Prosecution Insights
Last updated: April 19, 2026
Application No. 17/835,772

CYANO-CONTAINING ORGANOFLUOROBORATE ADDITIVES FOR LITHIUM ION BATTERIES

Non-Final OA §103§DP
Filed
Jun 08, 2022
Examiner
SMITH, NICHOLAS A
Art Unit
1752
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Apple Inc.
OA Round
2 (Non-Final)
64%
Grant Probability
Moderate
2-3
OA Rounds
3y 3m
To Grant
94%
With Interview

Examiner Intelligence

Grants 64% of resolved cases
64%
Career Allow Rate
577 granted / 909 resolved
-1.5% vs TC avg
Strong +31% interview lift
Without
With
+30.8%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
21 currently pending
Career history
930
Total Applications
across all art units

Statute-Specific Performance

§101
0.7%
-39.3% vs TC avg
§103
51.6%
+11.6% vs TC avg
§102
29.2%
-10.8% vs TC avg
§112
11.5%
-28.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 909 resolved cases

Office Action

§103 §DP
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 Claim Objections Due to Applicant’s Amendment, the previous claim objections have been withdrawn. Claim Objections Claim 4, 6-7 and 14-20 are objected to because of the following informalities: “of any claim 1” in claims 4, 14 and 18; “fluid claim 1” in claim 6; “electrolyte claim 1” in claim 7; and, claim 4 contains “potassium organotrifluoroborate (PCTFB)” whereas the specification names “potassium (cyanomethyl)trifluoroborate (PCTFB)” in [0011] of the specification. Claims 15-17 and 19-20 are objected to due to dependency. Appropriate correction is required. Response to Arguments Applicant's arguments filed 30 September 2025 have been fully considered. The previous rejection has been withdrawn because Ignatyen (US 20140155566 A1) discloses alkyl/alkenyl-cyano-fluoroborate ([0014]) with the formula: [Kt]z+z[(R1)4-x-y-vB(CN)x(NC)yFv]- , wherein x is 1, 2 or 3. Thus, Ignatyen discloses wherein the cyano group is substituted off of boron and such is a requirement of the invention. The instant claim requires compounds with boron only being bonded to either (a) F or (b) alkyl-groups with a cyano-group substituted. However, please see the new rejection below. 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. Claim(s) 1-2 and 11-21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Giroud (US 20110151317 A1) in view of Zhao (“Dual-functionalized ionic liquids: synthesis and characterization of imidazolium salts with a nitrile-functionalized anion”, Chem. Commun., 2004, 2500-2501), both as submitted on Applicant's Information Disclosure Statement filed 30 September 2025, and in further view of Kim (US 20170288268 A1). In regards to claim(s) 1-2, Giroud teaches ionic liquid electrolytes with an imidazolium ion and a quaternary ammonium ion ([0065]) with an anion containing a halogenic element (CH3BF3-, for instance, [0067]), but is silent with respect to the organotrifluoroborate claimed in Formula I and the wt. % of the additive. Giroud also discloses that the lowering the viscosity of the electrolyte is desirable via the solvent ([0165]), via the cation ([0105]) and via the anion ([0109]). Giroud also discloses that there is no limitation as to the choice of the anion of the ionic liquid ([0106]). Zhao pertains to ionic liquids (abstract) for many applications (top left, p. 2500) and notes their dual-functionalized ionic liquid exhibit very low viscosities. Zhao disclose the anion of Formula I, wherein m =3 and the alkyl group is saturated and branched (as explained in [0045] of the specification). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the anion of Giroud with the anion of Zhao because the substituted components were known, their functions were known in the art, one of ordinary skill in the art could have substituted one known component for another and that the results of the substitution would have been predictable (low viscosity). See MPEP 2143 I (B). 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.%. Giroud disclosed range overlaps the instantly claimed range and therefore establishes a case of prima facie obviousness. See MPEP 2144.05 I. It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to select the claimed range from the broader prior art range because prior art teaches the same utility over the entire range. However, Giroud in view of Zhao does not disclose wherein the electrolyte includes less than or equal to 3.5% weight 1,3,6-Hexanetricarbonitrile (HTCN). Kim teaches an electrolyte for a rechargeable lithium battery includes an organic solvent including C3 to C5 alkyl propionate, and the electrolyte further includes a lithium salt and a compound represented by Chemical Formula 1, wherein, in Chemical Formula 1, k, l, and m are independently integers of 0 to 20, k, l, and m are selected, so that Chemical Formula 1 has an asymmetric structure, n is an integer of 1 to 7, and R1, R2, R3, R4, R5, and R6 are independently hydrogen, an alkyl group, an alkoxy group, or a fluoroalkyl group (Kim Abstract). Kim also teaches an amount of about 0.05 wt% to about 10 wt% (at least 0.01 wt%) based on the total weight of the electrolyte for a rechargeable battery (Kim Para 0015). Kim also teaches examples of additive HTCN 2 wt% (Kim Table 1). It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to have modified Giroud in view of Zhao’s teachings with Kim’s for the benefit of improving electrochemical characteristics and thermal safety of a solvent, using an additive to delay ignition of the battery, decreasing thickness change of the battery, and the like (Kim Para 0007). In regards to claim(s) 11-13, Giroud discloses 1.6 mol/L LiPF6 (claim 22). In regards to claim(s) 14-20, Giroud discloses that the electrolyte may further contain organic solvents in order to lower the viscosity ([0164]-[0165]), however is silent on the specific types of solvents/additional additives as claimed. Kim teaches the carbonate-based solvent may be dimethyl carbonate (DMC), diethyl carbonate (DEC), dipropyl carbonate (DPC), methylpropyl carbonate (MPC), ethylpropyl carbonate (EPC), methylethyl carbonate (MEC), ethylene carbonate (EC), propylene carbonate (PC), butylene carbonate (BC), and the like, which may be used individually or in combination (Kim Para 0043). Kim also teaches The C3 to C5 alkyl propionate may be a propionic ester linked with a C3 to C5 alkyl group, and may be, for example, propyl propionate (PP), N-butyl propionate, tert-butyl propionate, isobutyl propionate, N-pentyl propionate, 2-pentyl propionate, tert-pentyl propionate, or isopentyl propionate, which may be used individually or in combination (Kim Para 0040). Kim also teaches ester-based solvent may be methyl acetate, ethyl acetate, n-propyl acetate, dimethylacetate, methylpropionate (MP), ethylpropionate (EP), decanolide, mevalonolactone, caprolactone, and the like, which may be used individually or in combination (Kim Para 0044). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute Giroud’s solvent with Kim’s solvent because the substituted components were known, their functions were known in the art, one of ordinary skill in the art could have substituted one known component for another and that the results of the substitution would have been predictable. See MPEP 2143 I (B). Regarding Claim 17, Kim discloses the electrolyte fluid wherein PC is 2 from 20 wt% of the total electrolyte fluid, EC is from 5 to 40 wt% of the total electrolyte fluid, PP is from 20 to 70 wt% of the total electrolyte fluid, and/or EP is from 10 to 50 wt% of the total electrolyte, see Kim Table 1 In regards to claim(s) 18-20, Kim teaches carbonate-based solvent may be ethylene carbonate (EC), propylene carbonate (PC) (Kim Para 0043). Kim also teaches the electrolyte for a rechargeable lithium battery may include one or more additives selected from fluoroethylene carbonate (FEC), vinylethylene carbonate (VEC), succinonitrile (SN), polysulfone (PS), and a combination thereof (Kim Para 0024). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute Giroud’s additives with Kim’s additives because the substituted components were known, their functions were known in the art, one of ordinary skill in the art could have substituted one known component for another and that the results of the substitution would have been predictable. See MPEP 2143 I (B). In regards to claim(s) 21, Giroud discloses a battery cell (Fig. 1; [0166]-[0182]) with a positive electrode (cathode) comprising positive active material and a current collector, a negative electrode (anode) comprising negative active material and a current collector, and a separator disposed between the electrode active materials, with the electrolyte fluid as taught by the prior art combination of Giroud, Zhao and Kim as explained above for claim 1. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer. Claims 1-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of copending Application No. 17/835758 in view of Kim. The reference claims are substantially similar to the instant claims, but are silent on HTCN. Kim is applied for the same reasons as stated above for instant claim 1 in the prior art rejection. This is a provisional nonstatutory double patenting rejection. Claims 1-3 and 5-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of copending Application No. 17/835766 in view of Kim. The reference claims (limited to Formula IV, however) are substantially similar to the instant claims, but are silent on HTCN. Kim is applied for the same reasons as stated above for instant claim 1 in the prior art rejection. This is a provisional nonstatutory double patenting rejection. Allowable Subject Matter Claims 3-10 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims, overcome any double patenting rejections and the above claim objections. In regards to claim(s) 3-4, while Ignatyen discloses potassium cyanomethyltrifluoroborate ([0480]), it is only a precursor to produce potassium cyanomethyldicyanofluoroborate, which is not the claimed electrolyte. Zhao is the closest prior art, which discloses one variation of the anion of Formula I, wherein m=3. There is no suggestion in the prior art to change to m = 1 or 2, or to produce an anion of Formula II, III or IV in an electrolyte fluid. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to NICHOLAS A SMITH whose telephone number is (571)272-8760. The examiner can normally be reached M-F 7:30am-3:30pm. 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, Srilakshmi Kumar can be reached at (571)272-7769. 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. /NICHOLAS A SMITH/Supervisory Primary Examiner, Art Unit 1752
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Prosecution Timeline

Jun 08, 2022
Application Filed
Jun 25, 2025
Non-Final Rejection — §103, §DP
Sep 30, 2025
Response Filed
Jan 26, 2026
Non-Final Rejection — §103, §DP (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

2-3
Expected OA Rounds
64%
Grant Probability
94%
With Interview (+30.8%)
3y 3m
Median Time to Grant
Moderate
PTA Risk
Based on 909 resolved cases by this examiner. Grant probability derived from career allow rate.

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