Prosecution Insights
Last updated: July 17, 2026
Application No. 17/436,746

CROSSLINKABLE SILOXANE COMPOUNDS FOR THE PREPARATION OF DIELECTRIC MATERIALS

Final Rejection §103
Filed
Sep 07, 2021
Priority
Mar 08, 2019 — EU 19161650.7 +1 more
Examiner
MALLOY, ANNA E
Art Unit
1737
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Merck Patent GmbH
OA Round
6 (Final)
46%
Grant Probability
Moderate
7-8
OA Rounds
0m
Est. Remaining
41%
With Interview

Examiner Intelligence

Grants 46% of resolved cases
46%
Career Allowance Rate
225 granted / 491 resolved
-19.2% vs TC avg
Minimal -5% lift
Without
With
+-4.8%
Interview Lift
resolved cases with interview
Typical timeline
3y 5m
Avg Prosecution
39 currently pending
Career history
541
Total Applications
across all art units

Statute-Specific Performance

§101
0.1%
-39.9% vs TC avg
§103
89.4%
+49.4% vs TC avg
§102
3.7%
-36.3% vs TC avg
§112
4.8%
-35.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 491 resolved cases

Office Action

§103
DETAILED ACTION Claims 1, 3, 4, and 7-12 are pending. Claim 1 has been amended, claims 5, 6, and 13 have been canceled, and claims 2 and 14-20 were previously canceled. 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 . 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, 3, 4, and 7-12 are rejected under 35 U.S.C. 103 as being unpatentable over Kazumasa et al. (WO2009054508) in view of Inata et al. (U.S. 2011/0319582). Translation previously provided. Kazumasa et al. teaches a condensate (A) of alkoxysilane represented by the following general formula (1): PNG media_image1.png 31 632 media_image1.png Greyscale [0014] where P is represented by the following general formula (2), Q represents an alkyl group, an aryl group, an aralkyl group, an alkenyl group, or hydrogen, R3 represents hydrogen or a monovalent organic group, R0 represents an alkyl group having 1 to 6 carbon atoms, x represents a positive number, y, z, and a represent 0 or a positive number and satisfy the conditions of x + y = 1, 0.3 ≦ x ≦ 1, 0 ≦ y ≦ 0.7, 0 ≦ z ≦ 2, and 0 ≦ a ≦ 1, P, Q, R0, and R3 in one molecular may each contain two or more different groups, and Q and R0, Q and R3, or and in one molecular may each be identical groups or different groups [0015]: PNG media_image2.png 160 365 media_image2.png Greyscale [0016] where R1 and R2 each independently represent hydrogen, a halogen atom, an alkyl group, an alkenyl group, or an aryl group, or R1 and R2 together form a 5- or 6-membered ring, and R represents a divalent group [0017] in which R is preferably an alkylene group, more preferably an alkylene group having 1 to 6 carbon atoms, and particularly preferably a linear alkylene group having 3 to 6 carbon atoms, from the viewpoint that the cured product of the composition has excellent scratch resistance and UV resistance [0026] and preferred examples of the maleimide group are formulae (5) to (10) [0020] where formula (7) is the following: PNG media_image3.png 160 270 media_image3.png Greyscale [0022]. Kazumasa et al. also teaches in the method for producing condensate (A), a maleimide group-containing trialkoxysilane represented by the general formula P-Si(OR)3 is referred to as a compound (p-1), a maleimide group-containing dialkoxysilane represented by the general formula P-Si(R0) (OR3)2 is referred to as a compound (p-2), and a silane compound represented by the general formula Q-Si(OR3)3 is referred to as a compound (q) [0037], specifically, Production Method 1: the compound (p) is hydrolyzed and condensed, or the compound (p) and the compound (q) are hydrolyzed and condensed. Hereinafter, the compound (p-1), the compound (p-2), and the compound (q), which are raw material compounds, will be described. The compound (p-1) may be any compound as long as it satisfies P-Si(OR3)3, and specific preferred examples thereof include compounds obtained by the production methods [1] to [4] [0038-0039] (claim 12) in which [1] includes: [1] An addition reaction product of a compound having a maleimide group and an ethylenically unsaturated group other than the maleimide group, and trialkoxysilane [0040] in which preferred examples of a compound having a maleimide group and an ethylenically unsaturated group includes the following formula (11) [0045]: PNG media_image4.png 139 380 media_image4.png Greyscale [0046] where R1 and R2 are as defined above. R7 means a group containing an ethylenically unsaturated group at the terminal. Preferred examples of R7 in the starting material production method [1] include an allyl group. The addition reaction product of the compound represented by the formula (11) and trialkoxysilane can be produced by a method such as a hydrosilylation reaction in the presence of a platinum-based catalyst [0047] which is equivalent to a first siloxane monomer represented by Formula (1) of instant claims 1, 3, and 4 when R1 and R2 are alkyl having 1 carbon atom, L1=L2=L3=OR where R is straight-chain alkyl having 1 to 30 carbon atoms, and Z is –(CH2)n- when n is 3 based on pages 55-56 of the instant specification; Compound (p-2) is a compound represented by P-Si(R0)(OR3)2. The compound (p-2) may be produced by replacing trialkoxysilane with alkyldialkoxysilane in [1] in the raw material production method which is equivalent to a first siloxane monomer represented by Formula (1) of instant claims 1, 3, and 4 when R1 and R2 are alkyl having 1 carbon atom, L1 is R which is a straight-chain alkyl having 1 to 30 carbon atoms, L2 and L3 are OR where R is a straight-chain alkyl having 1 to 30 carbon atoms, and Z is –(CH2)n- when n is 3; and the compound (q) is a compound represented by the general formula Q-Si(OR3)3. Specific examples of the compound (q) include the following examples. When Q is an alkyl group, specific examples thereof include methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, and ethyltripropoxysilane. When Q is an aryl group, specific examples thereof include phenyltrimethoxysilane, phenyltriethoxysilane, and phenyltripropoxysilane. When Q is an aralkyl group, specific examples thereof include benzyltrimethoxysilane, benzyltriethoxysilane, and benzyltripropoxysilane. When Q is a (meth) acryloyloxyalkyl group, specific examples thereof include γ-(metha)acryloyloxypropyl trimethoxysilane , γ-(metha)acryloyloxypropyl triethoxysilane , and γ-(metha)acryloyloxypropyl tripropoxysilane. When Q is an aminoalkyl group, specific examples thereof include compounds in which the (meth)acryloyloxy group in the above is replaced by an amino group. When Q is an alkenyl group, specific examples thereof include vinyltrimethoxysilane, vinyltriethoxysilane, and vinyltripropoxysilane. When Q is a hydrogen atom, specific examples thereof include trimethoxysilane, triethoxysilane, and tripropoxysilane [0061-0067] and methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane are preferable [0068] e.g. when compound (q) is methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltripropoxysilane phenyltrimethoxysilane, phenyltriethoxysilane, trimethoxysilane, triethoxysilane, and/or tripropoxysilane, they are equivalent to a third (or fourth) siloxane monomer of instant claims 7-10 represented by Structures T2 and F2 when L21-L23 (or L31-L33) are OR” (or OR’’’) where R” (or R’’’) are straight-chain alkyl having 1-3 carbon atoms and R21 (or R31) is a straight-chain alkyl having 1 or 2 carbon atoms, an aryl having 6 carbon atoms, or H respectively. Although Kazumasa et al. does not teach a specific example of a condensate (A) produced by method 1 as defined above, it would have been obvious to one of ordinary skill in the art to perform such a method using the above compounds through routine experimentation of substituting known methods as well as substituting known maleimides and arrive at the instant claims with a reasonable expectation of success. Kazumasa et al. does not teach a second siloxane monomer represented by Structure S1. However, Inata et al. teaches a curable composition comprising a reaction product (A) obtained by reacting an alkoxysilane compound (a1) represented by Formula (1) below (hereinafter, simply called `maleimide alkoxysilane (a1)`) and inorganic oxide microparticles (a2) in the presence of water and an organic solvent (hereinafter, simply called `reaction product (A)`): PNG media_image5.png 53 625 media_image5.png Greyscale [0022] wherein P denotes a group represented by Formula (2), which is described later, R3 denotes a hydrogen atom or a monovalent organic group, R0 denotes a monovalent organic group, a is 0 or a positive number and satisfies 0≤a<1, z is a positive number and satisfies 0.1≤z≤2, P, R0, and R3 may each comprise two or more different types of groups in one molecule, and R0 and R3 may each be identical groups or different groups in one molecule [0023] in which the maleimide alkoxysilane (a1) [hereinafter, also simply called (a1)], which is a starting material for the reaction product (A) of the present invention, is a compound represented by Formula (1) below. (a1) means, as described in detail later, either a condensation product of an alkoxysilane in which an alkoxysilane is partially hydrolyzed/condensed, or a mixture of this condensation product and an alkoxysilane monomer [0028-0029] wherein specific examples of the maleimide group in Formula (2) are shown in Formula (5) to Formula (10) [0036] such as the following formula (7): PNG media_image6.png 134 377 media_image6.png Greyscale [0036] which is equivalent to Kazumasa’s maleimide compound and a first siloxane monomer represented by Formula (1) of instant claims 1, 3, and 4. Inata et al. also teaches the reaction product (A) may contain a condensation product formed by co-condensation of a hydrolysable silane compound that is different from the maleimide alkoxysilane (a1). Furthermore, it may contain inorganic oxide microparticles that are surface-modified not only with the maleimide alkoxysilane (a1) but also with a hydrolysable silane compound that is different therefrom. Specific examples of the hydrolysable silane compound that is different from (a1) include tetramethoxysilane, tetraethoxysilane, tetraisopropoxysilane, methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatoropropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, p-styryltrimethoxysilane, p-styryltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltriethoxysilane, 3-[(3-ethyloxetan-3-yl)methoxy]propyltrimethoxysilane, 3-[(3-ethyloxetan-3-yl)methoxy]propyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, dimethyldimethoxysilane, dimethyldiethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldiethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldiethoxysilane, trimethylmethoxysilane, trimethylethoxysilane, tetrachlorosilane, methyltrichlorosilane, dimethyldichlorosilane, trimethylchlorosilane, hexamethyldisilazane, trimethoxysilane, and triethoxysilane [0118-0119] wherein tetramethoxysilane, tetraethoxysilane, and tetraisopropoxysilane are equivalent to a second siloxane monomer represented by Structure S1 of instant claim 1 when L11-L14 are OR’ when R’ is a straight-chain alkyl having 1-3 carbon atoms respectively; tetrachlorosilane is equivalent to a third (or fourth) siloxane monomer represented by Structures T1 and F1 of instant claims 7-10 when L21-L24 (or L31-L34) are halogen; methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, trimethoxysilane, and triethoxysilane are equivalent to a third (or fourth) siloxane monomer represented by Structures T2 and F2 of instant claims 7-10 when L21-L23 (or L31-L33) are OR” (or OR’’’) when R” (or R’’’) is a straight-chain alkyl having 1 or 2 carbon atoms and R21 (or R31) is a straight-chain alkyl having 1 carbon atom or an aryl group having 6 carbon atoms respectively; dimethyldichlorosilane is equivalent to a third (or fourth) siloxane monomer represented by Structures T3 and F3 of instant claims 7-10 when L21 and L22 (or L31 and L32) are halogen and R21 and R22 (or R31 and R32) are straight-chain alkyl having 1 carbon atom; and trimethylmethoxysilane, trimethylethoxysilane, and trimethylchlorosilane are equivalent to a third (or fourth) siloxane monomer represented by Structures T4 and F4 of instant claims 7-10 when L21 (or L31) is OR” (or OR’’’) when R” (or R’’’) is a straight-chain alkyl having 1 or 2 carbon atoms or L21 (or L31) is halogen and R21-R23 (or R31-R33) are straight-chain alkyl having 1 carbon atom respectively. It should be noted that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 65 USPQ 297 (1945). See MPEP 2144.07. In the instant case, both Kazumasa and Inata teach known polymers in which the selection of known silanes considered equally suitable for the preparation of said polymers is well known in the art. Furthermore, it is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose…[T]he idea of combining them flows logically from their having been individually taught in the prior art. In re Kerkhoven, 205 USPQ 1069 1072. In the instant case, it is well known in the art to combine multiple monomers in the production of a polymer. Therefore, 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 teachings of Kazumasa et al. to include other known silane monomers such as those taught by Inata et al. and arrive at the instant claims through routine experimentation of combining and/or substituting equally suitable silanes with a reasonable expectation of success. With regard to claim 11, Kazumasa et al. teaches, regarding formula (1), x represents a positive number, y, z, and a represent 0 or a positive number, and x+y=1, 0.3 ≤ x ≤ 1, 0 ≤ y ≤ 0.7, 0 ≤ z ≤ 2, and 0 ≤ a ≤ 1 are satisfied. Each of x, y, and z means the average value of [(P-SiO3/2)1-a (P-Si(R0)O2/2)a] unit, the (Q-SiO3/2) unit, and the (O1/2R3) unit in the entire condensation product (A), respectively, and a represents the mean ratio of (P-Si(R0)O2/2) units in the (P-SiO3/2)1-a (P-SiR0)O2/2)a] unit. The range of x is 0.3 ≦ x ≦ 1, preferably 0.5 ≦ x ≦ 1. When x is 0.3 or more, the curability of the composition is excellent, which is preferable. The range of y is 0 ≦ y ≦ 0.7, preferably 0 ≦ y ≦ 0.5. When y is at most 0.7, the curability of the composition will be excellent, such being preferred. The range of z is 0 ≦ z ≦ 2, preferably 0 ≦ z ≦ 1.5, and more preferably 0 ≦ z ≦ 1. When z is 2 or less, the condensate (A) can have a high molecular weight, and the cured product of the composition is excellent in scratch resistance, which is preferable. The range of a is 0 ≦ a ≦ 1, and preferably 0 ≦ a ≦ 0.5. When a is 0.5 or less, the cured product of the composition has excellent scratch resistance, which is preferable [0030] while Inata et al. teaches, regarding formula (1), a is 0 or a positive number and satisfies 0≦a<1, and z is a positive number and satisfies 0.1≦z≦2. a means the average proportion of (P--Si(R0)O2/2) units in the [(P--SiO3/2)1-a(P--Si(R0)O2,2)a] unit, and z is the average value of (O1/2R3) units in (a1) overall. The range of a is 0≦a<1, and preferably 0≦a≦0.5. It is preferable for a to be no greater than 0.5 since a cured material of the composition has excellent scratch resistance [0049-0051] and the range of z is 0.1≦z≦2, preferably 0.6≦z≦2, and more preferably 0.6≦z≦1.5. By setting z at 0.1 or greater, modification of the surface of colloidal silica is sufficient, and a cured material has excellent scratch resistance [0053] which overlaps the instantly claimed molar ratio between the first siloxane monomer and the entirety of all further siloxane monomers of 1:0.1 to 1:10. Response to Arguments Due to the amendment filed April 23, 2026 of instant claim 1, the 103 rejections over Kazumasa et al. and further in view of Ryang have been withdrawn. Applicant’s arguments with regard to these rejections have been considered but are moot due to the amendment of instant claim 1. Due to the cancelation of claim 13, the double patenting rejection over U.S. Patent No. 11,982,942 has been withdrawn. The objection to claim 3 has been withdrawn. 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 ANNA E MALLOY whose telephone number is (571)270-5849. The examiner can normally be reached 6:30-3:00 EST M-F. 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, Keith Walker can be reached at 571-272-3458. 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. /Anna Malloy/Examiner, Art Unit 1737 /KEITH WALKER/Supervisory Patent Examiner, Art Unit 1735
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Prosecution Timeline

Show 6 earlier events
Feb 10, 2025
Non-Final Rejection mailed — §103
Jun 05, 2025
Response Filed
Aug 01, 2025
Final Rejection mailed — §103
Nov 03, 2025
Request for Continued Examination
Nov 04, 2025
Response after Non-Final Action
Dec 23, 2025
Non-Final Rejection mailed — §103
Apr 23, 2026
Response Filed
Jun 18, 2026
Final Rejection mailed — §103 (current)

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