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 .
DETAILED ACTION
Claims 1-17 of N. Auner, et al., 17/926,842 (11/21/2022) are pending. Claims 3-4,6,10-13 and 17 are withdrawn as not reading on the elected species. Claims 1-2,5,7-9 and 14-16 are under examination on merits and are rejected.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Election/Restrictions
Pursuant to the election of species requirement, Applicant elected, without traverse, in the reply filed on 02/13/2026 the following species for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
The elected species of the method for producing a bifunctional monosilane intermediate of the general formula (II) SiR1R21HCI: redistribution reaction of an organoperchloromonosilane of the general formula (III) SiR1R22Cl2 with an organoperhydridomonosilane of the general formula (IV) SiR1R23H2 (IV);
The elected species of the compound of formula (I): MeSiBu2Hept;
The elected species of the compound of formula (II): MeSiBuHCl;
The elected species of the compound of formula (III): MeSiBuCl2;
The elected species of the compound of formula (IV): MeSiBuH2;
The elected species of the compound of formula (V): MeSiBu2Cl;
The elected species of the compound of formula (VI): MeSiBu2H;
Applicant amended claim 1 and added new claim 17 in the reply filed on 06/29/2026. Claims 1-2,5,7-9 and 14-16 read on the elected species, claims 3-4,6,10-13 and 17 are withdrawn as not read on the elected species. The elected species are searched and are determined to be free of prior arts; searching has been extended to other compounds as mentioned in the 103 rejections below. The provisional species election requirement is in effect.
Withdrawal Claim Rejections - 35 USC § 112(b)
Rejection of claims 1-2,5,7-9 and 14-16 under 35 U.S.C. 112(b) as being indefinite for multiple recitations of the exemplary claim language “preferably” is withdrawn in view of the claims have been amended by deletion of those languages.
Withdrawal Claim Rejections - 35 USC § 103
Rejection of claims 1-2,5,7,9 and 14-16 under 35 U.S.C. 103 as being unpatentable over a combination of A. Onopchenko, et al, 52(18), The Journal of Organic Chemistry, 4118-4121(1987)(“Onopchenko”); S. B. Amin, et al, 129(10), Journal of the American Chemical Society 2938-2953 (2007)(“Amin”) and K. R. Bakshi, et al, US 4595777 (1986)(“Bakshi”) is withdrawn in view of claims have been amended by deletion of “producing an intermediate of the general formula R4SiH3 by a hydrogenation reaction of a compound of the formula R4SiCl3” in the step c recited by claim 1. Regards Applicant argues that “None of the cited art teach or suggests the production of a bifunctional intermediate with H and Cl substituents, as recited in claim 1”, it should be note that the “producing an intermediate of the general formula R4SiH3 by a hydrogenation reaction of a compound of the formula R4SiCl3” is an alternative step for the preparation of the formula (VI) in step c of the claim 1 filed on 02/13/2026, therefore, in this condition both step a and step are not required for the claimed method.
Rejection of claims 1-2,5,7-9 and 14-16 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over a combination of R. Leguijt, et al, US 2015/0370062 A1 (2015)(“Leguijt”), K. Saxena, et al, 23(12), Applied Organometallic Chemistry, 535-540(2009)(“Saxena”), ABE Takeshi, et al, JP2017160160A (2017)(“Takeshi”), K. Oertle, et al, 26(45), Tetrahedron Letters, 5511-5514 (1985)(“Oertle”) and K. Mautner, et al, US 20110196165A1 (2011)(“ Mautner”) is withdrawn in view of reconsideration of prior arts. The rationales supporting the rejection on the ground that one ordinary skill would use the proposed method to prepare the proposed compound. While one ordinary skill has a motivation to modify the Leguijt Example 3 as proposed, however, one ordinary skill in the art would use the method taught by Leguijt (reacting of a silicon chloride with an alkyl Grignard agent of alkyl lithium) rather than the proposed method. Therefore, the rejection is withdrawn.
New Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1-2,5,7-9 and 14-16 are rejected under 35 U.S.C. 112(b) as being indefinite because claim 1 recites the limitation ". . . R1SiH3 obtained from step c) to a final hydrosilylation reaction . . . " in the step d. There is insufficient antecedent basis for this limitation in the claim because the instant claim 1 has been amended by deletion of the “producing an intermediate of the general formula R4SiH3 by a hydrogenation reaction of a compound of the formula R4SiCl3” in the step c recited by claim 1.
New 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.
Claims 1-2,5, 7, 9 and 14-16 are rejected under 35 U.S.C. 103 as being unpatentable over a combination of F. Kropfagans, et al. US5654459 (1997)(“Kropfagans”); V. Pandarus, et al. 21.1 Green Chemistry 129-140 (2019)(“Pandarus”); T. Beppu, et al. 869 Journal of Organometallic Chemistry 75-80 (2018)(“Beppu”); and R. Leguijt, et al, US 2015/0370062 A1 (2015)(“Leguijt”).
F. Kropfagans, et al. US5654459 (1997) (“Kropfagans”)
Kropfagans teaches a method of preparing (CH3)2HSiCl by reacting of (CH3)2SiCl2 and (CH3)2SiH2 in the presence of γ-Al2O3 at 160ºC.
PNG
media_image1.png
239
917
media_image1.png
Greyscale
Kropfagans at col. 4, Example 1, Table 1.
The Kropfagans method meets each and every limitation of the step a) recited in claim 1, 7, 9, wherein each of R1, R21-R23 in the general formula II-III is CH3.
V. Pandarus, et al. 21.1 Green Chemistry 129-140 (2019)(“ Pandarus”)
Pandarus teaches a method for synthesis of high purity silicone precursors by hydrosilylation of solvent-free olefins catalyzed by a hybrid catalyst consisting of mesoporous organosilica microspheres doped with Pt nanoparticles. Pandarus at Abstract.
Per Tables 6, Pandarus teaches the following reaction:
PNG
media_image2.png
326
1269
media_image2.png
Greyscale
Pandarus at page 134, Table 6, Entry 1-5.
The Pandarus product (nOct)Me₂SiCl maps of the general formula V recited in the step b) of claim 1 as both R1 and R2 is CH3, R31 is octyl group. Thus, the combination of Pandarus and Kropfagans meets each and every limitation of steps a)-b) recited in claim 1.
Per Table 7, Pandarus teaches the following reactions
PNG
media_image3.png
405
1226
media_image3.png
Greyscale
Pandarus at page 135, Table 7.
Pandarus fairly teaches one ordinary skill in the art that octadec-1-ene can react with different silanes (R3SiH) in the presence of the catalyst of SiliaCatPt(0) to form hydrosilylation product with a yield of 82-91%. The Pandarus method of Table 7 differs from the step d) recited in claim 1 in that none of the used silane in the Table 7 is the claimed formula VI recited in step d.
T. Beppu, et al. 869 Journal of Organometallic Chemistry 75-80 (2018)(“ Beppu”)
Beppu teaches a method of preparing of (nOct)Me₂SiH from (nOct)Me₂SiCl as indicated below:
PNG
media_image4.png
462
1454
media_image4.png
Greyscale
Beppu at page 76, right col. Table 2 and the Scheme under the Table 2.
The Beppu method comprises hydrogenation of the Pandarus product (nOct)Me₂SiCl to form the product of (nOct)Me₂SiH that maps the general formula VI recited in the step c) in claim 1 as both R1 and R2 is CH3, R32 is octyl group. Thus, the combination of Pandarus and Beppu meets each and every limitation of step c recited in claim 1.
Difference between the Combination of Kropfagans/Pandarus/Beppu and the Claims 1-2,5, 7, 9 and 14-16
The combination of Kropfagans, Pandarus and Beppu differs from the instant claim 1 only in that the combination does not teaches one ordinary skill in the art to conduct a hydrosilylation reaction by reacting of the Beppu product (nOct)Me₂SiH with a compound containing one or more C-C double bonds or C-C triple bonds to obtain the general formula (I) as recited in the step d) of claim 1.
R. Leguijt, et al, US 2015/0370062 A1 (2015) (“Leguijt”)
Leguijt teaches a compound that can be used as fluid in an electrowetting apparatus, which includes at least one compound selected from the group consisting of:
PNG
media_image5.png
115
295
media_image5.png
Greyscale
wherein each of R1, R2, R3 and R4 is independently an alkyl group. Leguijt at abstract.
Regarding the alkyl group, Leguijt teaches that
[0046] . . . a total number of carbon atoms contained by any one of the alkyl groups R1, R2, R3, R4 may be at most, i.e. less than or equal to, 30; in other words this total number may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 carbon atoms and may for example be in one of the ranges of 1 to 4 carbon atoms, 5 to 8 carbon atoms, 9 to 12 carbon atoms, 13 to 16 carbon atoms, 17 to 20 carbon atoms, 21 to 24 carbon atoms, 25 to 28 carbon atoms, and 27 to 30 carbon atoms. Where any of the alkyl groups R1, R2, R3 and R4 is a branched alkyl group, a longest chain of carbon atoms in any one of the alkyl groups R1, R2, R3 and R4 is at most, i.e. less than or equal to, 24 carbon atoms long. Therefore, such a longest chain may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms long and may for example have 3 to 6 carbon atoms, 7 to 10 carbon atoms, 11 to 14 carbon atoms, 15 to 18 carbon atoms, 19 to 22 carbon atoms or 21 to 24 carbon atoms.
Leguijt at page 4, [0046].
Therefore, one ordinary skill in the art would be appraised that by replacing any silane used in the Pandarus method of Table 7 with the Beppu product (nOct)Me₂SiH would arrive at a tetra alkyl-silane that is a species of the Leguijt compound
PNG
media_image6.png
259
249
media_image6.png
Greyscale
, which can be used as a fluid for an electrowetting apparatus.
Obviousness Rationales of the Claims
One ordinary skill in the art would arrive at the claimed invention before the effective filling date of the instant application because one ordinary skill in the art seeking a fluid for electrowetting apparatus is motivated to combine the methods taught by Kropfagans, Pandarus and Beppu and then use the Beppu product (nOct)Me₂SiH as a silane to react with
PNG
media_image7.png
114
235
media_image7.png
Greyscale
as taught by the Pandarus Table 7, thus arrive a method as indicated below.
PNG
media_image8.png
1707
1767
media_image8.png
Greyscale
The proposed tetraalkylsilane compound maps the general formula I recited in the step d) in claim 1 as both R1 and R2 is CH3, R3 is octyl group and R4 is octadecyl group. The proposed method meets each and every limitation of claims 1,7 and 9 therefore, claims 1, 7 and 9 are obvious. The rationales supporting the proposed method is “combining prior art elements according to known methods to yield predictable results” and “simple substitution of one known element for another to obtain predictable results”. MPEP2143.I (A) and MPEP2143.I (B). IT
One of ordinary skill is motivated to do so with a reasonable expectation of success because:
(i). Leguijt teaches the proposed compound can be used as a fluid for an electrowetting apparatus,
(ii). Kropfagans teaches the method of preparing (CH3)2HSiCl by reacting of (CH3)2SiCl2 and (CH3)2SiH2 in the presence of gamma-Al2O3 as catalyst;
(iii). Pandarus teaches the method of preparing of (nOct)(CH3)2SiCl by reacting of (CH3)2SiHCl with oct-1-ene in the presence of SiliaCatPt(0);
(iv). Beppu teaches the method of preparing of (nOct)(CH3)2SiH by hydrogenation of (nOct)(CH3)2SiCl; and
(v). Pandarus teaches that octadec-1-ene can react with different silanes (R3SiH) in the presence of the catalyst of SiliaCatPt(0) to form hydrosilylation product with a yield of 82-91%.
Claim 2 and claim 5 are obvious because as indicated above that R1-R4 in the proposed compound are three different saturated hydrocarbon groups (CH3, octyl group and octadecyl group).
Claims 14 and 16 are obvious because Pandarus teaches that hydrosilylation of olefins is catalyzed by SiliaCatPt(0) that is a Pt based catalyst.
Claim 15 is obvious because one ordinary skill in the art is also motivated to modify the proposed method by conducting the step c with LiAlH4 as a catalyst because Beppu also teaches that “Hydrosilanes are usually synthesized by the reduction of chlorosilanes and alkoxysilanes using strong reducing agents such as LiAlH4 and iBu2AlH”. Beppu at page 75, left col. line 1-3 of the second paragraph. LiAlH4 maps the MHX in claim 15 as M is two metals that are Li and Al, X is 4, therefore, claim 15 is obvious.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over a combination of F. Kropfagans, et al. US5654459 (1997)(“Kropfagans”); V. Pandarus, et al. 21.1 Green Chemistry 129-140 (2019)(“ Pandarus”); T. Beppu, et al. 869 Journal of Organometallic Chemistry 75-80 (2018)(“ Beppu”); and R. Leguijt, et al, US 2015/0370062 A1 (2015)(“Leguijt”) as applied to claim 1 above; further in view of T. Nitz, et al. WO2007101792A1 (2007)(“Nitz”).
The Combination of Kropfagans, Pandarus, Beppu and Leguijt
As discussed above that the combination of Kropfagans, Pandarus, Beppu and Leguijt teaches a method meeting each and every limitation of claim 1.
Difference between the Combination and the Instant Claim 8
The method taught by the combination differs from the instant claim 8 in that the catalyst used in step (a) is not the claimed catalyst.
T. Nitz, et al. WO2007101792A1 (2007) (“Nitz”)
Nitz is published in German, a copy of machine translation is attached as the second part of the reference, which results the total page of the full reference is 35, the format for citation of the full reference is xx/35.
Nitz teaches:
a continuous process for preparing organylhydrogenchlorosilanes of the general formula (1) RaSiHC13-a (1) from silanes of the general formula (2) RaSiC14-a (2) and silanes of the general formula (3) Ra-1SiHC14-a (3) in a reaction column in the presence of a catalyst which contains at least one fully organically substituted ammonium or phosphonium unit, where R is a hydrocarbon radical having from 1 to 10 carbon atoms and a is 1 or 2, with silane of the general formula (3) being introduced into the reaction column below the point of introduction of the silane of the general formula (2) and the silane of the general formula (1) is taken off at a point in the reaction column which has an elevated concentration of this silane.
Nitz at page 1/35, abstract.
Per Example 1, Nitz teaches that Bu4PCl is a catalyst can be used in his method. Nitz at page 35/35, Example 1.
One ordinary skill in the art would be appraised that the Nitz method also can be used to prepare Me2SiHCl from Me2SiCl2 and Me2SiH2 because they are species of the general formula RaSiHC13-a, RaSiC14-a and Ra-1SiHC14-a respectively wherein a is 2.
Obviousness Rationales of Claim 8
One ordinary skill in the art would arrive at the claimed invention before the effective filling date of the instant application because one ordinary skill in the art seeking a fluid for electrowetting apparatus is motivated to further modify the method taught the combination of Kropfagans, Pandarus, Beppu and Leguijt by preparation of Me2SiHCl from Me2SiCl2 and Me2SiH2 in the presence of at least one fully organically substituted ammonium or phosphonium unit such as Bu4PCl as taught by Nitz in the Example 1, thus arrive at a method meeting each and every limitation of claims 1 and 8, therefore, claims 1 and 8 are obvious.
One ordinary skill in the art has a motivation to do so with a reasonable expectation of success because Nitz teaches that Me2SiHCl can be prepared from Me2SiCl2 and Me2SiH2 in the presence of at least one fully organically substituted ammonium or phosphonium unit.
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 FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/FRANK S. HOU/Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
Prosecution Insights