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 .
Applicants’ remarks and amendments, filed on December 18, 2025, have been carefully considered. Claim 4 has been canceled; no new claims have been added.
Claims 1-3 and 5-10 remain presently pending in this application.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Applicants’ Priority Document was electronically retrieved on February 13, 2023.
Withdrawn Rejections
The following rejections of record, stated in the previous Office Action, have been withdrawn in view of Applicants’ amendment to claim 1 by the incorporation therein the subject matter of now-canceled claim 4:
The 35 U.S.C. 103 rejection of claims 1, 3, and 7-10 as being unpatentable over Funada et al. (U. S. Patent Publication No. 2011/0311886); and
The 35 U.S.C. 103 rejection of claims 1, 2, and 7-10 as being unpatentable over Xu et al. (CN 106299507) in view of Funada et al. (U. S. Patent Publication No. 2011/0311886).
Maintained Rejection
The following rejection of record, stated in the previous Office Action, is maintained. As Applicants’ have amended claim 1 by incorporating therein the subject matter of now-canceled claim 4, the references applied in said maintained rejection are considered to continue to read upon Applicants’ claims in their present form.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 3, 5, and 6 are rejected under 35 U.S.C. 103 as being unpatentable over Funada et al. (U. S. Patent Publication No. 2011/0311886) in view of Wang et al. (CN 103985904, English translation relied upon).
Regarding claims 1 and 3, Funada et al. teach a nonaqueous electrolyte comprising a solvent containing an halogenated carbonate ester, an electrolyte salt, and an antioxidant, wherein, based on the nonaqueous electrolyte, the content of the halogenated carbonate ester ranges from 0.1 to 50% by mass, more preferably from 1 to 10% by mass, and the content of the antioxidant is preferably from 0.01 to 5000 ppm. Examples of the halogenated carbonate ester include 4-fluoro-1,3-dioxolan-2-one (FEC; fluoroethylene carbonate; “auxiliary additive comprising a carbonate-based compound”). Examples of the electrolyte salt include lithium hexafluorophosphate (LiPF6) and lithium tetrafluoroborate (LiBF4). Examples of the antioxidant include a compound having a structure corresponding to the “additive represented by…Chemical Formula 2” in Applicants’ claim 1, and to the “additive…represented by Chemical Formula 4” in Applicants’ claim 3. See paragraphs [0015], [0028]-[0032], [0037]-[0039], [0046], [0047], and [0049] of Funada et al.
Further regarding claim 1, and also regarding claims 5 and 6, Funada et al. do not explicitly teach or suggest the presence of a sultone-based compound including either an alkyl sultone-based compound and an alkenyl sultone-based compound, as recited in these claims.
Regarding claim 1, Wang et al. teach a non-aqueous electrolyte comprising an organic solvent, lithium salts, and an additive, wherein the solvent is at least one of a cyclic carbonate or a chain-like carbonate, and the additive comprises 1,3-propanesultone (“alkyl sultone-based compound”), wherein, by weight, the organic solvent is 100 parts by weight, and the 1,3-propane sultone is 1 to 5 parts by weight. Examples of the cyclic and chain-like carbonates include ethylene carbonate, fluoroethylene carbonate, dimethyl carbonate, diethyl carbonate, and ethyl methyl carbonate. Wang et al. further teach the feasibility in the additive further containing conventional additives in amounts of 0.1 to 5 parts by weight. Exemplary conventional additives include vinylene carbonate, 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”); See the Abstract of Wang et al., as well as paragraph [0007]-[0010].
Exemplary lithium salts include LiPF6 and LiBF4; see paragraph [0013] of Wang et al.
Note that these organic solvents and lithium salts are also taught by Funada et al., as discussed above.
Motivated by these references’ teachings regarding non-aqueous electrolytes, said non-aqueous electrolytes having the same or similar components, it would have been obvious to one of ordinary skill in the art before the effective filing date of Applicants’ invention to modify the non-aqueous electrolyte of Funada et al. by incorporating therein, 1,3-propanesultone (“alkyl sultone-based compound”), 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”), as suggested by Wang et al., as, for example, 1,3-propane sultone can form a solid electrolyte interphase (SEI) film at the negative electrode, which can effectively improve the high-temperature storage characteristics of a lithium-ion secondary battery. See paragraph [0014] of Wang et al.
Further, motivated by these references’ teachings regarding non-aqueous electrolytes, said non-aqueous electrolytes having the same or similar components, it would have been obvious to one of ordinary skill in the art before the effective filing date of Applicants’ invention to modify the non-aqueous electrolyte of Funada et al. by incorporating therein, 1,3-propanesultone (“alkyl sultone-based compound”), 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”), as suggested by Wang et al., because it has been held that combining two or more materials disclosed by the prior art for the same purpose to form a third material that is to be used for the same purpose has been held to be a prima facie case of obviousness, see In re Kerkhoven, 205 U.S.P.Q. 1069. See also MPEP 2144.06(I).
Regarding claims 5 and 6, Wang et al., as stated above, teach that the non-aqueous electrolyte contains, 1 to 5 parts by weight 1,3-propane sultone, and 0.1 to 5 parts by weight conventional additive (e.g., propenyl-1,3-sultone).
By employing the amount of 5000 ppm antioxidant (5000 ppm = 0.5%) disclosed in Funada et al., and the amounts of 1,3-propane sultone (1 to 5 parts by weight) and the amount of conventional additive (e.g., propenyl-1,3-sultone; 0.1 to 5 parts by weight), the content of antioxidant relative to 1,3-propane sultone and propenyl-1,3-sultone can be determined:
0.5% antioxidant/1 pbw 1,3-propane sultone = 0.5, or 50%
0.5% antioxidant/5 pbw 1,3-propane sultone = 0.1, or 10%
0.5% antioxidant/0.1 pbw propenyl-1,3-sultone = 5, or 500%
0.5% antioxidant/5 pbw propenyl-1,3-sultone = 0.1, or 10%
Thus, for antioxidant/1,3-propane sultone, the percentage range of 10% to 50% overlaps the percentage range of “alkyl sultone-based compound…from 20 wt% to 100 wt%” in claim 5, and, for antioxidant/propenyl-1,3-sultone, the percentage range of 10% to 500% encompasses the percentage range of “alkenyl sultone-based compound…from 20 wt% to 170 wt%” in claim 6.
The subject matter as a whole would have been obvious to one having ordinary skill in the art at the time the invention was made to have selected the overlapping portion of the range disclosed by the reference because overlapping ranges have been held to be a prima facie case of obviousness. In re Malagari, 182 U.S.P.Q. 549. See also MPEP 2144.05.
“A prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prime facie case of obviousness.” In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003).
Funada et al. do not explicitly teach the limitations of Applicants’ claims regarding the content of the additive relative to a weight of the carbonate-based compound being in a range of from 10 wt% to 50 wt%, as recited in Applicants’ claim 1. However, as stated above, this reference teaches that, in the nonaqueous electrolyte, the content of the halogenated carbonate ester ranges from 0.1 to 50% by mass, more preferably from 1 to 10% by mass, and the content of the antioxidant is preferably from 0.01 to 5000 ppm.
By employing the amounts of 1-10% by mass of halogenated carbonate ester and the amount of 0.01-5000 ppm antioxidant (0.01-5000 ppm = 0.000001-0.5%), the amount of antioxidant (“additive”) relative to the amount of the halogenated carbonate ester (“auxiliary additive comprising a carbonate-based compound”) can be determined:
0.000001-0.5% by mass divided by 1-10% by mass is:
0.000001/1 = 0.000001 0.000001/10 = 0.0000001
0.5/1 = 0.5, or 50% 0.5/10 = 0.05, or 5%
Thus, 5000 ppm antioxidant in the electrolytic solution, divided by 1-10% by mass "auxiliary additive" results in a content of antioxidant based on auxiliary additive of 5% to 50%, which overlaps the claim limitation “wherein a content of the additive relative to a weight of the carbonate-based compound is in a range from 10 wt% to 50 wt%”.
The subject matter as a whole would have been obvious to one having ordinary skill in the art at the time the invention was made to have selected the overlapping portion of the range disclosed by the reference because overlapping ranges have been held to be a prima facie case of obviousness. In re Malagari, 182 U.S.P.Q. 549. See also MPEP 2144.05.
New Ground of Rejection
The following New Ground of Rejection is being made in view of Applicants’ amendment to claim 1 by the incorporation therein of now-canceled claim 4, and in view of the Examiner’s reconsideration of the cited references of record.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 2, and 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over Xu et al. (CN 106299507, English translation relied upon) in view of Funada et al. (U. S. Patent Publication No. 2011/0311886) and Wang et al. (CN 103985904, English translation relied upon).
Regarding claims 1 and 2, Xu et al teach an electrolyte solution comprising a lithium salt and a non-aqueous organic solvent, wherein the electrolyte further includes additives comprising flavonoid compounds having a formula corresponding to Chemical Formulae 1 and 3 in Applicants’ claims 1 and 2. An exemplary flavonoid compound is quercetin, which corresponds to Chemical Formulae 1 and 3 in Applicants’ claims 1 and 2 when, in Chemical Formula 1, A1 to A3 are a hydroxyl group, and R1 is a substituted C6 aryl group, and in Chemical Formula 3, A1 to A5 are all hydroxyl groups. See paragraphs [0009]-[0011] of Xu et al.
Regarding claim 7, Xu et al. teach that the amount of flavonoid compounds present in the electrolyte ranges from 0.002 to 0.1% by mass of the electrolyte. See paragraph [0025] of Xu et al. It is noted that this range shares a common endpoint with the range “0.1 wt% to 0.5 wt%”, as recited in claim 7.
It is considered that a prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. Titanium Metals Corp. of Amer.v.Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985).
Regarding claims 8 and 9, Xu et al. teach lithium salts such as LiPF6 and LiBF4, and non-aqueous organic solvents such as ethylene carbonate, dimethyl carbonate, diethyl carbonate, fluoroethylene carbonate, and ethyl methyl carbonate, as components in the electrolyte. See claim 9, paragraphs [0028] and [0030], and Example 1 of Xu et al.
Regarding claim 10, Xu et al. teach a lithium ion battery (“lithium secondary battery”) comprising a positive electrode (“anode”), a negative electrode (“cathode”), and the aforementioned electrolyte. See paragraphs [0019]-[0023] of Xu et al.
Although Xu et al. teach fluoroethylene carbonate as an exemplary organic solvent, this reference does not teach or suggest the employment of fluoroethylene carbonate as an “auxiliary additive comprising a carbonate-based compound”, nor does this reference teach the presence of said auxiliary additive comprising a carbonate-based compound, as recited in claim 1.
Funada et al. teach a nonaqueous electrolyte comprising a solvent containing an halogenated carbonate ester, an electrolyte salt, and an antioxidant, wherein, based on the nonaqueous electrolyte, the content of the halogenated carbonate ester ranges from 0.1 to 50% by mass, more preferably from 1 to 10% by mass, and the content of the antioxidant is preferably from 0.01 to 5000 ppm. Examples of the halogenated carbonate ester include 4-fluoro-1,3-dioxolan-2-one (FEC; fluoroethylene carbonate; “auxiliary additive comprising a carbonate-based compound”). Examples of the electrolyte salt include lithium hexafluorophosphate (LiPF6) and lithium tetrafluoroborate (LiBF4). See paragraphs [0015], [0028]-[0032], [0046], [0047], and [0049] of Funada et al.
Funada et al. further teach the feasibility in the aforementioned solvent containing an additional solvent, examples of which include ethylene carbonate, dimethyl carbonate, diethyl carbonate, and ethyl methyl carbonate. See paragraph [0034] of Funada et al.
Note that these solvents and electrolyte salts are also disclosed in Xu et al., as discussed above.
Motivated by these references’ common teachings regarding non-aqueous electrolytes, said non-aqueous electrolytes having the same or similar components, it would have been obvious to one of ordinary skill in the art to modify the electrolyte disclosed in Xu et al. by employing fluoroethylene carbonate as an auxiliary additive, as disclosed by Xu et al., or by incorporating therein fluoroethylene carbonate as an auxiliary additive, as suggested by Funada et al., because it has been held that combining two or more materials disclosed by the prior art for the same purpose to form a third material that is to be used for the same purpose has been held to be a prima facie case of obviousness, see In re Kerkhoven, 205 U.S.P.Q. 1069. See also MPEP 2144.06(I).
Additionally, Xu et al. do not teach or suggest the limitations of Applicants’ claims regarding the content of the additive relative to a weight of the carbonate-based compound being in a range of from 10 wt% to 50 wt%, as recited in Applicants’ claim 1.
However, by employing the amount of flavonoid by mass of the electrolyte taught by Xu et al. (0.002% to 0.1% by mass of the electrolyte; paragraph [0025]), and the amount of halogenated carbonate ester (fluoroethylene carbonate) taught by Funada et al. (0.1% by mass; paragraph [0032]), the amount of flavonoid (“additive”) relative to the amount of the fluoroethylene carbonate/halogenated carbonate ester (“auxiliary additive comprising a carbonate-based compound”) can be determined:
0.002-0.1% by mass divided by 0.1 % by mass is:
0.002/0.1 = 0.02, or 2% 0.1/0.1 = 1, or 100%
Thus, 0.1 % flavonoid in the electrolyte, divided by 0.1% by mass fluoroethylene carbonate/halogenated carbonate ester results in a content of flavonoid based on auxiliary additive of 2% to 100%, which encompasses the claim limitation “wherein a content of the additive relative to a weight of the carbonate-based compound is in a range from 10 wt% to 50 wt%”.
“A prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prime facie case of obviousness.” In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003).
Neither Xu et al. nor Funada et al. teach or suggest the presence of a sultone-based compound including an alkyl sultone-based compound and an alkenyl sultone-based compound, as recited in claims 1, 5, and 6.
Regarding claim 1, Wang et al. teach a non-aqueous electrolyte comprising an organic solvent, lithium salts, and an additive, wherein the solvent is at least one of a cyclic carbonate or a chain-like carbonate, and the additive comprises 1,3-propane sultone (“alkyl sultone-based compound”), wherein, by weight, the organic solvent is 100 parts by weight, and the 1,3-propane sultone is 1 to 5 parts by weight. Examples of the cyclic and chain-like carbonates include ethylene carbonate, fluoroethylene carbonate, dimethyl carbonate, diethyl carbonate, and ethyl methyl carbonate. Wang et al. further teach the feasibility in the additive further containing conventional additives in amounts of 0.1 to 5 parts by weight. Exemplary conventional additives include vinylene carbonate, 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”); See the Abstract of Wang et al., as well as paragraph [0007]-[0010].
Exemplary lithium salts include LiPF6 and LiBF4; see paragraph [0013] of Wang et al.
Note that these organic solvents and lithium salts are also taught by Xu et al. and Funada et al., as discussed above.
Motivated by these references’ teachings regarding non-aqueous electrolytes, said non-aqueous electrolytes having the same or similar components, it would have been obvious to one of ordinary skill in the art before the effective filing date of Applicants’ invention to modify the non-aqueous electrolyte of Xu et al. in view of Funada et al. by incorporating therein, 1,3-propanesultone (“alkyl sultone-based compound”), 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”), as suggested by Wang et al., as, for example, 1,3-propane sultone can form a solid electrolyte interphase (SEI) film at the negative electrode, which can effectively improve the high-temperature storage characteristics of a lithium-ion secondary battery. See paragraph [0014] of Wang et al.
Further, motivated by these references’ teachings regarding non-aqueous electrolytes, said non-aqueous electrolytes having the same or similar components, it would have been obvious to one of ordinary skill in the art before the effective filing date of Applicants’ invention to modify the non-aqueous electrolyte of Xu et al. in view of Funada et al. by incorporating therein, 1,3-propanesultone (“alkyl sultone-based compound”), 1,4-butane sultone (“alkyl sultone-based compound”) and propenyl-1,3-sultone (“alkenyl sultone-based compound”), as suggested by Wang et al., because it has been held that combining two or more materials disclosed by the prior art for the same purpose to form a third material that is to be used for the same purpose has been held to be a prima facie case of obviousness, see In re Kerkhoven, 205 U.S.P.Q. 1069. See also MPEP 2144.06(I).
Regarding claims 5 and 6, Wang et al., as stated above, teach that the non-aqueous electrolyte contains, 1 to 5 parts by weight 1,3-propane sultone, and 0.1 to 5 parts by weight conventional additive (e.g., propenyl-1,3-sultone).
By employing the amount of 5000 ppm antioxidant (5000 ppm = 0.5%) disclosed in Funada et al., and the amounts of 1,3-propane sultone (1 to 5 parts by weight) and the amount of conventional additive (e.g., propenyl-1,3-sultone; 0.1 to 5 parts by weight), the content of antioxidant relative to 1,3-propane sultone and propenyl-1,3-sultone can be determined:
0.5% antioxidant/1 pbw 1,3-propane sultone = 0.5, or 50%
0.5% antioxidant/5 pbw 1,3-propane sultone = 0.1, or 10%
0.5% antioxidant/0.1 pbw propenyl-1,3-sultone = 5, or 500%
0.5% antioxidant/5 pbw propenyl-1,3-sultone = 0.1, or 10%
Thus, for antioxidant/1,3-propane sultone, the percentage range of 10% to 50% overlaps the percentage range of “alkyl sultone-based compound…from 20 wt% to 100 wt%” in claim 5, and, for antioxidant/propenyl-1,3-sultone, the percentage range of 10% to 500% encompasses the percentage range of “alkenyl sultone-based compound…from 20 wt% to 170 wt%” in claim 6.
The subject matter as a whole would have been obvious to one having ordinary skill in the art at the time the invention was made to have selected the overlapping portion of the range disclosed by the reference because overlapping ranges have been held to be a prima facie case of obviousness. In re Malagari, 182 U.S.P.Q. 549. See also MPEP 2144.05.
“A prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prime facie case of obviousness.” In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003).
Response to Arguments
In response to Applicants’ arguments traversing the teachings of Funada et al., in that this reference (a) broadly lists various types of antioxidants and (b) teaches a content of antioxidant relative to the weight of the halogenated carbon ester in “an extremely broad range”, the Examiner respectfully submits that, as discussed above, Funada et al. teach exemplary antioxidants reading upon Chemical Formulae 2 and 4 in Applicants’ claims. Additionally, the amounts of antioxidant and of halogenated carbonate ester disclosed in Funada et al., each based on the amount of electrolyte solution, were employed to determine the amount of antioxidant relative to amount of halogenated carbonate ester, which was determined to range from 5% to 50%, which overlaps the range of “from 10 wt% to 50 wt%” recited in claim 1. Although, as Applicants argue, “the effects obtained when a content of the antioxidant relative to a weight of the halogenated carbonate ester is less than 10% can be regarded as being comparable to the effects observed in Comparative Example 2 of the present application”, Applicants have not convincingly shown how the remaining determined percentage range reading upon Applicants’ claimed range, e.g., the determined percentage of 50%, teaches away from the claimed invention.
In response to Applicants’ arguments traversing the teachings of Wang et al., the Examiner respectfully submits that this reference was and is relied upon for its teachings regarding the sultones recited in Applicants’ claims 1, 5, and 6, along with teaching the organic solvents and lithium salts both disclosed in Funada et al. and Xu et al., and also recited in Applicants’ claims. Although Wang et al. teaches an electrolyte composition “that necessarily includes three types of additives”, paragraph [0014] of this reference discusses each additive’s benefits, including that 1,3-propane sultone “can form a dense SEI film at the negative electrode, which can effectively improve the high-temperature storage characteristics of the lithium-ion secondary battery.”
In response to Applicants’ arguments traversing the teachings of Xu et al., in that this reference “does not disclose at all adjusting a content of the additive relative to a weight of the carbonate-based compound to improve battery performance”, the Examiner respectfully submits that the amount 0.002 to 0.1% by mass of flavonoid compounds (which corresponds to Applicants’ Chemical Formulae 1 and 3), as disclosed in Xu et al. shares a common endpoint with the claimed range of “0.1 wt% to 0.5 wt%”. In view of said shared common endpoint, requiring Xu et al. to adjust the content of said additive “to improve battery performance”, as argued by Applicants, is not deemed necessary. Applicants have not amended the claims to exclude the amount of additive disclosed in Xu et al.
In response to Applicants’ argument that “there is no real motivation presented in the cited references that would have lead the skilled person to combine all three references”, the Examiner respectfully submits that motivation to combine these references’ teachings, as stated above, is found in that these references are all directed to electrolytic solutions, each of which contain the same or similar components, e.g., the same or similar lithium salts and carbonate solvents.
In response to Applicants’ argument that the cited references’ combined teachings “fail to disclose an electrolyte composition further including alkyl sultone-based compounds and alkenyl sultone-based compounds”, the Examiner respectfully submits that Wang et al. teach the feasibility in the non-aqueous electrolyte containing an additive including 1 to 5 parts by weight 1,3-propane sultone, and also containing 0.1 to 5 parts by weight conventional additive (e.g., propenyl-1,3-sultone). See paragraphs [0007] and [0008] of Wang et al. In view of this teaching, the claim limitation “auxiliary additive further comprises a sultone-based compound including an alkyl sultone-based compound and an alkenyl sultone-based compound” is considered met by Wang et al. Further, although “Wang only describes experimental results obtained using a single additive”, as argued by Applicants, the Examiner respectfully submits that teachings of a reference are not limited to its preferred embodiments. In re Boe, 145 U.S.P.Q. 507 (CCPA 1966).
Applicants have not convincingly shown that the teachings of Funada et al., Xu et al., and Wang et al., as discussed above, do not teach or suggest Applicants’ claimed invention. For these reasons, Applicants’ arguments have been considered, but are not persuasive.
Conclusion
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/Patricia L. Hailey/Primary Examiner, Art Unit 1732 February 5, 2026