CTNF 18/639,477 CTNF 100238 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 6 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. Claim 6 recites the limitation “wherein the reacted units have a formula (III): PNG media_image1.png 252 238 media_image1.png Greyscale wherein ~~~ is an adjacent contorted polymeric structure.” The formulas included in claim 6 are illegible, rendering the scope of the claim indefinite. In order to promote compact prosecution, the Examiner has examined the structure found in Figure 1B, which is a higher quality depiction of said formula. Claim Rejections - 35 USC § 102 07-07-aia AIA 07-07 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 – 07-08-aia AIA (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. 07-12-aia AIA (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. 07-15 AIA Claim s 1-20 are rejected under 35 U.S.C. 102( a)(1 ) as being anticipated by Ansari, M. et al. Thermally Stable and High-Surface-Area Triptycene and Phenanthroline-Based Microporous Polymer for Selective CO2 Capture over CH4 and N2, Applied Polymer Materials , Vol. 6, no. 7 (March 20, 2024), pp. 3996-4004 (hereinafter referred to as Ansari). Although the publication names the two inventors of record, if the instant application names fewer joint inventors than a publication, it is not readily apparent from the publication that it is an inventor-originated disclosure and the publication is therefore treated as prior art under AIA 35 U.S.C. 102(a)(1). See MPEP § 2153.01(a) . Regarding claim 1 , Ansari teaches a microporous polymer material, comprising: a polymer comprising reacted units of a triptycene compound and a phenanthroline compound (Abstract “This work describes the design, characterization, and CO2 capture studies of a 3D-triptycene and phenanthroline-based microporous polymer (TPPM).”), wherein the polymer has a contorted polymeric structure (Scheme 1, TPPM is a contorted polymer ; Pg. 3997 “the incorporation of phenanthroline motif to design inflexible and contorted network polymers”); wherein a molar ratio of the triptycene compound to the phenanthroline compound is in a range of 1:1 and 1:4 (Section 2.2 “The synthesis of TPPM was carried out as follows: A mixture of triptycene (254 mg, 1 mmol), 2,9-dichloro-1,10-phenanthroline (373.5 mg, 1.5 mmol)” ; ratio of triptycene to phenanthroline is therefore 1:1.5); and wherein, in the polymer, the triptycene compound is covalently bonded to the phenanthroline compound (Scheme 1). Regarding claim 2 , Ansari teaches the microporous polymer material as applied to claim 1 above, wherein the triptycene compound has a formula (I): PNG media_image2.png 246 269 media_image2.png Greyscale wherein R1 to R12 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl, an optionally substituted aryl, and an optionally substituted heterocyclic aryl (Scheme 1, triptycene compound wherein R1 to R12 are each independently hydrogen atoms). Regarding claim 3 , Ansari teaches the microporous polymer as applied to claim 1 above, wherein the triptycene compound is 9,10-Dihydro-9,10-[1,2]benzenoanthracene (Scheme 2, triptycene has the IUPAC name of 9,10-Dihydro-9,10-[1,2]benzenoanthracene). Regarding claim 4 , Ansari teaches the microporous polymer as applied to claim 1 above, wherein the phenanthroline compound has a formula (II): PNG media_image3.png 191 240 media_image3.png Greyscale wherein R13 and R20 are reach independently a halogen atom (Scheme 1, 2,9-dichloro-1,10-phenanthroline has a halogen atom (chlorine) at positions R13 and R20); and wherein R14 to R19 are each independently selected from the group consisting of a hydrogen atom, a halogen atom, an optionally substituted alkyl, an optionally substituted aryl, and an optionally substituted heterocyclic aryl (Scheme 1, 2,9-dichloro-1,10-phenanthroline has a hydrogen atom at positions R14 to R19). Regarding claim 5 , Ansari teaches the microporous polymer as applied to claim 4 above, wherein the phenanthroline compound is 2,9-dichloro-1,10-phenanthroline (Scheme 1). Regarding claim 6 , Ansari teaches the microporous polymer as applied to claim 1 above, wherein the reacted units have a formula (III): PNG media_image4.png 242 245 media_image4.png Greyscale wherein ~~~ is an adjacent contorted polymeric structure (Scheme 1 depicts polymeric structure ; Section 3.1 “Additionally, the peak observed at 2960 cm -1 corresponds to the stretching vibration of triptycene bridge head -CH- groups indicating successful cross-linking.”). Regarding claim 7 , Ansari teaches the microporous polymer material as applied to claim 1 above, wherein particles of the microporous polymer material are in the form of microspheres having an average diameter in a range of 0.5 to 1 micrometer (Abstract “Morphological characterization of the polymer sample shows the formation of microspheres with diameters around 0.5-1 µm.”). Regarding claim 8 , Ansari teaches the microporous polymer material as applied to claim 7 above, wherein the microspheres are aggregated (Figs. 3a-3c show FESEM micrographs of aggregated microspheres). Regarding claim 9 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a Brunauer-Emmett-Teller (BET) surface area of 1100 to 1200 square meter per gram (Section 1 (Pg. 3997) “TPPM was found to be ultramicroporous with a high BET-specific surface area of 1120 m2/g.”). Regarding claim 10 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a total pore volume of 0.6 to 0.7 cubic centimeters per gram (Table 1 shows V tot for TPPM as 0.650 cm3/g). Regarding claim 11 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a micropore volume of 0.4 to 0.5 cm3/g (Table 1 shows V mic for TPPM as 0.445 cm3/g). Regarding claim 12 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a carbon dioxide isosteric heat of adsorption of 20 to 30 kJ/mol (Table 1 shows Q st for TPPM as 23 kJ/mol). Regarding claim 13 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a CO2 uptake of about 2.5 to 3 mmol/g of the microporous polymer material at about 273 K and 1 bar (Table 1 shows CO2 uptake at 273 K and 1 bar for TPPM as 2.76 mmol/g). Regarding claim 14 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a CO2 uptake of about 1.5 to 2.3 mmol/g at about 298 K and 1 bar (Table 1 shows CO2 uptake at 298 K and 1 bar for TPPM as 1.85 mmol/g). Regarding claim 15 , Ansari teaches the microporous polymer material as applied to claim 1 above, having a thermal degradation temperature of 350 to 420 ⁰C, wherein the thermal degradation temperature is determined at a weight loss of 10 percent by weight based on an initial weight of the microporous polymer material (Section 3.1 (Pg. 3999) “For TPPM, the thermal degradation temperature (T d = 10% weight loss under air) was 382 ⁰C.”). Regarding claim 16 , Ansari teaches a method for capturing carbon dioxide directly from a CO2-containing gaseous composition (Section 3.3 “We measured CO2 uptake isotherms at different temperatures to assess the CO2 capture capability of TPPM”), comprising: contacting and passing the CO2-containing gaseous composition through particles of the microporous polymer material of claim 1 (Fig. 6 shows adsorption isotherms of TPPM for CO2), thereby adsorbing at least a portion of CO2 from the CO2-containing gaseous composition onto surfaces of the microporous polymer material particles and forming a purified gas composition (Section 4 “TPPM showed a high CO2 uptake of 2.76 mmol/g at a 273 K temperature.”). Regarding claim 17 , Ansari teaches the method as applied to claim 16 above, wherein the CO2 is present in the CO2-containing gaseous composition in an amount of 5 to 60 vol.% based on a total volume of the CO2-containing gaseous composition (Section 3.4 “Therefore, we assessed TPPM’s performance for the separation of natural gas containing a CO2/CH4 mixture (50% CO2:50% CH4)”). Regarding claim 18 , Ansari teaches the method as applied to claim 16 above, wherein the CO2-containing gaseous composition comprises CO2 and N2 (Section 3.4 “Therefore, we assessed TPPM’s performance for the separation of … flue gas containing a CO2/N2 mixture (15/85, v/v)”), and wherein the microporous polymer material has a Henry’s Law selectivity for CO2 over N2 of about 20 to 27.8 at 270-300 K and 1 bar (Section 3.4 “TPPM displayed a promising CO2/N2 selectivity of 27.8 at 273 K and 1 bar pressure.”). Regarding claim 19 , Ansari teaches the method as applied to claim 16 above, wherein the CO2-containing gaseous composition comprises CO2 and CH4 (Section 3.4 “Therefore, we assessed TPPM’s performance for the separation of natural gas containing a CO2/CH4 mixture (50% CO2:50% CH4)”), and wherein the microporous polymer material has a Henry’s Law selectivity for CO2 over CH4 of about 3.8 to 5.8 at 270-300 K and 1 bar (Section 3.4 “The CO2/CH4 selectivity values were measured to be 5.8 and 3.8 at 273 and 298 K temperatures, respectively.”). Regarding claim 20 , Ansari teaches the method as applied to claim 16 above, further comprising: preparing the microporous polymer material by: mixing a triptycene compound, a phenanthroline compound, and an aluminum salt in an organic solvent to form a mixture (Section 2.2 “A mixture of triptycene, 2,9-dichloro-1,10-phenanthroline, and AlCl3 was placed in a 100 mL round-bottom flask with a three-necked adapter. The flask was purged with nitrogen and then filled with dry DCM (30 mL).”); wherein a molar ratio of the triptycene compound to the phenanthroline compound is in a range of 1:1 to 1:2 (Section 2.2 “A mixture of triptycene (254, 1 mmol), 2,9-dichloro-1,10-phenanthroline (373.5 mg, 1.5 mmol)” ; ratio of triptycene to phenanthroline is therefore 1:1.5); wherein a molar ratio of the triptycene compound to the aluminum salt is in a range of 1:2 to 1:8 (Section 2.2. “A mixture of triptycene (254, 1 mmol), 2,9-dichloro-1,10-phenanthroline (373.5 mg, 1.5 mmol), and AlCl3 (532 mg, 4 mmol)” ; ratio of triptycene to aluminum salt is therefore 1:4); heating and refluxing the mixture to form the microporous polymer material in the mixture (Section 2.2 “This reaction mixture was heated and stirred under reflux for 24 h.”); and separating the microporous polymer material from the mixture by filtering, washing, and drying (Section 2.2 “After cooling, the solid polymer was filtered through a glass frit and washed sequentially with DCM, water, methanol, THF, and acetone. … The brown-colored solid polymer was dried in a vacuum oven”). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL MARIE SLAUGOVSKY whose telephone number is (571)272-0188. The examiner can normally be reached Monday - Friday 8:30 am - 5:30 pm EST. 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 (571) 270-7872. 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. /RACHEL MARIE SLAUGOVSKY/Examiner, Art Unit 1776 /Jennifer Dieterle/Supervisory Patent Examiner, Art Unit 1776 Application/Control Number: 18/639,477 Page 2 Art Unit: 1776 Application/Control Number: 18/639,477 Page 3 Art Unit: 1776 Application/Control Number: 18/639,477 Page 4 Art Unit: 1776 Application/Control Number: 18/639,477 Page 5 Art Unit: 1776 Application/Control Number: 18/639,477 Page 6 Art Unit: 1776 Application/Control Number: 18/639,477 Page 7 Art Unit: 1776 Application/Control Number: 18/639,477 Page 8 Art Unit: 1776 Application/Control Number: 18/639,477 Page 9 Art Unit: 1776
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