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
Claims 1-47 are pending.
Claims 1, 22, 24-31, 36 and 37 are amended.
Response to Amendment
Applicant’s amendment filed on 12/02/2025 has been entered.
The 102 rejections from previous office action have been withdrawn.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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) 1-5, 10,11, 16-18, 21-29, 32- 37, 40-47 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al (US 20200099098 A1) in view of Wang et al (US 20200099103 A1; referred to as Wang 2).
Regarding Claim 1,
Wang teaches an electrolyte comprising a lithium salt (Paragraph 0090), an organic compound comprising fluoroethylene carbonate (Paragraph 0077), vinylene carbonate (table associated with paragraph 0164- image below), atleast one ester ES including ethyl propionate (solvent used in electrolyte as stated in Paragraph 0097; and table image below), and a nitrile additive composition (adiponitrile, butanedinitrile; table image below).
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Wang teaches that the nitrile additive in the electrolyte is present between 2% to 11 % by weight (Paragraph 0006). The presence of 2% of nitrile additive is within the claimed range of 0.1 to 2 mol% of NAC in the electrolyte. Furthermore, Wang 2 teaches an electrolyte mixture as well that comprises a multinitrile compound with ether bond present in the electrolyte at 0.1 to 5 wt % (Paragraph 0007). This range also overlaps with the claimed range. Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to the composition range of multinitrile compound in Wang 2 in the electrolyte mixture in order to provide an electrochemical device with excellent cycle, storage, and floating charge performance (Paragraph 0004).
Wang teaches that the electrolyte contains solvent mixtures that comprise chain carboxylate esters such as ethyl propionate (Paragraph 0097). Wang also teaches in the method of preparation that a basic electrolyte solution is formed from the solvents and lithium salt (Paragraph 0147). While the basic electrolyte in the example does not use ethyl propionate (it uses EC, PC, DEC as solvents), but based on the solvents listed in Paragraph 0097, the invention of Wang can utilize ethyl propionate in the basic electrolyte. Based on Table 1-1, the basic electrolyte is mixed with components A, B, C in given weight %. This shows that the % of basic electrolyte can be around 65% to 70%. Within this basic electrolyte the composition of ethyl propionate can be atleast 35 mol % as claimed since Wang teaches that the non-aqueous solvent may be used alone or in combination of two or more of the alternatives listed (Paragraph 0102). Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use the ethyl propionate in the electrolyte within the claimed range in order to inhibit the increase in internal resistance of electrochemical device (Paragraph 0138).
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Furthermore, Wang 2 teaches the presence of atleast one of ethyl propionate, propyl propionate in the electrolyte and it is present in a content of about 1 to 60 wt % based on the total weight of the electrolyte (Paragraph 0028). Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use the propionate composition in Wang 2 which overlaps with the claimed range.
Regarding Claims 2, 3, 4, 5, 10, 11, 16, 17, and 18,
Wang teaches nitrile compound chemical formulas (paragraphs 0045-47, and paragraphs 0051-0054) used in the electrolyte, and also explicitly teaches the same nitrile compounds as instant specification in Paragraphs 0049 and 0056 – adiponitrile, 1,5-dicyanopentane, 1,4-dicyano-2-butene, 1,3,6-hexanetricarbonitrile. The claims that describe further structure limitations (such as claim 4, 6 etc) are anticipated by the specific chemical compound that meets those limitations. Claim 2 states that a and b represent 1 which implies a dinitrile compound. Claim 16 states that ‘c’ represents 1 which implies a trinitrile compound. Wang also provides compounds of dinitrile and trinitrile type.
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Regarding Claim 21 and 23,
Wang teaches the use of LiPF6 as a lithium salt in the electrolyte (Paragraph 0090), and also provides Example using LiPF6 at 1.15 mol/L (Paragraph 0147).
Wang teaches that lithium difluoro(oxalate)borate can be used as an electrolyte salt (paragraph 0090).
Regarding Claim 22 and 24,
Wang teaches that the lithium salt concentration is in the range of about 0.8 – 3.0 mol/L. The claimed range is expressed as mol %. Hence, upon converting the range in Wang to mol %, the amount of lithium salt is around 9 to 25%. There is overlap between the range in Wang and the claimed range of 8 to 15 mol % of primary lithium salt LiPF6. In the same vein, Wang teaches more than one lithium salt can be selected wherein the total lithium salt content is between around 9 to 25 mol %. Hence, the additive lithium salt can be added in the claimed range of 0.2-2.4 mol%.
Regarding Claim 25 to Claim 28,
Wang teaches that the electrolyte contains solvent mixtures that comprise chain carboxylate esters such as ethyl propionate (Paragraph 0097). Wang also teaches in the method of preparation that a basic electrolyte solution is formed from the solvents and lithium salt (Paragraph 0147). While the basic electrolyte in the example does not use ethyl propionate (it uses EC, PC, DEC as solvents), but based on the solvents listed in Paragraph 0097, the invention of Wang can utilize ethyl propionate in the basic electrolyte. Based on Table 1-1, the basic electrolyte is mixed with components A, B, C in given weight %. This shows that the % of basic electrolyte can be around 65% to 70%. Within this basic electrolyte the composition of ethyl propionate can be such that it is within the range of 35 mol % to 75 mol %, or in the range of 39 mol% to 61 mol %, or atleast 39 mol %, or atleast 60 mol % since Wang teaches that the non-aqueous solvent may be used alone or in combination of two or more of the alternatives listed (Paragraph 0102). Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use the ethyl propionate in the electrolyte within the claimed range in order to inhibit the increase in internal resistance of electrochemical device (Paragraph 0138).
Regarding Claim 29,
Wang teaches the use of propyl propionate in table 2 and also stated in Paragraph 0008.
Regarding Claim 32,
Wang teaches a lithium ion battery comprising an anode, a cathode, a separator and the claimed electrolyte (Paragraph 0141-0151).
Regarding Claim 33 -37, and 40,
Wang teaches nitrile additives with 2 or 3 nitrile groups such as butanedinitrile, glutaronitrile, adiponitrile, 1,5-dicyanopentane, 1,6-dicyanohexane, 1,7-dicyanoheptane, 1,8-dicyanooctane, 1,9-dicyanononane, 1,10-dicyanodecane, 1,12-dicyanododecane, tetramethylbutanedinitrile, 2-methylglutaronitrile, 2,4-dimethylglutaronitrile, 2,2,4,4-tetramethylglutaronitrile, 1,4-dicyanopentane, 2,6-dicyanoheptane, 2,7-dicyanooctane, 2,8-dicyanononane, 1,6-dicyanodecane, 1,2-dicyanobenzene, 1,3-dicyanobenzene, 1,4-dicyanobenzene, 3,5-dioxa-pimelonitrile, 1,4-bis(cyanoethoxy)butane, ethylene glycol bis(2-cyanoethyl)ether, diethylene glycol bis(2-cyanoethyl)ether, triethylene glycol bis(2-cyanoethyl)ether, tetraethylene glycol bis(2-cyanoethyl)ether, 3,6,9,12,15,18-hexaoxaeicosanoic dinitrile, 1,3-bis(2-cyanoethoxy)propane, 1,4-bis(2-cyanoethoxy)butane, 1,5-bis(2-cyanoethoxy)pentane, ethylene glycol bis(4-cyanobutyl)ether, 1,4-dicyano-2-butene, 1,4-dicyano-2-methyl-2-butene, 1,4-dicyano-2-ethyl-2-butene, 1,4-dicyano-2,3-dimethyl-2-butene, 1,4-dicyano-2,3-diethyl-2-butene, 1,6-dicyano-3-hexene, 1,6-dicyano-2-methyl-3-hexene, or 1,6-dicyano-2-methyl-5-methyl-3-hexene. These satisfy the limitations of claim 34 and 35 related to the carbon atoms in the shortest chain between 2 adjacent nitrile groups.
Molecular weight is well known for these compounds and inherent to the chemicals listed above. Similarly, the density and boiling point of these nitrile compounds are known properties, as well as the property of being non-ionic. See MPEP 2112.01- Products of identical chemical composition can not have mutually exclusive properties.
Regarding Claims 41-45,
Wang teaches nitrile additives with 2 or 3 nitrile groups such as butanedinitrile, glutaronitrile, adiponitrile, 1,5-dicyanopentane, 1,6-dicyanohexane, 1,7-dicyanoheptane, 1,8-dicyanooctane, 1,9-dicyanononane, 1,10-dicyanodecane, 1,12-dicyanododecane, tetramethylbutanedinitrile, 2-methylglutaronitrile, 2,4-dimethylglutaronitrile, 2,2,4,4-tetramethylglutaronitrile, 1,4-dicyanopentane, 2,6-dicyanoheptane, 2,7-dicyanooctane, 2,8-dicyanononane, 1,6-dicyanodecane, 1,2-dicyanobenzene, 1,3-dicyanobenzene, 1,4-dicyanobenzene.
These compounds do not have a trifluoro group, tetrafluorobenzene group, thiophene group, carboxyl group, oxane group.
Regarding Claims 46 and 47,
Wang teaches the use of ethylene carbonate (non-fluorinated) in the electrolyte as shown in table below and Paragraph 0147.
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Claims 6-7 are rejected under 35 U.S.C. 103 as being unpatentable over Wang, in view of Wang 2 et al, further in view of Yamaguchi (JP 2013038029A – machine translation).
Wang does not teach the electrolyte with nitrile additive such that the X in the nitrile additive represents C1-6 alkylene, and R1 and R2 taken together represents a C3-6 cycloalkyl etc. Wang also does not expressly teach the nitrile compound as 1-(cyanomethyl)cyclopropane-1-carbonitrile.
However, Yamaguchi teaches the use of 1,1-dicyanocyclopentane (Paragraph 0052).
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This compound is different from the claimed chemical 1-(cyanomethyl)cyclopropane-1-carbonitrile.
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The compound in Yamaguchi has a cyclopentane structure, and does not have the additional carbon atom in one of the CN terminated chains. Yamaguchi has proposed the use of these cyclic nitrile compounds in order to improve the oxidation resistance of the electrolyte (Paragraph 0005). The instant specification also alludes to the use of nitrile additives that have properties of low oxidation and high reduction potentials to build stable CEI and SEI at high temperatures (instant spec; Paragraph 0171). Per MPEP 2144.09, a prima facie case of obviousness can be made when chemical compounds have very close structural similarities and similar utilities.
Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use these compounds as electrolyte additives in order to improve oxidation resistance of the electrolyte (Paragraph 0005).
Claims 8, 9 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al in view of Wang 2 et al.
Wang teaches that the R groups in formula 4 and 5 are alkylene groups further defined as linear or branched saturated hydrocarbon group (Paragraph 0030). Furthermore, Wang teaches the use of 1,6-dicyanoheptane, and 1,8-dicyanononane (paragraph 0049).
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These compounds are structurally similar to the claimed compound of 4,4-dimethylheptanedinitrile, and contain 9 carbon atoms in a branched structure which would be an offshoot of a branched nonane type compound.
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Wang teaches that the nitrile additive is capable of forming a protective film on the cathode that inhibits the decomposition of the solvent and inhibiting increase in internal resistance (paragraph 0005). Per MPEP 2144.09, a prima facie case of obviousness can be made when chemical compounds have very close structural similarities and similar utilities.
Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use these compounds as electrolyte additives.
Claim(s) 12, 13, 38, 39 are rejected under 35 U.S.C. 103 as being unpatentable over Wang in view of Wang 2, and further in view of Woo et al (KR 20210106817 A; machine translation).
Regarding Claims 12, 13,
Wang does not expressly teach the use of the chemical structure described in Claim 12, and the specific example in Claim 13 – 3-(2-cyanoethoxy)propanenitrile.
However, Woo teaches Formula 1 : NC-R1-R-R2-CN where R is a substituted or unsubstituted C 1 to C 20 alkylene group, a substituted or unsubstituted C 1 to C 20 alkenylene group, a substituted or unsubstituted C 1 to C 20 alkynylene group, a substituted or unsubstituted C 3 to 15 cyclic alkylene group, substituted or unsubstituted C3 to C15 arylene group, substituted or unsubstituted C3 to C15 heteroarylene group, -O-, -N=N- or -NR3- (the above R3 is hydrogen or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms), and R1 and R2 are each independently a substituted or unsubstituted C1-C20 alkylene group or a substituted or unsubstituted C1-C20 alkenylene group. Woo also provides chemical structure of a specific example as shown below.
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The claimed compound is a saturated version of the compound cited in Woo. These are similar chemical structures considering MPEP 2144.09. Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use 3-(2-cyanoethoxy)propanenitrile as electrolyte additive in order to improve cycle capacity characteristics and less cell swelling during storage at high temperatures (Paragraph 0012).
Regarding Claims 38 and 39,
Wang does not teach the use of a nitrile compound that includes a heteroarylene group of the type – imidazole or pyridine group.
However, Woo teaches the use of Compound 1a-3 (Paragraph 0102) with the following chemical structure
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This structure includes a heteroarylene group with N atom, and comprises the pyridine group. Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use a heterarylene group of imidazole/pyridine type in order to improve cycle capacity characteristics and less cell swelling during storage at high temperatures (Paragraph 0012).
Claim(s) 14 is rejected under 35 U.S.C. 103 as being unpatentable over Wang in view of Wang 2 , further in view of Lee et al (EP 3855549 B1; WO 2020/096411).
Wang does not teach a nitrile compound with heteroarylene structure, each of Y1 and Y2 represents a single C-C bond, and each of n1 and n2 represents 0.
However, Lee provides an electrolyte additive of Formula 1 (paragraph 0033) that has these structural limitations.
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This compound improves durability and high-temperature storage characteristics of the battery by forming a stable solid electrolyte interphase layer (Paragraph 0034). Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use such a compound as an electrolyte additive.
Claim(s) 19, 20 are rejected under 35 U.S.C. 103 as being unpatentable over Wang in view of Wang 2, further in view of Kim et al (US 20160301103 A1).
Wang does not explicitly teach the structural limitations of claim 19, and the specific chemical compound related to those limitations in Claim 20.
However, Kim teaches the use of a nitrile additive with the following structural limitations.
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Kim also specifically provides the structure of the following chemical compound.
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This chemical structure corresponds to 3-{[1,3-bis(2-cyanoethoxy)propan-2-yl]oxy} propanenitrile in the instant specification.
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Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in Kim as an additive in order to decrease a swelling phenomenon of a battery due to oxidation/decomposition of the electrolyte at a high voltage state (Paragraph 0010).
Claim(s) 30 and 31 are rejected under 35 U.S.C. 103 as being unpatentable over Wang in view of Wang 2, further in view of Ryu et al (US 20120100417A1).
Wang teaches that the basic electrolyte is made by combining EC, PC, DEC at a weight ratio of about 1:1:1 (Paragraph 0147). Wang also teaches the use of cyclic carbonate esters as non-aqueous solvent (Paragraph 0093). Wang does teach the use of vinylene carbonate as electrolyte (Paragraph 0074) but does not teach using it in the claimed range.
However, Ryu teaches the use of carbonate and ester based solvents in the electrolyte and further states that the mixture ratio can be appropriately controlled according to the desired battery performance which is widely understood to those skilled in the art (Paragraph 0051). Hence, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to use VC at the claimed ratio in order to meet the desired properties of the electrolyte for lithium ion batteries.
Allowable Subject Matter
Claim 15 is 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. The specific chemical compound of claim 15 is not found in prior art and also specifically in relation to providing beneficial effects as an electrolyte additive. Woo provides examples of heteroarylene nitrile compounds, but does not read upon the limitations of these claims. Lee provides a similar compound as the claimed one but the branched alkyl portion is attached to the N atom on the ring. Hence, it does not fully read upon this structure.
References of Interest
Kim et al (US 7858241-B2)
Wang et al (US 20200099103 A1)
Jeon et al (US 20120196191 A1)
Yamada et al (EP 4418350 A1)
Response to Arguments
Applicant’s arguments with respect to claim(s) 1 have been considered but are moot because the new ground of rejection does not rely on the combination of references applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant argues that Wang is silent as to the preferred ranges for the mass fractions of ethyl propionate in an electrolyte. Examiner contends that the rejection of amended claim 1 in the 103 section of this office action supports how Wang teaches the expected range of ethyl propionate in the electrolyte. Furthermore, the reference of Wang 2 also provides a range as detailed in the rejection.
Applicant argues that Wang’s example electrolytes do not meet the limitations of the amended claim 1 with regards to the mole fraction of NAC in the electrolyte. Examiner contends that the rejection of amended claim 1 in the 103 section of this office action supports how Wang teaches overlap in the content % of nitrile additive between Wang and claimed invention. Furthermore, the reference of Wang 2 also provides a range as detailed in the rejection.
Applicant argues that the example electrolytes show % quite large compared to the mole fraction in amended claim 1. Examiner points to rejection of amended claim 1 in this office action based on combination of references of Wang and Wang 2. A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. See MPEP 2123.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/SUHANI JITENDRA PATEL/Examiner, Art Unit 1783
/MARIA V EWALD/Supervisory Patent Examiner, Art Unit 1783