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 .
Status of Claims
This is a second non-final office action for application 17/830,951 in response to the argument(s)/amendment(s) filed on 06/02/2026. Claims 1-16 and 18-20 are under examination.
Withdrawn Objections
The amendment(s) to the claim(s), specification, and/or drawing(s) filed 06/02/2026 is acknowledged and the previous objections are withdrawn.
Response to Arguments
Applicant’s arguments filed on 06/02/2026 have been fully considered but are not persuasive. However, while the arguments are not a persuasive, a new search was still conducted and prior art more relevant to the claim scope was identified. This prior art, Cai et al (CN 109659612 A), has been incorporated into the rejection below as the secondary reference in the 35 U.S.C. 103 rejections replacing the previously relied upon reference Hu et al. (US-20200028213-A1). Due to a new reference being used this is a second Non Final Office action. The arguments were not found persuasive for the reasons set forth below.
The amendment changing the dependency of claim 15 does not overcome the rejection under 35 U.S.C. 112(d). Claim 1 already requires PS, FEC, and SN. Because claim 15 may be satisfied by those same components, claim 15 does not necessarily further limit claim 1. The rejection is maintained as set forth below. The rejection of claim 16 under 35 U.S.C. 112(d) is also maintained because claim 16 depends from claim 15.
Applicant’s unexpected results evidence has also been considered. The disclosed testing is limited principally to 1 wt% Pyr14CNFSI in one particular electrolyte formulation. The claims are substantially broader and encompass multiple compounds, anions, concentrations, additive amounts, and electrolyte formulations. In particular, only 1 wt% was tested for the range of claim 6, and no results were provided for the seven component additive combination of claim 16. The results therefore are not commensurate in scope with the claims.
Moreover, Han and Cai teach using the cited electrolyte components to improve cycling performance, high temperature performance, and impedance. Applicant has not shown that the degree of improvement would have been unexpected over the closest teachings of the prior art. To the extent Plots A-F contain testing not included in the original disclosure, that testing was presented only in attorney remarks and is afforded limited weight absent supporting evidence.
Accordingly, when the evidence is considered as a whole, it does not outweigh the evidence supporting obviousness. See claims 1-16 and 18-20 rejections below.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim Rejections - 35 USC § 112
Claims 15-16 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 15 depends from claim 1 and recites that “the additive” is selected from LiDFOB, PES, MMDS, PS, FEC, SN, HTCN, and a combination thereof. Claim 1 already requires PS, FEC, and SN. Claim 15 therefore may be satisfied solely by components already required by claim 1 and does not necessarily further limit the subject matter of claim 1. Claim 16 depends from claim 15 and includes the same defect.
Claim Rejections - 35 USC § 103
Claims 1-5, 7-12, 14-16 and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Han et al. (CN 103618111 A) and further in view of Cai et al. (CN 109659612 A).
Regarding Claim 1, Han discloses a battery cell (see e.g. "preparation of lithium secondary battery" in paragraph [93] on page 11) comprising:
a cathode (see e.g. "positive pole" in paragraph [19] on page 4) comprising a cathode active material disposed on a cathode current collector (see e.g. "the positive pole using in the present invention and negative pole comprise active material, conductive agent, collector, described active material and conductive agent are combined with described collector" in paragraph [70] on page 9);
an anode (see e.g. "Negative pole" in paragraph [20] on page 4) comprising an anode active material disposed on an anode current collector (see e.g. "the positive pole using in the present invention and negative pole comprise active material, conductive agent, collector, described active material and conductive agent are combined with described collector" in paragraph [70] on page 9), and
an electrolyte fluid (see e.g. "ionic liquid electrolyte" in Abstract on page 1) comprising:
a compound of Formula (I) (see e.g. "the general formula of ionic liquid is C +[A] -, the C of nitrile group-containing functional group wherein +cationic structural formula" in paragraph [50] and "R in structural formula 1, R 2, R 3and R 4 identical or not identical, have a substituting group Wei – (CH at least 2)ncN, n=1～10" in paragraph [52] on page 8 and the image below) and an anion (see e.g. "Anion" in paragraph [54] on page 8) wherein n is an integer greater than or equal to 1 and less than or equal to 10 (see e.g. "R in structural formula 1, R 2, R 3and R 4 identical or not identical, have a substituting group Wei – (CH at least 2) ncN, n=1～10" in paragraph [52] on page 8); and
propane sultone (PS) (see e.g. “PS” in claim 5 on page 15); and
fluoroethylene carbonate (FEC) (see e.g. "additive comprises... fluorinated ethylene carbonate" in paragraph [16] on page 4).
Han discloses a range that overlaps with the range claimed by the instant application. In the case where the prior art discloses a range that overlaps with the claimed range, a prima facie case of obviousness exists. See MPEP 2144.05 (I).
Han does not explicitly disclose that the anode is oriented towards the cathode such that the anode active material faces the cathode active material, that a separator is disposed between the cathode active material and the anode active material or that the electrolyte fluid further comprises succinonitrile (SN).
Cai, however, in the same field of endeavor, electrolyte stabilizing materials for use in battery cells, discloses a battery cell (see e.g. "lithium secondary battery " in paragraph [50] of Cai) wherein the anode is oriented towards the cathode such that the anode active material faces the cathode active material (see e.g. “anode pole piece obtained, isolation film, Cathode pole piece is folded in order, so that isolation film is in the centre of anode pole piece and cathode pole piece” in paragraph [50] of Cai)),
a separator is disposed between the cathode active material and the anode active material (see e.g. " isolation film is in the centre of anode pole piece and cathode pole piece” in paragraph [50] of Cai; the isolation piece is the separator), and
an electrolyte fluid that comprises succinonitrile (SN) (see e.g. "succinonitrile" in paragraph [40] of Cai).
Cai further teaches that when this particular electrolyte is added to a lithium ion battery, the anode can be stabilized which improves the high-temperature behavior and cycle performance of the lithium ion battery. At the same time, this also reduces membrane impedance, charging performance is improved, and safety is improved (see e.g. paragraph [43] of Cai). Therefore, it would have been obvious to a person of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the battery cell of Han et al. such that the anode is oriented towards the cathode such that the anode active material faces the cathode active material, a separator is disposed between the cathode active material and the anode active material and the electrolyte fluid further comprises succinonitrile (SN) as taught by Cai et al. in order to stabilize the anode and provide a battery lithium ion battery performance as suggested by Cai.
PNG
media_image1.png
139
138
media_image1.png
Greyscale
(Han, figure taken from disclosure)
Regarding Claim 2, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that n is an integer greater than or equal to 1 and less than or equal to 10 (see e.g. "(CH2)nCN，n=1～10" on page 14).
Han discloses a range that overlaps with the range claimed by the instant application. In the case where the prior art discloses a range that overlaps with the claimed range, a prima facie case of obviousness exists. See MPEP 2144.05 (I).
Regarding Claim 3, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that n is an integer greater than or equal to 1 and less than or equal to 10 (see e.g. "(CH2)nCN, n=1～10" on page 14).
Han discloses a range that overlaps with the point claimed by the instant application. In the case where the prior art discloses a range that overlaps with the claimed point, a prima facie case of obviousness exists. See MPEP 2144.05 (I).
Regarding Claim 4, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that the anion is selected from BF4-, PF6-, OTF (also commonly known as the triflate anion with chemical formula CF3SO3-), NTf2- (also commonly known as the bistriflimide anion or TFSI-), and N(SO2F)2- (also commonly known as the bis(fluorosulfonyl)imide anion or FSI-) (see e.g., "BF4-, PF6-, CF3SO3-, TFSI-, and FSI-" in paragraph [54] on page 8).
Regarding Claim 5, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses the compound is the compound of Formula (II), which is a five-membered ring structure containing a nitrogen atom also known as a pyrrolidine ring, attached to the nitrogen atom are two substituents, the first substituent is a four carbon nitrile group (i.e. (CH2)3CN) and the second substituent is a methyl group, with this compound there is also the anion N(SO2F)2- (also commonly known as the bis(fluorosulfonyl)imide anion or FSI-) (see e.g. "the C of nitrile group-containing functional group wherein +cationic structural" in paragraph [50] on page 8 and the image below which represents the pyrrolidine ring with two substituents attached to the nitrogen and "R in structural formula 1, R 2, R 3and R 4identical or not identical, have a substituting group Wei – (CH at least 2) ncN, n=1～10." in paragraph [52] on page 8; this represents the first substituent described above, the 4 carbon nitrile group, (CH2)3CN) and "R in structural formula 1, R 2, R 3or R 4bu Wei – (CH 2) during CN substituting group, R 1, R 2, R 3or R 4structure Wei – C mh 2m+1, m=1～10." in paragraph [53] on page 8; this represents the second substituent described above, the methyl group, C1H3 and "The anion [A]- is... FSI-" in paragraph [54] on page; this is the anion N(SO2F)2- ) on page 8).
Regarding Claim 7, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that the battery cell comprises an electrolyte salt selected from LiPF6, LiBF4, LiClO4, and LiN(SO2CF3)2 (also commonly known as LiTFSI) (see e.g. "LiPF6, LiBF4, LiTFSI, and LiCLO4" in paragraph [15] on page 4).
Regarding Claim 8, Han in view of Cai discloses the battery cell of claim 7 (see e.g. claim 7 rejection above).
Han further discloses that the salt comprises LiPF6 (see e.g. "LiPF6" in paragraph [15] on page 4).
Regarding Claim 9, Han in view of Cai discloses the battery cell of claim 7 (see e.g. claim 7 rejection above).
Han further discloses that the concentration of the electrolyte salt is 0.5 - 2 mol/L (see e.g. "0.5 - 2 mol/L" in paragraph [15] on page 4).
Han discloses a range that overlaps with the range claimed by the instant application. In the case where the prior art discloses a range that overlaps with the claimed range, a prima facie case of obviousness exists. See MPEP 2144.05 (I).
Regarding Claim 10, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that the electrolyte fluid comprises a solvent selected from ethylene carbonate (EC), dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC), ethyl propionate (EP), methyl acetate (MA), ethyl acetate (EA), propyl propionate (PP), and butyl acetate (BA) (see e.g. "ethylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, ethyl propionate, methyl acetate, ethyl acetate, propyl propionate, and butyl acetate" in paragraph [64] on page 9).
Regarding Claim 11, Han in view of Cai discloses the battery cell of claim 10 (see e.g. claim 10 rejection above).
Han further discloses that the solvent is selected from propylene carbonate PC, EC, PP or EP (see e.g., "propylene carbonate, ethylene carbonate, propyl propionate, and ethyl propionate" in paragraph [64] on page 9).
Regarding Claim 12, Han in view of Cai discloses the battery cell of claim 10 (see e.g. claim 10 rejection above).
Han further discloses that the solvent is selected from PC, EC, PP and EP (see e.g., "propylene carbonate, ethylene carbonate, propyl propionate, and ethyl propionate" in paragraph [64] on page 9). Regarding Claim 14, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han further discloses that the electrolyte fluid comprises an additive selected from vinyl ethylene carbonate (VEC) and fluoroethylene carbonate (FEC) (see e.g. "vinylethylene carbonate, fluorinated ethylene carbonate" in paragraph [16] on page 4).
Regarding Claim 15, Han in view of Cai discloses the battery cell of claim 14 (see e.g. claim 14 rejection above).
Han further discloses that the electrolyte fluid comprises an additive selected from fluoroethylene carbonate (FEC) (see e.g. "fluorinated ethylene carbonate" in paragraph [16] on page 4).
Regarding Claim 16, Han in view of Cai discloses the electrolyte fluid of claim 15 (see e.g. claim 15 rejection above).
Han further discloses that the additive comprises PS (see e.g. “PS” in claim 5 on age 15), and FEC (see e.g. "fluorinated ethylene carbonate" in paragraph [16] on page 4).
Han does not disclose that the additive comprises LiDFOB, PES, MMDS, SN and HTCN.
Cai, however, discloses an electrolyte solution that comprises LiDFOB, PES, MMDS, SN and HTCN (see e.g. “difluorine oxalic acid boracic acid lithium (LiODFB)” in paragraph [38] and “methane-disulfonic acid methylene ester (MMDS), propene sultone (PES), succinonitrile (SN)… three nitrile of hexane (HTCN)” in paragraph [40]).
Cai further teaches that when this particular electrolyte is added to a lithium ion battery, the anode can be stabilized which improves the high-temperature behavior and cycle performance of the lithium ion battery. At the same time, this also reduces membrane impedance, charging performance is improved, and safety is improved (see e.g. paragraph [43] of Cai). Therefore, it would have been obvious to a person of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the battery cell of Han et al. such that the electrolyte additive further comprises LiDFOB, PES, MMDS, SN and HTCN as taught by Cai et al. in order to stabilize the anode and provide a battery lithium ion battery performance as suggested by Cai.
Regarding Claim 18, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han in view of Cai does not disclose that the specific discharge capacity at 25 °C of the battery cell is higher than the specific discharge capacity at 25 °C of a battery cell comprising the electrolyte fluid that does not include a compound of Formula (I).
Han in view of Cai, however, discloses a battery cell that meets all of the claim limitations of claim 1 (see e.g. claim 1 rejection above). Claim 18 imparts no new structural or compositional limitations and because this battery cell has the claimed components and structure, then the properties of this battery cell must be inherent and tCais a prima facie case of obviousness exists. See MPEP 2112 (II).
Regarding Claim 19, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han in view of Cai does not disclose that the energy retention of the battery cell at cycle 200 is at least 20% higher than the energy retention of a battery cell comprising the electrolyte fluid in the absence of the compound of Formula (I).
Han in view of Cai, however, discloses a battery cell that meets all of the claim limitations of claim 1 (see e.g. claim 1 rejection above). Claim 18 imparts no new structural or compositional limitations and because this battery cell has the claimed components and structure, then the properties of this battery cell must be inherent and tCais a prima facie case of obviousness exists. See MPEP 2112 (II).
Regarding Claim 20, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han in view of Cai does not disclose that the RSS of the battery cell at cycle 200 is at least 40% decreased than a battery cell comprising the electrolyte fluid in the absence of the compound of Formula (I).
Han in view of Cai, however, discloses a battery cell that meets all of the claim limitations of claim 1 (see e.g. claim 1 rejection above). Claim 18 imparts no new structural or compositional limitations and because this battery cell has the claimed components and structure, then the properties of this battery cell must be inherent and tCais a prima facie case of obviousness exists. See MPEP 2112 (II).
Claims 6 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Han et al. (CN 103618111 A) in view of Cai et al. (CN 109659612 A) as applied to claims 1 and 10 above, and further in view of Oldiges et al. (Understanding transport mechanisms in ionic liquid/carbonate solvent electrolyte blends, 14 May 2018, Royal Society of Chemistry, Volume 20).
Regarding Claim 6, Han in view of Cai discloses the battery cell of claim 1 (see e.g. claim 1 rejection above).
Han in view of Cai does not disclose that the compound is in an amount between 0.1 wt% and 10.0 wt% of the total electrolyte fluid.
Oldiges, however, in the same field of endeavor, ionic liquid/carbonate solvent electrolyte blends, discloses an electrolyte fluid that contains an ionic liquid with an anion in a carbonate solvent containing electrolyte salts (see e.g. “ionic liquid (IL) 1-butyl-1-methylpyrrolidinium bis(trifluoromethyl sulfonyl)imide (Pyr14TFSI), ethylene carbonate (EC) and dimethyl carbonate (DMC) with the conducting salts lithium hexafluorophosphate (LiPF6) and lithium bis(trifluoromethyl sulfonyl)imide (LiTFSI)” in Abstract of Oldiges). While Oldiges does not disclose the exact ionic liquid of claim 1, Oldiges does disclose an analogous ionic liquid to the instant application. Furthermore, Oldiges discloses that the ionic liquid is 10 wt.% of the electrolyte fluid (see e.g. “IL fraction of 10 w%” in Ionic Conductivities section paragraph starting with “Using 1 M LiTFSI” of Oldiges).
Oldiges discloses a point that lies on the end point of the range claimed by the instant application. In the case where the prior art discloses a point that lies on the end point of the claimed range, a prima facie case of obviousness exists. See MPEP 2144.05 (I).
Oldiges also teaches that the electrolyte blend achieves balanced ion transport properties, with approximately equal transport and lithium ion transference numbers maintained across a broad concentration range (see e.g. “approximately equal transport and transference numbers” in Abstract of Oldiges). In addition, the blend demonstrates robust interfacial behavior and consistent performance regardless of the specific conducting salt used, which further reinforces its suitability for high-performance battery applications (see e.g. “improved interfacial behavior” in Conclusion of Oldiges). Therefore, it would have been obvious to a person of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the compound amount in the electrolyte fluid of Han et al. in view of Cai et al. such that the compound is in an amount of 10.0 wt% of the total electrolyte fluid as taught by Oldiges et al. in order to have an electrolyte blend that achieves balanced ion transport properties as well as a blend that demonstrates robust interfacial behavior and consistent performance regardless of conducting salt used as suggested by Oldiges.
Regarding Claim 13, Han in view of Cai discloses the battery cell of claim 10 (see e.g. claim 10 rejection above).
Han in view of Cai does not disclose that PC is from 2 to 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 fluid.
Oldiges, however, discloses that EC is 15 wt. %, 25 wt.%, 30 wt.%, and 35 wt.% of the total electrolyte fluid (see e.g. “(100-x) wt.% EC:DMC (1:1 by wt.), respectively, with x = 0, 10, 30, 40, 50, 70, and 100” in Sample Preparation section of Oldiges; when x (wt.% of ionic liquid) is 30 wt.%, 40 wt.%, 50 wt.%, and 70 wt.% then the corresponding wt.% of solvent would be 70 wt.%, 60 wt.%, 50 wt.%, and 30 wt.%, the ratio of EC to DMC is 1:1 by wt.%, and tCais the corresponding EC wt.% must be 15 wt. %, 25 wt.%, 30 wt.%, and 35 wt.% of the total electrolyte fluid).
Oldiges also teaches that the electrolyte blend achieves balanced ion transport properties, with approximately equal transport and lithium ion transference numbers maintained across a broad concentration range (see e.g. “approximately equal transport and transference numbers” in Abstract of Oldiges). In addition, the blend demonstrates robust interfacial behavior and consistent performance regardless of the specific conducting salt used, which further reinforces its suitability for high-performance battery applications (see e.g. “improved interfacial behavior” in Conclusion of Oldiges). Therefore, it would have been obvious to a person of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the amount of ethylene carbonate (EC) in the electrolyte fluid of Han et al. in view of Cai et al. such that the compound is in an amount of 15 wt. %, 25 wt.%, 30 wt.%, or 35 wt.% of the total electrolyte fluid as taught by Oldiges et al. in order to have an electrolyte blend that achieves balanced ion transport properties as well as a blend that demonstrates robust interfacial behavior and consistent performance regardless of conducting salt used as suggested by Oldiges.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JESSE EFYMOW whose telephone number is (571)270-0795. The examiner can normally be reached Monday - Thursday 10:30 am - 8:30 pm 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, 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.
/J.J.E./Examiner, Art Unit 1723
/NICHOLAS P D'ANIELLO/Primary Examiner, Art Unit 1723
Prosecution Insights