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 .
Continued Examination Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 December 31st, 2025 has been entered.
Response to Amendment
The Amendment filed December 31st, 2025 has been entered. Examiner acknowledges the addition of new claim 21. Claims 1-2 and 4-21 remain pending in the application.
Response to Arguments
Applicant's arguments filed December 31st, 2025 with respect to claims 1-20 have been fully considered but they are not persuasive.
Applicant argues that the cited prior art, particularly Zhou et al., is deficient because it relies on naturally occurring montmorillonite, whereas the presently claimed invention allegedly employs a synthetic magnesium hydroxide phyllosilicate, prepared by a bottom-up synthetic process, and having a defined octahedral magnesium cation interlayer positioned between tetrahedral organosilicate sheets. These arguments are not persuasive because claims 1-20 do not recite these limitations.
Applicant asserts that Zhou does not disclose a “true” single-layer nanosheet and further argues that modifying Zhou to yield single layers would render the reference unsuitable for its intended purpose. These arguments are not persuasive. Zhou expressly discloses exfoliation of layered materials into single-layer nanosheets, even if such layers are later reassembled for preferred applications. Claims 1-20 merely require “a single layer nanosheet 5 nanometers or less in thickness” and do not require that the nanosheet remain permanently isolated or unassembled. The fact that Zhou may prefer reassembled layered hybrids for CO2 capture does not preclude the disclosure of single-layer nanosheets nor negate their applicability to the claimed structure. The Examiner is not required to preserve the primary reference’s preferred embodiment when modifying the reference to meet the claimed invention, therefore the arguments concerning intended use and preferred performance in Zhou do not overcome the rejection.
Applicant further argues that Zhou relies on non-covalent electrostatic adsorption of ionic liquids and therefore fails to disclose covalently attached permanent cationic charges. While Zhou alone may not disclose covalent attachment, the rejection is based on Zhou in combination with Hao, Jiang, Beall and Benachour. Hao explicitly teaches covalent grafting of imidazolium-based ionic liquids onto inorganic substrates via silane chemistry, and Jiang and Benachour further demonstrate that covalent immobilization of ionic liquids on siliceous supports was well known in the art. Claims 1-20 broadly recite “surface is modified by covalent attachment with a plurality of charged organic moieties” and do not require any specific silicate framework beyond that already taught by the applied references. The combination reasonably supplies the covalent attachment limitation, as previously explained.
Applicant asserts that the claimed materials achieve complete and homogenous functionalization at every silicon site, allegedly distinguishing over Zhou. However, claims 1-20 do not recite full, uniform, or site-specific functionalization. In the absence of such limitations, partial or heterogenous functionalization as taught in the prior art falls within the scope of the claims.
In summary, arguments rely on structural, compositional, and synthetic limitations that are not recited in claims 1-20. Because claims 1-20 remain unchanged, the applied prior art combination continues to teach or suggest the claimed subject matter. The rejections under 35 U.S.C. §103 with respect to claims 1-20 are therefore maintained.
Allowable Subject Matter
Claim 21 objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
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 (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 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.
Claims 1-2, 4-7 and 9-20 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou "Designing Supported Ionic Liquids (ILs) within Inorganic Nanosheets for CO2 Capture Applications" in view of Xin and Hao, "Imidazolium-based ionic liquids grafted on solid surfaces", Jiang, "Magnetic nanoparticles supported ionic liquids for lipase immobilization: Enzyme activity in catalyzing esterification", Beall et al., "Analysis of Analysis of Oligonucleotide DNA Binding and Sedimentation Properties of Montmorillonite Clay Using Ultraviolet Light Spectroscopy" and Benachour, "Multifunctional Peptide-Conjugated Hybrid Silica Nanoparticles for Photodynamic Therapy and MRI" the combination of which will be referred to hereafter as “modified Zhou”.
Regarding claim 1, Zhou discloses a functionalized organic-inorganic hybrid material comprising: an inorganic metal silicate clay nanosheet having a surface and comprising an inorganic metal and a plurality of silicon atoms (Zhou abstract “montmorillonite (MMT) single-layer nanosheets, identified as silicate clays containing both Si and metal atoms); wherein the surface is modified by attachment with a plurality of charged organic moieties (Zhou p.5549 rt. col. par. 2 teaches immobilization of ionic liquids on MMT nanosheets, describing “the coassembly of single layer nanosheets with 1-n-butyl-3-methylimidazolium chloride (BMIMCl)”); and wherein the plurality of charged organic moieties has a plurality of non-covalent counterions associated with the plurality of charged organic moieties (Zhou BMIM+ is associated with counterions Cl-); wherein the plurality of charged organic moieties comprises one or more permanently charged cationic groups (Zhou p.5549 rt. col. par. 2 “BMIM+”); wherein the plurality of non-covalent counterions comprises one or more anionic groups (Zhou abstract “Chloride“); and wherein the inorganic metal silicate clay nanosheet is a single layer nanosheet (Zhou abstract, while elsewhere Zhou discloses intercalating the nanosheets into layers for Co2 adsorption, Zhou explicitly defines the nanosheet as a single layer).
Zhou does not disclose that the surface is modified by covalent attachment and wherein the plurality of charged organic moieties are covalently bound to the plurality of silicon atoms at the surface. Zhou also does not disclose that the single layer nanosheet is 5 nanometers or less in thickness.
Xin and Hao teach that immobilization of imidazolium-based ionic liquids on inorganic supports is conventionally achieved by covalent grafting through silane chemistry (Xin and Hao abstract “imidazolium based ILs covalently grafted to non-porous and porous inorganic materials” and Xin and Hao p.7172 rt. col. par. 2 “via the reaction between trimethoxysilyl functional group (of 1-n-butyl-3-[3-(triethoxysilanyl)propyl]-4,5-dihydroimidazolium) in ILs and the abundant silanol groups”). This teaches that “grafting” denotes covalent anchoring (to include “clays (e.g., montmorillonite)” as an option for the support [Xin and Hao p. 7173 left col. par. 2]) and supports organic moieties are covalently bound to the plurality of silicon atoms at the surface.
Benachour illustrates covalent peptide conjugation to siliceous nanoparticles (Benachour p. 891 rt col. last par. to p. 892), showing that functionalizing siliceous surfaces with charged organic moieties was conventional, further reinforcing that covalent organic modification of silicate surfaces was routine.
Jiang describes supported ionic liquids on inorganic nanoparticles, emphasizing covalent immobilization to enhance stability and prevent leaching, further reinforcing the motivation to apply covalent attachment in Zhou’s system.
Finally, Beall et al. confirm that the montmorillonite single layer nanosheet disclosed by Zhou is 5 nanometers or less in thickness (Beall et al. Introduction on p. 1 “~1nm thick”).
It would have been obvious to one of ordinary skill in the art at the time of filing to modify Zhou’s ionic-liquid/MMT nanosheet hybrids by employing the covalent grafting strategies taught y Xin and Hao, since both recognize that covalent immobilization prevents leaching of ionic liquids and enhances stability, recyclability, and durability of the hybrids. Beall confirms that Zhou’s selection of MMT defines nanosheet dimensions that inherently satisfy the thickness limitation. Jiang and Benachour confirm that covalent immobilization of ionic liquids and biomolecules on siliceous supports was common, providing further motivation to employ covalent anchoring for predictable performance benefits.
Regarding claim 2, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the plurality of non-covalent counterions accompany the plurality of charged organic moieties to maintain electric neutrality (Zhou p.5549 rt. col. par. 2 “BMIM+” where the charged imidazolium group is accompanied by Cl- to maintain electric neutrality).
Regarding claim 4, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the one or more cationic groups comprise imidazolium (Zhou p.5549 rt. col. par. 2 “BMIM+”), pyrrolidinium, pyridinium, cholinium, ammonium, phosphonium, sulfonium, a small biological species, a metal cation, a complex cation, or a combination thereof.
Regarding claim 5, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 4, wherein the small biological species comprises a saccharide, a peptide (Benachour abstract and p. 891 rt col. last par. to p. 892 teaches peptide conjugated hybrid silica nanoparticles prepared by silane coupling), or a combination thereof.
Regarding claim 6, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the one or more anionic groups comprise hexafluorophosphate, tetrafluoroborate, triflate, dicyanamide, methyl sulfate, dimethyl phosphate, acetate, trifluoroacetate, perchlorate, an amino acid, a carboxylate, bis(trifluoromethylsulfonyl)imide, an alkylsulfate, a sulfate, a halide (Zhou abstract “Chloride“ is a halide), a pseudo-halide, a chromophore, a complex anion, or a combination thereof.
Regarding claim 7, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 2, wherein the plurality of non-covalent counterions or the plurality of charged organic moieties further comprises a fluorescing fluorophore, wherein the fluorophore is a natural fluorophore, synthetic fluorophore, fluorescent protein, fluorescent peptide, nucleic acid, fluorogenic dye, reactive dye, or a combination thereof (Benachour title and abstract “MRI contrast”).
Regarding claim 9, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the plurality of charged organic moieties further comprises a covalently bound zwitterionic organic moiety, such as a betaine, amino acid (Benachour title, abstract, p. 891 teaches peptide maybe covalently grafted on DOTA-silica-nanoparticles which comprises amino acids), or a combination thereof.
Regarding claim 10, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the plurality of charged organic moieties further comprises a pendant reactive group, wherein the pendant reactive group comprises a vinyl group, alkene, alkyne, methacrylate, alkyl halide, amine, epoxide, aldehyde, ketone, sulfhydryl group, maleimide, carboxylate, isothiocyanate, NHS ester, sulfonyl chloride, tosylate ester, glyoxal, photoreactive cross-linker, or a combination thereof (Xin and Hao p. 7179 left col. par. 2 “vinyl-, vinylbenzyl- and allyl-substituted imidazolium”).
Regarding claim 11, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 10, wherein the pendant reactive group is covalently coupled to a fluorescent probe, contrast agent, oligomer, polymer, chelating, extracting, targeting, or therapeutic ligand, aptamer, nucleic acid, enzyme, peptide, lipid, nanoparticle, or natural or synthetic antibody, or a combination thereof (Xin and Hao disclose the copolymerization of both polycation and polyanion on silica suggesting this, Benachour discloses the pendant reactive group may comprise a peptide, while Jiang shows enzymes (lipase) interfacing with IL functionalized inorganic supports).
Regarding claim 12, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, further comprising one or more metal nanoparticles, bi-metallic nanoparticles, multi-metallic nanoparticles, or a combination thereof, wherein the one or more nanoparticles are supported on the surface of the inorganic metal silicate clay nanosheet (modified Zhou discloses the base hybrid, namely MMT single layer nanosheets, while Jiang teaches wherein metal nanoparticles such as iron oxide are stabilized on ionic-liquid modified supports and further used to immobilize biomolecules such as lipase, thus showing that metal nanoparticles can be incorporated into ionic-liquid functionalized hybrid materials. It would have been obvious to a person of ordinary skill in the art to apply Jiang’s teaching of supporting metal nanoparticles on IL-functionalized substrates to Zhou’s IL-modified nanosheet base, thereby producing the claimed hybrid material with metal nanoparticles supported on the surface).
Regarding claim 13, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the inorganic metal comprises Mg2+, Ca2+, Zn2+, Mn2+, Co2+, Ni2+, Cu2+, Ce3+, Fe3+, Al3+ or a lanthanide (Beall p. 1 introduction explains that montmorillonite clays are aluminosilicates containing Al3+ and other metal cations such as Ca2+, Mg2+ and Fe3+).
Regarding claim 14, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the inorganic metal silicate clay nanosheet is a 1:1 clay, and wherein the inorganic metal forms an octahedral oxide sheet and the plurality of silicon atoms form a tetrahedral sheet, or wherein the inorganic metal silicate clay nanosheet is a 2:1 clay (Zhou “montmorillonite” is a 2:1 clay), wherein the inorganic metal forms an octahedral oxide layer, and wherein the octahedral oxide layer is sandwiched on both sides by a tetrahedral sheet comprising the plurality of silicon atoms.
Regarding claim 15, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the functionalized organic-inorganic hybrid material has a completely or partially functionalized surface (Zhou abstract describes the addition of the BMIMCl functional groups to form the hybrids, therefore, since it cannot be unfunctionalized the surface must be completely or partially functionalized).
Regarding claim 16, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1, wherein the functionalized organic-inorganic hybrid material is incorporated within a film, self-supported membrane, conformal coating, network, bulk material, or a combination thereof (Zhou p. 5549 Fig. 2 describes the material being incorporated into an intercalated hybrid thin film).
Regarding claim 17, modified Zhou discloses a method of synthesizing a functionalized organic- inorganic hybrid material comprising: (i) reacting at least one non-ionic silane with at least one nucleophile to generate at least one ionic organosilane having a plurality of charged organic moieties; wherein the plurality of charged organic moieties are covalently bound to the organosilane (Xin and Hao p. 7172 rt. col. describe the preparation of trimethoxysilyl-functionalized imidazolium salts prepared by reacting nonionic silanes “trimethoxysilyl” with nucleophiles “silanol groups”, producing ionic organosilanes where the charged imidazolium group “1-n-butyl-3-[3-(triethoxysilanyl)propyl]-4,5-dihydroimidazolium” is covalently bound to the silane backbone, additionally, Jiang teaches in scheme 3 p. 104 reacting the alkyl-substituted imidazole, which retains a nitrogen in its nucleophilic state (b), with an anionic silane to generate at least one ionic organosilane having a plurality of charged organic moieties (c)); and (ii) reacting the ionic organosilane with a metal salt to form a functionalized organic-inorganic hybrid material comprising a clay nanosheet having a surface and comprising an inorganic metal and a plurality of silicon atoms (Xin and Hao p. 7181 rt. col. discloses that the Cl- which accompanies the covalently bonded imidazolium may be replaced by AuCl4- (the anionic portion of a metal salt) by anion exchange through reduction using NaBH4, additionally Jiang scheme 3 further teaches that the counterions may be exchanged by treatment with NaBF4 or KPF6 and then hydrolyzed/condensed onto SiO2 prepared Fe3O4 nanoparticles (metal salt) to form a functionalized organic-inorganic hybrid material which by suggestion of Zhou and Xin and Hao is comprising a clay nanosheet having a surface and comprising an inorganic metal and a plurality of silicon atoms); wherein the surface is modified by covalent attachment with the plurality of charged organic moieties; and wherein the plurality of charged organic moieties are covalently bound to the plurality of silicon atoms at the surface (Xin and Hao abstract and Jiang scheme 1 p. 104 suggests that grafting of Zhou may form a covalent attachment at the Si surface); wherein the plurality of charged organic moieties has a plurality of non-covalent counterions associated with the plurality of charged organic moieties (Zhou expresses counterions are Cl- while Jiang and Xin and Hao teaches a variety of these counterions are optional); wherein the plurality of charged organic moieties comprises one or more permanently charged cationic groups (Zhou BMIM+); wherein the plurality of non-covalent counterions comprises one or more anionic groups (Zhou Cl-); and wherein the inorganic metal silicate clay nanosheet is a single layer nanosheet 5 nanometers or less in thickness (Beall et al. confirms that the inorganic metal silicate clay nanosheet chosen as Zhou’s a single layer nanosheet (Zhou abstract “montmorillonite”) is less than 5nm or less in thickness).
Regarding claim 18, modified Zhou discloses the method of claim 17, wherein the method further comprises (iii) contacting the functionalized organic-inorganic hybrid material with water to form an aqueous solution (Zhou teaches that the ionic-liquid modified montmorillonite nanosheets are readily dispersed and processed in aqueous media (Zhou p. 5549 left col. par. 1 and 2); (iv) contacting the aqueous solution with one or more nanoparticles in the presence of a reducing agent; and (v) stabilizing the one or more nanoparticles on the surface of the functionalized organic- inorganic hybrid material (Xin and Hao p. 7181 rt. col. discloses that the Cl- which accompanies the covalently bonded imidazolium may be replaced by AuCl4- (the anionic portion of a metal salt) by anion exchange through reduction using NaBH4); or wherein the method further comprises (iii) dissolving the functionalized organic-inorganic hybrid material in water to form an aqueous solution (Zhou teaches that the ionic-liquid modified montmorillonite nanosheets are readily dispersed and processed in aqueous media (Zhou p. 5549 left col. par. 1 and 2); (iv) contacting the aqueous solution with a water-soluble polymer (suggested by Xin and Hao who explain that supported ionic liquids can be fabricated into membranes or coatings “SILMs or supported ionic liquid membranes” (p. 7172 rt. col. par. 3) by dispersing the IL-functionalized material in a polymer matrix (p. 7171 rt. col. par. 2); and (v) forming the functionalized organic-inorganic hybrid material into a film (SILM suggest by Xin and Hao p. 7172 rt. col. par. 3 described as SIL films).
Regarding claim 19, modified Zhou discloses a method of using a functionalized organic-inorganic hybrid material comprising: (i) preparing a functionalized organic-inorganic hybrid material by reacting at least one non-ionic silane with at least one nucleophile to generate at least one ionic organosilane having a plurality of charged organic moieties; wherein the plurality of charged organic moieties are covalently bound to the ionic organosilane (Xin and Hao p. 7172 rt. col. describe the preparation of trimethoxysilyl-functionalized imidazolium salts prepared by reacting nonionic silanes “trimethoxysilyl” with nucleophiles “silanol groups”, producing ionic organosilanes where the charged imidazolium group “1-n-butyl-3-[3-(triethoxysilanyl)propyl]-4,5-dihydroimidazolium” is covalently bound to the silane backbone, additionally, Jiang teaches in scheme 3 p. 104 reacting the alkyl-substituted imidazole, which retains a nitrogen in its nucleophilic state (b), with an anionic silane to generate at least one ionic organosilane having a plurality of charged organic moieties (c)); and reacting the ionic organosilane with a metal salt to form a functionalized organic-inorganic hybrid material comprising a clay nanosheet having a surface and comprising an inorganic metal and a plurality of silicon atoms (Xin and Hao p. 7181 rt. col. discloses that the Cl- which accompanies the covalently bonded imidazolium may be replaced by AuCl4- (the anionic portion of a metal salt) by anion exchange through reduction using NaBH4; additionally, Jiang further teaches that the counterions may be exchanged by treatment with NaBF4 or KPF6 and then hydrolyzed/condensed onto SiO2 prepared Fe3O4 nanoparticles (metal salt) to form a functionalized organic-inorganic hybrid material which by suggestion of Zhou and Xin and Hao is comprising a clay nanosheet having a surface and comprising an inorganic metal and a plurality of silicon atoms); wherein the surface is modified by covalent attachment with the plurality of charged organic moieties (Zhou BMIMCl modifies the surface of MMT by covalent attachment in view of Xin and Hao and/or Jiang); and wherein the plurality of charged organic moieties are covalently bound to the plurality of silicon atoms at the surface (Xin and Hao p.7172 rt. col. par. 2); and (ii) using the functionalized organic-inorganic hybrid material (Zhou describes assembly of the hybrid material into intercalated hybrids and drying to remove moisture followed by use of the hybrids to capture CO2).
Regarding claim 20, modified Zhou discloses the method of claim 19, wherein the using comprises: (iia) contacting a solution comprising one or more contaminants with a surface comprising the functionalized organic-inorganic hybrid material (Zhou p. 5549 describes assembly of the hybrid material into intercalated hybrids and drying to remove moisture followed by use of the hybrids to capture CO2); (iib) reducing the concentration of the one or more contaminants in the solution to form a treated solution (Zhou p. 5549 and Fig. 8 describes assembly of the hybrid material into intercalated hybrids and drying to remove moisture followed by use of the hybrids to capture CO2 which reduce the concentration of CO2 in the affected solution to produce a treated solution); and (iic) optionally, repeating step (iia) or step (iib) one or more times with the treated solution; or wherein the using comprises using the functionalized organic-inorganic hybrid material in a catalytic reaction (Zhou p. 5553 rt. col. describes the use to include serving as a catalyst for various reactions, additionally, Xin and Hao p. 7177 section 3.2.2. describe the use of SILs such as these as catalysts).
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over "modified Zhou" (Zhou in view of Xin and Hao, Jiang, Beall et al. and Benachour) as applied to claim 1 above, and further in view of Mateyawa, "Effect of the ionic liquid 1-ethyl-3-methylimidazolium acetate on the phase transition of starch: dissolution or gelatinization".
Regarding claim 8, modified Zhou discloses the functionalized organic-inorganic hybrid material of claim 1.
Although modified Zhou discloses that anionic groups are routinely substituted to comprise a variety of useful anions (Jiang, Xin and Hao) modified Zhou does not expressly disclose wherein the anionic group comprises an alkylsulfate, alkylsulfonate, alkylcarboxylate, alkylphosphate, or a combination thereof.
Mateyawa explicitly demonstrates the use of 1-ethyl-3-methylimidazolium acetate and cites examples of ILs previously used that contained the chloride ion were replaced with acetate (Mateyawa p. 521 left col. par. 2) demonstrating that substitution of anions, one in favor of another is a routine procedure well known within the art.
It would have been obvious to one of ordinary skill in the art at the time of filing to substitute the chloride counterion in Zhou’s IL-nanosheet hybrids with the other known and routine anions such as acetate, sulfate, sulfonate, pr phosphate. Mateyawa expressly demonstrates imidazolium acetate and Xin and Hao along with Jiang show that anion variation is standard practice in supported IL chemistry. A person of ordinary skill in the art would be motivated to select these anions to alter solubility, stability, or biocompatibility while expecting predictable results.
Conclusion
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/W.A.G./Examiner, Art Unit 1779
/Bobby Ramdhanie/Supervisory Patent Examiner, Art Unit 1779