Prosecution Insights
Last updated: May 29, 2026
Application No. 17/573,178

Heterocyclic Electrolyte Additives for Rechargeable Metal Batteries

Non-Final OA §102§103§112
Filed
Jan 11, 2022
Examiner
WEINER, LAURA S
Art Unit
1723
Tech Center
1700 — Chemical & Materials Engineering
Assignee
U.S. Army DEVCOM Army Research Laboratory
OA Round
5 (Non-Final)
85%
Grant Probability
Favorable
5-6
OA Rounds
0m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 85% — above average
85%
Career Allowance Rate
976 granted / 1144 resolved
+20.3% vs TC avg
Moderate +14% lift
Without
With
+13.6%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
29 currently pending
Career history
1188
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
50.8%
+10.8% vs TC avg
§102
15.9%
-24.1% vs TC avg
§112
17.5%
-22.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1144 resolved cases

Office Action

§102 §103 §112
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 . Continued Examination Under 37 CFR 1.114 A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 8-6-2025 has been entered. Response to Arguments Applicant’s arguments with respect to claim(s) 1-7, 10-16 and 19-20 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. Election/Restrictions The election species has been withdrawn. Claim Objections Claims 3, 13-16 and 20 are objected to because of the following informalities: Claim 3 is objected to because the claim should cite “wherein the solvent comprises the nonaqueous solvent”. Claims 13-16 are objected to because the claims are dependent on cancelled claim 9. Claim 20 is objected to because the claim should cite “wherein the metal of the anode comprises” or “wherein the anode comprising the metal comprises”. Appropriate correction is required. Claim Rejections - 35 USC § 112 The following is a quotation of the first paragraph of 35 U.S.C. 112(a): (a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention. The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112: The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention. Claims 1-7, 10-15 and 19-20 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the enablement requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention. There are many factors to be considered when determining whether there is sufficient evidence to support a determination that a disclosure does not satisfy the enablement requirement and whether any necessary experimentation is "undue." These factors include, but are not limited to: The breadth of the claims [wherein the at least one functional group on the five-membered nitrogen only azole ring comprises fluorine and can also contain a hydroxyl group or an ether or an alkene]; The nature of the invention; The state of the prior art; The level of one of ordinary skill; The level of predictability in the art; The amount of direction provided by the inventor [wherein the at least one functional group on the five-membered nitrogen only azole ring comprises fluorine comprising -CF3]; The existence of working examples; [wherein the at least one functional group on the five-membered nitrogen only azole ring comprises fluorine comprising -CF3, specifically only teaching 3.5-bis(trifluoromethyl)-1H-prazole]; and The quantity of experimentation needed to make or use the invention based on the content of the disclosure. In re Wands, 858 F.2d 731, 737, 8 USPQ2d 1400, 1404 (Fed. Cir. 1988). The specification does not provide direction/guidance on the least one functional group on the five-membered nitrogen only azole ring comprising a hydroxyl group or an ether or an alkene. Thus, the disclosed claim claiming the at least one functional group on the five-membered nitrogen only azole ring comprising a hydroxyl group or an ether or an alkene does not bear a reasonable correlation to the full scope of the claim. Taking these factors into account, undue experimentation would be required by one of ordinary skill in the art to practice the invention recited in the claim(s). Claims 1-7, 10-16 and 19-20 are 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. Claims 1 and 11 are rejected because it is unclear what is meant by the phrase “wherein the at least one functional group comprises a fluorine or a hydroxyl group, ‘or’ is an ether or an alkene” because of the use of ‘or’. Claim 1 is rejected because of the addition of the phrase “wherein the at least one functional group comprising a fluorine is -CF3 or comprises a S-F bond” because of the phrase added before stating “wherein the at least one functional group comprises a fluorine or a hydroxyl group, or is an ether or an alkene”. In addition, to the confusion is the phrase “wherein the at least one functional group substitution comprises a terminal -CF3 or -S-F functional group”. These phrases make the claim vague and indefinite. Claim 4 is rejected because it is unclear what is meant by “a hybrid of the protic and in aprotic solvent” because applicant has argued that this is not referring to an ionic solvent. This makes the claim vague and indefinite. Claim 11 is rejected because the claim does not further limit claim 10 which is dependent on claim 1 because the functional group limitation is already cited in claim 1. Claim 12 is rejected because of the phrase “wherein the at least one functional group comprising a fluorine is -CF3 or comprises a S-F bond”. The claim should cite “wherein the at least one functional group comprising the fluorine is -CF3 or the S-F bond”. Claim 13 is rejected because the claim does not further limit claim 1 becausewhen the 5 membered ring compound comprising a nitrogen only azole comprising an imidazole, pyrazole, 1,2,3-triazole or 1,2,4-triazole has at least one carbon on the ring attached to a functional group then inherently it would be capable of forming a radical under reducing conditions, oxidizing conditions and/or chemically with other electrolytes species and would be capable of subsequently undergoing radical condensation reactions. Therefore, this claim does not further limit claim 1. Claim 14 is rejected because the claim is redundant because the claim limitation is already cited in claim 1. Therefore, this claim does not further limit claim 1. Claim 15 is rejected because “a six-membered ring compound” cannot be present because claim 1 does not allow for this ring compound. 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. 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) 1-7, 10-16 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Aspern et al. “Methyl-group functionalization of pyrazole-based additives for advanced lithium-ion battery electrolytes” in view of Chen et al. (US 2019/0140320). Aspern et al. teaches on pages 6 and 8, a battery comprising a cathode, an anode comprising graphite and an electrolyte solutions comprising 1-methyl-3,5-bis(trifluoromethyl)-1H-pyrazole (MBTFMP) PNG media_image1.png 114 167 media_image1.png Greyscale or 3,5-bis(trifluoromethyl)-1H-pyrazole (BTFMP) PNG media_image2.png 117 166 media_image2.png Greyscale functional additives in a solution of 1 M LiPF6 [teaching claims 6-7] EC:EMC [teaching claims 2-5] where the additive is present in an amount of 5% [teaching claim 1] . Since Aspern et al. teaches the same heterocyclic compound having a five-membered nitrogen only azole ring comprising the specified pyrazole comprising a functional group comprising -CF3, then inherently the same molecular weight of the heterocyclic compound comprising 30-900 g/mol must also be obtained. In addition, the presently claimed property of the same molecular weight of the heterocyclic compound comprising 30-900 g/mol would obviously have been present once the Aspern et al. product is provided. In re Best, 195 USPQ 433 (CCPA 1977). In regard to claim 13, since Aspern et al. teaches the same heterocyclic compound having a five-membered nitrogen only azole ring comprising the specified pyrazole comprising a functional group comprising -CF3 in which at least one carbon on the ring is attached to a functional group, then inherently the five-membered ring compound would be capable of forming a radical under reducing conditions, oxidizing conditions and/or chemically with other electrolytes species and would be capable of subsequently undergoing radical condensation reactions must also be obtained. In addition, the presently claimed property of the five-membered ring compound would be capable of forming a radical under reducing conditions, oxidizing conditions and/or chemically with other electrolytes species and would be capable of subsequently undergoing radical condensation reactions would obviously have been present once the Aspern et al. product is provided. In re Best, 195 USPQ 433 (CCPA 1977). Aspern et al. discloses the claimed invention except for specifically teaching that that the anode comprises a metal comprising lithium. Chen et al. (US 2019/0140320) teaches in claims 1 and 5, an electrolyte composition comprising a heterocyclic compound in an amount of 0.01-5 wt%, an electrolyte salt and a solvent. Chen et al. teaches in claims 9-10, wherein the electrolyte salt comprises a lithium salt such as LiPF6, LiBF4, etc. and claims in claim 11, wherein the solvent is a non-aqueous solvent. Chen et al. teaches in [0059-0065 and 0068], a battery comprising a negative electrode comprising graphite, a cathode and an electrolyte solution. Chen et al. teaches in [0004], that the negative electrode material may comprise lithium metal, graphite, etc. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to use lithium metal instead of graphite as the negative active material because Chen et al. teaches that both these negative active materials can be used in the anode as explained above and one would expect therefore that these negative active materials would function in a similar way and give similar results. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Saruwatari et al. (US 2006/0204855) teaches in [0021], that the nonaqueous solvent contains an ionic liquid. Yada et al. (US 2009/0305136) teaches in [0044], that an ionic liquid can be used as a non-aqueous solvent of the non-aqueous electrolyte solution. Yu (US 2011/0064988) teaches in [0016], that the non-aqueous solvent preferably includes an ionic liquid; teaches in [0080], that using an ionic liquid as a non-aqueous solvent and teaches in claim 15, that the non-aqueous solvent includes ionic liquid. Lin et al. (WO 2018/191308) teaches secondary batteries with long cycle life comprising an aluminum metal anode. Lin et al. teaches in claim 1, a battery comprising a metal anode, a cathode and an electrolyte comprising a metal halide salt. Lin et al. teaches in [145], suitable ionic liquids can include N-heterocyclic compounds with 5-6 carbon atoms per molecule and teaches in [146], wherein the anions can be tetrafluoroborate, trifluoromethanesulfonate and bis(trifluoromethanesulfonyl)imide. Chang et al. (US 2020/0212489) teaches in claim 1, an electrolyte composition comprising a metal salt having the formula MiXj where X is F-, Cl-, Br-, BF4-, PF6-, etc.; an ionic liquid and an additive comprising a substituted or unsubstituted C5-C30 nitrogen-containing heterocyclic compound. Chang et al. teaches in claim 3, wherein the amount of the additive is from 0.5-20 weight percent based on the total weight of the metal salt and the ionic liquid (a non-aqueous solvent). Chang et al. teaches in claim 5, wherein the additive comprises a pyrazole, an imidazole, etc. Chang et al. teaches in claim 8, a battery comprising a positive electrode, a negative electrode and the electrolyte composition and teaches in claims 12-14, wherein the negative electrode comprises a metal comprising sodium, magnesium, calcium, zinc, etc. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Laura Weiner whose telephone number is (571)272-1294. The examiner can normally be reached 9 am-5 pm EST M-F. 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, Tong Guo can be reached at 571-272-3066. 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. /LAURA S. WEINER/ Primary Examiner Art Unit 1723 /Laura Weiner/Primary Examiner, Art Unit 1723
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Prosecution Timeline

Show 9 earlier events
Apr 29, 2025
Response Filed
May 20, 2025
Final Rejection mailed — §102, §103, §112
May 21, 2025
Interview Requested
Jun 04, 2025
Applicant Interview (Telephonic)
Jun 04, 2025
Examiner Interview Summary
Aug 06, 2025
Request for Continued Examination
Aug 11, 2025
Response after Non-Final Action
Apr 23, 2026
Non-Final Rejection mailed — §102, §103, §112 (current)

Precedent Cases

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

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Prosecution Projections

5-6
Expected OA Rounds
85%
Grant Probability
99%
With Interview (+13.6%)
3y 1m (~0m remaining)
Median Time to Grant
High
PTA Risk
Based on 1144 resolved cases by this examiner. Grant probability derived from career allowance rate.

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