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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections - 35 USC § 112
Claims 1-3, 6-7, 9, 12-21, 23-24 and 28-29 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.
Claims 1 and 20 recite the limitation "a phthalonitrile compound bearing, on the benzene ring thereof, at least one hydroxyl group". There is insufficient antecedent basis for this limitation in the claim, as the language of the claim does not preclude substitution on the phthalonitrile which allow for more than one benzene ring to be present in the structure. The applicant should review the claim language and amend as appropriate to correct this issue. For the purposes of examination, the claim will be interpreted to mean that the cyano functionality and the hydroxyl functionality must be on the same aromatic ring.
Claims 2-3, 6-7, 9, 12-19, and 28-29 are rejected based upon their dependence upon claim 1.
Claims 21 and 23-24 are rejected based upon their dependence on claim 20.
Claim Rejections - 35 USC § 103
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 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 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Zeng (European Polymer Journal (2009) v.45, p.1328-1335).
Regarding Claims 1 and 20,
Zeng teaches a cured resin comprised of a phthalonitrile compound of the following structure in scheme 1:
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which is subsequently cured at 225 °C for 30 minutes or more (Page 1331, right column to Page 1332, left column, first paragraph). While Zeng does not use a basic medium in this particular curing reaction, Zeng does teach that similar phthalonitrile resins can be cured through the use of organic amines and metal salts (Page 1328, right column, first paragraph). Zeng notes that these conditions are used to promote faster polymerization (Page 1328, right column, first paragraph), providing the ordinarily skilled artisan the motivation to use such catalysts in order to improve curing time and temperature. As such, it would have been obvious prior to the effective filing date of the instant application to have used a curing catalyst to cure the phthalonitrile-based resin with a reasonable expectation of success.
Claims 2 and 6-7 are rejected under 35 U.S.C. 103 as being unpatentable over Zeng (European Polymer Journal (2009) v.45, p.1328-1335) as applied to claims 1 and 20 above, and further in view of Padias (Journal of Polymer Science A: Polymer Chemistry (1986) volume 24 pages 1675-1683).
Regarding Claims 2 and 6-7,
Zeng teaches thermoset polymers derived from phthalonitrile and containing hydroxyl groups, but does not teach the use of phthalonitrile components where the hydroxyl group is ortho to nitrile groups. Padias teaches the formation of polymers from the following monomer:
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which Padias teaches are polymerized using a radical initiator (Page 1676, Polymerization Procedure paragraph) but notes that nitrile containing monomers can be polymerized under anionic conditions (Page 1675, Introduction Section, second paragraph). As Zeng teaches that polymerization of these resins occurs through an addition cure mechanism (Page 1328, Introduction Section, first paragraph) and further that inclusion of hydroxy groups on the phthalonitrile monomers can offer excellent mechanical and thermal properties without requiring additional additives (Page 1329, Introduction Section, left column, third paragraph), one of ordinary skill in the art would be motivated to include at least one of these groups. Further, as Padias demonstrates that this monomer can self-polymerize, it would have been obvious prior to the effective filing date of the instant application to have used the monomer taught by Padias to form a polymer as taught by Zeng with a reasonable expectation of success.
Claims 28-29 are rejected under 35 U.S.C. 103 as being unpatentable over Zeng (European Polymer Journal (2009) v.45, p.1328-1335) as applied to claims 1 and 20 above, and further in view of Sastri (Polymer Composites (1996) v.17, p.816-822).
Regarding Claims 28-29,
Zeng teaches the thermoset material as discussed above in regard to claim 1, however Zeng does not teach the use of carbon fiber filler. Sastri teaches that phthalonitrile resins can be combined with carbon fibers to create composites with improved thermal performance (Abstract). Sastri further teaches the phthalonitrile compound is formed into a prepreg with carbon fibers and an organic amine curing additive (Page 817, right column, final paragraph to page 818, left column, first and second paragraph). One of ordinary skill in the art, recognizing that other phthalonitrile resins can be used in the formation of carbon fiber containing composites, would be motivated to use the phthalonitrile compound of Zeng to form the composite due to the improved curing performance (Page 1329, left column, third paragraph). As such, it would have been obvious prior to the effective filing date of the instant application to have combined the resin of Zeng with the carbon fiber containing phthalonitrile polymer of Sastri to obtain the predictable result of a cured hydroxy-containing phthalonitrile resin containing carbon fibers with a reasonable expectation of success.
Allowable Subject Matter
Claims 3, 9, 12-19, and 21-24 contain allowable subject matter.
The following is a statement of reasons for the indication of allowable subject matter: The closest prior art is Zeng, Sastri, and Padias. While Zeng teaches a phthalonitrile compound that contains a hydroxyl group and can be cured into a polymer, Zeng does not teach compounds which are connected to benzaldehyde-type rings connected through an ether linkage nor the ortho relationship between the cyano functionality and the hydroxyl group(s). Similarly, Sastri teaches the formation of phthalonitrile polymers through the use of organic amine curing additives, but does not teach compounds containing free hydroxyl groups nor the required ortho substitution pattern. In neither Zeng or Sastri is there teaching or fair suggestion to utilize this substitution pattern. Sastri does not teach or fairly suggest the incorporation of aldehyde functionality and while Zeng notes specifically extending the functionality to amides and ketones, there is no teaching or fair suggestion to incorporate an aldehyde into the phthalonitrile compound. Finally, while Padias teaches the use of phthalonitrile compounds with the hydroxyl functionality ortho to the cyano functionality as required in the instant claims, Padias does not teach the functionalization of one of those hydroxyl groups with any other functionality nor does Padias teach or fairly suggest the use of additional compounds containing aldehyde functionality into the composition.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765