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 Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicants’ submission filed on 7/6/2025 has been entered.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Drawings
The drawings filed 2/17/2023 are accepted.
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.
Claim(s) 1-6, and 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over JP H10251516A (herein referred to as “Yang”) in view of Suzuki et al (US 2017/00009034).
Yang teaches a silane coupling agent comprising a silicon compound defined below and water and having a concentration of the silicon compound of from 0.01 to 10 wt.%: (teaching “the concentration of the silane oligomer composition in the water or the water / alcohol solution can be arbitrarily selected depending on the purpose of use but is generally 0.01 to 20 w / v%. Is preferred.”):
the silicon compound comprising a compound (I) represented by Formula (1) and a polycondensate of the compound (I) (see “Problem to be Solved” and 0005 teaching “The unreacted substances and low-condensation products remaining in A…”), wherein a ratio of contents of the compound (I) to a compound (II) is from 1/99 to 95/5 (teaching “the unreacted silane compound and a low condensate content of 20% or less”), the compound (II) being a polycondensate of the compound (I) and having a weight average molecular weight of from 200 to 10000 (teaching 250-5,000), Y represents a hydrocarbon group having from 1 to 10 carbons and containing a group reactive with organic matter (0008).
Yang teaches a method of manufacturing a silane coupling agent, the method comprising, by hydrolyzing a compound represented by Formula (2), obtaining a compound represented by Formula (1) in the presence of water (0021-0022; no solvent). Yang does not teach said reaction should occur a condition of pH 4 or lower. However, Suzuki teaches said reaction to form an alkoxysilane hydrolytic condensate is accomplished by keeping the temperature of the system to no higher than 20° C., adding the acid catalyst to adjust the pH to a range of 1.0 to 4.0 and preferably pH 1.5 to 3.0, and then mixing the alkoxysilane, to produce an alkoxysilane hydrolysate, and then further adjusting it so that the desired alkoxysilane hydrolytic condensates are present in the prescribed amounts (0123). Thus, it would have been obvious to one of ordinary skill in the art at the time the invention was filed to hydrolyzing a compound represented by Formula (2) as taught in Yang at a pH of less than 4. The motivation for doing so would have been that Suzuki teaches such pH conditions are typical for such a reaction. The resulting composition reads on the silane coupling agent of claim 2 having a pH of 4 or lower.
With regards to the method limitations which require specific reaction conditions including that the amount of water used is from 3 to 12 mol per mol of the compound represented by Formula (2), and that the proportion of organic solvent is controlled to 0.7 parts by weight or less per part by weight of the compound represented by Formula (2), the examiner notes said limitations are method limitations that do not patentably distinguish a claimed product from a product taught in the prior art unless the claimed method of making the product inherently results in a materially different produc.t In the present application, no such showing has been made.
With regard to claim 3, water evaporates much slower than n-butyl acetate, with a relative evaporation rate of approximately 0.30 (or 30%) compared to n-butyl acetate's rate of 1.00. Thus, it is understood to have an evaporation rate of 30 when the evaporation rate of butyl acetate is taken as 100. Alternatively, Yang teaches the composition further comprises a C1-C6 alcohol, which applicant discloses meets the claimed limitation.
With regards to claim 4, Yang teaches the composition further comprises a C1-C6 alcohol, which applicant discloses meets the claimed and SP limitations.
With regards to claim 5, Yang teaches the silane composition of claim 1 may be used as a surface treatment, herein understood to read on the claimed “surface modifier”.
With regard to claim 11, Yang teaches “the unreacted silane compound and a low condensate content of 20% or less” relative to the condensate. Said teaching is understood to anticipate the claimed teaching.
Claim(s) 7-10, 13, 15-17, 19 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over CN 109880583 (herein referred to as CN) in view of JP H10251516A (herein referred to as “Yang”) and Suzuki et al (US 2017/00009034).
With regards to claim 7, CN teaches a curable adhesive comprising and a silane coupling agent. The adhesive is useful for laminating chips or wafers to three dimensional laminates such as LED elements (herein understood to read on the claimed semiconductor device of claim 10). The curable composition comprises an epoxy group containing polyorganosilsequioxane (abstract).
CN teaches the adhesive may comprise a silane coupling agent but does not teach the coupling agent should comprise the claimed silicon compound of claim 1. However, Yang teaches the claimed silane compound and teaches it can be used as a silane coupling agent. Thus, it would have been obvious to one of ordinary skill in the art at the time the invention was filed to utilize the silane coupling agent of Yang as the silane coupling agent of the adhesive composition disclosed in CN. The motivation for doing so is that the courts have held it is prima facie obvious to substitute one equivalent component for another (See MPEP 2144.06).
Yang teaches a method of manufacturing a silane coupling agent, the method comprising, by hydrolyzing a compound represented by Formula (2), obtaining a compound represented by Formula (1) in the presence of water (0021-0022; no solvent). Yang does not teach said reaction should occur a condition of pH 4 or lower. However, Suzuki teaches said reaction to form an alkoxysilane hydrolytic condensate is accomplished by keeping the temperature of the system to no higher than 20° C., adding the acid catalyst to adjust the pH to a range of 1.0 to 4.0 and preferably pH 1.5 to 3.0, and then mixing the alkoxysilane, to produce an alkoxysilane hydrolysate, and then further adjusting it so that the desired alkoxysilane hydrolytic condensates are present in the prescribed amounts (0123). Thus, it would have been obvious to one of ordinary skill in the art at the time the invention was filed to hydrolyzing a compound represented by Formula (2) as taught in Yang at a pH of less than 4. The motivation for doing so would have been that Suzuki teaches such pH conditions are typical for such a reaction. The resulting composition reads on the silane coupling agent of claim 2 having a pH of 4 or lower.
With regard to claim 8, Yang teaches the silane composition is a functional additive, functioning as a coupling agent, but does not teach the silicon compound should be added in amounts from 0.01 to 40 parts by weight per 100 parts by weight of the curable compound. However, coupling agents are known in the art to be result effective variables that control the adhesion and distribution between two phases of a composite. Thus, it would have been obvious to one of ordinary skill in the art at the time the invention was made to optimize the amount of coupling agent added to the composition of CN. The motivation for doing so would have been to control the adhesion and distribution between two phases of a composite.
With regards to claim 9, CN teaches a laminate having a configuration in which a wafer and a wafer, a chip and a chip, or a wafer and a chip are laminated via the adhesive described in claim 7.
With regards to claim 10, CN teaches the adhesive is useful for laminating chips or wafers to three dimensional laminates such as LED elements (herein understood to read on the claimed semiconductor device of claim 10).
With regards to claim 13, With regard to claim 11, Yang teaches “the unreacted silane compound and a low condensate content of 20% or less” relative to the condensate. Said teaching understood to anticipate the claimed teaching.
With regards to claim 15, CN teaches the curable compound is an epoxy group-containing polyorganosilsesquioxane.
With regards to claim 16, CN teaches mixing the silicon coupling agent and the curable adhesive compound:
With regards to claim 17, Yang teaches “the unreacted silane compound and a low condensate content of 20% or less” relative to the condensate. Said teaching understood to anticipate the claimed teaching.
With regard to claim 19, CN teaches the curable compound is an epoxy group-containing polyorganosilsesquioxane.
With regards to claim 20, CN teaches a method comprising bonding a wafer and a wafer, a chip and a chip, or a wafer and a wafer together using the adhesive described in claim 7.
Response to Arguments
Applicants’ arguments filed 7/6/2026 have been fully considered but they are not persuasive.
Rejections under 35 U.S.C. § 103
With regards to the rejection of claims 1-6, 11, and 12 under 35 U.S.C § 103 as being unpatentable over Yang (JP H10251516A) in view of Suzuki (US 2017/00009034) and the rejection of claims 7-10 and 13-20 are rejected under 35 U.S.C § 103 as being unpatentable over CN(CN 109880583) in view of Yang and Suzuki, applicant requests reconsideration in light of the new claim set shown herein.
The Present Invention and Its Advantages
Applicants argue the accompanying Declaration under 37 C.F.R. § 1.132, including the resubmitted Certificate of Experimental Results, demonstrates the claimed invention requires maintaining a sufficiently high effective proportion of water during the hydrolysis stage while limiting the amount of organic solvent present during that stage. These conditions are important for actively generating compound (I), the complete hydrolysis product, and for obtaining the claimed [compound (T)/compound (II)] ratio. Said argument is noted but is not persuasive.
Applicant contends the Declaration/Certificate of Experimental Results confirms the technical significance of the conditions. Specifically, applicants contend in Comparative Example the
amount of ethanol present from the start of the reaction corresponded to approximately 0.99 parts by weight of ethanol per 1 part by weight of 3-glycidoxypropyltriethoxysilane. Although 6 equivalents of water were present, the conversion rate did not exceed approximately 20%, and the weight-average molecular weight remained below 200 even after 3 hours of heating. Applicant argues these results show that a high molar amount of water alone is insufficient. When a large amount of organic solvent is present from the initial stage of the reaction, hydrolysis and polycondensation do not proceed sufficiently, even if a large molar amount of water is added. The results also confirm that the compound (T)/compound (II) ratio does not satisfy the claimed range under the conditions of Comparative Example 1. In contrast, Example 1, in which ethanol was not added at the initial stage of the reaction, achieved 100% conversion and satisfied the claimed [compound (I)/compound (II)] ratio. Thus, controlling the organic solvent proportion during the initial hydrolysis stage is critical to achieving the claimed composition. Said argument is noted but is not persuasive. Even accepting, in arguendo, applicant’s arguments as persuasive, the arguments fail to establish that the claimed reaction conditions inherently result in a materially different product. For instance, the data presented fails to demonstrate the claimed reaction conditions result in a distinct product over the entirety of the claim scope. Applicant also notes that the comparative example is heated, but the claim is not limited with regards to the heating temperature or duration of said heating step Thus, it is unclear how the comparative example is sufficient to demonstrate the claimed method limitations inherently result in a patentably distinct product.
Applicants further ague the claimed invention also provides remarkable and unexpected results. Despite using a high water amount during hydrolysis and thereby producing a high silanol group concentration, applicants argue the present invention achieves both good storage stability and high adhesion strength, as shown in Tables 1 and 2 of the present specification and that the results would not have been predictable from the cited references. Said arguments are noted but are not persuasive. Initially, the examiner notes it is unclear how the data in Table 1 demonstrates the inventive composition has an “unexpected” storage stability. Furthermore, said argument is not persuasive as applicant has not demonstrated that the comparative examples are representative of the closest prior art or that the “unexpected” results are commensurate in scope with the pending claims.
(ii) Actual Disclosures in Cited References
Applicant argues Yang does not teach or suggest the claimed approach. Specifically, applicant argues a person of ordinary skill in the art would not have been motivated by Yang to intentionally increase the amount of water to the presently claimed range of from 3 to 12 mol per mol of the compound represented by Formula (2). Applicant further argues Suzuki does not cure these deficiencies because Suzuki does not teach or suggest using from 3 to 12 mol of water per mol of the compound represented by Formula (2) while simultaneously controlling the organic solvent amount to 0.7 parts by weight or less per part by weight of the compound represented by Formula (2), in order to generate and retain compound (I) within the claimed [compound (I)/compound (II)] ratio.. Said arguments are noted but are not persuasive as the courts have held a method of making a product does not patentably distinguish a claimed product from a product taught in the prior art unless applicant can demonstrate the method of making the product inherently results in a materially different product. In the present application, such a showing has not been made as detailed above. Thus, while Suzuki’s and Yang's approach may be different from the present invention, applicant has not demonstrated said differences inherently result in a materially different product.
Applicant further argues the present invention further differs from Yang in that the invention actively generates compound (I), a completely hydrolyzed product, and leaves a certain amount or more of compound (I) remaining so that the [compound (T)/compound (II)] weight ratio is from 1/99 to 95/5. Said argument is noted but is not persuasive. Specifically, the examiner took the position that Yang teaches the silicon compound comprising a compound (I) represented by Formula (1) and a polycondensate of the compound (I) (see “Problem to be Solved” and 0005 teaching “The unreacted substances and low-condensation products remaining in A…”), wherein a ratio of contents of the compound (I) to a compound (II) is from 1/99 to 95/5 (teaching “the unreacted silane compound and a low condensate content of 20% or less”), While applicant argues the present invention further differs from Yang in that the invention actively generates compound (I), a completely hydrolyzed product, and leaves a certain amount or more of compound (I) remaining so that the [compound (T)/compound (II)] weight ratio is from 1/99 to 95/, it is not clear what distinction applicant is attempting to make and how the examiner erred in applying the teachings of Yang.
Applicant argues the same deficiencies apply to the rejection based on CN 109880583 in view of Yang and Suzuki. The Office Action relies on Yang and Suzuki for features that are not taught or suggested by those references, including the claimed water amount, the claimed organic solvent limitation, and the claimed [compound (I)/compound (II)] ratio. Applicant argues CN 109880583 does not remedy these deficiencies or provide a reason to modify Yang in a manner directly contrary to Yang's teaching regarding storage stability. Said arguments are not persuasive for the reasons noted above. The examiner further notes claim 7 does not contain the same organic solvent limitation of claim 1; thus, applicant’s arguments with regards to claim 1 do not immediately seem relevant to claim 7.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KEVIN R KRUER whose telephone number is (571)272-1510. The examiner can normally be reached M-F 8am-5pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Callie Shosho can be reached at (571) 272-1123. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KEVIN R KRUER/Primary Examiner, Art Unit 1787
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