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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on December 8, 2025 has been entered.
Claim Rejections - 35 USC § 103
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.
Claims 1-5, 7, 9, 12-16 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Barder et al. (US Pat. 4,849,112) in view of Hamunen (US Pat. 7,202,372) and Aro et al. (Separation and Purification Technology 175 (2017) 469-480) as evidenced by Herrlinger et al. (Methods of Analysis for Tall Oil Products, The Journal of the American Oil Chemists Society, Vol. 36, 119-124, 1959).
Considering Claims 1, 3, and 9: Barder et al. teaches a process of removing components from a tall oil product (Abstract) comprising the step of providing a tall oil mixture (1:30-50); subjecting the tall oil mixture to simulated moving bed chromatography (5:20-51) to separate the sterol component from the feed mixture/two fraction (4:26-34); and recovering the two fractions (4:35-63). The sterol fraction is neutral and the raffinate is neutral depleted. Barder et al. teaches the process can be used generally on tall oil feeds (1:31-44), with tall oil pitch being preferred (3:40-45).
Barder et al. teaches the solid phase as being carbon coated alumina (3:13-20) with a portion of the alumina being retained (Example 1). Alternatively, Barder et al. teaches that alumina is a known support for the chromatography step, albeit with reduced stability compared with the carbon support. "A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use." In re Gurley, 27 F.3d 551, 554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994). See MPEP § 2123
Barder et al. does not teach using crude tall oil with sufficient specificity. However, Hamunen teaches removing sterols directly from the crude tall oil (1:13-18). Barder et al. and Hamunen are analogous art as they are concerned with the same field of endeavor, namely tall oil sterol removal. It would have been obvious to a person of ordinary skill in the art to have performed the separation of Barder et al. prior to the evaporation step to form the pitch, as in Hamunen, and the motivation to do so would have been, as Hamunen suggests, sterols are lost during the evaporation (2:63-3:14), thus a higher percentage of sterols can be recovered.
Barder et al. teaches removing sterol from the tall oil product. Herrlinger et al. teaches that crude tall oil typically has an acid number of 166-170 (Table I), and that the acid number increases with reduction of the unsaponifiables, i.e. the sterols (Table I). As such, the raffinate will contain a higher concentration of acids and lower concentration of sterols, and thus a higher acid number, i.e. above 170. The acid number is a result effective variable showing the degree of sterol removal. It would have been obvious to a person of ordinary skill in the art to have selected an acid number in the claimed range, and the motivation to do so would have been, to provide a pure product with lower content of sterols.
Barder et al. does not teach how the crude tall oil is produced. However, Aro et al. teaches the crude tall oil is prepared commercially by producing wood pulp through a Kraft pulping process; separating a black liquor from the wood pulp; separating a soap from the black liquor by soap skimming; and producing crude tall oil from the soap, where no distillation takes place prior to the production of the crude tall oil (“the crude tall oil is distilled after production”)(Section 3, Scheme 1). Aro et al. teaches removing solid components from the crude tall oil by centrifuge (Section 3.2). It would have been obvious to a person of ordinary skill in the art to have prepared the crude tall oil through the method of Aro et al., and the motivation to do so would have been, as Aro et al. suggests, it is a commercially available process for producing crude tall oil.
Considering Claim 2: Barder et al. teaches one of the fractions is a sterol fraction/unsaponifiables (4:26-34).
Considering Claim 4: Barder et al. teaches that the simulated moving bed chromatography is sequential (5:20-51).
Considering Claim 5: Barder et al. teaches using toluene for the solvent (Example 1).
Considering Claim 7: Barder et al. teaches recovering sterols from the absorbed fraction (4:25-34).
Considering Claim 16 and 18: Aro et al. teaches recovering the fatty acids and the tall oil rosin acids from the crude tall oil from which the sterols are removed (Scheme 1). The isolation can be performed with a packed column or through an esterification reaction (Section 4.3, Fig. 9 and 10). It would have been obvious to a person of ordinary skill in the art to have isolated the fatty acids and rosin acids from the neutral fraction of Barder et al., and the motivation to do so would have been to recover valuable products from the tall oil.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Barder et al. (US Pat. 4,849,112) in view of Hamunen (US Pat. 7,202,372) and Aro et al. (Separation and Purification Technology 175 (2017) 469-480) as evidenced by Herrlinger et al. (Methods of Analysis for Tall Oil Products, The Journal of the American Oil Chemists Society, Vol. 36, 119-124, 1959) as applied to claim 16 above, and further in view of the evidence of Cleary et al. (US Pat. 4,524,030).
Considering Claim 17: Barder et al., Humunen and Aro et al. teach the process of claim 16 as shown above.
Aro et al. teaches recovering the fatty acids and the tall oil rosin acids from the crude tall oil from which the sterols are removed (Scheme 1). The isolation can be performed with a packed column or through an esterification reaction (Section 4.3, Fig. 9 and 10). It would have been obvious to a person of ordinary skill in the art to have isolated the fatty acids and rosin acids from the neutral fraction of Barder et al., and the motivation to do so would have been to recover valuable products from the tall oil.
Aro et al. describes the process of Clearly et al. in the packed column embodiment (Section 4.3). Cleary describes the process as being a simulated moving bed process (8:28-52).
Claims 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Barder et al. (US Pat. 4,849,112) in view of Hamunen (US Pat. 7,202,372) and Aro et al. (Separation and Purification Technology 175 (2017) 469-480) as evidenced by Herrlinger et al. (Methods of Analysis for Tall Oil Products, The Journal of the American Oil Chemists Society, Vol. 36, 119-124, 1959).
Considering Claims 10 and 11: Barder et al. teaches a process of removing components from a tall oil product (Abstract) comprising the step of providing a tall oil mixture (1:30-50); subjecting the tall oil mixture to simulated moving bed chromatography (5:20-51) to separate the sterol component from the feed mixture/two fraction (4:26-34); and recovering the two fractions (4:35-63). The sterol fraction is neutral and the raffinate is neutral depleted. Barder et al. teaches the process can be used generally on tall oil feeds (1:31-44), with tall oil pitch being preferred (3:40-45).
Barder et al. teaches the solid phase as being carbon coated alumina (3:13-20) with a portion of the alumina being retained (Example 1). Alternatively, Barder et al. teaches that alumina is a known support for the chromatography step, albeit with reduced stability compared with the carbon support. "A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use." In re Gurley, 27 F.3d 551, 554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994). See MPEP § 2123.
Barder et al. does not teach using crude tall oil with sufficient specificity. However, Hamunen teaches removing sterols directly from the crude tall oil (1:13-18). Barder et al. and Hamunen are analogous art as they are concerned with the same field of endeavor, namely tall oil sterol removal. It would have been obvious to a person of ordinary skill in the art to have performed the separation of Barder et al. prior to the evaporation step to form the pitch, as in Hamunen, and the motivation to do so would have been, as Hamunen suggests, sterols are lost during the evaporation (2:63-3:14), thus a higher percentage of sterols can be recovered.
Barder et al. teaches removing sterol from the tall oil product. Herrlinger et al. teaches that crude tall oil typically has an acid number of 166-170 (Table I), and that the acid number increases with reduction of the unsaponifiables, i.e. the sterols (Table I). As such, the raffinate will contain a higher concentration of acids and lower concentration of sterols, and thus a higher acid number, i.e. above 170. The acid number is a result effective variable showing the degree of sterol removal. It would have been obvious to a person of ordinary skill in the art to have selected an acid number in the claimed range, and the motivation to do so would have been, to provide a pure product with lower content of sterols.
Barder et al. does not teach how the crude tall oil is produced. However, Aro et al. teaches the crude tall oil is prepared commercially by producing wood pulp through a Kraft pulping process; separating a black liquor from the wood pulp; separating a soap from the black liquor by soap skimming; and producing crude tall oil from the soap, where no distillation takes place prior to the production of the crude tall oil (“the crude tall oil is distilled after production”)(Section 3, Scheme 1). Aro et al. teaches removing solid components from the crude tall oil by centrifuge (Section 3.2). It would have been obvious to a person of ordinary skill in the art to have prepared the crude tall oil through the method of Aro et al., and the motivation to do so would have been, as Aro et al. suggests, it is a commercially available process for producing crude tall oil.
Response to Arguments
Applicant's arguments filed December 8, 2025 have been fully considered but they are not persuasive.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
While neither of the references teach subjecting crude tall oil to simulated moving bed chromatography, the combination of Barder et al. and Hamunen collectively teach this step. Barder et al. teaches removing sterols from a tall oil product through simulated moving bed chromatography, while Hamunen teaches removing the sterols from the crude tall oil. Thus the combination teaches performing simulated moving bed chromatography on the crude tall oil.
Aro et al. teaches the crude tall oil is prepared commercially by producing wood pulp through a Kraft pulping process; separating a black liquor from the wood pulp; separating a soap from the black liquor by soap skimming; and producing crude tall oil from the soap, where no distillation takes place prior to the production of the crude tall oil (“the crude tall oil is distilled after production”)(Section 3, Scheme 1).
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIAM J HEINCER whose telephone number is (571)270-3297. The examiner can normally be reached M-F 7:30-5:00.
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/LIAM J HEINCER/ Primary Examiner, Art Unit 1767