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 1-20 of J.C.H. Yim, et.al. US 18/209,952 (06/14/2023) are pending. Claims 15-20 are withdrawn as drawn to non-elected Group (II) or not read on the elected species. Claims 1-14 are under examination on merits and rejected.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I (claims 1-15 ), without traverse, in the reply filed on 01/05/2026. Claims 16-20 drawn to non-elected Group (II) are withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction is made as Final.
Pursuant to the election of species requirement, Applicant elected Ru(1,3,5,5-tetramethyl-1,3-cyclohexadiene)(CO)3, without traverse, as the species of the formula (NACD)-Ru-Lx in the reply filed on 01/05/2026 for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable. Claims 1-14 of the elected invention read on the elected species. The elected species was searched and determined to be unpatentable as discussed in the 103 rejection below. Claim 15 is withdrawn as not read on the elected species. The provisional election of species requirement is in Effect. Examiner extended searching on other compounds as discussed in the 102 rejection below.
Claim Objections
Improper Markush Language
Claims 3-4,8 and 10 are objected to because clarity can be improved by using standard Markush language to define the Markush groups. See MPEP § 2173.05(h). Treatment of claims reciting alternatives is not governed by the particular format used. § 2173.05(h)(I). However, the claims should be in grammatically correct form and close the Markush group with a terminal conjunction. Applicant may overcome this rejection by using the following standard language in defining a Markush grouping.
“wherein the alternative is selected from the group consisting of A, B, C and D”; or
“wherein the alternative is A, B, C or D”. See MPEP § 2173.05(h).
For example, with respect to variable Rx, Ry, and Rz , claim 3 should be amended as follows.
Rx, Ry, and Rz each is independently selected from the group consisting of H, C1-C6 linear alkyl, C1-C6 branched alkyl, C1-C6 cyclic alkyl, C1-C6 alkenyl, C1-C6 alkylphenyl, C1-C6 alkenylphenyl, aryl, F, Cl, Br, and I.
Numerous additional such instances of improper Markush language occur throughout 3-4,8 and 10. Applicant is asked to address the other instances of improper Markush language throughout the claims.
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).
Interpretation of the Claim Term “substituent”
Claim 2 recites the claim term “substituent” in the following context:
wherein R1 and R2 is a substituent covalently bound to a ring structure carbon via a carbon or silicon atom, and R1 and R2 may be the same or different,
wherein R3, R4, R5, R6, R7 and R8 each is independently selected from H or a covalently bound substituent, . . .
the specification does not provide definition for the claim term of “substituent”. The plain meaning of substituent is “an atom or group of atoms taking the place of another atom or group or occupying a specified position in a molecule”. See Oxford Dictionary of English (3ed, 2015). Therefore, according its plain meaning, the term of “substituent” is broadly and reasonably interpreted as any atom or any group of atoms.
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Claims 1 is rejected under 35 U.S.C. 112(b) as indefinite because the meaning of “L” recited in the formula of (NACD)-Ru-Lx is not clear. Claim 1 provides no definition or meaning for this term.
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.
(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 USC § 102 Rejection over Vaarstra
Claims 1-2, 4-5, 8-9 and 11-14 are rejected under 35 U.S.C. 102(a)(1)as being anticipated by B.A. Vaarstra, WO 00/12776A1 (2000)(“Vaarstra”).
Vaarstra teaches a method for applying a film of ruthenium or ruthenium oxide to the surface of a substrate by employing the techniques of chemical vapor deposition (CVD) to decompose a precursor of ruthenium having the formula of LvRuXz.
Where,
L is a neutral or monoanionic ligand selected from the group including linear, branched, or cyclic hydrocarbyls (e.g., allenyl, aryl, alkyl, dienyl, trienyl), cyclic alkenes, dienes, cyclic dienes, trienes. cyclic trienes, bicyclic alkenes, bicyclic dienes, bicyclic trienes, tricyclic alkenes, tricyclic dienes, tricyclic trienes, fluorinated derivatives thereof: combinations thereof, and derivatives thereof additionally containing heteroatoms such as a halide, Si, S, Se, P, As, N or O; and combinations thereof.
X is a pi-bonding ligand selected from the group consisting of CO, NO, CN, CS, nitriles, isonitriles, trialkylphosphines, trialkylphosphites, trialkylamines, and isocyanide.
Subscripts y and z can each have a value of from one (1) to three (3).
Vaarstra at page 3, line 23 to page 4, line 4, emphasis added.
Vaarstra teaches working examples, such as Examples I-II as follows:
EXAMPLE I
Preparation of (C6H8)Ru(CO)3
(C6H8)Ru(CO)3 was prepared by mixing 1.0 gm of Ru3(CO)12 (Strem Chemicals, Inc.. Newburyport, MA), 30 mis of benzene (Aldrich Chemical Co., Milwaukee, WI), and 0.45 ml of 1, 3-cyclohexadiene (3 equivalents, 4.69 mmol) (Aldrich Chemical Co., Milwaukee, WI) in a glass flask. . . . ..
EXAMPLE II
Ruthenium film deposition from (C6H8)Ru(CO)3
The precursor (C6H8)Ru(CO)3, prepared according to the description of Example I, was added to a glass bubbler equipped with a dip tube and an exit valve. The bubbler was added to a cold- walled research CVD reactor and a He carrier gas was plumbed into the bubbler. A wafer of p-type silicon was placed in the reactor and heated to 300° C. (as measured by a thermocouple in direct contact with the surface of the wafer). . . . ..
Vaarstra at page 11-12, Examples I-II, emphasis added.
Thus, Vaarstra teaches a compound of (C6H8)Ru(CO)3, CAS abstract indicates the compound (RN 12108-25-7) has a chemical structure as indicated below:
PNG
media_image1.png
254
242
media_image1.png
Greyscale
The Vaarstra compound (C6H8)Ru(CO)3 prepared in Example I maps the formula (NACD)-Ru-Lx in claims 1-2, 4-5, 8 as:
NACD is 1, 3-cyclohexadiene which maps the formula I in claims 2, 4-5, 8-9 as each of R1-R8 is hydrogen atom and m is 1;
L is CO, and
x is 3.
Which meets each and every limitation of claims 1-2, 4-5, 8 and 11, therefore, claims 1-2, 4-5, 8 and 111 are anticipated.
Claims 12-14 are also anticipated because the Vaarstra composition in Example II is a vapor phase composition and the composition comprises(C6H8)Ru(CO)3 and Helium as a carrier gas, which meets each and every limitation of claims 12-14.
35 USC § 102 Rejection over S. Gatineau
Claims 1-2, 4-5, 8-9 and 11 are rejected under 35 U.S.C. 102(a)(1)(a)(2)as being anticipated by S. Gatineau. US8357614B2 (2013)(“Gatineau”).
Gatineau teaches one ruthenium-containing precursor Ru(1-methyl-4-isopropyl-1,3-cyclohexadiene)(CO)3. Gatineau at col. 8, Example, Synthesis of Ru(1-methyl-4-isopropyl-1,3-cyclohexadiene)(CO)3.
The Gatineau precursor Ru(1-methyl-4-isopropyl-1,3-cyclohexadiene)(CO)3 maps the formula (NACD)-Ru-Lx in claims 1-2, 4-5, 8 as:
NACD is 1-methyl-4-isopropyl-1,3-cyclohexadiene which maps the formula I in claims 2, 4-5, 8-9 as each of R1-R2, R4-R5, and R7-R8 is hydrogen atom, R3 is methyl and R6 is isopropyl, and m is 1;
L is CO, and
x is 3.
Which meets each and every limitation of claims 1-2, 4-5, 8 and 11, therefore, claims 1-2, 4-5, 8 and 11 are anticipated.
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.
Claims 3, 6-7, 10 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over S. Gatineau, US8357614B2 (2013)(“Gatineau”) as applied above for the rejection of claim 2 further in view of E. A. Trifonova, et al. 785, Journal of Organometallic Chemistry , 106-111(2015) (“Trifonova”).
S. Gatineau. US8357614B2 (2013)(“Gatineau”)
Gatineau teaches ruthenium-containing precursors which may be thermally stable (in delivery conditions) for use in CVD and ALD depositions with high reactivity. The disclosed precursors are metal tricarbonyl complexes having the general formula LmRu(CO)3, wherein L is a linear or branched unsaturated hydrocarbon or a cyclic unsaturated hydrocarbon having two or more substituents; and m is 1 or 2. Gatineau at col. 3, line 35-42, emphasis added.
Gatineau teaches that the precursors may have the formula LRu(CO)3 and the Ls are bound to the Ru atom as depicted below, the L may be cyclohexadiene molecules having two or more substituents.
PNG
media_image2.png
140
226
media_image2.png
Greyscale
Gatineau at col. 3, line 48-57 and 60-61, emphasis added.
Gatineau teaches example of the ruthenium-containing precursors such as Ru(1-methyl-4-isopropyl-1,3-cyclohexadiene)(CO)3. Gatineau at col. 8, Example, Synthesis of Ru(1-methyl-4-isopropyl-1,3-cyclohexadiene)(CO)3. As mentioned that Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene meeting each and every limitation of claim 2.
Difference between Gatineau and the instant Claims 3, 6-7 and 10
The Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene differs from the instant claims 3, 6-7 in that each of R1 and R2 in it is hydrogen rather the claimed groups.
The Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene differs from the instant claim 10 in that it is none of the claimed species.
E. A. Trifonova, et al. 785, Journal of Organometallic Chemistry , 106-111(2015) (“Trifonova”)
Trifonova teaches that 1,3,5,5-tetramethylcyclohexadiene can be used as a ligand to form different cyclohexadienyl ruthenium complexes. See Trifonova at abstract and Scheme 1 at page 107. After study the chemical structure of1,3,5,5-tetramethylcyclohexadiene, one ordinary skill would be appraised that 1,3,5,5-tetramethylcyclohexadiene is a species of the ligand L taught by Gatineau and it can be used as an alternative of 1-methyl-4-isopropyl-1,3-cyclohexadiene.
Obviousness Rationales of the Claims 3, 6-7, 10 and the Elected Species
Obviousness of a claimed compound can also be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One of ordinary skill is motivated to select the Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene for further investigation because Gatineau teaches it as an example of the formula
PNG
media_image2.png
140
226
media_image2.png
Greyscale
and it can be used as a precursor for use in CVD and ALD depositions with high reactivity.
Having selected the Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene, one of ordinary skill is motivated to substitute the moiety of 1-methyl-4-isopropyl-1,3-cyclohexadiene with the 1,3,5,5-tetramethylcyclohexadiene as indicated below, thereby arriving at the elected species which falls within the chemical genera of instant claims 3, 6-7 and 10, therefore, claims 3, 6-7 and 10 are obvious.
PNG
media_image3.png
618
1493
media_image3.png
Greyscale
One ordinary skill has a motivation to do so with a reasonable expectation of success because:
(i). Trifonova teaches 1,3,5,5-tetramethylcyclohexadiene can be used as a ligand to form different cyclohexadienyl ruthenium complexes;
(ii). 1,3,5,5-tetramethylcyclohexadiene is a species of the ligand L taught by Gatineau and it can be used as an alternative of 1-methyl-4-isopropyl-1,3-cyclohexadiene; and
(ii). the proposed complex is a position isomer of the Gatineau precursor 1-methyl-4-isopropyl-1,3-cyclohexadiene, compounds which are position isomers are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. MPEP 2144.09.II.
Non-Statutory 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).
Claims 1-2, 4-5, 8-9 and 11-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 3 of US patent US8357614B2 (2013).
The conflicting claim 3 claims compounds including 1-methyl-4-isopropyl-1,3-cyclohexadiene, which falls within the chemical genera of instant claims 1-2, 4-5, 8-9 and 11 for the same reason as given in the 102 rejection above. As such, conflicting claim 3 anticipates the instant claims 1-2, 4-5, 8-9 and 11.
Terminal Disclaimer
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.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 The claim 11 preamble language “A composition” does not constitute a structural limitation. Neither the claim nor the specification require that a “composition” comprise materials or components in addition to the claimed compound of formula I. Thus, under its broadest reasonable interpretation, consistent with the specification, a “composition” encompasses a one-component composition (i.e., a composition that consists only of the claimed compound). MPEP § 2111.