DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission on 07/16/2026 has been entered. Upon entering the submission, new claims 27-31 are added. Claims 16-26 are cancelled. Claims 1-15, and 27-31 are pending, and under examination on the merits.
Declaration under Rule 37 C.F.R. §1.130(a)
Applicant’s submission of the Declaration under Rule 37 C.F.R. §1.130(a), filed on 06/09/2026 has been entered and considered.
Response to RCE Submission
Claim rejection under 35 U.S.C. §102(a)(1)
Applicant filed the Declaration under Rule 37 C.F.R. §1.130(a), which exempts the previously cited prior art as a prior art under 35 U.S.C. §102(b)(1)(A). The 102(a) rejection is hereby withdrawn.
Claim rejection under 35 U.S.C.§103(a)
In terms of Applicant’s 1st argument “The Record Contains No Articulated Reason to Combine”, the motivation for modifying Sekizkardes' polymer with the amidoxime moiety is taught and/or suggested by Patel et al. Specifically, Patel et al. discloses the first noninvasive functionalization of PIMs by the amidoxime functionality to increase carbon dioxide capacity without adversely affecting physicochemical properties. Amidoximes are known to be CO2-philic and our results challenge the common perception in which post-modifications are expected to diminish properties of the original solid (i.e., unmodified PIMs). See right column, p.9989. Patel et al. teaches Amidoxime-PIM-1 was used as an adsorbent for CO2 capture because of the presence of basic nitrogen, hydroxyl and intrinsic microporosity in the Amidoxime-PIM-1. Strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity. Functionalization of PIM-1 by amidoxime creates sites that have a strong affinity toward CO2 through its high quadruple moment with 8% enhancement. See right column, p.9990. Patel et al. teaches amidoxime-modified polymer intrinsic microporosity chemical sorbents (Amidoxime-PIM-1) for improving CO2 capture capacity up to 17% and micropore surface area by 20% without losing its film (e.g. fiber) forming ability (see Abstract at p.9989; and Fig. 1 at p.9990). Patel et al. also discloses the sorbent Amidoxime-PIM-1 has CO2 uptake selectivity over N2 under various pressures. See Figs. 2-3 at p.9990-9991. In addition, both Sekizkardes et al., Patel et al., and Applicant claimed sorbent materials are used for the same application of CO2 capture. Therefore, the record indeed contains articulated reason to combine the cited prior art references.
In terms of Applicant’s 2nd argument “the Record Contains No Finding of a Reasonable Expectation of Success”, Sekizkardes et al. discloses a polymer intrinsic microporosity (PIMs) chemical sorbents utilizing primary amine appendance through acid-base and hydrogen-bonding interactions. The amine-appended PIMs (e.g. PIM-1-C-TA) not only showed a nearly four-fold enhancement in CO2 loading capacity (36.4 cc/g at 0.15 bar and 298K) and very high CO2/N2 selectivity compared to neat PIM-1 but also proved to have stable performance when cycled between adsorption and desorption isotherms under both dry and humid conditions that are typical for postcombustion CO2 capture (see ABSTRACT at p.30987). In addition, Patel et al. discloses functionalization of PIMs by the amidoxime functionality increases carbon dioxide capacity without adversely affecting physicochemical properties. Amidoximes are known to be CO2-philic and our results challenge the common perception in which post-modifications are expected to diminish properties of the original solid (i.e., unmodified PIMs). See right column, p.9989. Patel et al. teaches Amidoxime-PIM-1 was used as an adsorbent for CO2 capture because of the presence of basic nitrogen, hydroxyl and intrinsic microporosity in the Amidoxime-PIM-1. Strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity. Functionalization of PIM-1 by amidoxime creates sites that have a strong affinity toward CO2 through its high quadruple moment with 8% enhancement. See right column, p.9990. Sekizkardes et al. and Patel et al. teach functionalization of PIMs by the amidoxime functionality increases carbon dioxide capacity without adversely affecting physicochemical properties; and utilizing primary amine appendance through acid-base and hydrogen-bonding interactions of the amine-appended PIMs (e.g. PIM-1-C-TA), which not only showed a nearly four-fold enhancement in CO2 loading capacity (36.4 cc/g at 0.15 bar and 298K) and very high CO2/N2 selectivity compared to neat PIM-1 but also proved to have stable performance when cycled between adsorption and desorption isotherms under both dry and humid conditions. Therefore, the reasonable expectation of success becomes obvious.
In terms of Applicant’s 3rd argument “The Unexpected-Results Analysis Rests on the Wrong Baseline”, there is no unexpected-results, because the results Applicant demonstrated are indeed expected for one ordinary skilled in the art based on the disclosures by Sekizkardes et al. and Patel et al.
In terms of Applicant’s 4th argument “Rebuttal Evidence Is Not Reached Until a Prima Facie Case Is Made Out”, a prima facie case is indeed made out based on the disclosures by Sekizkardes et al. and Patel et al. and articulation above and the previous Office actions.
Therefore, Applicant’s argument is not persuasive, and the 103(a) rejection is maintained.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claim 27 is rejected under 35 U.S.C. 112, first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor(s), at the time the application was filed, had possession of the claimed invention.
Specifically, 27 contains the phrase “wherein the alkyl amine comprises between 2 and 5 amine groups and has a molecular weight of between 31 and 300 daltons”. However, this limitation is not disclosed in the original disclosure. The present Specification [0017] discloses “Preferably the alkyl amine has a molecular weight of between 31 and 300 daltons, or 31 and 200 daltons.”, the specification does not disclose the alkyl amine having a molecular weight of between 31 and 300 daltons, or 31 and 200 daltons comprises between 2 and 5 amine groups. Therefore, new claim 27 introduces NEW MATTER. To overcome the rejection, Applicant needs to specifically point out the support for the amendment, or delete the new matter.
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.
Claim 27 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 pre-AIA the applicant regards as the invention.
Specifically, claim 27 contains the phrase “wherein the alkyl amine comprises between 2 and 5 amine groups and has a molecular weight of between 31 and 300 daltons”. However, the alkyl amine comprises between 2 amine groups having the smallest molecular weight is the amine compound of methanediamine (H2N-CH2-NH2), which has a molecular weight of 46.07 daltons, and cannot be 31 daltons. Therefore, claim 27 is indefinite.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 1-15 and 27-31 are rejected under 35 U.S.C. 103 as being unpatentable over Sekizkardes et al., ACS Applied Materials & Interface, (2019), v.11, p.30987-30991 in view of Patel et al., Chem. Comm., (2012), v.48, p.9989-9991.
Applicant’s claim 1 is drawn to a sorbent material, comprising: a polymer comprising an amidoxime moiety; and an alkyl amine disposed on a surface of the polymer.
Determination of the scope and content of the prior art (MPEP §2141.01)
Sekizkardes et al. discloses a polymer intrinsic microporosity (PIMs) chemical sorbents utilizing primary amine appendance through acid-base and hydrogen-bonding interactions. The amine-appended PIMs (e.g. PIM-1-C-TA) not only showed a nearly four-fold enhancement in CO2 loading capacity (36.4 cc/g at 0.15 bar and 298K) and very high CO2/N2 selectivity compared to neat PIM-1 but also proved to have stable performance when cycled between adsorption and desorption isotherms under both dry and humid conditions that are typical for postcombustion CO2 capture (see ABSTRACT at p.30987). Sekizkardes et al. also discloses a primary alkylamine appended polymer intrinsic microporosity PIM-1-C3-TA with pore size distribution Figure 1c
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. In addition, Sekizkardes et al. discloses CO2 uptake performance of primary alkylamine appended polymer intrinsic microporosity PIM-1-C1-TA, PIM-1-C2-TA, and PIM-1-C3-TA in Table 1. All the primary alkylamine appended polymers show enhanced CO2 capture capacity over the non-alkylamine appended polymer (PIM-1) under various temperatures and pressures, which demonstrates loading primary (alkyl)amines into the hydrolyzed PIMs resulted in a drastic increase in CO2 uptake capacity (see left column at p.30989). Sekizkardes et al. discloses CO2 uptake performance of PIM-1-C3-TA in Table 1 in Figure 2(A).
Patel et al. discloses the first noninvasive functionalization of PIMs by the amidoxime functionality to increase carbon dioxide capacity without adversely affecting physicochemical properties. Amidoximes are known to be CO2-philic and our results challenge the common perception in which post-modifications are expected to diminish properties of the original solid (i.e., unmodified PIMs). See right column, p.9989. Patel et al. teaches Amidoxime-PIM-1 was used as an adsorbent for CO2 capture because of the presence of basic nitrogen, hydroxyl and intrinsic microporosity in the Amidoxime-PIM-1. Strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity. Functionalization of PIM-1 by amidoxime creates sites that have a strong affinity toward CO2 through its high quadruple moment with 8% enhancement. See right column, p.9990. Patel et al. teaches amidoxime-modified polymer intrinsic microporosity chemical sorbents (Amidoxime-PIM-1) for improving CO2 capture capacity up to 17% and micropore surface area by 20% without losing its film (e.g. fiber) forming ability (see Abstract at p.9989; and Fig. 1 at p.9990). Patel et al. also discloses the sorbent Amidoxime-PIM-1 has CO2 uptake selectivity over N2 under various pressures. See Figs. 2-3 at p.9990-9991. Patel et al. discloses amidoxime-modified polymer intrinsic microporosity chemical sorbents can be powder (see p.9990). In addition, Patel et al. discloses the solubility of PIMs is one of the major benefits for casting robust, self-standing films by conventional solution-based polymer processing techniques. Membranes offer a low cost, more energy-efficient CO2 capture option. See left column, p.9989.
Ascertainment of the difference between the prior art and the claims (MPEP §2141.02)
The difference between Sekizkardes et al. and Applicant’s inventions is the prior art does not teach the amine-appended PIMs polymer absorbent (e.g. PIM-3-C-TA) comprising an amidoxime moiety, instead, a carboxylate and/or amide moieties.
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
However, the difference between the instantly claimed sorbent materials and the sorbent material of Sekizkardes et al. is further taught and/or suggested by Patel et al.
Patel et al. teaches functionalization of PIMs by the amidoxime functionality to increase carbon dioxide capacity without adversely affecting physicochemical properties. Amidoximes are known to be CO2-philic and our results challenge the common perception in which post-modifications are expected to diminish properties of the original solid (i.e., unmodified PIMs). See right column, p.9989. Patel et al. teaches Amidoxime-PIM-1 was used as an adsorbent for CO2 capture because of the presence of basic nitrogen, hydroxyl and intrinsic microporosity in the Amidoxime-PIM-1. Strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity. Functionalization of PIM-1 by amidoxime creates sites that have a strong affinity toward CO2 through its high quadruple moment with 8% enhancement. See right column, p.9990. Patel et al. teaches amidoxime-modified polymer intrinsic microporosity chemical sorbents (Amidoxime-PIM-1) for improving CO2 capture capacity up to 17% and micropore surface area by 20% without losing its film (e.g. fiber) forming ability (see Abstract at p.9989; and Fig. 1 at p.9990). Patel et al. also discloses the sorbent Amidoxime-PIM-1 has CO2 uptake selectivity over N2 under various pressures. See Figs. 2-3 at p.9990-9991. Patel et al. teaches Amidoxime-PIM-1 was used as an adsorbent for CO2 capture because of the presence of basic nitrogen, hydroxyl and intrinsic microporosity in the Amidoxime-PIM-1. Strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity. Patel et al. teaches functionalization of PIMs by the amidoxime functionality increases carbon dioxide capacity without adversely affecting physicochemical properties; and Sekizkardes et al. teaches utilizing primary amine appendance through acid-base and hydrogen-bonding interactions of the amine-appended PIMs (e.g. PIM-1-C-TA), which not only showed a nearly four-fold enhancement in CO2 loading capacity (36.4 cc/g at 0.15 bar and 298K) and very high CO2/N2 selectivity compared to neat PIM-1, but also proved to have stable performance when cycled between adsorption and desorption isotherms under both dry and humid conditions.
In addition, both Sekizkardes et al. and Patel et al. are drawn to sorbent materials used for CO2 capture. They are used for the same application of the presently claimed sorbent. One ordinary skilled in the art would have been motivated to modify the alkylamine modified polymers comprising carboxylate and/or amide moiety disclosed Sekizkardes with the moiety of amidoxime disclosed by Patel to further improve the absorbent’s CO2 uptake capacity and CO2 selectivity N2 in light of Patel’s disclosure (see Figs. 2-3 at p.9990-9991). Therefore, Sekizkardes et al. in view of Patel et al. would have rendered claims 1-3, 6, 9, and 11-15 obvious.
In terms of claims 4-5, and 7-8, Patel et al. discloses amidoxime-modified polymer intrinsic microporosity chemical sorbents (Amidoxime-PIM-1) for improving CO2 capture capacity up to 17% and micropore surface area by 20% without losing its film (e.g. fiber) forming ability (see Abstract at p.9989; and Fig. 1 at p.9990). Patel et al. also discloses the solubility of PIMs is one of the major benefits for casting robust, self-standing films by conventional solution-based polymer processing techniques. Membranes offer a low cost, more energy-efficient CO2 capture option. See left column, p.9989. Therefore, Patel et al. teaches and/or suggests the sorbent of claims 4-5, and 7-8 comprising sorbent fillers to enhance the performance of CO2 capture membranes or films by further including other CO2 absorbent such as porous silica, porous organic polymers.
In terms of claim 10, Patel et al. also discloses the solubility of PIMs is one of the major benefits for casting robust, self-standing films by conventional solution-based polymer processing techniques. Membranes offer a low cost, more energy-efficient CO2 capture option. Cutting a solid continuous structure having a dimension in at least one direction of at least 1 cm, or at least 5 cm is a routine operation for preparing self-standing films by conventional solution-based polymer processing techniques.
In terms of new claim 27 drawn to a sorbent material, comprising: a polymer comprising an amidoxime moiety; and an alkyl amine disposed on a surface of the polymer; wherein the alkyl amine comprises between 2 and 5 amine groups and has a molecular weight of between 31 and 300 daltons; and wherein the sorbent material is characterizable by a CO2 uptake of at least 35 cm3/g sorbent at 400 mbar CO2 at 298 K, Sekizkardes et al. discloses a polymer intrinsic microporosity (PIMs) chemical sorbents utilizing primary amine appendance through acid-base and hydrogen-bonding interactions. The amine-appended PIMs (e.g. PIM-1-C-TA) not only showed a nearly four-fold enhancement in CO2 loading capacity (36.4 cc/g at 0.15 bar and 298K) and very high CO2/N2 selectivity compared to neat PIM-1 but also proved to have stable performance when cycled between adsorption and desorption isotherms under both dry and humid conditions that are typical for post-combustion CO2 capture (see ABSTRACT at p.30987). The amine of the amine-appended PIMs (e.g. PIM-1-C3-TA) is
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, which comprises 4 amine groups, and has a molecular weight of 146 daltons. In terms of the sorbent material is characterizable by a CO2 uptake of at least 35 cm3/g sorbent at 400 mbar CO2 at 298 K, Sekizkardes et al. discloses an amine-appended PIM (PIM-1-C-TA) showed CO2 loading capacity of 36.4 cc/g at 0.15 bar and 298K. Furthermore, if the product is obvious over the product of the prior art references, the physical properties associated with the product would have been otherwise obvious product.
In terms of new claim 28 drawn to a sorbent material wherein the sorbent material is characterizable by an isosteric heat of adsorption for CO2 of about 50 to about 75 kJ/mol at a CO2 loading in the range of 20 to 50 cm3/g, Sekizkardes et al. discloses an amine-appended PIM (PIM-1-C-TA) showed CO2 loading capacity of 36.4 cc/g at 0.15 bar and 298K. In terms of isosteric heat of adsorption for CO2 of about 50 to about 75 kJ/mol at a CO2 loading in the range of 20 to 50 cm3/g, it would be an inherited property of the product at a CO2 loading in the range of 20 to 50 cm3/g. If the product is obvious over the prior art references, the physical properties associated with the product would have been otherwise obvious product.
In terms of new claim 29 drawn to a sorbent material wherein the alkyl amine comprises diethylenetriamine, Sekizkardes et al. teaches the amine is
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, which is an obvious analogous amine of diethylenetriamine.
In terms of new claim 30 characterizable by an isosteric heat of adsorption for CO2 of about 55 to about 70 kJ/mol at a CO2 loading in the range of 20 to 50 cm3/g, Sekizkardes et al. discloses an amine-appended PIM (PIM-1-C-TA) showed CO2 loading capacity of 36.4 cc/g at 0.15 bar and 298K. In terms of isosteric heat of adsorption for CO2 of about 50 to about 75 kJ/mol at a CO2 loading in the range of 20 to 50 cm3/g, it would be an inherited property of the product at a CO2 loading in the range of 20 to 50 cm3/g. If the product is obvious over the prior art references, the physical properties associated with the product would have been otherwise obvious product.
In terms of new claim 31 characterizable by a CO2 uptake of about 40 to about 50 cm3/g sorbent at 400 mbar CO2 at 298 K, Sekizkardes et al. discloses an amine-appended PIM (PIM-1-C-TA) showed CO2 loading capacity of 36.4 cc/g at 0.15 bar and 298K. In addition, Patel et al. discloses functionalization of PIMs by the amidoxime functionality to increase carbon dioxide capacity without adversely affecting physicochemical properties, and amidoximes are known to be CO2-philic and our results challenge the common perception in which post-modifications are expected to diminish properties of the original solid (i.e., unmodified PIMs). See right column, p.9989. Patel et al. teaches strong interactions between the porous polymeric networks and CO2 are essential for enhancing the CO2 adsorption capacity, and functionalization of PIM-1 by amidoxime creates sites that have a strong affinity toward CO2 through its high quadruple moment with 8% enhancement. See right column, p.9990. Patel et al. teaches amidoxime-modified polymer intrinsic microporosity chemical sorbents (Amidoxime-PIM-1) for improving CO2 capture capacity up to 17% and micropore surface area by 20% without losing its film (e.g. fiber) forming ability (see Abstract at p.9989; and Fig. 1 at p.9990). It becomes clear combining functionalization of PIM by amidoxime with amine-appendance disclosed by Sekizkardes et al. and Patel et al. would have greatly increase the CO2 capture capacity from 36.4 cc/g at 0.15 bar and 298K to the claimed range of about 40 to about 50 cm3/g sorbent at 400 mbar CO2 at 298 K.
Conclusions
Claims 1-15, and 27-31 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Yong L. Chu, whose telephone number is (571)272-5759. The examiner can normally be reached on M-F 8:30am-5:00pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amber R. Orlando can be reached on 571-270-3149. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300.
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/YONG L CHU/Primary Examiner, Art Unit 1731
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