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
This application claims the benefit of US Provisional 63309181 as reflected in the filing receipt mailed on 26 May 2023.
Information Disclosure Statement
The information disclosure statement (IDS) submitted is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
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.
Claims 19 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ereztech (“Bis(ethylbenzene)molybdenum”, 11 October 2021, The Wayback Machine, Pgs. 1-20).
Ereztech discloses the claims 19 and 20 limitations of a composition of Bis(ethylbenzene)molybdenum which is a mixture of C2H5XC6H6-x, where x=0-4) aka [(C2H5)XC6H6Ƞx]2Mo in a dark green liquid form having a purity of greater than 99%, and in the first instantly claimed formula Ar4 is benzene, Rg is alkyl, Rh-Rm are each independently hydrogen, and M is Mo, see Pg. 1, Synonym, Structure, Assay (purity), Form, and Appearance, meeting the composition, precursor, formula, liquid form, and within the purity range in instant application claim 19 and in instant application claim 20.
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.
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.
Claims 1-11 and 13-17 are rejected under 35 U.S.C. 103 as being unpatentable over Asirvatham et al. (“Synthesis of Bis(η6-alkylbenzene)molybdenum by Arene Metathesis”, 15 March 2001, Organometallics, Vol. 20, Pgs. 1687-1688, hereinafter Asirvatham) in view of Connor et al. (“Thermochemistry of bis-Arene- and Arenetricarbonyl-Chromium Compounds containing Hexamethylbenzene, 1,3,5-Trimethylbenzene and Naphthalene”, 1979, Journal of Organometallic Chemistry, Vol. 179, Pgs. 331-356, hereinafter Connor) and Umilin et al. (“Gas Chromatographic Analysis and Composition of Impurities in Bis-Ethylbenzenemolybdenum”, 1972, Consultants Bureau, Pgs. 1220-1222, hereinafter Umilin), as evidenced by Haynes, (“CRC Handbook of Chemistry and Physics”, 2017, 97th Edition, CRC Press, Pgs. 3-34, 3-174, 3-250).
Asirvatham teaches the claims 1, 4, 5, 7, 8, 10, 11, 13, and 15-17 limitations of the synthesis of bis(η6-alkylbenzene)molybdenum complexes where the arene in bis (arene) molybdenum complexes is replaced by an arene/aromatic solvents, such as ethylbenzene, isopropylbenzene, tert-butylbenzene, or toluene, at elevated temperatures to cleanly produce the corresponding bis(η6-alkylbenzene)-molybdenum complexes in 60-70% yield, see Pg. 1687, Col. 2-Pg. 1688, General Procedure. In a typical reaction, bis (arene) molybdenum complex, such as (η6-C6H6)2Mo, 100 mg, 0.4 mmol, and the aromatic solvent, 2 mL, such as ethylbenzene, isopropylbenzene, tert-butylbenzene, or toluene, are added to a Schlenk flask, the flask is sealed and placed in a 160 °C oil bath for 48 h, excess solvent is removed by vacuum transfer, and the product bis(η6-alkylbenzene)-molybdenum complex, such as (η6-C6H5R)2Mo, where R is ethyl aka bis (ethylbenzene) molybdenum, is recrystallized or sublimed, and typical isolated at yields of 60-70%, see Pg. 1687, Col. 2-Pg. 1688, General Procedure, and in order for recrystallization the product is inherently cooled to at least atmospheric temperature, see MPEP 2112, meeting:
The method of preparing a precursor, the bis(arene) metal complex, such as bis (benzene) molybdenum or bis (ethylbenzene) molybdenum, the first arene, the second arene, such as ethylbenzene, tert-butylbenzene, or toluene, heating the mixture, cooling, and precipitating/crystallizing the bis (first arene) metal complex and the bis (second arene) metal complex molybdenum product, such as bis (ethylbenzene) molybdenum or bis (benzene) molybdenum, bis (toluene) molybdenum, bis (tert-butylbenzene), in instant application claim 1 and in instant application claim 13;
The first instantly claimed formula of for example toluene and ethylbenzene, where Ra is alkyl and Rb-Rf are each independently hydrogen in instant application claim 4 and in instant application claim 15;
Within the temperature range in instant application claim 5;
The inherent cooling in instant application claim 7;
The instantly claimed formula of for example bis (ethylbenzene) molybdenum where Ar3 is ethylbenzene Ra is alkyl and Rb-Rf are each independently hydrogen, M is Mo in instant application claim 8;
The specific first arene and second arene, such as toluene, ethylbenzene, or tert-butylbenzene, in instant application claim 10 and in instant application claim 16;
Within the range of yield in instant application claim 11; and,
The first instantly claimed formula for example bis(η6-alkylbenzene)-molybdenum where Ar4 is benzene, Rg is alkyl, Rh-Rm are each independently hydrogen, M is Mo in instant application claim 17.
Asirvatham does not specifically teach synthesis of a variety of bis(η6-alkylbenzene)molybdenum complexes where the arene in the bis (arene) molybdenum complexes is replaced by a variety of differing arene/aromatic solvents. However, selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results, see MPEP 2144.04 IV.C., and selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07. Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified Asirvatham to replace the arene in any bis (arene) molybdenum complex with the desired substituted arene for the benefit of producing the molybdenum complex without mixtures of various isomers generally obtained if alkylbenzenes are employed in the FHS, see Asirvatham, Pg. 1687, Col. 2-Pg. 1688, General Procedure.
Asirvatham does not teach:
The instant application claims 1 and 13 limitations of a mixture of bis (arene) metal complexes;
The specific instant application claim 13 limitations of further reacting the obtained first metal complex to obtain a second metal complex; and,
The limitations in instant application claims 2, 3, 6, 9, and 14.
Asirvatham teaches mixtures of various isomers of alkyl and dialkyl bis(η6-arene)molybdenum complexes are generally obtained if alkylbenzenes are employed in the FHS; thus, a mixture of (η6-C6H6)-(η6-C6H5Et)Mo, (η6-C6H5Et)2Mo, (η6-C6H5Et)(η6-C6H4-Et2)Mo, and (η6-C6H4Et2)2Mo is obtained when ethylbenzene is employed in the FHS in order to synthesize bis (ethylbenzene) molybdenum, see Pg. 1687, Results and Discussion, i.e., the FHS synthesize of bis (ethylbenzene) molybdenum is a mixture of bis (arene) metal complexes.
Connor relating to arene displacement/exchange in metal complexes, such as [Cr(η-areneA)2] + 2 areneB → [Cr(η-areneB)2] + 2 areneA (6), by refluxing at elevated temperature and at the optimal pressure, where the arenes are selected based on their optimal temperature of enthalpy for displacement of the target arenes, and the arenes are benzene, ethylbenzene, 1,2-diethylbenzene, 1,2-di(l-methylethyl)benzene, 1,3,5-trimethylbenzene and 1,2,4 trimethylbenzene, Pg. 332, Introduction; Pg. 346, Substitution, redistribution and exchange reactions-Pg. 350, Tables 9, 15 & 16. Specifically, refluxing a solution of [Cr(η-C6H3Me3)2] in benzene at elevated temperature and atmospheric pressure results in [Cr(η-C6H6)2], equations (17) and (18) and the reverse exchange is obtained using benzene and a catalyst to create [Cr(η-C6H6)2] from [Cr(η-C6H3Me3)2], see specifically Pg. 348-Pg. 349, Ln. 3, benzene has a boiling point of 80 ◦C, ethylbenzene has a boiling point of 136 ◦C, 1,2-diethylbenzene has a boiling point of 183 ◦C as evidenced by Haynes, Pgs. 3-34, 3-174, 3-250, meeting:
Within the pressure range in instant application claim 6; and,
The further reacting a variety of metal (η-areneA)2 with a variety of areneB to obtain a variety of metal (η-areneB)2 in instant application claim 13.
Umilin relating to “bis-ethylbenzenemolybdenum” produced according to the Friedel-Crafts reductive reaction just like the analogous compound of chromium, containing a mixture of organometallic compounds, in which benzene or other aromatic hydrocarbons may be present as a ligand. The, see Pg. 1220, Pg. 1, First Para., comprises a mixture of benzeneethylbenzenemolybdenum, bis-ethylbenzenemolybdenum, ethylbenzenediethylbenzenemolybdenum, and bis-diethylbenzenemolybdenum, see Pg. 1221, Table 1, benzene has a boiling point of 80 ◦C, ethylbenzene has a boiling point of 136 ◦C, 1,2-diethylbenzene has a boiling point of 183 ◦C as evidenced by Haynes, Pgs. 3-34, 3-174, 3-250, meeting:
The mixture of bis (arene) metal complexes in instant application claim 1 and in instant application claim 13;
The boiling point limitations in instant application claim 2 and in instant application claim 14;
The formulas bis(η6-alkylbenzene)-molybdenum where Ar1 is benzene, R1 is alkyl, R2-R6 are each independently hydrogen or alkyl, Ar2 is benzene, R7 is alkyl, R8-R12 are each independently hydrogen or alkyl, Ar4 is benzene, Rg is alkyl, Rh-Rm are each independently hydrogen or alkyl, M is Mo in instant application claim 3; and,
The specific mixture of bis (arene) metal complexes in instant application claim 9.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the bis (arene) molybdenum complexes replaced by the arene/aromatic solvents of Asirvatham to specifically use the bis-ethylbenzenemolybdenum mixture as taught by Umilin as the starting bis (arene) molybdenum complex for arene displacement/exchange by a variety of arene solvents by modulating the temperature, pressure, and enthalpy of the target arenes to be displacement/exchange in order to produce the desired bis (arene) metal complex as taught by Connor with a reasonable predictability of success for the purpose of efficiently adjusting the thermodynamic conditions of the reaction in order to exchange the arene based on the specific arenes to exchange, how exothermic the reaction is, heat capacities, and heats of solution and of mixing, see Connor, Pg. 346, Substitution, redistribution and exchange reactions-Pg. 350, Tables 9, 15 & 16.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since Asirvatham, Umilin, and Connor all teach the preparation and composition of bis (arene) metal complexes, a person of ordinary skill in the art has good reason to arene exchange the desired starting bis (arene) metal complex with the desired arene, by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as those taught by Connor, for the benefit of efficiently adjusting the thermodynamic conditions of the reaction in order to exchange the arene based on the specific arenes to exchange, how exothermic the reaction is, heat capacities, and heats of solution and of mixing, see Connor, Pg. 346, Substitution, redistribution and exchange reactions-Pg. 350, Tables 9, 15 & 16 and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as the desired starting bis (arene) metal complex, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the optimal pressure for displacement, “or degree,” such as the boiling parameters of the arenes to be displaced, “or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as cooling to room temperature, “is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claims 12 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Asirvatham et al. (“Synthesis of Bis(η6-alkylbenzene)molybdenum by Arene Metathesis”, 15 March 2001, Organometallics, Vol. 20, Pgs. 1687-1688, hereinafter Asirvatham) in view of Connor et al. (“Thermochemistry of bis-Arene- and Arenetricarbonyl-Chromium Compounds containing Hexamethylbenzene, 1,3,5-Trimethylbenzene and Naphthalene”, 1979, Journal of Organometallic Chemistry, Vol. 179, Pgs. 331-356, hereinafter Connor) and Umilin et al. (“Gas Chromatographic Analysis and Composition of Impurities in Bis-Ethylbenzenemolybdenum”, 1972, Consultants Bureau, Pgs. 1220-1222, hereinafter Umilin), as applied to claims 1-11 and 13-17 in the 35 USC 103 rejection above, in further view of Hunks et al. (US20140220733, hereinafter Hunks).
Asirvatham does not teach the limitations of the instant application claims 12 and 18.
Hunks relating to the purification and purity problem to be solved of metal precursor complexes teaches it is known in the art to purify liquid bis (arene) metal complex precursor by filtration to achieve a purity of 98%, see Abstract; Paras. [0096];[0110], specifically the first structure shown in Para. [0110], meeting the liquid metal complex, separation, filtration, and within the purity range in instant application claim 12 and in instant application claim 18.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the bis (arene) molybdenum complexes replaced by the arene/aromatic solvents of Asirvatham to purify the bis (arene) molybdenum complex product as taught by Hunks with a reasonable predictability of success for the purpose of efficiently producing a bis (arene) metal complex with low impurities for CVD/ALD processes, see Hunks, Paras. [0010];[0096];[0144].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since both Asirvatham and Hunks teach the preparation and composition of bis (arene) metal complexes, a person of ordinary skill in the art has good reason to purify the complex, by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as those taught by Hunks, for the benefit of efficiently producing a bis (arene) metal complex with low impurities for CVD/ALD processes, see Hunks, Paras. [0010];[0096];[0144] and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Double Patenting
The nonstatutory 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 nonstatutory 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).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claim 19 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 15-18 of copending Application No. 18240151 to Kuiper (reference application, hereinafter Kuiper ‘151). Although the claims at issue are not identical, they are not patentably distinct from each other.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
The claims of Kuiper ‘151 recite the instant application claim 19 composition, precursor of the instantly claimed first formula, and within the purity range, see claims 15-18.
Claim 20 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 15-18 of copending Application No. 18240151 to Kuiper (hereinafter Kuiper ‘151) in view of Hunks et al. (US20140220733, hereinafter Hunks).
This is a provisional nonstatutory double patenting rejection.
The claims of Kuiper ‘151 recite the instant application claim 20 limitation of within the purity range, see claims 15-18.
The claims of Kuiper ‘151 do not recite the precursor is a liquid.
Hunks teaches it is known in the art to purify liquid bis (arene) metal complex precursor by filtration to achieve a purity of 98%, see Abstract; Paras. [0096];[0110], specifically the first structure shown in Para. [0110], meeting the liquid metal complex and within the purity range in instant application claim 20.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the bis (arene) metal complexes of the claims of Kuiper ‘151 to obtain a liquid form as taught by Hunks with a reasonable predictability of success for the purpose of efficiently producing a bis (arene) metal complex with low impurities for CVD/ALD processes, see Hunks, Paras. [0010];[0096];[0144].
Claim 19 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 19 and 20 of copending Application No. 19215290 to Kuiper (reference application, hereinafter Kuiper ‘290). Although the claims at issue are not identical, they are not patentably distinct from each other.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
The claims of Kuiper ‘290 recite the instant application claim 19 composition, precursor of the instantly claimed first formula, and within the purity range, see claims 19 and 20.
Claim 20 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 19 and 20 of copending Application No. 19215290 to Kuiper (hereinafter Kuiper ‘290) in view of Hunks et al. (US20140220733, hereinafter Hunks).
This is a provisional nonstatutory double patenting rejection.
The claims of Kuiper ‘290 recite the instant application claim 20 limitation of within the purity range, see claims 19 and 20.
The claims of Kuiper ‘290 do not recite the precursor is a liquid.
Hunks teaches it is known in the art to purify liquid bis (arene) metal complex precursor by filtration to achieve a purity of 98%, see Abstract; Paras. [0096];[0110], specifically the first structure shown in Para. [0110], meeting the liquid metal complex and within the purity range in instant application claim 20.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the bis (arene) metal complexes of the claims of Kuiper ‘290 to obtain a liquid form as taught by Hunks with a reasonable predictability of success for the purpose of efficiently producing a bis (arene) metal complex with low impurities for CVD/ALD processes, see Hunks, Paras. [0010];[0096];[0144].
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691