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 .
This action is responsive to Applicant’s amendment/remarks filed 11/20/2025.
Claims 1, 4, 13, 26-28, 31, 33, and 36 are currently pending.
Response to Amendment
The objection of claim 36 is withdrawn in view of the above amendment.
The rejection of claim 36 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite is withdrawn in view of the above amendment.
The rejections under 35 U.S.C. 102(a)(1,2) and 35 U.S.C. 103 over Robin et al. (US 9,840,685 B2) are withdrawn in view of the above amendment.
The rejections under 35 U.S.C. 102(a)(1,2) and 35 U.S.C. 103 over Shellef et al. (US 2019/0119609 A1) are withdrawn in view of the above amendment.
The various rejections on the grounds of nonstatutory double patenting as being unpatentable over the claims of U.S. Patent No. 9,840,685, U.S. Patent No. 10,289,469, and copending Application No. 18/686,470 are all withdrawn in view of the above amendment. It is noted that, upon careful review and consideration, the claims of U.S. Patent No. 10,289,469 fail to recite, articulate, or suggest a specific blend of methyl perfluoroheptene ether and HFE-7200 as amended in the instant claims.
However, the 103 rejection over Kontomaris et al. (US 10,287,469 B2) as previously set forth in the Office action mailed 06/24/2025 is maintained and has been revised below to reflect the changes in claim scope made by Applicant’s present claim amendments that narrow the claims by incorporating dependent claim limitation(s) into the independent claim.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 4, 13, 26-28, 31, 33, and 36 are rejected under 35 U.S.C. 103 as being unpatentable over Kontomaris et al. (US 10,287,469 B2).
As to claim 1, Kontomaris et al. teach working fluid compositions comprising alkyl perfluoroalkene ethers alone or in combination with additional compounds (abstract and col. 1 lines 52-59). Various embodiments and formulae for the alkyl perfluoroalkene ethers are disclosed (col. 5 line 53 to col. 6 line 5), however methoxyperfluoroheptene(s) (i.e., methyl perfluoroheptene ether(s)) are preferred (col. 6 lines 6-10). The additional compound may comprise a hydrofluoroether (col. 6 lines 20-23), and HFE-7200 is one suitable or preferred example of the additional hydrofluoroether (col. 6 lines 49-55).
While Kontomaris et al. fail to sufficiently meet the claimed composition under the meaning of anticipation (i.e., there are no working examples at-once containing both methyl perfluoroheptene ether and HFE-7200) the above cited teachings of Kontomaris et al. nevertheless render obvious the general composition/blend of components under a case of prima facie obviousness. At the time of the effective filing date it would have been obvious to a person of ordinary skill in the art to formulate and arrive at the claimed limitations from the cited teachings of Kontomaris et al. to obtain a sufficient alkyl perfluoroalkene ether-based working fluid composition with a reasonable expectation of success; as cited above, Kontomaris et al. expressly teach and prefer methyl perfluoroheptene ether as the main (alkyl perfluoroalkene ether) component of the composition and further teach providing HFE-7200 as a preferable additional hydrofluoroether compound for provision with the alkyl perfluoroalkene ether component.
While Kontomaris et al. also fail to teach the composition comprises about 60-80 wt.% of methyl perfluoroheptene ether and 20-40 wt.% HFE-7200, the cited teachings of Kontomaris et al. nevertheless encompass the relative amounts as claimed. As described above, Kontomaris et al. teach an alkyl perfluoroalkene ether-based working fluid where methyl perfluoroheptene ether is expressly taught and preferred as the main (alkyl perfluoroalkene ether) component of the composition and further teach providing HFE-7200 as a preferable additional hydrofluoroether compound for provision with the alkyl perfluoroalkene ether component. This amounts to a general condition that a blend of methyl perfluoroheptene ether and HFE-7200 is encompassed by the reference’s working fluid composition, and optimization or even simply varying of the relative amounts within the prior art’s general conditions amounts to routine experimentation. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). "The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages." In re Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382.
As to claim 4, Kontomaris et al. teach examples where “Vertrel® HFX-110” is provided as their alkyl perfluoroalkene ether component (see, e.g., col. 28 lines 50-56). Kontomaris et al. discloses Vertrel® HFX-110 is a mixture of methyl perfluoroheptene ether isomers available from E.I. DuPont de Nemours & Co., Wilmington, Del., USA (Id.). It is believed Kontomaris et al.’s Vertrel® HFX-110 mixture of methyl perfluoroheptene ether isomers is the same as and identical to the claimed methyl perfluoroheptene ether isomer mixture of about 50 wt.% 5-methoxy perfluoro-3-heptene, about 20 wt.% 3-methoxy perfluoro-3-heptene, about 20 wt.% 4-methoxy perfluoro-2-heptene, and about 8 wt.% 4-methoxy perfluoro-3-heptene. Applicant has the burden of showing Kontomaris et al.’s exemplary mixture of methyl perfluoroheptene ether isomers is not the same as the claimed mixture.
In any event (or furthermore), Kontomaris et al. teach the alkyl perfluoroalkene ethers comprise 5-methoxyperfluoro-3-heptene, 3-methoxyperfluoro-3-heptene, 4-methoxyperfluoro-2-heptene, 3-methoxyperfluoro-2-heptene, and mixtures thereof that are made by reacting a perfluoroalkene such as perfluoro-3-heptene in the presence of methanol as described in U.S. Patent No. 8,399,713 (col. 6 lines 6-10 and col. 5 lines 4-19). While this portion of Kontomaris et al. fail to specify the precise relative weight amounts/ratios of the four methyl perfluoroheptene ether isomers as claimed, the teachings of Kontomaris et al. nevertheless encompass the relative amounts as claimed. The cited portions of col. 5 & 6 (Id.) serve as a general condition that there exists a mixture of all four of 5-methoxy perfluoro-3-heptene, 3-methoxy perfluoro-3-heptene, 4-methoxy perfluoro-2-heptene, and 4-methoxy perfluoro-3-heptene as the reference’s “alkyl perfluoroalkene ethers” (note, the plurality of ethers indicating there is expressly a mixture of several compounds), and optimization or even simply varying of the relative amounts within the prior art’s general conditions amounts to routine experimentation. See also In re Aller & In re Peterson (Id.).
As to claim 13, while Kontomaris et al. fail to specify the kinematic viscosity of the composition, the claimed property that the composition exhibits a maximum kinematic viscosity of about 10 cSt or less would nevertheless would flow naturally from the above-cited/-combined teachings of the reference amounting to substantially the same exact composition as that claimed containing methyl perfluoroheptene ether and an additional hydrofluoroether, preferably or such as HFE-7200, (Id.).
As to claims 26 and 27, Kontomaris et al. teach providing the working fluid in heat pump apparatus for transferring heat to or from air, water, and other heat transfer media (abstract and col. 13 line 13 to col. 14 line 8). In the apparatus, heating is produced at a condenser where heat is extracted from the working fluid by condensing the (vapor) working fluid to a liquid working fluid and then cooling is produced at an evaporator where heat is absorbed to evaporate the liquid working fluid to a vapor working fluid during circulation of the working fluid (Id. at col. 13 lines 22-31). This reads on a process of condensing and evaporating the composition in the vicinity of a body to be cooled as well as a process of producing cooling by circulating the composition as a heat transfer fluid in the vicinity of a body to be cooled and removes heat from the vicinity of the body to be cooled. See also, for example, col. 3 lines 11-14, col. 15 lines 46-52 and Fig. 1.
As to claim 28, Kontomaris et al. teach providing the alkyl perfluoroalkene-based working fluid in heat pump apparatus for transferring heat to or from air, water, and other heat transfer media (Id. at abstract & col. 13 line 13 to col. 14 line 8), which read on providing the composition in a cooling fluid distribution unit, a refrigeration system, or a heat pump system. Kontomaris et al. further teach the alkyl perfluoroalkene-based working fluid may replace another pre-existing working fluid in the apparatus (col. 11 lines 28-48). This amounts to Kontomaris et al. teaching a method of replacing a heat transfer system in a cooling fluid distribution unit, a refrigeration system, or a heat pump system by providing the composition as a replacement for said heat transfer fluid.
As to claims 31, 33, and 36, Kontomaris et al. teach providing the working fluid in heat pump apparatus for transferring heat to or from air, water, and other heat transfer media (Id. at abstract & col. 13 line 13 to col. 14 line 8). This reads on a refrigeration system comprising the composition. The refrigeration system may comprise a chiller comprising the composition (col. 3 lines 11-16 & col. 11 lines 28-37; Fig. 1 & 2 encompass, if not directly depict, a chiller, too). Note that the limitation that the composition is suitable for use as a working fluid at a temperature of from about -135°C to about 110°C is merely an intended use limitation that does not distinguish nor limit the structure of the claimed composition from Kontomaris et al.’s compositions (comprising the same components of an alkyl perfluoroalkene ether and hydrofluoroether as claimed) and refrigeration apparatus thereof; in any event, Kontomaris et al. teach their composition is suitable for use as a working fluid at a temperature range overlapping that claimed (see, e.g., col. 7 & 14).
Response to Arguments
Applicant's arguments filed 11/20/2025 have been fully considered but they are not persuasive.
Regarding the 103 rejection over Kontomaris et al. (US 10,287,469 B2) Applicant argues the claimed subject matter is not a simple variation or optimization of general teachings from the prior art but rather one that produces an unforeseeable technical effect. Applicant elaborates the present application’s comparative showing (Example 4) demonstrates a blend of 70 wt.% methyl perfluoroheptene ether (MPHE) and 30 wt.% HFE-7200 exhibits a kinematic viscosity of 5.1188 cSt at a temperature as low as -95°C whereas pure MPHE exhibits a significantly higher kinematic viscosity of 11.179 cSt at the same temperature. In other words, Applicant alleges the claimed composition exhibits an unexpected result of a lower kinematic viscosity at a low temperature as compared to pure MPHE alone.
In response, the example(s) in the original specification are little probative value in the determining patentability of claims since they do not involve a comparison of applicant’s invention with the closest applied prior art. The comparative showing compares a blend of MPHE and HFE-7200 to MPHE alone whereas the prior art reference teaches blends of alkyl perfluoroalkene ether (e.g., MPHE) and an additional hydrofluoroether (e.g., HFE-7200) which is closer prior art than the present application’s comparative example of pure/100% MPHE component alone. See In re De Blawe, 222 USPQ 191 (FED. Cir. 1984), and In re Fenn, 208 USPQ 470 (CCPA 1981).
Even if, arguendo, the comparison was done between the applicant’s invention and the closest prior art, the claims are not deemed patentable over the reference of record since they are not commensurate in scope with the probative value of data in the examples. The comparative showing presents a single inventive blend of 70/30 MPHE/HFE-7200 (wt.%/wt.%) which is not commensurate in scope with the claimed blends of 60-80/20-40 MPHE/HFE-7200. There is insufficient data to permit a person having ordinary skill in the art to ascertain there is a trend that extends across the breadth of the claimed concentrations within the scope of the claims with reasonable certainty. Applicant has also not provided evidence and a reasoned argument explaining why the single tested blend is representative of the full scope of the claimed composition’s breadth. Additionally, even if a trend could be ascertained or exists, Applicant has not demonstrated criticality of the concentrations (i.e., that the claimed blends of 60-80/20-40 MPHE/HFE-7200 are critical over other blends of MPHE/HFE-7200 such as 90/10 and 50/50 or even 1/99 and 99/1).
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof. In re Kollman, 595 F.2d 48, 201 USPQ 193 (CCPA 1979). Evidence of nonobviousness consisted of comparing a single composition within the broad scope of the claims with the prior art. The court did not find the evidence sufficient to rebut the prima facie case of obviousness because there was "no adequate basis for reasonably concluding that the great number and variety of compositions included in the claims would behave in the same manner as the tested composition." In re Lindner, 457 F.2d 506, 509, 173 USPQ 356, 359 (CCPA 1972). To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960).
The comparative showing is also deficient in another manner. To establish the existence of unexpected results, Applicant must establish through the introduction of evidence both that (1) there is actually a difference between the results obtained through the claimed invention and those of closest prior art and (2) the observed difference would have been unexpected by a person having ordinary skill in the art. In re Freeman, 474 F.2d 1318, 1324 (CCPA 1973). In this case, Applicant has not provided evidence that, as of the application's effective filing date, a person having ordinary skill in the art would have considered the results presented in the data to have been unexpected or surprising. The arguments do not cite evidence regarding the unexpected nature of the observed differences.
Furthermore, because superiority alone is not sufficient to show that the result is unexpected, Pfizer, Inc. v. Apotex, Inc., 480 F.3d 1348, 1371 (Fed. Cir. 2007) (“[A]ny superior property must be unexpected to be considered as evidence of non-obviousness.”), Applicant has not provided evidence of the unexpected nature of the observed results.
The Office also notes the original specification discloses the 70/30 blend of MPHE/HFE-7200 has a freezing point of -118°C whereas pure MPHE has a freezing point of -88.4°C and pure HFE-7200 has a freezing point of -138°C (Table 5). The result/comparison demonstrates the claimed blend has a freezing point value between that of the individual components alone. A combination of a higher freezing point compound (MPHE) with a lower freezing point compound (HFE-7200) yielding a composition that freezes at a lower temperature than the higher freezing point compound (MPHE) and at a higher temperature than the lower freezing point compound (HFE-7200) is merely an expected beneficial result of their combination. "Expected beneficial results are evidence of obviousness of a claimed invention, just as unexpected results are evidence of unobviousness thereof." In re Gershon, 372 F.2d 535, 538, 152 USPQ 602, 604 (CCPA 1967).
Accordingly, the rejection is maintained for the reasons of record.
Prior Art Cited But Not Applied
The following prior art is made of record and not relied upon but is considered pertinent to Applicant’s disclosure:
Bartelt et al. (US 8,399,713 B2) teach alkyl perfluoroalkene ether compositions prepared by contacting a perfluoroalkene, such as perfluoro-3-heptene, perfluoro-2-heptene, perfluoro-2-hexene, perfluoro-3-hexene, or perfluoro-2-pentene with an alcohol such as methanol or ethanol in the presence of a strong base (abstract and col. 3 lines 33). In one embodiment, the products from the reaction of perfluoro-3-heptene with methanol comprise 5-methoxyperfluoro-3-heptene, 3-methoxyperfluoro-3-heptene, 4-methoxyperfluoro-2-heptene and 3-methoxyperfluoro-2-heptene (col. 3 lines 34-37). See also col. 16 lines 5-59 where a mixture of crude methyl perfluoroheptene ether products are formed by two separate reactions, combined, and distilled.
Petrov et al. (WO 2020/081334 A1) teach HFX-110 is the product of the reaction with perfluorinated heptenes with methanol (para. 0003).
The remaining references listed on Forms 892, 1449, and PCT 210 have been reviewed by the examiner and are considered to be cumulative to or less material than the prior art references relied upon or discussed above.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW R DIAZ whose telephone number is 571-270-0324. The examiner can normally be reached Monday-Friday 9:00a-5:00p EST.
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/MATTHEW R DIAZ/Primary Examiner, Art Unit 1761
/M.R.D./
January 12, 2026