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 Final Office action is based on the 18/139558 application originally filed April 26, 2023.
Claims 1, 3, 5, 6, 8, 10, 13, 14 and 19-26, filed February 02, 2026, are pending and have been fully considered. Claims 2, 4, 7, 9, 11, 12 and 15-18 have been canceled.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1, 3, 5, 6, 8, 10, 13, 14 and 19-26 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2, 12-16 and 20-22 and 24 of U.S. Patent No. 11,091,713. Although the claims at issue are not identical, they are not patentably distinct from each other because the present application and US Patent Number ‘713 claim and disclose throughout the specification overlapping components that define the method of producing an ester compound additive in a diesel fuel composition. Applicant is reminded that those portions of the specification which provide support for the patent claims may also be examined and considered when addressing the issue of whether a claim in an application defines an obvious variation of an invention claimed in the patent. In re Vogel, 422 F. 2d 438, 164 USPQ 619, 622 (CCPA 1970).
Claims 1, 3, 5, 6, 8, 10, 13, 14 and 19-26 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2, 7 and 9-12 of U.S. Patent No. 11,084,999. Although the claims at issue are not identical, they are not patentably distinct from each other because the present application and US Patent Number ‘999 claim and disclose throughout the specification overlapping components that define the method of producing an ester compound additive in a diesel fuel composition. Applicant is reminded that those portions of the specification which provide support for the patent claims may also be examined and considered when addressing the issue of whether a claim in an application defines an obvious variation of an invention claimed in the patent. In re Vogel, 422 F. 2d 438, 164 USPQ 619, 622 (CCPA 1970).
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) 1, 3, 5, 6, 8, 10, 13, 14 and 19-26 is/are rejected under 35 U.S.C. 103 as being unpatentable over Brewer et al. (WO 02/002720 A2) hereinafter “Brewer” in view of Reid (US 2010/0258070).
Regarding Claims 1, 3, 5, 6, 8, 10, 13, 14 and 19-26
Brewer discloses in the abstract, a method of increasing the lubricity of a liquid hydrocarbon fuel.
Brewer discloses on page 6 paragraph 6, the hydrocarbon fuel comprises diesel fuels and heating oils will typically contain less than 0.2% w/w sulphur and may contain, in addition to the additive compositions of this invention, any of the other additives commonly added as minor components, such as cetane improvers, cold flow improvers, detergent/dispersant additives, antifoam additives, dehazing additives, combustion improvers, antioxidants, etc.
Brewer further discloses on page 7 paragraph 1, the compounds of formula (I) may for example be prepared by reacting an anhydride of formula
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with an alcohol of formula R2OH and/or R3OH where R2 and R3 are as defined in Formula (I).
Brewer discloses on page 2 paragraph 6, a class of esterified alkenyl succinic acids which, while demonstrating excellent performance as lubricity additives, also offer improved compatibilities with other fuel and lubricant additives and reduced carryover between fuels in the distribution system, for example fuel pipelines, tankers, etc., as measured by their improved water separation characteristics.
Brewer discloses on page 2 paragraph 7 and page 3 paragraph 1, the compounds are represented by the general formula (I):
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where R1 is a C10-C150 alkenyl group, such as an olefin or polyolefin, one of R2 and R3 is -OH or the residue of a C1-20 monohydroxy alcohol and the other of R2 and R3 is -OH or the residue of either a C1-20 monohydroxy alcohol or a C1-20 polyhydroxy alcohol, with the proviso that R2 and R3 are not both -OH.
Brewer discloses on page 3, R1 is preferably a C16-C80 group and more preferably a polyisobutene (PIB) . The molecular weight of the PIB is preferably 200-2000, more preferably 260-1000, for example about 260, 320, 350, 550, 750 or 1000. Conventional PIBs and so-called "high-reactivity" PIBs (see for example EP-B-0 565 285) are suitable for use in the invention. High reactivity in this context is defined as a PIB wherein at least 50%, preferably 70% or more, of the terminal olefinic double bonds are of the vinylidene type.
Brewer further discloses on pages 3 and 4, R2 and R3 are -OH or the residues of alcohols, although R2 and R3 are not both simultaneously -OH, i.e. the compound is always at least semi-esterified. Partial esters of another type are also envisaged, i.e. compounds in which one carboxyl group is fully esterified and one carboxyl group is only partially esterified. In other words the invention encompasses mixtures of the fully and semi-esterified compounds in a variety of ratios. A good measure of the degree of esterification under these circumstances is given by the acid number, i.e. the amount of NaOH required to neutralize 1 g of the compound. This is generally less than 90 g NaOH/g, corresponding approximately to semi-esterification (although it is also dependent on molecular weight) , preferably less than 50 mg NaOH/g, for example less than 20 mg NaOH/g, less than 10 mg NaOH/g or less than 5 mg NaOH/g.
Brewer disclose on page 4, the R2 and R3 alcohols can be either be mono- or poly- hydroxy alcohols, i.e. alcohols having one, two or more hydroxy groups, in the case of polyhydroxy alcohols one of which esterifies the carboxylic acid moiety of the succinic acid. One or both of the groups R2 and R3 is derived from a monohydroxy alcohol . The monohydroxy alcohols are preferably HO-R4 where R4 "is a C1-20 straight or branched chain hydrocarbon. R2 and/or R3 preferably are methanol, ethanol, propanol or isopropanol. When only one of R2 and R3 is a monohydroxy alcohol the other is preferably (-OCH2CH2)-nOH, (-OCH2CHCH3)-nOH or -OCH2CHOHCH2OH with n = 1-10 and more preferably ethylene glycol or glycerol, i.e. n = 1, or diethylene glycol, i.e. n =2. Also useful are higher sugars, i.e. longer chain analogues of glycerol of formula -OCH2(-CHOH)-nCH2OH with n = 2-4.
Brewer discloses on page 5, the total dosages of the compounds of formula (I), when added to a fuel to give a combined lubricity enhancement, are conveniently between 5 and 5000 ppm, which overlaps the optionally substituted polycarboxylic acid or hydrocarbyl substituted anhydride and alcohol of formula H- (OR)n-OH are reacted in a ratio of from 1.5:1 to 1:1.5.
It is to be noted, Brewer discloses on page 4, the compounds of formula (I) may be added to middle distillate fuels of poor lubricity, such as those with poor inherent lubricity, and those which have been exposed to hydrotreatment or desulphurization processes thereby lowering the sulphur concentration to 0.5% w/w or less, e.g. 0.2 % w/w, 0.05 % w/w or lower, for example diesel fuels (typical distillation range 150-400 °C) and heating oils (typical distillation range 150-450 °C) , and also to gasolines (typical distillation range 30-210 °C) , kerosines (typical distillation range 140-300 °C) and heavy fuel oils (typical distillation range 300-600 °C) . An aspect of the invention thus comprises methods of increasing the lubricity of such fuels by addition of the compounds.
Brewer discloses the fuel comprises diesel fuel, typically in the distillation range of 150-400℃ but fails to specifically teach the fuel comprises biodiesel.
However, it is known in the art that diesel fuels in the distillation range of 150-400℃, include a renewable fuel made of a bio-fuel, as taught by Reid.
Reid discloses in the abstract, a diesel fuel composition.
Reid discloses 0138, the diesel fuel composition may comprise a petroleum-based fuel oil, especially a middle distillate fuel oil. Such distillate fuel oils generally boil within the range of from 110° C. to 500° C., e.g. 150° C. to 400° C. The diesel fuel may comprise atmospheric distillate or vacuum distillate, cracked gas oil, or a blend in any proportion of straight run and refinery streams such as thermally and/or catalytically cracked and hydro-cracked distillates. Reid discloses in paragraph 0140, the diesel fuel composition may comprise a renewable fuel such as a biofuel composition or biodiesel composition. Reid further discloses in paragraph 0141, 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, safflower oil, palm 25 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, in the presence of a catalyst. Reid discloses in paragraph 0142, the diesel fuel composition may comprise second generation biodiesel. Second generation biodiesel is derived from renewable resources such as vegetable oils and animal fats and processed, often in the refinery, often using hydroprocessing such as the H-Bio process developed by Petrobras. Second generation biodiesel may be similar in properties and quality to petroleum based fuel oil streams, for example renewable diesel produced from vegetable oils, animal fats etc. and marketed by ConocoPhillips as Renewable Diesel and by Neste as NExBTL. Reid discloses in paragraph 0143, the diesel fuel composition may comprise third generation biodiesel. Third generation biodiesel utilizes gasification and Fischer-Tropsch technology including those described as BTL (biomass-to-liquid) fuels. Third generation biodiesel does not differ widely from some second generation biodiesel, but aims to exploit the whole plant (biomass) and thereby widens the feedstock base. Reid discloses in paragraph 0144, the diesel fuel composition may contain blends of any or all of the above diesel fuel compositions.
Reid discloses in paragraph 0017, a diesel fuel composition comprising a nitrogen-containing detergent and a performance enhancing additive, wherein the performance enhancing additive is the product of a Mannich reaction between: (a) an aldehyde; (b) a polyamine; and(c) an optionally substituted phenol.
Reid discloses in paragraph 0174, the improvement in performance of the diesel engine having a high pressure fuel system may be measured by an improvement in fuel economy. Reid discloses in paragraph 0175, improvement in performance may also be assessed by considering the extent to which the use of the performance enhancing additive preferably reduces the amount of deposit on the injector of an engine having a high pressure fuel system.
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to use a middle distillate fuel having a distillation range of 150-450℃, which encompasses renewable diesel and bio-diesel fuel and known detergents, as taught by Brewer and Reid. The motivation to do so, is to use middle distillate fuel with low sulfur content with various fuel additives in order to improve the lubricity.
Response to Arguments
Applicant's arguments filed February 02, 2026 in view of Brewer and Reid have been fully considered but are not deemed persuasive.
Applicants argued: “The additional results in the Declaration provide inventive examples showing that additive compounds 1 and 2 are effective in fuel compositions comprising from 5 to 50 vol% HVO 1 in mineral diesel as well as in five different neat HVO fuels corresponding to 100% HVO (see table 4 of the Declaration). As the invention has been shown to work in fuel compositions comprising 5, 20, 50 and 100% HVO, the effects shown in the additional data can be extended to all amounts of HVO within this range. The HVO fuels tested demonstrate a range of properties, for example levels of isomerization (from 16 to 88%), as well as cloud points (from -23 to 18°C) and pour points (from -38°C to 18°C). The effects shown in the additional data can therefore be extended to substantially all types of HVO fuel. Therefore, the amended claims are commensurate with the additional results presented in the Declaration. The data in Table 4 of the Declaration shows results using a treat rate of from 75 ppm to 200 ppm, with a clear trend towards the higher treat rates providing improved lubricity. The claimed range of from 50 to 500 ppm provides a narrow scope around these results in which the skilled person would expect the claimed additives to behave predictably in line with this trend. Based on teachings of Brewer, a person of ordinary skill in the art would not be able to predict the advantageous performance of compounds as defined in the instant claims in the claimed renewable diesel compositions compared to compounds comprising residues of monohydroxy alcohols, as required by Brewer, since Brewer is silent on renewable diesel. Therefore, the amended claims are considered to be non-obvious over the prior art and patentable.”.
Applicants arguments and Declaration are not deemed persuasive. In view of the foregoing, when all of the evidence is considered, the totality of the rebuttal evidence of nonobviousness fails to outweigh the evidence of obviousness. Additionally, applicants also argue that examples and comparative examples defined in the specification/declaration. The examiner acknowledges these results, however, the examiner MAINTAINS the examples are insufficient to overcome the above rejection because the examples are not commensurate in scope with the claims because the examples are directed to specifics not literally defined by the claims, for example, the examples use specific amounts of hydrotreated vegetable oil (HVO) fuel and a specific ADDITIVE COMPOUND including specific anhydrides and alcohols (see Table 1) which are all not commensurate in scope with claim 1 at least. Additionally, a trend for the results cannot be determined due to the treat rates of the examples and comparative examples are similar in results (i.e. Table 4 Additive Compound 4 and 5 have close to the same results as Table 5 Comparative Compound 6 and 7). The examples no way allow the examiner to determine a trend for the results for any and all amounts of additive to fuel blend. Evidence of unexpected results must be clear and convincing. In re Lohr 137 USPQ 548. Evidence of unexpected results must be commensurate in scope with the subject matter claimed. In re Linder 173 USPQ 356. Therefore, it is maintained Brewer modified by Reid has met the limitations of the presently claimed invention.
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.
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 on 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 on 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
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