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
This office action is in response to Applicant' s communication filed on 11/19/25. Claims 1-22 and 26-28 are pending and are currently under examination. In view of Applicant's amendments to the claims filed 11/19/25, the objection and the 35 USC 112 rejection have been withdrawn. Claims 20-22 remain withdrawn. As a result, claims 1-19 and 26-28 are being examined in this Office Action.
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 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 of this title, 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 1-10, 13, 15-19 and 26-28 remain rejected under 35 U.S.C. 103 as being unpatentable over Noguchi et al. (JP 2001288139, pub date 10/16/2001, in applicant’s IDS filed 8/26/22, the English translation is used herein).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Noguchi et al. teaches a continuous process for producing high purity terephthalic acid by reacting p-xylene with molecular oxygen gas and a cobalt (Co), manganese (Mn) and bromine (Br) catalyst solution. The catalyst solution contains 120 to 3000 ppm cobalt, 1 to 300 ppm manganese. The amount of bromine is from 0.1 to 5 times the atomic ratio to cobalt. The ratio of Co to Mn wt % ratio is 1 : 0.001 to 1 : 2. The reaction temperature is from 140 to 210 degree C. The aqueous reaction medium contains a water concentration of 5 to 25% by weight. The average residence time is from 30 to 300 minutes (claims; page 4, paragraph 5; page 5, paragraph 10-11; page 6, paragraph 11).
Noguchi et al. exemplifies the use of air as the gaseous oxygen gas, which provides 21% of oxygen in the gaseous stream, and acetic acid as the solvent, to obtain in a first step, medium purity terephthalic acid, by using a catalyst. The catalyst contains 270 ppm Co, 170 ppm Mn and 500 ppm Br. Thus the calculated Br/(Co + Mn) wt % ratio is 1.1 : 1 and the Co to Mn wt % ratio is 1.6 : 1. The lower temperature oxygen treatment for the p-xylene oxidation was carried out at 191 degree C and 1.42 MPa (14.2 bar). The residence time was 33 minutes. The terephthalic acid was found to have a 4-carboxybenzaldehyde (4CBA) content of 248 ppm. Further purification gave a 4-carboxybenzaldehyde (4CBA) content of 1.7 ppm. (page 5, paragraph 8; Example 1, page 10-11, paragraph 28)
Noguchi et al. teaches the amount of p-xylene that is converted or oxidized to terephthalic acid is 95% by weight. Noguchi et al. isolates very high purity terephthalic acid with a transparency of 89% for medium purity terephthalic acid and a transparency of 97.3% for the final purity. The transparency is a function of the purity of terephthalic acid since the 4CBA impurity gives lower transparency or purity. (paragraph 7, claims, paragraph 2-4, 28, example 1)
With regard to applicant’s “homogeneous catalyst solution”, because Noguchi et all teaches the same components as applicant’s catalyst solution, it would be reasonable to expect the catalyst solution to be homogenous, especially since Noguchi et al. does not state the catalyst is heterogeneous, and because the reaction is performed in the liquid phase and not a biphasic solid/liquid phase.
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Noguchi et al. is deficient in the sense that it does not exemplify applicant’s amounts (ppm, wt% and ratio) for the Co, Mn and Br in the catalyst solution, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
However, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, to optimize the amount, ppm, wt% and ratios, of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield, in order to increase the yield and purity of the resulting product, terephthalic acid and because Noguchi et al. teaches ranges for the amount and ratios of Co, Mn and Br in the catalyst, the benefits of purifying the product reaction solution, and terephthalic acid product conversion from p-xylene. Formation of highly pure terephthalic acid in good yields by optimizing the reaction conditions and the amount of the reagents, including the catalyst, is old in the art, especially since terephthalic acid is produced on a large scale, since it a key raw material for polymers such as PET and PBT thermoplastics.
Furthermore, with regard to applicant’s limitations for the purity of the catalyst solution and the absence of impurities, such as iron, sodium, copper, or nickel, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to optimize the purity of the of catalyst solution since pure forms of known compound solutions are obvious, especially since the catalyst solutions are used in a reaction to form highly pure product, terephthalic acid. It would be reasonable to expect one of ordinary skill in the art to optimize the purity of the catalyst solution used as a reagent in the oxidation reaction, in order to optimize the resulting product purity of terephthalic acid. Furthermore, it would be reasonable to expect one to optimize and remove these metals impurities in the catalyst solution, in order to minimize side-oxidation reactions catalyzed by these metal impurities.
When claiming a purer form of a known compound, it must be demonstrated that the purified material possess properties and utilities not possessed by the unpurified material. Ex parte Reed, 135 U.S.P.Q. 34, 36 (P.O.B.A. 1961), on reconsideration, Ex parte Reed, 135 U.S.P.Q. 105 (P.O.B.A. 1961).
It has been well established that the mere purity of compound, in itself, does not render a substance unobvious Ex Parte Gray (BPAI 1989) 10 PQ2D 1922.
As stated in Aventis Pharma Deutschland Gmbh and King Pharmaceuticals, Inc., v. Lupin, Ltd., 84 USPQ2d 1197:
“The ‘reason or motivation’ need not be an explicit teaching that the claimed compound will have a particular utility; it is sufficient to show that the claimed and prior art compounds possess a ‘sufficiently close relationship . . . to create an expectation,' in light of the totality of the prior art, that the new compound will have ‘similar properties’ to the old.”
“However, if it is known that some desirable property of a mixture derives in whole or in part from a particular one of its components, or if the prior art would provide a person of ordinary skill in the art with reason to believe that this is so, the purified compound is prima facie obvious over the mixture even without an explicit teaching that the ingredient should be concentrated or purified….”
“Ordinarily, one expects a concentrated or purified ingredient to retain the same properties it exhibited in a mixture, and for those properties to be amplified when the ingredient is concentrated or purified; isolation of interesting compounds is a mainstay of the chemist’s art. If it is known how to perform such an isolation, doing so ‘is likely the product not of innovation but of ordinary skill and common sense.’”
Additionally, with regard to applicant's limitations regarding the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield, it is the position of the examiner that one of ordinary skill in the art, at the time of the invention, would through routine and normal experimentation determine the optimization of these limitations to provide the best effective variable depending on the result desired. Because the art teaches ranges for the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the benefits of purifying the reaction solution, and terephthalic acid product conversion from p-xylene, the examiner asserts that the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield are art recognized result-effective variables. Thus it would be obvious in the optimization process to optimize the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield. The applicant does not show any unusual and/or unexpected results for the limitations stated. Note that the prior art provides the same effect desired by the Applicant, the formation of highly pure terephthalic acid by oxidation of p-xylene with a Co, Mn and Br catalyst for the chemical industry.
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 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 of this title, 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 1-19 and 26-28 remain rejected under 35 U.S.C. 103 as being unpatentable over Noguchi et al. (JP 2001288139, pub date 10/16/2001, in applicant’s IDS filed 8/26/22, the English translation is used herein), in view of Hashimi et al. (US 7985875, pub date July 26, 2011, in applicant’s IDS filed 8/26/22).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Noguchi et al. teaches a continuous process for producing high purity terephthalic acid by reacting p-xylene with molecular oxygen gas and a cobalt (Co), manganese (Mn) and bromine (Br) catalyst solution. The catalyst solution contains 120 to 3000 ppm cobalt, 1 to 300 ppm manganese. The amount of bromine is from 0.1 to 5 times the atomic ratio to cobalt. The ratio of Co to Mn wt % ratio is 1 : 0.001 to 1 : 2. The reaction temperature is from 140 to 210 degree C. The aqueous reaction medium contains a water concentration of 5 to 25% by weight. The average residence time is from 30 to 300 minutes (claims; page 4, paragraph 5; page 5, paragraph 10-11; page 6, paragraph 11).
Noguchi et al. exemplifies the use of air as the gaseous oxygen gas, which provides 21% of oxygen in the gaseous stream, and acetic acid as the solvent, to obtain in a first step, medium purity terephthalic acid, by using a catalyst. The catalyst contains 270 ppm Co, 170 ppm Mn and 500 ppm Br. Thus the calculated Br/(Co + Mn) wt % ratio is 1.1 : 1 and the Co to Mn wt % ratio is 1.6 : 1. The lower temperature oxygen treatment for the p-xylene oxidation was carried out at 191 degree C and 1.42 MPa (14.2 bar). The residence time was 33 minutes. The terephthalic acid was found to have a 4-carboxybenzaldehyde (4CBA) content of 248 ppm. Further purification gave a 4-carboxybenzaldehyde (4CBA) content of 1.7 ppm. (page 5, paragraph 8; Example 1, page 10-11, paragraph 28)
Noguchi et al. teaches the amount of p-xylene that is converted or oxidized to terephthalic acid is 95% by weight. Noguchi et al. isolates very high purity terephthalic acid with a transparency of 89% for medium purity terephthalic acid and a transparency of 97.3% for the final purity. The transparency is a function of the purity of terephthalic acid since the 4CBA impurity gives lower transparency or purity. (paragraph 7, claims, paragraph 2-4, 28, example 1)
With regard to applicant’s “homogeneous catalyst solution”, because Noguchi et all teaches the same components as applicant’s catalyst solution, it would be reasonable to expect the catalyst solution to be homogenous, especially since Noguchi et al. does not state the catalyst is heterogeneous, and because the reaction is performed in the liquid phase and not a biphasic solid/liquid phase.
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Noguchi et al. is deficient in the sense that it does not exemplify applicant’s amounts (ppm, wt% and ratio) for the Co, Mn and Br in the catalyst solution, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield. Noguchi et al. is also deficient in the sense that it does not teach the flow rate for the reagent catalyst solution, a titanium lined reactor and a carbon dioxide outlet stream amount.
Hashimi et al. teaches a process for producing terephthalic acid by reacting p-xylene with air or oxygen gas, and a cobalt (Co) and manganese (Mn) catalyst solution, with a bromide catalyst promoter, achieving high conversion. Terephthalic acid is produced on a large scale, since it a key raw material for polymers such as PET and PBT thermoplastics. Hashimi et al. teaches typically 98% of xylene is reacted to give the product, terephthalic acid, in over 95% yield, with residence times of up to 120 min. Conversion of p-xylene was found to be almost 100%. Also 4-CBA is a troublesome impurity because terephthalic acid needs to be in very high purity to make polyesters. Titanium is often required for the equipment for corrosion protection. Hashimi et al. teaches a flow rates for the reagents, like the air/oxygen flow rate and controlling the carbon dioxide concentration in the off-gas with online gas analyzers to 1.3-1.5 vol %. (column 1, line 27-30; column 1, line 51 to column 2, line 5; example 1, column 5, lines 50 to column 6, line 51; claims)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, to optimize the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, and the terephthalic acid product yield, in order to increase the yield and purity of the resulting product, terephthalic acid and because Noguchi et al. teaches ranges for the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the benefits of purifying the product reaction solution, and terephthalic acid product conversion from p-xylene. Formation of highly pure terephthalic acid in good yields by optimizing the reaction conditions and the amount of the reagents, including the catalyst, is old in the art, especially since terephthalic acid is produced on a large scale, since it a key raw material for polymers such as PET and PBT thermoplastics.
It would also be prima facie obvious to one of ordinary skill in the art at the time of the invention, to optimize the amount of carbon dioxide in the gaseous outlet stream and the flow rate of reagents, such as the catalyst solution, in the oxidation of p-xylene to terephthalic acid, especially since Hashimi et al. teaches controlling the carbon dioxide concentration in the off-gas and the flow rates of the reagents, such as oxygen. It would be reasonable to expect that one of ordinary skill in the art would optimize both the reagent flow rates for the catalyst solution and the amount of carbon dioxide in the outlet off-gas, in order optimize the purity and yield, absent evidence of unexpected results.
Additionally, it would be reasonable to expect that titanium would be used in the reactor, since Hashimi et al. teaches it is a metal that is often used for corrosion protection for these type of oxidation reactions.
Furthermore, with regard to applicant’s limitations for the purity of the catalyst solution and the absence of impurities, such as iron, sodium, copper, or nickel, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to optimize the purity of the of catalyst solution since pure forms of known compound solutions are obvious, especially since the catalyst solutions are used in a reaction to form highly pure product, terephthalic acid. It would be reasonable to expect one of ordinary skill in the art to optimize the purity of the catalyst solution used as a reagent in the oxidation reaction, in order to optimize the resulting product purity of terephthalic acid. Furthermore, it would be reasonable to expect one to optimize and remove these metals impurities in the catalyst solution, in order to protect against corrosion of the reactor and minimize side-oxidation reactions catalyzed by these metal impurities.
When claiming a purer form of a known compound, it must be demonstrated that the purified material possess properties and utilities not possessed by the unpurified material. Ex parte Reed, 135 U.S.P.Q. 34, 36 (P.O.B.A. 1961), on reconsideration, Ex parte Reed, 135 U.S.P.Q. 105 (P.O.B.A. 1961).
It has been well established that the mere purity of compound, in itself, does not render a substance unobvious Ex Parte Gray (BPAI 1989) 10 PQ2D 1922.
As stated in Aventis Pharma Deutschland Gmbh and King Pharmaceuticals, Inc., v. Lupin, Ltd., 84 USPQ2d 1197:
“The ‘reason or motivation’ need not be an explicit teaching that the claimed compound will have a particular utility; it is sufficient to show that the claimed and prior art compounds possess a ‘sufficiently close relationship . . . to create an expectation,' in light of the totality of the prior art, that the new compound will have ‘similar properties’ to the old.”
“However, if it is known that some desirable property of a mixture derives in whole or in part from a particular one of its components, or if the prior art would provide a person of ordinary skill in the art with reason to believe that this is so, the purified compound is prima facie obvious over the mixture even without an explicit teaching that the ingredient should be concentrated or purified….”
“Ordinarily, one expects a concentrated or purified ingredient to retain the same properties it exhibited in a mixture, and for those properties to be amplified when the ingredient is concentrated or purified; isolation of interesting compounds is a mainstay of the chemist’s art. If it is known how to perform such an isolation, doing so ‘is likely the product not of innovation but of ordinary skill and common sense.’”
Additionally, with regard to applicant's limitations regarding the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, the terephthalic acid product yield, the amount of carbon dioxide in the gaseous outlet stream and the flow rate of reagents, such as the catalyst solution, it is the position of the examiner that one of ordinary skill in the art, at the time of the invention, would through routine and normal experimentation determine the optimization of these limitations to provide the best effective variable depending on the result desired. Because the art teaches ranges for the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the benefits of purifying the reaction solution, terephthalic acid product yield, controlling carbon dioxide in the gaseous outlet stream and the flow rate of reagents, the examiner asserts that the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, the terephthalic acid product yield, the amount of carbon dioxide in the gaseous outlet stream and the flow rate of reagents, such as the catalyst solution, are art recognized result-effective variables. Thus it would be obvious in the optimization process to optimize the amount, ppm, wt% and ratios of Co, Mn and Br in the catalyst, the amount of impurities such as 4-carboxybenzaldehyde (4CBD), iron, sodium, copper or nickel in the product and catalyst solution, the terephthalic acid product yield, the amount of carbon dioxide in the gaseous outlet stream and the flow rate of reagents, such as the catalyst solution. The applicant does not show any unusual and/or unexpected results for the limitations stated. Note that the prior art provides the same effect desired by the Applicant, the formation of highly pure terephthalic acid by oxidation of p-xylene with a Co, Mn and Br catalyst for the chemical industry.
Response to Arguments
Applicant’s arguments have been considered but are not persuasive for the following reasons:
The examiner acknowledges applicant’s argument that “It is respectfully submitted that at least a Co to Mn wt. % ratio was not recognized as a result-effective variable, i.e., a variable which achieves a recognized result. Therefore, the determination of the optimum or workable ranges of the Co to Mn wt. % ratio cannot be characterized as routine experimentation.” Applicant also argues that the selection of applicant’s narrower ranges would not have been an obvious modification and that Noguchi’s invention is fundamentally different, for example, by employing two oxidation stages.
The examiner does not agree with applicant’s arguments. The examiner contends that the Co to Mn wt. % ratio was recognized as a result-effective variable, since Noguchi teaches on page 5, paragraph 10: “The amount of the manganese component to be used is 0.001 to 2 times the amount of cobalt in terms of atomic ratio.” Thus clearly Noguchi envisions a ratio relationship between cobalt and manganese for their inventive catalyst, which would be recognized as a result-effective variable.
Furthermore, applicant’s narrower ranges for their catalyst composition are still within Noguchi’s teaching for the ranges for their catalyst. Absent evidence of unexpected results, the examiner maintains the obviousness of applicant’s narrower ranges for the composition of their catalyst.
Additionally, Noguchi’s invention is relevant to applicant’s invention, since applicant’s “comprising” language allows for additional steps. For example, Noguchi’s two oxidation stages merely utilizes two different temperatures.
The examiner acknowledges applicant’s argument showing the difference between applicant’s experiment 1 and their comparative experiment.
The examiner does not agree with applicant’s arguments. The examiner appreciates applicant’s performance benefit comparisons in Table 1 which compares their Experiment 1 with their comparative experiment. However, the applicant has not compared their invention with the closest prior art, which is Noguchi’s process for producing terephthalic acid. Furthermore, applicant’s claimed ranges are not commensurate in scope with applicant’s Experiment 1 in their Table 1, which utilizes a specific amount for each of the catalyst components.
Conclusion
Claims 1-22 and 26-28 are rejected.
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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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