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 Arguments
Applicant's arguments filed 4-6-2026 have been fully considered but they are not persuasive. The rejection of claims 1-3, 9, 10, 12, and 15-20 remain rejected under 35 U.S.C. 103 as being unpatentable over Theiste et al. (US 2020/0050070 A1) because as explained below, Theiste et al. teaches all the possibilities of the specified, specific 16 Formulas claimed in claim 16. Applicant argues that the previous Examiner used Theiste et al. which did not specifically group “R5 and R10” in Group “square”; group R2, R3, R7 and R8 in Group “circle” and group R1, R4, R6 and R9 in Group “triangle” thus does not teach the different groups. The new Examiner disagrees with Applicant’s argument because the reference, Theiste et al. does not have to put the variables in groups but must teach the claimed compound. The previous Examiner wrote a very comprehensive and in-detailed office action. Every element of each compound in every claim has been described in detail. Therefore, the rejection over the claims remains. The rejection of claims 1 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Geigle et al. (US 2023/0095542 A1) has been withdrawn.
Election/Restrictions
Applicant's election with traverse of Species group A: claim 3 and species group B: claim 9 in the reply filed on 11/10/2025 is acknowledged. The traversal is on the grounds that electing a single option from species Grouping A and a single option from Species Grouping B will not allow for the election of a single compound that defines all substituents R1-R10 in paragraph 1-2 of page 2 of Response to Election/Restriction (such as the structure shown on page 4). Applicant notes they are not independent or distinct because they overlap in scope in paragraph 3-4 of page 2.
This is not found persuasive, and the examiner respectfully disagrees because while there may be one compound that can be jointly read on by multiple of the claims, the overlap is so minimal and the species are so broad, that they may be considered distinct. For example, while claims 3 and 4 both share R1, R3, R4, R6, and R9 are hydrogen, R2, R5, R7, R8, and R10 may vary dramatically given the claim limitations. There are hundreds of possible compounds, given the claim limitations of claim 1 that may read on claim 3 and not claim 4 or vice versa. This results in an extensive search burden. This reasoning is consistent between the rest of the species in the traversed species groupings.
Additionally, the species restriction does not limit the claims so that the compound shown on page 4 cannot read on the claims. The restriction between the species is because the differing species claims, that are independent of each other, are so broad and distinct that it creates a significant search burden. The restriction requirement does not limit the scope of the individual species claims because they are independent from each other. If the applicant wishes to limit the scope of the claims to require the specific structure shown on page 4, not just as an optional species within a list, they may amend the elected claims. It is worthwhile to note however that the examiner addressed the structure shown on page 4 of the Response to Election/Restriction in the rejection below. For the above reason, applicant’s argument is not found persuasive. The requirement is still deemed proper and is therefore made FINAL.
Claims 4-8 and 11-14 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected species, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 11-10-2025. Claim 12 now withdrawn and should not have been examined because the claim depends from claim 11 which was withdrawn previously.
Claim Objections
Claim 17 is objected to because of the following informalities: The figures claimed in claim 17 should be labeled as Figures 1-16. Appropriate correction is required.
Claim Rejections - 35 USC § 103
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.
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, 9-10 and 15-20 rejected under 35 U.S.C. 103 as being unpatentable over Theiste et al. (US 2020/0050070 A1). This was cited in the IDS filed 7/6/2025.
Regarding claim 1, Theiste et al. teaches a compound represented by:
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(see e.g.
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in which E may be NR10 in Para. 24)
wherein:
R1, R2, R3, R4, R6, R7, R8, and R9 are each independently H, F, Cl, Br, I,
CF3, CN, OR11, SR11, NO2, alkyl, alkoxy, aryl, heteroaryl, amino, or ammonium, or any two adjacent groups of R3, R4, R8, and R9 may join to form a monocyclic, polycyclic, or heterocyclic group (see e.g. R2-R9 of the Theiste stricture are individually H, F, Cl, Br, I, CF3, CN, OR11, SR11, NO2, alkyl, alkoxy, aryl, heteroaryl, amino, or ammonium, or any two adjacent groups of R2-R9 may join to form a monocyclic, polycyclic, or heterocyclic group in Para. 24. R2-R9 match up to R1-R4 and R6-R9 of the claimed structure);
each R11 is independently H or alkyl (see e.g. R11 is individually H or alkyl
in Para. 24);
R5 and R10 are independently represented by (see e.g. R1 and where E may be NR10 in Para. 24):
-L1-A-L2-OR14 (see e.g. R1 and R10 of any of the compounds
of Theiste et al. may be
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in Para. 25);
each L1 is independently an C1-C8 alkylene group (see e.g. the
(CH2)n, an alkylene by its lack of double bonds and two points of attachment, to the very left of the structure above and also in Para. 25 in which n may be an integer between 1-12, overlapping the claimed range in a prima facie case of obviousness (see MPEP 2144.05));
each L2 is independently an C1-C8 alkylene group (see e.g. the
(CH2)n, an alkylene by its lack of double bonds and two points of attachment, to the right of the N+ in the structure above and also in Para. 25 in which x may be an integer between 1-12, overlapping the claimed range in a prima facie case of obviousness (see MPEP 2144.05));
each R14 is H or alkyl (see e.g. the H after the O to the very right of the structure above and in Para. 25);
A is an ammonium group represented by -N(R15)2+- (see e.g. the N+ in the center of the structure with branching R15 and R16 as shown in the structure above and in Para. 25);
each R15 is alkyl or alkylhydroxyl (see R15 and R16 may be alkyl in Para. 25 and alkyl is defined in the prior art so that it may include a substituent of a hydroxyl group in Para. 9); or
-L3-OR16 (the structure of R5 and R10 has been met by the other species);
each L3 is independently an C1-C8 alkylene group (the structure of R5 and R10 has been met by the other species); and
each R16 is H or alkyl (the structure of R5 and R10 has been met by the other species); and
at least one of R2, R3, R7, and R8 is a sterically hindered group (see e.g. R3, R4, R7, and R8 of the structure of Theiste may individually be an alkyl group in Para. 24 and an alkyl group is defined in the prior art in Para. 10 as including t-butyl, isopropyl, sec-butyl, isopentyl, and neopentyl as well as branched and comprising 1-12 carbons overlapping the claimed structures of isobutyl, 2-ethyl butyl, and 2-ethyl hexyl in a prima face case of obviousness (see MPEP 2144.05) because of the overlapping carbon range. The instant claim 2 defines these as sterically hindered structures).
Regarding claim 2, Theiste et al. teaches wherein the sterically hindered group is selected from tertiary butyl, isobutyl, isopropyl, 2-ethyl butyl, 2-ethyl hexyl, sec-butyl, isopentyl, and neopentyl (see e.g. R3, R4, R7, and R8 of the structure of Theiste may individually be an alkyl group in Para. 24 and an alkyl group is defined in the prior art in Para. 10 as including t-butyl, isopropyl, sec-butyl, isopentyl, and neopentyl as well as branched and comprising 1-12 carbons meeting isobutyl, 2-ethyl butyl, and 2-ethyl hexyl because it overlaps the claimed carbon range in a prima facie case of obviousness (see MPEP 2144.05).
Regarding claim 3, Theiste et al. teaches wherein R1, R3, R4, R6, R8, and R9 are each H (see e.g. R2, R4, R5, R6, R8, and R9 of the structure of Theiste et al. that matches these identified R groups may each be H in Para. 24).
Regarding claim 9, Theiste et al. teaches wherein at least one of R5 and R10 are independently represented by (see e.g. R1 and where E may be NR10 in Para. 24):
-L1-A-L2-OR14 (see e.g. R1 and R10 of any of the compounds
of Theiste et al. may be
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in Para. 25);
each L1 is independently an C1, C2, C3, C4, C5, C6, C7, or C8 alkylene
group (see e.g. the (CH2)n, an alkylene by its lack of double bonds and two points of attachment, to the very left of the structure above and also in Para. 25 in which n may be an integer between 1-12, overlapping the claimed range in a prima facie case of obviousness (see MPEP 2144.05));
each L2 is independently an C1, C2, C3, C4, C5, C6, C7, or C8 alkylene
group (see e.g. the (CH2)n, an alkylene by its lack of double bonds and two points of attachment, to the right of the N+ in the structure above and also in Para. 25 in which x may be an integer between 1-12, overlapping the claimed range in a prima facie case of obviousness (see MPEP 2144.05));
each R14 is H or alkyl (see e.g. the H after the O to the very right of the
structure above and in Para. 25);
A is an ammonium group represented by -N(R15)2+- (see e.g. the N+ in the
center of the structure with branching R15 and R16 as shown in the structure above and in Para. 25); and
each R15 is C1-C8 alkyl or C1-C8 alkylhydroxyl (see R15 and R16 may be
alkyl in Para. 25 and alkyl is defined in the prior art so that it may include a substituent of a hydroxyl group in Para. 9. The alkyl may have up to 20 but typically 12 carbons in Para. 9 which overlaps the claimed ranges in a prima facie case of obviousness (see MPEP 2144.05)).
Regarding claim 10, Theiste et al. teaches:
each L1 is independently an C2 or C4 alkylene group (see e.g. the (CH2)n,
an alkylene by its lack of double bonds and two points of attachment, to the very left of the structure above and also in Para. 25 in which n may be an integer between 1-12, overlapping the claimed values of 2 or 4 in a prima facie case of obviousness (see MPEP 2144.05));
each L2 is independently an C3 alkylene group (see e.g. the (CH2)n, an
alkylene by its lack of double bonds and two points of attachment, to the right of the N+ in the structure above and also in Para. 25 in which x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness (see MPEP 2144.05));;
each R14 is H (see e.g. the H after the O to the very right of the
structure above and in Para. 25);
A is an ammonium group represented by -N(R15)2+- (see e.g. the N+ in the
center of the structure with branching R15 and R16 as shown in the structure above and in Para. 25); and
each R15 is C1 alkyl or C2 alkylhydroxyl (see R15 and R16 may be
alkyl in Para. 25 and alkyl is defined in the prior art so that it may include a substituent of a hydroxyl group in Para. 9. The alkyl may have up to 20 but typically 12 carbons in Para. 9 which overlaps the claimed values of 1 or 2 in a prima facie case of obviousness (see MPEP 2144.05)).
Regarding claim 15, wherein the compound is ammonium salt with an anion (see e.g. for any of the viologens described, the counterion (anion) may be in Para. 22. Considering the viologen anodic material noted in Para. 23-25 is ammonium-based by the N+, of which is a cation, and is described to have an anion, thus making it an ammonium salt because of the anion and cation) comprising F-, Cl-, Br-, I-, BF4-, PF6-, SbF6-, AsF6-, ClO4-, SO3CF3-, N(CF3SO2)2-, C(CF3SO2)3-, N(SO2C2F5)2-, Al(OC(CF3)3)4-, BAr4-, or mixtures of anions thereof (the anion may be F-, Cl-, Br-, I-, BF4-, PF6-, SbF6-, AsF6-, ClO4-, SO3CF3-, N(CF3SO2)2-, C(CF3SO2)3-, N(SO2C2F5)2-, BAr4-, and may be a mixture of those listed in Para. 22), wherein Ar is an aryl or fluorinated aryl group (see e.g. wherein Ar is an aryl or a fluorinated aryl in Para. 22).
Regarding claim 16, Theiste et al. teaches wherein the compound is:
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(Figure 1) when
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in [0024], E may be NR10; R2, R4, R5, R6, R8, and R9 may be H and R3 and R7 may be alkyl. Theiste et. teaches in [0010], that alkyl may be t-butyl. Theiste et al. teaches in [0025] that R1 and R10 of any of the compounds may be
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and that the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH. n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness and x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness. Theiste et al. teaches in [0009], that R15 and R16 may be alkyl and alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Theiste et al. teaches wherein the compound is:
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(Figure 2) when
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in [0024], E may be NR10; R2, R3, R5, R6, R8, and R9 may be H and R4 and R7 may be alkyl. Theiste et al. teaches in [0010], that alkyl may be t-butyl. Theiste et al. teaches in [0025], that R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl. Theiste et al. teaches in [0009], that an alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Theiste et al. teaches wherein the compound may be:
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(Figure 3) when
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in [0024], E may be NR10; R2, R4, R5, R6, R8, and R9 may be H; and R3 and R7 may be alkyl. Theiste et al. teaches that alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl where in [0009], an alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Theiste et al. teaches where the compound may be:
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(Figure 4) when
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in [0024], E may be NR10 in Para. 24. R2, R3, R5, R6, R8, and R9 may be H and R4 and R7 may be alkyl. Theiste et al. teaches in [0010], that alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH. n may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl and in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
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(other species were met by Theiste et al.).
Theiste et al. teaches where the compound may be:
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(Figure 9), when
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in [0024], E may be NR10; R2, R4, R5, R6, R8, and R9 may be H and R3 and R7 may be alkyl and in [0010], alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness and R15 and R16 may be alkyl where in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 2 in a prima facie case of obviousness. Theiste et al. teaches in [0009-0010], that an alkyl may be substituted at any hydrogen bond with a hydroxy group, thus encompassing the claimed structure).
Theiste et al. teaches where the compound may be:
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(Figure 10) when
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in [0024], E may be NR10; R2, R3, R5, R6, R8, and R9 may be H and R4 and R7 may be alkyl wherein in [0010], teaches alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness and R15 and R16 may be alkyl where in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 2 in a prima facie case of obviousness and teaches in [0009-0010], that the alkyl may be substituted at any hydrogen bond with a hydroxy group, thus encompassing the claimed structure.
Theiste et al. teaches where the compound may be:
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(Figure 11) when
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in [0024], E may be NR10; R2, R4, R5, R6, R8, and R9 may be H and R3 and R7 may be alkyl where in [0010], teaches alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness and R15 and R16 may be individually alkyl where in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 and 2 in a prima facie case of obviousness. Theiste et a. teaches in [0009-0010], that the alkyl may be substituted at any hydrogen bond with a hydroxy group, thus encompassing the claimed structure.
Theiste et al. teaches where the compound may be:
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(Figure 12) when
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in [0024], E may be NR10; R2, R3, R5, R6, R8, and R9 may be H and R4 and R7 may be alkyl and in [0010] teaches alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 2 in a prima facie case of obviousness and R15 and R16 may be individually alkyl in in [0009], alkyl is defined as typically having 1-12 carbons, which overlaps the claimed values of 1 and 2 in a prima facie case of obviousness. Theiste et al. teaches that the alkyl may be substituted at any hydrogen bond with a hydroxy group, thus encompassing the claimed structure.
Theiste et al. teaches where the compound may be:
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(Figure 13) when
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in [0024], E may be NR10; R2, R4, R5, R6, R7, R8, and R9 may be H and R3 may be alkyl and teaches in [0010], teaches alkyl may be t-butyl. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl and in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Theiste et al. teaches where the compound may be:
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(Figure 14) when
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in which [0024], E may be NR10; R2, R3, R5, R6, R8, and R9 may be H and R4 and R7 may be individually alkyl and in [0010], teaches alkyl may be t-butyl or a C1-C20 or typically C1-C12 alkyl which overlaps the claimed value of 1 in a prima facie case of obviousness. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl and in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Theiste et al. teaches where the compound may be:
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(Figure 15) when
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in [0024], E may be NR10; R2, R3, R5, R7, R8, and R9 may be H and R4 and R6 may be individually alkyl and in [0010], and in [0010], teaches alkyl may be t-butyl or a C1-C20 or typically C1-C12 alkyl which overlaps the claimed value of 1 in a prima facie case of obviousness. Theiste et al. teaches in [0025], R1 and R10 of any of the compounds may be
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; the CH2 maps to the allylenes shown between the two Ns and the alkylenes between the N+ and OH; n may be an integer between 1-12, overlapping the claimed value of 4 in a prima facie case of obviousness; x may be an integer between 1-12, overlapping the claimed value of 3 in a prima facie case of obviousness and R15 and R16 may be alkyl where in [0009], alkyl is defined as typically having 1-12 carbons which overlaps the claimed value of 1 in a prima facie case of obviousness (see MPEP 2144.05)).
Regarding claim 17, Theiste et al. teaches an energy storage device (see e.g. energy storage device in Para. 18) comprising:
a cathodic material (see e.g. cathodic material in Para. 18); and
an anodic material (see e.g. anodic material in Para. 18);
wherein:
the cathodic material comprises a viologen covalently attached to,
or confined within, a first polymer matrix, the first polymer matrix configured to prevent or minimize substantial diffusion of the cathodic material (see e.g. the cathodic material may be a viologen covalently attached to, or confined within, a first polymer matrix, the first polymer matrix configured to prevent or minimize substantial diffusion of the cathodic material in the activated state in Para. 18); and
the anodic material comprises a phenazine compound (see e.g. the
anodic material is a phenazine in Para. 3 and 23) of claim 1 (see 103 rejection of claim 1 above and Para. 9-10 and 24-25) covalently attached to, or confined within, a second polymer matrix, the second polymer matrix configured to prevent or minimize substantial diffusion of the anodic material (see e.g. covalently attached to, or confined within, the second polymer matrix, the second polymer matrix configured to prevent or minimize substantial diffusion of the anodic material in the activated state in Para. 23).
Regarding claim 18, Theiste et al. teaches an energy storage device (see e.g. energy storage device in Para. 19) comprising:
a first cell comprising an anodic material (see e.g. a first cell including an anodic material in Para. 19);
a second cell comprising a cathodic material (see e.g. a second cell including a cathodic material in Para. 19);
a porous separator isolating the first cell from the second cell (see e.g. a porous separator isolating the first cell from the second cell); and
wherein:
the anodic material comprises the compound of claim 1 (see 103 rejection of claim 1 above and Para. 9-10 and 24-25); and
the cathodic material comprises a viologen (see e.g. the cathodic material may be a viologen in Para. 22).
Regarding claim 19, Theiste et al. teaches further comprising an electrolyte comprising a solvent and a metal salt or an ammonium salt (see e.g. the electrolyte may include a solvent and a salt. The salt may be a metal salt or an ammonium salt in Para. 31).
Regarding claim 20, Theiste et al. teaches wherein the separator comprises an ion exchange membrane or a size-exclusion membrane (see e.g. the separator includes an ion exchange membrane or a size-exclusion membrane in Para. 19).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
US 20150346573 A1 teaches a phenazine compound.
US 20020141032 A1 teaches a phenazine compound.
WO 2020035138 A1 teaches a phenazine compound.
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/LAURA S. WEINER/
Primary Examiner
Art Unit 1723
/Laura Weiner/Primary Examiner, Art Unit 1723