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 .
Claim Status
Claims 1-57 were filed on 1/5/2024. In a preliminary amendment filed on the same day, claims 1-10, 23, 24, 28-33, 36, 39-42, 44-46, and 51-57 were canceled, claims 11, 19-22, 25-27, 34, 35, 37, 38, 43, and 47-50 were amended. Claims 11-22, 25-27, 34, 35, 37, 38, 43, and 47-50 are pending.
Priority
The Application was filed on 1/4/2024 and claims the benefit of priority to:
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See filing receipt dated 8/14/2024.
Specification
The disclosure is objected to because of the following informalities:
there is an error in the US Patent No. recited at the end of [0022]. The specification recites 10,73287,446, which is not a valid US Patent No.
Appropriate correction is required.
Claim Objections
Claims 11, 17, 18, 47, 48, and 50 are objected to because of the following informalities:
In line 6 of step (i) of claim 11, the limitation “an substituted amine” should be amended to recite “a substituted amine”.
In claim 17, the word “dimethyltin” is misspelled as “dimethytin”.
In claim 18, the word “diethyltin” is misspelled as “diethytin”.
In line 5 of claim 47, the limitation “R5N(CR6)NR7, an imido (-N(COR8)(COR9), an alkynido” should be amended to recite: limitation “R5N(CR6)NR7), an imido (-N(COR8)(COR9)), and an alkynido”.
The same change should be made in line 5 of claim 48.
In line 14 of claim 50, the limitation “tBuSn(OtBu)3” should be amended to recite “tBuSn(OtBu)3”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 49 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 49 depends from claim 1, which defines X as Cl, Br, F, or I. However, claim 49 then indicates that “X is a ligand having a hydrolyzable bond with Sn”. Therefore, the scope of variable X is not clear in claim 49.
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 (i.e., changing from AIA to pre-AIA ) 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, 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.
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.
Claim(s) 11, 19, 22, 27, 35, 37, and 38 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alleston (“383. The preparation of some organotin(IV)compounds” J. Chem. Soc. 1962, p. 2050) as evidenced by Benzene (“Benzene Boiling Point”, downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Benzene#section=Boiling-Point&fullscreen=true., on 6/10/2026).
Applicant claims a process for preparing a diorganotin dihalide of formula R2SnX2 free of R4Sn, R3SnX and RSnX3 comprising:
i) forming a mixture of a diorganotin oxide of formula R2SnO with an organic solvent;
ii) adding an aqueous solution of an acid of the formula HX to the mixture of step (i) to form a biphasic mixture comprising an organic phase and an aqueous phase;
iii) stirring the biphasic mixture for a period of time;
iv) separating the organic phase and an aqueous phase of the biphasic mixture;
and
v) isolating the compound of the formula R2SnX2.
On p. 2052 Alleston teaches the following procedure (a) for producing dibutyltin di-iodide:
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Dibutyltin oxide, a compound of instant formula R2SnO, wherein both R are n-butyl (a linear C4 alkyl group) dissolved in a mixture of 54% aqueous hydrogen iodide (HX, wherein X is I-claim 22) and benzene (aromatic organic solvent-claim 19) is stirred for 1.5 hours (falling within the range of claim 27) at room temperature (approx. 23°C, falling within the ranges of claims 37-38) to produce dibutyltin di-iodide, a compound of instant formula R2SnX2 and R and X are the same as above, in a biphasic reaction system (water and benzene). Presumably the product is free of R4Sn, R3SnX, and RSnX3 by-products because they are not used as reactants in the process and Alleston is silent regarding their presence as impurities.
Alleston does not explicitly teach the claim order of addition of instant steps (i) and (ii) wherein the dibutyltin oxide and the benzene are mixed and then the aqueous solution of HI is added thereto.
It would have been prima facie obvious to arrive at the instantly claimed process with a reasonable expectation of success based on the teachings of Alleston before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the order of addition to form the biphasic reaction mixture because the selection of any order of mixing ingredients and/or performing process steps is prima facie obvious. See MPEP 2144.04(IV)(C). The reaction will not commence until all of the components are present, regardless of the order they are mixed.
Further regarding claim 35, Alleston teaches that the dibutyltin di-iodide is isolated from the benzene layer, after it has been washed with water and aqueous thiosulfate and then dried. Alleston does not explicitly teach how the dibutyltin di-iodide is separated from the benzene layer, however, the boiling point of the product is recited as being in the range of 124-134°C. This is significantly higher than that of benzene, which is 80°C as taught by the cited evidentiary reference. Therefore, it would have been prima facie obvious to separate the benzene from the product by distillation.
Claim(s) 12-18, 21, and 47-49 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alleston (“383. The preparation of some organotin(IV)compounds” J. Chem. Soc. 1962, p. 2050) as evidenced by Benzene (“Benzene Boiling Point”, downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Benzene#section=Boiling-Point&fullscreen=true., on 6/10/2026), as applied to claims 11, 19, 22, 27, 35, 37, and 38 above, and further in view of Wood (“Product Subclass 8: Tin Halides and Organotin Halides” Science of Synthesis, 2003, doi:10.1055/sos-SD-005-00250); Davies (“11. Organotin Halides” Organotin Chemistry, Second Edition, 2004); and Ingham (“Organotin compounds”, Chemical Reviews, 1960, p. 460).
Applicant claims the process wherein R is a methyl or ethyl group and X is Cl.
Alleston only teaches one example wherein R is butyl and X is I. Wood, Davies, and Ingham are all reviews of organotin compounds, in particular organotin halides.
In section 5.2.8.8.2 on p. 340, Wood reiterates the example of Alleston and teaches that the method can be generally applied to the treatment of diorganotin oxides and hydrogen halides:
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. Wood further teaches that the method is the second step in a two-step process to obtain highly purified R2SnX2 compound. See 4[Wingdings font/0xE0]36[Wingdings font/0xE0]4.
In section 11.1.3 on p. 168, Davies teaches that diorganotin oxides, R2SnO, react with halogen acids, HX to give the corresponding diorganotin dihalides, R2SnX2:
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. The Alleston example corresponds to equation 11-7 above.
Ingham teaches that organotin oxides can be readily converted to the corresponding diorganotin dihalide compounds, R2SnX2, by reaction with HX acids:
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, . See col. 2 on p. 488.
Wood (general introduction on p. 315), Davies (section 11.1 on p. 166), and Ingham (section VI on p. 522-524) also teach that organohalides are valuable synthetic starting materials in industrial chemistry, thus providing motivation to synthesize said compounds.
Further regarding compounds in claims 12-18 and 21, Wood, Davies, and Ingham all teach compounds of formula R2SnX2, wherein R is Me or Et, and X is Cl, Br, or I. For example:
In Wood, see Scheme 3 compound 1 on p. 318 and compound 8 on p. 334 ;
In Davies, see equation 11-1 on p. 166, Table 11-1 on p. 168, 11-15 on p . 169; Table 11-2 on p. 170; Table 11-3 on p. 171; and Table 11-5 on p. 173;
In Ingham, see Table 10 on p. 484-485 for compounds wherein both R are identical and Table 11 on p. 486, wherein each R is different.
It would have been prima facie obvious to combine the teachings of Alleston, Wood, Davies, and Ingham to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute diorganotin oxides, R2SnO, wherein R is methyl or ethyl, and HX acids, wherein X is Cl, Br, I, or F, in the process disclosed in Alleston (wherein R is n-butyl and X is I), because Wood, Davies, and Ingham all teach that such reactions are predictable. Wood, Davies, and Ingham further teach that compounds wherein R is methyl or ethyl and X is Cl are valuable synthetic intermediates, thus providing motivation to obtain the compounds using the predictable combined method of Alleston, Wood, Davies, and Ingham. Also see MPEP 2143(I)(B).
Further regarding claims 47 and 49, Ingham teaches that the diorganotin dihalide compound of instant formula R2SnX2 can be predictably reacted with metalloorganic oxides (ROM) to produce compounds of formula R2Sn(OR’)2. See col. 1 on p. 490.
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Table 17 on p. 495-498, as discussed in the first column on p. 494, teach specific examples of products formed using the above reaction, wherein the MOR’ nucleophile can be an alkoxide, phenoxide, alcohol or phenol. These products correspond to compounds of instant formula R2SnL2, wherein L is -OR1, and R1 is an aryl or alkyl.
Regarding claims 48 and 49, Wood teaches that compounds of formula R2SnX2 can react with tin(IV)halides of formula SnX4 to produce compounds of formula RSnX3. For exmaple, see p. 333:
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. Also see col. 12 of p. 486 of Ingham. One the organotin trihalide product (RSnX3) is produced, then the same process of Ingham as described with respect to claim 47 can be used with at least three equivalents of L to obtain the instantly claimed compound of formual RSnL3, wherein L is the same as above.
Claim(s) 50 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alleston as evidenced by Benzene in view of Wood, Davies, and Ingham, as applied to claims 11, 12-19, 21, 22, 27, 35, 37, 38, and 47-50 above, and further in view of Meyers (US2019/0137870, published on 5/9/2019).
Ingham teaches a genus which encompasses with the alkoxides of claim 50, but does not explicitly teach any of the claimed compounds.
Meyers is directed toward organometallic precursors for the formation of high-resolution lithography patterning coatings based on metal hydroxide chemistry. See abstract. In [0081], Meyers teaches the following exemplary suitable precursors:
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. All of the RSn(OtBu)3 compounds are included in claim 50 (see lines 18-21 of claim 50).
It would have been prima facie obvious for a person of ordinary skill in the art to combine the teachings of Alleston, Wood, Davies, Ingham, and Meyers to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to produce one of the compounds in claim 50 in the combined process because Meyers teaches said compounds are valuable precursors for the formation of high-resolution lithography patterning coatings. Further, the compounds could be predictably obtained using the methods of claims 47 and 48, which were discussed in the preceding rejection. Also see MPEP 2143(I)(B).
Claim(s) 20, 25, 26, 34, and 43 is/are rejected under 35 U.S.C. 103 as being unpatentable over Alleston as evidenced by Benzene in view of Wood, Davies, and Ingham, as applied to claims 11, 12-19, 21, 22, 27, 35, 37, 38, and 47-50 above, and further in view of Solvents (downloaded from https://web.archive.org/web/20200907224315/https://organicchemistrydata.org/solvents/ originally captured 9/7/2020 and downloaded 6/10/2026).
Applicant claims the method wherein the solvent is methylene chloride (dichloromethane, DCM, CH2Cl2) (claims 20, 25, 26); the compound of formula R2SnX2 is isolated using a solvent comprising toluene (claim 34); and that the yield of the compound of formula R2SnX2 is about or above 80% (claim 43).
None of the previously cited prior art explicitly teaches or suggest these limitations. However, Ingham teaches that organotin halides are generally readily soluble in organic solvents, with the exception of organotin fluorides. Ingham also provides a table including the physical data of several compounds of formula R2SnX2. See section 11.2 and Table 11.3 on p. 171. Additionally, Alleston teaches that the solvent for the reaction, benzene, is also the solvent used for isolation.
Solvents is directed toward the physical properties, including miscibility with water, of commonly used organic solvents, including both toluene and methylene chloride. See Table on p. 1-2. The benzene solvent used by Alleston is a one-carbon homolog of toluene (a benzene ring substituted by a methyl group) and has approximately the same density as benzene (0.88 g/mL vs. 0.87 g/mL). The two compounds are also shown to be only slightly miscible with water (0.18 for benzene vs. 0.05 for toluene), with toluene being even more hydrophobic than benzene.
According to Solvents, methylene chloride is another known organic solvent that is largely immiscible with water (1.32) and also denser than water (1.3 g/mL).
Therefore, both methylene chloride and toluene appear to be suitable substitutes for the benzene reaction and isolation solvent of Alleston.
It would have been prima facie obvious for a person of ordinary skill in the art to combine the teachings of Alleston, Wood, Davies, Ingham, and Solvents to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute the benzene solvent of Alleston for toluene or benzene because, as taught by Solvents, both are commonly used in organic chemistry and are largely immiscible with water. Therefore, substituting either of them for benzene will predictably result in a biphasic reaction process which will provide compounds of formula R2SnX2 with a reasonable expectation of success. Also see MPEP 2144.09 (especially regarding toluene and benzene) and MPEP 2143(I)(B).
Further regarding the 80% or higher yield of claim 43, the example in Alleston only obtains 51% yield (see 5.2.8.8.2 on p. 340 of Wood and 11.1.3 on p. 168 of Davies). However, this is only a single example, and the combination of references teaches all of the other claimed process limitations, including those of claims 25 and 26 which correspond to the examples in the specification as filed. Therefore, it is reasonable to expect that when compounds of R2SnX2 are obtained according to the combined process of the references, that yields of 80% and higher would be possible upon optimization according to the direction in the references. Also see MPEP 2144.05.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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