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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 7/20/2026 has been entered.
Status of Claims
The examiner acknowledges the amendments made to claims 1, 8, 12, 13, 15, 17, and 18 as well as the cancelation of claims 5, 11, 14, 16, and 20. Claims 1, 3, 6, 8, 12-13, 15, and 17-19 are pending.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 3, 6, 8, 12-13, 15, and 17-19 are rejected under 35 U.S.C. 103 as being unpatentable over Nakakoji (JP 2021-075656, IDS Foreign Patent Reference #1 from IDS dated 7/30/2024, using JPO Machine Translation).
Regarding Claims 1, 3, 6, 15, and 17-18,
Nakakoji teaches a compound that is a reaction product of an organic compound with two hydroxyl groups and an alkoxysilane (Paragraph 6) and further elaborates that the organic compound may be isosorbide (Paragraph 30) and further demonstrates its use in this capacity in Table 1 example 9.
In table 1 example 9 Nakakoji teaches an example where the isosorbide constitutes 33% by mole of the compound (equivalent to component e and to value h) with the remainder being represented by silane with a single non-alkoxy substituent (equivalent to component a and value f) and where no silicon species has 4 bonds to oxygen, (equivalent to d=0 and g=0). With regard to the requirement of containing a siloxane bond, Nakakoji teaches that the structure of the compound is of the following form:
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and also teaches that monoalkoxysilanes can be used to adjust the molecular weight of the silicon containing component (Paragraph 35). Additionally, Nakakoji teaches that the functional group ratio between the silane and the organic component is from 1:5 to 5:1 (Paragraph 55) and that the silicon atom in the above formula may have siloxane bonds (Paragraph 23).
Nakakoji teaches alkoxysilanes containing a variety of curable groups, which include 3-glycidoxypropyltrimethoxysilane and 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (Paragraph 38), meeting the requirements of claims 1 and 15. Nakakoji further teaches the use of isocyanate-containing silanes such as 3-isocyanatepropyltriethoxysilane (Paragraph 38) as well as amine-containing silanes such as N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and 3-aminophenyltrimethoxysilane (Paragraph 38), meeting the requirements of claims 1 and 17. While Nakakoji does not explicitly demonstrate the combination of an isosorbide reacted with an epoxy, isocyanate, or amine containing silane, Nakakoji does note that it is preferable to use 2-(3,4-epoxycyclohexyl)ethyltrimethoxy silane and 3-glycidoxypropyltrimethoxysilane (Paragraph 38) in addition to noting the use of amine and isocyanate-containing silanes. One of ordinary skill in the art would recognize that the reactive functional group on the silane determines the conditions required for curing and would be motivated to use a curable group that is fit for purpose for the desired application. It would have been obvious prior to the effective filing date of the instant application to have used an epoxy-containing silane as Nakakoji expresses a preference for this reactive group and additionally it would have been obvious prior to the effective filing date of the instant application to have used an isocyanate or amine-containing silane as the curable group in order to tailor the curing conditions to the desired application.
Regarding Claim 8,
Nakakoji teaches a compound meeting the requirements of the instant claims as discussed above in relation to claims 1, 3, and 6. Nakakoji further teaches that the compound is generated by the reaction of alkoxysilanes with the hydroxyl group of the organic compound (Paragraph 39), which would result in the formation of a silyl ether bond.
Regarding Claims 12 and 13,
Nakakoji teaches that the compound is formed through the reaction of the alkoxysilane which then reacts with a hydroxyl group of the organic component in a condensation reaction (Paragraph 39). Nakakoji also teaches that the compound may include siloxane bonds (Paragraph 23). While Nakakoji is silent on the formation of siloxane bonds, because Nakakoji teaches that the compound may have siloxane bonds and that the reactions taking place are hydrolysis and condensation, one of ordinary skill in the art would recognize that siloxane bonds would potentially form under the reaction conditions. Further, the conditions utilized by Nakakoji are broadly similar to those of the instant application, it would logically follow that similar reactions in similar proportions would be occurring. Combined with Nakakoji teaching that the functional group ratio is to be between 5:1 to 1:5 of the silane relative to the organic group (Paragraph 55), the ordinarily skilled artisan would realize that some siloxane bond formation occurs through the mechanisms of the instant claim. As such, it would have been obvious prior to the effective filing date of the instant application to have formed siloxane bonds in the organic-silane compound. Regarding the catalyst, Nakakoji teaches the use of acids such as hydrochloric, nitric, and sulfuric (Paragraph 49), bases such as potassium and sodium hydroxide (Paragraph 42) or barium hydroxide (Paragraph 43), and nitrogen-containing catalysts such as imidazole (Paragraph 48).
Regarding Claim 19,
Nakakoji teaches the organic-silane based compound as required in the instant claims as described in regard to claims 1, 3, 5-6, and 18 above. Nakakoji further teaches a composition containing this compound that contains a polymerization initiator (Paragraph 66), additives such as aluminum oxide (alumina, Paragraph 61), and carbon nanomaterials including graphene and fullerene (Paragraph 65), and other additives such as ethylene oxide polymers (Paragraph 72) and diethylene glycol and triethylene glycol (Paragraph 74). Nakakoji teaches that the initiator can be a photoacid generator (Paragraph 70).
Response to Arguments
Applicant's arguments filed 7/202/2026 have been fully considered but they are not persuasive for the following reasons.
On page 9, the applicant argues that Nakakoji does not teach a combination of a structural body comprising a siloxane bond and where the reactive group is an epoxy, amine, mercapto, carboxyl, nitro, sulfone, hydroxyl, urethane, ureide, isocyanate, oxetane, or combinations thereof. The examiner disagrees, as is pointed out in the above rejection, as Nakakoji teaches the use of isosorbides reacted with silanes that include amines, isocyanates, and epoxides (Paragraph 38). As Nakakoji is reacted the isosorbide with the silane and in particular with siloxanes in excess, the structure formed would include siloxane bonds as is also noted in the rejection above.
On page 10, the applicant argues that the technical feature is the formation of a “first structure” which is the reaction of a silane and isohexide with the required formula. However, as the examiner notes in the rejection, Nakakoji teaches a method that combines the required components in the required amounts and does so using conditions broadly similar to those of the instant claims and, as a result, would result in a compound that would meet the requirements.
Also on page 10, the applicant argues desirable properties that result from the use of compositions that meet the requirements of the instant claims. The examiner points out that the properties mentioned by the applicant do not appear as limitations in the current claims and that furthermore, these properties would be tied to the composition itself. As Nakakoji teaches the use of the required components within the required amounts, it would logically follow that the resulting compounds would possess these properties as well.
Additionally, on page 10, the applicant argues that by excluding methacrylates as the reactive group that Nakakoji does not teach the required structures, which is addressed above.
Finally, on page 10, the applicant argues that the same arguments apply to the other independent claims and would thus be allowable. These arguments have been addressed above and apply to the other independent claims as well, as these claims contain the same limitations to those of claim 1.
Ultimately, the applicant’s amendments, while removing the 102 rejection of the previous office action, do not preclude a rejection under 35 U.S.C. 103, which has been included in the current office action. As a result, the application remains rejected.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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/A.J.B./Examiner, Art Unit 1765
/HEIDI R KELLEY/Supervisory Patent Examiner, Art Unit 1765
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