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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement(s) (IDS) submitted on 10/19/2023 and 11/03/2023 have been considered by the examiner.
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) 14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Liu (US 20180072669 A1) .
Regarding claim 14, Liu teaches all the following elements:
Solution comprising the following components: (Liu teaches the synthesis of the desired formula II from formula I by making a solution, see below for specifics on the composition.)
a) water, (Liu [0313] teaches the mixture of formula I with water to form formula II at a 90.5% recovery rate, which also means there would be side products formed.)
b) N,N,N,2,2,6,6-hexamethyl-4-piperidinamine of formula (I) (The process of Liu includes mixing a compound that is formula 1 with halogens in order to methylate it and form a compound that meets the limitations of formula II, as well as side products.)
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c) optionally byproducts which are not compound of formula (I), compound of formula (II) or compound of formula (III), (Since this limitation is optional, it need not be specifically referenced by Liu. However, byproducts, including formula III, would inherently be produced during this process.)
d) 90 to 98.5 wt.-% according to the sum of the total weight amounts of components b) to e) of N,N,N,2,2,6,6-heptamethyl-4-piperidinaminium chloride of formula (II) (In the solution of Liu where there is a 90.5% recovery of formula II in the mixture, there would be between 0 and 9.5% of all side products as well as the original formula 1. Therefore, the amount of formula II compared to the rest of components b to e would anticipate the claimed range.)
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e) N,N,N,1,2,2,6,6,-octamethyl-4-piperidinaminium chloride of formula (Ill) (See below for argument that formula III would be an inherent side product in the process of Liu, which methylates formula I to form formula II.)
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wherein the water content is in the range from 40 to 70 wt.-% according to the solution (Liu paragraph 0313 states that the obtained white salt, of which there were 12.8g remaining after drying, was dissolved in 20mL deionized water. Before drying, this means there would be 60.98% water, based on the density of water meaning that there would be 20g water and 12.8g solids content. This would fall within the claimed range.)
and the mass ratio between component of the formula (I) to compound of formula (III) is smaller than 1 and the mass ration between compound of formula (III) to compound of formula (II) is smaller than 0.04. (While this specific ratio of formula I to III and formula II to III is not explicitly claimed, it is considered to be an inherent property of the mixture as the methylation of compound II would form side products that meet the limitations of claim 1, including the amount of remaining formula I and formula III.)
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Liu drawing shown on page 154 clearly depicts a process in which both formula I and formula II are derived in the synthesis of TEMPO products for use as a catholyte in an aqueous organic redox flow battery. Instant specification states that the product of formula III is a side product of the methylation of formula I to form formula II (“The compound of formula (Ill) is N,N,N,1,2,2,6,6-octamethyl-4-piperidinaminium chloride. It is obtained as side product during the methylation of compound of formula (I) with a methylation agent.” Instant spec page 7 lines 15-18) Therefore, the process of Liu, which forms formula II via the methylation of formula I, would inherently produce some amount of side product as well. This would also inherently be in a much smaller proportion than formula II. Liu cites in paragraph [0313] that there is a 90.5% recovery rate of compound 2, which means that there would be between a 0-9.5% by weight quantity of side product produced.
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 (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 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.
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(s) 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu (US 20180072669 A1) in view of Schubert (WO 2018028830),
Regarding claim 15, Liu is silent on the following elements:
The solution of claim 14, wherein the content of compound of formula (II) is in the range of 95 to 98.5 wt.-% according to the sum of the total weight amounts of components b) to e).
However, Schubert teaches all of the elements of claim 15 that are not found in Liu. Specifically, Schubert teaches a synthesis method of formula II which produces it at a 96% recovery rate.
The solution of claim 14, wherein the content of compound of formula (II) is in the range of 95 to 98.5 wt.-% according to the sum of the total weight amounts of components b) to e). (“Synthesis of N,N,N,2,2,6,6-heptamethylpiperidinyloxy-4-ammonium chloride (TEMPTMA, 4)… and the product 3 (133.7 g, 96%) was obtained as a white solid.” Schubert [0112]. A 96% quantity of formula II in comparison to all side products would anticipate the claimed range.)
Schubert and Liu are considered to be analogous because they are both within the same field of synthesis methods of TEMPO derivatives for use in electrolyte materials. Therefore, it would have been obvious to one of ordinary skill before the effective filing date of the claimed invention to modify the process of Liu to improve the recovery rate of formula II such that it falls within the range of 95-98.5% compared to all byproducts, as this would improve the efficiency of the process and therefore more efficiently provide desired results in a cell (“4-Ammonium-2,2,6,6-tetraalkylpiperidinyl salts are preferably used in the cathode compartment of redox flow batteries. Synthetically simple access to such compounds is desirable to improve the economics of electrochemical cells.” Schubert [0002])
Claim(s) 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu (US 20180072669 A1)
The solution of any of claim 14, wherein the content of water is in the range of 40 to 60 wt.-% according to the solution. (As described in claim 14, by adding 20mL to the mixture of compound I, which has been used to synthesize compound 2 at a 90.5 recovery rate, there would at one point be a solution which contains a 60.98% of water. This is close enough to the claimed range to constitute a prima facie case of obviousness via nearly overlapping.)
The examiner takes note of the fact that the prior art quantity of 60.98% water in a solution nearly overlaps claimed range of 40-60% for the same parameter. Absent any additional and more specific information in the prior art, a prima facie case of obviousness exists. In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379 (Fed. Cir. 2003). MPEP 2144.05.
Allowable Subject Matter
Claims 17-26 objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
Claim 17 is directed to a process of producing the solution of claim 14. While the teachings of Liu would inherently produce a mixture that meets the limitations of claim 14, there is nothing in the teachings of Liu specifically drawn to monitoring the quantities of each of the formula I, II, and side product III, in addition to the amount of water present in the resulting solution. The closes prior art is considered to be Liu as well as Schubert (WO 2018028830), which teaches a process for preparing 4-ammonium-2,2,6,6-tetraalkylpiperidinyl salts, but whose process does not include water or a monitoring process. After a thorough search, examiner does not find that there is any obvious combination of prior art which would encourage one of ordinary skill in the art to come to the process of claim 17, and therefore it is considered to be novel and allowable subject matter. Since claims 18-24 depend on claim 17, they are also considered to contain allowable subject matter
Claim 25 is directed to an electrolytic solution containing formulae IV, V, and VI in specified amounts. While Liu teaches the synthesis of 4-NMe-TEMPO, which is analogous to compound IV, and specifies that it is for use in a catholyte with desirable properties, it does not teach a specific electrolytic solution containing specified quantities of formula V and VI as well as the inclusion of an alkali metal cation. Schubert also teaches a similar compound for use in electrolyte, but fails to teach the same additional components of an electrolytic mixture. Thus, there is not considered to be a single reference or combination or references which would make obvious the electrolytic solution of claim 25 which is formed via the solution of claim 14 and also contains formula IV-VI as well as a metal cation, and therefore claim 25 is considered to be novel and contain allowable subject matter. Since claim 26 depends on claim 25, it is also considered to contain allowable subject matter.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 25-26 rejected on the ground of nonstatutory double patenting as being unpatentable over claims 17 of U.S. Patent Application No. 17915116. Although the claims at issue are not identical, they are not patentably distinct from each other because they require an electrolytic solution containing the same components, the main difference being the precursor solution used to make the electrolyte solution required in the instant claims. See below for comparison. Claim 26 rejected for dependence upon claim 25.
Instant claim 25:
Use of the solution according to claim 25 for the production of a electrolyte mixture comprising
A) water,
B) 20 to 55 wt.-% according to the total weight amount of the electrolyte mixture of compound 2,2,6,6-tetramethylammonio)-1-piperidinyloxy of formula (IV)
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(Iv)
C) 0.1 to 6 wt.-% according to the total weight amount of the electrolyte mixture of an alkali metal cation
D) 0.5 to 12.5 wt.-% according to the total weight amount of the electrolyte mixture of compound N,N,N,1,2,2,6,6-octamethyl-4-piperidinammonium-1-oxide of formula (V)
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(V
)E) 0.1 to 20 wt.-% according to the total weight amount of the electrolyte mixture of compound 2,2,6,6-hexamethyl-4-(dimethylamino)-1-piperdinyloxy-N-oxide of formula (VI)
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(VI)
Reference Claim 16:
A solution comprising
a) water,
b) 20 to 55 wt.-% according to the total weight amount of the solution of compound 2,2,6,6-tetramethyl-4-(trimethylammonio)-1-piperidinyloxy of formula (I), ##STR00014##
c) 0.1 to 6 wt.-% according to the total weight amount of the solution alkali metal cation
d) 0.5 to 12.5 wt.-% according to the total weight amount of the solution of compound N,N,N,1,2,2,6,6-octamethyl-4-piperidinammonium-1-oxide of formula (II) ##STR00015##
e) 0.1 to 20 wt.-% according to the total weight amount of the solution of compound 2,2,6,6-hexamethyl-4-(dimethylamino)-1-piperidinyloxy-N-oxide of formula (III) ##STR00016##
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BENJAMIN ELI KASS-MULLET whose telephone number is (571)272-0156. The examiner can normally be reached Monday-Friday 8:30am-6pm except for the first Friday of bi-week.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, NICHOLAS SMITH can be reached at (571) 272-8760. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/BENJAMIN ELI KASS-MULLET/Examiner, Art Unit 1752
/OLATUNJI A GODO/Primary Examiner, Art Unit 1752
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