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 .
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 11/27/2023 and 02/25/2025 have been considered by the Examiner.
Status of Claims
Claims 1-20, filed on 08/28/2023, are under consideration. Claims 1, 14 and 20 are independent.
Claim Objections
Claims 2 and 14 are objected to because of the following informalities: claimed structures G and J have the same chemical formula of 5-ethyl-7, 8, 11-trimethyl pentadecane. Appropriate correction to differentiate the chemical structure or to cancel the repeated structure is required.
Specification
The disclosure is objected to because of the following informalities: disclosed structures G and J have the same chemical formula of 5-ethyl-7, 8, 11-trimethyl pentadecane ([0006], [0084], [00137], [00147], [00163] and [00173]). Appropriate correction to distinguish the two chemical structures is required.
Claim Rejections - 35 USC § 112
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 1 and 14 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.
These claims are indefinite because it uses the term “olefin” in PAO to describe hydrogenated dimer (saturated hydrocarbons). Note that while polyalphaolefins typically refer to oligomers/olefins which include double bonds on the alpha carbon; this term is being used here to refer to saturated C20 hydrocarbons (last 2 lines of claim 1 and Specification at [0006]) which raises lack of clarity issue. More specifically, claim 1, last two lines, recite "hydrogenating the C20+ olefin portion to form polyalphaolefins comprising saturated C20 hydrocarbons". It is not clear how hydrogenating the olefins as recited would produce PAOs comprising saturated hydrocarbons because PAOs would be unsaturates and not saturates. Also, claim 14 recites, "A composition comprising polyalphaolefins wherein the polyalphaolefins comprises ..." However, the compounds listed are all alkanes. Hence, it is unclear if Applicant meant to recite PAOs or the alkanes recited in the claim.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 1, 10-11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Coffin et al. (US 2020/0207682).
Regarding claim 1, Coffin teaches a process to oligomerize branched C10 olefins including 3-propyl-1-heptene, 4-ethyl-1-octene, and/or 5-methyl-1-nonene (Abstract). In [0012], it is disclosed: “In an embodiment , a process can comprise a) contacting 1) a catalyst system and 2 ) a monomer feedstock comprising a branched C10 olefin monomer in a reaction zone ; and b ) forming olefin oligomers. In such embodiment, the process can further comprise removing a reaction zone effluent from the reaction zone… the process can further comprise isolating one or more fractions comprising all or a portion of the olefin oligomers from the reaction zone effluent... In such embodiments , the process can further comprise hydrogenating at least one of the one or more fractions comprising all or a portion of the olefin oligomers”. Coffin further teaches that dimers and trimers are formed as the oligomers [0038] and that a solid acid catalyst such as Amberlyst can be used ([0143]-[0144] and [0147]).
In summary, Coffin teaches contacting the same branched C10 monomers with solid acid catalyst, separate/isolate the C20+ oligomers including the dimer, and hydrogenating the oligomers to provide saturated hydrocarbons. These saturated hydrocarbons are equivalent to the claimed “polyalphaolefins”.
Note that while polyalphaolefins typically refer to oligomers/olefins which include double bonds on the alpha carbon; this term is being used here to refer to saturated C20 hydrocarbons (last 2 lines of claim 1 and Specification at [0006]).
Regarding claim 10, Coffins teaches the following branched C10 monomer composition ([0197] and Table 2, and [0219]). The disclosed 2-butyl-1-hexene amount of 11 mol% overlaps the claimed amount of least 3 mol%, the disclosed 3-propyl-1-heptene amount of 17 mol% overlaps the claimed amount of at least 8 mol%, the disclosed 4-ethyl-1-octene amount of 15 mol% overlaps the claimed amount of at least 6 mol%, and the disclosed 5-methyl-1-nonene amount of 38 mol% overlaps the claimed amount of at least 20 mol%. Thus, the instantly claimed ranges are anticipated by the reference as sufficiently supported by specific example(s)—See MPEP 2131.03.
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Regarding claim 11, Coffin teaches the compositions further comprises C14 olefin monomers at ratio to C10 monomers of about 0.05:1 to 0.12:1 (e.g. 5-12 mol% C14; [0224]-[0225]). The disclosed amount of 5-12 mol% C14 results in branched C10 amount of 88-95 mol% which anticipates the claimed amounts of at least 76 mol% of the one or more branched C10 monoolefins and at least 1 mol% C14 monoolefins.
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.
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.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Coffin as applied to claim 1 above, and further in view of Kreischer et al. (US 2018/0127332).
It is note that Coffin suggests that the monomer composition is obtained from ethylene trimerization technology [0197]. However, this reference is silent about the steps of making the composition from ethylene.
However, Kreischer teaches making C10 branched oligomers including 2-butyl-1-hexene, 3-propyl-1-heptene, and 5-methyl-1-nonene as well as C14 oligomers ([0034]- [0037]-[0038]) from ethylene oligomerization with a chromium catalyst [0058]: “the compositions disclosed herein can be prepared by a process comprising a) contacting 1) ethylene, 2) a catalyst system comprising i) a chromium containing compound, ii) a heteroatomic ligand, and iii) an alkylaluminum compound; b ) forming an oligomer product … ; c) discharging a reaction system effluent from the reaction system; … and e ) isolating the composition”.
Therefore, and before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to have incorporated the ethylene oligomerization method of Kreischer to make the C10 and C14 oligomers for the dimerization reaction of Coffin to make the C20+ hydrocarbons since because both references suggest using ethylene trimerization/oligomerization to make the C10 branched olefins, and because this involves applying known oligomerization technique with predictable results and a reasonable expectation of success—see MPEP 2143 I, 2143 A, 2143 D, and 2143.02.
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Coffin, in view of Kreischer, as applied to claim 12 above, and further in view of Lilga et al. (US 2016/0194257).
It is noted that Coffin and Kreischer do not teach wherein the ethylene is derived from ethanol, and wherein the ethanol is derived from a biomass, a plastic, a waste oil, a mixed solid waste stream, or a combination thereof.
However, Lilga discloses obtaining ethylene from ethanol derived from biological sources ([0040]-[0045] and Fig. 1) and oligomerizing the ethylene to make oligomers including C10 and C14 oligomers (Fig. 10 and Example 13).
Therefore, and before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to have used ethylene from bio-ethanol in the method of Coffin in view of Kreischer to make the C10 and C14 oligomers because this involves using a renewable ethylene feed for oligomerization with predictable results and a reasonable expectation of success—see MPEP 2143 I, 2143 A, 2143 D, and 2143.02.
Allowable Subject Matter
As allowable subject matter has been indicated, applicant's reply must either comply with all formal requirements or specifically traverse each requirement not complied with. See 37 CFR 1.111(b) and MPEP § 707.07(a).
Claims 2-9 and 15-19 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
As allowable subject matter has been indicated, applicant's reply must either comply with all formal requirements or specifically traverse each requirement not complied with. See 37 CFR 1.111(b) and MPEP § 707.07(a).
The following is a statement of reasons for the indication of allowable subject matter:
For claims 2 and 14-19, a search of chemical formulas did not locate any of the claimed saturated C20 hydrocarbons presented in Structures A-L.
For claims 3-7, no prior art teaches or suggests the polyalphaolefins have a kinematic viscosity at 100°C in a range of from about 1.9 cSt to about 2.2 cSt, a kinematic viscosity at 40°C in a range of from about 7.5 cSt to about 9.1 cSt, and a kinematic viscosity at -40°C in a range of from about 2500.0 cSt to about 3000.0 cSt, when measured in accordance with ASTM D7042 or ASTM D445. It is noted the Coffin discloses the olefin oligomers and/or the substantially hydrogenated olefin oligomers can have a 100°C kinematic viscosity of from 1.5 cSt to 225 cSt [0055] such as 1.8-2.2 cSt [0056]. However, the instant invention demonstrates that the combination of claimed kinematic viscosity values is obtained when using solid acid catalyst (Amberlyst as opposed to liquid catalyst such as alkyl aluminum or BF3; Specification at [00122]-[00126])
For claims 8-9 and independent claim 20, a search of pertinent prior art did not locate a teaching or suggestion for a process comprising: contacting one or more branched C10 monoolefins with a solid acid catalyst to produce an oligomer product comprising unreacted C10 monoolefins and a C20+ olefin portion comprising C20 dimers, wherein the one or more branched C10 monoolefins comprise 2-butyl-1-hexene, 3-propyl-1-heptene, 4-ethyl-1-octene, and 5-methyl-1-nonene, wherein the C20+ olefin portion comprises 85 wt% to 95 wt% of the C20 olefin dimers based on a total weight of the C20+ olefin portion without having to isolate the C20 olefin dimers from the other oligomers in the C20+ olefin portion.
The instant invention combines the use of solid acid catalyst with the branched C10 monoolefins to produce oligomers with 85-95 wt% selectivity: “It has been found that the solid acid catalyst has a high selectivity to the C20 olefin dimers in the C20+ olefin portion, in that, the C20+ olefin portion can contain from about 85 wt % to about 95 wt % C20 olefin dimers and only from about 5 wt % to about 15 wt % other oligomers (e.g., C30 olefin trimers and C40 olefin tetramers), without having to isolate the C20 olefin dimers from the other oligomers to obtain this high dimer concentration in the C20+ olefin portion. As such, the C20+ olefin portion can be introduced directly to a hydrogenation process without having to further isolate the C20 olefin dimers from the other oligomers” (Specification at [0072]).
Coffin does not disclose generic selectivity to dimer, and exemplifies using solid acid catalyst (Filtrol, [0206]-[0207) where the dimer selectivity is about 70% (based on dimer and trimer).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALI Z FADHEL whose telephone number is (571) 270-0267. The examiner can normally be reached M-F 9am-6pm PST.
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/ALI Z FADHEL/Primary Examiner, Art Unit 1772
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