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 .
DETAILED ACTION
Claims 1-15 of D. Hood et al., US 18/240,873 (Aug. 31, 2023) are pending. Claims 5-15 are withdrawn from further consideration as being drawn to the non-elected inventions of Groups (II) and (III). 37 CFR 1.142(b). Claims 1-4 are under examination on the merits. Claims 1 and 3 are rejected. Claims 2 and 4 are objectionable.
Election/Restrictions
Grounds For Restriction
There are two criteria for a proper requirement for restriction between patentably distinct inventions: (A) The inventions must be independent or distinct as claimed; and (B) There would be a serious burden on the examiner if restriction is not required. MPEP § 803(I). In the instant case, restriction to one of the following inventions is required under 35 U.S.C. 121:
Group (I) Claims 1-4 drawn to drawn to a compound comprising Formula 1, classified in C01G23/00, C01G25/00; OR C01G27/00, depending on the metal atom;
Group (II) Claims 5-9 drawn to drawn to drawn to a compound comprising Formula 3, classified in C07F17/00; or
Group (III) Claims 10-15 drawn to drawn to drawn to a compound comprising Formula 5, classified in C07F17/00.
Inventions (I) - (III) Are Directed to Distinct Inventions
Inventions (I)-(III) are directed to related products. The related inventions are distinct if: (1) the inventions as claimed are either not capable of use together or can have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions as claimed are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions as claimed have a materially different design, mode of operation, function, or effect because they are directed to different, non-overlapping Markush genera. Furthermore, the inventions as claimed do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Search Burden
Where the inventions as claimed are shown to be independent or distinct the examiner, in order to establish reasons for insisting upon restriction, must explain why there would be a serious search and/or examination burden on the examiner if restriction is not required. In order to demonstrate a serious search burden. MPEP § 808.02. A serious burden may be shown where it is necessary to search for one of the inventions in a manner that is not likely to result in finding art pertinent to the other invention(s), e.g., searching different electronic resources, or employing different search queries, a different field of search is shown, even though the two are classified together. MPEP § 808.02. Patents need not be cited to show different fields of search. MPEP § 808.02.
In the instant case, there is a search burden between inventions (I)-(III) because these Groups are directed to compounds of different Markush formulae. As such, searching requires generating different search queries using CAS/CAPLUS software. Further electronic searching is required respecting these different compounds within other databases, such as electronic patent databases, textbooks/electronic libraries, Google and Google Scholar.
Further, Group (I) is separately classified. MPEP § 808.02. This shows that this invention has attained recognition in the art as a separate subject for inventive effort, and also a separate field of search. MPEP § 808.02. Patents need not be cited to show separate classification. MPEP § 808.02.
Election by Telephone
During an interview with Eric Nielson on January 5, 2026 to request an oral election to the above restriction requirement, Applicant elected Group (I), claims 1-4, drawn to a compound comprising Formula (I). Affirmation of this election must be made by applicant in replying to this Office action. Claims 5-15 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to the non-elected inventions of Groups (II) and (III).
Reply and Traversal
Affirmation of Applicant’s above telephonic election must be made by applicant in replying to this Office action.
Restriction for examination purposes as indicated is proper because all the inventions listed in this action are independent or distinct for the reasons given above and there would be a serious search and/or examination burden if restriction were not required
The election of an invention may be made with or without traverse. To reserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the restriction requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable upon the elected invention.
Should applicant traverse on the ground that the inventions are not patentably distinct, applicant should submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. In either instance, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III).
Structural Interpretation of Certain Claim 1 Chemical Groups
It is first noted that the claim 1 transitional phrase “comprising” is open-ended and does not exclude additional, unrecited chemical structure from Formula 1. MPEP § 2111.03(I). For example, additional metal ligands and substituent groups are not excluded from Formula 1.
Claim 1 recites the following chemical groups:
Claim 1 . . . L1 is a C1-C15 fluoroalkyl, C1-C15 alkoxide containing at least one fluoro group, C2-C15 amide containing at least one fluoro group, C2-C15 carboxylate containing at least one fluoro group, or F; and
L2-L4 are each independently a C1-C15 alkyl, C2-C15 amide, C1-C15 alkoxide, C1-C15 carboxylate, C5-C15 amidinate, C5-C15 guanidinate, C5-C15 [Symbol font/0x62]-diketonate, C5-C15 [Symbol font/0x62]-ketoiminate, C5-C15 [Symbol font/0x62]-diketiminate, C1-C15 fluoroalkyl, C1-C15 alkoxide containing at least one fluoro group, C2-C15 amide containing at least one fluoro group, C2-C15 carboxylate containing at least one fluoro group, F, Cl, Br, I, or H.
The specification does not discuss the meaning of the claim 1 carbon-number ranges (for example, C5-C15 amidinate). This carbon-number nomenclature is broadly and reasonably interpreted as requiring the claimed carbon number bonded to the recited functional group, where the carbon atoms may be saturated or unsaturated and substituted with any chemical group. This interpretation is, of course, subject to the transitional phrase “comprising” (as discussed above).
The specification does not structurally define any of “C5-C15 amidinate, C5-C15 guanidinate, C5-C15 [Symbol font/0x62]-diketonate, C5-C15 [Symbol font/0x62]-ketoiminate, C5-C15 [Symbol font/0x62]-diketiminate” nor does the specification disclose any species comprising these groups. However, the structural meaning of these groups is well known in the art as the following bidentate ligands:
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where R is any chemical group. See, D. Dhakal et al., 32 Journal of Vacuum Science & Technology A (2014) ([Symbol font/0x62]-diketonate); F. Edelmann, 61 Advances in Organometallic Chemistry, 55-57 (2013) (amidinate and guanidinate); M. Zhong et al., 49 Dalton Trans., 1351-1364 (2020) ([Symbol font/0x62]-ketoiminate); R. Webster, 46 Dalton Trans., 4483-4498 (2017) ([Symbol font/0x62]-diketiminate).
The claim 1 group “C2-C15 amide” (undefined by the specification) is interpreted consistently with its common usage in organometallic chemistry as an amine conjugate base (i.e., -NR1R2), where the nitrogen is bonded directly to the metal atom and R1 and R2 are any chemical group. For example, Li-N(i-Pr)2 is referred to in the organmetallic art as lithium diisopropylamide. See e.g., M. Lappert et al., 105 Journal of the American Chemical Society, 302-304 (1983). This interpretation is consistent with the specification. See e.g., specification at pages 11-12, [0050].
It is further noted that the claimed L1-L4 groups “C1-C15 alkoxide” and “C2-C15 carboxylate” have an open, anionic oxygen, and are therefore reasonably interpreted as bonded to the metal by way of a direct covalent bond between the anionic oxygen and the metal atom. This interpretation is consistent with the specification. See e.g., specification at page 24, [00119].
Claim Objections
Claims 2 and 4 are 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.
Rejections 35 U.S.C. 112(b)
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.
A decision on whether a claim is indefinite under 35 U.S.C. 112(b) requires a determination of whether those skilled in the art would understand what is claimed when the claim is read in light of the specification. MPEP § 2173.02.
Unclear Claim Language
Claim 1 is rejected under 35 U.S.C. 112(b) as being indefinite because the following highlighted claim 1 recitation of “independently” with respect to the bidentate groups “C5-C15 amidinate, C5-C15 guanidinate, C5-C15 [Symbol font/0x62]-diketonate, C5-C15 [Symbol font/0x62]-ketoiminate, C5-C15 [Symbol font/0x62]-diketiminate” is inconsistent with its plain meaning:
Claim 1 . . . L1 is a C1-C15 fluoroalkyl, C1-C15 alkoxide containing at least one fluoro group, C2-C15 amide containing at least one fluoro group, C2-C15 carboxylate containing at least one fluoro group, or F; and
L2-L4 are each independently a C1-C15 alkyl, C2-C15 amide, C1-C15 alkoxide, C1-C15 carboxylate, C5-C15 amidinate, C5-C15 guanidinate, C5-C15 [Symbol font/0x62]-diketonate, C5-C15 [Symbol font/0x62]-ketoiminate, C5-C15 [Symbol font/0x62]-diketiminate, C1-C15 fluoroalkyl, C1-C15 alkoxide containing at least one fluoro group, C2-C15 amide containing at least one fluoro group, C2-C15 carboxylate containing at least one fluoro group, F, Cl, Br, I, or H.
MPEP § 2173. As discussed in Claim Interpretation above, the art teaches that each of the bidentate ligands “C5-C15 amidinate, C5-C15 guanidinate, C5-C15 [Symbol font/0x62]-diketonate, C5-C15 [Symbol font/0x62]-ketoiminate, C5-C15 [Symbol font/0x62]-diketiminate” occupies two valence positions of the metal (i.e., forms a ring with the metal atom), which is inconsistent with the meaning of “independently” in claim 1.
Claim Rejections - 35 USC § 102 (AIA )
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
35 U.S.C. 102(a)(1) Rejection over V. Tuskaev et al., 71 Russian Chemical Bulletin. 76-82 (Jan. 2022) (“Tuskaev”)
Claims 1 and 3 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by V. Tuskaev et al., 71 Russian Chemical Bulletin. 76-82 (Jan. 2022). Tuskaev disclose the following compounds 2 and 3.
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Tuskaev at page 77, col. 2. Each of these compounds falls within the genus of claim 1, Formula 1, where M is titanium, L1 is “C1-C15 alkoxide containing at least one fluoro group” and L2-L4 are “C1-C15 alkoxide” and “C1-C15 alkoxide containing at least one fluoro group”.
Tuskaev compound 3 meets each and every limitation of claims 1 and 3 when “L1-L4 are each independently 1,1,1,3,3,3-hexafluoro-2-propoxide”.
35 U.S.C. 102(a)(1)/(2) Rejection over S. Kataoka et al., WO 2016/143428 (2016) (“Kataoka”)
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by S. Kataoka et al., WO 2016/143428 (2016) (“Kataoka”). Kataoka discloses the following compound:
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Kataoka at page 48. This compound falls within the genus of claim 1, Formula 1, where M is zirconium, L1 is “C2-C15 carboxylate containing at least one fluoro group” and L2-L4 are “C1-C15 carboxylate” and “C2-C15 carboxylate containing at least one fluoro group”.
35 U.S.C. 102(a)(1) Rejection over Y. Okuzumi et al., GB 1009310 (1964) (“Okuzumi”)
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Y. Okuzumi et al., GB 1009310 (1964). Okuzumi discloses the following three compounds
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Okuzumi at page 5, col. 1, lines 50-60, see also, CAS Abstract and Indexed Compounds, Y. Okuzumi et al., GB 1009310 (1964).
Each of these compounds clearly falls within the genus of claim 1 when M is titanium and L1 is “C2-C15 carboxylate containing at least one fluoro group”.
35 U.S.C. 102(a)(1) Rejection over D. Bradley et al., 13 Chemical Communications (London), 284 (1965) (“Bradley”)
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by D. Bradley et al., 13 Chemical Communications (London), 284 (1965) (“Bradley”). Bradley discloses the following dialkoxybis(acetylacetonato)titanium compound.
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Bradely at page 284 (third species listed in the Table); see also, CAS Abstract, D. Bradley et al., 13 Chemical Communications (London), 284 (1965). This compound falls within the genus of claim 1, Formula 1, where M is titanium, L1 is “C1-C15 alkoxide containing at least one fluoro group” and L2-L4 are “C1-C15 alkoxide containing at least one fluoro group” and “C5-C15 [Symbol font/0x62]-diketonate”.
35 U.S.C. 102(a)(1) Rejection over M. Morstein et al., 5 Chemical Vapor Deposition, 151-158 (1999) (“Morstein”)
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by M. Morstein et al., 5 Chemical Vapor Deposition, 151-158 (1999) (“Morstein”). Morstein discloses the following complex cis-Zr(acac)2(hfip)2.
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Morstein at page 152, Fig. 1. This species falls within the genus of claim 1, Formula 1, where M is zirconium, L1 is “C1-C15 alkoxide containing at least one fluoro group” and L2-L4 are “C1-C15 alkoxide containing at least one fluoro group” and “C5-C15 [Symbol font/0x62]-diketonate”.
Subject Matter Free of the Art of Record
Claims 2 and 4 are free of the art of record. The closest art of record to claim 2 is S. Meiere et al., US 7,956,207 (2011). Meiere discloses organometallic compounds represented by the formula (R4R3N)xM(NR1R2)y, wherein M is a metal, R1-R4 are different and are each a hydrocarbon group or a heteroatom-containing group. Meiere at col. 2, lines 29-55. Meiere discloses that these compounds are useful as precursors for deposition of metal films. Meiere at col. 15, lines 30-55. The closest species disclosed by Meiere are the following, tetrakis(diethylamino)hafnium, tetrakis(diethylamino)zirconium, and tetrakis(diethylamino)-titanium:
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Meiere at col. 10, lines 5-10. Meiere differs from claim 2 in that Meiere does not teach fluorinated hydrocarbons as substituents. Claim 2 is not obvious because neither Meiere nor secondary art motivates one of ordinary skill to substitute the above species with multiple fluorine groups so as to arrive at the compound of claim 2 1
The closest art of record to claim 4 is S. Kataoka et al., WO 2016/143428 (2016) (“Kataoka”). Kataoka discloses the following compound:
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Kataoka at page 48. Kataoka teaches that this compound was used as an additive in an electrolyte solution in the production of a battery. Kataoka at page 82 of 85 (English-language machine translation). Species A-11 differs from claim 4 in that two of the four groups are trifluoroacetate. Claim 4 is not obvious because neither Kataoka nor secondary art motivates one of ordinary skill to structurally modify the above species A-11 so as to arrive at a compound falling within the scope of claim 4, where all four groups are trifluoroacetate.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM.
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 In the chemical arts, a "lead compound" obviousness analysis is often applied; the “lead compound” analysis requiring initial motivation to select a prior art compound and thereafter still further motivation to make the specific structural modifications thereto so as to arrive at a claimed compound. See MPEP § 2143(B) (discussing “lead compound cases” in Examples 9-11 with respect to pharmaceutical applications). However, the MPEP warns against applying the lead compound analysis rigidly in view of the flexible approach stated in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) see also, MPEP § 2143(B), Example 11 (citing Altana Pharma AG v. Teva Pharm. USA, Inc., 566 F.3d 999, 91 USPQ2d 1018 (Fed. Cir. 2009) a ‘restrictive view of the lead compound test would present a rigid test similar to the teaching-suggestion-motivation test that the Supreme Court explicitly rejected in KSR’).