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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 02/04/2024 has been entered. Upon entering the submission, claims 1, 9, 11, and 17 are amended. Claims 4, 6, and 10 are cancelled. Claims 1-3, 5, 7-9, and 11-20 are pending.
Response to RCE Submission
Claim objection
Applicant’s amendment to claim 9 obviates the objection. The objection is hereby withdrawn.
Claim rejection under 35 U.S.C.§112(b)
Applicant’s amendments to claims 1, 9, 11, and 17 obviate the rejection. The rejection is hereby withdrawn.
Claim rejection under 35 U.S.C.§102(a)(1)
Applicant amended claim 1 by further defining a functionalized surface comprising 35 to 50 percent of a total surface area of the functionalized surface from 10 to 50 percent of a total surface area; and wherein the functionalized surface has a bromine content of at least 1.0 percent by weight. In addition, Applicant argues: 1) the cited Martin reference does not disclose or suggest that any brominated portion comprises 35 to 50 percent of the total surface area; and the Patent Office's calculation extrapolating Martin's 3.53 percent bromine content to 23.3 percent surface coverage relies on an improper linear extrapolation from Applicant's specification. The specification describes one specific sample prepared under specific conditions using thionyl bromide where a particular bromine content corresponded to a particular surface coverage. However, the relationship between bulk bromine content and surface coverage percentage is not linear and depends on the bromination mechanism, reagents, reaction conditions, and surface structure; 2) Martin employs N-bromosuccinimide in carbon tetrachloride, which operates through a radical mechanism, whereas Applicant's specification describes thionyl bromide proceeding through an ionic mechanism involving bromosulfite ester intermediates and carbocation formation. These mechanistic differences lead to different bromination patterns and surface coverage percentages even at similar bulk bromine contents; 3) More fundamentally, Martin's 3.53 percent bromine content is insufficient to achieve 35 to 50 percent surface coverage. Applicant's Table 3 in Example 1 demonstrates that achieving even 16.6 percent surface coverage required 2.5 percent bromine content. Achieving 35 to 50 percent surface coverage necessarily requires substantially higher bromine content, approaching or exceeding 4 to 5 percent based on Applicant's experimental data.
Applicant’s amendment and arguments have been fully considered, but are not sufficient to overcome the rejection.
Regarding Applicant’s 1st argument, Applicant fails to provide any reasonable evidence to support their argument that the Patent Office's calculation extrapolating Martin's 3.53 percent bromine content to 23.3 percent surface coverage relies on an improper linear extrapolation from Applicant's specification. Actually, the calculation applied in the Office Action is consistent with Applicant’s specification, and supported by Applicant’s evidence provided in their argument, which will be articulated in the following response to Applicant’s 3rd argument.
Regarding Applicant’s 2nd argument, the claimed limitation of the functionalized surface comprising brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface has nothing to do with the chemical reaction mechanism involved in bromination of the nanoscale diamond because the percentage of brominated portion of the functionalized surface is a chemical characteristic of the product, which is not decided by the preparation methods. See the similar analysis of the limitation “Product-by-process” at MPEP§2113.
Regarding Applicant’s 3rd argument, Applicant argued that Applicant's Table 3 in Example 1 demonstrates that achieving even 16.6 percent surface coverage required 2.5 percent bromine content. Achieving 35 to 50 percent surface coverage necessarily requires substantially higher bromine content, approaching or exceeding 4 to 5 percent based on Applicant's experimental data. Applicant’s argument is not persuasive. Actually, Applicant’s acknowledgment that achieving 16.6 percent surface coverage requires 2.5 percent bromine content further supports for Office’s previous analysis base on the same calculation of Martin's 3.53 percent bromine content to 23.3 percent surface coverage as following: (3.53%/2.5%)x16.6%=23.4%, which is consistent with the Examiner’s previous calculation of Martin's 3.53% bromine content is calculated to have a 23.3% Br coverage. Therefore, Martin's 3.53% bromine content having a 23.3% Br coverage reads on amended claim 1 wherein a brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface, and wherein the functionalized surface has a bromine content of at least 1.0 percent by weight. The remaining functionalized surface comes from hydroxyl group see Martin’s Scheme 3 at p.4510. The rejection is maintained.
Claim rejection under 35 U.S.C.§103(a)
Applicant’s amendment and argument have been fully considered, but not sufficient to overcome the rejection base on the similar analysis above. The rejection is maintained.
Claim Rejections - 35 USC § 112 (New)
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claims 1-3, 5, 7-9, and 11-20 are rejected under 35 U.S.C. 112, first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor(s), at the time the application was filed, had possession of the claimed invention.
Specifically, claim 1 is amended to include “a functionalized surface comprising 35 to 50 percent of a total surface area of the functionalized surface”. However, this amendment is not described in the original disclosure. It is not clear what this phrase means because “a functionalized surface” is assumed to have the same meaning of “a total surface area of the functionalized surface”, and cannot be further defined as having only 35 to 50 percent of the same functionalized surface. The original claim 1 filed on 11/17/2022 is drawn to a functionalized nanoscale diamond comprising: a functionalized surface comprising: a brominated portion; and a hydroxylated portion. The original claim 1 does not contain the limitation “comprising 35 to 50 percent of a total surface area of the functionalized surface”. Claims 2-3, 5, 7-9, and 11-26 depending on claim 1 are rejected accordingly.
In addition, claim 17 is drawn to an aminated nanoscale diamond comprising a functionalized surface comprising: an aminated portion comprising 35 to 50 percent of a total surface area of the functionalized surface; and a brominated portion or a hydroxylated portion. However, “an aminated portion comprising 35 to 50 percent of a total surface area of the functionalized surface” is not described in the original disclosure. The original claim 17 filed on 11/17/2022 is drawn to an aminated nanoscale diamond comprising a functionalized surface comprising: an aminated portion. In addition, Applicant’s specification [0071] describes “The exchange of a Br3d signal at ~2.5% to a N1s signal at ~7.8% is suggestive of a complete SN1 or E1 nucleophilic substitution by NH₃·THF under anhydrous conditions … We estimate that 36-52% of surface carbon atoms were aminated which translates to 6.5-9.5 amines/nm²”. However, the specification does not describe the claimed limitation “an aminated nanoscale diamond comprising a functionalized surface comprising: an aminated portion comprising 35 to 50 percent of a total surface area of the functionalized surface; and a brominated portion or a hydroxylated portion”. Claims 18-20 depending on claim 17 are rejected accordingly.
To overcome the rejection, Applicant to specifically point out the support in the original disclosure to support the amended claims, or cancel the New Matter.
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-3, 5, 7-9, and 11-16 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 pre-AIA the applicant regards as the invention.
Specifically, amended claim 1 contains a phrase “a functionalized surface comprising 35 to 50 percent of a total surface area of the functionalized surface”. It is not clear what this phrase means because “a functionalized surface” is assumed to have the same meaning of “a total surface area of the functionalized surface”, and cannot be further defined as having only 35 to 50 percent of the same functionalized surface. The original claim 1 filed on 11/17/2022 is drawn to a functionalized nanoscale diamond comprising: a functionalized surface comprising: a brominated portion; and a hydroxylated portion. The original claim 1 does not contain the limitation “comprising 35 to 50 percent of a total surface area of the functionalized surface”.
In addition, amended claim 1 contains a phrase “wherein the functionalized surface has a bromine content of at least 1.0 percent by weight”. However, the term “1.0 percent by weight” fails to define what weight it refers to. The term “1.0 percent by weight” can be interpreted as: 1) at least 1.0 percent by weight of functionalized nanoscale diamond, or 2) at least 1.0 percent by weight of pristine nanoscale diamond. The metes and bounds of amended claim 1 are not clear. Therefore, amended claim 1 is indefinite. The examiner interpreted the term “at least 1.0 percent by weight” as “at least 1.0 percent by weight of functionalized nanoscale diamond”.
Claims 2-3, 5, 7-9, and 11-16 depending on claim 1 are rejected, accordingly.
Claim Rejections - 35 USC § 102 (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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-3, 7-8, 13, and 16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Martin et al., Chemistry of Materials, (2009), v.21, p.4505-4514.
Amended claim 1 is drawn to a functionalized nanoscale diamond comprising: a functionalized surface comprising 35 to 50 percent of a total surface area of the functionalized surface: a brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface; and a hydroxylated portion comprising 10 to 40 percent of a total surface area of the functionalized surface, wherein the functionalized nanoscale diamond exhibits enhanced reactivity toward nucleophilic substitution reactions compared to non-functionalized nanoscale diamond, and wherein the functionalized surface has a bromine content of at least 1.0 percent by weight.
Because amended claim 1 is indefinite, the examiner interprets the term “at least 1.0 percent by weight” as “at least 1.0 percent by weight of functionalized nanoscale diamond”.
Claim 8 is drawn to a method of making the functionalized nanoscale diamond of claim 1, the method comprising contacting a nanoscale diamond with a brominating agent to form the functionalized nanoscale diamond.
Martin et al. discloses a functionalized nanoscale diamond comprising: a functionalized surface comprising: a brominated portion; and a hydroxylated portion, and a method for preparing the functionalized nanoscale diamond comprising treating diamond nanoparticles under deep Fenton oxidation reaction (right column, p.4505) to introduce hydroxyl groups on the surface of the diamond nanoparticles, which is further treated with NBS/CCl4 to convert some of the hydroxyl groups on the surface of the diamond nanoparticles into the bromide groups. See Scheme 3 at p.4510
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, wherein 50% of the hydroxyl groups are replaced with bromine group. Martin (right column p.4506) discloses after deep Fenton oxidation, the carbon percentage of pristine npD (95.87%) was reduced (93.28%) after deep Fenton (oxidation) treatment. This decrease in the carbon (2.59%) as a reflection of the introduction oxygen functionalities by the Fenton reaction with HO-npD has mostly preserved the diamond crystal structure. In addition, Martin discloses bromination of HO-npD (“Bromination of HO-npD”, right column at p.4509), and the percentage of carbon in Br-npD respect to the HO-npD was reduced from 93.28 to 89.75%, this fact being compatible with the presence of 3.53% bromine. This percentage of bromine corresponds to 0.44 mmol/g, with surface functionalization and corresponds at least to one bromine atom per 170 carbon atoms.
On the other hand, Applicant’s Specification [0108] discloses ND-Br-1 with 0.5% Br content is determined to have a 3.3% Br coverage. Based on this description, the HO-npD disclosed by Martin with the presence of 3.53% bromine is calculated to have a 23.3% Br coverage [(3.53%/0.5%)x3.3%=23.3%], which reads on the limitation “a brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface” of amended claim 1. Therefore, Martin et al. anticipates claims 1-3, 5, 7-8, and 13.
In terms of claim 16, wherein the method is free of contacting the nanoscale diamond with a catalyst, Martin et al. teaches a method for preparing the functionalized nanoscale diamond comprising contacting a nanoscale diamond (HO-npD) with a brominating agent (NBS) to form the functionalized nanoscale diamond (Br-npD) in a solvent of CCl4, without using a catalyst, namely free of contacting the nanoscale diamond with a catalyst.
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 5, 7, 9, 11-12, 14-15, and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Martin et al., Chemistry of Materials, (2009), v.21, p.4505-4514 in view of Melendrez et al., “Brominated nanoscale diamond enables room temperature and catalysis free functionalization chemistry”, Materials Research Society Meeting, Supporting Online Information, (November 2020), 31 pages, and Khan et al., Diamond & Related Materials, (2016), v.61, p32-40.
Determination of the scope and content of the prior art (MPEP §2141.01)
Martin et al. discloses a functionalized nanoscale diamond comprising: a functionalized surface comprising: a brominated portion; and a hydroxylated portion, and a method for preparing the functionalized nanoscale diamond comprising treating diamond nanoparticles under Fenton reaction to introduce hydroxyl groups on the surface of the diamond nanoparticles, which is further treated with NBS/CCl4 to convert some of the hydroxyl groups on the surface of the diamond nanoparticles into the bromide groups. See Scheme 3 at p.4510
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. In addition, Martin teaches the percentage of carbon in Br-npD respect to the HO-npD was reduced from 93.28 to 89.75%, this fact being compatible with the presence of 3.53% bromine. This percentage of bromine corresponds to 0.44 mmol/g, see “Bromination of HO-npD”, right column at p.4509.
Ascertainment of the difference between the prior art and the claims (MPEP §2141.02)
The difference between Applicant’s claims 5 and Martin et al. is that the prior art does not specially teach the brominated portion comprises 20 to 40 percent of a total surface area of the functionalized surface. Instead, Martin et al. teaches the percentage of carbon in Br-npD respect to the HO-npD was reduced from 93.28 to 89.75%, this fact being compatible with the presence of 3.53% bromine. This percentage of bromine corresponds to 0.44 mmol/g.
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
However, the difference is further taught and/or suggested by Martin et al. and/or Melendrez et al. because Martin et al. teaches a bromination method by treating HO-npD with a brominating agent NBS in CCl4 for converting -OH groups on the surface of the HO-npD into Br- group. In addition, Martin teaches the percentage of carbon in Br-npD respect to the HO-npD was reduced from 93.28 to 89.75%, this fact being compatible with the presence of 3.53% bromine. This percentage of bromine corresponds to 0.44 mmol/g, see “Bromination of HO-npD”, right column at p.4509. On the other hand, Applicant’s Specification [0108] discloses ND-Br-1 with 0.5% Br content is determined to have a 3.3% Br coverage. Based on this description, the HO-npD disclosed by Martin with the presence of 3.53% bromine is calculated to have a 23.3% Br coverage [(3.53%/0.5%)x3.3%=23.3%], which reads on the limitation “a brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface” of amended claim 1. Making the brominated portion comprises 20 to 40 percent of a total surface area of the functionalized surface are routine experimentation for one ordinary skilled in the art.
In addition, Melendrez et al. teaches another method for making ND-Br (i.e., Br-npD) by reacting ND-OH (i.e., HO-npD) with thionyl bromide (SOBr2), see “ND-Br synthesis/purification”. It would have been obvious for one ordinary skilled in the art to optimizing the reaction conditions disclosed by Melendrez et al. to make the claimed functionalized nanoscale diamond of claim 5.
In terms of claim 7, Martin et al. teaches a method of preparing HO-npD through Fenton reaction; and Melendrez et al. teaches another method for making ND-OH (i.e., HO-npD) by oxidized ND (i.e., npD) in an open air, see “Alcohol-rich HPHT Nanodiamond (ND-OH) preparation and storage”. It would have been obvious for one ordinary skilled in the art to optimizing the reaction conditions disclosed by Melendrez et al. and Martin et al. to make the claimed functionalized nanoscale diamond of claim 7.
In terms of claim 9, wherein the brominating agent comprises SOBr, Melendrez et al. teaches a method for making ND-Br (i.e., Br-npD) by reacting ND-OH (i.e., HO-npD) with thionyl bromide (SOBr2), see “ND-Br synthesis/purification”.
In terms of claims 11-12, Khan et al. teaches using ball milling technique for treating nano-diamonds, see p.32-34.
In terms of claims 14-15, Melendrez et al. teaches a method for making ND-Br (i.e., Br-npD) by reacting ND-OH (i.e., HO-npD) with thionyl bromide (SOBr2) using the catalyst of pyridine, see “ND-Br synthesis/purification”.
In terms of claims 17-20, Martin et al. teaches an aminated nanoscale diamond
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, wherein the amino group R is an arylamine having a tertiary amino group -N(CH3)2. See Scheme 4 at p.4511. In addition, Martin et al. teaches a bromination method of functionalizing nanoscale diamond by treating HO-npD with a brominating agent NBS in CCl4 for converting -OH groups on the surface of the HO-npD into Br- group. Martin teaches the percentage of carbon in Br-npD respect to the HO-npD was reduced from 93.28 to 89.75%, this fact being compatible with the presence of 3.53% bromine. This percentage of bromine corresponds to 0.44 mmol/g, see “Bromination of HO-npD”, right column at p.4509. On the other hand, Applicant’s Specification [0108] discloses ND-Br-1 with 0.5% Br content is determined to have a 3.3% Br coverage. Based on this description, the HO-npD disclosed by Martin with the presence of 3.53% bromine is calculated to have a 23.3% Br coverage [(3.53%/0.5%)x3.3%=23.3%], which reads on the limitation “a brominated portion comprising 10 to 50 percent of a total surface area of the functionalized surface” of amended claim 1. Making the brominated portion comprises 20 to 40 percent of a total surface area of the functionalized surface are routine experimentation for one ordinary skilled in the art.
Furthermore, Melendrez et al. teaches a method for making ND-Br (i.e., Br-npD) by reacting ND-OH (i.e., HO-npD) with thionyl bromide (SOBr2), see “ND-Br synthesis/purification”. Melendrez et al. teaches a method for making ND-NH2 (i.e., H2N-npD) by reacting the resulting ND-Br with propargylamine, and make aminated nanoscale diamond containing two different amines, see “ND-NH2 preparation (including both ammonia solution, condensed ammonia and gas phrase)”. It would have been obvious for one ordinary skilled in the art to optimizing the reaction conditions disclosed by Martin et al. in view of Melendrez et al. to make the claimed aminated nanoscale diamond of claims 17-20.
Conclusions
Claims 1-3, 5, 7-9, and 11-20 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.
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/YONG L CHU/Primary Examiner, Art Unit 1731
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