CTNF 18/668,928 CTNF 101380 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Rejections - 35 USC § 112 07-30-02 AIA 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. The following is a quotation of 35 U.S.C. 112 (pre-AIA), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. 07-34-01 Claim 19 is 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. The claim recites “CO 2 /CH 2 selectivity. However, the specification does not clearly identify the CH 2 species or provide a recognized methodology for determining CO 2 /CH 2 selectivity. CH 2 is not a conventional stable gas specie ordinarily used in adsorption selectivity measurements, and the specification does not adequately explain how such selectivity is measures, read or calculated. As such, one of ordinary skill in the art would not be able to determine the scope of the claims with reasonable certainty. MPEP 2173.02 and 2173.05. Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-23-aia AIA 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 non-obviousness. 07-21-aia AIA Claim s 1-3, 6, 7, 20 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou et al. CN 114950159 A, August 30, 2022 (hereinafter “Zhou”) in view of Tan et al. Chemical Society Reviews, 2017 (hereinafter “Tan”) . Regarding claim 1 , Zhou discloses aromatic polymer material formed through superacid-catalyzed polymerization reactions involving aromatic compounds and rigid twisted monomers. Specifically, Zhou discloses that the rigid twisted structural monomer may include triptycene and derivatives thereof (paragraphs 0021-0022). The monomer system may include dihydroxy phenolic compounds such as resorcinol (e.g., 1, 3-resorcinol, paragraph 0021). Zhou detaches that incorporation of rigid twisted monomers into aromatic polymer structures reduces tight chain packing and increases free volume and permeability of the resulting polymer material (paragraphs 0014 and 0040). However, Zhou fails to disclose that the triptycene units and dihydroxy phenol units are covalently bonded through a secondary carbon linker within a microporous hyper-crosslinked polymer network. Tan discloses hyper-crosslinked porous polymer materials formed through Friedel-Crafts “knitting” reactions in which aromatic monomers are covalently interconnected through methylene bridges and related carbon-based crosslinking groups (pages 3322-3325), thereby forming rigid microporous polymer framework. Tan further discloses that triptycene based monomers are suitable building blocks for such hyper-crosslinked microporous polymer systems because their rigid three-dimensional structure promotes intrinsic microporosity and high surface area (pages 3332-3333). Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the aromatic polymer system of Zhou by employing the hyper-crosslinking and methylene-linking chemistry taught by Tan in order to covalently connect the triptycene-containing units and dihydroxy phenol containing units through secondary carbon linkers to produce microporous polymer network with enhanced porosity, and adsorption/separation properties. The proposed modification applies known Friedel-Crafts hyper-crosslinking techniques to aromatic monomer systems for their predictable result of increasing microporosity and transport performance in porous polymer materials. Regarding claim 2 , Zhou fails to disclose a method for capturing CO 2 , comprising: contacting a CO 2 -containing gas stream with the porous particles of the microporous polymer of claim 1 to trap molecules of CO 2 in the CO 2 -containing gas stream in the molecular structure of the microporous polymer, wherein the microporous polymer includes reacted units of triptycene, reacted units of dimethoxymethane, and resorcinol. However, Tan discloses the method for carbon dioxide capture (page 3340) and use of dimethoxymethane/formaldehyde dimethyl acetal as a methylene-forming crosslinking agent in Friedel-Crafts hyper-crosslinking reactions for preparing porous aromatic polymer adsorption materials (pages 3323-3324). It would have been obvious to one of ordinary skill in the art at the time of the invention to employ dimethoxymethane the carbon-linking agent in the aromatic polymer system of Zhou in order to form a highly microporous hyper-crosslinked polymer network containing triptycene and resorcinol units for use in carbon dioxide adsorption and gas separation applications. Further, contacting carbon dioxide containing gas stream with a porous microporous polymer material to adsorb or trap carbon dioxide represents intended use of porous adsorption materials having high surface area and microporosity. MPEP 2144.07. Regarding claim 3 , Zhou and Tan fails discloses that the microporous polymer contains oxygen in an amount 20 to 30 atomic percent (at. %) based on a total atom count of the microporous polymer. However, it would have been obvious to one of ordinary skill in the art at the time of the invention that incorporation of hydroxyl-containing aromatic monomers such as resorcinol into a hyper-crosslinked aromatic polymer framework would inherently introduce oxygen atoms into the resulting polymer composition. Further, optimizing the relative monomer ratios and degree of hydroxyl incorporation to obtain a desired oxygen content within the claimed range would have constituted routine optimization of a result effective variable, particularly where oxygen-containing functional groups are known to affect adsorption and separation performance of porous polymer materials. MPEP 2144.05. Regarding claim 6 , Zhou fails to disclose that the porous particles are in the form of spheres with a diameter of 0.2 to 2 micrometers (µm). However, Tan discloses that the hyper-crosslinked polymers can be prepared in a variety of physical forms depending on the synthetic strategy and processing condition, including spheres (pages 3335-3336). Figure 8 show the sphere diameter that ranges between 837-1364 nanometer (0.8-1.36 µm). It would have been obvious to one of ordinary skill in the art at the time of the invention to prepare the porous triptycene-containing polymer system of Zhou in spherical particulate form as taught by Tan, because spherical porous particles have known morphologies for hyper-crosslinked porous polymer materials and provide predictable advantages in adsorption accessibility, particle packing, and processibility. Also, it would have been obvious to one of ordinary skill in the art to form a sphere with a diameter within the claimed range, as optimization of sphere diameter constitutes routine optimization of a result-effective variable. MPEP 2144.05(II). Regarding claim 7 , Zhou fails to disclose that the spheres are aggregated. However, Tan discloses porous polymer nanoparticle with spherical morphologies that aggregate (pages 3334 and 3336). It would have been obvious to one of ordinary skill in the art at the time of the invention that porous polymer microspheres formed through methods described by Tan may exist in aggregated form due to interparticle interactions, solvent removal, and packing effects occurring during formation and isolation of the porous particle. Regarding claim 20 , Zhou discloses the preparation of aromatic porous polymer materials using superacid-catalyzed polymerization reactions involving aromatic compounds and rigid twisted structural monomers including triptycene. Zhou discloses rigid twisted structural compound may be triptycene or derivatives thereof (paragraphs 0021-0022). Zhou further discloses carrying out the polymerization in dichloromethane with trifluoromethanesulfonic acid catalyst, followed by methanol precipitation, filtration, washing, and drying to obtain the aromatic polymer (paragraphs 0025-0029; See examples 1-5). Tan discloses synthesis of hyper-crosslinked porous polymers through Friedel-Crafts knitting reactions using aromatic monomers and external crosslinkers to generate methylene-linked microporous polymer frameworks (page 3329). Tan discloses the use of Lewis acid catalysts including FeCl 3 and that the polymerization reactions are commonly conducted in organic solvent under reflux conditions, followed by solvent washing, alcohol treatment, and drying to isolate the porous polymer product (paragraphs 3324-3329). Therefore, it would have been obvious to one of ordinary skill in the art at the time of the claimed invention to employ the know Friedel-Crafts hyper-crosslinking methodology taught by Tan using dimethoxymethane and iron salt catalysts in the triptycene-containing aromatic polymer system disclosed by Zhou in order to obtain a rigid methylene-linked microporous polymer framework having enhanced porosity and gas adsorption properties. Selection of particular monomer ratios, catalyst loadings, reflux durations, washing conditions, alcohol treatment steps, and drying temperature constitutes routine optimization of result-effective process variable affecting polymer crosslinking and pore structure. MPEP 2144.05(II). Additionally, it is noted that claim 20 is written as a product-by-process claim. The claim limitations regarding how the device is made are product by process limitations and are given weight to the extent that the product defines structure. It is the examiner' s belief that the above references teach the same basic structure. See In re Brown , 459 F.2d 531, 535, 173 USPQ 685, 688 (CCPA 1972) (see also MPEP 2113) . 07-21-aia AIA Claim s 4 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou et al. and Tan, in view of claim 1, in further view of Swager et al. U.S. Pub. No. 20190375887 A1, December 12, 2019 (hereinafter “Swager”) . Regarding claim 4 , Zhou fails to disclose that the microporous polymer has a thermal degradation temperature of 350 to 400 degrees Celsius (°C), wherein the thermal degradation temperature is determined at a weight loss of 10 wt. % based on an initial weight of the microporous polymer. However, Swager discloses a thermogravimetric analysis (TGA) characterization of porous polymer compositions useful for gas separation applications (paragraph 0066). Specifically, Swager discloses TGA traces for both ROMP polymers showed excellent thermal stability. CF.sub.3-ROMP degradatio n started at approximately 380°C, while OMe-ROMP degradatio n started at approximately 350°C (paragraph 0143). Figures 14A-14C shows that the porous polymer compositions maintain substantial thermal stability and undergo thermal degradation at approximately the 350-450°C temperature region before substantial thermal degradation occurs, thereby evidencing that high thermal resistance of rigid aromatic porous polymer frameworks containing bulky contorted aromatic structures. It would have been obvious to one of ordinary skill in the art at the time of the invention that the highly aromatic and hyper-crosslinked porous polymer systems taught by Zhou and Tan from rigid triptycene-containing monomers would exhibit elevated thermal degradation temperatures due to the rigid aromatic backbone and extensive crosslinking of the polymer framework, as evidenced by the TGA thermal stability data disclosed by Swager. Further, optimization of the thermal degradation temperature through routine adjustment of aromatic monomer composition and crosslink density constitutes routine optimization of a result-effective variable. MPEP 2144.05 . 07-21-aia AIA Claim s 5, 8-19 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou et al. and Tan, in view of claim 1, in further view of Hassan et al. Microporous and Mesoporous Materials, 2022 (hereinafter “Hassan”) . Regarding claim 5 , Zhou fails to disclose that the microporous polymer has a char yield at 800°C of 55 to 65 wt. % based on an initial weight of the microporous polymer. However, Hassan discloses triptycene-based porous fluorinated polymers useful for carbon dioxide capture and gas storage applications. Hassan specifically discloses that the resulting porous polymer systems exhibit high thermal stability with decomposition temperatures greater than 400°C and high char yields at 800°C as determined by TGA. Hassan explicitly discloses that char yield for the polymers were more than 60% at 800°C (fig. 2, pages 3 and 6). Hassan further explains that the char yield and thermal stability arise from the rigid aromatic triptycene-containing polymer framework and extensive aromatic character of the porous polymer network. It would have been obvious to one of ordinary skill in the art at the time of the invention to know that the highly aromatic and extensively crosslinked porous polymer systems formed from triptycene-containing monomers, as taught by Zhou and Tan, would exhibit substantial char yield upon thermal decomposition due to the rigid aromatic polymer backbone and high crosslink density, as further evidenced by Hassan. Further, optimization of char yield through selection of aromatic monomer composition, hydroxyl-containing aromatic content, and degree of crosslinking constitutes routine optimization of a result effective variable. Also, discovering an optimum char yield range through routine experimentation is within the ordinary skill in the art. MPEP 2144.05(II). Regarding claim 8 , Zhou fails to disclose that the porous particles have a Brunauer-Emmett-Teller (BET) surface area of 800 to 850 square meters per gram (m 2 g −1 ). However, Hassaan discloses the porous polymer materials having high BET surface area associated with microporous triptycene-containing polymer frameworks. Hassan further discloses that the triptycene-based porous microspheres exhibit BET surface area within the range (773 – 1295 m 2 g −1 ) typically associated with highly porous adsorption materials. (fig. 4, page 6). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, that the porous triptycene-containing polymer system taught by Zhou and Hassan would possess high BET surface area due to the rigid contorted aromatic framework and intrinsic microporosity of the polymer network. Also, optimization of BET surface area through adjustment of monomer composition, pore structure and polymerization conditions constitute routine optimization of a recognized result effective variable affecting adsorption performance and gas transport properties. Discovering an optimum BET surface area within the claimed range through routine experimentation is within the ordinary skill in the art. MPEP 2144.05(II). Regarding claim 9 , Zhou fails to disclose that the porous particles have a total pore volume of 0.400 to 0.600 cubic centimeters per gram (cc/g). However, Hassan discloses that the total pore volume of the porous polymers TFPP1, TFPP2 and TFPP3 were calculated as 0.59 cc/g, 0.53 cc/g and 0.92 cc/g, respectively (page 6). The total pore volume explicitly disclosed by Hassan fall within the claimed ranged of 0.400 to 0.600 cc/g. It would have been obvious to one of ordinary skill in the art at the time of the claimed invention, that the porous triptycene containing polymer systems formed from rigid aromatic monomers would exhibit pore volumes within the claimed range due to the intrinsic microporosity and contorted aromatic framework structure of the polymers. Regarding claim 10 , Zhou fails to disclose the porous particles have a micropore volume of 0.300 to 0.400 cm 3 g −1 . However, Hassan discloses triptycene-based porous fluorinated polymers exhibiting predominant microporosity and substantial micropore characteristics. Specifically, Hassan discloses that the predominant pores in the porous organic polymers are in the microporous range with dimensions less than 1.0 nm and further disclose total pore volumes of the porous polymers TFPP1, TFPP2 and TFPP3 were calculated as 0.59 cc/g, 0.53 cc/g and 0.92 cc/g, respectively (page 6). It would have been obvious to one of ordinary skill in the art at the time of the invention to optimize the micropore volume of the triptycene-containing porous polymer system of Zhou to a value within the claimed range through routine adjustment of monomer composition, fluorine content, crosslink density, and polymerization conditions, because micropore volume is a result-effective variable affecting adsorption and gas storage properties. MPEP 2144.05. Regarding claim 11 , Zhou fails to disclose that the porous particles have a micropore volume of 65 to 75 percent (%). However, Hassan discloses porous triptycene-based polymer systems exhibiting predominant microporosity with pore dimensions less than 1.0 nm and substantial microporous character associated with the porous polymer framework (page 6). The adsorption isotherms and pore size distribution analyses confirm that the predominant pores in the polymeric networks are micropores. It would have been obvious to one of ordinary skill in the art at the time of the invention to optimize the relative microporous fraction of the porous polymer systems of Zhou to a value within the claimed range because the proportion of microporosity relative to total pore volume depends upon result-effective variables including monomer selection, degree of crosslinking, and polymerization parameters. MPEP 2144.05(II). Regarding claim 12 , Zhou fails to disclose that the microporous polymer has a carbon dioxide (CO 2 ) isosteric heat of adsorption (Q st ) of 30 to 35 kilojoules per mole (kJ mol −1 ). However, Hassan discloses that the Q st value for CO 2 for the porous organic polymer were calculated using isotherms at 273 and 298 K while employing the Clausius-Clapeyron equation (Table 1 and Fig. 6c and d). The Q st values for CO 2 at zero coverage were found to be in between 24.5 and 31.0 kJ/mol (page 6). This Q st values falls within the claimed range, therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to arrive at a microporous polymer having a CO 2 Q st within the claimed range. Regarding claim 13 , Zhou fails to disclose that the microporous polymer has a CO 2 uptake of 120 to 125 milligrams per gram (mg g −1 ) at a pressure of 1 bar and a temperature of 273 kelvin (K). However, Hassan discloses the CO 2 uptakes of porous organic polymer were found in range of 115–160 mg/g at 273 K and at 1 bar pressure (Table 1, Fig. 5a, page 6). The CO 2 uptake values substantially overlap and is immediately adjacent to the claimed range. It would have been obvious to one of ordinary skill in the art to arrive at a microporous polymer having a CO 2 uptake within the claimed range. Regarding claim 14 , Zhou fails to disclose that the microporous polymer has a CO 2 uptake of 75 to 80 milligrams per gram (mg g −1 ) at a pressure of 1 bar and a temperature of 298 K. However, Hassan discloses the CO 2 uptakes of porous organic polymer were found in range of 60-90 mg/g at 298 K and at 1 bar pressure (Table 1, Fig. 6a, page 6). The CO 2 uptake values substantially overlap and is immediately adjacent to the claimed range. It would have been obvious to one of ordinary skill in the art to arrive at a microporous polymer having a CO 2 uptake within the claimed range. Regarding claim 15 , Zhou fails to disclose that the microporous polymer has a CO 2 uptake of 50 to 60 mg g −1 at a pressure of 1 bar and a temperature of 313 K. However, Hassan discloses that the porous organic polymer with CO 2 uptakes in the range of 115–160 mg/g at 273 K and 60–90 mg/g at 298 K at 1 bar pressure (Table 1). Hassan discloses that the adsorption capacity predictably decreases with increasing temperature due to reduced physisorption interactions between CO 2 molecules and the porous polymer framework (page 6). It would have been obvious to one of ordinary skill in the art at the time of the invention that increasing the temperature from 298 K to 313 K would predictably decrease the CO 2 uptake capacity of the porous polymer system disclosed by Hassan, because physisorption based adsorption decreases with increasing temperature. Also, optimization of adsorption conditions and operating temperature constitutes routine optimization of a result-effective variable. MPEP 2144.05(II). Regarding claim 16 , Zhou fails to disclose the microporous polymer has a methane (CH 4 ) uptake of 10 to 15 mg g −1 at a pressure of 1 bar and a temperature of 273 K. However, Hassan discloses the CH 4 uptakes of porous organic polymer were found in range of 13.0-17.5 mg/g at 273 K and at 1 bar pressure (Table 1, Fig. 5c, page 6). The CH 4 uptake values substantially overlap and is immediately adjacent to the claimed range. It would have been obvious to one of ordinary skill in the art to arrive at a microporous polymer having a CH 4 uptake within the claimed range. Regarding claim 17 , Zhou fails to disclose the microporous polymer has a CH 4 uptake of 5 to 10 mg g −1 at a pressure of 1 bar and a temperature of 298 K. However, Hassan discloses the CH 4 uptakes of porous organic polymer were found in range of 6.0-9.5 mg/g at 298 K and at 1 bar pressure (Table 1, Fig. 6b, page 6). The CH 4 uptake values substantially overlap and is immediately adjacent to the claimed range. It would have been obvious to one of ordinary skill in the art to arrive at a microporous polymer having a CH 4 uptake within the claimed range. Regarding claim 18 , Zhou fails to disclose that the microporous polymer has a selectivity of CO 2 /N 2 from 35 to 40 at a temperature of 273 K. However, Hassan discloses that the CO 2 /N 2 selectivity of the porous polymer systems was estimated using the initial slope ratios from Henry’s law constant for single carbon dioxide and methane or nitrogen adsorption isotherms recorded at 273 K. Figure 7 show CO 2 /N 2 selectivity in the range 24–37 at 273 K. The disclosed selectivity falls within the claimed range (35-40 at 273 K), therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to arrive at a microporous polymer having CO 2 /N 2 selectivity within the claimed range. Regarding claim 19 , Zhou fails to disclose that the microporous polymer has a selectivity of CO 2 /CH 4 from 3 to 5 at a temperature of 273 K. However, Hassan discloses that the CO 2 /CH 4 selectivity of the porous polymer systems was estimated using the initial slope ratios from Henry’s law constant for single carbon dioxide and methane or nitrogen adsorption isotherms recorded at 273 K. Table 1 show CO 2 /CH 4 selectivity in the range 5 to 7 at 273 K. The disclosed selectivity falls within the claimed range (3 to 5 at 273 K); therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to arrive at a microporous polymer having CO 2 /CH 4 selectivity within the claimed range. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to MIRIAM N EZELUOMBA whose telephone number is (571)272-0110. The examiner can normally be reached Monday-Friday 8:00am-4:30pm. 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, Jennifer Dieterle can be reached at 5712707872. 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. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /M.N.E./Examiner, Art Unit 1776 /Jennifer Dieterle/Supervisory Patent Examiner, Art Unit 1776 Application/Control Number: 18/668,928 Page 2 Art Unit: 1776 Application/Control Number: 18/668,928 Page 3 Art Unit: 1776 Application/Control Number: 18/668,928 Page 4 Art Unit: 1776 Application/Control Number: 18/668,928 Page 5 Art Unit: 1776 Application/Control Number: 18/668,928 Page 6 Art Unit: 1776 Application/Control Number: 18/668,928 Page 7 Art Unit: 1776 Application/Control Number: 18/668,928 Page 8 Art Unit: 1776 Application/Control Number: 18/668,928 Page 9 Art Unit: 1776 Application/Control Number: 18/668,928 Page 10 Art Unit: 1776 Application/Control Number: 18/668,928 Page 11 Art Unit: 1776 Application/Control Number: 18/668,928 Page 12 Art Unit: 1776 Application/Control Number: 18/668,928 Page 13 Art Unit: 1776 Application/Control Number: 18/668,928 Page 14 Art Unit: 1776 Application/Control Number: 18/668,928 Page 15 Art Unit: 1776
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