DETAILED ACTION
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 .
Election/Restrictions
Applicant’s election without traverse of Group I, directed to claims 1-14, in the reply filed on 02/02/2026 is acknowledged.
Claims 15-19 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 02/02/2026.
Claim Objections
Claim 4 is objected to because of the following informalities:
Claim 4 recites, “the formation ratio of [A] is formed at a weight ratio of 0.05 to 1.0 as [A]/[B]” wherein [A] is a stand-in for “the ZIF-8 metal-organic framework in which a reaction site is formed” and [B] is a stand-in for “the ZIF-8 metal-organic framework in which a reaction site is not formed,” which contains grammatical errors which cloud the clarity of the stated limitation.
To cure the grammatical deficiencies of the claim it is suggested that the claim limitation is restated in one of the following formats:
A ratio of A/B is 0.05 to 1.0 by weight;
A formation ratio of [A] with respect to [B] by weight is 0.05 to 1;
A formation ratio of [A] is formed as a weight ratio of 0.05 to 1.0 as represented by [A]/[B];
or an equivalent which better describes the intended scope of the claim.
Furthermore, it is unclear if the recited ratio is to be interpreted as a single value (0.05 : 1), or a range of ratios(0.05-1 : 1). For the purposes of examination, the recited limitation has been interpreted as a range of values.
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 2, 4, 7, 9 and 12 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.
Claim 2 recites the limitation "the bond of the ZIF-8 metal-organic framework" in lines 2-3. There is insufficient antecedent basis for this limitation in the claim. For the purposes of examination, the limitation has been interpreted to refer to bonds between zinc atoms and the nitrogen atoms of methylimidazole ligands.
Claim 4 recites the limitation “the formation ratio” in line 2. There is insufficient antecedent basis for this limitation in the claim.
Claim 7 recites the limitation “the yield of carbonate” in line 2. There is insufficient antecedent basis for this limitation in the claim.
Claim 9 recites the limitation “the yield of carbonate” in line 2. There is insufficient antecedent basis for this limitation in the claim.
Claim 12 recites the limitation “the BET surface area” in line 2. There is insufficient antecedent basis for this limitation.
Claim Rejections - 35 USC § 102
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.
Claims 1 and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mu et al. (J. Mater. Chem., 2012, 22, 12246).
With regard to claim 1, Mu et al. teaches a ZIF-8 molecular-organic framework (MOF; pp. 12246, Abstract) with water molecules provided inside the ZIF-8 MOF (pp. 12246, Abstract a& pp. 12247, Section 2.2.1) which reads to the instantly claimed ZIF-8 MOF catalyst composite comprising a ZIF-8 MOF and water molecules.
With regard to claim 11, Mu et al. teaches samples of ZIF-8 MOFs containing 16.34 wt%, 27.71 wt%, and 30.64 wt% of water within the ZIF-8 MOF (pp. 12246, Abstract, pp. 12250, left col. & Fig. 12). The samples taught comprise water within the framework which is within the instantly claimed range of 0.005-0.35 weight ratio (i.e. 0.5-35 wt%) of water molecules with respect to the ZIF-8 MOF catalyst composite.
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.
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 2-4 and 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Mu et al. as applied to claim 1 above, and further in view of Zhang et al. (Microporous and Mesoporous Materials, 2019, 288, 109568).
With regard to claim 2, Mu et al. does not teach that the water molecules provided within the ZIF-8 MOF catalyst composite dissociate at least a portion of the bonds of the ZIF-8 MOF to form a ZIF-8 MOF with a reaction site. However, Zhang et al. teaches that at a low ZIF-8/water ratio (pp. 2, right col., lines 44-46) or when ZIF-8 MOF is in the presence of water and a reaction-accelerating acid such as CO2 (pp. 4, right col., lines 5-18), partial hydrolysis of the Zn-N bonds in the ZIF-8 MOF occurs to generate a material with partially coordinated Zn and imidazole (i.e. ZIF-8 MOF in which a reaction site is formed) and coordinated Zn and imidazole (i.e. ZIF-8 MOF in which a reaction site is not formed). Therefore, it would have been obvious to one of ordinary skill in the art at the time of invention that during the exposure of the ZIF-8 MOF to water, either during initial synthesis or through a post-synthetic process which provides water molecules to the interspaces of the ZIF-8 MOF (e.g. Section 2.2.1 of Mu et al.), the water molecules dissociate a portion of Zn-N framework bonds through the hydrolysis mechanism described by Zhang et al.
With regard to claim 3, Mu et al. does not teach that the ZIF-8 MOF catalyst composite comprises a portion of ZIF-8 MOF with a first reaction site including a Zn-OH bond and a second reaction site including a N-H bond as instantly claimed. However, Zhang et al. teaches that in the ZIF-8 MOF, hydrolysis of the Zn-N bonds of ZIF-8 results in the formation of -OH coordinating to Zn (Zn-OH bond) and -H coordinating to the nitrogen of a methylimidazole ligand (N-H bond; pp. 4, right col., lines 62-64). Therefore, it would have been obvious to one of ordinary skill in the art that a ZIF-8 MOF comprising water molecules in the framework which then undergoes partial hydrolysis would, in some capacity, form modified reaction sites comprising a Zn-OH bond and a N-H bond as instantly claimed.
With regard to claim 4, Mu et al. does not teach that the ZIF-8 MOF comprises a weight ratio of 0.05-1.0 ZIF-8 MOF comprising Zn-OH/N-H active sites with respect to pristine ZIF-8 MOF, i.e. 2.5-50 wt% of the ZIF-8 MOF composite contains hydrolyzed Zn-N bonds. However, the maximum amount of water which can be provided within the ZIF-8 MOF is 38 wt% with respect to the overall composition, at which point the pore volume of the ZIF-8 MOF is completely filled with water molecules (pp. 12251, left col., lines 10-12). The highest reported ZIF-8 MOF sample has a water content of 35.13 wt% (pp. 12251, left col., lines 12-13). Therefore, at a maximum, the water present in the ZIF-8 MOF reported by Mu et al. could hydrolyze 35 wt% of the ZIF-8 MOF, or roughly 54.1% of the available ZIF-8 MOF, which would result in a maximum weight ratio of 1.05:1 ZIF-8 MOF comprising a formed reaction site to pristine ZIF-8 MOF. As demonstrated by the work of Zhang et al., such complete hydrolysis of the ZIF-8 MOF without additional water or accelerants would be unlikely, as the XRD patterns of the ZIF-8 MOF composite with 35.13 wt% water does not show characteristic phase transformations from partial hydrolysis of the framework (see Fig. 12 of Mu et al. compared to Fig 2. of Zhang et al.). Assuming that hydrolysis of a portion of the Zn-N bonds in the ZIF-8 MOF containing water occurs, the weight ratio of ZIF-8 MOF comprising a formed reaction site to pristine ZIF-8 MOF would necessarily be greater than 0. Therefore, the theoretical maximum weight ratio of ZIF-8 MOF comprising a formed reaction site to pristine ZIF-8 MOF is 0<x<1.05:1.0, which significantly overlaps the claimed weight ratio of 0.05-1.0:1. A person of ordinary skill in the art would be motivated to optimize such a composition’s weight ratio of modified ZIF-8 MOF to pristine ZIF-8 MOF in order to achieve improved gas adsorption associated with water inclusions in the framework (as posited by Mu et al.; pp. 12246, Abstract) and minimize losses in porosity and specific surface area from partial hydrolysis as explained by Zhang et al. (see pp. 3, left col. line 10 – right col., line 4). It would have been obvious to one having ordinary skill in the art at the time the invention was made to choose the instantly claimed ratio of modified and pristine ZIF-8 MOF through process optimization, since it has been held that there the general conditions of a claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. See In re Boesch, 205 USPQ 215.
With regard to claims 13 and 14, the examiner recognizes that all of the claimed physical properties are not positively stated by the reference (Mu et al. nor Zhang et al. disclose XPS data). Note however that the references teach all of the claimed molecular components and process conditions and thus, the claimed effects and physical properties would implicitly be achieved by the claimed ingredients/carrying out the disclosed process (i.e. hydrolysis of Zn-N bonds to form Zn-Oh and N-H). XPS analysis measures the binding energies of atoms which are inherent to the atomic species (including electronic state) and surrounding chemical environment. The ZIF-8 MOF including water (i.e. the ZIF-8 MOF catalyst composite), as taught by Mu et al., after undergoing Zn-N bond cleavage and subsequent hydrolysis as described by Zhang et al. as a naturally occurring process (i.e. a mixture of ZIF-8 MOF in which a reaction site is formed and ZIF-8 MOF in which a reaction site is not formed), would necessarily have XPS binding energies between 1,022.3-1,022.5 eV and 531.8-520 eV, associated with the bound Zn and O atoms respectively (as per Fig. 4 of the instant specification) and have a ratio of said peaks to peaks centered at 398.3 eV and 1021.1 eV, associated with fully coordinated Zn and methylimidazole in ZIF-8 (also as per Fig. 4 of the instant specification), would also be between 0.4 and 0.8. If it is applicant’s position that this would not be the case, evidence would need to be presented to support applicant’s position.
Claims 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over Mu et al. and Zhang et al. as applied to claim 3 above, and further in view of Zhu et al. (Catalysis Communications, 2013, 32, pp. 36-40).
With regard to claim 5, Mu et al. does not teach that the produced water-containing ZIF-8 MOF catalyzes a cycloaddition reaction between CO2 and an epoxide at Zn-OH or N-H active sites. However, Zhu et al. teaches that ZIF-8 MOFs catalyze the cycloaddition of CO2 to styrene oxide (an epoxide) to form styrene carbonate (pp. 26, Abstract). Zhu et al. teach that the Zn ions of the ZIF-8 MOF act as Lewis acid sites and contribute to catalysis of the cycloaddition, and that nitrogen atoms on the imidazole ring (the N which bonds to Zn within the framework) act as Lewis base sites adsorbs and likely activates CO2, also contributing to the cycloaddition catalysis (pp. 38, left col., lines 4-6). Specifically, Zhu et al. observes that the basic sites (i.e. nitrogen) contribute more heavily to catalysis (pp. 39, left col., lines 2-5) because of the importance of adsorption and activation of the stable CO2 molecule at the active site for initiating cycloaddition (pp. 39, right col., lines 4-16).
A person of ordinary skill in the art would therefore see that ZIF-8 MOFs have art-recognized suitability for catalyzing cycloaddition of CO2 to an epoxide and that catalysis specifically occurs at Zn ion and N atoms associated with the active sites instantly recited. The Zn-OH bond and N-H bonds obtained via hydrolysis of ZIF-8 MOFs would not prevent coordinated Zn from acting as a Lewis acid or coordinated N atoms on imidazole rings from acting as a Lewis base, and a person of ordinary skill in the art could reasonably expect a ZIF-8 MOF containing hydrolyzed bonds and/or free water molecules to catalyze a cycloaddition in the same manner as the ZIF-8 MOF taught by Zhu et al. Furthermore, a person of ordinary skill in the art would be motivated to use the water-containing ZIF-8 MOF taught by Mu et al. because of the increased rates and volumes of gas adsorption observed (pp. 12246, Abstract). While the study by Mu et al. is directed to methane gas adsorption, they note the same effect to previously have been observed in relation to CO2 gas adsorption (pp. 12246, right col., lines 13-18). Therefore, it would have been obvious to one of ordinary skill to apply the ZIF-8 MOF containing water, taught by Mu et al., as a catalyst for the cycloaddition of CO2 to styrene oxide, taught by Zhu et al., in order to improve catalytic efficiency through increased CO2 adsorption, which is noted as a key step for the cycloaddition reaction.
With regard to claim 6, Mu et al. does not teach that the disclosed ZIF-8 MOF containing water molecules catalyzes the cycloaddition of CO2 to epichlorohydrin, ethylene oxide, styrene oxide, or propylene oxide. However, as noted above, Zhang et al. teaches that ZIF-8 MOFs catalyze the cycloaddition of CO2 to styrene oxide as instantly claimed. As stated in regard to claim 5, a person of ordinary skill in the art would expect, with a reasonable degree of success, that the ZIF-8 MOF containing water taught by Mu et al. would catalyze cycloaddition of CO2 to styrene oxide at one of the recited active sites at least (Zn-OH or N-H).
With regard to claim 7, Mu et al. teaches that as the content of water molecules increases in the ZIF-8 MOF, the gas storage capacity of the MOF increases (pp. 12250, left col., lines 12-16) and the specific volume overall increases (pp. 12251, left tight col., line 11-pp. 12251, left col., line 9). Mu et al. does not teach that an increase in water content within the ZIF-8 MOF would lead to an increased yield of a carbonate during cycloaddition of CO2 to an epoxide. However, as adsorption of CO2 is understood to be a strong contributor to the efficacy of catalysis of bimolecular reactions involving CO2 (Zhu et al., pp. 39, right col., lines 4-16), a person of ordinary skill in the art, with a reasonable expectation of success, would increase the water content in the ZIF-8 MOF and observe an increased yield of styrene carbonate, as a result of cycloaddition catalysis, because of improved CO2 gas adsorption and subsequent CO2 activation.
With regard to claim 8, Mu et al. does not teach that the ZIF-8 MOF containing water molecules catalyzes cycloaddition of CO2 to an epoxide and yields chloropropene carbonate, ethylene carbonate, styrene carbonate or propylene carbonate as a product. However, as noted above, Zhang et al. teaches that ZIF-8 MOFs catalyze the cycloaddition of CO2 to styrene oxide and yields exclusively styrene carbonate (pp. 37, left col., lines 39-40). As stated in regard to claim 5, a person of ordinary skill in the art would expect, with a reasonable degree of success, that the ZIF-8 MOF containing water as taught by Mu et al. would catalyze cycloaddition of CO2 to styrene oxide at one of the recited active sites at least (Zn-OH or N-H) and yield styrene carbonate as the product, as taught by Zhu et al.
With regard to claim 9, a person of ordinary skill in the art using the ZIF-8 MOF containing water molecules taught by Mu et al. as a catalyst for the cycloaddition of CO2 to an epoxide yielding a cyclic carbonate would have found it obvious to calculate a yield with respect to carbonate/epoxide because it is standard convention to calculate yield with respect to the limiting reagent and as taught by Zhu et al., the limiting reagent was styrene oxide (the epoxide; pp. 37, right col., lines 23-26).
With regard to claim 10, Mu et al. does not teach that the ZIF-8 MOF containing water catalyzes cycloaddition of CO2 to an epoxide and produces a carbonate in a yield of 20-99%. However, as noted above, Zhang et al. teaches that ZIF-8 MOFs catalyze the cycloaddition of CO2 to styrene oxide and yields exclusively styrene carbonate (pp. 37, left col., lines 39-40) with yields of between 37-70%, which is within the instantly claimed range. As stated in regard to claim 5, a person of ordinary skill in the art would expect, with a reasonable degree of success, that the ZIF-8 MOF containing water as taught by Mu et al. would catalyze cycloaddition of CO2 to styrene oxide at one of the recited active sites at least (Zn-OH or N-H) and yield styrene carbonate in yields around 37-70%, as taught by Zhu et al. Furthermore, It would have been obvious to one having ordinary skill in the art at the time the invention was made to arrive at the instantly claimed carbonate yield through routine optimization of reaction conditions (pressure, time, temperature) or physical properties of the MOF (SSA, porosity, water content via synthesis), since it has been held that there the general conditions of a claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art. See In re Boesch, 205 USPQ 215.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Mu et al. as applied to claim 1 above, and further in view of Tanaka et al. (J. Phys. Chem. C, 2015, 119, pp. 28430-28439).
With regard to claim 12, Mu et al. teaches a ZIF-8 MOF containing water particles with a BET surface area of 1,273 m2/g (pp. 12247, Section 2.1), which is outside the instantly claimed range of 1,300-1,600 m2/g. However, a difference of 27 m2/g with regard to highly porous/high specific area materials is negligible and a person of ordinary skill in the art would expect the ZIF-8 MOF employed by Mu et al. to share the same properties as the instantly claimed ZIF-8 MOF containing water molecules with a BET surface area of, for example, 1,300 m2/g. Such an assumption is validated in the prior art with regard to ZIF-8 specifically. In a gas adsorption study of ZIF-8 MOFs, Tanaka et al. teach a selection of ZIF-8 MOFs with BET surface areas ranging from 1520-1730 m2/g (see Table 2). The difference in BET surface area between the samples, including a 200 m2/g difference between samples, is considered to be “nearly identical” for the purposes of quantitative study (pp. 28431, right col., lines 40-42) and that the observed variance would not cause a functional structural or chemical difference to the material’s adsorption or diffusion properties (pp. 28433, left col., lines 11-15). Therefore, a prima facie case of obviousness exists between the instantly claimed range and the properties of the commercial material of Mu et al. due to their mere closeness because one skilled in the art would have expected them to have the same functionality. See MPEP § 2144.05.I.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Tian et al. (J. Phys. Chem. C, 2014, 118, pp. 14449-14456); Hu et al. (ChemCatChem, 2019, 11, pp. 3212-3219).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MORDECAI M LEAVITT whose telephone number is (571)272-6637. The examiner can normally be reached Monday-Friday 8AM-5PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, CHRISTINA JOHNSON can be reached at (571) 272-1176. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MORDECAI M LEAVITT/Examiner, Art Unit 1742
/MONICA A HUSON/Primary Examiner, Art Unit 1742
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