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 .
Response to Amendment
The Amendment filed April 8, 2026 has been entered. Claims 1, 2, 4-9, 12 and 14-22 remain pending in the application.
Response to Arguments
Applicant's arguments filed April 8, 2026 have been fully considered but they are not persuasive.
Applicant argues that independent claims 1, 17 and 20 have been amended to require specific structural arrangement within the final SOF, namely that 3-hydroxypropane sulfonic acid is comprised in a terminal, non-bridging capping segment bonded to the SOF framework through a linker or single covalent linkage, or in a capping segment that terminates a branch of the SOF framework, with the sulfonic acid group pendant from the framework. Applicant further argues that the cited references do not teach or suggest this claimed architecture.
As an initial matter, Applicant’s assertion that no new matter has been added is not persuasive for the reasons set forth in the rejection under 35 U.S.C. 112(a) below. The portions of the specification identified by the Applicant generally describe structured organic films, capping segments, ionic capping segments, capping molecules having one reactive functionality, and possible hydroxysulfonic acid species. However, the originally filed disclosure does not clearly describe the particular final SOF architecture now recited in claims 1, 17, and 20, in which 3 hydroxypropane sulfonic acid itself is comprised in the specified terminal, non-bridging, branch-terminating capping segment configuration with a pendant sulfonic acid group. The support relied upon by Applicant is an assembly of separate generic teachings rather than a clear written description of the claimed final structural arrangement. Accordingly, Applicant’s remarks do not overcome the written description rejection of claims 1, 17 and 20.
With respect to the rejection under 35. U.S.C. 103, Applicant’s arguments are also not persuasive. Applicant’s argument appears to treat the rejection as relying merely on the simple presence of a sulfonic-acid-containing species in a film or polymer. However, the rejection is not based merely on the presence of a sulfonic-acid-containing species. Rather, Cote teaches the relevant capped SOF architecture, including capping units that are bonded to and interrupt the SOF framework. Cote further teaches capping units having only a single suitable or complementary functional group that participates in the SOF-forming reaction and therefore cannot bridge further adjacent molecular building blocks. Cote also teaches that, upon curing, the single reactive functional group of the capping unit reacts with the molecular building block and locally terminates or caps the extension of the SOF framework (Cote col. 5). Thus, Cote teaches the terminal, non-bridging, branch-terminating capping segment arrangement relied upon by Applicant.
Applicant’s argument that Cote, Ito, and Griffing do not disclose 3-hydroxypropane sulfonic acid arranged in the claimed structural manner is not persuasive because the rejection relies on the combined teaching of the cited references, not on any one reference individually. Cote teaches the capped SOF framework and the monofunctional capping architecture. Ito evidences that sulfonic-acid-containing end-capping agents were known for imparting highly polar/ionic functionality to polymeric structures. Griffing teaches 3-hydroxypropane-1-sulfonate as a known sulfonate-containing species used in forming sulfonate-modified polymeric films and further teaches sulfonate-containing compounds having a reactive functional group together with a sulfonate group. It would have been obvious to one of ordinary skill in the art to use the known 3-hydroxypropane sulfonic acid/sulfonate species taught by Griffing as the anionic capping species in the capped SOF of Cote in order to impart ionic sulfonate functionality to the SOF, as suggested by the combined teachings of Cote, Ito, and Griffing.
Applicant’s argument that the claimed subject matter requires the sulfonic acid group to be pendant from the framework is likewise not persuasive. Cote teaches that the capping unit may react through a single suitable or complementary functional group to bond to the SOF framework, while other chemical moieties or functional groups on the capping unit are not suitable or complementary to participate in the SOF-forming reaction and do not bridge further adjacent molecular building blocks (Cote col. 5). Griffing’s 3-hydroxypropane sulfonic acid/sulfonate species includes a hydroxyl functionality and a sulfonic acid/sulfonate functionality. When used as Cote’s monofunctional anionic capping species, the hydroxyl-derived functionality provides the reactive linkage to the SOF framework, while the sulfonic acid/sulfonate group remains as the ionic functionality pendant from the framework. This result is the predictable use of a known sulfonate-containing compound for its known purpose of imparting ionic character to film-forming polymeric materials.
Applicant further argues that neither Ito nor Griffing remedies the alleged deficiency of Cote. This argument is not persuasive because Ito and Griffing are not relied upon to replace Cote’s capped SOF architecture. Cote supplies the capped SOF framework, including the monofunctional, non-bridging, branch-terminating capping unit arrangement. Ito and Griffing are relied upon for their teachings regarding sulfonic-acid/sulfonate functionality and the selection of the particular 3-hydroxypropane sulfonic acid/sulfonate species. The references therefore address different aspects of the claimed subject matter, and the rejection is based on their combined teachings as a whole.
Applicant has not provided persuasive evidence of criticality, unexpected results, teaching away, or unpredictability associated with selecting 3-hydroxypropane sulfonic acid/sulfonate as the anionic capping species in Cote’s capped SOF. Nor has Applicant shown that the claimed arrangement produces a result different in kind from the predictable result of using a known hydroxysulfonate species as a monofunctional ionic capping unit in Cote’s SOF framework. Accordingly, the amendments and arguments do not overcome the rejection of independent claims 1, 17 and 20 under 35 U.S.C. 103. With respect to dependent claims 2, 5-7, 9, 12, 18 and 21-22 Applicant has argued that these claims are allowable by virtue of their dependency from allegedly allowable claims 1, 17 or 20, however this argument is not persuasive because rejections of independent claims 1, 17 and 20 are maintained.
With respect to claims 4, 15 and 19, Applicant argues that Izuhara does not cure the alleged deficiencies of Cote, Ito and Griffing. This is not persuasive because, as discussed above, the base combination of Cote, Ito, and Griffing teaches or renders obvious the subject matter of claims 1 and 17. Izuhara is relied upon for the additional limitations concerning the concentration of anionic capping segments and/or ion exchange capacity. Therefore rejections of 4, 15 and 19 are maintained.
With respect to claims 8 and 14 Applicant argues that Berghofer and Wikipedia do not cure the alleged deficiencies of Cote, Ito, and Griffing. This argument is not persuasive because the base rejection of claim 1 is maintained for the reasons discussed above, therefore the rejection of claims 8 and 14 is maintained.
With respect to claim 16, Applicant argues that Swager does not cure the alleged deficiencies of Cote, Ito and Griffing. This argument is not persuasive because the base rejection of claim 1 is maintained for the reasons discussed above and therefore, the rejection of claim 16 is maintained.
For at least the reasons discussed above, Applicant’s arguments have not over the rejections under 35 U.S.C. 112(a) and 35 U.S.C. 103.
Claim Rejections - 35 USC § 112
Claims 1, 2, 4-9, 12 and 14-22 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Regarding claim 1, the claim recites, in part “wherein the 3-hydroxypropane sulfonic acid is comprised in a terminal, non-bridging capping segment that is bonded to a framework of the SOF through a linker, a sulfonic acid group being pendant from the framework”. The originally filed disclosure does not reasonably convey to one of ordinary skill in the art that Applicant was in possession of a structured organic film having 3-hydroxypropane sulfonic acid arranged in this specific final structural configuration. The specification generally describes SOFs having capping segments, generally describes that capping segments may locally interrupt the SOF framework, generally describes that capping segments may have one functional group suitable for reaction during SOF formation, and generally lists 3-hydroxypropane-1-sulfonic acid as one illustrative hydroxysulfonic acid derivative that may be used among various anionic species. However, the disclosure does not clearly describe an embodiment in which 3-hydroxypropane sulfonic acid itself is comprised in a terminal, non-bridging capping segment bonded to the SOF framework through a linker, with the sulfonic acid group being pendant from the framework. At most, the disclosure requires picking the specific 3-hydroxypropane sulfonic acid from a list of possible sulfonic acid or sulfinic acid derivatives and then combining that selection with separate, generic descriptions of capping segment behavior. Such piecemeal support does not reasonably convey possession of the claimed final SOF architecture. Accordingly, claim 1 lacks adequate written description support.
Regarding claim 17, the claim recites, in part “wherein the 3-hydroxypropane sulfonic acid is comprised in a terminal, non-bridging capping segment that is bonded to a framework of the SOF through a linker, a sulfonic acid group being pendant from the framework”. The originally filed disclosure does not reasonably convey to one of ordinary skill in the art that Applicant was in possession of a structured organic film having 3-hydroxypropane sulfonic acid arranged in this specific structural arrangement. Although the specification generally describes capping segment molecules having one functional group suitable for reaction during SOF formation, this disclosure is not the same as a clear written description of 3-hydroxypropane sulfonic acid being comprised in a terminal, non-bridging capping segment bonded to the SOF framework through a single covalent linkage in the final SOF. The disclosure also does not clearly identify the sulfonic acid group being pendant from the framework in this claimed final structure. Rather, the disclosure separately provides generic capping segment descriptions and separately identifies 3-hydroxypropane-1-sulfonic acid as an illustrative hydroxysulfonic acid derivative. The specification therefore does not demonstrate possession of the claimed combination of the specific species, the terminal/non-bridging capping-segment configuration, the single covalent linkage to the SOF framework, and the pendant sulfonic acid group. Accordingly, claim 17 lacks adequate written description support.
Regarding claim 20, the claim recites, in part “wherein the 3-hydroxypropane sulfonic acid is comprised in a capping segment that terminates a branch of the SOF framework, the capping segment being bonded to the framework, and a sulfonic acid group being pendant from the framework”. The originally filed disclosure does not reasonably convey to one of ordinary skill in the art that Applicant was in possession of the claimed SOF in which 3-hydroxypropane sulfonic acid is specifically comprised in a capping segment that terminates a branch of the SOF framework with the sulfonic acid group pendant from the framework. The specification generally describes capping segments and ionic capping segments as closing off or terminating branches of an SOF network and generally identifies 3-hydroxypropane sulfonic acid as one possible hydroxysulfonic acid species. However, the disclosure does not clearly describe the specific claimed embodiment in which the 3-hydroxypropane sulfonic acid species in incorporated into the final SOF as the branch-terminating capping segment, is bonded to the framework, and has the sulfonic acid group pendant from the framework. The support relied upon for the amendment is therefore an assembly of separate generic teachings rather than a disclosure of the claimed final structural arrangement. Accordingly, claim 20 lacks adequate written description support.
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.
Claims 1-2, 5-7, 9, 12, 17-18 and 20-22 are rejected under 35 U.S.C. 103 as being unpatentable over Cote (US-8318892-B2) in view of Ito (EP-3476883-A1) and further in view of Griffing (US3018272).
Regarding claim 1, Cote discloses a structured organic film (SOF), comprising:
a plurality of segments (Cote abstract), wherein at least one of the plurality of segments comprises:
PNG
media_image1.png
208
386
media_image1.png
Greyscale
(Cote col. 17 lines 15-26); a plurality of linkers (Cote abstract); and a plurality of capping segments (Cote "capping unit" shown as circles in Fig. 1 and col. 2 line 11); and wherein at least one or more of the plurality of capping segments comprises at least one anionic species (Cote col. 4 lines 32-34 describe that the capping units may comprise a single type or two or more types of functional groups and col. 4 lines 1-3 list the possible groups including tosylates which are anionic); and wherein the anionic species is comprised in a terminal, non-bridging capping segment (Cote col. 5 teaches that capping units may be monofunctionalized and may comprise only a single suitable or complementary functional group that participates in a chemical reaction to link together segments and is therefore not suitable for bridging) that is bonded to a framework of the SOF through a linker (Cote col. 8 additionally teaches that a linker is a chemical moiety that emerges in a SOF upon chemical reaction between functional groups present on molecular building blocks and/or a capping unit, and that the linker may be a “covalent bond, single atom, or a group of covalently bonded atoms”).
Cote does not disclose that the anionic species comprises 3-hydroxypropane sulfonic acid, nor does Cote expressly disclose the specific 3-hydroxypropane sulfonic acid species arranged such that a sulfonic acid group is pendant from the SOF framework.
Ito discloses an aromatic polysulfone which can be applied as a film (lto abstract), comprising: a plurality of segments (Ito par. [0013] "repeating unit"); a plurality of linkers (Ito par. [0022] "repeating unit (2)"); and terminal end-capping groups (Ito par. [0096] "end capping agent"). Ito further teaches that highly polar functional groups, including sulfonic acid groups, may be present at the terminal of a polymer and that a terminal functional group of a polymer may be replaced with a compound having a highly polar functional group after polymerization. Thus demonstrating that sulfonic-acid-containing compounds were known to be useful terminal/end-capping agents for imparting highly polar/ionic functionality to polymeric structures.
Griffing is directed to film- and fiber-forming polymers incorporating sulfonate groups as polymer-incorporated ionic species and is reasonably pertinent to the present application because it addresses the same technical problem of introducing anionic sulfonate functionality into polymeric films to impart ionic properties (Griffing col. 1-2 and examples). Griffing explicitly teaches that sulfonate-containing compounds may be incorporated into polymeric structures as functional modifiers and that such sulfonate species may comprise alkylene sulfonates in which the sulfonate group is separated from the polymer backbone by multiple carbon atoms. Griffing further discloses compounds containing at least one functional group together with at least one sulfonate group, including monohydric alcohols containing at least one sulfonic acid group, and expressly discloses the use of 3-hydroxypropane-1-sulfonate as a sulfonate species added during polymer formation, stating that “0.8 part of sodium 3-hydroxypropane-1-sulfonate is added” to a polyester reaction mixture to form a sulfonate-modified polymer film (Griffing Example 11). Griffing further teaches that such sulfonate salt modifiers are functionally interchangeable on a molar basis (Griffing col. 9 lines 31-36) and may be selected from a known class of sulfonate-containing compounds (Griffing col. 1 lines 47-51) to impart ionic character to polymeric films (Griffing, col. 11 par. 2-3 discusses the properties of dye penetration and physical properties imparted which is due to the ionic character present in the films). Thus Griffing teaches the particular known hydroxysulfonate species corresponding to the claimed 3-hydroxypropane sulfonic acid, wherein the hydroxyl functionality provides a reactive group capable of incorporation into a polymer-forming reaction and the sulfonic acid/sulfonate functionality provides the anionic group. When this known hydroxysulfate species is used as Cote’s monofunctional capping unit, the hydroxyl-derived portion would provide the single linkage/linker to the SOF framework, while the sulfonic acid/sulfonate group would remain pendant from the SOF framework rather than serving as a bridging linkage to another molecular building block.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the structured organic film of Cote, as informed by Ito, by employing a known sulfonate species as taught by Griffing. Cote teaches structured organic films having capping segments that are terminal, non-bridging, and locally terminate or cap the extension of the SOF framework by reacting through a single functional group. Cote further teaches that such capping units may include anionic functional groups, but leaves the specific identity of the anionic species open to routine selection. Ito teaches that sulfonic-acid-containing compounds are suitable terminal/end-capping agents for imparting ionic functionality to polymeric structures. When selecting an appropriate sulfonate species for use an anionic capping segment in Cote’s structured organic films, a person of ordinary skill in the art would have looked to Griffing, which addresses the same problem of introducing sulfonate functionality into film-forming polymers and expressly identifies 3-hydroxypropane-1-sulfonate as one such conventional sulfonate species suitable for incorporation into polymeric films. Because Cote already teaches monofunctional capping units that cannot bridge further adjacent molecular building blocks and locally terminate/cap the SOF framework, the substitution of Griffing’s known 3-hydroxypropane sulfonic acid/sulfonate species as the anionic capping unit would predictably result in a terminal, non-bridging capping segment bonded to the SOF framework through a linker or single covalent linkage, with the sulfonic acid/sulfonate group pendant from the framework. Accordingly, the use of 3-hydroxypropane sulfonic acid as the anionic species in the capping segments of Cote’s structured organic film represents the predictable use of a known sulfonate compound for its established purpose, with a reasonable expectation of success, rather than an inventive selection, and therefore would have been obvious to one of ordinary skill in the art.
Regarding claim 2, the combination of Cote, Ito and Griffing discloses the SOF of claim 1, comprising a plurality of capping segments (Cote col. 4 lines 32-34 "capping units").
Regarding claim 5, the combination of Cote, Ito and Griffing discloses the SOF of claim 1, wherein a thickness of the SOF is from about 100 nm to about 500 μm (Cote claim 22 describes multisegmented thickness can be between 20nm to 5mm).
Regarding claim 6, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1, wherein at least one of the plurality of capping segments (Cote indicates in col. 6 line 67 an embodiment in which there are at least three other capping segments) further comprises a sulfonic acid (Griffing Example 11 “sodium 3-hydroxypropane-1-sulfonate”).
Regarding claim 7, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1, wherein at least one of the plurality of capping segments further comprises a linear alkyl derivative (Griffing Example 11 “sodium 3-hydroxypropane-1-sulfonate”).
Regarding claim 9, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1, wherein at least one of the plurality of capping segments further comprises a benzene derivative (Cote col. 57-58 table 2 provides many examples).
Regarding claim 12, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1, wherein at least one of the plurality of capping segments further comprises a naphthalene derivative (Cote teaches that the capping unit may comprise a mixture of capping units, including a first capping unit and a second capping unit having different structures, and that the identity of the chemical moieties or functional groups on the capping units may be varied to form a mixture of capping units while Griffing teaches naphthalene sulfonate derivatives as known sulfonate containing modifiers, specifically sodium 1,8-di(carbomethoxy)naphthalene-3-sulfonate (Griffing Example 1)).
Regarding claim 17, the combination of Cote, Ito and Griffing discloses or renders obvious a structured organic film (SOF), comprising: a plurality of segments (Cote abstract), wherein at least one of the plurality of segments comprises:
PNG
media_image1.png
208
386
media_image1.png
Greyscale
(Cote col. 17 lines 15-26); a plurality of linkers (Cote abstract); and a plurality of capping segments (Cote "capping unit" shown as circles in Fig. 1 and col. 2 line 11), wherein at least one or more capping segments comprises at least one anionic species (Cote col. 4 lines 32-34 describe that the capping units may comprise a single type or two or more types of functional groups and col. 4 lines 1-3 list the possible groups including tosylates which are anionic), the anionic species comprising 3-hydroxypropane sulfonic acid (Griffing Example 11 “sodium 3-hydroxypropane-1-sulfonate”); and wherein the 3-hydroxypropane sulfonic acid is comprised in a terminal, non-bridging capping segment (Cote col. 5 teaches that capping units may be monofunctionalized and may comprise only a single suitable or complementary functional group that participates in a chemical reaction to link together segments and is therefore not suitable for bridging) that is bonded to a framework of the SOF through a single covalent linkage (Cote col. 8 additionally teaches that a linker is a chemical moiety that emerges in a SOF upon chemical reaction between functional groups present on molecular building blocks and/or a capping unit, and that the linker may be a “covalent bond, single atom, or a group of covalently bonded atoms”), a sulfonic acid group being pendant from the framework (when Griffing’s 3-hydroxypropane sulfonate/sulfonic acid species is used as the anionic capping species in Cote’s monofunctional capping unit, the species is present as a terminal, non-bridging capping segment bonded to the SOF framework through a single covalent linkage/linker formed from the single reactive functional group of the capping segment, with the sulfonic acid/sulfonate group remaining pendant from the framework).
Regarding claim 18, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 17, wherein: at least one of the plurality of segments further comprises: at least one or more capping segments comprises a linear alkyl derivative, a benzene
derivative, a naphthalene derivative, or a combination thereof (Griffing Example 11 “sodium 3-hydroxypropane-1-sulfonate” and Cote col. 57-58 table 2 provides many examples).
Regarding claim 20, the combination of Cote, Ito and Griffing discloses a structured organic film (SOF), comprising: a plurality of segments (Cote abstract); a plurality of linkers (Cote abstract); and a plurality of capping segments (Cote "capping unit" shown as circles in Fig. 1 and col. 2 line 11), wherein: at least one of the plurality of segments comprises:
PNG
media_image1.png
208
386
media_image1.png
Greyscale
(Cote col. 17 lines 15-26); and at least one or more capping segments comprises at least one anionic species (Cote col. 4 lines 32-
34 describe that the capping units may comprise a single type or two or more types of
functional groups and col. 4 lines 1-3 list the possible groups including tosylates which are
anionic), the anionic species comprising 3-hydroxypropane sulfonic acid (Griffing Example 11 “sodium 3-hydroxypropane-1-sulfonate”) wherein the 3-hydroxypropane sulfonic acid is comprised in a capping segment that terminates a branch of the SOF framework (Cote col. 5 teaches that capping units may be monofunctionalized and may comprise only a single suitable or complementary functional group that participates in a chemical reaction to link together segments and is therefore not suitable for bridging), the capping segment being bonded to the framework, and a sulfonic acid group being pendant from the framework (when Griffing’s 3-hydroxypropane sulfonate/sulfonic acid species is used as the anionic capping species in Cote’s monofunctional capping unit, the species is present as a terminal, non-bridging capping segment bonded to the SOF framework through a single covalent linkage/linker formed from the single reactive functional group of the capping segment, with the sulfonic acid/sulfonate group remaining pendant from the framework).
Regarding claim 21, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1, wherein the anionic species further comprises 4-hydroxybenzene sulfonic acid (Ito par. [0097] and since Cote allows multiple capping units/functional groups or varied capping-unit structures, adding Ito’s 4-hydroxybenzene sulfonic acid as an additional ionic capping/end-capping species would have been obvious).
Regarding claim 22, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 17, wherein the anionic species further comprises 4-hydroxybenzene sulfonic acid (Ito par. [0097] and since Cote allows multiple capping units/functional groups or varied capping-unit structures, adding Ito’s 4-hydroxybenzene sulfonic acid as an additional ionic capping/end-capping species would have been obvious).
Claims 4, 15 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Cote (US-8318892-B2) in view of Ito (EP-3476883-A1) and Griffing (US3018272) as applied to claim 1 and 17 above, and further in view of Izuhara (CA2833684-A1).
Regarding claim 4, the combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1.
Neither Cote, Ito nor Griffing discloses wherein a concentration of anionic capping segments in the SOF is from about 0.1 to about 5.0 molar equivalents of anionic capping segments as compared to a concentration of nonionic segments in the SOF.
Izuhara teaches an analogous ratio of ionic-group-containing units to nonionic units, specifically a molar content ratio of A1/A2 of 0.2 or more and 5 or less, and teaches that this range is useful for achieving sufficient proton conductivity while maintaining hot water resistance and physical durability (Izuhara par. [0096]).
It would have been obvious to one of ordinary skill in the art prior to the effective
filing date of the claimed invention to apply Izuhara’s known ration of ionic-group-containing units to nonionic units to the anionic capping segments of the SOF of Cote, as modified by Ito and Griffing, in order to obtain a predictable concentration of ionic functionality suitable for ion-exchange/proton-conductive film applications while maintaining durability.
Regarding claim 15, the combination of Cote, Ito and Griffing and further in view of Izuhara discloses the SOF of claim 1, wherein the structured organic film (SOF) has an ion exchange capacity (IEC) of from about 0.25 mEq/g to about 5.00 mEq/g (Izuhara par. [0095]).
Regarding claim 19, the combination of Cote, Ito and Griffing and further in view of Izuhara discloses the SOF of claim 17 as discussed above, wherein the structured organic film (SOF) has an ion exchange capacity (IEC) of from about 0.25 mEq/g to about 5.00 mEq/g (Izuhara par. [0095]).
Claims 8 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Cote (US-8318892-B2) in view of Ito (EP-3476883-A1) and Griffing (US3018272) as applied to claim 1 and claim 12 above, and further in view of Berghofer (US-11053193-B2) and wikipedia.org.
Regarding claim 8, the combination of Cote, Ito and Griffing discloses the SOF of claim 1.
Neither Cote, Ito nor Griffing discloses wherein at least one of the plurality of capping segments further comprises a hydroxysulfinic acid.
However, Ito discloses that the capping segments are used to produce at least one highly polar functional group at its terminal, for which the use of 4-hydroxybenzene sulfinic acid in place of the 4-hydroxybenzene sulfonic acid or 3-hydroxypropane sulfinic acid in place of 3-hydroxypropane sulfonic acid would be analogous. Sulfonic acids and sulfinic acids are both oxoacids of sulfur and differ by only one oxygen atom on sulfur (Wikipedia.org) and they mimic each other in size and polarity. Both compounds are in the same magnitude of acidity in water and both are common compounds which can replace one another without a significant change in reaction conditions which is why they are often provided as alternatives in industrial applications (for example “Berghofer” US-11053193-B2 abstract and throughout). It would have been obvious to one of ordinary skill in the art at the time of filing to combine the teaching of Berghofer with the SOF of Cote as suggested by Ito to include at least one of the plurality of capping segments further comprises a hydroxysulfinic acid.
Regarding claim 14, the combination of Cote, Ito and Griffing discloses the SOF of claim 12, wherein at least one of the plurality of capping segments further comprises a hydroxynaphthalene sulfonic acid, a hydroxysulfinic acid (see rejection of claim 8 above), or a combination thereof.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Swager (US-20220282041-A1) in view of Cote (US-8318892-B2) in view of Ito (EP-3476883-A1) and Griffing (US3018272) as applied to claim 1 above.
Regarding claim 16, Swager discloses an ion-exchange membrane (Swager par. [0164]), comprising a structured organic film (SOF) (Swager par. [0165] "a layer or film of a poly(aryl ether)", comprising: a plurality of segments (Swager "monomer" and "comonomer" claim 1); a plurality of linkers (Swager "cross-linking units" par. [0202]); and a plurality of capping segments (Swager "endcapping agent" par. [0210]); wherein at least one or more of the plurality of segments and/or at least one or more of the plurality of capping segments comprises at least one anionic species.
Swager does not disclose the structured organic film (SOF) of claim 1.
The combination of Cote, Ito and Griffing discloses the structured organic film (SOF) of claim 1. Neither Cote, Ito, nor Griffing disclose an ion-exchange membrane.
It would have been obvious to one of ordinary skill in the art at the time of filing to combine the ion exchange membrane of Swager with the plurality of segments of Cote and the 3-hydroxypropane-1-sulfonic acid/sulfonate capping segments of Griffing. All are in the analogous art of capped structured organic or polymer films used for the transport or exchange of ions. There would have been a reasonable expectation of success as the use of sulfonated or carboxylated films for ionic conduction are well understood in polymer and membrane arts. The advantages of using the structurally robust, functionalized films of the combination of Cote, Ito and Griffing as a selective ion exchange layer or coating would have been recognized by a person of ordinary skill in the art and this would have provided the motivation to combine them.
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 WILLIAM ADDISON GEISBERT whose telephone number is (703)756-5497. The examiner can normally be reached Mon-Fri 7:30-5:00 EDT.
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) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Bobby RAMDHANIE can be reached at (571)270-3240. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/W.A.G./Examiner, Art Unit 1779
/Bobby Ramdhanie/Supervisory Patent Examiner, Art Unit 1779
Prosecution Insights