DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
Acknowledgement has been made of applicant’s claim for priority under 35 USC 119 (a-d). The certified copy has been filed on 06/20/2023.
Information Disclosure Statement
The Information Disclosure Statements (IDS) filed 06/20/2023 and 09/09/2025 have been placed in the application file and the information referred to therein has been considered.
Drawings
The drawings received 06/20/2023 are acceptable for examination purposes.
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.
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.
Claim 1 are rejected under 35 U.S.C. 103 as being unpatentable over Chen at al. “Tunable multi-cations-crosslinked poly(arylene piperidinium)-based alkaline membranes with high ion conductivity and durability” Journal of Membrane Science 588 (2019) 117120 (Chen) in view of Lee et. al, “Fluorene-Based Hydroxide Ion Conducting Polymers for Chemically Stable Anion Exchange Membrane Fuel Cells” ACS Macro Lett. 2015, 4, 453−457 (Lee).
Regarding claim 1, Chen discloses polyarene based cross- linked polymer represented by following Formula A:
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Chen does not expressly disclose wherein each of aryl-1 and aryl-2 is independently selected from a group consisting of fluorenyl, phenyl, bi phenyl, terphenyl and quaterphenyl, at least one of them being fluorenyl and wherein counter-ion at ammonium group is hydroxide
Lee teaches novel fluorene based polymer comprising alkylammonium group with hydroxide counter-ion. Lee also teaches that polymeric-anion exchange membrane exhibit high hydroxide -ion conductivity and high chemical stability (Abstract) .Since Chen and Lee are in the same field of endeavor (anion-exchange membranes) and are directed to solving the same problem, i.e. making polymers suitable for preparation of polymer exchange membranes it would have been obvious to one of ordinary skill in the art, at the time of the effective filing date of invention, to utilize fluorenyl group of as at least one of aryl groups (analogs of claimed aryl-1 r aryl-2) of Chen as well as hydroxide counter in of Lee instead of bromide counter-ion of Chen in order to obtain polymeric material suitable for preparation of anion exchange membranes with reasonable expectation of success
Regarding claim 2, Chen discloses wherein crosslinking degree x=5 , 5, 10 and 20 (p.3. right col., para 2.5).
Regarding claim 3, Chen discloses wherein ammonium-based crosslinking agent) is a multi-ammonium compound having at least one ammonium cation. (para 2.2).
Regarding claim 4, Chen discloses a method for preparing a cross-linked copolymer, comprising:
(I) a step of obtaining a polymer solution by dissolving a piperidine-introduced polyfluorene-based block copolymer in an organic solvent;
(II) a step of forming a quaternary piperidinium salt by reacting the mixture solution with an excess amount of methyl iodide
(III) a step of obtaining mixture solution by adding an ammonium-based crosslinking agent solution to the polymer solution and stirring the same;
(IV) a step of obtaining a polymer in solid phase by precipitating, washing and drying the polymer solution with the quaternary piperidinium salt formed (para 2.5).
Chen does not expressly disclose step of reaction with MeI as on step III, however
selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results. In re Gibson, 39 F.2d 975,5 USPQ 230 (CCPA 1930); MPEP § 2144.04. Asso, Chen does not expressly disclose a polymer of step I as a fluorene based polymer.
Lee teaches novel fluorene based polymer comprising alkylammonium group with hydroxide counter-ion. Lee also teaches that polymeric-anion exchange membrane exhibit high hydroxide -ion conductivity and high chemical stability (Abstract) .Since Chen and Lee are in the same field of endeavor (anion-exchange membranes) and are directed to solving the same problem, i.e. making polymers suitable for preparation of polymer exchange membranes. it would have been obvious to one of ordinary skill in the art, at the time of the effective filing date of invention, to incorporate fluorenyl group of as at least one of aryl groups in the starting polymer of Chen to obtain polymeric material suitable for preparation of anion exchange membranes with reasonable expectation of success.
Regarding claim 5, Chen discloses dimethyl sulfoxide (para 2.5).
Regarding claim 6, Chen discloses DBDMAH (para 2.5).
Regarding claim 7,modified Chen discloses polyfluorene-based anion exchange membrane having a cross- linked structure, which is obtained from the polyfluorene-based cross-linked copolymer ( Chen. Abstract, para 2.6).
Regarding claim 8,modified Chen discloses the invention as discussed above as applied to claim 1. In addition, modified Chen discloses the method comprising steps of (a) a step of obtaining a polymer solution by dissolving the polyfluorene-based cross-linked copolymer in an organic solvent; (b) a step of obtaining a membrane by filtering the polymer solution, casting on a glass plate and then drying the same; and (c) a step of converting counterions to OH- ions by immersing the obtained membrane in a 1 M NaOH solution (Chen, para 2.6). Chen does not expressly disclose a filtering the polymer solution, however, it would have been obvious to one or ordinary skill in the art before the effective filing date of the claimed invention to include an filtration step of the polymer solution in case of apparency of insoluble impurities in order to obtain anion exchange membranes with good anion conductivity.
Regarding claim 9 ,modified Chen discloses wherein the organic solvent of the step (a) is dimethyl sulfoxide or dimethylformamide (para 2.6).
Regarding claim 10 ,modified Chen discloses the invention as discussed above as applied to claim 8 and incorporated therein. Modified Chen does not expressly disclose wherein the polymer solution of the step (a) has a concentration of 2-30 wt.%. However, since the criticality of such concentration the polymer solution- a position claimed by Applicant is not supported by any showing of criticality of such placement in the instant specification, nor did Applicant stated that such placement serves any specific purpose or performs any specific function other that the function disclosed in modified Chen (see para 2.5 and 2.6), it would have been obvious top those skilled in the art at the time the invention was made to optimize said concentration as an obvious design choice, and as such it does not impact the patentability of claim 10.
Regarding claim 12,modified Chen discloses a membrane electrode assembly (Chen, para 2.7.9).
Regarding claim 13, modified Chen discloses an alkaline fuel cell (Chen. Title, para 3.5, Conclusion,).
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Chen at al. “Tunable multi-cations-crosslinked poly(arylene piperidinium)-based alkaline membranes with high ion conductivity and durability” Journal of Membrane Science 588 (2019) 117120 (Chen) in view of Lee et. al, “Fluorene-Based Hydroxide Ion Conducting Polymers for Chemically Stable Anion Exchange Membrane Fuel Cells” ACS Macro Lett. 2015, 4, 453−457 (Lee) and further in view of KR 20120113822 to Nho (Nho, machine translation)
Regarding claim 11,modified Chen discloses the invention as discussed above as applied to claim 8 and incorporated therein. Modified Chen also a step of slowly removing the organic solvent in an oven at 80°C for 24 hours (para 2.6) but does not expressly disclose the step of completely removing the organic solvent by heating in a vacuum oven at 120-150 °C for 24 hours (p.2).
Nho teaches a for preparation of a polymer electrolyte membrane, comprising a method of removing of remaining solution (DMSO) in vacuum at 100-140oC for 14 h. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. MPEP 2144.05. Therefore, It would have been obvious to one or ordinary skill in the art before the effective filing date of the claimed invention to optimize a temperature and time in the step of complete removing DMSO of modified Chem within parameters disclosed by Nho in order to completely remove DMSO.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Chen at al. “Tunable multi-cations-crosslinked poly(arylene piperidinium)-based alkaline membranes with high ion conductivity and durability” Journal of Membrane Science 588 (2019) 117120 (Chen) in view of Lee et. al, “Fluorene-Based Hydroxide Ion Conducting Polymers for Chemically Stable Anion Exchange Membrane Fuel Cells” ACS Macro Lett. 2015, 4, 453−457 (Lee) and further in view of CN 102952265 to Zhu ( Zhu machine translation)
Regarding claim 14, modified Chen discloses the invention as discussed above as applied to claim 1 and incorporated therein. Modified Chen does not expressly disclose water electrolysis device.
Zhu teaches a cross linked polymer anion exchange membrane (Abstract). Zhu also teaches that such type f membrane can be use in different type of process, including water electrolysis (para 2). As such device for such electrolysis is implicitly deposed by Zhu. Therefore, it would have been obvious to one or ordinary skill in the art before the effective filing date of the claimed invention to use chemically stable and having high hydroxide conductivity the polyfluorene-based anion exchange membrane having a cross-linked structure of modified Chen in the water electrolysis device of Zhu in order to expand applicability of the membrane and improve life time of the water electrolysis device.
Conclusion
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/Alexander Usyatinsky/Primary Examiner, Art Unit 1751