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 .
DETAILED ACTION
Claims 1-19 of J. Hermeke et al., US 18/043,708 (Aug. 19, 2021) are pending and under examination. Claims 1-19 are rejected.
Request for Continued Examination
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 February 24, 2026 has been entered.
Claim Rejections - 35 USC § 103
The following is a quotation of AIA 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 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 AIA 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 1-19 are rejected under AIA 35 U.S.C. 103 as being unpatentable over C. Buesing et al., US 2004/0092758 (2004) (“Buesing”) in view of D. Brunelle, US 5,132,423 (1992) (“Brunelle”); Z. Li et al., CN 108250233 (2018) (“Li”) and J. de la Zerda et al., Journal of the Chemical Society, Perkin Transactions 2, 823-826 (1986) (“Zerda”).
C. Buesing et al., US 2004/0092758 (2004) (“Buesing”)
Buesing teaches that bis-3-(triethoxysilyl)propyltetrasulfide (TESPT)
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is a commercially successful product. Buesing at page 2, [0013].
Buesing teaches a process for producing organosilicon compounds having the formula (RO)3-mRm-Si-Alk-Sn-Alk-SiRm(OR)3-m (where Alk represents a divalent hydrocarbon and n is an integer with a value of 2-8, preferably 3-8, representing the average sulfur-chain length, i.e., the sulfur rank), comprising the steps of (I) heating and reacting:
(A) a sulfide compound having the formula M2Sn or MHS wherein H is hydrogen, M is ammonium or an alkali metal, and n is 1-8, with
(B) a silane compound having the formula (RO)3-m-Rm-Alk-X wherein X is halogen, and
(C) sulfur, in the presence of a phase transfer catalyst and an aqueous phase containing a buffer or a basic compound, to form a product mixture. Buesing at page 1, [0006].
Buesing’s general process can be represented schematically as follows:
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[0018] Phase transfer catalysts suitable for use according to the invention are quaternary onium cations. Some representative examples of quaternary onium salts yielding quaternary ammonium cations that can be used as phase transfer catalysts are described in U.S. Pat. No. 5,405,985 (Apr. 11, 1995) which was noted above, among which are tetrabutylammonium bromide (TBAB), tetrabutylammonium chlo ride (TBAC), tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetraphenylarsonium bromide, and tetraphenylarSonium chloride. The preferred quaternary onium salts according to this invention are TBAB and TBAC, most preferably TBAB.
Buesing at page 2, [0018].
Buesing teaches that the silane compound (B) can be reacted with the sulfide compound (A) in the presence or absence of a solvent. Busing at page 2, [0017]. Buesing teaches that at the end of the reaction, a product mixture is produced containing an organic phase, an aqueous phase, and some precipitated solid materials including various salts such as NaCl, Na2HPO4, and NaHCO3, or their analogous potassium salts, formed during the reaction. The organic phase consists of the desired sulfur containing organosilicon compound. Buesing at page 3, [0023].
Buesing further teaches that:
[0029] If desired, the dried organic phase can be subjected to some additional steps for improving its final purity and appearance.
Buesing at page 4, [0029]. Buesing further teaches that organic solvents, such as toluene, xylene, benzene, heptane, octane, nonane, decane, and chlorobenzene, preferably toluene, may be used. Buesing at page 2, [0017].
In working Example 1, Buesing teaches an embodiment of the process, which is summarized by the Examiner below:
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Buesing at page 4, [0032]. Buesing further teaches that:
[0029] If desired, the dried organic phase can be subjected to some additional steps for improving its final purity and appearance.
Buesing at page 4, [0029]. Buesing performs working Example 2 in essentially the same manner as Example 1 (with some variation in reaction temperatures) to obtain a product-containing upper organic phase, but adds the step of:
[0033] . . . The organic phase was then transferred to a stripping apparatus, where it was stripped to remove residual water, and agitated via a stir bar at 30 mm Hg and 100-101 degrees Celsius for 166 minutes. The organic phase was then filtered to produce 434.12 g of a clear, light-yellow product.
Differences between Buesing and Claim 1
Buesing Example meets each and every method step limitation of claim 1:
Claim 1. A process for preparing one or more polysulfane silanes of the formula (I)
(R1)3-mR2mSi-R3-Sx-R3-SiR2m(OR1)3-m the process comprising:
reacting at least one halosilane of formula (II):
(R1)3-mR2mSi-R3-Hal II
with M(SH)y and/or MzS and sulfur, in the presence of a phase transfer catalyst, a base, and an aqueous phase. . .
where the 3-chloropropyl)triethoxysilane meets the limitations of formula II (R1)3-mR2mSi-R3-Hal, the NaHS meets the claim limitation of M(SH)y and Buesing employs sulfur in in an aqueous reaction mixture.
Buesing differs in the nature of the phase transfer catalysts employed; that is Buesing does not teach the claim 1 limitation of:
claim 1 . . . wherein the phase transfer catalyst is an alkylguanidinium catalyst of the formula (III):
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wherein Y is an element of main group 5 . . .
D. Brunelle, US 5,132,423 (1992) (“Brunelle”)
Brunelle teaches a method for effecting reaction in a non-polar organic solvent between a highly polar compound which is insoluble in said solvent and a substantially non-polar compound which is soluble therein, which comprises conducting said reaction in the presence of at least one hexaalkylguanidinium salt as a phase transfer catalyst. Brunelle at col. 2, lines 33-40. Brunelle teaches that the present invention is capable of use in connection with an extremely broad spectrum of reactions between organic chemicals. Brunelle at col. 2, lines 41-43. Significantly, Brunelle directs one of ordinary skill to a particular subset of reactions, as follows:
Accordingly, the invention is a method for effecting reaction in a non-polar organic solvent between a highly polar compound which is insoluble in said solvent and a substantially non-polar compound which is soluble therein, which comprises conducting said reaction in the presence of at least one guanidinium or α,[Symbol font/0x77]-bis(pentaalkylguanidinium)alkane salt as a phase transfer catalyst.
Brunelle at col. 2, lines 33-40 (emphasis added).
Brunelle teaches that
Certain guanidinium and α,[Symbol font/0x77]-bis(pentaalkylguanidinium)alkane salts may be employed as phase transfer catalysts in reactions between polar and non-polar compounds. The use of these salts frequently increases the reaction rate and yield substantially as compared with the use of previously known phase transfer catalysts in comparable amounts. In addition, said guanidinium salts have a high degree of thermal stability and thus do not undergo substantial decomposition during the displacement reaction. This means less color formation in the product and the potential for recycling of catalyst, decreasing the cost of the process.
Brunelle at col. 2, lines 20-32 (emphasis added).
In this regard, Brunelle notes that prior art quaternary ammonium phase transfer catalysts have stability problems.
Many types of phase transfer catalysts are known, including quaternary ammonium and phosphonium salts as disclosed in . . .
. . .
In the third place, decomposition of the phase transfer catalyst usually occurs during the reaction, necessitating frequent replacement thereof and resulting in the formation of by-products which cause discoloration of the product and may lead to undesirable side reactions.
Brunelle at col. 1, lines 48-66.
Brunelle teaches that the hexaalkylguanidinium salt genus of formula (VI) are effective phase transfer catalysts:
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wherein each of R5, R6, R7 and R8 is a primary alkyl radical or at least one of the R5-R6 and R7-R8 combinations with the connecting nitrogen atom forms a hetero cyclic radical, R9 is a primary alkyl radical, R10 is a primary alkyl or bis(primary alkylene) radical, X is an anion and n is 1 or 2.
The alkyl radicals suitable as R5-9 are primary alkyl radicals, generally containing about 1-12 and preferably about 2-6 carbon atoms.
. . .
R10 is usually an alkyl radical of the same structure or a C2-12 alkylene radical in which the terminal carbons are primary; most preferably, it is C2-6 alkyl or C4-8 straight chain alkylene.
Brunelle at col. 4, lines 35-66 (emphasis added).
Brunelle discloses hexaethylguanidinium chloride as an exemplary species of his phase transfer catalysts of formula (VI). Brunelle at cols. 5-6, Example 1.
In working Examples 13-20, Brunelle demonstrates species of hexaalkylguanidinium salts of formula (VI) (1 to 0.25 mol%) as phase transfer catalysts, in various anhydrous organic solvents (Examples 13-20 summarized below). Brunelle at col. 8, lines 43-68 (data in Table II).
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Brunelle at col. 8, lines 43-68 (data in Table II). Per Table II, the percent yields of Example 13-20 ranged from 87% to 100%. Brunelle at col. 9, Table (II). In Examples 28-29, Brunelle demonstrates the stability of hexaethylguanidinium bromide (1 mmol) by in refluxing chlorobenzene or o-dichlorobenzene, respectively, with sodium p-cresoxide (2 mmol) for 2 hours, where the catalyst recovery ranged from 84-88%. Brunelle at col. 9, lines 44-59 (Examples 28-29).
Z. Li et al., CN 108250233 (2018) (“Li”)
An English-machine language translation (Google Translate) is attached as the second half of reference Li. Li thus consists of 24 total pages (including the English-language portion). Accordingly, this Office action references Li page numbers in the following format “xx of 24”.
Li is cited here for the teaching that the Brunelle guanidinium-type phase transfer catalysts are suitable equivalents for the synthesis of Si-69, i.e., Li teaches hexabutylguanidinium chloride, hexabutylguanidinium bromide, hexaethylguanidinium bromide, tripentylguanidinium chloride, or tripentylguanidinium bromide. However, Li does not teach a working example where the Brunelle guanidinium-type phase transfer catalysts are employed.
Li teaches a method for preparing silane coupling agent Si-69 in an aqueous phase. Li at page 13 of 24 Abstract. Li teaches that Si-69 remains the most widely used sulfur-containing silane coupling agent, holding an irreplaceable position in the tire industry. Li at page 16 of 24, last three lines.
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See, CAS Abstract for Si-69 (1984) (CAS No. 40372-72-3). Li teaches that the chain length of sulfur in polysulfide silanes can range from 1 to 10 and in reality, it is impossible to obtain complete disulfide or tetrasulfide. Li at paragraph bridging pages 16-17. Li teaches that therefore; suppliers generally indicate the average chain length of sulfur in their products. Li teaches, for example, that the average chain lengths of sulfur in Degussa's Si-69 and Si-75 are 3. 75 and 2.35, respectively. Id.
Li teaches synthesis of Si-69 by first (steps 1-3), mixing sodium sulfide solution with buffer solution, and adding elemental sulfur, with a molar ratio of elemental sulfur to sodium sulfide of 2.6- 3.2: 1, stirring at 200-800 r/min at 35-95 °C until dissolved, and reacting for 5-60 min to obtain a reddish-brown inorganic phase solution containing polysulfides. Li at page 19 of 24, [0013] (steps 1-3). Next, Li teaches the following phase transfer catalyst steps (IV) and (V):
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Li at page 7 of 23, [0013]. Which translates to: 1
IV. Dissolve the phase transfer catalyst and KI in water, such that the total combined mass of the phase transfer catalyst and KI constitutes 0.5% to 10% of the mass of the γ-chloropropyltriethoxysilane, thereby preparing a catalyst solution with a mass fraction of 1% to 20%.
V. Add the catalyst solution dropwise into an inorganic phase solution containing polysulfides over a period of 1 to 30 minutes; subsequently, add dropwise γ-chloropropyltriethoxysilane (with a purity of 98% or higher), maintaining a molar ratio of γ-chloropropyltriethoxysilane to sodium polysulfide of 1.7–2.2:1. Conduct the reaction at a temperature of 50–95°C, with the dropwise addition taking place over a period of 0.5 to 2.5 hours, while stirring at a speed of 300–1200 rpm. Thereafter, carry out refluxing, taking samples at regular intervals for analysis via gas chromatography.
Li at page 19 of 24, [0013] (steps 4-5).
In working Example 1, Li teaches synthesis of Si-69 employing sodium sulfide pentahydrate and elemental sulfur, where the phase transfer catalyst dodecyltrimethylammonium bromide/KI, which can be summarized as follows.
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Li at pages 16-17 of 19. Where, as stated above, the phase transfer catalyst (i.e., 1119-94-4) is the following dodecyltrimethylammonium bromide and potassium iodide (KI):
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Li does not teach a working example where the Brunelle guanidinium-type phase transfer catalysts are employed.
However, in the following paragraph, Li teaches the instantly claimed guanidinium phase transfer catalysts are suitable for the synthesis of Si-69 in LI’s reaction steps (IV) and (V): hexabutylguanidinium chloride, hexabutylguanidinium bromide, hexaethylguanidinium bromide, tripentylguanidinium chloride, or tripentylguanidinium bromide. Li at page 8 of 24, [0017].
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Li at page 8 of 24, [0017]. This paragraph is translated by Examiner using Google Translate as follows.2
[0017] In Step 4, the phase-transfer catalyst is one or a mixture of several of the following: benzyltriethylammonium chloride, trioctylmethylammonium chloride, triethylhexylammonium bromide, triethyloctylammonium bromide, tetramethylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium bromide, benzyltriethylammonium chloride, benzyltriethylammonium bromide, dodecyltrimethylammonium chloride, dodecyltrimethylammonium bromide, 18-crown-6, 15-crown-5, polyethylene glycol dialkyl ether, hexabutylguanidinium chloride, hexabutylguanidinium bromide, hexaethylguanidinium bromide, tripentylguanidinium chloride, or tripentylguanidinium bromide.
Per footnote 2, see also, Li at page 20 of 24, [0017]. In sum, Li teaches the equivalency of Buesing’s quaternary ammonium cations (such as tetrabutylammonium bromide (TBAB)) and the Brunelle guanidinium-type phase transfer catalysts in phase transfer catalyzed synthesis of Si-69.
J. de la Zerda et al., Journal of the Chemical Society, Perkin Transactions 2, 823-826 (1986) (“Zerda”)
Zerda teaches that quaternary ammonium salts are subject to base catalyzed Hoffman degradation occurs, even at ambient and sub-ambient temperatures, to provide a tertiary amine (i.e., R3N) and olefin as side products.
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Zerda at page 823, col. 1.
Obviousness Rationale
Respecting claim 1, one of ordinary skill is motivated to replace the tetra-n-butylammonium bromide catalyst of Buesing Example 1 with Brunelle’s hexaalkylguanidinium salt of formula (VI)
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for example, any of hexabutylguanidinium chloride, hexabutylguanidinium bromide, hexaethylguanidinium bromide, tripentylguanidinium chloride, or tripentylguanidinium bromide as taught by Li or hexaethylguanidinium chloride. Brunelle discloses hexaethylguanidinium chloride as an exemplary species of his phase transfer catalysts of formula (VI). Brunelle at cols. 5-6, Example 1.
One of ordinary skill is so motivated in view of Brunelle’s teaching that they are effective phase transfer catalysts with high thermal stability and give high yields in phase transfer catalyzed reactions and Li’s teaches the equivalency of Buesing’s quaternary ammonium cations (such as tetrabutylammonium bromide (TBAB)) and the Brunelle guanidinium-type phase transfer catalysts in phase transfer catalyzed synthesis of Si-69. One of ordinary skill arrives at each and every limitation of claim 1.
In regard to motivation, Brunelle teaches that:
The use of these [guanidinium] salts frequently increases the reaction rate and yield substantially as compared with the use of previously known phase transfer catalysts in comparable amounts. In addition, said guanidinium salts have a high degree of thermal stability and thus do not undergo substantial decomposition during the displacement reaction
Brunelle at col. 2, lines 24-30 (emphasis added).
One or ordinary skill is particularly motivated by Brunelle’s and Zerda’s teaching of the instability of quaternary ammonium phase transfer catalysts under basic conditions. Brunelle at col. 1, lines 48-66; Zerda at page 823, col. 1. And in view of the high stability taught by Brunelle’s hexaalkylguanidinium salts of formula (VI) under basic conditions. Brunelle at col. 9, lines 44-59 (Examples 28-29); Id. at col. 2 lines 27-30.
Claim 2 is obvious because both Buesing and Li teaches sodium as the metal “M”, that is Buesing teaches NaHS, per claim 1 “M(SH)y” and Li teaches Na2S per claim 1 “MzS”; and both Buesing and Li teach the reactant 3-chloropropyl)triethoxysilane, where per claim 1 R1 is ethoxy, m is 0, R3 is (CH2)3 and “Hal” is Cl in claim 1 formula (II) (R1)3-mR2mSi-R3-Hal.
The limitations of claims 3-7 are clearly met by practice of the prior art as proposed above; for example, where hexaethylguanidinium chloride (as taught by Buesing) or hexaethylguanidinium bromide (as taught by Li) is used as the phase transfer catalyst in the process of Buesing.
The limitations of claim 8 are clearly met because Buesing Example 1 employs sodium hydroxide (NaOH) which meets the claim 8 formula of M(OH)w.
Claim 9 is obvious because Buesing teaches that the aqueous phase may comprise a buffer, where preferably, the buffer consists of Na3PO4, Na2CO3, or K2CO3. Buesing at page 3, [0019].
Claim 10 is obvious because Buesing teaches Example 1 at a reaction temperature of 73 to 85 °C, which falls within the claim 10 range.
Claim 11 is obvious because the above proposed modification of Brunelle employs, for example, hexaethylguanidinium chloride and NaOH as the base.
The limitations of claim 12 are clearly met by use of, hexaethylguanidinium chloride as proposed above.
Claims 13-15, directed to the following hexaalkylguanidinium chlorides are obvious for the following reasons.
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Brunelle teaches that the full range of hexaalkylguanidinium salt genus of formula (VI) are effective phase transfer catalysts:
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wherein each of R5, R6, R7 and R8 is a primary alkyl radical or at least one of the R5-R6 and R7-R8 combinations with the connecting nitrogen atom forms a hetero cyclic radical, R9 is a primary alkyl radical, R10 is a primary alkyl or bis(primary alkylene) radical, X is an anion and n is 1 or 2.
The alkyl radicals suitable as R5-9 are primary alkyl radicals, generally containing about 1-12 and preferably about 2-6 carbon atoms.
. . .
R10 is usually an alkyl radical of the same structure or a C2-12 alkylene radical in which the terminal carbons are primary; most preferably, it is C2-6 alkyl or C4-8 straight chain alkylene.
Brunelle at col. 4, lines 35-66 (emphasis added).
See also hexaalkylguanidinium species disclosed in Brunelle Examples 13-20. Brunelle at col. 8, lines 43-68 (data in Table II). Here the carbon number of the claim 13-15 alkyl groups falls within the alkyl group carbon number range taught as suitable by Brunelle. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05. Further, the claimed hexaalkylguanidinium species, Li’s species (i.e., hexabutylguanidinium chloride, hexabutylguanidinium bromide, hexaethylguanidinium bromide, tripentylguanidinium chloride, or tripentylguanidinium bromide, and Brunelle’s species are all homologs. MPEP § 2144.09.3 One of ordinary skill would be apprised by Brunelle’s teaching of preferred alkyl groups for formula (IV) that the hexaalkylguanidinium species of claims 13-15, which are homologs of hexaethylguanidinium chloride (as proposed above), would be functional catalyst equivalents. Claims 13-15 are therefore obvious over the cited art.
The further limitations of claims 16-18 are clearly met as discussed above.
Claim 19 is obvious for the following reasons. Claim 19 recites:
Claim 19: The process of claim 1, wherein halosilane of formula II and M(SH)y are reacted in a molar ratio of between 1.0:0.35 and 1.0: 3.0,
Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.05(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
In Example 1, Buesing teaches 460 g (1.91 mol) of 3-chloropropyltriethoxysilane (claim 1, formula II) and 114.14 g aqueous NaSH solution consisting of 44.96 percent NaSH (i.e., 0.91 mol of claim 1 formula M(SH)y). Buesing’s molar ratio of formula II (1.91 mol) to M(SH)y (0.91 mol) calculates 1 to 2, which falls within the claimed range. The claim 19 range is therefore obvious over Buesing because one of skill in the art is motivated to optimize within the claimed range in view of the fact that Buesing’s Example 1 is performed within the claimed range. MPEP § 2144.05(II)(A).
Applicant’s Argument
Applicant notes the following excerpt of Brunelle, which directs one of ordinary skill to a particular subset of reactions, as follows:
Accordingly, the invention is a method for effecting reaction in a non-polar organic solvent between a highly polar compound which is insoluble in said solvent and a substantially non-polar compound which is soluble therein, which comprises conducting said reaction in the presence of at least one guanidinium or α,[Symbol font/0x77]-bis(pentaalkylguanidinium)alkane salt as a phase transfer catalyst.
Reply at page 8 (citing Brunelle at col. 2, lines 33-40 (emphasis in Applicant’s Reply)). Applicant emphasizes that a polar solid phase (polar compound(s)) is being transferred into a non-polar liquid phase (non-polar solvent). Reply at page 8. Applicant argues that insofar as the phase transfer catalyst of Brunelle is taught to facilitate transfer of a polar compound into a non-polar liquid, there is no suggestion that such a phase transfer catalyst would facilitate the transfer of a non-polar liquid into a polar liquid. Reply at page 8.
This argument is not persuasive for the following reasons. Here Applicant is arguing that one of ordinary skill would not predict that Brunelle’s hexaalkylguanidinium salt of formula (VI) would transfer the non-polar organic 3-chloropropyltriethoxysilane into the polar aqueous sodium polysulfide reagent polar phase. Applicant is correct because Brunelle’s hexaalkylguanidinium salts comprise organic-soluble aliphatic nitrogen cations (just as do Buesing’s quaternary ammonium cations, e.g., TBAB) and are clearly not expected to interact with, let alone, draw non-charged, non-polar organics into an aqueous phase. But that is not the issue here. Rather it is the opposite, where the aliphatic phase transfer catalyst cations interact with and draw the negatively charged sulfide reagents (such as Na+HS-) into the organic 3-chloropropyltriethoxysilane phase so that they may react.
So, for example, Buesing (including Example 1) is directed to a two-phase reaction mixture (i.e., a non-polar organic 3-chloropropyltriethoxysilane phase and a polar aqueous Na+HS- phase). Buesing at page 1, [0005]. In Example 1, Buesing’s aqueous-phase, sodium polysulfide reagent is required react with the non-polar organic-phase 3-chloropropyltriethoxysilane (claim 1, formula II) as follows:
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reacts with the organic soluble4, non-polar phase:
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Buesing at page 4, [0032].
One of ordinary skill would recognize that the purpose of Buesing’s Example 1 PTC tetrabutylammonium bromide (TBAB) (having aliphatic nitrogen cations) is to bring the negatively charged polar sodium polysulfide reagent (of the aqueous phase) into the non-polar organic phase (i.e., 3-chloropropyltriethoxysilane) so that they may react with each other. The above Brunelle excerpt clearly suggests to one of ordinary skill that the more thermally stable hexaalkylguanidinium salt genus of formula (VI) can be effective to draw a polar compound into a non-polar phase in the same manner as quaternary ammonium cations; that is, they both comprise aliphatic nitrogen cations.
Brunelle specifically states this:
Certain guanidinium and α,[Symbol font/0x77]-bis(pentaalkylguanidinium)alkane salts may be employed as phase transfer catalysts in reactions between polar and non-polar compounds. The use of these salts frequently increases the reaction rate and yield substantially as compared with the use of previously known phase transfer catalysts in comparable amounts. In addition, said guanidinium salts have a high degree of thermal stability and thus do not undergo substantial decomposition during the displacement reaction.
Brunelle at col. 2, lines 20-32 (emphasis added).
Thus, Buesing (including Buesing Example 1) is the exact situation described by the Brunelle excerpt at col. 2, lines 33-40 (where the polar polysulfide reagent is not soluble in the non-polar 3-chloropropyltriethoxysilane resulting in a two-phase mixture). Note that Buesing’s reaction involves a distinct organic phase and a distinct aqueous phase. Brunelle at page 1, [0005]; Id. at page 3, [0023]; Id. at page 3, [0025]. In sum, one of ordinary skill would understand that the reason a phase transfer catalyst (e.g., TBAB) is even employed by Buesing in the first place is that the polar polysulfide reagent is non- or poorly soluble in the non-polar 3-chloropropyltriethoxysilane. Accordingly, one of ordinary skill would have a reasonable expectation that Brunelle’s hexaalkylguanidinium salts of formula (VI) would effectively catalyze the reaction of Buesing in a similar or improved fashion over Buesing’s quaternary ammonium phase transfer catalysts.
Furthermore, Brunelle teaches that non-polar organic solvents may be employed:
[0017] The silane compound (B) can be reacted with the sulfide compound (A) in the presence or absence of a solvent, or alternatively, with the sulfide compound (A) and sulfur (C) in combination. The silane compound (B) can also be dispersed in an organic solvent to form an organic phase. some representative examples of organic solvents include toluene, xylene, benzene, heptane, octane, nonane, decane, and chlorobenzene, preferably toluene.
Brunelle at page 2, [0017] (emphasis added).
So, while Buesing Example 1 does not employ a non-polar organic solvent, Buesing teaches that a non-polar organic solvent can be used in which the phase transfer process is the same as described above.
Non-Statutory Double Patenting
The non-statutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A non-statutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
Non-Statutory Double Patenting Rejection over H. Droege et al., US 12/540,146 (2026), US 17/760,115 (2021)
Claims 1-19 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 2 and 4 of H. Droege et al., US 12/540,146 (2026), US 17/760,115 (2021) in view of C. Buesing et al., US 2004/0092758 (2004) (“Buesing”); Z. Li et al., CN 108250233 (2018) (“Li”); D. Brunelle, US 5,132,423 (1992) (“Brunelle”) and J. de la Zerda et al., Journal of the Chemical Society, Perkin Transactions 2, 823-826 (1986) (“Zerda”) as set forth in the above § 103 rejection.
The combination of conflicting claims 2 and 4 teaches the following reaction:
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Where conflicting claim 2 defines the variable R1, R2, and R3 with the same identities as instant claim 1.
Conflicting claims 2 and 4 meet each and every limitation of instant claim 1 except the conflicting claims do not teach the instant claim 1 limitation of:
Instant claim 1 . . . wherein the phase transfer catalyst is an alkylguanidinium catalyst of the formula (III):
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wherein Y is an element of main group 5 . . .
The instant claims are obvious over and patentably indistinct from conflicting claims 2 and 4 for the following reasons. One of ordinary skill is motivated to choose to synthesize the following compound from within the genus of conflicting claim 2:
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in view of the utility taught by Buesing.
One of ordinary skill is further motivated to perform conflicting claim 1 with the instant claim 1 limitation of:
instant claim 1 . . . wherein the phase transfer catalyst is an alkylguanidinium catalyst of the formula (III):
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wherein Y is an element of main group 5 . . .
for the same reasons discussed above in the § 103 rejection. By practice of conflicting claim 1 as proposed above, one of ordinary skill thereby arrives at each and every limitation of instant claim 1. Instant claim 1 is therefore obvious over and patentably indistinct from conflicting claims 2 and 4 in view of the cited art. The further limitations of instant dependent claims 2-19 are obvious for the same reasons discussed above in the § 103 rejection.
Applicant’s Argument
Applicant cites the same argument as for the § 103 rejection. This argument is not persuasive for the same reasons discussed above.
Non-Statutory Double Patenting Rejection over J. Hermeke et al., US 17/787,278 (2020)
Claims 1-19 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 1 and 2 of J. Hermeke et al., US 17/787,278 (2020), published as US 2023/0039979 (2023), in view of C. Buesing et al., US 2004/0092758 (2004) (“Buesing”); D. Brunelle, US 5,132,423 (1992) (“Brunelle”); Z. Li et al., CN 108250233 (2018) (“Li”) and J. de la Zerda et al., Journal of the Chemical Society, Perkin Transactions 2, 823-826 (1986) (“Zerda”) as set forth in the above § 103 rejection. The rejection is provisional because, while the issue fees have been paid, the conflicting claims have not been patented.
Conflicting claim 1 is directed to the same process as instantly claimed and teaches each and every limitation of instant claim 1 except that conflicting claim 1 does not teach the instant claim 1 limitation of:
Instant claim 1 . . . wherein the phase transfer catalyst is an alkylguanidinium catalyst of the formula (III):
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wherein Y is an element of main group 5 . . .
Rather conflicting claim 1 recites
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The instant claims are obvious over and patentably indistinct from conflicting claims 1 and 2 for the following reasons. One of ordinary skill is motivated to choose to synthesize the following compound from within the genus of conflicting claims 1 and 2:
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in view of the utility taught by Buesing.
One of ordinary skill is further motivated to perform conflicting claim 1 with the instant claim 1 limitation of:
instant claim 1 . . . wherein the phase transfer catalyst is an alkylguanidinium catalyst of the formula (III):
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wherein Y is an element of main group 5 . . .
for the same reasons discussed above in the § 103 rejection. By practice of conflicting claim 1 as proposed, one of ordinary skill thereby arrives at each and every limitation of instant claim 1. Instant claim 1 is therefore obvious over and patentably indistinct from conflicting claims 1 and 2 in view of the cited art. The further limitations of instant dependent claims 2-19 are obvious for the same reasons discussed above in the § 103 rejection.
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 For a more accurate translation of this portion of Li, a character-to-text translation was performed by the Examiner by copying and pasting the Chinese characters directly into Google Translate (text).
2 This character-to-text translation was performed by the Examiner by copying and pasting the Chinese characters directly into Google Translate. The English machine translation of Z. Li et al., CN 108250233 (2018) (“Li”) attached to the IDS at paragraph [0017] recites “hexabutylguanidine chloride, hexabutylguanidine bromide, hexaethylguanidine bromide, tripiridinylguanidine chloride, or tripiridinylguanidine bromide”; that is, “guanidine” versus the above “guanidinium”. Li at page 20 of 24, [0017]
3 Obviousness of a claimed compound can also be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2144.09; MPEP § 2143(I)(B). Also, Compounds which are position isomers or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. MPEP § 2144.09(II); In re Shetty, 195 USPQ 753, 756 (CCPA 1977) (involving the factual situation of an ethylene versus methylene linkage noting that “a person skilled in chemical and/or pharmaceutical arts would not hesitate to extend the alkylene linkage of the prior art compound”)
4 Buesing specifically suggests the non-polarity, organic-solvent solubility, and aqueous non-solubility of the silane reactant by the statement “The silane compound (B) can also be dispersed in an organic solvent to form an organic phase”, where non-polar solvents “toluene, xylene, benzene, heptane, octane, nonane, decane, and chlorobenzene, preferably toluene” are suggested by Buesing. Buesing at page 2, [0017].