DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
The application claims priority to foreign application IN202321001371 filed on 6 January 2023.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 11 March 2023 and 15 April 2024 are acknowledged and considered.
Claim Rejections - 35 USC § 112
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 1 and 9 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 1 recites the limitation "… when the neutralization step F is performed…" in lines 6-7. The most recent claims submitted do not have a neutralization step F. The limitation in Step F of claim 1 recites “F) drying the granules under reduced pressure.” There is insufficient antecedent basis for this limitation in the claim. Applicant may delete the reference to step F) in claim 1 in order to overcome the rejection. Appropriate correction is requested.
Claim 9 recites the limitation “… wherein the micronized granules are subjected to…“ in line 2. Claim 1 recites “granules” and does not specify at any of steps A)-F) “micronized granules.” There is insufficient antecedent basis for this limitation in the claim. Furthermore, it is unclear which steps of claim 1, claim 9 is further limiting. In other words, it is unclear where the “micronized granules” exist in steps B) through F) of claim 1. The intent is unclear in light of the complexity of the rejection so no amendment has been suggested. Appropriate clarification is requested.
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.
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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Reierson (EP Patent No. 0675076B1) and Duesterloh (US Patent No. 11,224,563) in view of Schwerin (EP Publication No. EP1120456A1), further in view of Iveson (“Nucleation, growth and breakage phenomena in agitated wet granulation processes: a review” Powder Technology, 117, 3-39. Published 4 June 2001.).
Reierson teaches that fatty alcohol based anionic phosphate esters enriched in monoalkyl ester content relative to dialkyl content, have superior performance via improved detergency and low skin irritation, with respect to surfactant esters used in cosmetic and personal hygiene cleansers (¶ [0002]). Conventional reactions of phosphorous oxychloride, to produce enriched monoalkyl esters, are not ideal because they are not selective and produce undesirable alkyl chloride by-products (¶ [0020]). Reierson teaches a phosphating agent, in the range of 118% to about 125% (expressed as an effective equivalent percent polyphosphoric acid (PPA)) (¶ [0051]), can be prepared separately or in situ to produce phosphate ester compositions in a single step, solventless process, wherein the ratio of monoalkyl acid phosphate to dialkyl acid phosphate is greater than 80:20 with levels of free phosphoric acid and residual alcohol less than 6% (claim 4). This phosphation reagent, in contrast to the commercially available 115%-117% PPAs alone, is not required to have the acid in excess relative to the alcohol to achieve good conversion rates and low residual alcohol content (¶ [0034]). Examples of the preferred alcohols for the phosphating reaction are lauryl, myristyl, cetyl alcohols, etc. (¶ [0060). In an example reaction, lauryl alcohol was added to the phosphation reagent mixture and was warmed to 87°C and maintained for 290 minutes and quenched with water (¶ [0064]).
Reierson does not teach forming the salts of the resulting surfactant mixture by reacting the mixture with metal hydroxides nor does it teach converting a surfactant mixture to granules.
Duesterloh teaches topical compositions comprising a cetyl phosphate surfactant mixture consisting essentially of mono- and/or di- cetyl esters of phosphoric acid or salts thereof, cetyl alcohol, inorganic phosphate, heavy metals, and water. The inorganic phosphate content is <0.7 wt% (Abstract). It similarly states that conventional reactions of reacting cetyl alcohol with phosphorus oxychloride is not an attractive option because of the unwanted organochlorine impurities, and that new methods of reacting cetyl alcohol and phosphorpentoxide or phosphoric acid have been brought to market, albeit with formulation incompatibilities (column 1, lines 18-33). Duesterloh explicitly states that it would be well understood to a person skilled in the art to reduce the amount of inorganic phosphate in the cetyl phosphate surfactant mixture to generate particularly stable compositions (column 3, lines 16-19). The claimed percentages of the potassium cetyl phosphate surfactant mixture is recited: 70-90 wt% of a potassium salt of monocetyl phosphate ester, 0.5-12 wt% of a potassium salt of dicetyl phosphate ester, 0-15 wt% of cetyl alcohol, and 0-0.7 wt% of an inorganic phosphate (claim 1). The preparation of the surfactant mixture involves reacting cetyl alcohol dissolved in cyclohexane with pyrophosphoric acid (the simplest form of polyphosphoric acid) diluted in cyclohexane. After the reaction is complete, it is quenched and washed with water, and the cyclohexane is removed in vacuo. The crude product is further quenched with 50% KOH in water at 50°C and recrystallized in methanol to provide the desired surfactant mixture (column 6, lines 25-39).
Reierson and Duesterloh are considered analogous art to the claimed invention because they are in the same field of optimizing reaction conditions to exclude organochloride impurities, generating mixtures enriched with monoalkyl phosphate esters, and minimizing the impurities of the residual alcohol and free phosphoric acid. Therefore, it would have been prima facie obvious to a person having ordinary skill in the art (PHOSITA) before the effective filing date of the invention, to implement solventless reaction conditions wherein cetyl alcohol is reacted with a phosphation reagent composition in the range of 118% to about 125% (expressed as an effective equivalent percent PPA) (¶ [0051]) as taught by Reierson and neutralize the reaction mixture with 50% KOH solution to generate surfactant mixture salts as taught by Duesterloh. A PHOSITA would have been motivated to use solventless reaction conditions by reacting fatty alcohol with the phosphation reagent as taught by Reierson to generate surfactant mixtures enriched with monoalkyl phosphate ester, low residual alcohol, and free phosphoric acid impurities, and further convert the surfactant mixture to salt form by neutralizing the acid impurity as taught by Duesterloh.
Duesterloh does not teach solventless reactions, reactions of alcohol with PPA, nor does it teach converting the resulting surfactant mixture of potassium cetyl phosphate esters, cetyl alcohol, and inorganic phosphate to granules.
Schwerin teaches that phosphoric esters are unique in that they possess excellent detergent properties and high ecotoxicological compatibility. Solid water-free forms of these phosphate esters are desirable so that they can be incorporated in powder detergents, dentifrices, or syndet soaps (¶ [0002]). The teachings also state that simultaneous drying and granulation of the aqueous alkyl phosphate pastes leads to high bulk density wherein more than 50% by weight of all particles have a diameter of less than 600 µm (¶ [0007]). Furthermore, Schwerin teaches granulation of cetyl monophosphate potassium salt (¶ [0012]).
Reierson, Duesterloh, and Schwerin are all considered analogous art= because they are in the same field of using monoalkyl phosphate ester mixtures in industrial applications to provide for good detergency in formulations of powder detergents, topicals, syndet soaps, etc. Therefore, it would have been prima facie obvious to a PHOSITA before the effective filing date of the claimed invention, to synthesize cetyl phosphate ester mixtures enriched with monocetyl phosphate esters relative to dicetyl phosphate esters, and low residual alcohol and phosphoric acid, by reacting cetyl alcohol with a phosphation reagent (118%-125% PPA) in view of Reierson, convert them to salts by neutralizing with a metal hydroxide in view of Duesterloh, followed by subsequent conversion of the reaction mixture to granules through the teachings of Schwerin. A PHOSITA would have been motivated to produce a surfactant mixture enriched with monoalkyl phosphate esters and minimal impurities, having good detergent properties before converting the mixture to granules to meet the demand for obtaining solid-water free forms of said mixture to incorporate into detergents, dentifrices, and syndet soap.
Schwerin does not teach the process of making alkyl phosphate ester mixtures high in monocetyl phosphate esters or ageing granules.
Iveson teaches that granulation finds application in a wide range of industries including mineral processing, agricultural products, detergents, pharmaceuticals, foodstuffs, and specialty chemicals (page 4, first indented paragraph). The wet granulation process has three stages: wetting and nucleation, consolidation and growth, and breakage and attrition (Abstract). Granules collide with other granules as they gradually consolidate. As a result of this consolidation their size and porosity are reduced, which squeezes out entrapped air and may even squeeze liquid binder to the surface. Consolidation is taught to have a complex effect on the mechanical properties wherein the granule yield stress increases as the granule porosity decreases as result of liquid binder escaping to the surface. It is further discussed that porosity of granules initially decreases quickly and then levels to a stable equilibrium value (page 17, 4.2 Granule consolidation).
Schwerin and Iveson are considered to be analogous art because they are in the same field of optimization of parameters for granulation for industrial applications. Therefore, it would have been prima facie obvious to a PHOSITA before the effective filing date of the claimed invention, to synthesize cetyl phosphate ester mixtures enriched with monocetyl phosphate esters in view of Reierson and Duesterloh and convert the reaction mixture to granules through the teachings of Schwerin to allow for purification through the natural consolidation of granules as taught by Iveson. A PHOSITA would be motivated to obtain an alkyl phosphate ester surfactant mixture enriched with monoalkyl phosphate ester and convert it to granules because there is a need for these types of surfactants in cosmetics, hygiene cleansers, or topicals, as taught in Reierson and Duesterloh, and have them available in a solid water-free form, as taught in Schwerin. Through routine optimization (MPEP §2144.05 (II)(A)), it would have been prima facie obvious to a PHOSITA to allow the granules to consolidate to remove impurities from said granules, as taught by Iveson. The resulting granules would be readily available to incorporate into powder detergents, dentifrices, or syndet soaps (see above citations in Schwerin).
Iveson does not teach synthesis of monoalkyl phosphate esters, granulation, or explicitly the ageing of granules.
Regarding claim 1, Reierson teaches that cetyl alcohol (C16) is one of the preferred alcohols that can be reacted with the phosphation reagent composition, (118%-125% equivalent percent PPA), to obtain a cetylphosphate surfactant mixture containing at least a 90:10 mixture of MAP:DAP with residual alcohol and acid individually being less than 6% (claim 4). The equivalent percent of PPA of the phosphation reagent overlaps with the range instantly claimed and would therefore overlap with the chain length in Formula III (MPEP §2144.06). Schwerin teaches converting an aqueous paste of cetyl monophosphate potassium salt to granules utilizing a fluidized bed dryer (see above citations). The term “ageing” is not defined in the specification and is given its broadest reasonable interpretation (MPEP §2111.01(I)). Furthermore, the limitation in the instant claim reads “… C) ageing the granules of alkyl phosphates for maximum 10 days;” which does not exclude any timeframe less than 10 days. Iveson teaches that consolidation of granules leads to densification of granules and deposition of impurities to the surface of said granules. It would have been routine for a PHOSITA to allow time for the granules to consolidate and allow impurities, like free phosphoric acid, to redeposit at the surface of the granules, wash away impurities by wetting the granules with water, and subsequently dry the granules (MPEP §2144.05(II)(A)).
Regarding claims 2-3 and 13, Reierson teaches that equimolar amount of alcohol-phosphorus is desired for the reaction with the phosphation reagent to proceed. This reagent, in contrast to the commercially available 115%-117% PPA alone, is not required to have the acid in excess relative to the alcohol to achieve good conversion rates and low residual alcohol content (¶ [0034]). However, it would have been routine for a PHOSITA to use slight excess of commercially available PPA relative to the fatty alcohol to ensure minimal dialkyl phosphate ester production (MPEP 2144.05(II)(A)). An example reaction taught by Reierson is lauryl alcohol added to the phosphation reagent mixture which was warmed to 87°C and maintained for 290 minutes and subsequently quenched with water (¶ [0064]) which overlaps with the temperature range instantly claimed (MPEP §2144.05(I)).
Regarding claims 4 and 14, Schwerin teaches that after granulation of aqueous pastes of phosphate ester mixtures, the particles have a diameter of <600 µm, which overlaps with the range instantly claimed (MPEP §2144.05(I)).
Regarding claims 5 and 15, Schwerin teaches that that the granules can be cooled rapidly from 20-60s to temperatures between 30 to 40°C with ambient air, which overlaps with the range instantly claimed (¶ [0010], last sentence) (MPEP §2144.05(I)).
Regarding claim 6, Reierson, Duesterloh, Schwerin, and Iveson do not teach ageing or consolidation for a minimum of 1 day. However, ageing of the granules to allow for consolidation of the granules is taught by Iveson and would have been routine to a PHOSITA to arrive at the timeframe of ageing instantly claimed (MPEP §2144.05(II)(A)).
Regarding claims 7-9, Reierson, Duesterloh, Schwerin, and Iveson do not teach the wetting of granules after ageing of a maximum 10 days with water at a temperature of 0°C to 50°C, the wetting time being less than 2 minutes, or that the micronized granules are subject to water treatment at solid to water ratios between 10:80 w/w to 40:80 w/w. However, Schwerin teaches the aqueous paste of the alkyl phosphate salts have a solid content of at least 20%, the conversion to granules would not inherently alter this composition and thus overlaps with the range instantly claimed (MPEP §2144.05(I)). Wetting and overwetting of granules with water as taught by Iveson, would lead a PHOSITA, through routine optimization (MPEP §2144.05(II)(A)), to wash the granules and limit the time of contact to prevent overwetting of the granules, which would make an undesired slurry (page 25, second column, top paragraph).
Regarding claims 10 and 19-20, Duesterloh teaches neutralizing the crude reaction mixture with 50% KOH in water at 50°C. Schwerin teaches granulation of alkylphosphate ester surfactant mixtures. It would have been prima facie obvious to a PHOSITA to neutralize the crude alkylphosphate mixtures taught in Duesterloh and incorporate the teachings of Schwerin to have the crude alkylphosphate mixture in granular form. In other words, it would have been routine to a PHOSITA through these teachings, to granulate a reaction mixture enriched with monoalkyl phosphate ester and necessarily neutralize it the same as if it were in solution, to quench the unwanted acid impurity to allow for a compatible and safe formulation for topical compositions. Furthermore, it would have been routine to a PHOSITA to dry the resulting neutralized mixture under reduced pressure to remove any solvent impurities (MPEP §2144.05(II)(A)).
Regarding claims 11-12, Duesterloh teaches the product obtained by the process in claim 1 albeit through a different process and not being in granular form (MPEP §2113(II)). Additionally, the compositions of monocetyl and dicetyl phosphate ester, free acid, and alcohol overlap with the percentages instantly claimed (see above citations) (MPEP §2144.05(I)).
Regarding claim 16, Reierson, Duesterloh, Schwerin, and Iveson do not teach ageing or consolidation for a minimum of 5 days. However, ageing of the granules to allow for consolidation of the granules is taught by Iveson and would have been routine to a PHOSITA to arrive at the timeframe of ageing instantly claimed (MPEP §2144.05(II)(A)).
Regarding claims 17-18, Reierson, Duesterloh, Schwerin, and Iveson do not teach the wetting of granules after ageing of maximum 10 days with water at a temperature of <5°C. However, it would have been routine to a PHOSITA to lower the temperature of the water and reduce the time the water contacts the granules to prevent solubilizing the surfactant mixture granules (MPEP §2144.05(II)(A)).
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAHIL CHANDER AGGARWAL whose telephone number is (571)272-7755. The examiner can normally be reached 7am-5pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam C Milligan can be reached at (571) 270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAHIL CHANDER AGGARWAL/Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623
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