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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Response to Amendment
Applicant’s Amendment filed 10/01/2025 has been entered and is being considered. Claim 3 has been canceled and some of its subject matter moved up into now-amended claim 1.
Response to Arguments
Applicant’s Amendments to the claims necessitate the withdrawal of all 35 USC 103 rejections as made in the prior Non-final Rejection furnished, as they have changed the scope of the independent claim so as to negate the references used.
Applicant’s Arguments directed to superior unexpected results are appreciated, but after consideration are not persuasive. Assertions of unexpected results must be both of statistical and practical significance, and further must be commensurate with the scope of the claims. The Examiner is convinced the assertions are of practical significance as improvements in pattern accuracy and L/S parameter optimization are clearly advantageous. However, the scope of the examples is much narrower than the embodiments encompassed by the claim language - the examples use a single POSS component (B), a single resin component (A) OPE 2st 1200, and a narrow set of 3 components (C) and 2 components (D). The claim language of claims 1 and dependent claims therefrom however are directed to genera of compounds for each of (A)-(D) – it is difficult to say with certainty that the entire scope of the claims would exhibit the alleged superior unexpected results Applicant attests to in their examples when the examples use a narrow range of embodiments. If applicant wishes to narrow the scope of the claims
After further search and consideration, a new grounds of rejection is made over Moxy, Liu, and Wada et al (US2012003437 A1), and additionally over Moxy, Liu, and Wada and further in view of Birsak. Applicant’s amendments have necessitated the new grounds of rejection.
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.
Claim(s) 1, 4-5, and 7-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al (US 20200071477 A1, published 03/05/2020), Moxey et al (US 20180037495 A1), and Wada et al (US 20120003437 A1) .
Regarding Claims 1, 4-5, 7, 8, and 10, Liu teaches a halogen-free low dielectric resin composition comprising a polyphenylene ether that has an unsaturated functional group, a crosslinking agent which has an unsaturated functional group, and a phosphorus compound (Abstract).
Liu teaches a base resin having a polyphenylene ether structure (A) discussed from [0010]-[0021] and [0041]-[0048]:
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Wherein A1 and A2 are a group selected from below:
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X and Y are independently absent, or carbonyl, or alkenyl-containing groups
Subscript m and n are independently an integer from 0-100 so long as both m and n are not 0 at the same time.
Z is absent, aryl, oxo, carbonyl, thiocarbonyl, -(S=O)-, -(SO2)-, or –(CR35R36) where R35 and R36 are independently H or C1-C12 alkyl.
The resin reads upon the claimed polyphenylene ether resin (A) where:
For where X is O, X and Y are absent, R31-R34 are H, A1 and A2 are
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, the resin of Liu reads upon the claimed polymer (1) for where X is an unsubstituted phenyl group; Y represents (2) where R4-R7 are H; m is 1, n is 1, and q is 2.
Liu also teaches a crosslinking agent, wherein a crosslinking agent refers to a component having an unsaturated functional group and being capable of undergoing a crosslinking reaction with the polyphenylene ether resin to form a network structure. Examples of these crosslinking agents include polyfunctional acrylates, polyfunctional styrenes, and others outlined from [0050]-[0062].
Additional components include the phosphorus compound (C) (see [0063]-[0089]), epoxy resin, fillers such as silica and aluminum oxide, polymerization initiators (used to start the curing process when exposed to light as discussed in [0042], discussed to be present in an amount of 0-3 wt% of the non-solvent portions of the composition in [0097]-[0098] - claim 5), and curing agents and accelerators. Further additional components include elastomeric polymers to improve the toughness of the composition, such as acrylonitrile-butadiene-styrene (claims 7 and 8).
The composition is coated onto a substrate and dried to generate a semi-cured prepreg, wherein the prepreg is used to prepare a laminate (a cured product – claim 10).
Liu does not teach a specific embodiment that meets the structural limitations of the claimed compound (B) as delimited by formula (3)
This limitation is met by Moxey.
Moxey teaches a UV-curable coating material comprising an organosilica compounds such as POSS or an oligomeric octahedral silsesquioxane which is functionalized with a UV-curable functional group, at least one UV-curable crosslinker (Abstract).
Moxey’s coating composition comprises an organosilica compound, a cross-linker, a plasticizer, a silicone resin, and a photoinitiator (see [0038]-[0106]). Photoinitiators include phenone-type initiators such as 1-hydroxycyclohexyl phenyl ketone 2-hydroxy-2-methylpropiophenone.
Organosilica compounds contemplated include a methacrylate POSS compound (polyhedral oligomeric siloxane) as shown below:
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The reference ascribes improved heat resistance and mechanical strength in cured products to the presence of the POSS compound, whose chains act like nanoscale reinforcing fibers ([0130]).
Neither Liu nor Moxey teach a photoinitiator that is an oxime ester or an acylphosphine oxide.
This limitation is met by Wada.
Wada discloses a photosensitive composition comprising a polymer obtained from a silsesquioxane (Abstract), wherein the polymer is formed from silsesquioxanes described from [0019]-[0026], [0041]-[0104], wherein the silsesquioxanes may be one of a structure Q-1 through Q-7 described in [0047], having polymerizable groups such as vinyl, acryl, methacryl, alkynyl, and/or a group described in Table 1 at [0086].
Wada’s composition is dissolved in a solvent as described in [0130]-[0131], where a photopolymerization initiator is also present in the composition as described from [0135]-[0209], where photopolymerization initiators described include peroxides, ketone compounds such as phenones, ketoxime ethers, oxime compounds such as oxime esters, and acylphosphine oxide compounds. Liu is concerned with peroxide initiators (Liu [0096]-[0097]) and Moxey discusses ketone/phenone polymerization initiators (Moxey [0081]). Wada discloses the genera of Liu and Moxey alongside acylphosphine oxides and oxime esters – the reference considers these genera to be equivalent for use, and as such these genera are considered art-recognized equivalents. A person of ordinary skill in the art would have found it obvious to use the acylphosphine oxide and/or oxime ester initiators of Wada in addition to or in place of the initiators of Moxey and/or Liu with recognition that art-recognized equivalents are generally expected to behave similarly and without detriment. Wada discloses the mass of the photoinitiators may be present in the composition at 1-40 mass%.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by combining the taught composition of Liu with the POSS compound of Moxey and the acylphosphine oxide and/or oxime ester initiators of Wada, such incorporation allowing the provision of a composition for a cured product having improved heat resistance and mechanical strength imparted by the POSS compound.
Regarding Claim 4, Liu teaches the limitations of the claim as discussed above regarding claim 1, but fails to teach the compound (B) as delimited by the claim.
This limitation is met by Moxey as discussed above regarding claim 1 and for brevity will not be reproduced here. The limitation of the ratio discussed by the body of the claim is not discussed by Liu either, but the general weight% incorporation of various components are discussed by both Lie and Moxey.
Liu discloses that the polyphenylene ether resin may be present in an amount ranging from 30% to 65% by weight (see [0048]) and crosslinking compounds may be incorporated into the composition at a ratio of A:B of 95:5 to 5:95 [ see (0060 of Liu]).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by combining the taught composition of Liu with the POSS compound of Moxey, such incorporation allowing the provision of a composition for a cured product having improved heat resistance and mechanical strength imparted by the POSS compound.
Regarding Claim 9, the claim language is drawn to a composition – specifically that of claim 1. The body of the claim describes a use of the composition and does not delimit such, and further does not transform or further limit the composition of claim 1 to which the claim is drawn. As such, any composition in prior art or arrived at from prior art that embraces the claimed composition embraces the method recited in the body of the claim herein. As was set forth regarding claim 1 above, an ordinarily skilled artisan would have found it obvious to arrive at a composition for a cured product having improved heat resistance and mechanical strength imparted by the POSS compound.
Regarding Claims 11-14, these claims all various recite products or apparatus in the preamble, wherein the body of these claims’ claimed limitations are limited to “the cured product according to claim 10”. As there is no recitation as to distinguishing features beyond the cured product according to claim 10, the preambles of claims 11-14 are being interpreted as “intended use”.
The cured product of claim 10 has been rendered obvious as discussed above regarding claims 1 and 10. A person of ordinary skill in the art thus would have found it obvious to arrive at the claimed invention(s) of claims 11-14 in view of the taught composition of Liu and Moxey as described above regarding claims 1 and 10 to arrive at a composition for a cured product having improved heat resistance and mechanical strength imparted by the POSS compound.
Claim(s) 2 and 6 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al (US 20200071477 A1, published 03/05/2020), Moxey et al (US 20180037495 A1), and Wada et al (US 20120003437 A1) as applied to claim 1 above, and further in view of Birsak et al (US 20060041086 A1).
Regarding Claim 2, Liu et al. teaches a suitable difunctional acrylate monomer employed in the present invention may include cyclohexane dimethanol di(meth)acrylate [0053], however fails to teach the required bifunctional acrylic resin represented by the instant formula (3).
This limitation is met by Birsak
Birsak et al. teaches functionalized poly(arylene ether) compositions, comprising a
poly(arylene ether) compound [0014] and an olefinically unsaturated monomer, such as
cyclohexanediol di(meth)acrylate and ethoxylated (2) bisphenol A di(meth)acrylate
[0028]. Therefore, Birsak et al. teaches that cyclohexanediol di(meth)acrylate and
ethoxylated (2) bisphenol A di(meth)acrylate are functional equivalents for the purpose
of functioning as a difunctional acrylate monomer, for use in poly(arylene ether)
compositions.
It is prima facie obvious to substitute art-recognized functional equivalents known for the same purpose (See MPEP § 2144.06), and a person of ordinary skill in the art would thus consider it obvious to arrive at the claimed invention by substituting the cyclohexanediol dimethacrylate compound of Liu, as regarding the composition of claim 1 in Liu and Moxey, for the ethoxylated (2) bisphenol A dimethacrylate compound of Birsak.
Regarding Claim 6, Liu and Moxey. teach a suitable difunctional acrylate monomer employed in the present invention may include cyclohexane dimethanol di(meth)acrylate [Liu - 0053]. Liu also teaches that crosslinking compounds may be present in an amount ranging from 10 to 35 wt%, wherein as discussed regarding Moxey and Liu above in claim 1, the methacrylic POSS compound from Moxey-[0120] functions as a crosslinking compound.
However, Liu and Moxey fail to teach the required bifunctional acrylic resin represented by the instant formula (3) and the ratio of (B) to (D).
This limitation is met by Birsak
Birsak et al. teaches functionalized poly(arylene ether) compositions, comprising a
poly(arylene ether) compound [0014] and an olefinically unsaturated monomer, such as
cyclohexanediol di(meth)acrylate and ethoxylated (2) bisphenol A di(meth)acrylate
[0028]. Therefore, Birsak et al. teaches that cyclohexanediol di(meth)acrylate and
ethoxylated (2) bisphenol A di(meth)acrylate are functional equivalents for the purpose
of functioning as a difunctional acrylate monomer, for use in poly(arylene ether)
compositions.
The olefinically unsaturated monomers of Birsak, function as a crosslinker. Moxey discloses that crosslinkers may be present in 0-75 wt% of the composition, wherein the methacrylate POSS compound comprises 5-45 wt% - a ratio of crosslinker to POSS+crosslinker here covers a range from 0.00 to 0.61, falling within the claimed range.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by combining the taught composition of Liu with the POSS compound and initiators of Moxey and Wada, such incorporation allowing the provision of a composition for a cured product having improved heat resistance and mechanical strength imparted by the POSS compound.
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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/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734