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 1/14/26. Claims 1-19 are pending.
Applicant’s election without traverse of Group 1, claims 1-16 in the reply filed on 1/14/26 is acknowledged. Thus claims 17-19 are withdrawn from further consideration being drawn to the nonelected invention.
Applicant’s election of the following compound is acknowledged herewith:
PNG
media_image1.png
228
188
media_image1.png
Greyscale
PNG
media_image2.png
586
364
media_image2.png
Greyscale
Thus, additionally, claim 3 is hereby withdrawn from consideration being non-readable on the elected species. The search has not been extended to determine the patentability of the other species encompassed by the claims.
Claims 3 and 17-19 are withdrawn. As a result, claims 1-2 and 4-16 are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
PNG
media_image3.png
60
422
media_image3.png
Greyscale
Objections
Claim 1 is objected to because of the following informalities:
Claim 1 recites “lithium single-ion monomer“, but also just “single-ion monomer“ without the “lithium”. The examiner recommends instead for continuity to recite “lithium single-ion monomer“ throughout the claim.
The disclosure is objected to because of the following informalities:
The figures are blurry and difficult to discern. For example, paragraphs 70-71 have the following indiscernible figures:
PNG
media_image4.png
204
416
media_image4.png
Greyscale
PNG
media_image5.png
190
406
media_image5.png
Greyscale
The drawings are also objected to because of the same reason. Below is applicant’s Scheme 1 which is blurry:
PNG
media_image6.png
214
558
media_image6.png
Greyscale
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Appropriate correction is required.
Claim Rejections – 35 USC 112.2
The following is a quotation of the second paragraph of 35 U.S.C. 112:
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.
Claims 1-2 and 4-16 are rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention.
Claims 1 and 6 are indefinite because of the claim language “suitable to act as a quenching base”. The specification doesn’t define the metes and bounds of what would be suitable to be a quenching base, such that one would know what is included and what is excluded.
Claim 5 is indefinite because of the claim language “stable nitrogen-based organic cation”. The specification doesn’t define the metes and bounds of what would be stable as a nitrogen-based organic cation, such that one would know what is included and what is excluded.
Claims 1, 13 and 15 are indefinite because of the claim language “lithium single-ion monomer”. The specification doesn’t define the metes and bounds of what would be considered a lithium single-ion monomer, such that one would know what is included and what is excluded. The metes and bounds of the term “lithium single-ion monomer” is not known to those of ordinary skill in the art. If applicant is broadly claiming the vast number of possible compounds that contain lithium, as a single-ion, along with the ability to be a possible monomer, then the applicant should explicitly state this. This admission might then require a further rejection by the examiner.
Claim 8 is indefinite because it recites "sulfonate”. There is no antecedent basis for "sulfonate” in claim 1, from which claim 8 depends.
Claim 12 is indefinite because of the claim recites a “lithium single-ion monomer” but the formula does not require the presence of lithium, since the monovalent cation M can also be H+, Na+, K+, Rb+ or Cs+. Furthermore the claim is indefinite since H+ (otherwise known as a proton) is not generally considered a “monovalent cation”, nor a “lithium single-ion monomer”.
Claim 16 is indefinite because it recites a multi-step process in the reaction scheme, which includes reaction of a sulfonate with oxalyl chloride as the first step. There is no antecedent basis for this multi-step process, which includes a first reaction of a sulfonate with oxalyl chloride in claim 1, from which claim 16 depends.
The dependent claims are rejected as being dependent on a rejected claim.
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 1-2. 4-7, 10 and 12-15 are rejected under 35 U.S.C. 103(a) as being unpatentable over Fuji et al. (WO 2018021185, pub date 02/01/2018; the English translation is used herein), in view of Phan et al. (Polym. Chem., 2016, 7, 6901).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Fuji et al. exemplifies the synthesis of sulfonimide derivatives, specifically lithium 4-styrenesulfonyl(trifluoromethylsulfonyl)imide (reads on applicant’s lithium single-ion monomer when R1=R1=R3=H, L1 is absent, R4 is a phenyl group, Rf=CF3, M=Li+), with the product structure below:
PNG
media_image7.png
150
64
media_image7.png
Greyscale
Fuji et al. exemplifies adding trifluoromethanesulfonamide (reads on applicant’s fluorinated sulfonamide when Ra=CF3) to a lithium hydride solution (reads on applicant’s compound that is suitable to act as a quenching base and a lithium cation source), then adding to this solution, a solution of styrenesulfonyl chloride (reads on applicant’s sulfonyl chloride when R1=R1=R3=H, L1 is absent, R4 is a phenyl group). The resulting reaction solution is stirred for 17 hours, then the inorganic salts were removed by filtration, then distilled and evaporated to give the lithium 4-styrenesulfonyl(trifluoromethylsulfonyl)imide product, with the structure as shown above. (page 8, Example 1, 3rd paragraph)
Fuji et al. teaches when water was not added and the reaction was allowed to stand at room temperature for 1 hour, spontaneous polymerization proceeded. Fuji et al. also teaches the use of silica gel, chromatograph analysis and Gel Permeation Chromatograph (GPC) analysis in their synthesis and purification procedures. Fuji et al. teaches the equivalency of lithium hydroxide and lithium hydride as bases. (page 4, 2nd paragraph; page 10, Comparative Example 3, 3rd paragraph; page 6, 4th paragraph; page 7, 4th paragraph to last paragraph)
Fuji et al. also teaches the equivalency of the 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone) and the 4-vinylphenyl carbon backbone (also known as styrene carbon backbone) for R3 in their sulfonyl halide (compound (4), see the structure below), used in the synthesis of their sulfonimide derivatives. (page 2, 2nd to the last paragraph; page 3, 2nd paragraph)
PNG
media_image8.png
112
168
media_image8.png
Greyscale
With regard to applicant’s limitation for a simultaneous reaction, it would be reasonable to expect Fuji et al.’s synthesis of lithium 4-styrenesulfonyl(trifluoromethylsulfonyl)imide to read on this limitation, since all reactants are added to the same reaction vessel and subsequently stirred for 17 hours to react. Even if it does not, it would be obvious to add all the reactants to a single reaction vessel for a simultaneous reaction since, as indicated in MPEP 2144.04 IV. C., the order of prior art process steps is prima facie obvious in the absence of new or unexpected results.
With regard to applicant’s limitation for purifying the lithium single-ion monomer, removing the LiCl byproduct and running a silica gel flash chromatography, it would be reasonable to expect Fuji et al.’s synthesis to read on these limitations, since Fuji et al. teaches distillation, removal of the inorganic salts from the reaction, the use of silica gel, chromatograph analysis and Gel Permeation Chromatograph (GPC) analysis in their synthesis and purification procedures. Even if it does not, it would be obvious to purify the lithium single-ion monomer, remove the LiCl byproduct and run a silica gel flash chromatography, since these are standard purification procedures in synthetic chemistry.
With regard to applicant’s limitation for the method not requiring synthesis of a (stable) nitrogen based organic cation, it would be reasonable to expect Fuji et al. to read on this limitation, since Fuji et al. does not teach the synthesis of a nitrogen based organic cation.
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Fuji et al. is deficient in the sense that it does not exemplify applicant’s elected species for the lithium single-ion monomer, with a 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone). Instead Fuji et al. exemplifies the 4-vinylphenyl carbon backbone (also known as styrene carbon backbone) for the lithium single-ion monomer. However, Fuji et al. does teach the equivalency of the 3-acryloyloxypropyl carbon backbone and the 4-vinylphenyl carbon backbone for the sulfonyl halide, used in their synthesis of the sulfonimide derivatives.
Nevertheless, Phan et al. does exemplify the propyl acrylate carbon backbone. And Phan et al. also teaches the equivalency of the propyl acrylate carbon backbone (ASTFSIK) and the styrene carbon backbone (SSTFSILi) in the synthesis of their sulfonimide derivatives (which corresponds to applicant’s single-ion monomer), see the structures below. Phan et al. also teaches because of the poor solubility of the potassium salt of (SSTFSIK), the potassium salt monomer was converted to the lithium salt monomer by lithium hydroxide (LiOH) in methanol to give the lithium salt monomer version (SSTFSILi). (page 6902, Scheme 1; page 6903, first column, 3rd paragraph to the second column first paragraph; page 6904, Table 1, first column, second paragraph to the last paragraph, Scheme 2; page 6905, first column, second paragraph)
PNG
media_image9.png
70
164
media_image9.png
Greyscale
(ASTFSIK) Potassium salt monomer with a 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone)
PNG
media_image7.png
150
64
media_image7.png
Greyscale
(SSTFSILi) Lithium salt monomer with a 4-vinylphenyl carbon backbone (also known as styrene carbon backbone)
Phan et al. teaches the conversion of the sulfonyl chloride reactant (first compound in the following scheme below) to the resulting (ASTFSIK) product (last compound in the following scheme) (see scheme below). Thus, Phan et al. teaches the formation of (ASTFSIK), which contains the propyl acrylate carbon backbone in the sulfonimide derivative product (which corresponds to applicant’s single-ion monomer), by the reaction of the sulfonyl chloride (also known as sulfonyl halide) reactant. (page 6904, Scheme 2)
PNG
media_image10.png
188
526
media_image10.png
Greyscale
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 Phan et al.’s propyl acrylate carbon backbone for Fuji et al.’s styrene carbon backbone with a reasonable expectation of success, since Phan et al. teaches the equivalency of the propyl acrylate carbon backbone and the styrene carbon backbone for their sulfonimide derivatives (which corresponds to applicant’s lithium single-ion monomer). Furthermore, Fuji et al. also teaches a similar equivalency of the 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone) and the 4-vinylphenyl carbon backbone (also known as styrene carbon backbone) for their sulfonyl halide, used in the synthesis of their sulfonimide derivatives.
Thus both Phan et al. and Fuji et al. show how it is old in the art to use compounds that have either a 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone) or a 4-vinylphenyl carbon backbone (also known as styrene carbon backbone) for the sulfonyl chloride reactant which is then transformed to the corresponding sulfonimide derivative product (which corresponds to applicant’s lithium single-ion monomer).
It would also be obvious to substitute lithium hydride (LiH) for lithium hydroxide (LiOH) with a reasonable expectation of success, since Fuji et al. teaches the equivalency of lithium hydroxide and lithium hydride as bases.
Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982).
Absent evidence of unexpected results for applicant’s particular process steps, it would be obvious to synthesize the more highly soluble lithium salt of the sulfonimide derivative with a 3-acryloyloxypropyl carbon backbone (also known as propyl acrylate carbon backbone) from the simultaneous reaction of the propyl acrylate sulfonyl chloride with trifluoromethanesulfonamide and lithium hydroxide, with a reasonable expectation of success.
Conclusion
No claim is 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.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691