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 .
Response to Amendment
Applicant’s claim amendments and remarks filed June 10, 2026 are entered and have
been fully considered. Claims 3 and 4 have been amended to overcome the objection and 112b rejection, therefore they are withdrawn. Applicant has amended claim 1 and added new claims 17-19, therefore claims 1-19 are now pending.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 5 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 5 fails to include all the limitations of claim 1 from which it depends because it states the at least one terminal group that is not a silyl containing group is optional in line 6 of the claim, but claim 1 has been amended to require the terminal group that is not a silyl containing group.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Boday et al, US20120045955A1.
Regarding claim 1, Boday teaches a resin composition with a curable polymer, abstract. Boday exemplifies a synthesis method of producing the polymer shown in ¶[0032] where a chlorosilane is reacted with a monohydroxyl phenol forming one of the terminal ends, and is then polymerized with another hydroxyl phenol forming the PPO units along the backbone. The other end is further reacted to obtain a (meth)acryloxy terminal group, shown in bottom right column.
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This is an intermediate polymer that is further reacted on page 6, where the silyl terminal group is removed, but this intermediate polymer product reads on the claimed sizing agent bifunctional poly(arylene ether) with a silyl terminal group and one non-silyl terminal group where it comprises (meth)acrylate, and the limitation of a sizing agent is an intended use of the polymer.
Claims 1-2, 4, 9-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yamada et al, CN109694474A (Yamada-1).
Regarding claim 1, Yamada-1 teaches an organosilicon modified polyphenylene ether, ¶¶[0002, 0020]. The PPE has a general formula of formula (2) shown below, page 2 of original document.
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On terminal group is silyl containing, and the other terminal is not silyl containing, the R7 is a hydrocarbon group with a polymerizable reactive group, ¶[0027], where the polymerizable group is acryloxy, methacryloxy, styryl, vinyl or epoxy, ¶[0042].
Specifically in example 1-1, ¶¶[0176-0177], commercial PPO Sabic SA90-100 is reacted with 2-isocyanate ethyl methacrylate and 3-isocyanate propyltrimethoxysilane, producing a PPO with a methacryloxy group on one end and a trimethoxysilyl group on the other end, ¶[0179]. This silyl modified PPO reads on the claimed sizing agent because a sizing agent improves adhesion and compatibility, and Yamada’s resin is an adhesive which is impregnated into glass cloth and sandwiched between copper foils ¶¶[0254-0255] and improves the adhesion between the resin material and the copper foil ¶[0011].
Regarding claims 2, 4, 9, and 17-19, Yamada-1 teaches the silane modified PPO of example 1-1 is combined with a methacryloxy functional PPE, commercial SA9000 from Sabic ¶[0238], in curable compositions which reads on the auxiliary PPO with non-silyl containing terminal functional groups of claims 4, and 17-19. A varnish is formed in example 2-1, by combining the methacryloxy-PPE, the silane modified PPO of example 1-1, curing agents, crosslinkers, and organic resins, ¶[0253].
Regarding claim 10, Yamada-1 teaches that the organic resins in the varnish compositions are polybutadiene (Ricon 156) and styrene-butadiene copolymer (Ricon 100) ¶¶[0243-0244], which are unsaturated polymers.
Regarding claim 11-16, Yamada-1 teaches impregnating glass cloth (reinforcing agent of claim 14 and substrate of claim 12) with the composition, heating and obtaining a prepreg blank ¶[0254]. Then sandwiching the prepreg between copper foils (claim 15) to form a laminate which is then heated and pressurized to form a cured article ¶[0255] (reads on claims 11, 13, and 16).
Claim 17 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yamada et al, JP2018016709 (Yamada-2).
Regarding claim 17, Yamada-2 teaches a composition comprising a polyphenylene ether functionalized with an organosilane ¶¶[0001, 0010]. Where the modified PPE can have structure 1 or 2 shown below, where the silyl containing group is one terminal group, see page 2 of original document.
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Where R3 and R4 are independently a halogen, an alkoxy, alkylthio, or haloalkoxy group with 1-12 carbon atoms, ¶[0010], reads on the PPE being bifunctional, additionally, in formula (2) the hydroxyl terminal group reads on the optional terminal group that is not silyl containing. Furthermore, the silane modified PPE reads on the claimed sizing agent because a sizing agent is a compatibilizer used in composites, and Yamada teaches the resin is used as an adhesive for copper foil, ¶¶[0009, 0011].
The organic resin blended with the silane terminated PPE can be an additional polyphenylene ether resin, ¶[0065]. See example 2-1 ¶[0085], where a commercial PPO, SA90-100 from Sabic which is hydroxyl terminated, is blended with epoxy resin, the silane terminated PPE made in example 1-1 (¶[0067]), and cyanate ester, this forms a thermoset curable composition in the form of a varnish.
Claim Rejections - 35 USC § 103
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 3 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Yamada et al, CN109694474A (Yamada-1).
Regarding claims 3 and 5, Yamada-1 teaches the composition according to claim 1 as explained above. Yamada-1 exemplifies 3-isocyanate propyltrimethoxysilane in the examples ¶[0176] as the modifying silane, but in the broader disclosure, Yamada teaches that the A1 and A2 groups between the silicon and phenyl ring (structure shown below from page 2 of original document) can also represent a single bond for A1 and a divalent hydrocarbon groups without heteroatoms, unsubstituted or substituted with 1-20 carbon atoms for A2, and the R1 and R2 independently represent alkyl groups of 1-10 carbon atoms, ¶[0027], which reads on the silyl containing terminal groups of claims 3 and 5.
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Yamada-1 further teaches the silane modified PPO is combined with a methacryloxy functional PPE, commercial SA9000 from Sabic ¶[0238], in curable compositions which reads on the auxiliary PPO with non-silyl containing terminal functional groups of claim 5.
It is prima facie obvious to substitute one material for another to obtain predictable results when the materials fulfill the same use and function. “[I]t is prima facie obvious to substitute equivalents, motivated by the reasonable expectation that the respective species will behave in a comparable manner or give comparable results in comparable circumstances.” In re Ruff 118 USPQ 343; In re Jezel 158 USPQ 99; “the express suggestion to substitute one equivalent for another need not be present to render the substitution obvious.” In re Font, 213 USPQ 532
Therefore it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have practiced the invention of Yamada-1 substituting the 3-isocyanate propyltrimethoxysilane of example 1-1 with a silane that produces the connecting groups A1 and A2 of a single bond and a 1-20 carbon hydrocarbon group with the motivation of producing another permutation of a silane modified PPO used in thermoset adhesive compositions for copper foil laminates as taught by Yamada-1.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Tsukahara et al, JPH05163344A.
Regarding claim 17, Tsukahara teaches a composition comprising a silyl modified polyphenylene ether which is made from reacting an alkenyl functional polyphenylene ether with a silane of formula (I) , ¶[0005]. In example 1, ¶[0037], an alkenyl functional PPE is reacted with trimethoxysilane, ¶[0037], where 100% of the allyl groups have reacted. This silyl-modified PPE reads on the poly(arylene ether) of claim 17. The silyl modified PPE reads on the claimed sizing agent because a sizing agent is also known as a compatibilizer, and Tsukahara teaches the modified PPE is useful as a compatibilizer for polymer alloys, adhesives ¶¶[0001, 0024, 0043].
Tsukahara does not explicitly teach mixing an auxiliary PPE resin with the silyl modified PPE resins in the examples, but Tsukahara does teach that the silyl modified PPE is useful as a compatibilizer for polyphenylene ethers, ¶[0001]. Although it is mentioned generally and the functionality is not specified, it would be obvious to the skilled artisan that the additional PPE would have some functionality different from the silyl group, and PPE with hydroxyl functionality is well known in the fields of applications that Tsukahara lists in ¶[0001]. Therefore the suggestion of using the silyl modified PPE as a compatibilizer for PPE renders obvious the auxiliary PPE resin with functional groups that are not the silyl containing groups.
Allowable Subject Matter
Claims 7-8 are allowable for reasons given in the previous office action dated 5/14/2026 where Tsukahara and Yamada-2 are concerned.
Claim 6 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: Yamada-1 does not teach or suggest the method of making the bifunctional PPE by polymerizing a monohydric phenol with an alkenyl monohydric phenol and then reacting the sizing agent precursor with the silyl containing compound. In ¶[0177] and the subsequent examples, the PPE is made by reacting hydroxyl bifunctional PPE SA90-100 polymer with phenol 3,5-tert-butyl-4-hydroxytoluene and then functionalizing with 2-isocyanate ethyl methacrylate and then the isocyanato silane to add the silyl terminal group in example 1-1. Or Yamada-1 teaches reacting the SA90-100 with 3,5-tert-butyl-4-hydroxytoluene and then allyl bromide in example 1-9, ¶[0211], which is then reacted with more 3,5-tert-butyl-4-hydroxytoluene and the isocyanato silane. Yamada-1 also does not teach the methods of claims 7 and 8 because the PPE is not redistributed and does not use an alkenyl monohydric phenol compound.
Response to Arguments
In light of the amended claim 1, the previous rejections under 102 anticipated by Tsukahara, Zhang, and Yamada-2 and under 103 over Tsukarahara, and over Zhang are withdrawn because they no longer read on the claims 1-6, 9-16. Applicant’s arguments are regarding the previous rejections of 1-6, and 9-16 and their application to the amended claims, consequently they are now moot.
New claim 17, which is a combination of original claims 1 and 2, is rejected under 102 as being anticipated by Yamada et al, JP2018016709 (now referred to as Yamada-2) and under 103 over Tsukahara because they were previously applied to original claims 1 and 2.
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.
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/V.L.S./Examiner, Art Unit 1766
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765
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