DETAILED ACTION
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
Claim 1 is objected to because of the following informalities:
With regard to claim 1, the claim recites in the preamble “method to synthesize a substituted dibenzocyclooctane”. However, the last two steps of the claimed method each result in a substituted dibenzocyclooctane, a diiodo-substituted and a divinyl-substituted compound, and thus the recitation in the preamble of only a “substituted” compound could cause confusion regarding the desired product. For clarity, the Examiner suggests amending the preamble to recite “method to synthesize a divinyl-substituted dibenzocyclooctane”.
Appropriate correction is required.
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.
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 1-5 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.
With regard to claim 1, the claim recites in lines 9-10 “using a triethylsilane/trifluoroacetic acid mixture”. This phrasing is unclear, because typically the use of a slash “/” indicates “and/or”, but the claim then further recites that it is a mixture. Thus, the claim is indefinite.
For purposes of examination, the Examiner will consider that it is a step using both triethylsilane and trifluoroacetic acid, based on the synthesis step in paragraph [0019] of the instant specification.
With regard to claims 2-5, the claims are rejected as being dependent on a rejected base claim.
Claim Rejections - 35 USC § 102
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 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kiker (A Regioselective Route to Negative Coefficient of Thermal Expansion Materials for Tuning Epoxy Thermomechanics, December 2021).
With regard to claims 1-3, Kiker teaches the following scheme (page 4, Scheme 2).
PNG
media_image1.png
444
847
media_image1.png
Greyscale
This scheme is identical to the process steps of instant claims 1 and 2 in the claimed order. Compound 5 has the divinyl substituents in positions 2 and 9, as claimed in instant claim 3.
Claim Rejections - 35 USC § 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.
Claims 4 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Kiker (A Regioselective Route to Negative Coefficient of Thermal Expansion Materials for Tuning Epoxy Thermomechanics, December 2021) as applied to claim 1 above, and further in view of Redline et al. (US 2021/0387987) and Soga et al. (US 2020/0321634).
With regard to claims 4 and 5, Kiker teaches the process for making the divinyl-substituted dibenzocyclooctane 5 above. Kiker further teaches that compounds comprising the dibenzocyclooctane (DBCO) moiety are useful as a compound which harnesses conformational structure change to reduce CTE (coefficients of thermal expansion) mismatch in thermoset polymers (page 2, first full paragraph).
Kiker does not explicitly teach crosslinking a thermosetting resin with the compound 5 to form a thermoset.
Redline teaches forming thermoset polymers by crosslinking (paragraph [0003]) where the thermoset polymer is produced by reacting a curative with a resin comprising epoxy, acrylates, methacrylates, unsaturated polyesters, vinyl esters, and urethanes (instant claim 5) (paragraph [0032]). Redline further teaches that the curative can be di-substituted with a variety of reactive groups, comprises a dibenzocyclooctane (DBCO) moiety (paragraphs [0032] and [0009]), and that the curative fine tunes CTE (paragraph [0009]). Redline does specifically teach that the variety of reactive groups of the curative include vinyl groups, as in compound 5. However, divinyl aromatic compounds are known as reactive crosslinking agents in similar thermoset polymers, as taught by Soga (paragraphs [0054] and [0035]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to crosslink the compound 5 comprising the divinyl groups with a resin to form a thermoset polymer, as claimed, because Kiker and Redline each teach that DBCO derivatives can be used as curatives in thermosetting polymers to reduce CTE, Redline teaches that DBCO moieties with a variety of reactive groups can be used in the crosslinking, and Soga teaches that it is known that divinyl groups are reactive to crosslink with resins for thermosetting resin production.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, In Suk Bullock can be reached at 571-272-5954. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/Alyssa L Cepluch/Examiner, Art Unit 1772
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772
Prosecution Insights