Prosecution Insights
Last updated: July 17, 2026
Application No. 18/642,892

PHOSPHINE-IMINO-QUINOLINE AND RELATED LIGANDS FOR USE IN ETHYLENE OLIGOMERIZATION PROCESSES

Non-Final OA §103
Filed
Apr 23, 2024
Priority
Apr 27, 2023 — provisional 63/498,538
Examiner
NGUYEN, TAM M
Art Unit
1771
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Chevron Phillips Chemical Company L.P.
OA Round
1 (Non-Final)
77%
Grant Probability
Favorable
1-2
OA Rounds
6m
Est. Remaining
89%
With Interview

Examiner Intelligence

Grants 77% — above average
77%
Career Allowance Rate
752 granted / 975 resolved
+12.1% vs TC avg
Moderate +12% lift
Without
With
+11.5%
Interview Lift
resolved cases with interview
Typical timeline
2y 8m
Avg Prosecution
48 currently pending
Career history
1051
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
79.3%
+39.3% vs TC avg
§102
3.1%
-36.9% vs TC avg
§112
7.2%
-32.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 975 resolved cases

Office Action

§103
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 . Election/Restrictions Applicant’s election of Group I, claims 1, 2 and 21-32, in the reply filed on 4/16/2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Claim Rejections - 35 USC § 103 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. 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, 2, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al., “Controlling Polyethylene Molecular Weights and Distributions Using Chromium Complexes Supported by SNN-Tridentate Ligands,” Macromolecules 2022, 55, 2433–2443. Wang teaches SNN-tridentate ligands L1–L6 and chromium complexes Cr1–Cr6 having a quinoline-imine ligand framework containing a sulfur donor substituent attached to the quinoline-containing core (Scheme 1, pp. 2434–2435). Wang teaches a heteroatomic ligand compound comprising a quinoline-imine scaffold wherein sulfur is present as a thioether substituent corresponding to X = S and y = 1, and wherein the ligand contains substituents corresponding to R1–R11, including hydrogen, alkyl, aryl, substituted aryl, and halogenated aryl substituents (Scheme 1; section “Synthesis of Ligands L1–L6,” pp. 2434–2435). Wang further teaches hydrocarbyl sulfur substituents including iPr and 2,6-dimethylphenyl attached through sulfur to the quinoline core, corresponding to (R12)y X where X = S and y = 1 (Scheme 1; ligands L1–L6). Wang additionally teaches methyl substituents and hydrogen substituents on the aromatic rings and teaches alkyl-, aryl-, and substituted aryl-containing embodiments overlapping the recited substituent scope of claim 2, including methyl, phenyl, substituted phenyl, and trifluoromethyl-substituted phenyl groups (pp. 2435–2436; Table 1). Wang does not expressly teach the exact substituent selections recited in claims 1, 2, and 21 in every possible combination. However, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to utilize the disclosed substituent variations and hydrogen substitution patterns in the Wang ligands because Wang expressly teaches tuning steric and electronic properties of the quinoline-imine sulfur-containing ligands through routine substituent modification for catalyst optimization (section 2.2.1, pp. 2435–2436). Claims 1 and 22–32 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al., “Phosphine-Iminoquinoline Iron Complexes for Ethylene Polymerization and Copolymerization,” Organometallics 2017, 36, 3758–3764. Zhang teaches phosphine-iminoquinoline PNN ligands and corresponding iron complexes having a quinoline-imine ligand framework bearing phosphine substituents (Abstract; Scheme 1, pp. 3758–3759). Zhang expressly teaches phosphine-iminoquinoline ligands generated by coupling iminoquinolines with secondary diaryl- and dialkylphosphines R′2PH, thereby teaching phosphorus-containing substituents corresponding to (R12)2P, i.e., X = P and y = 2 (Scheme 1; section “Results and Discussion,” p. 3758). Zhang further teaches substituent variation including hydrogen, methyl, isopropyl, tert-butyl, phenyl, methoxy-substituted phenyl, trifluoromethyl-substituted phenyl, and related hydrocarbyl substituents on both the quinoline-imine framework and phosphine substituents (Table 1; ligand syntheses 6a–6j, pp. 3760–3762). Zhang does not expressly teach every specific positional arrangement and substituent combination recited in claims 22–32, including the exact recited hydrogen-placement limitations and every enumerated R12 species. However, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to employ the recited substituent selections because Zhang expressly teaches modification of phosphine and aryl substituents to tune steric and electronic properties of phosphine-iminoquinoline ligands for catalyst performance optimization (pp. 3759–3761). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAM M NGUYEN whose telephone number is (571)272-1452. The examiner can normally be reached Mon - Frid. 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, Prem C Singh can be reached at 571-273-6381. 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. /TAM M NGUYEN/Primary Examiner, Art Unit 1771
Read full office action

Prosecution Timeline

Apr 23, 2024
Application Filed
May 12, 2026
Non-Final Rejection mailed — §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
77%
Grant Probability
89%
With Interview (+11.5%)
2y 8m (~6m remaining)
Median Time to Grant
Low
PTA Risk
Based on 975 resolved cases by this examiner. Grant probability derived from career allowance rate.

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