DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
2. Claims 1, 6-7, 11, 13-17, 22, 24, 26, 28, 31, 33, 35-36, 38, 41, 43 are currently pending. Claims 26, 28, 31, 33, 35-36, 38 have been elected in the response filled on 06/03/2025. This office action is in response to response filed on 12/10/2025.
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.
3. Claim(s) 26, 28, 31, 33, 35 is/are rejected under 35 U.S.C. 103 as being unpatentable over Veige (WO 2015/191571 A1; listed on the IDS filed on 11/03/2023 and all citations refer to the copy of this document provided by applicant on this date) or alternatively Veige in view of Kobayashi (US 4,452,959).
Concerning claim 26, 31, 35 Veige teaches a polymerization of alkynes using a tridentate pincer ligand metal complex to form high molecular weight polymers at high rates and the poly alkyne is indicated to be able to be a macrocyclic poly (alkyne) (pg 4 lines 5-15). The alkyne is indicated to be able to be unsubstituted, monosubstituted or disubstituted (pg 6 lines 23-25), and it should be noted that unsubstituted alkyne would be acetylene. The poly (alkynes) prepared by this method can display one or more geometries across the double bonds of the poly(alkyne) backbone (pg 6 lines 15-20).
The polymerization reaction is indicated to occur upon combining the trianionic pincer ligand supported metal-alkylidyne complex to an alkyne monomer in a fluid state which can be in solution (pg 6 liens 20-25).
Veige specifically teaches that that a catalyst complex having a structure of (pg 6 lines 10-15 and pg 7 lines 5-15)
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Has particularly high activity and can be used to make cyclic polymers (pg 7 lines 25-30).
Moreover Veige teaches an example in which this catalyst is indicated to be used in conjunction with a solvent of toluene, where a phenyl acetylene solution in toluene with having a total volume of 2.218 mL is mixed with a catalyst solution of the above indicated catalyst and toluene having a catalyst concentration of 1 mg/mL to polymerize a cyclic polymer from phenyl acetylene which has an absolute number average molecular weight of 68,000 Da (pg 13 lines 20-30 and pg 14 lines 1-5 and Table 4). It should be noted that the phenyl acetylene monomer unit would have a molecular weight of approximately 102.15 g/mol which would indicate that the number average polymer would have a number of polymerized monomer units of approximately 665.7 which is a number of polymerized units that is within the claimed range of the number of polymerized monomer units of at least 80.
It should be noted that this exemplary method differs from the method indicated in the non elected clam 1 and claim 7 only in that phenyl acetylene is used instead of acetylene and no mention is made of the cyclic poly acetylene including the trans isomer. The same catalyst, solvent and catalyst concentration as is claimed in these non elected claims is used.
As such the exemplary polymer differs from claimed polymer only in that phenyl acetylene is used as the monomer instead of acetylene and Veige is silent as to the amount of trans double bonds in the polymer. However as is stated above Veige states that an unsubstituted alkyne can be used to make the polymer, which would correspond to the use of acetylene as a monomer.
The particular amount of trans double bonds in a polyacetylene polymer would depend on the catalyst and conditions of polymerization which are used to make the polyacetylene polymer. However as is stated above Veige provides an example of the catalyst and polymerization conditions which are the same as that indicated by applicant to give the claimed trans cyclic poly acetylene.
"[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). See MPEP 2112.I.
There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). See MPEP 2112.II.
"[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his [or her] claimed product. Whether the rejection is based on ‘inherency’ under 35 U.S.C. 102, on ‘prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same." In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). See MPEP 2112.V.
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the exemplary cyclic polymerization of Veige to use acetylene instead of phenylacetylene because Veige teaches that the alkyne which is used in the polymerization can be unsubstituted which would correspond to an acetylene monomer, and the catalyst and polymerization conditions provided Veige are the same as those indicated by applicant would provide the claimed trans-cyclic polyacetylene and so would provide the claimed trans double bond amounts.
Alternatively in the case where the amount of the trans double bonds is not inherently formed by the catalyst and conditions provided by Veige, it would be obvious to provide the claimed trans double bonds to the cyclic polyacetylene polymer of Veige.
Veige as is stated above is silent as to the amount trans bonds in the polymer. Veige teaches that polyacetylenes are organic polymers that can display electrical conductivity (pg 2 lines 10-15).
Kobayashi is drawn to polyacetylenes (abstract) and teaches that the acetylene polymer has low electrical resistance , and that the specific resistance of the polyacetylene is higher when its cis structure content is high but decreases with an increasing content of the trans structure, with articles comprising only a trans structure being possible and showing photoconductivity (Column 9 lines 50-55). It is taught that in general the three dimensional structure of the acetylene polymer can be controlled by the polymerization temperature and that when the polymerization temperature is low a high cis content is formed but when the polymerization temperature is higher an acetylene polymer having a higher trans content is formed (column 7 lines 15-30).
It would have been obvious to one of ordinary skill in the art at the time of filling to use acetylene as the monomer of the poly cyclic polymer of Veige because Veige teaches that the alkyne which is used in the polymerization can be unsubstituted which would correspond to an acetylene monomer and to alter the polycyclic acetylene polymer to have as high a trans form as possible by increasing the temperature of the polymerization as taught by Kobayashi for the purpose of improving the electrical properties of the polymer which Veige indicates are important.
Concerning claim 28 Viege teaches that intermolecular cross coupling of two separate chains inevitably leads to linear impurities ( pg 3 lines 5-15) and teaches that the poly unsaturated cyclic polymer is free of linear impurities (claim 6). This and the indication of the same catalyst and polymerization conditions of Viege as is argued above would provide the claimed less than 5% crosslinking defects as the amount of crosslinking defect would be the result of the catalyst and polymerization conditions.
"[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). See MPEP 2112.I.
There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). See MPEP 2112.II.
"[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his [or her] claimed product. Whether the rejection is based on ‘inherency’ under 35 U.S.C. 102, on ‘prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same." In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). See MPEP 2112.V.
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.
As such the polymer of Veige would teach the claimed limitation
Concerning claim 33 Veige or Veige in view of Kobayashi teaches the trans cyclic polyacetylene of claim 31 as is stated above.
Venge does not particularly teach the average conjugation length of the polymer.
However Venge teaches that intermolecular cross coupling of two separate chains inevitably leads to linear impurities ( pg 3 lines 5-15) and teaches that the poly unstatured cyclic polymer is free of linear impurities (claim 6). The average conjugation length of the a polyacetylene polymer would be related to the length of the polymer chain and the amount of defects in the polymer chain as without defects the conguation length of an acetylene polymer would the degree of polymerization of the polymer, and the amount of defects in a polymer chain would be dependent on the catalyst and polymerization conditions used.
Veige as stated above teaches an example in which this catalyst is indicated to be used in conjunction with a solvent of toluene, where a phenyl acetylene solution in toluene with having a total volume of 2.218 mL is mixed with a catalyst solution of the above indicated catalyst and toluene having a catalyst concentration of 1 mg/mL to polymerize a cyclic polymer from phenyl acetylene which has an absolute number average molecular weight of 68,000 Da (pg 13 lines 20-30 and pg 14 lines 1-5 and Table 4). It should be noted that the phenyl acetylene monomer unit would have a molecular weight of approximately 102.15 g/mol which would indicate that the number average polymer would have a number of polymerized monomer units of approximately 665.7 which is a number of polymerized units that is within the claimed range of the number of polymerized monomer units of at least 80.
"[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). See MPEP 2112.I.
There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). See MPEP 2112.II.
"[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his [or her] claimed product. Whether the rejection is based on ‘inherency’ under 35 U.S.C. 102, on ‘prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same." In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). See MPEP 2112.V.
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.
As such the polymer of Veige or Veige in view of Kobayashi which is made by the same catalyst and under the same conditions as indicated by applicant would have the claimed average conjugation length.
4. Claim(s) 36, 38 is/are rejected under 35 U.S.C. 103 as being unpatentable over Veige (WO 2015/191571 A1; listed on the IDS filed on 11/03/2023 and all citations refer to the copy of this document provided by applicant on this date) or alternatively Veige in view of Kobayashi (US 4,452,959) as applied to claim 1 above, and further in view of Pedretti (US 4,600,756).
Concerning claims 36 and 36 Veige or alternatively Veige in view of Kobayashi teaches the trans-cyclic polyacetylene of claim 26.
Veige teaches that polyacetylenes are organic polymers that can display electrical conductivity (pg 2 lines 10-15).
Pedretti is drawn to polyacetylene films (abstract) and teaches that the poly acetylene is subjected to isomerization for converting into the predominant trans form prior to doping with iodine and the isomerization is carried out at a temperature in the neighborhood of 200 °C of a few minutes by maintaining the polyacetylene under a helium stream (column 7 lines 60-68 and column 8 lines 25-35). The isomerized polyacetylene after the doping with iodine is indicated to be able to attain a specific electric conductivity of up to about 2,000 ohm-1 cm-1 (column 7 lines 50-60 and column 8 lines 30-35), which would be at very least be an overlapping range with the claimed range of at least 100 ohm-1 cm-1 .
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). See MPEP 2144.05.I.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the trans-cyclic polyacetylene polymer of Veige or alternatively Veige in view of Kobayashi to include the dopant with iodine as taught by Pedretti for the purpose of providing improved conductivity of the polyacetylene polymer which is at very least an overlapping range with the claimed range.
Response to Arguments
5. Applicant's arguments filed 12/10/2025 have been fully considered but they are not persuasive. Applicant argues with regard to the rection over Veige in view of Kobayashi and Viege in view of Kobayashi and further in view of Pedretti that In order to establish a prima facie case of obviousness the burden is on the office to i)establish that the cited references teach or suggest all claim limitations ii)establish a suggestion or motivation to combine reference teaches which has a rational underpinning in the refences themselves or general knowledge in the art, and iii) there must be a reasonable expectation of success. Applications submits that the rational provided by the office that would assertedly motivate one of ordinary skill in the art to combine Veige, Kobayashi and Pedretti to arrive at the claimed subject matter is insufficient to support a prima facie case of obviousness and the person of ordinary skill in the art would not have a reasonable expectation of success when combining Veige Kobayashi and Pedretti. The office action asserts that it would have been obvious to one of ordinary skill int eh art at the time of filling to alter the exemplary cyclic polymerization of Veige to use acetylene instead of phenyl acetylene because Veige teaches that the alkyne which is used in the polymerization can be unsubstituted. The action also asserts that the person of ordinary skill int eh art would have been motivated to provide a polymer of modified Veige having as high a trans form as possible for the purpose of improving electrical properties of the polymer which Veige indicates are important. Pedretti is cited int eh action for purportedly teaching to include the dopant with iodine as taught by Pedretti in the polymer of modified Veige for the purpose of providing improved conductivity of the polyacetylene polymer. Although Veige generally discloses unsubstituted alkyne monomers can be polymerized, Veige does not disclose or suggest that the polymer having at least 50 polymerized monomer units as claimed can be prepared from such monomers. Instead Veige only demonstrates the polymerization of monosubstituted of disubstituted alkyne monomers. As the office action states the number of polymerized monomer units can be approximated based on molecular weight of the polymer and the monomers polymerized. However the person of ordinary kill int eh art would also recognize that the polymerization of specific substituted alkynes is not predictive or instructive regarding the polymerization of different substituted alkynes let alone acetylene due to the expected difference in reactivity between each monomer and a given catalyst. In particular the person of ordinary skill int eh art would recognize that the identity of substituents on monomers can affect polymer synthesis. For example the size and steric effects of substituents as well as the electronic effects of the substituents can influence the reactivity of various monomers with a given catalyst. Thus while Veige demonstrates that a wide variety of monomers can be polymerized the person of ordinary skill in the art would also recognize that the demonstrated polymerizations of substituted alkynes do not provide a clear pattern of reactivity, let alone a suggestion that the polymerization of any monomer would necessarily result in a polymer including at last 50 monomer units. Given the differences in monomer scope from table 1 of Veige the person of ordinary skill in the art would not be able to infer the properties Mw, TON % yield or number of monomer polymerized for poly (acetylene) thus it cannot be said that modifying the methods of Veige to polymerize acetylene would provide a trans-cyclic poly acetylene having at least 50 polymerized monomer units as claimed with any expectation of success.
This argument is not found to be persuasive as Veige is indicated to be drawn to a tridentate pincer ligand metal complex which is used for the polymerization of alkynes and provides high molecular weight polymers formed at high rates (pg 4 lines 5-15). Veige indicates that the alkyne can be unsubstituted, mono substituted , or disubstituted (pg 6 lines 20-25). The only unsubstituted alkyne is acetylene, so since unsubstituted alkynes are specifically mentioned Veige particularly teaches that the method can be used for acetylene. And Veige indicates that the polymerization can occur with a large turnover of monomer per catalyst, a high degree of polymerization and a high yield of polymer though this is indicated to vary with the nature of the polymer catalyst and conditions of the polymerization (pg 7 lines 1-5). Moreover the cyclic polymerization is indicated to be ring expansion polymerization of alkyne (pg 7 lines 15-20) which is indicated to be represented by the scheme of (Figure 7)
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.
This would indicate that even if reactivity of the catalyst with a particular monomer such as acetylene is lower than with the indicated monomer of phenyl acetylene that the formation of a particular molecular weight of a polymer would be a function of time with greater time providing greater molecular weight and increased degree of polymerization. As such one of ordinary skill in the art would expect to be able to make polymers with the same or similar degrees of polymerization to the exemplary polymer of Veige using acetylene instead of phenyl acetylene because Veige specifically indicates that unsubstituted alkynes (which specifically is only acetylene) can be used with the indicated polymerization method and catalysts, and the process of making a cyclic polymer using the indicated catalyst of Veige is indicated to be a ring expansion polymerization of alkynes which would allow the polymer made from reactants with less reactivity to be made having similar degrees of polymerization by increasing the time of the polymerization, and the entire process of Veige is indicated to be used to provide a high degree of polymerization, thereby providing a reasonable expectation of success.
"The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain." In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983). See MPEP 2123.I.
A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Labs., Inc. 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989), cert. denied, 493 U.S. 975 (1989). See MPEP 2123.I.
Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). See MPEP 2123.II.
As such the rejection provided above is maintained.
Applicant further argues that Kobayahi and Pedretti do not remedy the deficiencies of Veige. Kobayashi discloses the preparation of linear poly (acetylene from acetylene gas using a catalyst system with a transition metal compound and an organometallic compound similar to a Ziegler Natta catalyst. Kobayashi does not suggest of disclose using the catalyst of Veige to form cyclic poly(acetylene). As Veige does not demonstrate forming cyclic poly (Acetylene) and Kobayashi does not discloses or suggest using the Veige catalyst to prepare cyclic poly(acetylene) the person of ordinary skill int eh art would have no reasonable expectation of providing a cyclic poly(acetylene) having at least 50 polymerized monomer units based on the disclosure of Beige and Kobayashi. Similarly Pedretti discloses acetylene polymer films but does not disclose the Veige catalyst. Thus as with Kobayashi Pedretti does not and cannot provide a reasonable expectation of providing a cyclic poly(acetylene ) having at least 50 polymerized monomer units using the catalyst di closed in Veige.
This argument is not found to be persuasive because as is indicated in the discussion of the arguments concerning the rejections of Veige, Veige provides one of ordinary skill in the art at the time of filling a reasonable expectation of success concerning using acetylene instead of phenyl acetylene to make a high degree of polymerization cyclic polymer. As such since Kobayashi and Pedretti are used to teach different parts of the claims the rejections provided above are maintained.
Conclusion
6. Claims 26, 28, 31, 33, 35,-36, 38 are rejected. No claims are currently allowable.
THIS ACTION IS MADE FINAL. 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 DAVID L MILLER whose telephone number is (571)270-1297. The examiner can normally be reached M-F 9:30-6:00.
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/DAVID L MILLER/Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763