DETAILED ACTION
Status of Application
This action is responsive to non-provisional application filed 12/19/2023. Original claims 1-32 are currently pending and under examination herein.
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 . However, 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 a 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.
Objection – Claims
Claims 15-16 are objected to because of the following informalities: omission of appropriate conjunction –and-- between the final two members of the Markush groups directed to “heterocyclic Lewis base” and “catalyst compounds” formulae recited in the respective claims. See claim 15, antepenult. line and claim 16, line 3.
Claim 16 is objected to because of the following informalities: “R5” in lines 31-32 should read –R5-- to agree with the corresponding variable notation appearing in antecedent Formulae 1, 2 and 4 (cf., line 4).
Claim 17 is objected to because of the following informalities: a redundant recitation of “reactor” is noted in line 1 of the claim.
Claims 18-19 are objected to because of the following informalities: a redundant recitation of “the” is noted in line 1 of each claim.
Appropriate correction of the above-noted claims is required.
Claim Rejections – 35 U.S.C. 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 2-17 and 19 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.
Regarding Claim 2, the claim provides the limitation to “the single-site catalyst compound” in line 1. There is no proper and sufficient antecedent basis for this limitation in the claim nor in parent claim 1. In this latter regard, it is noted that claim 1 recites “a catalyst compound” to introduce a group of three subclasses of catalyst compounds, only the first of which is defined as a “single-site” metallocene. It is unclear whether “single-site” in claim 2 is intended to add a further limitation to the other two group members or whether it merely makes explicit what is an intrinsic characteristic common to the overall group of “catalyst compound” selections recited in claim 1. To resolve this issue, it is suggested that “single-site” be deleted from claim 2 (i.e., “wherein the [[single-site]] catalyst compound is the post metallocene…”; cf., claim 16, line 1).
Dependent claims 3-15 inherit the indefiniteness ascribed to parent claim 2 supra.
Regarding Claim 16, the claim contains broad recitations of a particular range or limitation followed by one or more of the linking terms "preferably" and "more preferably" and then narrower recitation(s) of the corresponding range or limitation. See claim 16, lines 7, 14, 27-28 and 36. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP§ 2173.05(d). More specifically, it is unclear whether the features introduced by such linking term(s) are intended to be restrictive to the corresponding broader recitation(s), or merely exemplary of the remainder of the claims, and therefore not required. For purposes of substantive examination, the features introduced by the aforementioned linking terms are being treated as merely exemplary of the corresponding broader recitations, in accordance with the principal of giving the broadest reasonable interpretation to pending claims. See MPEP § 2173.01(1). However, clarification and appropriate correction are required.
Further regarding Claim 16, the claim is incomplete, hence indefinite, due to lack of explicit definitions for variables R6 (in Formula 2) and R7-R10 (in Formulae 3, 5). As far as can be discerned, the claim provides explicit definitions only for the variables R1-R5 and R11-R19 appearing in one or more of recited Formulae 1 through 5. For purposes of substantive examination, an assumption has been made that R6 is defined as per paragraph [0128] and that R7-R10 are defined as per paragraphs [0129] and [0131] of the instant specification; however, clarification and appropriate correction are required.
Regarding Claims 16 and 19, the phrase "such as" in each claim (see claim 16, line 33-34; claim 19, final line) renders the claims indefinite because it is unclear whether the subject matter following the phrase is intended to be part of the claimed invention. See MPEP § 2173.05(d).
Regarding Claim 17, the claim recites “optional hydrocarbon solvent and hydrogen” in lines 2-3. It is unclear whether the claim should be narrowly construed to only the hydrocarbon solvent being an optional (i.e., non-essential) reaction condition or broadly read to cover reaction conditions wherein both said solvent and hydrogen may be permissibly omitted. For purposes of substantive examination, an assumption has been made that among the recited reaction conditions, only “hydrocarbon solvent” may be optionally omitted. However, clarification at least by way of explanation is required.
Common Ownership Notice
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 Rejections – 35 U.S.C. 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.
Claims 1, 18-24, 29, and 32 are rejected under 35 U.S.C. 103 as being unpatentable over Sita et al (US 2004/0110632 A1) (hereinafter, ‘Sita’).
Regarding Claims 1, 18, and 23-24: reference to Sita is directed to an olefin polymerization pre-catalyst, an activated catalyst and a process for preparing a polyolefin, comprising reacting an olefin with an activated olefin polymerization catalyst composition, under conditions that result in the formation of a polyolefin; wherein the catalyst composition comprises an acetamidinate metal complex (pre-catalyst) having the formula:
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-wherein M is Ti, Zr or Hf, and R1-R4 are as defined in paragraphs [0010]-[0017] thereof. Inasmuch as the described pre-catalyst is an organometallic compound containing only one π-bonded cyclopentadienyl moiety or substituted cyclopentadienyl moiety, the compound qualifies as a “half metallocene,” per present claim 1 (cf., Spec., [0019]). Sita in Example III details polymerization of 1-hexene in the presence of solid-supported catalytic beads comprising Cp*ZrCl2[t-BuNC(Me)NEt] and [PhNHMe2]+[B(C6F5)4]- activator (i.e., a NCA salt, per claim 18) to form isotactic poly(1-hexene) having a PDI of 1.06 (see [0023], 0070]).
The teachings of Sita differ from the claimed subject matter only in that Sita fails to specifically disclose polymerizing vinylcyclobutane (VCB) to produce a VCB polymer having a PDI of less than 3.0. However, in regards to polyolefins producible according to the Sita invention, Sita generally teaches those made from olefin monomers such as ethylene and linear or branched higher α-olefin monomers containing 3 to about 20 carbon atoms; in addition, homopolymers, co-polymers and block co-polymers that have high isotacticity and low polydispersities may be made, with “low polydispersity” being, for example, from about 1.01 to 2.0 (see [0064]). Sita then mentions propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 1-octene, 3,5,5-trimethyl-1-hexene, vinylcyclohexane, 3-methylbutene, 3-methyl-1-pentene, vinylcyclobutane, vinylcyclopentane, vinylcyclooctane, 1-decene and enantiomerically pure β-citronellene as suitable higher α-olefin monomers (see id.). Sita’s enumerated higher α-olefin monomers are seen to constitute an acceptable number (15 species) to form a reasonable expectation of success (see MPEP § 2143(E)) such that those of ordinary skill may select vinylcyclobutane (VCB) through routine testing on the basis of the defined monomeric compounds and the desired properties of the polymer product. Accordingly, at the time of effective filing, it would have been obvious to one of ordinary skill in the art to modify Sita by substituting 1-hexene in Example III by VCB to obtain, predictably, a VCB homopolymer having a narrow PDI as claimed. The motivation to do so and a reasonable expectation of success stem from the teachings of Sita identifying VCB as one of a relatively small number of alternative selections for higher α-olefin monomers that may be used to make homopolymers, co-polymers and block co-polymers that have high isotacticity and low polydispersities, e.g., 1.01 to 2.0 [per claims 1 and 23-24].
Regarding Claim 19, Sita renders obvious the process of claim 1 as discussed above. Further, although not directly reporting molar ratio of the activator relative to catalyst in Example III, Sita does teach that when the activating co-catalyst is an ionic salt of the formula [A+][-BR64] (as in Example III) or a boron alkyl of the formula BR63, the molar ratio of boron atoms contained in the ionic salt or the boron alkyl to total metal atoms contained in the olefin polymerization pre-catalyst is generally in the range of from about 0.9:1 to about 1.5:1, preferably in the range of from about 1:1 to about 1.1:1 (see [0059]). The disclosed ranges each substantially overlap the open-ended range recited in claim 19 for the
corresponding parameter (“greater than 1:1”), and it has consistently been held that even a slight overlap in ranges establishes a prima facie case of obviousness. See MPEP 2144.05. Thus, it would have been obvious to one of ordinary skill in the art to further modify Sita by adjusting the molar ratio of activating co-catalyst to pre-catalyst in Example III to any value within the disclosed ranges including those falling within the range claimed herein and thereby arrive at the claimed invention.
Regarding Claim 20, Sita renders obvious the process of claim 1 as discussed above. Sita in Example III utilizes a species of “half-metallocene” pre-catalyst supported on chloromethylated polystyrene beads instead of on an inorganic support material as claimed (e.g., alumna, zirconia, silica). However, Sita generally teaches that the acetamidinate metal complex may be covalently bonded to a support material (see [0034]-[0035]), which Sita broadly defines as including inorganic oxide support materials and organic solid supports, including polystyrene and functionalized polystyrenes (see [0032]). As specific examples of the inorganic oxide support materials, Sita lists: talcs, silicas, titania, silica/chromia, silica/chromia/titania, silica/alumina, zirconia, aluminum phosphate gels, silanized silica, silica hydrogels, silica xerogels, silica aerogels, montmorillonite clay and silica co-gels (see id.). All of the listed support material are considered equivalents for the purposes of Sita. It would have been obvious to one of ordinary skill in the art to further modify Sita by substituting chloromethylated polystyrene beads by, e.g., a silica, zirconia or silica/alumina solid support as claimed, as all these support materials are considered to be equivalents known for the same purpose. Simple substitution of one known element for another to obtain predictable results, provides the rationale for a prima facie case of obviousness. See MPEP § 2143. Further, the resulting process will meet all the requirements of claim 20.
Regarding Claims 21-22 and 29/32, Sita renders obvious the process of claim 1 as discussed above. Sita also generally teaches polyolefins producible according to the Sita invention include homopolymer, co-polymers or block co-polymers of ethylene and linear or branched higher α-olefin monomers containing 3 to about 20 carbon atoms, with suitable examples of the latter including vinylcyclobutane as noted above (see [0064]). In addition, Sita teaches that olefin polymer according to that invention may also be based on, or contain conjugated or non-conjugated dienes, such as hydrocarbon dienes (linear, branched, or cyclic) having from 4 to about 20 carbon atoms (see id.). In light of such teachings, those of ordinary skill would have reasonably expected the Sita invention to be applicable to copolymerizing VCB with C2-C20 alpha-olefins like ethylene and/or C4-C30 dienes to obtain polyolefins displaying comparable values of isotacticity and polydispersity to Sita’s poly(1-hexene) (PDI = 1.06, per Example III). Accordingly, at the time of effective filing, it would have been obvious to one of ordinary skill in the art to further modify Sita’s Example III by contacting the VCB monomer in the presence of one or more C2-C20 alpha-olefins and/or one or more C4-C30 dienes [for claims 21, 22] with a reasonable expectation of success in obtaining a copolymer comprising VCB and corresponding olefin comonomer(s) units, having a PDI of less than 3.0 [for claims 29, 32].
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Sita as applied to claim 1 above, and further in view of Sita et al (US 2014/0073752 A1).
Regarding Claim 17, Sita renders obvious the process of claim 1 as discussed above. Sita does not disclose, in a single embodiment, the essential reaction conditions claimed, namely a reactor pressure from 0.07 MPa to 7 MPa, a reactor temperature from 20oC to 250oC and hydrogen. However, concerning hydrogen, Sita clearly teaches that such may be used as a chain-transfer agent in the disclosed process (see [0063]). In light of this teaching, it would have been obvious to one of ordinary skill in the art to further modify Sita’s Example III by including hydrogen in an amount optimized to control the relevant molecular weight parameters in order to obtain the low polydispersity polyolefin contemplated by Sita (see [0064]).
As to reactor temperature/pressure, it is acknowledged that in Sita Example III, the polymerization is performed at -10oC, rather than at a reactor temperature from 20oC to 250oC as claimed, and no pressure condition is reported. Nevertheless, in analogous art relating to production of polyolefins of low molecular weight and narrow molecular weight distribution (see [0003]), Sita et al teach that a mixture of a metallocene pre-catalyst, a first olefin monomer, a second olefin monomer, a first co-catalyst, a second co-catalyst, and a metal alkyl may be subject to a reaction temperature from about -25oC to about 40oC; and in one embodiment, to a temperature of about 25oC (see [0012]-[0015], [0082], and [0098]-[0099] (Example 1)). Sita et al further teach that the aforementioned mixture can be contacted at any pressure, and in particular, embodiments where the pressure is between about 0 psi to about 40 psi, about 2 psi to about 30 psi, about 3 psi to about 20 psi, or about 4 psi to about 10 psi (see [0086]). Each of the disclosed ranges overlaps the claimed range for reactor pressure (“from 0.07 MPa to 7 MPa” or from 10.15 psi to 1015.26 psi), and it has consistently been held that even a slight overlap in ranges establishes a prima facie case of obviousness. See MPEP 2144.05.
Moreover, it is noted that the metallocene pre-catalyst of Sita et al may be an acetamidinate metal complex analogous in molecular structure to Sita’s pre-catalyst (see Sita et al at [0054], [0098] and cf., Sita at [0008]) and that the first and second co-catalysts used in Example 1 of Sita et al fall within the scope of activators preferred by Sita (viz., [PhNHMe2]+[B(C6F5)4]- and B(C6H5)3; see Sita et al at [0098] and cf. Sita at [0057]). Given the similarity in catalytic reaction conditions and olefin monomers, those of ordinary skill would have reasonably expected the pressure/temperature conditions prescribed by Sita et al to be suitable for conducting the process of Sita. Accordingly, at the time of effective filing, it would have been obvious to one of ordinary skill in the art to further modify Sita’s Example III by performing the polymerization under reaction conditions including a reactor pressure and temperature within the respective ranges recited in claim 17, as taught by Sita et al.
Potentially Allowable Subject Matter
Claims 2-16 would be allowable if amended or rewritten to overcome the rejection under 35 U.S.C. 112 and objections (re: claims 15-16) set forth in this Office action and to include all the limitations of the base claim and any intervening claim.
Claims 25-28 and 30-31 are objected to as being dependent on a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claim.
The closest prior art to Sita and Sita et al, discussed above, does not describe the inventions of claims 2-16, 25-28 and 30-31, or provide proper rationale for modifying either of their respectively disclosed inventions into the invention of any one of said claims.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/08-14-26
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