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 .
Election/Restrictions
Applicant’s election without traverse of Group I (Claims 1-9, 12-14, 20, 23-27, 31, 59, 67-68, and 70) in the reply filed on 02/23/2026 is acknowledged.
Claim 69 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 02/23/2026.
Claim Objections
Claims 1, 14, and 23 are objected to because of the following informalities:
Claim 1:
there are no spaces between the carbon notations and carbon group title (for example, claim 1 states “C3-C8cycloalkyl” instead of “C3-C8 cycloalkyl”).
In the R1 limitations, the carbon notations for the alkoxy is C1-4 not C1-C4.
Claim 14:
“bond between Y and L” should be “bond between Y+ and L”.
Claim 23:
There is nothing indicating what
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means (for example, like what is shown in claim 14).
Appropriate correction is required.
Claim Interpretation
Claim 3 recites “optionally”.
The Examiner notes MPEP 2173.05(h) II:
“Another alternative format which requires some analysis before concluding whether or not the language is indefinite involves the use of the term "optionally." In Ex parte Cordova, 10 USPQ2d 1949 (Bd. Pat. App. & Inter. 1989) the language "containing A, B, and optionally C" was considered acceptable alternative language because there was no ambiguity as to which alternatives are covered by the claim. A similar holding was reached with regard to the term "optionally" in Ex parte Wu, 10 USPQ2d 2031 (Bd. Pat. App. & Inter. 1989).”
The Examiner notes the recitation of optionally is clear in claim 3.
Calculation Explanation
In the rejections below, calculations for the weight percent of the electrolyte additives are done.
The calculations for the weight percent of the compound/sulfonate anions are done by identifying the molar masses of each component, adding the molar masses of the anion and cation for the total ionic liquid molar mass, assume a 100g sample of the electrolyte, calculating the mass fraction of the sulfonate anion in the ionic liquid, and calculating the mass of the sulfonate anion in the grams of the electrolyte after water is removed from the 100g.
For Example (taken from the rejection of claim 1 below). The ionic liquid electrolyte can contain water, an anion, and a cation. The anion can be MES and the cation can be tetramethylammonium.
MES has a molar mass of approximately 195.24 g/mol. Tetramethylammonium has a molar mass of approximately 74.15 g/mol. In total, the ionic liquid from the mixture of both has a molar mass of 269.39 g/mol.
The MES component accounts for 72.47 % of the total mass of the ionic liquid above.
If water makes up 50 wt. % of the ionic liquid electrolyte, then the ionic liquid makes up the other 50 wt. %. If there are 100 g of the electrolyte, then 50g make up the part for the ionic liquid. The amount of MES in the ionic liquid electrolyte would be calculated by multiplying 50g by 0.7274. This calculates out to be 36.37 g, therefore, the weight percent of MES in the ionic liquid electrolyte would be approximately 36 wt %.
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.
Claims 1-7, 12-14, 20, 23-26, 31, 59, 67-68, and 70 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wolfe et al (US 20120321967 A1, as given in the 06/06/2023 IDS).
Regarding claim 1, Wolfe discloses an aqueous electrolyte composition comprising an electrolyte additive of Formula A, or a salt, zwitterion, cation, or anion thereof:
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wherein:
R is L-R1, L-Y+, C3-C8cycloalkyl, C3-C8heteroarylalkyl, or C3- C8heterocycloalkyl;
L is a linear C1-C6alkylene, branched C1-C6alkylene, C3-C8cycloalkylene, or C3-C8heterocycloalkylene;
wherein L is optionally substituted with one to four -OH;
R1 is selected from -OH, C1-C4alkoxy, -C(O)OR2, -NR2C(O)R3, -NR4aR4b, hydroxyC1-C4alkyl, -S(O)R5, C3-C8cycloalkyl, and C3- C8heterocycloalkyl;
R2 and R3 are independently selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, aryl, heteroaryl, and arylC1-C4alkyl;
wherein R2 and R3 with the exception of hydrogen are independently optionally substituted with one to four R6;
R4a and R4b are independently, in each instance, selected from hydrogen,C1-C6alkyl, hydroxyCl-C4alkyl, -CR7R8R9, -CH2C(O)R10, cycloalkyl, aryl, heteroaryl, and arylC1-C4alkyl; or
R4a and R4b are taken together with the nitrogen to which they are attached form a 6-membered heterocycloalkyl or heteroaryl optionally substituted with one to four R6;
R5 is -OH, C14alkyl, aryl, or heteroaryl;
R6, when present, is independently, in each instance, selected from C1-C6alkyl,-NH2, halogen, -OH, hydroxyCl-C4alkyl, and -C(O)OR11;
R7, R8, and R9 are independently, in each instance, selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, -CH2C(O)R10, and hydroxyC1-C4alkyl;
R10 is selected from -NH2, -OH, and C1-C4alkyl;
R11 is selected from hydrogen and C1-C4alkyl;
Y+ is selected from -N+R12R13R14, C3-C8heteroaryl containing at least one quaternary nitrogen, and C3-C8heterocycloalkyl containing at least one quaternary nitrogen; and
R12, R13, and R14 are independently selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, hydroxyC1-C4alkyl, and -CR7R8R9;or
R12 and R13 are taken together with the nitrogen to which they are attached to form a 6-membered heterocycloalkyl or 6-membered heteroaryl optionally substituted with one to four R6 (electrolyte for zinc air battery including an ionic liquid, P33, 61; ionic liquid including the buffers described in P31 and shown in the figures following (Good’s buffers such as MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES and corresponding sulfonate ions (by removing the hydrogen from the OH of the compounds)); see entire disclosure and especially P31-32, 61);
and wherein the electrolyte additive is present in the aqueous electrolyte at a concentration equal to, or greater than, 0.01 weight percent (wt %) to less than, or equal to, 40 wt % (water is present in the ionic liquid electrolyte at 0.1-50 wt %; see entire disclosure and especially P33, 35; P32 lists a number of suitable cations that are with the compounds above to form the ionic liquid (protic or aprotic); the cation used for the calculations below is selected as tetramethylammonium;
if water is assumed at 50 wt. % and MES and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, MES is present in approximately 36 wt. %; if water is assumed at 50 wt. % and HEPES and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, HEPES is present in approximately 38 wt. %; if water is assumed at 50 wt. % and HEPPS and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, HEPPS is present in approximately 39 wt. %; if water is assumed at 50 wt. % and MOPS and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, MOPS is present in approximately 37 wt %; if water is assumed at 50 wt. % and TAPS and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, TAPS is present in approximately 38 wt %; if water is assumed at 50 wt. % and TAPSO and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, TAPSO is present in approximately 39 wt %; if water is assumed at 50 wt. % and TES and tetramethylammonium are used together at a 1:1 ratio in 100g of the electrolyte, TES is present in approximately 38 wt %).
Regarding claim 2, Wolfe discloses wherein the electrolyte additive of formula A is a compound of formula I:
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(MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES; see entire disclosure and especially P31 and the figures following).
Regarding claim 3, Wolfe discloses wherein the electrolyte additive of formula A is a compound of formula IV:
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and wherein the electrolyte composition optionally further comprises one or more anions selected from C1", Br, I', ClO₄; C₂HO₄; HSO4; HCO2, CICH₂CO₂; Cl₃CCO₂; HOCH₂CO₂; CF₃CO₂", H₂PO₄; CH₃SO₃", PhSO₃", p-CH₃-Ph-SO₃,
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,
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, and combinations thereof (MOPS; see entire disclosure and especially P31 and the figures following).
Regarding claim 4, Wolfe discloses wherein the electrolyte additive of formula A is a compound of formula II:
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(the sulfonate anion of MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES; Wolfe says the hydrogen can be removed from the OH in the compounds seen in P31 and the figures following).
Regarding claim 5, Wolfe discloses wherein the electrolyte additive of formula I is a compound of formula IIb or IIc:
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(the battery is a zinc-air battery that would produce Zn2+ to coordinate with the sulfonate anion of MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES; Wolfe says the hydrogen can be removed from the OH in the compounds seen in P31 and the figures following).
Regarding claim 6, Wolfe discloses wherein the electrolyte additive of formula II further comprises a quaternary ammonium cation (the battery is a zinc-air battery that would produce Zn2+ to coordinate with the sulfonate anion of MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES).
Regarding claim 7, Wolfe discloses wherein the electrolyte additive has the following structure
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(the sulfonate anion of MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES; Wolfe says the hydrogen can be removed from the OH in the compounds seen in P31 and the figures following).
Regarding claim 12, Wolfe discloses wherein compound of formula IV is a compound of formula III
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(the sulfonate anion of MOPS; Wolfe says the hydrogen can be removed from the OH in the compounds seen in P31 and the figures following).
Regarding claim 13, Wolfe discloses wherein the electrolyte additive has the following structure
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(the sulfonate anion of MOPS; Wolfe says the hydrogen can be removed from the OH in the compounds seen in P31 and the figures following).
Regarding claim 14, Wolfe discloses wherein Y+ is
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; and where
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indicates the bond between Y+ and L (HEPES, TAPS, TAPSO ,TES; see entire disclosure and especially P31 and the figures following).
Regarding claim 20, Wolfe discloses wherein the compound of formula A is a compound of formula V:
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(MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES; see entire disclosure and especially P31 and the figures following; note: R in formula V can be L-R1 or L-Y+ such as those in claims 2 and 3).
Regarding claim 23, Wolfe discloses wherein R is
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(MES, MOPS; see entire disclosure and especially P31 and the figures following).
Regarding claim 24, Wolfe discloses wherein the electrolyte additive is selected from
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(HEPES, TAPS, TES are known to exist in zwitteronic form; see entire disclosure and especially P31 and the figures following).
Regarding claim 25, Wolfe discloses wherein the electrolyte additive is selected from
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(TAPS, TAPSO are known to exist in zwitterionic form; see entire disclosure and especially P31 and the figures following).
Regarding claim 26, Wolfe discloses wherein the electrolyte additive is selected from
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(TAPS, TAPSO are known to exist in zwitterionic form; see entire disclosure and especially P31 and the figures following).
Regarding claim 31, Wolfe discloses wherein the electrolyte additive is selected from
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(MES is known to exist in zwitterionic form; see entire disclosure and especially P31 and the figures following).
Regarding claim 59, Wolfe discloses a process for making a zinc battery, comprising contacting an aqueous electrolyte composition of claim 1 with a zinc-battery electrode (see entire disclosure and especially P13, 38, 47-48).
Regarding claim 67, Wolfe discloses wherein the electrolyte additive is present in the aqueous electrolyte at a concentration equal to, or greater than, 0.01 weight percent (wt %) to less than, or equal to, 30 wt % (water is present in the ionic liquid electrolyte at 0.1-50 wt %; see entire disclosure and especially P33, 35; P32 lists a number of suitable cations that are with the compounds above to form the ionic liquid (protic or aprotic); the cation used for the calculation is selected as 1-methylimidazo[1,2-a]pyridinium; if water is assumed at 50 wt. % and MES and 1-methylimidazo[1,2-a]pyridinium are used together at a 1:1 ratio in 100g of the electrolyte, MES is present in approximately 27.5 wt. %).
Regarding claim 68, Wolfe discloses wherein the electrolyte additive is present in the aqueous electrolyte at a concentration equal to, or greater than, 0.01 weight percent (wt %) to less than, or equal to, 35 wt % (water is present in the ionic liquid electrolyte at 0.1-50 wt %; see entire disclosure and especially P33, 35; P32 lists a number of suitable cations that are with the compounds above to form the ionic liquid (protic or aprotic); the cation used for the calculation is selected as 1-methylimidazo[1,2-a]pyridinium; if water is assumed at 50 wt. % and MES and 1-methylimidazo[1,2-a]pyridinium are used together at a 1:1 ratio in 100g of the electrolyte, MES is present in approximately 27.5 wt. %).
Regarding claim 70, Wolfe discloses wherein the electrolyte additive of formula II further comprises a quaternary ammonium cation (the battery is a zinc-air battery that would produce Zn2+ to coordinate with the sulfonate anion of MES, HEPES, HEPPS, MOPS, TAPS, TAPSO, TES).
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.
Claims 1, 8, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Kuriyama et al (US 20140134477 A1).
Regarding claims 1, 8, and 9, Kuriyama discloses an aqueous electrolyte composition comprising an electrolyte additive of Formula A, or a salt, zwitterion, cation, or anion thereof:
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wherein:
R is L-R1, L-Y+, C3-C8cycloalkyl, C3-C8heteroarylalkyl, or C3- C8heterocycloalkyl;
L is a linear C1-C6alkylene, branched C1-C6alkylene, C3-C8cycloalkylene, or C3-C8heterocycloalkylene;
wherein L is optionally substituted with one to four -OH;
R1 is selected from -OH, C1-C4alkoxy, -C(O)OR2, -NR2C(O)R3, -NR4aR4b, hydroxyC1-C4alkyl, -S(O)R5, C3-C8cycloalkyl, and C3- C8heterocycloalkyl;
R2 and R3 are independently selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, aryl, heteroaryl, and arylC1-C4alkyl;
wherein R2 and R3 with the exception of hydrogen are independently optionally substituted with one to four R6;
R4a and R4b are independently, in each instance, selected from hydrogen,C1-C6alkyl, hydroxyCl-C4alkyl, -CR7R8R9, -CH2C(O)R10, cycloalkyl, aryl, heteroaryl, and arylC1-C4alkyl; or
R4a and R4b are taken together with the nitrogen to which they are attached form a 6-membered heterocycloalkyl or heteroaryl optionally substituted with one to four R6;
R5 is -OH, C14alkyl, aryl, or heteroaryl;
R6, when present, is independently, in each instance, selected from C1-C6alkyl,-NH2, halogen, -OH, hydroxyCl-C4alkyl, and -C(O)OR11;
R7, R8, and R9 are independently, in each instance, selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, -CH2C(O)R10, and hydroxyC1-C4alkyl;
R10 is selected from -NH2, -OH, and C1-C4alkyl;
R11 is selected from hydrogen and C1-C4alkyl;
Y+ is selected from -N+R12R13R14, C3-C8heteroaryl containing at least one quaternary nitrogen, and C3-C8heterocycloalkyl containing at least one quaternary nitrogen; and
R12, R13, and R14 are independently selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, hydroxyC1-C4alkyl, and -CR7R8R9;or
R12 and R13 are taken together with the nitrogen to which they are attached to form a 6-membered heterocycloalkyl or 6-membered heteroaryl optionally substituted with one to four R6 (as drawn to claim 1), wherein R1 is selected from -OH and -C(O)OR2 and R2 is selected from hydrogen, methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, and tert-butyl (as drawn to claim 8), and wherein R1 is -OH (as drawn to claim 9) (“The nonaqueous electrolyte contains a nonaqueous solvent, an electrolyte, at least one hydroxyalkylsulfonic acid”, P30; “2-hydroxyethanesulfonic acid”, P33; see entire disclosure and especially P30, 33, 42);
and wherein the electrolyte additive is present in the aqueous electrolyte at a concentration equal to, or greater than, 0.01 weight percent (wt %) to less than, or equal to, 40 wt % (“The concentration of the hydroxyalkylsulfonic acid in the nonaqueous electrolyte is, for example, from 0.01 to 10% by mass”, P34).
Claims 1 and 27 rejected under 35 U.S.C. 103 as being unpatentable over Mizuno et al (US 20230110251 A1).
Regarding claims 1 and 27, Mizuno discloses an aqueous electrolyte composition comprising an electrolyte additive of Formula A, or a salt, zwitterion, cation, or anion thereof:
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wherein:
R is L-R1, L-Y+, C3-C8cycloalkyl, C3-C8heteroarylalkyl, or C3- C8heterocycloalkyl;
L is a linear C1-C6alkylene, branched C1-C6alkylene, C3-C8cycloalkylene, or C3-C8heterocycloalkylene;
wherein L is optionally substituted with one to four -OH;
R1 is selected from -OH, C1-C4alkoxy, -C(O)OR2, -NR2C(O)R3, -NR4aR4b, hydroxyC1-C4alkyl, -S(O)R5, C3-C8cycloalkyl, and C3- C8heterocycloalkyl;
R2 and R3 are independently selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, aryl, heteroaryl, and arylC1-C4alkyl;
wherein R2 and R3 with the exception of hydrogen are independently optionally substituted with one to four R6;
R4a and R4b are independently, in each instance, selected from hydrogen,C1-C6alkyl, hydroxyCl-C4alkyl, -CR7R8R9, -CH2C(O)R10, cycloalkyl, aryl, heteroaryl, and arylC1-C4alkyl; or
R4a and R4b are taken together with the nitrogen to which they are attached form a 6-membered heterocycloalkyl or heteroaryl optionally substituted with one to four R6;
R5 is -OH, C14alkyl, aryl, or heteroaryl;
R6, when present, is independently, in each instance, selected from C1-C6alkyl,-NH2, halogen, -OH, hydroxyCl-C4alkyl, and -C(O)OR11;
R7, R8, and R9 are independently, in each instance, selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, -CH2C(O)R10, and hydroxyC1-C4alkyl;
R10 is selected from -NH2, -OH, and C1-C4alkyl;
R11 is selected from hydrogen and C1-C4alkyl;
Y+ is selected from -N+R12R13R14, C3-C8heteroaryl containing at least one quaternary nitrogen, and C3-C8heterocycloalkyl containing at least one quaternary nitrogen; and
R12, R13, and R14 are independently selected from hydrogen, C1-C6alkyl, aryl, arylC1-C4alkyl, cycloalkyl, hydroxyC1-C4alkyl, and -CR7R8R9;or
R12 and R13 are taken together with the nitrogen to which they are attached to form a 6-membered heterocycloalkyl or 6-membered heteroaryl optionally substituted with one to four R6 (as drawn to claim 1), wherein the electrolyte additive is selected from
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(as drawn to claim 27)
(“The phosphazene compound (A) contained in the non-aqueous electrolyte solution…contains at least one of…a phosphazene compounds represented by the following Formula (2)”, P53; “In Formula (2), each of Y− and Z− independently represents an anion in which a proton is removed from an inorganic acid or an active hydrogen compound”, P55; “The active hydrogen compound is not limited as long as it can yield an anion excluding a proton, and the active hydrogen compound may be…a compound having an active hydrogen atom bonded to an oxygen atom”, P57; “Examples of the compound having an active hydrogen atom bonded to an oxygen atom include…sulfonic acids having from 1 to 20 carbon atoms”, P60; “Examples of the sulfonic acids having from 1 to 20 carbon atoms include … 3-pyridinesulfonic acid”, P63; see entire disclosure and especially P63);
and wherein the electrolyte additive is present in the aqueous electrolyte at a concentration equal to, or greater than, 0.01 weight percent (wt %) to less than, or equal to, 40 wt % (“wherein a content of the phosphazene compound (A) is from 0.1% by mass to 2.0% by mass with respect to a total amount of the non-aqueous electrolyte solution for a battery”, P18).
Conclusion
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/MARY GRACE HARRIS/Examiner, Art Unit 1729