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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 January 19, 2026 has been entered.
Priority
Acknowledgment is made of applicant’s claim for foreign priority (EP19210947.8 Filed on 22 November 2019) under 35 U.S.C. 119 (a)-(d). Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 6 objected to because of the following informalities:
The indentation of Claim 6 should be corrected for consistency with the remaining claims.
The limitation “Claim1” should be corrected to read “Claim 1” for a missing space.
Appropriate correction is required.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determining the scope and contents of the prior art.
Ascertaining the differences between the prior art and the claims at issue.
Resolving the level of ordinary skill in the pertinent art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-8, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over KUNTZ et al (US3933753, hereinafter KUNTZ) in view POSS et al. (US20050131141A1, hereinafter POSS).
Regarding Claim 1, KUNTZ discloses a method of producing an alkenylaromatic polymer bearing α-ketoaldehyde (–CO–CHO) groups, where the polymer is derived from monomers of the general formula CH₂=C(R′)–Ar(R″), R′ is hydrogen or methyl, and R″ is hydrogen, methyl, or ethyl, as shown in FIG. 1 (Col. 1, Lns. 8–34).
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FIG. 1 of KUNTZ
Monomers include styrene, α-methylstyrene, m-vinyltoluene, and m-ethylstyrene. Ethylenic comonomers include ethylene, propylene, butadiene, and isoprene, and crosslinking monomers include divinylbenzene (Col. 1, Lns. 35–45).
The corresponding haloacetyl-containing alkenylaromatic polymer is reacted with dimethyl sulfoxide to introduce α-ketoaldehyde groups. The degree of conversion is controlled by the amount of sulfoxide and the reaction duration, and the optimum reaction conditions are determined by simple experiments (Col. 1, Ln. 46 – Col. 2, Ln. 38).
The haloacetyl-containing polymer is prepared through a phenacyl-halide route. A polyalkenylacetophenone is prepared by acetylating an alkenylaromatic polymer using acetyl chloride in the presence of aluminum chloride, and the polyalkenylacetophenone is halogenated with a halogen in the presence of a hydracid to form the polyalkenylphenacyl halide starting material (Col. 2, Ln. 46 – Col. 3, Ln. 29).
Example 1 illustrates acetylation of polystyrene to form poly(p-vinylacetophenone), followed by halogenation with hydrobromic acid and bromine to form poly(p-vinylphenacyl bromide), and subsequent oxidation with DMSO to form α-ketoaldehyde (–COCHO) functionalities on the aromatic ring (Col. 7, Ln. 38 – Col. 9, Ln. 51). The resulting polystyrylglyoxal sorbent binds urea in aqueous solution, with Examples 5 and 6 reporting urea uptake values of 51.5 g/kg and 61.5 g/kg under pH 7 and pH 10 conditions, respectively (Col. 12, Lns. 5–23). These values correspond to approximately 0.86 mmol/g and 1.02 mmol/g of urea, respectively.
Regarding the recited incubation conditions for determining urea binding capacity, the conditions define how the capacity is measured and do not add a separate production step to the claimed method. KUNTZ’s Examples 5 and 6 demonstrate that the produced polystyrylglyoxal sorbent is evaluated by incubation with aqueous urea solution, with reported uptake values corresponding to approximately 0.86 mmol/g and 1.02 mmol/g of urea, respectively.
Regarding the monomers of general formula (I) as recited in step (i), the sequence of acetylation, halogenation, and oxidation described in Example 1 modifies a polystyrene backbone to produce polymer units bearing α-ketoaldehyde (–COCHO) functionalities. These modified units correspond in structure to the polymer units that would result from converting non-PGA-type monomers into PGA-type monomers as recited in step (iii). The resulting phenylglyoxal-functionalized polymer binds urea in aqueous solution, demonstrating the same functional utility as the claimed PGA-type sorbent. Starting from monomers that provide acetophenone-type and phenacyl-halide-type units structurally similar to KUNTZ’s intermediate units (–COCH₃ and –COCH₂Br) would have been an obvious simplification of the known method, as it reduces the number of required post-polymer modifications while still achieving the same functionalized structure.
However, KUNTZ does not explicitly disclose the produced sorbent having a urea binding capacity of more than 1.85 mmol/g as determined under the recited incubation conditions.
POSS discloses similar macromolecular compositions comprising ketoaldehyde-functionalized polymers capable of chemically binding constituents of a fluid. The macromolecular ketoaldehydes include synthetic polymers such as polystyrene-based resins bearing reactive aldehyde groups for use as sorbents (¶[0008]). The polyvinylacetophenone polystyrene-divinylbenzene co-polymer resin is treated in DMSO with hydrobromic acid and heated, yielding the ketoaldehyde-functionalized resin (¶[0048]).
The experiments report urea uptake values under different incubation protocols:
Experiment
Urea condition
Time
Temp
Uptake
Reference
Experiment 3 / 7–12
60 mg/dL
8 h
37°C
8.8, 20.8, 45, and 47.3 mg/g
(¶[0073])
Experiment 14
505.8 mg/dL
24 h
50°C
109 mg/g
(¶[0077])
Experiment 15
1 g/L
2.5 h or 15 h
37°C
3.2, 19.8, 4.0, 12.8, and 7.5 mg/g
(¶[0079]); Table 2
Experiment 16
0.5 mol/L
15 h
37°C
90, 79, 17.15, and 30 mg/g
(¶¶[0080]–[0081]); Table 3
The 109 mg/g value from Experiment 14 corresponds to approximately 1.82 mmol/g based on a urea molar mass of 60.06 g/mol.
The ketoaldehyde-functionalized polystyrene-based sorbents disclosed by POSS provide guidance on how structurally similar reactive-aldehyde sorbents exhibit different urea uptake under different incubation protocols. In view of KUNTZ’s phenylglyoxal-functionalized polystyrylglyoxal sorbent, a person skilled in the art would have looked to POSS’s urea-uptake data to predictably optimize the measured urea binding capacity of KUNTZ’s produced sorbent.
Regarding the claimed urea binding capacity of more than 1.85 mmol/g under the recited incubation conditions, the claimed value is a measured performance result tied to the recited incubation protocol. POSS shows measured urea uptake depends on incubation protocols, including initial urea concentration, time, and temperature. Experiment 14 already reaches about 1.82 mmol/g using a 24-hour protocol. It would have been obvious to a person skilled in the art to optimize the incubation conditions, including urea concentration and temperature, to obtain the claimed measured urea binding capacity. Optimization of a known result-effective variable is obvious absent evidence that the selected value or conditions are critical or produce an unexpected result (In re Aller, 220 F.2d 454 (CCPA 1955); In re Peterson, 315 F.3d 1325 (Fed. Cir. 2003)).
Therefore, it would have been obvious to a person having ordinary skill in the art, prior to the effective filing date of the claimed invention, to apply the urea-uptake data and incubation-protocol guidance disclosed by POSS to optimize the measured urea binding capacity of the sorbent produced by KUNTZ.
Regarding Claim 2, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ illustrates acetylation of polystyrene to form poly(p-vinylacetophenone), followed by halogenation with hydrobromic acid and bromine to form poly(p-vinylphenacyl bromide), and subsequent oxidation with DMSO to form α-ketoaldehyde (–COCHO) functionalities on the aromatic ring (Col. 7, Ln. 38 – Col. 9, Ln. 51). These structures correspond to polymer units formed from the monomers recited in Claim 2, including 1-(4-ethenylphenyl)ethan-1-one (–COCH₃), 2-bromo-1-(4-ethenylphenyl)ethan-1-one (–COCH₂Br), and 1-(4-ethenylphenyl)ethan-1,2-dione (–COCHO), respectively.
Regarding Claim 3, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses sequential modification of a polystyrene backbone via acetylation, halogenation, and oxidation to introduce pendant side chains (Col. 7, Ln. 38 – Col. 9, Ln. 51). The pendant side chains fall within the scope of formula (II-p) of the instant application, including –COCH₃ (h¹ = h² = h³ = H), –CO–CHO (h¹ and h² together form ═O, h³ = H), and –COCH(OH)₂ (h¹ = h² = –OH, h³ = H). Using such intermediates as monomers instead of modifying the polymer after formation would have been an obvious process simplification, as it reduces the number of required post-polymer modification steps while achieving the same α-ketoaldehyde-functionalized polymer structure taught by KUNTZ.
Regarding Claims 4 and 5, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. KUNTZ discloses polymerizing monomers of the general formula shown in FIG. 1 with optional ethylenic comonomers and optional crosslinking by 0.1 to 30 mol % of a polyvinyl monomer such as divinylbenzene (Col. 1, Lns. 35–63).
Regarding Claim 6, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses that the conversion to the ketoaldehyde functionality includes a halogenation step, in which acetylated polystyrene is halogenated with hydrobromic acid and bromine to a phenacyl halide (–COCH₂Br), followed by oxidation with dimethyl sulfoxide to yield α-ketoaldehyde (–COCHO) units (Col. 7, Ln. 38 – Col. 9, Ln. 57). This corresponds to a conversion in step (iii) that comprises halogenation.
Regarding Claim 7, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses oxidation of a phenacyl bromide-functionalized polymer using dimethyl sulfoxide to introduce phenylglyoxal (–COCHO) groups. The resulting polymer contains 0.72 phenylglyoxal group per phenyl ring (Col. 9, Lns. 54–57). This indicates that approximately 72% of the polymerized monomer units have been converted into PGA-type monomers, which reads upon at least the claimed alternative of more than 70%.
Regarding Claim 8, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses preparation of poly(p-vinylacetophenone) by acetylating polystyrene, followed by further modification to form –COCH₃, –COCHO, and –COCH(OH)₂ side-chain groups (Col. 7, Ln. 38 – Col. 9, Ln. 51). The disclosed structures fall within Claim 8 because the vinyl substituent has Q = H, the side-chain groups include –COCH₃ (h¹ = h² = h³ = H), –COCHO (h¹ and h² = ═O, h³ = H), and –COCH(OH)₂ (h¹ = h² = –OH, h³ = H), and X = O.
Regarding Claim 16, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 4. KUNTZ discloses copolymerizing monomers of formula (I) with up to 50 mol % of a non-aromatic ethylenic comonomer and optionally 0.1–30 mol % of a polyvinyl crosslinker. Examples include styrene and α-methylstyrene, butadiene as a non-aromatic ethylenic comonomer, and divinylbenzene as a polyvinyl crosslinker (Col. 1, Lns. 35–63).
Regarding Claim 17, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses oxidation with dimethyl sulfoxide, in which poly(p-vinylphenacyl bromide) is treated in DMSO for 15 hours to convert phenacyl halide units to α-ketoaldehyde (–COCHO) groups and yield polystyrylglyoxal (Col. 7, Ln. 38 – Col. 9, Ln. 51).
Regarding Claims 18 and 19, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 6. Example 1 of KUNTZ discloses halogenation of poly(p-vinylacetophenone) using hydrobromic acid in acetic acid together with bromine to form a phenacyl halide intermediate (–COCH₂Br), followed by oxidation in dimethyl sulfoxide to yield α-ketoaldehyde (–COCHO) units (Col. 7, Ln. 38 – Col. 9, Ln. 51).
Regarding Claim 20, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 1. Example 1 of KUNTZ discloses aromatic-ring units formed during the sequence: acetylated units –COCH₃, phenacyl halide units –COCH₂Br, oxidized phenylglyoxal units –COCHO, and the hydrated aldehyde –COCH(OH)₂ (Col. 7, Ln. 38 – Col. 9, Ln. 51). These correspond to the h¹/h² alternatives as follows: –COCH₃ maps to h¹ = h² = H; –COCHO maps to h¹ and h² = ═O; –COCH(OH)₂ maps to h¹ = h² = –OH.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over KUNTZ in view of POSS as applied to claim 4 above, and further in view of DICKEY et al. (US2475424, hereinafter DICKEY).
Regarding Claim 21, modified KUNTZ makes obvious a method of producing a phenylglyoxaldehyde (PGA)-type sorbent of Claim 4. However, modified KUNTZ does not explicitly disclose “the comonomers are one or more selected from the group consisting of N,N′-methylenebisacrylamide (NMAA), N-methyl vinylsulfonamide, and N,N-dimethyl vinylsulfonamide.”
DICKEY discloses polymeric N-alkylsulfonyl and N-arylsulfonyl vinylamines and a process for their preparation (Col. 1, Lns. 1–3). The sulfonyl-vinylamine compounds can be copolymerized with one or more unsaturated compounds including vinylsulfon-dimethylamide (i.e., N,N-dimethyl vinylsulfonamide; Col. 1, Lns. 47–55).
In Example 6, a sulfonyl vinylamine is copolymerized with styrene using benzoyl peroxide at 80 °C to yield a moldable copolymer with styrene present from 1 to 99 parts. In Example 7, N-methyl-N-methylsulfonyl-vinylamine is copolymerized with methyl methacrylate using benzoyl peroxide at 60 °C to yield a moldable solid with monomer proportions variable from 1 to 99 parts (Col. 4, Lns. 4–47).
The N,N-dimethyl vinylsulfonamide disclosed by DICKEY is an ethylenically unsaturated comonomer compatible with copolymerization with styrene- and methacrylate-type monomers and provides a polar sulfonamide-containing comonomer for adjusting copolymer polarity and hydrophilicity. In view of KUNTZ’s copolymer framework, a person skilled in the art would have selected N,N-dimethyl vinylsulfonamide as a comonomer to adjust copolymer polarity and hydrophilicity, as its demonstrated copolymerization with styrene- and methacrylate-type monomers shows predictable compatibility with ethylenically unsaturated comonomer systems.
Therefore, it would have been obvious to a person having ordinary skill in the art, prior to the effective filing date of the claimed invention, to include N,N-dimethyl vinylsulfonamide, as disclosed by DICKEY, as a comonomer in the method of producing the PGA-type sorbent by modified KUNTZ.
Response to Arguments
Applicant’s arguments, see Remarks filed January 19, 2026, have been fully considered but are not persuasive. The rejection of Claims 1–8 and 16–21 under 35 U.S.C. § 103 is updated and maintained over KUNTZ, POSS, and DICKEY.
Applicant’s reliance on Table 5 of the instant specification is not persuasive because Claim 1 is directed to a method of producing a PGA-type sorbent, while the recited urea binding capacity is a measured product-performance property under an assay protocol, not a separate method step. Urea uptake is affected by known variables such as urea concentration, incubation temperature, and incubation time. Reciting a specific adjacent numerical threshold does not establish patentability where the prior art provides a close value and the claimed result is obtained by routine adjustment of known result-effective variables. Table 5 does not establish that the claimed threshold or assay conditions are critical over the closest prior art, nor does it show unexpected results commensurate with the full scope of Claim 1 (MPEP §§ 2144.05, 716.02(d), 716.02(e)).
Conclusion
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/TAK L. CHIU/Examiner, Art Unit 1777
/KRISHNAN S MENON/Primary Examiner, Art Unit 1777
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