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 Objections
Claims 61, 62 & 63 are objected to as being dependent upon a rejected base claim, but would be allowable* if rewritten in independent form including all the limitations of the base claims and any intervening claims.
*Note: claim 62 must also be amended to overcome the indefiniteness rejection under 35 U.S.C. § 112 detailed herein
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.
Claims 62 is rejected under 35 U.S.C. § 112(b) as being indefinite.
Regarding claim 62, the structure depicted in claim 62 contains an open-ended parenthesis by the enol ether portion of the structure but does not have a closed parenthesis. This is in contrast to the open and closed parenthesis around the cycloalkenyl portion of the structure. Therefore, it is unclear what structure is being implied by the claimed formula. For examination purposes, the claim was examined & interpreted as the open-ended parenthesis being there was a mistake.
Claim Rejections - 35 USC § 102/103
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 42 – 44, 46 – 49, 52 – 55, 60 & 64 are rejected under 35 U.S.C. § 102(a)(2) as being anticipated by, or in the alternative, under 35 U.S.C. § 103 as being obvious over Kuhnle et al. (US 2001/0006988 A1).
Regarding claims 42, 43, 48 & 52, Kuhnle teaches methods for forming polymers, said method comprising the use of a ruthenium carbene complex as a ROMP catalyst to open a cycloalkenyl monomer of Formula (I) (Abstract). Said monomer may be dihydrofurans such as 2,3-dihydrofuran (p. 2, [0022], [0025]). Kuhnle describes contacting a cycloalkenyl monomer with a ruthenium carbene ROMP catalyst (p. 1, [0012]-[0014]). In further embodiments, polymers may be prepared via copolymerization of said monomer with at least one further olefinically unsaturated monomer, such as norbornene (p. 2, [0027]-[0028]). Kuhnle discloses 2,3-dihydrofuran with sufficient specificity to anticipate the claimed enol ether, by teaching the use of a ROMP (ruthenium complex) catalyst to open a cycloalkenyl monomer (norbornene) in the presence of an enol ether (2,3-dihydrofuran), yielding a copolymer.
In the alternative, as Kuhnle teaches subjecting identical monomers to ROMP in the presence of the same catalyst, it would have been obvious to select 2,3-dihydrofuran based on its art-recognized suitability for its intended use. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
As the prior art teaches identical methods, the claimed relative change in rate will necessarily occur. Chemical compositions and their properties are inseparable. Products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP § 2112.01.
Regarding claim 44, Kuhnle provides embodiments of the ruthenium carbene complexes (p. 2 & 3, [0037]). The embodiment depicted in Formula (VI) reads on the ruthenium complex as required by the claim.
Regarding claims 46 & 47, the cycloalkenyl monomer in Kuhnle may be substituted or unsubstituted norbornene and/or dicyclopentadiene (p. 2, [0028]).
Regarding claim 49, Kuhnle describes the polymerization may be done with or without a solvent (p. 6, Claims 18 & 19).
Regarding claims 53 & 54, Kuhnle teaches norbornene being reacted with ROMP catalyst in the presence of 2,3-dihydrofuran. The solution is polymerized at 35°C (p. 4, [0068]).
Regarding claim 55, Kuhnle teaches forming cured coatings from their invention (p. 3, [0043]) and said coating will inherently be chemical resistant as Kuhnle teaches coatings compositionally identical to the coatings as claimed.
Regarding claim 60, Kuhnle teaches the use of various dihydrofurans (p. 1, [0025]). The DHF taught by Kuhnle read on the enol ether as required by the claim when R18, R20, R21 & R22 are hydrogen and R19 & R23 represent the same C1-C6 alkyl group.
Regarding claim 64, Kuhnle teaches methods of forming polymers via ROMP (Abstract; p. 1, [0011]). Various methods are disclosed, some without a solvent and some with a solvent (see, for instance, example 2 (p. 4, [0053]) & example 12 (p. 5, [0103])). The increased temperature employed in various examples may be considered the as the stimulus in the instant claim 64. Kuhnle teaches the used of various DHF(s), reading on the enol ether as claimed. As Kuhnle teaches subjecting identical monomers to ROMP in the presence of the same catalyst, the claimed relative change in rate will necessarily occur.
Claims 45 & 51 are rejected under 35 U.S.C. § 103 as being obvious over Kuhnle et al. (US 2001/0006988 A1) in view of Grubbs et al. (US 6,515,084 B2).
Regarding claim 45, Kuhnle remains as applied above. Kuhnle teaches the use of a ruthenium(II) complex as the metathesis catalyst but is silent on the catalysts as required by the claim.
In the same field of endeavor, Grubbs studied highly active and stable ruthenium and osmium metal carbene complex compounds, their synthesis and use as catalysts for olefin metathesis reactions (col. 1, lines 25-27). Grubbs explored introducing functional groups via metathesis with ruthenium complexes, teaching the use of the ROMP catalysts as required by the claim (col. 14, line 32 – co. 15, line 7).
It would have been obvious to one of ordinary skill in the art at the time of filing to select anyone of the ruthenium catalysts disclosed by Grubbs, as the ROMP catalyst in Kuhnle, as Grubbs expressly teaches their use as suitable for introduction of functional groups. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Regarding claim 51, Kuhnle remains as applied above. Kuhnle teaches the use of cyclooctene, norbornene, dicyclopentadiene (p. 2, [0028]), but is silent on 1,5-cyclooctadiene as required by the claim.
In the same field of endeavor, Grubbs studied highly active and stable ruthenium and osmium metal carbene complex compounds, their synthesis and use as catalysts for olefin metathesis reactions (col. 1, lines 25-27). Grubbs expressly relates ROMP with cyclooctene and 1,5-cyclooctadiene (col. 16, line 63 – col. 17, line 6).
It would have been obvious to substitute cyclooctene in Kuhnle with 1,5-cyclooctadiene for the cyclic monomer, as Grubbs teaches cyclooctene in parallel with 1,5-cyclooctadiene. It is prima facie obvious to substitute equivalents where the equivalence is recognized by the prior art. See MPEP § 2144.06. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Claims 50, 56 & 57 are rejected under 35 U.S.C. § 103 as being obvious over Kuhnle et al. (US 2001/0006988 A1) in view of Feast et al. (US 6,677,418 B1).
Regarding claim 50, Kuhnle remains as applied above. Kuhnle teaches the use of cyclic monomers, such as norbornene, however, is silent on a cyclic monomer as required by the claim.
In the same field of endeavor, Feast teaches processes for making copolymers via a ROMP catalyst and a strained (poly)cyclic monomer (Abstract). Most preferred cyclic monomer for this use is norbornene substituted in the 5 and 6 positions (col. 3, lines 17-21) but Feast also provides generic formulae (I) & (II) for suitable cyclic monomers:
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190
336
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Where X is a linear bridging group (–COOR2COO–) or a fused bridging group as defined by:
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150
398
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Where two R1 groups of formula (I) may together form a cyclic amide or anhydride (col. 3, line 17 – col. 4, line 10).
Abiding by the above definitions and express disclosures of preference to norbornene substituted in the 5 & 6 positions, it would have been obvious to one of ordinary skill in the art at the time of filing to select the substituted norbornene taught by Feast, for use as the cyclic monomer in Kuhnle as Kuhnle states norbornene (substituted or unsubstituted) may be used in this capacity. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside the ranges disclosed by the prior art. See MPEP § 2144.05. It is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP § 2144.07.
Modification of Kuhnle in view of Feast as detailed above reads on limitations established by the claim 50.
Regarding claims 56 & 57, maintaining the modification of Kuhnle in view of Feast previously detailed, Kuhnle provides several additives which may be further included in the resultant polymer such as talc, ground limestone or phenyl ethers (p. 3, [0039]). The method taught by Feast may further employ any suitable reinforcing fibers (col. 6, lines 55-58). Feast teaches the processes according to the invention are suitable for preparing composites such as coatings (col. 5, lines 10-15).
The above disclosures read on all limitations established by claims 56 & 57.
Claims 58 & 59 are rejected under 35 U.S.C. § 103 as being obvious over Kuhnle et al. (US 2001/0006988 A1) in view of Luchterhandt et al. (US 2010/0036015 A1).
Regarding claims 58 & 59, Kuhnle remains as applied above, however, remains silent on the size requirements as required by the claims.
In the same field of endeavor, Luchterhandt teaches compositions polymerizable via ring-opening metathesis polymerization (ROMP) comprising at least one monomer and an initiator (Abstract), further stating the advantages of also incorporating a ruthenium complex (p. 1-2, [0016]). Luchterhandt details additives which may also be incorporated, including fillers and fibers. Luchterhandt states said fillers may be nanoshaped and provides size ranges suitable for these fillers from several microns down to a few nanometers (p. 11, [0087]-[0088]).
In view of Luchterhandt describing said fillers as nanoshaped, it would have been obvious to one of ordinary skill in the art at the time of filing to employ the range of “a few nanometers” as a guide for the fillers utilized in Kuhnle, as Luchterhandt demonstrates fillers of this nature (i.e., type & dimensions) to be suitable in similar compositions with similar end uses. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside the ranges disclosed by the prior art. See MPEP § 2144.05.
Allowable Subject Matter
Claims 61, 62 & 63 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claims.
The claims are drawn to a method of making a polymer by contacting one or more cycloalkenyl monomers with a ring-opening metathesis catalyst in the presence of an enol ether to provide a polymerizable solution and initiating polymerization of the one or more cycloalkenyl monomers with the enol ether to provide a copolymer.
The closest prior art is attributed to Kuhnle et al. (US 2001/0006988 A1) and Grubbs et al. (US 6,515,084 B2).
Kuhnle teaches methods for forming polymers, said method comprising the use of a ruthenium carbene complex as a ROMP catalyst to open a cycloalkenyl monomer of Formula (I) (Abstract). Said monomer may be dihydrofurans such as 2,3-dihydrofuran (p. 2, [0022], [0025]). Kuhnle describes contacting a cycloalkenyl monomer with a ruthenium carbene ROMP catalyst (p. 1, [0012]-[0014]). In further embodiments, polymers may be prepared via copolymerization of said monomer with at least one further olefinically unsaturated monomer, such as norbornene (p. 2, [0027]).
Kuhnle fails to teach structures reading on the structures as claimed as the enol ether is a single constituent whereas Kuhnle teaches repeating enol ether units.
In the same field of endeavor, Grubbs teaches ruthenium and osmium metal carbene complex compounds, their synthesis and use as catalysts for olefin metathesis reactions (col. 1, lines 25-27). Grubbs explored introducing functional groups via metathesis with ruthenium complexes, teaching the use of the ROMP catalysts as required by the claim (col. 14, line 32 – co. 15, line 7).
Even if one of ordinary skill in the art were motivated to modify Kuhnle in view of Grubbs, the product obtained from such modification would fall outside the scope of the formula recited in claims 61-63.
A thorough search of the prior art neither revealed nor identified any other reference or combination of references, including the closest prior art of Kuhnle et al. (US 2001/0006988 A1) and Grubbs et al. (US 6,515,084 B2), which would anticipate, fairly teach, suggest or otherwise motivate one of ordinary skill in the art to arrive at the claimed invention. The teachings of Kuhnle & Grubbs are inadequate & insufficient (independently or in view of one another) for one of ordinary skill in the art to anticipate or render obvious the method that is claimed in the instant application.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CHRISTIAAN ROELOFSE whose telephone number is (571)272-2825. The examiner can normally be reached Monday-Friday 8:00-4:00 EST.
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/CHRISTIAAN ROELOFSE/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762
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