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 .
This Office action is in response to the amendment filed 12/3/2025. Claims 1, 4-5 and 7 are amended; and claims 7-16 are withdrawn from consideration as being drawn to non-elected invention. Accordingly, claims 1-16 are currently pending in the application.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim Rejections - 35 USC § 102/103
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.
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 1-3 and 6 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Fujita et al (JP 2018-024856 A).
Regarding claims 1 and 2, Fujita et al disclose (meth)allyl ether represented by the formula:
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wherein R1 is an alkyl group, R2 is hydrogen and “a” is an integer of 1 to 3 and “n” is a real number from 1 to 10 (overview) which reads on oligomer in present claim 1 wherein R1 is an unsaturated group, and n = 1-10. Hence, oligomer with n = 0 is present in amount of 0% (i.e., reads on oligomer with n = 0 in amount of less than 80% which includes 0%)
Fujita et al are silent with respect to the amount of alkali metal ion.
However, see example 1, of Fujita et al, wherein sodium hydroxide aqueous solution is added to reaction mixture and after the reaction is complete, water, DMSO and the like are distilled off under heating and reduced pressure. Then acetic acid was added for neutralization and repeatedly washed with water and confirmed that the aqueous layer became neutral (paragraph 0075). Therefore, it is the Office’s position that (meth)allyl ether of Fujita et al inherently includes alkali metal ion such as Na+ (i.e., reads on alkali metal ion in present claim 1 and Na+ ion in present claim 2) in smaller amounts of 1 ppm to 15 ppm. Case law holds that a material and its properties are inseparable. In re Spada, 911 F.2d 705,709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
In light of the above, it is clear that Fujita et al anticipate the present claims.
Alternatively, in the event any differences can be shown for the product of present claims, as opposed to the product taught by Fujita et al, such differences would have been obvious to one of ordinary skill in the art as a routine modification of the product to remove as much of the alkali metal ion as desired by washing repeatedly with water. As a practical matter, the Patent Office is not equipped to manufacture products by the myriad of processes put before it and then obtain prior art products and make physical comparisons therewith." In re Brown, 459 F.2d 531, 535, 173 USPQ 685, 688 (CCPA 1972).
Regarding claim 3, it is noted that vinyl benzyl halide is not used in the process of preparing (meth)allyl ether in example 1 of Fujita et al (i.e., reads on 3000 ppm or less of vinyl benzyl halide in present claim 3 which includes 0 ppm of vinyl benzyl halide).
Regarding claim 6, see example 1, of Fujita et al, wherein the obtained (meth)allyl ether is of formula
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in which n = 2 (paragraph 0075). It is noted that molecular weight of (meth)allyl ether when n = 2 is calculated to be 680 g/mol
Claim Rejections - 35 USC § 103
Claims 1-2 and 4-6 are rejected under 35 U.S.C. 103 as being unpatentable over Zupancic et al (US 4,824,920) in view of Wang et al (US 4,707,558).
Regarding claims 1 and 4-5, Zupancic et al teach resins having the formula:
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wherein P =
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with R1, R2, R3 and R4 = hydrogen, a=0, b=0, m, n, s, t = 0 or an integer and m + n + s + t = 1 to 10; A =
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and R5 = H (col. 3, lines 33-68 and col. 4, lines 1-21) which reads on oligomer in present claim 1 when A =
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(unsaturated group in present claim 1, chemical formula 2-1 to 2-3 in present claim 4 and unsaturated group in present claim 5); n, s, t = 0 and p = 1 to 10 (i.e., reads on n = 1 to 10 in present claims 1 and 5), b = 0, R2, R3 and R4 = hydrogen (i.e., reads on the oligomer in present claims 1 and 4-5). See example 1, wherein potassium hydroxide solution is added during the preparation of vinyl benzyl ether (col. 7, lines 45-68).
Zupancic et al are silent with respect to amount of alkali metal.
However, Wang et al in the same field of endeavor teach preparation of monomers and oligomers containing a plurality of vinyl benzyl ether groups (title). See example 1, wherein the sodium hydroxide is added to the reaction mixture. After maintaining the reaction mixture at 450C for 2 hours, the reaction mixture was cooled to room temperature and dry ice was added to neutralize any excess base. The solution was washed several times with water until the pH of material was 7 (col. 5. lines 15-52). Therefore, in light of the teachings in Wang et al, it would have been obvious to one skilled in art prior to the filing of present application to use any known method of neutralizing the reaction mixture to obtain low amounts of sodium (i.e., alkali metal ion in present claim 1 and Na+ ion in present claim 2), absent evidence to the contrary.
Regarding claim 6, see example, wherein the oligomer has molecular weight in the presently claimed range (see Table 1 in col. 8).
Response to Arguments
The objections and rejections under 35 U.S.C. 112(b) and 112(d) as set forth in paragraphs 7, 9 and 12, of office action mailed 9/5/2025, in view of the amendments to claims 1, 4 and 5.
Applicant's arguments filed 12/3/2025 have been fully considered but they are not persuasive. Specifically, applicant argues that amount of alkali metal ion of 1 ppm to 15 ppm is important in influencing the effect of resin on the enhanced dielectric constant and higher glass transition temperatures compared to comparative examples 1-3.
In response, there are several variables between the inventive examples and comparative examples. For e.g., comparative examples 1 and 2 include 100 wt% or oligomer with n = 0 and differences in the amount of alkali metal. It is not clear if the differences in dielectric constant and glass transition temperatures can be attributed to the resin or the content of alkali metal in the resin. Additionally, comparative example 3, which includes oligomer where n = 0 is 40% as in inventive example exhibits similar properties. Hence, it is the Office’s position that impact of alkali metal on said properties are not convincing.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KARUNA P REDDY whose telephone number is (571)272-6566. The examiner can normally be reached 8:30 AM to 5:00 PM M-F.
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, Arrie (Lanee) Reuther can be reached at 571-270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KARUNA P REDDY/Primary Examiner, Art Unit 1764
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