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 .
Formal Matters
Applicant’s response to the election /restriction requirement in the reply filed on 21 July 2026 is acknowledged and has been fully considered. Claims 21-40 are pending. Claims 21-28 and 30-40 are under consideration in the instant office action. Claim 29 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and/or species, there being no allowable generic or linking claims.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 14 July 2026, 23 December 2024, 29 July 2024, and 13 May 2024 are noted and the submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the examiner has considered the information disclosure statement. Signed copies are attached herein.
Election Restriction
Applicant’s election without traverse of the below listed species in the reply filed on 21 July 2026 is acknowledged.
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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.
Note: The claims are examined only with respect to the elected species listed below:
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Claims 21-28 and 30-40 are rejected under 35 U.S.C. 103 as being unpatentable over Winn (US 2020/0329704) in view of Hope et al. (Inorganica Chimica Acta 363 (2010) 935–943) and Hughes et al. (US Patent No. 7,007,805, IDS reference, 05/13/2024).
Applicants’ claims
Applicants claim an antimicrobial composition and products comprising the antimicrobial composition.
Determination of the Scope and Content of the Prior Art
(MPEP 2141.01)
Winn teaches a composition blend comprising caprylohydroxamic acid, or a salt and/or a complex thereof, and at least one alcohol (see claim 1). The compositions preferably include at least one vicinal diol in amounts of, for example, about 0.001% by weight to about 99.999% by weight of the blend of the hydroxamic acid, salt or complex thereof with the at least one alcohol. The hydroxamic acid, salt or complex thereof preferably is present in an amount of about 0.001% to about 99.999% by weight of the noted blend. If precursors for hydroxamic acids, salts or complexes are used as components according to one aspect of the invention, the weight percentages described herein and further below, refer to the amount of formed compound desired in the blends in the compositions, wherein the compounds are formed from the precursor reaction or combination (paragraph 0027). The most preferred vicinal diols for use in the compositions described herein when used in cosmetic, toiletry and pharmaceutical applications are medium-chain length, linear vicinal diols that demonstrate antimicrobial activity at relatively low use-levels. Such diols include 1,2-pentanediol, 1,2-hexanediol, caprylyl glycol, and 1,2-decanediol. Other vicinal diols useful in the compositions described herein include molecules derived from glycerin (paragraph 0025). Other similar functional groups that meet the criteria of being compatible with and/or suggested for use in cosmetic, toiletry and/or pharmaceutical formulations are also within the scope of the invention. Such hydroxamic acids may also be synthesized from natural oils using lipase catalysis as well as other hydroxamic synthesis techniques known or to be developed in the art. Examples of such alkylhydroxamic acids include, but are not limited to hexanohydroxamic acid, caprylohydroxamic acid, caprohydroxamic acid, laurohydroxamic acid and mixtures and combinations thereof, and most preferably is caprylohydroxamic acid. It should be noted herein that precursors, such as hydroxy acids in combination with, for example, hydroxylamine hydrochloride or a similar compounds which can react within solution and/or in the formulation to form the various hydroxamic and alkylhydroxamic acids, salts and/or complexes thereof as are known in the art may also be used instead of a direct additive within the scope of the invention (paragraph 0023). In one preferred embodiment, caprylyl glycol is blended with caprylohydroxamic acid. In another preferred embodiment, caprylyl glycol is blended with caprylohydroxamic acid and further blended with one or more glycols or vicinal diols that are liquid at room temperature, such that the entire blend is liquid and therefore easy to blend into a cosmetic, toiletry or pharmaceutical emulsion. Such liquid glycols and vicinal diols include ethylhexylglycerin, 1,2-hexanediol, 1,2-pentanediol, propylene glycol, butylene glycol, and hexylene glycol (paragraph 0035). It is preferred herein, that in preferred cosmetic, toiletry or pharmaceutical compositions, that the at least one hydroxamic acid is present in an amount of about 0.01 to about 10 percent by weight, and more preferably from about 0.1 to about 5 weight percent of a blend of the at least one alkylhydroxamic acid with the at least one vicinal diol and any optional solubilizing agent and/or water as noted herein. While only one alkylhydroxamic acid is necessary, such materials as described above may be used alone or in combinations with each other and with one or more vicinal diols. The amount of the alkylhydroxamic acid and the vicinal diol components in the blend should be selected so as to preferably provide a ratio of alkylhydroxamic acid(s) to vicinal diol(s) in the blend which is to be provided to the composition of about 99.999:0.001 to about 0.001:99.999 and more preferably about 10.00:0.01 to about 0.01:10.00, and most preferably about 10.0:0.1 to about 0.1:10.0 (paragraph 0036). The personal care and pharmaceutical formulations, if liquid based (such as gels, hydrogels, lotions, shampoos and the like) will also preferably include water as part of the liquid base. The formulations and compositions may include other additives as well, such as without limitation, at least one humectant, at least one emulsifier and/or thickener, chelating agent(s), gelling agent(s), amino acid(s), emollient(s), various solvents, free radicals and initiators, sunscreen UVA and/or UVB blocking agents, antioxidants, other preservatives, waxes, polymers and copolymers, inorganic and organic pigments and/or one more fragrances, coloring agent(s), herbs, natural extracts, essential oils, pharmaceutical drug products, and other additives commonly used in such formulations (paragraph 0039). The personal care and pharmaceutical compositions herein may be lotion-based, oil-in-water emulsions, water-in-oil emulsions, water-in-silicone emulsions, silicon-in-water emulsions, gels, solids, liquids, cream based, oil based, aqueous/alcoholic or glycolic solution based, dispersions, suspensions or syrups, microemulsions or a liposome-based formulations (paragraph 0040). The composition blend according to claim 16, wherein the at least one alcohol is a propanediol (see claim 19). The personal care and pharmaceutical compositions herein may be lotion-based, oil-in-water emulsions, water-in-oil emulsions, water-in-silicone emulsions, silicon-in-water emulsions, gels, solids, liquids, cream based, oil based (which the examiner notes is nonaqueous), aqueous/alcoholic or glycolic solution based, dispersions, suspensions or syrups, microemulsions or a liposome-based formulations (paragraph 0040). In personal care products, the compositions are preferably present in amounts of about 0.01 to about 10.00% by weight of the personal care product. In pharmaceutical products, the compositions are preferably present in an amount of from about 0.01 to about 10.00% by weight of the pharmaceutical product (paragraph 0030).
Ascertainment of the Difference Between Scope of the Prior Art and the Claims
(MPEP 2141.02)
Winn does not explicitly teach the elected potassium hydrogen caprylhydroxamate. This deficiency is cured by the teachings of Hope et al. and Hughes.
Hope et al. teach spectroscopic characteristics of n-octanohydroxamic acid and the potassium compound of that acid have been investigated by XRD, XPS, FTIR and Raman spectroscopy. XRD revealed that the acid is in the keto Z conformation with the alkyl chains oriented along the z-direction and hydrogen bonding between hydroxamate moieties. Vibrational spectra confirm this conclusion. Chemical analysis, XRD and XPS established that the potassium compound is the acid salt KH(C7H9CONO)2. The crystal structure showed that the hydroxamate groups are also in the keto Z conformation and this is supported by vibrational spectra. In the acid salt, the two hydroxamate moieties are connected by a symmetrical O–H–O short hydrogen bonded linkage between the two hydroxamate oxygen atoms and this explains the absence of a discernible O–H stretch band in the vibrational spectra. Identification of the vibrational bands displayed is supported by deuteration and 15N substitution (see abstract). Hope et al. teach crystal data for potassium hydrogen n-octanohydroxamate (see page 936). Hope et al. confirms the structure and stoichiometry of potassium hydrogen n-octanohydroxamate. Hope et al. teach pure crystal of potassium hydrogen n-octanohydroxamate which does not include any free hydroxylamine.
Hughes teaches a method of collecting mineral values from an aqueous ore slurry by froth flotation, the method comprising the step of adding an aqueous fatty hydroxamate composition to the aqueous ore slurry wherein the pH of said aqueous fatty hydroxamate composition is at least 11 and said aqueous fatty hydroxamate composition is essentially free of water insoluble solvents and removing the froth and associated mineral values (see claim 1). We have found that the efficiency of the hydroxamate reagent in recovery of particulate metals by the flotation method is dependent upon pH. Recovery of copper and many other metals is enhanced when the pH of the flotation liquor is in the vicinity of or about the pKa of the Bronstead acid which is the fatty hydroxamic acid. The working pH may be higher than the pKa (ca. 9). The recovery of copper using hydroxamate is enhanced significantly when the pH of the ore slurry is at least about 8.5 and more preferably from 8.5 to 13, most preferably 10 to 13. The hydroxamate composition of the invention is also found to be an effective collector at pH well below that of its pKa. As for instance, it recovers tin cassiterite (SnO2) at optimum pH from 4 to 5. In this instance, the reagent might have a relatively less solubility, however, as far our structural analysis the reagent functionality should still be accessible in reactive chelating mode. It is possible the zeta potential of tin mineral (˜4.5) induced hydroxamate adsorption process in a faster rate at lower pH. Since the hydroxamate reagent has limited solubility at pH 4–5 it is not able to form the reactive aggregate as it occurred at higher pH in the case copper recovery. It is found that with increasing temperature from 20 to 30° C. there is a significant improvement in the tin recovery process which may be offset in part by increasing the more soluble C-6 content of hydroxamate. Generally increasing the temperature increases the grade and recovery of the flotation process (column 4, lines 41-67). The hydroxamate composition of the invention may be prepared by increasing the pH of hydroxamates prepared by process known in the art. For example, in one embodiment a fatty acid derivative such as a lower alkyl (e.g., methyl or ethyl ester of a C6 to C14 fatty acid (which the examiner notes that capryl is C8) is reacted with hydroxylamine in aqueous solution. The hydroxylamine may be formed in situ from hydroxylamine salts in the presence of an alkaline aqueous solution which is typically an aqueous solution of alkali metal hydroxide (column 5, lines 15-24). A method according to claim 1 wherein the counter ion is sodium, potassium or a mixture of sodium and potassium (claim 10). The final resulting product of the reaction is potassium hydrogen caprylhydroxamate as evidenced by Applicant’s own specification example 1 which discloses in Example 1 that potassium hydrogen caprylhydroxamate, was prepared via reaction of methyl caprylate and hydroxylamine according to the procedure described by Hughes (US 7,007,805). The resulting salt was isolated via filtration, purified by washing with methanol, and dried to a 15 constant weight.
Finding of Prima Facie Obviousness Rational and Motivation
(MPEP 2142-2143)
It would have been prima facie obvious to a person of ordinary skill in the art before the effective filing date of the instant invention to modify the teachings of Winn by utilizing or selecting the potassium salt of the caprylhydroxamic acid for use in the proposed products because first Winn clearly suggests the salt forms of caprylhydroxamic acid. Furthermore, Hope et al. establishes the identity, stoichiometry and solid-state characteristics of potassium hydrogen form of caprylhydroxamic acid, making it an available and characterizable equivalent as described above. Additionally, Hope et al. teach that XPS data were also obtained for the same sample of potassium hydrogen n-octanohydroxamate after it had been stored at ambi ent temperature for 10 months, and after the same specimen had been subjected to the X-ray and flood gun beams during intervals in an overall period of 16 h (see page 939). Furthermore, one of ordinary skill in the art needed detail for preparation of the salt form Hughes teaches a method of collecting mineral values from an aqueous ore slurry by froth flotation, the method comprising the step of adding an aqueous fatty hydroxamate composition to the aqueous ore slurry wherein the pH of said aqueous fatty hydroxamate composition is at least 11 and said aqueous fatty hydroxamate composition is essentially free of water insoluble solvents and removing the froth and associated mineral values (see claim 1). We have found that the efficiency of the hydroxamate reagent in recovery of particulate metals by the flotation method is dependent upon pH. Recovery of copper and many other metals is enhanced when the pH of the flotation liquor is in the vicinity of or about the pKa of the Bronstead acid which is the fatty hydroxamic acid. The working pH may be higher than the pKa (ca. 9). The recovery of copper using hydroxamate is enhanced significantly when the pH of the ore slurry is at least about 8.5 and more preferably from 8.5 to 13, most preferably 10 to 13. The hydroxamate composition of the invention is also found to be an effective collector at pH well below that of its pKa. As for instance, it recovers tin cassiterite (SnO2) at optimum pH from 4 to 5. In this instance, the reagent might have a relatively less solubility, however, as far our structural analysis the reagent functionality should still be accessible in reactive chelating mode. It is possible the zeta potential of tin mineral (˜4.5) induced hydroxamate adsorption process in a faster rate at lower pH. Since the hydroxamate reagent has limited solubility at pH 4–5 it is not able to form the reactive aggregate as it occurred at higher pH in the case copper recovery. It is found that with increasing temperature from 20 to 30° C. there is a significant improvement in the tin recovery process which may be offset in part by increasing the more soluble C-6 content of hydroxamate. Generally increasing the temperature increases the grade and recovery of the flotation process (column 4, lines 41-67). The hydroxamate composition of the invention may be prepared by increasing the pH of hydroxamates prepared by process known in the art. For example, in one embodiment a fatty acid derivative such as a lower alkyl (e.g., methyl or ethyl ester of a C6 to C14 fatty acid (which the examiner notes that capryl is C8) is reacted with hydroxylamine in aqueous solution. The hydroxylamine may be formed in situ from hydroxylamine salts in the presence of an alkaline aqueous solution which is typically an aqueous solution of alkali metal hydroxide (column 5, lines 15-24). A method according to claim 1 wherein the counter ion is sodium, potassium or a mixture of sodium and potassium (claim 10). The final resulting product of the reaction is potassium hydrogen caprylhydroxamate as evidenced by Applicant’s own specification example 1 which discloses in Example 1 that potassium hydrogen caprylhydroxamate, was prepared via reaction of methyl caprylate and hydroxylamine according to the procedure described by Hughes (US 7,007,805). The resulting salt was isolated via filtration, purified by washing with methanol, and dried to a 15 constant weight. Furthermore, in the case where the amount of ingredients or concentrations "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). Furthermore, differences in concentration or size will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233,235 (CCPA 1955). An ordinary skilled artisan would have had a reasonable chance of success in combining the teachings of Winn, Hope et al., and Hughes because all of the references teach caprylhydroxamic acid based compounds and/or compositions.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, as evidenced by the references, especially in the absence of evidence to the contrary.
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.
Claims 21-28 and 31-36 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 12-20 of U.S. Patent No. 12,016,942 (‘942) in view of Winn (US 2020/0329704) and Hope et al. (Inorganica Chimica Acta 363 (2010) 935–943). Claim 21 recites an antimicrobial composition comprising a potassium hydrogen alkylhydroxamate salt and a medium chain terminal diol, wherein the potassium hydrogen alkylhydroxamate salt is present in an amount greater than 0.01 wt%, based on total weight of the antimicrobial composition. Claim 22 recites the antimicrobial composition of claim 21, wherein the potassium hydrogen alkylhydroxamate salt is of a formula KH(AH)₂, wherein K is potassium, H is hydrogen, and AH is a C₆ to C₁₀ alkylhydroxamate anion. Dependent claims thereof recited additional features that further define the base claim regarding the specific potassium hydrogen alkylhydroxamate salt and the specific medium chain alkyl diol. 942’ in claim 12 recites an antimicrobial composition comprising: a medium chain terminal diol, KH(AH)2, wherein K is potassium, H is hydrogen, and AH is a C6 to C10 alkylhydroxamate anion; and a C6-C10 alkylhydroxamic acid, wherein the antimicrobial composition has a free hydroxylamine concentration of less than 200 ppm. Claims 13 -21 recite further features defining the major components of claim 12 of ‘942. The difference between instant claim 21 and claim 12 of ‘942 is the recitation of “wherein the antimicrobial composition has a free hydroxylamine concentration of less than 200 ppm”. This deficiency is cured by Winn and Hope as explained above which are incorporated herein by reference. Winn teaches the salt form of caprylhydroxamic acid and Hope et al. clearly teach potassium hydrogen caprylhydroxamate. The advantages listed above the prima face argument section are incorporated herein by reference in their entirety from the 35 USC 103 section.
Conclusion
No claims are allowed.
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/TIGABU KASSA/Primary Examiner, Art Unit 1619
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