DETAILED ACTION
Status of Application
This action is responsive to continuing application filed 06/23/2023 as a continuation of
PCT/JP2021/047710, filed 12/22/2021. Original claims 1-11 are currently pending and under examination herein.
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 . However, 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 a 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.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) filed on 06/23/2023, 08/30/2023, 11/15/2024, and 08/04/2025 are in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies
of the IDS are included with the mailing/transmittal of this Office action.
Foreign Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections – 35 U.S.C. 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 10 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.
Regarding Claim 10, the claim recites “tetrafluoroethylene/perfluoro(alkyl vinyl ether) copolymer” as a species of fluoropolymer producible by the method of parent claim 1. This creates an indefiniteness issue because claim 1 stipulates that “in the solvent, a content of a fluorine-containing compound (2) represented by formula: R3-CF=CF-R4-OR2 … is 1.00% by mass or less based on a content of the fluorine-containing compound ether compound (1)” (see lines 8-17) and said formula literally reads on perfluoro(alkyl vinyl ethers) (where R3 is F, R4 is a single bond and R2 is perfluoroalkyl). Thus, it is unclear how a perfluoro(alkyl vinyl ether) can be selected as a possible comonomer in the claimed method, given the positive limitation on content of said compound (2) having a formula inclusive of that very comonomer. Clarification of this apparent inconsistency between claim 10 and the base claim is required.
Common Ownership Notice
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.
Claim Rejections – 35 U.S.C. 103
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.
Claims 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over JP 2005-029704A (‘JP ‘704’) (citing infra to corresponding machine-generated translation) or JP 2012-241128A (‘JP ‘128’) (citing infra to corresponding machine-generated translation), each taken in view of Flynn, et al (WO 2007/030314 A2), Henry, et al (Integrated Environmental Assessment and Management, 14(3), pp. 316-334 and Supplemental Data, pp. 1-12) and Sigma-Aldrich: “Hexafluoroisopropyl methyl ether” (‘Sigma-Aldrich’).
Regarding Claims 1 and 9; JP ‘704 discloses (see ¶¶ [0029]-[0030] (Examples 1, 2)) the copolymerization of tetrafluoroethylene (TFE), ethylene (E) and perfluorobutyl ethylene in CF3CH2-O-CF2CHF2 or CHF2CF2CH2-O-CF2CHF2 as solvent, wherein both compounds correspond to claimed formula for compound (1) (where R1 and R2 are each a partially fluorinated alkyl group). The solvent compounds are selected for their low ozone depletion potential and low chain transfer constants and are said to provide polymers with high molecular weights (¶¶ [0006], [0009]). JP ‘128 similarly discloses (see ¶ [0055] (Example 1)) the copolymerization of TFE and hexafluoropropylene (HFP) in CH3OCH(CF3)2 as solvent, wherein the compound also corresponds to claimed formula for compound (1) (where R1 is a non-fluorinated alkyl group and R2 is a partially fluorinated alkyl group). The polymerization produces a fluororesin [per claim 9] having a MFR (5 kg/372oC) of 20 g/10 min, a value commensurate with MFRs reported in inventive examples of the present specification.
Both JP ‘704 and JP ‘128 differ from the claimed subject matter in failing to disclose the content of fluorine-containing olefin compound (2) in the solvent.
However, in the same technical field, Flynn et al describe the preparation of partially fluorinated alkyl ethers with ≥ 99% purity (see Examples 3-4 on pp. 20-21 and Example 11 on p. 25). The described preparation includes treatment of a recovered reactor product (i.e., intermediate) to remove the olefin of the desired final product. Thus, in Example 3, for instance, the recovered reactor product contained the olefin of the desired hydrofluoroether, CF3CFHCF₂CH(CH₃)OCF₂CFHCF3, and this olefin was removed through a treatment as detailed on page 21, lines 2-9, resulting in a material of purity = 99%. While no olefin formula is mentioned in Example 3, Flynn et al in Example 2 do identify the olefin of the desired product, CF₃CFHCF₂CH₂OCF2CFHCF3, as having formula CF₃CFHCF₂CH₂OCF=CFCF3. Hence, by analogy, the olefin of the desired hydrofluoroether in Example 3 would be represented by formula CF₃CFHCF₂CH(CH3)OCF=CFCF3, which corresponds to claimed formula for compound (2) (where R4 represents a single bond, R2 represents a partially fluorinated alkyl group and R3 represents a completely fluorinated alkyl group). Flynn et al further suggest use of the described partially fluorinated alkyl ethers as solvents in the polymerization of fluorinated monomers (see p. 4, 3rd para and p. 17, 1st full para).
It is moreover well known in the art that in the polymerization of TFE, the purity of the monomers and reaction medium is essential for favorable progress of the reaction and to achieve high molecular weight, as confirmed by Henry et al; see in particular Supplemental Data Content on pages 6-7 (“Fluoromonomer purity is essential to achieve high molecular weight fluoropolymers. For example, one of the routes in which, the high molecular weight PTFE (for expanded PTFE) is produced requires 99.999% pure tetrafluoroethylene (TFE) monomer (gas) for polymerization. Very pure/deionized water is required for polymerization. Polymerization aids, ranging from 0.01% to 0.5% of the weight of water in the reactor, are used depending on the rate and degree of polymerization (Ebnesajjad, 2000).”) Further in regards to high purity reaction medium, it is also well known that the solvent used in JP ‘128 is commercially available in high purity form, viz., ≥ 99% anhydrous as confirmed by Sigma-Aldrich.
As shown by Henry et al, an ordinarily skilled practitioner would have known that highly pure monomers and reaction media are essential for successful polymerization processes, especially in the field of fluoropolymer preparation. Thus, one so skilled would have been expected to seek to provide a fluoroolefin polymerization process in which all reactants and components of the reaction medium are as pure as possible. To that end, it would have been obvious to one of ordinary skill in the art at the time of effective filing to substitute the solvents used in JP ‘704 or JP ‘128 by a fluorine-containing ether compound (1) as claimed herein and taught by Flynn et al, in the expectation of achieving a process for the polymerization of TFE, CTFE or VDF that proceeds rapidly and leads to fluoropolymer of higher molecular weight.
Regarding Claims 2, 4 and 6; JP ‘704 or JP ‘128 in view of Flynn et al, Henry et al and Sigma-Aldrich renders obvious the method according to claim 1 as discussed above. Flynn et al further disclose wherein the fluorine-containing ether compound (1) is a fluorine-containing ether compound (1-1), a fluorine-containing ether compound (1-2), or a fluorine-containing ether compound (1-3); see, e.g., Example 3, wherein the prepared partially fluorinated alkyl ether, CF3CFHCF₂CH(CH₃)OCF₂CFHCF3, corresponds to claimed formula for compound (1-3) (of claim 6) where R2 is a partially fluorinated alkyl group. And as the formula for compound (1-3) defines a subgenus of compounds encompassed by the claimed formulae for said compound (1-1) and said compound (1-2), Flynn et al is considered to meet the requirements of claims 2 and 4 as well.
Regarding Claims 3, 5 and 7; JP ‘704 or JP ‘128 in view of Flynn et al, Henry et al and Sigma-Aldrich renders obvious the method according to claims 2, 4, and 6, respectively, as discussed above. Flynn et al further disclose wherein the fluorine-containing ether compound (2) is a fluorine-containing ether compound (2-1-1), a fluorine-containing ether compound (2-2-1), or a fluorine-containing ether compound (2-3-1); see, e.g., Example 3, wherein the olefin of the desired hydrofluoroether in Example 3, presumably represented by formula CF₃CFHCF₂CH(CH3)OCF=CFCF3, corresponds to claimed formula for compound (2-3-1) (of claim 7) where R2 is a partially fluorinated alkyl group. And as the formula for compound (2-3-1) defines a subgenus of compounds encompassed by the claimed formulae for said compound (2-2-1) and said compound (2-1-1), Flynn et al is considered to meet the requirements of claims 3 and 5 as well.
Regarding Claim 8, JP ‘704 or JP ‘128 in view of Flynn et al, Henry et al and Sigma-Aldrich renders obvious the method according to claim 1 as discussed above. JP ‘128 further discloses wherein the solvent further comprises water (see ¶¶ [0041] and [0055] (Example 1)).
Regarding Claim 10, JP ‘704 or JP ‘128 in view of Flynn et al, Henry et al and Sigma-Aldrich renders obvious the method according to claim 1 as discussed above. JP ‘128 further discloses wherein the fluoropolymer is a tetrafluoroethylene/perfluoro(alkyl vinyl ether) copolymer; specifically a TFE/PAVE copolymer as a preferred fluoropolymer (see ¶ [0031]).
Regarding Claim 11, JP ‘704 or JP ‘128 in view of Flynn et al, Henry et al and Sigma-Aldrich renders obvious the method according to claim 1 as discussed above. Flynn et al further disclose in Example 3, for instance, that the recovered reactor product contained the olefin of the desired hydrofluoroether, CF3CFHCF₂CH(CH₃)OCF₂CFHCF3, and that this olefin was removed by treating the reactor product with anhydrous HF (corresponding to claimed “halogenating agent”) in the presence of the desired hydrofluoroether (corresponding to claimed “fluorine-containing ether compound (1)), and fractionating the resulting material using a 10-plate Oldershaw column to obtain a material of purity = 99% (see pp. 20-21, bridging para). While the byproduct compound resulting from such anhydrous HF treatment is not identified, the disclosed treatment effectively removes olefin byproduct in a similar manner to the present invention (cf., ¶¶ [0096], [0103]-[0104]) of as-filed specification); therefore, it is plausible to infer that the treatment implicitly results in a compound (4) as claimed, in particular a halogen adduct, which is then separated from the resulting material to prepare the desired hydrofluoroether.
Conclusion
Pending claims 1-11 are rejected. No claims are in condition for allowance at this time.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/01-24-26