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 .
Claim 13 is pending as amended on July 31, 2025. Support for amended claim 13 is partially found in specification [0070], [0083], [0084], and [0085].
Claims 1-12 and 14-18 stand withdrawn from consideration.
The new grounds of rejection set forth below were necessitated by the amendment of claim 13 further limiting the maleimide resin structure and including a silane coupling agent. Therefore, this action is properly made final.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in the action can be found in a prior Office action.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claim 13 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 13 has been amended to recite the limitation “X is an aromatic divalent hydrocarbon group” in line 23. Specification [0085] describes X as “X is an aliphatic or aromatic divalent hydrocarbon group containing 1 to 30 carbon atoms or a single bond.” This does not support amended claim 13 because amended claim 13 encompasses species where X is an aromatic divalent hydrocarbon group with more than 30 carbon atoms. Because claim 13 as presently drafted is not commensurate in scope with the support provided in [0085], the written description requirement of 35 USC 112(a) has not been complied with. This is a new matter rejection.
Response to Arguments
Applicant’s arguments filed July 31, 2025 have been fully considered.
In view of the amendments to the claims, the rejections as they were previously set forth has been overcome. Amended claim 13 overcomes the rejection over Hitoshi (JP-2010229274-A) in view of Nakamura (JP-2017186551-A) and Torii (US 2019/0276585 A1) by narrowing the structure of the maleimide resin and including a silane coupling agent. However, claim 13 is not allowable because a new ground of rejection is made over Hitoshi (JP-2010229274-A) in view of Nakamura (JP-2017186551-A), Torii (US 2019/0276585 A1), and Watanabe (JP-2019108557-A).
Applicant argues (page 12) that Hitoshi in view of Nakamura does not disclose or suggest the combination of components of the present invention or the relationship between the combination and technical effects realized thereby. In particular, Hitoshi in view of Nakamura does not teach the claimed silane coupling agent or suggest that the silane coupling agent improves copper foil adhesive strength while maintaining a low dielectric constant. In this case, the examiner agrees that Hitoshi in view of Nakamura and Torii does not teach the claimed silane coupling agent and the original rejection over Hitoshi in view of Nakamura and Torii has been withdrawn. However, a new rejection has been made over Hitoshi in view of Nakamura, Torii, and Watanabe.
Watanabe teaches a resin composition for adhesive films (Watanabe, [0065]). Similar to Hitoshi, the composition of Watanabe comprises OPE-2st resins (Watanabe, [0019]), polyimide resins (Watanabe, [0035]), maleimide compounds (Watanabe, [0058]), and inorganic fillers such as alumina, silica, boron nitride, barium titanate, strontium titanate, aluminum hydroxide, and magnesium hydroxide (Watanabe, [0039]). Watanabe further teaches that the filler is preferably surface-treated with a surface treatment agent to improve moisture resistance and dispersibility (Watanabe, [0042]). Watanabe teaches that surface treatment with a styrylsilane-based coupling agent, such as p-styryl trimethoxysilane, is preferable because it is excellent in lowering the dielectric loss tangent (Watanabe, [0043]). The rejection under 35 USC § 103 laid out below relies upon modifying Hitoshi by substituting the filler of Hitoshi for the filler treated with p-styryl trimethoxysilane of Watanabe, leading to a cured film reading on claim 13.
The MPEP section 2144, subsection IV states, “The reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. See, e.g., In re Kahn, 441 F.3d 977, 987, 78 USPQ2d 1329, 1336 (Fed. Cir. 2006).” Consequently, a teaching of the technical effect of improved adhesion while maintaining a low dielectric constant is not required to provide motivation for the combination if Watanabe teaches a different motivation. In this case, Wantanabe teaches that fillers treated with p-styryl trimethoxysilane have the advantages of improving moisture resistance and dispersibility as well as lowering the dielectric loss tangent. Therefore, one of ordinary skill in the art would have had motivation to substitute the filler of Hitoshi for the filler treated with p-styryl trimethoxysilane of Watanabe.
Claim Rejections - 35 USC § 103
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Hitoshi (JP-2010229274-A, English translation provided with 2/28/2025 Office action) in view of Nakamura (JP-2017186551-A, Cite No. 8 on 3/02/2022 IDS, English translation provided with 5/08/2025 Office action), Torii (US 2019/0276585 A1), and Watanabe (JP-2019108557-A, English translation provided).
Hitoshi teaches a cured film produced by curing a thermosetting resin composition (The resin composition… may be used in the form of a film. Thereafter, by heating at about 180°C for several hours, the resin composition of the present invention can be obtained, Hitoshi, [0074]; the resin composition film was heated at 180°C for 2 hours to obtain a resin composition film, Hitoshi, [0099]). Hitoshi teaches that the resin composition contains at least (A) an elastomer selected from polyimide, (B) a compound having a maleimide group, and (C) a compound having a vinylbenzyl group (Hitoshi, [0007]). The compound having a vinylbenzyl group is exemplified by a commercially available phenyleneether oligomer (Hitoshi, [0091]). Hitoshi therefore teaches a thermosetting resin composition comprising the components of (A1), (B), and (C): a polyimide resin (A1), a phenylene ether resin (B), and a maleimide resin (C).
Hitoshi teaches a polyimide resin as component (A1), but Hitoshi does not teach a polyimide resin containing a diamine residue as represented by the formula (8) and/or the formula (9).
However, Nakamura teaches a polyimide that exhibits a high storage modulus of rigidity under B-stage temperature conditions (Nakamura, [0014]). Nakamura further teaches that the polyimide and a film-like adhesive obtained are particularly suitable for use in high-frequency printed wiring board because the adhesive is less likely to ooze out or flow out the B-stage and has good heat-resistant adhesion and low dielectric characteristics (Nakamura, [0014]). B-stage temperature is about 180°C (Nakamura, [0007]).
The polyimide of Nakamura contains diamine residues represented by chemical formulae 4-9 shown below (The polyimide of the present invention is a polyimide comprising… diamine containing dimer diamine (b1), Nakamura, [0016]; A non-limiting structural formula of the dimer diamine is shown below, Nakamura, [0019]):
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454
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Wherein m+n=6 to 17, p+q=8 to 19, and a broken line portion means a carbon-carbon single bond or a carbon-carbon double bond (Nakamura, [0019]).
Nakamura formulae 4-7 read on a polyimide resin containing a diamine residue represented by instant formula (8):
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wherein in the formula (8), a (Nakamura n), b (Nakamura m), c (Nakamura p), and d (Nakamura q) are each an integer and satisfy the relations of a + b = 6 to 17, c + d = 8 to 19, and each broken line represents either a carbon- carbon single bond (bonds indicated by 1-7 above) or a carbon-carbon double bond (bonds indicated by 2, 3, and 6 above).
Nakamura formulae 8-9 read on a polyimide resin containing a diamine residue represented by instant formula (9):
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wherein in the formula (9), e (Nakamura m-1), f (Nakamura n), g (Nakamura p), and h (Nakamura q) are each an integer and satisfy the relations of e +f = 5 to 16 (subtracting 1 from range of Nakamura because e corresponds to Nakamura m-1), g + h = 8 to 19, and each broken line represents either a carbon- carbon single bond or a carbon-carbon double bond.
In order to satisfy a + b = 6 to 17, a and b can be in the range of 0 to 17, overlapping the claimed range of 1 or higher. In order to satisfy c + d = 8 to 19, c and d can be in the range of 0 to 19, overlapping with the claimed range of 1 or higher. Similarly, in order to satisfy e +f = 5 to 16, e and f can be 0 to 16, overlapping with the claimed range of 1 or higher. In order to satisfy g + h = 8 to 19, g and h can be 0 to 19, overlapping with the claimed range of 1 or higher. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the polyimide of Hitoshi for the polyimide of Nakamura. One would have been motivated to make this substitution because the polyimide of Nakamura exhibits a high storage modulus of rigidity under B-stage temperature conditions and is suitable for high-frequency printed wiring board applications (Nakamura, [0014]).
With respect to the phenylene ether resin (B), Hitoshi exemplifies a commercially available phenylene ether oligomer “OPE 2ST” manufactured by Mitsubishi Chemical Corporation as a compound having a terminal vinylbenzyl group (Hitoshi, [0091]). A phenylene ether oligomer with a terminal vinylbenzyl group reads on a phenylene ether resin having a least one crosslinkable functional group consisting of vinyl group located at a molecular chain end.
Hitoshi is silent as to the phenylene ether resin molecular weight.
However, Torii teaches a resin composition that can provide a product of low dielectric tangent, high mechanical strength, and high adhesiveness (Torii, Abstract). The composition of Torii comprises “OPE-2St-1200” manufactured by Mitsubishi Gas Chemical Company as a polyphenylene ether resin (Torii, [0101]). Torii further teaches that “OPE-2St-1200” has a number average molecular weight of 1200 (Torri, [0101]) and that a number average molecular weight in the range of 200 to 3,000 can inhibit volatilization during drying and inhibit the melt viscosity of the resin composition from excessively increasing (Torii, [0102]).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have substituted the “OPE 2ST” with unspecified molecular weight of Hitoshi for the “OPE-2St-1200” with a number average molecular weight of 1,200 of Torii. One would have been motivated to make this substitution in order to select a molecular weight appropriate for inhibiting volatilization during drying and preventing the melt viscosity of the resin composition from excessively increasing. A phenylene ether resin having a number average molecular weight of 1200 falls within the claimed range of 500 or more and 5,000 or less.
With respect to the maleimide resin (C), Hitoshi teaches that the resin composition contains a compound having a maleimide group (Hitoshi, [0007]). As an example of a specific compound having a maleimide group, Hitoshi teaches an oligomer of phenylmethane maleimide represented by formula 12 below (Hitoshi, [0042-0043]):
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where n12 indicates a natural number. This compound reads on polymaleimide resin molecules having N maleimide groups where N corresponds to Hitoshi n12+2. Given that Hitoshi teaches that formula 12 represents an oligomer and n12 indicates a natural number, Hitoshi teaches N is at least 2. This overlaps with the claimed range of each N is an integer number and the average of N’s is larger than 2 and smaller than 30. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Hitoshi teaches that the resin composition may further contain a filler (Hitoshi, [0069]). The fillers of Hitoshi include alumina, silica, boron nitride, barium titanate, strontium titanate, aluminum hydroxide, and magnesium hydroxide (Hitoshi, [0070]). Hitoshi does not teach a silane coupling agent.
However, Watanabe teaches a resin composition for adhesive films (Watanabe, [0065]). Similar to Hitoshi, the composition of Watanabe comprises OPE-2st resins (Watanabe, [0019]), polyimide resins (Watanabe, [0035]), maleimide compounds (Watanabe, [0058]), and inorganic fillers such as alumina, silica, boron nitride, barium titanate, strontium titanate, aluminum hydroxide, and magnesium hydroxide (Watanabe, [0039]). Watanabe further teaches that the filler is preferably surface-treated with a surface treatment agent to improve moisture resistance and dispersibility (Watanabe, [0042]). Watanabe teaches that surface treatment with a styrylsilane-based coupling agent, such as p-styryl trimethoxysilane, is preferable because it is excellent in lowering the dielectric loss tangent (Watanabe, [0043]).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the filler of Hitoshi for the filler treated with p-styryl trimethoxysilane of Watanabe. One would have been motivated to make this substitution in order to improve moisture resistance and dispersibility as well as lower the dielectric loss tangent. Substituting the filler of Hitoshi for the p-styryl trimethoxysilane treated filler of Watanabe in the composition of modified Hitoshi results in a cured film that reads on a film produced by curing a thermosetting resin comprising a silane coupling agent (F)(p-styryl trimethoxysilane) reading on formula (12):
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Wherein in formula (12), X is an aromatic divalent hydrocarbon group (aromatic ring with 6 carbon atoms); the R13 groups are identical each other and are each an alkoxy group containing 1 carbon atom; i is 1; and 3 of the R13 groups are an alkoxy group containing 1 carbon atom.
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 AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766