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 .
The amendment filed 8/13/2026 has been entered. Claim 3 has been canceled. Claims 1-2 and 4-18 are 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 § 103
Claims 1-2 and 4-18 are rejected under 35 U.S.C. 103 as being unpatentable over Tohjima (WO2021/100658A1, also published as US2023/0002547A1, which again is being utilized as an English language equivalent for the WO document for the below cited sections) for generally the reasons recited in the prior office action and restated below with respect to the amended claims, wherein it is further noted that in addition to the two maleimide resins specifically referenced in the prior office action, Tohjima also teaches other suitable maleimide resins that read upon the claimed maleimide compound (A) as recited in amended claim 1, and given that one having ordinary skill in the art before the effective filing date of the claimed invention would have been motivated to select from any of the maleimide resins taught by Tohjima, the Examiner takes the position that absent any clear showing of criticality and/or unexpected results with respect to the amended maleimide group equivalent range of 200-300 g/mol, the claimed invention as amended would (still) have been obvious over the teachings of Tohjima given that it is prima facie obviousness to simply substitute one known element for another to obtain predictable results and/or prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success.
As discussed in the prior office action, Tohjima teaches a compound of formula (1) as shown below and described in Paragraphs 0011-0014 (encompassing the instantly claimed Formula (2) as recited in amended claim 1) as well as a curable resin composition containing the compound of formula (1) (Paragraph 0014) and a cured product thereof having low dielectric properties and useful for producing a printed wiring substrate, a build-up laminated board, and glass fiber reinforced plastics substrate (Paragraphs 0001 and 0018).
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(1)
Tohjima specifically teaches exemplified compounds of formula (1) in the working examples that read upon the instantly claimed hydrocarbon-based compound (B) represented by the instantly claimed Formula (2) of amended claim 1, including Example 2 which results in the below compound with n = 1.7; Example 4 which produces the below compound with n = 2.6; and Example 10 which produces the below compound with n = 1.9.
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Example 2
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Example 10
Tohjima also teaches that the curable resin composition may contain any known material as a curable resin other than the compound represented by the formula (1), with examples of the (other) curable resin including a phenol resin such as any known polyphenylene ether (PPE) compound (as in instant claim 6), an epoxy resin (as in instant claim 6), an amine resin, an active alkene-containing resin, and a cyanate ester resin (as in instant claim 6); using one kind of these resins or a plurality thereof in combination (Paragraphs 0061, 0069, and 0072-0073), with specific examples of the active alkene-containing resin including maleimide compounds as recited in Paragraph 0081 including 4,4′-diphenylmethanebismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 179 g/mol) and m-phenylenebismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 134.11 g/mol) as noted in the prior office action, as well as polyphenylmethanemaleimide (i.e., a maleimide compound having a benzene ring in a molecule), 2,2′-bis[4-(4-maleimide phenoxy) phenyl] propane (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 285.3 g/mol as in amended claim 1 and a benzene ring equivalent of 200 g/mol or less as in instant claim 2), 3,3′-dimethyl-5,5′-diethyl-4,4′-diphenylmethane bismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 221.3 g/mol as in amended claim 1), 4-methyl-1,3-phenylenebismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 141.13 g/mol), 4,4′-diphenylether bismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 179 g/mol), 4,4′-diphenylsulfonebismaleimide (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 204.19 g/mol as in amended claim 1), 1,3-bis(3-maleimidephenoxy) benzene (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 226.2 g/mol as in amended claim 1 and a benzene ring equivalent of 200 g/mol or less as in instant claim 2), and 1,3-bis(4-maleimidephenoxy) benzene (i.e., a maleimide compound having a benzene ring in a molecule and having a calculated maleimide group equivalent of about 226.2 g/mol as in amended claim 1 and a benzene ring equivalent of 200 g/mol or less as in instant claim 2) as recited in Paragraph 0081.
Tohjima teaches that the usage amount of the (other) curable resin is preferably 10 times by mass or less, more preferably 5 times by mass or less, and particularly preferably 3 times by mass or less relative to the usage amount of the compound represented by the formula (1), and a lower limit of preferably 0.5 times by mass or more, and more preferably 1 time by mass or more (Paragraph 0070), wherein preferably the content of the PPE compound (e.g., “a reactive compound (C) that reacts with at least one of the maleimide compound (A) or the hydrocarbon-based compound (B)” as in instant claim 5 and more particularly “a polyphenylene ether compound” as in instant claim 6) is 10 to 90 mass %, and more preferably 20 to 80 mass%, based on the total mass of the curable resin components (Paragraph 0078, wherein when utilized in combination with any of the maleimide compounds of Paragraph 0081 reading upon the claimed maleimide compound (A) as taught by Tohjima, the amounts taught by Tohjima overlap and thus render obvious the claimed mass contents as recited in instant claims 4 and 7-8). Hence, given that Tohjima specifically teaches exemplified compounds reading upon the instantly claimed hydrocarbon-based compound (B) as represented by the claimed Formula (2) of amended claim 1, and clearly teaches that said compounds can be mixed with maleimide compounds reading upon the claimed maleimide compound (A), (A-1), and/or (A-2) as recited in amended claims 1-2, and preferably a curable PPE compound as in instant claims 5-6, in amounts as in instant claims 4 and 7-8, to form a curable resin composition, the Examiner maintains her position that the instantly claimed invention as recited in instant claims 1-2 and 4-8 would have been obvious over the teachings of Tohjima given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success.
With respect to instant claim 9, Tohjima teaches that inorganic fillers may be added to the curable resin composition, if necessary, thereby rendering instant claim 9 obvious over the teachings of Tohjima (Paragraph 0098).
With respect to instant claim 10, Tohjima teaches that the curable resin composition may contain a phosphorus-containing compound as a flame retardation-imparting component, thereby rendering instant claim 10 obvious over the teachings of Tohjima (Paragraph 0095).
With respect to instant claim 11, although Tohjima does not specifically teach that “a cured product of the resin composition” has a ratio of storage modulus properties as instantly claimed, given that the claimed limitation is based upon the “cured” composition and that the curable resin composition taught by Tohjima is capable of providing said storage modulus properties, particularly given that Tohjima teaches and/or suggests the same components and in contents as instantly claimed such that it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to reasonably expect similar properties and/or to utilize routine experimentation to determine the optimum content of each curable component to provide the desired properties for a particular end use, the Examiner takes the position that absent any clear showing of criticality and/or unexpected results, the claimed invention as recited in instant claim 11 would have been obvious over the teachings of Tohjima.
With respect to instant claims 12-18, Tohjima teaches that the curable resin composition may be utilized to produce a prepreg by impregnating the curable composition into a fibrous base material as in instant claim 12 (also reading upon the broadly claimed support film of instant claim 13) and cured product thereof; and can also be used to produce a film that can be used as an interlayer insulating layer in a multilayer substrate by coating on a release film as a “support” film as in instant claim 13 and performing B-stage formation to produce a sheet-shaped adhesive layer (Paragraphs 0105-0107), thereby reading upon the claimed prepreg and film as recited in instant claims 12 and 13, respectively. Further, with respect to instant claims 14-18, Tohjima teaches that the curable resin composition which produces a “cured product thereof has excellent properties in high heat resistance and low dielectric properties” (Paragraph 0018) can be utilized as an insulating material for electric or electronic compounds (Paragraph 0149), or as an insulating layer in a multilayer substrate as noted above; and also teaches that one or more of the prepregs can be utilized to produce a laminated board that can be used as a metal foil-clad laminated board by laminating with a layer made of a metal foil, such as a copper foil; and given that Tohjima also teaches that the laminated board may be utilized for an electric and electronic device, particularly as a printed wiring board (Entire document, particularly Paragraphs 0101, 0105-0110), the claimed invention as recited in instant claims 12-18 would have been obvious over the teachings of Tohjima.
Claims 1-2 and 4-18 are rejected under 35 U.S.C. 103 as being unpatentable over Tohjima, as applied above and in further view of Sugiyama (WO2020/004211A1, please refer to the attached machine translation for the below cited sections). The teachings of Tohjima are discussed in detail above, and incorporated herein by reference, wherein it is again noted that Tohjima clearly teaches that the resin composition may comprise a maleimide resin reading upon the claimed maleimide compound (A) as recited in amended claims 1-2, in combination with the compound of formula (1) reading upon the claimed hydrocarbon-based compound (B) represented by the claimed Formula (2), and may further comprise a PPE compound, an epoxy resin, an amine resin, and/or a cyanate ester resin as discussed above, and although Tohjima specifically recites exemplified maleimide resins having a maleimide group equivalent within the claimed range of 200 g/mol or more and 300 g/mol or less as recited in amended claim 1, Tohjima does not specifically limit the maleimide resin to one having a maleimide group equivalent within the instantly claimed range. However, Sugiyama teaches a similar resin composition that exhibits a variety of excellent properties such as excellent heat resistance and excellent electrical characteristics, as well as a prepreg, a metal foil-clad laminate, a resin sheet, and a printed wiring board produced therefrom (Abstract, Paragraph 0001), e.g., as in Tohjima, wherein the resin composition taught by Sugiyama contains a cyanate ester compound (A) (e.g., similar to the other curable resin taught by Tohjima); a bismaleimide compound (B) that is specifically represented by formula (1) (Abstract), which tends to improve the electrical properties and heat resistance of the resin composition (Paragraph 0015), alone or in combination with other bismaleimide compound(s) other than bismaleimide compound (B) (Paragraph 0022), e.g., similar to the non-limiting bismaleimide compound(s) taught by Tohjima; and one or more other resin components such as epoxy resins, phenolic resins, compounds having polymerizable groups (e.g., the compound of formula 1 of Tohjima), modified polyphenylene ethers terminally modified by substituents containing carbon-carbon unsaturated double bonds, elastomers, and active ester compounds (e.g., similar to the other curable resins as taught by Tohjima) to further enhance properties of the resin composition (Paragraph 0022). Sugiyama specifically teaches that the equivalent amount of unsaturated imide groups (e.g., maleimide group equivalent) in the bismaleimide compound of formula (1) as well as the equivalent amount of unsaturated imide groups in the other maleimide compound(s) that may be utilized in the resin composition such as 4-methyl-1,3-phenylenebismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyletherbismaleimide, 4,4'-diphenylsulfonebismaleimide, 1,3-bis(3-maleimidophenoxy) benzene, 1,3-bis(4-maleimidophenoxy)benzene, and polyphenylmethanemaleimide (e.g., same as those recited by Tohjima), is preferably 200 g/eq or more, and preferably 400 g/eq or less, wherein when a plurality of other maleimide compounds are contained, the weighted average unsaturated imide group equivalent is taken into consideration of the mass of each other maleimide compound contained in the resin composition (Paragraphs 0018 and 0027-0028), with working examples specifically utilizing bismaleimide compounds having a maleimide equivalent within the claimed range of 200 to 300 g/mol as recited in amended claim 1, with the copper laminates of working Examples 3 and 4 having good properties including low dielectric (Dk and Df) properties, a high Tg and low heat loss (Examples). Hence, given that Sugiyama is of the same field of endeavor as Tohjima, with both concerned with heat resistance and electrical properties of the resin composition, and that Tohjima does not specifically limit the maleimide compound that may be incorporated into the resin composition, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to utilize the maleimide compound(s) taught by Sugiyama, particularly as in the working examples, in the resin composition taught by Tohjima given that it is prima facie obviousness to simply substitute one known element for another to obtain predictable results and/or prima facie obviousness to use a known technique to improve similar devices in the same way, thereby reading upon and/or rendering obvious the claimed invention as recited in instant claims 1-2 and 4-18 over the teachings of Tohjima and in further view of Sugiyama.
Double Patenting
Claims 1-2 and 4-18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 3-18 of copending Application No. 18/561065 (reference application, printed as US2024/0270885A1) for generally the reasons recited in the prior office action and restated below with respect to the amended claims in both applications. Although the claims at issue are not identical, they are not patentably distinct from each other because copending claim 1 is similarly directed to a resin composition comprising a maleimide compound (A) and a hydrocarbon-based compound (B) of the Chemical Formula (1) that encompasses the claimed Formula (2) as recited in amended claim 1, and given that the maleimide compound (A) of copending claim 1 has an indane structure which includes a benzene ring in a molecule thereof, the only difference between copending claim 1 and instant claim 1 is that copending claim 1 does not specifically recite that the maleimide compound (A) has a maleimide group equivalent of 200-300 g/mol. However, given the equivalent weight of a basic indane structure, and more particularly the equivalent weights of the maleimide compound (A1) represented by Chemical formula (3) as recited in copending claim 3, reading upon and/or overlapping the equivalent weights of instant claims 1-2 and hence rendering the claimed equivalent weights obvious to one skilled in the art, the Examiner maintains her position that absent any clear showing of criticality and/or unexpected results, the claimed invention as recited in amended claims 1-2 would have been obvious over copending claim 1, or alternatively, copending claim 3, given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success.
With respect to instant claims 4-10 and 12-18, copending claims 5-11 and 12-18, respectively, recite all of the limitations thereof, and hence instant claims 4-10 and 12-18 would have been obvious over copending claims 5-11 and 12-18, respectively. With respect to instant claim 11, given that the claimed limitation is based upon a cured product of the resin composition and that the resin composition of copending claim 1 comprises the same components as in instant claim 1 from which instant claim 11 depends, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to reasonably expect the resin composition of copending claim 1 to be capable of providing similar properties wherein one skilled in the art would have been motivated to determine the optimum content of each component to provide the desired properties for a particular end use. Hence, absent any clear showing of criticality and/or unexpected results, instant claim 11 would have been obvious over copending claim 1, or copending claim 5 which recites parts by mass with respect to (A) and (B).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-2 and 4-11 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 7, and 9-11 of copending Application No. 18/561591 (printed as US2024/0263003A1) in view of Sugiyama. Copending claim 1, as amended, is directed to a resin composition comprising a hydrocarbon-based compound (A1) represented by the same Formula (2) as recited in amended claim 1, a styrenic polymer (B) different from (A1), and a reactive compound (C) that reacts with at least one of the hydrocarbon-based compound (A1) or the styrenic polymer (B) (similar to instant claim 5), and although copending claim 7 recites that the reactive compound (C) includes at least one selected from a group that includes a bismaleimide as well as other reactive compounds as recited in instant claims 5-6, copending claim 1 or copending claim 7 does not recite that the resin composition includes a maleimide compound having a benzene ring in a molecule and having a maleimide group equivalent of 200-300 g/mol as recited in amended claim 1. However, given that such maleimide compounds are known to be utilized in the art with similar reactive compounds as recited in copending claim 1 or copending claim 7, in place of and/or with a styrene-based copolymer (as in copending claim 1) as evidenced by Sugiyama (Entire document, particularly Abstract, Paragraphs 0001, 0007, 0014-0018, 0022-0028, 0038, and 0057), the claimed invention as recited in instant claims 1-2 as well as 5-6 would have been obvious over copending claim 1 or copending claim 7 in view of Sugiyama given that it is prima facie obviousness to simply substitute one known element for another to obtain predictable results and/or prima facie obviousness to combine prior art elements according to known methods to yield predictable results. With respect to instant claims 4 and 8, and instant claim 7, copending claims 5 and 9 recite similar parts by mass for the hydrocarbon-based compound and the reactive compound(s), respectively, and given that one having ordinary skill in the art before the effective filing date of the claimed invention would have been motivated to utilize any amount(s) within the ranges of the copending claims or as typical in the art as evidenced by Sugiyama, the Examiner takes the position that absent any clear showing of criticality and/or unexpected results, instant claims 4 and 8, and instant claim 7 would have been obvious over copending claims 5 and 9, respectively, in view of Sugiyama. With respect to instant claims 9-10, copending claims 10-11, respectively, recite the same limitations thereof, and hence, instant claims 9-10 would have been obvious over copending claims 10-11 in view of Sugiyama. Further, with respect to instant claim 11, given that the claimed limitation is based upon a cured product of the resin composition and that the resin composition of copending claim 1 or copending claim 7 in view of Sugiyama comprises the same components as in instant claim 1 as amended, from which instant claim 11 depends, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to reasonably expect the resin composition of copending claim 1 or copending claim 7 in view of Sugiyama to be capable of providing similar properties wherein one skilled in the art would have been motivated to determine the optimum content of each component to provide the desired properties for a particular end use. Hence, absent any clear showing of criticality and/unexpected results, instant claim 11 would have been obvious over copending claim 1 or copending claim 7 in view of Sugiyama.
This is a provisional nonstatutory double patenting rejection.
Response to Arguments
Applicant's arguments filed 8/13/2026 have been fully considered but they are not persuasive and/or moot in view of the additional remarks with respect to the teachings of Tohjima and/or the new grounds of rejection presented above in further view of Sugiyama. More specifically, the Applicant argues that although Tohjima lists several examples of maleimide compounds in Paragraph 0081, “the reference [allegedly] contains absolutely no teaching or suggestion to select a maleimide compound having a maleimide group equivalent of 200-300 g/mol, nor does it suggest that selecting such a compound would provide any particular technical advantage” (see page 9, last paragraph). However, the Examiner respectfully disagrees given that Tohjima clearly recites maleimide compounds in Paragraph 0081 that have a maleimide group equivalent within the amended range as discussed in detail above, and given that Tohjima clearly teaches that any of the exemplified maleimide compounds may be utilized, Tohjima does provide a teaching and/or suggestion to select a maleimide compound having a maleimide group equivalent of 200-300 g/mol as instantly claimed, especially given that it is prima facie obviousness to choose from a finite number of identified, predictable solutions, with a reasonable expectation of success. The Applicant also argues that with respect to the technical problem described by Tohjima, e.g., versus the properties achieved by the present invention, “Tohjima contains neither disclosure nor prompting regarding rigidity achieved by the present invention, namely, that the cured product exhibits a ratio of storage modulus Z2/Z1 of 0.7 or more, where Z1 denotes a storage modulus at 25°C and Z2 denotes the storage modulus at 260°C in dynamic viscoelastic measurement” (see page 10, second paragraph). However, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). Hence, given that Tohjima clearly teaches all of the components as utilized in the instantly claimed resin composition, and/or that Tohjima in view of Sugiyama provides a clear teaching and/or suggestion of utilizing a maleimide compound having a maleimide group equivalent as instantly claimed, the Examiner takes the position that absent any clear showing of criticality and/or unexpected results with respect to the instantly claimed invention, particularly with respect to the amended range of 200-300 g/mol, the claimed invention as recited in amended claims 1-2 and 4-18 would have been obvious over the teachings of Tohjima taken alone or in further view of Sugiyama.
With respect to the obviousness-type double patenting rejections, Applicant’s arguments have been fully considered but are not persuasive in view of the amended rejections as presented above with respect to the amended claims over copending Appl. Nos. 18/561065 and 18/561591.
Any objection or rejection from the prior office action not restated above has been withdrawn by the Examiner in light of Applicant’s claim amendments and arguments filed 8/13/2026.
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 MONIQUE R JACKSON whose telephone number is (571)272-1508. The examiner can normally be reached Mondays-Thursdays from 10:00AM-5:00PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Callie Shosho can be reached at 571-272-1123. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MONIQUE R JACKSON/Primary Examiner, Art Unit 1787
Prosecution Insights