Prosecution Insights
Last updated: July 17, 2026
Application No. 18/379,954

FLUORINE SUBSTITUTED ETHERS AND COMPOSITIONS, METHODS AND USES INCLUDING SAME

Non-Final OA §103
Filed
Oct 13, 2023
Priority
Oct 13, 2022 — provisional 63/415,683
Examiner
CAI, JIAJIA JANIE
Art Unit
1761
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Honeywell International Inc.
OA Round
1 (Non-Final)
28%
Grant Probability
At Risk
1-2
OA Rounds
11m
Est. Remaining
46%
With Interview

Examiner Intelligence

Grants only 28% of cases
28%
Career Allowance Rate
13 granted / 46 resolved
-36.7% vs TC avg
Strong +18% interview lift
Without
With
+18.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 8m
Avg Prosecution
38 currently pending
Career history
97
Total Applications
across all art units

Statute-Specific Performance

§103
83.1%
+43.1% vs TC avg
§102
2.5%
-37.5% vs TC avg
§112
2.5%
-37.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 46 resolved cases

Office Action

§103
CTNF 18/379,954 CTNF 98162 Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Response to Election/Restrictions Applicant's election of Group I (claims 1-18) without traverse in the reply filed on 05/26/2026 is acknowledged. Claims 1-20 are currently pending. Claims 19 and 20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being withdrawn to a non-elected invention, and non-elected species of the invention, there being no allowable generic or linking claims. Claims 1-18 are currently under examination. Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1-18 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara (US 2018/0020570 A1, hereinafter Fujiwara) in view of Nappa (US 2006/0237683 A1, hereinafter Nappa), as evidenced by “3,3,4,4,5,5,6,6,6-Nonafluorohexene Information” (“Environmental risk evaluation report: 3,3,4,4,5,5,6,6,6-Nonafluorohexene (Perfluorobutylethylene; PFBE)”, from Environment Agency in UK, 2023, hereinafter “3,3,4,4,5,5,6,6,6-Nonafluorohexene Information”) . Regarding claims 1 and 10 , Fujiwara teaches a method of cooling an electronic device by immersing the electronic device while it is operating in a liquid coolant, heat transfers between the electronic device and the liquid coolant ([0005], [0033], Fig. 1). Fujiwara also teaches that the liquid coolant is preferably a carbon-fluoride-based liquid ([0040]). Fujiwara does not teach that the liquid coolant comprises at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane. However, Nappa teaches that a heat transfer composition comprises about 1 wt.% to about 99 wt.% of 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 1 wt.% to about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (claim 3, Table 3), which overlaps with the claimed ranges of “at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane”. Nappa also teaches that the heat transfer composition can comprise about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (Table 6, p. 18, right column), which falls within the claimed ranges of “at least about 10% by weight”. Nappa also teaches that an azeotropic or near-azeotropic composition is that the vapor produced by partial evaporation or distillation of the liquid has the same or substantially the same composition as the liquid from which it is evaporated or distilled ([0092]-[0093]). Thus, the heat transfer composition of Nappa is a liquid. Nappa further teaches that the heat transfer composition can be used as a cooling medium in heat transfer, refrigeration and air-conditioning systems ([0003]). Nappa further teaches that the heat transfer composition can also be used in cleaning applications by immersion of the device in a bath containing the composition for residue removal ([0003], [0232]). Therefore, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to provide the heat transfer composition such as the heat transfer composition comprising about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane as taught by Nappa as the liquid coolant which is a carbon-fluoride-based liquid in Fujiwara, in order to cool the electronic device by immersing the electronic device while it is operating in the heat transfer composition with a reasonable expectation of success, because the heat transfer composition of Nappa comprising about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane is an azeotropic or near-azeotropic composition and is a liquid, the heat transfer composition of Nappa can be used as a cooling medium in a heat transfer system, and the heat transfer composition of Nappa can immerse a device in a bath containing this composition as recognized by Nappa. Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art. Regarding claims 8 and 17 , Nappa teaches that the heat transfer composition can comprise about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (Table 6, p. 18, right column), which falls within the claimed ranges of “at least about 50% by weight”. Regarding claims 2-5 and 11-14 , Nappa teaches that the heat transfer composition can comprise about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (Table 6, p. 18, right column). Nappa does not teach that the heat transfer composition has a dielectric constant less than about 5 at 20 GHz, a dielectric constant of about 3.4 at 20 GHz, a boiling point of from about 35° C to about 80° C, nor a boiling point of about 46° C. However, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to reasonably expect that the claimed dielectric constant and the claimed boiling point would flow naturally from the teaching of Nappa, because Nappa’s composition comprising about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane is substantially the same heat transfer composition comprising at least about 10% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, or at least about 50% by weight of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane as claimed, and also because instant Table 2 and instant US [0100]-[0101] of the instant invention proves that the dielectric constant and boiling point properties of the heat transfer composition are related/inherent to the fluoroether product (e.g. 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane), are not from co-frigerant(s)/impurities. Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art. Regarding claims 6 and 15 , the instant invention discloses that 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane has a GWP of less than 500 (instant Table 2). Nappa teaches that the heat transfer composition can comprise about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)- 1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (Table 6, p. 18, right column). The “3,3,4,4,5,5,6,6,6-Nonafluorohexene Information” as an evidentiary reference shows that 3,3,4,4,5,5,6,6,6-nonafluorohexene (PFBE) has a GWP of 0.16 (p. 52, § 9.5 Greenhouse gas hazard). Thus, the heat transfer composition of Nappa comprising about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane has a GWP of less than 500, which falls within the claimed range of “500 or less”. Regarding claims 7 and 16 , Nappa teaches that the heat transfer composition can comprise about 1 wt.% 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene and about 99 wt.% of 3-(difluoromethoxy)-1,1,1,2,2-pentafluoropropane, and this heat transfer composition is an azeotropic or near-azeotropic composition (Table 6, p. 18, right column). Nappa also teaches that the heat transfer composition is non-flammable ([0009]). Regarding claims 9 and 18 , Fujiwara teaches a method of cooling an electronic device by immersing the electronic device while it is operating in a liquid coolant ([0005], [0033], Fig. 1), and the electronic device is a data center ([0030]). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to JIAJIA JANIE CAI whose telephone number is 571-270-0951. The examiner can normally be reached Monday-Friday 8:30 am - 5:00 pm. 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, Angela Brown-Pettigrew can be reached on 571-272-2817. 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. /JIAJIA JANIE CAI/Examiner, Art Unit 1761 /ANGELA C BROWN-PETTIGREW/Supervisory Patent Examiner, Art Unit 1761 Application/Control Number: 18/379,954 Page 2 Art Unit: 1761 Application/Control Number: 18/379,954 Page 3 Art Unit: 1761 Application/Control Number: 18/379,954 Page 4 Art Unit: 1761 Application/Control Number: 18/379,954 Page 5 Art Unit: 1761 Application/Control Number: 18/379,954 Page 6 Art Unit: 1761 Application/Control Number: 18/379,954 Page 7 Art Unit: 1761 Application/Control Number: 18/379,954 Page 8 Art Unit: 1761
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Prosecution Timeline

Oct 13, 2023
Application Filed
Jun 18, 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
28%
Grant Probability
46%
With Interview (+18.1%)
3y 8m (~11m remaining)
Median Time to Grant
Low
PTA Risk
Based on 46 resolved cases by this examiner. Grant probability derived from career allowance rate.

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