DETAILED ACTION
Applicant’s response filed on 11/06/2025 has been fully considered. Claims 1-19 are pending. Claim 1 is amended. Claims 10-13 and 15-18 are withdrawn. Claim 19 is new.
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
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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.
Claims 1-9 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (Yang et al., “Zwitterionic poly(arylene ether sulfone) copolymer/poly(arylene ether sulfone) blends for fouling-resistant desalination membranes” and Supporting Information, Journal of Membrane Science, 2018, vol. 561, p. 69-78) in view of Chen et al. (Chen et al., “Partially fluorinated poly(arylene ether)s bearing long alkyl sulfonate side chains for stable and highly conductive proton exchange membranes”, Journal of Membrane Science, 2018, vol. 549, op. 12-22, made of record on 06/06/2025).
Regarding claims 1-4, 6, 7, and 9, Yang teaches an amphiphilic copolymer poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) (PAES-co-SBAES) (p. 69) that is
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(p. 72), wherein the PAES-co-SBAES has a Mn of 9,770 g/mol, 9,370 g/mol, 6,760 g/mol, or 4,950 g/mol (Supporting Information, p. 1, Table S1), and is synthesized according to the following reaction scheme:
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(p. 72), which reads on a copolymer (P1) comprising: recurring units (RP1) of formula (M), recurring units (R*P1) of formula (N), and 205, 213, 296, or 404 µeq/g of hydroxyl end groups, wherein R1 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali metal sulfonate, alkaline earth metal sulfonate, alkali metal phosphonate, alkaline earth metal phosphonate, amine and quaternary ammonium, each i is independently selected from 0, and T is independently selected from -C(CH3)2- as claimed, wherein T in recurring units (RP1) is selected from -C(CH3)2- as claimed, wherein I is zero for each R1 of recurring units (RP1) and recurring units (R*P1) as claimed, wherein recurring units (RP1) are according to formula (M1) as claimed, the copolymer (P1) of claim 1, having a number average molecular weight (Mn) of 9,770 g/mol, 9,370 g/mol, 6,760 g/mol, or 4,950 g/mol, as determined by GPC as claimed. The µeq/g of hydroxyl end groups is based on the calculations:
(2 eq/mol) / (9,770 g/mol) * 1,000,000 µeq/eq = 205 µeq/g
(2 eq/mol) / (9,370 g/mol) * 1,000,000 µeq/eq = 213 µeq/g
(2 eq/mol) / (6,760 g/mol) * 1,000,000 µeq/eq = 296 µeq/g
(2 eq/mol) / (4,950 g/mol) * 1,000,000 µeq/eq = 404 µeq/g
Yang does not teach that GN is selected from the claimed group, that Q is as claimed, and that R2 is as claimed. However, Chen teaches sulfonated fluorinated poly(arylene ether)s (SPAEs) (p. 13) that are
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, wherein
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, wherein the SFPAE is synthesized according to the following scheme
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(p. 14). Yang and Chen are analogous art because both references are in the same field of endeavor of a copolymer that is a poly (aryl ether sulfone) copolymer. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Chen’s compound that is
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, wherein
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, to substitute for a fraction of Yang’s
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in Yang’s reaction scheme, such that Chen’s compound and Yang’s DABA are reacted in separate reaction schemes, such that
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, wherein
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, substitutes for the
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moiety in Yang’s
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in the reaction scheme in which Chen’s compound is reacted, and to react Chen’s compounds that are
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with the product of the previous reaction, such that
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, wherein
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, substitutes for the
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moiety in Yang’s
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. The proposed modification would read on wherein GN is selected from formula GN1, each j is independently selected from 3, Q is independently selected from -C(CH3)2-, each R2 is independently selected from –(CH2)q-SO3Na with q being selected from 3 as claimed, wherein Q in formula (GN1) is selected from -C(CH3)2- as claimed, wherein R2 in formula (GN1) is independently selected from –(CH2)3-SO3Na as claimed. One of ordinary skill in the art would have been motivated to do so because Chen teaches that the long alkyl sulfonate side chains (p. 21) in the
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(p. 14) are beneficial for providing for easy aggregation of the pendant sulfonate groups during membrane preparation (p. 21), that phase separations in PEMs (p. 13) that are proton exchange membranes (p. 12) can be promoted by engineering the sulfonic acid groups at the end of long side chains of the polymers (p. 13), that aromatic polymers with long and flexible alkyl sulfonate side chains are beneficial for being useful for high performance PEMs (p. 13), that the extended side chains are beneficial for hydrophilic-hydrophobic phase separation based on the assumption that the pendant sulfonate groups have excellent tendency to aggregate into ion clusters during membrane preparation (p. 13), and that the formation of 7 spacing atoms between the sulfonate group and aromatic backbone is beneficial for the aggregation of sulfonated groups (p. 16), which would have been desirable for Yang’s copolymer because Yang teaches that the copolymer is incorporated into a desalination membrane (p. 76), and that the membranes are fabricated via a non-solvent induced phase separation process (p. 69, 70).
Regarding claim 5, Yang teaches that in the synthesis of the PAES-co-SBAES copolymers, 33.06 mmol of BPA, 1.74 mmol of DABA, and 34.8 mmol of DCDPS are reacted (p. 70), which reads on wherein the molar ratio of recurring units (RP1)/recurring units (R*P1) is 95/5. The molar ratio is based on the calculation (33.06 / (33.06 + 1.74) * 100) / (1.74 / (33.06 + 1.74) * 100) = 95 / 5
Regarding claim 8, Yang does not teach that the copolymer (P1) of claim 1 comprises collectively at least 50 mol.% of the recurring units (RP1) and (R*P1), based on the total number of moles in the copolymer (P1). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Chen’s compound that is
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, wherein
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, to substitute for a fraction of Yang’s
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in Yang’s reaction scheme, such that Chen’s compound and Yang’s DABA are reacted in separate reaction schemes in identical molar amounts, such that
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, wherein
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, substitutes for the
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moiety in Yang’s
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in the reaction scheme in which Chen’s compound is reacted, and to react Chen’s compounds that are
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with the product of the previous reaction, such that
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, wherein
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, substitutes for the
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moiety in Yang’s
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. The proposed modification would read on the copolymer (P1) of claim 1 comprises collectively at least 50 mol.% of the recurring units (RP1) and (R*P1), based on the total number of moles in the copolymer (P1) as claimed. One of ordinary skill in the art would have been motivated to do so because Chen teaches that the long alkyl sulfonate side chains (p. 21) in the
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(p. 14) are beneficial for providing for easy aggregation of the pendant sulfonate groups during membrane preparation (p. 21), that phase separations in PEMs (p. 13) that are proton exchange membranes (p. 12) can be promoted by engineering the sulfonic acid groups at the end of long side chains of the polymers (p. 13), that aromatic polymers with long and flexible alkyl sulfonate side chains are beneficial for being useful for high performance PEMs (p. 13), that the extended side chains are beneficial for hydrophilic-hydrophobic phase separation based on the assumption that the pendant sulfonate groups have excellent tendency to aggregate into ion clusters during membrane preparation (p. 13), and that the formation of 7 spacing atoms between the sulfonate group and aromatic backbone is beneficial for the aggregation of sulfonated groups (p. 16), which would have been desirable for Yang’s copolymer because Yang teaches that the copolymer is incorporated into a desalination membrane (p. 76), and that the membranes are fabricated via a non-solvent induced phase separation process (p. 69, 70).
Regarding claim 19, Yang teaches that in the PAES-co-SBAES, the DABA:BPA:DCDPS is 9:81:100 (Supplemental Information, p. 1, Table S1), which reads on wherein the molar ratio of the recurring units (RP1) to the recurring units (R*P1) is 9/1 as claimed. The molar ratio is based on the calculation (81 / 9) / (9 / 9) = 9 / 1.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (Yang et al., “Zwitterionic poly(arylene ether sulfone) copolymer/poly(arylene ether sulfone) blends for fouling-resistant desalination membranes” and Supporting Information, Journal of Membrane Science, 2018, vol. 561, p. 69-78) in view of Chen et al. (Chen et al., “Partially fluorinated poly(arylene ether)s bearing long alkyl sulfonate side chains for stable and highly conductive proton exchange membranes”, Journal of Membrane Science, 2018, vol. 549, op. 12-22, made of record on 06/06/2025) as applied to claim 1, and further in view of McGrath et al. (US 2007/0163951 A1).
Regarding claim 14, Yang in view of Chen renders obvious at least one copolymer (P1) according to claim 1 as explained above.
Yang does not teach an epoxy resin composition comprising at least one epoxy compound and the at least one copolymer (P1) according to claim 1. However, McGrath teaches a tetrafunctional epoxy resin that is used for cross-linking BPS-xx copolymers [0120], wherein the term BPS-XX denotes a general sulfonated copolymer structure having a sulfonated poly(arylene ether sulfone) [0058]. Yang and McGrath are analogous art because both references are in the same field of endeavor of a poly(aryl ether sulfone) copolymer. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to combine McGrath’s tetrafunctional epoxy resin with Yang’s amphiphilic copolymer poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) (PAES-co-SBAES). The proposed modification would read on an epoxy resin composition comprising at least one epoxy compound and the at least one copolymer (P1) according to claim 1 as claimed. One of ordinary skill in the art would have been motivated to do so because McGrath teaches that the tetrafunctional epoxy resin is beneficial for cross-linking BPS-xx copolymers [0120], wherein the term BPS-XX denotes a general sulfonated copolymer structure having a sulfonated poly(arylene ether sulfone) [0058], which would have beneficial for cross-linking and/or modifying mechanical properties of Yang’s amphiphilic copolymer poly(arylene ether sulfone-co-sulfobetaine arylene ether sulfone) (PAES-co-SBAES), which would have been desirable for Yang’s PAES-co-SBAES because Yang teaches that the PASE-co-SBAES is used in a desalination membrane incorporating the PAES-co-SBAES (p. 76), which would have required good mechanical properties to some extent.
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 1-8 and 19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3 and 5-8 of U.S. Patent No. 12,157,797 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because the patent claims a copolymer (P1) comprising: recurring units (RP1) of formula (M)
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, recurring units (R*P1) of formula (N):
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, wherein each R1 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali, or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine and quaternary ammonium, each i is independently selected from 0 to 4, T is selected from the group consisting of a bond, -CH2-, -O-. -SO2-, -S-, -C(O)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, -CH(CH3)(CH2CH2COOH)-, -N=N-, -RaC=CRb-, where each Ra and Rb, independently of one another, is a hydrogen or a C1-C12-alkyl, C1-C12-alkoxy, or C6-C18-aryl group, -(CH2)m-, -(CF2)m- with m being an integer from 1 to 6, an aliphatic divalent group, linear or branched, of up to 6 carbon atoms, and combinations thereof, GN is selected from the group consisting of at least one of the following formulas formulae:
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,
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,
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,
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, each k is independently selected from 0 to 4, each j is independently selected from 3 to 7, each R2 is independently selected from the group consisting of: (CH2)u-COOH with u being selected from 1 to 5, (CH2)k-OH with k being selected from 1 to 5, (CH2)p-NRaRb, with p being selected from 1 to 5, and Ra and Rb being independently a C1-C6 alkyl or H, with the proviso that Ra and Rb are not both CH3, (CH2)a-SO3Na with q being selected from 1 to 5, (CH2)a-COCH3, with a being selected from 0 to 10, (CH2)r-Si(OCH3)3, with r being selected from 1 to 5, (CH3)s-(CF2)t-CF3, with s being selected from 1 to 5 and t being selected from 1 to 10, CO-Rc, with Rc being a C1-C5 alkyl or H, (CH2)v-CH3, with v being selected from 5 to 30, and (CH2)w-Ar, with w being selected from 1 to 10 and Ar comprising one or two aromatic or heteroaromatic rings (claim 1), which reads on a copolymer (P1) comprising: recuring units (RP1) of formula (M), and recuring units (R*P1) of formula (N) as claimed.
The patent does not claim that the copolymer (P1) further comprises at least 50 µeq/g of hydroxyl end groups, amine end groups, or acid end groups. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to modify the patent’s copolymer (P1) to have at least 50 µeq/g of hydroxyl end groups. The proposed modification would read on the copolymer (P1) further comprising at least 50 µeq/g of hydroxyl end groups as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because the patent claims that the copolymer (P1) comprises recurring units (RP1) of formula (M)
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, and recurring units (R*P1) of formula (N):
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(claim 1), each of which would have a hydroxyl end group when present at the end of the patent’s copolymer (P1). Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Claims 1-8 and 19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 6, 7, and 9 of U.S. Patent No. 12,454,599 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because the patent claims a polymer adduct obtained by crosslinking a copolymer (P1) comprising: recurring units (RP1) of formula (M):
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recurring units (R*P1) of formula (N):
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wherein GN is selected from at least one of the following formulas:
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each R1 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali, or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, amine, and quaternary ammonium, each i is independently selected from 0 to 4, R2 is –(CH2)r-Si(OCH3)3, with r being selected from 1 to 5, R3 is an alkyl group, an aryl group, or a halogen group, each k is independently selected from 0 to 4, each j is independently selected from 3 to 7, and T and Q are independently selected from the group consisting of a bond, -O-, -SO2-, -S-, -C(O)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, -C(CH3)(CH2CH2COOH)-, -N=N-, -RaC=CRb-, where each Ra and Rb independently of one another, is a hydrogen or a C1-C12-alkyl, C1-C12-alkoxy, or C60C18-aryl group, -(CH2)m- and –(CF2)m- with m being an integer from 1 to 6, an aliphatic divalent group, linear or branched, of up to 5 carbon atoms, and combinations thereof (claim 1), which reads on a copolymer (P1) comprising: recuring units (RP1) of formula (M), and recuring units (R*P1) of formula (N) as claimed.
The patent does not claim that the copolymer (P1) further comprises at least 50 µeq/g of hydroxyl end groups, amine end groups, or acid end groups. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to modify the patent’s copolymer (P1) to have at least 50 µeq/g of hydroxyl end groups. The proposed modification would read on the copolymer (P1) further comprising at least 50 µeq/g of hydroxyl end groups as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because the patent claims that the copolymer (P1) comprises recurring units (RP1) of formula (M):
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and recurring units (R*P1) of formula (N):
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(claim 1), each of which would have a hydroxyl end group when present at the end of the patent’s copolymer (P1). Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Response to Arguments
Applicant’s arguments, see p. 11-18, filed 11/06/2025, with respect to the rejection of claims 1-9 under 35 U.S.C. 103 as being unpatentable over Chen et al. (Chen et al., “Partially fluorinated poly(arylene ether)s bearing long alkyl sulfonate side chains for stable and highly conductive proton exchange membranes”, Journal of Membrane Science, 2018, vol. 549, op. 12-22) in view of Yang et al. (Yang et al., “Zwitterionic poly(arylene ether sulfone) copolymer/poly(arylene ether sulfone) blends for fouling-resistant desalination membranes”, Journal of Membrane Science, 2018, vol. 561, p. 69-78) have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Yang et al. (Yang et al., “Zwitterionic poly(arylene ether sulfone) copolymer/poly(arylene ether sulfone) blends for fouling-resistant desalination membranes” and Supporting Information, Journal of Membrane Science, 2018, vol. 561, p. 69-78) in view of Chen et al. (Chen et al., “Partially fluorinated poly(arylene ether)s bearing long alkyl sulfonate side chains for stable and highly conductive proton exchange membranes”, Journal of Membrane Science, 2018, vol. 549, op. 12-22, made of record on 06/06/2025).
Applicant’s arguments, see p. 11-12, filed 11/06/2025, with respect to claim 14 have been considered and are responded to by the new grounds of rejection that is set forth in this Office action.
Applicant's arguments filed 11/06/2025 have been fully considered but they are not persuasive. In response to the applicant’s argument that the combination of Chen and Yang does not render claims 1-9 unpatentable (p. 12-17), the applicant is referring to the combination of Chen in view of Yang. However, the rejection that is set forth in this Office action is a combination of Yang in view of Chen, which renders obvious claims 1-9 and 19 as explained in the rejection.
Applicant’s arguments, see p. 17, filed 11/06/2025, with respect to claim 19 have been considered and are responded to by the new grounds of rejection that is set forth in this Office action.
Correspondence
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/DAVID T KARST/Primary Examiner, Art Unit 1767