Hael,
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 of cationic exchange polymer matrix materials in the reply filed May 8, 2026 is acknowledged. Applicant states that Claim 4 is directed to an anionic exchange polymer matrix material and further acknowledges that Claim 4 was held in abeyance pending election. Since Applicant elected cationic exchange polymer matrix materials, Claim 4 remains withdrawn from further consideration pursuant to 37 CFR 1.142(b).
Applicant is advised that Claim 4 should be identified in the claim listing as withdrawn or withdrawn currently amended, rather than currently amended. If Applicant intends to pursue both cationic exchange polymer matrix materials and anionic exchange polymer matrix materials without a species election, Applicant may amend the elected claim scope to recite a single claim encompassing both alternatives, provided such amendment is otherwise proper.
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.
Claims 12 and 13 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.
Claim 12 recites the limitation “wherein the one or more types of PAFs are selected from PAF-1, PAF-1-CH₃, PAF-1-CH₂OH, PAF-1-CH₂-phthalimide, PAF-1-CH₂N═CMe₂, PAF-1-CH₂Cl, PAF-1-SH, PAF-1-ET, PAF-1-NMDG, PAF-1-SMe, PAF-1-CH₂NH₂, and PAF-1-CH₂AO.” This limitation renders the claim indefinite because Claim 12 depends from Claim 1, and Claim 1 requires the one or more types of PAFs to comprise nodes having Formula II linked by linking ligands having Formula III. The listed PAF species in Claim 12 must therefore satisfy the Formula II node requirement of Claim 1.
The indefiniteness arises from Applicant’s amendment to Claim 1. Previously, the node limitation appeared in Claim 11 and permitted nodes having Formula I or Formula II. Claim 12 was not dependent from Claim 11 and therefore was not limited by that Formula I or Formula II node requirement. As currently amended, Claim 1 now requires the one or more types of PAFs to comprise nodes having Formula II linked by linking ligands having Formula III. However, Claim 12 continues to recite PAF-1 and PAF-1 derivatives without clarifying whether those listed species possess the required Formula II node structure. Accordingly, the scope of Claim 12 is unclear.
Claim 13 recites the limitation “wherein the one or more types of PAFs are selected from PAF-1-SH, PAF-1-ET, PAF-1-NMDG, PAF-1-SMe, PAF-1-CH₂NH₂, and PAF-1-CH₂AO.” This limitation renders the claim indefinite because Claim 13 further limits the PAF-1 derivatives recited in Claim 12 to a narrower subset, while Claim 1 requires the one or more types of PAFs to comprise nodes having Formula II linked by linking ligands having Formula III. As discussed above with respect to Claim 12, Claim 13 does not clarify whether the listed PAF-1 derivatives possess the required Formula II node structure. Accordingly, the scope of Claim 13 is unclear.
In view of the indefiniteness set forth above, Claims 12 and 13 have not been treated under 35 U.S.C. 102 or 103 because the scope of the recited PAF-1 and PAF-1 derivative species cannot be reasonably ascertained in view of the Formula II node requirement of Claim 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.
Claims 1, 3, 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over ZHANG et al. (Anion Substitution in Porous Aromatic Frameworks Boosting Molecular Permeability and Selectivity for Membrane Acetylene Separation, 2020, hereinafter ZHANG) In view of ZHANG et al. (CN110336052, hereinafter ZHANG-052) and REN et al. (Synthesis of a porous aromatic framework for adsorbing organic pollutants application, 2011, hereinafter REN).
Regarding Claim 1, ZHANG discloses an anion substitution strategy in an ionic porous aromatic framework (iPAF-1), where F⁻ and OH⁻ replace Cl⁻ while retaining high porosity. The basic anions confined in the pores attract acidic acetylene strongly and preferentially, and the prepared membranes exhibit improved acetylene separation performance, including sevenfold acetylene permeability and fivefold permselectivity for acetylene over ethylene and ethane (Abstract, Pg. 1).
The anion substitution in iPAF-1 is carried out by counterion exchange, where OH⁻ and F⁻ anions are chosen as the counterions to replace the parent Cl⁻. The small anion diameters preserve the pore volume of the parent material, and for membrane applications iPAF-1 is further processed into mixed matrix membranes through incorporation of nanoparticles in a polymer matrix, with gas separation properties investigated by permeations of C₂H₂, C₂H₄, and C₂H₆ unary and binary gases (Pg. 2, Col. 1).
The mixed matrix membranes are fabricated using iPAF-1-OH as the representative filler, where iPAF-1-OH fillers are blended with 6FDA-ODA to yield a free-standing continuous membrane. The iPAF-1-OH particles are tightly embedded in 6FDA-ODA with no visible phase segregation, and the iPAF-1-OH/6FDA-ODA mixed matrix membranes show improved C₂H₂/C₂H₄ permselectivity from 2.4 to 12.1 owing to the OH⁻ functionality within the PAF’s pore (Pg. 4).
However, ZHANG does not explicitly disclose that the polymer matrix comprises an ion exchange polymer matrix material.
ZHANG-052 discloses a hybrid matrix type cation exchange membrane (¶[0002]). The sulfonated modified polymers include sulfonated polyether ether ketone (SPEEK), perfluoro sulfonic acid membrane (Nafion), and sulfonated polysulfone (SPES) (¶[0014]).
The sulfonated modified polymer is prepared by dissolving the polymer in concentrated sulfuric acid, precipitating the reaction mixture into ice water, washing the resulting solid until neutral, and drying to obtain the sulfonated modified polymer, where sulfonation provides sufficient proton exchange sites (¶[0017]).
The mixed matrix type cation membrane is prepared by adding sulfonated polyether sulfone and TpBD-Me₂ to NMP and stirring to disperse, casting the obtained casting solution onto a clean and flat glass plate and allowing it to flow into a film, peeling off the film from the glass plate and immersing it in H₂SO₄ solution, washing away the free ions on the film surface, and obtaining a mixed matrix type cation membrane comprising TpBD-Me₂ dispersed in sulfonated polyether sulfone (¶[0064]).
The cation exchange membrane disclosed by ZHANG-052 addresses poor ion selectivity, tensile strength, and swelling resistance by introducing functionalized framework materials into polymers containing sulfonate groups to provide ion selectivity and size stability (¶[0010]). In view of ZHANG’s mixed matrix membrane that incorporates porous framework particles into a polymer matrix, a person skilled in the art would substitute the polymer matrix material in the mixed matrix membrane with a sulfonated modified polymer material to predictably obtain an ion exchange composite membrane.
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 use sulfonated polysulfone, as disclosed by ZHANG-052, as the ion exchange polymer matrix material in the composite membrane by ZHANG.
However, modified ZHANG does not explicitly disclose that the one or more types of PAFs comprise a series of nodes having Formula II linked by linking ligands having Formula III.
REN discloses PAF-5 synthesized from 1,3,5-tris(4-bromophenyl)benzene using a Yamamoto-type Ullmann reaction, where PAF-5 is composed only of phenyl rings and exhibits high stability, high surface area, and ability to adsorb organic chemical pollutants (Abstract).
In Synthesis of PAF-5, 1,3,5-tris(4-bromophenyl)benzene is added to a solution containing Ni(cod)₂ and 2,2′-bipyridyl in dehydrated DMF, and the mixture is stirred to obtain a deep purple suspension. After concentrated HCl is added, the crude product is filtered, washed, and dried in vacuum to give PAF-5 as an off-white powder (Pg. 2).
In the Results and Discussion, to synthesize PAF-5 composed only of phenyl rings, 1,3,5-tris(4-bromophenyl)benzene with D3h symmetry is employed as the monomer. The phenyl rings are connected together using Ni(0)-catalyzed Yamamoto-type Ullmann cross-coupling chemistry to form an expected layered hexagonal structure, and PAF-5 possesses a highly porous texture through the Yamamoto homocoupling reaction. Scheme 1 illustrates the cross-coupling reaction used to produce the extended framework, with the center phenyl rings represented in a different style (Pg. 2).
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Scheme 1 of REN
The center phenyl rings represented in Scheme 1 correspond to the Formula II nodes, with each center phenyl ring including three branch points at the 1,3,5 positions. The bromine atoms in 1,3,5-tris(4-bromophenyl)benzene serve as coupling sites in the monomer and are not part of the final PAF framework. After Yamamoto-type Ullmann cross-coupling, the coupled phenyl rings form the final phenylene linking ligands between the center phenyl rings, corresponding to Formula III.
The PAF-5 scaffold disclosed by REN addresses adsorption of organic chemical pollutants by employing an all-phenyl porous aromatic framework to provide high surface area, permanent porosity, high stability, and organic chemical pollutant adsorption capability (Abstract). In view of modified ZHANG’s composite membrane that incorporates porous framework particles into a polymer matrix, a person skilled in the art would prepare the porous framework particles using the PAF-5 synthesis method to predictably obtain stable, high-surface-area porous aromatic framework particles for adsorbing organic pollutants.
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 apply the PAF-5 synthesis method, as disclosed by REN, in preparation of the porous framework particles in the composite membrane by modified ZHANG.
Regarding Claim 3, modified ZHANG makes obvious the composite membrane of Claim 1. ZHANG-052 discloses a hybrid matrix type cation exchange membrane (¶[0002]).
Regarding Claim 5 and 6, modified ZHANG makes obvious the composite membrane of Claim 1. ZHANG-052 discloses sulfonated modified polymers including sulfonated polyether ether ketone, perfluoro sulfonic acid membrane, and sulfonated polysulfone (¶[0014]).
Regarding Claim 7, modified ZHANG makes obvious the composite membrane of Claim 1. ZHANG discloses that the particle size of iPAF-1-OH in ethanol is 44 ± 13 nm (Pg. 4, Col. 2), which overlaps the claimed particle size range “from 50 nm to 300 nm in diameter.”
Regarding Claim 8, modified ZHANG makes obvious the composite membrane of Claim 1. ZHANG discloses that incorporating iPAF-1-OH nanoparticles into 6FDA-ODA yielded a free standing and continuous membrane with an even iPAF-1-OH distribution (Pg. 4, Col. 2).
Regarding Claims 9 and 10, modified ZHANG makes obvious the composite membrane of Claim 1. ZHANG discloses mixed matrix membranes with different iPAF-1-OH contents of 6 wt.% to 21 wt% (Pg. 4, Col. 2), which is within the claimed PAF loading range “from 5 wt. % to 40 wt. %” (Claim 9) and overlaps the claimed PAF loading range “from 10 wt. % to 25 wt. %” (Claim 10).
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over ZHANG in view of ZHANG-052 and REN as applied to claim 1 above, and further in view of PAN et al. (Luminescent and Swellable Conjugated Microporous Polymers for Detecting Nitroaromatic Explosives and Removing Harmful Organic Vapors, 2019, hereinafter PAN).
Regarding Claim 11, modified ZHANG makes obvious the composite membrane of Claim 1. However, modified ZHANG does not explicitly disclose that “the linking ligands comprise a polyamine.”
PAN discloses that Buchwald-Hartwig coupling creates C-N bonds in CMP polymer networks by cross-coupling arylamines with aryl halides, and that organic building blocks having different functional groups allow fine-tuning of specific surface area and porosity (Introduction; Pg. 48352).
In Results and Discussion, the synthesis route for LPCMP1-4 is depicted in Scheme 1.
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Scheme 1 of PAN
Optimization experiments showed that LPCMP1-NS, synthesized using the triamine building block, exhibited a BET surface area more than five times higher than other BH-based CMPs synthesized using the same core. Addition of sodium nitrate increased the BET specific surface area from 275 m² g⁻¹ to 1280 m² g⁻¹ (Pgs. 48354-48355).
In porosity studies, LPCMP1 and LPCMP3, synthesized using 1,3,5-tris(4-aminophenyl)benzene as the building block, possess BET specific surface areas much higher than LPCMP2 and LPCMP4. The difference in BET surface area may result from the amino groups in the benzene building blocks being more active during BH cross-coupling, producing polymers with a higher cross-linking degree. The choice of building block is crucial for specific surface area and pore size, and the surface area and pore size are tunable by changing the building blocks (Pg. 48357).
The di-amine linkers disclosed by PAN are used in the prior amine-CMP approach as linkers with cores having multiple bromo groups, and combinations of tri- and tetrabromo and amine building blocks are used to synthesize BH CMPs and control surface area, pore size, and porosity (Introduction; Pg. 48353).
In view of modified ZHANG’s porous framework particles prepared using REN’s PAF-5 scaffold, where a multifunctional aromatic monomer is coupled to form a covalent porous aromatic framework, a person skilled in the art would recognize the significance of applying a di-amine linker approach to the PAF-5 scaffold, where cores having multiple bromo groups are coupled with di-amine linkers to form C-N bonds in a porous framework network and the selection of amine linkers and building blocks controls surface area, pore size, and porosity, to predictably tune the porous framework structure.
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 use di-amine linkers, as disclosed by PAN, as the linking ligands in the composite membrane by modified ZHANG.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over ZHANG in view of ZHANG-052 and REN as applied to claim 1 above, and further in view of LI et al. (Mercury nano-trap for effective and efficient removal of mercury(II) from aqueous solution, 2014, hereinafter LI).
Regarding Claim 14, modified ZHANG makes obvious the composite membrane of Claim 1. However, modified ZHANG does not explicitly disclose that “the one or more types of PAFs bind to a targeted ion selected from Hg²⁺, Nd³⁺, Cu²⁺, Pb²⁺, UO₂²⁺, B(OH)₃, Fe³⁺, and AuCl₄⁻.”
LI discloses a porous organic polymer based mercury “nano-trap” made by functionalizing porous aromatic framework 1, also known as porous polymer network 6, with thiol groups that are well-known to bind Hg(II) strongly, where the thiol-functionalized porous aromatic framework 1 is formed by chloromethylation followed by treatment with sodium hydrosulfide (Pg. 2, Col. 2).
In Hg(II) sorption studies, PAF-1-SH rapidly captures Hg(II) ions, where the residual Hg(II) concentration in solution was smaller than 0.4 ppb, a single treatment can reduce mercury concentration below acceptable limits in drinking water standards, and the distribution coefficient Kd is among the highest for sorbent materials for Hg(II) adsorption reported thus far (Pg. 3, Col. 1).
In selectivity tests, PAF-1-SH effectively adsorbs Hg(II), and other background metal ions Ca(II), Zn(II), Mg(II) and Na(I) do not appreciably bind to PAF-1-SH, such that PAF-1-SH remains effective in the presence of high concentrations of these ions (Pg. 4, Col. 2).
The PAF-1-SH disclosed by LI remains effective in the presence of high concentrations of background metal ions Ca(II), Zn(II), Mg(II), and Na(I) while effectively adsorbing Hg(II) (Pg. 4, Col. 2). In view of ZHANG’s mixed matrix membrane, where PAF particles are embedded in a polymer matrix as functional filler particles, a person skilled in the art would recognize the significance of providing thiol-functionalized PAF particles to predictably provide strong and selective Hg(II) binding in the presence of competing background metal ions.
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 use thiol-functionalized PAF particles, as disclosed by LI, as the embedded porous aromatic framework particles in the composite membrane by modified ZHANG.
Response to Arguments
Applicant’s arguments, see Remarks, filed May 8, 2026, with respect to the previous rejections under 35 U.S.C. 102 and 35 U.S.C. 103 have been fully considered and are persuasive. Therefore, the previous rejection has been withdrawn. However, upon further consideration, a new ground of rejection under 35 U.S.C. 103 is made in view of ZHANG, ZHANG-052, REN, PAN and LI.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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 1771
/PREM C SINGH/Supervisory Patent Examiner, Art Unit 1771
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