Prosecution Insights
Last updated: August 15, 2026
Application No. 18/446,490

ESTER-BASED COMPOUND HAVING LOW TRACTION COEFFICIENT, LUBE BASE OIL COMPRISING SAME COMPOUND, AND LUBRICANT COMPOSITION COMPRISING SAME COMPOUND

Non-Final OA §103
Filed
Aug 09, 2023
Priority
Sep 30, 2022 — RE 10-2022-0125252
Examiner
SAWYER, JENNIFER C
Art Unit
1691
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
SK Enmove Co. Ltd.
OA Round
1 (Non-Final)
69%
Grant Probability
Favorable
1-2
OA Rounds
0m
Est. Remaining
60%
With Interview

Examiner Intelligence

Grants 69% — above average
69%
Career Allowance Rate
385 granted / 560 resolved
+8.8% vs TC avg
Minimal -9% lift
Without
With
+-9.0%
Interview Lift
resolved cases with interview
Typical timeline
2y 9m
Avg Prosecution
48 currently pending
Career history
604
Total Applications
across all art units

Statute-Specific Performance

§101
0.6%
-39.4% vs TC avg
§103
49.5%
+9.5% vs TC avg
§102
13.4%
-26.6% vs TC avg
§112
26.2%
-13.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 560 resolved cases

Office Action

§103
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 This office action is in response to applicant’s communication filed on 6/23/26. Claims 1-10 are pending in this application. Applicant’s election without traverse of Group II, claims 5-10 in the reply filed on 6/23/26 is acknowledged. Thus claims 1-4 are withdrawn from further consideration being drawn to the nonelected invention. . As a result, claims 5-10 are being examined in this Office Action. Priority The applicant claims benefit as follows: PNG media_image1.png 76 416 media_image1.png Greyscale Objections Claim 10 is objected to because of the following informality: In claim 10, the claim language “The lubricant composition of claim 9, the lubricant composition comprises greater than 0 wt% and less than 50 wt% of the compound based on the total weight of the lubricant composition” is grammatically incorrect. The examiner instead recommends “The lubricant composition of claim 9, wherein the lubricant composition comprises greater than 0 wt% and less than 50 wt% of the compound based on the total weight of the lubricant composition.” Appropriate correction is required. 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 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 of this title, 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 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over Kamuro et al. (US 6093683, pub date July 25, 2000), hereinafter “Kamuro,” in view of Otsuki et al. (JP 6908030, pub date July 21, 2021, in applicant’s IDS filed 8/9/23) (also see the Machine English Translation and the Partial English Translation), hereinafter “Otsuki.” Determination of the Scope and Content of the Prior Art (MPEP §2141.01) Kamuro teaches a jasmonic acid derivative represented by formula (1) (see formula below), wherein R1 represents a pentyl group or a pentenyl group and R2 represents a hydrogen atom or an alkyl group. Kamuro further teaches that the alkyl group for R2 includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decanyl group. Kamuro further teaches that such jasmonic acid derivatives are known compounds and can be produced by an ordinary process. (Kamuro: Abstract; col. 1, lines 50-67; col. 2, lines 1-20). PNG media_image2.png 172 404 media_image2.png Greyscale Kamuro further exemplifies the following compounds in which R1 is a pentyl group and R2 is a heptyl and octyl, respectively. (Table 2, No 2-6 and 2-7 and Table 3, No 3-6 and 3-7): PNG media_image3.png 232 462 media_image3.png Greyscale PNG media_image4.png 196 474 media_image4.png Greyscale The compound of Kamuro reads on applicant’s compound represented by Formula 1, when applicant’s R1 is nonyl or decyl alkyl, applicant’s R2 is hydrogen, applicant’s R3 and R5 are bonded together to form a hydrocarbon ring having 5 carbon atoms, and applicant’s R4 is pentyl alkyl. Kamuro’s jasmonic acid derivative has the same cyclopentanone acetic ester structure as applicant’s claimed Formula 1 species, wherein Kamuro’s ester alkyl group corresponds to applicant’s ester-side R1 group. (Kamuro: Abstract; col. 1, lines 50-67; col. 2, lines 1-20). Otsuki teaches a lubricant and lubrication method. Otsuki teaches that lubricants are used in a wide range of objects, including industrial machinery, because they reduce friction and wear between two sliding solids. Otsuki further teaches that the lubricant contains a compound represented by formula (1) as a base oil and is excellent in biodegradability. (Otsuki Machine English Translation: Technical Field; Background Art; Description of Embodiments; Lubricant section; pages 2-5). Otsuki formula (1) structure is the following (Otsuki JP patent, abstract, page 1): PNG media_image5.png 128 304 media_image5.png Greyscale Otsuki teaches that jasmonic acid ester and dihydrojasmonate ester are preferable compounds for the lubricant, and that methyl jasmonate and methyl dihydrojasmonate are more preferable because these compounds are excellent in biodegradability, have low flammability and toxicity, are excellent in safety, and have high chemical stability and excellent fluidity. Otsuki further teaches that the content ratio of the compound is usually 50 mass% or more, preferably 80 mass% or more, more preferably 95 mass% or more, 99 mass% or more, and may be 100 mass% with respect to 100 mass% of the lubricant. (Otsuki Machine English Translation: Compound section; Content Ratio section; page 4). Otsuki exemplifies a lubricant using CLAI GEON, methyl dihydrojasmonate containing 98.0 mass% or more, and teaches that the lubricant had good biodegradability, with a BOD of 88% after 28 days. Otsuki further teaches that the lubricant was applied to a mechanical seal portion and, after continuous operation for one year, no wear was observed on the sliding surfaces and the leakage amount was on the order of several ppm, comparable to mineral oil generally used as a lubricant. (Otsuki Partial English Translation: paragraph [0042], Example 1). Ascertainment of the Difference Between Scope the Prior Art and the Claims (MPEP §2141.012) Kamuro is deficient in the sense that it does not expressly teach using its jasmonic acid derivative compound as a lube base oil or lubricant composition. Instead, Kamuro teaches the jasmonic acid derivative compound as a plant growth promoter. Otsuki cures this deficiency. Otsuki exemplifies methyl dihydrojasmonate as a lubricant and teaches the use of jasmonic acid ester and dihydrojasmonate ester compounds as the base oil of a lubricant. Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143) Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to utilize Kamuro’s known jasmonic acid derivative compound, including the nonyl or decyl ester compound, as the compound/base oil in Otsuki’s lubricant, since Otsuki teaches that jasmonic acid ester and dihydrojasmonate ester compounds are useful as lubricant base oils having biodegradability, low toxicity, low flammability, high chemical stability and excellent fluidity. Thus, a person of ordinary skill in the art would have been motivated to use the structurally similar jasmonic acid ester compounds of Kamuro in the lubricant of Otsuki with a reasonable expectation of success. Furthermore, the similarity of Kamuro’s jasmonic acid ester compounds and Otsuki’s jasmonic acid ester/dihydrojasmonate ester lubricant compounds suggests the compounds would have similar properties and utilities. Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982). With regard to claim 5, Kamuro teaches the claimed Formula 1 compound species as discussed above, and Otsuki teaches a lube base oil/lubricant comprising a jasmonic acid ester or dihydrojasmonate ester compound as a base oil. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to provide a lube base oil comprising Kamuro’s jasmonic acid ester compound in view of Otsuki’s teaching that such jasmonic acid ester/dihydrojasmonate ester compounds are useful as lubricant base oils. With regard to claim 6, although Kamuro and Otsuki do not expressly teach the recited traction coefficient of 0.04 or less under applicant’s claimed measuring conditions, the claimed traction coefficient would be an inherent property of, or at least would have been reasonably expected from, the lube base oil comprising the same or substantially the same long-chain jasmonic acid ester compound. Applicant’s own disclosure confirms that, with the use of alcohols having 9 or more carbon atoms, a traction coefficient of 0.04 or less was achievable under the conditions of a load of 38 N, a temperature of 100° C., a speed of 1000 mm/s, and an SRR of 100%. (Applicant’s Published Application US 20240132436: paragraphs [0072]-[0077]; Table 3). With regard to claim 7, although Kamuro and Otsuki do not expressly teach the recited flash point of 200° C. or higher for the exact claimed lube base oil, the claimed flash point would be an inherent property of, or at least would have been reasonably expected from, the lube base oil comprising the same or substantially the same long-chain jasmonic acid ester compound. Applicant’s own disclosure teaches that the use of alcohols having 9 or more carbon atoms provides the claimed long-chain ester compounds and reports flash points above 200° C. for such compounds. (Applicant’s Published Application US 20240132436: paragraphs [0072]-[0077]; Table 3). With regard to claim 8, Otsuki teaches the content ratio of the jasmonic acid ester/dihydrojasmonate ester compound in the lubricant is usually 50 mass% or more, preferably 80 mass% or more, more preferably 95 mass% or more, 99 mass% or more, and may be 100 mass% with respect to 100 mass% of the lubricant. Therefore, Otsuki teaches the claimed amount of at least 50 wt% based on the total weight of the lube base oil. With regard to claim 9, Kamuro teaches the claimed Formula 1 compound species as discussed above, and Otsuki teaches a lubricant comprising a jasmonic acid ester or dihydrojasmonate ester compound as a base oil and optionally further containing additives. Thus, it would have been obvious to one of ordinary skill in the art at the time of the invention to provide a lubricant composition comprising Kamuro’s jasmonic acid ester compound in view of Otsuki’s teaching that jasmonic acid ester/dihydrojasmonate ester compounds are useful as lubricants having excellent biodegradability and reduced environmental load. Thus, claims 5-9 are prima facie obvious over Kamuro in view of Otsuki. Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Kamuro et al. (US 6093683, pub date July 25, 2000), hereinafter “Kamuro,” in view of Otsuki et al. (JP 6908030, pub date July 21, 2021, in applicant’s IDS filed 8/9/23) (also see the Machine English Translation and the Partial English Translation), hereinafter “Otsuki” as applied to claim 9 above, and further in view of Gao et al. (US 2016/0130524, pub date May 12, 2016), hereinafter “Gao.” Determination of the Scope and Content of the Prior Art (MPEP §2141.01) Kamuro and Otsuki teach the lubricant composition comprising the claimed jasmonic acid ester compound as discussed above. Gao teaches a low viscosity ester lubricant composition. Gao teaches that the effective lubrication performance of the composition is due to the presence of low viscosity esters. Gao further teaches that the low viscosity ester base stocks can be present in lubricating compositions from 5 wt% to 100 wt% based on the total weight of the composition, and that the balance of the composition can be selected from conventional lubricating base stocks and additives. (Gao: paragraphs [0020]-[0021], [0033]). Gao further teaches lubricant compositions optionally containing polymers for the purpose of adjusting viscosity, wherein the composition may have a polymeric viscosity modifier in an amount of 5 wt% to 35 wt% and an amount of low viscosity ester at 95 wt% to 5 wt% based on the total weight of the composition. (Gao: paragraph [0034]; claims 8-14). Ascertainment of the Difference Between Scope the Prior Art and the Claims (MPEP §2141.012) Kamuro in view of Otsuki is deficient in the sense that it does not expressly teach that the lubricant composition comprises greater than 0 wt% and less than 50 wt% of the compound based on the total weight of the lubricant composition. Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143) However, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to utilize the ester compound of Kamuro/Otsuki in a lubricant composition in an amount greater than 0 wt% and less than 50 wt%, since Gao teaches that low viscosity esters are useful in lubricant compositions and can be present from 5 wt% to 100 wt% based on the total weight of the composition, which reads on the amounts within the claimed range. Gao further teaches blending the ester with polymeric viscosity modifiers, conventional lubricating base stocks, and additives for the purpose of adjusting viscosity and providing effective lubrication performance. Furthermore, Otsuki teaches that lubricant additives may be used to impart desired properties to the lubricant, and Gao teaches that low viscosity ester lubricant compositions may be formulated with polymeric viscosity modifiers and other conventional lubricant components. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to formulate the jasmonic acid ester compound of Kamuro/Otsuki in an amount of greater than 0 wt% and less than 50 wt% in a lubricant composition, in order to obtain the known benefit of using ester components in lubricant formulations while adjusting the remaining lubricant components for viscosity and performance. Note that the discovery of an optimum value of a result effective variable in a known composition is ordinarily within the skill of the art. Especially since Gao teaches that the amount of ester in a lubricant composition may vary broadly, including amounts within the claimed range of greater than 0 wt% and less than 50 wt%, and teaches that the composition may be balanced with conventional lubricant components and viscosity modifiers. Therefore, the claimed amount of the ester compound would have been an obvious optimization of the lubricant composition. Thus, claim 10 is prima facie obvious over Kamuro in view of Otsuki and further in view of Gao. Conclusion No claim is allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST. If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. Jennifer Cho Sawyer Patent Examiner Art Unit: 1691 /RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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Prosecution Timeline

Aug 09, 2023
Application Filed
Jul 31, 2026
Non-Final Rejection mailed — §103 (current)

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Prosecution Projections

1-2
Expected OA Rounds
69%
Grant Probability
60%
With Interview (-9.0%)
2y 9m (~0m remaining)
Median Time to Grant
Low
PTA Risk
Based on 560 resolved cases by this examiner. Grant probability derived from career allowance rate.

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