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 and Other Notes
Claims 1–24 are pending.
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 paragraph numbers cited in this Office Action in reference to the instant application are referring to the paragraph numbering of the PG-Pub of the instant application. See US 2024/0317690 A1.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 24 May 2024, 12 August 2024, 10 December 2024, and 16 December 2025 were filed before the mailing of a first Office Action on the merits. The submissions comply with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1–24 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the limitations "R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2." It is unclear if the final five phrase (i.e., R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2) are a single alternative limitation in conjunction with the list of alternatives recited or only the immediately adjacent phrase (i.e., R8 and R9 are absent and X1 is an oxygen atom in Formula V) is used in conjunction with the list of alternatives.
Claim 1 recites the limitations "R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V." It is unclear what R8 and R9 represent when X1 is not a carbon atom, nitrogen atom, or oxygen atom. Claim 1 uses the contingent phrases "when X1 is a carbon atom" and "when X1 is a nitrogen atom" and X1 is not required to be one of a carbon atom nor nitrogen atom; and X1 being an oxygen atom is in a list of alternatives. X1 is not required to be a carbon atom, nitrogen atom, nor oxygen atom; and R8 and R9 are not defined when X1 is not a carbon atom, nitrogen atom, or oxygen atom. Therefore, the substituents of X1, R8, and R9 are not defined and unclear.
Claims 2–17 are directly or indirectly dependent from claim 1 and includes all the limitations of claim 1. Therefore, claims 2–17 are also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 18 recites the limitation "a compound as defined in claim 1" and includes all the limitations of claim 1. Therefore, claim 18 is also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 19 recites the limitation "a compound as defined in claim 1" and includes all the limitations of claim 1. Therefore, claim 18 is also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 20 is directly dependent from claim 19 and includes all the limitations of claim 19. Therefore, claim 20 is also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 21 recites the limitation "an electrode material as defined in claim 18" and includes all the limitations of claim 18. Therefore, claim 21 is also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 22 recites the limitation "an electrolyte composition as defined in claim 19" and includes all the limitation of claim 19. Therefore, claim 22 is also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 23 and 24 are directly or indirectly dependent from claim 22 and include all the limitations of claim 22. Therefore, claims 23 and 24 are also indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 4, 5, and 15–24 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Miyake et al. (US 2003/0096163 A1, hereinafter Miyake).
Regarding claim 1, Miyake discloses a compound as defined in any one of Formulae II to V (see Li (CF3SO2) N2 (COCF3), [0022]):
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(see Li (CF3SO2) N2 (COCF3), [0022])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 4, Miyake discloses all the claim limitations as set forth above and further discloses a compound:
wherein R5 is an unsubstituted C1-6alkyl group or a fluorinated C1-6alkyl group (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 5, Miyake discloses all the claim limitations as set forth above and further discloses a compound:
wherein R6 is a fluorinated C1-6alkyl group or a fluorinated C6aryl group (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 15, Miyake discloses all the claim limitations as set forth above and further discloses a compound:
wherein M is Li, Na, or K and n is 1 (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 16, Miyake discloses all the claim limitations as set forth above and further discloses a compound:
wherein M is Li and n is 1 (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 17, Miyake discloses all the claim limitations as set forth above and further discloses a compound:
wherein said compound is selected from:
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or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 18, Miyake discloses an electrode material comprising an additive (14) and at least one electrochemically active material (11a, [0038]), wherein the additive comprises:
a compound as defined in any one of Formulae II to V (see Li (CF3SO2) N2 (COCF3), [0022]):
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(see Li (CF3SO2) N2 (COCF3), [0022])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 19, Miyake discloses an electrolyte (14) composition comprising
a compound as defined in any one of Formulae II to V (see Li (CF3SO2) N2 (COCF3), [0022]):
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(see Li (CF3SO2) N2 (COCF3), [0022])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 20, Miyake discloses all the claim limitations as set forth above and further discloses an electrolyte composition, further comprising
a compatible solvent or a compatible solvating polymer (see non aqueous electrolyte, [0020]).
Regarding claim 21, Miyake discloses an electrochemical cell (10) comprising an electrolyte (14), an electrode (11a) and a counter-electrode (12), wherein the electrode (11a) or counter-electrode (12) comprises an electrode material, wherein the electrode material (11a) comprises an additive (14) and at least one electrochemically active material (11a, [0038]), wherein the additive comprises:
a compound as defined in any one of Formulae II to V (see Li (CF3SO2) N2 (COCF3), [0022]):
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(see Li (CF3SO2) N2 (COCF3), [0022])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 22, Miyake discloses an electrochemical cell (10) comprising an electrolyte (14), an electrode (11a) and a counter-electrode (12), wherein the electrolyte (14) comprises an electrolyte composition (10), wherein the electrolyte composition (14) comprises:
a compound as defined in any one of Formulae II to V (see Li (CF3SO2) N2 (COCF3), [0022]):
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(see Li (CF3SO2) N2 (COCF3), [0022])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see Li (CF3SO2) N2 (COCF3), [0022]).
Regarding claim 23, Miyake discloses all the claim limitations as set forth above and further discloses an electrochemical cell:
wherein said electrochemical cell (10) is a battery, an electrochromic device, or a capacitor (FIG. 3, [0038]).
Regarding claim 24, Miyake discloses all the claim limitations as set forth above and further discloses an electrochemical cell:
wherein said battery (10) is a lithium or lithium-ion battery (FIG. 3, [0038]).
Claims 1, 6, and 7 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Bouchet et al. (US 2019/0088997 A1, hereinafter Bouchet).
Regarding claim 1, Bouchet discloses a compound as defined in any one of Formulae II to V (see lithium maleimide-sulfonyl(trifluoromethyl-sulfonyl)imide, P10/C1/L31) :
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(see lithium maleimide-sulfonyl(trifluoromethyl-sulfonyl)imide, P10/C1/L31)
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl ; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see lithium maleimide-sulfonyl(trifluoromethyl-sulfonyl)imide, P10/C1/L31).
Regarding claim 6, Bouchet discloses all the claim limitations as set forth above and further discloses a compound:
wherein R7 is a fluorine atom or is selected from fluorine substituted C1-6alkyl groups (see lithium maleimide-sulfonyl(trifluoromethyl-sulfonyl)imide, P10/C1/L31).
Regarding claim 7, Bouchet discloses all the claim limitations as set forth above and further discloses a compound:
wherein L1 is a covalent bond or a linker selected from optionally substituted C6aryl groups (see lithium maleimide-sulfonyl(trifluoromethyl-sulfonyl)imide, P10/C1/L31).
Claims 1, 2, 3, 8, and 12 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Coad et al. (Synthesis and Characterization of Derivatives and Dimers of 4,5-Dicyanoimidazole, hereinafter Coad)
Regarding claim 1, Coad discloses a compound as defined in any one of Formulae II to V (6a-c, Scheme 2, P2813):
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(6a-c, Scheme 2, P2813)
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl ; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (6a-c, Scheme 2, P2813).
Regarding claim 2, Coad discloses all the claim limitations as set forth above and further discloses a compound:
wherein at least one of R1 and R2 is CN (6a-c, Scheme 2, P2813).
Regarding claim 3, Coad discloses all the claim limitations as set forth above and further discloses a compound:
wherein both of R1 and R2 are CN (6a-c, Scheme 2, P2813).
Regarding claim 8, Coad discloses all the claim limitations as set forth above and further discloses a compound:
wherein X1 is a carbon atom (6a-c, Scheme 2, P2813).
Regarding claim 12, Coad discloses all the claim limitations as set forth above and further discloses a compound:
wherein X1 is a nitrogen atom (6a-c, Scheme 2, P2813).
Claims 1 and 8–10 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Coad et al. (US 2012/0121806 A1, hereinafter Norman)
Regarding claim 1, Norman discloses a compound as defined in any one of Formulae II to V (see 2,4,5-trimethyl-imidazolate lithium salt, [1274]):
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(see 2,4,5-trimethyl-imidazolate lithium salt, [1274])
wherein, R1 and R2 are independently selected from H, F, CN, NO2, and optionally substituted alkyl ; R5 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R6 is selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; R7 is selected from a fluorine atom and optionally substituted C1-6alkyl; R8 and R9 are each independently F, CN or optionally substituted C1-6alkyl when X1 is a carbon atom in Formula IV or V; or R8 is absent and R9 is an optionally substituted SO2alkyl or optionally substituted C1-6alkyl when X1 is a nitrogen atom in Formula IV or V; or R8 and R9 are absent and X1 is an oxygen atom in Formula V; L1 is a covalent bond, or a linker selected from optionally substituted C1-6alkyl and optionally substituted C6aryl; m is an integer selected from 0 or 1; and (Mn+)1/n is a metal cation, wherein M is an alkali metal or alkaline earth metal and n is 1 or 2; or a tautomer thereof (see 2,4,5-trimethyl-imidazolate lithium salt, [1274]).
Regarding claim 8, Norman discloses all the claim limitations as set forth above and further discloses a compound:
wherein X1 is a carbon atom (see 2,4,5-trimethyl-imidazolate lithium salt, [1274]).
Regarding claim 9, Coad discloses all the claim limitations as set forth above and further discloses a compound:
wherein at least one of R8 and R9 is CN or optionally substituted C1-6alkyl (see 2,4,5-trimethyl-imidazolate lithium salt, [1274]).
Regarding claim 10, Norman discloses all the claim limitations as set forth above and further discloses a compound:
wherein R8 and R9 are both CN or optionally substituted C1-6alkyl (see 2,4,5-trimethyl-imidazolate lithium salt, [1274]).
Allowable Subject Matter
Claims 11, 13, and 14 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
The cited art of record, alone or in combination does not disclose, teach, or suggest the following distinguishing feature:
A compound wherein both of R8 and R9 are CN or optionally substituted C1-6alkyl when X1 is a carbon atom, or R8 is absent and R9 is a fluorine substituted SO2alkyl when X1 is a nitrogen atom.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sean P Cullen, Ph.D. whose telephone number is (571)270-1251. The examiner can normally be reached Monday to Thursday 6:00 am to 4:00 pm CT, Friday 6:00 am to 12:00 pm CT.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Basia A Ridley can be reached at (571)272-1453. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Sean P Cullen, Ph.D./Primary Examiner, Art Unit 1725
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