Prosecution Insights
Last updated: April 19, 2026
Application No. 18/352,106

NITRILE ADDITIVES FOR ELECTROLYTES OF BATTERIES INCLUDING LITHIUM- AND MANGANESE-RICH POSITIVE ELECTRODES

Non-Final OA §102§103
Filed
Jul 13, 2023
Examiner
EOFF, ANCA
Art Unit
1722
Tech Center
1700 — Chemical & Materials Engineering
Assignee
GM Global Technology Operations LLC
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 10m
To Grant
91%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
982 granted / 1230 resolved
+14.8% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 10m
Avg Prosecution
48 currently pending
Career history
1278
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
47.1%
+7.1% vs TC avg
§102
20.0%
-20.0% vs TC avg
§112
20.0%
-20.0% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1230 resolved cases

Office Action

§102 §103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 1-20 are pending. Information Disclosure Statement The examiner would like to note that some of the references cited in the Information Disclosure Statement filed on July 13, 2023 have not been considered because the publication numbers of the references are not correct. Claim Objections Claim 5 is objected to because of the following informalities:the limitation “Tyrphostin 1” in claim 5 should be amended to recite “(4-methoxybenzylidene) malononitrile (Tyrphostin 1)” (see the attached “Tyrphostin 1”). Appropriate correction is required. Claim Rejections - 35 USC § 102 The following is a quotation of the appropriate paragraph of 35 U.S.C. 102 that forms 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. Claims 1, 10, and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yang et al. (CN 109786833A, with attached machine translation). With regard to claim 1, Yang et al. teach a lithium-ion battery comprising a positive electrode including Li2MnO3, a negative electrode, and an electrolyte (Example 7 in par.0047). The electrolyte comprises 1,2-difluoroethylene carbonate and ethyl methyl carbonate, 2mass% 1,2,3-tris-(2-cyanoethoxy)propane, 4mass% of fluoroethylene carbonate, and 12.5wt% LiPF6 (Example 7, par.0046). Li2MnO3 is a “lithium- and manganese-rich oxide” in claim 1, as defined in par.0039 of the specification of the instant application. 1,2-difluoroethylene carbonate and ethyl methyl carbonate are “organic solvents” in claim 1, and LiPF6 is “an inorganic lithium salt in the organic solvents” in claim 1. LiPF6 also meets the limitations of claim 14. 1,2,3-tris-(2-cyanoethoxy)propane is “a nitrile additive in the organic solvent” in claim 1, and the amount of 1,2,3-tris-(2-cyanoethoxy)propane is within the range in claim 10. Therefore, the lithium-ion battery in Example 7 of Yang et al. anticipates the batteries in claims 1, 10, and 14 of the instant application. 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 11 is rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (CN 109786833A, with attached machine translation). With regard to claim 11, Yang et al. teach the lithium-ion battery of claim 1 (see paragraph 6 above). The electrolyte comprises 4mass% of fluoroethylene carbonate (Example 7, par.0046), and this amount is not within the claimed range. However, Yang et al. teach that the electrolyte may comprise the fluoroethylene carbonate in an amount of 0.1-4mass% (claim 6). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to include fluoroethylene carbonate in an amount as low as 0.1mass% in the electrolyte of Yang et al. Claims 1, 4, 5, 10, and 12-20 are rejected under 35 U.S.C. 103 as being unpatentable over Yoon et al. (EP 3 041 077 A1) in view of Jung et al. (US 2008/0248397). With regard to claims 1, 14, and 15, Yoon et al. teach a secondary battery comprising: -a negative electrode comprising graphite and silicon oxide (SiO); -a positive electrode comprising LiCoO2; -an electrolyte comprising EC, EMC, DEC mixed in a volume 3:2:5, 1M LiPF6, 1.5wt% VC and 5wt% FEC as additives (Example 1 in par.0043-0045). The negative electrode meets the limitations of claim 15. The positive electrode in the battery of Example 1 does not contain a lithium- and manganese-rich oxide. However, Yoon et al. teach that LiMn2O3 is functionally equivalent to LiCoO2 as positive electrode active material (par.0029). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to use LiMn2O3 as positive electrode active material in the positive electrode in Example 1 of Yoon et al. Li2MnO3 is a “lithium- and manganese-rich oxide” in claims 1 and 15, as defined in par.0039 of the specification of the instant application. EC (ethylene carbonate) is a “cyclic carbonate organic solvent” in claim 15. EMC (ethyl methyl carbonate) and DEC (diethyl carbonate) are “linear carbonate organic solvents” in claim 15, LiPF6 is “an inorganic lithium salt in the organic solvents” in claim 1, and meets the limitations of claims 14 and 15. Yoon et al. fail to teach that the electrolyte comprises a nitrile additive. Jung et al. teach an electrolyte for a rechargeable lithium battery including an organic solvent, a lithium salt, and an additive including vinylene carbonate, fluoroethylene carbonate, and a nitrile-based compound. The rechargeable lithium battery including the electrolyte has improved storage stability (abstract). Jung et al. further teach that the nitrile-based compound may be succinonitrile (Example 1 in par.0078). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to include succinonitrile in the electrolyte of Yoon et al., in order to improve the storage stability of the battery. Therefore, the secondary battery of Yoon modified by Jung is equivalent to the batteries in claims 1, 14, and 15 of the instant application. With regard to claim 4, succinonitrile is a dinitrile additive of formula NC-R1-CN, wherein R1 is an ethylene group. With regard to claim 5 and 16, succinonitrile meets the claims limitations. With regard to claim 10, Jung et al. teach that the electrolyte may comprise succinonitrile in an amount of 1wt% (par.0078). This amount is within the claimed range. With regard to claim 12, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that during the cycling of the battery the nitrile additive decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode that isolates the electroactive material from physical contact with the electrolyte (par.0015). The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the cycling of the battery succinonitrile of Yoon modified by Jung decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode that isolates the electroactive material from physical contact with the electrolyte. "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999) (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY) With regard to claim 13, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that during the cycling of the battery the nitrile additive decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode. The interphase layer comprises an imino-functional organic compound, a cyano-functional organic compound, or a combination thereof (par.0020-0021). The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the charging of the battery succinonitrile of Yoon modified by Jung forms an interphase layer on surface of the electroactive material of the positive electrode and the interphase layer comprises an imino-functional organic compound, a cyano-functional organic compound, or a combination thereof (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY). With regard to claim 17, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that during the cycling of the battery the nitrile additive decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode that isolates the electroactive material from physical contact with the electrolyte (par.0015). The nitrile additive may decompose and form a second interphase layer on the electroactive material of the anode (par.0020). The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the cycling of the battery succinonitrile of Yoon modified by Jung decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode that isolates the electroactive material from physical contact with the electrolyte, and an interphase on the electroactive material of the negative electrode (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY). With regard to claim 18, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that an electrochemical oxidation of the nitrile may occur at the positive electrode during the charging of the battery. A first interphase layer is formed on the positive electrode active material and comprises an imino-functional organic compound, a cyano-functional organic compound, or a combination thereof (par.0020-0021). The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the charging of the battery succinonitrile of Yoon modified by Jung undergoes electrochemical oxidation at the positive electrode, forms an interphase layer on surface of the electroactive material of the positive electrode, and the interphase layer comprises an imino-functional organic compound, a cyano-functional organic compound, or a combination thereof (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY). With regard to claim 19, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that during the cycling of the battery the nitrile additive decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode that isolates the electroactive material from physical contact with the electrolyte (par.0015). The first interphase layer comprises LiF (par.0022). The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the cycling of the battery succinonitrile of Yoon modified by Jung decomposes and forms an interphase layer on surface of the electroactive material of the positive electrode and the first interphase layer comprises LiF (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY). With regard to claim 20, the electrolyte of Yoon modified by Jung comprises succinonitrile (see par.0078 of Jung et al.). The specification of the instant application teaches that the electrochemical reduction of the nitrile additive may occur at the negative electrode during the charge of the battery and the second interphase layer may comprise by-products of the electrochemical reduction of the nitrile additive (par.0023).The nitrile additive may be succinonitrile (par.0008). Absent a record to the contrary, it is expected that during the charging of the battery succinonitrile of Yoon modified by Jung undergoes electrochemical reduction and decomposes and forms an interphase layer on surface of the electroactive material of the negative electrode and the interphase layer may comprise by-products of the electrochemical reduction of succinonitrile (MPEP 2112.I. SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY). Claims 1-7, 10, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Kinoshita et al. (EP 3 764 451 A1). With regard to claims 1, 10, and 14, Kinoshita et al. teach a lithium ion secondary battery comprising a positive electrode, a negative electrode, and an electrolyte (par.0712). The positive electrode contains a positive electrode active material, such as Li2MnO3 (par.0720). The electrolyte comprises LiPF6 and a mixture of ethylene carbonate (EC) and ethyl methyl carbonate (EMC) (par.0867). The electrolyte may comprise a nitrile compound (par.0521), which is added to the electrolyte in an amount of 0.2 to 7mass% in order to further improve the high temperature storage characteristics and safety of the battery at high voltage (par.0547). Kinoshita et al. fail to specifically teach the battery in claim 1. However, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to obtain the battery in claim 1, because Kinoshita et al. teach the components of the lithium-ion secondary battery and provide examples for each component. Li2MnO3 is a “lithium- and manganese-rich oxide” in claim 1, as defined in par.0039 of the specification of the instant application. Ethylene carbonate (EC) and ethyl methyl carbonate (EMC) are the “organic solvents” in claim 1, and LiPF6 is “an inorganic lithium salt in the organic solvents” in claim 1. LiPF6 also meets the limitations of claim 14. The amount of nitrile included in the electrolyte is within the range in claim 10. Therefore, the batteries in claims 1, 10, and 14 are obvious over the lithium ion secondary battery of Kinoshita et al. With regard to claims 2 and 3, Kinoshita et al. teach that the nitrile compound may be acetonitrile, propionitrile, or benzonitrile (0540). These nitriles are mononitriles of formula R-CN, wherein R is an alkyl group or an aryl group in claim 2. With regard to claims 4 and 5, Kinoshita et al. teach that the nitrile compound may be malononitrile, succinonitrile, or adiponitrile (par.0531). These nitriles are dinitriles of formula CN-R1-CN, wherein R1 is a methylene group, ethylene group or a tetramethylene group in claim 4. With regard to claims 6 and 7, Kinoshita et al. teach that the nitrile compound may be 1,3,6-hexanetricarbonitrile (par.0532). This is a trinitrile in claim 6, wherein R1 is an ethylene group and R2 is a trimethylene group. Claims 1, 8-10, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Yu et al. (US 2013/0004861). With regard to claims 1 and 14, Yu et al. teach a lithium secondary battery including a positive electrode, a negative electrode, and a non-aqueous electrolyte (par.0015). The positive electrode may comprise a positive electrode active material such as LiaMnGbO2, wherein 0.90 ≤a≤1.8, 0.001≤b≤0.1, and G is Al, Cr, Mn, Fe, Mg, La, Ce, Sr, or V (par.0016). The non-aqueous electrolyte comprises is prepared by dissolving LiPF6 in an organic solvent (par.0077). Yu et al. further teach that the non-aqueous electrolyte comprises as an additive a compound of formula (1): PNG media_image1.png 78 106 media_image1.png Greyscale (abstract). Yu et al. fail to specifically teach the battery in claim 1. However, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to obtain the battery in claim 1, because Yu et al. teach the components of the lithium secondary battery and provide examples for each component. LiaMnGbO2, wherein 0.90 ≤a≤1.8, 0.001≤b≤0.1, and G is Al, Cr, Mn, Fe, Mg, La, Ce, Sr is a “lithium- and manganese-rich oxide” in claim 1, as defined in par.0039 of the specification of the instant application. LiPF6 is “an inorganic lithium salt in the organic solvents” in claim 1, and meets the limitations of claim 14. Therefore, the batteries in claims 1 and 14 are obvious over the lithium secondary battery of Yu et al. With regard to claims 8 and 9, Yu et al. teach that the examples of compound of formula (1) include tetracyanoethylene (par.0021). Tetracyanoethylene is a tetranitrile in claim 8 wherein R1 is a vinylene group, and meets the limitations of claim 9. With regard to claim 10, Yu et al. teach that the electrolyte comprises a compound of formula (1) in an amount of 0.01 to 10 wt% based on the total weight of the electrolyte. This amount is within the claimed range. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Honbou et al. (US 2012/0270092) teach a lithium-ion secondary battery comprising a separator, a positive electrode, a negative electrode, and an electrolyte comprising a compound of formula (1): PNG media_image2.png 108 144 media_image2.png Greyscale (abstract). The compound of formula (1) may be 4-methoxybenzonitrile (par.0023, par.0043). Kim et al. (US 2003/0068562) teach an electrolyte for a lithium secondary battery, wherein the electrolyte includes a lithium salt, a non-aqueous organic solvent and a compound of formula (1): PNG media_image3.png 94 140 media_image3.png Greyscale (abstract). Wang et al. (US 2019/0036168) teach an electrolyte comprising an electrolyte salt and an additive, and the additive comprises a multinitrile compound (abstract). The multinitrile compound may be represented by the formulas: PNG media_image4.png 270 398 media_image4.png Greyscale (par.0014). Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANCA EOFF whose telephone number is (571)272-9810. The examiner can normally be reached Mon-Fri 10am-6:30pm. 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, Niki Bakhtiari can be reached at (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. /ANCA EOFF/ Primary Examiner, Art Unit 1722
Read full office action

Prosecution Timeline

Jul 13, 2023
Application Filed
Feb 22, 2026
Non-Final Rejection — §102, §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

1-2
Expected OA Rounds
80%
Grant Probability
91%
With Interview (+11.3%)
2y 10m
Median Time to Grant
Low
PTA Risk
Based on 1230 resolved cases by this examiner. Grant probability derived from career allow rate.

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