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 amendments filed 12/24/25 do not overcome the rejections set forth in the office action mailed 9/29/25. The discussions of the rejections have been updated as necessitated by the amendments. Newly added claims 21-23 are rejected below over the references of record. New grounds of rejection under 35 USC 112(d), necessitated by the amendments, have also been set forth below.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 8 and 15 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 8 requires each of R1 and R2 to contain 10 to 14 carbon atoms. Claim 2, from which claim 8 requires, has been amended to contain this limitation. Claim 8 therefore failed to further limit claim 2.
Claim 15 requires each of R1 and R2 to contain 8 to 14 carbon atoms. Claim 3, from which claim 15 depends, has been amended to require that each of R1 and R2 contain 10 to 14 carbon atoms, a narrower range than claim 3. Claim 15 therefore fails to further limit claim 3.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 103
Claims 2-3, 8-9, 15, and 20-23 are rejected under 35 U.S.C. 103 as being unpatentable over Bush (U.S. PG Pub. No. 2021/0009912) in view of Kiiski (U.S. PG Pub. No. 2019/0136145) and Davies (U.S. Pat. No. 5,833,722).
In paragraph 41 Bush discloses a fuel composition that is useful at fueling an engine. In paragraph 43 Bush discloses that the fuel can comprise a blend of a hydrotreated vegetable oil (HVO) and biodiesel. In paragraph 42 Bush discloses that the biodiesel can be a transesterified oil or fat from plants and animals such as rapeseed and soybean methyl ester, meeting the limitations of the biodiesel of claims 2-3.
In paragraph 63 Bush discloses that the composition can comprise a cold flow improver which can be a comb polymer, and in paragraph 68 discloses that the comb polymer can be obtained by the polymerization of fumaric acid with vinyl acetate, followed by esterification of the acid function with an alcohol having at least 10 carbon atoms. Units derived from vinyl acetate meet the limitations of the units of formula (I) in component (a) of claims 2-3, where R is a methyl group, and units derived from the esterified fumaric acid meet the limitations of the units of formula (II) in component (a) of claims 2-4 and 15 where the R1 and R2 groups have at least 10 carbon atoms, overlapping the ranges recited for the R1 and R2 groups in claims 2-3, 8, and 15. In paragraph 72 Bush discloses that the cold flow improver is present in concentration ranges overlapping or encompassing the range recited for the component (a) of claims 2-3 as well as newly added claims 21-22.
In paragraph 45, Bush discloses that the fuel is present in greater than 50% by weight of the composition, or greater than 95% by weight of the composition. When the fuel is a blend of HVO and biodiesel, the concentration ranges for both components leading to a total amount consistent with the above ranges will encompass the ranges recited in claims 2-3.
The differences between Bush and the currently presented claims are:
i) Bush does not specifically disclose that the HVO is obtained by the hydrodeoxygenation of vegetable oils and animal fats.
ii) Bush does not specifically disclose cold flow comb polymers having the molecular weight recited in claims 2-3 and 23, and comprising the units of formula (I) and formula (II) in the amounts recited in claims 9 and 20.
iii) Some of the ranges of Bush overlap or encompass the claimed ranges rather than falling within them.
With respect to i), in paragraph 64 Kiiski discloses that hydrotreated vegetable oil (the HVO of Bush) usually involves hydrodeoxygenation of a feedstock which can be vegetable oil, as well as hydroisomerization. The inclusion of an HVO obtainable by a process including a step of hydrodeoxygenation of a vegetable oil as the HVO in the composition of Bush meets the limitations of the HVO component of amended claims 2-3, and would have been obvious to one of ordinary skill in the art since Kiiski teaches that the products have a high paraffin content, leading to a higher cetane number.
With respect to ii), In column 1 lines 6-8 Davies discloses diesel fuels, and in column 7 lines 4-10 discloses that the compositions can comprise comb polymers. In column 8 lines 10-28 Davies discloses that the comb polymers can be copolymers of alkyl fumarates and vinyl acetate, where the alkyl groups have 12 to 20 carbon atoms, within the scope of the comb polymers of Bush and overlapping the number of carbon atoms in the R1 and R2 groups of claims 2-3, 8, and 15, where the comb polymers have a particularly preferred number average molecular weight of 1,000 to 30,000, encompassing the ranges recited in claims 2-3 and newly added claim 23, and where the copolymer can be derived from an equimolar mixture of fumaric acid and vinyl acetate, leading to copolymers where both units are present in an amount of 50 mol%, meeting the limitations of claims 9 and 20.
It would have been obvious to one of ordinary skill in the art to use the comb polymers of Davies as the comb polymers of Bush and Kiiski, since Davies teaches that they are suitable comb polymers for use in compositions which can be diesel fuels, and since they fall within the scope of the comb polymers of Bush.
With respect to iii), 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);”
The compositions of claims 3, 15, and 20 are therefore rendered obvious by Bush in view of Kiiski and Davies, and since the compositions must be prepared by adding “dosing” the additives into the fuel, the method of claims 2 and 8-9 are rendered obvious as well. As the method and composition of Bush, Kiiski, and Davies meets the method and compositional limitations of the claims, they will provide fuel compositions possessing the properties of claims 2-3.
Claims 6, 10, and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Bush in view of Kiiski and Davies as applied to claims 2-3, 8-9, 15, and 20-23 above, and further in view of Sneddon (U.S. PG Pub. No. 2012/0030994).
The discussion of Bush, Kiiski, and Davies in paragraph 5 above is incorporated here by reference. Bush, Kiiski, and Davies disclose a composition and method meeting the limitations of claims 2-3, and disclose that the composition can comprise various additives, but do not specifically disclose the reaction product of a polycarboxylic acid having at least one tertiary amino group and a primary or secondary amine.
Sneddon, in paragraphs 1 and 26, discloses additives which are effective at improving the flow properties and filterability of biodiesel-containing (Bx) fuels above the cloud point. In paragraph 58 Sneddon discloses that a preferred additive includes the reaction product of EDTA (ethylenediaminetetraacetic acid) with hydrogenated tallow amine in a 1:4 mole ratio, meeting the limitations of component (b) of amended claims 6 and 17, and the specific additive of claim 10. The inclusion of the reaction product of Sneddon in the composition of Bush therefore meets the limitations of claims 6, 10, and 17.
It would have been obvious to one of ordinary skill in the art to include the reaction product of Sneddon in the composition of Bush, Kiiski, and Davies, in order to impart the improved cold flow and filterability properties taught by Sneddon.
Claims 7, 11, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Bush in view of Kiiski and Davies as applied to claims 2-3, 8-9, 15, and 20-23 above, and further in view of Krull (AU 2021243166 A1).
The discussion of Bush, Kiiski, and Davies in paragraph 5 above is incorporated here by reference. Bush, Kiiski, and Davies disclose a composition and method meeting the limitations of claims 2-3, and disclose that the composition can comprise various additives, but do not specifically disclose the reaction product of a secondary amine and a copolymer of maleic anhydride and an α-olefin.
From page 8 line 19 through 10 line 7, Krull discloses fuel oil compositions comprising a low-temperature additive which comprises at least one oil-soluble amide-ammonium salt of a polycarboxylic acid with a mono- and/or dialkylamine. On page 2 lines 6-8 Krull discloses that fuel oils include second-generation biofuels, which Krull indicates on page 1 lines 17-29 include HVO, as in the composition of Bush. On page 11 lines 3-6 and 25-27 Krull discloses that the polycarboxylic acid used to prepare the amide-ammonium salt can be a copolymerized dicarboxylic acid, preferably copolymers of maleic anhydride. From page 11 line 31 through page 12 line 10 Krull discloses that preferred comonomers include α-olefins, and that octadecene, a C18 olefin, is a preferred α-olefin. On page 13 lines 11-13 Krull discloses that secondary amines are preferred amines, and discloses on page 13 lines 20-23 that ditallowamine is a particularly preferred secondary amine. In Table 2A (Example A1) on page 40 Krull indicates that the copolymer of maleic anhydride and α-olefin is reacted with 2 equivalents of ditallowamine to arrive at the amide-ammonium salt. The reaction products of maleic anhydride, α-olefin, and secondary amine meet the limitations of component (c) of amended claims 7 and 18. When the α-olefin is octadecene, the secondary amine is ditallowamine, and the copolymer is reacted with 2 equivalents of ditallowamine, claim 11 is met as well. The inclusion of the additive composition of Krull in the composition of Bush, Kiiski, and Davies therefore meets the limitations of claims 7, 11, and 18.
It would have been obvious to one of ordinary skill in the art to include the additive composition of Krull in the composition of Bush, Kiiski, and Davies, since Krull discloses on page 36 lines 1-16 that the additive composition imparts various advantages to low-sulfur diesel fuels, and teaches in the other cited sections that such fuels can comprise HVO.
Claims 2-3, 8-9, 15, and 20-23 are rejected under 35 U.S.C. 103 as being unpatentable over Bush (U.S. PG Pub. No. 2021/0009912) in view of Kuronen ( WO 2021/094655 A1), Kiiski (U.S. PG Pub. No. 2019/0136145) and Davies (U.S. Pat. No. 5,833,722).
In paragraph 41 Bush discloses a fuel composition that is useful at fueling an engine. In paragraph 43 Bush discloses that the fuel can comprise a blend of a hydrotreated vegetable oil (HVO) and biodiesel. In paragraph 42 Bush discloses that the biodiesel can be a transesterified oil or fat from plants and animals such as rapeseed and soybean methyl ester, meeting the limitations of the biodiesel of claims 2-3.
In paragraph 63 Bush discloses that the composition can comprise a cold flow improver which can be a comb polymer, and in paragraph 68 discloses that the comb polymer can be obtained by the polymerization of fumaric acid with vinyl acetate, followed by esterification of the acid function with an alcohol having at least 10 carbon atoms. Units derived from vinyl acetate meet the limitations of the units of formula (I) in component (a) of claims 2-3, where R is a methyl group, and units derived from the esterified fumaric acid meet the limitations of the units of formula (II) in component (a) of claims 2-4 and 15 where the R1 and R2 groups have at least 10 carbon atoms, overlapping the ranges recited for the R1 and R2 groups in claims 2-3, 8, and 15. In paragraph 72 Bush discloses that the cold flow improver is present in concentration ranges overlapping or encompassing the range recited for the component (a) of claims 2-3 and newly added claims 21-22.
The differences between Bush and the currently presented claims are:
i) In paragraph 45, Bush discloses that the fuel is present in greater than 50% by weight of the composition, or greater than 95% by weight of the composition. Bush does not specifically disclose concentrations for the individual biodiesel and renewable diesel components.
ii) Bush does not specifically disclose that the HVO is obtained by the hydrodeoxygenation of vegetable oils and animal fats.
iii) Bush does not specifically disclose cold flow comb polymers having the molecular weight recited in claims 2-3, and comprising the units of formula (I) and formula (II) in the amounts recited in claims 9 and 20.
iv) Some of the ranges in the cited references overlap or encompass the claimed ranges rather than falling within them.
With respect to i), from page 25 line 28 through page 26 line 11, Kuronen discloses a diesel fuel blend (Diesel fuel blend II), which comprises a biodiesel (“diesel fuel of the present invention”), and a renewable diesel fuel. The renewable diesel fuel can be present in 75 to 99% or 50 to 75% by weight of the blend, implying that the biodiesel can be present in amounts of 1 to 25% or 25 to 50% by weight of the blend. As discussed above, Bush discloses that the composition can comprise greater than 95% by weight of the fuel, and when then the fuel of Bush is a blend of biodiesel and renewable diesel in the proportions disclosed by Kuronen, the concentration of biodiesel will be 0.95 to about 25%, or 23.75 to about 50% by weight of the overall composition, and the concentration of diesel fuel will be 71.25 to about 99%, or 47.5 to about 75% by weight of the composition. The concentrations by volume will be similar to the concentrations by weight, since the fuels are the predominant component of the composition and will have similar densities, and the concentration ranges of the biodiesel and renewable diesel will therefore overlap the ranges recited in claims 2-3.
It would have been obvious to one of ordinary skill in the art to formulate the biodiesel/renewable diesel blend in the composition of Bush to contain biodiesel and renewable diesel in the amounts taught by Kuronen, since Kuronen teaches on page 26 lines 8-11 that this leads to improved cold properties such as cloud point and freezing point.
With respect to ii), in paragraph 64 Kiiski discloses that hydrotreated vegetable oil (the HVO of Bush) usually involves hydrodeoxygenation of a feedstock which can be vegetable oil, as well as hydroisomerization. The inclusion of an HVO obtainable by a process including a step of hydrodeoxygenation of a vegetable oil as the HVO in the composition of Bush meets the limitations of the HVO component of amended claims 2-3, and would have been obvious to one of ordinary skill in the art since Kiiski teaches that the products have a high paraffin content, leading to a higher cetane number.
With respect to iii), In column 1 lines 6-8 Davies discloses diesel fuels, and in column 7 lines 4-10 discloses that the compositions can comprise comb polymers. In column 8 lines 10-28 Davies discloses that the comb polymers can be copolymers of alkyl fumarates and vinyl acetate, where the alkyl groups have 12 to 20 carbon atoms, within the scope of the comb polymers of Bush and overlapping the number of carbon atoms in the R1 and R2 groups of claims 2-3 and 8, where the comb polymers have a particularly preferred number average molecular weight of 1,000 to 30,000, encompassing the ranges recited in claims 2-3 as well as newly added claim 23, and where the copolymer can be derived from an equimolar mixture of fumaric acid and vinyl acetate, leading to copolymers where both units are present in an amount of 50 mol%, meeting the limitations of claims 9 and 20.
It would have been obvious to one of ordinary skill in the art to use the comb polymers of Davies as the comb polymers of Bush and Kiiski, since Davies teaches that they are suitable comb polymers for use in compositions which can be diesel fuels, and since they fall within the scope of the comb polymers of Bush.
With respect to iv), 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);”
The compositions of claims 3, 15, and 20 are therefore rendered obvious by Bush in view of Kuronen, Kiiski and Davies, and since the compositions must be prepared by adding “dosing” the additives into the fuel, the method of claims 2 and 8-9 are rendered obvious as well. As the method and composition of Bush, Kiiski, and Davies meets the method and compositional limitations of the claims, they will provide fuel compositions possessing the properties of claims 2-3.
Claims 6, 10, and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Bush in view of Kuronen, Kiiski, and Davies as applied to claims 2-3, 8-9, 15, and 20-23 above, and further in view of Sneddon (U.S. PG Pub. No. 2012/0030994).
The discussion of Bush, Kuronen, Kiiski, and Davies in paragraph 8 above is incorporated here by reference. Bush, Kuronen, Kiiski, and Davies disclose a composition and method meeting the limitations of claims 2-3, and disclose that the composition can comprise various additives, but do not specifically disclose the reaction product of a polycarboxylic acid having at least one tertiary amino group and a primary or secondary amine.
Sneddon, in paragraphs 1 and 26, discloses additives which are effective at improving the flow properties and filterability of biodiesel-containing (Bx) fuels above the cloud point. In paragraph 58 Sneddon discloses that a preferred additive includes the reaction product of EDTA (ethylenediaminetetraacetic acid) with hydrogenated tallow amine in a 1:4 mole ratio, meeting the limitations of component (b) of amended claims 6 and 17, and the specific additive of claim 10. The inclusion of the reaction product of Sneddon in the composition of Bush, Kuronen, Kiiski, and Davies therefore meets the limitations of claims 6, 10, and 17.
It would have been obvious to one of ordinary skill in the art to include the reaction product of Sneddon in the composition of Bush, Kuronen, Kiiski, and Davies, in order to impart the improved cold flow and filterability properties taught by Sneddon.
Claims 7, 11, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Bush in view of Kiiski and Davies as applied to claims 2-3, 8-9, 15, and 20-23 above, and further in view of Krull (AU 2021243166 A1).
The discussion of Bush, Kuronen, Kiiski, and Davies in paragraph 8 above is incorporated here by reference. Bush, Kuronen, Kiiski, and Davies disclose a composition and method meeting the limitations of claims 2-3, and disclose that the composition can comprise various additives, but do not specifically disclose the reaction product of a secondary amine and a copolymer of maleic anhydride and an α-olefin.
From page 8 line 19 through 10 line 7, Krull discloses fuel oil compositions comprising a low-temperature additive which comprises at least one oil-soluble amide-ammonium salt of a polycarboxylic acid with a mono- and/or dialkylamine. On page 2 lines 6-8 Krull discloses that fuel oils include second-generation biofuels, which Krull indicates on page 1 lines 17-29 include HVO, as in the composition of Bush. On page 11 lines 3-6 and 25-27 Krull discloses that the polycarboxylic acid used to prepare the amide-ammonium salt can be a copolymerized dicarboxylic acid, preferably copolymers of maleic anhydride. From page 11 line 31 through page 12 line 10 Krull discloses that preferred comonomers include α-olefins, and that octadecene, a C18 olefin, is a preferred α-olefin. On page 13 lines 11-13 Krull discloses that secondary amines are preferred amines, and discloses on page 13 lines 20-23 that ditallowamine is a particularly preferred secondary amine. In Table 2A (Example A1) on page 40 Krull indicates that the copolymer of maleic anhydride and α-olefin is reacted with 2 equivalents of ditallowamine to arrive at the amide-ammonium salt. The reaction products of maleic anhydride, α-olefin, and secondary amine meet the limitations of component (c) of amended claims 7 and 18. When the α-olefin is octadecene, the secondary amine is ditallowamine, and the copolymer is reacted with 2 equivalents of ditallowamine, claim 11 is met as well. The inclusion of the additive composition of Krull in the composition of Bush, Kuronen, Kiiski, and Davies therefore meets the limitations of claims 7, 11, and 18.
It would have been obvious to one of ordinary skill in the art to include the additive composition of Krull in the composition of Bush, Kuronen, Kiiski, and Davies since Krull discloses on page 36 lines 1-16 that the additive composition imparts various advantages to low-sulfur diesel fuels, and teaches in the other cited sections that such fuels can comprise HVO.
Response to Arguments
Applicant's arguments filed 12/24/25 have been fully considered but they are not persuasive. Applicant argues that the Bush reference does not identify the problem solved by the current invention. However, as discussed above and in previous office actions, Bush, Kuronen, Kiiski, and Davies meets the method and compositional limitations of the claims, including the specific claimed biodiesel and renewable diesel components and the claimed copolymer, they will provide fuel compositions possessing the properties of claims 2-3. Applicant argues that the specific blends of HVO and biodiesel in the claimed amounts are not disclosed, but as mentioned in paragraph 5 above, Bush discloses that the fuel is present in greater than 50% by weight of the composition, or greater than 95% by weight of the composition, and can be a blend of HVO and biodiesel, in which case the concentration ranges for each individual component will encompass the ranges recited in claims 2-3. Additionally, the Kuronen reference discussed in paragraph 8 above provides more specific motivation to use a blend of biodiesel and renewable diesel in amounts overlapping the claimed ranges.
Applicant argues that Bush discloses numerous types of cold flow improvers and one of ordinary skill in the art would not have motivation to select the claimed comb polymers. However, "the prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed…." In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004).
Applicant argues that the Kiiski and Davies references are directed to different problems than that addressed by the current invention, but all the cited references, like the current invention, are in the lubricant field, and the rejections set forth motivations for combining the reference, which have not been addressed by applicant.
Applicant argues that the claimed method and composition produces unexpectedly superior results, and that the amendments make the claim scope more reflective of the examples supplied in the specification and Golisz declaration filed 8/27/25. While the claims have been narrowed, several issues identified in the office action mailed 9/29/25 still apply. In order to successfully overcome a prima facie such a showing must be commensurate in scope with the claims. See MPEP 716.02(d). In this case, the independent claims allow for the additive to comprise a copolymer selected from a broad class of copolymers, for the composition to comprise the copolymer in an amount of 5 to 350 ppm, and for the composition to contain the biodiesel and renewable diesel in broad concentration ranges. The inventive examples provided by applicant contain 104 to 250 ppm of a specific copolymer, and a specific base oil blend of 80% renewable diesel and 20% biodiesel. One of ordinary skill in the art would not be able to conclude from this limited data that superior results would be maintained across the full scope of the claims. Claim 22 recites a narrower copolymer concentration range more reflective of the inventive examples, but the other deficiencies still apply, and claim 22 only limits the composition claim 3. While claims 2-3 also require the fuel to have a filter blocking tendency of less than 2, this only limits the claims to those which produce superior results if compositions outside the scope of the claim cannot also achieve this property. The data provided in the declaration of Golisz contains some comparative examples that do not have the claimed filter blocking tendency, but the declaration does not establish, for example, that compositions comprising the cold flow improver in amounts of more than 350 ppm (within the ranges disclosed in paragraph 72 of Bush) would not produce the claimed filter blocking tendency, or that compositions comprising relative amounts of biodiesel and renewable diesel outside the claimed ranges would not produce the claimed filter blocking tendency. The data in the declaration also does not necessarily establish that comparative examples comprising “Additive B” in amounts within the claimed range could not produce the claimed filter blocking tendency, since the comparative examples only contain 190 and 285 ppm of the additive, and demonstrate that the filter blocking tendency test result varies significantly with concentration. Applicant therefore has not established that the claimed composition and method would produce unexpected results commensurate in scope with the claims, and does not overcome the prima facie cases of obviousness set forth in the rejections.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 JAMES C GOLOBOY whose telephone number is (571)272-2476. The examiner can normally be reached M-F, usually about 10:00-6:30.
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/JAMES C GOLOBOY/Primary Examiner, Art Unit 1771