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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 02/26/2026 has been entered.
Status of the Application
Claims 1-5 and 8-14 are pending and under current examination.
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 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 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-5 and 8-14 are rejected under 35 U.S.C. 103 as being unpatentable over Langer (The Journal of Organic Chemistry, 23(1):50-58, 1958; as provided by the applicant on IDS dated 01/26/2023), and Grinberg (Russian Journal of Applied Chemistry, 84(11):1909-1913 (2011); as provided by the applicant on IDS dated 01/26/2023) in combination.
Determining the scope and contents of the prior art
Langer teaches synthesis of alkoxysilane using hexamethyldisilazane and an alcohol (with examples, such as ethanol, propanol etc., same as in the instant claims) and how availability of proton (i.e., presence of an acid) may catalyze the reaction:
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Since the reaction taught by the cited prior art is same, the NH3 released or contained in the reaction mixture is same as in the instant claims, whether or not measured or recognized by the cited prior art. Thus, the cited prior art reads on the limitation of the instant claims.
Langer further teaches synthesis of alkoxysilane using trimethylchlorosilane with alcohol (with examples, such as ethanol, propanol etc., same as in the instant claims):
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and how the reaction equilibrium shifts to completion by addition of amine (entire article). According to the reaction taught by the cited prior art, Formula (2) and amine used are equivalent and thus reads on the limitation of the instant claims. Because of increased efficiency of reaction for preparation of alkoxysilane from silazane in presence of proton and increased efficiency of reaction for preparation of alkoxysilane from chlorosilane in presence of ammonia, Langer further teaches coupling both reactions i.e., silazane with alcohol and chlorosilane with alcohol and using undesirable byproduct NH3 and HCl of these reactions respectively and producing a byproduct ammonium salt, which is easily separable:
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(entire article). According to the reaction taught by the cited prior art, Formula (2) (1 equivalent) and NH3 released in situ (1 equivalent) are equivalent and thus reads on the limitation of the instant claims. Langer further teaches how presence of acid in silazane reaction for making alkoxysilane is catalyzed by the presence of acid (entire article)
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. Langer further teaches that after the reaction, precipitate of ammonium chloride was filtered and washed and the organic layer with product is further purified by distillation.
Ascertaining the differences between the prior art and the claims at issue
Langer teaches separate reactions of (1) silazane with alcohol forming alkoxy silane with advantage of using acid, (2) reaction of trimethylchlorosilane with alcohol forming alkoxy silane with advantage of using amine and (3) coupling of these reactions for forming easily separable byproduct ammonium chloride, which is separated from the reaction by filtration. However, the cited prior is silent about doing reaction (1) followed by adding reactants of reaction (2) and reaching to reaction (3); separating ammonium salt using aqueous solvent; acid catalyst for reaction one is acid, such as HCl; measuring ammonia from reaction (1); and two different alcohols are used in reaction (1) and reaction (2).
Resolving the level of ordinary skill in the pertinent art
With regard to the difference of doing reaction (1) followed by adding reactants of reaction (2) and reaching to reaction (3)- Langer teaches separate reactions of (1) silazane with alcohol forming alkoxy silane with advantage of using acid, (2) reaction of trimethylchlorosilane with alcohol forming alkoxy silane with advantage of using amine and (3) coupling of these reactions for forming easily separable byproduct ammonium chloride, which is separated from the reaction by filtration. With the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill with a reasonable expectation of success that coupling of reaction (1) and (2) may be done by combining both reactions together in one step as taught by the cited prior art or reaction (1) may be done separately followed by combining with reaction (2) to form alkoxysilane with same advantage of using byproduct of one reaction to catalyze the co-reaction.
Further, case law has established that one step process is obvious over two step process, because in the one pot process the multi-steps manipulated in one step, which mean the reactant and intermediates further proceed to the next step for the completion to achieve the final product.
It is well established that batch and continuous processes are not patentably distinct. See, e.g., In re Dilnot, 319 F.2d 188, 138 USPQ 248 (CCPA 1963).
Additionally, case law has established that “Since the claimed process and article produced therby are no more than a selective combination of prior art teachings, done in a manner obvious to one of ordinary skill in the art, since each step of the process appears to be realtively complete in itself and there is no indication of an interaction between steps of such a type that would lead one of ordinary skill in the art to doubt that a substitution of alternative steps known to the art could be made”. In re Mostovych 144USPQ 38 (1964). Thus, the cited prior art meets limitation of the instant claims.
With regard to the difference of separating ammonium salt using aqueous solvent- Langer teaches filtration of the salt and distillation of the organic layer for further purification. Since separation of inorganic salt such as ammonium chloride, NaCl etc., through filtration as taught by Langer or by dissolving in aqueous solvent, such as water as taught by Grinberg (entire article, especially page 1909) or combination of both to achieve purity of product is carried out routinely in the field of organic chemistry, it would have been prima facie obvious to a person of ordinary skill in the art that either filtration or dissolution in aqueous solvent or both may be carried out to purify product from inorganic salt impurities.
With regards to the difference of using acid, such as HCl-Langer teaches that silazane reaction with alcohol (1) is catalyzed by an acid. Further, Langer teaches ammonia released in the reaction (1) is neutralized by HCl formed through reaction of chlorosilane and alcohol (2) forming ammonium chloride in the combined reaction. Thus, it would have been prima facie obvious to a person of ordinary skill in the art reaction (1), if desired may be catalyzed by acid and acid, such as HCl as suggested by the cited prior art.
With regards to use of two different alcohols used in reaction (1) and reaction (2)-Langer teaches reaction (1) of silazane with different examples of alcohols forming alkoxy silane and reaction (2) of chlorosilane with examples of different alcohols forming alkoxy silane. Thus, it would have been prima facie obvious to a person of ordinary skill in the art that depending on desired product either same alcohol or different alcohols may be utilized to form alkoxysilane or mixtures of alkoxysilane.
With regards to measuring ammonia produced in reaction (1)- Langer teaches increased efficiency of reaction (1) for preparation of alkoxysilane from silazane in presence of proton and increased efficiency of reaction for preparation of alkoxysilane from chlorosilane in presence of ammonia, Langer further teaches coupling both reactions i.e., silazane with alcohol and chlorosilane with alcohol and using undesirable byproduct NH3 and HCl of these reactions respectively and producing a byproduct ammonium salt, which is easily separable. Since reaction (1) is catalyzed by presence of proton (due to consumption of byproduct of the reaction NH3) and reaction (2) is catalyzed by NH3 (due to consumption of product HCl and shift of equilibrium), it would have been prima facie obvious to a person of ordinary skill in the art to measure amount or theoretically predict amount of NH3 and HCl in reaction (1) and (2) respectively to drive the reaction. Thus, the cited prior art meets all limitations of the instant claims.
Therefore, combination reads applicants claims.
Based on the above established facts, it appears that the combination of teachings of above cited prior art read applicants’ process.
Therefore, all the claimed elements were known in the prior art and one skilled person in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art at the time of the invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness
To establish a prima facie case of obviousness, three basic criteria must be met: (1) the prior art reference must teach or suggest all the claim limitations; (2) there must be some suggestion or motivation, either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, to modify the reference or to combine reference teachings; and (3) there must be a reasonable expectation of success; and (MPEP § 2143).
In this case, Langer teaches separate reactions of (1) silazane with alcohol forming alkoxy silane with advantage of using acid, (2) reaction of trimethylchlorosilane with alcohol forming alkoxy silane with advantage of using amine and (3) coupling of these reactions for forming easily separable byproduct ammonium chloride, which is separated from the reaction by filtration and Grinberg teaches separation of ammonium chloride using aqueous medium.
So, the combination of prior art read applicants claims.
In KSR International Vo. V. Teleflex Inc., 82 USPQ2d (U.S. 2007), the Supreme Court particularly emphasized “the need for caution in granting a patent based on a combination of elements found in the prior art,” (Id. At 1395) and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “[t]he combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” (Id. At 1395). See MPEP 2143 - Examples of Basic Requirements of a Prima Facie Case of Obviousness [R-9].
In this case at least prong (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success would apply.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.” KSR, 550 U.S. at ___, 82 USPQ2d at 1397. If any of these findings cannot be made, then this rationale cannot be used to support a conclusion that the claim would have been obvious to one of ordinary skill in the art. It is well within the skill of the organic chemist to recognize the fact that applicants claimed process is nothing but the combination of known individual chemical processes. Further, there is a reasonable expectation of success that NH4Cl may be separated from the reaction mixture by filtration or use of aqueous solvent and can be made by combination of the above cited prior art.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking the advantage of the teaching of the above cited references and to make the instantly claimed process with a reasonable expectation of success. Modifying such parameters is prima facie obvious because an ordinary artisan would be motivated to develop an alternative process for economic reasons or convenient purposes from a known individual reaction steps, and to arrive applicants process with a reasonable expectation of success, since it is within the scope to modify the process through a routine experimentation.
Response to Arguments
Applicant’s remarks, filed on 02/26/2026, have been fully considered but not found persuasive.
Applicant argued that NH3 is volatile and some of NH3 gas escapes from first mixture thereby reducing amount of NH4Cl to be removed. Applicant argued over measuring amount of NH3 and using Formula 2 equivalent to measured NH3 and how excess of formula 2 in the reaction may produce side products. Applicant also argued that how halogen, such as Cl is not present in Formula 1 and thereby NH3 is available to produce additional product. Applicant argued using specific examples of formula I as HMDS, formula 2 as TMCS, formula 3 as ethanol producing TMES as formula 4 that according to process of the instant claims NH3 is generated and discharged outside of the reaction system and residual NH3 is removed through step 2 producing a small amount of NH4Cl, which is dissolved in aqueous solvent for separation from the product Vs Langer’s process generating a large amount of NH4Cl generating problem.
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This is not found persuasive and the instant claims stand rejected under 103. This is because applicant is arguing over a limitation “that NH3 is discharged from reaction mixture 1 thereby producing less NH4Cl at the end of step 2”, not recited in the instant claims. The instant claims also lead to formation of NH4Cl salt at the end of step 2. In contrast to applicant’s argument, Langer nowhere teaches “too much amount of NH4Cl”. Importantly, Langer also teaches using one equivalent of compound same as Formula (2), which is same equivalent as amount of NH3 released in situ from reaction of Formula (1) with alcohol. Langer teaches separate reactions of (1) silazane with alcohol forming alkoxy silane with advantage of using acid, (2) reaction of trimethylchlorosilane with alcohol forming alkoxy silane with advantage of using amine and (3) coupling of these reactions for forming easily separable byproduct ammonium chloride, which is separated from the reaction by filtration. With the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill with a reasonable expectation of success that coupling of reaction (1) and (2) may be done by combining both reactions together in one step as taught by the cited prior art or reaction (1) may be done separately followed by combining with reaction (2) to form alkoxysilane with same advantage of using byproduct of one reaction to catalyze the co-reaction.
Further, case law has established that one step process is obvious over two step process, because in the one pot process the multi-steps manipulated in one step, which mean the reactant and intermediates further proceed to the next step for the completion to achieve the final product.
It is well established that batch and continuous processes are not patentably distinct. See, e.g., In re Dilnot, 319 F.2d 188, 138 USPQ 248 (CCPA 1963).
Additionally, case law has established that “Since the claimed process and article produced therby are no more than a selective combination of prior art teachings, done in a manner obvious to one of ordinary skill in the art, since each step of the process appears to be relatively complete in itself and there is no indication of an interaction between steps of such a type that would lead one of ordinary skill in the art to doubt that a substitution of alternative steps known to the art could be made”. In re Mostovych 144USPQ 38 (1964). Thus, the cited prior art meets limitation of the instant claims.
Applicant argued that NH3 escape is a natural consequence and it is not required to be expressly recited in claim 1.
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This is not found persuasive and the instant claims stand rejected. This is because (1) a reaction can be carried out in reactor that may not allow gas or NH3 to escape; (2) the instant specification specifically recites benefitting from presence of NH3 to carry out reaction with Formula (2) and alcohol, same as the cited prior art.
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Since NH3 is made as an essential part of carrying out the reaction, raises the question if the NH3 was allowed to escape from the process. If NH3 was allowed to escape, it must be present in the specification and in the claims; (3) all process steps, examples and specified example in the argument uses exactly one equivalent of Formula (2), which is same as 1 equivalent of NH3 released and raises question about any escape of NH3.
Applicant argued that Grinberg does not disclose step 1 and 2 of the instant claims. Grinberg uses NaOH aqueous solution for separation instead of aqueous solvent.
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This is not found persuasive and the instant claims are obvious in view of the cite prior art. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In this case, Langer teaches the applicant’s process with a difference of removing NH4Cl salt from the product through filtration and not through liquid-liquid separation, a known and routinely used process in the organic chemistry and Greenberg was used to provide that such process is a well-known process for separating salts soluble in aqueous media. Specifically, Langer teaches filtration of the salt and distillation of the organic layer for further purification. Since separation of inorganic salt such as ammonium chloride, NaCl etc., through filtration as taught by Langer or by dissolving in aqueous solvent, such as water as taught by Grinberg (entire article, especially page 1909) or combination of both to achieve purity of product is carried out routinely in the field of organic chemistry, it would have been prima facie obvious to a person of ordinary skill in the art that either filtration or dissolution in aqueous solvent or both may be carried out to purify product from inorganic salt impurities. With regards to applicant’s argument regarding aqueous solution vs aqueous solvent-the instant claims recite “comprising” and may include any step or ingredient in the step. With regards to applicant’s argument amount additional teaching of Greenberg about NaOH particles, additional teaching of Greenberg regarding other compounds, by products etc. does not preclude teaching of Greenberg that liquid-liquid separation is a well-known process carried out routinely in chemistry.
Applicant argued over comparative data that comparative examples are similar to Langer reflux time and distillation steps:
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This is not found persuasive and the instant claims stand rejected. This is because (1) contrary to applicant’s argument no reflux conditions are recited in the instant claims. Thus applicant is arguing and compsring limitations not recited in the instant claims; (2) applicant comparaison is not a true comparison as applicant is picking and choosing process parts of the cited prior art. If applicant needs to provide comparative data, applicant may compare complete process of the cited prior art Vs instant claims; (3) Neither comparative 2 nor comparative 3 represents process of the cited prior art.
Conclusion
No Claim is allowed.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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