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.
Status of Claims
The examiner acknowledges the amendments to claims 1, 12, 16, and 20. Claims 1-3, 6-7, 9, 12-21, 23-24, and 28-29 are pending.
Claim Interpretation
Claims 1 and 20 are interpreted to be product-by-process claims as they are directed towards a resin that the claim language states can be obtained via a polycondensation reaction. As a result, only the final product can be used to determine the patentability. See MPEP 2113.I.
Claim Rejections - 35 USC § 112
The applicant has amended claims 1 and 20. As a result, the previous 112 rejections are withdrawn.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 Claim 1,
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). Though not required as the claim is constructed as a product-by-process claim, Zeng does not use a basic medium in this particular curing reaction, but 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. Zeng also teaches that compounds such as phenol can be used as curing additives (Page 1328, right column, first paragraph), meeting the requirements of claim 20.
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, contain allowable subject matter.
Claims 3, 9, and 12-19 and 21-24 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.
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.
Response to Arguments
Applicant's arguments filed 6/1/2026 have been fully considered but they are not persuasive for the following reasons.
On pages 8 and 9, the applicant argues that claims 1 and 2 are not obvious over Zeng because Zeng does not teach the synthetic route used by the applicant. The examiner disagrees that the synthetic route differentiates the applicant’s claim over the prior art. Firstly, the examiner notes that the language of claim 1 requires “a resin that can be obtained by…” which does not in fact require the resin to be obtained in this fashion, only that it can be obtained this way. Because of this, any resin that meets the requirement of a phthalonitrile compound comprising a benzene ring bearing two cyano groups and at least one hydroxyl group polymerized in any fashion, so long as it could be generated using the method noted in the claim, would read on the material of the claim. Further, as noted above, the claim is constructed as a product-by-process claim, which requires that only the product itself is used to determine the patentability unless the applicant can demonstrate that the processes would result in different materials. As a result, the resin taught by Zeng meets the requirements of the instant claim as it is generated through the use of a hydroxyl-substituted phthalonitrile as noted in the rejection above. Further, though not required by the claims, Zeng also notes that the curing reactions can be sluggish and are often promoted using curing additives such as organic amines, which are utilized by the applicant. While the applicant argues that polymerizing the resin and then curing in separate steps is different from the prior art, the applicant does not provide evidence that the product obtained would be of differing composition nor properties.
The applicant also offers arguments that the secondary references do not address the synthetic process, however these arguments are moot on the basis of the synthetic process not being relevant for the reasons described above.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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
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