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
This application claims priority to U.S. Provisional Application Serial No. 63/386,231, filed on December 6, 2022.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 12/05/2023, 02/09/2024, 05/01/2024, 05/23/2024, 07/16/2024, 08/05/2024, 09/19/2024, 01/09/2025, and 03/27/2025 were filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Status of the Application
Applicant's election without traverse of Group I, claims 1-19 in the reply filed 04/13/2026 is acknowledged.
Claims 1-22 are pending. Claims 20-22 have been withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Claims 1-19 are currently under examination.
Specification
The disclosure is objected to because of the following informalities: IDS dated 09/19/2024 is missing name of patentee.
Appropriate correction is required.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-13 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Li (Novel silicone aliphatic amine curing agent for epoxy resin: 1,3-Bis(2-aminoethylamino methyl, tetramethyldisiloxane. 1. Non-isothermal cure and thermal decomposition property 2012, pgs. 75-81).
Li teaches the characterization and synthesis of 1,3-bis(2-aminoethylamino methyl) tetramethyl disiloxane (SFA), wherein ethylenediamine and chloromethyl ethoxy dimethyl silane are combined with a magnetic stirrer for a total of 4 hours in a first reaction prior to a second reaction wherein the raw product from the first reaction and distilled water are combined for a period of 2 hours to form the SFA product at 76% yield (2.2, pg. 76). Li’s compound of SFA anticipates the compound of formula I and formula IV (R18 and R19) and the 7th compound of instant claim 3 where R12-15 are methyl, R16 and R17 are CH2, R25-26, R29-32 and R36 are H, R33 and R34 are C and m is 0.
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1,3-bis(2-aminoethylaminomethyl) tetramethyl disiloxane (SFA)(Above)
Applicants disiloxane compound of instant claim 3 (Below)
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Regarding claim 4, Li’s use of ethylenediamine (bottom right) anticipates the compound of formula II of the instant claims where R1-2 and R5-8 are H, R9 and R10 are C and n is 0.
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Regarding claims 5 and 6, Li’s disclosure of chloromethylethoxydimethylsilane (Bottom Right) anticipates the compound of formula III (Bottom Left) of the instant claims where R24 is a C2 alkyl, R21-22 are methyl, R23 is CH3 and R20 is Cl.
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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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claim 1-19 is rejected under 35 U.S.C. 103 as being unpatentable over Li (Novel silicone aliphatic amine curing agent for epoxy resin: 1,3-Bis(2-aminoethylamino methyl, tetramethyldisiloxane. 1. Non-isothermal cure and thermal decomposition property 2012, pgs. 75-81) in view of Lee (Organic–inorganic hybrid materials from a new octa(2,3-epoxypropyl)silsesquioxane with diamines, Polymer, Volume 46, Issue 7,2005).
The instant claims are directed to a method of preparing an aminoalkyl-substituted disiloxane by:
I) forming a mixture of a di- or polyamine containing at least one primary amine group; and a silane;
II) reacting the mixture in a first reaction by stirring for a period of 1 second to 12 hours
Ill) adding a hydrolysis agent of water to the mixture over a period of 1 second to 12 hours; and
IV) reacting the mixture in a second reaction to form the aminoalkyl-substituted
disiloxane. Followed by purifying the aminoalkyl-substituted disiloxane and at least one step involves adjusting temperature by cooling the mixture.
Li et al. teach the characterization and synthesis of 1,3-bis(2-aminoethylaminomethyl) tetramethyl disiloxane (SFA), wherein ethylenediamine and chloromethylethoxydimethylsilane are combined with a magnetic stirrer for a total of 4 hours in a first reaction prior to a second reaction of the raw product and distilled water are combined for a period of 2 hours wherein the SFA was produced at 76% yield with vacuum distillation (2.2, pg. 76). Li discloses “Lee and Chen [8] synthesized a POSS-contained epoxy resin, octa(2,3-epoxypropyl)silsesquioxane, from octa-allylsilsesquioxane with m-chloroperebenzoic acid, and cured them with methylenedianiline (DDM). The cured materials showed storage modulus of 1.8 GPa (30°C)” (introduction, pg. 75).
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Applicants disiloxane compound of instant claim 3 (Below)
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However, Li et al. fail to disclose a one pot synthesis or adding the hydrolysis agent dropwise or cooling the mixture in the second synthesis.
Lee et al. teach a one pot synthesis of Octaallylsilsesquioxane (OA) wherein “[i]nto a 100 ml three-necked round bottom flask were added 10.29 g H2O (0.571 mmol), 0.8 g concentrated HNO3, and 2.93 g DMSO (0.038 mmol). 30.94 g ATMS (0.181 mol) and another 5.87 g (0.075 mol) DMSO were mixed and placed in an addition funnel and added dropwise into the flask in 3 h at 60 °C. Upon completion of addition, the mixture was allowed to react for 6 h and then cool to room temperature, kept in dark at ambient for crystallization around 10 days.” (2.2, pg. 2165) Lee also discloses “Although the yield of present synthesis is only 1.75%, the crystalline product is essentially pure and does not require sophisticated purification process” (2.2, pg. 2165)
Therefore, it would have been prima facie obvious to a person of ordinary skill in the art, prior to the effective filing date of the instant application, to combine Li’s methods of synthesizing 1,3-bis(2-aminoethylaminomethyl) tetramethyl disiloxane (SFA) using the reagents of ethylenediamine and chloromethylethoxydimethylsilane using known techniques of stirring, purification by vacuum distillation and adjusting temperature, with Lee’s disclosure of dropwise addition of water through an addition funnel in a one pot process to synthesize an aminoalkyl-substituted disiloxane because a skilled artisan would have considered the methods Li referenced Lee’s methods of synthesizing octa(2,3-epoxypropyl)silsesquioxane and would have also seen the synthesis of Octaallylsilsesquioxane (OA), adapting the process for the required application such as scalability, cost, purity or synthesis time of SFA. See MPEP 2144.05(II)
A person of ordinary skill in the art would have been motivated to synthesize the aminoalkyl-substituted disiloxane of 1,3-bis(2-aminoethylaminomethyl) tetramethyl disiloxane
(SFA),by following Li’s disclosure of forming a mixture of a di- or polyamine containing at least one primary amine group; and a silane using the reagents of ethylenediamine and chloromethyl ethoxydimethylsilane and reacting the mixture in a first reaction by stirring for a period of 3 hours followed by 1 hour. Followed by adding a hydrolysis agent of water to the mixture over a period of 3 hours as disclosed by Lee and reacting the mixture in a second reaction to form the aminoalkyl-substituted disiloxane followed by purifying the aminoalkyl-substituted disiloxane by either vacuum distillation of crystallization and optimizing the temperature of the reaction by cooling the mixture. A skilled artisan, following the teachings of Li and Lee would have had a reasonable expectation of success in synthesizing the compound of an aminoalkyl-substituted disiloxane of SFA.
Conclusion
All claims are rejected, no claims are allowed.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERNESTO VALLE JR whose telephone number is (703)756-5356. The examiner can normally be reached 0730-1700 M-F EST, 1st Friday off.
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/E.V./Examiner, Art Unit 1623
/SAMANTHA L SHTERENGARTS/Primary Examiner, Art Unit 1623
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