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 .
Claim Rejections - 35 USC § 103
Claims 1, 4-5, 7, 20, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Hashimoto (U.S. Pat. No. 5,298,038) in view of Cherpeck (U.S. PG Pub. No. 2012/0151830).
In column 1 lines 10-16 Hashimoto discloses a fuel composition comprising an additive. Hashimoto discloses that the fuel can be gasoline or light oil useful for a diesel engine, meeting the limitations of the hydrocarbon-based fuel of claim 12. In Syntheses 8-10 (column 11 line 45 through column 12 line 40), Hashimoto discloses additives which meet the limitations of the amine-based detergent of amended claim 1 where R1 is a branched alkyl group having 14 or 16 carbons, R2 is hydrogen, and m is 3. In column 10 lines 23-24 Hashimoto discloses that the additive is present in an amount of 1 to 20,000 ppm, encompassing the ranges recited in claims 1, 5, and in the examples (column 15 lines 13-15) Hashimoto discloses compositions comprising 100, 200, and 400 ppm of the additive, within the ranges recited in claims 1 and 5. In column 10 lines 25-27 Hashimoto discloses that the composition can comprise a metal deactivator (“metal-inactivating agent”) and a demulsifier (“anti-emulsifying agent”), as recited in claim 7. Hashimoto does not disclose the inclusion of a further nitrogen-containing detergent, and does not specifically disclose the boiling points of the solvent.
Cherpeck discloses in paragraph 65 compositions comprising a major amount of hydrocarbons boiling in the gasoline range, and preferably 50 to 1000 ppm of a nitrogen-containing detergent additive. In paragraph 66 Cherpeck discloses that the nitrogen-containing detergent can be a hydrocarbyl-substituted amine where the hydrocarbyl group has a number average molecular weight of about 700 to 3,000, encompassing the range recited for the polyisobutenyl amine of amended claim 1, and where preferred hydrocarbyl-substituted amines are polyisobutenyl amines, as recited in amended claim 1, and can be polyisobutenyl monoamines, meeting the limitations of claim 4, or polyamines, as recited in claim 20. In paragraph 67 Cherpeck discloses that the nitrogen-containing detergent can be an alkylphenyl poly(oxyalkylene)monoamine where the oxyalkylene can be oxybutylene, the alkyl group on the alkylphenyl moiety preferably has 1 to 24 carbon atoms, and there are 5 to 100 oxyalkylene repeat units, overlapping the ranges recited for the alkylphenol-substituted poly(oxybutylene) of amended claim 1. Cherpeck further discloses that an especially preferred alkyl group has 12 carbon atoms, within the range recited in amended claim 1. In paragraph 70 Cherpeck discloses that the nitrogen-containing detergent can be a Mannich reaction product, where the alkyl-substituted hydroxyaromatic reactant is preferably a polyalkylphenol where the polyalkyl group has an average molecular weight of 600 to 3000, and the amine can be diethylene triamine, meeting the limitations of the Mannich reaction product of amended claim 1, as well as newly added claims 25-26. Cherpeck discloses that an especially preferred Mannich reaction product is prepared from a polyisobutylphenol where the polyisobutyl group has an average molecular weight of 1000, within the range recited for the polyalkyl group of amended claim 1. In paragraphs 71-72 Cherpeck discloses that the nitrogen-containing detergent can be a polyalkylphenoxyaminoalkane where the polyalkyl group has an average molecular weight of 600 to 5000, overlapping the range recited for the polyalkyl group of the polyalkylphenoxyaminoethane of amended claim 1, and the preferred structure has an aminoethane as the aminoalkane moiety, meeting the limitations of the polyalkylphenoxyaminoalkane of amended claim 1. The nitrogen-containing detergent concentration of 50 to 1000 ppm disclosed by Cherpeck encompasses the range recited in amended claim 1. See MPEP 2144.05(I): “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976);” "[A] prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prima facie case of obviousness." In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003). The inclusion of one or more of the above-described nitrogen-containing detergents of Cherpeck in the composition of Hashimoto, in the concentration disclosed by Cherpeck, produces a composition meeting the limitations of claims 1, 4-5, 7, 20, and 25.
It would have been obvious to one of ordinary skill in the art to include the nitrogen-containing detergent(s) of Cherpeck in the composition of Hashimoto, since Cherpeck teaches that they are effective detergents for gasoline fuel compositions, and it would have been obvious to one of ordinary skill in the art to include the nitrogen-containing detergent(s) of Cherpeck in the concentration range disclosed by Cherpeck since Cherpeck teaches that it is a suitable concentration range for the detergents in a gasoline fuel.
Claims 1, 4-5, 7-8, 11, 20, 22, and 25-26 are rejected under 35 U.S.C. 103 as being unpatentable over Wolf (U.S. PG Pub. No. 2013/0227878) in view of Cherpeck (U.S. PG Pub. No. 2012/0151830).
In paragraph 26 Wolf discloses an oxygenated gasoline composition comprising a gasoline blend stock, meeting the limitations of the hydrocarbon-based fuel boiling in the gasoline range of claims 1, and a corrosion inhibitor. In paragraph 35 Wolf discloses that the corrosion inhibitor can comprise an amine, and in paragraph 37 Wolf discloses that the amine can be ether amines meeting the limitations of the amine-based detergents of claims 1 and 8, noting that Wolf discloses numerous specific hydrocarbyloxypropylamine compounds, corresponding to the amine-based detergent of amended claim 1 where m is 3, and that Wolf discloses that the hydrocarbyl group can be branched, as recited in amended claim 1. In paragraph 155 Wolf discloses that the composition can further comprise corrosion inhibitors, metal deactivators and demulsifiers, as recited in claim 7. In paragraph 188 Wolf discloses that the corrosion inhibitors can be formulated as a concentrate using at least one organic solvent, as recited in claim 8, where the solvent is present in an amount of 15 to 65% by weight, overlapping the range recited in claim 8 and implying an additive concentration overlapping the range recited in claim 8. In paragraphs 188-191 Wolf discloses numerous suitable organic solvents having boiling points within the range recited in claim 8. In paragraph 190 Wolf discloses that 2-n-butoxyethanol, which has a boiling point of 171° C, is a preferred solvent. The differences between Wolf and the currently presented claims are:
i) Wolf does not specifically disclose compositions comprising the amine-based detergent in amounts within the claimed ranges in terms of ppm.
ii) In paragraph 155, Wolf discloses that the composition can comprise detergents, but does not disclose the specific nitrogen-containing detergents of amended claims 1 and 8.
With respect to i), in paragraph 56 Wolf discloses a composition comprising the corrosion inhibitor in an amount of 3 to 50 ptb (pounds per thousand barrels). One barrel is about 159 liters, and 3 to 50 pounds is about 1.36 to about 22.68 kg, so 3 to 50 pounds per thousand barrels is about 8.55 to about 142.6 mg/L. In Table 6 Wolf discloses base gasolines with densities of about 0.75 kg/L, which will not be substantially affected by the inclusion of small amounts of alcohols as oxygenates. The corrosion inhibitor of Wolf is therefore present in an amount of about 11.4 to about 190.1 ppm (mg/kg) by weight. For the concentration of amine-based detergent in the composition of Wolf to not overlap the ranges recited in claims 1 and 5, the tricarboxylic acid component of the corrosion inhibitor would have to make up more than 73.7% (190.1-50/190.1) of the corrosion inhibitor. In paragraph 56 Wolf discloses that the compositions have an acid/amine equivalence ratio of 1.00 to about 3.00. Since a tricarboxylic acid has three acid groups, and the amines of Wolf have one amine group, the mole ratio of tricarboxylic acid to amine of Wolf therefore ranges from about 0.33 to 1.00. Given these mole ratios, and the fact that the amines disclosed in paragraph 37 of Wolf can comprise a long-chain hydrocarbyl group, the corrosion inhibitor of Wolf clearly does not require more than 73.7% by weight of the tricarboxylic acid component, and the concentration range of the amine-based detergent in the composition of Wolf overlaps the ranges recited in claims 1 and 5. See MPEP 2144.05(I): “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976);”
With respect to ii), Cherpeck discloses in paragraph 65 compositions comprising a major amount of hydrocarbons boiling in the gasoline range, and preferably 50 to 1000 ppm of a nitrogen-containing detergent additive. In paragraph 66 Cherpeck discloses that the nitrogen-containing detergent can be a hydrocarbyl-substituted amine where the hydrocarbyl group has a number average molecular weight of about 700 to 3,000 and where preferred hydrocarbyl-substituted amines are polyisobutenyl amines, as recited in amended claims 1 and 8, and can be polyisobutenyl monoamines, meeting the limitations of amended claims 4 and 11, or polyamines, as recited in newly added claims 20 and 22. In paragraph 67 Cherpeck discloses that the nitrogen-containing detergent can be an alkylphenyl poly(oxyalkylene)monoamine where the oxyalkylene can be oxybutylene, the alkyl group on the alkylphenyl moiety preferably has 1 to 24 carbon atoms, and there are 5 to 100 oxyalkylene repeat units, overlapping the ranges recited for the alkylphenol-substituted poly(oxybutylene) of amended claim 1. Cherpeck further discloses that an especially preferred alkyl group has 12 carbon atoms, within the range recited in amended claim 1. In paragraph 70 Cherpeck discloses that the nitrogen-containing detergent can be a Mannich reaction product, where the alkyl-substituted hydroxyaromatic reactant is preferably a polyalkylphenol where the polyalkyl group has an average molecular weight of 600 to 3000, and the amine can be diethylene triamine, meeting the limitations of the Mannich reaction product of amended claim 1, as well as newly added claims 25-26. Cherpeck discloses that an especially preferred Mannich reaction product is prepared from a polyisobutylphenol where the polyisobutyl group has an average molecular weight of 1000, within the range recited for the polyalkyl group of amended claim 1. In paragraphs 71-72 Cherpeck discloses that the nitrogen-containing detergent can be a polyalkylphenoxyaminoalkane where the polyalkyl group has an average molecular weight of 600 to 5000, overlapping the range recited for the polyalkyl group of the polyalkylphenoxyaminoethane of amended claim 1, and the preferred structure has an aminoethane as the aminoalkane moiety, meeting the limitations of the polyalkylphenoxyaminoalkane of amended claim 1. The nitrogen-containing detergent concentration of 50 to 1000 ppm disclosed by Cherpeck encompasses the range recited in amended claim 1. See MPEP 2144.05(I): “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976);” "[A] prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prima facie case of obviousness." In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003).
The inclusion of one or more of the above-described nitrogen-containing detergents of Cherpeck as the detergent in the composition of Wolf, in the concentration disclosed by Cherpeck, produces a composition meeting the limitations of claims 1, 4-5, 7-8, 11, 20, 22, and 25-26.
It would have been obvious to one of ordinary skill in the art to include the nitrogen-containing detergent(s) of Cherpeck as the detergent in the composition of Wolf, since Cherpeck teaches that they are effective detergents for gasoline fuel compositions, and it would have been obvious to one of ordinary skill in the art to include the nitrogen-containing detergent(s) of Cherpeck in the concentration range disclosed by Cherpeck since Cherpeck teaches that it is a suitable concentration range for the detergents in a gasoline fuel.
In light of the above, claims 1, 4-5, 7-8, 11, 20, 22, and 25-26 are rendered obvious by Wolf in view of Cherpeck.
Claims 8, 11, and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Hashimoto in view of Cherpeck as applied to claims 1, 4-5, 7, 20, and 25 above, and further in view of Youn (U.S. Pat. No. 6,525,221).
The discussion of Hashimoto and Cherpeck in paragraph 2 above is incorporated here by reference. Hashimoto and Cherpeck disclose a fuel composition comprising a combination of the amine-based detergent and the nitrogen-containing detergent of claims 8 and 11, where the amine-based detergent of Hashimoto and the nitrogen-based detergent of Cherpeck also meet the limitations of claims 21-22. Hashimoto and Cherpeck do not specifically disclose an additive concentrate comprising a solvent having the boiling point recited in claim 8.
Youn, in column 1 lines 16-25, discloses a fuel composition comprising a nitrogen-containing detergent. In column 8 lines 41-55 Youn discloses that the detergent can be formulated as a concentrate using an organic solvent having a boiling point of 65 to 205° C, as recited in claim 8, and that the detergent is present in the concentrate in an amount of 30 to 80% by weight, leaving a solvent amount of 20 to 70% by weight, both overlapping the ranges recited in claim 8. Forming a concentrate of the amine-based detergent of Hashimoto and the nitrogen-containing detergent of Cherpeck in the organic solvent of Youn, in the relative amounts disclosed by Youn, meets the limitations of claims 8, 11, and 22.
It would have been obvious to one of ordinary skill in the art to form a concentrate with the detergents of Hashimoto and Cherpeck in the organic solvent of Youn, since you teaches that detergent additives for hydrocarbon fuels can be formulated as concentrates in said organic solvent, and in order to store the additives as a concentrate which can be added to fuels in varying concentrations depending on the application.
Claims 12, 15-16, 18, 23-24, and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Hashimoto in view of Cherpeck as applied to claims 1, 4-5, 7, 20, and 25 above, and further in view of Avery (U.S. PG Pub. 2002/0120171).
The discussion of Hashimoto and Cherpeck in paragraph 2 above is incorporated here by reference. Hashimoto and Cherpeck disclose a method of supplying to an engine a fuel composition meeting the compositional limitations of claims 12, 15-16, 18, 23-24, and 27. Hashimoto discloses in column 1 lines 10-12 that the fuel can be gasoline, and in the abstract and column 2 lines 7-15 and the abstract Hashimoto discloses that additive is effective for cleaning the injection nozzle of coking. Hashimoto and Cherpeck do not specifically disclose supplying the fuel composition to a gasoline direct injection (GDI) engine.
Avery discloses in paragraph 5 that injector coking is a major concern with GDI engines. It therefore would have been obvious to one of ordinary skill in the art to supply the composition of Hashimoto and Cherpeck to a GDI engine, since Hashimoto teach that it is effective in reducing injector coking.
Claims 12-13, 15-16, 18, 23-24, and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Wolf in view of Cherpeck as applied to claims 1-2, 4-5, 7-8, 11, 20, 22, and 25-26 above, and further in view of Henly (U.S. Pat. No. 6,361,573).
The discussion of Wolf and Cherpeck in paragraph 3 above is incorporated here by reference. Wolf and Cherpeck discloses an oxygenated gasoline composition meeting the compositional limitations of the fuel used in the method of claims 12-13, 15-16, 18, 23-24, and 27, but does not specifically disclose supplying the composition to a gasoline direct injection engine.
Henly, in column 1 lines 6-12, discloses fuel compositions which comprise gasoline and a dispersant additive. In column 7 lines 12-28 Henly discloses that the base fuel can be an oxygenated gasoline, where the oxygenating agent can be various compounds disclosed in paragraph 54 of Wolf. In column 8 lines 41-67 Henly discloses that the compositions comprising the additive have improved lubricity, and that this is particularly important due to the increased use of oxygenated gasolines and gasoline direct injection technology.
It would have been obvious to one of ordinary skill in the art to include the additive of Henly in the composition of Wolf and Cherpeck, and to supply the resulting fuel composition to a gasoline direct injection engine, since Henly discloses that the additive provides enhanced lubricity, is useful in combination with oxygenated gasolines, and addresses an issue important in gasoline direct injection engines.
Response to Arguments
Applicant's arguments filed 10/20/25 have been fully considered but they are not persuasive. Applicant argues that in light of the claim amendments and the declaration filed 10/20/25, the claimed composition and method demonstrates superior results commensurate in scope with the claims. While the declaration establishes that the compounds used in the inventive examples fall within the scope of the claims, and the claims have been amended to be more reflective of the compounds used in the examples, applicant still has not established commensurateness in scope with respect to the concentration of nitrogen-containing detergent and amine-based detergent. The inventive examples all contain 50 ppm of the amine-based detergent and 200 ppm of the nitrogen-based detergent. Applicant notes that these concentrations are at the low bound of the claimed ranges and argues that one of ordinary skill in the art would expect the performance of an additive to be maintained or improved at higher concentrations. The alleged unexpected result here is that the inclusion of the nitrogen-containing detergents, which have little or no injector flow restoration ability of their own, to a composition comprising the amine-containing detergent, leads to a greater-than-expected improvement in injector flow restoration. In order to demonstrate unexpected results commensurate in scope with the claims, applicant needs to demonstrate not only that the performance of the inventive composition would be maintained at higher additive concentrations, but that the performance would continue to be greater than expected at higher additive concentrations. The data supplied by applicant indicates that the amine-containing detergents exhibit significant injector flow restoration performance on their own, and that performance would also be expected to increase at higher additive concentrations; eventually the performance of both the inventive compositions and the individual additives will reach a maximum or a plateau. One of ordinary skill in the art therefore cannot conclude solely from the data provided by applicant that the inventive compositions and method will continue to produce superior results even at the upper bounds of the claimed concentration ranges. Applicant points to the data supplied in examples 11A and 11B of the specification as indicating that an increase in amine-containing detergent from 150 ppm to 750 ppm leads to a reduced volume of injector tip deposits at both a low concentration and a high-concentration of nitrogen-containing detergent, but these figures, aside from being a different test than that performed in the declaration, do not include a comparison with compositions comprising the amine-containing detergent alone; it is not clear that the compositions comprising 750 ppm of the amine-containing detergent in combination with the nitrogen-containing detergent lead to reduced deposits relative to compositions comprising 750 ppm of the amine-containing detergent alone. Figures 11A and 11B also indicate that the performance enhancement of going from 0 to 150 ppm of amine-containing detergent is greater than the enhancement of going from 150 to 750 ppm of amine-containing detergent, particularly for the composition comprising a low amount of nitrogen-containing detergent. Applicant also argues that the claimed concentration ranges are “typical concentrations for detergent additives in fuels and this not overly broad or unreasonable”, but this does not allow one to draw conclusions about the injector flow restoration performance at different detergent concentrations.
At several points in the remarks, applicant cites a non-patent publication by Srivastava. This publication has not been cited in an Information Disclosure Statement and no copy has been furnished by applicant.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/JAMES C GOLOBOY/Primary Examiner, Art Unit 1771