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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of Claims
The examiner acknowledges the amendments to claims 1, 6, 8, 14, and 18 as well as the cancellation of claims 2, 4, 7, and 9-10. Claims 1, 3, 5-6, 8, and 11-20 are pending.
Specification
The applicant has amended the specification to correct the noted errors. The objection to the specification has been withdrawn.
Claim Rejections - 35 USC § 112
The applicant has amended claim 6. As a result, the previous rejection under 112(b) has been withdrawn.
Claim Rejections - 35 USC § 102
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, 5-6, 8, 11 and 18-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nakakoji (JP 2021-075656, IDS Foreign Patent Reference #1 from IDS dated 7/30/2024, using JPO Machine Translation).
Regarding Claims 1, 3, 5-6 and 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. Nakakoji also teaches that the silane components can contain hydrogen, hydroxy, alkoxy, aliphatic and aromatic hydrocarbyl groups (Paragraph 33). Nakakoji further teaches that the silanes useful in the compound generated include curing groups including amine-containing silanes such as 3-aminopropyltrimethoxysilane, 3-aminophenyltrimethoxysilane (Paragraph 38), isocyanate containing silanes such as 3-isocyanatepropyltriethoxysilane (Paragraph 38), acrylate-containing silanes such as 3-methacryloxypropyl trimethoxysilane (Paragraph 38), epoxide-containing silanes such as gamma-glycidoxypropyltrimethoxysilane and beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (Paragraph 38) as well as vinyltrimethoxysilane and tetraethoxysilane (Paragraph 38) which meet the requirements of claim 5. 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).
Regarding Claim 11,
Nakakoji teaches that the compound may be generated from isosorbide (Paragraph 30) and alkoxysilanes of various types (Paragraph 38) as discussed above in regard to claims 1-6. Nakakoji further teaches that silanes may be used in combination (Paragraph 34) and additionally teaches that a combination containing a trialkoxysilane or a tetraalkoxysilane is preferrable (Paragraph 34) in order to obtain a branched structure (Paragraph 34). Nakakoji further 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).
Regarding Claim 8,
Nakakoji teaches a compound meeting the requirements of the instant claims as discussed above in relation to claims 1, 3, and 5-6. 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 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,Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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).
Claim Rejections - 35 USC § 103
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 12-17 and 20 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) as applied to claims 1-11 and 18-19 above.
Regarding Claims 12-13 and 20,
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 Claims 14-17,
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 14 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 16 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.
Response to Arguments
Applicant's arguments filed 4/16/2026 have been fully considered but they are not persuasive for the following reasons.
On page 14, the applicant argues that Nakakoji fails to teach all of the requirements of claim 1, specifically the molar ratios of organic group to silane and the number of silanes bonded to only oxygen. The examiner disagrees. While Nakakoji does not specifically mention these ratios, example 9 of table 1, which is formed through the reaction of 4.15 g of isosorbide (MW=146.142, 0.028 mol) and 14.32 g of 3-(trimethoxysilyl)propyl methacrylate (MW=248.35, 0.0576 mol), has an organic component fraction of 0.33 and a silyl component fraction of 0.67. As there is no component in this example with 4 Si-O bonds, g=0. Thus, while it is not explicitly stated, Nakakoji demonstrates a composition which meets the requirements. The prior art is not required to explicitly state that the composition meets the requirements when the examples demonstrate adherence to these requirements. With regard to the unexpected results, the examiner notes that the effects noted by the applicant to be associated with meeting the criteria above would be inherent in the composition of Nakakoji, as specifically example 9 of table 1 meets these criteria. "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). See MPEP 2112.I.
On page 15, the applicant argues that Nakakoji excludes water and therefore the reaction cannot be a hydrolysis reaction and that no siloxane bonds are formed. The examiner disagrees. While the applicant points to Nakakoji’s preference to exclude water in paragraph 53, this does not require the exclusion of water. Additionally, as Nakakoji uses base, specifically barium hydroxide (which the applicant includes in claim 13), the first step in the reaction between the components would be a deprotonation, as acid-base chemistry is faster than other reactions, which the ordinarily skilled artisan would no doubt be aware of. Thus, water would necessarily be generated in the first step of the reaction. Further, the applicant’s own specification notes “For the hydrolysis reaction, water may be additionally introduced.” (Paragraph 88), which would seem to indicate that water is not required to be added, undercutting this argument. As a result, in order for the applicant’s argument that no siloxane bonds are formed to be true, it would logically follow that because the applicant’s own conditions match those of Nakakoji, that this same issue would arise in the composition as detailed by the applicant as well.
In conclusion, Nakakoji demonstrates compositions that meet the requirements of the claims as detailed by the applicant and, as a result, the rejection is maintained.
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 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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Heidi Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.J.B./Examiner, Art Unit 1765 /HEIDI R KELLEY/Supervisory Patent Examiner, Art Unit 1765
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