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 1-3, 5-6, 8-20 of D.M. Ermert, et al. US 18/204,210 (05/31/2024) are pending, under examination on the merits and are rejected.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III).
Interpretation of the Claims Term “adduct”.
All the claims recite the term of “adduct”, the specification does not provide definition for the claimed “adduct”. The closest information disclosed by the specification as follows:
[008] The present disclosure uses coordinating solvents to form isolable alkyltintricholoride adducts alkylSnCl3(solv)1-2, which effectively provide a synthon for producing the desired tris(dimethylamido)alkyl tin products of interest in high- purity. The methods of the present disclosure require fewer reagents and steps than the current processes to manufacture alkyltintricholoride adducts and therefore presents a faster and less expensive process.
Specification at page 8, [0008] and [0012], emphasis added.
The prior art Yoder teaches that:
Recent studies have shown that organotin mono- and di-halides form predominantly l/l adducts in solution with a variety of monodentate bases. Preliminary results from our laboratory indicate that organotin trihalides also form l/l adducts, but that other species, including 1/2 adducts, are also formed with stronger bases.
C.H. Yoder, et al. 346 Journal of organometallic chemistry 165-170 (1988)(“Yoder”), page 165, line 1-5, emphasis added.
The prior art Tarassoli teaches that:
Organotin(IV) compounds containing electronegative atoms such as halogen show Lewis acidic character and the tin atom increases its coordination number from four to five or six by addition of neutral organic donor ligands.
A.Tarassoli, et al, 2 Inorganic Chemistry Communications, 595-598(1999)(“Tarassoli”), page 596, line 3-6, emphasis added.
Therefore, according to the teachings from arts and consistent with the information disclosed by the specification, the term “adduct” is broadly and reasonably interpreted as a complex formed through the formation of a coordinate covalent bond between the claimed RSnX3 which acts as a Lewis acid and an electron pair donor ligand which acts as a Lewis base.
Withdrawn Claims Rejections 35 U.S.C. 112(b)
Rejection of claims 1-3, 7-9, 11-13 and 17-20 pursuant to 35 U.S.C. 112, as indefinite because the claim term “alkyltintrihalide” is unclear is withdrawn in view of claims 1, 11 and 20 have been amended and the structure of RSnX3 in the instant claims is clear.
Withdrawn Claim Rejections - 35 USC § 112(d)
Rejection of claims 3 and 13 under 35 U.S.C. 112(d) is withdrawn because the instant claims 3 and 13 are amended to depend on claim 1 and claim 11 respectively.
Withdrawn Claim Rejections - 35 USC § 102
Rejection of claims 1-5, 7-10 under 35 U.S.C. 102(a)(1) as being anticipated by R. Barbieri, et al, (1971). 32 Journal of Organometallic Chemistry, 97-106 (1971)(“Barbieri”) is withdrawn in view of the instant claim 1 has been amended with a limitation of “wherein the solvent, solution, or combination thereof comprises at least one of tetrahydrofuran (THF),dimethoxyethane (DME), or any combination thereof” that is not met by Barbieri.
Rejection of claims 1-4, 6-7 and 9- under 35 U.S.C. 102(a)(1) as being anticipated by G. Chen, et al, 53 Science China Chemistry 1294-1301 (2010)(“Chen”) is withdrawn in view of the instant claim 1 has been amended with the limitation of X in the formula RSnX3 is Cl or I, which is not met by Chen.
Rejection of claims 1, 4-5, 11, 15, 18-20 under 35 U.S.C. 102(a)(2) as being anticipated by D. Kuiper, et al, US11,697,660B2(2023)(“Kuiper”) in view of both Kuiper and the instant application have a common assignee Entegris, Inc.. Per 35 U.S.C. §102(b)(2)(C), Kuiper is not qualified as a prior art.
Withdrawn Claim Rejections -Double Patenting
Rejection of claims 1, 4-5, 11, 15, 18-20 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 6-9 and 11 of US11697660B2 is withdrawn in view of the Terminal Disclaim filed by Applicant on 02/09/2026.
Claims Objections
Claim 1 is objected to on the grounds of improper parentheticals, for example “(THF)” in claim 1. While Applicant may intend that the parenthetical phrase as abbreviation, it is at best superfluous and better practice is to amend so as to remove the parentheticals to avoid confusion as to whether Applicant improperly intends preferences within the claim. See MPEP § 2173.05(d). Correction of all such parentheticals throughout the claims is required.
New Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 9 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claims upon which they depend on respectively, or for failing to include all the limitations of the claims upon which they depend.
Claim 9 is depending on claim 1 which limits the claimed solvent as:
comprises at least one of tetrahydrofuran (THF),dimethoxyethane (DME), or any combination thereof
Claim 9 further limits the solvent in claim 1 as:
The method of claim 1, wherein the solvent comprises at least one of acetic acid, acetone, acetonitrile, benzene, butanol, butanone, t-butyl alcohol, carbon tetrachloride, chlorobenzene, chloroform, cyclohexane, 1,2-dichloroethane, diethylene glycol, diethyl ether, diethylene glycol dimethyl ether, dimethoxyethane, dimethylformamide, dimethyl sulfoxide, 1,4- dioxane, ethanol, ethyl acetate, ethylene glycol, glycerin, heptane, methanol, methyl t-butyl ether, methylene chloride, N-methyl-2-pyrrolidinone, petroleum ether, propanol, pyridine, tetrahydrofuran, triethylamine, water, xylene, any isomer thereof, or any combination thereof.
When tetrahydrofuran and/or dimethoxyethane is elected as the solvent in claim 9, it has the same solvent as that of claim 1, therefore, claim 9 can not further limit claim 1.
New Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-3, 5, 9-10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by V.S. Petrosyan, et al. 52.2 Journal of Organometallic Chemistry 321-331(1973)(“Petrosyan”) evidenced with O. A. Reutov, et al. 52.2 Journal of Organometallic Chemistry 315-319 (1973)(“Reutov”).
Petrosyan teaches a complex of MeSnCl3•2THF. Petrosyan at page 327, Table 5, Entry 3. Petrosyan also teaches that complex is prepared by mixing the necessary stoichiometric amounts of the components or used the method reported by Reutov. Petrosyan at page 330-331, Experimental.
The evidence from Reutov indicates that the solid complexes are prepared through mixing of organotin halide with the corresponding solvent. See Reutov at Summary.
Thus, Petrosyan teaches a method of preparing of complex of MeSnCl3•2THF through:
(i). obtaining MeSnCl3 that maps the claimed RSnX3 as R is methyl and X is Cl;
(ii).obtaining THF that is a solvent; and
(ii). contacting MeSnCl3 with THF thus forms MeSnCl3.
Which meets each and every limitation of claims 1-3, 5 and 9-10, therefore, claims 1-3, 5 and 9-10 are anticipated.
Maintained 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 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.
Rejection of claims 1-3, 5-6, 8-20 under 35 U.S.C. 103 as being unpatentable over S.T. Meyers, et al, US20170102612A1 (2017)(“Meyers”) in view of K.S. Moon, et al, KR20200079731A (2020)(Moon”) is maintained. The rejection is modified according to the claims amendment.
S.T. Meyers, et al, US20170102612A1 (2017)(“Meyers”)
Meyer teaches compounds of RnSnX(4-n) which can be used as a precursor to produce organotin oxide hydroxide photoresists by hydrolysis in solution or in-situ hydrolysis and may also be suitable for vapor deposition of organotin oxide hydroxide photoresists with desirable properties. Meyer at page 10, [0080], line 1-6. Meyer teaches examples of the compound RnSnX(4-n) such as (CH3)2CHSn(NMe2)3, and (CH2)2CHSn(NMe2)3. Meyer at page 10, [0080], line 14-15.
Meyer also teaches a method of preparation of (CH3)2CHSn(NMe2)3 as follows:
Under argon, a 1-L Schlenk-adapted round bottom flask was charged with LiNMe2 (81.75 g, 1.6 mol, Sigma-Aldrich) and anhydrous hexanes (700 mL, Sigma-Aldrich) to form a slurry. A large stir bar was added and the vessel sealed. An addition funnel under positive argon pressure was charged with iPrSnCl3 (134.3 g, 0.5 mol, Gelest) via syringe and then attached to the reaction flask. The reaction flask was cooled to −78° C and the iPrSnCl3 was then added dropwise over a period of 2 hours. The reaction was warmed to room temperature overnight while stirring. The reaction produces a by-product solid. After settling, the solid was filtered under positive argon pressure through an in-line cannula filter. The solvent was then removed under vacuum, and the residue distilled under reduced pressure (50-52° C., 1.4 mmHg) to give a pale yellow liquid (110 g, 75% yield).
Meyer at page 14, [0112], line 4-20, emphasis added.
The Meyer method is schematically summarized by Examiner as indicated below.
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273
1883
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Meyer fairly teaches one ordinary skilled artisan that the reaction between iPrSnCl3 and LiNMe2 in hexane is an exothermic reaction and iPrSnCl3 needs to be slowly added to the solution of LiNMe2.
The Meyer method comprises:
obtaining iPrSnCl3;
obtaining a lithium dialkylamide which is LiNMe2 ; and
form a tris(dialkylamido)alkyl tin product which is (CH3)2CHSn(NMe2)3.
Difference between Meyer and the Claims
The Meyer method differs from the independent claim 1 in that Meyer does not teaches to contact of iPrSnCl3 with a solvent, a solution, or any combination thereof, wherein the solvent,solution, or combination thereof comprises at least one of tetrahydrofuran, dimethoxyethane, or any combination thereof so as to form an adduct of iPrSnCl3.
The Meyer method differs from the independent claim 11 in that Meyer does not teaches to contact of an adduct of iPrSnCl3 with LiNMe2 to form (CH3)2CHSn(NMe2)3.
The Meyer method differs from the independent claim 20 in that Meyer does not teaches to:
(i). contact of iPrSnCl3 with a solvent, a solution, or any combination thereof, wherein the solvent,solution, or combination thereof comprises at least one of tetrahydrofuran (THF), dimethoxyethane (DME), or any combination thereof so as to form an adduct of iPrSnCl3 so as to form so as to form an adduct of iPrSnCl3; and
(ii). contact of an adduct of iPrSnCl3 with LiNMe2 to form (CH3)2CHSn(NMe2)3.
K.S. Moon, et al, KR20200079731A (2020)(Moon”)
Moon is published in Korean, a copy of machine translation is attached as the second part of the reference resulting the total page of the full reference is 34, the citation format is xx/34.
Moon teaches a method of preparation of the compound formula 5 from the formula A-4 which is iPrSnCl3 as follows:
The compound of formula A-4 (5 g, 18.6 mmol) of Synthesis Example 5 was dissolved in 50 ml of THF, and the temperature was lowered to 0° C. in an ice bath. Then, 2-methylallyl magnesium chloride (2-methylallyl MgCl) 0.5M THF solution (62 mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 12 hours to obtain a compound represented by the following Chemical Formula 5 in a yield of 90%.
Moon at page 16/34, [0137]-[0141] and page 32/34, paragraph 2. The Moon method is schematically summarized by Examiner as indicated below.
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373
1488
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Moon fairly teaches one ordinary skilled artisan that THF can be used as a solvent to prepare a solution of iPrSnCl3 for a reaction to break the Sn-Cl bond of iPrSnCl3.
Obviousness Rationales of Claims 1-3, 5-6, 8-20
It would have been prima facie obvious for one skilled artisan to arrive at the instantly claimed invention based on the teachings from Meyer and Moon with a reasonable expectation of success before the effective filing date of the claimed invention.
One ordinary skilled artisan seeking synthesis of iPrSn(NMe2)3 for organotin oxide hydroxide photoresists is motivated to modify the Meyer method through preparation of a solution of iPrSnCl3 in THF and then adding the iPrSnCl3 solution dropwise to the solution of LiNMe2 in hexanes to form the desired product iPrSn(NMe2)3.
One ordinary skilled artisan is motivated to do so with a reasonable expectation of success because:
Meyer teaches the reaction between iPrSnCl3 and LiNMe2 in hexane is an exothermic reaction and iPrSnCl3 needs to be slowly added to the solution of LiNMe2;
Moon teaches that THF can be used as a solvent to prepare a solution of iPrSnCl3 for a reaction to break the Sn-Cl bond of iPrSnCl3;
Adding a solution of iPrSnCl3 in THF to the solution of LiNMe2 can further slowdown the addition rate of iPrSnCl3 so that can make the reaction occurs at more mild condition.
Claims 1, 9, 11, 17- 20 are obvious because iPrSnCl3 is a Lewis acid and THF is a Lewis base, therefore, there is a reasonable expectation of a adduct is formed between iPrSnCl3 and THF. Further, the proposed method is substantially same as the Example 3 in the specification except EtSnCl3 is used in the Example 3. See specification page 20, [00143]-[00144].
Claims 2-3 and 12-13 are obvious because THF is not an amine.
Claim 5 is obvious because iPrSnCl3 maps the formula RSnX3 in claims 4-5 as R is isopropyl and X is Cl.
Claims 6 and 16 are obvious because one ordinary skilled artisan is also motivated to use the proposed method to prepare (CH2)2CHSn(NMe2)3 with (CH2)2CHSnCl3 as the starting material because Meyer teaches that (CH2)2CHSn(NMe2)3 is another example compound can be used to produce organotin oxide hydroxide photoresists.
Claim 8 is obvious because one ordinary skill is motivated to further modify the proposed method by using a mixture of THF and hexane to make a solution of iPrSnCl3 given Meyer teaches the reaction is conducted in the presence of hexane.
Claim 10 and 14-15 are obvious because as mentioned above that the proposed method is substantially same as the Example 3 in the specification except EtSnCl3 is used in the Example 3. See specification page 20, [00143]-[00144], therefore, there is a reasonable expectation that the similar adduct product is formed.
Applicant’s Arguments
Applicant argues on the ground that Meyers teaches to use of iPrSnCl3 rather the claimed adduct to react to form iPrSn(N(CH3)2)3. Remarks at page 7-8, Response to 35 U.S.C. §103.
This argument has been fully considered but not persuasive. While Meyers teaches to use of iPrSnCl3 direct to react to from iPrSn(N(CH3)2)3, the proposed method is first to form a solution of iPrSnCl3 in THF, and then add the solution of solution of iPrSnCl3 in THF dropwise to the solution of the solution of LiNMe2 in hexane. As mentioned in the previous Office action that given iPrSnCl3 is a Lewis acid and THF is a Lewis base, an adduct is necessarily formed in solution, by a Lewis acid base reaction. Once the iPrSnCl3(THF) adduct is formed and added into the solution of with LiNMe2 in hexane, it reacts with LiNMe2 to form the product. 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). This is a procedural burden shifting. The requirement that the prior art necessarily teaches the alleged inherent (functional) element still remains. MPEP § 2112(IV). However, the burden is shifted to Applicant to demonstrate the alleged inherent element is not necessarily present in the cited prior art.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692