DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Claims 1-12 were filed on 7/17/2023. In a preliminary amendment filed on the same day, claims 1-12 were amended. Claims 1-12 are pending.
Priority
The application was filed on 7/17/2023 and claims the benefit of priority to:
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See filing receipt dated 5/31/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 9 is objected to because of the following informalities: in line 2, the word “of” should be deleted. Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 11-12 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 11 recites: “a mixture comprising compounds according to general formulae (IIa) and (IIb)
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Or their respective alkali metal salts, in a molar ratio in the range of from 2 to 15% by weight glycolic acid, referring to the sum of compounds according to general formulae (IIa) and (IIb), and less than 0.1% by weight of oxalic acid, or their respective alkali metal salts, wherein R1 is selected from H and C1-C6-alkyl, non-substituted or substituted with one or more moieties selected from COOH and O-R4, with R4 being selected from H and C1-C4-alkyl and wherein the percentages refer to the respective sodium salts”.
There are two issues with the claim (underlined above). The first is that a “molar ratio” between (IIa) and (IIb) is claimed as a weight percentage of glycolic acid (which does not correspond to either (IIa) or (IIb)). The term “molar ratio” requires a ratio between moles of each compound. Therefore, this limitation is indefinite. Presumably the molar ratio, if being claimed, is intended to be the same as that of claim 10 (10:1 to 1:1), and the 2 to 15 wt% refers to the glycolic acid content in the composition; however this is not clear from the current claim language.
The second issue is the wherein clause at the end of the claim. It is not clear if all of compounds (IIa), (IIb), glycolic acid, and oxalic acid are required to be sodium salts or if the limitation is intended to convey that the alkali metal is sodium if present.
This issue is further compounded in claim 12, which depends from claim 11. Claim 12 recites that the R1 groups are “optionally partially or fully neutralized with alkali”. It is not clear if the alkali here is also limited to sodium and if it can be optional based on the final line of claim 11.
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) 1-5, 8, and 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kiyoura (JPS5377009A, published 7/8/1978, of record in the IDS filed 8/17/2023) in view of Mallat (“Oxidation of Alcohols with Molecular Oxygen on Solid Catalysts” Chem. Rev. 2004, 104, p. 3037) and Ramprasad (US 6046356, published 4/4/2000, of record in the IDS filed on 8/17/2023).
A translation of Kiyoura was provided with the IDS copy on 8/17/2023, however, a new translation is also provided herein, which contains line numbers for ease of discussion.
The Applicant claims a process for synthesizing compounds with the general formula (II) or their respective alkali metal salts, comprising oxidizing compounds of general formula (I) with oxygen (O2) in the presence of a heterogeneous catalyst comprising Pt and one promoter selected from cadmium (Cd), thallium (Tl), lead (Pb) and/or bismuth (Bi) and at a temperature in the range of from -10 to +40°C:
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Kiyoura teaches a process for producing an aminocarboxylic acid by oxidizing a methanolamine (diethanolamine) or triethanolamine N(CH2CH2OH)3 with an oxygen containing gas in an aqueous solution (claim 2) comprising the use of a palladium (Pd) or platinum (Pt) catalyst and a hydroxide of an alkali or alkaline earth metal (a base). See abstract and claims. Triethanolamine is a compound of instant formula (I) wherein R1 and R2 are ethyl, C2 alkyl, substituted by OR4, and R4 is H. Though the text recites “methanolamine”, the products produced in the examples (sodium salt of beta-hydroxyethylglycine HN(-CH2-CH2OH)(-CH2COO-) and the barium salt of iminodiacetic acid HN(CH2COO-)2) require diethanolamine HN(-CH2-CH2-OH)2 as a reactant. See lines 96-119 of the translation. Diethanolamine is a compound of instant formula (I) wherein R1 is H and R2 is -CH2-CH2-OH. Thus, triethanolamine and diethanolamine also meet the limitations of claim 8.
The Pd or Pt catalyst is heterogeneous and is preferably carried on a suitable carrier, such as activated carbon of alumina (claim 4). See lines 57-66 of the translation. The reaction is carried out at a temperature from room temperature to 100°C or more, preferably 40-80°C, and with a pressure of normal pressure to 10 kg/cm2 (about 1 to about 10 bar), wherein when the gas used is pure oxygen, the oxygen partial pressure is equivalent to the total pressure. See lines 88-94 of the translation. These ranges overlap with or encompass those in claims 1 and 5. The examples appear to be carried out at temperature of 40°C or 60°C and a pressure of 1 atm (bar). See original patent text and translation of the examples.
The concentration of the hydroxide base can be controlled so that there is partial oxidation (<1 mole -OH : 1 mol OH in reactant) or full oxidation (≥ 1 mole -OH : 1 mol OH in reactant), or a mixture thereof, of the ethanolamines to produce the corresponding alkali or alkaline earth metal salt of the oxidized product. These values overlap with those of claim 3. Thus, when triethanolamine is fully oxidized (at least 1:1 molar ratio of -OH base : OH group on triethanolamine), it will produce nitrilotriacetic acid, and salts thereof. See lines 66-88 of the translation. Nitrilotriacetic acid is a compound of instant formula (II) wherein R1 and R3 are both -CH2-COOH (C1 alkyl substituted by COOH). The partially oxidized products of triethanolamine correspond to the mono- (wherein R1 and R3 are the same as in formula (I), -CH2-CH2-OH) and di-acetic acid (wherein one of R1 and R3 is -CH2-CH2-OH and the other is -CH2-COOH) compounds. The mono-acid oxidation product of triethanolamine is also referred to as “bis-beta-hydroxyethyl glycine” in Kiyoura.
In example 3, Kiyoura teaches reacting triethanolamine with a substoichiometric amount of NaOH to produce the sodium salt of bis-beta-hydroxyethyl-glycine and then with a stoichiometric (1:1) amount of NaOH to produce sodium nitrilotriacetate. See lines 121-127 of the translation. Likewise, as discussed above, the products of examples 1-2, starting from diethanolamine, are the sodium salt of beta-hydroxyethylglycine HN(-CH2-CH2OH)(-CH2COO-), the partially oxidized product (wherein one of R1 and R3 is H and the other is -CH2-CH2-OH), and the barium salt of iminodiacetic acid HN(CH2COO-)2, the fully oxidized product (wherein one of R1 and R3 is -H and the other is -CH2-COOH). See lines 96-119.
These products meet the limitations of claim 9, wherein R1 is either H or -CH2-COOH or salts thereof. Kiyoura teaches that all products are produced in about 70% yield in the examples and that “the aminocarboxylic acids obtained by the method of the present invention are compounds having alcohol, amine and carboxyl group in the molecule, and can be used in various organic synthesis raw materials, emulsifying agents, surfactants, bactericidal disinfectants, washing agents and builders”. See lines 39-43 of the translation.
Kiyoura does not explicitly teach that the Pt or Pd catalyst further comprises a Cd, Tl, Pb, and/or Bi promotor.
Mallat is a review of the oxidation of alcohols with molecular oxygen on solid catalysts. See introduction section on p. 3037-3038. Supported platinum-group metals are discussed in section 2.1 on p. 3038-3042. In the beginning of section 2.1.1. on p. 3038, Mallat teaches that “Pt-group metals can activate alcohols and molecular oxygen under close to ambient conditions and produce the corresponding carbonyl compounds or carboxylic acids in high yields. Today, various bi- and multimetallic catalysts are applied that are more active, more selective, and less prone to deactivation than monometallic catalysts.
The most commonly used catalysts consist of Pt or Pd as active components and Bi or Pb as promoters, on carbon and alumina supports. Ru and Rh are usually applied without promoters. Besides Bi and Pb, a variety of promoter metals have been
suggested, including Cd, Co, Cu, Se, Ce, Te, Sn, Au, and Ru. The non-noble metal
promoters are inactive under reaction conditions, and their deposition onto the active sites should result in lower oxidation rates. Still, promotion of Pt or Pd may lead to a considerable rate enhancement (Scheme 1) and to a remarkable shift in the product
distribution (Scheme 2)”.
In section 2.1.4 on p. 3042, Mallat further teaches that the selective oxidation of an alcoholic OH group has been attained in the presence of nitrogen containing functional groups, including amino, quaternary ammonium, acetamino, nitro, nitrile, and N- and S-containing heteroaromatic groups. See second paragraph. In section 4.2 on p. 3052, Mallat also teaches that the promoted Pt-group metals are the most commonly used catalysts for the oxidative synthesis of carboxylic acids (as salts) in aqueous alkaline media, including the oxidation of a broad range of functionalized primary alcohols. The oxidation of a choline salt or hydroxide to a betaine is particularly exemplified:
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. Choline is analogous to the compound of instant formula (I), wherein the nitrogen atom is quaternized and holds a positive charge to produce a betaine rather than a salt of a compound of formula (II) at the end of the reaction.
Thus, Mallat teaches that Cd, Pb, and Bi are well-known predictable promoters for solid Pt catalysts in the oxidation of alcohols, including those with amine functionality, with molecular oxygen in aqueous medium in the presence of a base.
Ramprasad is directed toward the oxidation of an aqueous solution of a choline salt in the presence of a base and a supported noble metal catalyst at temperatures from about 20°C to 100°C and pressures from atmospheric to about 100 psi (about 1 to 7 bar-claim 5) to produce a betaine. See abstract and claims. As discussed above with respect to Mallat, choline salts are analogous to the compounds of instant formula (I). Ramprasad is cited as reference 188 in Mallat (see p. 3056 and discussion thereof in section 4.2 on p. 3052). Ramprasad teaches that the reaction is preferably carried out in the presence of a Pt or Pd supported catalyst comprising a Cd, Bi, or Pb promoter. See claims.
It would have been prima facie obvious to combine the teachings of Kiyoura, Mallat, and Ramprasad 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 include a Cd, Pb, and/or Bi promoter in the Pt catalyst of Kiyoura because both Mallat and Ramprasad teach that the use of said promoters is well-known and predictable in the art to increase the rate of reaction and/or selectively of the reaction and also the catalyst life. Mallat teaches the predictability of this oxidation reaction over a broad range of alcohols, including those containing amine groups and analogous quaternary ammonium groups, and Ramprasad teaches a specific example wherein a choline (alcohol bearing a quaternary ammonium group) salt is oxidized to the corresponding betaine using oxygen in the presence of a base in aqueous solution at mild temperatures which overlap with that claimed. Therefore, there is a reasonable expectation of success that including one of the known promoters taught by Mallat and Ramprasad into the supported Pt catalyst of the di- and tri-ethanolamine oxidation process of Kiyoura will predictably improve the selectivity and/or reaction rate of the process and/or catalyst life. Also see MPEP 2143(I)(A).
Claim(s) 6, 7, and 10-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kiyoura (JPS5377009A, published 7/8/1978, of record in the IDS filed 8/17/2023) in view of Mallat (“Oxidation of Alcohols with Molecular Oxygen on Solid Catalysts” Chem. Rev. 2004, 104, p. 3037) and Ramprasad (US 6046356, published 4/4/2000, of record in the IDS filed on 8/17/2023), as applied to claims 1-5, 8, and 9 above, and further in view of Baumann (US 2012/0264973, published on 10/18/2012), as evidenced by DiGuilio (US 6075168, published 6/13/2000), and Ebner (US 5627125, published on 5/6/1997).
The combination of Kiyoura, Mallat, and Ramprasad teaches reacting compounds of instant formula (Ia) of claim 8 to produce compounds of formula (IIa) or formula (IIb) in claim 9.
Kiyoura further teaches that the equivalents of base added to the reaction affects the selectivity of the product produced. For example, if a full oxidation product of triethanolamine is desired, then at least 1 mol of hydroxide (from the base) per 1 mole of -OH on the triethanolamine would be required. If less than 1 mol of hydroxide from the base is used, partially oxidized products, such as that of compound (IIb) are formed. Mixtures of (IIa) and (IIb) can also be formed based on the quantity of base used and the selectivity of the reaction. Thus, it is obvious from the teachings of Kiyoura that the stoichiometry of the base in the reaction is a results effective variable that will affect the distribution of products produced from the reaction and the skilled artisan could predictably control the product composition, such as to produce a combination of products of formula (IIa) and (IIb) as required by claims 10-12, with a reasonable expectation of success. Also see MPEP 2144.05.
Kiyoura also teaches that all products are produced in about 70% yield in the examples and that “the aminocarboxylic acids obtained by the method of the present invention are compounds having alcohol, amine and carboxyl group in the molecule, and can be used in various organic synthesis raw materials, emulsifying agents, surfactants, bactericidal disinfectants, washing agents and builders”. See lines 39-43 of the translation. Therefore, even in reactions wherein the full oxidation product (such as compounds of instant formula (IIa)) is desired, partially oxidized products, such as those of instant formula (IIb) are expected to be present. However, as Kiyoura indicates that indicates that all of the products produced from the oxidation reaction have the same utility, then any combination of partially oxidized and fully oxidized compounds is desirable.
Kiyoura additionally mentions that the raw material ethanolamines are industrially produced from the reaction between ethylene oxide and ammonia. See lines 43-45 of the translation.
Mallat teaches that a wide variety of primary alcohols, including aminoalcohols and quaternary ammonium alcohols (such as those in Ramprasad), can be predictably oxidized with molecular oxygen in the presence of a base in aqueous solutions using supported Pt catalysts. Mallat further exemplifies that the oxidation reaction also applies to glycols, including the oxidation of ethylene glycol (HO-CH2-CH2-OH) to produce glycolic acid/glycolate (HO-CH2-COOH). See Scheme 2 on p. 3039 and discussion thereof. Also see Tables 15 and 16 on p. 3054 and discussion thereof in section 4.4 on p. 3053.
The combination of Kiyoura, Mallat, and Ramprasad do not explicitly teach i) the use of compounds of instant claim 6 to produce compounds of instant claim 12; ii) that glycols are present in the compounds of instant formula (I) as required by claim 7; and iii) the specific mixture of compounds (IIa), (IIb), glycolic acid (HO-CH2-COOH), and optionally oxalic acid (HO2C-CO2H) as required by claims 10-12.
Baumann is directed a two-stage process for producing aminopolycarboxylates (3) according to the following scheme:
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. See [0013]. Baumann teaches a first step wherein an aminoacid (1) is reacted with ethylene oxide to produce intermediate ethanolamine compounds (2) and then a second step wherein the intermediates (2) are catalytically converted to (3) in the presence of a base. The first stage is fully discussed in [0019-0038] and the second stage is fully discussed in [0039-0046]. Baumann teaches that the intermediates (2) formed under the first stage conditions are preferably subjected to the second stage oxidative dehydrogenation reaction without further purification. See [0006-0008, 0015-0017, and 0039].
Baumann exemplifies the preparation of methylglycine-N,N-diacetic acid trisodium salt (MGDA-Na3) as a desired compound of formula (3). See [0048-0070]. Baumann teaches that alanine (H2N-CH(CH3)-COOH, 1) is reacted with ethylene oxide to produce intermediate (2) which is oxidized in the presence of a base to produce MGDA-Na3 (3), wherein R in compounds (1) to (3) in the above Scheme is methyl (C1 alkyl). MGDA-Na3 is a trisodium salt of the compound of instant formula (IIa) in claims 10-12 wherein R1 is CH3-CH(COONa) (and R3 is -CH2-CO2Na in the compound (II) of claim 1). Compound (2) of Baumann, when R is methyl, corresponds to a compound of instant formula (I) in claim 1 and formula (Ia) in claim 8 wherein R1 is CH3-CH(COOH) and R2 is -CH2-CH2-OH is and the sodium salt thereof, as required by claim 6. Baumann teaches that MGDA-Na3, and other compounds of formula (3) and mixtures thereof, can be used directly as additives in industrial cleaning formulations as surfactants and as chelators for heavy metal cations. See [0046].
Thus, Baumann provides motivation to use compounds of instant claim 6 to produce products of instant claims 10-12.
Baumann also teaches the same ethoxylation process as that in the specification as filed for producing the MGDA intermediate of formula (II). See [0049] of Baumann vs. p. 11, lines 1-15 of the instant specification. The instant specification teaches that under identical conditions, 4.6 wt% ethylene glycol and 0.3 wt% diethylene glycol are produced and present in the compounds of instant formula (I). This indicates that the intermediate of Baumann inherently comprises ethylene glycol and diethylene glycol in the claimed percentages (claim 7). Also see MPEP 2112. This is further supported by the teachings of DiGuilio.
DiGuilio is directed toward an analogous process to that of Baumann and Kiyoura for producing ethanolamines in a reactive distillation column to reduce by-products. See abstract. DiGuilio is cited to teach that it is known in the art that the reaction of ethoxylation of ammonia with ethylene oxide produces a mixture of ethanolamines and a variety of co-product impurities such as ethylene glycol. See col. 1, lines 1-17. Thus, DiGuilio establishes that ethylene glycol is a known by-product of the reactions of Baumann and Kiyoura.
Ebner discloses an analogous process for oxidizing a primary alcohol to a carboxylic acid salt in an aqueous solution in the presence of a base hydroxide and a catalyst consisting essentially of an alkali resistant support, an anchor metal selected from the group consisting of platinum, palladium, ruthenium, and gold and an element selected from the group consisting of copper, cobalt, nickel, and cadmium. See abstract. This catalyst system is analogous to the catalyst system of Kiyoura, Mallat, and Ramprasad. In the examples, Ebner teaches that the disclosed catalytic system can oxidize both diethanolamine to disodium iminodiacetic acid (DSIDA) (examples 4-5) and ethylene glycol to sodium glycolate (example 11).
Thus, Ebner teaches that ethylene glycol can be oxidized to sodium glycolate under the same conditions as diethanolamine is oxidized to disodium diacetic acid. This is consistent with the teachings of Mallat regarding the predictability of using supported Pt catalysts to oxidize a variety of different alcohols to carboxylic acids under similar conditions.
It would have been prima facie obvious to combine the teachings of Kiyoura, Mallat, Ramprasad, and Baumann, as evidenced by DiGuilio, and Ebner to arrive at the instantly claimed processes with a reasonable expectation of success before the effective filing date of the claimed inventions. A person of ordinary skill would have been motivated to use compounds of claim 6 in the combined process of Kiyoura, Mallat, and Ramprasad to produce compounds of claims 10-12 because Baumann teaches that said compounds can be used as industrial surfactants and chelating agents, especially due to the presence of the carboxylate groups. Therefore, producing a commercially valuable product using a known and predictable process is not inventive. It is further obvious from the teachings of Kiyoura that the stoichiometry of the base in the reaction is a results effective variable that will affect the distribution of products produced from the reaction and the skilled artisan could predictably control the product composition, such as to produce a combination of products of formula (IIa) and (IIb) as required by claims 10-12, with a reasonable expectation of success. Kiyoura also teaches that all products are produced in about 70% yield in the examples and that “the aminocarboxylic acids obtained by the method of the present invention are compounds having alcohol, amine and carboxyl group in the molecule, and can be used in various organic synthesis raw materials, emulsifying agents, surfactants, bactericidal disinfectants, washing agents and builders”. See lines 39-43 of the translation. Therefore, even in reactions wherein the full oxidation product (such as compounds of instant formula (IIa)) is desired, partially oxidized products, such as those of instant formula (IIb) are expected to be present as the yield and conversion are not 100%. However, as Kiyoura indicates that indicates that all of the products produced from the oxidation reaction have the same utility, then any combination of partially oxidized and fully oxidized compounds is desirable. Also see MPEP 2143(I)(B).
Regarding the presence of glycols, specifically ethylene glycol, as an impurity in the compound of instant formula (I), as the conditions of Baumann are identical to those in the specification as filed for producing the compound of instant formula (I), then the glycols are presumed to be inherently present in the intermediate mixture of Baumann in the percentages of claim 7. Also see MPEP 2112. This assumption is further supported by evidentiary teachings of DiGuilio who teaches that ethylene glycol is a well-known impurity in the ethoxylation reactions of Baumann. Therefore, if the alkoxylation step of Baumann were used to produce the starting material of instant formula (I) in the combined process of Kiyoura, Mallat, and Ramprasad, then ethylene oxide would be expected to be present in starting material (I). It is further noted that Kiyoura discloses the same process for the production of compounds of instant formula (I). Combining a well-known process for producing a reactant with another well-known and predictable process for using the reactant is prima facie obvious. Also see MPEP 2143(I)(A).
Baumann further teaches that the compound of instant formula (I) having a glycol impurity is carried directly through to the oxidation step because of its purity when prepared according to the first stage conditions of Baumann. Therefore, if the alkoxylation process of Baumann was combined with the oxidation process of Kiyoura, Mallat, and Ramprasad, then the skilled artisan would also expect the ethylene glycol impurity to be carried through the oxidation reaction. As evidenced by Mallat and Ebner, the ethylene glycol is expected to be oxidized under the same conditions as ethanolamines to produce glycolic acid, as required by claims 10-12. Therefore, in addition to a mixture of partially and fully oxidized products of instant formulae (IIa) and (IIb) in any combination, the skilled artisan would also expect glycolic acid to be present in the final mixture as a by-product in similar amounts to the glycol by-products present in instant formula (I), when obtained using the ethoxylation process of Baumann.
Conclusion
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692