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 .
Response to Amendment
In response to the amendment received on 06/24/2026:
Claims 1-17 and 20-21 are pending in the current application. Claims 1, 3, 6, 14, and 15 have been amended. Claims 20-21 are newly added.
Response to Arguments
Applicant’s arguments, see Remarks Page 9, filed 06/24/2026, with respect to the objections to the specification have been fully considered. The objections have been withdrawn in light of the amendments to the specification.
Applicant’s arguments, see Remarks Page 9, filed 06/24/2026, with respect to the objections to the claims have been fully considered. The objections have been withdrawn in light of the amendments to the claims.
Applicant’s arguments, see Remarks Page 10, filed 06/24/2026, with respect to the rejections under 35 U.S.C. 112(b) have been fully considered. The rejections have been withdrawn in light of the amendments to the claims.
Applicant’s arguments, see Remarks Pages 10-13, filed 06/24/2026, with respect to the rejections under 35 U.S.C. 102/103 have been fully considered. The rejections have been withdrawn in light of Applicant’s arguments.
Claim Interpretation
The following is a quotation of 35 U.S.C. 112(f):
(f) Element in Claim for a Combination. – An element in a claim for a combination may be expressed as a means or step for performing a specified function without the recital of structure, material, or acts in support thereof, and such claim shall be construed to cover the corresponding structure, material, or acts described in the specification and equivalents thereof.
The following is a quotation of pre-AIA 35 U.S.C. 112, sixth paragraph:
An element in a claim for a combination may be expressed as a means or step for performing a specified function without the recital of structure, material, or acts in support thereof, and such claim shall be construed to cover the corresponding structure, material, or acts described in the specification and equivalents thereof.
Claim 1 recites “electrical conductive means for establishing electrical conduction between said positive electrode and said negative electrode” and “means capable of establishing flow of the electrolyte solutions past said positive and negative electrodes”.
The claims in this application are given their broadest reasonable interpretation using the plain meaning of the claim language in light of the specification as it would be understood by one of ordinary skill in the art. The broadest reasonable interpretation of a claim element (also commonly referred to as a claim limitation) is limited by the description in the specification when 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph, is invoked.
As explained in MPEP § 2181, subsection I, claim limitations that meet the following three-prong test will be interpreted under 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph:
(A) the claim limitation uses the term “means” or “step” or a term used as a substitute for “means” that is a generic placeholder (also called a nonce term or a non-structural term having no specific structural meaning) for performing the claimed function;
(B) the term “means” or “step” or the generic placeholder is modified by functional language, typically, but not always linked by the transition word “for” (e.g., “means for”) or another linking word or phrase, such as “configured to” or “so that”; and
(C) the term “means” or “step” or the generic placeholder is not modified by sufficient structure, material, or acts for performing the claimed function.
Use of the word “means” (or “step”) in a claim with functional language creates a rebuttable presumption that the claim limitation is to be treated in accordance with 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph. The presumption that the claim limitation is interpreted under 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph, is rebutted when the claim limitation recites sufficient structure, material, or acts to entirely perform the recited function.
Absence of the word “means” (or “step”) in a claim creates a rebuttable presumption that the claim limitation is not to be treated in accordance with 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph. The presumption that the claim limitation is not interpreted under 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph, is rebutted when the claim limitation recites function without reciting sufficient structure, material or acts to entirely perform the recited function.
Claim limitations in this application that use the word “means” (or “step”) are being interpreted under 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph, except as otherwise indicated in an Office action. Conversely, claim limitations in this application that do not use the word “means” (or “step”) are not being interpreted under 35 U.S.C. 112(f) or pre-AIA 35 U.S.C. 112, sixth paragraph, except as otherwise indicated in an Office action.
Applicant’s specification states “The redox flow battery, according to the present invention, comprises electrical conductive means for establishing electrical conduction between said positive electrode and said negative electrode in order to permit the redox flow battery, according to the present invention, to be charged and discharged. In a particular embodiment, the electrical conduction means include wiring means, i.e., the presence of wiring and associated bonding pads and the like sufficient for establishing electrical conduction. However, the electrical conductive means for establishing electrical conduction do not necessarily have to be in the form of wiring” (Page 5).
Therefore the “electrical conductive means for establishing electrical conduction between said positive electrode and said negative electrode” is being interpreted by the examiner as wiring or other structures sufficient for establishing electrical conduction.
Applicant’s specification states “Further, the redox flow battery also comprises means capable of (i.e., having design features for) establishing flow of the first aqueous-based electrolyte solution and the second aqueous-based electrolyte solution past, or through, said positive and negative electrodes, respectively. Such means may e.g. be a pump or other means resulting in a flow or pressure difference” (Page 3).
Therefore the “means capable of establishing flow of the electrolyte solutions past said positive and negative electrodes” is being interpreted by the examiner as a pump or other means resulting in a flow or pressure difference.
Claim 1 recites “wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt”.
Applicant’s specification states “When stating that at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt, the first and/or second aqueous-based electrolytes is formed from the ammonium-based salt, or comprises the ammonium-based salt” (Page 5).
Therefore, this description from Applicant is what the Examiner bases the interpretation of “wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt” on.
Claim 1 recites “a naphthalene diimide (NDI) or a modified NDI”.
Page 27 of Applicant’s specification shows the following figure:
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Pages 40 and 41 of Applicant’s specification states “The four different redox flow batteries were assembled according to table 4 below. For all four redox flow batteries, the negative electrolyte was based on NDI (denoted NDI-1) or modified NDI (denoted NDI-2) in a potassium chloride (KCI) - potassium phosphate (KPh) solution or NDI-1 and NDI-2 in an ammonium chloride (AmCI) - ammonium phosphate (AmPh) solution, while the positive electrolyte was based on BTMAP-Fc in a KCI-KPh solution and BTMAP-Fc in an AmCI-AmPh solution”, and “NDI-1 had the specific formula: 2,7-bis(3- (dimethylamino)propyl)benzo[Imn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone and NDI-2 had the specific formula: 4,9-bis(dimethylamino)-2,7-bis(3- (dimethylamino)propyl)benzo[Imn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone”.
From Applicant’s specification, it appears Applicant’s term “a naphthalene diimide (NDI)” refers to a naphthalene diimide compound that can have modifications/functionalization on the nitrogen, but not on the core rings of the naphthalene, and “a modified NDI” refers to a naphthalene diimide compound that can have modifications of substituents onto the rings of the naphthalene (given the compounds noted “NDI” on Page 27 includes modifications to the nitrogen, “NDI-1”, referred to as NDI, is a compound including modifications to the nitrogen, and NDI-2, referred to as a modified NDI, is a compound that is core-functionalized).
Further, prior art, such as Kobaisi et al (Functional Naphthalene Diimides: Synthesis, Properties, and Applications), notes a NDI as being able to include a hydrogen, alkyl, or aryl to the nitrogen (see 1 in the figure below) and a cNDI as a compound able to include R-groups attached to the rings of the naphthalene (see 4 in the figure below).
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Therefore, the term “a naphthalene diimide (NDI)” in the claims is being interpreted as a naphthalene diimide compound that has modifications/functionalization on the nitrogen, but not on the core rings of the naphthalene, and the term “a modified NDI” is being interpreted as a naphthalene diimide compound that can have modifications of substituents onto the core rings of the naphthalene.
Claim Objections
Claims 10 and 14 are objected to because of the following informalities:
Claim 10 recites the limitation “wherein at least one of R2, R3, R5 and R6 is a group or molecule comprising more than a hydrogen atom, or is different to a hydrogen atom, or wherein at least one of R2, R3, R5 and R6 is an amino or cyano group”. The phrase “different to” is grammatically incorrect.
Claim 14 states “firsr” when it should state “first”.
Appropriate correction is required.
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.
Claim 8, thus claims 9-10, 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 8, the claims sets forth a formula for “the modified NDI”. However, as set forth in the claim interpretation sections above, the term “a naphthalene diimide (NDI)” in the claims is being interpreted as a naphthalene diimide compound that has modifications/functionalization on the nitrogen, but not on the core rings of the naphthalene, and the term “a modified NDI” is being interpreted as a naphthalene diimide compound that can have modifications of substituents onto the core rings of the naphthalene.
Claim 8 is rendered indefinite because the formula I provided for “the modified NDI” reads on naphthalene diimide structures that do not require modifications of substituents onto the core rings of the naphthalene.
For example, Applicant’s own structure noted as “NDI” on Page 27 of the specification (see figure provided below) is able to be met by the formula set forth in claim 8. In this case, the NDI (for example, the middle NDI set forth in the figure below) would meet formula I wherein R1 is group R7, being a hydrocarbyl group having one to twenty carbon atoms, and being substituted by one, two, or three substituents selected from: - amino group -NR8R9R10, wherein R10 is present when the amino group is quaternized, and wherein R8, R9 and R10, if R10 present, are independently selected from hydrogen atom and hydrocarbyl group R11 having one to six carbon atoms, or R8 and R9 forming together with the nitrogen, or together with the nitrogen and a further nitrogen in either of R8 or R9, a hetero ring having four to six carbon atoms.
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Since claims 9-10 depend from claim 8, they are rejected for the same reasons.
Regarding claim 10, claim 10 recites “wherein at least one of R2, R3, R5 and R6 is a group or molecule comprising more than a hydrogen atom, or is different to a hydrogen atom, or wherein at least one of R2, R3, R5 and R6 is an amino or cyano group”.
It is not clear what “more than a hydrogen atom” means. Does the phrase mean the R-groups are a hydrogen atom alongside another element/group? It is unclear what “more” means.
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, 6-13, 15, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1).
Regarding claim 1, Nuckolls discloses a redox flow battery (redox flow battery; see entire disclosure and especially P13, 57, 62, 64) comprising:
a positive compartment comprising a positive electrode in contact with a first electrolyte solution comprising a positive electrolyte dissolved in a first solvent (cathode cell 2 including a catholyte 21 and a cathode 42 in Fig. 6A, P64; see also entire disclosure and especially P8, 12, 56, 60, 64, 81),
a negative compartment comprising a negative electrode in contact with a second electrolyte solution comprising a negative electrolyte dissolved in a second solvent (anode cell 1 including an anolyte 11 and an anode 41 in Fig. 6A, P64; see also entire disclosure and especially P8-9, 12, 56, 60, 64, 81)
electrical conductive means for establishing electrical conduction between said positive electrode and said negative electrode, and an external load for directing electrical energy into or out of the redox flow battery (see Fig. 6A wherein the cathode 42 and anode 41 are connected to a load source (drawn to the claimed external load; while Nuckolls does not explicitly state ‘electrical conductive means’, given the cathode and anode are connected to a load source, it is inherent that some structure sufficient for establishing electrical conduction is utilized to establish electrical conduction between the cathode and anode);
a separator component that separates the first electrolyte solution in the positive compartment from the second electrolyte solution in the negative compartment and substantially prevents the positive electrolyte in the positive compartment and the negative electrolyte in the negative compartment from intermingling with each other, while permitting the passage of non-redox-active species between the electrolyte solutions in the positive and negative compartments (“The ion exchange membrane 10 prevents ions of active materials of the catholyte 11 and the anolyte 12 from being mixed with each other and permits only ions of a charge carrier of a supporting electrolyte to be transferred”, P64; see Fig. 6A); and
means capable of establishing flow of the electrolyte solutions past said positive and negative electrodes, respectively (“The anolyte 11 and the catholyte 21 respectively circulate through pumps 31 and 32”, P64; see Fig. 6A).
Regarding the first electrolyte solution being a first aqueous-based electrolyte solution wherein the positive electrolyte is dissolved in a first aqueous-based solvent and the second electrolyte solution being a second aqueous-based electrolyte solution wherein the negative electrolyte is dissolved in a second aqueous-based solvent:
Nuckolls discloses the redox flow battery can be an aqueous redox flow battery (P57). Nuckolls discloses the catholyte and anolyte can include an electrolyte solution as set forth in Nuckols’s disclosure (P13). Nuckolls discloses an electrolyte solution can include a solvent and an electrolyte wherein the electrolyte is soluble in the solvent (P8). Nuckolls discloses the solvent can be an aqueous solvent (P12). Nuckolls discloses the catholyte can include a ferrocene derivative or a cyclopropenium compound (P60, 64, 81). Nuckolls discloses the anolyte can include triethylammonium tail naphthalene diimide (P9, 56, 60, 81-82).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have selected the redox flow battery of Nuckolls to be an aqueous redox flow battery, selected the materials forming the first electrolyte solution (catholyte) to be a positive electrolyte of a ferrocene derivative or cyclopropenium compound dissolved in an aqueous solvent, and selected the materials forming the second electrolyte solution (anolyte) to be a negative electrolyte of triethylammonium tail naphthalene diimide dissolved in an aqueous solvent, given Nuckolls discloses their redox flow battery can be an aqueous redox flow battery, Nuckolls discloses their electrolyte solutions can be used for a catholyte and anolyte, Nuckolls teaches a catholyte can include a ferrocene derivative or a cyclopropenium compound, Nuckolls teaches an anolyte can include triethylammonium tail naphthalene diimide, and the selection of known materials, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the art. See In re Leshin, 125 USPQ 416 (CCPA 1960) (see MPEP § 2144.07).
From this modification, modified Nuckolls would further meet the limitations wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt (given triethylammonium tail naphthalene diimide (NDI) is an ammonium-based salt, therefore, the second aqueous-based electrolyte is based on an ammonium-based salt) and wherein the negative electrolyte is an organic redox-active molecule, wherein the organic redox-active molecule is a naphthalene diimide (NDI) (given triethylammonium tail naphthalene diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
Regarding claims 6-10 and 21, the claims further limit the modified NDI, however, these claims do not require that the modified NDI is the organic redox-active molecule provided in the redox flow battery. Therefore, given the organic redox-active molecule of modified Nuckolls can be chosen to be “a naphthalene diimide (NDI)” (rather than “a modified NDI”) as set forth in claim 1 above, from which claims 6-10 and 21 depends, these claims are not required to be met by modified Nuckolls.
The Examiner wishes to note, in view of the 112b of claim 8 above, the triethylammonium tail naphthalene diimide of modified Nuckolls would meet the structure according to formula I in claim 8.
Regarding claims 11-13, modified Nuckolls meets the limitations wherein the battery is configured such that the NDI, or modified NDI, is reduced with two electrons in the negative compartment, creating an NDI dianion or hydroNDl (claim 11), wherein the NDI dianon or reduced NDI is an original reduced NDI having a first structure, and wherein the battery is configured such that the original reduced NDI is restructured into a restructured reduced NDI having a second structure different from said first structure, the restructured reduced NDI having a different reduction potential compared to the original reduced NDI (claim 12), and wherein the difference in reduction potential between the original reduced NDI and the restructured reduced NDI determines the voltage of the battery (claim 13), given the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 1 (is substantially identical to) and the NDI is triethylammonium tail naphthalene diimide (NDI). Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Regarding claim 15, modified Nuckolls meets the limitations wherein a pH of at least one of the first and second aqueous-based electrolyte solutions is adjusted during cycling due to the proton-coupled electron transfer of the NDI or the modified NDI, given the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 1 (is substantially identical to) and the NDI is triethylammonium tail naphthalene diimide (NDI). Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Claims 2-3 are rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) as applied to claim 1, further in view of Liu et al (US 20180072669 A1).
Regarding claim 2, Nuckolls discloses the catholyte (positive electrolyte) can include a ferrocene derivative or a cyclopropenium compound (P60, 64, 81). However, modified Nuckolls does not meet the limitation wherein the ammonium-based salt comprises at least one of the following: ammonium chloride, ammonium phosphate.
In a similar field of endeavor, Liu teaches an aqueous organic redox flow battery (AORFB) (P13). Liu teaches (ferrocenylmethyl)trimethylammonium chloride (FcNCl) being used within an AORFB as a redox active material (P14, 105). Liu teaches fast electrochemical kinetic results indicate that FcNCL may be a useful redox active material in AORFBs (P235).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Liu and selected the material of the positive electrolyte (catholyte) of modified Nuckolls to be (ferrocenylmethyl)trimethylammonium chloride (FcNCl), given Liu teaches these as a material to be used within an AORFB as a useful redox active material and the selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the art. See In re Leshin, 125 USPQ 416 (CCPA 1960) (see MPEP § 2144.07).
From this modification, modified Nuckolls would meet the limitations wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt wherein the ammonium-based salt comprises at least ammonium chloride (given (ferrocenylmethyl)trimethylammonium chloride (FcNCl) is provided within the first aqueous-based electrolyte).
Regarding claim 3, Nuckolls discloses the catholyte (positive electrolyte) can include a ferrocene derivative or a cyclopropenium compound (P60, 64, 81). However, modified Nuckolls does not meet the limitation wherein the other one of the first and second aqueous-based electrolytes is based on an ammonium salt.
In a similar field of endeavor, Liu teaches an aqueous organic redox flow battery (AORFB) (P13). Liu teaches (ferrocenylmethyl)trimethylammonium chloride (FcNCl) being used within an AORFB as a redox active material (P14, 105). Liu teaches fast electrochemical kinetic results indicate that FcNCL may be a useful redox active material in AORFBs (P235).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Liu and selected the material of the positive electrolyte (catholyte) of modified Nuckolls to be (ferrocenylmethyl)trimethylammonium chloride (FcNCl), given Liu teaches these as a material to be used within an AORFB as a useful redox active material and the selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the art. See In re Leshin, 125 USPQ 416 (CCPA 1960) (see MPEP § 2144.07).
From this modification, modified Nuckolls would meet the limitations wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt and wherein the first aqueous-based electrolyte is based on an ammonium salt (given (ferrocenylmethyl)trimethylammonium chloride (FcNCl) is provided within the first aqueous-based electrolyte).
Claims 5-6, 8, 10, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) as applied to claim 1, further in view of Vadehra et al (Naphthalene Diimide Based Materials with Adjustable Redox Potentials: Evaluation for Organic Lithium-Ion Batteries).
Regarding claim 5, modified Nuckolls meets the limitation wherein the second aqueous-based electrolyte solution comprises the organic redox-active molecule of a naphthalene diimide (NDI), which can be considered a first organic redox-active molecule (given triethylammonium tail naphthalene diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
However, modified Nuckolls does not meet the limitation wherein the second aqueous-based electrolyte solution comprises at least two different organic redox-active molecules dissolved in the second aqueous-based solvent, wherein a second organic redox-active molecule being a modified NDI is provided alongside the first organic redox-active molecule.
Vadehra teaches the promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries (Abstract).
Vadehra teaches naphthalene diimides (NDIs) with different aromatic (X) and imide (R) substituents (Page 7152). Vadehra teaches the core can include hydrogen, NMe2, F, and CN substituents (see Fig. 1 on Page 7152). Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties (Page 7156, Right Column).
Vadehra teaches all samples of the core-modified NDIs created in their study exhibited two redox waves and could be reversibly cycled (Page 7154, Left Column). Vadehra teaches aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight (Page 7157, Left Column).
Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials. Therefore, while Vadehra mentions the use of their core-modified NDIs as electrode materials, one of ordinary skill in the art would recognize/understand these core-modified NDIs could also be utilized as anolyte materials. Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, F.).
Furthermore, it would be obvious to one of ordinary skill in the art to try to use these core-modified NDIs as anolyte materials, given Nuckolls already teaches the use of naphthalene diimides and their derivatives as use as anolyte materials and Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties. The Supreme Court decided that a claim can be proved obvious merely by showing that the combination of known elements was obvious to try. In this regard, the Supreme Court explained that, “[w]hen there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill in the art has a good reason to pursue the known options within his or her technical grasp.” An obviousness determination is not the result of a rigid formula disassociated from the consideration of the facts of the case. Indeed, the common sense of those skilled in the art demonstrates why some combinations would have been obvious where others would not. Therefore, choosing from a finite number of identified, predictable solutions, with a reasonable expectation for success, is likely to be obvious to a person if ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, E.).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Vadehra and provided, alongside the first organic redox-active molecule, a second organic redox-active molecule of a modified NDI, such as the modified NDIs as taught by Vadehra, given Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials, Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties, and Vadehra teaches core-modified NDIs wherein the aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight.
Regarding claim 6, modified Nuckolls does not meet the limitation wherein the modified NDI is a substituted NDI (given triethylammonium tail naphthalene diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
Vadehra teaches the promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries (Abstract).
Vadehra teaches naphthalene diimides (NDIs) with different aromatic (X) and imide (R) substituents (Page 7152). Vadehra teaches the core can include hydrogen, NMe2, F, and CN substituents (see Fig. 1 on Page 7152). Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties (Page 7156, Right Column).
Vadehra teaches all samples of the core-modified NDIs created in their study exhibited two redox waves and could be reversibly cycled (Page 7154, Left Column). Vadehra teaches aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight (Page 7157, Left Column).
Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials. Therefore, while Vadehra mentions the use of their core-modified NDIs as electrode materials, one of ordinary skill in the art would recognize/understand these core-modified NDIs could also be utilized as anolyte materials. Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, F.).
Furthermore, it would be obvious to one of ordinary skill in the art to try to use these core-modified NDIs as anolyte materials, given Nuckolls already teaches the use of naphthalene diimides and their derivatives as use as anolyte materials and Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties. The Supreme Court decided that a claim can be proved obvious merely by showing that the combination of known elements was obvious to try. In this regard, the Supreme Court explained that, “[w]hen there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill in the art has a good reason to pursue the known options within his or her technical grasp.” An obviousness determination is not the result of a rigid formula disassociated from the consideration of the facts of the case. Indeed, the common sense of those skilled in the art demonstrates why some combinations would have been obvious where others would not. Therefore, choosing from a finite number of identified, predictable solutions, with a reasonable expectation for success, is likely to be obvious to a person if ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, E.).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Vadehra and substituted the NDI of modified Nuckolls with a modified NDI, such as the modified NDIs as taught by Vadehra, given Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials, Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties, Vadehra teaches core-modified NDIs wherein the aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight, and the simple substitution of one known element for another is likely to be obvious when predictable results are achieved. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, B.).
Regarding claim 7, modified Nuckolls meets the limitation wherein the modified NDI comprises an amino group (if the aryl substitution of the modified NDI of Vadehra is NMe2).
Regarding claims 8 and 10, modified Nuckolls does not meet the limitation wherein the modified NDI has a structure according to the claimed formula I (given triethylammonium tail naphthalene diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
Vadehra teaches the promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries (Abstract).
Vadehra teaches naphthalene diimides (NDIs) with different aromatic (X) and imide (R) substituents (Page 7152). Vadehra teaches the core can include hydrogen, NMe2, F, and CN substituents (see Fig. 1 on Page 7152). Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties (Page 7156, Right Column). Vadehra teaches the compounds as shown in Fig. 1 below:
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Vadehra teaches all samples of the core-modified NDIs created in their study exhibited two redox waves and could be reversibly cycled (Page 7154, Left Column). Vadehra teaches aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight (Page 7157, Left Column).
Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials. Therefore, while Vadehra mentions the use of their core-modified NDIs as electrode materials, one of ordinary skill in the art would recognize/understand these core-modified NDIs could also be utilized as anolyte materials. Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, F.).
Furthermore, it would be obvious to one of ordinary skill in the art to try to use these core-modified NDIs as anolyte materials, given Nuckolls already teaches the use of naphthalene diimides and their derivatives as use as anolyte materials and Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties. The Supreme Court decided that a claim can be proved obvious merely by showing that the combination of known elements was obvious to try. In this regard, the Supreme Court explained that, “[w]hen there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill in the art has a good reason to pursue the known options within his or her technical grasp.” An obviousness determination is not the result of a rigid formula disassociated from the consideration of the facts of the case. Indeed, the common sense of those skilled in the art demonstrates why some combinations would have been obvious where others would not. Therefore, choosing from a finite number of identified, predictable solutions, with a reasonable expectation for success, is likely to be obvious to a person if ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, E.).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Vadehra and substituted the NDI of modified Nuckolls with a modified NDI, such as the modified NDIs as taught by Vadehra, given Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials, Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties, Vadehra teaches core-modified NDIs wherein the aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight, and the simple substitution of one known element for another is likely to be obvious when predictable results are achieved. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, B.).
If the modified NDI from Vadehra used in modified Nuckolls is chosen to be compound 13 from Vadehra Fig. 1, modified Nuckolls meets the limitations of formula I in claim 8 wherein R1, R2, R4 and R5 are hydrogen atoms and R3 and R6 are cyano groups. Since R3 and R6 are cyano groups, they are different to a hydrogen atom, as set forth in claim 10.
Regarding claim 21, modified Nuckolls does not meet the limitation wherein the modified NDI is a core-aminated NDI (given triethylammonium tail naphthalene diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
Vadehra teaches the promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries (Abstract).
Vadehra teaches naphthalene diimides (NDIs) with different aromatic (X) and imide (R) substituents (Page 7152). Vadehra teaches the core can include hydrogen, NMe2, F, and CN substituents (see Fig. 1 on Page 7152). Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties (Page 7156, Right Column).
Vadehra teaches all samples of the core-modified NDIs created in their study exhibited two redox waves and could be reversibly cycled (Page 7154, Left Column). Vadehra teaches aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight (Page 7157, Left Column).
Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials. Therefore, while Vadehra mentions the use of their core-modified NDIs as electrode materials, one of ordinary skill in the art would recognize/understand these core-modified NDIs could also be utilized as anolyte materials. Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, F.).
Furthermore, it would be obvious to one of ordinary skill in the art to try to use these core-modified NDIs as anolyte materials, given Nuckolls already teaches the use of naphthalene diimides and their derivatives as use as anolyte materials and Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties. The Supreme Court decided that a claim can be proved obvious merely by showing that the combination of known elements was obvious to try. In this regard, the Supreme Court explained that, “[w]hen there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill in the art has a good reason to pursue the known options within his or her technical grasp.” An obviousness determination is not the result of a rigid formula disassociated from the consideration of the facts of the case. Indeed, the common sense of those skilled in the art demonstrates why some combinations would have been obvious where others would not. Therefore, choosing from a finite number of identified, predictable solutions, with a reasonable expectation for success, is likely to be obvious to a person if ordinary skill in the art. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, E.).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Vadehra and substituted the NDI of modified Nuckolls with a modified NDI, such as the modified NDIs as taught by Vadehra, given Nuckolls already discloses the use of naphthalene diimides and their derivatives as use as anolyte materials, Vadehra teaches aryl-substitution can control cycling performance and redox potential by influencing solubility and electronic properties, Vadehra teaches core-modified NDIs wherein the aryl substitution with CN, F, and Me2N groups allows the redox potential of the NDIs to be tailored between 2.9 and 2.3 V vs Li/Li+ without significantly affecting the solubility or molecular weight, and the simple substitution of one known element for another is likely to be obvious when predictable results are achieved. See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, B.).
If the modified NDI from Vadehra used in modified Nuckolls is chosen to be compound 13 from Vadehra Fig. 1, the aryl substitution includes a NMe2 substituent, and therefore, the modified NDI can be considered a core-aminated NDI.
Claims 3, 16-17, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) as applied to claim 1, further in view of Potash et al (On the Benefits of a Symmetric Redox Flow Battery).
Regarding claim 3, modified Nuckolls does not meet the limitation wherein the other one of the first and second aqueous-based electrolytes is based on an ammonium salt.
In similar field of endeavor, Potash teaches “There are several clear practical benefits to using a symmetric RFB electrolyte. The most significant benefit is that physical crossover of electro-active species does not result in mixing of disparate chemical compounds. This feature dramatically simplifies charge rebalancing from electrolyte crossover, since it does not require chemical separations. An SRFB has an additional benefit, however, in that there exists neither chemical nor electrical potential gradients between the negative and positive electrolyte chambers in the discharged state, and so the driving force for mixing or adventitious side-reactions is negligible. This implies that a discharged SRFB cell could be stored indefinitely without degradation” (Page A340 Left Column under “Definition, Properties, and Advantages of the SRFB”).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Potash and modified the redox flow battery of modified Nuckolls to be a symmetrical redox flow battery by utilizing the triethylammonium tail naphthalene diimide in both the anolyte and catholyte, such that both the first and second aqueous-based electrolytes is based on an ammonium salt (the triethylammonium tail naphthalene diimide), given Potash teaches symmetrical redox flow batteries simplifies charge rebalancing from electrolyte crossover and has the potential to be stored indefinitely without degradation.
Regarding claim 16, modified Nuckolls does not meet the limitation wherein the positive electrolyte is the same as the negative electrolyte, forming a symmetrical redox flow battery.
In similar field of endeavor, Potash teaches “There are several clear practical benefits to using a symmetric RFB electrolyte. The most significant benefit is that physical crossover of electro-active species does not result in mixing of disparate chemical compounds. This feature dramatically simplifies charge rebalancing from electrolyte crossover, since it does not require chemical separations. An SRFB has an additional benefit, however, in that there exists neither chemical nor electrical potential gradients between the negative and positive electrolyte chambers in the discharged state, and so the driving force for mixing or adventitious side-reactions is negligible. This implies that a discharged SRFB cell could be stored indefinitely without degradation” (Page A340 Left Column under “Definition, Properties, and Advantages of the SRFB”).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Potash and modified the redox flow battery of modified Nuckolls to be a symmetrical redox flow battery as claimed, such as by utilizing the triethylammonium tail naphthalene diimide in both the anolyte and catholyte, given Potash teaches symmetrical redox flow batteries simplifies charge rebalancing from electrolyte crossover and has the potential to be stored indefinitely without degradation.
Regarding claim 17, modified Nuckolls meets the limitations wherein the battery is configured such that the NDI, or modified NDI, is reduced with two electrons in the negative compartment, creating an NDI dianion or hydroNDl, wherein the NDI dianon or reduced NDI is an original reduced NDI having a first structure, and wherein the battery is configured such that the original reduced NDI is restructured into a restructured reduced NDI having a second structure different from said first structure, the restructured reduced NDI having a different reduction potential compared to the original reduced NDI, and wherein charging of the battery results in the following reactions: - in the negative compartment: NDI + 2e- + ND12- and ND12-+ NDI*2- or NDI + 2e- + 2H++ NDIH2 and NDIH2+ NDIH2*, wherein NDI*2- and NDIH2* are forms of the restructured reduced NDI; - in the positive compartment: NDI*2-+ NDI* + 2e- and NDI* + NDI or NDIH2* + NDI* + 2e- + 2H+ and NDI* + NDI, wherein NDI* is the oxidised condition of the restructured reduced NDI, given the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 16 (is substantially identical to) and the NDI is triethylammonium tail naphthalene diimide (NDI). Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Regarding claim 20, modified Nuckolls does not meet the limitation wherein both of the first and second aqueous-based electrolytes are based on a same ammonium-based salt.
In similar field of endeavor, Potash teaches “There are several clear practical benefits to using a symmetric RFB electrolyte. The most significant benefit is that physical crossover of electro-active species does not result in mixing of disparate chemical compounds. This feature dramatically simplifies charge rebalancing from electrolyte crossover, since it does not require chemical separations. An SRFB has an additional benefit, however, in that there exists neither chemical nor electrical potential gradients between the negative and positive electrolyte chambers in the discharged state, and so the driving force for mixing or adventitious side-reactions is negligible. This implies that a discharged SRFB cell could be stored indefinitely without degradation” (Page A340 Left Column under “Definition, Properties, and Advantages of the SRFB”).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Potash and modified the redox flow battery of modified Nuckolls to be a symmetrical redox flow battery by utilizing the triethylammonium tail naphthalene diimide in both the anolyte and catholyte, thereby providing wherein both of the first and second aqueous-based electrolytes are based on a same ammonium-based salt, given Potash teaches symmetrical redox flow batteries simplifies charge rebalancing from electrolyte crossover and has the potential to be stored indefinitely without degradation.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) in view of Potash et al (On the Benefits of a Symmetric Redox Flow Battery) as applied to claim 16, further in view of Wiberg et al (Electrochemical Evaluation of a Napthalene Diimide Derivative for Potential Application in Aqueous Organic Redox Flow Batteries; showing a “First Published” date of 06 August 2019 on Page 1).
Regarding claim 17, modified Nuckolls includes the catholyte (positive electrolyte) and anolyte (negative electrolyte) can include a derivative of naphthalene diimide (see the rejection of claim 16 above).
In a similar field of endeavor, Wiberg teaches a quaternary amine-functionalized naphthalene diimide (NDI) moiety is synthesized and considered as a redox-active species for application in aqueous organic redox flow batteries (Abstract, Page 1). Wiberg teaches the molecule reaches a solubility of 0.68 M in water and reversibly delivers two electrons at attractive potentials for flow battery applications (Abstract, Page 1).
Wiberg teaches to make NDI water-soluble at higher pH, the material was dissolved in chloroform through which chloromethane was bubbled, after which the pure NDI with quaternary amine sidechains precipitated out of solution (Results and Discussion, Page 3).
Wiberg teaches the synthesis of N,N′-Bis-[(3-Dimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide, then teaches five grams of this material is dissolved in 100 mL of chloroform through which excess chloromethane was bubbled (Experimental Section, Pages 14-15). Wiberg teaches material started precipitating after 30 min of stirring, and the solution was left at room temperature overnight before the mixture was filtered and dried, affording a quantitative amount of the off-white product of N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide (Experimental Section, Pages 14-15).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Wiberg and substituted the positive electrolyte (catholyte) and negative electrolyte (anolyte) of modified Nuckolls with N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide or selected the material of the positive electrolyte (catholyte) and negative electrolyte (anolyte) of modified Nuckolls to be N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide, given Wiberg teaches this material as a quaternary amine-functionalized naphthalene diimide (NDI) moiety considered as a redox-active species for application in aqueous organic redox flow batteries, the simple substitution of one known element for another is likely to be obvious when predictable results are achieved (See KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) (see MPEP § 2143, B.)), and the selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the art (See In re Leshin, 125 USPQ 416 (CCPA 1960) (see MPEP § 2144.07)).
Therefore, modified Nuckolls meets the limitations wherein the battery is configured such that the NDI, or modified NDI, is reduced with two electrons in the negative compartment, creating an NDI dianion or hydroNDl, wherein the NDI dianon or reduced NDI is an original reduced NDI having a first structure, and wherein the battery is configured such that the original reduced NDI is restructured into a restructured reduced NDI having a second structure different from said first structure, the restructured reduced NDI having a different reduction potential compared to the original reduced NDI, and wherein charging of the battery results in the following reactions: - in the negative compartment: NDI + 2e- + ND12- and ND12-+ NDI*2- or NDI + 2e- + 2H++ NDIH2 and NDIH2+ NDIH2*, wherein NDI*2- and NDIH2* are forms of the restructured reduced NDI; - in the positive compartment: NDI*2-+ NDI* + 2e- and NDI* + NDI or NDIH2* + NDI* + 2e- + 2H+ and NDI* + NDI, wherein NDI* is the oxidised condition of the restructured reduced NDI, given Wiberg teaches their material reversibly delivers two electrons at attractive potentials for flow battery applications, the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 16 (is substantially identical to), and the NDI is N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide. Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Claims 1, 4, 6-13, 15, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) in view of Wiberg et al (Electrochemical Evaluation of a Napthalene Diimide Derivative for Potential Application in Aqueous Organic Redox Flow Batteries; showing a “First Published” date of 06 August 2019 on Page 1).
Regarding claim 1, Nuckolls discloses a redox flow battery (redox flow battery; see entire disclosure and especially P13, 57, 62, 64) comprising:
a positive compartment comprising a positive electrode in contact with a first electrolyte solution comprising a positive electrolyte dissolved in a first solvent (cathode cell 2 including a catholyte 21 and a cathode 42 in Fig. 6A, P64; see also entire disclosure and especially P8, 12, 56, 60, 64, 81),
a negative compartment comprising a negative electrode in contact with a second electrolyte solution comprising a negative electrolyte dissolved in a second solvent (anode cell 1 including an anolyte 11 and an anode 41 in Fig. 6A, P64; see also entire disclosure and especially P8-9, 12, 56, 60, 64, 81)
electrical conductive means for establishing electrical conduction between said positive electrode and said negative electrode, and an external load for directing electrical energy into or out of the redox flow battery (see Fig. 6A wherein the cathode 42 and anode 41 are connected to a load source (drawn to the claimed external load; while Nuckolls does not explicitly state ‘electrical conductive means’, given the cathode and anode are connected to a load source, it is inherent that some structure sufficient for establishing electrical conduction is utilized to establish electrical conduction between the cathode and anode);
a separator component that separates the first electrolyte solution in the positive compartment from the second electrolyte solution in the negative compartment and substantially prevents the positive electrolyte in the positive compartment and the negative electrolyte in the negative compartment from intermingling with each other, while permitting the passage of non-redox-active species between the electrolyte solutions in the positive and negative compartments (“The ion exchange membrane 10 prevents ions of active materials of the catholyte 11 and the anolyte 12 from being mixed with each other and permits only ions of a charge carrier of a supporting electrolyte to be transferred”, P64; see Fig. 6A); and
means capable of establishing flow of the electrolyte solutions past said positive and negative electrodes, respectively (“The anolyte 11 and the catholyte 21 respectively circulate through pumps 31 and 32”, P64; see Fig. 6A).
Regarding the first electrolyte solution being a first aqueous-based electrolyte solution wherein the positive electrolyte is dissolved in a first aqueous-based solvent and the second electrolyte solution being a second aqueous-based electrolyte solution wherein the negative electrolyte is dissolved in a second aqueous-based solvent:
Nuckolls discloses the redox flow battery can be an aqueous redox flow battery (P57). Nuckolls discloses the catholyte and anolyte can include an electrolyte solution as set forth in Nuckolls’s disclosure (P13). Nuckolls discloses an electrolyte solution can include a solvent and an electrolyte wherein the electrolyte is soluble in the solvent (P8). Nuckolls discloses the solvent can be an aqueous solvent (P12). Nuckolls discloses the catholyte can include a ferrocene derivative or a cyclopropenium compound (P60, 64, 81). Nuckolls discloses the anolyte can include a derivative of naphthalene diimide (P9, 56, 60, 81-82).
In a similar field of endeavor, Wiberg teaches a quaternary amine-functionalized naphthalene diimide (NDI) moiety is synthesized and considered as a redox-active species for application in aqueous organic redox flow batteries (Abstract, Page 1). Wiberg teaches the molecule reaches a solubility of 0.68 M in water and reversibly delivers two electrons at attractive potentials for flow battery applications (Abstract, Page 1).
Wiberg teaches to make NDI water-soluble at higher pH, the material was dissolved in chloroform through which chloromethane was bubbled, after which the pure NDI with quaternary amine sidechains precipitated out of solution (Results and Discussion, Page 3).
Wiberg teaches the synthesis of N,N′-Bis-[(3-Dimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide, then teaches five grams of this material is dissolved in 100 mL of chloroform through which excess chloromethane was bubbled (Experimental Section, Pages 14-15). Wiberg teaches material started precipitating after 30 min of stirring, and the solution was left at room temperature overnight before the mixture was filtered and dried, affording a quantitative amount of the off-white product of N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide (Experimental Section, Pages 14-15).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have selected the redox flow battery of Nuckolls to be an aqueous redox flow battery, selected the materials forming the first electrolyte solution (catholyte) to be a positive electrolyte of a ferrocene derivative or cyclopropenium compound dissolved in an aqueous solvent, and selected the materials forming the second electrolyte solution (anolyte) to be a negative electrolyte of N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide dissolved in an aqueous solvent, given Nuckolls discloses their redox flow battery can be an aqueous redox flow battery, Nuckolls discloses their electrolyte solutions can be used for a catholyte and anolyte, Nuckolls teaches a catholyte can include a ferrocene derivative or a cyclopropenium compound, Nuckolls teaches an anolyte can include a derivative of naphthalene diimide, Wiberg teaches N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide as a quaternary amine-functionalized naphthalene diimide (NDI) moiety considered as a redox-active species for application in aqueous organic redox flow batteries, and the selection of known materials, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the art. See In re Leshin, 125 USPQ 416 (CCPA 1960) (see MPEP § 2144.07).
From this modification, modified Nuckolls would further meet the limitations wherein at least one of the first and second aqueous-based electrolytes is based on an ammonium-based salt (given N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide is an ammonium-based salt, therefore, the second aqueous-based electrolyte is based on an ammonium-based salt) and wherein the negative electrolyte is an organic redox-active molecule, wherein the organic redox-active molecule is a naphthalene diimide (NDI) or a modified NDI (given N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide is a NDI that does not have modifications/functionalization on the core rings of the naphthalene; see the claimed interpretation above).
Regarding claim 4, modified Nuckolls includes the anolyte (negative electrolyte) being N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide (see claim 1 above with the modification from Wiberg) and the second aqueous-based solvent being water (see Nuckolls P12, 57).
Therefore, modified Nuckolls meets the limitation wherein the organic redox-active molecule has a solubility at room temperature of at least 0.4 M in the second aqueous-based electrolyte solution (given, Wiberg teaches their molecule reaches a solubility of 0.68 M in water (Abstract, Page 1)).
Regarding claims 6-10 and 21, the claims further limit the modified NDI, however, these claims do not require that the modified NDI is the organic redox-active molecule provided in the redox flow battery. Therefore, given the organic redox-active molecule of modified Nuckolls can be chosen to be “a naphthalene diimide (NDI)” (rather than “a modified NDI”) as set forth in claim 1 above, from which claims 6-10 and 21 depends, these claims are not required to be met by modified Nuckolls.
The Examiner wishes to note, in view of the 112b of claim 8 above, the N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide of modified Nuckolls would meet the structure according to formula I in claims 8-9.
Regarding claims 11-13, Nuckolls discloses the anolyte (negative electrolyte) being N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide (see claim 1 above with the modification from Wiberg).
Therefore, modified Nuckolls meets the limitations wherein the battery is configured such that the NDI, or modified NDI, is reduced with two electrons in the negative compartment, creating an NDI dianion or hydroNDl (claim 11), wherein the NDI dianon or reduced NDI is an original reduced NDI having a first structure, and wherein the battery is configured such that the original reduced NDI is restructured into a restructured reduced NDI having a second structure different from said first structure, the restructured reduced NDI having a different reduction potential compared to the original reduced NDI (claim 12), and wherein the difference in reduction potential between the original reduced NDI and the restructured reduced NDI determines the voltage of the battery (claim 13), given Wiberg teaches their material reversibly delivers two electrons at attractive potentials for flow battery applications, the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 1 (is substantially identical to), and the NDI is N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide. Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Regarding claim 15, modified Nuckolls meets the limitations wherein a pH of at least one of the first and second aqueous-based electrolyte solutions is adjusted during cycling due to the proton-coupled electron transfer of the NDI or the modified NDI, given the redox flow battery of modified Nuckolls meets all of the structural limitations of claim 1 (is substantially identical to) and the NDI is N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide. Regarding product and apparatus claims, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. The Courts have held that it is well settled that where there is a reason to believe that a functional characteristic would be inherent in the prior art, the burden of proof then shifts to the applicant to provide objective evidence to the contrary. See In re Schreiber, 128 F.3d at 1478, 44 USPQ2d at 1478, 44 USPQ2d at 1432 (Fed. Cir. 1997) (see MPEP § 2112.01, I.).
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Nuckolls et al (US 20200259199 A1) in view of Wiberg et al (Electrochemical Evaluation of a Napthalene Diimide Derivative for Potential Application in Aqueous Organic Redox Flow Batteries; showing a “First Published” date of 06 August 2019 on Page 1) as applied to claim 1, further in view of Khataee et al (Differential pH as a method for increasing cell potential in organic aqueous flow batteries).
Regarding claim 14, modified Nuckolls does not meet the limitation wherein the second aqueous-based electrolyte solution has a pH that: (i) is lower than a pH of the first aqueous-based electrolyte solution, and (ii) has a value of at least pH 2.
Khataee teaches in aqueous flow batteries, high battery cell potentials close to the electrochemical window of water are paramount for high cycle efficiency, power and energy density (Abstract). Khataee teaches the standard potential of many organic redox species has a strong dependence of pH and opens the possibility for increasing the cell potential by pH tuning (Abstract).
From the teaching of Khataee, one of ordinary skill in the art would recognize that the pH of the organic redox species used in aqueous flow batteries, and such the pH of the two electrolytes (anolyte and catholyte), are result-effective variables dependent upon the standard potential of the electrolytes and the desired cell potential of the redox flow battery. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have optimized, through routine experimentation, the pH of the first aqueous-based electrolyte solution and the second aqueous-based electrolyte solution in order to reach the desired standard potential of the electrolytes and the desired cell potential of the redox flow battery. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” See In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). The discovery of an optimum value of a known result effective variable, without producing any new or unexpected results, is within the ambit of a person of ordinary skill in the art. See In re Boesch, 205 USPQ 215 (CCPA 1980) (see MPEP § 2144.05, II.).
Furthermore, the catholyte (first aqueous-based electrolyte solution’s positive electrolyte) of modified Nuckolls can be a ferrocene derivative while the anolyte (second aqueous-based electrolyte solution’s negative electrolyte) can be N,N′-Bis-[(3-Trimethylamino)Propyl]-1,4,5,8-Naphthalenetetracarboxylic Acid Diimide (see the rejection of claim 1), similar to Applicant’s own examples utilizing a ferrocene-based positive electrolyte alongside a NDI-based negative electrolyte (Applicant’s specification at Pages 40-42).
In view of Khataee and the similarities between modified Nuckolls and Applicant’s own species being used, one of ordinary skill in the art would expect that because a ferrocene-based catholyte species is used in Nuckolls with the NDI-based anolyte species of Nuckolls, the pH would be optimized and one of ordinary skill in the art would arrive at the claimed invention, i.e. where the anolyte has a lower pH than the catholyte.
Further, regarding the limitation wherein the second aqueous-based electrolyte solution has a pH that has a value of at least pH 2:
Wiberg teaches “Based on the CVs, a pH of 6.4 was chosen for BE, which was considered a good compromise between keeping the reduction potential away from that of the HER while simultaneously avoiding hydrolysis of NDI. However, as the NDI hydrolysis is reversible, cycling at a higher pH might be beneficial to further avoid the HER” (Bulk Electrolysis section, Page 12).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have utilized the teaching of Wiberg and selected/tailored the pH of the second aqueous-based electrolyte solution of modified Nuckolls to be 6.4, given Wiberg teaches a pH of 6.4 is a good comprise between keeping the reduction potential away from that of the HER while simultaneously avoiding hydrolysis of NDI.
Conclusion
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/MARY GRACE HARRIS/Examiner, Art Unit 1729
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