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 with traverse of Group I, claims 1-16 in the reply filed on 14 Aug 2026 is acknowledged. The traversal is on the ground(s) that the combination of Kwabi et al. (Kwabi, David G., et al. "Alkaline quinone flow battery with long lifetime at pH 12." Joule 2.9 (2018): 1894-1906) with Narayan et al. (US 2014/0370403) is invalid. Applicant argues that Narayan et al.’s finding that the solubility of quinones in water increases through the use of hydroxyl substituents does not suggest a motivation to combine Narayan et al.’s teachings with those of Kwabi et al., because solubility of the quinone-based negolyte does not inherently lead to the improvement of cyclability, capacity, and energy density that is addressed in Applicant’s instant invention. Further, argues Applicant, Narayan et al. does not conduct battery tests under near-real conditions.
This is not found persuasive because Narayan et al.’s teaching of an improved solubility for a quinone electrolyte material in and of itself would be a desired quality such that one of ordinary skill in the art would have found sufficient motivation to combine Narayan et al.’s teachings with those of Kwabi et al. (see e.g. Kwabi et al.: pg. 1895, para 1).
The requirement is still deemed proper and is therefore made FINAL.
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 1-16 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.
Regarding claim 1, the phrase “optionally substituted” in lines 9, 11-12, and 13-14 renders the claim indefinite, because it is unclear if the substitution is required to satisfy the claim or not. Claims 2-16 are similarly rejected because they require all of the limitations of claim 1.
Regarding claim 8, the phrase “optionally substituted” in lines 2-3 renders the claim indefinite, because it is unclear if the substitution is required to satisfy the claim or not.
Regarding claim 9, the phrase “optionally substituted” in line 2 renders the claim indefinite, because it is unclear if the substitution is required to satisfy the claim or not.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 13 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Regarding claim 13, it is unclear how the claimed compound of formula (I) further limits the compound already described in claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claim(s) 1-11, 13-14, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Stahl et al. (WO 2018/160618).
As to claim 1, Stahl et al. discloses a redox flow battery (see e.g. flow battery, [0051]) comprising at least one aqueous electrolyte comprising a fermented compound of formula (I)
and/or an ion of compound (I), and/or a salt of compound (I), and/or a reduced form of the anthraquinone member of compound (I) (see e.g. the compound shown in Illustration 1 below, taken from pg. 14 of Stahl et al., note that the claimed compound may be an ion of compound (I)),
PNG
media_image1.png
101
159
media_image1.png
Greyscale
PNG
media_image2.png
153
242
media_image2.png
Greyscale
Illustration 1: reproduction of a compound from pg. 14 of Stahl et al. (left) and compound (I) of the instant claim (right).
wherein: X1, X2, X3, X4, X5, X6, X7 and X8 are independently selected from the group consisting of a hydrogen atom, a halogen atom, an ether group of formula -O-A', a linear, cyclic or branched, saturated or unsaturated, optionally substituted, hydrocarbon group comprising from 1 to 10 carbon atoms, a OH group, a -R1 group and a -O-A-R1 group, A' represents a linear, cyclic or branched, saturated or unsaturated, optionally substituted, hydrocarbon group comprising from 1 to 10 carbon atoms (see e.g. Illustration 1 and pg. 14 of Stahl et al.. X1 and X3-X8 are hydrogen atoms, X1 is a group that reads on an -O-A-R1 group);
A represents a linear, cyclic or branched, saturated or unsaturated, optionally substituted, hydrocarbon group comprising from 1 to 10 carbon atoms (see e.g. Illustration 1 and pg. 14 of Stahl et al., A is a linear hydrocarbon group of 2 saturated carbon atoms);
R1 represents COOH, SO3H, or a salt thereof (see e.g. Illustration 1, pg. 14 of Stahl et al., and para [0044] of Stahl et al., R1 may a salt of SO3H);
and wherein one and only one of X1, X2, X3, X4, X5, X6, X7 and X8 is -O-A-R1 (see e.g. Illustration 1 and pg. 14 of Stahl et al., only one of the X components is of the form -O-A-R1).
The compound illustrated in pg. 14 of Stahl et al. differs from the claimed compound (I) in that none of X1, X2, X3, X4, X5, X6, X7 and X8 are OH. Stahl et al. does not explicitly show a compound in which one to three of X1, X2, X3, X4, X5, X6, X7 and X8 is OH.
However, Stahl et al. teaches that the X1, X2, X3, X4, X5, X6, X7 and X8 components of the above compound may each independently be an OH of hydroxy group (see e.g. Stahl et al. [0042]). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing one to three of X2, X3, X4, X5, X6, X7 and/or X8 with OH, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one to three of the H atoms with OH would fail to yield any new benefit that would not have been reasonably expected by said artisan.
As to claim 2, Stahl et al. teaches the redox flow battery according to claim 1, wherein one and only one of X1, X2, X3, X4, X5, X6, X7 and X8 is OH and wherein one and only one of X1, X2, X3, X4, X5, X6, X7 and X8 is -O-A-R1 (see e.g. Stahl et al.: [0042], any one of R1-R8, which correspond to X1-X8, may independently be OH and the rest may be H atoms or an -O-A-R1 group as set forth above. One and only one of the eight groups is an -O-A-R1 group).
As to claim 3, Stahl et al. teaches the redox flow battery according to claim 1 or 2, wherein one and only one of X3 and X8 is OH (see e.g. Stahl et al.: [0042], any one of R1-R8, which correspond to X1-X8, may be OH), and one and only one of X3 and X8 is -O-A-R (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
As to claim 4, Stahl et al. teaches the redox flow battery according to claim 1, wherein X3 is OH (see e.g. Stahl et al.: [0042], any one of R1-R8, which correspond to X1-X8, may be OH), and X8 is -O-A-R1 (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
As to claim 5, Stahl et al. teaches the redox flow battery according to claim 1, X8 is OH (see e.g. Stahl et al.: [0042], any one of R1-R8, which correspond to X1-X8, may be OH). Stahl et al. explicitly shows embodiments in which the X1 and X2 positions are of the form -O-A-R1, and does not depict an embodiment in which X3 is -O-A-R1. However, para [0042] of Sthal teaches that any of the R1-R8 groups (which correspond to X1-X8) may be the -O-A-R1 group (i.e., the sulfonate moiety and linking group, see Stahl et al.: [0042]). It would therefore have been obvious to one of ordinary skill in the art to modify the compound shown in Illustration 1 above by moving the -O-A-R1 group from the X1 position to the X3 position.
As to claim 6, Stahl et al. teaches the redox flow battery according to claim 1, wherein two of X3, X6, and X8 are OH (see e.g. Stahl et al.: [0042], any two of R1-R8, which correspond to X1-X8, may independently be OH), and wherein one and only one of X3, X6 and X8 is -O-A-R1 (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
As to claim 7, Stahl et al. teaches the redox flow battery according to claim 1, wherein three of X3, X5, X6, and X8 are OH (see e.g. Stahl et al.: [0042], any three of R1-R8, which correspond to X1-X8, may independently be OH), and wherein one and only one of X3, X5, X6 and X8 is -O-A-R1 (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
As to claim 8, Stahl et al. teaches the redox flow battery according to claim1, wherein X1 is a -O-CH2-CH2-SO3 group (see e.g. Illustration 1 above and pg. 14 of Stahl et al.), which is not a group that represents a linear, cyclic or branched, saturated or unsaturated, optionally substituted, hydrocarbon group comprising from 1 to 10 carbon atoms.
However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other such that the -O-CH2-CH2-SO3 group is in position X8 and X1 is a hydrogen atom. Additionally, Stahl et al. teaches that any of the groups X1-X8 that do not include a sulfonate moiety way independently be an alkyl, a cycloalkyl, a thioether, a hydroxy, an amino, or hydrogen, or combinations thereof. It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to modify the structure shown in Illustration 1 above by moving the -O-CH2-CH2-SO3 group to position X8 and to replace the hydrogen at X1 with a 2-carbon alkyl group, which reads on a linear saturated hydrocarbon group because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by in this manner would fail to yield any new benefit that would not have been reasonably expected by said artisan.
As to claim 9, Stahl et al. teaches the redox flow battery according to claim 1, wherein A represents (CH2)n, optionally substituted, wherein n is an integer selected from 1 to 10 (see e.g. Illustration 1 and pg. 14 of Stahl et al., the (CH2)2 linkage reads on A).
As to claim 10, Stahl et al. teaches the redox flow battery according to any one of claim 1, wherein said -O-A-R1 group represents O-(CH2)n-COOH or O-(CH2)n- SO3H wherein n is from 1 to 10 (see e.g. Illustration 1 and pg. 14 of Stahl et al., the O-(CH2)2-SO3- group reads on the claimed -O-A-R1 group at least when the compound is an ion of formula (I)).
As to claim 11, Stahl et al. teaches the redox flow battery according to claim 1, wherein R1 is selected from the group consisting of CO2H, CO2-M+, SO3H and SO3-M+, M+ being selected from the group consisting of Li+, Na+, K+ and NH4 (see e.g. Illustration 1 and pg. 14 of Stahl et al., the R1 group of Stahl et al. is SO3-, which reads on an ionized form of SO3H. Note that claim 1 states that the claimed compound may be an ion of compound (I)).
As to claim 13, Stahl et al. teaches the redox flow battery according to claim 1, wherein said compound of formula (I) has the structure shown in claim 1 wherein X1, X2, X3, and X8 are as defined in claim 1 (see e.g. Illustration 1 and pg. 14 of Stahl et al. and the rejection of claim 1 set forth above).
As to claim 14, Stahl et al. teaches the redox flow battery according to claim 1, wherein said compound of formula (I) has the structure shown in Illustration 1 above (see e.g. Illustration 1 and pg. 14 of Stahl et al.). This compounds reads on the first structure shown in claim 14, except the group at position at X3 of Stahl et al. is a hydrogen atom rather than an -OH group (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
However, Stahl et al. teaches that the X3 component of the above compound may be an OH of hydroxy group (see e.g. Stahl et al. [0042]). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing X3 with OH, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one of the H atoms with OH would fail to yield any new benefit that would not have been reasonably expected by said artisan.
As to claim 16, Stahl et al. teaches the redox flow battery according to claim 1, wherein -O-A-R1 is as defined in claim 1, wherein said compound of formula (I) has the structure shown in Illustration 1 above (see e.g. Illustration 1 and pg. 14 of Stahl et al.). This compounds reads on the first structure shown in claim 14, with two differences:
(1) the group at position at X3 of Stahl et al. is a hydrogen atom rather than an -OH group and
(2) the group at position at X1 of Stahl et al. is a hydrogen atom rather than a -CH3 group, and
(see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
Regarding (1), Stahl et al. teaches that the X3 component of the above compound may be an OH or hydroxy group (see e.g. Stahl et al. [0042]). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing X3 with OH, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one of the H atoms with OH would fail to yield any new benefit that would not have been reasonably expected by said artisan.
Regarding (2), Stahl et al. teaches that the X1 component of the above compound may be a CH3 group (see e.g. Stahl et al. [0042], Stahl et al. teaches that R1, which reads on X1, may be an alkyl group, which reads on a methyl CH3 group). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing X1 with CH3, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one of the H atoms with CH3 would fail to yield any new benefit that would not have been reasonably expected by said artisan.
Claim(s) 12 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Stahl et al. (WO 2018/160618) as applied to claim 1 above, and further in view of Narayan et al. (US 9,614,245).
As to claim 12, Stahl et al. teaches the redox flow battery according to claim 1. However, in Stahl et al.’s redox flow battery, X2 represents an alkyl, a cycloalkyl, a thioether, a hydroxy, an amino, or hydrogen, or combinations thereof (see e.g. Stahl et al.: [0042]), and Stahl et al. does not teach an embodiment in which X2 represents a -R1 group.
Narayan et al., also working on the problem of electrolytes for redox flow batteries, teaches an electrolyte comprising a structurally similar compound (see e.g. Narayan et al.: claim 1, claim 17, and Illustration 2 below). Narayan et al. also states that the R22 group, which is an analogue of the instantly-claimed X2 group, may be selected from “functional groups that increases water solubility selected from the group consisting of -SO3H, -PO3H2, -COOH,” (see e.g. Narayan et al.: claim 17).
PNG
media_image3.png
162
287
media_image3.png
Greyscale
Illustration 2: reproduction of a compound from claim 1 of Narayan et al..
Stahl et al. states that it is desirable for redox mediators to have high solubility, and that the solubility of a quinone can be improved via the addition of substituent groups (see e.g. Stahl et al.: [0004], [0039]).
It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to modify the compound of Stahl et al. by substituting the X2 group with an R1 group comprising -SO3H or -COOH in the manner taught by Narayan et al.. Said artisan would have been motivated to make such a substitution because Stahl et al. teaches that it is preferable for the compound to be water-soluble, and Narayan et al. teaches that -SO3H or -COOH are functional groups that increase water solubility.
As to claim 15, Stahl et al. teaches the redox flow battery according to claim 1, wherein -O-A-R1 is as defined in claim 1, wherein said compound of formula (I) has the structure shown in Illustration 1 above (see e.g. Illustration 1 and pg. 14 of Stahl et al.). This compounds reads on the first structure shown in claim 14, with three differences:
(1) the group at position at X3 of Stahl et al. is a hydrogen atom rather than an -OH group and
(2) the group at position at X1 of Stahl et al. is a hydrogen atom rather than a -CH3 group, and
(3) the group at position at X2 of Stahl et al. is a hydrogen atom rather than a -COOH group (see e.g. Illustration 1 and pg. 14 of Stahl et al.. In this example, X1 is -O-A-R1. However, the X1 and X8 positions are chemically identical via mirror symmetry, and as such one of ordinary skill in the art would therefore have found it obvious to swap the X1 and X8 groups with each other).
Regarding (1), Stahl et al. teaches that the X3 component of the above compound may be an OH or hydroxy group (see e.g. Stahl et al. [0042]). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing X3 with OH, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one of the H atoms with OH would fail to yield any new benefit that would not have been reasonably expected by said artisan.
Regarding (2), Stahl et al. teaches that the X1 component of the above compound may be a CH3 group (see e.g. Stahl et al. [0042], Stahl et al. teaches that R1, which reads on X1, may be an alkyl group, which reads on a methyl CH3 group). Therefore, one of ordinary skill in the art prior to the filing date of the claimed invention would have found it obvious to modify the compound illustrated above by replacing X1 with CH3, because such a substitution is taught by Stahl et al., and modifying the compound illustrated above by replacing one of the H atoms with CH3 would fail to yield any new benefit that would not have been reasonably expected by said artisan.
Regarding (3), Narayan et al., also working on the problem of electrolytes for redox flow batteries, teaches an electrolyte comprising a structurally similar compound (see e.g. Narayan et al.: claim 1, claim 17, and Illustration 2 above). Narayan et al. also states that the R22 group, which is an analogue of the instantly-claimed X2 group, may be selected from “functional groups that increases water solubility selected from the group consisting of -SO3H, -PO3H2, -COOH,” (see e.g. Narayan et al.: claim 17).
Stahl et al. states that it is desirable for redox mediators to have high solubility, and that the solubility of a quinone can be improved via the addition of substituent groups (see e.g. Stahl et al.: [0004], [0039]).
It would therefore have been obvious to one of ordinary skill in the art prior to the filing date of the claimed invention to modify the compound of Stahl et al. by substituting the X2 group with -COOH in the manner taught by Narayan et al.. Said artisan would have been motivated to make such a substitution because Stahl et al. teaches that it is preferable for the compound to be water-soluble, and Narayan et al. teaches that - COOH is a functional group that increases water solubility.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Huskinson et al. (WO 2014/052682), Aziz et al. (US 2021/0009497), and Hartwig et al. (WO 2019/072385) all teach similar categories of quinone-based electrolyte materials for a redox flow battery.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALBERT HILTON whose telephone number is (571)272-4068. The examiner can normally be reached Monday - Friday 8:00 AM - 5:00 PM EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Tong Guo can be reached at (571)-272-3066. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/A.M.H./Examiner, Art Unit 1723
/BACH T DINH/Primary Examiner, Art Unit 1726 09/11/2026
Prosecution Insights