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 .
Response to Arguments
Applicant’s arguments, see pages 8-9, filed 14 July 2026, with respect to the 112 rejections have been fully considered and are persuasive. The 112 rejections of claims 1-20 have been withdrawn.
Applicant's arguments filed 14 July 2026 regarding the 103 rejections have been fully considered but they are not persuasive. The rejection is being reapplied to include claims 2, 4, 10-13, and 15.
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.
Claims 1, 2, and 4-20 are rejected under 35 U.S.C. § 103 as being unpatentable over Tong et al. (US 7,005,087, hereinafter “Tong”) in view of Blatch et al. (US 9,884,951, hereinafter “Blatch”) and further in view of Blaschke et al. (US 7,182,839, hereinafter “Blaschke”).
Claim 1 recites a composition for mitigating monomer polymerization comprising a dispersing agent comprising an imidazoline or derivative thereof, a solvator agent comprising a phthalate or derivative thereof, and a promoter agent comprising an acylamide or derivative thereof.
Tong teaches aminoalkyl imidazoline antifoulants for preventing fouling in (meth)acrylic acid processes. Tong teaches that the imidazoline antifoulants may be used neat or blended with a suitable solvent and further teaches use in combination with polymerization inhibitors, dispersant antifoulants, and solvents. Tong expressly states that these components may be injected together as part of a single combined formulation. See Tong, claims 1 and 7-10; specification discussing solvent formulations and combined injection.
Blatch teaches the use of phthalate solvents for reducing polymer fouling, agglomeration, precipitation, and deposition in acrylate, methacrylic acid, and methacrylate processes. Blatch teaches phthalates having ester substituents independently selected from hydrogen, alkyl, alkaryl, or aryl and expressly identifies dimethyl phthalate and diethyl phthalate. Blatch further demonstrates that dimethyl phthalate maintains polymer in a dispersed state in an acidic methyl methacrylate process stream. See Blatch, claims 1 and 9-18 and Example 1.
Blaschke teaches treating fouling-agent-containing process streams with N,N-disubstituted amides which act as dispersants for the fouling agents and prevent agglomeration and deposition. Blaschke teaches a broad structural genus of such amides and expressly teaches N,N-dialkyl amides as antifouling agents. See Blaschke, claims 10 and 17-37.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify Tong's combined imidazoline antifoulant formulation by employing the phthalate solvent taught by Blatch and the N,N-disubstituted amide dispersant taught by Blaschke. Tong expressly contemplates combining its imidazoline antifoulant with solvents and dispersant antifoulants in a single formulation. Blatch identifies phthalates as effective solvents for maintaining polymer foulant in a dispersed state in closely related acrylic and methacrylic process streams, and Blaschke identifies N,N-disubstituted amides as effective dispersants for inhibiting polymer-derived fouling. The respective components would have been expected to retain their recognized antifouling, solvation, and dispersion functions upon combination.
Regarding claim 2, the additional Formula I limitations do not patentably distinguish the composition. Tong expressly teaches aminoalkyl imidazolines of Formula I wherein the linking group R is C1-C6 alkylene, n is an integer from 1 to about 9, R1, R2, and R3 are independently selected from alkyl, alkenyl, aryl, alkylaryl, arylalkyl, aminoalkyl, and aminoaryl groups, and R4 includes hydrogen, carboxyalkyl, imidazoline, alkyl, and alkylaryl alternatives. See Tong, claim 1. Tong's C1-C6 alkylene falls within the broader alkylene genus presently recited in claim 2, and its substituent classes overlap the alternatives recited in claim 2. Tong's n=1-9 embodiments likewise fall within amended claim 2 notwithstanding claim 2's additional inclusion of n=0. Thus, the additional structural limitations of claim 2 would have been obvious in the applied combination.
Regarding claim 4, claim 4 further limits R of Formula I to C1-C10 alkylene. Tong expressly teaches C1-C6 alkylene for the corresponding linking group. See Tong, claim 1. The disclosed C1-C6 genus lies within the C1-C10 range of claim 4. Therefore, claim 4 does not distinguish over Tong in combination with Blatch and Blaschke.
Regarding claim 5, Tong expressly teaches imidazolines prepared from oleic acid and teaches tall-oil-fatty-acid-derived imidazolines. In Example 3, Tong employs oleic acid/DETA imidazoline and reports a substantial reduction in polymer formation and deposition. Tong further teaches TOFA-derived imidazoline species, including hydroxyethyl-containing imidazoline chemistry. Thus, Tong teaches or at least suggests the species recited in claim 5.
Regarding claim 6, Blatch teaches the claimed phthalate structural class. Blatch's Formula 1 provides R1 and R2 independently selected from hydrogen, alkyl, alkaryl, or aryl and specifically provides C1-C12 alkyl embodiments. See Blatch, claims 9-10. The disclosed dimethyl and diethyl phthalate species are encompassed by the structural genus of claim 6.
Regarding claim 7, Blatch expressly teaches dimethyl phthalate and diethyl phthalate, both of which are expressly recited alternatives in claim 7. See Blatch, claims 11-15. Disclosure of a species falling within the claimed closed group is sufficient to meet that alternative.
Regarding claim 8, Blaschke teaches N,N-disubstituted amides having substituents selected from hydrogen, alkyl, alkenyl, aryl, aralkyl, and alkaryl groups. The disclosed amide genus therefore encompasses compounds within Formula III of claim 8. See Blaschke, claims 17-37.
Regarding claim 9, Blaschke teaches the N,N-disubstituted-amide class and expressly identifies N,N-dimethylformamide and N,N-dimethylacetamide in the solvent-recovery system. The rejection does not depend on characterizing DMF or DMAc themselves as Blaschke's preferred antifoulant; rather, Blaschke's express identification of the species together with its teaching of the encompassing N,N-disubstituted-amide dispersant class would have suggested the claimed amide species to one of ordinary skill in the art.
Regarding claim 10, the amount of promoter agent does not establish patentability. Blaschke teaches that an additive may contain up to 100% N,N-dimethylamide and expressly identifies a preferred formulation containing 10% N,N-dimethyl amide, 40% butyl carbitol, and 50% water. Thus, the prior art expressly recognizes the concentration of the amide active ingredient as a formulation variable and teaches an amount falling squarely within the claimed 0.1-99.9 wt.% range.
Further, Blaschke instructs that the optimum amount of dispersant for a particular system is readily determined by a simple dosage test and evaluates increasing doses to determine the amount providing optimum fouling control. Accordingly, selecting the concentration of the amide promoter within the broad range recited in claim 10 would have constituted routine optimization of a variable expressly recognized in the art as affecting the desired fouling-control result. See MPEP § 2144.05.
Regarding claim 11, the claimed concentrations of the dispersing agent and solvator agent likewise do not render the composition nonobvious. Tong teaches using its imidazoline antifoulant either neat or formulated with solvent and expressly recognizes formulation concentration as relevant to handling, injection, and distribution. Blatch teaches phthalate concentrations from about 10 ppm to about 1 wt.% in the process fluid and about 100-1000 ppm where the phthalate is used to disperse or prevent polymer agglomeration, precipitation, or deposition. The references thus expressly teach varying the amounts of the imidazoline and phthalate components according to their desired antifouling and solvation effects. Once the components are placed together in Tong's contemplated single combined formulation, selection of workable concentrations of each within the extremely broad 0.1-99.9 wt.% interval would have been within ordinary formulation skill. No criticality of the claimed concentration interval is apparent from the claim itself.
Regarding claim 12, Tong teaches preferred imidazoline treatment dosages of about 30-300 ppm and broader dosages of about 1-10,000 ppm. Blatch teaches about 100-1000 ppm phthalate when employed to disperse or prevent polymer agglomeration. These disclosed effective dosage ranges readily provide dispersing-agent-to-solvator-agent ratios within the claimed 1:10 to 10:1 range when the components are administered together in the single combined formulation expressly contemplated by Tong. For example, a Tong dosage of 30 ppm imidazoline together with 100 ppm phthalate corresponds to a 3:10 relative active-weight ratio, which falls within claim 12.
Moreover, both references expressly recognize component amount as affecting the desired fouling-control result. Accordingly, adjustment of the relative amounts to obtain an effective combined treatment would have amounted to optimization of recognized result-effective variables. MPEP § 2144.05 requires factual support and articulated reasoning for such an optimization rationale; those requirements are met here by the references' disclosed dosage ranges and express teachings regarding selection of effective amounts.
Regarding claim 13, Tong expressly claims a composition comprising (meth)acrylic acid and an aminoalkyl imidazoline. See Tong, claim 1. Thus, Tong directly teaches an imidazoline-containing composition further comprising a monomer. Blatch additionally treats process fluids employed in the preparation of acrylate, methacrylic acid, and methacrylate monomers. The further inclusion of a monomer therefore does not distinguish the claim from the applied combination.
Regarding claim 14, Tong teaches acrylic acid and methacrylic acid process streams, while Blatch expressly teaches acrylate, methacrylic acid, methacrylate, methacrylamide, and other ethylenically unsaturated or vinyl monomer systems. See Blatch, claims 1 and 7-8. Accordingly, the ethylenically unsaturated monomer limitation of claim 14 would have been obvious.
Regarding claim 15, the claim recites alternative monomers including methacrylic acid, methyl methacrylate, acrylic acid, and acrylic acid esters. Tong expressly teaches acrylic acid and methacrylic acid and processes involving their esters. Blatch expressly teaches methyl methacrylate, methacrylic acid, acrylates, and methacrylates. Because claim 15 is written in the alternative, disclosure of one or more of the expressly recited monomers is sufficient to meet the limitation.
Regarding claim 16, Tong expressly teaches combining its imidazoline antifoulants with one or more polymerization inhibitors. See Tong, claims 7 and 9 and the discussion of combined formulations. Claim 16 recites a polymerization inhibitor “or” an antioxidant; therefore, Tong's disclosure of the polymerization-inhibitor alternative satisfies the claim.
Regarding claim 17, Tong teaches adding its imidazoline antifoulant to polymerizable (meth)acrylic-acid process streams. Tong further reports reduced polymer formation and deposition when its imidazoline treatments are used. Blatch teaches adding the phthalate to corresponding monomer-processing streams, and Blaschke teaches adding an N,N-disubstituted amide in an amount effective to inhibit fouling. Even if the phrase “inhibiting polymerization of a monomer” is accorded patentable weight, the combined teachings provide a reasonable expectation that the resulting composition would reduce polymer formation and associated fouling. Blaschke additionally recognizes that its amide dispersant's observed fouling inhibition may result in part from limiting polymerization of reactants in the stream.
Regarding claim 18, Tong teaches compatible formulations and process streams containing water, acetic acid, acrylic acid, methacrylic acid, acrylic and methacrylic esters, and organic extraction solvents. Blatch expressly teaches aqueous sulfuric-acid process fluids together with the phthalate solvent. Accordingly, the acid, organic-solvent, and water alternatives of claim 18 are taught or suggested by the references.
Regarding claim 19, Tong teaches acrylic acid, methacrylic acid, acrolein, and acrylonitrile processing systems. Blatch expressly teaches foulants derived from ethylenically unsaturated or vinyl monomers, including acrylic acid, acrylates, methacrylic acid, methacrylates, and methacrylamide. The additional limitation therefore does not distinguish the claim.
Regarding claim 20, Tong teaches adding its imidazoline antifoulant at about 1-10,000 ppm, preferably about 10-1000 ppm and more preferably about 30-300 ppm. Blatch teaches phthalate concentrations of about 10 ppm to about 1 wt.% and about 100-1000 ppm for dispersing or preventing agglomeration. Blaschke teaches that an effective dispersant amount typically is about 1-1000 ppm and preferably about 10-100 ppm. These known effective treatment ranges permit combined dosages falling within the claimed total-composition range of about 0.01-10,000 ppm. The references also expressly direct the artisan to determine effective treatment amounts based upon observed fouling performance. Accordingly, selecting an effective total dosage within the broad claimed range would have constituted routine optimization of known result-effective treatment amounts.
For the reasons above, the differences between claims 1, 2, and 4-20 and the combined teachings of Tong, Blatch, and Blaschke amount to the selection and combination of known antifouling, solvating, and dispersing components and the selection of workable amounts and proportions thereof for their known functions. The references provide both a reason to make the combination and a reasonable expectation that each component would retain its known function. Accordingly, claims 1, 2, and 4-20 would have been obvious under 35 U.S.C. § 103.
Allowable Subject Matter
Claim 3 objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
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/DEBORAH D CARR/Primary Examiner, Art Unit 1691
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