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 .
Status of the Application
Receipt of the Response and Amendment after Non-Final Office Action filed 5 December 2025 is acknowledged.
Applicant has overcome the following by virtue of amendment of the claims: (1) the objection to claim 52 has been withdrawn; (2) the 112(b) rejection of claim 47 has been withdrawn.
The status of the claims upon entry of the present amendment stands as follows:
Pending claims: 1-15, 17-20, 22, 24, and 45-56
Withdrawn claims: 1-15, and 17-20
Previously canceled claims: 16, 21, 23, 25-44
Newly canceled claims: None
Amended claims: 47 and 52
New claims: None
Claims currently under consideration: 22, 24, and 45-56
Currently rejected claims: 22, 24, and 45-56
Allowed claims: None
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
References:
Note: The names of the references “Dundford” and “Dunford” cited in the previous Office Action have been corrected hereinbelow. “Dundford” in the previous action has been corrected to “Dunford”, and the previous “Dunford” is corrected to “Dunford 2” throughout the present Office Action. Changes are to the name only. The cited documents remain the same.
Mandal 1985 (Mandal, B., Majumdar, S. G., & Maity, C. R. (1985). Effect of Refined Hydrogenated Karanja Oil on Lipid Metabolism in Adult Male Albino Rats. Acta Alimentaria, 14(1), 3-13, cited on the IDS filed on 28 November 2022)
Mandal 1984 (Mandal, B., Majumdar, S. G., & Maity, C. R. (1984). Chemical and Nutritional Evaluation of Pongamia glabra Oil and Acacia auriculaeformis Oil. JAOCS, 61(9), 1447-1449, cited on the IDS filed on 28 November 2022)
Gautam et al. (Gautam, K., Gupta, N. C., & Sharma, D. K. (2013). Physical characterization and comparison of biodiesel produced from edible and non-edible oils of Madhuca indica (mahua), Pongamia pinnata (karanja), and Sesamum indicum (til) plant oilseeds. Biomass Conv Bioref, 4, 193-200.)
Boerner et al. (US 10,577,558 B2)
Dunford (Dunford, (2016). Edible Oil Quality, Available online at <https://extension.okstate.edu/fact-sheets/edible-oil-quality.html>, 4 pages, cited on the IDS filed on 28 November 2022)
Klonoff (Klonoff, D. C. (2007). Replacements for Trans Fats—Will There Be an Oil Shortage? J Diabetes Sci Technol, (1)3, 415-422.)
Heymann et al. (US 2019/0144778 A1)
Sulzer (Sulzer (2025). Kühni Agitated Columns from Sulzer. 3 pages. Accessed on 3 April 2025 from https://www.news-medical.net/Kuhni-Agitated-Columns-from-Sulzer)
Dunford 2 (Dunford, N. (2016, July). Oil and Oilseed Processing II. OSU Extension. https://extension.okstate.edu/fact-sheets/oil-and-oilseed-processing-ii.html)
Claims 22, 24, 52-53, and 55-56 are rejected under 35 U.S.C. 103 as being unpatentable over Mandal 1985 in view of Gautam, Boerner, Dunford, and Klonoff and as evidenced by Mandal 1984.
Regarding claim 22, Mandal 1985 teaches method for producing a pongamia oil composition (p. 4, § 1.1 “Preparation of RHKO”), comprising:
Chemically separating dehulled pongamia oilseeds to produce crude pongamia oil, and a seedcake that is at least partially deoiled – “Deep brown colored KO [i.e., karanja oil, a.k.a. pongamia oil] was extracted from the ground karanja seed by Soxhlet solvent (petroleum ether, 60-80 °C) extraction method” (p. 4, ¶ 4),
wherein the crude pongamia oil comprises pongamia oil, karanjin, pongamol, other furanoflavonoids, and other unsaponifiable matter – These components are seen to be inherent features of a crude pongamia oil as evidenced by Fig. 3A and paragraph [0021] of the instant specification.
extracting the crude pongamia oil with alcohol to produce the pongamia oil composition – “The remaining brown coloured oil was first steam distilled and then refined by alcohol…” (p. 4, ¶ 4),
wherein the composition is edible and non-bitter tasting – “…the refined hydrogenated karanja oil (RHKO) could be incorporated in foods as a fat ingredient” (p. 3, Abstract and p. 11, ¶ 3) indicates that the composition is edible, and “…the hydrogenated product…was found to be devoid of bitterness…” (p.4, ¶ 4),
has less than or equal to about 400 ppm of karanjin and less than or equal to about 400 ppm pongamol – “The product RHKO, was also free from the toxic pongamol and karanjin, examined by following the usual tests…” (pp. 4-5, bridging paragraph). The limitation “as determined by HPLC-DAD analysis of an acetone extract obtained from the pongamia oil composition” is not required to be met as there is no recitation that the analysis is performed as a step of the claimed method. As written, the claim requires that oil composition comprises less than or equal to about 400 ppm of each karanjin and pongamol, which is met by the method of Mandal;
less than or equal to about 1% by weight of unsaponifiable matter – as evidenced by Mandal 1984, a karanja oil refined by the method of Mandal 1985 (p.1447, col. 2, ¶ 2) has: “Unsaponifiable fraction 0.6%” (p. 1448, col. 1, Table 1, line 2, “Karanja”).
Mandal 1985 does not teach mechanically separating dehulled pongamia oilseeds to produce crude pongamia oil and a seedcake that is at least partially deoiled, that the oil is extracted with ethanol at a temperature of about 50 °C to about 70 °C, that the ratio of solvent to crude pongamia oil is between 1:1 and 20:1, that the oil composition comprises a peroxide value of less than or equal to about 5 meq/kg; a p-anisidine value of less than or equal to about 10; and less than or equal to about 5% by weight of trans fatty acids.
However, Gautam discloses a pongamia oil extracted from the oilseeds by pressing that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3). Extraction of oil by pressing oilseeds inherently results in a crude oil and a seedcake that is at least partially deoiled.
It would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to have substituted the chemical separation of the pongamia oilseeds disclosed by Mandal 1985 with the mechanical pressing process disclosed by Gautam to produce a crude pongamia oil and a seedcake that is at least partially deoiled as claimed, see MPEP § 2143(I)(B). First, Mandal 1985 teaches chemically separating oil from pongamia oilseeds – “Deep brown colored KO [i.e., karanja oil, a.k.a. pongamia oil] was extracted from the ground karanja seed by Soxhlet solvent (petroleum ether, 60-80 °C) extraction method” (p. 4, ¶ 4). Gautam discloses a pongamia oil extracted from the oilseeds by pressing (i.e., mechanical separation) that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3). Since both chemical and mechanical separation result in a crude pongamia oil and an implicit at least partially deoiled seedcake, one of ordinary skill in the art could have substituted one known method for the other with predictable results.
Regarding the ethanol extraction, temperature, and solvent ratio, Boerner teaches a method of combined digestion and extraction of oil-containing seeds with ethanol, wherein the oilseeds have an oil content of greater than or equal to 30 mass %, and wherein the mass ratio of oilseed to ethanol is 1:3 to 1:8, preferably 1:5 (col. 5, lines 5-35). Boerner further teaches that the extraction is carried out at a temperature of about 70 °C (col. 7, lines 5-7). The process eliminates the largely anti-nutritive substances from the oil, as well as the bitter and color compounds (col. 7, lines 61-64).
At the lowest oil content of 30%, the ratios of solvent to crude oil disclosed by Boerner equate to 10:1 to 26:1. The claimed range of 1:1 to 20:1 overlaps the disclosed range. In a case where the claimed ranges overlap or lie inside ranges disclosed by the prior art, a prima facie case of obviousness exists, MPEP § 2144.05(I).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the karanja/pongamia oil alcohol extraction of the method of Mandal 1985 according to the teachings of Boerner to comprise extraction of the crude karanja/pongamia oil with ethanol at a temperature of about 70 °C at a ratio of solvent to crude pongamia oil of between 10:1 and 26:1. One of ordinary skill in the art would have been motivated to consult Boerner for more details on the alcohol extraction as none are supplied by Mandal 1985. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Mandal 1985 teaches that the alcohol extraction results in a product “free from the toxic pongamol and karanjin, examined by following the usual tests…” (pp. 4-5, bridging paragraph), and Boerner teaches that extracting seed oil with ethanol eliminates the largely anti-nutritive substances from the oil, as well as the bitter and color compounds (col. 7, lines 61-64). It is seen that the pongamol and karanjin would be extracted by the ethanol taught by Boerner.
Regarding the peroxide value and p-anisidine value, Dunford discloses that “…peroxide value (PV) and p-anisidine value (AV) are commonly used in industry to report edible oil quality.” (p. 197-1, col. 2, ¶ 1). “Refined oils usually have a PV of <1 meq/kg. Oils are considered oxidized when PV >3 meq/kg.” (p. 197-2, col. 1, “Peroxide Value”, ¶ 2). “Refined oils should have AV <5.” (p. 197-2, col. 1, “p-Anisidine Value”, ¶ 2).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the method of Mandal 1985 to produce a refined karanja/pongamia oil having a peroxide value of less than or equal to about 5 meq/kg and a p-anisidine value of less than or equal to about 10 as claimed, according to the teachings of Dunford. One of ordinary skill in the art would have been motivated to produce such an oil composition to ensure the product reached known oil quality parameters. Since adhering to quality parameters is indicative of producing a successful product, one of ordinary skill in the art would have had a reasonable expectation of success for doing so.
Regarding the trans fatty acid content, Klonoff teaches that trans fats in the diet are associated with an increased risk of coronary artery disease (p. 416, col. 1, ¶ 2), and that trans fats are formed when liquid oils are converted into solid fats through partial hydrogenation of their unsaturated fatty acids (p. 416, col. 2, ¶ 2).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the method of Mandal 1985 to reduce or remove the hydrogenation step to provide a karanja/pongamia oil with minimal trans fatty acid content, including less than or equal to about 5% by weight of trans fatty acids as claimed. First, Mandal 1985 is concerned with producing an edible karanja oil, and does so by first refining to remove its color, bad odor and toxic constituents, and then hydrogenating it (p. 4, ¶ 3); the oil is already refined to an edible state before hydrogenation. Since Klonoff teaches that hydrogenation of liquid oils results in the formation of trans fats (p. 416, col. 2, ¶ 2), and that trans fats in the diet are associated with an increased risk of coronary artery disease (p. 416, col. 1, ¶ 2), one of ordinary skill in the art would have been motivated to reduce or omit the hydrogenation of the detoxified, refined karanja/pongamia oil to provide an edible oil composition with lower health risk factors. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because hydrogenation as performed by Mandal 1985 is subsequent to detoxifying the oil, so the un-hydrogenated oil could be used as a dietary additive.
For these reasons, claim 22 is rendered obvious.
Regarding claim 24, Mandal 1985 teaches method for producing a pongamia oil composition (p. 4, § 1.1 “Preparation of RHKO”), comprising:
a) Chemically separating dehulled pongamia oilseeds to produce crude pongamia oil, and a seedcake that is at least partially deoiled – “Deep brown colored KO [i.e., karanja oil, a.k.a. pongamia oil] was extracted from the ground karanja seed by Soxhlet solvent (petroleum ether, 60-80 °C) extraction method” (p. 4, ¶ 4),
wherein the crude pongamia oil comprises pongamia oil, karanjin, pongamol, other furanoflavonoids, and other unsaponifiable matter – These components are seen to be inherent features of a crude pongamia oil as evidenced by Fig. 3A and paragraph [0021] of the instant specification.
b) separating the crude pongamia oil into a raffinate and a solvent-rich light phase by liquid-liquid extraction using immiscible solvent – “The remaining brown coloured oil was first steam distilled and then refined by alcohol…” (p. 4, ¶ 4). “Refined by alcohol” is seen to be a liquid-liquid extraction of the karanja/pongamia oil using an immiscible solvent (i.e., alcohol).
d) wherein the composition is edible and non-bitter tasting – “…the refined hydrogenated karanja oil (RHKO) could be incorporated in foods as a fat ingredient” (p. 3, Abstract and p. 11, ¶ 3) indicates that the composition is edible, and “…the hydrogenated product…was found to be devoid of bitterness…” (p.4, ¶ 4),
has less than or equal to about 400 ppm of karanjin and less than or equal to about 400 ppm pongamol – “The product RHKO, was also free from the toxic pongamol and karanjin, examined by following the usual tests…” (pp. 4-5, bridging paragraph). The limitation “as determined by HPLC-DAD analysis of an acetone extract obtained from the pongamia oil composition” is not required to be met as there is no recitation that the analysis is performed as a step of the claimed method. As written, the claim requires that oil composition comprises less than or equal to about 400 ppm of each karanjin and pongamol, which is met by the method of Mandal;
less than or equal to about 1% by weight of unsaponifiable matter – as evidenced by Mandal 1984, a karanja oil refined by the method of Mandal 1985 (p.1447, col. 2, ¶ 2) has: “Unsaponifiable fraction 0.6%” (p. 1448, col. 1, Table 1, line 2, “Karanja”).
Mandal 1985 does not teach that the method is a continuous countercurrent method, a) mechanically separating dehulled pongamia oilseeds to produce crude pongamia oil and a seedcake that is at least partially deoiled; b) separating the crude pongamia oil into a raffinate and a solvent-rich light phase at a temperature of about 50 °C to about 70 °C, wherein the ratio of solvent to crude pongamia oil is between 1:1 and 20:1, wherein the raffinate comprises pongamia oil and residual solvent, wherein the solvent comprises ethanol, and wherein the solvent-rich light phase comprises solvent and residual pongamia oil; c) cooling the raffinate to separate the residual solvent from pongamia oil; d) isolating at least a portion of the pongamia oil in the cooled raffinate to produce the pongamia oil composition, wherein the oil composition comprises a peroxide value of less than or equal to about 5 meq/kg; a p-anisidine value of less than or equal to about 10; and less than or equal to about 5% by weight of trans fatty acids; e) separating at least a portion of the solvent from the solvent-rich light phase; and f) combining the isolated solvent with additional crude pongamia oil for liquid-liquid extraction.
However, Gautam discloses a) mechanically separating dehulled pongamia oilseeds to produce crude pongamia oil and a seedcake that is at least partially deoiled – a pongamia oil extracted from the oilseeds by pressing that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3). Extraction of oil by pressing oilseeds inherently results in a crude oil and a seedcake that is at least partially deoiled.
It would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to have substituted the chemical separation of the pongamia oilseeds disclosed by Mandal 1985 with the mechanical pressing process disclosed by Gautam to produce a crude pongamia oil and a seedcake that is at least partially deoiled as claimed, see MPEP § 2143(I)(B). First, Mandal 1985 teaches chemically separating oil from pongamia oilseeds – “Deep brown colored KO [i.e., karanja oil, a.k.a. pongamia oil] was extracted from the ground karanja seed by Soxhlet solvent (petroleum ether, 60-80 °C) extraction method” (p. 4, ¶ 4). Gautam discloses a pongamia oil extracted from the oilseeds by pressing (i.e., mechanical separation) that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3). Since both chemical and mechanical separation result in a crude pongamia oil and an implicit at least partially deoiled seedcake, one of ordinary skill in the art could have substituted one known method for the other with predictable results.
Regarding the continuous countercurrent method and details of the liquid-liquid extraction, Boerner teaches a method of combined digestion and extraction of oil-containing seeds with ethanol (col. 5, lines 5-35). The method “is conceived as a multistep continuous or quasi continuous method” and may be operated in inverse flow (i.e., countercurrent) (col. 6, lines 46-49, Fig. 2). Boerner further teaches:
b) separating the crude oil into a raffinate and a solvent-rich light phase by liquid-liquid extraction using immiscible solvent wherein the solvent comprises ethanol – “The extraction of the oil is carried out with ethanol…Thereby all alcohol soluble constituents in the cell matrix and those in the dissolved and displaced oil dissolve into the ethanol. The dispersed oil droplets form a downward sediment in the solvent and form a separate oil phase [i.e., an oil raffinate below a solvent-rich light phase].” (col. 7, lines 43-51),
at a temperature of about 50 °C to about 70 °C – “Preferably the extraction is carried out at ambient pressure and temperature of about 70 °C.” (col. 7, lines 5-7),
wherein the ratio of solvent to crude oil is between 1:1 and 20:1 – “wherein cell digestion and extraction are carried out in a defined mass-ratio of oilseed to ethanol of 1:3 to 1:8, preferably at 1:5” (col. 5, lines 33-35), wherein the oilseeds have an oil content of greater than or equal to 30 mass % (col. 5, line 9). Therefore, at the lowest seed oil content of 30%, the preferred ratio of solvent to oilseed 5:1 disclosed by Boerner equates to a solvent to crude oil ratio of about 17:1, which lies inside the claimed range;
wherein the raffinate comprises oil and residual solvent – “The replaced oil (oil1)…contains approximately 6-9% ethanol.” (col. 10, lines 21-22), and
wherein the solvent-rich light phase comprises solvent and residual oil – “The orange-red miscella forms the upper phase and the free oil sinks to the bottom.” (col. 9, lines 35-36). “Miscella (mixture) is designated as a mixture of organic extraction/solvent and oil, which is an intermediate product in the production of plant oils.” (col. 5, lines56-58);
c) cooling the raffinate to separate the residual solvent from oil – “The oil dissolved in the ethanol can also be separated by lowering its solubility at reduced temperature.” (col. 5, lines 42-43). It is seen to be within the scope of what is disclosed by Boerner that cooling can also be applied to separate residual solvent from oil based on lower solubility at decreased temperature.
d) isolating at least a portion of the pongamia oil in the cooled raffinate to produce the oil composition – “After cooling, the liquid extract is separated into miscella, extraction mix, and free oil.” (col. 7, lines 53-54). The free oil is seen as the oil composition;
e) separating at least a portion of the solvent from the solvent-rich light phase – “For the solvent recovery, the entire miscella [i.e., solvent-rich light phase] and the extract mix are gently evaporated in a rotation evaporator.” (col. 9, lines 63-66);
f) combining the isolated solvent with additional crude oil for liquid-liquid extraction – The removed ethanol is returned to the extraction cycle (i.e., introduced to additional crude oil). (col. 9, lines 63-66).
The process eliminates the largely anti-nutritive substances from the oil, as well as the bitter and color compounds (col. 7, lines 61-64).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the karanja/pongamia oil alcohol extraction of the method of Mandal 1985 according to the teachings of Boerner to comprise the so disclosed claimed steps and features as a suitable way to remove undesirable compounds. One of ordinary skill in the art would have been motivated to consult Boerner for more details on the alcohol extraction as none are supplied by Mandal 1985. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Mandal 1985 teaches that the alcohol extraction results in a product “free from the toxic pongamol and karanjin, examined by following the usual tests…” (pp. 4-5, bridging paragraph), and Boerner teaches that extracting seed oil with ethanol eliminates the largely anti-nutritive substances from the oil, as well as the bitter and color compounds (col. 7, lines 61-64). It is seen that the pongamol and karanjin would be extracted by the ethanol taught by Boerner.
Regarding the peroxide value and p-anisidine value, Dunford discloses that “…peroxide value (PV) and p-anisidine value (AV) are commonly used in industry to report edible oil quality.” (p. 197-1, col. 2, ¶ 1). “Refined oils usually have a PV of <1 meq/kg. Oils are considered oxidized when PV >3 meq/kg.” (p. 197-2, col. 1, “Peroxide Value”, ¶ 2). “Refined oils should have AV <5.” (p. 197-2, col. 1, “p-Anisidine Value”, ¶ 2).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the method of Mandal 1985 to produce a refined karanja/pongamia oil having a peroxide value of less than or equal to about 5 meq/kg and a p-anisidine value of less than or equal to about 10 as claimed, according to the teachings of Dunford. One of ordinary skill in the art would have been motivated to produce such an oil composition to ensure the product reached known oil quality parameters. Since adhering to quality parameters is indicative of producing a successful product, one of ordinary skill in the art would have had a reasonable expectation of success for doing so.
Regarding the trans fatty acid content, Klonoff teaches that trans fats in the diet are associated with an increased risk of coronary artery disease (p. 416, col. 1, ¶ 2), and that trans fats are formed when liquid oils are converted into solid fats through partial hydrogenation of their unsaturated fatty acids (p. 416, col. 2, ¶ 2).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the method of Mandal 1985 to reduce or remove the hydrogenation step to provide a karanja/pongamia oil with minimal trans fatty acid content, including less than or equal to about 5% by weight of trans fatty acids as claimed. First, Mandal 1985 is concerned with producing an edible karanja oil, and does so by first refining to remove its color, bad odor and toxic constituents, and then hydrogenating it (p. 4, ¶ 3); the oil is already refined to an edible state before hydrogenation. Since Klonoff teaches that hydrogenation of liquid oils results in the formation of trans fats (p. 416, col. 2, ¶ 2), and that trans fats in the diet are associated with an increased risk of coronary artery disease (p. 416, col. 1, ¶ 2), one of ordinary skill in the art would have been motivated to reduce or omit the hydrogenation of the detoxified, refined karanja/pongamia oil to provide an edible oil composition with lower health risk factors. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because hydrogenation as performed by Mandal 1985 is subsequent to detoxifying the oil, so the un-hydrogenated oil could be used as a dietary additive.
For these reasons, claim 24 is rendered obvious.
Regarding claims 52 and 53, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 24.
Mandal 1985 does not teach that the separating of at least a portion of the solvent from the solvent-rich light phase is performed in an evaporator (re: claim 52) and that the separating of solvent is evaporated from the residual pongamia oil under vacuum (re: claim 53).
However, Boerner teaches “…the recovery of the ethanol is carried out by means of vacuum evaporation.” (col. 7, lines23-24).
Therefore, it would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to carry out the separation of at least a portion of the solvent-rich light phase according to the method of Mandal 1985 as modified by the teachings of Boerner described regarding claim 24 above in vacuum evaporator as further taught by Boerner with the same motivation and with the same expectation of success as described regarding claim 24 above, rendering claims 52 and 53 obvious.
Regarding claim 55, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 24.
Mandal 1985 does not teach that the method further comprises isolating the residual pongamia oil in the solvent-rich light phase; and distilling solvent from the isolated residual pongamia oil to produce additional pongamia oil composition.
However, Boerner teaches isolating the residual pongamia oil in the solvent-rich light phase – “For the solvent recovery, the entire miscella and the extract mix are gently evaporated in a rotation evaporator. After removal of the ethanol which is returned to the extraction cycle, a liquid oil phase (oil2) [i.e., residual oil] and an orange-red solid phase, the so-called bottom product (consisting of oil, phospholipids, oligosaccharides, phenolic compounds and glucosinolate) remains in the rotation evaporator.” (col. 2 line 63 – col. 10, line 2);
and distilling solvent from the isolated residual pongamia oil to produce additional pongamia oil composition – “The bottom product is thereafter washed with acetone. An acetone insoluble phase, consisting of phospholipids and the oligosaccharides remains and is separated. In the following step of refining/distillation of the acetone, besides a liquid oil phase (oil3), a solid phase is also obtained.” (col. 10, lines 3-7). Oil3 is additional oil composition.
It would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to apply the known technique of isolating additional oil from solvent-rich light phase as taught by Boerner to improve the alcohol extraction of Mandal 1985 to yield predictable results, see MPEP 2143(I)(D). First, Mandal 1985 teaches the base method of an alcohol extraction of karanja/pongamia oil as described regarding claim 24 above. Since Boerner teaches the known technique of isolating additional oil from the solvent-rich light phase of an ethanol extraction of seed oil (col. 2 line 63 – col. 10, line 7), the technique is applicable to the method of Mandal 1985, and one of ordinary skill in the art would have recognized that applying the known technique would have yielded the predictable result of increasing the overall yield of the refined karanja/pongamia oil composition, resulting in an improved system.
Claim 55 is therefore rendered obvious.
Regarding claim 56, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 24.
Mandal 1985 does not teach that the crude pongamia oil is mechanically separated pongamia oil.
However, Gautam discloses a pongamia oil extracted from the oilseeds by pressing that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3).
It would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to have substituted the chemical separation of the pongamia oilseeds disclosed by Mandal 1985 with the mechanical pressing process disclosed by Gautam to produce a crude pongamia oil and a seedcake that is at least partially deoiled as claimed, see MPEP § 2143(I)(B). First, Mandal 1985 teaches chemically separating oil from pongamia oilseeds – “Deep brown colored KO [i.e., karanja oil, a.k.a. pongamia oil] was extracted from the ground karanja seed by Soxhlet solvent (petroleum ether, 60-80 °C) extraction method” (p. 4,¶ 4). Gautam discloses a pongamia oil extracted from the oilseeds by pressing (i.e., mechanical separation) that is used as a crude oil for subsequent processing (p. 194, col. 2, ¶ 3). In this way, the crude oil of the method is mechanically separated pongamia oil.
Claim 56 is therefore rendered obvious.
Claims 45-49 are rejected under 35 U.S.C. 103 as being unpatentable over Mandal 1985 in view of Gautam, Boerner, Dunford, and Klonoff, and as evidenced by Mandal 1984 as applied to claims 22 and 24 above, and further in view of Heymann.
Regarding claims 45 and 46, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 22.
The cited prior art does not teach that the ratio of solvent to crude pongamia oil is between about 1:1 and about 5:1 (re: claim 45) or that the ratio of solvent to crude pongamia oil is between about 3:1 and about 4:1 (re: claim 46).
However, Heymann teaches a method for extracting fatty acids from triglyceride oils ([0018]) using immiscible polar solvents such as water, ethanol, methanol, or mixtures thereof ([0029]) in a ratio of the volume of the aqueous phase (i.e., solvent/ethanol) to the volume of the triglyceride oil from 1.5:1 to 4:1 ([0075]).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to further modify the karanja/pongamia oil alcohol extraction of the method of Mandal 1985 in view Boerner described above according to the teachings of Heymann to comprise extraction of the crude karanja/pongamia at a ratio of solvent to crude pongamia oil of between 3:1 and 4:1 as claimed. One of ordinary skill in the art would have been motivated to consult Heymann for more details on the alcohol extraction as none are supplied by Mandal 1985, and Boerner discusses ratios with respect to the amount of oilseed to solvent. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Heymann teaches preferred ratios of 1.5:1 to 4:1 of a solvent, which may be ethanol ([0029]), in an extraction of triglyceride oil ([0075]).
Claims 45 and 46 are therefore rendered obvious.
Regarding claim 47, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 22.
Mandal 1985 as modified by Boerner implicitly teaches that the crude pongamia oil and the ethanol form a mixture since the two liquids are combined to perform an extraction as described above.
The cited prior art is silent regarding the duration of mixing, and as such does not teach that the mixture is agitated for at least 30 minutes.
However, Heymann teaches a method for extracting fatty acids from triglyceride oils ([0018]) using immiscible polar solvents such as ethanol ([0029]), and that “[t]he mixing, such as for example the contacting in the column in the case of continuous contacting, may be adjusted by a person skilled in the art such that as large a fraction as possible of the triglyceride oil phase T1 migrates into the aqueous phase W1. Accordingly, the contacting is carried out, for example, for 1 second to 2 hours, particularly 30 seconds to 1 hour, preferably 1 to 50 minutes…” ([0076]).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to further modify the karanja/pongamia oil alcohol extraction of the method of Mandal 1985 in view Boerner described above according to the teachings of Heymann to comprise mixing/agitating the mixture of crude pongamia oil and the ethanol for at least 30 minutes as claimed. One of ordinary skill in the art would have been motivated to consult Heymann for more details on the alcohol extraction as Mandal 1985 and Boerner are silent regarding the mixing time. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Heymann teaches that the triglyceride oil and the solvent are mixed for a duration of “1 second to 2 hours, particularly 30 seconds to 1 hour, preferably 1 to 50 minutes…” ([0076]). The claimed range of at least about 30 minutes overlaps the disclosed ranges. In a case where the claimed ranges overlap or lie inside ranges disclosed by the prior art, a prima facie case of obviousness exists, MPEP § 2144.05(I).
Therefore, claim 47 is rendered obvious.
Regarding claims 48 and 49, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 24.
The cited prior art does not teach that the ratio of solvent to crude pongamia oil is between about 1:1 and about 5:1 (re: claim 48) or that the ratio of solvent to crude pongamia oil is between about 3:1 and about 4:1 (re: claim 49).
However, Heymann teaches a method for extracting fatty acids from triglyceride oils ([0018]) using immiscible polar solvents such as water, ethanol, methanol, or mixtures thereof ([0029]) in a ratio of the volume of the aqueous phase (i.e., solvent/ethanol) to the volume of the triglyceride oil from 1.5:1 to 4:1 ([0075]).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to further modify the karanja/pongamia oil alcohol extraction of the method of Mandal 1985 in view Boerner described above according to the teachings of Heymann to comprise extraction of the crude karanja/pongamia at a ratio of solvent to crude pongamia oil of between 3:1 and 4:1 as claimed. One of ordinary skill in the art would have been motivated to consult Heymann for more details on the alcohol extraction as none are supplied by Mandal 1985, and Boerner discusses ratios with respect to the amount of oilseed to solvent. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Heymann teaches preferred ratios of 1.5:1 to 4:1 of a solvent, which may be ethanol ([0029]), in an extraction of triglyceride oil ([0075]).
Claims 48 and 49 are therefore rendered obvious.
Claims 50-51 are rejected under 35 U.S.C. 103 as being unpatentable over Mandal 1985 in view of Gautam, Boerner, Dunford, and Klonoff, and as evidenced by Mandal 1984 as applied to claims 22 and 24 above, and further in view of Heymann as evidenced by Sulzer.
Regarding claims 50 and 51, Mandal 1985, Gautam, Boerner, Dunford, and Klonoff teach the method of claim 24 comprising the continuous liquid-liquid extraction.
The cited prior art does not teach that the continuous liquid-liquid extraction is performed using a forced agitated column (re: claim 50), that the forced agitated column is a forced agitated trayed column, the raffinate exits the column at the bottom, and the solvent-rich light phase exits the column at the top (re: claim 51).
However, Heymann teaches a method for extracting fatty acids from triglyceride oils ([0018]) using immiscible polar solvents such as ethanol ([0029]), and that “[i]t is also possible to mix T1 [i.e., the oil] and W1 [i.e., the solvent] continuously in countercurrent flow, for example in a column...The column may be a sieve tray column, a structured packing column or an agitated column such as, for example, a Kühni column or a Scheibel column.” ([0066]). As evidenced by Sulzer, a Kühni column is an agitated trayed column (p. 1, Title and Image). It is considered that the column is forced as the liquids are continuously passed through the column.
Heymann further teaches, “[i]n the continuous processes in countercurrent flow in a column, for example, the triglyceride oil T1 is introduced at or at least close to the bottom end of the column and the aqueous solution W1 is introduced at or at least close to the top end of the column ([0068]), and “[t]he aqueous phase W2, which has an increased content of fatty acids compared to W1, is then discharged at or close to the bottom end of the column, and a triglyceride oil phase T2, which has a reduced content of fatty acids compared to T1, is then discharged at or close to the top end of the column.” ([0069]). In this example, the solvent W is water (density = 1.000 g/mL) as “preference is given to using water as a solvent” ([0029]), which is heavier than oil (pongamia oil density = 0.925-0.950 g/mL). In an ethanol extraction, the ethanol solvent (density = 0.789 g/mL) is lighter than oil, and would naturally rise to the top. Therefore, one of ordinary skill in the art would have recognized that in a countercurrent ethanol extraction of pongamia oil, the flow should be arranged such that the raffinate (i.e., oil) exits the column at the bottom, and the solvent-rich light phase exits the column at the top.
Therefore, it would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to further modify the method of Mandal 1985 from that described regarding claim 24 to employ a forced agitated trayed column, such as the Kühni column disclosed by Heymann, wherein the raffinate exits the column at the bottom, and the solvent-rich light phase exits the column at the top during the continuous liquid-liquid extraction. In looking to Boerner for information regarding the alcohol extraction, one of ordinary skill in the art would have found that Boerner employs a reactor for the continuous extraction of oil from oilseed with ethanol (Fig. 3, and col. 9, lines 10-12). While the principles of Boerner remain applicable to a liquid-liquid extraction of karanja/pongamia oil with ethanol, one of ordinary skill in the art would have been motivated to consult Heymann for details regarding a suitable apparatus for a liquid-liquid extraction of the karanja/pongamia oil with ethanol. One of ordinary skill in the art would have had a reasonable expectation of success for doing so because Heymann teaches a employing a Kühni column for continuous countercurrent extraction of triglyceride oil with an ethanol solvent, wherein the heavy phase is exits the column at the bottom and the light phase exits the column at the top as described above.
Claims 50 and 51 are therefore rendered obvious.
Claim 54 is rejected under 35 U.S.C. 103 as being unpatentable over Mandal 1985 in view of Gautam, Boerner, Dunford, and Klonoff as applied to claim 53 above, and further in view of Dunford 2.
Regarding claim 54, Mandal 1985, Gautam, Boerner, Dunford, Klonoff, and Heymann teach the method of claim 53.
The cited prior art does not teach that the method further comprises condensing the solvent, and stripping the solvent of any accumulated water in a stripping column.
However, Dunford 2 teaches that “[s]olvent recovery from miscella (oil + solvent) is carried out in distillation columns. An additional stripping column, which is heated indirectly with steam, removes residual solvent and moisture [i.e., water] in the oil. Solvent vapors from distillation and stripping columns are condensed and recycled to the extractor.” (p. 3, ¶ 3).
It would have been obvious for one of ordinary skill in the art, before the effective filing date of the claimed invention, to apply the known technique of condensing and stripping the solvent of any accumulated water in a stripping column according to the teachings of Dunford 2 to improve the modified alcohol extraction of Mandal 1985 as described regarding claim 53 to yield predictable results, see MPEP 2143(I)(D). First, Mandal 1985 teaches the base method of an alcohol extraction of karanja/pongamia oil as described regarding claim 53 above. Since Dunford 2 teaches the known technique of solvent recovery using a stripping column in oil desolventizing (p. 3, ¶ 3), the technique is applicable to the method of Mandal 1985, and one of ordinary skill in the art would have recognized that applying the known technique would have yielded the predictable result of recovering a more pure solvent for subsequent use in the continuous extraction process, resulting in an improved system.
Claim 54 is therefore rendered obvious.
Response to Arguments
Claim Objections:
Applicant has overcome the objection to claim 52 by amendment. Accordingly, the objection has been withdrawn.
Claim Rejections – 35 U.S.C. § 112:
Applicant has overcome the 35 U.S.C. § 112(b) rejection of claim 47 based on amendment to the claim. Accordingly, the 35 U.S.C. § 112(b) rejection has been withdrawn.
Claim Rejections – 35 U.S.C. § 103: Applicant’s arguments filed on 10 October 2025 have been fully considered, but they are not persuasive.
Applicant first argued that the claimed methods address an unmet need in the art: no one has made an edible pongamia oil (p. 10, ¶ 3), and the claimed methods address this unmet need by providing pongamia oil compositions that “are edible, non-bitter, and have an overall acceptable sensory profile in humans (e.g., with respect to taste and smell) (pp. 10-11, bridging ¶).
Applicant’s argument has been considered, but it is not persuasive. MPEP § 716.04 addresses “Long-Felt Need and Failure of Others”. MPEP § 716.04(I) states, “The claimed invention must satisfy a long-felt need which was recognized, persistent, and not solved by others. Establishing long-felt need requires objective evidence that an art recognized problem existed in the art for a long period of time without solution”, and “[s]econd, the long-felt need must not have been satisfied by another before the invention by the inventor.” Applicant has not established that there is an unmet need and their assertion that “no one has made an edible pongamia oil” contradicts the teaching of Mandal 1985 that says: “In the present study raw KO was refined by removing its colour, bad colour and toxic constituents and then it was hydrogenated to upgrade it as an EDIBLE OIL.” (p. 4, ¶ 3). Applicant does not appear to have established a recognition that a PROBLEM existed without solution (prong 1) or that another did not already solve the alleged need (prong 2). Applicant’s invention appears to be an alternative method to make an edible pongamia oil.
Applicant next argued that the refined hydrogenated karanja oil described in Mandal 1985 has a compositional profile which falls outside the scope of the claims in that the hydrogenation results in approximately 20% of trans fats (p. 11, ¶ 4 – p. 12), and that the proposed modification of Mandal 1985 to remove the hydrogenation step based on the teachings in Klonoff changes the principle of operation of Mandal 1985 and also renders Mandal 1985 unsatisfactory for its intended purpose (p. 13, ¶ 1 – p. 14 ¶ 2). Applicant argued that the proposed modification of the method of Mandal 1985 with the teachings of Klonoff is made with impermissible hindsight (p. 13, ¶ 2).
Applicant’s arguments have been considered, but they are not persuasive. While it is recognized that the amount of trans fats in the oil composition of Mandal 1985 is higher than the claimed range, the teachings of Klonoff that hydrogenation of liquid oils results in the formation of trans fats, which are associated with an increased risk of coronary artery disease provide motivation to reduce or omit the hydrogenation of the detoxified, refined karanja/pongamia oil to lower the health risk factors of the oil. As such, Applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning is not persuasive. It must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Regarding the argument that the combination of references is improper due to modifying the principle of operation, rendering Mandal 1985 unsatisfactory for its intended purpose, Applicant appears to rely on p. 4, ¶ 3 of Mandal 1985, which says “then it was hydrogenated to upgrade it as an edible oil” as implicitly teaching that it was not an edible oil before hydrogenation. However, p. 4, ¶ 1, says “inactivating the toxins by processing KO to upgrade it as an edible oil” and seems to imply simply removing the toxins get to the point of being an edible oil, which supports the position in the rejection. The phrase on p. 4, ¶ 3 can still be true if an edible oil is the result of the first refining step; the hydrogenation step can upgrade an edible oil to what would still be an edible oil. As such, modifying the method of Mandal 1985 based on the teaching in Klonoff would not require modifying the principle of operation of the method of Mandal 1985. Simply cutting out a processing step and not having the result of the processing step materialize, as expected, does not amount to changing the principle of operation of a method, even if the title of the reference refers to hydrogenated oil. Similarly, the proposed modification does not render the invention of Mandal 1985 unsatisfactory for its intended purpose because the unhydrogenated, refined oil is still an edible oil, which “could be incorporated in foods as a fat ingredient” (See Mandal 1985, last sentence and Remarks, p. 14, ¶ 2). It is therefore maintained that a prima facie case of obviousness exists.
Applicant next argued that none of the remaining secondary references cure the deficiencies set forth with respect to Mandal 1985 alone or in combination with Klonoff (p. 15, ¶ 4 – p. 20).
Applicant’s argument has been considered, but it is moot because the combination of Mandal 1985 and Klonoff is deemed to be proper as described above.
Applicant next argued that the oil in evidentiary reference Mandal 1984 is not considered to be edible and Mandal 1984 acknowledges that the methods described therein do not result in “complete detoxification” and that suitable methods in the art to do so are needed (p. 15, last ¶ - p. 16, ¶ 1).
Applicant’s argument has been considered, but it is not persuasive. The excerpt on p. 16 seems to indicate only that “complete detoxification” is desired, without reference to hydrogenation. It is unclear how hydrogenation would be involved in removing toxins. One of ordinary skill in the art would recognize that the alcohol extraction of Mandal 1985 would extract flavonoids including karanjin and pongamol, which Mandal 1985 identifies as toxic flavonoids (p. 3, bottom ¶).
Applicant next argued that Boerner is cited for teaching the use of ethanol as an extraction solvent based on impermissible hindsight (p. 17, ¶ 1).
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). Boerner demonstrates that ethanol extraction of oils was known in the art before the effective filing date of the claimed invention, and the teachings are broadly applicable to seed oils, which would include pongamia oil. As Mandal 1985 is not specific as to the alcohol, the teachings of Boerner are relevant and would have been an obvious choice for one of ordinary skill in the art taking into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made.
Applicant next argued that Dundford (now “Dunford”) does not provide any guidance to a skilled artisan how to obtain the p-anisidine value and peroxide value, particularly in pongamia oil (p. 17, ¶ 4).
Applicant’s argument has been considered, but it is not persuasive. Dunford teaches that refined oils have those claimed parameters, such that “refining” an oil is implicitly how you would achieve those values. A skilled practitioner would be able to consult the art in achieving such values. Further, both peroxide value and p-anisidine value are measures of oxidation in fat, such that values that fall within the claimed ranges should be achievable via conventional methods for preventing/minimizing oxidation in fat (e.g., normal considerations such as minimizing processing “harshness”/environmental exposure/time of processing/etc.).
Applicant next argued that Heymann is cited for teaching the use of immiscible polar solvents such as water, ethanol, methanol, or mixtures thereof in a ratio of the volume of the aqueous phase to the volume of triglyceride oil from 1.5:1 to 4:1 based on impermissible hindsight (p. 18, ¶ 5 – p. 19, ¶ 1).
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). Heymann demonstrates that immiscible polar solvent extraction of oils using the ratio of 1.5:1 to 4:1 was known in the art before the effective filing date of the claimed invention, and the teachings are broadly applicable to triglyceride oils, which would include pongamia oil. As Mandal 1985 is not specific as to the alcohol, the teachings of Heymann are relevant and would have been an obvious choice for one of ordinary skill in the art taking into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made.
For at least these reasons, the rejections of claims 22, 24, and 45-56 under 35 U.S.C. § 103 are maintained.
Conclusion
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.
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/JAMES P. SHELLHAMMER/Examiner, Art Unit 1793
/EMILY M LE/Supervisory Patent Examiner, Art Unit 1793