DETAILED ACTION
Status of Application
This action is responsive to non-provisional application filed 07/05/2023. Original claims 1-20 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.
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. 102
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.
Claims 1, 9, and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Guo, et al (CrystEngComm, 2017, 19, 4905) (‘Guo’).
Regarding Claim 1, Guo discloses a new anion conducting covalent organic framework (COF) with quaternary ammonium ion covalently tethered to the pore walls of the COF through bromination and quaternization (Abs.). Guo discloses a structured organic film (Abs., covalent organic framework; Page 4906, Col. 2, COFs compressed into membranes (film)). Guo discloses the SOF comprises a plurality of segments and a plurality of linkers (Abs., Page 4906, Scheme 1, 1,3,5-triformylphloroglucinol (Tp) are the linkers and 3,3’-dimethyl-[1,1’-biphenyl]-4,4’-diamine (BD-Me) are the segments; wherein the linkers connect at least one of the plurality of segments). Guo discloses wherein at least one or more of the plurality of segments comprises an ionic species (id., BD-Me segments comprise quaternary ammonium species). Guo on page 4908 further discloses that only 16.05% of the methyl groups on the BD-Me segments were brominated, which provides attachment points for the quaternary amines; hence, approximately 84% of the segments were nonionic (i.e., non-brominated) segments, with a ratio of cationic/nonionic of 16/84 = 0.2. As such, Guo is found to fully disclose an embodiment of the claimed SOF, wherein at least one or more of the plurality of segments comprises an ionic (cationic) species and at least one or more of the plurality of segments comprises a nonionic species.
Regarding Claim 9, Guo further discloses wherein a thickness of the SOF is from about 250 nm to about 500 µm (Page 4906, Col. 2, 50-micron thickness of the membrane).
Regarding Claim 11, Guo further discloses an ion-exchange membrane comprising the SOF of claim 1 (Abs., covalent organic framework; Page 4906, Col. 2, COFs compressed into membranes (i.e., film)).
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.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Guo in view of Beh, et al (US 2022/0223885 A1) (‘Beh’).
Regarding Claim 10, Guo discloses the SOF of claim 1 as discussed above. However, Guo is silent as to wherein the SOF has an ion exchange capacity (IEC) of from about 0.25 mEq/g to about 5.00 mEq/g. Nevertheless, in the same technical field, Beh discloses an electrochemical device comprising first and second types of membranes (Abs.). The membrances may be cation or anion exchange membranes ([0043]). For anion exchange membranes, the ion conducting groups cam by quaternary amine ([0073]). The ion exchange capacity may be between 0.4 – 3 mEq/g ([0074]).
It would have been obvious to one of ordinary skill in the art at the time of effective filing to modify the ion exchange membrane of Guo such that the structured organic film (SOF) has an ion exchange capacity (IEC) of from about 0.25 mEq/g to about 5.00 mEq/g, as claimed, since such a range is typical of anion exchange membranes with quaternary ammonium cations.
Claims 1, 2, 7, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Cote, et al (US 8318892 B2) (‘Cote’).
Regarding Claims 1, 2 and 7, Cote discloses a capped structured organic film comprising a plurality of segments and a plurality of linkers arranged as a covalent organic framework, wherein the structured organic film may be a multi-segment thick structured organic film (Abs.). Cote discloses a structured organic film (SOF) comprising a plurality of segments and a plurality of linkers (Abs.), wherein at least one of the linkers connects at least one of the plurality of segments (col. 8, lines 9-30; for example, two hydroxyl (-OH) groups are used to connect segments in a SOF via an oxygen atom (ether linker)). Cote also discloses the SOF comprising a plurality of capping segment (Col. 3, lines 1-10) [for claim 7]. Cote further provides concrete examples of the synthesis of SOFs with linking between N,N,N′,N′-tetrakis-[(4-hydroxymethyl)phenyl]-biphenyl-4,4′-diamine building blocks and capping units (Cols. 61-64, Tables 3-6); wherein the linked segment derived from N,N,N′,N′-tetrakis-[(4-hydroxymethyl)phenyl]-biphenyl-4,4′-diamine corresponds to the segment structure shown in claim 2.
Cote differs from the claimed subject matter only in failing to disclose, in a single embodiment, a SOF wherein at least one or more of the plurality of segments comprises an ionic species. However, Cote generally teaches that added functionality may be imparted to SOFs by the selection molecular building blocks wherein the molecular compositions provide the added functionality in the resultant SOF (Col. 11, line 57 et seq.). As some examples of the properties that may represent an “added functionality” of a SOF, Cote mentions hydrophobic, hydrophilic, lipophobic, lipophilic, photochromic and/or electroactive properties (Col. 12, lines 23-27). In the case of hydrophilic properties, Cote teaches to use molecular building blocks bearing polar substituents, for example, hydroxyl, amino, ammonium, and carbonyl (Col. 14, lines 24-30). Cote thus teaches an ionic species (ammonium) among a finite number of alternative choices for the polar substituent of molecular building blocks that may be used to obtain a SOF with hydrophilic properties as added functionality. The disclosed alternatives are seen to constitute an acceptable number to form a reasonable expectation of success (see MPEP 2143(E)) such that those of ordinary skill may select ammonium through routine testing on the basis of the exemplified polar substituents and the desired hydrophilicity of the resultant SOF. Accordingly, at the time of effective filing, it would have been obvious to one of ordinary skill in the art seeking to obtain a SOF with hydrophilic added functionality to have modified any of the exemplified SOFs of Cote by including therein a molecular building block bearing an ammonium species. Further, the predictable outcome of the proposed modification would be a SOF wherein at least one or more of the plurality of segments comprises an ionic (ammonium cation) species, and at least one or more of the plurality of segments comprises a nonionic species, as claimed.
Regarding Claim 9, Cote further discloses wherein a thickness of the SOF is from about 250 nm to about 500 µm; for example, film having a thickness ranging from 6 to 7 microns (Col. 62, Example 15).
Claim Rejections – 35 U.S.C. 102/103
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.
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.
Claims 19-20 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Kang, et al (Journal of Membrane Science 475 (2015) 384-394) (‘Kang’).
Regarding Claim 19, Kang has already disclosed a free-standing polysilsesquioxane (PSSQ) film made by subjecting ladder-like poly(phenyl-co-glycidoxypropyl) silsesquioxanes with a phenyl:glycidoxy copolymer ratio of 6:4 (LPG64) to thermal crosslinking with octa(aminophenyl)-T8-silsesquioxane (OAPS) with different concentrations of OAPS; see Abstract and Fig. 2 (Schematic for the crosslinking reaction between LPG64 and OAPS). As clearly depicted in Fig. 2, the crosslinked product (LPG64/OAPS Composite) comprises a plurality of segments (of LPG84) and a plurality of linkers (OAPS), wherein at least one of the plurality of linkers connects at least one of the plurality of segments. And while the free-standing PSSQ film of Kang is described as an inorganic-organic hybrid (see, e.g., p. 385, 2nd full para. of left-hand column), it is noted the claim term “SOF” is defined by Applicant as inclusive of embodiments wherein the SOF comprises at least one atom of an element that is not carbon, such as at least one atom selected from, inter alia, oxygen, nitrogen and silicon (cf., Spec., [0023]). Accordingly, claim 19 is properly construed as readable on a free-standing SOF comprising the same non-carbon atoms as are present in the free-standing PSSQ-based film of Kang.
Further as to the recited functional limitation (“wherein the free-standing [SOF] can be folded without cracking at a fold line”), Kang in Fig. 9 shows pictures of the LPG64 and the crosslinked LPG64/OAPS membranes, reproduced below:
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In reference to this figure, Kang notes that its LPG64 membrane was found to have excellent free-standing film forming ability and flexibility; and in addition, that the crosslinked LPG64/OAPS membranes also seemed to have enough robustness to handle and test (see pp. 389-390, bridging para.). In particular as to the crosslinked LPG64 + OAPS (90/10) and (80/20) membranes, the right-hand side of Fig. 9 depicts both membranes in folded conformation with no discernible cracking. Furthermore, Kang notes that the PSSQ must have imperceptibly few uncondensed silanol groups, as Si-OH groups render significant film shrinkage, causing film cracks (p. 385, 3rd sentence of 2nd full para. of left-hand column). Kang then observes that the initial copolymerization molar feed ratio of 6:4, confirmed via H-NMR, is reflective of a high degree of condensed siloxane structures (p. 387, 1st full para. of right-hand column), thus implying the disclosed free-standing film is resistant to cracking (owing to few non-condensed Si-OH groups). Based on the above disclosures, Kang is considered to describe a free-standing SOF that implicitly fulfills the claim requirement of being folded without cracking at a fold line.
Regarding Claim 20, it is acknowledged that Kang is silent as to claimed features wherein:
the free-standing structured organic film is flexible and water-swellable and stable without tearing
during exposure to water; and the free-standing structured organic film is flexible and stable without tearing subsequent to water exposure and drying. However, Kang teaches a free-standing PSSQ-based film comprising a crosslinked composite of LPG64 segments connected by OAPS linkers, as discussed above. Given the identity of crosslinked structure between Kang and the present invention, the claimed properties are reasonably presumed to inhere in the disclosed free-standing films, absent objective evidence to the contrary. Where, as here, a reference discloses all the limitations of a claim except for a property or function, and examiner cannot determine whether or not the reference inherently possesses properties which anticipate or render obvious the claimed invention, basis exists for shifting the burden of proof to applicant. See, In re Fitzgerald et al, 205 USPQ 594, 596 (CCPA 1980) and MPEP 2112.01.
Allowable Subject Matter
Claims 3-6, 8, and 12 are objected to as being dependent on a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claim.
Claims 13-18 are allowed.
The closest prior art to Guo et al, Beh et al, and Cote et al, discussed above, does not describe the inventions of instant claims 3-6, 8, and 12-18, or provide proper rationale to modify any of their respective inventions into the invention of any one of said claims.
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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Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/05-14-26
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