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.
Specification
The disclosure is objected to because of the following informalities:
On page 3 paragraph 12, page 15 paragraph 84, and page 16 paragraph 86 the applicant refers to a compound as isomanide, however there does not appear to be a compound by this name.
On page 17 in paragraph 87, the applicant refers to a paper cyclic group, but it is unclear what this terminology means.
On page 19 in paragraph 96, the applicant refer to a compound as isoprondiamine, however there does not appear to be a compound by this name.
On page 22 in paragraph 98, the compound para-aminobenzoic acid appears to be missing a hyphen in its name. In the same paragraph, the applicant appears to be missing a space between the words a and reducing as well as having an extra space following formic acid. Finally, on page 23 in the same paragraph, the final sentence is not phrased in a grammatically correct fashion.
On page 23 in paragraph 99, the applicant refers to a compound as ditoliliodonium hexafluorophosphate salt, but there does not appear to be a compound by this name.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 6 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
In claim 6, the applicant limits the isohexide to be “at least one of isosorbide, isomanide, isoidide, or a combination thereof”, however it is unclear what compound isomanide represents, rendering the claim indefinite. The applicant is required to revise the claim language to clarify what compounds can be utilized.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-11 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 1-6 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 claims 2 and 5. In table 1 example 9 Nakakoji teaches an example where the isosorbide constitutes 33% by mole of the compound (equivalent to component e) with the remainder being represented by silane with a single non-alkoxy substituent (equivalent to component a), meeting the requirements of claim 4.
Regarding Claims 7 and 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 Claims 8-10,
Nakakoji teaches a compound meeting the requirements of the instant claims as discussed above in relation to claims 1-6. 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 1-6 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).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 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 hydrolysis 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.
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
/JOHN M COONEY/Primary Examiner, Art Unit 1765