Prosecution Insights
Last updated: October 04, 2026
Application No. 18/530,818

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

Non-Final OA §102
Filed
Dec 06, 2023
Examiner
SERVAGNO, SANTINO MICHALE
Art Unit
Tech Center
Assignee
UChicago Argonne LLC
OA Round
1 (Non-Final)
Grant Probability
Favorable
1-2
OA Rounds

Examiner Intelligence

Grants only 0% of cases
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Career Allowance Rate
0 granted / 0 resolved
-60.0% vs TC avg
Minimal +0% lift
Without
With
+0.0%
Interview Lift
resolved cases with interview
Typical timeline
Avg Prosecution
23 currently pending
Career history
10
Total Applications
across all art units
This examiner has no resolved cases yet (career too new); statute-level performance unavailable. The Grant Probability card shows Tech Center averages instead.

Office Action

§102
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 . Information Disclosure Statement The information disclosure statement (IDS) submitted on 12/06/2023 has been considered by the examiner. 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. Claims 1-20 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Nitta et al. (US 2024/0322244 A1). Regarding claim 1, Nitta discloses a battery that cycles lithium ions (Nitta Fig. 1), the battery comprising: a negative electrode comprising an electroactive negative electrode material (Para. [0081] lists the materials comprising the anode as a mixture of silicon-comprising active materials.); a positive electrode spaced apart from the negative electrode and comprising a high-voltage positive electrode material (Para. [0175] states a separator is interposed in a space between the anode and the cathode within the lithium-ion battery. Para. [0068] of the instant specification defines “high-voltage” as being greater than or equal to 4.5 V vs. Li+/Li. Nitta para. [0109] lists a plethora of “high-voltage positive electrode materials” such as lithium cobalt oxides, lithium nickel cobalt aluminum oxides, lithium nickel cobalt manganese aluminum oxides, lithium nickel oxides, amongst others, which may be charged above 4.5 V vs. Li/Li+ or 4.6 V vs. Li/Li+.) and an electrolyte infiltrating the positive electrode (Para. [0009] states that too high salt concentration will increase wetting time during manufacturing wherein the liquid electrolyte wetting time is the time it takes for the liquid electrolyte to infiltrate the electrodes/separators.), the electrolyte comprising: an organosulfur compound (Para. [0144] lists organosulfur compounds which may comprise the solvent composition which may include ethyl methyl sulfone (EMS), sulfolane, and dimethyl sulfoxide.), a fluorinated aromatic co-solvent (Para. [0015] lists the aromatic fluorinated compounds which may be used as diluents and/or co-solvents which includes trifluorotoluene (TFT) ELY #24 in Table 4 depicts TFT as an aromatic co-solvent.), a solid electrolyte interphase (SEI) former (Para. [0111] states that the addition of some known SEI-forming additives to the Li-ion battery may improve SEI stability during cycling. Para. [0172] states that SEI builders including FEC, VC and/or EC may be added to the electrolyte at relatively low mole fractions to attain high cycle life for the battery.), and at least one lithium salt (Para. [0117] lists the lithium-based salt compounds that may be used as the primary lithium salt within the Li-ion battery electrolyte.). Regarding claim 2, Nitta further discloses wherein the fluorinated aromatic co-solvent comprises a fluoroalkyl-substituted benzene, a fluoroalkoxy-substituted benzene, or a combination thereof (ELY #4 in Table 3 and ELY #24 in table 4 shows trifluorotoluene (TFT) as a suitable co-solvent within the Li-ion battery electrolyte.). Regarding claim 3, Nitta further discloses wherein the fluorinated aromatic co-solvent comprises an aromatic hydrocarbon represented by formula (3): wherein: R6, R7, R8, R9, R10, and R11 are each individually H, halogen, alkyl, alkenyl, alkynyl, aryl, alkoxy, alkenoxy, alkynoxy, aryloxy, heterocyclyloxy, alkyl-heterocyclyloxy, hydroxyl, carboxyl, ester, or ether, and at least one of R6, R7, R8, R9, R10, and R11 is a fluoroalkyl or a fluoroalkoxy, the fluoroalkyl having the formula -CnHxFy or -CH2CnHxFy, and the fluoroalkoxy having the formula -CH2OCnHxFy or -CF2OCnHxFy, where n is an integer from 1 to 5, x is an integer from 0 to 11, y is an integer from 1 to 11, and the sum of x and y is 2n+1 (ELY #4 in Table 3 and ELY #24 in table 4 shows trifluorotoluene (TFT) as a suitable co-solvent within the Li-ion battery electrolyte. TFT fulfills the definition of a fluoroalkyl substituent which possesses the formula -CnHxFy, wherein n=1, x=o, and y=3 and the sum of x+y=3 and the sum of 2n+1=3.). Regarding claim 4, Nitta further discloses wherein the fluorinated aromatic co-solvent constitutes, by volume, greater than or equal to 10% and less than or equal to 90% of the electrolyte (Table 3 displays trifluorotoluene (TFT) in ELY #4 with a volume percent of 42.25 compared to the total volume of the electrolyte composition.). Regarding claim 5, Nitta further discloses wherein the organosulfur compound comprises an acyclic sulfoxide represented by formula (1): wherein: R1 and R2 are each individually H; halogen; an unsubstituted or fluorinated alkyl, alkenyl, alkynyl, silyl, siloxy, aryl, aralkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl, or cycloalkylalkyl; -OR3; -C(O)R3; -C(O)OR3; -OC(O)R3; and R3 is H or an unsubstituted or fluorinated alkyl, alkenyl, alkynyl, aryl, aralkyl, or heterocyclyl. (Para. [0144] states that the solvent composition in the battery electrolyte contains one, two, or more sulfur-containing compounds which may include sulfoxides such as dimethyl sulfoxide.). Regarding claim 6, Nitta further discloses wherein the organosulfur compound comprises a cyclic or acyclic sulfone represented by formula (2): wherein: R1 and R2 are each individually H; halogen; an unsubstituted or fluorinated alkyl, alkenyl, alkynyl, silyl, siloxy, aryl, aralkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl, or cycloalkylalkyl; -OR3; -C(O)R3; -C(O)OR3; -OC(O)R3; R4 and R5 are each individually H; halogen; an unsubstituted or fluorinated alkyl, alkenyl, alkynyl, silyl, siloxy, aryl, aralkyl, heterocyclyl, heterocyclylalkyl, cycloalkyl, or cycloalkylalkyl; -OR3; -C(O)R3; -C(O)OR3; -OC(O)R3; or R4 and R5 together form a 5 or 6 membered substituted or unsubstituted heterocyclic ring including the sulfur (S) atom; X and Y are each individually -C(R3)-, -O-, or -N-; and R3 is H or an unsubstituted or fluorinated alkyl, alkenyl, alkynyl, aryl, aralkyl, or heterocyclyl. (Para. [0144] states that the solvent composition in the battery electrolyte contains one, two, or more sulfur-containing compounds which may include acyclic or cyclic sulfones such as ethyl methyl sulfone (EMS) and sulfolane. Para. [0190] states that ELY #19 has sulfolane as a diluent/co-solvent.). Regarding claim 7, Nitta further discloses wherein the organosulfur compound comprises an acyclic sulfone selected from the group consisting of ethyl methyl sulfone (EMS), dimethylmethanesulfonamide (DMMA), methyl isopropyl sulfone (MIS), dimethyl sulfate (DMS), methyl methanesulfonate (MMS), and methanesulfonyl fluoride (MSF) (Para. [0144] states that the solvent composition in the battery electrolyte contains one, two, or more sulfur-containing compounds which may include acyclic sulfones such as ethyl methyl sulfone (EMS).). Regarding claim 8, Nitta further discloses wherein the organosulfur compound comprises a cyclic sulfone selected from the group consisting of sulfolane and 1,3-propane sultone (Para. [0144] states that the solvent composition in the battery electrolyte contains one, two, or more sulfur-containing compounds which may include cyclic sulfones such as sulfolane. Para. [0190] states that ELY #19 has sulfolane as a diluent/co-solvent.). Regarding claim 9, Nitta further discloses wherein the organosulfur compound constitutes, by volume, greater than or equal to 10% and less than or equal to 90% of the electrolyte (Para. [0145] states that the electrolyte may be comprised of the organosulfur compound at a mole fraction in a range of about 20-50 mol% of the electrolyte while, in other aspects, the electrolyte may be comprised of the organosulfur compound at a mole fraction in a range of about 50-70 mol% of the electrolyte.). Regarding claim 10, Nitta further discloses wherein the SEI former comprises a cyclic carbonate selected from the group consisting of ethylene carbonate (EC), fluoroethylene carbonate (FEC), vinylene carbonate (VC), and vinyl ethylene carbonate (VEC) (Para. [0172] states that SEI builders including FEC, VC and/or EC may be added to the electrolyte at relatively low mole fractions to attain high cycle life for the battery). Regarding claim 11, Nitta further discloses wherein the SEI former constitutes, by volume, greater than or equal to 5% and less than or equal to 50% of the electrolyte (Para. [0130] states that FEC comprises, as a mole fraction, a range between 0.1% to about 20%; VC may be in the range of about 0.05 mol % to about 2.00 mol %; and EC may be employed in the electrolyte composition as a mole fraction between 1 mol % to 5 mol %. Examples are presented in Table 2 which shows ELY #1, ELY #2, and ELY #3 with mol % of FEC at 21.8%, 19.4%, and 22.4%. Table 3 displays FEC mol% for ELYs #4-10 at 12%.). Regarding claim 12, Nitta further discloses wherein the at least one lithium salt comprises lithium hexafluorophosphate (LiPF6), lithium bis(fluorosulfonyl)imide (LiFSI), lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), or a combination thereof (Para. [0117] lists LiPF6, LiFSI, and LiTFSI as the primary salts in the various electrolyte compositions.). Regarding claim 13, Nitta further discloses wherein the at least one lithium salt is present in the electrolyte at a concentration of greater than or equal to 0.5 Molar and less than or equal to 2 Molar (Table 3 shows LiPF6 as the exemplary salt in ELYs #4 to #10 at a concentration of 0.95 M. Para. [0190] states that ELYs #11 to #36 have LiPF6 at a concentration of 1.15 M.). Regarding claim 14, Nitta further discloses wherein the electrolyte is substantially free of acyclic hydrofluoroethers (Table 2 provides the components present in electrolyte compositions for ELYs #1 to #3, all of which show no presence of hydrofluoroethers. Table 3 provides the components present in electrolyte compositions for ELYs #4 to #10, all of which show no presence of hydrofluoroethers.). Regarding claim 15, Nitta further discloses wherein the electroactive negative electrode material comprises graphite, silicon, silicon oxide, or an elemental lithium metal film (Para. [0175] states that the anode of the lithium-ion battery is comprised of Si-comprising particles such as Si-C nanocomposite particles comprising carbon and silicon wherein the silicon is arranged as the active material particles and the carbon as the inactive or substantially inactive part of the scaffolding matrix.). Regarding claim 16, Nitta discloses a battery that cycles lithium ions (Nitta Fig. 1), the battery comprising: a negative electrode comprising an electroactive negative electrode material comprising graphite (Para. [0175] lists the one of the materials that may comprise the electroactive material of the negative electrode as graphite carbon particles with the carbon-comprising graphite as the active material, which is substantially free of silicon.); a positive electrode spaced apart from the negative electrode and comprising a high-voltage positive electrode material (Para. [0175] states a separator is interposed in a space between the anode and the cathode within the lithium-ion battery. Para. [0068] of the instant specification defines “high-voltage” as being greater than or equal to 4.5 V vs. Li+/Li. Nitta para. [0109] lists a plethora of “high-voltage positive electrode materials” such as lithium cobalt oxides, lithium nickel cobalt aluminum oxides, lithium nickel cobalt manganese aluminum oxides, lithium nickel oxides, amongst others, which may be charged above 4.5 V vs. Li/Li+ or 4.6 V vs. Li/Li+.) and an organosulfur-based electrolyte (Para. [0145] states that the electrolyte may be comprised of the organosulfur compound at a mole fraction in a range of about 50-70 mol% of the electrolyte.) infiltrating the negative electrode and the positive electrode (Para. [0009] states that too high salt concentration will increase wetting time during manufacturing wherein the liquid electrolyte wetting time is the time it takes for the liquid electrolyte to infiltrate the electrodes/separators.), the organosulfur-based electrolyte comprising: an organosulfur compound comprising an acyclic sulfoxide, an acyclic sulfone, a cyclic sulfone, or a combination thereof (Para. [0144] lists organosulfur compounds which may comprise the solvent composition which may include ethyl methyl sulfone (EMS), sulfolane, and dimethyl sulfoxide.), a fluorinated aromatic co-solvent comprising a fluoroalkyl-substituted benzene, a fluoroalkoxy-substituted benzene, or a combination thereof (Para. [0015] lists the aromatic fluorinated compounds which may be used as diluents and/or co-solvents which includes trifluorotoluene (TFT) ELY #24 in Table 4 depicts TFT as an aromatic co-solvent.), a solid electrolyte interphase (SEI) former (Para. [0111] states that the addition of some known SEI-forming additives to the Li-ion battery may improve SEI stability during cycling. (Para. [0172] states that SEI builders including FEC, VC and/or EC may be added to the electrolyte at relatively low mole fractions to attain high cycle life for the battery.), and a lithium salt (Para. [0117] lists the lithium-based salt compounds that may be used as the primary lithium salt within the Li-ion battery electrolyte.). Regarding claim 17, Nitta further discloses wherein the organosulfur compound constitutes, by volume, greater than or equal to 10% and less than or equal to 90% of the electrolyte (Para. [0145] states that the electrolyte may be comprised of the organosulfur compound at a mole fraction in a range of about 20-50 mol% of the electrolyte while, in other aspects, the electrolyte may be comprised of the organosulfur compound at a mole fraction in a range of about 50-70 mol% of the electrolyte.). Regarding claim 18, Nitta further discloses wherein the fluorinated aromatic co-solvent constitutes, by volume, greater than or equal to 10% and less than or equal to 90% of the electrolyte (Table 3 displays trifluorotoluene (TFT) in Example ELY #4 with a volume percent of 42.25 compared to the total volume of the electrolyte composition.). Regarding claim 19, Nitta further discloses wherein the SEI former comprises a cyclic carbonate selected from the group consisting of ethylene carbonate (EC), fluoroethylene carbonate (FEC), vinylene carbonate (VC), and vinyl ethylene carbonate (VEC), and wherein the SEI former constitutes, by volume, greater than or equal to 5% and less than or equal to 50% of the electrolyte (Para. [0172] states that SEI builders including FEC, VC and/or EC may be added to the electrolyte at relatively low mole fractions to attain high cycle life for the battery. Para. [0130] states that FEC comprises, as a mole fraction, a range between 0.1% to about 20%; VC may be in the range of about 0.05 mol % to about 2.00 mol %; and EC may be employed in the electrolyte composition as a mole fraction between 1 mol % to 5 mol %. Examples are presented in Table 2 which shows ELY #1, ELY #2, and ELY #3 with mol % of FEC at 21.8%, 19.4%, and 22.4%. Table 3 displays FEC mol% for ELYs #4-10 at 12%.). Regarding claim 20, Nitta further discloses wherein the at least one lithium salt comprises lithium hexafluorophosphate (LiPF6), lithium bis(fluorosulfonyl)imide (LiFSI), lithium bis(trifluoromethanesulfonyl)imide (LiTFSI), or a combination thereof, and wherein the at least one lithium salt is present in the electrolyte at a concentration of greater than or equal to 0.5 Molar and less than or equal to 2 Molar (Para. [0117] lists LiPF6, LiFSI, and LiTFSI as the primary salts in the various electrolyte compositions. Table 3 shows LiPF6 as the exemplary salt in ELYs #4 to #10 at a concentration of 0.95 M. Para. [0190] states that ELYs #11 to #36 have LiPF6 at a concentration of 1.15 M.). Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Farnham et al. (US 2002/0110735 A1) discloses an electrolyte composition comprising octafluorotoluene as a fluorine additive, LiPF6 as the lithium salt at a concentration of 1 M and ethylene carbonate (EC). Olschimke (US 2009/0197167 A1) discloses an electrolyte composition comprising 2,6-bis(trifluoromethyl)benzonitrile as the fluorinated aromatic compound utilized as an additive and LiPF6 as the lithium salt. Yoshimura (US 2024/0194947 A1) discloses an electrolytic solution wherein, in a plurality of embodiments, said electrolytic solution comprises of a plurality of fluorine-containing compounds wherein the fluorine-containing compounds comprise of an aromatic group possessing a trifluoromethyl substituent. Burshtain et al. (US 2019/0207270 A1) discloses an electrolyte infiltrating the positive electrode wherein the positive electrode possesses pores and the liquid electrolyte infiltrates said pores. Yushin et al. (US 2019/0081359 A1) discloses a battery electrolyte composition that may include ethyl methyl sulfone and various sulfoxides as solvents. Jiang et al. (US 2008/0026290 A1) discloses a battery comprising of an electrolyte composition wherein sulfolane may be included as a solvent. Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to SANTINO M SERVAGNO whose telephone number is (571)270-0847. The examiner can normally be reached M-Th 8:00 am - 5:00 pm, F 8:00 am - 4:00 pm. 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, Joshua Allen can be reached at (571) 270-3176. 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. /SANTINO MICHALE SERVAGNO/Examiner, Art Unit 1713 /JOSHUA L ALLEN/Supervisory Patent Examiner, Art Unit 1713
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Prosecution Timeline

Dec 06, 2023
Application Filed
Aug 11, 2026
Non-Final Rejection mailed — §102 (current)

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1-2
Expected OA Rounds
Grant Probability
Low
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Based on 0 resolved cases by this examiner. Grant probability derived from career allowance rate.

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