DETAILED ACTION
Notice of Pre-AIA or AIA Status
This Office action is based on the 18/241,559 application filed 1 September 2023, which is being examined under the first inventor to file provisions of the AIA .
Claims 1-20 are pending and have been fully considered.
Claim Interpretation
Applicant is reminded “[u]nder a broadest reasonable interpretation (BRI), words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. The plain meaning of a term means the ordinary and customary meaning given to the term by those of ordinary skill in the art at the relevant time. The ordinary and customary meaning of a term may be evidenced by a variety of sources, including the words of the claims themselves, the specification, drawings, and prior art. However, the best source for determining the meaning of a claim term is the specification - the greatest clarity is obtained when the specification serves as a glossary for the claim terms.” Phillips v. AWH Corp., 415 F.3d 1303, 1315, 75 USPQ2d 1321, 1327. In the instant case, for sensing applications appears to mean “generat[ing] unique IR spectral features” as discussed in paragraph 0013 of the published application (“[t]he disclosed invention establishes the fundamental materials science driving IR spectral signatures and adsorbent performance to produce a new material class intended for sensing applications and robust adsorbent applications from gas and liquid phase media. The custom developed porous materials are designed to generate unique IR spectral features for sensing…”), which spectral features include “narrow[ing] the OH vibrational stretch” [see paragraph 0040 of the published application].
Claim Objections
Claim 8 is objected to because of the following informalities: claim 8 depends on itself, which is improper. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
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.
Claims 1-20 are 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.
Claims 1, 9, and 14 recite “an absorbent for sensing applications from gas and liquid phase media.” See claim interpretation above. It is not clear what IR spectral signature or features are meant by the term for sensing applications. Therefore, the meets and bounds of the claimed invention cannot be determined.
Claim 15 recites “wherein the sorbent moiety is intercalated into the pores of the metal organic framework during the formation of the metal organic framework.” However, claim 14, from which 15 depends, recites “…providing a metal organic framework; intercalating the sorbent moiety into the pores of the metal organic framework…” Claim 14 clearly limits the invention to intercalation of a provided (i.e., pre-made) metal organic framework. Claim 15 makes it unclear what it means to “provide a metal organic framework” and leads to confusion as to the scope of the claimed invention.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Long et al (US 2014/0294709).
Long et al discloses “[i]n order to demonstrate the functionality of metal-organic frameworks featuring coordinatively-unsaturated metal centers for separating gases, a mmen-CuBTTri framework as shown in FIG. 1 was constructed and tested. A sample of CuBTTri…was suspended in 10 mL of anhydrous hexane under nitrogen, and 75.4 .mu.L…of N,N' dimethylethylenediamine (mmen) was added via micropipette with stirring. The compound immediately turned blue and the suspension was heated at reflux for 18 hours under nitrogen. The solid was collected by filtration and washed with successive aliquots of hexane…to remove unreacted diamine. The solid was then dried under reduced pressure to remove hexane…The grafted material, mmen-CuBTTri, was then activated by heating at 50o C. for 24 hours under a dynamic vacuum… In order to demonstrate the functionality of metal-organic frameworks featuring coordinatively-unsaturated metal centers for separating gases, a mmen-CuBTTri framework as shown in FIG. 1 was constructed and tested. The mmen-CuBTTri and men-CuBTTri adsorbents were initially tested in the context of separating a mixture stream including CO2 and N2 to obtain a stream richer in N2 as compared to the mixture stream, with the adsorption of CO2 in the frameworks at low pressures”[paragraphs 0070-0072 & 0074-0075]. The sample of CuBTTri corresponds to the providing step of instant claim 1. The reaction with mmem corresponds to the grafting step. The mmen-CuBTTri adsorbent corresponds to the produced adsorbent material and the mixture stream including CO2 and N2 corresponds to the gas phase media. The adsorption of CO2 may certainly be used for sensing CO2.
Claim Rejections - 35 USC § 103
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.
Claim(s) 1, 4-5, and 7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Servalli et al in Chemical Communications (2012, vol 48, pp 1904-1906).
Servalli et al discloses “a method that enables (near) quantitative introduction of functional groups into the pores of MOFs at fast rates. To achieve this, we sought solvent-free vapor-phase PSM [post-synthetic modification—Examiner’s insertion—see 1st paragraph of reference] (VP-PSM), a general, efficient, and versatile route to perform reaction of—for example—amino-functionalized MOFs with aldehydes and anhydrides by vapor diffusion (Scheme 1)” [see paragraph preceding Scheme 1 on page 1904].
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The reference further discloses “[t]o illustrate that our VP-PSM method is generally applicable to MOFs with other topology than MOF-5, we performed VP-PSM of UiO-66-NH2 with salicylaldehyde…,” which yields the compound, UIO-66-SI in Table 1 that corresponds to the adsorbent material of the instant application, in the upper right hand corner of Scheme 1, wherein the imine bond is clearly shown. With respect to the sensing application requirement, Servalli discloses “PSM is a versatile method that allows control of the number and types of functional groups introduced into a single framework and that has widened the design and testing of modified MOFs in gas sorption” [see 1st paragraph of reference]. Therefore, the sensing applications from gas and liquid phase media would have been obvious to one of ordinary skill in the art. Additionally, Servalli et al discloses “[t]o improve the sorption properties of the material, we designed a material that has the same MOF-5 topology, which features only one type of functional group, and with a comparable surface area of the material before and after PSM. We synthesised MIXMOF-5-NH2 with 12% amino groups by mixing 2-aminoterephthalic acid and terephthalic acid in a 1:4 ratio with Zn(NO3)2 in DMF under solvothermal conditions. MIXMOF-5-NH2 features a BET surface area of 3120 m2 g-1, slightly higher than the published value of similar MIXMOFs. Thereafter, we performed the same solvent exchange as described for IRMOF-3. VP-PSM with salicylaldehyde at 100 oC proceeded with quantitative yield (Table 1, run 2) and produced MIXMOF-5-SI in which the chelating groups were randomly and homogeneously distributed within the framework and that had a BET surface area of 2820 m2 g-1, only 10% lower than the starting amino MIXMOF” [2nd and 3rd paragraphs on right hand side of page 1905]. The MIXMOF-5-SI also corresponds to the adsorbent material of the instant application. Recall, the teaching above (“to improve sorption properties…”).
With respect to claim 5, note the following phenol moiety associated with UiO-66-NH2:
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Claim(s) 1, 4-5, and 7-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Maspoch Comamala et al (EP 3,335,788), hereafter referred to as Maspoch.
With respect to claims 1, 4-5, and 7-8, reference is made to the preceding discussion concerning PSM of UiO-66-NH2 with salicylaldehyde. Maspoch discloses “[a] series of ethanolic colloidal suspensions containing UiO-66-NH2 [synthesized as described above…and the aldehydes 4-pyridinecarboxaldehyde (4PC), 2-pyridinecarboxaldehyde (2PC) and salicylaldehyde (Sal) were initially prepared…Each suspension was then spray-dried…A yellow powder was collected after 5 min. The resulting solid was then dispersed in 20 mL of ethanol and precipitated by centrifugation. This process was repeated four times. The final product was washed one time with acetone and dried for 12 h at 85 °C. The different samples were named as (UiO-66-4PC)x, (UiO-66-2PC)x and (UiO-66-Sal)x (where x is 3, 5, 10 and 15, depending on the equivalents of aldehyde used)” [paragraph 0038; example 3]. The reference further discloses “[t]he modified MOF obtainable by the process of the invention may be suitable for several applications, such as acting as catalysts in chemical industrial reactions, for gas absorption, for pollutant removal, for sensor technology” [paragraph 0034]. Maspoch further discloses “[n]on-limitative appropriate MOFs are UiO-66-NH2, ZIF-90, MIL-101-NH2, MIL-53-NH2, IRMOF-3, UiO-67-NH2, UiO-67-CHO…” [paragraph 0021].
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Li et al in the Journal of the American Chemical Society (2013, vol 135, pp 11688-11691).
Li et al discloses “[a] stepwise ligand exchange strategy is utilized to prepare a series of isoreticular bio-MOF-100 analogues. Specifically, in situ ligand exchange with progressively longer dicarboxylate linkers is performed on single crystalline starting materials to synthesize products with progressively larger mesoporous cavities. The new members of this series of materials, bio-MOFs 101−103, each exhibit permanent mesoporosity and pore sizes ranging from ∼2.1−2.9 nm and surface areas ranging from 2704 to 4410 m2/g” [abstract] and “[t]o realize this design strategy, we first studied the conversion between bio-MOF-101 and bio-MOF-100 (Figure 1A,B). Bio-MOF-101 was thoroughly washed with N,N’-dimethylformamide (DMF) and subsequently soaked in a 0.05 M H2-BPDC/DMF/NMP (DMF:NMP = 1:1 ; NMP = N-methylpyrolidinone) solution for 24 h in a 75 °C oven; the solution was removed, replaced with a fresh H2-BPDC solution, and the mixture was again heated at 75 °C for 24 h. Upon inspection using an optical microscope, the product crystals were mostly transparent and slightly cracked (Figure 1B). 1H NMR spectra of the dissolved crystalline product revealed only the presence of adenine and BPDC linkers; no NDC was detected, indicating that it was completely replaced by BPDC (Figure S1). Having successfully converted bio-MOF-101 to bio-MOF 100 through ligand exchange…” [last paragraph on page 11688 and 1st paragraph on page 11689] and “bio-MOF-101, adsorbs the least amount of N2 and has a calculated pore volume of 2.83 cc/g. The bio-MOF-100 sample prepared herein adsorbed 2444 cc/g N2” [2nd paragraph on left hand side of page 11690]. The bio-MOF-100 corresponds to the producing (or produced) step of instant claim 9. The step wise ligand exchange corresponds to the grafting step of the same.
Claim(s) 1, 9, and 12-13 is/are rejected under 35 U.S.C. 103 as being unpatentable over Du et al (CN 114736895).
Note: in the discussion that follows, reference will be made to the machine translation of the aforementioned reference.
With respect to claims 1, 9, and 12, Du et al discloses [step 2 of example 1:] “synthesizing UiO-66-NH2 @ Lps (i.e., performing ligand exchange reaction by strong ligand)…taking 45 mg of 2-amino terephthalic acid strong ligand) dissolved in 1.5mL mass fraction of 4 % of potassium hydroxide solution, then using hydrochloric acid with concentration of 1 M to adjust the pH value of the solution to neutral. Adding 72mg UiO-66-F4 @Lps powder prepared in the step (1) to the solution, stirring for 12h, carrying out fully ligand exchange reaction. 12000rpm centrifuging for 5 min, collecting solid, particulate matter deionized water washing for several times, removing free tetrafluoride terephthalic acid ligand, then freezing and drying, time is 12 hours, obtain brown solid end product immobilized enzyme UiO-66-NH2 @ Lps” [see bottom of page 4 and top of page 5 of translation]. The reference further discloses “the obtained composite material immobilized enzyme is suitable for most process scene based on enzyme catalysis, industry comprises industrial biological catalysis, analysis diagnosis, sensing test and so on” [see bottom of page 3 of translation]. The UiO-66-NH2 corresponds to the adsorbent material of the instant application and its use as a sensing test renders obvious the requirement of an adsorbent material for sensing applications from gas and liquid phase media. The “adding…UiO-66-F4…corresponds to the providing step of instant claims 1 and 9, and the ligand exchange reaction corresponds to the grafting step, which is performed post-synthesis of the UiO-66-F4.
With respect to claim 13, note that UiO-66 and UiO-67 are art-recognized equivalents [see above]. Therefore, it would have been obvious to one of ordinary skill in the art to substitute the latter for the former because one of ordinary skill in the art would have found it obvious to substitute one MOF for an equivalent MOF used in the art.
Claim(s) 14 and 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Al-Naddaf et al in Industrial and Engineering Chemistry Research (2018, vol 57, pp 17470-17479).
Al-Naddaf et al discloses “the storage of methane in nanocomposite adsorbents comprising metal−organic framework (MOF) and graphene oxide (GO) was investigated. Three different sets of MOF-GO nanocomposites comprising HKUST-1 and pristine GO, reduced GO (rGO), and carboxyl-functionalized GO (fGO) were developed by the solvothermal method, and their methane storage characteristics were assessed through high-pressure methane adsorption measurements. The formation of MOF-GO nanocomposites was confirmed by XRD, FTIR, XPS, SEM, and TEM” [abstract]. The reference further discloses “Figure 6d displays the parallel GO sheets within the composite structure. These images clearly confirm the occurrence of intercalation of GO in the MOF structure for this nano composite” [1st paragraph on left hand side of page 17475] and “[a] one-pot synthesis method was used to prepare the nanocomposites, in a similar way to that of pristine HKUST-1. Initially, 10 wt % of GO, rGO, and fGO was added to the mixture of HKSUT-1 precursors before hydrothermal synthesis. The mixtures were then heated to 110 °C for 20 h, after which they were cooled down to room temperature, filtered and washed extensively with dichloromethane. Lastly, the resulting products were dried under a vacuum at 150 °C for 24 h. This is common synthesis procedure for MOF-GO composites that has been widely used by other researchers. The nanocomposites were denoted as HKUST-1@GO, HKUST-1@rGo, and HKUST-1@fGO” [last paragraph on page 17471]. Since the MOF-GO nanocomposites serve as methane adsorbents, the sensing applications from gas and liquid phase media would have been obvious to one of ordinary skill in the art.
Claim(s) 14-16 and 19-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Britt (US 2020/0274080 A1).
Britt discloses “[a] film, and a light-emitting device (e.g., an OLED) incorporating the film as an emission layer, have luminescent emitters that are maintained in a desired orientation by incorporating them into a crystalline framework material, such as a metal-organic framework (MOF)” [abstract] and “the crystalline framework material is a metal-organic framework comprising metallic structural units linked by organic structural units” [paragraph 0030] and “the metal-organic framework comprises a unit described by the formula…UiO-66, UiO-67, or UiO-68” [paragraph 0037] and “[t]he luminescent emitter can be intercalated after preparation of the metal-organic framework via known methods such as vapor deposition and/or adsorption and/or post-synthetic functionalization” [paragraph 0095] and “[a]n alternative method for preparing the crystalline framework material comprises the steps of (i) preparing a metal-organic framework using an organic structural unit; and (ii) adsorbing a luminescent emitter at the internal surface of the metal-organic framework. The luminescent emitter may also be adsorbed to one of the building blocks before it is used to prepare a metal-organic framework. In accordance with this alternative method, the luminescent emitter is not chemically bonded to the metal-organic framework, but instead adsorbed to the surface of the framework structure, and in some cases, to the internal surface of pores of the framework structure. Adsorption can, for instance, be performed from the gas phase, or from solution” [paragraph 0063]. Adsorbing at the internal surface renders obvious diffusion as recited in instant claim 16. A light emitting device renders obvious an adsorbent material for sensing applications from gas and liquid phase media.
Allowable Subject Matter
Claims 2-3, 6, 10-11, and 17-18 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: with respect to claim 2, the cited prior art does not disclose post synthetic modification by click chemistry; with respect to claim 3, the prior art does not appear to disclose the recited carboxylic acid. The nearest prior art appears to be Xie et al (CN 112898585). Xie et al discloses “[a] chiral metal-organic framework material, which is obtained by in-situ condensation of the Zr-based MOFs material UiO-66-NH2 as a precursor through D-tartaric acid or L-tartaric acid and an amino group in UiO-66-NH2…The present invention is stable, porous Zr-based MOFs material[;] UiO-66-NH2 is a matrix[;] tartaric acid is a chiral source[;] a chiral UiO-tart newMOFs material is obtained by in-situ post-modification technology, and is further equipped as a chromatographic column to achieve a good effect in the splitting of various chiral molecules” [see page 2 of translation] and “[i]f MOFs containing amino groups are mater[i]al (such as UiO-66-NH2—Examiner’s insertion], tartaric acid can be grafted onto MOFs by using the [post-modification—Examiner’s insertion] technology, which is an ideal strategy for constructing and regulating novel chiral MOFs functional materials…” [see bottom of page 1 of translation]. Xie et al further discloses “[m]etal-organic framework materials (MOFs) are novel functional materials with periodic porous crystal structures, and their structures and functions can realize system regulation, and have important application prospects in fields such as energy, catalysis, photoelectric, and sensing. The chiral MOFs can also synergistically provide chiral active sites while having ordinary MOFs material structures and performance advantages, and exhibit powerful application prospects in fields such as asymmetric catalysis and chiral recognition splitting. If the chiral MOFs are used as a fixed phase in the preparation of the novel chiral chromatographic column, the chiral resolution efficiency and the disassembly component of the chromatographic column can be significantly improved, and the advantages of the MOFs function can be used to realize the system development of various chromatographic columns, and have an important pushing effect in the fields such as basic research and chiral resolution applications” [see page 1 of translation]. The splitting of chiral molecules in a chromatographic column corresponds to the sensing applications from gas and liquid phase media. However, tartaric acid is a dicarboxylic acid. Therefore, a benzamide is not formed. With respect to claims 6, 10-11, and 18-19, the prior art does not teach the recited phenol or phenol-based compound, bisphenol, or the fluorinated phenol.
Conclusion
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/BRIAN A MCCAIG/Primary Examiner, Art Unit 1772
11 March 2026