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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on August 25, 2025 has been entered.
Response to Amendment
The Amendment filed August 25th, 2025 has been entered. Examiner acknowledges the cancellation of Claim 13 and the addition of new Claims 21-22. Claims 1-2, 4-9, 12 and 14-22 remain pending in the application. Applicant’s amendments to the Claims have overcome each and every 103 rejection previously set forth in the Non-Final Office Action mailed July 31st, 2024. Therefore, the objections and rejections have been withdrawn. However, upon further consideration in light of these amendments, a new grounds of rejection is made in view of 35 USC § 103.
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:
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(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).
Cote does not disclose that the anionic species comprises 3-hydroxypropane sulfonic acid.
Ito discloses a structured organic film (SOF)(lto abstract "aromatic polysulfone" which can be applied as a film), comprising: a plurality of segments (Ito par. [0013] "repeating unit"); a plurality of linkers (Ito par. [0022] "repeating unit (2)"); and a plurality of capping segments (Ito par. [0096] "end capping agent"); wherein at least one or more of the plurality of capping segments comprises at least one anionic species, the anionic species comprising
4-hydroxybenzene sulfonic acid (Ito par. [0097]), 3-hydroxypropane sulfonic acid, or a combination thereof.
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, importantly disclosing 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).
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 may include anionic functional groups, but leaves the specific identity of the anionic species open to routine design choice. Ito teaches that sulfonic-acid-containing compounds are suitable end-capping agents for imparting ionic functionality to polymeric structures. When selecting an appropriate sulfonate species for use an anionic capping segment in such polymeric 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 teaches that sulfonate salt modifiers are selected from a known class of compounds that are functionally interchangeable on a molar basis. Griffing expressly identifies 3-hydroxypropane-1-sulfonate as one such conventional sulfonate species suitable for incorporation into polymeric films. 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 (Ito par. [0097]).
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 (Cote col. 57-58 table 2 provides many examples).
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 col. 22 line 24).
Regarding claim 17, the combination of Cote, Ito and Griffing discloses a structured organic film (SOF), comprising: a plurality of segments (Cote abstract), wherein at least one of the plurality of segments comprises:
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(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”).
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 (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:
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(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”).
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]).
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]).
Claims 4, 15, 17 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 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 discloses a structured organic film (SOF), comprising: a plurality of segments (Izuhara par. [0017]); a plurality of linkers (Izuhara par. [0092]); and optionally a plurality of capping segments (Izuhara par. [0132]); 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, wherein a concentration of anionic capping segments (Izuhara par. [0017] discloses the ionic group containing segments (A1) include a constituent unit as represented by the general formula S1 shown in Chemical formula 3 and where X4 is defined as an ionic species and later is described in claim 8 to be sulfonic acid the ion of which is an anion) 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 par. [0096] described as the molar content ratio of A1/A2 being 0.2 or more and 5 or less).
Izuhara further discloses that this range is important to ensure sufficient proton conductivity under low humidify conditions, insufficient hot water resistance, or insufficient physical durability (Izuhara par. [0096]). As the SOF of Cote can be used in electronic devices such as solar cells, radio frequency identification tags, organic light emitting devices, photoreceptors, thin film transistors and the like (Cote col. 34 lines 46-48) these are qualities which would be advantageous and under the suggestion of Izuhara It would have been obvious to one of ordinary skill in the art at the time of filing to combine the ratio of the anionic capping segments of Izuhara with the SOF of Cote, Ito and Griffing and with the information disclosed by Izuhara that this range is important to ensure sufficient proton conductivity under low humidify conditions, insufficient hot water resistance, or insufficient physical durability there would have been motivation to provide such a ratio.
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 17, the combination of Cote, Ito and Griffing and further in view of Izuhara discloses a structured organic film (SOF), comprising: a plurality of segments (Cote abstract), wherein at least one of the plurality of segments comprises:
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(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”).
Regarding claim 19, the combination of Cote, Ito and Griffing and further in view of Izuhara discloses the SOF of claim 17, 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]).
Claim 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 disclose 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 and appreciate full deprotonation 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-hydroxybenzene sulfonic acid 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
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.
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/W.A.G./Examiner, Art Unit 1779
/Bobby Ramdhanie/Supervisory Patent Examiner, Art Unit 1779