DETAILED ACTION
Status of Application
This action is responsive to national-stage application filed 11/13/2023. The concurrently filed preliminary amendment having been entered, original claims 1, 2 and 9, and amended claims 3-8 and 10-15 are currently pending and under examination herein.
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 . However, 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 a 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.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) accompanying the application papers is in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies of the IDS are included with the mailing/transmittal of this Office action.
Foreign Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections – 35 U.S.C. 103
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 1-6, 8-12, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over JP S51 34295A (‘JP ‘295’; citing infra to machine-generated English language translation, furnished herewith) in view of Tsuhara et al (US 2018/0100055 A1) (‘Tsuhara’).
Regarding Claims 1-3, JP ‘295 discloses a method for producing anion exchangers (as acknowledged by Applicant, see page 2, first para. of instant specification). As disclosed, the method involves reacting a vinyl aromatic polymer with an organic nitrile and formaldehyde in a Friedel-Crafts catalyzed alkylation to produce an intermediate acylamino-methylated vinyl aromatic polymer, which is then hydrolyzed to convert the acylaminomethyl group into an aminomethyl group to afford an aminomethyl-substituted vinyl aromatic polymer (see ¶¶ [0002]-[0003]). The intermediate and obtained hydrolysate correspond respectively to instant formulae (IV) and (I), and acetonitrile is listed among examples of the organic nitrile used in the disclosed method (see ¶ [0003]) [for claims 2, 3].
As such, JP ‘295 differs from the present invention only in the use of polystyrene as the vinyl aromatic polymer reactant instead of chloromethylated, vinylaromatic polymer of instant formula (II). However, in analogous art relating to a method of producing an iminodiacetic acid chelating resin with excellent separation capacity (¶ [0001]), Tsuhara teaches a production method comprising steps of: a) chloromethylating a styrene-divinyl benzene (DVB) copolymer to obtain a crosslinked chloromethyl styrene-DVB copolymer; b) aminating the chloromethylated styrene copolymer in presence of iminodiacetonitrile and potassium iodide; and c) hydrolyzing the aminated crosslinked styrene copolymer using aqueous sodium hydroxide solution, to obtain the chelate resin (see ¶¶ [0159]-[0169] (Examples 2-7, Table 1)). Tsuhara thus demonstrates the viability of a chloromethylated styrene copolymer corresponding to instant formula (II) in an analogous reaction scheme involving an acetonitrile derivative followed by hydrolysis of an aminated intermediate. In light of such teaching and given JP ‘295’s broad disclosure indicating that the vinyl aromatic polymer used as raw material in the method of that invention includes “a vinyl compound having an aromatic nucleus” followed by mention of several alkyl-substituted styrene compounds like ethylstyrene and vinyltoluene (see ¶ [0003]), one of ordinary skill would have had a reasonable expectation of a chloromethylated analogue being similarly utile as the vinyl aromatic polymer raw material. Given a reasonable expectation of equivalent performance, it would have been prima facie obvious to one of ordinary skill in the art at the time of effective filing to modify the method of JP ‘295 by replacing the vinyl aromatic polymer with a chloromethylated vinyl aromatic polymer of instant formula (II) as taught by Tsuhara, and thereby arrive at the present invention.
Regarding Claims 4-6, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. JP ‘295 further discloses specific species of metal(II) and metal(III) salts as the employed metal-containing catalyst, specifically Lewis acids such as aluminum chloride, ferric chloride (i.e., iron (III) chloride) and zinc bromide (see ¶ [0003]), as claimed.
Regarding Claims 8-9, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Further, in modified JP ‘295, the employed chloromethylated, vinylaromatic polymer of formula (II) would be a chloromethylated styrene-divinylbenzene copolymer of formula (II) as taught by Tsuhara.
Regarding Claim 10, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. JP ‘295 further teaches that the amount of nitrile, formaldehyde and catalyst are used in an amount of from 3 to 70 mol, preferably from 3 to 1 mol, per mol of the aromatic nucleus present in the polymer (see ¶ [0003]), and in modified JP ‘295, the same ranges would necessarily apply to the amount of chlorine in the substituted chloromethylated, vinylaromatic polymer of formula (II) as taught by Tsuhara.
Regarding Claim 11, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Further, the aforementioned disclosed ranges overlap claimed range for amount of catalyst, and in modified JP ‘295, the same ranges would necessarily apply to the amount of chlorine in the substituted chloromethylated, vinylaromatic polymer of formula (II) as taught by Tsuhara.
Regarding Claim 12, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Tsuhara further characterizes the styrene-divinyl benzene (DVB) copolymer used in Examples 1-6 (Table 1) as having degree of crosslinking (%) ranging from 5 to 6, and defines degree of crosslinking to mean a ratio of a crosslinking aromatic monomer to the total amount of a monovinyl aromatic monomer and a crosslinking aromatic monomer (see ¶¶ [0051]-[0052]). Accordingly, the reported crosslinking degrees are seen to reflect a copolymer composition where the proportions styrene and DVB correspond to mol% values within the respective ranges claimed for monovinylaromatic monomer and polyvinylaromatic monomer.
Regarding Claim 14, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above, and Tsuhara teaches that the hydrolysis in step b) is performed at a temperature of 80oC to 250oC, specifically 80oC (see ¶ [0169] (Table 1), Examples 1-6).
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over JP ‘295 in view of Tsuhara as applied to claim 1 above, and further in view of Feng et al (Journal of Chemical Research 2018, vol. 42, July, 383-386) (‘Feng’).
Regarding Claim 7, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Neither reference directly discloses that the employed metal-containing catalyst is zinc (II) perchlorate. Nevertheless, JP ‘295 broadly teaches to use known Friedel-Crafts catalysts, including Lewis acids (see ¶ [0003]). Feng describes the synthesis of amides from nitriles and halohydrocarbons, including PhCH2Cl, employing zinc (II) perchlorate hexahydrate [Zn(ClO4)2 · 6H2O] (see p. 383, final para of left-hand column). Feng shows that the employment of Zn(ClO4)2 · 6H2O led to a cleaner reaction of benzyl chloride and benzonitrile and produced amide 1a with the highest yield of 92% after 5h, compared to the same reaction using Zn(OTf)2 (see p. 383, first full para of right-hand column and p. 384, Table 1, entry 4). Feng further recognizes Zn(ClO4)2 · 6H2O as an economically effective catalyst for the synthesis of amides from nitriles with halohydrocarbons under mild protocol conditions (see p. 384, first full para of right-hand column). Motivated by an expectation of a similar improvement in product yield and favorable economics, it would have been obvious to one of ordinary skill in the art at the time of effective filing to further modify the method of JP ‘295 by performing the acylamino-methylation reaction in the presence of a zinc (II) perchlorate as taught by Feng.
Claims 13 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over JP ‘295 in view of Tsuhara as applied to claim 1 above, and further in view of Harris (US 5231115).
Regarding Claim 13, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Neither reference directly discloses that the chloromethylated, vinyl aromatic polymer of formula (II) is produced according to recited step 1a). Tsuhara does, however, teach to use a styrene crosslinked polymer that is a gel type or a porous type (¶ [0050]). Further, in the same technical field, Harris generally teaches to produce porous copolymer beads by a seeded polymerization process employing gel copolymer seed particles prepared by polymerization of at least one first monovinylidene monomer and a crosslinking aromatic monomer (see Abs. and Col. 2, lines 35-40). Harris in Example 1 details the seed preparation conditions as including suspending in a continuous aqueous suspension medium, a first monomer solution comprising styrene, a divinylbenzene solution and two particular free radical initiators, and reacting the suspended monomer mixtures to obtain the seed particles. Given the continuous suspension medium, it is implicit that the monovinylaromatic compound (styrene) and the polyvinylaromatic compound (DVB) existed as monomer droplets during the polymerization, per claimed step 1a). Harris then teaches to convert the porous copolymer beads to anion-exchange resins by conventional methods, including a chloromethylation reaction (see Col. 11, line 62 et seq.). Given the applicability of the seeded polymerization process of Harris to produce porous copolymer beads suitable for conversion to anion-exchange resins, it would have been obvious to one of ordinary skill in the art at the time of effective filing to further modify the method of JP ‘295 by utilizing the chloromethylated vinyl aromatic polymer of instant formula (II) as taught by Tsuhara, and produced according to claimed steps 1a) and 1b) as per Harris.
Regarding Claim 15, JP ‘295 in view of Tsuhara renders obvious the process as claimed in claim 1 as discussed above. Neither reference directly discloses that step a) employs a chloromethylated, macroporous, vinylaromatic polymer formula (II). However, in Harris Example 1 the recovered, porous copolymer beads are characterized by an average pore radius of 320 Angstroms (see Col. 11, lines 36-44), for an average pore diameter of 640 Angstroms, which equates to 64 nm, a value well within the preferred range given in the instant specification (at p. 4, lines 19-22) for average diameter of the pores of the macroporous polymers of the chloromethylated, vinylaromatic polymers of claimed formula (II). Accordingly, the proposed further modification of JP ‘295 discussed above with respect to claim 13 would have been expected to fulfill the “macroporous” requirement of claim 15.
Conclusion
Claims 1-15 are rejected. No claims are in condition for allowance at this time.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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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) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/06-26-26
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