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 .
The amendment dated 11/28/2025 has been considered and entered. The response was considered but was not found to be persuasive. Therefore, the previous rejections are maintained.
Claim Rejections - 35 USC § 102/103
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.
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.
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.
Claims 17 – 19, 21 – 25, 27, 30, 31, 33 – 39, 41 are rejected under 35 U.S.C. 102(a)(1) as anticipated by Graupner (WO 03/076554) or, in the alternative, under 35 U.S.C. 103 as obvious over Graupner (WO 03/076554)
In regards to claim 17, Graupner teaches gasoline additives comprising hydrocarbyl amine for reducing injector nozzle fouling in a direct injection spark ignition engine. The hydrocarbyl group of the hydrocarbyl amine is linear or branched (page 3 lines 26 – 35). The hydrocarbylamine has a linear or branched hydrocarbyl group with molecular weight of from 140 to 255 (i.e., equivalent to C10 to C18 alkyl) (abstract, page 5 lines 3 – 11). The hydrocarbylamine is preferably linear C9-17 alkylamine of a formula (I) (page 4 lines 1 – 6). Since linear and branched hydrocarbyl groups are taught, it appears that branched C13 alkylamines would be quickly envisaged or would be obvious. Such groups would be expected to have the branching properties of the claim. Even, where the branching properties as claimed are overlapped, obviousness exists. When the composition is used in the direct injection gasoline engine, it provides the of reducing injector nozzle fouling as discussed above.
In regards to claim 18, Graupner teaches fuel additive of the claim and thus provides the method of improving storage stability and/or formulability of a fuel additive package for gasoline.
In regards to claim 19, Graupner teaches the method and composition which further comprises conventional additives such as detergent (dispersants) etc., as discussed in US 5,855,629 by Grundy et al. which is incorporated by reference (Graupner, page 7 lines 1 – 7). Grundy recites additives such as Mannich reaction products in minor amounts of 10% or less or 0.1% or less (column 9 lines 39 – 56).
In regards to claim 21, Graupner teaches the gasoline composition having the claimed ingredient as previously stated.
In regards to claim 22, Graupner teaches the composition which can comprise the additives of Grundy as previously stated. Grundy teaches Mannich products can be present at 0.1% (1000 ppm) or less which overlaps the claimed range. The use of the dispersant in the amounts recited by Grundy would be obvious as Graupner incorporates Grundy by reference.
In regards to claim 23, Graupner teaches the gasoline composition having conventional additives but does not particularly recite the quaternary additive of the claim. Greenfield et al. (US 2017/0107438) is added to teach the claimed additive. Greenfield teaches quaternary ammonium salts useful in fuel or lubricant composition for use in internal combustion engines [abstract, 0001]. The composition is useful for reducing or preventing injector deposits [0032 – 0036]. The fuel is gasoline or diesel composition and comprises the imide quaternary salt (imide quat) in amounts of 5 to 1000 ppm [0028]. The imide can have cations of the structures below
PNG
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344
475
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Greyscale
PNG
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529
480
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Greyscale
While the anion is not particularly recited, quaternary ammonium compounds intrinsically comprises anions. Greenfield teaches compounds are prepared using C4 to C10 hydrocarbyl containing dicarboxylic (i.e., polycarboxylic) acids or their anhydrides or C1 to C5 alcohol-derived mono or diesters [0048]. The remnant of the dicarboxylic acid, anhydride or ester forms the anion equivalent to A- of the claim.
Thus, persons of ordinary skill in the art at the time the claims were filed would have found it obvious to have used the quaternary ammonium salt of Greenfield in the composition of Graupner, as Greenfield teaches that they are useful for improving injector deposits in gasoline compositions similar to the purpose of Graupner.
In regards to claims 24, 25, 27, 30, 31, 34, 35, Graupner in view of Greenfield teaches the composition comprising the ammonium compound of the claim. Greenfield teaches compounds are prepared using C4 to C10 hydrocarbyl containing dicarboxylic (i.e., polycarboxylic) acids or their anhydrides or C1 to C5 alcohol-derived mono or diesters [0048]. The remnant of the dicarboxylic acid, anhydride or ester forms the anion equivalent to A- of the claims. The hydrocarbyl group of the quaternizing agent is equivalent to R5 of the claims. The groups attached to the quaternary nitrogen (N+) are equivalent to the 4 organic residues of claim 23. Each of R6, R7 and R8 are preferably hydrocarbon comprising at least 20 carbon atoms and are equivalent to R2 to R4 of the claims. The group equivalent to R2 of the claim is R23-imide-R24 [0089, 0090]. The hydrocarbyl group (R24) attached to the imide is polyisobutylene (PIB) and has a number average molecular weight of from 1300 to 3000 [0049, 0221 – 0223].
In regards to claim 33, Graupner teaches the gasoline composition having the branched alkylamine having the claimed limitation as previously discussed.
In regards to claim 36, Graupner in view of Greenfield teaches the composition. Greenfield teaches the quaternizing agent is an oxalate such as dimethyl oxalate [0011].
In regards to claims 37 – 39, Graupner teaches the composition can comprise nitrogen-detergent including polyalkenyl polyamines such as polyisobutylene polyamine and wherein the nitrogen-based detergents can have hydrocarbyl groups with molecular weights of 750 to 6000 (page 7 lines 19 – 25). The polyisobutylene are prepared from isobutene. The claimed products are taught, and the process of forming them does not carry patentable weight.
In regards to claim 41, Graupner teaches the composition having aromatic hydrocarbon content of from 10 to 60% by volume (page 6 lines 10 – 15).
Allowable Subject Matter
Claim 40 is allowed.
The following is a statement of reasons for the indication of allowable subject matter: The closest prior art on the record by Graupner (WO 03/076554) or Greenfield et al. (US 2017/0107438) fails to teach the claimed additive structures.
Claims 26, 28, 29 are 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.
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive.
Applicant argues that Graupner fails to teach branched C13 alkylamines as claimed. The argument is not persuasive.
Graupner teaches hydrocarbyl amines having molecular weights of from 140 to 255 daltons which encompasses linear or branched C10 to C18 alkyl groups. Thus, while linear alkyl groups are preferred, both are encompassed by the molecular weights provided.
Applicant argues that the use C13 branched alkylamine in oil is superior and unexpected better than the corresponding linear alkylamines as discussed in the declaration by Marc Walter dated 11/28/2025. The argument is not persuasive.
The sole inventive example in the declaration is not commensurate in scope with the claims.
While the claims allow for the use of the branched alkylamine at any suitable amount, or preferably at from 10 to 3000 ppmw, the sole inventive example recites a composition having 5.31 wt% (53,100 ppmw) which does not support the breadth of the claimed range, nor demonstrates criticality at the lower and upper amounts of 10 and 3000 ppmw.
The argument is not persuasive.
The inventive examples having a C13 branched alkylamine is compared with dodecylamine which is a C12 linear alkylamine rather than a C13 linear alkylamine for demonstrating superior properties strictly stemming from the different between linear and branched amines and not from chain length or molecular weight.
Applicant previously argued that dodecylamine is the closest prior art. The argument was not persuasive.
Graupner teaches hydrocarbyl amines with the hydrocarbyl group having molecular weights of from 140 to 255 which encompasses C13 alkylamines. Therefore, the closest prior art of Graupner allows for the use of C13 linear and branched hydrocarbyl amines such as alkylamines.
Thus, applicant fails to provide an inventive example that is commensurate in scope with the claims and compared to the closest prior art for demonstrating unexpected results sufficient to rebut the case of obviousness.
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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/TAIWO OLADAPO/Primary Examiner, Art Unit 1771