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 .
Election/Restrictions
Applicant’s election without traverse of Group I (claims 1-8) and species i (compound (A) represented by Formula (1)) in the reply filed on 11/6/2025 is acknowledged.
Groups II-VIII (claims 9-15) and species ii-iii (compound (B) and (C)) are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 11/6/2025.
Response to Amendment
The amendment filed on 3/20/2026 has been entered. Claim(s) 1 and 5 is/are currently amended. Claim(s) 1-15 is/are pending with claim(s) 9-15 withdrawn from consideration. Claim(s) 1-8 is/are under examination in this office action.
Response to Arguments
Applicant's argument, filed on 3/20/2026, with respect to 103 rejection has been fully considered. The argument about the difference between the claimed compound (A) with Formula (1) and prior art’s TEMPO is moot in view of the new grounds of rejection presented below.
Applicant argued that the claimed resin composition imparts low dielectric properties, a low coefficient of thermal expansion, and a high Tg (glass transition temperature) to its cured product. In this regard, Dershem fails to teach that free-radical compounds such as TEMPO can achieve the above-mentioned merits of the presently claimed invention. One of skill in the art would have no expectation of success in achieving the merits of the presently claimed invention even if one were to start with TEMPO and change its structure to match that of the claimed compound.
In response, the recited low dielectric properties, a low coefficient of thermal expansion, and a high Tg are not part of the claims. Even if they are incorporated into the claims, they are properties of the product. “Products of identical chemical composition cannot have mutually exclusive properties." A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. “When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not.” In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990)). See MPEP 2112.01. Since the prior art teaches the same product as the current invention, the recited property is expected to be present.
Claim Objections
Claims 6 and 8 are objected to because of the following informalities: the recited “the free radical compound” should be --the radical compound--, since claim 1 recites “a radical compound” rather than “one free radical compound”. Appropriate correction is required.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
Claim(s) 1-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Aoki et al (WO 2020158849 A1, US version US 20220098404 A1 is referenced herein) in view of Cao et al (“Nitroxide-Mediated Radical Polymerization of Styrene in Emulsion”, Polymer Journal, Vol. 33, No. I, pp 75-80 (2001)).
Regarding claims 1-5, Aoki teaches a thermosetting resin composition (X) [0019].
The composition (X) comprises a styrene-based elastomer (E) which is a styrene ethylene butylene styrene block copolymer, Septon V9827 manufactured by Kuraray (Elastomer 1 in Examples 1-3 and 8-25) [0160, Tables 1-4].
As evidenced by the applicant [0052 spec.], Septon V9827 meets the claimed styrenic block copolymer as specified in claims 2-3.
The thermosetting resin composition (X) comprises a radically polymerizable unsaturated compound (A) [0024] containing compound (A2) which is polyphenylene ether which is terminal-modified with a substituent having a carbon-carbon unsaturated double bond [0035-0036], expressed by formula (5) [0043]:
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wherein R4 is a hydrogen atom or an alkyl group.
Therefore, the compound (A2) reads on the claimed radical polymerizable compound, as specified in claims 4-5.
The thermosetting resin composition (X) comprises an organic radical compound (C) represented by formula (11) [0068]:
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wherein R is hydrogen or a hydroxyl group. An example is Organic radical compound 1 (2,2,6,6-tetramethylpiperidine 1-oxyl) [0156] (TEMPO).
Pertinent to the same problem, Cao teaches several TEMPO derivatives as free radicals for radical polymerization, including TEMPO and BTEMPO [Scheme 1, p.75]. It is prima facie obvious to substitute equivalents for the same purpose where the equivalence is recognized by the prior art. See MPEP 2144.06. Since Cao recognized TEMPO and BTEMPO are equivalent as free radicals for the same purpose of radical polymerization, it would have been obvious for one of ordinary skilled in the art at the time of filing to substitute TEMPO with BTEMPO in Aoki’s composition.
BTEMPO reads on the claimed radical compound (A) represented by Formula (1), wherein XA represents a benzoyloxy group.
Regarding claim 6, Aoki teaches Organic radical compound 1 used in Examples 14, 15, 18 in the amount of 0.49, 0.10, and 0.49 parts with respect to 70 parts of the compound (A) and 30 parts of the elastomer (E) [Tables 2-3]. This is equivalent to 0.49, 0.10, and 0.49 parts with respect to 100 parts by mass of a sum of the styrenic block copolymer and the radical polymerizable compound, falling within the claimed range of 0.001 to 1 part.
Regarding claim 7, Aoki teaches that the composition (X) suitably contains a thermal radical polymerization initiator (B) [0059].
Regarding claim 8, Aoki’s Example 14 contains 0.14 part of Organic radical compound 1 and 1.58 part of thermal radical polymerization initiator 1 [Table 2]. Therefore, the mass ratio of the free radical compound to the reaction initiator is 0.14:1.58 or 0.09:1.0, falling within the claimed range of 0.001 : 1.0 to 0.1 : 1.0.
Claim(s) 1-4 and 6-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Tochihira et al (US 20180258324 A1) in view of Dershem et al (US 20130187095 A1) and Cao et al (“Nitroxide-Mediated Radical Polymerization of Styrene in Emulsion”, Polymer Journal, Vol. 33, No. I, pp 75-80 (2001)).
Regarding claims 1-4, Toshihira teaches a thermosetting adhesive composition for semiconductor components [0003].
The composition comprises a component (C) that is a thermoplastic elastomer that is a copolymer of a polyolefin block and a polystyrene block [0030], including polystyrene-poly(ethylene/propylene) block copolymer [0084], having molecular weight of particularly preferably 10,000 to 200,000. Thus, the component (C) reads on the claimed styrenic block copolymer as specified in claims 2-3.
The composition comprises a component (A) a vinyl compound having a polyphenylene ether skeleton represented by formula (1) [0052], which has vinyl groups (having a carbon-carbon unsaturated double bond) at the chain terminals. Therefore, the component (A) reads on the claimed radical polymerizable compound as specified in claim 4.
Toshihira does not teach the claimed free radical compound (A).
In the same field of endeavor, Dershem teaches a thermosetting adhesive composition for semiconductor components [0003], comprising an inhibitor to extend the useful shelf life of adhesive compositions containing TEMPO (2,2,6,6-tetramethyl-1-piperidnyloxy, free radical) [0041].
It would have been obvious to one of ordinary skill in the art at the time of filing to add TEMPO to Toshihira’s composition to extend the useful shelf life of adhesive composition.
Pertinent to the same problem, Cao teaches several TEMPO derivatives as free radicals for radical polymerization, including TEMPO and BTEMPO [Scheme 1, p.75]. It is prima facie obvious to substitute equivalents for the same purpose where the equivalence is recognized by the prior art. See MPEP 2144.06. Since Cao recognized TEMPO and BTEMPO are equivalent as free radicals for the same purpose of radical polymerization, it would have been obvious for one of ordinary skilled in the art at the time of filing to substitute TEMPO with BTEMPO in the composition of Toshihira in view of Dershem.
BTEMPO reads on the claimed radical compound (A) represented by Formula (1), wherein XA represents a benzoyloxy group.
Regarding claim 6, Dershem teaches that the amount of TEMPO is in the range of 100 to 2000 ppm relative to the weight of total base resin [0041]. This equals 0.01 part to 0.2 part relative to the weight of total base resin, which falls within the claimed range of 0.001 to 1 part.
Regarding claim 7, Dershem teaches that the composition may contain a curing initiator [0032]. It would have been obvious to one of ordinary skill in the art at the time of filing to add an initiator in Toshihira’s composition, as it is expressly disclosed as being useful in this capacity. It has been established that selection of a known material based on its suitability for its intended use is prima facie obvious (Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945)). See MPEP 2144.07.
Regarding claim 8, Dershem teaches 0.1-5 wt% of initiator based on total weight of the composition [0032]. Dershem also teaches 0.01 part to 0.2 part of TEMPO relative to the weight of total base resin as stated above. Therefore, the mass ratio of the free radical compound to the reaction initiator is in the range of 0.002:1 to 2:1, as calculated by the examiner, overlapping the claimed range of 0.001 : 1.0 to 0.1 : 1.0. A prima facie case of obviousness exists where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" (MPEP 2144.05.I).
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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JIANGTIAN XU whose telephone number is (571)270-1621. The examiner can normally be reached Monday-Thursday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Robert Jones can be reached on (571) 270-7733. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/JIANGTIAN XU/Primary Examiner, Art Unit 1762
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