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 29 January 2024 is acknowledged. Claims 1-3, 10, 12-14, 23, 25-27, 34-38, 40, 41, 43, and 44 as amended are pending.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-3, 10, 13, 14, 23, 25-27, 35, 37, 38, 40, 41, 43, and 44 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Each of claims 1, 25, and 35 each have been amended on 29 January 2024 to add the proviso “wherein at least one of Q1-Q5 is an alkyl”. At the time the application was filed (1 August 2022, the filing date of PCT/IL2022/050830), the specification did not contain this proviso. While species that are classified as alkyl are disclosed for Q1-Q5, there are alkyl species (such as cycloalkyl) not previously disclosed for Q1-Q5. As such, the proviso includes species not disclosed as of the filing date.
The Office recommends amending the proviso to list species originally disclosed for Q1-Q5, such as “linear branched alkyl”.
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.
Claims 1-3 and 25-27 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhang et al., “Phosphine-Iminoquinoline Iron Complexes for Ethylene Polymerization and Copolymerization,” Organometallics 36, 3758-3764 (2017) (“Zhang”).
As to claims 1-3, Zhang discloses the iron complex
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(p. 3758). This differs from structure A1 by not having iron (III) as recited, nor the double bond linkage from the heterocyclic nitrogen group, nor CH2-R4. However, it is deemed to be an isomer where the recited double bond linkage and Fe(III) (as required by claim 2) is an isomer of the Fe(II) pyridyl structure of Zhang, he Ar group is an isomer of a group bonded directly to the nitrogen heterocyle group, the atoms from the imine group are an isomer of a heterocyclyl group that may be a substituent for R1, R2, or Q1-Q5, the chlorine atomsisomeric with the halide substitutents of Q1-Q6, and where alkyl groups of the Ar groups are isomeric with the CH2-R4 group, and where R1 and R1 are the same as required by claim 3. As such, the structure of Zhang is an isomer of a structure of formula A1 of claims 1-3.
As to claims 25-27, Zhang discloses the complex
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(p. 3758), which has an Fe(II) center as required by claims 26 and has R1 and R2 identical as required by claim 27. This compound does not have the structure of recited formula A3, but is an isomer thereof; that is, the Ar group is an isomer of the same groupbonded directly to the pyridyl group, the atoms from the imine group are an isomer of a heterocyclyl group that may be a substituent for R1, R2, or Q1-Q5. Since the structure is an isomer of a structure of formula A3, it meets the claims.
Claim 35 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chen et al., "New Bulky Phosphino-Pyridine Ligands. Palladium and Nickel Complexes for the Catalytic Polymerization and Oligomerization of Ethylene" Organometallics, 22 (24), 4893-4899 (2003) (“Chen”).
As to claim 35, Chen teaches compounds 4a and 4b (p. 4893, Chart 1), which meets recited formula B1 where R1 and R2 are either Mes or o-Tol, which are both alkylaryl groups, R3 is H, n is 3, each of Q6 are hydrogen, each of Q1, Q3, and Q5 are linear alkyl, and thus at least one of Q1-Q5 is alkyl.
Claim 35 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mannava et al. "Nickel-Mediated Dehydrogenative Aryl-Aryl Homocoupling of a Bulky Phosphino-Pyridine" Organometallics 38 (23), 4554-4559 (2019) (“Mannava”).
As to claim 35, Mannava teaches a ligand having the structure
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(abstract). While the structure differs from the drawn structure of recited formula B1 by not having an alkyl group at one of Q1-Q5, it is an isomer of a structure of formula B1 (for example, a methyl group from the tBu group moved to the Ph group would put it in the structure of formula B1).
Allowable Subject Matter
Claims 12, 34, and 36 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.
Claims 10, 13, 14, 23, 37, 38, 40, 41, 43, and 44 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), 1st paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: the prior art, including the references discussed above, does not teach or suggest compounds recited in these claims. While the structures of claim 36 are within the broad definition of a ligand compound disclosed in WO 2008/085653 A1, that reference does not provide sufficient rationale to arrive at these specific structures. The prior art of Zhang cited above does not suggest the equilibrium structures of claim 10, nor the method of metathesis polymerization of claim 13 and its dependent claims.
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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