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 with traverse of Group VI, claims 31 - 35 in the reply filed on January 22, 2026 is acknowledged. The traversal is on the ground(s) that the claims of Group V is a sub-species of Group VI (claims 26 – 30) and claims 26 30 have been amended to depend from claims 31 and 32. This is found persuasive because of Applicants arguments and the claim amendments.
The requirement is still deemed proper and is therefore made FINAL.
Clams 26 – 35 and 37 – 40 are under Examination.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 26 and 27 are rejected under 35 U.S.C. 112(d), as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claims 26 and 27 fail to reference a preceding claim and further fails to limit the previously set forth claim. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claims 28 – 30, 37 and 38 are rejected for being dependent upon a rejected base claim.
Claim Rejections - 35 USC § 102
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 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.
Claim(s) 26, 27, 28 and 31 are rejected under 35 U.S.C. 102(a)(1) & (a)(2) as being anticipated by Terrell (US 3,862,240).
The rejected claims cover, inter alia:
a) the method for preparing a partial fluorinated ether having the structure
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, with R1 – R4 as defined, by reacting with a fluorohydrin. (claim 26 & 31).
b) the compound of claim 27
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, where R1 – R4 as defined.
c) a composition comprising the compound with the structure of claim 27. (claim 28).
However, Terrell discloses aliphatic ether compounds of the formula CHF2-CH2-O-CF2-CHX, wherein X = CL or F. (abstract & col. 1, ln 9 – 11). The compound can be 2,2-difluoroethyl 2’-chloro-1’,2’-trifluoroethyl ether. Example 1 discloses the method of preparation wherein difluoro ethanol is used. (col.. 1, ln 62 to col. 2, ln 11).
This example illustrates the preparation of 2,2-difluoroethyl 2'-chloro-1',1',2'-trifluoroethyl ether. Potassium hydroxide (6 g., 0.095 mole) was added to a solution of commercially obtained 2,2-difluoroethyl (i.e., CHF2 CH2 OH) (24.6 g., 0.3 mole) in dimethylsulfoxide to give a yellow solution. Commercially obtained, gaseous chloroperfluoroethane (i.e., CF2 = CFCl) was then bubbled into the reaction mixture while maintaining the temperature at 50.degree.-60.degree.C. When no more CF2 =CFCl reacted, the reaction mixture was washed with water and the organic product distilled to give CHF2 CH2 OCF2 CHFCl.
Further, the ether of Terrell can be combined with oxygen and use as inhalation anesthetics. (col.2,ln 39 – 42).
Claim Rejections - 35 USC § 102
Claim(s) 27 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Coe et al. (Journal of Fluorine Chemistry, (80) 2, 1996).
Claim 27 is discussed above.
Coe discloses chloropolyfluorodiethyl ethers on pages 89 – 90 some examples are below.
Ethane, 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)-
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Ethane, 1,1'-oxybis[1,2,2-trifluoro-
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Ethane, 1-chloro-1,1,2,2-tetrafluoro-2-(1,2,2-trifluoroethoxy)-
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Ethane, 1-(2-chloro-1,2,2-trifluoroethoxy)-1,1,2,2-tetrafluoro-
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Ethane, 1-(2-chloro-1,2-difluoroethoxy)-1,2,2-trifluoro-
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Claim Rejections - 35 USC § 102
Claim(s) 27 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Anderson, et al. (Journal of Fluorine Chemistry, (77), 1996).
Claim 27 is discussed above.
Anderson discloses perfluoroalkyl hypobromite in Table 1, for Example.
Propane, 2-(2-bromo-1,1-dichloro-2,2-difluoroethoxy)-1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-
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Claim Rejections - 35 USC § 102
Claim(s) 26, 27 and 31 are rejected under 35 U.S.C. 102(a)(1) & (a)(2) as being anticipated by Chaabouni et al. (Synthetic Communications, 1989, 19(15), pp. 2683-2689; and Cheminform abs. 1990, 21, no 16, Abstract 077, 2 pages).
Claim(s) 26, 27 and 31 are discussed above.
Chaabouni teaches the following.
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, (Cheminform abstract & Table 1 of Synthetic Communications).
Claim Rejections - 35 USC § 102
Claim(s) 27, 28, 29 and 30 are rejected under 35 U.S.C. 102(a)(1) & (a)(2) as being anticipated by Arthur et al. (WO 2015/051131).
The rejected claims cover, inter alia:
b) the compound of claim 27
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, where R1 – R4 as defined.
c) a composition comprising the compound with the structure of claim 27. (claim 28).
d) a solvent composition comprising the compound with the structure of claim 27. (claim 29).
e). a coolant composition comprising the composition of claim 28. (claim 30).
However, Arthur discloses fluorinated ethers with the following structure:
Ethane, 2-(2,2-difluoroethoxy)-1,1,1-trifluoro-
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and
Propane, 3-(2,2-difluoroethoxy)-1,1,2,2-tetrafluoro-
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. (pp. 5, ln 21- 23). Further, the fluorinated compound of Arthur, is admixed with at least one electrolyte salt to form and electrolyte composition. (pp.9, ln 27 – 29). The fluorinated ethers of Arthur and a co-solvent can be combined in various ratios to form a solvent mixture as used in the electrolyte composition. (pp. ll, ln 3 – 6). Lastly, Arthur states that fluorinated ethers have used as heat transfer fluid. (pp. 1, ln 14 -15).
Claim Rejections - 35 USC § 102
Claim(s) 32 is rejected under 35 U.S.C. 102(a)(1) & (a) (2) as being anticipated by Tapscott et al. (US 5,993,682).
The rejected claim covers, inter alia, a compound with the following structure.
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, wherein R1 – R5 are as defined in the claims. In this instance R5 is CF3.
However, Tapscott discloses
Ethane, 1,1,1,2,2-pentafluoro-2-(trifluoromethoxy)-
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, with R5 = CF3 and R1 – R4 =F. (col. 12, ln 53 – 54).
Claim Rejections - 35 USC § 102
Claim(s) 32 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hudlicky et al. (Journal of Fluorine Chemistry, 102, 2000).
Clams 32 is discussed above.
However, Hudlicky discloses fluorinated ethers in Figure 1. (pp. 364).
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Claim Rejections - 35 USC § 102
Claim(s) 32, 33 and 35 are rejected under 35 U.S.C. 102(a)(1) & (a)(2) as being anticipated by Roberts (US 6,655,160).
The rejected clams cover, inter alia:
a) a compound with the structure
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, wherein R1 – R4 are as claimed and R5 is CF3. (claim 32).
b) a composition comprising the compound of with the structure of claim 32. (claim 33).
c) a coolant composition comprising the composition of claim 33.
Roberts discloses Ethane, 1,1,1,2,2-pentafluoro-2-(trifluoromethoxy)-
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. Further, the ether is used in a refrigerant composition. (col. 2, ln 10 - 25).
Claim Rejections - 35 USC § 102
Claim(s) 32 and 33 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by DiLoreto et al. (Journal of Fluorine Chemistry, 74, 1995).
Rejected claims 32 and 33 are discussed above.
However, DiLoreto discloses trifluoromethyl 1,1,2,2-tetrachloro-2-fluoroethyl ether and its use in a battery or the like. (Fig 1, entire document).
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Claim Rejections - 35 USC § 102
Claim(s) 32, 33 and 34 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bryantsev et al. (Journal of Fluorine Chemistry, 160, 2013).
Rejected claims 32 and 33 are discussed above. Claim 34 discloses a solvent composition of the compound of claim 33.
However, Table VII of Bryantsev disclose fluorinated ethers. Further, the fluorinated ethers of Bryantsev are discloses as having use as a solvent with an electrolyte composition for Li-air systems. (entire document).
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 26, 37 – 38, 31, 39 and 40 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for ether synthesis via acid catalyzed dehydration of fluorohydrin, does not reasonably provide enablement for ether synthesis occurring via on the following techniques:
i. Alkoxy-de-halogenation-reaction of an alkyl halide with a fluorohydrin ;ii. Alkoxy-de-sulphonyloxy-substitution-reaction of an fluorohydrin sulphate with an alkoxide or fluorohydrin alkoxide; iii. Hydro, alkoxy-de-diazo-disubstitution-reaction of a fluorohydrin with a diazo compound; iv. Alkoxy-de-hydroxylation-dehydration of two alcohols to yield an ether; v. Hydroxy or alkoxy-de-alkoxylation-transetherification of a (fluorohydrin)ether with an alcohol or fluorohydrin; and/or vi. Alkoxy-de-hydroxylation-reaction of an alcohol or fluorohydrin with an oxonium compound. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention commensurate in scope with these claims.
The test for enablement is whether one skilled in the art could make and use the claimed invention from the disclosures in the specification coupled with information known in the art without undue experimentation (United States v. Telectronice, 8, USPQ2D 1217 (Fed. Cir, 1988). Whether undue experimentation is needed is not based upon a single factor but rather in a conclusion reached by weighing many factors. The factors to be considered in determining whether a disclosure meets the enablement requirements of 35 U.S.C. 112, first paragraph, have been described in In re Wands, 858 F.2d 731, 8 USPQ2d 1400 (Fed. Cir., 1988). The court in Wands states, “Enablement is not precluded by the necessity for some experimentation, such as routine screening. However, experimentation needed to practice the invention must not be undue experimentation. The key word is ‘undue’, not ‘experimentation’” (Wands, 8 USPQ2sd 1404). Clearly, enablement of a claimed invention cannot be predicated on the basis of quantity of experimentation required to make or use the invention. “Whether undue experimentation is needed is not a single, simple factual determination, but rather is a conclusion reached by weighing many factual considerations” (Wands, 8 USPQ2d 1404). Among these factors are: (1) the nature of the invention; (2) the breadth of the claims; (3) the state of the prior art; (4) the predictability or unpredictability of the art; (5) the relative skill of those in the art; (6) the amount of direction or guidance presented; (7) the presence or absence of working examples; and (8) the quantity of experimentation necessary.
While all of these factors are considered, a sufficient amount for a prima facie case is discussed below.
(1) The nature of the invention and (2) the scope of the claims:
The nature of the claims are drawn to a) the method for preparing a partial fluorinated ether having the structure
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, with R1 – R4 as defined, by reacting with a fluorohydrin. (claim 26 & 31). Additionally, the nature of the invention a’) the method for preparing a partial fluorinated ether having the structure
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, with R1- R5 as defined. (claim 31) With the fluorohydrin having either of the following structures.
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,with R – R4 as defined in claims 26 and 31.
The scope of the invention in the claims is that the fluorinated ethers can be prepared by any of the following methods:
i. Alkoxy-de-halogenation-reaction of an alkyl halide with a fluorohydrin ;ii. Alkoxy-de-sulphonyloxy-substitution-reaction of an fluorohydrin sulphate with an alkoxide or fluorohydrin alkoxide; iii. Hydro, alkoxy-de-diazo-disubstitution-reaction of a fluorohydrin with a diazo compound; iv. Alkoxy-de-hydroxylation-dehydration of two alcohols to yield an ether; v. Hydroxy or alkoxy-de-alkoxylation-transetherification of a (fluorohydrin)ether with an alcohol or fluorohydrin; and/or vi. Alkoxy-de-hydroxylation-reaction of an alcohol or fluorohydrin with an oxonium compound.
(3) The state of the prior art:
Terrell discloses in Example 1 the preparation of 2,2-difluoroethyl 2'-chloro-1',1',2'-trifluoroethyl ether. Potassium hydroxide (6 g., 0.095 mole) was added to a solution of commercially obtained 2,2-difluoroethyl (i.e., CHF2 CH2 OH) (24.6 g., 0.3 mole) in dimethylsulfoxide to give a yellow solution. Commercially obtained, gaseous chloroperfluoroethane (i.e., CF2 = CFCl) was then bubbled into the reaction mixture while maintaining the temperature at 50.degree.-60.degree.C. When no more CF2 =CFCl reacted, the reaction mixture was washed with water and the organic product distilled to give CHF2 CH2 OCF2 CHFCl. (US 3,862,240).
Chaabouni discloses
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(Cheminform abs. 1990, 21, no 16, Abstract 077, 2 pages; and Table 1 of Synthetic Communications).).
(4) the predictability or unpredictability of the art: Chemistry is unpredictable. In reMarzocchi, 439 F2d 220, 169 USPQ 367 para. 3. However, the "predictability or lack thereof” in the art refers to the ability of one skilled in the art to extrapolate the disclosed or know results to the claimed invention. If one skilled in the art can readily anticipate the effect of a change within the subject matter to which the claimed invention pertains, then there is predictability in the art. MPEP 2164.03.
(5) The relative skill of those in the art: One of ordinary skill is a practicing organic chemist.
(6) The amount of direction or guidance presented and (7) the presence or absence of working examples:
The specification has provided guidance for ring opening of 2.3-epoxy-1.1.1.3-tetrafluoropropane with Olah's reagent. Also, the Preparation of di-(1.1.1.3-tetrafluoropropyl) carbonate with phosgene.
However, the specification does not provide a process for preparing the compounds:
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or
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. Further, the physical properties, etc. of the compounds having the above structures cannot be understood only from the method of producing the predetermined fluorinated alcohol. Also, the methods are different from preparing a fluorohydrin and the method for preparing a fluorinated carbonate.
(8) The quantity of experimentation necessary:
Considering the state of the art as discussed by the references above, particularly with regards to the difference is the reactants and reaction conditions required for preparing a partially fluorinated ether by methods i. – vi. and the high unpredictability in the art as evidenced therein, and the lack of guidance provided in the specification, one of ordinary skill in the art would be burdened with undue experimentation to practice the invention commensurate in the scope of the claims.
Art Made of Record
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. KR10-2018-0117868 (KR102160704, Park Chang Hun et al.).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y. Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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