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 .
Status of the Application
Claims 1-6, 10-15 and 17-25 are pending and under current examination.
Amendment necessitated new claim rejection as set forth below.
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 1-6, 10-15 and 17-25 are rejected under 35 U.S.C. 103 as being unpatentable over Jantke (US2020/0270284 A1), Young (Cyanide Remediation; Current and Past Technologies, 1995; as provided by the applicant on IDS dated 11/14/2022) and Armarego (“Purification of Organic Chemicals-Aliphatic Compounds”, Elsevier Science & Technology, 2009, pg 98; as provided by the applicant on IDS dated 11/14/2022) and Frank (EP2221310 A1; as provided by the applicant on IDS dated 11/14/2022) in combination.
Determining the scope and contents of the prior art
Jantke teaches a method of making R1xR2SiX(3-x), with example of 4-(Dialkylchlorosilyl)-Butyronitrile, X=Cl, R1=CH3, R2=NCD, D=divalent hydrocarbon group; and x=2 (same product as in the instant claim 15); comprising reacting pure olefinic nitrile with example of allyl cyanide (3-butenenitrile) (0.45mol) (same reactant as in the instant claims 1-6, 10-15 and 17-25), having less than 0.1 part by weight of HCN (less than 100ppm), preferably less than 0.01 part by weight of HCN (less than 10ppm),
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hydridosilane, with example of dimethylchlorosilane (0.54mol) (same reactant as in the instant claims 1-3, 6, 10-15 and 17-25) in the presence of platinum catalyst with example of Karstedt’s catalyst in solvent (same catalyst as in the instant claims 1-6, 10-15 and 17-25) that provides 35micromol or 78ppm Pt based on allyl nitrile (i.e., 78ppm based on 0.45mol of allyl nitrile; hydridosilane used=0.54mol, thus Pt based on A, B and C (total moles of Pt based catalyst (0.000035M (negligible), allylnitrile (0.45M, Pt is 78ppm based on allylnitrile) and hydridosilane(0.54M is 1.2 of 0.45 ) =~65ppm)), at temperature of 60C-120C with example of 80-100C (entire application, especially paragraphs 0015-0018, 0023-0045, and claims).
Ascertaining the differences between the prior art and the claims at issue
Jantke teaches a method of making R1xR2SiX(3-x) using reactants pure olefinic nitrile, hydridosilane, Karstedt’s catalyst in solvent, and temperature as in the instant claims, but fails to teach the process of purification of olefinic nitrile from cyanide impurity; olefinic nitrile impurity before and after purification, such 7.5ppm, 5.2ppm; reduction in cyanide impurity in step2; hydridosilane with X as methoxy group; and use of promoter in the process.
Resolving the level of ordinary skill in the pertinent art
With respect to purification of olefinic nitrile from cyanide impurity; olefinic nitrile impurity before and after purification, such 7.5ppm, 5.2ppm; reduction in cyanide impurity in step2- Jantke teaches using purified olefinic nitrile having impurity of HCN as less than 100ppm or preferably less than 10ppm. Thus, given the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that the process requires using pure olefinic nitrile devoid of HCN impurity or impurity of HCN less than 100ppm or preferably less than 10ppm. Further, less than 10ppm impurity of HCN of the cited prior art encompass range of 7.5ppm and 5.2ppm or close to 7.5ppm and 5.2ppm
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) (The prior art taught carbon monoxide concentrations of "about 1-5%" while the claim was limited to "more than 5%." The court held that "about 1-5%" allowed for concentrations slightly above 5% thus the ranges overlapped.); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997) (Claim reciting thickness of a protective layer as falling within a range of "50 to 100 Angstroms" considered prima facie obvious in view of prior art reference teaching that "for suitable protection, the thickness of the protective layer should be not less than about 10 nm [i.e., 100 Angstroms]." The court stated that "by stating that ‘suitable protection’ is provided if the protective layer is ‘about’ 100 Angstroms thick, [the prior art reference] directly teaches the use of a thickness within [applicant’s] claimed range."). See also In re Bergen, 120 F.2d 329, 332, 49 USPQ 749, 751-52 (CCPA 1941) (The court found that the overlapping endpoint of the prior art and claimed range was sufficient to support an obviousness rejection, particularly when there was no showing of criticality of the claimed range).
Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985) (Court held as proper a rejection of a claim directed to an alloy of "having 0.8% nickel, 0.3% molybdenum, up to 0.1% iron, balance titanium" as obvious over a reference disclosing alloys of 0.75% nickel, 0.25% molybdenum, balance titanium and 0.94% nickel, 0.31% molybdenum, balance titanium. "The proportions are so close that prima facie one skilled in the art would have expected them to have the same properties."). See also Warner-Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S. 17, 41 USPQ2d 1865 (1997) (under the doctrine of equivalents, a purification process using a pH of 5.0 could infringe a patented purification process requiring a pH of 6.0-9.0); In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%); In re Scherl, 156 F.2d 72, 74-75, 70 USPQ 204, 205-206 (CCPA 1946) (prior art showed an angle in a groove of up to 90° and an applicant claimed an angle of no less than 120°); In re Becket, 88 F.2d 684 (CCPA 1937) ("Where the component elements of alloys are the same, and where they approach so closely the same range of quantities as is here the case, it seems that there ought to be some noticeable difference in the qualities of the respective alloys."); In re Dreyfus, 73 F.2d 931, 934, 24 USPQ 52, 55 (CCPA 1934)(the prior art, which taught about 0.7:1 of alkali to water, renders unpatentable a claim that increased the proportion to at least 1:1 because there was no showing that the claimed proportions were critical); In re Lilienfeld, 67 F.2d 920, 924, 20 USPQ 53, 57 (CCPA 1933)(the prior art teaching an alkali cellulose containing minimal amounts of water, found by the Examiner to be in the 5-8% range, the claims sought to be patented were to an alkali cellulose with varying higher ranges of water (e.g., "not substantially less than 13%," "not substantially below 17%," and "between about 13[%] and 20%"); K-Swiss Inc. v. Glide N Lock GmbH, 567 Fed. App'x 906 (Fed. Cir. 2014)(reversing the Board's decision, in an appeal of an inter partes reexamination proceeding, that certain claims were not prima facie obvious due to non-overlapping ranges); In re Brandt, 886 F.3d 1171, 1177, 126 USPQ2d 1079, 1082 (Fed. Cir. 2018)(the court found a prima facie case of obviousness had been made in a predictable art wherein the claimed range of "less than 6 pounds per cubic feet" and the prior art range of "between 6 lbs./ft3 and 25 lbs./ft3" were so mathematically close that the difference between the claimed ranges was virtually negligible absent any showing of unexpected results or criticality.).
"[A] prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prima facie case of obviousness." In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003). See also In re Harris, 409 F.3d 1339, 74 USPQ2d 1951 (Fed. Cir. 2005) (claimed alloy held obvious over prior art alloy that taught ranges of weight percentages overlapping, and in most instances completely encompassing, claimed ranges; furthermore, narrower ranges taught by reference overlapped all but one range in claimed invention). However, if the reference’s disclosed range is so broad as to encompass a very large number of possible distinct compositions, this might present a situation analogous to the obviousness of a species when the prior art broadly discloses a genus. Id. See also In re Baird, 16 F.3d 380, 383, 29 USPQ2d 1550, 1552 (Fed. Cir. 1994) ("[a] disclosure of millions of compounds does not render obvious a claim to three compounds, particularly when that disclosure indicates a preference leading away from the claimed compounds."); MPEP § 2144.08; and subsection III.D below for an additional discussion on consideration of prior art disclosures of a broad range.
A range can be disclosed in multiple prior art references instead of in a single prior art reference depending on the specific facts of the case. Iron Grip Barbell Co., Inc. v. USA Sports, Inc., 392 F.3d 1317, 1322, 73 USPQ2d 1225, 1228 (Fed. Cir. 2004). The patent claim at issue was directed to a weight plate having 3 elongated openings that served as handles for transporting the weight plate. Multiple prior art patents each disclosed weight plates having 1, 2 or 4 elongated openings. 392 F.3d at 1319, 73 USPQ2d at 1226. The court stated that the claimed weight plate having 3 elongated openings fell within the "range" of the prior art and was thus presumed obvious. 392 F.3d at 1322, 73 USPQ2d at 1228. The court further stated that the "range" disclosed in multiple prior art patents is "a distinction without a difference" from previous range cases which involved a range disclosed in a single patent since the "prior art suggested that a larger number of elongated grips in the weight plates was beneficial… thus plainly suggesting that one skilled in the art look to the range appearing in the prior art." Id. [AltContent: rect]
Based on Jantke teaching, a person of ordinary skill in the art would be motivated to use purified olefinic nitrile or purify olefinic nitrile from HCN impurity before the reaction in case of unavailability of pure olefinic nitrile, or availability of old batch of olefinic nitrile having HCN impurities using procedures already known in chemistry, such as taught by Young and Armarego. Further, it is routine in chemistry to purify compounds or use pure compounds in reactions to increase yield, selectivity of product formation, to avoid side reactions etc.
Young teaches removal of HCN impurities from different chemicals using processes, such as using metals such as copper and iron, adsorption on activated carbon hydrolysis/distillation (entire article, especially pages 104-110).
Armarego teaches purification of allyl cyanide from final traces of HCN by distillation. Thus, based on guidance by Jantke, Young and Armarego, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that allyl cyanide used in reaction with hydridosilane requires must be pure olefinic nitrile devoid of HCN impurity or impurity of HCN as less than 100ppm and such starting material may be made pure using procedures already known in chemistry, such as taught by Young and Armarego. Further, purification of chemicals is routine in chemistry to avoid side reactions, deactivating catalysts, or increasing stability of reactants and products or good quality of product or increasing yield of reaction etc. Further, it would have been prima facie obvious to a person of ordinary skill in the art that combination of such purification process may lead to increased purity of allyl cyanide compared to the starting allyl cyanide, such as less than 40ppm etc.
“Since the claimed process and article produced thereby 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.
With regards to limitation of using hydridosilane with X as methoxy- Jantke teaches hydrosilation reaction, an addition reaction, using hydridosilane, dimethylchlorosilane, i.e., X=Cl. Since Jantke teaches basic reaction hydrosilation, an addition reaction, using hydridosilane, it would have been prima facie obvious to a person of ordinary skill in the art that hydrosilation reaction may use any hydridosilane having Cl or OMe.
This deficiency is further cured by Frank.
In the same field of endeavor, Frank teaches hydrosilation reaction between hydridosilane having halogen or alkoxy group and olefinic reactant in presence of platinum catalyst and a promoter, carboxylic acid (entire patent, especially abstract, page 3-5). Thus, based on the guidance provided by Jantke and Frank, it would have been prima facie obvious to a person of ordinary skill in the art that hydrosilation reaction may use any hydridosilane having Cl or OMe. Thus, the cited prior art meets limitation of the instant claims.
With regards to using promoter in the reaction -Jantke is silent about using promoter in the reaction. This deficiency is cured by Frank.
In the same field of endeavor, Frank teaches hydrosilation reaction between hydridosilane having halogen or alkoxy group and olefinic reactant in presence of platinum catalyst and a promoter, carboxylic acid (entire patent, especially abstract, page 3-5). Thus, based on the guidance provided by Jantke and Frank, it would have been prima facie obvious to a person of ordinary skill in the art that hydrosilation reaction may use promoter in the reaction. Thus, the cited prior art meets limitation of the instant 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, Jantke teaches a method of making R1xR2SiX(3-x) using reactants pure olefinic nitrile, hydridosilane, Karstedt’s catalyst in solvent, and temperature as in the instant claims; Young teaches removal of HCN impurities from different chemicals using processes, such as using metals such as copper and iron, adsorption on activated carbon hydrolysis/distillation; Armarego teaches purification of allyl cyanide from final traces of HCN by distillation; and Frank teaches hydrosilation reaction between hydridosilane having halogen or alkoxy group and olefinic reactant in presence of platinum catalyst and a promoter, carboxylic acid. 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 olefinic nitrile used in the hydrosilation process may be purified 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 amendment and remarks, filed on 01/22/2026, have been fully considered but not found persuasive.
Applicant argued that Jantke teaches allyl cyanide T has a technical grade purity with 0.01 to 5 parts by weight of crotonitrile with further impurities such as HCN etc. Applicant argued that Jantke in paragraph 0019 teaches a complete conversion and thus, suggest away from purification from HCN impurity.
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This is not found persuasive and the instant claims stand rejected. This is because contrary to applicant’s argument, Jantke teaches a method of making R1xR2SiX(3-x), with example of 4-(Dialkylchlorosilyl)-Butyronitrile, X=Cl, R1=CH3, R2=NCD, D=divalent hydrocarbon group; and x=2 (same product as in the instant claim 15); comprising reacting pure olefinic nitrile with example of allyl cyanide (3-butenenitrile) (0.45mol) (same reactant as in the instant claims 1-6, 10-15 and 17-25), having less than 0.1 part by weight of HCN (less than 100ppm), preferably less than 0.01 part by weight of HCN (less than 10ppm),
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.
Thus, purity of olefinic nitrile used in the reaction by the cited prior art is same as the instant claims. Jantke teaches full conversion of its purified olefinic nitrile preferably with less than 10ppm of HCN impurity, which is same or close to 7.5 and 5ppm of impurity of the instant claims Further, applicant is arguing over purity with respect to other impurities, wherein the other impurities or purification is not recited in the instant claims. Thus, applicant is arguing over limitation not recited in the instant claims.
Applicant argued over comparative examples that applicant used olefinic nitrile of Jantke and conversion was significantly hindered Vs the purified A.
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This is not found persuasive and the instant claims stand rejected. This is because applicant only argued but provided no evidence wherein Jantke teaches using 2M3BN with 45ppm impurity. Jantke preferably teaches to use 2M3BN with impurity less than 10ppm. Further, the instant claims 1-6, 10-15, 19-25 have same impurity level or more compared to Jantke.
Applicant argued that based on above argument a person of ordinary skill in the art would have not been motivated to purify olefinic nitrile and combine Jantke with Young and Armarego. Applicant argued against the references Jantke, Young, Armarego and Frank individually.
This is again not found persuasive. This is because Jantke teaches using purified olefinic nitrile having impurity of HCN as less than 100ppm. Thus, given the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that the process requires using pure olefinic nitrile devoid of HCN impurity or impurity of HCN less than 100ppm or preferably less than 10ppm. Based on this teaching, a person of ordinary skill in the art would be motivated to use purified olefinic nitrile or purify olefinic nitrile from HCN impurity before the reaction in case of unavailability of pure olefinic nitrile, or availability of old batch of olefinic nitrile having HCN impurities using procedures already known in chemistry, such as taught by Young and Armarego. Further, it is routine in chemistry to purify compounds or use pure compounds in reactions to increase yield, selectivity of product formation, to avoid side reactions etc.
Young teaches removal of HCN impurities from different chemicals using processes, such as using metals such as copper and iron, adsorption on activated carbon hydrolysis/distillation (entire article, especially pages 104-110).
Armarego teaches purification of allyl cyanide from final traces of HCN by distillation. Thus, based on guidance by Jantke, Young and Armarego, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that allyl cyanide used in reaction with hydridosilane requires must be pure olefinic nitrile devoid of HCN impurity or impurity of HCN as less than 100ppm and such starting material may be made pure using procedures already known in chemistry, such as taught by Young and Armarego. Further, purification of chemicals is routine in chemistry to avoid side reactions, deactivating catalysts, or increasing stability of reactants and products or good quality of product or increasing yield of reaction etc. Further, it would have been prima facie obvious to a person of ordinary skill in the art that combination of such purification process may lead to increased purity of allyl cyanide compared to the starting allyl cyanide, such as less than 40ppm etc.
“Since the claimed process and article produced thereby 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.
Frank teaches hydrosilation reaction between hydridosilane having halogen or alkoxy group and olefinic reactant in presence of platinum catalyst and a promoter, carboxylic acid (entire patent, especially abstract, page 3-5). Thus, based on the guidance provided by Jantke and Frank, it would have been prima facie obvious to a person of ordinary skill in the art that hydrosilation reaction may use any hydridosilane having Cl or OMe. Thus, the cited prior art meets limitation of the instant claims.
With regards to using promoter in the reaction -Jantke is silent about using promoter in the reaction. This deficiency is cured by Frank.
In the same field of endeavor, Frank teaches hydrosilation reaction between hydridosilane having halogen or alkoxy group and olefinic reactant in presence of platinum catalyst and a promoter, carboxylic acid (entire patent, especially abstract, page 3-5). Thus, based on the guidance provided by Jantke and Frank, it would have been prima facie obvious to a person of ordinary skill in the art that hydrosilation reaction may use promoter in the reaction.
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).
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.
Conclusion
No Claim is allowed.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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