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 . Per amendment dated 6/2/26, claims 1, 4-7, 11, 13 and 15 are currently pending in the application.
The terminal disclaimer filed on 6/4/26 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of US Pat. 12,024,576 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Claim Objections
Claims 1 and 4 are objected to because of the following:
Claim 1 recites two Ar groups including “A” group, “x” terms in the aryl structures denoting the number of carbons in the linking group between the aryl rings. The claim further recites structures of each of R1...Rn, which also include “A” and “x”, with “A” being of a different scope than the previously defined term. The claim language may be amended to identify the two “A” groups differently so as to improve clarity.
Additionally, the first wherein clause should be amended to recite “wherein Ar1…Arn are different aryls”, in the Markush listing for the recited aryl species, the term “and” should be inserted between the last two species, and in various groups recited for R1...Rn, the last two species should be separated by “or”.
Furthermore, in the recited R1...Rn species, the term “or” should be inserted between the last two species.
In claim 4, the strike through lines must be clearly depicted through the structures in the first two rows. Additionally, upon further consideration, the Markush listing in the claim should include the term “and” only separating the last two species, i.e., preceding term “combinations”, and all other species should be separated only by a comma. Furthermore, the phrase “wherein R include” should be replaced with “wherein R includes”.
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.
Claims 1, 4-7, 11, 13 and 15 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 is indefinite for the following reasons:
“A” following the Markush listing for the aryl groups is defined as an “alkyl”. Likewise, “A” is defined as an alkyl in the groups recited for R1...Rn. The claim is indefinitely because “A” in all the structures is present only as a linking group and therefore, cannot be an alkyl group.
The Markush listing for the aryl groups includes “z”, however it is not defined in the claimed language. Likewise, following the Markush listing, R’ is defined as including H, an alkyl group or combinations thereof, and X as including a halide. However, the aryl species or the R1...Rn species in the claim do not include the term “R’”. While the recited R1...Rn species include “x” and “X”, it is unclear if the definitions of “x” defined following the Markush listing is applicable to “x” in the R1...Rn species, and if “X” defined after the Markush listing is intended for the group in R1...Rn species.
Claim 13 depends on claim 1 and recites the limitation ‘having a halide counter anion or a metal counter cation”. However, none of the recited FG groups in claim 1 include a halide counter anion.
Claims 4-7, 11, 13 and 15 are subsumed by rejected base claim 1 and are therefore, included in this rejection. For the purpose of examination and applying art, in view of the disclosure, Examiner interprets claim 1 “alkyl” (as “A” in Ar groups and FG species) is interpreted to mean “alkylene” linking group, “x” in R1...Rn species as ranging from 2 to 20, “x” as ranging from 0 to 20, and “z” in the aryl group as being “2 or 3”.
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.
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by
Olvera al. (Macromolecules, 7245-7256 (2013), of record).
Olvera teaches aromatic fluorinated polymers comprising the following units (Ab., Scheme 1, page 7246).
PNG
media_image1.png
496
878
media_image1.png
Greyscale
The reference further teaches copolymers 2a(A+B) and 2b(A+B), having a Mw of 50.27x10-4 and 25.81x10-4 (pages 7246-7247, Scheme 1, Table 1). Disclosed copolymers include biphenyl (Ar1) and terphenyl (Ar2/Arn), and
PNG
media_image2.png
52
144
media_image2.png
Greyscale
as R1/Rn, with x being 0 or 1. Disclosed polycondensation reactions for preparing the copolymers must inherently provide for random copolymers as in the claimed invention because the aryl monomers involved in the polycondensation are structurally similar.
In the alternative, although Olvera is silent on random copolymers, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the date invention, to reasonably expect copolymers formed by polycondensation reaction to be random copolymers on the basis that biphenyl and terphenyl involved in polycondensation have structural similarities and therefore have similar reactivities, absent evidence to the contrary.
Claim 1 is rejected under is rejected under 35 U.S.C. 103 as being unpatentable over Xu et al. (CN112940226A, CN document and machine translation).
Xu teaches a Friedel Crafts reaction between an aryl compound represented by formula (III) or (IV) and a ketone compound of formula (V) shown below, in a first step for preparing a polyelectrolyte material;
PNG
media_image3.png
150
228
media_image3.png
Greyscale
(III),
PNG
media_image4.png
132
254
media_image4.png
Greyscale
(IV),
PNG
media_image5.png
178
104
media_image5.png
Greyscale
(V)
PNG
media_image6.png
198
364
media_image6.png
Greyscale
wherein R3-R10 is H, C1-C10 alkyl or halogen, and m=0-3; R1 and R2 may be any of (c), (d) or (e), and r is an integer from 0 to 10. Thus, disclosed ketone compounds include methyl 1,1,1-trifluoroacetone. Formula (III) includes biphenyl and biphenyls with an R substituent as claimed. Additionally, disclosed synthetic route for Example 1 involves the following first step:
PNG
media_image7.png
68
632
media_image7.png
Greyscale
Disclosed Examples 2 and 3 teach copolymers formed by reacting 2,2’-dimethyl biphenyl, p-terphenyl or m-terphenyl, and 1,1,1-trifluoroacetone, for subsequent halogenation and incorporating cation exchange groups, i.e., copolymers formed in the first step may have two different aryl groups. It is noted that 2,2’-dimethyl biphenyl is also an isomer of the claimed biphenyl having R groups.
Although Xu is silent on a random copolymer comprising claimed aryl groups in a single embodiment, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the date invention, to prepare copolymers from any of the aryl compounds within the scope of formula (III), including a biphenyl or a substituted biphenyl, in combination with a p-terphenyl or m-terphenyl. Additionally, it would be obvious to a skilled artisan that the copolymers to be inherently random, or in alternatively, reasonably expect them to be random on the basis that the aryl monomers involved have structural similarities and therefore would be expected to have similar reactivities, absent evidence to the contrary.
Moreover, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Response to Arguments
In view of the amendment and terminal disclaimer dated 6/4/24, the objections and claim rejections based on Tao et al. are withdrawn, while Olvera et al. as applied to claim 1 is maintained herein above.
It is noted the preamble in claim 1 is drawn to a copolymer but the range recited for a1…an has a lower limit of 1 in formula (I), and encompasses compounds having a number of repeating units as low as 2 or 3, which compounds do not read on a copolymer. Additionally, features of claims 4 and 6 necessarily require copolymers having a crosslinking group and an ionic group, respectively, while claim 1 encompasses compounds devoid of such groups. Although examiner is not levying new grounds of rejections under 112(b) in order to maintain compact prosecution, Applicant is alerted to the issues for future reference.
Regarding Olvera, Applicant argues that the R groups now recited in claim 1 do not include any of the R groups in Schemes 1 or 2, as identified on p. 11 of the Office Action.
In response, it is noted that in Table 1, polymer identified as 2a(A+B) is obtainable by reacting ketone (a) (methyl trifluoromethyl ketone) and aryl compounds (A) (biphenyl) and (B) (p-terphenyl) presented in Scheme 1. Biphenyl and p-terphenyl fall within the scope of R groups recited in amended claim 1. Likewise, polymer 2b(A+B) is obtainable from ethyl trifluoromethyl ketone, biphenyl and p-terphenyl. Therefore, Examiner maintains that the claimed aryl groups fall within the scope of Olvera.
Regarding Xu et al., although some of the arguments are moot of view of the withdrawal of rejections, the reference would be applicable to claim 1 for reasons presented herein above. Applicant argues that Xu doe not disclose that the R groups are different to form random copolymers.
In response, Xu’s reaction scheme [0090] and Examples 1-3 clearly teach forming copolymers by reacting two different aryl groups with a ketone compound in the first step. It is noted that the Ar groups in Formula (I) of amended claim 1 now excludes aryls having R’ substituents (with x as 0) ( which previously read on Xu’s 2,2’-dimethyl biphenyl). However, the general disclosure discloses aryl compounds of overlapping scope, in addition to isomers of claimed species. Thus, reacting two different aryls with a ketone must inherently produce a random copolymer because they have structural similarities and therefore, have similar reactivities.
Conclusion
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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action.
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
Prosecution Insights