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, 21, 23, 24, 29-43, and 45-49 of A. Nishimura et al., US 18/024,818 (Sept. 7, 2021) are pending. Claims 3, 6-8, 15, 19, 21, 23, 24, 29-38, 43, and 45 to non-elected Groups (II)-(VII) are withdrawn from consideration pursuant to 37 CFR 1.142(b). Claim 49 is withdrawn as not reading on the elected species of lithium aluminum hydride. Claims 1, 2, 4, 5, 9-14, 16-18, 39-42, and 46-48 are under examination on the merits and are rejected.
Election/Restrictions
Applicant elected Group (I), (now claims 1, 2, 4, 5, 9-14, 16-18, 39-42, and 46-49), without traverse, in the Reply to Restriction Requirement filed on November 28, 2025. Claims 3, 6-8, 15, 19, 21, 23, 24, 29-38, 43, and 45 to non-elected Groups (II)-(VII) are withdrawn from consideration pursuant to 37 CFR 1.142(b). In view of the foregoing, the Examiner’s restriction/election requirement is maintained as FINAL.
Pursuant to the election of species requirement, Applicant elected,
(1) a single species of halosilane raw material (CO): dodecachlorocyclohexasilane;
(2) a single species of reducing agent (R2): lithium aluminum hydride; and
(3) a single species of a hydrogenated polysilane compound (CX): cyclohexasilane
without traverse. Of the elected group, claims 1, 2, 4, 5, 9-14, 16-18, 39-42, and 46-48 read on the elected species. The elected species was searched and found to be obvious under § 103 as set forth below. The search was not further extended. In view of cited art, the election of species requirement is maintained in effect and claim 49 is provisionally withdrawn from consideration pursuant to 37 CFR 1.142(b) as not reading on the elected species of lithium aluminum hydride. See, MPEP § 803.02.
The Claimed Invention
Specification working Example 1-1 is summarized by the Examiner below to give context to the claim 1 language.
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Specification at pages 100-102.
In Example 1-1, the specification teaches that the workup and distillation (i.e., steps (3) and (4) of the above schematic summary) was conducted per claim 1 steps (T3)/(T4) as follows:
After the reaction, the resulting reaction solution was slowly added dropwise to a 10% aqueous sulfuric acid solution cooled to 0°C.
After stirring at room temperature for 30 minutes, a clear colorless solution containing no solids in both the organic and aqueous layers was obtained.
After allowing the solution to stand, the aqueous layer was removed by liquid separation and the organic layer was collected, and the organic layer was concentrated under reduced pressure to obtain 5.7 g of a crude product. At this time, no solids were observed adhering to the top of the concentrator or the cooler for solvent condensation.
The crude product was further purified by distillation under reduced pressure in a 100-mL glass distillation apparatus to obtain 2.8 g of colorless, transparent cydohexasilane with an area purity of 98% by gas chromatography (GC). At this time, there were no solids adhering to the top of the distillation apparatus or the cooler for condensation after distillation.
Specification at lines bridging pages 101-102 (emphasis added).
Withdrawal Claim Rejections 35 U.S.C. 112(b)
Rejection of claims pursuant to 35 U.S.C. 112, as indefinite because the claim 1 removing step (T2) is unclear is withdrawn in view of Applicant’s amendment.
Withdrawal Claim Rejections 35 U.S.C. 102
Rejection of claims under 35 U.S.C. 102(a)(1) as being anticipated by X. Lu et al., 27 Chemistry of Materials, 6053-6058 (2015) (“Lu”) and E. Hengge et al., 16 Angewandte Chemie International Edition, 403 (1977) are withdrawn in view of Applicant’s amendments for the following reasons. Both Hengge and Lu differ from claim 1, as amended, in the same respect. That is Hengge and Lu each filter the reaction solids resulting from the LiAlH4 (which are per claim 1 “the resulting material of the reducing agent (R2)”). Thus, both Hengge and Lu do perform a “separating step of a solid and a liquid”, which is not permitted by claim 1 as amended. That is, neither Hengge nor Lu meet the claim 1 reducing agent removal limitation as bolded below
Claim 1 . . . a removing step in which a reaction solution of the reducing step (P1) is subjected to at least two steps to remove the reducing agent (R2) and/or a resulting material of the reducing agent (R2) contained in the reaction solution, wherein
the removing step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) is carried out without a (T1) separating step of a solid and a liquid . . .
Rejection of claims under 35 U.S.C. 102(a)(2) as being anticipated by R. Elgammal et al., US 2022/0153595 (2022) (“Elgammal”) are withdrawn in view of Applicant’s amendments because Elgammal does teach either of claim 1 step combination of (T2)/(T4) or the step combination of (T3)/(T4), as these steps have been amended.
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, 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(a) 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, 2, 4, 5, 9-14, 16-18, 39-42, and 46-48 are rejected under AIA 35 U.S.C. 103 as being unpatentable over E. Hengge et al., 16 Angewandte Chemie International Edition, 403 (1977) or X. Lu et al., 27 Chemistry of Materials, 6053-6058 (2015) (“Lu”) as equally applicable primary references in view of the below cited Secondary Art Teaching Acid Workup of Lithium Aluminum Hydride Reactions (i.e., references Stapp, Karabatsos, Field, and/or Eliel) in further view of S. Imoto et al., US 2017/0158518 (2017) (“Imoto”) and A. Elangovan et al., US 8,975,428 (2015) (“Elangovan”).
E. Hengge et al., 16 Angewandte Chemie International Edition, 403 (1977)
Hengge teaches that starting from dodecaphenylcyclohexasilane, reaction with AlCI3/HCl cleaves the Si-Ph bonds to dodecachlorocyclohexasilane (Si6Cl12) (where Si6Cl12 is elected species (C1)). Hengge at page 403, paragraph bridging cols. 1-2. Hengge teaches that Si6Cl12 can be smoothly hydrogenated to unsubstituted cyclohexasilane (Si6H12) (elected species (CX)) with pure LiAlH4 (elected species of reducing agent (R2)) in benzene/ether. Hengge at page 403, col. 2.
Hengge teaches the following one-pot experimental procedure:
Procedure
Benzene (200ml) and AlCl3 (1 g, 7.5mmol) are added to Si6Ph12 (4g, 3.6 mmol). HCl is passed into this stirred suspension until a clear solution is obtained. AlCl3 is filtered off, and a freshly prepared 0.5 M ethereal solution of LiAIH4 (100ml) is added to the vigorously stirred filtrate with ice-cooling (1 h). Stirring is continued at room temperature, the ether removed, and the precipitate filtered off; residual benzene is drawn off at 1 torr. At 0.01 torr and 80°C Si6H12 condenses over as a colorless liquid, yield 0.39g (60%).
Hengge at page 403, col. 2 (emphasis added).
Hengge is summarized as follows.
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In summary, Hengge teaches that Si6Cl12 (the elected species (C1)) is formed in situ followed by reduction with lithium aluminum hydride (LiAlH4) (the elected species of reducing agent (R2)) to cyclohexasilane (Si6H12) (the elected species (CX)).
X. Lu et al., 27 Chemistry of Materials, 6053-6058 (2015) (“Lu”)
Lu discloses synthesis of cyclohexasilane (Si6H12) as follows:
[(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14] (116.95 g, 91.2 mmol) was added to a jacketed reaction vessel and charged with diethyl ether (450 mL). The mixture was thoroughly stirred with an overhead mixer and cooled to 10 °C. LiAlH4 (455.8 mmol, 442.5 mL) as a 1.03 M solution in diethyl ether was slowly added to the reaction via cannula. The reaction mixture was maintained at 20 °C and stirred for 16 h.
Solids were removed by filtration and washed with diethyl ether (200 mL). The filtrate was concentrated under vacuum and the crude product was extracted with pentane (100 mL). The pentane extract was washed at room temperature with 9N H2SO4 (3 × 50 mL) by dropwise addition and was accompanied by vigorous gas evolution. The organic layer was dried over Na2SO4, filtered, and fractionally distilled under reduced pressure to give cyclohexasilane (14.0 g, 77.5 mmol, 85%, >99% pure by 1H NMR).
Lu at pages 6053-6054 (emphasis added).
Lu’s above process is summarized by the Examiner as follows:1
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Lu at pages 6053-6054. In summary, Lu teaches that [(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14] (which is per claim 1 “a salt of the polyhalosilane compound (C2)”) is formed is reduced by lithium aluminum hydride (LiAlH4) (the elected species of reducing agent (R2)) to cyclohexasilane (Si6H12) (the elected species (CX)).
Differences between Hengge or Lu and Claim 1
Both Hengge and Lu differ from claim 1 in the same respect. That is Hengge and Lu each filter the reaction solids resulting from the LiAlH4 (which are per claim 1 “the resulting material of the reducing agent (R2)”). Thus, both Hengge and Lu do perform a “separating step of a solid and a liquid”, which is not permitted by claim 1 as amended. That is, neither Hengge nor Lu meet the claim 1 reducing agent removal limitation as bolded below
Claim 1 . . . a removing step in which a reaction solution of the reducing step (P1) is subjected to at least two steps to remove the reducing agent (R2) and/or a resulting material of the reducing agent (R2) contained in the reaction solution, wherein
the removing step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) is carried out without a (T1) separating step of a solid and a liquid . . .
Secondary Art Teaching Acid Workup of Lithium Aluminum Hydride Reactions
Claim 1 recites the following (T3)/(T4) as an alternative for the claim 1 “removing step in which a reaction solution of the reducing step (P1) is subjected to at least two steps to remove the reducing agent (R2)”.
a (T3) contacting step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) with an acid aqueous solution, and
a (T4) distilling step of the hydrogenated polysilane compound (CX).
The secondary art discussed below teaches that such contacting of a lithium aluminum hydride reaction mixture with an aqueous acid (e.g., sulfuric acid) is a conventional workup procedure whereby the resulting two-layer, extractable mixture is convenient for product isolation and does not require a separating step of a solid and a liquid (e.g., no filtration required).
P. Stapp et al., 24 The Journal of Organic Chemistry, 1798-1800 (1959) (“Stapp”)
Stapp teaches reduction of 3-butyl-3-propyloctanoic acid to (I) to 3-butyl-3-propyl-1-octanol (II) using an excess of lithium aluminum hydride, followed by destruction of the excess hydride with ethyl acetate, prior to hydrolysis, according to conventional procedures. Stapp at 1798, col. 2. Stapp teaches the following procedure.
Reduction of S-butyl-8-propyloctanoic acid (I). In a 2-1. three necked flask fitted with a condenser protected by a drying tube, a mercury-sealed stirrer, and an addition funnel, were placed 11.4 g. (.30 mole) of lithium aluminum hydride and 500 ml. of dry ether, and the mixture was stirred until a uniform slurry was obtained. A solution of 48.4 g. (.20 mole) of 3-butyl-3-propyloctanoic acid in 150 ml. of dry ether was added dropwise over a period of 2 hr., stirred for an additional 4 hr. and allowed to stand overnight.
The excess hydride was destroyed by the dropwise addition of 200 ml. of a 50% solution of ethyl acetate in dry ether. The mixture was hydrolyzed with 500 ml. of 10% sulfuric acid, the layers separated, and the aqueous layer extracted with ether. The combined ether layers were "washed with water, 10% sodium bicarbonate solution, again with water, dried over magnesium sulfate, and filtered. The ether was removed at atmospheric pressure and the residue distilled under reduced pressure through a short Vigreux column. There was obtained 47.4 g. of a colorless oil . . .
Stapp at page 1799, col. 2. Here, after the reduction, Stapp uses 10% aqueous sulfuric acid to “hydrolyze” the solid lithium aluminum hydride salt/byproducts so as to form an ether-extractable product mixture followed by distillation of the product. This is the same aqueous sulfuric-acid workup procedure for LiAlH4 described in the instant specification’s working example for reduction of cyclic halosilane to cyclic hydrogenated silane.2 The Examiner asserts that in Stapp’s above procedure, the sulfuric acid dissolves the lithium aluminum hydride by products resulting in a two-phase mixture where the product is extracted with ether. Thus, Stapp does not employ nor require, a separating step of a solid and a liquid (e.g., no filtration required).
Thus, Stapp meets the claim 1 limitation of:
Claim 1 . . . the removing step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) is carried out without a (T1) separating step of a solid and a liquid . . .
MPEP 2112(V) (citing In re Schreiber, 128 F.3d 1473, 1478, 44 USPQ2d 1429, 1432 (Fed.Cir.1997)).
G. Karabatsos et al., 33 The Journal of Organic Chemistry, 619-621 (1968) (“Karabatsos”
Karabatsos teaches reductions of aryl halides with lithium aluminum hydride. Karabatsos at abstract. Karabatsos teaches the following general procedure.
Procedure.—The following general procedure was used for the reductions. Lithium aluminum hydride, 0.36 g (10 mmoles), was added to 25 ml of dry solvent in a 50-ml single-necked, round-bottomed flask that was fitted with a condenser and drying tube. The aromatic halide (10 mmoles) was added to the hydride slurry and the resulting mixture was refluxed or heated at constant temperature for 24 hr. After reaction, the unreacted hydride was quenched by careful dropwise addition of water.
Next, 30 ml of 10% sulfuric acid was added followed by extraction with three 75-ml portions of ether. The ether extract was washed with 25 ml of saturated sodium bicarbonate solution and four 50-ml portions of water, dried over anhydrous magnesium sulfate, and evaporated.
Karabatsos at page 621, col. 2 (emphasis added). Here as in Stapp above, after the reduction, Karabatsos uses 10% aqueous sulfuric acid to process the solid lithium aluminum hydride salt/byproducts so as to form an ether-extractable product mixture.
L. Field et al., 16 The Journal of Organic Chemistry, 946-953 (1951) (“Field”)
Field teaches lithium aluminum hydride reduction of reduction of certain sulfonyl halide, anhydride, and amide derivatives of sulfonic acids. Field at page 946, 1st paragraph. Field teaches the following workup after lithium aluminum hydride reduction.
Excess hydride remaining after reactions was decomposed by addition of alcohol-ether or water, followed by 10 ml. of 10% sulfuric acid. After the hydrogen thus evolved had been measured, an excess of 10-20% sulfuric or hydrochloric acid was added to dissolve the precipitate.
The organic layer was separated, transferred to a fresh separatory-funnel, and extracted with a 5-10% aqueous sodium hydroxide solution. The ether solution was dried over sodium sulfate and concentrated to give the “neutral fraction.”
Field at page 950, 3rd paragraph. Field teaches one of ordinary skill that the precipitated salts resulting from a lithium aluminum hydride reduction are dissolvable using 10-20% sulfuric or hydrochloric acid so as to provide an extractable two-phase system.
E. Eliel et al., 82 Journal of the American Chemical Society, 1367-1372 (1960) (“Eliel”)
Eliel teaches reductions of 4-t-butylcyclohexanone with lithium aluminum hydride. Eliel at Abstract. Eliel teaches that additions of ketone to the mixed hydrides were carried out at room temperature and reaction mixtures were hydrolyzed with water and dilute sulfuric acid. Eliel at page 1371, col. 2, lines 11-14.
Reduction of 4-t-Butylcyclohexanone. (a) In the Presence of Excess Mixed Hydride.—To a solution of 13.34 g. (0.1 mole) of anhydrous aluminum chloride in 100 ml. of anhydrous ether was added 23.3 ml. (0.0275 mole) of 1.18 M ethereal lithium aluminum hydride. After stirring the homogeneous solution for 0.5 hour, a solution of 15.4 g. (0.1 mole) of 4-t-butylcyclohexanone in 100 ml. of anhydrous ether was added dropwise over a period of one hour.
The mixture was boiled for 2 hours, excess hydride destroyed with 20 ml. of water, and the precipitate formed dissolved in 45 ml. of 10% sulfuric acid. Extraction, drying over potassium carbonate and concentration gave 14.7 g. (94% yield) of 4-t-butylcyclohexanol. Infrared analysis (vide infra) showed the material to contain 81-82% trans and 18-19% cis isomer and ketone to be absent.
Eliel at page 1371, col. 2. Eliel teaches one of ordinary skill that the precipitated salts resulting from a lithium aluminum hydride reduction are dissolvable using 10-20% sulfuric or hydrochloric acid so as to provide an extractable two-phase system.
S. Imoto et al., US 2017/0158518 (2017) (“Imoto”)
Imoto teaches distilling crude cyclohexasilane to obtain purified cyclohexasilane, the absolute pressure during distillation is set to 2 kPa or less, and the heating temperature of crude cyclohexasilane is set to 25 to 100° C to give pure cyclohexasilane at a rate of 98% by mass or more and 100% by mass or less. Imoto at Abstract; Id. at page 2, [0015].
A. Elangovan et al., US 8,975,428 (2015) (“Elangovan”)
Elangovan is cited here as motivating one of ordinary skill to seek and improve methods of producing cyclohexasilane (Si6H12) in view of its substantial utility.
Elangovan teaches that cyclohexasilane (Si6H12) can be employed as a liquid precursor for electronics grade silicon materials and devices and that cyclohexasilane is a relatively benign, liquid phase alternative to gaseous SiH4 and/or corrosive trichlorosilane (HSiCl3) in the various processes and technologies adopted in silicon based electronic industries. Elangovan at col. 1, lines 30-36. Elangovan teaches that the tetradecahalocyclohexasilane dianion, such as a tetradecachlorocyclohexasilane dianion, can be chemically reduced to cyclohexasilane. The reduction reaction can be carried out by contacting the compound containing the tetradecahalocyclohexasilane dianion with a metal hydride reducing agent in an organic solvent at temperatures from -110 to 150° C, where suitable reducing agents include lithium aluminum hydride and diisobutylaluminum hydride. Elangovan at col. 5, lines 18-23.
Obviousness Rationale
One of ordinary skill seeking cyclohexasilane (Si6H12), in view of the utility taught by Elangovan, is motivated to modify the procedure of either of Hengee or Lu by isolating the cyclohexasilane (Si6H12) from the resulting LiAlH4 reaction mixture (obtained according to Hengee or Lu) by contacting the lithium aluminum hydride reaction mixture with an aqueous acid (e.g., sulfuric acid) in the conventional workup procedure taught by secondary references Stapp, Karabatsos, Field, and/or Eliel resulting in a two-layer organic/aqueous phase, extracting the cyclohexasilane (Si6H12) from the organic/aqueous phase with an organic solvent (as taught by Lu or the secondary references), and then distilling the resulting cyclohexasilane (Si6H12) as taught by Lu or Imoto. One of ordinary skill is so motivated because (for example in a larger scale preparation) a filtration step is avoided. Practice of Hengee or Lu as proposed above meet each and every limitation of claim 1, including either of alternative (T2)/(T4) or (T3)/(T4):
Claim 1 . . . a removing step in which a reaction solution of the reducing step (P1) is subjected to at least two steps to remove the reducing agent (R2) and/or a resulting material of the reducing agent (R2) contained in the reaction solution, wherein
the removing step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) is carried out without a (T1) separating step of a solid and a liquid, and comprises:
a (T2) liquid-liquid phase separating step of one liquid and another liquid, wherein the reaction solution, a concentrated solution of the reaction solution, or a washing solution of the reaction solution or the concentrated solution of the reaction solution is subjected to the (T2) liquid-liquid phase separating step, and
a (T4) distilling step of the hydrogenated polysilane compound (CX); or
a (T3) contacting step of the reducing agent (R2) and/or the resulting material of the reducing agent (R2) with an acid aqueous solution, and
a (T4) distilling step of the hydrogenated polysilane compound (CX).
The further limitations of claims 2, 4 and 5 are clearly met by practice of Hengge or Lu as proposed above.
The further limitations of claims 9-12 are clearly met by practice of Hengge or Lu as proposed above because Lu’s reducing step (P1) is carried out in the presence of diethyl ether and Hengge’s reducing step (P1) is carried out in an ether/benzene mixture.
Respecting claim 13, Elgammal employs about 100 ml (0.1 L) of ether per 10 mmol (0.01 mol) of halosilane [NEt4]2 [Si6Cl14], which falls within the claim 13 range. And Hengge employs a total volume of ether/benzene of about 300 ml (0.3 L) of ether per 3.6 mmol (0.0036 mol) of halosilane Si6Cl12, which also falls within the claim 13 range. Claim 13 is therefore obvious.
Respecting claim 14, Lu teaches that in the reduction step, 0.0912 mol of halosilane [(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14] is employed in 450 ml + 442.45) of ether (0.8925 liters for a molar concentration of 0.102 mol/L, which is close to, but does not meet the claim 14 limitation of “wherein a molar concentration of the halosilane raw material (CO) in the reducing step (P1) is 0.150 mol/L or higher”. Thus, the difference is one of reactant concentration. Claim 14 is obvious because a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP § 2144.05. Further, 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)). Here, one of ordinary skill seeking to optimize or develop workable ranges for the concentration of the starting cyclic chlorosilane is motivated to increase its molar concentration (for example to within the claimed range of “0.150 mol/L or higher”) to increase efficiency by reducing the amount of solvent needed.
The further limitations of claim 16 are clearly met by practice of Hengge or Lu as proposed above
The further limitations of claims 17 and 18 are met by practice of Lu as proposed above because Lu’s reduction of [(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14] of with lithium aluminum hydride forms an aluminum complex as a byproduct. These appear to be the “solids were removed by filtration”. Lu at pages 6053, col. 2. This is evidenced by V. Ponomarev et al., 21 Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 1328-1331 (1972). Ponomarev teaches that the reduction of chlorosilanes by lithium aluminum hydride (LiAlH4) occurs with formation of the aluminum complex and/or aluminum chloride complex as follows.
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Ponomarev at page 1330. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). The further limitations of claims 17 and 18 are met by practice of Hengge as proposed above because Hengge’s reduction of Si6Cl12 (i.e., dodecachlorocyclohexasilane) with lithium aluminum hydride forms an aluminum complex as a byproduct for the same reasons just discussed for Lu.
The further limitations of claims 39-42 and 46 are clearly met respecting Hengge. Respecting claim 39-40, Hengge’s Si6Cl12 (i.e., dodecachlorocyclohexasilane) meets the structural limitations of claim 1 (C1).
Claim 1 . . . a polyhalosilane compound (C1) comprising a Si-Si bond and a Si-X bond (X represents a halogen atom) in the same molecule . . .
and it is per claim 40 “a cyclic halosilane compound” and Hengge’s product (Si6H12) is, per claim 40, “a cyclic hydrogenated silane compound”. Respecting claims 41 and 42, Hengge’s product (Si6H12) is “cyclohexasilane”. Respecting claim 46, Hengge teaches reduction of Si6Cl12 (i.e., dodecachlorocyclohexasilane) to Si6H12. The limitations of claims 39-42 are clearly met. Lu’s [(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14] meets the structural limitations of claim 1 (C1) or (C2).
Claim 1 . . . a polyhalosilane compound (C1) comprising a Si-Si bond and a Si-X bond (X represents a halogen atom) in the same molecule,
a salt of the polyhalosilane compound (C2), and
and it is per claim 40 “a cyclic halosilane compound” and Lu’s product (Si6H12) is, per claim 40, “a cyclic hydrogenated silane compound”. Respecting claims 41 and 42, Lu’s product (Si6H12) is “cyclohexasilane”.
The limitations of claim 47 and 48 are clearly met by practice of Hengge or Lu as proposed above.
Conclusion
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.
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 For the structure of [(Et2NCH2CH2)2NEt·H2SiCl]2[Si6Cl14], see S. Choi et al., 123 Journal of the American Chemical Society, 8117-8118 (2001).
2 In working Example 1-1, the specification teaches that the following workup and distillation was conducted after the LiAlH4 reduction of cyclic halosilane to cyclic hydrogenated silane (per claim 1 steps (T3)/(T4)) as follows:
After the reaction, the resulting reaction solution was slowly added dropwise to a 10% aqueous sulfuric acid solution cooled to 0°C.
After stirring at room temperature for 30 minutes, a clear colorless solution containing no solids in both the organic and aqueous layers was obtained.
After allowing the solution to stand, the aqueous layer was removed by liquid separation and the organic layer was collected, and the organic layer was concentrated under reduced pressure to obtain 5.7 g of a crude product. At this time, no solids were observed adhering to the top of the concentrator or the cooler for solvent condensation.
The crude product was further purified by distillation under reduced pressure in a 100-mL glass distillation apparatus to obtain 2.8 g of colorless, transparent cydohexasilane with an area purity of 98% by gas chromatography (GC). At this time, there were no solids adhering to the top of the distillation apparatus or the cooler for condensation after distillation.
Specification at lines bridging pages 101-102.
Prosecution Insights