NANOCARBON MATERIAL DISPERSION COMPOSITION

DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 on 08/17/2026 has been entered. Upon entering the submission, claims 1, and 7-8 are amended. Claims 3-5, 9-11, and 13-18 are cancelled. New claims 19-32 are added. Claims 1-2, 6-8, 12, and 19-32 are pending. Response to RCE Submission Claim rejection under 35 U.S.C.§103(a) Applicants amended claim 1 by further defining the claimed nanocarbon material dispersion composition modified by a group represented by “Formula (1) below and/or a group containing a polyglycerin chain, wherein the group containing a polyglycerin chain is a group in which a hydrogen atom of a hydroxy group in at least a part of a polyglyceryl group is substituted with a monovalent organic group, -X1-R1 (1) where in Formula (1), X1 represents -Si-, -NH-, -O-, -O-C(=O)-, -C(=O)-O-, -NH-C(=0)-, -C(=O)-NH-, or -S-, and a bond extending left from X1 binds to the nanocarbon material; R1 represents a substituted or unsubstituted monovalent hydrocarbon group, and an atom that binds to X1 is a carbon atom”. In addition, Applicants argued that in the surface-modifying group "-X-R (1)" disclosed in Komatsu (the `926 publication), R is a polyglyceryl group. In contrast, in the group represented by Formula (1) of the present invention ("-X1-R1 (1)"), R1 is a monovalent hydrocarbon group. Since a polyglyceryl group is formed by the polymerization of glycerin, it is evident that its structure contains oxygen atoms. On the other hand, it is also evident to a person skilled in the art that a "hydrocarbon group" refers to a group composed of carbon and hydrogen, which does not contain oxygen atoms. Therefore, Komatsu (the `926 publication) does not disclose the "group represented by Formula (1)" of instant claims 1, 7, and/or 8 as a surface-modifying group for nanodiamond particles. Komatsu (the `926 publication) discloses a group represented by -X-R (where R is a polyglyceryl group); that is, "a group containing a polyglycerin chain." However, Komatsu does not in any way teach or suggest "a group containing a polyglycerin chain, wherein the hydrogen atoms of at least some of the hydroxy groups in a polyglyceryl group are substituted with monovalent organic groups," as presently claimed. Applicants’ amendments and arguments have been considered but not sufficient to overcome the rejection. Komatsu (the `926 publication) does not disclose a polyglyceryl group is formed by the polymerization of glycerin (also called glycerol PNG media_image1.png 101 274 media_image1.png Greyscale ). Instead, Komatsu (the `926 publication) teaches a polyglyceryl group is formed by polymerization of glycerin PNG media_image2.png 75 151 media_image2.png Greyscale . For example, Komatsu (the `926 publication [0030]) discloses a nanodiamond prepared from material graphite through the explosion process or high-temperature high-pressure process is known to have carboxyl groups on its surface due to side reactions occurring in the preparation; and a ND-COO--R can be produced by subjecting glycidol PNG media_image2.png 75 151 media_image2.png Greyscale to ring-opening polymerization directly with the carboxyl groups present on the surface of the material nanodiamond, see [0030] “Production of ND-COO-R” as an example. When a glycidol goes through ring-opening polymerization, the newly formed resulting ring-opened glycidols would go through polymerization reaction PNG media_image3.png 366 890 media_image3.png Greyscale , see Figure 3 of Mohammadifar et al., ACS Macro Letters, (2017), v.6, p.35-40. The resulting polyglyceryl group in the production of ND-COO-R disclosed by the `926 publication reads on the limitation “wherein the group containing a polyglycerin chain is a group in which a hydrogen atom of a hydroxy group in at least a part of a polyglyceryl group is substituted with a monovalent organic group”, wherein the monovalent organic group is “ PNG media_image4.png 63 68 media_image4.png Greyscale ” or “ PNG media_image5.png 68 74 media_image5.png Greyscale ”. In addition, Komatsu (the `926 publication [0033]) discloses a surface-modified nanodiamond ND-S--R in which by applying an ultraviolet ray (254 nm) to the surface of a hydrogenated nanodiamond (ND-H) to form a free radical, allowing a suitable alkyl mercaptan or dialkyl disulfide to trap the free radical to thereby introduce an alkylthio group onto the surface of the nanodiamond, wherein the alkylthio group reads on “ -X1-R1 (1) where in Formula (1), X1 represents -S-, and a bond extending left from X1 binds to the nanocarbon material; R1 represents a substituted or unsubstituted monovalent hydrocarbon group (alkyl group). Therefore, Applicants’ amendments and arguments are not sufficient to overcome the rejection, and the rejection is maintained. Claim Rejections - 35 USC § 103 (revised) In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action: A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102 of this title, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made. The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 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, 6-8, 12, and 19-32 are rejected under 35 U.S.C. 103 as being unpatentable over JP2015113278A (“the `278 publication”) to Fujimura et al. in view of US2010/261926 (“the `926 publication”) to Komatsu et al., Popov et al., Nanoscale Research Letters, (2017), v.12, p.561 (1-6), and Mohammadifar et al., ACS Macro Letters, (2017), v.6, p.35-40. Applicants’ claim 1 is drawn to a nanocarbon material dispersion composition comprising a dispersion medium and a nanocarbon material dispersed at nano-scale in the dispersion medium, the nanocarbon material comprising a nanodiamond particle and a graphene layer formed on a surface of the nanodiamond particle, wherein the nanocarbon material has a wavenumber, which corresponds to a peak-top value in a wavenumber range of 1580+50 cm-1 in a Raman spectrum, from 1585 cm-1 to 1630 cm-1; and the nanocarbon material has a peak that appears at 2θ = 43 to 44° in an XRD analysis, wherein the nanocarbon material comprises a surface-modified nanocarbon material in which a surface of the nanocarbon material is modified by a group represented by Formula (1) below and/or a group containing a polyglycerin chain, wherein the group containing a polyglycerin chain is a group in which a hydrogen atom of a hydroxy group in at least a part of a polyglyceryl group is substituted with a monovalent organic group, -X1-R1 (1) where in Formula (1), X1 represents -Si-, -NH-, -O-, -O-C(=O)-, -C(=O)-O-, -NH-C(=0)-, -C(=O)-NH-, or -S-, and a bond extending left from X1 binds to the nanocarbon material; R1 represents a substituted or unsubstituted monovalent hydrocarbon group, and an atom that binds to X1 is a carbon atom. The `278 publication [0001, English translation] discloses a method for producing diamond microparticles having excellent water dispersibility, an aqueous dispersion of diamond microparticles with excellent water dispersibility obtained by heat treatment under an inert gas atmosphere, and an aqueous dispersion of diamond microparticles (i.e., a nanocarbon material dispersion composition comprising a dispersion medium and a nanocarbon material dispersed at nano-scale in the dispersion medium) obtained by the method thereof. The `278 publication [0002] discloses the diamond microparticles, particularly those produced by the explosion method, have a core-shell structure consisting of a SP3 diamond core and a SP2 graphite shell, and the shell structure has aqueous functional groups such as -COOH and -OH. In the low concentration range of 1 to 2 wt.% of the diamond microparticles, they are relatively dispersible in water, but in the high concentration range of 3 to 10 wt.% they do not disperse uniformly in water and precipitate, which causes a problem when used in the processing of high-concentration aqueous dispersion. In order to prepare diamond microparticles having excellent high-concentration water dispersibility, the `278 publication [0004] discloses diamond microparticles having excellent high-concentration water dispersibility can be produced by heat treating diamond microparticles in an inert gas atmosphere at a temperature in the range of 700-900°C with high hardness, abrasion resistance, high thermal conductivity, high refractive index, etc. In addition, the `278 publication [0041] discloses a polishing slurry using a diamond microparticle water dispersion with good dispersity, excellent polishing efficiency and productivity can be uniformly applied to the surface of fibers or films with diamond particles having little aggregation such that it is possible to produce fibers or films with excellent hardness and abrasion resistance. In terms of the claimed limitation “wherein the nanocarbon material has a wavenumber, which corresponds to a peak-top value in a wavenumber range of 1580 ± 50 cm-1 in a Raman spectrum, from 1585 cm-1 to 1630 cm-1 ”, the present specification [0020 and 0022] describes the nanocarbon material preferably shows peaks in the G-band (generally in the range from 1550 to 1650 cm-1 in a Raman spectrum, and the presence of such peaks means that a graphene structure or a structure similar to a graphene structure is present, that a structure derived from a defect in a graphene structure or a structure similar to a structure derived from a defect in a graphene structure is present, and that a functional group is included; and when the wavenumber corresponding to the peak-top value is within the range from 1585 cm-1 to 1630 cm-1, the nanocarbon material has good dispersibility in the dispersion medium. This limitation of a peak-top value in a wavenumber range of 1580 ± 50 cm-1 in a Raman spectrum, from 1585 cm-1 to 1630 cm-1 is further known and further described in Popov et al., see Figs. 3-4, 5a, and 8). In terms of the claimed limitation “the nanocarbon material has a peak that appears at 2θ = 43 to 44° in an XRD analysis”, the specification [0026] describes the presence of the peak (at 2θ = 43 to 44° in an XRD analysis) means that the nanocarbon material has a diamond structure, which is also described in the `278 publication. Furthermore, since the aqueous dispersion of the heat-treated diamond microparticles disclosed in the `278 publication comprising a core-shell structure consisting of a SP3 diamond core and a SP2 graphite shell with excellent high-concentration water dispersibility, and prepared by the same method involving explosion method, and following heat method at a temperature in the range of 700-900°C, the two limitations of Raman spectrum and XRD peak are inherited properties of the aqueous diamond microparticles dispersion composition, wherein the dispersion medium is water. In terms of the limitation “wherein the nanocarbon material comprises a surface-modified nanocarbon material in which a surface of the nanocarbon material is modified by a group represented by Formula (1) below and/or a group containing a polyglycerin chain, wherein the group containing a polyglycerin chain is a group in which a hydrogen atom of a hydroxy group in at least a part of a polyglyceryl group is substituted with a monovalent organic group, -X1-R1 (1) where in Formula (1), X1 represents -Si-, -NH-, -O-, -O-C(=O)-, -C(=O)-O-, -NH-C(=0)-, -C(=O)-NH-, or -S-, and a bond extending left from X1 binds to the nanocarbon material; R1 represents a substituted or unsubstituted monovalent hydrocarbon group, and an atom that binds to X1 is a carbon atom”, the `278 publication teaches diamond microparticles have a core-shell structure consisting of an SP3 diamond core and an SP2 graphite shell, and that the shell structure (graphite) has aqueous functional groups, such as -COOH and -OH (para. [0002]), wherein the functional group -COOH reads on the Formula (I) -X-R, wherein X is carbonyl group (-CO), and R is a monovalent organic group (-OH); or X is an ether bond (-COO-), and R is a monovalent organic group (-H). In addition, a surface of the nanocarbon material is modified by a group represented by Formula (I) below: -X-R is further taught and/or suggested by the `926 publication. Specifically, the `926 publication (claims 1-3) teaches a surface-modified nanodiamond comprising a base nanodiamond and at least one polyglycerol-chain-containing group present on at least a surface portion of the base nanodiamond, the polyglycerol-chain-containing group represented by following Formula (1) -X-R wherein X represents one member selected from the group consisting of single bond, -NH-, -O-, -COO-, -PH(=O)O-, and -S-; and R represents a polyglyceryl group. The `926 publication [0014] teaches the surface-modified nanodiamond has significantly improved solubility or dispersibility and dispersion stability in water and/or polar organic solvents, can thereby be handled with remarkably improved handleability, and can be used in various uses as a stable solution or dispersion in water or a polar organic solvent or can be subjected to any of chemical reactions and physical reactions in water and/or a polar organic solvent. The `926 publication teaches the polyglyceryl group is formed by polymerization of glycerin PNG media_image2.png 75 151 media_image2.png Greyscale . For example, Komatsu (the `926 publication [0030]) discloses a nanodiamond prepared from material graphite through the explosion process or high-temperature high-pressure process is known to have carboxyl groups on its surface due to side reactions occurring in the preparation; and a ND-COO--R can be produced by subjecting glycidol PNG media_image2.png 75 151 media_image2.png Greyscale to ring-opening polymerization directly with the carboxyl groups present on the surface of the material nanodiamond, see [0030] “Production of ND-COO-R” as an example. When a glycidol goes through ring-opening polymerization, the newly formed resulting ring-opened glycidols would go through polymerization reaction PNG media_image3.png 366 890 media_image3.png Greyscale , see Figure 3 of Mohammadifar et al. The resulting polyglyceryl group in the production of ND-COO-R disclosed by the `926 publication reads on the limitation “wherein the group containing a polyglycerin chain is a group in which a hydrogen atom of a hydroxy group in at least a part of a polyglyceryl group is substituted with a monovalent organic group”, wherein the monovalent organic group is “ PNG media_image4.png 63 68 media_image4.png Greyscale ” or “ PNG media_image5.png 68 74 media_image5.png Greyscale ”. In addition, the `926 publication [0033] discloses a surface-modified nanodiamond ND-S--R in which by applying an ultraviolet ray (254 nm) to the surface of a hydrogenated nanodiamond (ND-H) to form a free radical, allowing a suitable alkyl mercaptan or dialkyl disulfide to trap the free radical to thereby introduce an alkylthio group onto the surface of the nanodiamond, wherein the alkylthio group, which reads on “ -X1-R1 (1) where in Formula (1), X1 represents -S-, and a bond extending left from X1 binds to the nanocarbon material; R1 represents a substituted or unsubstituted monovalent hydrocarbon group (alkyl group). One ordinary skilled in the art would have been motivated to further modify the nanocarbon material disclosed by the `278 publication with the modification group of the `926 publication through the method disclosed by the `926 publication (claims 4-6 and Example 1) in view of Mohammadifar et al. Therefore, the `278 publication in view of Popov et al., the `926 publication and Mohammadifar et al. would have rendered claims 1, and 7 obvious. In terms of claim 2, wherein the nanocarbon material has an average dispersed particle size (D50) of 100 nm or less that is obtained by a dynamic light scattering method, the `278 publication [0050] discloses the BD (diamond microparticle product) produced in Example 1 was crushed using zirconia to obtain BD with a median diameter of 50 nm. This BD had a medium diameter of 50 nm and specific gravity of 2.55 g/cm3. In terms of claim 6, wherein the dispersion medium comprises water, an aliphatic hydrocarbon, an aromatic hydrocarbon, an alicyclic hydrocarbon, an alcohol, an ether, an ester, an ionic liquid, or a lubricant base, the `278 publication [0001] discloses a method for producing diamond microparticles having excellent water dispersibility, an aqueous dispersion of diamond microparticles with excellent water dispersibility obtained by heat treatment under an inert gas atmosphere, and an aqueous dispersion of diamond microparticles. Wherein the dispersion medium comprises water. In terms of claim 8, the `278 publication [0041] discloses a polishing slurry using a diamond microparticle water dispersion with good dispersity, excellent polishing efficiency and productivity can be uniformly applied to the surface of fibers or films with diamond particles having little aggregation such that it is possible to produce fibers or films with excellent hardness and abrasion resistance, wherein the base material is fibers or films, and the coating film is the aqueous dispersion of the heat-treated diamond microparticles disclosed in the `278 publication. In terms of claim 12, wherein the dispersion medium comprises water, an aliphatic hydrocarbon, an aromatic hydrocarbon, an alicyclic hydrocarbon, an alcohol, an ether, an ester, an ionic liquid, or a lubricant base, the `278 publication [0001] discloses a method for producing diamond microparticles having excellent water dispersibility, an aqueous dispersion of diamond microparticles with excellent water dispersibility obtained by heat treatment under an inert gas atmosphere, and an aqueous dispersion of diamond microparticles, wherein the dispersion medium comprises water. In terms of claims 19, and 27, the `926 publication [0014] teaches the surface-modified nanodiamond has significantly improved solubility or dispersibility and dispersion stability in water and/or polar organic solvents, can thereby be handled with remarkably improved handleability, and can be used in various uses as a stable solution or dispersion in water or a polar organic solvent or can be subjected to any of chemical reactions and physical reactions in water and/or a polar organic solvent. This gives a nanodiamond material that is usable in engineering applications such as materials for polishing agents and dressers adopted to CMP (Chemical Mechanical Polishing); plating materials for corrosion-resistant electrodes adopted to fuel cells; materials for forming very hard surface coating layers typically of cutting tools; and highly heat-resistant and highly thermally conductive materials. In terms of claims 20, 22, 25, 28 and 30, the `926 publication [0039] discloses the amount of a chemically modifying group to be introduced onto a nanodiamond to give a surface-modified nanodiamond modified on surface with at least one polyglycerol-chain-containing group represented by Formula (1) is such that the amount of chemically modified portions each containing at least one polyglycerol chain is preferably from 4 to 750 parts by weight, more preferably from 9 to 380 parts by weight, and furthermore preferably from 13 to 150 parts by weight, per 100 parts by weight of the nanodiamond-structure matrix (base nanodiamond). The ratio of the amount of chemically modified portions containing at least one polyglycerol chain introduced onto the surface to the amount of the nanodiamond-structure matrix can be determined through the determination of a weight change during heat treatment of the surface-modified nanodiamond using a differential thermogravimetric analyzer (TG-DTA) or through the determination of the ratio in CHNO (carbon, hydrogen, nitrogen, and oxygen) composition between them by elemental analysis. In terms of claims 21, 23-24, 26, 29, and 31-32, the present specification [0020 and 0022] describes the nanocarbon material preferably shows peaks in the G-band (generally in the range from 1550 to 1650 cm-1 in a Raman spectrum, and the presence of such peaks means that a graphene structure or a structure similar to a graphene structure is present, that a structure derived from a defect in a graphene structure or a structure similar to a structure derived from a defect in a graphene structure is present, and that a functional group is included; and when the wavenumber corresponding to the peak-top value is within the range from 1585 cm-1 to 1630 cm-1, the nanocarbon material has good dispersibility in the dispersion medium. This limitation of a peak-top value in a wavenumber range of 1580 ± 50 cm-1 in a Raman spectrum, from 1585 cm-1 to 1630 cm-1 is known and described in Popov et al., see Figs. 3-4, 5a, and 8). Conclusions Claims 1-2, 6-8, 12, and 19-32 are rejected. Telephone Inquiry Any inquiry concerning this communication or earlier communications from the examiner should be directed to Yong L. Chu, whose telephone number is (571)272-5759. The examiner can normally be reached on M-F 8:30am-5:00pm. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amber R. Orlando can be reached on 571-270-3149. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300. Status Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). /YONG L CHU/Primary Examiner, Art Unit 1731