Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Applicant’s election without traverse of Group I and Species A (Claims 1-5, and 12-14) in the reply filed on December 09, 2025 is acknowledged.
Claim 6-11 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on December 09, 2025.
Priority
Acknowledgment is made of applicant’s claim for foreign priority (KR10-2020-0178395, filed on December 18, 2020, KR10-2021-0168178, filed on November 30, 2021) under 35 U.S.C. 119 (a)-(d). Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 5 objected to because of the following informalities:
The phrase “at least one of them being” should be corrected to read “at least one of the segments being” to improve clarity and consistency.
The phrase “x + y + z + m = 1[[)]].” should be corrected to read “wherein x + y + z + m = 1.” to provide proper clause introduction and correct parenthesis formatting.
Appropriate correction is required.
Claim Interpretation
Claim 5 recites: (a) “each of A, B, C and D segments is independently a compound selected from the following formulas”; (b) the segments “may be identical to or different from each other”; and (c) “x, y, z and m are molar ratios in the repeating unit of the polymer ionomer” such that “x + y + z + m = 1”. The specification describes Chemical Formula 1 as a repeating unit having segments A–D selected from listed structures, with the variables x, y, z, and m defining the molar ratios of the selected segments in that repeating unit (Pgs. 12–13). Accordingly, under broadest reasonable interpretation, Claim 5 does not require four distinct segment structures, and one or more of the recited segments may be the same segment structure, and the molar ratio limitation is satisfied where the selected segment structures, including any repetitions among the four labeled positions A, B, C, and D, are present in molar ratios that sum to 1.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determining the scope and contents of the prior art.
Ascertaining the differences between the prior art and the claims at issue.
Resolving the level of ordinary skill in the pertinent art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-4, and 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over YAN et al. (US20190036143A1, hereinafter YAN) in view of WANG et al. (CN106784946A, hereinafter WANG).
Regarding Claim 1, YAN discloses hydroxide exchange polymers capable of forming anion-exchange membranes (AEMs) and ionomers for use in anion exchange membrane fuel cells (¶[0003]).
In particular, a method for preparing a reinforced hydroxide exchange membrane includes wetting a porous substrate, applying a homogeneous solution of a poly(aryl piperidinium) polymer onto the wetted substrate by any known membrane formation technique such as casting, spraying, or doctor knifing, drying, and then exchanging anions with hydroxide ions, and the membrane may be impregnated multiple times by repeating the wetting, applying, and drying steps (¶¶[0069]-[0070]).
A reinforced hydroxide exchange membrane is provided to increase mechanical robustness for stability through wet and dry cycles in a fuel cell, and comprises a porous substrate impregnated with a poly(aryl piperidinium) polymer; suitable porous substrates include PTFE, polypropylene, polyethylene, and poly(ether ketone), and can have a porous microstructure of polymeric fibrils including nodes interconnected by fibrils (¶¶[0076]-[0078]).
However, YAN does not explicitly disclose “a polyfluorene-based anion exchange membrane”.
WANG discloses a cross-linked anion exchange membrane material with cationic functionalized polyfluorene ether nitrile for fuel cells and its preparation method (¶[0002]).
In particular, a polyfluorene ether nitrile polymer containing benzyl bromide (–CH₂Br) groups is dissolved in a solvent to form a solution, reacted with a quaternizing reagent to obtain a cationic functionalized polyfluorene ether nitrile solution, and then a quaternization crosslinking reagent is added before the resulting film-forming solution is spread on a glass substrate, dried, and removed in water to obtain a cationic functionalized polyfluorene ether nitrile crosslinked anion exchange membrane material (¶¶[0024]-[0028]).
Advantageously, the large-volume rigid aromatic ring fluorene group disclosed by WANG increases interchain spacing and provides larger free volume, which is beneficial for water molecule storage and improves ionic conductivity (¶[0030]). In view of YAN’s anion-exchange membranes, a person skilled in the art would incorporate a polyfluorene-based anion exchange membrane material as the impregnating polymer to obtain the stated benefit.
Therefore, it would have been obvious to a person having ordinary skill in the art, prior to the effective filing date of the claimed invention, to incorporate a polyfluorene-based anion exchange membrane material, as disclosed by WANG, into the anion-exchange composite membranes by YAN.
Regarding Claim 2, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses that the porous substrate can comprise polytetrafluoroethylene, polypropylene, or polyethylene (¶[0077]-[0078]).
Regarding Claim 3, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses preparing the reinforced hydroxide exchange membrane by impregnating the porous substrate with the anion exchange polymer solution, optionally repeating the impregnation, to increase the mechanical robustness for stability through the wet and dry cycles, with the porous substrate having the porous microstructure including the nodes interconnected by the fibrils (¶¶[0069]-[0070]; ¶[0076]; ¶[0078]-[0079]).
Although YAN does not explicitly disclose “the porous polymer support has a pore size of 0.01–0.5 μm and a porosity of 50–90%”, these parameters are result-effective variables obtained from routine optimization. In view of YAN’s reinforced-membrane impregnation process and wet/dry-cycle robustness objective, a person having ordinary skill in the art would have optimized the pore size and porosity to achieve predictable impregnation/retention of the polymer within the porous polymer support while maintaining such robustness.
Regarding Claim 4, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses that the porous substrate of the reinforced hydroxide exchange membrane can be polytetrafluoroethylene (PTFE) (¶[0077]), which is a fluorinated porous polymer support.
Regarding Claim 12, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses membrane-electrode assemblies are fabricated by depositing an electrode onto both sides of a membrane and completing the assembly with a gasket, gas diffusion layers, and flow fields (¶[0096]). WANG discloses a cross-linked anion exchange membrane material with cationic functionalized polyfluorene ether nitrile for fuel cells (¶[0002]).
Regarding Claim 13, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses anion/hydroxide exchange membranes for fuel cells (¶¶[0081]-[0084]). WANG discloses a cross-linked anion exchange membrane material with cationic functionalized polyfluorene ether nitrile for fuel cells (¶[0002]).
Regarding Claim 14, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1. YAN discloses that anion/hydroxide exchange membranes can be used in electrolyzers including water electrolyzers, and in electrolysis including H₂/O₂ production (¶[0085]).
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over YAN and WANG as applied to claim 1 above, and further in view of SALMA et al. (Alkaline stability of ether bond free fluorene-based anion exchange polymer containing cycloaliphatic quaternary ammonium groups, Published on July 12, 2020, hereinafter SALMA).
Regarding Claim 5, modified YAN makes obvious the polyfluorene-based anion exchange composite membrane of Claim 1.
YAN discloses that the poly(aryl piperidinium) polymer comprises structural units including a piperidinium quaternary ammonium unit having two R₁₀ substituents and a counter-anion X⁻, an alternative bicyclic quaternary ammonium unit with counter-anion X⁻, a rigid aromatic segment comprising linked aromatic rings with substituents R₇₀–R₁₆₀ and repeat index n, and optionally an aromatic unit bearing a trifluoromethyl substituent and substituents R₂₀–R₆₀ (¶[0055]). WANG discloses polyfluorene-based anion exchange membranes in Example 1 using 9,9-bis(3,5-methyl-4-hydroxyphenyl)fluorene (DMHPF) monomer (¶¶[0043]-[0044]).
However, modified YAN does not explicitly disclose that the polyfluorene-based anion exchange membrane is a polyfluorene-based copolymer ionomer having a repeating unit represented by Chemical Formula 1.
SALMA discloses that a quaternary piperidinium cation is incorporated into an aryl-ether-bond-free fluorene-based polymer via flexible alkyl side chains to synthesize an anion exchange membrane (AEM) (Abstract, Pg. 1).
In Synthesis of monomers and polymers, a facile synthetic procedure is described for synthesizing a piperidinium-functionalized fluorene-based anion exchange membrane (AEM) polymer, including synthesizing poly[(9,9-bis(6ʹ-bromohexyl)fluorene)-co-(9,9-bis(6ʹ-octyl)fluorene)] (PFBr) via Pd-catalyzed Suzuki cross-coupling and converting PFBr to poly[(9,9-bis(6ʹ-(N-methylpiperidinium)hexyl)fluorene)-co-(9,9-bis(6ʹ-octyl)fluorene)]bromide (PF-PipBr) by reacting PFBr with N-methylpiperidine (§ 2.2, § 2.2.1, § 2.2.2, Pg. 2–3).
The PF-PipBr membrane is fabricated by casting a 4 wt% solution of the polymer in DMF onto a clean PTFE sheet, drying, and obtaining a membrane thickness of 70–80 μm, and the PF-PipBr membranes are converted to OH⁻ form by immersion in argon-saturated 1 M NaOH aqueous solution, exchanging the NaOH solution, soaking in argon-saturated DI water, and washing with degassed DI water until neutral pH (§ 2.3, § 2.4, Pg. 3, Col. 1-2).
Advantageously, the N-methylpiperidinium cations incorporated into the polyfluorene backbone via alkyl side chains as disclosed by SALMA provide high alkaline stability and high ionic conductivity (Pg. 2, Col. 2). In view of modified YAN’s anion-exchange composite membrane, a person skilled in the art would incorporate the piperidinium-functionalized fluorene-based anion exchange polymer as the impregnating polymer for the porous polymer support to obtain high alkaline stability and high ionic conductivity.
Regarding the claimed repeating-unit structure with A, B, C, and D segments and molar ratios summing to 1, the fluorene-based anion exchange polymers disclosed by WANG and SALMA include a polyfluorene backbone and cationic functionality, and the overall polymer composition is governed by the relative amounts of the repeating structural motifs. Thus, describing the repeat structure using four labeled segments rather than three does not require a different chemistry in kind, because one of the repeating motifs satisfies more than one of the labeled segment positions A, B, C, and D. The molar ratios of repeating units in any copolymer sum to 1 by definition, and therefore this limitation is satisfied where the copolymer composition is expressed as molar ratios of repeating units.
Therefore, it would have been obvious to a person having ordinary skill in the art, prior to the effective filing date of the claimed invention, to incorporate the piperidinium-functionalized fluorene-based anion exchange polymer, as disclosed by SALMA, into the anion-exchange composite membrane by modified YAN.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAK L. CHIU whose telephone number is (703)756-1059. The examiner can normally be reached M-F: 9:00am - 6:00pm (CST).
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/TAK L. CHIU/Examiner, Art Unit 1777
/KRISHNAN S MENON/Primary Examiner, Art Unit 1777