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 .
Claim Status
Claims 1-2, 7, 11, 14-15, 17-19, 21, 25, 29, 33, 35, 40, 42,45, 47, 51, and 53 are pending.
Claims 1-2, 7, 11, 14-15, 17-19, 21, 25, 29, 33, 35, 40, 42,45, 47, 51, and 53 have been amended.
Claims 3-6, 8-10, 12-13, 16, 20, 22-24, 26-28, 30-32, 34, 36-39, 41, 43-44, 46, 48-50, 52, and 54-61 have been cancelled.
Thus, claims 1-2, 7, 11, 14-15, 17-19, 21, 25, 29, 33, 35, 40, 42,45, 47, 51, and 53 represent all claims currently under consideration.
Priority
Domestic Priority data as claimed by Applicant:
This application is a 371 of PCT/US2022/078895 (10/28/2022)
which claims benefit of 63/273,686 (10/29/2021)
Specification
The specification is objected to as failing to provide proper antecedent basis for the claimed subject matter. See 37 CFR 1.75(d)(1) and MPEP § 608.01(o). Correction of the following is required:
Claim 2 recites “The method of claim 1, wherein the method is substantially free of any acid or oxidant.” Although the specification describes that the presently claimed methods do not require treatment of the CNTs with concentrated acids or strong acid before amination (Specification; 0007, 0015, 0027, and 0049), the specification does not mention the term “oxidant” or make reference to a method that is “substantially free of any acid or oxidant”, as recited in claim 2.
Claim Objections
Claim 11 is objected to because of the following informalities:
In line 3, “or” should read “and”.
Claim 17 is objected to because of the following informalities:
In line 2, “watersolvent” should read “water-solvent”.
Claim 18 is objected to because of the following informalities:
In line 2, “watersolvent” should read “water-solvent”.
Claim 25 is objected to because of the following informalities:
In lines 3-4, “wherein the CNT comprises” should read “wherein the CNT nanomaterial comprises”.
Claim 35 is objected to because of the following informalities:
In line 2, “the alkylaminating reagent is an alkyl or alkenyl group” should read “the alkylaminating reagent comprises an alkyl or alkenyl group”.
Claim 51 is objected to because of the following informalities:
In lines 1-3, “obtained in a method of claim 1” should read “obtained in the method of claim 1”.
Claim 53 is objected to because of the following informalities:
In lines 1-3, “obtained in a method of claim 25” should read “obtained in the method of claim 25”.
In line 3, “group” should read “groups”.
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 17-18 and 42 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.
The term “high boiling” in claim 17 is a relative term which renders the claim indefinite. The term “high boiling” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. The limitation “any high boiling glycol” in line 3 is rendered indefinite by the use of the term “high boiling”.
Claim 18 recites “wherein the deionized watersolvent mixture has a deionized water content in the range of 0%-30% by volume” in lines 1-3. However, it is unclear how one could possess a deionized water-solvent mixture that has a deionized water content of 0% by volume, and this ambiguity renders the instant claim indefinite.
Claim 42 recites the phrase “any high boiling glycol” in line 3. However, it is unclear as written as to what constitutes a “high boiling glycol”. The term “high boiling” is not adequately defined in the instant specification, and this ambiguity renders the instant claim indefinite.
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 51 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bartha-Vári et al. (“Aminated Single-walled Carbon Nanotubes as Carrier for Covalent Immobilization of Phenylalanine Ammonia-lyase”; Period. Polytech. Chem. Eng. 2017, 61, 59-66; published 01-13-2017; IDS of 01-06-2025, NPL Cite No. C4).
Claim 51 recites “An aminated CNT, obtained in a method of claim 1, wherein the mass ratio of amine functional groups to mass of CNT is in the range of 0.001 to 0.05”. For the purposes of examination, the phrase “obtained in a method of claim 1” is being interpreted as a product-by-process limitation. MPEP § 2113(I) states that “[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” The process limitation of claim 51 is only defining the process of the product-by-process limitations and does not appear to impart any further structural features to the claimed product.
Further regarding claim 51, Bartha-Vári discloses the preparation of aminated single walled carbon nanotubes (SwCNTNH2), and elemental analysis data showed ~4.8% NH2 content for the SwCNTNH2 (Abstract; page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups). This elemental analysis further corresponds to ~95.2% carbon by mass. Therefore, the mass ratio of amine functional groups to the mass of CNT is 0.05, and this ratio resides within the instantly claimed range and thus anticipates the instant claim.
Claim 53 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Basiuk et al. (“Direct Solvent-Free Amination of Closed-Cap Carbon Nantubes: A Link to Fullerene Chemistry”; Nano Lett. 2017, 4, 863-866; published 04-14-2004; IDS of 01-06-2025, NPL Cite No. C5).
Claim 53 recites “An alkylaminated CNT, obtained in a method of claim 25, wherein the mass ratio of alkylamine group to CNT is in the range of 0.005 to 0.05”. For the purposes of examination, the phrase “obtained in a method of claim 25” is being interpreted as a product-by-process limitation. MPEP § 2113(I) states that “[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” The process limitation of claim 53 is only defining the process of the product-by-process limitations and does not appear to impart any further structural features to the claimed product.
Further regarding claim 53, Basiuk discloses the preparation of multiwalled carbon nanotubes (MWNTs) aminated with octadecylamine (ODA). 100 mg of MWNTs and 20 mg ODA were placed together in a reactor and heated to 150-170 ºC for 2 h, and excess unreacted ODA was removed afterward. Thermogravimetric analysis (TGA) of the ODA-MWNTs in the temperature interval 250-400 ºC showed the steepest weight loss due to organics decomposition for ODA-MWNTs (~5%) and corresponds to the weight of the MWNTs functionalized with ODA (Abstract; page 864, Col. 1, paragraphs 2-3 and Col. 2, Figure 1).
This TGA analysis corresponds to ~5% ODA-MWNTs and ~95% carbon by mass. Therefore, the mass ratio of alkylamine groups to CNT is 0.05, and this ratio resides within the instantly claimed range and thus anticipates the instant claim.
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.
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 1-2, 7, 11, 14-15, 17-19, 21, 25, 29, 33, 40, 42, 45, 47, 51, and 53 are rejected under 35 U.S.C. 103 as being unpatentable over Wunch et al. (US 2020/0087150 A1; published 03-19-2020), in view of Huang et al. (“Graphene: learning from carbon nanotubes”; J. Mater. Chem. 2011, 21, 919-929; published 10-20-2010) and Bartha-Vári et al. (“Aminated Single-walled Carbon Nanotubes as Carrier for Covalent Immobilization of Phenylalanine Ammonia-lyase”; Period. Polytech. Chem. Eng. 2017, 61, 59-66; published 01-13-2017; IDS of 01-06-2025, NPL Cite No. C4).
Regarding claims 1 and 25, Wunch teaches facile direct functionalization of pristine graphene nanoparticles. In particular, Wunch teaches a method for preparing an aminated graphene wherein the aminated graphene is obtained in a reaction by reacting graphene with an aminating reagent in a solvent or a solvent-deionized water mixture.
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The solvent is selected from the group consisting of: ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, a triol based solvent and combinations thereof. The deionized water-solvent mixtures includes at least one of the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, and a triol based solvent. The mass percentage of carbon in the graphene starting material is in the range of 99.0%-99.9%. The aminating reagent may be urea, ethylenediamine, para-phenylenedianiline, diethylamine, trimethylamine or a combination thereof. In an embodiment, Wunch teaches successful amination of pristine graphene using a mixture of ethylene glycol and urea under reflux at 180 ºC and 1 atmospheric pressure. In an alternate embodiment, a de-ionized water-solvent mixture is mixed with graphene and the aminating agent. The ratio of the graphene and the urea is in the range of 0.1-4.0 by weight, and the obtained aminated graphene compound has a mass percentage of amine functional groups (-NH2) in the range of 1%<-NH2<50% and a mass percentage of carbon is in the range of 30%<C %<99% (Title; 0007-0008, 0011, and 0043-0044; claims 1, 6, 8-10, 13, and 20; Figure 1).
Wunch does not teach the preparation of an aminated carbon nanotube (CNT) comprising reacting a CNT nanomaterial, as recited in instant claim 1; the preparation of an alkylaminated CNT comprising reacting a CNT nanomaterial, as recited in instant claim 25; or wherein the CNT comprises a mass percentage of carbon in the CNT nanomaterial in the range of 95.0%-99.9%, as recited in claims 1 and 25.
However, Huang teaches that graphene has many fascinating properties and potential applications with the greatest degree of similarity to its “brother” carbon nanotubes (CNTs). Carbon nanotubes are considered as the seamless wrapping of graphene, so it is easy to understand that graphene and carbon nanotubes have many similar physical and chemical properties. Graphene has nearly the same chemical properties as carbon nanotubes as their similar extended conjugated polyaromatic system. The difference is based on their different geometric structures. Their similarities promote the rapid development of graphene through applying the research strategies of carbon nanotubes to graphene (Abstract; page 919, Col. 1, paragraph 2; page 920, Fig. 1; page 922, Col. 1, paragraph 2).
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Thus, Huang teaches that CNTs are cylinders of graphene, which is the substrate being aminated in the method of Wunch.
Further regarding claims 1 and 25, Bartha-Vári teaches aminated single-walled carbon nanotubes (SwCNTNH2) and its preparation method. The reaction mixture contained SwCNT (400 mg), urea (400 mg), and dimethyl formamide (DMF, 5 mL). The reaction was carried out in a microwave assisted reactor at 300 ºC for 1 h. Elemental analysis data showed ~4.8% NH2 content for the aminated single walled carbon nanotubes (SwCNTNH2) (Abstract; page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups; page 65, Col. 1, paragraph 1). This elemental analysis further corresponds to ~95.2% carbon by mass. Therefore, the mass ratio of amine functional groups to the mass of CNT is 0.05. Thus, Bartha-Vári teaches that CNTs can be directly aminated under analogous conditions to that of Wunch to obtain products with a similar degree of amination, based on the reported mass ratios.
The prior art as taught by Wunch and Huang are analogous because they reside in the overlapping technical field of graphene-derived nanomaterials. In addition, the methods of Wunch and Bartha-Vári are analogous because they both teach the direct amination of nanometric allotropes of carbon (i.e., graphene and CNTs, respectively) using urea as an aminating reagent, in a manner consistent with the instantly claimed invention. Since Huang teaches that CNTs are cylinders of graphene, which is the substrate being aminated in the method of Wunch, the skilled artisan could predictably apply the amination method of Wunch to CNTs with a reasonable expectation of success. This is further supported by the teachings of Bartha-Vári, who teaches that CNTs can be aminated under analogous conditions to that of Wunch to obtain aminated CNTs with a similar degree of amination. Thus, the skilled artisan could predictably substitute the graphene nanoparticles of Wunch with the CNTs of Huang as further supported by Bartha-Vári to arrive at an alternative direct amination method of CNTs with a reasonable expectation of success. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results. See MPEP § 2143(I)(B).
Further regarding claim 25, Wunch teaches the use of an alkylamine, diethylamine, as an aminating reagent (0008). Therefore, the skilled artisan could predictably arrive at an alternative method for preparing an alkylaminated CNT based on the combined teachings of Wunch, Huang, and Bartha-Vári with a reasonable expectation of success.
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to have substituted the graphene nanoparticles of Wunch with the CNTs of Huang based on the supportive teachings of Bartha-Vári to arrive at the invention of claims 1 and 25. The motivation to do so would permit the skilled artisan to predictably pursue, with a reasonable expectation of success, an alternative production method for preparing aminated CNTs, as described above.
Regarding claim 2, the method of Wunch comprises aminating reagent and solvent, and does not use any acid or oxidant (0043-0044; claim 1).
Regarding claims 7 and 29, Bartha-Vári teaches the use of single-wall carbon nanotubes with an inner diameter of 0.8-1.6 nm, and outer diameter of 1-2 nm, and a length of 5-30 mm (page 60, Col. 1, paragraph 4). The CNT diameter taught by Bartha-Vári is close to the instantly claimed range. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” In addition, The CNT length taught by Bartha-Vári overlaps with the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 11 and 14, Wunch and Bartha-Vári both teach the use of urea as an aminating reagent (Wunch; 0043-0044; claim 8; Bartha-Vári; page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups).
Regarding claims 15 and 40, Wunch teaches a ratio of graphene and urea of 0.1-4.0 by weight (0008, claim 9). In addition, Bartha-Vári teaches a reaction mixture with 400 mg SwCNT and 400 mg urea (page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups), and therefore teaches a 1:1 weight ratio of CNT to urea. Thus, the cited prior art teaches weight ratios that overlap with or reside within the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 17 and 42, Wunch teaches that the deionized water-solvent mixtures includes at least one of the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, and a triol based solvent (0008; claim 10).
Regarding claim 18, Wunch teaches wherein the deionized water-solvent mixture has a deionized water content in the range of 5%-60% by volume, preferably 25%-50% by volume (0008; claim 11). These ranges overlap with the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 19, 21, 45, and 47, Wunch teaches that the temperature of the reaction is in the range of 150-250° C, preferably at 200° C at 1 atmospheric pressure, under reflux in air or under reflux in inert conditions. In an embodiment, Wunch teaches successful amination of pristine graphene using a mixture of ethylene glycol and urea under reflux at 180 ºC and 1 atmospheric pressure where reflux may be in air or in inert conditions (0009 and 0043; claim 14). The temperature range of Wunch is identical to the instantly claimed range and the reaction temperature in the embodiment of Wunch resides within the instantly claimed range. See MPEP § 2144.05(I).
Regarding claim 33, Wunch teaches the use of diethylamine (a dialkylamine), as an aminating reagent (0008).
Regarding claims 51 and 53, Wunch teaches that the aminated graphene compound has a mass percentage of amine functional groups (-NH2) in the range of 1%<-NH2<50%, and the mass percentage of carbon is in the range of 30%<C %<99% (0011 and claim 20). Therefore, several embodiments exist that would permit the skilled artisan to arrive at the instantly claimed amine/alkylamine functional groups to CNT mass ratio through means of routine optimization that is non-inventive in nature. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.”
Further regarding claims 51 and 53, since the processes of claims 1 and 25 are rendered obvious over Wunch, Huang, and Bartha-Vári, then the product obtained from these processes as recited in claims 51 and 53 must also be obvious.
Claim 35 is rejected under 35 U.S.C. 103 as being unpatentable over Wunch et al. (US 2020/0087150 A1; published 03-19-2020), in view of Huang et al. (“Graphene: learning from carbon nanotubes”; J. Mater. Chem. 2011, 21, 919-929; published 10-20-2010) and Bartha-Vári et al. (“Aminated Single-walled Carbon Nanotubes as Carrier for Covalent Immobilization of Phenylalanine Ammonia-lyase”; Period. Polytech. Chem. Eng. 2017, 61, 59-66; published 01-13-2017; IDS of 01-06-2025, NPL Cite No. C4) as applied to claims 1-2, 7, 11, 14-15, 17-19, 21, 25, 29, 33, 40, 42, 45, 47, 51, and 53 above, and further in view of Basiuk et al. (“Solvent-Free Derivatization of Pristine Multi-Walled Carbon Nanotubes with Amines”; J. Nanosci. Nanotech. 2005, 5, 984-990; published 06-01-2005; IDS of 01-06-2025, NPL Cite No. C6; hereinafter “Basiuk-2”).
Regarding claim 35, claim 25 is rendered obvious over Wunch, in view of Huang and Bartha-Vári, as detailed above.
Although Wunch teaches the use of diethylamine as an alkylaminating reagent (0008), Wunch, Huang, and Bartha-Vári do not explicitly teach an alkylaminating reagent comprising alkyl groups of C5 to C20 hydrocarbons, as recited in claim 35.
However, Basiuk-2 teaches the direct amination of multi-walled carbon nanotubes (MWCNTs) with nonylamine, dodecylamine, octadecylamine, 4-phenylbutylamine, and 1,8-octanediamine at a temperature of 150-170 ºC. Basiuk-2 further teaches that MWCNTs are hampered by their low solubility, and covalent functionalization is most frequently employed to increase nanotube solubility and dispersability in organic (and sometimes aqueous) solvents. Octadecylamine-MWCNTs synthesized exhibited an enhanced dispersability in propanol (Abstract; page 984, Col. 1, paragraph 1; page 985, Col. 1, paragraph 2 and Col. 2, Section 2.2: MWCNT Derivatization). The alkylaminating reagents nonylamine, dodecylamine, and octadecylamine taught by Basiuk-2 comprise alkyl groups of C9, C12, and C18 hydrocarbons, respectively, and therefore reside within the genus of instant claim 35.
The prior art as taught by Basiuk-2, Wunch, Huang, and Bartha-Vári are analogous because they reside in the overlapping technical field of graphene-derived nanomaterials. In addition, the methods of Basiuk-2, Wunch and Bartha-Vári are analogous because they teach the direct amination of graphene-derived nanomaterials (i.e., graphene and CNTs, respectively), in a manner consistent with the instantly claimed invention. As such, the skilled artisan would be sufficiently motivated to modify Wunch, Huang, and Bartha-Vári to incorporate the teachings of Basiuk-2 to implement the use of nonylamine, dodecylamine, and octadecylamine as alkylaminating reagents to pursue aminated CNTs with enhanced solubility and dispersability with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to obtain predictable results. See MPEP § 2143(I)(A).
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to have modified the method of Wunch, Huang, and Bartha-Vári to incorporate the teachings of Basiuk-2 to arrive at the claimed invention. The motivation to do so would permit the skilled artisan to predictably pursue, with a reasonable expectation of success, aminated CNTs with enhanced solubility and dispersability, as described above.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed methods. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Double Patenting Rejections
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. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); 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); 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) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) 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. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-2, 7, 11, 14-15, 17-19, 21, and 51 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 7-8, 13, and 15-17 of U.S. Patent No. 11,111,150 B2 (hereinafter patent ‘150), in view of Huang et al. (“Graphene: learning from carbon nanotubes”; J. Mater. Chem. 2011, 21, 919-929; published 10-20-2010) and Bartha-Vári et al. (“Aminated Single-walled Carbon Nanotubes as Carrier for Covalent Immobilization of Phenylalanine Ammonia-lyase”; Period. Polytech. Chem. Eng. 2017, 61, 59-66; published 01-13-2017; IDS of 01-06-2025, NPL Cite No. C4).
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding claim 1, claim 1 of patent ‘150 teaches a method for preparing an aminated graphene comprising reacting graphene with urea in a solvent or a solvent-deionized water mixture, and wherein the ratio of the graphene and the urea is in the range of 0.1-4.0 by weight. In addition, claim 7 of patent ‘150 teaches the method of claim 1 wherein the solvent is selected from the group consisting of: ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, a triol based solvent and combinations thereof. Furthermore, claim 13 of patent ‘150 teaches a method for preparing an aminated graphene comprising a reaction by reacting graphene with an aminating reagent in a solvent-deionized water mixture, wherein the solvent-deionized water mixture includes at least one solvent selected from the group consisting of: ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, and a triol based solvent. In addition, claim 5 of patent ‘150 teaches wherein the mass percentage of carbon in the graphene used in the amination method step is in the range of 99.0% 99.9%, and claim 17 of patent ‘150 teaches that the obtained aminated graphene compound has a mass percentage of amine functional groups (-NH2) in the range of 1%<-NH2<50% and a mass percentage of carbon is in the range of 30%<C %<99%.
Patent ‘150 does not teach the preparation of an aminated carbon nanotube (CNT) comprising reacting a CNT nanomaterial, as recited in instant claim 1, or wherein the CNT comprises a mass percentage of carbon in the CNT nanomaterial in the range of 95.0%-99.9%, as recited in claim 1.
These deficiencies are addressed by Huang and Bartha-Vári, whose teachings are incorporated herein as detailed above in the 103 rejection for claim 1.
Huang teaches that CNTs are cylinders of graphene, which is the substrate being aminated in the method of patent ‘150, and Bartha-Vári teaches that CNTs can be directly aminated under analogous conditions to that of patent ‘150 to obtain products with a similar degree of amination, based on the reported mass ratios.
The prior art as taught by patent ‘150 and Huang are analogous because they reside in the overlapping technical field of graphene-derived nanomaterials. In addition, the methods of patent ‘150 and Bartha-Vári are analogous because they both teach the direct amination of nanometric allotropes of carbon (i.e., graphene and CNTs, respectively) using urea as an aminating reagent, in a manner consistent with the instantly claimed invention. Since Huang teaches that CNTs are cylinders of graphene, which is the substrate being aminated in the method of patent ‘150, the skilled artisan could predictably apply the amination method of patent ‘150 to CNTs with a reasonable expectation of success. This is further supported by the teachings of Bartha-Vári, who teaches that CNTs can be aminated under analogous conditions to that of patent ‘150 to obtain aminated CNTs with a similar degree of amination. Thus, the skilled artisan could predictably substitute the graphene nanoparticles of patent ‘150 with the CNTs of Huang as further supported by Bartha-Vári to arrive at an alternative direct amination method of CNTs with a reasonable expectation of success. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results. See MPEP § 2143(I)(B).
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to have substituted the graphene nanoparticles of patent ‘150 with the CNTs of Huang based on the supportive teachings of Bartha-Vári to arrive at the invention of claim. The motivation to do so would permit the skilled artisan to predictably pursue, with a reasonable expectation of success, an alternative production method for preparing aminated CNTs, as described above.
Regarding claim 2, the method of patent ‘150 comprises aminating reagent and solvent, and does not explicitly teach the use of acid or an oxidant (claims 1 and 13). Furthermore, Bartha-Vári teaches a method for direct CNT amination wherein the reaction mixture consists of 400 mg SwCNT and 400 mg urea in DMF solvent (page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups). Therefore, based on theses combined teachings, the skilled artisan would be sufficiently motivated to pursue a direct CNT amination method that is substantially free of any acid or oxidant with a reasonable expectation of success, as recited in the instant claim.
Regarding claim 7, Bartha-Vári teaches the use of single-wall carbon nanotubes with an inner diameter of 0.8-1.6 nm, and outer diameter of 1-2 nm, and a length of 5-30 mm (page 60, Col. 1, paragraph 4). The CNT diameter taught by Bartha-Vári is close to the instantly claimed range. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” In addition, The CNT length taught by Bartha-Vári overlaps with the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 11 and 14, patent ‘150 and Bartha-Vári both teach the use of urea as an aminating reagent (claims 1 and 16 of patent ‘150; Bartha-Vári; page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups).
Regarding claim 15, claim 1 of patent ‘150 teaches a ratio of graphene and urea of 0.1-4.0 by weight. In addition, Bartha-Vári teaches a reaction mixture with 400 mg SwCNT and 400 mg urea (page 60, Col. 2, Section 2.2.1: Functionalization of SwCNT with amino groups), and therefore teaches a 1:1 weight ratio of CNT to urea. Thus, the cited prior art teaches weight ratios that overlap with or reside within the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claim 17, claims 1, 7, and 13 of patent ‘150 teach that the deionized water-solvent mixtures includes at least one of the group consisting of ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, any high boiling glycol, and a triol based solvent.
Regarding claim 18, claim 15 of patent ‘150 teaches wherein the deionized water-solvent mixture has a deionized water content in the range of 5%-60% by volume. This range overlaps with the instantly claimed range. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 19 and 21, claim 8 of patent ‘150 teaches that the temperature of the reaction is in the range of 150-250° C, at 1 atmospheric pressure, under reflux in air or under reflux in inert conditions. The temperature range of patent ‘150 is identical to the instantly claimed range.
Regarding claim 51, patent ‘150 teaches that the aminated graphene compound has a mass percentage of amine functional groups (-NH2) in the range of 1%<-NH2<50%, and the mass percentage of carbon is in the range of 30%<C %<99% (claim 17). Therefore, several embodiments exist that would permit the skilled artisan to arrive at the instantly claimed amine/alkylamine functional groups to CNT mass ratio through means of routine optimization that is non-inventive in nature. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.”
Further regarding claim 51, since the process of claim 1 is rendered obvious over patent ‘150, Huang, and Bartha-Vári, then the product obtained from this process as recited in claim 51 must also be obvious.
Claims 25, 29, 33, 35, 40, 42, 45, 47, and 53 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 7-8, 13, and 15-17 of U.S. Patent No. 11,111,150 B2 (hereinafter patent ‘150), in view of Huang et al. (“Graphene: learning from carbon nanotubes”; J. Mater. Chem. 2011, 21, 919-929; published 10-20-2010) and Bartha-Vári et al. (“Aminated Single-walled Carbon Nanotubes as Carrier for Covalent Immobilization of Phenylalanine Ammonia-lyase”; Period. Polytech. Chem. Eng. 2017, 61, 59-66; published 01-13-2017; IDS of 01-06-2025, NPL Cite No. C4) as applied to claims 1-2, 7, 11, 14-15, 17-19, 21, and 51 above, and further in view of Basiuk et al. (“Solvent-Free Derivatization of Pristine Multi-Walled Carbon Nanotubes with Amines”; J. Nanosci. Nanotech. 2005, 5, 984-990; published 06-01-2005; IDS of 01-06-2025, NPL Cite No. C6; hereinafter “Basiuk-2”).
Regarding claims 25, 33, and 35, patent ‘150, Huang, and Bartha-Vári do not teach a method for preparing an alkylaminated CNT comprising reacting an alkylaminating reagent as recited in claim 25; wherein the alkylaminating reagent is a monoalkyl amine, monoalkenyl amine, dialkyl amine or dialkenyl amine as recited in claim 33; or an alkylaminating reagent comprising alkyl groups of C5 to C20 hydrocarbons, as recited in claim 35.
However, Basiuk-2 teaches the direct amination of multi-walled carbon nanotubes (MWCNTs) with nonylamine, dodecylamine, octadecylamine, 4-phenylbutylamine, and 1,8-octanediamine at a temperature of 150-170 ºC. Basiuk-2 further teaches that MWCNTs are hampered by their low solubility, and covalent functionalization is most frequently employed to increase nanotube solubility and dispersability in organic (and sometimes aqueous) solvents. Octadecylamine-MWCNTs synthesized exhibited an enhanced dispersability in propanol (Abstract; page 984, Col. 1, paragraph 1; page 985, Col. 1, paragraph 2 and Col. 2, Section 2.2: MWCNT Derivatization). The alkylaminating reagents nonylamine, dodecylamine, and octadecylamine taught by Basiuk-2 are monoalkyl amines that comprise alkyl groups of C9, C12, and C18 hydrocarbons, respectively, in a manner consistent with the limitations of claims 25 and 33 and the recited genus of claim 35 detailed above.
The prior art as taught by Basiuk-2, patent ‘150, Huang, and Bartha-Vári are analogous because they reside in the overlapping technical field of graphene-derived nanomaterials. In addition, the methods of Basiuk-2, patent ‘150, and Bartha-Vári are analogous because they teach the direct amination of graphene-derived nanomaterials (i.e., graphene and CNTs, respectively), in a manner consistent with the instantly claimed invention. As such, the skilled artisan would be sufficiently motivated to modify patent ‘150, Huang, and Bartha-Vári to incorporate the teachings of Basiuk-2 to implement the use of nonylamine, dodecylamine, and octadecylamine as alkylaminating reagents to pursue aminated CNTs with enhanced solubility and dispersability with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to obtain predictable results. See MPEP § 2143(I)(A).
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to have modified the method of patent ‘150, Huang, and Bartha-Vári to incorporate the teachings of Basiuk-2 to arrive at the claimed invention. The motivation to do so would permit the skilled artisan to predictably pursue, with a reasonable expectation of success, aminated CNTs with enhanced solubility and dispersability, as described above.
Regarding claims 29, 40, 42, 45, 47, and 53, these claims are rendered obvious for the reasons detailed in the double patenting rejections of claims 7, 15, 17, 19, 21, and 51 above.
Conclusion
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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