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 .
Election/Restrictions
Claims 19-23 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 05/19/2026.
Claim Objections
Claim 9 is objected to because of the following informalities:
Claim 9 recites a “Structural Formula 5”. While Structural Formula 1-3 has been previously recited, Structural Formula 4 was not previously recited for. Therefore, Examiner suggests amending “Structural Formula 5” to “Structural Formula 4”.
Appropriate correction is required.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-3 and 11-18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jewrajka et al. (“Influence of the formed interface during preparation of poly(vinylidene fluoride) blend cation exchange membrane on the electro-chemical properties and performance”, Desalination, 531, 115682, 2022).
Regarding claim 1, Jewrajka teaches a method for producing a self-assembly polymer membrane by non-solvent induced film formation (NIFF) (see “2.2.2. Preparation of PVDF/PMMA-co-PSSNa-1 blend membrane by NIPS Process” on pg. 3 and Scheme 1 (B) on pg. 4), the method comprising:
(a) preparing a polymer solution by mixing an ionized polymer with an organic solvent (“concentration of polymer in the casting solution was 16.5% and 22.2% (w/w) using DMSO and DMF as casting solvents separately… PMMA-co- PSSNa-1 (15.54 g) was dissolved in DMSO (30 mL) and the resulting solution was stirred at ambient temperature for 2 h”- see pg. 4 and sulfonated PMMA-co-PSSNa in scheme 1 on pg. 4);
(b) preparing a substrate on which a polymer solution coating layer is formed by coating the polymer solution on the substrate (see casting on fabric under Scheme 1 on pg. 4 and “Next, the solution was cast on a nonwoven fabric (thickness = 100 μm) by the semiautomated
casting machine at a speed of 1 m/min. The gap between the blade and the surface was adjusted to obtain cast membranes of thickness in the range 50–60 μm without the fabric thickness” on pg. 3); and
(c) forming an ionized polymer membrane by immersing the substrate on which the polymer solution coating layer is formed in a non-solvent without going through a drying process under elevated temperature conditions (“The cast film was then passed through water bath of temperature ca. 25 ◦C. The casting was performed at the humidity of about 30%. The time span between casting the solution and contacting to water bath was about 20 s. The cast film was then removed from the gelation bath after 30 min and was washed with fresh water. Thus, we prepared each type of membrane of dimension 14 cm in width and 10 m in length.”- see pg. 3 and Scheme 1(B) on pg. 4).
Regarding claim 2, Jewrajka teaches the method of claim 1, wherein in (a), the organic solvent has a boiling point of 150℃ or higher and is selected from a group consisting of dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) (“concentration of polymer in the casting solution was 16.5% and 22.2% (w/w) using DMSO and DMF as casting solvents separately… PMMA-co- PSSNa-1 (15.54 g) was dissolved in DMSO (30 mL) and the resulting solution was stirred at ambient temperature for 2 h”- see pg. 4 and sulfonated PMMA-co-PSSNa in scheme 1 on pg. 4).
Regarding claim 3, Jewrajka teaches the method of claim 1, wherein the ionized polymer is an ionized form of a polymer of poly(styrenesulfonic acid) (see “We report
the preparation of CEMs by NIPS process from the blend of PVDF and poly(methyl methacrylate)-co-poly(styrene sulfonic acid) sodium salt copolymers (PMMA-co-PSSNa) containing varying weight fractions of PVDF and PMMA-co-PSSNa copolymer” on pg. 2).
Regarding claim 11, Jewrajka teaches the method of claim 1, wherein in (a), the polymer solution contains 22.5 wt% of the ionized polymer (“concentration of polymer in the casting solution was 16.5% and 22.2% (w/w) using DMSO and DMF as casting solvents separately… PMMA-co- PSSNa-1 (15.54 g) was dissolved in DMSO (30 mL) and the resulting solution was stirred at ambient temperature for 2 h”- see pg. 4).
Regarding claim 12, Jewrajka teaches the method of claim 1, wherein the organic solvent of (a) is dimethyl sulfoxide (DMSO) (“The concentration of the polymer in the casting solutions was 22.2% (w/w). THF (20.7% w/w) and dioxane (13 and 23% w/w) were added as co-solvents separately with DMF or DMSO to prepare the membranes.”- see pg. 5), and the non-solvent of (c) is water (“Neat water was used as non-solvent in the gelation bath”- see pg. 5).
Regarding claim 13, Jewrajka teaches the method of claim 1, wherein in (b), the polymer solution coating layer has a thickness of 50 to 60 ㎛ (“The gap between the blade and the surface was adjusted to obtain cast membranes of thickness in the range 50–60 μm without the fabric thickness”- see pg. 3)
Regarding claim 14, Jewrajka teaches the method of claim 1, wherein in (b), the coating is applied by any one scheme selected from doctor blade (“The gap between the blade and the surface was adjusted to obtain cast membranes of thickness in the range 50–60 μm without the fabric thickness”- see pg. 3)
Regarding claim 15, Jewrajka teaches the method of claim 1, wherein in (c), the coating layer of the polymer solution forms a gel region by gelation at a contact surface with the non-solvent (“The membranes were prepared by casting the solution on both sides of the fabric followed by NIPS process using water as a gelation medium”- see pg. 5).
Regarding claim 16, Jewrajka teaches the method of claim 15, wherein the gel region configured to prevent the non-solvent from penetrating into the ionized polymer and allow the organic solvent to escape from the ionized polymer (“in order to prepare a membrane with an extremely dense structure and no water passage at low pressure, a co-solvent (dioxane or THF) was added to the casting solution”- see pg. 5).
Regarding claim 17, Jewrajka teaches the method of claim 1, further comprising, after (c), (d) ion-exchanging a counter ion of the ionized polymer membrane after the ionized polymer membrane is spontaneously separated from the substrate (see “Water desalination by ED process” on pg. 9).
Regarding claim 18, Jewrajka teaches the method of claim 17, wherein the ion exchanging exchanges the counter ion with a chloride ion (Cl-) by adding sodium chloride (NaCl) (see “Water desalination by ED process” on pg. 9).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 4 is rejected under 35 U.S.C. 103 as being unpatentable over Jewrajka et al. (“Influence of the formed interface during preparation of poly(vinylidene fluoride) blend cation exchange membrane on the electro-chemical properties and performance”, Desalination, 531, 115682, 2022- see attached), and further in view of Li et al. (“Soluble poly(aryl piperidinium) with extended aromatic segments as anion exchange membranes for alkaline fuel cells and water electrolysis”, Journal of Membrane Science, 642, 119966, 2022- see attached) and Li et al. (“Soluble poly(aryl piperidinium) with extended aromatic segments as anion exchange membranes for alkaline fuel cells and water electrolysis- Supporting Information”, Journal of Membrane Science, 642, 119966, 2022- see attached) .
Regarding claim 4, Jewrajka teaches the method of claim 3. While Jewrajka fails to teach
the ionized polymer is a quaternized poly(aryl piperidinium)(q-PAP), wherein in the Structural Formula 1, m1 is a repeating unit number, which is an integer from 1 to 10, n1 is a repeating unit number, which is an integer from 50 to 200, and X- is a hydroxide ion (OH-) or a chloride ion (Cl-), Jewrajka does teach a polymer membrane with electrochemical properties for electrolysis applications such as water desalination, prompting one of ordinary skill to look to related art for polymer membranes of different material with improved electrochemical properties.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties, Li uses solution casting to form a membrane from a quaternized poly(aryl piperidinium)(q-PAP) (see modified Figure 1 below), wherein in the Structural Formula 1, m1 is a repeating unit number, which is an integer of 3, n1 is a repeating unit number, which is an integer of 83 (the molar mass of the single repeating unit is ~417 g/mol and the molecular weight in Table S2 of the supporting information is 35,300, resulting in a number of repeat units of 35,300/417= 83), and X- is a hydroxide ion (OH-). The q-PAP polymeric membrane of Li exhibits roughly around 7 to 60 times increase in membrane conductivity (see OH- conductivity at 20 °C for PTP-83 in Figure 8 in comparison to the membrane conductivity values shown in Table 2 of Jewrajka on pg. 9).
Therefore, it would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to use the non-solvent induced film formation method of Jewrajka to form a self-assembly polymer membrane comprising the q-PAP of Li, for the benefit of forming polymeric membranes with improved membrane conductivity. There would have been a reasonable expectation of success to form the quaternized poly(aryl piperidinium)(q-PAP) membrane by a non-solvent induced film formation method, since Jewrajka teaches forming membranes using either a solvent casting method or non-solvent induced film formation method (see Scheme 1 of Jewrajka). Further, Jewrajka teaches that membranes formed by the non-solvent induced film formation method exhibited better water desalination performance than those prepared by the solvent casting method (“Hence, with similar composition and ionic group content, CEM2-P membrane prepared by NIPS process exhibited much better water desalination performance than that of the CEM2-S membrane prepared by solvent evaporation method”- see pg. 9 of Jewrajka), prompting one of ordinary skill in the art to use the non-solvent induced film formation method to further improve the electrochemical properties.
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Claim(s) 5-8 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Jewrajka et al. (“Influence of the formed interface during preparation of poly(vinylidene fluoride) blend cation exchange membrane on the electro-chemical properties and performance”, Desalination, 531, 115682, 2022- see attached), Li et al. (“Soluble poly(aryl piperidinium) with extended aromatic segments as anion exchange membranes for alkaline fuel cells and water electrolysis”, Journal of Membrane Science, 642, 119966, 2022- see attached) and Li et al. (“Soluble poly(aryl piperidinium) with extended aromatic segments as anion exchange membranes for alkaline fuel cells and water electrolysis- Supporting Information”, Journal of Membrane Science, 642, 119966, 2022- see attached), and further in view of Jannasch et al. (“Poly(arylene piperidinium) Hydroxide Ion Exchange Membranes: Synthesis, Alkaline Stability, and Conductivity”, Advanced Functional Materials, 28, 1702758, 2018).
Regarding claim 5, Jewrajka modified with Li teaches the method of claim 4.
Further, Li teaches wherein in the Structural Formula 1, the m1 is the repeating unit number of 3, the n1 is the repeating unit number of 83, and the X- is the hydroxide ion (OH-) (see rejection of claim 4 above).
While Li fails to teach the n1 is a repeating unit from 100 to 150, it would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to synthesize a quaternized poly(aryl piperidinium) with n1 being a repeating unit from 100 to 150 through routine optimization (see MPEP 2144.05.II). Li teaches forming co-polymers with varying quaternized poly(aryl piperidinium) weight fractions yields varying molecular weights (see Table S2 and “2.2 Polymerization” on pg. 2 of Li).
Further, in the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties Jannasch teaches the molecular weight of the polymers is increased by carrying out the polymerization with a stoichiometric excess of mPip (see “However, the polymerizations were carried out with a stoichiometric excess of mPip in order to increase the molecular weight of the polymers” under Polymerization portion of Experimental section on pg. 8). Therefore, it is within the scope of one of ordinary skill to optimize the quaternized poly(aryl piperidinium) weight fractions or mPip monomer concentration to vary the molecular weight such that the n1 repeating unit is from 100 to 150.
Regarding claim 6, Jewrajka modified with Li and Jannasch teaches the method of claim 4.
Li notes previous work where replacing methyl iodide with alkyl halides or QA-based halides in Menshutkin reactions can achieve comb-shaped poly(arylene piperidinium) with ion-conducting channels that display high conductivity and stability (“Also, by the replacement of methyl iodide with alkyl halides or QA-based halides in Menshutkin reactions, comb-shaped poly(arylene piperidinium) with ion-conducting channels can be obtained, displaying high conductivity and stability”- see pg. 2), but fails to explicitly teach the quaternized poly(aryl piperidinium) in its instant study is produced according to a Menshutkin reaction.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties Jannasch teaches wherein in (a), the quaternized poly(aryl piperidinium)(q-PAP) is produced according to a Menshutkin reaction by adding a halogenated alkyl to poly(aryl piperidinium) (see “Quaternization: PBPip and PTPip were quaternized via Menshutkin reactions with iodomethane, 1-bromobutane, 1-bromohexane, and 1-bromooctane to form cationic PTPipQn, with different length of the extender chains (n = 1, 4, 6, and 8, respectively)” under Experimental Section on pg. 8 and Scheme 1a) on pg. 2). The quaternized poly(aryl piperidinium of Jannasch contain exclusively aromatic and piperidine rings in the stiff backbone structure and is devoid of any weak benzylic hydrogens or aryl ether bonds, resulting in excellent alkaline stability (Abstract: Film-forming PAPipQs are subsequently prepared in Menshutkin reactions with methyl, butyl, hexyl, and octyl halides, respectively. AEMs based on poly(terphenyl dimethylpiperidinium) show the best performance with no structural degradation detectable by 1H NMR spectroscopy after storage in 2 m aq. NaOH at 60 °C after 15 d, and a mere 5% ionic loss at 90 °C).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art for the quaternized poly(aryl piperidinium)(q-PAP) of Jewrajka modified with Li and Jannasch to be produced according to a Menshutkin reaction by adding a halogenated alkyl to poly(aryl piperidinium), as taught by Jannasch, for the benefit of producing a quaternized poly(aryl piperidinium)(q-PAP) with high conductivity and alkaline stability.
Regarding claim 7, Jewrajka modified with Li and Jannasch teaches the method of claim 6.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties Jannasch teaches the poly(aryl piperidinium) (PAP) represented by the Structural Formula 2 is polymerized under an acid catalyst according to a Friedel-Crafts condensation reaction with N-methyl-4-piperidone using a monomer represented by Structural Formula 3, wherein in the Structural Formula 3, m2 is the repeating unit number, which is the integer from 2, 4, 6, or 8 (“In the present work we utilized Friedel–Craft type reactions of mPip and electron-rich phenyl monomers to produce polymers containing exclusively aromatic and piperidine rings in the stiff backbone structure”- see Results and Discussions on pg. 2 and annotated Scheme1a) below). The quaternized poly(aryl piperidinium of Jannasch contain exclusively aromatic and piperidine rings in the stiff backbone structure and is devoid of any weak benzylic hydrogens or aryl ether bonds, resulting in excellent alkaline stability (Abstract: Film-forming PAPipQs are subsequently prepared in Menshutkin reactions with methyl, butyl, hexyl, and octyl halides, respectively. AEMs based on poly(terphenyl dimethylpiperidinium) show the best performance with no structural degradation detectable by 1H NMR spectroscopy after storage in 2 m aq. NaOH at 60 °C after 15 d, and a mere 5% ionic loss at 90 °C).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art for the quaternized poly(aryl piperidinium)(q-PAP) of Jewrajka modified with Li and Jannasch to be produced polymerized under an acid catalyst according to a Friedel-Crafts condensation reaction with N-methyl-4-piperidone using a monomer represented by Structural Formula 3, wherein in the Structural Formula 3, m2 is the repeating unit number, which is the integer from 2, 4, 6, or 8, as taught by Jannasch, for the benefit of producing a quaternized poly(aryl piperidinium)(q-PAP) with high conductivity and alkaline stability.
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Regarding claim 8, Jewrajka modified with Li and Jannasch teaches the method of claim 7.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties Jannasch teaches wherein the monomer represented by the Structural Formula 3 is p-terphenyl (see “Scheme 1. Synthetic pathways to a) PAPipQs based on biphenyl or p-terphenyl, and carrying different alkyl extender chains” on pg. 2). The quaternized poly(aryl piperidinium of Jannasch contain exclusively aromatic and piperidine rings in the stiff backbone structure and is devoid of any weak benzylic hydrogens or aryl ether bonds, resulting in excellent alkaline stability (Abstract: Film-forming PAPipQs are subsequently prepared in Menshutkin reactions with methyl, butyl, hexyl, and octyl halides, respectively. AEMs based on poly(terphenyl dimethylpiperidinium) show the best performance with no structural degradation detectable by 1H NMR spectroscopy after storage in 2 m aq. NaOH at 60 °C after 15 d, and a mere 5% ionic loss at 90 °C).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art for the monomer of Jewrajka modified with Li and Jannasch to be p-terphenyl, as taught by Jannasch, for the benefit of producing a quaternized poly(aryl piperidinium)(q-PAP) with high conductivity and alkaline stability.
Regarding claim 10, Jewrajka modified with Li and Jannasch teaches the method of claim 7.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties Jannasch teaches wherein the acid catalyst includes trifluoromethanesulfonic acid (see TFSA in annotated Scheme 1 in the rejection of claim 8 above). The TFSA acid catalyst significantly enhances the reactivity of the piperidone (“The reactivity of the piperidone is significantly enhanced by the protonation of the ketone group and the adjacent basic nitrogen by TFSA to form a superelectrophilic dication, which rapidly condenses with electron-rich aromatic compounds”- see pg. 2).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art for the acid catalyst of Jewrajka modified with Li and Jannasch to include trifluoromethanesulfonic acid, as taught by Jannasch, for the benefit of significantly enhancing the reactivity of the piperidone.
Claim(s) 9 is rejected under 35 U.S.C. 103 as being unpatentable over Jewrajka et al. (“Influence of the formed interface during preparation of poly(vinylidene fluoride) blend cation exchange membrane on the electro-chemical properties and performance”, Desalination, 531, 115682, 2022- see attached), and further in view of Vengatesan et al. (“Quaternized poly (styrene-co-vinylbenzyl chloride) anion exchange membranes for alkaline water electrolysers”, Journal of Power Sources, 284, 361-368, 2015).
Regarding claim 9, Jewrajka teaches the method of claim 3. While Jewrajka fails to teach the ionized polymer is a quaternized poly(4-vinylbenzyl-b-styrene) (PVBC-b-PS) block copolymer represented by Structural Formula 5, wherein in the Structural Formula 5, m3 and m4 are each independently a repeating unit number, which is an integer from 20 to 150, and X- is a hydroxide ion (OH-) or a chloride ion (Cl-), Jewrajka does teach a polymer membrane with electrochemical properties for electrolysis applications such as water desalination, prompting one of ordinary skill to look to related art for polymer membranes of different material with improved electrochemical properties.
In the same field of endeavor pertaining to forming polymeric membranes with electrochemical properties, Vengatesan teaches the ionized polymer is a quaternized poly(4-vinylbenzyl-b-styrene) (PVBC-b-PS) block copolymer represented by Structural Formula 5, wherein in the Structural Formula 5, m3 and m4 are each independently a repeating unit number (see annotated Figure 1 below), which is an integer from 20 to 150(see “Three different types of copolymers were synthesized by varying styrene to VBC molar ratios, i.e. 1:0.16, 1:0.33, 1:1, and the corresponding co-polymers were denoted as SV e 0.16, SV e 0.33 and SV e 1, respectively” under 2.2 Synthesis of poly (ST-co-VBC) co-polymer and amination on pg. 362 where a 1:1 ratio would equate to m=50 and n=50 and a 0.33:1 ratio would equate to m=33 and n=77), and X- is a hydroxide ion (OH-) (see annotated Figure 1 below). The membrane of Vengatesan exhibits a high ion conductivity of 6.8 mS cm-1 (Abstract: “The synthesized co-polymers are identified by FTIR and 1H-NMR analysis. Hydroxide (OH-) ion conductivity of the anion exchange membrane with styrene to VBC ratio of 1: 0.33 is as high as 6.8 x 10-3 S cm-1 in de-ionised water at 25 C”) together with good mechanical properties that allowed for stable performance for almost 200 hours when assembled as an anion exchange membrane (see “exhibits good mechanical properties together with high ionic conductivity… The cell performance increases as the electrolyser temperature is increased from 25 C to 65 C. Overall, the single cell was operated for almost 200 h and it shows reasonably a stable performance” under conclusions on pg. 367).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to modify the ionized polymer of Jewrajka to be a quaternized poly(4-vinylbenzyl-b-styrene) (PVBC-b-PS) block copolymer, as taught by Vengatesan, for the benefit of forming anion exchange membranes with high conductivity and stable performance over a couple hundred hours. There would have been a reasonable expectation of success to form the quaternized poly(4-vinylbenzyl-b-styrene) (PVBC-b-PS) block copolymer membrane by a non-solvent induced film formation method, since Jewrajka teaches forming membranes using either a solvent casting method or non-solvent induced film formation method (see Scheme 1 of Jewrajka). Further, Jewrajka teaches that membranes formed by the non-solvent induced film formation method exhibited better water desalination performance than those prepared by the solvent casting method (“Hence, with similar composition and ionic group content, CEM2-P membrane prepared by NIPS process exhibited much better water desalination performance than that of the CEM2-S membrane prepared by solvent evaporation method”- see pg. 9 of Jewrajka), prompting one of ordinary skill in the art to use the non-solvent induced film formation method to further improve the electrochemical properties.
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Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ARIELLA MACHNESS whose telephone number is (408)918-7587. The examiner can normally be reached Monday - Friday, 6:30-2:30 PT.
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/ARIELLA MACHNESS/Examiner, Art Unit 1743
Prosecution Insights