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 .
Detailed Action
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 filed on 8/12/26 has been entered.
Due to applicant’s claim amendments filed 5/28/26, the 103 rejection over Abney et al. set forth in the Office Action of 5/28/26 is withdrawn. However, new rejections are in order as shown below.
Claims 1-21 are pending. Claims 17-21 have been withdrawn.
Claims 1-16 are currently under examination.
Claim Objections
Claim 1 is objected to because of the following informalities:
Claim 1 recites “mixing a base porous material comprising a porous structure and a labile ligand with a functionalizing agent to form a slurry.” The wording is confusing. It can be read as a base porous material that comprises a porous structure and a labile ligand. It can also be read as a base porous material that comprises a porous structure and a labile-ligand-with-a-functionalizing-agent. The examiner suggests the following claim wording: “mixing, with a functionalizing agent, a base porous material comprising a porous structure and a labile ligand, to form a slurry.” Appropriate correction is required.
Claim Rejections – 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112:
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 of carrying out his invention.
Claims 1-16 are rejected under 35 U.S.C. 112, first paragraph, as failing to comply with the written description requirement. The claims contain 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 inventors, at the time the application was filed, had possession of the claimed invention.
Claim 1 recites “functionalizing the open metal sites in the slurry with the functionalizing agent to form a functionalized porous material comprising the functionalizing agent coordinated to the open metal sites.” Claim 1 no longer recites a drying step.
There is no support in the specification as filed for forming the functionalized porous material in the slurry, without drying. Each disclosure of forming the product ties the product to the drying step:
Reference to applicant’s specification refers to applicant’s PGPub: US 20240299905
For examples see Paragraph [0005] and paragraph [0055] which recite “and drying the slurry to form a functionalized porous material comprising the functionalizing agent coordinated to the open metal sites.” Similarly, also see paragraphs [0013], [0015], [0029] and examples 1-7, which also recite drying of the slurry.
Thus the amendment to claim 1 raises an issue of new matter. The dependent claims are rejected as being dependent on a rejected claim.
The following is a quotation of the second paragraph of 35 U.S.C. 112:
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.
Claims 11 and 12 are rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention.
Claim 11 recites “wherein the slurry is dried at a temperature of about 20 °C to about 150 °C and a pressure of about 101,325 pascals to about 100 pascals to form the functionalized porous material.” Claim 12 recites similar language. However, claim 1 states that the functionalizing step forms the functionalized porous material. Claims 11 and 12 state that the drying step forms it. It is unclear whether “the functionalized porous material” of claims 11 and 12 is the same material as that of claim 1, or a second material formed by a second step. The metes and bounds of claims 11 and 12 are thus unclear. Appropriate correction is required.
Claim Rejections – 35 USC 102/103
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 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. 1 03(a) are summarized as follows:
Applicant Claims
Determining the scope and contents of the prior art.
Ascertaining the differences between the prior art and the claims at issue, and resolving the level of ordinary skill in the pertinent art.
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 1-5, 7-9 and 15-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by or, in the alternative, under 35 U.S.C. 103(a) as being obvious over Siegelman et al. (“Controlling Cooperative CO2 Adsorption in Diamine-Appended Mg2(dobpdc) Metal–Organic Frameworks,” J. Am. Chem. Soc. 2017, 139, 10526-10538, and Supporting Information, pub date Aug. 2, 2017).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Siegelman et al. teaches the metal-organic framework (MOF) Mg2(dobpdc), where dobpdc is 4,4′-dioxidobiphenyl-3,3′-dicarboxylate, see below. The MOF has one-dimensional hexagonal channels lined with open Mg(II) metal sites. Thus Mg2(dobpdc) is a porous structure having open metal sites and a plurality of pores. (abstract; page 10527, Figure 1a and figure notes)
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Siegelman et al. teaches making Mg2(dobpdc) by reacting the metal salt Mg(NO3)2·6H2O with the organic bridging ligand H4dobpdc in a 55:45 methanol:DMF reaction solvent at 120 °C for 20 hours. The crude solid is soaked three times in DMF and then soaked three times in methanol. This gives “[t]he methanol-solvated framework.” (page 10527, last paragraph to page 10528, first paragraph)
Siegelman et al. teaches an activation-free grafting method:
“For all subsequent experiments, it was found that identical CO2 adsorption performance could be achieved through direct diamine-grafting of methanol-solvated Mg2(dobpdc), enabling rapid sample preparation by eliminating time-consuming activation of the parent framework. In this rapid procedure, approximately 30 mg of methanol-solvated Mg2(dobpdc) was isolated by filtration, washed with 30 mL of toluene, and submerged in 5 mL of a 20% (v/v) solution of diamine in toluene. After 12 h, the solid was isolated by filtration and washed with 30 mL of fresh toluene to remove excess diamine.” (page 10528, 3rd paragraph)
Siegelman et al. further teaches that methanol is the bound solvent, and that the diamine is grafted while the methanol is still bound:
“After washing the as-synthesized framework with DMF and exchanging the bound solvent with methanol, diamine-appended Mg2(dobpdc) analogues were rapidly prepared by submerging aliquots of the framework in 20% (v/v) solutions of diamine in toluene. While previous reports of diamine-appended M2(dobpdc) frameworks stipulated removal of bound solvent molecules by heating in vacuo at 250 °C prior to diamine grafting, we determined that functionalization with diamines could be achieved directly with methanol-solvated Mg2(dobpdc). In this activation-free procedure, a greater excess of diamine (~50 equiv per MgII site) is typically required, as compared to ~10 equiv in the procedure involving activation.” (page 10529, right column, first paragraph)
Thus the bound methanol sits on the open metal sites and competes with the diamine for those sites. This is why Siegelman et al. needs five times more diamine when the framework is not activated. The diamine displaces the bound methanol from the open metal sites.
Siegelman et al. teaches that a solid suspended in a 20% (v/v) diamine in toluene solution is a “slurry.” (page 10529, right column, first paragraph)
Siegelman et al. teaches nine diamines in Table 1, including N,N′-diethylethylenediamine (“e-2-e”), N,N-diethylethylenediamine (“ee-2”), N,N′-diisopropylethylenediamine (“i-2-i”) and N,N-diisopropylethylenediamine (“ii-2”). All nine analogues were prepared by the activation-free procedure from methanol-solvated Mg2(dobpdc). (page 10529, Table 1 see below)
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Siegelman et al. teaches that the diamine coordinates to the open metal site through a metal-nitrogen bond, as shown by the first coordination spheres in the single crystal structures. (page 10530, Figure 2, see below)
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Siegelman et al. teaches that grafting goes to completion. Diamine loading was confirmed by 1H NMR of digested samples and by a CO2 saturation loading of 1 CO2 per diamine-Mg(II) site. (page 10530, last paragraph; Supporting Information, page S-15, Figure S10)
Siegelman et al. teaches that samples were desolvated by heating in vacuo at 120 °C for 12 hours. (page 10528, second paragraph)
The methanol bound to the open metal sites would be considered the “labile ligand.” The diamine would be considered the “functionalizing agent.” The toluene would be considered the “slurry solvent.”
With regard to the boiling temperatures, Siegelman et al. plots the boiling point of each of the nine diamines in Figure S8 of the Supporting Information. (Supporting Information, page S-14, Figure S8) Methanol has a boiling point of 64.7 °C, as set forth in the Office Action of 5/28/26. Figure S8 plots m-2-m, that is mmen, at about 120 °C, which matches the mmen boiling point of 120 °C already of record in the Office Action of 5/28/26.
From Figure S8, the diamine boiling points and the resulting differences over methanol are as follows:
• e-2-e, about 152 °C, a difference of about 87 °C over methanol;
• ee-2, about 145 °C, a difference of about 80 °C over methanol;
• i-2 and i-2-i, about 137 °C and about 170 °C, differences of about 72 °C and about 105 °C over methanol; and
• ii-2, about 170 °C, a difference of about 105 °C over methanol.
Each of these differences falls within applicant’s claimed range of about 50 °C to about 150 °C in claim 1 and within applicant’s claimed range of about 60 °C to about 120 °C in claim 3. Thus the boiling temperature relationship of claims 1 and 3 is an inherent property of the diamine and bound methanol pairings that Siegelman et al. actually prepared.
With regard to claim 1, Siegelman et al. teaches mixing a base porous material, methanol-solvated Mg2(dobpdc), with a functionalizing agent, a diamine, to form a slurry. The porous structure, Mg2(dobpdc), has open metal sites and a plurality of pores. The labile ligand, methanol, is coordinated to the open metal sites, since Siegelman et al. calls methanol the “bound solvent” and needs a five-fold larger diamine excess to displace it. The second boiling temperature of the diamine is about 50 °C to about 150 °C higher than the first boiling temperature of methanol, as set forth above. The open metal sites are functionalized in the slurry with the diamine to form a functionalized porous material comprising the diamine coordinated to the open metal sites, as shown by the metal-nitrogen bonds and the near-quantitative diamine loading.
With regard to claim 2, Mg2(dobpdc) is a metal-organic framework material.
With regard to claim 3, the boiling temperature difference is about 87 °C for e-2-e, about 80 °C for ee-2, about 72 °C for i-2, and about 105 °C for i-2-i and ii-2. Each falls within about 60 °C to about 120 °C.
With regard to claims 4 and 5, the labile ligand of Siegelman et al. is methanol. The framework is described as “methanol-solvated,” and the bound solvent was exchanged to methanol. Thus the labile ligand is 100 wt% methanol, which is greater than about 50 wt%.
With regard to claim 7, the functionalizing agents of Siegelman et al. are diamines. (page 10529, Table 1)
With regard to claim 8, the open metal sites of Mg2(dobpdc) are Mg ions.
With regard to claim 9, the mixing of Siegelman et al. is conducted in the presence of a slurry solvent, toluene.
With regard to claim 15, Siegelman et al. obtains near-quantitative diamine loading, washes the grafted solid with fresh toluene, and desolvates at 120 °C in vacuo. The bound methanol is displaced by the diamine. A material bearing two diamines per Mg2(dobpdc) formula unit cannot also hold 40 wt% or more methanol. Thus a labile ligand content of less than 40 wt% in the functionalized porous material is an inherent property of the product of Siegelman et al.
With regard to claim 16, Siegelman et al. prepares the base porous material by a reaction of the metal salt Mg(NO3)2·6H2O with the organic bridging ligand H4dobpdc in a reaction solvent comprising methanol, which is the labile ligand. (page 10527, last paragraph to page 10528, first paragraph )
In the alternative, claims 1-5, 7-9 and 15-16 are rejected under 35 U.S.C. 103 as being unpatentable over Siegelman et al. To the extent any limitation above is not expressly disclosed, it would have been prima facie obvious to one of ordinary skill in the art at the time of the invention to graft any one of the nine diamines of Table 1 directly onto methanol-solvated Mg2(dobpdc), because Siegelman et al. expressly instructs that this can be done and prepared all nine analogues in that manner. Selecting one member from a small list of fully worked examples is prima facie obvious.
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 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 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over Siegelman et al. (“Controlling Cooperative CO2 Adsorption in Diamine-Appended Mg2(dobpdc) Metal–Organic Frameworks,” J. Am. Chem. Soc. 2017, 139, 10526-10538, and Supporting Information, pub date Aug. 2, 2017), in view of Abney et al. (US 20220048929, pub date Feb. 17, 2022).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
The teachings of Siegelman et al. have been discussed previously within this office action.
Abney et al. teaches a MOF with open metal sites, in which ligands append to and detach from those open metal sites. Abney et al. teaches soaking the MOF in water, methanol or ethanol, which act as coordinating solvents that bind to the open metal sites. Abney et al. teaches that where the coordinating solvent is not washed away with a non-coordinating solvent such as toluene, the coordinating solvent remains bound, and that water is more tightly bound than methanol. (paragraphs 77, 116-117, 120)
Abney et al. teaches that flooding an adsorbent with amine dissolved in organic solvent requires “large quantities of organic solvent …, creating a safety hazard, unnecessary hazardous waste stream, and incurring additional expense.” (paragraph 69)
Abney et al. teaches removal of entrained solvent at 100 °C. Abney et al. also teaches that the synthesis is run from room temperature to about 250 °C at ambient pressure, and that the pressure can be reduced to volatilize the ligands and the solvent. (paragraphs 11, 59-60, 71, 105)
Abney et al. teaches that the MOF is handled as a solvent-wet cake on a glass frit, or as a solvent-wet solid collected by centrifugation. (paragraphs 98, 103, 116)
Abney et al. teaches that “the number of ligands (B) will be equivalent to the number of metal sites,” and exemplifies 2.5 molar equivalents of the amine relative to the MOF. (paragraphs 55, 98)
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Siegelman et al. is deficient in the sense that it does not teach a labile ligand comprising greater than about 50 wt% water. Siegelman et al. is further deficient in the sense that it does not teach mixing in the absence of a solvent, drying the slurry at the claimed temperatures and pressures, the claimed weight ratio of labile ligand to porous structure, or the claimed molar ratio of functionalizing agent to open metal sites.
Abney et al. cures these deficiencies, as described above.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to modify the diamine grafting process of Siegelman et al. with the coordinating solvent, solvent handling, solvent removal and amine loading teachings of Abney et al. Both references are directed to the same field, the appending of amine ligands to the open metal sites of a MOF for CO2 capture. Both use the same reactants, reagents and process steps as the applicant.
With regard to claim 6, Abney et al. teaches that water is a coordinating solvent that binds to the open metal sites of the MOF and is more tightly bound than methanol. It would have been obvious to one of ordinary skill in the art to use water in place of methanol as the bound labile ligand of Siegelman et al., since Abney et al. teaches water, methanol and ethanol as equivalent coordinating solvents for the same open metal sites.
Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982). Water has a boiling point of 100 °C, as set forth in the Office Action of 5/28/26, so the difference over the e-2-e boiling point of about 152 °C in Figure S8 is about 52 °C, which falls within the range of claim 1.
With regard to claim 10, Abney et al. teaches that use of large quantities of organic solvent to deliver amine to a MOF creates a safety hazard, an unnecessary hazardous waste stream, and additional expense. Thus it would have been obvious to one of ordinary skill in the art to leave out the toluene of Siegelman et al. and mix the solvent-wet framework with the diamine alone, in order to cut solvent cost, waste and hazard. A reasonable expectation of success exists because the diamine itself is a liquid and is already present in large excess.
With regard to claims 11 and 12, Siegelman et al. teaches desolvating the grafted material by heating in vacuo at 120 °C for 12 hours. Abney et al. teaches removing entrained solvent at 100 °C, working at ambient pressure, and reducing the pressure to volatilize solvent and ligand. It would have been obvious to one of ordinary skill in the art to remove the liquid from the grafted slurry by heating under reduced pressure rather than by filtration, since both are conventional ways to separate a solid product from a solvent. The claimed temperatures and pressures overlap the ranges disclosed by the art. Further, the drying temperature and the drying pressure are art recognized result-effective variables that control residual solvent content and drying rate. Thus it would be obvious in the optimization process to optimize the drying temperature and the drying pressure.
With regard to claim 13, Abney et al. handles the MOF as a solvent-wet cake or as a solvent-wet solid collected by centrifugation. The amount of coordinating solvent held with the solid before the amine is added is an art recognized result-effective variable, because it sets how much solvent competes for the open metal sites and how thick the resulting slurry is. Thus it would be obvious in the optimization process to optimize the weight ratio of labile ligand to porous structure within the claimed range of about 25:1 to about 0.5:1.
With regard to claim 14, Abney et al. teaches that the number of amine ligands will be equivalent to the number of metal sites, and uses 2.5 molar equivalents of amine relative to the MOF. It would have been obvious to one of ordinary skill in the art to lower the large diamine excess of Siegelman et al. toward the near-stoichiometric ratio taught by Abney et al., in order to cut reagent cost and cut the amount of excess amine that must be washed out. Applicant’s own specification states at paragraph [0027] that “[a] molar ratio of the functionalizing agent relative to the open metal sites in the porous structure is at least 1 to achieve 100% coverage of open metal sites.”
Note also that the order of steps does not impart patentability. The applicant does not show any unusual and/or unexpected results for the limitations stated. Note that the prior art provides the same effect desired by the applicant, the formation of an amine functionalized MOF in which the amine functionalizing agent is coordinated to the open metal sites and the labile ligand has been displaced.
Response to Arguments
Applicant’s arguments have been considered but are not persuasive for the following reasons:
The examiner acknowledges applicant’s argument that the mmen/water and mmen/ethanol pairings of the prior Office Action give boiling temperature differences of about 20 °C and 42 °C, which fall outside the claimed range. The examiner agrees. However this argument is moot in view of the new rejections.
The examiner acknowledges applicant’s argument that Abney et al. teaches only vapor-phase appending and teaches away from solvent mediated appending.
The examiner does not agree with applicant’s arguments. Abney et al. states that “[a]ppending or re-appending the ligand to the metal-organic framework can be performed in solution (liquid) or using the novel vapor-phase methods described herein.” (paragraph 78) Abney et al. also combines the already-formed framework of Formula I with the ligand (B) in a suitable solvent in step 2 of scheme 1, exemplified as 2-ampd in toluene. (paragraphs 64-66) Abney et al. further immerses the stripped MOF-274 in a 20 vol% solution of 2-ampd in toluene and obtains 100.3% to 103% amine loading. (paragraphs 122-125) Thus Abney et al. does teach solution-phase appending of an amine to an already-formed framework.
Further, “the prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed….” (MPEP 2143.01) Also “disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments.” In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). (MPEP 2124)
The examiner acknowledges applicant’s argument that Abney et al. teaches a ligand exchange in the opposite direction, so that no reasonable expectation of success can exist.
The examiner does not agree with applicant’s arguments. This argument is moot in view of the new rejections.
The examiner further notes that applicant’s amendment removed the drying step from claim 1. Claim 1 as amended no longer requires drying, filtration or isolation. Claim 1 as amended therefore reads on the conventional soak-and-graft procedures of the art, including that of Siegelman et al.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. See In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the conflicting application or patent is shown to be commonly owned with this application. See 37 CFR 1.130(b).
Effective January 1, 1994, a registered attorney or agent of record may sign a terminal disclaimer. A terminal disclaimer signed by the assignee must fully comply with 37 CFR 3.73(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission.
Claims 1-16 are rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-10 of US 12303865 (Gosselin et al., pub date May 20, 2025), in view of Siegelman et al. (“Controlling Cooperative CO2 Adsorption in Diamine-Appended Mg2(dobpdc) Metal–Organic Frameworks,” J. Am. Chem. Soc. 2017, 139, 10526-10538, and Supporting Information, pub date Aug. 2, 2017).
The teachings of Siegelman et al. have been discussed previously within this office action.
Claim 1 of US 12303865 is directed to a process for preparing an aminated MOF product, comprising making a crude base MOF from a cationic metal salt and a polytopic organic ligand in water, isolating a purified base MOF by rinsing with a cake filter press using water and a first cosolvent, further filtering and purifying the base MOF, obtaining an aminated MOF by an amination reaction between the filtered and purified base MOF and at least one alkyl-functionalized amine in a solvent system comprising at least one second cosolvent, stirring and optionally heating, and isolating the purified aminated MOF.
Claim 3 of US 12303865 recites that the first, second and third cosolvents are selected from acetonitrile, ethyl acetate, toluene, methanol, ethanol, 1-propanol and 2-propanol.
Claim 7 recites that the cationic metal salt is a salt of a polycationic metal including Mg.
Claims 8-10 recite that the alkyl-functional amine is a polyamine selected from a diamine, triamine and tetramine, used in less than 20, less than 10, or less than 5 molar equivalents.
Although the claims at issue are not identical, they are not patentably distinct from each other. The instant claims recite mixing a base porous material bearing a coordinated labile ligand with a functionalizing agent to form a slurry, and functionalizing the open metal sites in that slurry.
Claim 1 of US 12303865 recites the same operation, namely an amination reaction between a filtered and purified base MOF and an amine in a cosolvent system with stirring. The rinsed and filtered base MOF of claim 1 carries the first cosolvent, which is methanol or acetonitrile under claim 3, as the bound coordinating solvent, that is, applicant’s labile ligand.
The instant claims differ in that they recite a boiling temperature difference of about 50 °C to about 150 °C between the amine and the bound solvent. This difference is an inherent property of the species already claimed in US 12303865, and is taught by Siegelman et al., which pairs methanol-solvated Mg2(dobpdc) with diamines boiling about 72 °C to about 105 °C above methanol.
The instant claims further differ in that they omit the cake filter press isolation steps. Omitting a step and its attendant function is an obvious variation. The remaining limitations of instant claims 2-16, directed to the MOF material, the labile ligand identity, the amine identity, the metal, the presence or absence of slurry solvent, the drying temperature and pressure, the ratios, and the preparation of the base porous material, are taught or rendered obvious by claims 1-10 of US 12303865 in view of Siegelman et al., and are obvious matters of routine optimization.
Accordingly, instant claims 1-16 are not patentably distinct from claims 1-10 of US 12303865, in view of Siegelman et al.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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/JENNIFER C SAWYER/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
