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 .
Information Disclosure Statement
Receipt is acknowledged of the Information Disclosure Statement filed 17 July 2024 and 14 March 2025.The Examiner has considered the reference cited therein to the extent that each is a proper citation. Please see the attached USPTO Form.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 2 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With regard to claim 2, the phrase "preferably" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
With regard to claim 2, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 2 recites the broad recitation the additional compound is greater than 0 and less than 1%, and the claim also recites greater than 0 and less than 0.4% and greater than 0 and less than 0.1% which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 4-5, 8 are rejected under 35 U.S.C. 1029(a)(1) and (a)(2) as being anticipated by Kopko (WO-2017184975-A1).
With regard to claims 1 and 4, Kopko teaches a composition comprising Z-1,3,3,3-tetrafluoropropene (i.e., R-1234ze(Z) hereinafter, also known as HFO-1234ze(Z)) and E-1,1,1,4,4,4-hexafluuoro-2-butene (i.e., R-1336mzz(E) hereinafter, also known as HFO-1336mzz(E)) (para [0018]). The disclosure satisfies the limitation requiring Z-1,3,3,3-tetrafluoropropene and an additional compound.
With regard to claim 5, as stated above, Kopko teaches a composition comprising R-1234ze(Z) and R-1336mzz(E) (para [0018]), thereby satisfying the requirement for composition (ii) comprising Z-1,3,3,3-tetrafluoropropene and E-1,1,1,4,4,4-hexafluuoro-2-butene.
With regard to claim 8, Kopko teaches that this chemical blend forms a substantially-azeotropic mixture characterized by a low global warming potential (Abstract).
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 2-3, 6, 7, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Kopko (WO-2017184975-A1).
The teachings of Kopko are discussed above.
With regard to claim 2, while Kopko does not explicitly teach an additional compound amount of less than 1%. Kopko does teaches that the mole ratio of R-1234ze(Z) to R-1336mzz(E) is in the range of 1 :99 to 67:33 (claim 20). This disclosure encompasses a 1% concentration but does not explicitly state a value strictly less than 1%. However, Kopko further teaches due to the substantially azeotropic behavior of the R-1234ze(Z) and R-1336mzz(E) mixture—demonstrated by a substantially uniform temperature glide across the entire composition range—the ratio of these components may be tailored to provide a nonflammable refrigerant with acceptable global warming potential (GWP hereinafter) (para [0060]). Kopko further notes the balance of the mixture comprises an effective amount of R-1336mzz(E) to produce a nonflammable or nearly nonflammable azeotropic or near-azeotropic mixture while simultaneously controlling a low temperature glide which can be minimized or maintained below a predetermined value (para [0032]).
With regard to the concentration of the additional component, Kopko offers the motivation to tailor and optimize the ratio of cis-1 ,3,3,3-tetrafluoropropene to trans-1 ,1 , 1 ,4,4,4- hexafluoro-2-butene to provide a nonflammable mixture with low temperature glid and an acceptable GWP (paras [0032 and 0060]). Therefore, modifying the ratio of cis-1 ,3,3,3-tetrafluoropropene to trans-1 ,1 , 1 ,4,4,4- hexafluoro-2-butene can be optimized to achieve the desired nonflammable and GWP limits via a routine optimization. The case law has held that discovering an optimum value of a result effective variable involves only routine skill in the art. In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980). Thus, it would have been obvious to one having ordinary skill in the art before the effective filling date, to modify the ratio as disclosed by Kopko to arrive at the claimed invention.
With regard to claims 3 and 6, Kopko does not explicitly teach that the chemical blend further comprises another compound. However, Kopko teaches that the composition may include other ingredients that, in character and/or amount, do not adversely affect the advantageous aspects of the mixture as a refrigerant (para [0032]). Furthermore, Kopko notes refrigerant technology advances, alternatives to HCFC-123 continue to emerge. Specifically, Kopko identifies R-1233zd(E) (i.e., trans-CF3CH=CHCI or HFO-1233zd(E)), as one alternative, noting that its significantly higher vapor pressure requires the use of an ASME pressure vessel, rendering it unsuitable for retrofit applications. Kopko discloses R-1336mzz(Z) (i.e., rans-CF3CH=CHCF3, or trans-1 , 1 , 1 ,4,4,4-hexafluoro-2-butene, also known as HFO-1336mzz(E)), as another alternative, Kopko notes that its lower vapor pressure and lower speed of sound reduces chiller capacity (para [0008]). Kopko further exemplifies with a mixture comprising R-1336mzz(Z) (para [0012]). Additionally, Kopko teaches that the utilization an azeotrope with methylene chloride (i.e.,R-30 hereinafter, also known as HCC-30) as a balancing solvent yields properties similar to CFC-11 (i.e., trichlorofluoromethane). This azeotrope can serve as a retrofit fluid for legacy chillers—particularly those with open-drive motors where motor insulation compatibility is not a concern (para [0070]).
Furthermore, Kopko teaches that other formulation variations may include the combination of alternatives hydrofluoroolefins (HFOs) that may produce effective mixtures include other isomers of R-1233zd, other isomers of R- 1234ze, R-1234yf (CH2=CFCF3 or 2,3,3,3-tetrafluoropropene, also known as HFO-1234yf), R-1336mzz(Z), and combinations thereof. Lastly, Kopko notes other mixtures are expected to have relatively large temperature glide, making them more suitable for use in refrigeration systems with tube-side evaporation and condensation (para [0063]). Accordingly, the disclosure of R-1233zd and R-1336mzz(Z), R-1234yf, HCC-30 encompasses the claimed additional compounds, thereby reading on the requirements for further compounds within compositions (ii), (a), and (b).
With regard to the additional compound, it would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention that Kopko’s chemical blend can be modified. Specifically, a person having ordinary skill in the art would be motivated to introduce additional compounds—such as R-1233zd, R-1234yf, R-30, and/or R-1336mzz(Z)—into Kopko’s composition. Kopko would guide one having ordinary skill in the art to employ additional components that do not adversely affect the advantageous aspect of the main mixture (para [0032]). Furthermore, Kopko would guide one having ordinary skill in the art to utilize listed components like R-1233zd, R-1336mzz(Z), R-1234yf, and/or R-30 as alternative design variations (para [0063]). Therefore, a person of ordinary skill in the art would have been motivated to modify Kopko’s composition to leverage the predictable, effective properties of these compounds.
With regard to claim 7, Kopko teaches that the composition comprises 1 to 67 mol.% of R-1234ze(Z) and the balance being an effective amount of R-1336mzz(E) (para [0032]). This disclosure yields a composition of 1 to 67 mol.% R-1234ze(Z) and 33 to 99% of R-1336mzz(E), which overlaps the claimed range (para [0032]).
With regard to the ranges, it would have been obvious to one of ordinary skill in the art before the effective filling date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP §2144.05(I). Therefore, the invention as a whole would be obvious to a person of ordinary skill in the art.
With regard to claim 9, Kopko teaches that the chemical blend can further comprise a lubricant selected from poly-alpha- olefins, polyalkene glycols, polyol esters and/or polyvinyl ethers, and combinations thereof (para [0041], claim 21).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Aja A Walker whose telephone number is (571)272-0037. The examiner can normally be reached Monday - Friday 7-5.
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 at 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.
/A.A.W./Examiner, Art Unit 1761
/TANISHA DIGGS/Primary Examiner, Art Unit 1761 August 19, 2026
Prosecution Insights