DETAILED ACTION
Status of Application
This action is responsive to nonprovisional application filed 03/28/2023. Original claims 1-20 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) filed on 01/03/2024, 04/15/2024, 10/04/2024, 01/27/2025 and 01/06/2026 are 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.
Objection – Claim(s)
Claim 17 is objected to because of the following informalities: referring to line 5, “and” should read –or-- to clarify that the enumerated groups represent alternative selections for R4 (cf., penultimate line of same claim). Appropriate correction is required.
Claim Rejections – 35 U.S.C. 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 3 and 20 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.
Regarding Claim 3, recitation of “R1” in reference to “[t]he composition of claim 1” engenders confusion, as no precedent is provided in the base claim for this variable. For purposes of substantive examination, it is presumed that claim 3 was intended to depend from claim 2, wherein R1 first appears in recited formula (I); however, clarification and appropriate correction are required.
Regarding Claim 20, recited limitation to “the step of purging …” lacks proper and sufficient antecedent basis in the claim, or in any claim upon which claim 20 depends (currently, claim 17). For purposes of substantive examination, it is presumed that claim 20 was intended to depend from claim 19, wherein precedent is provided for “purging”; however, clarification and appropriate correction are required.
Common Ownership Notice
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim Rejections – 35 U.S.C. 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 8-10, 12-14 and 16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sakamoto et al (US 2001/0005755 A1) (‘Sakamoto’).
Regarding Claims 1 and 16, reference to Sakamoto relates to the stabilizing of N-oxyl compounds that have been added to vinyl compounds as a polymerization inhibitor, by allowing the N-oxyl compound in the vinyl compounds to co-exist with an N-hydroxy-2,2,6,6-tetramethylpiperidine compound and a 2,2,6,6-tetramethylpiperidine compound ([0006], [0008]). Sakamoto in Example 1 describes an acrylic acid solution composition comprising 4-hydroxy-2,2,6,6-tetramethylpiperidinoxyl (4H-TEMPO) and 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine (1,4DH-TEMP) in equal concentrations of 100 ppm ([0028] (TABLE 1). As such, the described composition comprises specific species of instant “first inhibitor compound comprising a stable nitroxide radical” (4H-TEMPO) and “second inhibitor compound comprising a hydroxylamine” (1,4DH-TEMP) [for claim 1] which co-exist at concentrations well within the claimed ranges for concentration of each inhibitor compound [for claim 16].
Regarding Claims 8-10, the aforementioned concentrations of 4H-TEMPO and 1,4DH-TEMP in Example 1 of Sakamoto equate to 0.01% by weight of each compound in the described composition, which falls within the claimed ranges for “first inhibitor compound” and “second inhibitor compound,” respectively [for claims 8, 9]. Further, given their close proximity in respective molecular weights (4H-TEMPO: 172.24 g/mol; 1,4DH-TEMP: 173.25 g/mol) and the breadth of claimed mole ratio range (about 100:1 to about 1:100), it is plausible to infer that the reported concentrations (100 ppm) will equate to mole ratio values within the clamed range as well [for claim 10].
Regarding Claims 12-13, Sakamoto in Example 1 further describes the composition further comprising an ethylenic unsaturated monomer, namely acrylic acid.
Regarding Claim 14, Sakamoto further describes adding to a vinyl compound (monomer) a composition comprising the N-oxyl compound and the N-hydroxy-2,2,6,6-tetramethylpiperidine ([0022]) in accordance with the claimed method.
Claims 1, 12 and 14-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Loyns et al (US 9133288 B2) (‘Loyns’).
Regarding Claim 1 and 16, reference to Loyns is directed to compositions for retarding polymerization reactions, the compositions comprising at one quinone compound (i) and at least one hydroxylamine (ii) and optionally at least one stable free radical compound (iii) (col. 5, lines 33-40 and 62 et seq.). Loyns concretely describes a vinyl aromatic monomer composition comprising 210 ppm DBHA and 35 ppm Hydroxy tempo (col. 9 line 54 et seq. (TABLE 2) Exp. No. 15) [for claim 16]; wherein DBHA and Hydroxy tempo are abbreviations for N,N-dibenzylhydroxylamine and 4-hydroxy-2,2,6,6-tetramethylpiperidine, respectively (col. 7, lines 19-20 and col. 8, lines 12-13). As such, the described composition comprises specific species of instant “first inhibitor compound comprising a stable nitroxide radical” (Hydroxy tempo) and “second inhibitor compound comprising a hydroxylamine” (DBHA) [for claim 1].
Regarding Claim 12, Loyns in Exp. 15 further describes a vinyl aromatic monomer composition further comprising an ethylenic unsaturated monomer, namely styrene (col. 9, 51-52).
Regarding Claim 14, Loyns in Exp. 15 further describes adding a polymerization retarder mixture (i.e., composition) comprising 210 ppm DBHA and 35 ppm Hydroxy tempo to a vinyl aromatic monomer in accordance with the claimed method.
Regarding Claim 15, Loyns discloses the method of claim 14 as discussed above, and further discloses providing the monomer within one or more carrier solvents and/or co-solvents which are added to process streams comprising ethylenically unsaturated compounds (col. 7, lines 30-51).
Claims 17-18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CN 113024447A (‘CN ‘447’) (citing infra to corresponding machine translation, furnished herewith).
Regarding Claims 17-18, CN ‘447 discloses a synthetic method for preparing 2,2,6,6-tetramethylpiperidine nitroxide radical-4-yl acetate (corresponding to claimed formula (III) where R3 is -O· and R4 is a C1 alkyl (methyl) ([0017]-[0018]). Disclosed embodiments describe reacting (i.e., treating) a 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy free radical (corresponding to claimed formula (IIIa)) with ester reactants ([0020]-[0021]). Examples 1-3 thereof ([0035]-[0040]) detail synthetic methods wherein the ester reactant is ethyl acetate (corresponding to claimed formula (IIIb) where R4 is a C1 alkyl (methyl) and R5 is C2 alkyl) and wherein the 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy free radical is treated with ethyl acetate in the presence of a catalyst (e.g., tetrabutyl titanate) and heat (e.g., temperature of 78oC maintained for 6 hours, per Example 1) [for claim 18].
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 1-9, 11-12, and 14-16 are rejected under 35 U.S.C. 103 as being unpatentable over Masere et al (US 2020/0017610 A1) (‘Masere’).
Regarding Claim 1, reference to Masere is directed to compositions and methods for inhibiting polymerization of monomers, wherein the compositions and methods use a polymerization inhibitor, a polymerization retarder, and an amine compound, wherein the amine compound acts as a stabilizer which improves the functionality of the polymerization inhibitor and stabilizer when used together ([0011]). In disclosed embodiments, the polymerization inhibitor is a nitroxide or hydroxylamine-containing compound ([0035]). More specifically, Masere teaches that the nitroxide containing compound can be a compound having a piperidinoxy group group according to formula XVI ([0047]) and that the hydroxylamine-containing compound can be a compound having a piperidinol group according to formula XVII ([0049]).
Masere differs from the claimed subject matter in failing to disclose, in a single embodiment, a composition comprising first inhibitor compound comprising a stable nitroxide radical; and second inhibitor compound comprising a hydroxylamine. However, Masere does disclose embodiments wherein specific species of compounds according to each of formulae XVI and XVII, namely 4-acetate TEMPOH and 4-acetate TEMPO, are included in separate styrene solutions in admixture with QMPh (as polymerization retarder) with or without a stabilizer compound ([0137]-[0140] (Examples 10-11), [0145]-[0146] (Example 14)). As such, Masere teaches 4-acetate TEMPOH and 4-acetate TEMPO as individually effective in inhibiting polymerization of styrene monomer. Accordingly, at the time of effective filing, it would have been obvious to one or ordinary skill in the art to modify the composition of Masere by utilizing as the polymerization inhibitor a combination of nitroxide and hydroxylamine-containing compounds, specifically 4-acetate TEMPO and 4-acetate TEMPOH, respectively, with a reasonable expectation of obtaining a composition displaying equivalent activity in inhibiting monomer polymerization. See MPEP 2144.06 (prima facie obvious to combine two composition each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose).
Regarding Claims 2-3, the 4-acetate TEMPO included in aforementioned modified composition of Masere corresponds to claimed formula (I) where R1 is -C(O)(C1 to C22 alkyl).
Regarding Claims 4-5, the 4-acetate TEMPOH included in aforementioned modified composition of Masere corresponds to claimed formula (II) where R2 is -C(O)(C1 to C22 alkyl).
Regarding Claims 6-7, the 4-acetate TEMPO and 4-acetate TEMPOH included in aforementioned modified composition of Masere correspond respectively to the first compound depicted in each of said claims.
Regarding Claims 8-9, Masere renders obvious the composition of claim 1 as discussed above. Masere further discloses embodiments wherein the composition includes the polymerization inhibitor in an amount in the range of 5 to 50% (wt) ([0089]), which amount is subsumed by the claimed ranges for concentration of first and second inhibitor compound. In light of such disclosure, an ordinarily skilled artisan would have been led to modify the composition of Masere by adding a combination of nitroxide and hydroxylamine-containing compounds, such as 4-acetate TEMPO and 4-acetate TEMPOH, in relative proportions adjusted to provide the prescribed amount of 5 to 50 wt.% of polymerization inhibitor. And given the breadth of the claimed ranges, one would reasonably expect such selected amounts of the respective compounds to fall within scope of said claims.
Regarding Claim 11, Masere renders obvious the composition of claim 1 as discussed above. Masere further claims embodiments wherein the inhibitor may be a combination of nitroxide compounds selected from 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO), 4-hydroxy-2,2,6,6-tetramethylpiperidinyl-1-oxyl (HTMPO), 4-oxo-2,2,6,6-tetramethylpiperidinyl-1-oxyl(OTEMPO), and 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one, (page 17, claim 11). TEMPO and HTMPO correspond to species of the additional compounds recited in present claim 11 and as discussed above, Masere teaches that nitroxide containing compounds having a piperidinoxy group and hydroxylamine-containing compounds having a piperidinol group are individually effective as monomer polymerization inhibitors. Accordingly, at the time of effective filing, it would have been obvious to one or ordinary skill in the art to further modify the composition of Masere by including one or both of TEMPO and HTMPO as an additional polymerization inhibitor compound, with a reasonable expectation of the resultant composition displaying comparable effectiveness in inhibiting monomer polymerization.
Regarding Claim 12, the aforementioned examples of Masere further disclose a composition comprising an ethylenic monomer, namely styrene.
Regarding Claims 14-15, Masere renders obvious the composition of claim 1 as discussed above. Masere further teaches a method comprising adding the disclosed composition to a monomer ([0016], [0096]) [for claim 14], wherein the monomer is provided within a solution ([0084], [0116]) [for claim 15]. In light of such teachings, it would have been obvious to one of ordinary skill in the art to practice the disclosed method utilizing the aforementioned modified composition of Masere, with a reasonable expectation of success.
Regarding Claim 16, Masere renders obvious the method of claim 14 as discussed above. Masere further discloses embodiments wherein at a polymerizable monomer concentration in the range of 50 to 200 ppm, the inhibitor can be introduced to provide an amount in the range of 15 to 60 ppm, and at a polymerizable monomer concentration in the range of 100 to 150 ppm, the inhibitor can be introduced to provide an amount in the range of 25 to 50 ppm ([0100]); wherein both disclosed ranges for inhibitor amount are embraced by the claimed ranges for concentration of each of the first and second inhibitor compound. In light of such disclosure, an ordinarily skilled artisan would have been led to modify the method of Masere by adding to the monomer a composition comprising a combination of nitroxide and hydroxylamine-containing compounds, such as 4-acetate TEMPO and 4-acetate TEMPOH, in proportions adjusted to provide the prescribed amount of inhibitor based on the monomer concentration. Further, given the breadth of the claimed concentration ranges, one would reasonably expect such selected amounts of the respective compounds to fall within scope of claim 16.
Potentially Allowable Subject Matter
Claim 19 is objected to as being dependent on a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claim.
Claim 20 would be allowable if amended or rewritten to overcome the rejection under 35 U.S.C. 112 set forth in this Office action and to include all the limitations of the base claim and any intervening claim.
The closest prior art to CN ‘447, discussed above, does not describe the inventions of instant claims 19-20, or provide proper rationale for modifying its disclosed invention into the invention of instant claim 19 or 20.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Robert Jones, can be reached at (571) 270-7733. The appropriate fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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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/04-02-26