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 .
Priority
The instant application was filed on 3/28/2024 and claims the benefit of priority to:
PNG
media_image1.png
168
1028
media_image1.png
Greyscale
See filing receipt dated 10/22/2024.
Claim Status
Claims 1-9 were filed on 3/28/2024. In a preliminary amendment filed on the same day, claims 1-9 were canceled and claims 10-17 were newly added. Claims 10-17 are pending.
Claim Rejections - 35 USC § 102
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 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.
Claim(s) 10 and 12-14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Crivello (US 4675426, published on 6/23/1987).
Crivello teaches free-radical initiators of the following formula and their preparation:
PNG
media_image2.png
280
478
media_image2.png
Greyscale
. See col. 1, lines 44-57. R and R1 are the same or different C6-14 aromatic organic radicals, or can be joined together to form divalent aryl radicals. R2 is a monovalent radical selected from C1-8 alkyl, C1-8 alkenyl, C1-8 haloalkyl, C1-8 alkoxy, or C6-13 aryl and R3 is a monovalent radical selected from hydrogen and R2 radicals. See col. 1, line 57-col. 2, line 10. Phenyl is recited as one of seven exemplary aryl radicals for R and R1; propyl (C3 alkyl) and butyl (C4 alkyl) are recited as two of twelve exemplary radicals for R2 and R3. See col. 2, lines 11-21. Crivello specifically exemplifies the following compound:
PNG
media_image3.png
146
200
media_image3.png
Greyscale
, wherein R and R1 are phenyl and R2 and R3 are tert-butyl (C4 alkyls).
Crivello teaches two procedures for producing the compounds. See example 1 in col. 5-6. In the first:
“A mixture was stirred for 12 hours under substantially anhydrous conditions under nitrogen consisting of 18.2 grams (g) (0.1 mole) of benzophenone, 50 mL of tetrahydrofuran, 12.9 g (0.1 mole) of dimethyldichlorosilane, 1.2 g magnesium metal, and 5 mL of hexamethylphosphoramide. The tetrahydrofuran was removed with the aid of a rotary evaporator and approximately 100 mL of methylene chloride was added to the mixture and the solution filtered through a sintered glass filter to remove the magnesium salts. The filtrate was then stripped under reduced pressure leaving a solid residue. The residue was crystallized from absolute ethanol giving a colorless crystalline product having a melting point of 134.degree.-136.degree. C. after drying at 6.degree. C. in vacuo. The product was identified as 2,2-dimethyl-4,4,5,5-tetraphenyl-1,3-dioxa-2-silole based on its proton and .sup.13 C-NMR spectra as well as by the parent peak at M/e=435 and its elemental analysis.”
In the second:
“An alternate procedure was used to prepare the same cyclic silylpinecole. There was added 50 mL tetrahydrofuran to a fluid which was being stirred under a nitrogen atmosphere consisting of 4.8 g (0.2 mole) magnesium metal, 9.1 g (0.05 mole) benzophenone and 2.4 g (0.009 mole) of mercuric chloride. A rapid exotherm ensued with the temperature rising to the boiling point of the tetrahydrofuran. The reaction appeared to be over in 15 minutes and 9.9 g (0.1 mole) of dimethylchlorosilane was added to the solution with stirring. Another exothermic reaction took place and the temperature was controlled with the aid of a water bath. The mixture was allowed to stir for 5 minutes after completing the addition of the silane, then 100 mL ethylether was added to precipitate the magnesium salts. The reaction mixture was filtered through a sintered glass filter and the filtrate placed in a rotary evaporator to remove the solvents. There was obtained a colorless crystalline solid which was washed several times with absolute ethanol. Based on method of preparation and proton NMR and .sup.13 C-NMR, there was obtained a 54% yield of 5.8 g of the above cyclic silyl pinacolate.”
In the first embodiment, all of the reagents are mixed together and reacted. In the second embodiment, a mixture of magnesium metal, benzophenone, and mercuric chloride in THF were reacted, and then the dimethyl chlorosilane was added thereto.
Crivello teaches that the compound of formula
PNG
media_image3.png
146
200
media_image3.png
Greyscale
, the last entry in the Table in col. 6-7 is made using one of the two above processes. This would correspond to a process in which benzophenone (Ph(C=O)Ph) is reacted with a silane of instant formula (I), wherein R1 and R2 are tert-butyl, C4 alkyl groups. Thus, Crivello anticipates instant claims 10, 12, and 13. Further regarding claim 14, tetrahydrofuran (THF) and hexamethylphosphoramide (HMPA) are both aprotic solvents. Also see MPEP 2131.
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) 10, 12-14, and 16, is/are rejected under 35 U.S.C. 103 as being unpatentable over Crivello (US 4675426, published on 6/23/1987).
Crivello was discussed above and its teachings are incorporated herein by reference. Regarding claim 10, though Crivello only exemplifies one example wherein R2 and R3 are both C4 alkyl, thus anticipating the claim, Crivello also teaches that R2 and R3 can be C1-C8 alkyl. Therefore, Crivello also contemplates other embodiments that fall within the claimed process wherein instant R1 and R2 are C1-C8 alkyl groups.
Regarding claim 16, Crivello teaches two processes and only one of those in which the benzophenone and magnesium reductant are combined and then silane of the general formula (I) is added. Though Crivello teaches that the compound of formula
PNG
media_image3.png
146
200
media_image3.png
Greyscale
is prepared using one of the processes, Crivello does not explicitly teach which of the two processes is used.
It would have been prima facie obvious to arrive at the instantly claimed process before the effective filing date of the claimed invention based on the teachings of Crivello with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would be motivated to pre-mix the benzophenone and Mg reductant before adding the silane because such is explicitly suggested by Crivello. Crivello teaches two known and predictable reactions to arrive at the disclosed products, therefore preparing any of the example compounds using either process would be predictable.
Claim(s) 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Crivello (US 4675426, published on 6/23/1987), as applied to claims 10, 12-14, and 16 above, and further in view of Wolfers (US 4145507, published on 3/20/1979).
Crivello teaches the use of dichlorodisubstituted silanes in the disclosed process (those wherein in instant formula (I), R1 and R2 are not Cl). Crivello does not explicitly teach the use of compounds of instant formula (I) wherein R1 is Cl.
Wolfers teaches mixtures obtained by reaction of an alpha-aryl ketone or of an arylaldehyde and the equivalent amount of a base metal in an inert aprotic solvent with a di-, tri-, or tetra-chlorosilane or a chlorinated polyorganosilane or -siloxane work as initiators for free radical-initiated polymerization reactions. See abstract. Wolfers teaches that this corresponds to chlorosilanes of formula (VII) and (VIII) in col. 2:
PNG
media_image4.png
446
462
media_image4.png
Greyscale
. Compounds of formula (VII) are analogous to those of instant formula (I) wherein R1 and R2 are C1-C2 alkyl radicals and compounds of formula (VIII) are analogous to those of instant formula (I) wherein R1 is a C1-C2 alkyl radical and R2 is Cl. Wolfers also teaches that the aryl ketone includes benzophenone and that the base metal includes magnesium. See Table in col. 4-5.
It would have been prima facie obvious to combine the teachings of Crivello and Wolfers to arrive at the 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 use a trichlorosilane in the process of Crivello, because Wolfers teaches that when benzophenone is reacted with Mg in the presence of a dichlorosilane or a trichlorosilane, both produce initiators for free radical-initiated polymerization reactions. This is the same intended use of the compounds as Crivello. Therefore, using a trichlorosilane of instant formula (I) in the process of Crivello, wherein the alkyl group can be a C1-C8 alkyl, with predictably produce other radical initiators. Also see MPEP 2143(I)(B).
Claim(s) 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Crivello (US 4675426, published on 6/23/1987), as applied to claims 10, 12-14, and 16 above, and further in view of Ley (“4 Preparation of Activated Magnesium”, Ultrasound Synthesis, 1989, p. 33-38).
Crivello teaches that the reaction includes HMPA or mercuric chloride as an activating agent for the Magnesium metal. Crivello does not explicitly teach the use of iodine.
Ley teaches that in Grignard reactions, the initiation of the reaction between the organohalide and magnesium are many and varied and include the addition of a crystal of iodine or a few drops of 1,2-dibromoethane to the use of highly coordinating solvents, or freshly turned magnesium metal. See first paragraph on p. 33.
It would have been prima facie obvious to combine the teachings of Crivello and Ley to arrive at the 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 iodine of Ley for the HMPA or mercuric chloride taught by Crivello, because all are known to activate elemental magnesium for radical reactions. Therefore, replacing one known activating agent of magnesium for another is prima facie obvious and predictable. Also see MPEP 2143(I)(B).
Claim(s) 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Crivello (US 4675426, published on 6/23/1987), as applied to claims 10, 12-14, and 16 above, and further in view of Ager (“Dichlorodimethylsilane” eROS, first published on 5/15/2001, and downloaded from https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rd116 on 8/14/2026).
Crivello teaches that the product of the reaction is isolated by either removing THF under vacuum, replacing it with methylene chloride to precipitate Mg salts, removing the salts, removing the methylene chloride solvent by vacuum, and crystallizing the product; or adding diethyl ether to the reaction mixture to precipitate the Mg salts, removing the salts, removing the diethyl ether solvent by vacuum, and crystallizing the product. Crivello does not teach that the reaction is worked up by adding water, neutralizing with a weak base, and removing the aqueous phase.
Ager is an encyclopedia entry regarding dichlorodimethylsilane, a compound of instant formula (I) wherein R1 and R2 are methyl (C1 alkyl). This compound is analogous to the silane compound of Crivello wherein R1 and R2 are tert-butyl (C4 alkyl). Ager teaches that the chlorosilane reacted with water and other protic species with the evolution of hydrogen chloride (an acid).
It would have been prima facie obvious to combine the teachings of Crivello and Ager 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 replace the work-up described in Crivello with that claimed because i) Crivello teaches that the reaction produces magnesium salts which are insoluble in non-polar organic solvents and need to be filtered from the reaction and are therefore presumed to be soluble in water; and ii) that when water reacts with silyl chlorides, it produces acid hydrochloric acid as taught by Ager. Therefore, the skilled artisan, seeking an alternative work-up, would recognize that the addition of water to the mixture containing an organic solvent would also remove the magnesium salts from the reaction, though producing HCl as a by-product. However, acid-base neutralization reactions are well known in the art and it would have been obvious for the skilled artisan to use a basic aqueous wash, comprising either a strong or weak base, though a weak base should produce less of a risk of an exotherm, to remove the Mg salts and quench an HCl generated in situ. Further, separating the aqueous phase from the organic phase by extraction will predictably retain the desired product in the organic layer while removing the Mg salts in the aqueous layer without having to do a filtration procedure. Therefore, replacing one well-known work-up method with another is a predictable way to obtain the desired product. Also see MPEP 2143(I)(B).
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
Prosecution Insights