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 .
Detailed Action
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 8/25/26 has been entered.
Claims 1-20 are pending in this application. Claims 5 and 16 remain withdrawn from further consideration. As a result, claims 1-4, 6-15 and 17-20 are being examined in this Office Action. The prior 103 rejection is withdrawn in view of applicant’s amendment. However, based on a new search in response to applicant's amended claims, a new 103 rejection is in order.
Objections
Claim 20 is objected to because the phrase about 3 to about 5 equivalents dimethylsulfate relative to the metal salt is grammatically incomplete. The phrase also writes dimethyl sulfate as one word. Suggested wording is: the di(C1-3 alkyl) sulfate is dimethyl sulfate, and the effective amount is about 3 to about 5 equivalents relative to the metal salt of bis(fluorosulfonyl)imide. Appropriate correction is required.
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 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 of this title, 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 1-4, 6-15 and 17-20 remain rejected under 35 U.S.C. 103 as being unpatentable over Honda et al. (US 20120022269, pub date Jan. 26, 2012), in view of Yang et al. (US 20190058211, pub. date Feb. 21, 2019).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Honda et al. teaches a batch method for producing fluorine-containing N-alkylsulfonylimide compounds by alkylating a fluorine-containing sulfonylimide salt with a dialkyl sulfate. Honda et al. exemplifies synthesis of N-methyl bis(fluorosulfonyl)imide, Me-FSI, by reacting potassium bis(fluorosulfonyl)imide with dimethyl sulfate. Honda et al. places 86.4 g, 685.5 mmol, of dimethyl sulfate, 10.0 g, 45.7 mmol, of potassium bis(fluorosulfonyl)imide, and 4.0 g, 45.7 mmol, of dioxane in a flask. The mixture is stirred for 2 hours at 100 degrees C. Honda et al. reports 4.0 g of Me-FSI after phase separation and 2.6 g more after extraction, for a total yield of 74%. Honda et al. further teaches purification by distillation. Honda et al. teaches alkylating-agent-to-salt ratios of 50:1 to 1:1, temperatures of 0 to 200 degrees C, preferably 50 to 150 degrees C, and reaction times of 0.5 to 200 hours, preferably 1 to 50 hours. (Abstract; paragraphs 38-52, 73, 77 and 83.)
Yang et al. teaches mixing one or more salts selected from LiFSI, NaFSI and KFSI with a solvent comprising DME. Yang et al. teaches that the salt and DME form a bound moiety. Yang et al. therefore establishes that DME directly associates with and provides a compatible solvent for the same FSI salts used in Honda et al. Yang et al. exemplifies LiFSI in DME at about 5 M and also teaches a comparative LiFSI-DME electrolyte at about 1.5 M. (Abstract; paragraphs 8, 60-69 and 72; claim 1.)
See the scheme below from applicant’s specification on page 9, Scheme 1, which also illustrates Honda et al.’s synthesis of N-methyl bis(fluorosulfonyl)imide ((FSO2)2NCH3) (MeFSI) by reacting bis(fluorosulfonyl)imide potassium salt (FSO2)2N−K+, with the methylating agent dimethylsulfuric acid (aka dimethyl sulfate) ((CH3O)2SO2 or Me2SO4):
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Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Honda et al. is deficient in the sense that Example 10 uses dioxane and does not expressly use DME as the solvent.
Yang et al. does not perform Honda et al.'s alkylation reaction, but Yang et al. expressly teaches the same FSI salts in DME and teaches direct salt-DME association.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to use Yang et al.'s DME solvent in Honda et al.'s alkylation of an FSI salt with dimethyl sulfate. Yang et al. expressly teaches that LiFSI, NaFSI and KFSI may be mixed with DME and that DME associates with the metal cation and FSI salt. One of ordinary skill therefore would have had reason to use DME as a compatible liquid medium for Honda et al.'s FSI-salt alkylation, with a reasonable expectation that the salt would be present in and interact with the DME medium. The resulting process would use DME without added dioxane and would provide Honda et al.'s Me-FSI product.
Honda et al. also teaches ranges that overlap or encompass the claimed sulfate amount, temperature and time. Honda et al. teaches a dialkyl-sulfate-to-FSI-salt molar ratio of 50:1 to 1:1, a temperature of 0 to 200 degrees C, preferably 50 to 150 degrees C, and a reaction time of 0.5 to 200 hours, preferably 1 to 50 hours. Selection of the claimed overlapping amounts, temperatures and times would have been obvious through routine optimization because Honda et al. identifies each as a reaction variable. Yang et al. also expressly teaches LiFSI in DME at 1.5 M, which meets the endpoint of claim 12.
With regard to claims 2-4, Honda et al. teaches potassium and lithium FSI salts, while Yang et al. expressly teaches LiFSI, NaFSI and KFSI in DME.
With regard to claims 6-8, Honda et al.'s preferred 50 to 150 degrees C range overlaps the claimed temperature ranges.
With regard to claims 9-11 and 20, Honda et al.'s 1:1 to 50:1 ratio encompasses the claimed sulfate equivalents, and Honda et al. specifically uses dimethyl sulfate.
With regard to claim 12, Yang et al. teaches a 1.5 M LiFSI-DME composition.
With regard to claims 13-15, Honda et al.'s preferred 1 to 50 hour range overlaps the claimed time ranges.
With regard to claim 17, Honda et al. performs the reaction in a flask as a batch process.
With regard to claims 18-19, Honda et al. teaches separation, extraction and distillation of the product. Accordingly, the combination teaches or renders obvious the limitations of the dependent claims.
Response to Arguments
Applicant’s arguments have been considered but are not persuasive for the following reasons:
Applicant argues that Honda et al. uses dioxane and does not teach using DME or ethyl acetate.
Applicant's argument is not persuasive because the rejection does not rely on Honda et al. alone to teach DME. Honda et al. is relied upon for the same FSI-salt alkylation with dimethyl sulfate to form Me-FSI. Yang et al. is relied upon for expressly teaching LiFSI, NaFSI and KFSI with DME as the solvent and for teaching direct salt-DME association. Honda et al. does not criticize, discredit or discourage DME.
Applicant argues that the prior rejection did not provide a reasonable expectation that DME would work in Honda et al.'s reaction.
The present rejection addresses that argument. Yang et al. expressly places the same FSI salts in DME and teaches that the salt and DME associate. Thus, the expectation that DME is compatible with and provides a liquid medium for the FSI salt comes from the prior art and not from applicant's disclosure.
Applicant argues that Table 1 shows surprising and unexpected yields.
The argument is not persuasive. Honda et al. reports a total Me-FSI yield of 74%. Applicant reports 79.46% Me-FSI for DME and 71.59% for ethyl acetate. Applicant has not shown that the difference between Honda et al.'s reported 74% yield and the reported DME yield is statistically or practically significant. Applicant's lower-yield reproduction of the traditional procedure does not establish that Honda et al.'s disclosure is inoperative.
Furthermore, the evidence is not commensurate in scope with claim 1. Claim 1 covers alkali and alkaline-earth salts, alkyl and alkenyl sulfates, alkyl and alkenyl products, a range above one through ten equivalents, and DME, ethyl acetate or combinations. Table 1 tests KFSI with five equivalents of dimethyl sulfate to make Me-FSI under selected conditions. The data does not establish unexpected results across the scope of claim 1.
Applicant argues that the rejection is based on hindsight.
Applicant's argument is not persuasive. Honda et al. provides the same Me-FSI-forming alkylation, and Yang et al. independently teaches the same FSI salts in DME. The reason to use DME and the reasonable expectation of salt-DME compatibility therefore come from the prior art.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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/JENNIFER C SAWYER/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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