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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 7/24/2026 has been entered.
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Groups II-VIII (claims 9-15) and species ii-iii (compound (B) and (C)) are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 7/24/2026 has been entered. Claim(s) 1 is/are currently amended. Claim 6 is canceled. Claim(s) 1-5 and 7-15 is/are pending with claim(s) 9-15 withdrawn from consideration. Claim(s) 1-5 and 7-8 is/are under examination in this office action.
Response to Arguments
Applicant's argument, filed on 7/24/2026, with respect to claim objection has been fully considered and is persuasive. The claim objection is withdrawn.
Applicant's argument, filed on 7/24/2026, with respect to 103 rejection has been fully considered but is not persuasive.
Applicant argued that the TEMPO disclosed in Aoki and Dershem corresponds to Free Radical Compound 3 in the present application. As demonstrated by the results of Example 3 in Table 1 of the present specification, compositions containing Free Radical Compound 3 exhibit a lower Tg and a somewhat higher coefficient of thermal expansion as compared with compositions containing other free radical compounds (Examples 1, 2, and 4). Therefore, even if TEMPO and BTEMPO were shown to have equivalent radical polymerization performance in styrene systems, such disclosure in Cao does not reasonably suggest that TEMPO would provide performance equivalent to BTEMPO with respect to achieving the high Tg and low coefficient of thermal expansion attained by the present invention.
In response, the examiner is not convinced that the difference in Tg of 5 degrees (240-235) is significant. Similarly, the examiner is not convinced that the difference in coefficient of thermal expansion of 1 (36-35) is significant. In fact, applicant treated Examples 1, 2, 3, and 4 as positive examples, all having good circuit filling properties, as opposed to Comparative Examples, and never mentioned any difference in performance among these positive examples in the specification. This further supports the examiner's position that TEMPO and BTEMPO are equivalents and deliver the same performance of the product.
Applicant argued that claim 1 now specifies that the free radical compound is contained in a relatively small amount. By incorporating the free radical compound within this specific range, the present invention advantageously and more reliably provides a resin composition capable of producing a cured product having low dielectric properties, high Tg, and low coefficient of thermal expansion, while also exhibiting excellent moldability, as evidences in paragraph [0149] of the present specification. There would have been no expectation of successfully achieving such properties in light of the cited art. Unlike the teachings of the present disclosure, Aoki broadly discloses that the content of Organic Radical Compound (C) (corresponding to the "free radical compound" of the presently claimed invention) may be 0.01-5.0 mass% relative to the radically polymerizable unsaturated bond-containing compound (A) (corresponding to the "radical polymerizable compound" of the presently claimed invention), with even the most preferred range being 0.05- 3.0 mass% (see paragraph [0078] of Aoki). Moreover, in the Examples disclosed in Aoki, the amount of Organic Radical Compound (C) is at least 1.4 parts by mass relative to 100 parts by mass of the combined amount of radically polymerizable unsaturated bond-containing compound (A) and elastomer (E) (corresponding to the "styrene-based block copolymer" of the present invention) in most examples (see Tables 1-3 of AOKI). Furthermore, as evident from comparisons between Examples 11 and 12, Examples 15 and 19, and Examples 18 and 19 of Aoki, the invention disclosed in Aoki teaches that larger amounts of Organic Radical Compound (C) result in lower linear thermal expansion coefficients, lower dielectric dissipation factors, and higher temperatures at which minimum melt viscosity is observed. In addition, Aoki explains that a higher temperature for exhibiting minimum melt viscosity is preferable (preferably 140°C or higher) because it facilitates maintaining low viscosity when the resin sheet is heated and melted (see paragraph [0108], etc.). Thus, Aoki contains no suggestion whatsoever that it would be preferable to use the organic radical compound in the low amounts required by the present invention. Rather, Aoki affirmatively suggests that larger amounts are preferable. Aoki provides no expectation of successfully achieving the noted properties in the reduced range of the presently recited invention.
In response, Aoki teaches 0.49, 0.10, and 0.49 parts in the examples, falling within the claimed range. Therefore, the recited resin composition capable of producing a cured product having low dielectric properties, high Tg, and low coefficient of thermal expansion, while also exhibiting excellent moldability, are expected from Aoki in view of Cao. Even though Aoki teaches some examples that fall outside the claimed range, Applicant did not establish criticality of the claimed range with unexpected results. See MPEP2144.05.III.
Applicant argued that in these Examples 14, 15, and 18 relied upon by the Examiner, the free radical compound used (Organic Radical Compound 1) is TEMPO, which corresponds to Free Radical Compound 3 used in the Examples of the present specification. As discussed above, compositions containing Free Radical Compound 3 exhibit lower Tg and somewhat higher coefficients of thermal expansion than compositions containing other free radical compounds (Examples 1, 2, and 4).
In response, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). The 103 rejection is not based on Aoki alone, but rather based on Aoki in view of Cao, which teaches BTEMPO. The examiner has already established that TEMPO and BTEMPO are equivalents. It would have been obvious to one of ordinary skill in the art at the time of filing to use 0.49, 0.10, and 0.49 parts of BTEMPO in the prior art composition.
Applicant argued that regarding the combination of Tochihira, Dershem, and Cao, the cited paragraph merely states that the free radical compound may be included in an amount of 100- 2000 ppm relative to the total base resin. Further, the Examples of Dershem do not confirm any effect achieved by using free radical compound such as BTEMPO. Therefore, Applicant respectfully submits that the same arguments discussed above with respect to the combination of Aoki and Cao are reasonably applied against the combination involving Dershem. Applicant respectfully concludes that the presently claimed invention would not have been obvious from the cited references, alone or in combination.
In response, 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]. The base resin is a thermosetting resin including vinyl ethers, styrenic compounds, allyl functional compounds and the like [0034]. Therefore, Dershem's total base resin corresponds to Toshihira's component (C) that is a thermoplastic elastomer and component (A) a vinyl compound. This 100 to 2000 ppm 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.
Applicant argued that Cao merely states that, in the radical polymerization of styrene, polymerization mediated by BTEMPO is uncontrolled and identical to conventional radical emulsion polymerization. Concretely, Cao does not state that BTEMPO is equivalent to TEMPO. Rather, unlike TEMPO or ATEMPO, BTEMPO is unacceptable as prior art. Indeed, a closer review of Cao shows that BTEMPO does not exhibit the favorable nitroxide-mediated polymerization behavior demonstrated by TEMPO or ATEMPO in emulsion polymerization, as evidenced by the experimental results and tables.
In response, the data in Table I of Cao indicates the difference between BTEMPO and other TEMPO derivatives in living radical polymerization in the presence of nitroxides. Cao concluded that BTEMPO performs differently from the other TEMPO derivatives in living radical polymerization, but BTEMPO behaves identical to TEMPO in a conventional polymerization without nitroxides [abstract, P79 first para.]. Applicant’s examples are conventional polymerization without nitroxides. Therefore, BTEMPO is expected to perform identical to TEMPO.
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) 1-5 and 7-8 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]. Cao teaches that BTEMPO performs identically to TEMPO in a conventional radical polymerization [abstract and P79 first para.]. 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.
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. The examiner has already established that TEMPO and BTEMPO are equivalents as stated above. It would have been obvious to one of ordinary skill in the art at the time of filing to use 0.01 part to 0.2 part of BTEMPO in Aoki’s composition.
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 7-8 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.
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. The examiner has already established that TEMPO and BTEMPO are equivalents as stated above. It would have been obvious to one of ordinary skill in the art at the time of filing to use 0.01 part to 0.2 part of BTEMPO in Toshihira’s composition.
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
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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