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
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 03/16/2026 has been entered.
Response to Amendment
Applicant’s amendment and remarks in the reply filed 03/16/2026 are noted with appreciation.
Claims 1-25 and 28-30 remain pending.
Support for the amendment to independent claim 15 can be found, inter alia, at [0009] of the originally-filed specification.
Election/Restrictions
Claims 1-14 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 05/05/2025.
Response to Arguments
Applicants remarks in the reply filed 03/16/2026 have been noted with appreciation, but are moot in view of the new grounds of rejection set forth herein below.
Applicant has replaced the term “catalyst” with “a metal-free or photoreactive compound.” While such a characterization is supported by the originally-filed specification as noted above, no evidence has yet been presented as to whether this “compound” effects hydrosilylation, crosslinking, or both, in the method of forming a silicon and carbon containing film on a substrate. Applicant’s Schemes 1-3, presented at [0045] – [0047] of the Spec., clearly supports the former, but the later is still a viable interpretation of the claims, as written, since there is no link in the claims to what the “compound” is actually doing in the process.
Claim Objection
Claim 15 is objected to because of the following informalities: Azobis(cyclohexanecarbonitrile should read Azobis(cyclohexanecarbonitrile). Appropriate correction is required.
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 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) 15-25 and 28-30 is/are rejected under 35 U.S.C. 103 as being unpatentable over US 4,689,252 A in view of any one of WO 03/037963 A1, US 2009/0311012 A1, or US 2013/0172427 A1, further in view of US 2021/0198429 A1.
Claim 15
US 252 teaches a process for forming a coating on a substrate [6:61-66] comprising:
producing a film-forming polymer composition by polymerization of a reaction mixture of a first compound containing at least two unsaturated groups [2:10-17 (“[t]he polysilazane composition of the present invention comprises at least one polysilazane (1) containing . . . at least 2 SiR2 groups per molecule, wherein R2 is an unsaturated hydrocarbon radical”)], and a second compound containing at least two hydrosilyl functional groups [2:60-68 (“[i]n addition to the polysilazane (1) . . . at least one polysilazane (2) containing, per molecule, at least two (preferably at least 3) moieties chosen from . . . (1c) above”); 2:25 (“formula (1c) —X—Si(H)(R1)2, in which R1, which in (1c) may be identical or different, is selected from the group consisting of hydrogen, a saturated hydrocarbon, aryl, alkylaryl and arylalkyl”)];
forming a solution containing the film-forming polymer composition [6:40-46 (“when the intention is to use the composition[] to coat . . . a substrate, the composition must then be dissolved in an organic solvent”)]; and
contacting the composition with the substrate to form a coating [6:61-66; claims 31 and 32].
Applicant correctly notes that US 252 teaches the use of a metal complex “which effectively promotes the addition of SiH groups to the SiR2 group” (i.e., hydrosilylation) [6:9-31].
a. The claimed catalysts are known as equivalent the metal complexes taught by US 252 as hydrosilylation catalysts.
i. WO 03/037963 A1 teaches, in addition to the metal complexes taught by US 252, the following “conventionally known hydrosilylation catalyst[s]”: “benzoyl peroxide . . . and other peroxide polymerization initiators; 2,2’-azobis(isobutyronitrile), 1,1-azobis(cyclohexane-1-carbonitrile) . . . [and] 2,2’-azobisdimetylvaleronitrile” [p. 37 of original document].
ii. US 2009/0311012 A1 teaches, in addition to the metal complexes taught by US 252, the following “examples of hydrosilylation catalyst[s]”: “organic peroxides such as benzoyl peroxide . . . di-tert-butyl peroxide; and the azo compounds such as 2,2’-azobisisobutyronitrile . . ., 2,2’-azobis(2,4-dimethylvaleronitrile), and the like” [0038].
iii. US 2013/0172427 A1 teaches, when reacting a polyorganosiloxane (I) with, e.g., a vinyl-group containing monomer (IV) (i.e., a hydrosilylation reaction), “thermal or photoinitiators selected from but not limited to . . . azo compounds such as azobisisobutyronitrile and azobis-2,4-dimethylvaleronitrile; and organic peroxide compounds such as benzoyl peroxide . . ., methyl ethyl ketone peroxide . . ., and di-tert-butyl peroxide” [0051].
iv. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the process of US 252 so as to substitute, for the metal complex hydrosilylation catalyst, any of 2,2'-Azobis(2,4-dimethylvaleronitrile), 1,1'- Azobis(cyclohexanecarbonitrile), di-tert- butyl peroxide, benzoyl peroxide, and methyl ethyl ketone peroxide. One of ordinary skill in the art would have been motivated to do so by the desire and expectation of successfully catalyzing the hydrosilylation reaction based on the teaching of WO 963 and US 012 (i) that these compounds are equivalent to the metal complexes taught by US 252 for this purpose (MPEP § 2143(I)(B)) and/or (ii) that these compounds are known in the prior art as suitable for use as hydrosilylation catalysts (MEPEP § 2143(I)(A)).
b. The claimed catalysts would advantageously accomplish hydrosilylation at lower cost that metal complexes taught by US 252, which contain precious metals such as Pt.
i. In the alternative, it would have been obvious to substitute the claimed compounds for the metal complexes taught by US 252 with the expectation of reducing catalyst cost, as precious metals like Pt are expensive. The expectation of some advantage is the strongest rationale for combining references. MPEP § 2144(II).
US 252 does not explicitly refer to the polymer as a polycarbosilazane. Nevertheless, it is clear that the catalyzed polymerization reaction between the polysilazanes (1) and (2), wherein polysilazane (1) includes at least two unsaturated hydrocarbon radicals [supra] and polysilazane (2) includes at least 2, preferably at least 3 moieties containing hydrocarbon groups [supra] results in a polycarbosilazane, even if the term is not expressly used to describe it. See also [2:55] where X in moiety (1c) can “denote[] —Si— or N—, with at least 50% of the Xs being N—.”
US 252 does not teach that the coating is applied to the substrate by spin-on coating, spray coating, dip coating, or slit coating.
US 429 teaches that polycarbosilazane polymer containing compositions (solutions) can be deposited onto substrates by “contacting the solution with the substrate via spin-on coating, spray coating, dip coating, or slit coating technique” [0054].
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to utilize, as the coating technique of US 252, spin-on coating, spray coating, dip coating, or slit coating. One of ordinary skill in the art would have been motivated by the desire and expectation of successfully forming a coating of the polycarbosilazane composition on the surface of the substrate because US 429 teaches that these as techniques for doing so. See MPEP § 2143(I)(A).
Claim 16
US 252 teaches a pre-baking step “in an inert atmosphere from about 50° to 300°C . . . for a period of 1 minute to 24 hours,” followed by subsequent hard baking “in a vacuum, under pressure or in an inert atmosphere, with a temperature of 1,500°-2,000°C” [7:1-6 and 27-30].
US 252 does not teach that the hard baking is a heat-induced radical reaction or a UV-vis photo-induced radical reaction in an atmosphere of O2, O3, H2O, H2O2, N2O, NO, air, compressed air, or combinations thereof at a temperature range of 200-1000°C to convert the silicon and carbon containing film to a SiOC or SiOCN containing film.
US 429 teaches a method for coating a substrate with a polycarbosilazane polymer [supra]. The method further comprises a pre-baking the silicon and carbon containing film (i.e., the polycarbosilazane film) under N2 atmosphere at a temperature ranging from approximately 50°C to 400°C [0057] for approximately 1 minute to approximately 30 minutes [0144], then hard baking the silicon and carbon containing film (i.e., the polycarbosilazane film) by a heat-induced radical reaction or a UV-vis photo-induced radical reaction in an atmosphere of O2, O3, H2O, H2O2, N2O, NO, air, compressed air, or combinations thereof at a temperature range of 200-1000°C to convert the silicon and carbon containing film to a SiOC or SiOCN containing film [0058]. The hard baking treatment results in a dielectric film having a low-k value [0058].
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the pre-bake/hard-bake process of US 252 so as to perform the hard bake as a heat-induced radical reaction or a UV-vis photo-induced radical reaction in an atmosphere of O2, O3, H2O, H2O2, N2O, NO, air, compressed air, or combinations thereof at a temperature range of 200-1000°C to convert the silicon and carbon containing film to a SiOC or SiOCN containing film. One of ordinary skill in the art would have been motivated to do so by the desire and expectation of forming a dielectric film having a low-k value, thereby making the composition useful in an electronic device such.
Claim 17
US 252 teaches hydrosilylation [e.g., 2:17 and 2:58].
Claim 18
US 252 teaches that the unsaturation includes ≡SiH/≡SiR2 (i.e., alkynyl) [2:18] and alkene (which, because R2 and R3 in formulas (IIa), (IIb), and (IIc) are terminal moieties, reads on vinyl groups) or alkyne (i.e., alkynyl) unsaturation [2:50].
Claim 19
While US 252 teaches a variety of compounds containing unsaturated groups, it does not specifically teach the claimed tetravinylsilane, dimethyldivinylsilane, trivinylmethylsilane, 2,4,6-trimethyl-2,4,6-trivinylcyclotrisilazane, 1,3,5-trivinyl-1,3,5-trimethylcyclotrisiloxane, and octavinyloctasilasesquioxane. US 252 does not specifically prohibit these compounds either.
It is the Primary Examiner’s position that it would have been obvious to one of ordinary skill in the art to utilize any unsaturated group-containing compound in the production of the polycarbosilazane of US 252, including those recited in the claims. One of ordinary skill in the art would have been motivated to utilize such a compound by the desire and expectation of successfully producing the coating film.
Claims 20-23
US 252 teaches a polysilazane containing two, preferably three groups (1b) —X—SiHR1—X, where R1 can be hydrogen. This corresponds to two, preferably three —SiH2— groups. Moreover, US 252 teaches a polysilazane containing two, preferably three groups (1c) —X—SiH(R1)2, where R1 can be hydrogen. This corresponds to two, preferably three —SiH3 groups.
Claims 24 & 25
US 252 teaches a polysilazane containing preferably three moieties (1c) —X—SiH(R1)2, where R1 can be hydrogen and X can be N—, which gives N(SiH3)3.
Claim 28
US 252 teaches an organic solvent such as benzene, toluene, hexane, cyclohexane, isopropyl ether, ethyl ether, dichloromethane, and chlorobenzene [6:43-46].
Claim 29
US 252 teaches adding an additional polysilazane (3) having two, preferably three of the moieties (Ia)-(Ic) and (IIa)-(IIc), which satisfies all of the limitations of this claim.
Claim 30
As noted in ¶29, US 252 teaches at least N(SiH3)3. It is the Primary Examiner’s position that the structures containing two, preferably three of the moieties (Ia)-(Ic) and (IIa)-(IIc), is inclusive of all of the other structures recited in this claim as well.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. US 4,322,518 A and WO 2008/121151 A1 are cited as representative of the state of the prior art.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to WILLIAM P FLETCHER III whose telephone number is (571)272-1419. The examiner can normally be reached Monday-Friday, 9 AM - 5 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Duane Smith can be reached at (571) 272-1166. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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WILLIAM PHILLIP FLETCHER III
Primary Examiner
Art Unit 1759
/WILLIAM P FLETCHER III/Primary Examiner, Art Unit 1759
24 March 2026