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 .
DETAILED ACTION
This Office action is based on the 18/980967 application originally filed December 13, 2024.
Amended claims 1-25, filed June 29, 2026, are pending and have been fully considered. Claims 1-13 and 25 are withdrawn from consideration due to being drawn to a nonelected invention.
Claim Rejections - 35 USC § 103
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 the 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.
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.
Claim(s) 14-24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Taylor et al. (US 2021/024844) hereinafter “Taylor” in view of Cohrs et al. (US 2007/0221539) hereinafter “Cohrs” and Ross et al. (US 2022/0403268) hereinafter “Ross”.
Regarding Claims 14, 15 and 17-19
Taylor discloses in the abstract, fuel performance additives, fuels including such additive, methods of improving the demulsibility of fuels using fuel performance additives, and the use of a fuel performance additive to improve the demulsibility of fuel where such fuels are gasoline or diesel and further include a quaternary ammonium salt obtained from at least the reaction of a nitrogen containing compound having at least a tertiary amino group and a quaternizing agent.
Taylor discloses in paragraph 0008, fuel performance additives, fuels including such additive, methods of improving the demulsibility of fuels using fuel performance additives, and the use of a fuel performance additive to improve the demulsibility of fuel where such fuels are gasoline or diesel.
Taylor further discloses in paragraph 0040, the fuel performance additives herein also include at least one quaternary ammonium salt, which is known to have a detrimental effect on fuel demulsification. Such salts may be formed through a reaction of a nitrogen containing compound having at least a one tertiary amino group and a suitable quaternizing agent.
Taylor discloses in paragraph 0010, the demulsifier component of the fuel performance additives herein includes at least two separate or distinct alkoxylated phenol formaldehyde polymers. Suitable alkoxylated phenol formaldehyde polymers may be obtained from a variety of sources and, while not wishing to be limited by theory, are believed to include alkyl phenol formaldehyde alkoxylates as described below and include ethylene oxide and/or propylene oxide derived alkoxylation and, in some approaches, may have a molecular weight of about 1,000 to about 5,000 g/mol. In other approaches, the alkoxylated phenol formaldehyde polymers may be dissolved in or provided within a solvent, such as aromatic solvents like C6 to C10 aromatic hydrocarbons.
Taylor discloses in paragraph 0070, the fuel performance additives and fuels including such additives may also include one or more optional components as needed for a particular application. For example, the additives and/or fuels may contain conventional quantities of cetane improvers, octane improvers, corrosion inhibitors, cold flow improvers (CFPP additive), pour point, depressants, solvents, demulsifiers, lubricity additives, friction modifiers, amine stabilizers, combustion improvers, detergents, dispersants, antioxidants, heat stabilizers, conductivity improvers, metal deactivators, marker dyes, organic nitrate ignition accelerators, cycloaromatic manganese tricarbonyl compounds, carrier fluids, and the like. In some aspects, the compositions described herein may contain about 10 weight percent or less, or in other aspects, about 5 weight percent or less, based on the total weight of the additive concentrate, of one or more of the above additives. Similarly, the fuels may contain suitable amounts of conventional fuel blending components such as methanol, ethanol, dialkyl ethers, 2-ethylhexanol, and the like.
It is to be noted, Taylor discloses in paragraph 0077, the fuel performance additives may be applicable to the operation of diesel, jet, or gasoline fuels. In one approach, the fuel performance additives including the demulsifier blends herein are well suited for diesel or gasoline and, particularly, gasoline. The fuels may include any and all middle distillate fuels, diesel fuels, biorenewable fuels, biodiesel fuel, fatty acid alkyl ester, gas-to-liquid (GTL) fuels, gasoline, jet fuel, alcohols, ethers, kerosene, low sulfur fuels, synthetic fuels, such as Fischer-Tropsch fuels, liquid petroleum gas, bunker oils, coal to liquid (CTL) fuels, biomass to liquid (BTL) fuels, high asphaltene fuels, fuels derived from coal (natural, cleaned, and petcoke), genetically engineered biofuels and crops and extracts therefrom, and natural gas. “Biorenewable fuels” as used herein is understood to mean any fuel which is derived from resources other than petroleum. Such resources include, but are not limited to, corn, maize, soybeans and other crops; grasses, such as switchgrass, miscanthus, and hybrid grasses; algae, seaweed, vegetable oils; natural fats; and mixtures thereof.
It is to be noted, Taylor discloses a demulsifier of the fuel performance additives herein includes alkoxylated phenol formaldehyde polymers for various fuels, including bunker oils and high asphaltene fuels but fails to disclose the claimed molecular weight and ethylene and propylene oxide moiety amounts of the alkoxylated phenol formaldehyde.
However, Cohrs discloses in the abstract, crude oils and products which have been produced therefrom and comprise distillation residues, comprising at least one alkylphenol-aldehyde resin.
Cohrs discloses in paragraph 0029, alkylphenol-aldehyde resin for improving the cold flowability of crude oils and products which have been derived therefrom and comprise distillation residues.
Cohrs discloses in paragraph 0063, alkylphenol-aldehyde resins are suitable for improving the properties of crude oils and products derived therefrom. Derived products are understood here to mean the mineral oil fractions which are produced from crude oil and comprise distillation residues, such as heating oil, fuel oil, bunker C oil and bitumen.
Cohrs discloses in paragraph 0048, alkylphenol resins have molecular weights, preferably measured by means of gel permeation chromatography against poly(styrene) standards in THF, of from 400 to 25 000 g/mol. The polydispersity Mw/Mn is preferably between 1.2 and 9.0.
Cohrs discloses in paragraph 0057, for use as a demulsifier, alkylphenol-formaldehyde resins with C2-C40-alkyl radicals of the alkylphenol. The alkyl radicals may be linear or branched. Particularly suitable alkylphenol-aldehyde resins derive from branched alkyl radicals having from 4 to 9 carbon atom, includes nonyl. The mean molecular weight determined by means of GPC is between 700 and 20 000 g/mol. The degree of polymerization n is preferably from 1 to 20. The terminal R1 radicals derive preferably from lower alkyl esters of unsaturated fatty acids and in particular from methyl esters of vegetable oils and fats. In a preferred embodiment, the R1 radicals derive from fatty acids which, after the condensation, are reacted with alkylene oxides. The degree of alkoxylation is up to 500 mol, of alkylene oxide per OH group or carboxyl group. Particularly preferred alkylene oxides are ethylene oxide, propylene oxide and mixtures thereof. In the case of mixed alkoxylates, the alkoxylation can be effected either sequentially or randomly. The molar ratio between ethylene oxide and propylene oxide is preferably between 1:10 and 10:1. The dosage rates are preferably between 0.1 and 1000 ppm, based on the oil content of the emulsion.
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art the alkoxylated alkyl phenol formaldehydes of Taylor and Cohrs would encompass the molecular weight and ethylene and propylene oxide moiety amounts of the alkoxylated alkyl phenol formaldehyde of Taylor and Cohrs. Through the teachings of Taylor and Cohrs the motivation includes using the alkoxylated alkyl phenol formaldehydes as demulsifiers that aid in improving the demulsibility of the emulsion in the fuel.
Taylor discloses the fuel is a biorenewable diesel but fails to further disclose the fuel includes hydrogenated vegetable oil in the claimed amount.
However, it is known in the art for biorenewable diesel fuel comprise hydrogenated vegetable oils, as taught by Ross.
Ross discloses in paragraphs 0200 and 0216, a fuel composition comprising additives including an quaternary ammonium salt.
Ross discloses in paragraphs 0201-0208, the diesel fuel composition may comprise a renewable fuel such as a biofuel composition or biodiesel composition. The diesel fuel composition may comprise 1st generation biodiesel. First generation biodiesel contains esters of, for example, vegetable oils, animal fats and used cooking fats. This form of biodiesel may be obtained by transesterification of oils, for example rapeseed oil, soybean oil, canola oil, safflower oil, palm oil, corn oil, peanut oil, cotton seed oil, tallow, coconut oil, physic nut oil (Jatropha), sunflower seed oil, used cooking oils, hydrogenated vegetable oils or any mixture thereof, with an alcohol, usually a monoalcohol, usually in the presence of a catalyst. The diesel fuel composition may comprise second generation biodiesel. The diesel fuel composition may contain blends of any or all of the above diesel fuel compositions. In some embodiments the diesel fuel composition may be a blended diesel fuel comprising bio-diesel. In such blends the bio-diesel may be present in an amount of, for example up to 0.5%, up to 1%, up to 2%, up to 3%, up to 4%, up to 5%, up to 10%, up to 20%, up to 30%, up to 40%, up to 50%, up to 60%, up to 70%, up to 80%, up to 90%, up to 95% or up to 99%.
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art that the renewable diesel fuels of Taylor encompass the renewable diesel fuel of Ross due to both Taylor and Ross disclosing the diesel fuel comprising first, second and third generation bio-diesel fuels used in effective amounts for improving synergistic performance.
Regarding Claim 16
Taylor discloses in paragraph 0036, this demulsifier blend may be added to a fuel performance additive in amounts suitable to provide demulsification in the presence of quaternary ammonium salts. In some approaches, the demulsifier blend may be about 0.1 to about 2 weight percent of the fuel performance additive and, when added to a fuel, may provide about 0.25 to about 5 ppm of the demulsifier blend to the fuel.
Taylor discloses in paragraph 0052, the fuels may contain, on an active ingredient basis, an amount of the quaternary ammonium salt (or reaction product as described herein) in the range of about 1 ppm to about 100 ppm, of the quaternary ammonium salt.
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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding Claims 20-23
Taylor discloses in paragraph 0040, the fuel performance additives herein also include at least one quaternary ammonium salt, which is known to have a detrimental effect on fuel demulsification. Such salts may be formed through a reaction of a nitrogen containing compound having at least a one tertiary amino group and a suitable quaternizing agent.
Taylor discloses in paragraph 0041, a suitable quaternary ammonium salt is obtained from the reaction between an alkyl carboxylate and an amide or imide compound obtained by reacting to a hydrocarbyl substituted acylating agent and an amine.
Taylor further discloses in paragraph 0041, the formed quaternary ammonium salt of this aspect may be that of Formula V below:
PNG
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184
571
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Greyscale
wherein A is a hydrocarbyl linker with 2 to 10 carbon units and including one or more carbon units thereof independently replaced with a bivalent moiety selected from the group consisting of —O—, —N(R′)—, —C(O)—, —C(O)O—, and —C(O)NR′. R8, R9, and R10 are independently alkyl groups containing 1 to 8 carbon atoms; and R′ is independently a hydrogen or a group selected from C1-6 aliphatic, phenyl, or alkylphenyl. R11 and R12 are independently a hydrogen, an acyl group, or a hydrocarbyl substituted acyl group. If one of R11 or R12 is hydrogen, then the other of R4 and R5 is the acyl group or the hydrocarbyl substituted acyl group. If both R11 and R12 include carbonyl moieties, then one of R11 and R12 includes the acyl group and the other of R11 and R12 includes the hydrocarbyl substituted acyl group, and R11 and R12 together with the N atom to which they are attached, combine to form a ring moiety. In other approaches, R11 and R12 together with the N atom to which they are attached, combine to form a hydrocarbyl substituted succinimide. M− may be a carboxylate. Taylor discloses in paragraph 0051, examples of suitable carboxylates may include, but not limited to, maleate, citrate, fumarate, phthalate, 1,2,4-benzenetricarboxylate, 1,2,4,5-benzenetetra carboxylate, nitrobenzoate, nicotinate, oxalate, aminoacetate, and salicylate. As noted above, preferred carboxylates include oxalate, salicylate, and combinations thereof.
Taylor discloses in paragraph 0044, suitable exemplary tertiary amine for forming the fuel additives herein may be selected from 3-(2-(dimethylamino)ethoxy)propylamine, N,N-dimethyl dipropylene triamine, and mixtures thereof.
Regarding Claim 24
Taylor discloses in paragraph 0005, a weight ratio of the quaternary ammonium salt to the demulsifier component of about 5:1 to about 1:1.
Response to Arguments
Applicant’s arguments, filed June 29, 2026, with respect to the rejection(s) of claim(s) 14-24 under Taylor et al. (US 2021/024844) hereinafter “Taylor” in view of Ross et al. (US 2022/0403268) hereinafter “Ross” have been fully considered and are persuasive due to Taylor failing to teach the claimed molecular weight and ethylene and propylene oxide moiety amounts of the alkoxylated alkyl phenol formaldehyde. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Taylor et al. (US 2021/024844) hereinafter “Taylor” in view of Cohrs et al. (US 2007/0221539) hereinafter “Cohrs” and Ross et al. (US 2022/0403268) hereinafter “Ross”.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Burgess et al. (US 2013/0104826) discloses in the abstract, a gasoline composition comprising, as an additive, one or more quaternary ammonium salt(s) (i) formed by the reaction of a compound of formula (A): and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2): wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R.sup.1 is an alkyl, aryl or alkylaryl group having up to 36 carbon atoms; R.sup.2 and R.sup.3 are the same or different alkyl groups having from 1 to 36 carbon atoms; X is an alkylene group having from 1 to 20 carbon atoms; n is from 0 to 20; m is from 1 to 5; and R.sup.4 is hydrogen or a C.sub.1 to C.sub.36 alkyl group.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LATOSHA D HINES whose telephone number is (571)270-5551. The examiner can normally be reached Monday thru Friday 9:00 AM - 6:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem Singh can be reached at 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Latosha Hines/Primary Examiner, Art Unit 1771
