Prosecution Insights
Last updated: April 19, 2026
Application No. 18/026,878

MOLECULARLY POROUS CROSS-LINKED MEMBRANES

Non-Final OA §102§103§112
Filed
Mar 21, 2023
Examiner
CHIU, TAK LIANG
Art Unit
1777
Tech Center
1700 — Chemical & Materials Engineering
Assignee
King Abdullah University Of Science And Technology
OA Round
1 (Non-Final)
53%
Grant Probability
Moderate
1-2
OA Rounds
3y 8m
To Grant
90%
With Interview

Examiner Intelligence

Grants 53% of resolved cases
53%
Career Allow Rate
17 granted / 32 resolved
-11.9% vs TC avg
Strong +37% interview lift
Without
With
+37.2%
Interview Lift
resolved cases with interview
Typical timeline
3y 8m
Avg Prosecution
37 currently pending
Career history
69
Total Applications
across all art units

Statute-Specific Performance

§101
1.4%
-38.6% vs TC avg
§103
42.3%
+2.3% vs TC avg
§102
17.6%
-22.4% vs TC avg
§112
37.1%
-2.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 32 resolved cases

Office Action

§102 §103 §112
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 II , Claims 11-23 in the reply filed on October 20, 2025 is acknowledged. Claim s 1-5, and 9-10 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention , there being no allowable generic or linking claim.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 October 20, 2025 . Priority Applicant’s claim for the benefit of a prior-filed application (has PRO 63079590 , filed on September 17, 2020; is 371 of PCT/IB2021/058510 , filed on September 17, 2021) under 35 U.S.C. 119(e) or under 35 U.S .C. 120, 121, 365(c), or 386(c) is acknowledged. Claim Objections Claim 12 objected to because of the following informalities: The phrase “are trianglamine” should be corrected to read “are trianglamine s ” to fix agreement and avoid scope confusion. Claim 13 objected to because of the following informalities: The phrase “linked with” should be corrected to read “linked to ” to use standard claim language and improve clarity. Claim 14 objected to because of the following informalities: The phrase “a acyl chloride” should be corrected to read “ an acyl chloride” to fix the article. Claim 21 objected to because of the following informalities: The phrase “naphthalene dicarboxylic acid dichloride cyclopropane tricarboxylic acid chloride” should be corrected to read “naphthalene dicarboxylic acid dichloride , cyclopropane tricarboxylic acid chloride” to clarify the Markush list. Claim 23 objected to because of the following informalities: The phrase “from 2-5” should be corrected to read “from 2 to 5” to improve clarity of the stated range. Appropriate correction is required. 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. Claim s 14 and 23 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 14 recites the limitation “the macrocycle ring.” There is insufficient antecedent basis for this limitation in the claim. Claim 23 recites the limitation “reactive macrocycles.” There is insufficient antecedent basis for this limitation in the claim. It is unclear whether the “reactive macrocycles” are the same as the reactive macrocycle monomers recited in the independent claim. Claim Rejections - 35 USC § 102 / § 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 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. 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: 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. Claims 11, and 14-15 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over WANG et al. (CN106345318B, hereinafter WANG). Regarding Claim 11 and 14 , WANG discloses a composite membrane for water treatment (¶[0002]). The composite membrane comprises a polymer support layer and a polyamide active layer, and the polyamide active layer comprises a polymerized cyclodextrin amino derivative and a polyacyl chloride ( 多元 酰氯 ), such as trimesoyl chloride (TMC). The cyclodextrin amino derivatives are used as aqueous monomers for interfacial polymerization to provide high water flux and good hydrophilicity, and the cyclodextrin amino derivative comprises at least two substituents RO–CH₂–CH(OH)–CH₂–NHR, with R being a hydrogen atom or a C1 to C6 organic amine (¶¶[0007]–[0008]). In Example 1, a cyclodextrin amino derivative is obtained by substituting hydroxyl groups in β cyclodextrin, with an average degree of substitution of 5, and the polymer support layer is a polyacrylonitrile microfiltration membrane. An aqueous solution contains 5% by mass cyclodextrin amino derivative and 1% by mass triethylamine, and an organic phase solution in n hexane contains trimesoyl chloride as solute. The support layer is soaked in the aqueous solution, and after removing surface moisture, the upper surface is brought into contact with the organic phase solution so interfacial polymerization occurs on the surface to form an amide from amino and polyacyl chloride groups, forming a polyamide composite film (¶¶[0043]–[0046]). Cyclodextrin has a cyclic cavity structure and good hydrophilicity, and the cyclic cavity has an inner diameter of about 0.6 nm to 1.0 nm, permitting water molecules to pass through the cyclic cavity structure. If the polyamide active layer contains a cyclodextrin structure, a composite membrane with high water flux and high selectivity can be obtained (¶[0029]). Regarding Claim 15 , WANG discloses a polyamide molecularly porous cross-linked membrane of Claim 11. WANG discloses that if the contact time with the polyacyl chloride solution is too long, the polyamide active layer formed by the interfacial polymerization reaction will be too thick, thereby reducing the water flux of the composite membrane (¶[0041]). The limitation “the membrane is less than 10 nm thick” is considered a result-effective variable that affects permeability and solute rejection in thin film composite membranes. WANG indicates that an overly thick polyamide active layer reduces water flux, and a person skilled in the art would routinely optimize the film thickness for WANG’s membrane to meet the desired performance requirements, including reducing the thickness to less than 10 nm (In re Aller, 220 F.2d 454, 456–57; 1955). Claims 12 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over WANG as applied to claim 11 above, and further in view of CHAIX et al. (“Trianglamine-Based Supramolecular Organic Framework with Permanent Intrinsic Porosity and Tunable Selectivity” 2018, hereinafter CHAIX) . Regarding Claim 12 , WANG discloses a polyamide molecularly porous cross-linked membrane of Claim 11. However, WANG does not explicitly disclose "the amine macrocycle monomers are trianglamine." CHAIX discloses a metal free trianglamine based supramolecular organic framework, T-SOF-1, having permanent intrinsic porosity and high affinity to CO₂, and tuning pore aperture dimensions by guest encapsulation for CO₂/CH₄ separation (Abstract, Pg. 14571). Schiff base macrocycles, including trianglamines, provide macrocyclic building blocks, and a supramolecular organic framework based on trianglamine, T-SOF-1, is described with permanent porosity for gas capture and selective separation, with pore size tuned by molecular guest encapsulation, wherein trianglamines can be readily prepared, purified, and scaled up at low cost. Trianglamine (T) is prepared by reacting (R, R)-1,2-diaminocyclohexane with terephthaladehyde, followed by reduction, and ¹H and ¹³C NMR confirm the structure and purity of the prepared trianglamine (Pg. 14571, Col. 2). Figure 1 illustrates the crystal structure of T-SOF-1 with a hexagonal arrangement of trianglamines and tubular packing that defines triangular channels running along the c axis (Pg. 14572). FIG. 1 of CHAIX et al. Advantageously, metal free assembly of trianglamines provides macrocycle based supramolecular organic frameworks with permanent porosity and notable CO₂ adsorption capabilities, and guest encapsulation tunes pore size and selectivity for CO₂/CH₄ separation in which only CO₂ is adsorbed at ambient conditions (Pg. 14573, Col. 1). A person skilled in the art would incorporate trianglamine as the amine macrocycle monomer in WANG’s interfacial polymerization to form the porous polyamide thin film. Trianglamine provides multiple amine reaction sites for covalent amide formation with a polyacyl chloride crosslinker and provides intrinsic porosity, improving separation performance in comparable membranes ( KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398; 2007 ). 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 select trianglamine, as disclosed by CHAIX, as the amine macrocycle monomers in the polyamide thin film composite membrane by WANG. Regarding Claim 13 , modified WANG makes obvious a polyamide molecularly porous cross-linked membrane of Claim 12. CHAIX discloses that T-SOF-1 includes a high ratio of secondary ammonium groups, including 6 NH₂⁺ groups per macrocycle, decorating the accessible inner pore of nanotubular channels with an aperture size of about 6 Å, providing a favorable environment for CO₂ capture (Pg. 14573, Col. 1). Regarding the limitation “each trianglamine is covalently linked with four trianglamines,” CHAIX shows trianglamine provides multiple amine reaction sites, and WANG’s interfacial polymerization forms covalent amide linkages from amino and polyacyl chloride groups. Incorporating the hexafunctional trianglamine having six reactive secondary amine sites into WANG’s polyacyl chloride crosslinking yields a highly crosslinked network, and each trianglamine is linked to four other trianglamines as an inherent statistical connectivity outcome of dense network formation. Claims 16-23 are rejected under 35 U.S.C. 103 as being unpatentable over WANG as in view of CHAIX . Regarding Claim 16-18, 20 and 21 , WANG discloses a composite membrane for water treatment (¶[0002]). The composite membrane comprises a polymer support layer and a polyamide active layer, and the polyamide active layer comprises a polymerized cyclodextrin amino derivative and a polyacyl chloride, such as trimesoyl chloride (TMC). The cyclodextrin amino derivatives are used as aqueous monomers for interfacial polymerization to provide high water flux and good hydrophilicity, and the cyclodextrin amino derivative comprises at least two substituents RO–CH₂–CH(OH)–CH₂–NHR, with R being a hydrogen atom or a C1 to C6 organic amine (¶¶[0007]–[0008]). In Example 1, a cyclodextrin amino derivative is obtained by substituting hydroxyl groups in β cyclodextrin, with an average degree of substitution of 5, and the polymer support layer is a polyacrylonitrile microfiltration membrane. An aqueous solution contains 5% by mass cyclodextrin amino derivative and 1% by mass triethylamine, and an organic phase solution in n hexane contains trimesoyl chloride as solute. The support layer is soaked in the aqueous solution, and after removing surface moisture, the upper surface is brought into contact with the organic phase solution so interfacial polymerization occurs on the surface to form an amide from amino and polyacyl chloride groups, forming a polyamide composite film (¶¶[0043]–[0046]). Cyclodextrin has a cyclic cavity structure and good hydrophilicity, and the cyclic cavity has an inner diameter of about 0.6 nm to 1.0 nm, permitting water molecules to pass through the cyclic cavity structure. If the polyamide active layer contains a cyclodextrin structure, a composite membrane with high water flux and high selectivity can be obtained (¶[0029]). However, WANG does not explicitly disclose reactive macrocycle monomers having at least two amine groups in the ring as recited in Claim 16, that at least one reactive macrocycle monomer is a trianglamine of Formula I having the defined A aromatic moieties and R substituents as recited in Claim 17, or that each A is independently selected from the aromatic moieties of Formula IIA–IID with the dashed bond attachment, X, and R¹–R⁴ variables as recited in Claim 18. CHAIX discloses a metal free trianglamine based supramolecular organic framework, T-SOF-1, having permanent intrinsic porosity and high affinity to CO₂, and tuning pore aperture dimensions by guest encapsulation for CO₂/CH₄ separation (Abstract, Pg. 14571). Schiff base macrocycles, including trianglamines, provide macrocyclic building blocks, and a supramolecular organic framework based on trianglamine, T-SOF-1, is described with permanent porosity for gas capture and selective separation, with pore size tuned by molecular guest encapsulation, wherein trianglamines can be readily prepared, purified, and scaled up at low cost. Trianglamine (T) is prepared by reacting (R, R)-1,2-diaminocyclohexane with terephthaladehyde, followed by reduction, and ¹H and ¹³C NMR confirm the structure and purity of the prepared trianglamine (Pg. 14571, Col. 2). Figure 1 illustrates the crystal structure of T-SOF-1 with a hexagonal arrangement of trianglamines and tubular packing that defines triangular channels running along the c axis (Pg. 14572). It is reasonably interpreted that terephthaladehyde provides an unsubstituted phenyl moiety for each A, and that each R is nothing, such that the carbon atom to which the R group would be attached is bonded to at least two hydrogens as recited in Claim 17, and wherein the unsubstituted phenyl moiety corresponds to Formula IIA with the dashed bond as the point of attachment and R1, R2, R3, and R4 as hydrogen as recited in Claim 18. The amino groups of trianglamines are protonated and interact with Cl− ions through N−H+···Cl− ionic H bonds, consolidating nanotubular packing with additional C−H···Cl− and π–π interactions between adjacent macrocycles, and hexagonal packing affords smaller channels of about 4.5 Å with one dimensional channels occupied by water. The nanotubular inner pore is decorated with secondary ammonium groups, including 6 −NH2+ groups per macrocycle, confined in an aperture of about 6 Å, providing a favorable environment for CO2 capture (Pg. 14573, Col. 1). Advantageously, metal free assembly of trianglamines provides macrocycle based supramolecular organic frameworks with permanent porosity and notable CO₂ adsorption capabilities, and guest encapsulation tunes pore size and selectivity for CO₂/CH₄ separation in which only CO₂ is adsorbed at ambient conditions (Pg. 14573, Col. 1). A person skilled in the art would incorporate trianglamine as the amine macrocycle monomer in WANG’s interfacial polymerization to form the porous polyamide thin film. Trianglamine provides multiple amine reaction sites for covalent amide formation with a polyacyl chloride crosslinker and provides intrinsic porosity, improving separation performance in comparable membranes ( KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398; 2007 ). 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 select trianglamine, as disclosed by CHAIX, as the reactive macrocycle monomers having at least two amine groups in the ring in the polyamide thin film composite membrane by WANG. Regarding Claim 19 , modified WANG makes obvious a polyamide molecularly porous cross-linked membrane of Claim 17. CHAIX discloses that trianglamine is prepared by reacting (R, R)-1,2-diaminocyclohexane with terephthaladehyde, followed by reduction (Pg. 14571, Col. 2). Regarding Claim 22 , modified WANG makes obvious a molecularly porous cross linked membrane of Claim 16. WANG indicates that contact time with the polyacyl chloride solution affects formation of the polyamide active layer (¶[0041]). Regarding the limitation “a percentage of reacted amine groups of the reactive macrocycles is at least 50%,” the recited percentage is considered a result effective variable for the interfacial polymerization reaction. A person skilled in the art would adjust interfacial polymerization conditions, including contact time and reactant concentrations, to achieve a desired percentage of reacted amine groups, including at least 50%, while meeting membrane performance requirements (In re Aller, 220 F.2d 454, 456–57; 1955). Regarding Claim 23 , modified WANG makes obvious a molecularly porous cross linked membrane of Claim 16. WANG discloses that contact time with the polyacyl chloride solution affects formation of the polyamide active layer (¶[0041]). CHAIX discloses that trianglamine includes secondary ammonium groups, including 6 −NH2+ groups per macrocycle (Pg. 14573, Col. 1). Regarding the limitation “reactive macrocycles having from 2 to 5 reacted amine groups per macrocycle,” the recited number of reacted amine groups per macrocycle is considered a result effective variable for controlling cross link density in the interfacial polymerization reaction. A person skilled in the art would adjust interfacial polymerization conditions, including contact time and reactant concentrations, to react a desired subset of the available amine groups per macrocycle, including from 2 to 5, while meeting membrane performance requirements (In re Aller, 220 F.2d 454, 456–57; 1955). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT TAK L. CHIU whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (703)756-1059 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT M-F: 9:00am - 6:00pm (CST) . Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, FILLIN "SPE Name?" \* MERGEFORMAT PREM C. SINGH can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (571)272-6381 . The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /TAK L CHIU/ Examiner, Art Unit 1777 /KRISHNAN S MENON/ Primary Examiner, Art Unit 1777
Read full office action

Prosecution Timeline

Mar 21, 2023
Application Filed
Dec 18, 2025
Non-Final Rejection — §102, §103, §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
53%
Grant Probability
90%
With Interview (+37.2%)
3y 8m
Median Time to Grant
Low
PTA Risk
Based on 32 resolved cases by this examiner. Grant probability derived from career allow rate.

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