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 .
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.
Claim(s) 27 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737.
Regarding claim 27, Nawar discloses a redox flow battery (flow battery, see Title, Abstract) comprising a gaseous anolyte, an anode, a cathode, and, as a liquid catholyte, an organic redox active species having at least one electron directing moiety (hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3); wherein
the gaseous anolyte is a hydrogen anolyte and a 2H+ + 2e- ⇌ H2 (gas) redox reaction takes place at the anode (hydrogen electrode, see Abstract, p.4-5, Fig. 3); and
the redox flow battery comprises a catholyte compartment comprising the cathode, wherein the redox flow battery is configured to enable removal of gaseous anolyte from the catholyte compartment (cell is purged, see p.3, such that the fuel cell is configured to enable removable of anolyte/catholyte); and
the redox flow battery comprises an anolyte compartment comprising the anode, wherein the redox flow battery is configured to enable removal of liquid catholyte from the anolyte compartment (cell is purged, see p.3, such that the fuel cell is configured to enable removable of anolyte/catholyte).
Claim(s) 27 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst.
Regarding claim 27, Huskinson discloses a redox flow battery (see Title, Abstract) comprising a gaseous anolyte, an anode, a cathode, and, as a liquid catholyte, an organic redox active species having at least one electron directing moiety (p-benzoquinone in acidic solution as a positive electrode material and a hydrogen negative electrode, see Abstract, p.102-103, Fig. 2); wherein
the gaseous anolyte is a hydrogen anolyte and a 2H+ + 2e- ⇌ H2 (gas) redox reaction takes place at the anode (hydrogen negative electrode, see Abstract, p.102-103, Fig. 2); and
the redox flow battery comprises a catholyte compartment comprising the cathode, wherein the redox flow battery is configured to enable removal of gaseous anolyte from the catholyte compartment (cell is purged, see p.103, such that the fuel cell is configured to enable removable of anolyte/catholyte); and
the redox flow battery comprises an anolyte compartment comprising the anode, wherein the redox flow battery is configured to enable removal of liquid catholyte from the anolyte compartment (cell is purged, see p.103, such that the fuel cell is configured to enable removable of anolyte/catholyte).
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1, 3, 5, 10, 13, 17, 19-22, 24, 26 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013.
Regarding claim 1, Nawar discloses a redox flow battery (flow battery, see Title, Abstract) comprising a gaseous anolyte, an anode, a cathode, and, as a liquid catholyte, an organic redox active species having at least one electron directing moiety (hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3);
wherein the gaseous anolyte is a hydrogen anolyte and a 2H+ + 2e- ⇌ H2 (gas) redox reaction takes place at the anode (hydrogen electrode, see Abstract, p.4-5, Fig. 3); and
wherein an
X
n
+
m
+
m
e
-
⇌
X
n
redox reaction takes place at the cathode, wherein
X
n
+
m
is the organic redox active species,
X
n
is spent organic redox active species and
m
is an integer (reduction and oxidation mechanism for p-benzoquinone/p-hydroquinone, see p.1, Fig. 1, see p.4-5, Fig. 3).
However, Nawar does not disclose the organic redox active species is not unsubstituted parabenzoquinone.
Marshak discloses application of quinone redox chemistry for flow batteries, wherein quinones provide the ability to tune the redox and solubility properties of the molecules through incorporation of various substituent groups onto the aromatic ring (see p.1, Fig. 1). Marshak further discloses these substituted quinones are strong candidates for large-scale energy storage in a flow battery (see p.1).
Nawar and Marshak are analogous art because they are concerned with the same field of endeavor, namely quinone redox couples for flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify Nawar by adding substituent groups onto the aromatic ring of the p-benzoquinone/p-hydroquinone redox couple because Marshak teaches tuning the properties of the quinone redox couple to achieve a wider range of reduction potentials while maintaining rapid and reversible electrochemical kinetics.
Regarding claim 3, modified Nawar discloses all of the claim limitations as set forth above. Marshak further discloses the organic redox active species is selected from a carbocyclic compound, a heterocyclic compound, a polymer, a dendrimer, a dendron and a metallocene (substituted quinone, see Fig. 1).
Regarding claim 5, modified Nawar discloses all of the claim limitations as set forth above. Marshak further discloses the organic redox active species comprises an optionally substituted moiety having the formula:
PNG
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156
270
media_image1.png
Greyscale
in which each E, independently, is an electron directing moiety; and k is 1, 2, 3 or 4 (substituted quinone, see Fig. 1).
Regarding claim 10, modified Nawar discloses all of the claim limitations as set forth above. Marshak further discloses the or each electron directing moiety is an electron withdrawing group independently selected from a sulfonyl, haloalkyl, cyano, sulfonate, nitro, ammonium, carbonyl, carboxylic acid, acyl halide, C-linked ester, C-linked amide or a halide group (substituted quinone, see Fig. 1).
Regarding claim 13, modified Nawar discloses all of the claim limitations as set forth above. Marshak further discloses the or each electron directing moiety is an electron donating group- independently selected from a phenoxide, amine, ether, phenol, N-linked amide, O-linked ester, alkyl, phenyl or a vinyl group (substituted quinone, see Fig. 1).
Regarding claim 17, modified Nawar discloses all of the claim limitations as set forth above. Nawar further discloses the catholyte comprises an acid (H2SO4, see p.2); and the catholyte has a pH of at most about 6 (low pH aqueous solution using quinone/hydroquinone on the positive electrode, see p.6).
Regarding claim 19, modified Nawar discloses all of the claim limitations as set forth above. Nawar further discloses an ion exchange membrane (Nafion membrane, see p.4-5).
Regarding claim 20, modified Nawar discloses all of the claim limitations as set forth above. Nawar further discloses the redox flow battery comprises at least one of a graphitic anode or cathode (graphite, see p.2).
Regarding claim 21, modified Nawar discloses all of the claim limitations as set forth above. Nawar further discloses the anode comprises platinum, palladium, iridium, ruthenium, rhenium, rhodium, osmium, or combinations thereof (platinum, Pt-Ru, see p.2).
Regarding claim 22, modified Nawar discloses all of the claim limitations as set forth above. Nawar further discloses the redox flow battery is a reversible flow battery configured to operate in a power delivery mode in which it generates electrical power by the reaction of redox active species and in an energy storage mode in which it consumes electrical power to generate said redox active species (reversibility, Abstract, see p.1).
Regarding claim 26, modified Nawar discloses all of the claim limitations as set forth above. Marshak further discloses m is selected from 1 and 2 (2, see Fig. 1).
Regarding claim 24, Nawar discloses a method of use of a catholyte in a redox flow battery (flow battery, see Title, Abstract; hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3) comprising a hydrogen anolyte as a gaseous anolyte and an anode and a cathode, (hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3), the method comprising:
providing an organic redox active species having at least one electron directing moiety, as a liquid catholyte (hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3);
incorporating the liquid catholyte into the redox flow battery (hydrogen-quinone fuel cell, benzoquinone/hydroquinone mixture past the quinone electrode on the positive side, H2 flowing past the hydrogen electrode, see p.4-5, Fig. 3);
performing a 2H+ + 2e- ⇌ H2 (gas) redox reaction at the anode (hydrogen electrode, see Abstract, p.4-5, Fig. 3); and
performing an
X
n
+
m
+
m
e
-
⇌
X
n
redox reaction at the cathode, wherein
X
n
+
m
is the organic redox active species,
X
n
is spent organic redox active species and
m
is an integer (reduction and oxidation mechanism for p-benzoquinone/p-hydroquinone, see p.1, Fig. 1, see p.4-5, Fig. 3).
However, Nawar does not disclose the organic redox active species is not unsubstituted parabenzoquinone.
Marshak discloses application of quinone redox chemistry for flow batteries, wherein quinones provide the ability to tune the redox and solubility properties of the molecules through incorporation of various substituent groups onto the aromatic ring (see p.1, Fig. 1). Marshak further discloses these substituted quinones are strong candidates for large-scale energy storage in a flow battery (see p.1).
Nawar and Marshak are analogous art because they are concerned with the same field of endeavor, namely quinone redox couples for flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify Nawar by adding substituent groups onto the aromatic ring of the p-benzoquinone/p-hydroquinone redox couple because Marshak teaches tuning the properties of the quinone redox couple to achieve a wider range of reduction potentials while maintaining rapid and reversible electrochemical kinetics.
Claim(s) 4, 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 17, 19-22, 24, 26 above, and further in view of Hartwig et al. (WO 2018/146342 A1, refer to English equivalent US 2019/0393506 A1).
Regarding claim 4, modified Nawar discloses all of the claim limitations as set forth above. However, Nawar does not disclose the organic redox active species is selected from an optionally substituted polythiophene, polyaniline or polypyrrole.
Hartwig discloses redox active compounds for use as redox flow battery electrolytes, such as redox active quinone compounds used as posilytes (see Title, Abstract, [0087], [0088]-[0144]). Hartwig further discloses quinone compounds are advantageously capable of undergoing reversible and fast electrochemical transformations, the rate comparable to the vanadium redox couple, and that mixtures of redox active compounds have the advantage that more expensive and/or difficult to produce compounds can be mixed with less expensive and/or difficult to product compounds but retain or excel desired redox properties of single redox active compounds ([0089]-[0090], [0161]). Hartwig further discloses aryl groups include thiophene, pyrrole ([0030]).
Modified Nawar and Hartwig are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate thiophene, pyrrole in the catholyte of Nawar because Hartwig teaches reducing cost while maintaining performance.
Regarding claim 15, modified Nawar discloses all of the claim limitations as set forth above. However, Nawar does not further disclose the or each electron donating group is, independently, an optionally substituted alkyl group.
Hartwig discloses redox active compounds for use as redox flow battery electrolytes, such as redox active quinone compounds used as posilytes (see Title, Abstract, [0087], [0088]-[0144]). Hartwig further discloses quinone compounds are advantageously capable of undergoing reversible and fast electrochemical transformations, the rate comparable to the vanadium redox couple, and that mixtures of redox active compounds have the advantage that more expensive and/or difficult to produce compounds can be mixed with less expensive and/or difficult to product compounds but retain or excel desired redox properties of single redox active compounds ([0089]-[0090], [0161]). Hartwig further discloses the or each electron donating group is, independently, an optionally substituted alkyl group (see list of electron-donating groups [0109]).
Modified Nawar and Hartwig are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate optionally substituted alkyl group in the catholyte of Nawar because Hartwig teaches reducing cost while maintaining performance.
Claim(s) 6-7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 17, 19-22, 24, 26 above, and further in view of Huskinson et al. (US 2015/0243991 A1), hereinafter Huskinson ‘991.
Regarding claim 6, modified Nawar discloses all of the claim limitations as set forth above. However, modified Nawar does not further disclose the organic redox active species comprises an optionally substituted moiety having the formula:
PNG
media_image2.png
133
145
media_image2.png
Greyscale
Huskinson ‘991 discloses a flow battery comprising organic quinone species which cost a factor of three less per kWh than vanadium metal ions (see Title, Abstract, [0057]-[0068]), wherein other redox active species include vanadium, manganese, etc ([0069]). Huskinson further discloses 1,2-dihydroxybenzene-3,5-disulfonic acid ([0061]).
Brandon and Huskinson ‘991 are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate 1,2-dihydroxybenzene-3,5-disulfonic acid in the catholyte of Nawar because Huskinson ‘991 teaches reducing cost.
Regarding claim 7, modified Nawar discloses all of the claim limitations as set forth above. However, modified Nawar does not further disclose the organic redox active species is optionally substituted:
PNG
media_image3.png
140
360
media_image3.png
Greyscale
.
Huskinson ‘991 discloses a flow battery comprising organic quinone species which cost a factor of three less per kWh than vanadium metal ions (see Title, Abstract, [0057]-[0068]), wherein other redox active species include vanadium, manganese, etc ([0069]). Huskinson further discloses 1,2-dihydroxybenzene-3,5-disulfonic acid ([0061]).
Brandon and Huskinson ‘991 are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate 1,2-dihydroxybenzene-3,5-disulfonic acid in the catholyte of Nawar because Huskinson ‘991 teaches reducing cost.
Claim(s) 8-9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 17, 19-22, 24, 26 above, and further in view of Wang et al. (US 2018/0269516 A1).
Regarding claim 8, modified Nawar discloses all of the claim limitations as set forth above. However, modified Nawar does not further disclose the organic redox active species comprises an optionally substituted moiety having the formula:
PNG
media_image4.png
140
152
media_image4.png
Greyscale
in which each R is independently selected from carboxylic acid (-COOH), - C(O)Oalkyl or hydrogen; each E independently is an electron directing moiety;
PNG
media_image5.png
32
37
media_image5.png
Greyscale
is either a double or single bond; wherein n and m are independently 0, 1 or 2; and wherein n + m is at least 1.
Wang discloses redox species such as TEMPO, etc. in redox flow cells (see Title, Abstract, [0029]). Wang further discloses lower voltage operation and improved efficiency resulting a lower operating cost ([0023]).
Modified Nawar and Wang are analogous art because they are concerned with the same field of endeavor, namely flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate TEMPO in the catholyte of Nawar because Wang teaches lower operating cost.
Regarding claim 9, modified Nawar discloses all of the claim limitations as set forth above. However, modified Nawar does not further disclose the organic redox active species is optionally substituted:
PNG
media_image6.png
146
128
media_image6.png
Greyscale
in which each R is independently carboxylic acid -(COOH), -C(O)Oalkyl or hydrogen;
and
PNG
media_image5.png
32
37
media_image5.png
Greyscale
is either a double or single bond.
Wang discloses redox species such as TEMPO, etc. in redox flow cells (see Title, Abstract, [0029]). Wang further discloses lower voltage operation and improved efficiency resulting a lower operating cost ([0023]).
Modified Nawar and Wang are analogous art because they are concerned with the same field of endeavor, namely flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate TEMPO in the catholyte of Nawar because Wang teaches lower operating cost.
Claim(s) 1, 3, 5, 10, 13, 18-22, 24, 26 is/are rejected under 35 U.S.C. 103 as being unpatentable over Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013.
Regarding claim 1, Huskinson discloses a redox flow battery (see Title, Abstract) comprising a gaseous anolyte, an anode, a cathode, and, as a liquid catholyte, an organic redox active species having at least one electron directing moiety (p-benzoquinone in acidic solution as a positive electrode material and a hydrogen negative electrode, see Abstract, p.102-103, Fig. 2);
wherein the gaseous anolyte is a hydrogen anolyte and a 2H+ + 2e- ⇌ H2 (gas) redox reaction takes place at the anode (hydrogen negative electrode, see Abstract, p.102-103, Fig. 2); and
wherein an
X
n
+
m
+
m
e
-
⇌
X
n
redox reaction takes place at the cathode, wherein
X
n
+
m
is the organic redox active species,
X
n
is spent organic redox active species and
m
is an integer (Fig. 1).
However, Huskinson does not disclose the organic redox active species is not unsubstituted parabenzoquinone.
Marshak discloses application of quinone redox chemistry for flow batteries, wherein quinones provide the ability to tune the redox and solubility properties of the molecules through incorporation of various substituent groups onto the aromatic ring (see p.1, Fig. 1). Marshak further discloses these substituted quinones are strong candidates for large-scale energy storage in a flow battery (see p.1).
Huskinson and Marshak are analogous art because they are concerned with the same field of endeavor, namely quinone redox couples for flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify Huskinson by adding substituent groups onto the aromatic ring of the p-benzoquinone/p-hydroquinone redox couple because Marshak teaches tuning the properties of the quinone redox couple to achieve a wider range of reduction potentials while maintaining rapid and reversible electrochemical kinetics.
Regarding claim 3, modified Huskinson discloses all of the claim limitations as set forth above. Marshak further discloses the organic redox active species is selected from a carbocyclic compound, a heterocyclic compound, a polymer, a dendrimer, a dendron and a metallocene (substituted quinone, see Fig. 1).
Regarding claim 5, modified Huskinson discloses all of the claim limitations as set forth above. Marshak further discloses the organic redox active species comprises an optionally substituted moiety having the formula:
PNG
media_image1.png
156
270
media_image1.png
Greyscale
in which each E, independently, is an electron directing moiety; and k is 1, 2, 3 or 4 (substituted quinone, see Fig. 1).
Regarding claim 10, modified Huskinson discloses all of the claim limitations as set forth above. Marshak further discloses the or each electron directing moiety is an electron withdrawing group independently selected from a sulfonyl, haloalkyl, cyano, sulfonate, nitro, ammonium, carbonyl, carboxylic acid, acyl halide, C-linked ester, C-linked amide or a halide group (substituted quinone, see Fig. 1).
Regarding claim 13, modified Huskinson discloses all of the claim limitations as set forth above. Marshak further discloses the or each electron directing moiety is an electron donating group- independently selected from a phenoxide, amine, ether, phenol, N-linked amide, O-linked ester, alkyl, phenyl or a vinyl group (substituted quinone, see Fig. 1).
Regarding claim 18, modified Huskinson discloses all of the claim limitations as set forth above. Huskinson further discloses the catholyte comprises an alkali (KCl, see p.102); and the catholyte has a pH of at least about 7 (near pH 7, see p.102).
Regarding claim 19, modified Huskinson discloses all of the claim limitations as set forth above. Huskinson further discloses an ion exchange membrane (Nafion membrane, see p.102).
Regarding claim 20, modified Huskinson discloses all of the claim limitations as set forth above. Huskinson further discloses the redox flow battery comprises at least one of a graphitic anode or cathode (graphite, see p.102).
Regarding claim 21, modified Huskinson discloses all of the claim limitations as set forth above. Huskinson further discloses the anode comprises platinum, palladium, iridium, ruthenium, rhenium, rhodium, osmium, or combinations thereof (platinum, Pt-Ru, see p.102).
Regarding claim 22, modified Huskinson discloses all of the claim limitations as set forth above. Huskinson further discloses the redox flow battery is a reversible flow battery configured to operate in a power delivery mode in which it generates electrical power by the reaction of redox active species and in an energy storage mode in which it consumes electrical power to generate said redox active species (reversible, Abstract, see p.101-104).
Regarding claim 26, modified Huskinson discloses all of the claim limitations as set forth above. Marshak further discloses m is selected from 1 and 2 (2, see Fig. 1).
Regarding claim 24, Huskinson discloses a method of use of a catholyte in a redox flow battery (see Title, Abstract) comprising a hydrogen anolyte as a gaseous anolyte and an anode and a cathode (p-benzoquinone in acidic solution as a positive electrode material and a hydrogen negative electrode, see Abstract, p.102-103, Fig. 2), the method comprising:
providing an organic redox active species having at least one electron directing moiety, as a liquid catholyte (p-benzoquinone in acidic solution as a positive electrode material and a hydrogen negative electrode, see Abstract, p.102-103, Fig. 2);
incorporating the liquid catholyte into the redox flow battery (p-benzoquinone in acidic solution as a positive electrode material and a hydrogen negative electrode, see Abstract, p.102-103, Fig. 2);
performing a 2H+ + 2e- ⇌ H2 (gas) redox reaction at the anode (hydrogen negative electrode, see Abstract, p.102-103, Fig. 2); and
performing an
X
n
+
m
+
m
e
-
⇌
X
n
redox reaction at the cathode, wherein
X
n
+
m
is the organic redox active species,
X
n
is spent organic redox active species and
m
is an integer (Fig. 1).
However, Nawar does not disclose the organic redox active species is not unsubstituted parabenzoquinone.
Marshak discloses application of quinone redox chemistry for flow batteries, wherein quinones provide the ability to tune the redox and solubility properties of the molecules through incorporation of various substituent groups onto the aromatic ring (see p.1, Fig. 1). Marshak further discloses these substituted quinones are strong candidates for large-scale energy storage in a flow battery (see p.1).
Nawar and Marshak are analogous art because they are concerned with the same field of endeavor, namely quinone redox couples for flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify Nawar by adding substituent groups onto the aromatic ring of the p-benzoquinone/p-hydroquinone redox couple because Marshak teaches tuning the properties of the quinone redox couple to achieve a wider range of reduction potentials while maintaining rapid and reversible electrochemical kinetics.
Claim(s) 4, 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 18-22, 24, 26 above, and further in view of Hartwig et al. (WO 2018/146342 A1, refer to English equivalent US 2019/0393506 A1).
Regarding claim 4, modified Huskinson discloses all of the claim limitations as set forth above. However, Huskinson does not disclose the organic redox active species is selected from an optionally substituted polythiophene, polyaniline or polypyrrole.
Hartwig discloses redox active compounds for use as redox flow battery electrolytes, such as redox active quinone compounds used as posilytes (see Title, Abstract, [0087], [0088]-[0144]). Hartwig further discloses quinone compounds are advantageously capable of undergoing reversible and fast electrochemical transformations, the rate comparable to the vanadium redox couple, and that mixtures of redox active compounds have the advantage that more expensive and/or difficult to produce compounds can be mixed with less expensive and/or difficult to product compounds but retain or excel desired redox properties of single redox active compounds ([0089]-[0090], [0161]). Hartwig further discloses aryl groups include thiophene, pyrrole ([0030]).
Modified Huskinson and Hartwig are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate thiophene, pyrrole in the catholyte of Huskinson because Hartwig teaches reducing cost while maintaining performance.
Regarding claim 15, modified Huskinson discloses all of the claim limitations as set forth above. However, Huskinson does not further disclose the or each electron donating group is, independently, an optionally substituted alkyl group.
Hartwig discloses redox active compounds for use as redox flow battery electrolytes, such as redox active quinone compounds used as posilytes (see Title, Abstract, [0087], [0088]-[0144]). Hartwig further discloses quinone compounds are advantageously capable of undergoing reversible and fast electrochemical transformations, the rate comparable to the vanadium redox couple, and that mixtures of redox active compounds have the advantage that more expensive and/or difficult to produce compounds can be mixed with less expensive and/or difficult to product compounds but retain or excel desired redox properties of single redox active compounds ([0089]-[0090], [0161]). Hartwig further discloses the or each electron donating group is, independently, an optionally substituted alkyl group (see list of electron-donating groups [0109]).
Modified Huskinson and Hartwig are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate optionally substituted alkyl group in the catholyte of Huskinson because Hartwig teaches reducing cost while maintaining performance.
Claim(s) 6-7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 18-22, 24, 26 above, and further in view of Huskinson et al. (US 2015/0243991 A1), hereinafter Huskinson ‘991.
Regarding claim 6, modified Huskinson discloses all of the claim limitations as set forth above. However, modified Huskinson does not further disclose the organic redox active species comprises an optionally substituted moiety having the formula:
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Huskinson ‘991 discloses a flow battery comprising organic quinone species which cost a factor of three less per kWh than vanadium metal ions (see Title, Abstract, [0057]-[0068]), wherein other redox active species include vanadium, manganese, etc ([0069]). Huskinson ‘991 further discloses 1,2-dihydroxybenzene-3,5-disulfonic acid ([0061]).
Huskinson and Huskinson ‘991 are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate 1,2-dihydroxybenzene-3,5-disulfonic acid in the catholyte of Huskinson because Huskinson ‘991 teaches reducing cost.
Regarding claim 7, modified Huskinson discloses all of the claim limitations as set forth above. However, modified Huskinson does not further disclose the organic redox active species is optionally substituted:
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.
Huskinson ‘991 discloses a flow battery comprising organic quinone species which cost a factor of three less per kWh than vanadium metal ions (see Title, Abstract, [0057]-[0068]), wherein other redox active species include vanadium, manganese, etc ([0069]). Huskinson ‘991 further discloses 1,2-dihydroxybenzene-3,5-disulfonic acid ([0061]).
Huskinson and Huskinson ‘991 are analogous art because they are concerned with the same field of endeavor, namely redox flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate 1,2-dihydroxybenzene-3,5-disulfonic acid in the catholyte of Huskinson because Huskinson ‘991 teaches reducing cost.
Claim(s) 8-9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., as applied to claims 1, 3, 5, 10, 13, 18-22, 24, 26 above, and further in view of Wang et al. (US 2018/0269516 A1).
Regarding claim 8, modified Huskinson discloses all of the claim limitations as set forth above. However, modified Huskinson does not further disclose the organic redox active species comprises an optionally substituted moiety having the formula:
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in which each R is independently selected from carboxylic acid (-COOH), - C(O)Oalkyl or hydrogen; each E independently is an electron directing moiety;
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is either a double or single bond; wherein n and m are independently 0, 1 or 2; and wherein n + m is at least 1.
Wang discloses redox species such as TEMPO, etc. in redox flow cells (see Title, Abstract, [0029]). Wang further discloses lower voltage operation and improved efficiency resulting a lower operating cost ([0023]).
Modified Huskinson and Wang are analogous art because they are concerned with the same field of endeavor, namely flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate TEMPO in the catholyte of Huskinson because Wang teaches lower operating cost.
Regarding claim 9, modified Huskinson discloses all of the claim limitations as set forth above. However, modified Huskinson does not further disclose the organic redox active species is optionally substituted:
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in which each R is independently carboxylic acid -(COOH), -C(O)Oalkyl or hydrogen;
and
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is either a double or single bond.
Wang discloses redox species such as TEMPO, etc. in redox flow cells (see Title, Abstract, [0029]). Wang further discloses lower voltage operation and improved efficiency resulting a lower operating cost ([0023]).
Modified Huskinson and Wang are analogous art because they are concerned with the same field of endeavor, namely flow batteries.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to incorporate TEMPO in the catholyte of Huskinson because Wang teaches lower operating cost.
Response to Arguments
Applicant's arguments filed 11/3/2025 have been fully considered but they are not persuasive.
With respect to applicant’s arguments directed to Brandon et al. (WO2017/103578A1, and its English equivalent US 2018/0366759A1) (see Remarks filed 11/3/2025), said reference is no longer relied upon to teach or suggest any of the instant claims. Instead a new combination of Nawar, Saraf, et al. “Benzoquinone-Hydroquinone Couple for Flow Battery.” MRS Proceedings, vol. 1491, 2013, https://doi.org/10.1557/opl.2012.1737. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013., and Huskinson, B., et al. “Novel Quinone-Based Couples for Flow Batteries.” ECS Transactions, vol. 53, no. 7, 2 May 2013, pp. 101–105, https://doi.org/10.1149/05307.0101ecst. in view of Marshak, Michael P., et al. "Applications of quinone redox chemistry for flow batteries." 224th ECS Meeting. Retrieved from https://ecs.confex.com/ecs/224/webprogram/Paper24639.html. 2013. are relied upon to teach the instant claims as set forth above.
Applicant’s arguments with respect to claim(s) 1, 3-10, 13, 15, 17-22, 24, 26-27 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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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/James Lee/Primary Examiner, Art Unit 1725 2/6/2026