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 Objections
Claim 6 is objected to because of the following informalities: the term “non-5-en” should be written as “non-5-ene.” Appropriate correction is required.
Claim 11 is objected to because of the following informalities: the chemical structure recited in Claim 11 should be explicitly marked/labeled with the phrase “Formula I.” Appropriate correction is required.
Claim 12 is objected to because of the following informalities: the chemical structure recited in Claim 12 should be explicitly marked/labeled with the phrase “Formula IA.” Appropriate correction is required.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-4, 7-14, 16, 19-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Scanlon et al. (US 8,974,974).
Regarding Claim 1, Scanlon teaches an electrolyte for a rechargeable lithium battery (Abstract). Scanlon teaches that the electrolyte comprises a lithium salt (“metallic salt”) and a “diamondoid salt” comprising a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (“diamondoid-functionalized cationic core comprising a cationic core and a diamondoid group covalently bound to the cationic core”) (col. 2 lines 18-46, col. 3 lines 27-47, Example 1).
Regarding Claim 2, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (“the cationic core” is “a nitrogen-containing heterocyclic moiety”).
Regarding Claim 3, Scanlon teaches the instantly claimed invention of Claim 2, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the nitrogen-containing heterocyclic moiety comprises a “5-membered ring”).
Regarding Claim 4, Scanlon teaches the instantly claimed invention of Claim 3, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the 5-membered ring is “imidazole”).
Regarding Claim 7, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (“any other position on the cationic core not occupied by the diamondoid group” is an “R group” as instantly claimed).
Regarding Claim 8, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the cationic core is “a nitrogen-containing heterocyclic moiety” and “any other position on the cationic core not occupied by the diamondoid group” is an “R group” as instantly claimed).
Regarding Claim 9, Scanlon teaches the instantly claimed invention of Claim 8, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the nitrogen-containing heterocyclic moiety comprises a “5-membered ring”).
Regarding Claim 10, Scanlon teaches the instantly claimed invention of Claim 9, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the 5-membered ring is “imidazole”).
Regarding Claim 11, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the diamondoid-functionalized cationic core has “Formula I” with “R1, R2, R3, R4, and R5” as instantly claimed).
Regarding Claim 12, Scanlon teaches the instantly claimed invention of Claim 11, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the diamondoid-functionalized cationic core has “Formula IA” with “R1, R2, R3, and R4” as instantly claimed).
Regarding Claim 13, Scanlon teaches the instantly claimed invention of Claim 12, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the diamondoid-functionalized cationic core has Formula IA with “R1, R2, R3, and R4” as instantly claimed).
Regarding Claim 14, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the diamondoid-functionalized cationic core is “1,3-bis(adamantan-1-yl)imidazolium”).
Regarding Claim 16, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the diamondoid salt comprises a 1,3-bis(1-adamantyl)imidazolium cation and a lithium-phthalocyanine counter anion or a lithium-porphyrin counter anion covalently bonded to said cation (the diamondoid salt has “1 or 2 diamondoid groups covalently bound to the cationic core”).
Regarding Claim 19, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
As previously described (See Claim 1), the electrolyte a lithium salt (the metallic salt is “lithium salt”).
Regarding Claim 20, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
Scanlon teaches that the electrolyte is included in an electrochemical device (Abstract, col. 6 lines 12-17). For example, Scanlon teaches that the electrochemical device is a rechargeable lithium battery comprising a positive electrode, a negative electrode, and the electrolyte in contact with one or both of said electrodes (the electrochemical device comprises “an electrode, a counter electrode in electrical communication with the electrode, and the electrolyte of claim 1 in contact with the electrode, the counter electrode, or both”).
Regarding Claim 21, Scanlon teaches the instantly claimed invention of Claim 20, as previously described.
As previously described (See Claim 20), the electrochemical device is a rechargeable lithium battery (the electrochemical device is “a lithium-ion battery”).
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Scanlon et al. (US 8,974,974), and further in view of Shadrikova et al. (“Adamantylation of pyridine derivatives”).
Regarding Claim 5, Scanlon teaches the instantly claimed invention of Claim 2, as previously described.
Scanlon does not explicitly teach a 6-membered ring as instantly claimed.
However, Shadrikova teaches adamantane-functionalized pyridinium salts (Abstract, Page 1586). Shadrikova teaches that the salts include a 6-membered pyridine ring functionalized with adamantane (Page 1586). Shadrikova teaches that such functionalized salts provide for a broadened spectrum of conformational rigidity and lipophilicity characteristics.
Therefore, it would have been obvious before the effective filing date of the claimed invention that one of ordinary skill in the art would form the nitrogen-containing heterocyclic moiety of Scanlon such that it comprises a 6-membered pyridine ring functionalized with adamantane (as opposed to the 5-membered imidazole ring functionalized with adamantane) , as taught by Shadrikova, given that such a modification would provide for a broadened spectrum of conformation rigidity and lipophilicity characteristics.
Regarding Claim 6, Scanlon, as modified by Shadrikova, teaches the instantly claimed invention of Claim 5, as previously described.
As previously described (See Claim 5), the 6-membered ring is pyridine.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Scanlon et al. (US 8,974,974), and further in view of Ito et al. (JP 2019-147741, using the accompanying machine translation for citation purposes).
Regarding Claim 17, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
Scanlon does not explicitly teach that the diamondoid salt is non-symmetric.
However, Ito teaches an imidizaolium salt represented by formula (1), wherein “R1” in the formula is a cycloalkyl group ([0007]-[0010]). Ito teaches that the salt is functional as a replacement for N,N’-bis(1-adamantyl)imidazolium salts which are difficult to use industrially due to high manufacturing cost ([0003]-[0006]).
Therefore, it would have been obvious before the effective filing date of the claimed invention that one of ordinary skill in the art would form the diamondoid salt of Scanlon so as to be non-symmetric (i.e. replace one of the adamantane groups of Scanlon with a cycloalkyl R1 group as in Ito), as taught by Ito, given that such a non-symmetric diamondoid salt would be easier to use industrially because of a lower manufacturing cost versus N,N’-bis(1-adamantyl)imidazolium salts.
Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Scanlon et al. (US 8,974,974), and further in view of Richter et al. (“Synthesis of Diamantane-Derived N-Heterocyclic Carbenes and Applications in Catalysis,” provided by Applicant in the 01/10/24 IDS).
Regarding Claim 18, Scanlon teaches the instantly claimed invention of Claim 1, as previously described.
Scanlon does not explicitly teach that the diamondoid group is other than adamantane
However, Richter teaches diamantane-substituted imidazolium salts (Abstract). As illustrated in Figure 2, Richter teaches that as opposed to being substituted with adamantane, the salts are substituted with diamantane (Last paragraph of Page 193 to first paragraph of Page 194). Richter teaches that the diamantane-substituted salts exhibit increased steric demand and increased lipophilicity characteristics (Last paragraph of Page 195).
Therefore, it would have been obvious before the effective filing date of the claimed invention that one of ordinary skill in the art would use diamantane (“diamond group is other than adamantane”), as taught by Richter, as the diamondoid group of Scanlon, given that a diamantine-substitute salt would help provide for increased steric demand and lipophilicity characteristics.
Claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Scanlon et al. (US 8,974,974), and further in view of Masel et al. (US 2016/0369415).
Regarding Claim 22, Scanlon teaches the instantly claimed invention of Claim 20, as previously described.
Scanlon does not explicitly teach that the electrochemical device is a CO2 electrolyzer.
However, Masel teaches a CO2 electrolyzer (Abstract). Masel teaches that the electrolyzer comprises imidazolium materials which enhance the performance of CO2 electrolyzers ([0061]-[0064]).
Therefore, it would have been obvious before the effective filing date of the claimed invention that one of ordinary skill in the art would form the electrochemical device of Scanlon as a CO2 electrolyzer, as taught by Masel, given that the adamantane-substituted imidazolium material would help provide for enhanced CO2 electrolyzing performance.
Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Scanlon et al. (US 8,974,974).
Regarding Claim 23, Scanlon teaches the instantly claimed invention of Claim 20, as previously described.
Scanlon does not explicitly teach the instantly claimed method.
However, and as previously described (See Claim 20), Scanlon teaches that the electrolyte is included in an electrochemical device which is a rechargeable lithium battery comprising a positive electrode, a negative electrode, and the electrolyte in contact with one or both of said electrodes.
Therefore, it would have been obvious before the effective filing date of the claimed invention that one of ordinary skill in the art would operate the rechargeable lithium battery of Scanlon in the instantly claimed manner, given that Scanlon’s battery is rechargeable and therefore would be intended to, and be configured to, function (i.e. charge and discharge) via application of an electrical load or a voltage between the positive and negative electrode.
Allowable Subject Matter
Claim 15 is 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.
The following is a statement of reasons for the indication of allowable subject matter:
Claim 15 further limits the electrolyte of Claim 1 by explicitly requiring that the diamondoid-functionalized cationic core is 3-(adamantan-1-yl)-1-methylimidazolium.
The prior art references of record, as previously described, neither teach nor suggest the instantly claimed core material. In particular, Scanlon, Shadrikova, and Richter each disclose adamantane-based materials, but none of said materials have a methyl functional group as instantly claimed positioned in the instantly claimed location of the diamondoid-functionalized cationic core.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW W VAN OUDENAREN whose telephone number is (571)270-7595. The examiner can normally be reached 7AM-3PM EST M-F.
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/MATTHEW W VAN OUDENAREN/Primary Examiner, Art Unit 1728
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