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 .
Applicant’s preliminary amendment dated 30 November 2023 is acknowledged. Claims 1-16 as amended are pending.
Claim Objections
Claim 8 is objected to because of the following informalities: the phrase “cause the cyclopentene be boiling” should be “cause the cyclopentene to be boiling”. Appropriate correction 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 2, 6, and 7 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 2 recites a formula for a carbene including a substituent Q that is undefined.
Claim 6 recites a formula for the carbyne compound that appears to show a triple bond to X (halogen atom). However, the examples of the specification show a metal carbyne linkage. As such, while the recitation of claim 6 appears clear on its face, the conflict with the specification makes it unclear whether the apparent linkage is required for the claim.
Claim 7 recites the second co-catalyst at an amount of no more than 30 equivalents. It is presumed that these are in comparison with another component; however, since there are two other components recited, it is unclear to what this limit is being compared.
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(s) 1-3, 8, 10, and 13 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US 3,689,433 (“Kroll”).
As to claim 1, Kroll teaches contacting a carbene complex with a metallic element, preferably aluminum, so as to activate the carbene complex (2:32-40). Kroll exemplifies a carbene complex contacted with methylaluminum dichloride to prepare a catalyst for cyclopentene polymerization (9:60-75). As such, the methylaluminum dichloride is considered to be a cocatalyst sufficient to activate the carbene.
As to claims 2 and 3, Kroll teaches carbene complex of the recited formula where M is W, Q is oxygen, R2 is methyl, R1 is ethyl (9:1-10), which meet the limitations of claims 2 and 3.
As to claims 8 and 10, Kroll teaches adding a monomer, cyclopentene, a cyclic olefin, and isolating (extracting) a polymer (9:60-75).
As to claim 13, Kroll teaches ambient conditions, thus suggesting the reaction is carried out in air.
Claim(s) 1-5, 8, 10, 11, and 15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chauvin et al., “Catalysis of Olefin Transformation by Tungsten Complexes, 5*”, Makromol. Chem. 177, 2637-3646 (1976) (“Chauvin”).
This reference was in applicant’s IDS dated 30 November 2023.
As to claim 1, Chauvin teaches contacting a carbene complex with AlEtCl2, an aluminum activator, under conditions to activate a catalyst for polymerization (Tab. 5).
As to claims 2-5 and 15, the carbene complex is (CO)5W0C(OC2H5)C6H5], which meets the recited formula of claim 2 where Q is oxygen, R2 is ethyl, R1 is phenyl as required by claims 2 and 15, such that R2 is alkyl as required by claim 3, and which meets the 9th structure of claim 4, where R2 is ethyl, and meets the second formula of claim 5.
As to claims 8 and 10, Chauvin teaches addition of cyclopentene, a monomer, and obtaining a polymer.
As to claim 11, Table 5 teaches a trans content of 83%.
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO 2020/099750 A1 (“Rouen”).
This reference is in applicant’s IDS dated 30 November 2023.
As to claim 1, Rouen teaches contacting a ruthenium carbene catalyst with an activator chosen from Lewis acids (abstract), which may be an aluminum halide (translation, p. 8), thus an aluminum activator in amounts to activate the catalyst.
Claims 1, 8, and 10 are rejected under 35 USC 102(a)(1) as being anticipated by EP 0864595 A1 (“Stelzer”).
As to claim 1, Stelzer teaches an activation method of a catalyst (5:37-46) by contacting a reaction product of aluminoxanes or alkylaluminums with a Schrock catalyst based on alkylidene (carbene) or alkylidyne (carbyne) complexes of transition elements (p. 3).
As to claims 8 and 10, Stelzer teaches the use of the catalyst for polymerization of cyclic olefins (5:53-55), and teaches precipitation thereof, thus extracting the polymer (examples, p. 8).
Claims 1-5, 8, 15, and 16 are rejected under 35 USC 102(a)(1) as being anticipated by Liu et al., “Studies on Organomolybdenum and Tungsten Compounds,” Kexue Tongbao 32(23), 1622-1625 (1987) (“Liu”).
As to claim 1, Liu teaches a catalyst system formed by contacting carbene compound and AlCl3, an aluminum activator (abstract, p. 1622). Liu teaches the system is sufficient to catalyze polymerization of alkynes, and thus it is presumed that the two compounds are contacted in such manner to activate the carbene catalyst.
As to claims 2-5 and 15-16, Liu teaches a carbene that is (CO)5W:C(OEt)R where R is methyl, phenyl, furan, or thiophene (Table I). These compounds meet the formula of claim 2 where Q is O, R2 is ethyl as required by claims 2 and 3, M is W, R1 is linear hydrocarbyl chain, or cyclic hydrocarbon or heteroatom containing ring structure as required by claims 2 and 15-16. These compounds meet the first, second, third, and ninth structure of claim 4, and the second structure of claim 5.
As to claim 8, Liu teaches polymerizing in the aforementioned catalyst system and obtaining properties, thus extracting a polymer (p. 1623).
Claims 1, 6, 8, 10, and 14 are rejected under 35 USC 102(a)(1) as being anticipated by JP S52-112000 A (“Kobayashi”).
A partial machine translation of the corresponding JP publication JP S60-43366 B2 is enclosed.
As to claim 1, Kobayashi teaches a method polymerizing a norbornene derivative with a catalyst obtained from a carbyne complex (thus a precatalyst) and organometallic compound (abstract), preferably an organoaluminum compound (translation, p. 6). Since the resulting material effects polymerization, the contacting is presumed to allow activation of the carbyne complex by the aluminum activator.
As to claim 6, for the purposes of applying prior art, it is presumed that the carbyne carbon is attached to M rather than X. Kobayashi teaches an example of contacting diethyaluminum dichloride, an aluminum cocatalyst, with phenylcarbynetetracarbonyltungsten bromide, which meets the recited formula where M is W, X is Br, R is cyclic aromatic.
As to claims 8 and 10, Kobayashi teaches the catalyst is for polymerization of norbornene derivatives, therefore cyclic olefin, and recovery of resulting polymer (abstract; translation, p. 8, discussing recovery of polymer).
As to claim 14, Kobayashi teaches the method may include alpha olefins, such as ethylene, 1-hexene, 1-octene as molecular weight regulators (translation, pp.7-8); while not stated as chain transfer agents, these are the same types of compounds acknowledged by applicant’s specification as chain transfer agents.
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.
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.
Claims 7, 8, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2020/099750 A1 (“Rouen”).
The discussion of Rouen with respect to claim 1 is incorporated by reference.
As to claim 7, while not exemplified, Rouen teaches the activator may be combinations, and includes transition metal halides and main group halides (translation, p. 8), and thus the use in combination with the recited second activators (cocatalysts) is contemplated by Rouen. Further, Rouen teaches molar ratio of activator to catalyst between 10:1 and 1:10, and thus suggests less than 30 equivalents of activator per 1 equivalent of catalyst.
As to claims 8 and 10, Rouen teaches using the catalyst for polymerization of monomers, in particular ring opening metathesis polymerization of cyclic olefins (translation, pp. 8-9), and therefore these are an obvious end use suggested by Rouen.
Claims 9 and 12 are rejected under 35 U.S.C. 103 as being obvious over US 3,689,433 (“Kroll”).
The discussion of Kroll with respect to claim 8 is incorporated by reference.
As to claim 9, Kroll teaches polymerization of cyclopentene. While not exemplified, Kroll teaches a wide range of reaction temperatures (7:50-55), which includes temperatures at which cyclopentene would be boiling (55 degrees as acknowledged by applicant’s specification), and as such, preparing a polymer in conditions of boiling cyclopentene is an obvious modification in the teachings of Kroll.
As to claim 12, Kroll teaches high molecular weight polymer from reacting with carbene in the presence of aluminum catalyst, including 585,000 (11:5-17). While it is not stated whether this is weight average molecular weight, it is clear that molecular weights in the recited range can be obtained by the method, and as such, the recited Mw is an obvious modification suggested by Kroll.
Claim 9 is rejected under 35 U.S.C. 103 as being obvious over JP S52-112000 A (“Kobayashi”).
The discussion of Kobayashi with respect to claim 8 is incorporated by reference. As to claim 9, while not exemplified, Kobayashi teaches the use of additional cyclic olefin monomers, including cyclopentene (translation, p. 5), and teaches polymerization at temperatures up to 150 degrees C (translation, p. 7), which includes temperatures acknowledged in applicant’s specification to boil cyclopentene. As such, polymerizing cyclopentene under such conditions is an obvious modification within the teaching of Kobayashi.
Claim 12 is rejected under 35 U.S.C. 103 as being obvious over Liu et al., “Studies on Organomolybdenum and Tungsten Compounds,” Kexue Tongbao 32(23), 1622-1625 (1987) (“Liu”).
The discussion of Liu with respect to claim 8 is incorporated by reference.
As to claim 12, Liu teaches polymerizations resulting in polymers having Mn of 10,000 to 12,000 g/mol (Table 4). While this is in number average molecular weight, given the broad range recited (up to 700,000) for Mw, obtaining a polymer in the recited Mw would be an obvious modification over the polymerizations of Liu, given that Mw is equal to or greater than Mn.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KREGG T BROOKS whose telephone number is (313)446-4888. The examiner can normally be reached Monday to Friday 9 am to 5:30 pm.
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/KREGG T BROOKS/ Primary Examiner, Art Unit 1764
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