DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 1-21 are currently pending in the application.
Drawing
The drawing is objected to for the following:
It should be identified as Fig. 1, to make it consistent with the description in [0017] of the specification.
Specification
The disclosure is objected to because of the following informality:
Paragraph [0001] in the disclosure should be amended to clarify that the present application is a Continuation of US Appl. No. 18/164,980 (now matured into patent no. US 12,024,576 B2).
Appropriate correction is required.
Claim Objections
Claim 3 and 4 objected to because of the following informalities:
In the Markush listing of claim 3, the term “and” should be inserted between the last two structures, and the term “or” should be inserted between the last two species of FG. Additionally, for the various FG species, subscripts and superscripts should be shown accurately.
In claim 4, the term “and” should be inserted between the last two species of the Markush listing.
Appropriate corrections and/or clarifications are required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
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.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 1-7, 11-15, 19-21 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the following:
PNG
media_image1.png
425
1071
media_image1.png
Greyscale
Claim 1 is indefinite because it is not clear what “n” corresponds to in Formula 1. It is unclear as to how many repeating units with different aryl groups “n” are required to be present in the claimed formula, and whether “n” should be 4 at a minimum because the formula includes at least four repeating with different aryl groups and a lower limit for each of a1, a2, a3 and an is 1.
Claim 1 recites the limitations “an alkyl group, e.g., CH2 or CH2CH3” (twice) and “a halide, e.g., Br”. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 1 recites the broad recitations “an alkyl group” and “a halide”, and the claim also recites “e.g., CH2 or CH2CH3” and “e.g., Br”, which are the narrower statements of the corresponding range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
In claim 1 is indefinite because A and A’ may be an alkyl group in the claim. However, in the recited structures, A is a linking group while A’ is a member of an aromatic ring.
Claims 2-7, 11-15, 19-21 are subsumed by rejected base claim 1 and are therefore, included in this rejection.
For the purpose of examination, in view of paragraph [0006] in the specification which discloses n is 2 to 20, and in view of copolymer structures recited in claims 8-10, Examiner interprets n in Formula 1 of claim 1 as ranging from 2 to 20. Additionally, in view of the teaching “A includes S, O, NH, SO2, an alkyl group, e.g. -CH2” in paragraph [0006], Examiner interprets A to include an alkylene group, and A’ as including a nitrogen atom.
Claim 2 is indefinite because it recites the limitations “an alkyl group, e.g., CH2 or CH2CH3” (thrice), and “a halide, e.g. F”, for reasons stated in paragraph 8 above. Claim 2 is also indefinite because A is defined as an alkyl group but it is present only as linking groups in the recited structures. For reasons stated in paragraph and 9 above, Examiner interprets A in claim 2 to include an alkylene group.
Claim 4 is indefinite for the recitation “an alkyl group, e.g., CH2 or CH2CH3” for reasons stated in paragraph 8 above.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 5, 8, 10, 17 and 18 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 5 recites the limitation “wherein the degree of crosslinking is from 0% to 100%”. A lower limit of 0% for the degree of crosslinking would read on an uncrosslinked copolymer. However, claim 4 depends on claim 3 which recites the limitation “The copolymer of claim 2, wherein R1, R2, R3, …..Rn are crosslinked by a crosslinking agent”. Therefore, claim 4 does not necessarily limit the scope of claim 3.
Claim 8 is as follows:
PNG
media_image2.png
238
628
media_image2.png
Greyscale
Within the two repeating units, the aryl group may be Ar1 or Ar2, i.e., both may be same (Ar1 or Ar2). However, according to claim 1, Ar1 and Ar2 are different aryl groups. Therefore, claim 8 does not further limit the scope of claim 1.
Claim 10 depends on claim 8 and recites the following:
PNG
media_image3.png
202
704
media_image3.png
Greyscale
In Formula IV, a, b, c and d are each independently 1 to 1,000,000, i.e., a, b, c and d may have different values, independently, within the claimed range. In other words, the number of aryl and non-aryl fragments within each repeating unit may be different. However, claim 10 depends on claim 8 which recites Formula II according to which, the repeating units must include the same number of aryl and non-aryl fragments within. Thus, claim 10 does not necessarily limit the scope of claim 8. Claims 17 and 18 depend on rejected base claim 8 and are therefore, subsumed by this rejection.
Applicants may cancel or amend the claims to place the claims in proper dependent form, rewrite the claims in independent form, or present a sufficient showing that the dependent claims complies with the statutory requirements.
Claim Rejections - 35 USC § 102 and 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 1, 3, 5-7, 11-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by
Tao et al. (Journal of Membrane Science, 120432 (4th Feb., 2022), cited in the IDS).
Regarding claim 1, Tao teaches poly(p-quaterphenylene alkylene)-based ionomers for conductive membranes of the following formula (Ab., pages 1-3, 5, , Scheme 1, Table 1):
PNG
media_image4.png
712
710
media_image4.png
Greyscale
wherein x refers to the mol%. Disclosed copolymers include two different Ar groups (read on Ar1 and Ar2), and necessarily include at least one unit of x and at least one unit of y. Additionally, disclosed pendant alkylammonium chloride groups in the copolymer correspond to R1 and R2 in claimed Formula 1 as
PNG
media_image5.png
53
113
media_image5.png
Greyscale
, wherein x=5, FG=NR3+X-, R=alkyl and X = halide (Cl-), and R1 and R2 in claim 3 correspond to
PNG
media_image6.png
56
182
media_image6.png
Greyscale
, wherein A= CH2, and n=1. It is further noted that the copolymers are prepared by superacid catalyzed hydroxyalkylation polymerization (Section 2.2), i.e., by substantially the same polymerization method as disclosed in the instant specification [0032], and therefore, the copolymers disclosed in Tao’s Scheme 1 must inherently be random copolymers as in the claimed invention.
Regarding claims 5 and 6, noting that the degree of crosslinking in claim 5 may be 0, disclosed copolymers in Scheme 1 have IEC with the claimed range (Scheme 1).
Regarding claims 7 and 11, Tao teaches anion membranes for fuel cells (reads on electrochemical device) (Sections-1, 2.6, 2.11, 3.2, 3.6, 4).
Regarding claim 13, Tao teaches anion exchange membrane comprising a halide counter anion (Scheme 1, Section 2.6).
Regarding claims 12, 14 and 15, given that Tao’s copolymers meet the claimed compositions limitations and are prepared by substantially the same polymerization method as disclosed in the instant specification, the disclosed copolymers must inherently have the claimed mechanical stress, swelling ratio and conductivity in water.
In light of above, presently cited claims are anticipated by the reference.
Claims 1-3, 5-7, 9, 11-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Xu et al. (CN112940226A, CN document and machine translation).
Regarding claims 1-3, 5, 7, 9, 11, 13, 16, Xu teaches a polyelectrolyte material comprising a group represented by formula:
PNG
media_image7.png
110
226
media_image7.png
Greyscale
,
wherein Ar may be any of the following groups (a) and (b), with n being the degree of polymerization;
PNG
media_image8.png
168
746
media_image8.png
Greyscale
,
R3-R10 being H, C1-C10 alkyl or halogen, and m=0-3;
R1 and R2 may be any of (a) to (g); Q is a cation exchange group, such as (h) shown below:
PNG
media_image9.png
114
192
media_image9.png
Greyscale
wherein, R11-R13 may be H, C1-C10 alkyl, and x1= (Ab., claims, pages 6-10).
Disclosed Examples 2 and 3 are drawn to copolymers formed by reacting 2,2-dimethyl biphenyl, and any of p-terphenyl, m-terphenyl or biphenyl, and 1,1,1-trifluoroacetone, in the presence of trifluoromethane sulfonic acid, for subsequent halogenation and incorporating cation exchange groups, i.e., the reference teaches copolymers having two different aryl groups (Examples, Fig.1-2).
Disclosed copolymers of the alkaline polyelectrolyte type are suitable for fuel cells, electrodialysis etc. (Ab., page 12).
Xu is silent on a copolymer of the claimed formula in one single embodiment as claimed,
At the outset, it is noted that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
Given the generic teaching in Xu on polyelectrolyte material comprising units of Formula (II) above, and the teaching on copolymers comprising two different aryl groups, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare copolymers within the scope of the claimed invention. For instance, said copolymers may comprise two or more aryl groups of formula (a) and/ (b), providing for Formula 1 with claimed Ar1, Ar2 etc., R1 as CF3, and R2 may be, for e.g.,
PNG
media_image10.png
80
122
media_image10.png
Greyscale
bonded to
PNG
media_image9.png
114
192
media_image9.png
Greyscale
, providing for claimed R1=
PNG
media_image11.png
64
104
media_image11.png
Greyscale
.
Regarding claims 6, 12, 14, 15, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the date of the claimed invention, to reasonably expect copolymers formed from polycondensation reaction to be random copolymers on the basis that they may be prepared by similar polymerization reaction, and the copolymers comprising multiple Ar units and R1 as to have the claimed properties, absent evidence to the contrary. As a practical matter, the Patent Office is not equipped to manufacture products by the myriad of processes put before it and then obtain prior art products and make physical comparisons herewith.” In re Brown, 459 F.2d 531, 535, 173 USPQ 685, 688 (CCPA 1972).
Claims 1, 2 and 5 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by
Olvera al. (Macromolecules, 7245-7256 (2013), cited in the IDS), or under 35 U.S.C. 103 as being unpatentable over Olvera al.
Olvera teaches aromatic fluorinated polymers comprising the following units (Ab., Scheme 1, pages 7247-7251, Tables 1-3, 6, 7, Fig. 5, 6, Schemes-1 and 2).
PNG
media_image12.png
496
878
media_image12.png
Greyscale
Disclosed copolymers 2a, 2b and 2c based on A and B aryl groups in Table 1 fall within the scope of copolymers of claim 1. For instance, in the disclosed copolymers 2a and 2b, biphenyl reads on Ar1 of Formula 1, a terphenyl unit reads on Ar2, with (a) and (b) providing for R1=R2 =
PNG
media_image13.png
52
144
media_image13.png
Greyscale
, with x being 0 or 1. Disclosed copolymers are prepared by polycondensation reaction in the presence of a strong acid, such as those of the instant disclosure, and therefore, must inherently be random copolymers. It is noted that the degree of crosslinking in claim 5 may be 0.
In light of above, presently cited claims are anticipated by the reference.
In the alternative, although Olvera is silent on the copolymers being random copolymers, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the date of the claimed invention, to reasonably expect copolymers formed from polycondensation reaction to be random copolymers on the basis they meet compositional requirement of the claimed copolymer and are prepared by similar polymerization reaction, absent evidence to the contrary.
Claims 19-21 are rejected under 35 U.S.C. 103 as being unpatentable over either Tao et al. (Journal of Membrane Science, 120432 (2022), cited in the IDS) or Xu et al. (CN112940226A, CN document and machine translation), in view of Kim et al. (US 10,622,657 B1).
The discussions on Tao and Xu from preceding paragraphs as applied to claim 1 are incorporated herein by reference.
Tao and Xu are silent with regard to a membrane comprising a dopant.
As stated in paragraph 30 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Tao and Xu teach anion exchange copolymers for use in membranes for fuel cells, and polymers comprising quaternary ammonium ions. In the same field of endeavor, the secondary reference to Kim teaches proton exchange membrane (PEM) fuel cells, said membrane comprising a phosphoric acid-doped cationic-functionalized membrane comprising copolymers comprising quaternary ammonium ions, wherein the doped PEMs can conduct protons through stable ionic pair complexes and enable fuel cell operation at temperatures of from 80oC to 220oC (Ab., col. 2, line 44-col. 6, line 55, ref. claims 1-2).
In view of the advantages disclosed in Kim, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to further include a phosphoric acid dopant in Tao’s or Xu’s membranes.
Claims 4 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over either Tao et al. (Journal of Membrane Science, 120432 (2022), cited in the IDS) or Xu et al. (CN112940226A, CN document and machine translation), in view of Kohl et al. (US 2021/0363291 A1).
The discussions on Tao and Xu from preceding paragraphs as applied to claim 1 are incorporated herein by reference.
Tao and Xu are silent with regard to a crosslinked copolymer.
As stated in paragraph 30 above, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists.
Tao and Xu, each teach anion exchange membranes for fuel cell applications (Tao-page 21. 1, Bae-Ab.), such as those comprising quaternary ammonium cations (Tao-page 3, Scheme 1, Bae- reference claims). In the same field of endeavor, the secondary reference to Kohl teaches anion exchange membranes comprising polymers comprising quaternary ammonium cations (Ab.), that are optionally crosslinked to improve the structural stability of the polymers (Ab.). Kohl further teaches saturated C2-C10 alkyl chain branched or unbranched with at least two amine functional groups as suitable crosslinking agents, including ethylene diamine, propyl 1 diamine, butyl diamine, 1,5-pentanediamine, 1,6-hexanediamine (read on , R being H) and N,N,N",N'-tetramethyl-1,6-hcxancdiamind (TMHDA) ([0119-0121], Examples).
Given the teaching in Kohl on advantages of a crosslinking agent, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to crosslink Tao's of Xu’s copolymers prepared from a combination of aromatic compounds, with crosslinking agents as taught by Kohl so as to provide improved structural stability.
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 1-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-18 of U.S. Patent No. US 12,024,576 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because copolymers of patent claims 1, 3-7 are fully encompassed by copolymers of instant claims 1-6, 8-10, and
limitations of instant claims 7, 11-21 are met by patent claims 2, 8-18.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
CN 113956445 A (CN document and machine translation) teaches anion exchange membranes comprising branched copolymers comprising multiple aryl units in the backbone for use in devices, such as fuel cells.
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to Satya Sastri at (571) 272 1112. The examiner can be reached Monday-Friday, 9AM-5.30PM (EST). If attempts to reach the examiner by telephone
are unsuccessful, the examiner's supervisor, Mr. Robert Jones can be reached at (571)-270-
7733. The fax phone number for the organization where this application or proceeding is
assigned is (571) 273 8300.
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 https://ppair-my.uspto.gov/pair/PrivatePair. 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.
/Satya B Sastri/
Primary Examiner, Art Unit 1762