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 .
Claim Status
Claims 1-23 were filed on 11/27/2023. In a preliminary amendment filed on the same day, claims 1-23 were canceled and claims 24-44 were newly added. Claims 24-44 are pending.
Priority
The application was filed on 11/27/2023 and claims the benefit of priority to:
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See filing receipt dated 4/22/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claims 24, 25, 27, 30, 35, 41, and 44 are objected to because of the following informalities:
In claim 24, the phrase “or esters thereof” should be inserted after the word “acids” in line 2. The text of the claim recites that the composition comprises fatty acids or esters thereof, therefore this should also be recited in the preamble.
In b) of claim 24, the word “is” should be inserted after the word “thereof” in the first line.
In line 3 of claim 25, the word “or” should be deleted and replaced with “and”.
Claim 27 recites “wherein 10-ring channels (with 10-membered ring openings)”. The limitations in the parentheses do not appear to further limit the limitation “10-ring channels” and should be deleted. Otherwise, this would appear to be a range within a range indefinite limitation. See MPEP § 2173.05(c).
In line 1 of claim 30, the word “have” should be deleted.
In claim 35, the phrase “the process further comprising” should be inserted after the word “wherein” in line 1.
In line 1 of claim 41, the word “wherein” should be deleted and replaced by “comprising”.
In line 2 of claim 41, the word “comprise” should be deleted and replaced by “comprising”.
In line 1 of claim 44, the word “further” should be deleted.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 26 and 34 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 26 states “wherein the catalyst has 10-ring linear channels without interconnecting channels” and then states “which otherwise creates intersection spaces of more than 6.2 angstroms”. It is not clear i) if the catalyst can have interconnecting channels or not and ii) if the catalyst can have intersection spaces of more than 6.2 angstroms. The first part of the claim appears to unambiguously recite that the catalyst does not have interconnecting channels, however the claim then uses the phrase “which otherwise creates intersection spaces of more than 6.2 angstroms”. Does this mean that there can be interconnecting channels present if the intersection spaces are 6.2 angstroms or less? Can intersection spaces of more than 6.2 angstroms be present if they are not caused by “interconnecting channels”? According to the discussion in [0022] of the specification as filed, this is an inherent feature of the described zeolite catalysts. Therefore, it appears as if Applicant is intending to indicate that there are no interconnecting channels and there are no intersection spaces of more than 6.2 angstroms. However, this is not clear from the present claim language, which appears to be conditional (which otherwise creates…).
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
In the present instance, claim 34 recites the broad recitation “water or light alcohols”, and the claim also recites “(methanol, ethanol)” which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claim 34 recites a list of additives or catalysts selected from the group consisting of dichloromethane, …the Lewis base catalyst triphenyl phosphine, the Lewis base catalyst triethylenediamine, a combination of Lewis base catalyst triphenylphosphine, the Lewis base catalyst triethylenediamine and metalloaluminophosphate molecular sieves.” The scope of the italicized limitation is unclear because it is not clear if the combination comprising i) triphenylphosphine, triethylenediamine, and metalloaluminophosphate or ii) triphenylphosphine and triethylenediamine, wherein metalloaluminophosphate is the final alternative in the Markush group. When the phrasing “selected from the group consisting of” is used to define a group, the penultimate and final options should be separated by the word “and”, such as “selected from the group consisting of A, B, and C”. This Markush group of claim 34 is missing at least one “and”.
Claim Rejections - 35 USC § 112(d)
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 36-37 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 36 does not further limit claim 24 because all of the recited limitations are explicitly recited in claim 24.
Claim 37 recites that the ratio of monobranched to polybranched C10-24 fatty acids or esters ranges from 1.5:1 to 5:1 by weight. This range improperly broadens the range of claim 24, which requires the upper limit of the range to be “smaller than 5:1”, thus excluding the range of 5:1.
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
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 24-29 and 31-44 is/are rejected under 35 U.S.C. 103 as being unpatentable over Petersen (WO2015/144232A1, published on 10/1/2015, of record in the IDS filed on 11/27/2023) as evidenced by Kerstens (“State of the Art and Perspectives of Hierarchical Zeolites: Practical Overview of Synthesis Methods and Use in Catalysis” Advanced Materials, 2020, 2004690, first published 9/23/2020).
Applicant claims a process for preparing a composition comprising branched C10-C24 fatty acids with a) at least 70% by weight of mono and polybranched C10-C24 fatty acids or esters thereof, b) a ratio of monobranched/polybranched C10-C24 fatty acids or esters thereof smaller than 5:1 by weight based upon the total weight of the composition, and c) an amount of oligomers ranging from only 0.1 to 8.5% by weight based upon the total weight of the composition, wherein a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), based upon the total weight of the starting material is heated in the presence of a zeolite catalyst, which has 10-ring linear channels without intersecting channels.
Petersen teaches catalysts and methods for skeletal isomerization of unsaturated fatty acids. See abstract. The method comprises reacting at least one linear unsaturated C16-26 carboxylic acid and/or ester with a zeolite catalyst to produce branched fatty acids. See abstract and claims 12-16. Petersen teaches that “alkyl-branched fatty acids are useful because of their interesting properties for various applications in the field of cosmetics, lubricants, hydraulic fluids or bio-based fuels, such as in the production of soaps, paints and coatings, fabric softeners and fuel additives.”. See p. 1, lines 7-14. Petersen teaches that existing processes require cumbersome control and isolation processes and the yield of the skeletal isomerized products and/or selectivity of the reaction is low. Petersen teaches that “there is a need for a new process that overcomes these disadvantages, i.e. a process for the preparation of branched fatty acids from straight chain unsaturated fatty acid feedstocks with a high conversion rate, an increased selectivity towards branched monomeric isomers and which employs a durable and reusable catalyst. Furthermore, there is a need for a new catalyst that can be used in such processes and methods of producing such catalyst.” See p. 2, lines 1-18.
Petersen teaches that the starting material can comprise 100% by weight of the linear monoethylenically unsaturated C10-C24 fatty acids, based on the total weight of the starting materials. See Example 2 on p. 20-21, which employs 100% of 90% purity oleic acid (C18 fatty acid) or rape seed fatty acid as the starting material. This falls within the range of “at least 80% by weight” in claim 1. Also see MPEP 2144.05.
Petersen teaches that the zeolite catalyst is selected from one of the following with Bronsted acid sites:
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See claims 1-11. Petersen teaches the preparation of inventive catalysts in Example 1 on p. 1-20, which are prepared from mordenite (CBV21A, with a SiO2/Al2O3 ratio of 20), ferrierite (CP914C, with a SiO2/Al2O3 ratio of 20), and ZSM-5 (CBV 2314 with a SiO2/Al2O3 ratio of 23). See Method A of p. 17. Petersen teaches the catalysts are used in the H+ forms (as a result of reaction with a strong protic acid, HCl). Table 1 on p. 19 and Table 2 on p. 20 show the catalysts used in the catalytic skeletal isomerization of Example 2.
As evidenced by Kerstens:
Mordenite (MOR) has a framework that includes 12-MR channels in the [001] direction, which are interconnected by 8-MR channels (section 4.1 on p. 22);
Ferrierite (FER) is a 2D zeolite with intersecting 10- and 8-MR channels (section 3.3 on p. 7);
ZSM-5 (MFI) has 10-MR openings which make zig-zag channels along the [100] axid and also has straight intersecting channels along the [010] axis (section 3.4 on p. 8); and
ZSM-23 (MTT) is a unidimensional 10-MR zeolite which are needle or rod shaped with teardrop shaped pore channels/diameters/openings (0.45 x 0.52 nm-claim 29) running parallel to the longest dimension of the crystal.
Therefore, while none of the zeolites exemplified in example 2 of Petersen meet the claimed limitations of a zeolite catalyst which has 10-ring linear channels without intersecting channels, Petersen does teach that ZSM-23 is an acceptable alternative. As evidenced by Kerstens and [0022-0024] of the specification as filed, ZSM-23 does meet the limitations of claims 24-29.
Petersen teaches that the isomerization is carried out continuous by heating the fatty acid (oleic or rape seed fatty acid) in the presence of a fixed bed of catalyst at 250°C and under the exclusion of oxygen. See Example 2 on p. 20-21. These are the same conditions as used in the inventive examples as evidenced by [0090-0109], wherein ZSM-23 is taught in example 4 in [0106-0109]. Petersen teaches that the molar yield% of the skeletal isomerized products range from 10.2 to 92.4%. Petersen teaches that the isomerized products were isolated by distillation, which meets the limitations of claim 35, wherein the separating and isolating occurs during distillation. See Example 2 on p. 20-21.
Petersen does not explicitly teach that the product comprises a) at least 70% by weight of mono and polybranched C10 -C24 fatty acids or esters; b) a weight ratio of monobranched to polybranched fatty acids or esters is smaller than 5:1; and c) an amount of oligomers ranging from only 0.1 to 8.5% by weight. However, as Petersen teaches molar yields of up to 92.4%, the products of Petersen would appear to fall within the ranges of limitations a and c.
It would have been prima facie obvious to arrive at the instantly claimed process based on the teachings of Petersen with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to substitute ZSM-23 for the zeolite catalysts in example 2 in Petersen because Petersen explicitly suggests as much and teaches limited number of options for the catalyst. Therefore, using ZSM-23 in the reaction of Petersen will predictably lead to skeletal isomerization of oleic acid to produce a mixture of mono and polybranched fatty acids or esters. As discussed above, though Petersen is silent regarding limitations a) to c) of claim 24, the conditions of Petersen are substantially identical to those in the inventive examples 1-4 of the specification as filed. Therefore, if ZSM-23 were used, as suggested by Petersen, in the process of Petersen, then the product produced should also be substantially similar, if not identical, to that claimed. Carrying out substantially identical reactions on identical products is will predictably produce the same results absent evidence to the contrary. Likewise, the compositions produced in claims 36-44 all appear to be inherent to the reaction of Petersen which employs ZSM-23 as evidenced by example 4 of the specification as filed. Also see MPEP 2112.
Further regarding claims 31-34, Petersen does not require the use of any other catalysts or additives, therefore Petersen appears to meet the limitations of the claims.
Subject Matter free from the Prior Art
Claim 30 appears to be free from the prior art. Claim 30 specifies “wherein the 10-ring channels of the catalyst have opening that are in the range of 5.5 –5.9 x 4.4 –4.7 angstroms”. According to the specification as filed, see [0022-0024 and 0029] and section 3.2. ZSM-22 of Kerstens on p. 6, a claimed zeolite having these dimensions is ZSM-22, having a TON framework (compared to the MTT framework of ZSM-23, taught by Petersen). Petersen does not teach or suggest the use of ZSM-22 specifically, and nor does there appear to be any motivation to employ this catalyst in the claimed reaction. As evidenced by examples 1-3 of the specification as filed this is the best performing catalyst. Therefore, it would not have been obvious to modify the prior art to predictably arrive at the claimed reaction.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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