosity is beneficial for electrolytes ([0075] and [0105]–[0109]). Substituting the ionic liquid of Giroud’s with the ionic liquid of Zhao’s results in the structure of Formula I where m = 1 and the “M+” is an imidazolium ion. Giroud teaches that the electrolyte that contains the ionic compound, an organic solvent (in an amount of 5-20% by mass of the electrolyte [0165]), a conducting salt [0072], and small percentage of anionic surfactant [0143]. In this case, the content of the organotrifluoroborate would be overlapping with the claimed range of at least 0.01 wt.%. Moreover, "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). Furthermore, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). See MPEP 2144.05 (I). Therefore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the present invention to substitute the ionic liquid of Zhao in place of the ionic liquid of Giroud in order to create an electrolyte that has low viscosity to improve electrolyte performance. Furthermore, Giroud teaches a cathode comprising a cathode active material disposed on a cathode current collector ([0168] and Figure 1, #3), an anode comprising an anode active material disposed on an anode current collector ([0168] and Figure 1, #1) and a separator disposed between them ([0180] and Figure 1, #2). As seen in Figure 1, the two electrodes are facing each other, and the liquid electrolyte is disposed between the cathode and anode. The liquid electrolyte may be comprised of the ionic liquid [0163]. Figure 1 is depicted below: PNG media_image2.png 415 1081 media_image2.png Greyscale Regarding claims 12-14, Giroud teaches that the electrolyte may be comprised of LiPF6 in a range of 0.1M – 10M ([0072] and [0074]), which overlaps with the claimed range of 0.8M to 1.6M. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). See MPEP 2144.05 (I). Regarding claims 18-20, Giroud teaches that a mixture of conducting salts may be used in the electrolyte, including LiODBF [0072]. LiODBF is an alternative acronym for LiDFOB. Therefore, Giroud teaches using LiDFOB as a component or additive of the electrolyte. Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over modified Giroud as applied to claim 1 above, and further in view of Ignatyen (US 2014/0155566 A1). Giroud is silent on whether or not potassium may be used as a cation. Ignatyen teaches ionic liquids and is therefore analogous art to Giroud. Ignatyen teaches that both imidazolium ions ([0016]) and inorganic ions such as potassium ([0014]) may be used as a cation in ionic fluids. Combining potassium and Zhao’s anion results in the creation of potassium organotrifluoroborate. Therefore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the present invention to use potassium organotrifluoroborate as an ionic liquid in an electrolyte with a reasonable expectation of success. Claims 15-17 are rejected under 35 U.S.C. 103 as being unpatentable over Giroud in view of Zhao as applied to claim 1 above, and further in view of Abe (US 20090136838 A1) and Su (US 2020/0044285 A1). Giroud teaches that the electrolyte comprising of an ionic liquid “may further contain other components such as organic solvents…currently used in electrolytes such as carbonates” ([0164]-[0165]), but is silent on specific organic solvents or carbonates. Su and Giroud teach non-aqueous electrolytes and therefore are analogous art. Su teaches that an electrolyte fluid may be a mixture of propylene carbonate (PC), ethylene carbonate (EC), and other solvents (0054]), thus it would be prima facie obvious to use them as solvents in Giroud’s electrolyte based on their suitability for their intended use. See MPEP 2144.07. Abe and Giroud teach non-aqueous electrolytes and therefore are analogous art. Abe teaches that using propyl propionate (PP) and ethyl propionate (EP) as solvents in an electrolyte fluid obtains excellent low-temperature output characteristics, especially in temperatures under -20 ℃ ([0027]–[0029]). Therefore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the present invention to combine the solvents of modified Giroud, Su, and Abe such that the electrolyte comprises of Giroud’s ionic liquid, the PC and EC taught by Su, and the PP and EP taught by Abe in order to improve battery function in sub-zero temperatures. Response to Arguments Applicant's arguments filed July 14th, 2025 have been fully considered but they are not persuasive. The Applicant alleges that the Examiner argues that the imidazolium ion of Giroud is functionally equivalent to the presently claimed organotrifluoroborate of Formula (I). However, Giroud’s imidazolium ion corresponds with the cation “M+” present within Formula (I). Zhao teaches the required anion present within Formula (I). Furthermore, this allegation argument addresses Giroud alone and does not address the combination of Giroud and Zhao. 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 RYAN K BLACKWELL-RUDASILL whose telephone number is (571)270-0563. The examiner can normally be reached Monday - Friday 9:00 a.m. - 5:00 p.m. 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, Niki Bakhtiari can be reached on 571-272-3433. 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. /R.B.R./ Examiner, Art Unit 1722 /ANCA EOFF/Primary Examiner, Art Unit 1722
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Prosecution Timeline

Jun 08, 2022
Application Filed
Apr 14, 2025
Non-Final Rejection mailed — §103
Jul 14, 2025
Response Filed
Apr 30, 2026
Final Rejection mailed — §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

3-4
Expected OA Rounds
71%
Grant Probability
99%
With Interview (+41.7%)
3y 4m (~0m remaining)
Median Time to Grant
Moderate
PTA Risk
Based on 17 resolved cases by this examiner. Grant probability derived from career allowance rate.

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