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
This office action is in response to applicant’s communication filed on 6/3/26. Applicant’s amendments to claims 1, 3, 4, 11 and 15 have 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 Claims 5 and 16 remain withdrawn from further consideration.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 The objection to claim 11 is withdrawn in view of applicant’s amendment.
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 FunnyChemical (“The Usages of 1,2-Dimethoxyethane”, 2014, Retrieved from: https://funnychemical.webnode.page/news/the-usages-of-1-2-dimethoxyethane/)
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 dialkylsulfuric acid. Honda et al. exemplifies the 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). In a flask equipped with a stirring bar, a condenser tube, and a thermometer, 86.4 g (685.5 mmol) of dimethylsulfuric acid, 10.0 g (45.7 mmol) of bis(fluorosulfonyl)imide acid potassium salt, and 4.0 g (45.7 mmol) of dioxane were placed. Then, the content of the flask was stirred for 2 hours at 100 degree C. After pouring 150 g of ion-exchange water, the content of the flask was stirred for 1 hour at 70 degree C. After the stirring, by separating with a separating funnel, 4.0 g of N-methyl bis(fluorosulfonyl)imide (lower layer), which was the intended product, was obtained (yield: 45%). Furthermore, after extracting the aqueous phase (upper phase) with chloroform, by concentrating the solvent, 2.6 g of the intended product was obtained (total yield: 74%). Furthermore, Honda et al. teaches similar products were purified by distillation. (abstract; paragraphs 38-52, 73, 77, 83).
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 it does not expressly teach applicant’s claimed solvent substantially free of dioxane or applicant’s 1,2-dimethoxyethane (DME) solvent. Instead Honda et al. teaches the dioxane solvent in Example 10.
FunnyChemical teaches the benefits of using DME. DME is an excellent inert aprotic solvent and useful as a solvent for chemical reactions that undergo nucleophilic substitution. FunnyChemical teaches DME is a suitable media for a number of chemical reactions. FunnyChemical further teaches that DME is used as a higher boiling alternative to diethyl ether and tetrahydrofuran as an aprotic neutral polar solvent. FunnyChemical further teaches that DME is stable both in acidic and alkali media. (page 1)
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 substitute Honda et al.’s dioxane solvent with FunnyChemical’s DME solvent, since Honda et al.’s synthesis reaction of MeFSI is an alkylation reaction of bis(fluorosulfonyl)imide potassium salt with dimethyl sulfate to provide N-methyl bis(fluorosulfonyl)imide, and FunnyChemical teaches that DME is an excellent inert aprotic polar solvent suitable for chemical reactions and useful for nucleophilic substitutions. Thus it would be obvious to try to utilize DME’s excellent solvent properties in Honda et al.’s synthesis of the MeFSI product.
Furthermore, Honda et al. already teaches that alkylation of the fluorine-containing sulfonylimide acid or acid salt proceeds using a dialkylsulfuric acid or dialkylcarbonic acid alkylating agent, and Honda et al. teaches molar ratios, reaction temperatures, reaction times, acidic conditions, and purification conditions that overlap or render obvious the presently claimed ranges. Honda et al. teaches the alkylating agent may be added to the fluorine-containing sulfonylimide acid or salt in a molar ratio of 50:1 to 1:1. Honda et al. teaches a preferable reaction temperature ranges from 0 to 200 degree C and an even more preferable reaction temperature ranges from 50 to 150 degree C. Honda et al. teaches a preferable reaction time ranges from 0.5 to 200 hours and an even more preferable reaction time ranges from 1 to 50 hours. Honda et al. further teaches filtration, separation, extraction, and distillation of the product.
Additionally, with regard to applicant’s limitations regarding the reaction time, temperature, purification by distillation, amounts and equivalents of dialkyl sulfate and bis(fluorosulfonyl)imide metal salt, it is the position of the examiner that one of ordinary skill in the art, at the time of the invention, would through routine and normal experimentation determine the optimization of these limitations to provide the best effective variable depending on the results desired. Because Honda et al. already teaches the reaction time, temperature, purification by distillation, amounts of dialkyl sulfate and bis(fluorosulfonyl)imide metal salt, the examiner asserts that the reaction time, temperature, purification by distillation, amounts and equivalents of dialkyl sulfate and bis(fluorosulfonyl)imide metal salt, are art recognized result-effective variables. Thus it would be obvious in the optimization process to optimize the reaction time, temperature, purification by distillation, amounts and equivalents of dialkyl sulfate and bis(fluorosulfonyl)imide metal salt. The applicant does not show any unusual and/or unexpected results for these limitations. Note that the prior art provides the same effect desired by the applicant, the formation of MeFSI by alkylation of dialkyl sulfate and bis(fluorosulfonyl)imide metal salt.
Response to Arguments
Applicant’s arguments have been considered but are not persuasive for the following reasons:
Applicant argues that Honda describes a method of synthesis of N-methyl bis(fluorosulfonyl)imide using dioxane, and that Honda is bereft of any teaching of synthesizing N-methyl bis(fluorosulfonyl)imide using any solvent other than dioxane.
Applicant’s argument is not persuasive because the rejection does not rely on Honda alone to teach the DME solvent. Honda et al. is relied upon for teaching the same alkylation reaction between bis(fluorosulfonyl)imide potassium salt and dimethyl sulfate to form N-methyl bis(fluorosulfonyl)imide. FunnyChemical is relied upon for teaching the benefits of DME as an excellent inert aprotic polar solvent and as a good solvent for nucleophilic substitutions. The fact that Honda et al. exemplifies dioxane does not teach away from using DME, since Honda et al. does not criticize, discredit, or otherwise discourage the use of DME or other inert aprotic solvents.
Applicant argues that FunnyChemical merely teaches DME in a laundry list of different chemical reactions and does not teach replacing dioxane with DME in Honda’s synthesis.
Applicant’s argument is not persuasive because obviousness does not require an express teaching to bodily incorporate the secondary reference into the primary reference. Rather, the prior art need only provide an apparent reason to combine the known elements in the fashion claimed. Here, Honda et al. teaches the known synthesis of MeFSI by alkylation of an FSI metal salt with dimethyl sulfate, while FunnyChemical teaches that DME is an excellent inert aprotic polar solvent, suitable for chemical reactions, and a good solvent for nucleophilic substitutions. Therefore, one of ordinary skill in the art would have had reason to utilize DME in Honda et al.’s alkylation reaction with a reasonable expectation of success.
Applicant argues that DME and dioxane are not homologs.
Applicant’s argument has been considered. However, the rejection does not require DME and dioxane to be homologs. The rejection is maintained because FunnyChemical provides an independent teaching of DME’s suitability as an inert aprotic polar solvent for chemical reactions and nucleophilic substitutions, and Honda et al. provides the corresponding MeFSI-forming alkylation reaction. Therefore, the combination of Honda et al. and FunnyChemical renders the claimed process obvious.
Applicant argues that the Examiner’s rejection is based on impermissible hindsight.
Applicant’s argument is not persuasive. The motivation to use DME is not derived from applicant’s disclosure, but from FunnyChemical’s teaching that DME is an excellent inert aprotic polar solvent suitable for chemical reactions and a good solvent for nucleophilic substitutions, in combination with Honda et al.’s teaching of an alkylation reaction that produces MeFSI. Thus, the rejection is based on the facts gleaned from the prior art and not on applicant’s disclosure.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 extension fee 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 date of this final action.
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 Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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