DETAILED ACTION
Response to Amendment/Arguments
Claims 1, 3-18, 20, and 22-23 are currently pending. Claims 2, 19, and 21 are cancelled. Claims 12-18, 20, and 22-23 are withdrawn from further consideration as being drawn to a non-elected invention. No claim has been amended.
Applicant's arguments filed 2/2/26 have been fully considered but they are not persuasive.
The Applicant argues that “Zhao fails to disclose a macrocycle comprising a substituted or unsubstituted phenanthrenequinone unit. Zhao discloses a battery including a series of quinones combined with conductive additives and dispersants on a metal foil, 3M Zn(CF₃SO₃)₂, and a Zn foil. No evidence is presented that demonstrates a person of skill in the art would have known to make the necessary, substantial changes to the materials of Zhao to reach the instant claims. First, a person of skill in the art would have to specifically select 9, 10-PQ from all of the quinones disclosed in Zhao. Next, they would have to fundamentally change the molecular structure of 9,10-
PQ such that it forms a macrocycle, preserving the quinone functional groups and arranged with connecting bonds as claimed. The Office has not provided any evidence that a skilled artisan would have known to pursue these specific modifications, nor that they would have reasonably expected success in doing so. There is no suggestion in either reference regarding how to modify any quinone to form a macrocycle. Zhao teaches no transformations of quinones. Nalluri discloses rigid chiral triangles
assembled from pyromellitic diimide and naphthalene diimide-based redox-active units, which are not quinones. Neither Zhao nor Nalluri provides any suggestion for forming the claimed macrocycle with 9,10-PQ, or for modifying the molecular structure of 9,10-PQ at all. The Office has not shown that the combination of Zhao and Nalluri would reasonably result in the claimed macrocycle. Nothing in the art suggests that the combination would inherently or predictably yield the claimed macrocycle comprising a substituted or unsubstituted phenanthrenequinone unit and a hydrated zinc complex.
Moreover, the battery experiments of Nalluri were conducted in an organic monovalent-
cation electrolyte rather than aqueous bivalent-cation electrolyte of the present invention. Given the numerous ways chemical structures can be modified as well as choices for electrolytes, the particular changes resulting in the instant claims are not obvious.”.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). The Zhao reference is relied upon for teaching a cathode comprising an unsubstituted phenanthrenequinone unit (subunit) and a hydrated zinc complex. Next, Zhao discloses only five quinone compounds: (1,4-NQ), (9,10-AQ), (C4Q), (1,2-NQ), and (9,10-PQ). Since all of these quinone compounds are suitable as cathodic materials in aqueous ZBs (zinc batteries) (see “Results”), one of ordinary skill in the art would have been able to choose from a finite number of predictable solutions with a reasonable expectation of success. Nalluri teaches isosceles triangles comprising subunits such as NDI or PMDI and a method of preparing isosceles triangles (macrocycle) by stepwise condensations between commercially available compounds. Since the method of preparing a macrocycle such as an isosceles triangle is known in the art, one of ordinary skill in the art would have been able to prepare a macrocycle that is an isosceles triangle of 9,10-phenanthrenequinone and the results would have been predictable to one of ordinary skill in the art. Even if the battery experiments of Nalluri were conducted in an organic monovalent-cation electrolyte rather than aqueous bivalent-cation electrolyte, based upon the similarities in terms of rechargeable batteries, one of ordinary skill in the art would have been able to apply the teachings of Nalluri to improve the electrochemical performance of rechargeable batteries such as aqueous rechargeable zinc batteries. Therefore, the Office maintains the contention that the combination of Zhao and Nalluri results in the claimed macrocycle comprising an unsubstituted phenanthrenequinone unit and a hydrated zinc complex.
The Applicant further argues that “Moreover, the battery experiments of Kim were conducted in an organic trivalent-cation electrolyte rather than aqueous bivalent-cation electrolyte of the present invention. Given the numerous ways Zhao's materials can be modified as well as choices for electrolytes and the lack of suggestion in either reference, there is no basis to conclude that a skilled artisan would specifically combine Zhao with Kim in the manner required to reach the claimed macrocycle. Thus, the particular changes resulting in the instant claims are not obvious. Furthermore, the instant application discloses unexpected results that are indicative of non-obviousness. Kim predicts that PQ derivatives cannot be fully reduced to a dianionic state and only
a 3-electron reduced state can be accessed for the triangular macrocycle. Kim, p.53. In contrast, the current application discloses a triangular macrocycle that can be reduced fully to the dianionic state in each PQ unit and each reduced PQ unit may interact with a zinc dication. Specification, para. [0062]. Because Kim teaches that PQ derivatives cannot be fully reduced to a dianionic state and only a 3-electron reduced state, those of ordinary skill cannot reasonably expect that the PQ unit would be reduced to the dianionic state. As a result, the combination of Zhao and Kim fail to suggest such a property”.
In response, the Office disagrees that there is no basis to conclude that a skilled artisan would specifically combine Zhao with Kim in the manner required to reach the claimed macrocycle. Firstly, both Zhao and Kim teach phenanthrenequinone (PQ) based compound as active materials. So, even if Zhao teaches aqueous batteries and Kim teaches organic batteries, one of ordinary skill in the art would have recognized that the teachings of Kim would be applicable to the Zhao 9,10-phenanthrenequinone and zinc complex to form a triangular macrocycle comprising 9,10-phenanthrenequinone and zinc complex in order to utilize a rigid triangular macrocycle that increases the specific capacity and the cyclability as a consequence of its layered architecture and the minimization of solvent effects (pg. 57, “Conclusions”). Lastly, with respect to the argument that “the current application discloses a triangular macrocycle that can be reduced fully to the dianionic state in each PQ unit and each reduced PQ unit may interact with a zinc dication”, this argument is not commensurate in scope with the claims because the present claims do not require a triangular macrocycle that can be reduced fully to the dianionic state in each PQ unit.
Therefore, upon further consideration, claims 1 and 3-11 stand rejected under the following 103 rejections.
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, 3-7, and 9-11 are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al (“High-Capacity Aqueous Zinc Batteries Using Sustainable Quinone Electrodes”, Science Advances, 2018, 4, eaao1761) in view of Nalluri et al ("Chiral redox-active isosceles triangles", Journal of the American Chemical Society, 138, (2016), 5968-5977).
Regarding claims 1, 3-7, and 9-11, Zhao et al discloses a cathode (electrode) comprising: a cathodic material comprising a 9,10-phenanthrenequinone and [Zn(H2O)6]2+ (hydrated zinc complex) that is planar; a conductive additive (electron-conducting additive); and polyvinylidene fluoride (binder material / PVDF), and a thin titanium foil (substrate) (“RESULTS” and “Battery testing”).
However, Zhao et al does not expressly teach a macrocycle comprising a substituted or unsubstituted phenanthrenequinone (claim 1); wherein the macrocycle comprising three substituted or unsubstituted phenanthrenequinone units in a triangular arrangement (claim 4); wherein the macrocycle comprises
PNG
media_image1.png
326
346
media_image1.png
Greyscale
(claim 5).
Nalluri et al teaches the concept of forming isosceles triangle that is a macrocycle comprising three units in a triangular arrangement as an electrode-active material in lithium-ion batteries (pg. 5969).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Zhao cathodic material to include a macrocycle comprising three unsubstituted phenanthrenequinone units in a triangular arrangement; wherein the macrocycle comprises
PNG
media_image1.png
326
346
media_image1.png
Greyscale
in order to improve the redox-active characteristics and high thermal stability of the cathodic material, thereby improving rate capabilities and cycling performance of the battery (pg. 5969).
Claims 1, 3-7, and 9-11 are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al (“High-Capacity Aqueous Zinc Batteries Using Sustainable Quinone Electrodes”, Science Advances, 2018, 4, eaao1761) in view of Kim et al ("Rechargeable aluminum organic batteries", Nature Energy, Vol. 4, (2019), 51-59).
Regarding claims 1, 3-7, and 9-11, Zhao et al discloses a cathode (electrode) comprising: a cathodic material comprising a 9,10-phenanthrenequinone and [Zn(H2O)6]2+ (hydrated zinc complex) that is planar; a conductive additive (electron-conducting additive); and polyvinylidene fluoride (binder material / PVDF), and a thin titanium foil (substrate) (“RESULTS” and “Battery testing”).
However, Zhao et al does not expressly teach a macrocycle comprising a substituted or unsubstituted phenanthrenequinone (claim 1); wherein the macrocycle comprising three substituted or unsubstituted phenanthrenequinone units in a triangular arrangement (claim 4); wherein the macrocycle comprises
PNG
media_image1.png
326
346
media_image1.png
Greyscale
(claim 5).
Kim et al teaches the concept of forming PQ- - 3AlCl2 which is a macrocycle comprising three unsubstituted phenanthrenequinone units in a triangular arrangement and an aluminum complex (zinc complex) as an electrode active material (“Design and synthesis of PQ derivatives” and Fig. 1b).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was made to modify the Zhao cathodic material to include a macrocycle comprising three unsubstituted phenanthrenequinone units in a triangular arrangement; wherein the macrocycle comprises
PNG
media_image1.png
326
346
media_image1.png
Greyscale
in order to utilize a rigid triangular macrocycle that increases the specific capacity and the cyclability as a consequence of its layered architecture and the minimization of solvent effects (pg. 57, “Conclusions”).
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al in view of Nalluri et al as applied to claim 7 above, and further in view of Hojo et al (US 2010/0196758).
However, Zhao et al as modified by Nalluri et al does not expressly teach an electron-conducting additive that is acetylene black (claim 8).
Hojo et al discloses a positive electrode comprising acetylene black as a conductive agent (electron-conducting additive) ([0190]).
Therefore, the invention as a whole would have been obvious to one of ordinary skill in the art at the time the invention was made because the disclosure of Hojo et al indicates that acetylene black is a suitable material for use as conductive agent. The selection of a known material based on its suitability for its intended use has generally been held to be prima facie obvious (MPEP §2144.07). As such, it would be obvious to use acetylene black.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al in view of Kim et al as applied to claim 7 above, and further in view of Hojo et al (US 2010/0196758).
However, Zhao et al as modified by Kim et al does not expressly teach an electron-conducting additive that is acetylene black (claim 8).
Hojo et al discloses a positive electrode comprising acetylene black as a conductive agent (electron-conducting additive) ([0190]).
Therefore, the invention as a whole would have been obvious to one of ordinary skill in the art at the time the invention was made because the disclosure of Hojo et al indicates that acetylene black is a suitable material for use as conductive agent. The selection of a known material based on its suitability for its intended use has generally been held to be prima facie obvious (MPEP §2144.07). As such, it would be obvious to use acetylene black.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TONY S CHUO whose telephone number is (571)272-0717. The examiner can normally be reached Monday - Friday, 9:00am - 5:30pm.
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, Jonathan Leong can be reached at 571-270-1292. 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.
/T.S.C/Examiner, Art Unit 1751
/JONATHAN G LEONG/Supervisory Patent Examiner, Art Unit 1751 5/1/2026
Prosecution Insights