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 .
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 (i.e., changing from AIA to pre-AIA ) 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.
Continued Examination Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 filed on 6 July 2026 has been entered.
Election/Restrictions
Claims 6-12 stand withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed 23 October 2025.
Claim Amendments
Applicants amendments to the claims filed on 6 July 2026 have been entered and considered for this action.
New Examiner
This application has been transferred to a new examiner, Nicholas Piro of Art Unit 1738, who can be reached at 571-272-6344.
Response to Arguments
Applicant’s arguments, see pages 7-8 of the reply filed 6 July 2026, with respect to the rejection of claims 1-5 under 35 USC § 103 have been fully considered and are persuasive. Therefore, the prior rejections have been withdrawn. However, upon further consideration, new grounds of rejection are made in view of Cloete et al. (Inorg. Chem. 2013, 52, 2268−2270), Kim et al. (Appl. Organometal. Chem. 2019, 33, e4829), and Lee (WO 2019/235799 A1), as analyzed below.
Specification
The disclosure is objected to because of the following informalities:
Many of the images in the specification are difficult to read and should be replaced. Specifically, the figures in paragraphs [0060]-[0063], [0133], [0249], [0298] should be replaced with more clear versions.
Appropriate correction is required.
Claim Objections
Claims 1 and 3 are objected to because of the following informalities:
The images in claims 1 and 3 are blurry and should be replaced with more clear versions.
Appropriate correction is required.
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 1-3 are rejected under 35 U.S.C. 103 as being unpatentable over Cloete et al. (Inorg. Chem. 2013, 52, 2268−2270) in view of Kim et al. (Appl. Organometal. Chem. 2019, 33, e4829).
Regarding claim 1, Cloete teaches a ligand compound represented by the following formula (Scheme 1),
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which fits the structure of Formula 1 in the instant claim where Cy is cyclohexyl, a cycloalkyl of 6 carbon atoms.
Cloete also teaches that this ligand can be used in conjunction with chromium for the oligomerization of ethylene, and that the cHex ligand shows good selectivity for 1-octene (Table 1).
The structure of R1 to R4 in the ligand of Cloete is phenyl, which does not meet the limitations on R1 to R4 of the instant claim.
However, Kim studies the same tetramerization reaction of ethylene to 1-octene (Section 2.6) using similar PNP ligands (Scheme 5). Kim also teaches that substitution of the phenyl groups in the para position with bulky substituents having a negligible electronic effect led to dramatic improvements in catalytic activity (dramatic improvement was achieved via the introduction of a bulky substituent with a negligible electronic effect such as –SiMe3; p. 8, ¶ 2). Kim further teaches that attachment of more bulky –SiMe2(CH2)7CH3 or –Si(nBu)3 further improved the activity (p. 8, ¶ 2).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to introduce on the phenyl groups in the catalysts of Cloete para-substitution of -Si(nBu)3, thereby arriving at R1 to R4 being
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which meets the limitation on R1 to R4 recited in the instant claim (column 3, row 1).
One of ordinary skill in the art would have been motivated to modify the ligands of Cloete such because Kim teaches that this substitution leads to improved catalytic activity.
Regarding claims 2 and 3, modified Kim teaches the ligand of claim 1, where the Cy group is cyclohexyl, meeting the limitations of claims 2 and 3 (cyclohexyl is group (a) in the claim).
Claims 1-3 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (WO 2019/235799 A1; foreign patent document #10 on the IDS filed 28 February 2023) in view of Cloete et al. (Inorg. Chem. 2013, 52, 2268−2270). An English language equivalent of WO 2019235799 A1 is US 2021/0229084 A, and latter is referenced in the analysis below.
Regarding claim 1, Lee teaches compound represented by the following formula ([0049]),
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where R1 is a alkyl group, and in particular teaches an embodiment where R1 is butyl ([0080]), meeting the limitation on R1-R4 represented by the compound in column 3, row 1 of the table in the instant claim.
Lee also teaches that this ligand can be used in conjunction with chromium for the oligomerization of ethylene to 1-octene ([0108]).
Lee does not teach the substituent on nitrogen being specifically a cycloalkyl group, as required by the instant claim.
However, Cloete teaches similar ligand to Lee also for the oligomerization of ethylene (Scheme 1 and Table 1). Cloete further teaches that the nitrogen group can be substituted with cycloalkyl groups such as cyclohexyl (Scheme 1), and the cyclohexyl variant shows good selectivity for 1-octene (Table 1).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use a cyclohexyl substituent as the R group on nitrogen in the ligands of Lee, thereby arriving at the instant invention. One of ordinary skill in the art would have been motivated to do because Cloete teaches that this substitution leads to improved selectivity for 1-octene.
Regarding claims 2 and 3, modified Lee teaches the ligand of claim 1, where the Cy group is cyclohexyl, meeting the limitations of claims 2 and 3 (cyclohexyl is group (a) in the claim).
Double Patenting
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).
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.
Claims 1-3 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of copending Application No. 18/570,345. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the ‘345 application recite ligands based upon the structure below that meet the limitations of the instant claims.
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This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-3 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2 of U.S. Patent No. 11,148,127 in view of Cloete et al. (Inorg. Chem. 2013, 52, 2268−2270).
Claim 1 of the ‘127 patent recites ligand of the formula
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where R and R1 are C1-C60 alkyl groups. Claim 2 of the ‘127 application further recites that R1 may be butyl, which meets the limitations on R1-R4 of the instant claim.
The ‘127 patent does not specifically require that the substituent on nitrogen being a cycloalkyl group, as required by the instant claim.
However, Cloete teaches similar ligands to the ‘127 patent also for the oligomerization of ethylene (Scheme 1 and Table 1). Cloete further teaches that the nitrogen group can be substituted with cycloalkyl groups, and cyclohexyl in particular, with good selectivity for 1-octene (Table 1).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use a cyclohexyl substituent as the R group on nitrogen in the ligands of ‘127 patent, thereby arriving at the invention of instant claims 1-3. One of ordinary skill in the art would have been motivated to do because Cloete teaches that this substitution leads to improved selectivity for 1-octene.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Nicholas A Piro whose telephone number is (571)272-6344. The examiner can normally be reached Mon-Fri, 8:00 am-5:00 pm.
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/NICHOLAS A. PIRO/Assistant Examiner, Art Unit 1738
/PAUL A WARTALOWICZ/Primary Examiner, Art Unit 1735
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