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 .
Priority
Acknowledgment is made of applicant's claim for foreign priority based on an application filed in the Republic of Korea on January 17, 2023. It is noted, however, that applicant has not filed a certified copy of the KR10-2023-0007418 application as required by 37 CFR 1.55.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The 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 1-10, 14, and 15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by He et al. (CN 116178370 A, machine translation relied upon herein and hereinafter “He ’370”).
Regarding claims 1-4, He ’370 discloses a naphthalene diimide compound represented by Chemical Formula 1 (paragraphs n0042-n0047 and n0063-n0068, NPr-NDI where R is b, n=1, and m=1 and see original paragraph 0069 for NPr-NDI structure), wherein L1, L2, L3, and L4 are all C3 alkylene groups, and R1, R2, R3, and R4 are all C1 alkyl groups.
Regarding claim 5, He ’370 discloses the limitations of claim 1. He ’370 further discloses wherein the naphthalene diimide compound is represented by Chemical Formula 1-1 (paragraphs n0042-n0047 and n0063-n0068, NPr-NDI where R is b, n=1, and m=1 and see original paragraph 0069 for NPr-NDI chemical formula).
Regarding claim 6, He ’370 discloses the limitations of claim 1. He ’370 further discloses an electrolyte solution for a redox flow battery comprising the naphthalene diimide compound according to claim 1 (paragraph n0034, naphthalimide derivatives as anolyte).
Regarding claim 7, He ’370 discloses the limitations of claim 6. He ’370 further discloses the electrolyte solution further comprising a solvent (paragraph n0034, naphthalimide derivative dissolved in 2M NaCl).
Regarding claim 8, He ’370 discloses the limitations of claim 7. He ’370 further discloses wherein the solvent is an aqueous solvent (paragraph n0034, naphthalimide derivative dissolved in 2M NaCl).
Regarding claim 9, He ’370 discloses the limitations of claim 8. He ’370 further discloses wherein the aqueous solvent is sodium chloride (paragraph n0034, 2M NaCl).
Regarding claim 10, He ’370 discloses the limitations of claim 6. He ’370 further discloses the electrolyte solution further comprising a supporting electrolyte (paragraph n0034, 2M NaCl).
Regarding claim 14, He ’370 discloses the limitations of claim 6. He ’370 further discloses a redox flow battery comprising the electrolyte solution for a redox flow battery according to claim 6 (paragraph n0034, neutral aqueous organic flow battery with naphthalimide derivative as the anolyte).
Regarding claim 15, He ’370 discloses the limitations of claim 14. He ’370 further discloses wherein the redox flow battery comprises: a positive electrode cell comprising a positive electrode and a positive electrode electrolyte solution (paragraphs n0096-n0100, positive electrode components and ferrocene solution); a negative electrode cell comprising a negative electrode and a negative electrode electrolyte solution (paragraphs n0096-n0100, negative electrode components and naphthalimide derivative solution); and a separator disposed between the positive electrode cell and the negative electrode cell (paragraphs n0096, anion exchange membrane), and the negative electrode electrolyte solution is the electrolyte solution for a redox flow battery (paragraphs n0034 and n0096-n0100, naphthalimide derivative as anolyte).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The 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.
Claims 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over He et al. (CN 116178370 A, machine translation relied upon herein and hereinafter “He ’370”) in view of Liu et al. (US 2018/0072669 A1).
Regarding claim 11, He ’370 discloses the limitations of claim 6. He ’370 does not disclose the electrolyte solution further comprising an electrode active material.
Liu et al. discloses the electrolyte solution further comprising an electrode active material (paragraph 0143, second redox active material that may include V3+/V2+).
He ’370 and Liu et al. are considered to be analogous art because they are in the same field of aqueous organic redox flow batteries. The viologen compound of Liu et al. is an organic molecule that may be used in the second redox active material in combination with V3+/V2+ (paragraph 0143), and performs an analogous function to the naphthalene diimide compound of He ’370. It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the electrolyte solution of He ’370 with the teachings of Liu et al. according to known methods to yield the predictable result of an electrolyte solution composed of a combination of a naphthalene diimide compound and a vanadium-based compound, and one of ordinary skill in the art would have a reasonable expectation of success in doing so (see MPEP §2143(I)(A)).
Regarding claim 12, modified He ’370 discloses the limitations of claim 11, and further discloses wherein the electrode active material contains a 2-valent to 5-valent vanadium-based compound (Liu et al. paragraph 0143, second redox active material that may be a combination including V3+/V2+).
Regarding claim 13, modified He ’370 discloses the limitations of claim 12, and further discloses wherein the 2-valent to 5-valent vanadium-based compound comprises one or two or more selected from the group consisting of V2+, V3+, VO2+, and VO2+ (Liu et al. paragraph 0143, second redox active material that may be a combination including V3+/V2+).
Claims 1-10, 14, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Wiberg et al. (WO 2020201405 A1) in view of He et al. (CN 114874211 A, machine translation relied upon herein and hereinafter “He ’211”).
Regarding clams 1-4, Wiberg et al. discloses a quaternary ammonium NDI salt with two ammonium groups (page 36, example 4a), wherein L1 and L3 are C3 alkylene groups and R2 and R3 are C1 alkyl groups. Wiberg et al. does not disclose a naphthalene diimide compound represented by Chemical Formula 1, with four ammonium groups, L2, L4, R1, and R4.
He ’211 discloses a class of perylene diimide-based derivatives (paragraph n0066-n0068 and see original paragraph 0067 for structure) with six ammonium groups, wherein L1, L2, L3, and L4 are all C2 alkylene groups and R1, R2, R3, and R4 are C1 alkyl groups. He ’211 also discloses that the introduction of quaternary ammonium salts can improve water solubility and increase molecular size, which provides narrow band gaps and fast dynamic characteristics and blocks permeation of electrolyte, improving battery stability (n0034 and n0175).
Wiberg et al. and He ’211 are considered to be analogous to the claimed invention because they are in the same field of naphthalene diimide compounds. It would have been obvious to one of ordinary skill in the art to have applied the known improvement of introducing additional quaternary ammonium salts as taught by He ’211 to the quaternary ammonium NDI salt of Wiberg et al. to yield the naphthalene diimide compound represented by Chemical Formula 1, wherein L1, L2, L3, and L4 are all C3 alkylene groups, and R1, R2, R3, and R4 are all C1 alkyl groups (see MPEP § 2143(I)(C)). Compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. See In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977) (see MPEP § 2144.09(II)). One of ordinary skill in the art would have recognized the number of quaternary ammonium salts as a result-effective variable with predictable result of improving water solubility and battery stability. Varying the number of quaternary ammonium salts by varying reactants would have been routine optimization, and one of ordinary skill in the art would have had a reasonable expectation of success in formulating a four quaternary ammonium salt NDI compound due to the prior art’s disclosure of two and six quaternary ammonium salt NDI compounds (see MPEP § 2144.05(II)).
Regarding claim 5, modified Wiberg discloses the limitations of claim 1. Modified Wiberg further discloses wherein the naphthalene diimide compound is represented by Chemical Formula 1-1 (L1, L2, L3, and L4 are all C3 alkylene groups, and R1, R2, R3, and R4 are all C1 alkyl groups as described above).
Regarding claim 6, modified Wiberg discloses the limitations of claim 1. Wiberg et al. further discloses an electrolyte solution for a redox flow battery comprising the naphthalene diimide compound according to claim 1 (page 7 paragraph 3, aqueous-based electrolyte solution comprising modified naphthalene diimide NDI).
Regarding claim 7, modified Wiberg discloses the limitations of claim 6. Wiberg et al. further discloses the electrolyte solution further comprising a solvent (page 3 paragraph 5, aqueous-based electrolyte solutions comprising water, or water in admixture with water-soluble co-solvents and/or supporting electrolytes).
Regarding claim 8, modified Wiberg discloses the limitations of claim 7. Wiberg et al. further discloses wherein the solvent is an aqueous solvent, a non-aqueous solvent, or a mixture of two or more thereof (page 3 paragraph 5, aqueous-based electrolyte solutions comprising water, or water in admixture with water-soluble co-solvents and/or supporting electrolytes).
Regarding claim 9, modified Wiberg discloses the limitations of claim 8. Wiberg et al. further discloses wherein the aqueous solvent is one or more of potassium chloride, sodium chloride, ammonium chloride, sulfuric acid, and phosphoric acid (page 4 paragraph 2, supporting electrolytes), and the non-aqueous solvent is one or more of ethanol, methanol (page 3 paragraph 5, alcohols); acetonitrile, propionitrile, butyronitrile (page 4 paragraph 1, nitrile solvents); dimethyl sulfoxide (page 4 paragraph 1, sulfoxide solvents), sulfolane (page 4 paragraph 1, sulfone solvents); N,N-dimethylformamide, dimethylacetamide, N-methylpyrrolidone (page 4 paragraph 1, amide solvents); 1,2-dimethoxyethane, tetrahydrofuran (page 4 paragraph 1, ether solvents); dimethyl carbonate, diethyl carbonate, propylene carbonate, ethylene carbonate, methyl ethyl carbonate (page 4 paragraph 1, carbonate solvents); acetone (page 4 paragraph 1, ketone solvents); 1,4-butyrolactone, and ethyl acetate (page 4 paragraph 1, ester solvents).
Regarding claim 10, modified Wiberg discloses the limitations of claim 6. Wiberg et al. further discloses the electrolyte solution further comprising a supporting electrolyte (page 3 paragraph 5 and page 4 paragraph 2, supporting electrolytes).
Regarding claim 14, modified Wiberg discloses the limitations of claim 6. Wiberg et al. further discloses a redox flow battery comprising the electrolyte solution for a redox flow battery according to claim 6 (page 2 paragraph 1, redox flow battery comprising second aqueous-based electrolyte solution).
Regarding claim 15, modified Wiberg discloses the limitations of claim 14. Wiberg et al. further discloses wherein the redox flow battery comprises: a positive electrode cell comprising a positive electrode and a positive electrode electrolyte solution (page 2 paragraph 1, positive compartment comprising a positive electrode in contact with a first aqueous-based electrolyte solution); a negative electrode cell comprising a negative electrode and a negative electrode electrolyte solution (page 2 paragraph 1, negative compartment comprising a negative electrode in contact with a second aqueous-based electrolyte solution); and a separator disposed between the positive electrode cell and the negative electrode cell (page 2 paragraph 1, separator component that separates the aqueous-based electrolyte solutions), and the negative electrode electrolyte solution is the electrolyte solution for a redox flow battery (page 2 paragraph 1, second aqueous-based electrolyte solution comprising an organic redox-active molecule that is a naphthalene diimide).
Claims 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over Wiberg et al. (WO 2020201405 A1) in view of He et al. (CN 114874211 A, machine translation relied upon herein and hereinafter “He ’211”) as applied to claim 6 above, and further in view of Liu et al. (US 2018/0072669 A1).
Regarding claim 11, modified Wiberg discloses the limitations of claim 6. Modified Wiberg does not disclose the electrolyte solution further comprising an electrode active material.
Liu et al. discloses the electrolyte solution further comprising an electrode active material (paragraph 0143, second redox active material that may include V3+/V2+).
The viologen compound of Liu et al. is an organic molecule that may be used in the second redox active material in combination with V3+/V2+ (paragraph 0143), and performs an analogous function to the naphthalene diimide compound of modified Wiberg. It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the electrolyte solution of modified Wiberg with the teachings of Liu et al. according to known methods to yield the predictable result of an electrolyte solution composed of a combination of a naphthalene diimide compound and a vanadium-based compound, and one of ordinary skill in the art would have a reasonable expectation of success in doing so (see MPEP §2143(I)(A)).
Regarding claim 12, modified Wiberg discloses the limitations of claim 11, and further discloses wherein the electrode active material contains a 2-valent to 5-valent vanadium-based compound (Liu et al. paragraph 0143, second redox active material that may be a combination including V3+/V2+).
Regarding claim 13, modified Wiberg discloses the limitations of claim 12, and further discloses wherein the 2-valent to 5-valent vanadium-based compound comprises one or two or more selected from the group consisting of V2+, V3+, VO2+, and VO2+ (Liu et al. paragraph 0143, second redox active material that may be a combination including V3+/V2+).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jackie Liang whose telephone number is (571)-272-0880. The examiner can normally be reached M-F 8:30AM - 4:30PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey T. Barton can be reached at (571)-272-1307. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.L./Examiner, Art Unit 1726
/JEFFREY T BARTON/Supervisory Patent Examiner, Art Unit 1726 27 March 2026
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