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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 04/14/2026 has been entered.
Response to Amendment
This is a non-final office action in response to Applicant's remarks and amendments filed on 04/14/2026. Claims 1 and 2 are currently amended. Claims 11, 12, 17-22, 24-25, 27-32, and 34-35 remain withdrawn. Claims 1-3, 5-6, and 36 are pending review in this action.
The 35 U.S.C. § 103 rejections in the previous Office Action are withdrawn.
New grounds of rejection necessitated by Applicant's amendments are presented below.
Response to Arguments
Applicant argues Zhang does not disclose or suggest any compound of Formula (1) where R’ is trifluoroethyl as required by amended claim 1. In addition, one of ordinary skill in the art would not be motivated to select a cyclic ether as the fluorinated solvent of Zhang because Zhang discloses a nearly infinite number of choices of ethers for the solvents, which have widely different structures and thus would likely have unpredictable properties. The experimental examples of Zhang use a linear ether as a solvent. This would suggest to a person of ordinary skill in the art a preference toward linear polyfluorinated alkyl ethers and away from cyclic ethers.
The Examiner respectfully disagrees. Although Zhang does not disclose a compound where R’ is trifluoroethyl, the new ground of rejection relies on Yamazaki to teach said compound as a known alternative to the non-polar fluorinated compounds taught by Zhang. Regarding Applicant’s argument that Zhang teaches nearly infinite ether compounds, Examiner notes that Zhang names a mere 12 illustrative solvents ([0025]), including the 2-trifluoromethyl-1,3-dioxolane cited in the previous rejection. The use of a linear ether in example embodiments is a non-limiting choice and should not be considered as excluding or teaching away from the other disclosed solvents.
Applicant’s arguments with respect to claim 36 are moot because the new ground of rejection does not rely on Dong.
Claim Rejections - 35 USC § 103
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 and 2 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang (US 2017/0033406 A1; previously cited) in view of Yamazaki (US 2021/0194057 A1).
Regarding claim 1, Zhang discloses a nonaqueous battery electrolyte formulation ([0023]), consisting of: a metal electrolyte salt ([0028]); optionally, a solvent selected from the group consisting of dimethoxyethane ([0026]); and optionally a film-forming agent additive (additive that further enhances the formation of a solid electrolyte interphase, [0029]).
Zhang discloses that the electrolyte includes a non-polar fluorinated ether solvent ([0023]) such as 2-trifluoromethyl-1,3-dioxolane, which is a compound of Formula (1) wherein R’ is CF3 and wherein each R is H, or 2,2-bis(trifluoromethyl)-1,3-dioxolane ([0025]), but does not disclose a compound of Formula (1) wherein R’ is trifluoroethyl; and wherein each R is, independently, selected from the group consisting of H, F, Cl, CF3, alkyl, and fluoroalkyl.
Yamazaki teaches an electrolyte solution ([0018]) comprising 2,2-bis(trifluoromethyl)-1,3-dioxolane or 2-(trifluoroethyl)dioxolane ([0416]). A person having ordinary skill in the art before the effective filing date of the invention would have found it obvious to have substituted 2-(trifluoroethyl)dioxolane, which is a compound of Formula (1) wherein R’ is trifluoroethyl and each R is H, for the fluorinated ether solvent of Zhang because Yamazaki teaches that 2-(trifluoroethyl)dioxolane is a known alternative to the 2,2-bis(trifluoromethyl)-1,3-dioxolane of Zhang. In addition, Zhang teaches that the formulation may be modified beyond the disclosed embodiments ([0055]) and it has been held that the simple substitution of one known element for another is likely to be obvious when predictable results are achieved ([MPEP § 2143B]). Regarding claim 2, Zhang in view of Yamazaki teaches wherein each R is H (2-(trifluoroethyl)dioxolane, Yamazaki: [0416]).
Claims 3, 5-6, and 36 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang (US 2017/0033406 A1) in view of Yamazaki (US 2021/0194057 A1), as applied to claim 1 above, and as evidenced by ACS (CAS SciFinder Substance Detail: 110-71-4, 21324-40-3, 117971-08-1, and 409071-16-5, 2026).
Regarding claim 3, Zhang in view of Yamazaki teaches wherein the metal electrolyte salt is a salt of lithium (Zhang: [0028]).
Zhang in view of Yamazaki does not disclose wherein the metal electrolyte salt is present in an amount of from 0.1 to 20 wt% relative to a total mass of the formulation.
However, Zhang teaches that the metal electrolyte salt is present in a concentration of from about 0.1M to about 3.0M ([0028]). ACS evidences that the density of 2-(trifluoroethyl)dioxolane is 1.25 g/cm3 (p. 3) and the molar mass of LiPF6, one of the lithium salts taught by Zhang ([0028]), is 151.9 g/mol (p. 2). Assuming a basis of 0.1 L of electrolyte, the formulation would include 125g of 2-(trifluoroethyl)dioxolane. The lithium salt would be added in an amount of 1.52g to obtain a concentration of 0.1M and in an amount of 45.6g to obtain a concentration of 3.0M. Zhang therefore teaches wherein the metal electrolyte salt is present in an amount of from 0.12 to 27 wt% relative to a total mass of the formulation, overlapping the claimed range of from 0.1 to 20 wt% and establishing a prima facie case of obviousness [MPEP § 2144.05(I)].
Regarding claim 5, Zhang in view of Yamazaki teaches wherein the metal electrolyte salt is a salt of lithium selected from the group consisting of lithium hexafluorophosphate (LiPF6), lithium tetrafluoroborate (LiBF4). lithium perchlorate (LiClO4), lithium triflate (LiSO2CF3), lithium bis(fluorosulfonyl)imide (LiFSI, Li(FSO2)2N), and lithium bis(trifluoromethanesulfonyl)imide (LiTFSI, Li(CF3SO2)2N) (Zhang: [0028]).
Regarding claim 6, Zhang in view of Yamazaki teaches the formulation according to claim 1, further comprising the solvent (dimethoxyethane or DME, Zhang: [0026]) in an amount of from 14wt% to 93wt% of a liquid component of the formulation. (Zhang teaches that a volume ratio of the non-polar fluorinated ether solvent (2-(trifluoroethyl)dioxolane, see rejection of claim 1) to the solvent (DME) is from about 1:9 to about 9:1 ([0027]). ACS evidences that the room temperature densities of these components are 1.25 g/cm3 and 0.863 g/cm3, respectively (p. 1 and 3). A volume ratio of 2-(trifluoroethyl)dioxolane:DME of 1:9 therefore corresponds to a weight ratio of 1.25:7.77 and a volume ratio of 9:1 to a weight ratio of 11.25:0.863, and Zhang in view of Yamazaki teaches that the formulation comprises the solvent in an amount of 14wt% to 93.0wt%, which reads on the claimed range of from 0.1wt% to 99.9wt%).
Regarding claim 36, Zhang in view of Yamazaki teaches (see Zhang) the film-forming additive (additive that further enhances the formation of a solid electrolyte interface, [0029]) may include Li[BF2(C2O4)] (LiBFOB) and is present in a concentration of from about 0.1M to about 0.4M ([0029]), but does not disclose wherein the film-forming additive is selected from the group consisting of vinylene carbonate (VC), ethylene sulfite (ES), lithium bis(oxalato)borate (LiBOB), cyclohexylbenzene (CHB), ortho-terphenyl (OTP), and combinations thereof; and wherein the film-forming additive is present in an amount of from 0.1 to 3 wt% relative to a total mass of the formulation.
However, Zhang further teaches that the metal electrolyte salt is present in a concentration of from about 0.1M to about 3.0M ([0028]). ACS evidences that the density of 2-(trifluoroethyl)dioxolane is 1.25 g/cm3 (p. 3), the molar mass of LiPF6, one of the lithium salts taught by Zhang ([0028]), is 151.9 g/mol (p. 2), and the molar mass of LiBFOB is 144 g/mol (p. 4). Assuming a basis of 0.1 L of electrolyte, the formulation would include 125g of 2-(trifluoroethyl)dioxolane. The lithium salt would be added in an amount of 1.52g to obtain a concentration of 0.1M and in an amount of 45.6g to obtain a concentration of 3.0M. The film-forming additive LiBFOB would be added in an amount of 1.44g to obtain a concentration of 0.1M and in an amount of 5.76g to obtain a concentration of 0.4M. Zhang therefore teaches wherein the film forming additive is present in an amount of from 0.84 to 4.35 wt% relative to a total mass of the formulation, overlapping the claimed range of from 0.1 to 3 wt% and establishing a prima facie case of obviousness [MPEP § 2144.05(I)].
Yamazaki further teaches LiBFOB (lithium difluoro(oxalate)borate) and LiBOB as film-forming additives ([0179]). A person having ordinary skill in the art before the effective filing date of the invention would have found it obvious to have modified the electrolyte of Zhang in view of Yamazaki by substituting LiBOB for LiBFOB with a reasonable expectation of success because Yamazaki teaches that both compounds are preferred film-forming additives ([0179]). The simple substitution of one known element for another is likely to be obvious when predictable results are achieved ([MPEP § 2143B]).
Conclusion
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/C.C.D./Examiner, Art Unit 1723 /TIFFANY LEGETTE/Supervisory Patent Examiner, Art Unit 1723
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