DETAILED ACTION
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 04/20/2026 has been entered.
Status of Rejections
All previous rejections are withdrawn.
New grounds of rejection are presented.
Claims 1-15 and 17-21 are pending and under consideration for this Office Action.
Claim Rejections - 35 USC § 112
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-15 and 17-21 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1: The product claimed in claim 1 is considered unclear. The claim claims a membrane that comprises a cation exchange layer that “includes a cured product of at least one compound of Formula (I)”. On page 9 of the arguments filed on 04/20/2026, the Applicant states that the product “does not include the hydrolyzed product”. However, the Applicant also states “In other words, the bipolar membrane defined in claim 1 represents an intermediate production, which can subsequently converted into a further product only if the hydrolysis step is performed”. Based on the Applicant’s comments, the hydrolysis step is an optional element/step. The claim uses “comprising” as the transitional phrase and MPEP § 2111.03 I states ‘The transitional term "comprising"…is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. See, e.g., Mars Inc. v. H.J. Heinz Co., 377 F.3d 1369, 1376, 71 USPQ2d 1837, 1843 (Fed. Cir. 2004)’. Therefore, it is unclear if the membrane of claim 1 would include the intermediate product as well as the hydrolyzed product formed from the optional process step. Furthermore, the claim scope is unclear because it is not clear what the resulting product or composition is required in the claim.
Any claims dependent on the above claim are rejected for their dependence.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-11 and 16-21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Melin et al (WO 2010106021 A1, SEARCH translation used for citations) in view of Sawada et al (“Block-type proton exchange membranes prepared by a combination of radiation-induced grafting and atom-transfer radical polymerization”, Journal of Membrane Science, 532, 2017, pages 105-114).
Li et al (“Enhancement of thermal stability of poly(divinylbenzene) microspheres”, Materials Letters, Volume 62, Issue 2, 31 January 2008, Pages 179-182), Zhu (“Investigation on Dynamic Mechanical Properties of Crosslinked Poly(styrene-co-divinylbenzene) Bulk Copolymers: Effect of Divinylbenzene Content”, Polymers & Polymer Composites, Vol. 20, Nos. 1 & 2, 2012), and EBM (“Cross Linking Polymerization Explained”, 2024, pages 1-8) cited as evidence for claim 1.
Love (“Polymeric Biomaterials”, Biomaterials, 2017) cited as evidence for claim 4.
Claim 1: Melin discloses a bipolar membrane (see e.g. abstract) comprising an anion exchange layer (AEL) and a cation exchange layer (CEL) (see e.g. page 7, paragraph starting with “The bipolar membrane”).
Melin discloses that the CEL can be “poly (styrene-co-divinylbenzenes)” (see e.g. page 8, paragraph starting with “In a further embodiment”) having the formula shown below as evidenced by Chemical Book:
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with sulfonic acid groups (see e.g. page 8, paragraph starting with “In a further embodiment”). Poly(styrene-co-divinylbenzenes) is a thermoset (see e.g. page 179, col 2 of Li: “DVB contains two active pendant ethylene groups and is easily polymerized to form thermosetting polydivinylbenzene materials with various morphologies including spherical shape”) crosslinked polymer (see e.g. abstract of Zhu). According to EBM, thermosets are crosslinked during curing processes (see e.g. page 3, “Thermosetting polymers”). Furthermore, the instant application states that divinylbenzenes are suitable materials for the invention (see e.g. Table 3 of the instant specification).
Melin does not explicitly teach the CEL includes a product of at least one compound of Formula (I):
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wherein: X is of the formula -OCnH2n+1 or -OCqH2q-1, wherein n has a value of 1 to 6 and q has a value of 5 or 6; and m has a value of 1 or 2”. Additionally, the claim limitation is a product-by-process limitation. MPEP § 2113 states ‘"[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985)’.
Sawada teaches an ion exchange polymer (see e.g. abstract), making it analogous art (see MPEP § 2141.01(a) I). The polymer of Sawada comprises the following compound:
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(see e.g. page 106, “Poly(EtSS)” on Scheme 1), which can be further processed via hydrolysis. The polymer formed by the method of Sawada “exhibited higher proton conductivities and water contents than those of the conventional RIGP-PEMs” (see e.g. abstract). Therefore, it would be obvious to a person having ordinary skill in the art before the effective filing date of the instant invention to use the polymer and method of forming the polymer taught in Sawada for the CEL of Melin because the polymer of Sawada satisfies the requirements of Melin and has higher proton conductivities and water contents. MPEP § 2144.07 states ‘The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)’.
Claim 2: Melin in view of Sawada teaches that the CEL includes a cured product of at least the following ingredients:
The compound of Formula (I) (see e.g. rejection of claim 1 above); and at least two of the following:
a compound comprising at least two ethnecically unsaturated groups (divinyl benzene) (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”))
an anionic monomer comprising one and only one ethylenically unsaturated group (sulfonated styrene, Melin - see e.g. page 8, paragraph starting with “In a further embodiment”).
Claim 3: Melin in view of Sawada teaches that the curable composition from which the CEL is obtainable can comprise: (a) ~50 wt% of component (a) (styrene); (b) ~50 wt% of component (b) (divinyl benzene) (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”)); (e) with the rest of the weight being the anionic monomer (see e.g. page 8, paragraph starting with “In a further embodiment”).
Claim 4: Melin in view of Sawada teaches that the cured product includes (a), (b), and (e) (see rejection of claim 2 above). However, Melin does not explicitly teach that the product includes (d), a radical initiator. However, the instant specification states that the radical initiator is an optional part (see e.g. [0016] of the instant PGPub). Furthermore, Love states that “Radical polymerization is effective in polymerizing a range of polyolefins, polystyrene, acrylates, and other vinyl polymers that contain unsaturated alkene chemistry. Radical chemistry requires a radical initiator”. As stated above, Melin discloses the polymer is poly (styrene-co-divinylbenzenes). Therefore, it would have been obvious to a person having ordinary skill in the art before the effective filing date of the instant invention that the product of Melin is substantially similar to one including (a), (b), (d) and (e).
Claim 5: Melin in view of Sawada teaches that the molar ratio of component (a) and component (b) is in the range ~1:1 (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 6: Melin in view of Sawada teaches that the curable composition from which the CEL is obtainable comprises at least 60wt% of curable compounds (see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 7: Melin in view of Sawada teaches discloses that the AEL includes a curable product of at least a curable cationic compound (polystyrene with tertiary amine groups, see e.g. Melin - page 7, paragraph starting with “In one embodiment”).
Claim 8: Melin in view of Sawada teaches that the AEL includes a cured product of at least the following ingredients: (a2) a curable cationic compound comprising at least two ethylenically unsaturated groups (divinylbenzenes, see e.g. Melin - page 7, paragraph starting with “In one embodiment”)
The other limitations claiming “optionally (b2) a compound comprising one and only one ethylenically unsaturated group; optionally (c2) a solvent; and optionally (d2) a radical initiator” are all optional and considered non-limiting. MPEP § 2143.03 states ‘Language that suggests or makes a feature or step optional but does not require that feature or step does not limit the scope of a claim under the broadest reasonable claim interpretation’.
Claim 9: The limitation is limiting the process and not the product and is not considered limiting as the resulting products of the instant invention and Melin are considered obvious over one another.
Claim 10: Melin in view of Sawada teaches that the molar ratio of component (a2) to component (b2) is in the range ~1:1 (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 11: Melin in view of Sawada teaches the AEL includes a cured product of component (a2) (divinylbenzenes, see e.g. Melin - page 7, paragraph starting with “In one embodiment”) and at least (b2) (“poly (styrene-co-divinylbenzenes)”, see e.g. page 8, paragraph starting with “In a further embodiment”)).
Claim 17: Melin in view of Sawada teaches a method of using the membrane according to claim 1 (see rejection of claim 1 above) for the production the acids and bases (see Melin - e.g. page 2, paragraph starting with “Modules”).
Claim 18: Melin in view of Sawada teaches that the curable composition from which the CEL is obtainable comprises ~50 wt% of component (a) (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 19: Melin in view of Sawada teaches that the curable composition from which the CEL is obtainable comprises ~50 wt% of component (b) (“poly (styrene-co-divinylbenzenes)”, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 20: Melin in view of Sawada teaches that component (b) comprises an aromatic group (divinylbenzene, see e.g. Melin - page 8, paragraph starting with “In a further embodiment”).
Claim 21: Melin in view of Sawada teaches that component (b) comprises at least two vinyl groups (divinylbenzene, Melin - see e.g. page 8, paragraph starting with “In a further embodiment”).
Claim(s) 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Melin in view of Sawada as applied to claim 8 and in further in view of Kaminaga et al (US 20170128931 A1).
Claim 12: Melin does not explicitly teach that component (a2) is of Formula (II):
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wherein: L1 is an alkylene group or an alkenylene group; Ra, Rb, Rc, and Rd are each independently an alkyl group or an aryl group, or Ra and Rb, and/or Rc and Rd may, together with the atoms to which they are attached, form a ring; n1 and n2 each independently represent an integer of 1 to 10; and X1- and X2- each independently represent an anion.
As stated above, Melin teaches that the AEL can be a polystyrene with tertiary amine groups (see e.g. page 7, paragraph starting with “In one embodiment”). Kaminaga teaches an anion exchange polymer (see e.g. abstract and [0043]) formed by curing (see e.g. [0138]) the following compound:
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The polymer of Kaminaga has high performance with small defects and sufficient mechanical strength (see e.g. [0008]). Therefore, it would be obvious to a person having ordinary skill in the art before the effective filing date of the instant invention to modify Melin in view of Sawada to use the polymer of Kaminaga because the polymer of Kaminaga satisfies the requirements of Melin and has high performance with small defects and sufficient mechanical strength. MPEP § 2144.07 states ‘The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)’.
Claim(s) 13-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Small et al (US 20200078736 A1) in view of Kaminaga and Sawada.
Claim 13: Small discloses a process for manufacturing a membrane comprising the steps:
applying an AEL composition to a support (see e.g. abstract; [0022]);
forming an anion exchange layer (AEL) (see e.g. [0022]);
applying a CEL composition to the AEL (see e.g. abstract; [0022]); and
forming a cation exchange layer (CEL) on the AEL (see e.g. [0022]);
Small does not explicitly teach that AEL comprises a curable cationic compound that is cured to form the AEL. Small teaches using cationic polymers comprising amine-functional groups (see e.g. [0019]). Kaminaga teaches an anion exchange polymer (see e.g. abstract and [0043]) formed by curing (see e.g. [0138]) the following compound:
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The polymer of Kaminaga has high performance with small defects and sufficient mechanical strength (see e.g. [0008]). Therefore, it would be obvious to a person having ordinary skill in the art before the effective filing date of the instant invention to modify the method of Small to use the polymer of Kaminaga because the polymer of Kaminaga satisfies the requirements of Small and has high performance with small defects and sufficient mechanical strength. MPEP § 2144.07 states ‘The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)’.
Small does not explicitly teach that the CEL composition comprises a compound of Formula (I) as defined in claim 1 and is cured to form the CEL. Small teaches using polymers comprising sulfonate functional groups (see e.g. [0019]).
Sawada teaches an ion exchange polymer (see e.g. abstract) formed by comprising curing a curable composition (heat treatment at 95 oC, see e.g. page 107, col 2, section 2.4) comprising the following compound:
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(see e.g. page 106, “Poly(EtSS)” on Scheme 1). The polymer formed by the method of Sawada “exhibited higher proton conductivities and water contents than those of the conventional RIGP-PEMs” (see e.g. abstract). Therefore, it would be obvious to a person having ordinary skill in the art before the effective filing date of the instant invention to use the polymer and method of forming the polymer taught in Sawada for the polymer of Small because the polymer of Sawada satisfies the requirements of Small and has higher proton conductivities and water contents. MPEP § 2144.07 states ‘The selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)’.
Claim 14: Small in view of Kaminaga and Sawada teaches that the process further comprises the step of hydrolysing at least some the -SO2X groups in the compounds of Formula (I) to - SO2OH groups (see e.g. Sawada - page 107, col 2, paragraph 2.4; Scheme 1).
Claim 15: Small in view of Kaminaga and Sawada teaches that that the AEL composition comprises the following ingredients: (a2) a curable cationic compound comprising at least two ethylenically unsaturated groups (divinylbenzenes, see e.g. Kaminaga - page 7, paragraph starting with “In one embodiment”).
The other limitations claiming “optionally (b2) a compound comprising one and only one ethylenically unsaturated group; optionally (c2) a solvent; and optionally (d2) a radical initiator” are all optional and considered non-limiting. MPEP § 2143.03 states ‘Language that suggests or makes a feature or step optional but does not require that feature or step does not limit the scope of a claim under the broadest reasonable claim interpretation’.
Response to Arguments
Applicant's arguments filed 04/20/2026 have been fully considered but they are not persuasive.
On page(s) 7-10, the Applicant argues that Melin does not read on claim 1 because “The subject matter of claim 1, therefore, does not include the hydrolyzed product described in Melin”. This is not considered persuasive because it is not clear if the claim, as claimed, includes the hydrolyzed product or not. See the rejection of claim 1 under 35 USC 112(b) above.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER W KEELING whose telephone number is (571)272-9961. The examiner can normally be reached 7:30 AM - 4:00 PM. 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, Luan Van can be reached at 571-272-8521. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ALEXANDER W KEELING/Primary Examiner, Art Unit 1795
