WO2020262367A1 - Ｎε－長鎖アシルリジン結晶の製造方法及びその結晶を含有する組成物 - Google Patents

Ｎε－長鎖アシルリジン結晶の製造方法及びその結晶を含有する組成物 Download PDF

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WO2020262367A1
WO2020262367A1 PCT/JP2020/024572 JP2020024572W WO2020262367A1 WO 2020262367 A1 WO2020262367 A1 WO 2020262367A1 JP 2020024572 W JP2020024572 W JP 2020024572W WO 2020262367 A1 WO2020262367 A1 WO 2020262367A1
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Prior art keywords
lysine
powder
lauroyl lysine
crystal
crystals
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PCT/JP2020/024572
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English (en)
French (fr)
Japanese (ja)
Inventor
ビスワス シュヴェンドゥ
直弥 山戸
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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Priority to JP2021527635A priority Critical patent/JP7679769B2/ja
Priority to KR1020227002566A priority patent/KR20220027995A/ko
Priority to CN202080046815.7A priority patent/CN114026062B/zh
Priority to EP20831974.9A priority patent/EP3992175B1/en
Publication of WO2020262367A1 publication Critical patent/WO2020262367A1/ja
Priority to US17/646,027 priority patent/US12221403B2/en
Anticipated expiration legal-status Critical
Priority to US19/005,604 priority patent/US20250136541A1/en
Priority to JP2025028747A priority patent/JP2025071320A/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/022—Powders; Compacted Powders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/622—Coated by organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention relates to a method for producing an N ⁇ -long-chain acylidine crystal and a composition containing the crystal.
  • Powder raw materials that can exhibit both water repellency and oil repellency at the same time are important in cosmetics and various industrial applications. However, it has been considered difficult to obtain an inexpensive powder raw material that can simultaneously exert these functions and has a low environmental load.
  • inorganic powders such as talc, mica, sericite, titanium oxide, zinc oxide, iron oxide, aluminum oxide, barium sulfate, boron nitride, silica, synthetic gold mica (synthetic mica), starch, cellulose, fatty acid salts, etc.
  • Organic powders such as bamboo and wood powders are used for the purposes of imparting smoothness, improving hiding power, coloring, and absorbing and scattering light.
  • Powders surface-treated with fluorine-containing molecules exhibit excellent water and oil repellency, but due to the presence of perfluorine compounds and low molecular weight fluorine compounds as impurities, there are problems of accumulation in the environment and human body and toxicity. It has been pointed out. Further, the powder surface-treated with fluorine-containing molecules has a problem that it does not fit well on the skin and is not excellent in makeup lasting and usability. Further, the powder surface-treated with fluorine-containing molecules has an extremely low oil repellency in the presence of water, so that there is a problem that the powder gets wet with sweat and sebum when used in cosmetics.
  • N ⁇ -lauroyl lysine crystals which are amino acid-derived raw materials that do not disperse in water and are not soluble in oil, are attached to the powder surface to give the powder the function of N ⁇ -lauroyl lysine crystals. Consideration is being given to granting. It is important that the surface of the powder is completely covered with N ⁇ -lauroyl lysine crystals.
  • the 90% particle size D90 (number-based distribution) of general powder is often 20 ⁇ m or less
  • commercially available N ⁇ -lauroyl lysine crystals (“Amihope LL” manufactured by Ajinomoto Co., Ltd.)
  • the 90% particle diameter D90 (number-based distribution) is 15.7 ⁇ m
  • the median diameter and average particle diameter of the volume-based distribution are 14.3 ⁇ m and 15.3 ⁇ m, respectively.
  • the median diameter of the volume-based distribution of N ⁇ - octanoyl lysine crystals (“Amihope” OL manufactured by Ajinomoto Co., Inc.) is 20 ⁇ m.
  • a general powder is stably covered with N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine crystals by simply mixing them. It's hard to be done.
  • a simple dry treatment method is known in which the powder is simply mixed with N ⁇ -lauroyl lysine crystals and the surface of the powder is treated with N ⁇ -lauroyl lysine crystals (International Publication No. 2011/025252).
  • this method the coverage of N ⁇ -lauroyl lysine crystals was poor, and as a result, sufficiently excellent water repellency and oil repellency could not be realized.
  • N epsilon - for the purpose of improving the coverage of lauroyl lysine crystalline
  • the fine powder was simply mixed with the powder, the powder surface N epsilon - lauroyl lysine crystalline
  • the method of processing with is being studied.
  • N ⁇ -lauroyl lysine crystals are pulverized by a wet pulverization method (Japanese Patent Laid-Open No. 09-323914, Japanese Patent No. 4826049) and mixed with an inorganic powder.
  • crystallization is performed by dropping a base solution of N ⁇ -lauroyl lysine into a solution such as hydrochloric acid whose pH is maintained at 2 to 5. It has been reported that crystals of N ⁇ -lauroyl lysine having an average projected diameter of 0.5 ⁇ m were obtained (Japanese Unexamined Patent Publication No. 08-337519). By mixing the crystals with the powder, it is possible to improve the adhesive force of the mixed powder to the skin and the usability of the mixed powder.
  • the reason why the water repellency and oil repellency of the powder cannot be improved by using the N ⁇ -lauroyl lysine crystals obtained by this method is that the particle size of the mixed N ⁇ -lauroyl lysine crystals is large.
  • the projected diameter measured by a microscope and the average particle diameter measured by a light scattering method or the like may differ from each other in terms of measurement principle.
  • N ⁇ -lauroyl lysine crystals having an average particle diameter (volume reference distribution) of 3 to 15 ⁇ m have been obtained (Patent No. 4826049).
  • N ⁇ -lauroyl lysine crystals obtained by this method sufficiently excellent water repellency and oil repellency cannot be realized.
  • N ⁇ -lauroyl lysine is adhered to the powder surface by wet treatment (Japanese Patent Laid-Open No. 4-63844, JP-A-61-10503).
  • N ⁇ -lauroyl lysine itself is sparingly soluble, it is once dissolved in a strong alkali, strong acid or solvent, and the solution is gradually added to the acid or alkaline powder dispersion to gradually add the powder surface in the powder dispersion.
  • N ⁇ -lauroyl lysine can be neutralized and crystallized. By filtering and drying the dispersion after crystallization, a powder having N ⁇ -lauroyl lysine attached to the surface can be obtained.
  • a certain level of water repellency and oil repellency can be obtained, but the degree is not sufficient.
  • this method has a problem that many organic solvents need to be used and repeated dissolution / drying steps need to be performed, so that it cannot be produced at low cost. Furthermore, in the case of powders such as silica and starch that dissolve in solvents, acids and alkalis, there is also the problem that the powder surface cannot be treated with N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine crystals. is there.
  • An object of the present invention is to obtain a technique capable of imparting water-repellent and oil-repellent functions to the powder while improving the soft feel of the powder and producing the powder at low cost.
  • the present inventors have found for the first time that the above problems can be solved by producing N ⁇ -long-chain acylidine crystals by a specific method, and have completed the present invention. .. That is, the present invention is as follows. [1] N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal having a 90% particle size D90 of the number reference distribution of 2.8 ⁇ m or less.
  • N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal according to [1], wherein the median diameter or the average particle size of the volume reference distribution is 2.8 ⁇ m or less.
  • N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal having a bulk density of 0.34 g / mL or less.
  • [4] Prepare a solution in which one or more types of N ⁇ -long-chain acylidine are dissolved in one or more selected from water-soluble organic solvents and / or an acidic or basic solvent containing water, and prepare the solution at 20 ° C. or lower.
  • a method for producing a non-pulverized N ⁇ -long-chain acyl lysine crystal which comprises crystallization of an N ⁇ -long-chain acyl lysine crystal by dropping it into an acidic solution having a pH of 0.2 or more and lower than pH 2.0 at a temperature.
  • the processed powder obtained by. [12]
  • the powder includes resin powder, silicon-containing powder, metal oxide, carbon-containing powder, fluorine-containing powder, metal salt, boron-containing powder, crystalline or non-crystalline powder of composite powder [ 11] The treated powder according to.
  • N and covers the treated powder surface epsilon - of the crystals of lauroyl lysine, particle size 1.8 ⁇ m or less of N epsilon - according to the proportion of lauroyl lysine crystals is 90% or more [11] or [12] Processed powder.
  • N ⁇ -long chain acylidine crystal of the present invention one or more types of N ⁇ -long chain acyl lysine are dissolved in an acidic or basic solvent containing one or more selected from water-soluble organic solvents and / or water.
  • an acidic or basic solvent containing one or more selected from water-soluble organic solvents and / or water.
  • N epsilon - solution of the long-chain acyl-lysine is N epsilon - may be obtained by dissolving crystalline long chain acyl-lysine is reacted with fatty acid and lysine, it may be used those obtained as a reaction solution not crystallize it can.
  • the long-chain acyl group of N ⁇ - long-chain acyl lysine is a saturated or unsaturated fatty acid acyl having 8 to 22 carbon atoms, for example, octanoyl, lauroyl, myristol, palmitoyl, stearoyl, octyldodecyl, oleyl, behenyl, coconut oil fatty acid acyl. , Palm kernel oil fatty acid acyl, beef fat fatty acid acyl and the like, but lauroyl and octanoyl are preferable in that they can be obtained for general purposes.
  • water-soluble organic solvent examples include acetone, methanol, ethanol, propanol, butanol, isopropanol and the like, and acetone, methanol, isopropanol and butanol are preferable. These water-soluble organic solvents may be used alone or in combination of two or more. When the water-soluble organic solvent and water are used in combination, the ratio is not particularly limited, and the water-soluble organic solvent / water can be used in the range of 0/100 to 100/0 by weight, but 55 / It is 45 to 70/30.
  • the acid used in the acidic solvent may be either an organic acid or an inorganic acid, and examples thereof include sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, citric acid, lactic acid, glutamic acid, and pyrrolidonecarboxylic acid, but sulfuric acid and hydrochloric acid are preferable.
  • the base used in the basic solvent may be either an organic base or an inorganic base, for example, sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, ammonia, triethylamine, triethanolamine, monoethanolamine. , Ppyridine, arginine, lysine and the like, but sodium hydroxide and potassium hydroxide are preferable.
  • the amount of the acid or base in the acidic or basic solvent is not particularly limited as long as N ⁇ -long-chain acyllysine can be dissolved.
  • the temperature at the time of crystallization is not particularly limited as long as it is 20 ° C.
  • the temperature is preferably 15 ° C. or lower, more preferably 10 ° C. or lower, and particularly preferably 8 ° C. or lower.
  • the lower limit of the temperature at the time of crystallization may be equal to or higher than the freezing point of the solvent.
  • the acidic solution used for crystallization can be prepared with the above-mentioned acid.
  • the pH of the acidic solution is 0.2 or more and lower than 2.0, preferably 0.7 to 1.3, and more preferably 0.8 to 1.1.
  • the method of picking up and drying the produced crystals can be carried out by a commonly used method.
  • the N ⁇ -long-chain acyllysine crystals thus obtained functioned as a stable pearlizing agent in the cleansing composition, and the skin and hair were further washed with the cleansing composition containing such crystals. If so, the conditioning effect of hair and skin is improved. Further, when the crystals are contained in the cleaning agent composition, the slimy feeling at the time of cleaning the cleaning agent can be suppressed. Further, when the crystals are used in a milky lotion, the moist feeling and glossiness of the milky lotion can be improved. Further, by treating the powder with the crystals, it is possible to impart water-repellent and oil-repellent functions to the powder while improving the softness of the feel of the powder and the gloss at the time of application.
  • the crystals are preferably N epsilon - lauroyl lysine mixed crystals - lauroyl lysine crystalline, or N epsilon - octanoyl lysine and N epsilon.
  • N epsilon - octanoyl lysine and N epsilon - lauroyl lysine mixed crystals N epsilon - octanoyl lysine emissions and N epsilon - may be a mixture of lauroyl lysine each single crystal, N epsilon - octanoyl lysine emissions and N epsilon - May be a eupsilon of lauroyl lysine.
  • N epsilon - octanoyl lysine and N epsilon - lauroyl lysine in the mixed crystal N epsilon - the octanoyl lysine is preferably in a proportion of less than 99 mass percentage.
  • the content of N ⁇ - octanoyl lysine is more preferably 5 to 75%, further preferably 15 to 45%, and most preferably 20 to 30%.
  • Lauroyl lysine crystalline, and N ⁇ - - N ⁇ of the present invention octanoyl lysine and N epsilon - lauroyl lysine mixed crystals, 90% particle diameter D90 of the number-based distribution is less than 2.8 .mu.m.
  • the crystals of the present invention function as a stable pearlizing agent in the cleansing composition, and when the skin and hair are washed with the cleansing composition containing such crystals, the 90% particle size D90 is 3 ⁇ m or more. Compared with N ⁇ -lauroyl lysine crystals, the conditioning effect of hair and skin is improved.
  • the crystal of the present invention when the crystal of the present invention is contained in the cleaning agent composition, the slimy feeling at the time of cleaning the cleaning agent can be suppressed.
  • the crystals of the present invention can improve the moist feeling and glossiness of the emulsion when used in the emulsion.
  • by treating the powder with the crystals of the present invention it is possible to impart water-repellent and oil-repellent functions to the powder while improving the softness of the feel of the powder and the gloss at the time of application.
  • the 90% particle size D90 is preferably 0.01 to 2.8 ⁇ m, more preferably 0.05 to 1 ⁇ m, and even more preferably 0.1 to 0.7 ⁇ m.
  • Lauroyl lysine crystalline, and N ⁇ - - N ⁇ of the present invention octanoyl lysine and N epsilon - lauroyl lysine mixed crystal further median diameter or the volume-based distribution average particle diameter is less than 2.8 .mu.m.
  • the median diameter or the average particle diameter is preferably 0.01 to 2.8 ⁇ m, more preferably 0.05 to 2.0 ⁇ m, and further preferably 0.07 to 1.5 ⁇ m.
  • N epsilon of the present invention - lauroyl lysine crystalline, and N epsilon - octanoyl lysine and N epsilon - bulk density of lauroyl lysine mixed crystals is less 0.34 g / mL.
  • the crystals of the present invention function as a stable pearlizing agent in the cleansing composition, and when the skin and hair are washed with the cleansing composition containing such crystals, the bulk density is 0.35 g / mL or more.
  • the conditioning effect of hair and skin is improved as compared with N ⁇ -lauroyl lysine crystals and the like.
  • the crystal of the present invention when the crystal of the present invention is contained in the cleaning agent composition, the slimy feeling at the time of cleaning the cleaning agent can be suppressed.
  • the crystals of the present invention can improve the moist feeling and glossiness of the emulsion when used in the emulsion.
  • by treating the powder with the crystals of the present invention it is possible to impart water-repellent and oil-repellent functions to the powder while improving the softness of the feel of the powder and the gloss at the time of application.
  • the bulk density is preferably 0.01 to 0.32 g / mL, more preferably 0.05 to 0.30 g / mL, still more preferably 0.1 to 0.25 g / mL.
  • the median diameter, average particle diameter, and 90% particle diameter D90 of the N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal of the present invention are laser diffraction / scattering type particle size distribution measuring devices. Can be determined by measuring the number-based or volume-based particle size distribution using.
  • the median diameter means the particle diameter at the point where the distribution curve of the accumulated passage amount intersects the horizontal axis of 50%, and the 90% particle diameter D90 intersects the horizontal axis of the distribution curve of the accumulated passage amount% of 90%. It means the particle size of the point to be used.
  • the average particle size means the arithmetic mean particle size of the distribution.
  • the "number-based distribution” represents the particle size distribution calculated based on the number of particles counted when calculating the frequency of each particle size of the particle size distribution, and is the "volume-based distribution”. Refers to the particle size distribution calculated based on the value obtained by counting the volumes of particles assumed to be spherical when calculating the frequency of each particle size of the particle size distribution.
  • the N epsilon - provides a composition comprising 0.01 to 99.9 ratio lauroyl lysine mixed crystals - lauroyl lysine crystalline or N epsilon - octanoyl lysine and N epsilon.
  • the composition of the present invention can be used as a composition for industrial use. For example, it can be blended with a printing or writing ink, a pencil lead, or the like in order to improve the color development, adhesion, and durability of the pigment. Further, it can be blended in paint from the viewpoint of preventing oxidation of pigments, improving water repellency, and improving dispersibility, and can also be blended in tires and paper.
  • composition of the present invention can also be used as a cosmetic or an external preparation.
  • the cosmetic or external preparation can be prepared in any form applicable to, for example, a desired site (eg, skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method.
  • Cosmetics or external preparations for skin, lips, eyelashes and nails include, for example, sunscreens, body powders, sunscreens such as sprays, foundations, primers, body colors, bronzer, face powders, manicures, teak colors, makeup bases, etc.
  • Makeup cosmetics such as concealers, lip color, lip liner, lip cosmetics such as lip sticks, eye makeup cosmetics such as eye liner, eye shadow, eyebrow, mascara, milky lotion, lotion, cream, gel, beauty liquid, etc. Leave-on cosmetics and face masks.
  • Examples of cosmetics or external preparations for hair include hair styling products, hair emulsions, hair treatments, hair conditioners, and hair lotions.
  • Examples of cosmetics or external preparations for the scalp include hair growth agents.
  • Preferred cosmetics include, for example, make-up makeup, eye makeup makeup, lip cosmetics, and leave-on cosmetics.
  • Preferred external preparations include, for example, ointments, creams, mousses and gels.
  • the composition of the present invention can be used as a cleaning agent composition.
  • the cleaning composition is not particularly limited as long as it is a cleaning composition containing a surfactant, and the effects of the present invention can be exhibited. More preferable examples include face wash, body soap, soap, cleansing balm, cleansing oil and other skin wash, shampoo and other hair wash, dish wash wash, vegetable wash wash, machine wash wash and other cleansers. Examples include the composition.
  • the treated powder of the present invention can be obtained by mixing the powder and the above-mentioned N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal.
  • the powder is not particularly limited as long as it is used for industrial purposes or cosmetics (pigments, pigments, resins, pearls), but examples thereof include resin powders such as nylon beads, silicone beads, and polyethylene beads; Iron oxide (yellow pigment), iron oxide (red pigment), iron oxide (black pigment), tin oxide, chromium oxide, cobalt oxide, zinc oxide, pigment grade zinc oxide, titanium oxide, pigment grade titanium oxide, zirconium oxide, oxidation Metal oxides such as aluminum, cerium oxide, fine particle titanium oxide, ultrafine titanium oxide, fine particle zinc oxide, fine particle iron oxide; Silicates (silicic acid (Al / Ca / Na), silicic acid (Na / Mg), sericite, mica, talc, kaolin, bentonite, aluminum silicate, magnesium silicate, cubic sodium aluminosilicate, silicon dioxide, hydrous silica Silicon oxide-containing powders such as silicon oxide and silicic acid anhydride (leaf flake silica, non-porous silica,
  • the powder may be subjected to surface treatment such as silicone treatment, fluorine compound treatment, silane coupling agent treatment, silane treatment, organic titanate treatment, fatty acid treatment, metal soap treatment, oil preparation treatment, amino acid treatment and the like.
  • the resin powder, silicon-containing powder, metal oxide, carbon-containing powder, fluorine-containing powder, metal salt, boron-containing powder, crystalline or non-crystalline powder of the composite powder are used after the treatment. It is preferable in terms of improving water repellency and oil repellency.
  • Mixing of the powder and the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and the N ⁇ -lauroyl lysine mixed crystal can be carried out by mixing in a mixer for 1 minute or more.
  • the mixing time is preferably 1 minute or longer, more preferably 10 minutes or longer.
  • the mixing time is preferably 60 minutes or less from the viewpoint that the product can be produced at low cost without reducing the productivity.
  • Mixers include high-speed stirring mixers such as Henschel mixers, household mixers, and high-share mixers, W-type mixers, CV-type mixers, V-type mixers, locking mixers, and other containers. Compression / shearing of rotary mixer, ribbon stirring type, double shaft paddle type, biaxial planetary stirring type, conical screw type mechanical stirring type mixer, air flow stirring type mixer, Julia mixer, Nauter mixer, Nobilta, etc. An impact type mixer or the like can be used, and a high speed stirring type mixer is preferable from the viewpoint of inexpensive production and versatility.
  • high-speed stirring mixers such as Henschel mixers, household mixers, and high-share mixers, W-type mixers, CV-type mixers, V-type mixers, locking mixers, and other containers. Compression / shearing of rotary mixer, ribbon stirring type, double shaft paddle type, biaxial planetary stirring type, conical screw type mechanical stirring type mixer, air flow stirring type mixer, Julia mixer, Nauter mixer, Nobilta, etc.
  • the mixing may also be carried out by pulverizing the powder and the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal.
  • the pulverization is performed by pulverizing the powder and the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal using a coarse crusher, a medium crusher, a crusher, or the like for 1 minute or more. Can be carried out.
  • the crushing time is preferably 1 minute or longer, more preferably 10 minutes or longer.
  • Crushers include, for example, jaw crushers, medium crushers include, for example, cutter mills and rakers, and crushers include, for example, roller mills, jet mills, hammer mills, pin mills, rotary mills, attritors, bead mills, atomizers, etc. It can be used, but is not limited to these. From the viewpoint of inexpensive production and versatility, jet mills, pin mills, rotary mills, atomizers, bead mills and the like are preferable.
  • the solvent having a boiling point of 130 ° C. or lower has a mass ratio of 10% with respect to the entire mixture. It may be used in the following range, but it is preferable not to use it.
  • the treated powder is N ⁇ -lauroyl lysine crystal or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal at a mass ratio of 0.01 to 99.9, preferably 0.1 to 80 mass ratio. More preferably, it is contained in a mass ratio of 1 to 15.
  • N epsilon - lauroyl lysine N epsilon crystal treated covers the surface of the treated powder - among crystals of lauroyl lysine, particle size of more than 90% crystallinity is equal to or less than 1.8 .mu.m, preferably 1 It is 5.5 ⁇ m or less, more preferably 1.2 ⁇ m or less.
  • N epsilon - octanoyl lysine and N epsilon - N covers the surface of the lauroyl lysine mixed crystals treated with the treated powder epsilon - octanoyl lysine and N epsilon - of lauroyl lysine mixed crystals, 90%
  • the particle size of the above crystals is 2.8 ⁇ m or less, preferably 2.5 ⁇ m or less, and more preferably 1.8 ⁇ m or less.
  • the powder treated with the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal of the present invention has water repellency. Further, the powder treated with the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal of the present invention has oil repellency.
  • the powder treated with the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal of the present invention has a soft focus effect.
  • the treated powder is obtained by mixing the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal with the powder at a ratio of 5% by mass to 40% or more of the powder surface area.
  • Preferably 50% may be prepared by a method comprising coating with N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals.
  • the coverage area ratio can be obtained by image analysis using software such as ImageJ.
  • the mixing can be carried out by mixing in a mixer for 1 minute or longer.
  • the mixing time is preferably 1 minute or longer, more preferably 10 minutes or longer.
  • the mixing time is preferably 60 minutes or less from the viewpoint that the product can be produced at low cost without reducing the productivity.
  • Mixers include high-speed stirring mixers such as Henschel mixers, household mixers, and high-share mixers, W-type mixers, CV-type mixers, V-type mixers, locking mixers, and other containers. Compression / shearing of rotary mixer, ribbon stirring type, double shaft paddle type, biaxial planetary stirring type, conical screw type mechanical stirring type mixer, air flow stirring type mixer, Julia mixer, Nauter mixer, Nobilta, etc. An impact type mixer or the like can be used, and a high speed stirring type mixer is preferable from the viewpoint of inexpensive production and versatility.
  • the mixing may also be carried out by pulverizing the powder and the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal.
  • the pulverization is performed by pulverizing the powder and the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal using a coarse crusher, a medium crusher, a crusher, or the like for 1 minute or more. Can be carried out.
  • the crushing time is preferably 1 minute or longer, more preferably 10 minutes or longer.
  • the mixing time is preferably 60 minutes or less from the viewpoint that the product can be produced at low cost without reducing the productivity.
  • Crushers include, for example, jaw crushers, medium crushers include, for example, cutter mills and rakers, and crushers include, for example, roller mills, jet mills, hammer mills, pin mills, rotary mills, attritors, bead mills, atomizers, etc. It can be used, but is not limited to these. From the viewpoint of inexpensive production and versatility, jet mills, pin mills, rotary mills, atomizers, bead mills and the like are preferable.
  • a solvent having a boiling point of 130 ° C. or lower may be used at a mass ratio of 10% or less with respect to the entire treated powder, but in that it can be easily produced at low cost while reducing the environmental load. It is preferably carried out by dry mixing which does not require a solvent.
  • the present invention provides a composition containing the above-mentioned treated powder at a mass ratio of 0.01 to 99.9.
  • the composition of the present invention can be used as a composition for industrial use. For example, it can be blended with a printing or writing ink, a pencil lead, or the like in order to improve the color development, adhesion, and durability of the pigment. Further, it can be blended in paint from the viewpoint of preventing oxidation of pigments, improving water repellency, and improving dispersibility, and can also be blended in tires and paper. It can also be used as a lubricant for machines.
  • the composition of the present invention can also be used as a cosmetic or an external preparation.
  • the cosmetic or external preparation can be prepared in any form applicable to, for example, a desired site (eg, skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method.
  • Cosmetics or external preparations for skin, lips, eyebrows, nails include, for example, sunscreens, body powders, sunscreens such as sprays, foundations, primers, body colors, bronzer, face powders, manicures, teak colors, makeup bases, etc.
  • Makeup cosmetics such as concealers, lip color, lip liner, lip cosmetics such as lip sticks, eye makeup cosmetics such as eye liner, eye shadow, eyebrow, mascara, milky lotion, lotion, cream, gel, beauty liquid, etc. Leave-on cosmetics and face masks.
  • Examples of cosmetics or external preparations for hair include hair styling products, hair emulsions, hair treatments, hair conditioners, and hair lotions.
  • Examples of cosmetics or external preparations for the scalp include hair growth agents.
  • Preferred cosmetics include, for example, make-up makeup, eye makeup makeup, lip cosmetics, and leave-on cosmetics.
  • Preferred external preparations include, for example, ointments, creams, mousses and gels.
  • the composition of the present invention can be used as a cleaning agent composition.
  • the cleaning composition is not particularly limited as long as it is a cleaning composition containing a surfactant, and the effects of the present invention can be exhibited.
  • More preferable examples include face wash, body soap, soap, cleansing balm, cleansing oil and other skin wash, shampoo and other hair wash, dish wash wash, vegetable wash wash, machine wash wash and other cleansers.
  • Examples include the composition.
  • the crystals or treated powders of the present invention are preservatives such as caprylyl glycol, glyceryl caprylate, phenoxyethanol, chlorphenesin, pentylene glycol, hexylene glycol, methylparaben, and propylparaben, as long as these effects are not impaired.
  • Antioxidants such as tocopherol, vitamin C, BHT; chelating agents such as ethylenediamine tetraacetate; binders such as ethyl cellulose and hydroxypropyl cellulose; thickeners such as xanthan gum, carbomer, polyacrylate cloth polymer; dibutylethylhexanoylglutami Oil gelling agents such as de, dibutylelauroyl glutamid, dextrin palmitate, polyamide 3; moisturizers such as glycerin, 1,3-butylene glycol; polyoxyethylene or polysorbate emulsifiers, fatty acid polyglyceryl, sorbitan fatty acid ester, etc. Emulsifiers; can be blended with oils such as ester oils and hydrocarbon oils.
  • Particle size distribution and particle size measurement method A laser diffraction / scattering type particle size distribution measuring device (Partica LA-950 manufactured by HORIBA) was used, and the particle size distribution was measured using the volume cumulative value. Various particle diameters of the number-based distribution and the volume-based distribution were obtained by analyzing the measurement results using the software attached to the device. 20 mg of N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals are added to 5 g of isopropyl alcohol and exposed to ultrasonic waves for 30 minutes using an ultrasonic device with an output of 300 Watt. Crushed and dispersed.
  • this dispersion was added to 500 mL isopropyl alcohol according to the procedure of the apparatus, and a dispersion sample having an appropriate concentration was prepared while checking the transparency. While circulating this sample at a flow rate of 10 mL / min, ultrasonic waves were applied for 30 minutes to disperse it to primary particles, and after degassing, the particle size distribution and various particle diameters of N ⁇ -lauroyl lysine crystals in the sample were degassed. Asked.
  • the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal were crushed by stirring with a mixer for 2 minutes or more.
  • the bulk density of the obtained crystals was measured using a powder rheometer FT-4 (manufactured by Freeman Technology TM ). Specifically, a certain amount of N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals were measured in a holder, and then conditioning was performed according to the usage procedure.
  • the bulk density was measured from the volume after conditioning and the mass of the N ⁇ -lauroyl lysine crystal or the N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystal from the following formula.
  • Bulk density mass after conditioning / volume after conditioning (g / mL)
  • Beads made of partially stabilized zirconia (PSZ) (diameter 1.5 mm) were used as beads, and the filling rate of the beads was 70% (v / v) with respect to the volume.
  • PSD partially stabilized zirconia
  • the powder obtained after pulverization was dried and pulverized with a mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 1 shows the bulk density and various particle diameters of the obtained crystals.
  • Beads made of partially stabilized zirconia (PSZ) (diameter 1.5 mm) were used as beads, and the filling rate of the beads was 70% (v / v) with respect to the volume.
  • PSD partially stabilized zirconia
  • the powder obtained after pulverization was dried and pulverized with a high-speed mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 1 shows the bulk density and various particle diameters of the obtained crystals.
  • Table 1 summarizes the particle size and physical properties of the fine powder N ⁇ -lauroyl lysine crystals obtained in Comparative Examples 1-1 to 1-4.
  • Example 2-2 After dissolving 5.7 g of sodium hydroxide in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, heat to about 50 ° C., and then add 36.4 g of commercially available N ⁇ -lauroyl lysine crystals. It was melted at the same temperature. Then, a solution of N ⁇ -lauroyl lysine was applied to an aqueous hydrochloric acid solution (150 mL) having a concentration of 0.085 mol / L, which was continuously cooled to 0 ° C. or lower, for 25 minutes while maintaining the pH at 0.8 to 1.1. And dropped.
  • the pH was adjusted to 7.0 with sodium hydroxide, the precipitated crystals were filtered, and dried under reduced pressure to obtain 36.0 g of white crystals.
  • the obtained white crystals were dried and crushed with a high-speed mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 2-1 shows the bulk density and various particle diameters of the obtained crystals.
  • Example 2-3 Commercially available N epsilon - lauroyl lysine commercial N epsilon instead of crystal - octanoyl lysine crystals and N epsilon - lauroyl lysine crystalline 1: except for using a ratio of 1, N epsilon according to the method of Example 2-2 - Octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals (1: 1) were obtained. Table 2-2 shows the bulk density and various particle diameters of the obtained mixture.
  • Example 2-4 Commercially available N epsilon - lauroyl lysine commercial N epsilon instead of crystal - octanoyl lysine crystals and N epsilon - lauroyl lysine crystalline 1: except for using a ratio of 3, N epsilon according to the method of Example 2-2 - Octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals (1: 3) were obtained. Table 2-2 shows the bulk density and various particle diameters of the obtained mixture.
  • Example 2-5 Commercially available N epsilon - commercial instead of lauroyl lysine crystalline N epsilon - octanoyl lysine crystals and N epsilon - lauroyl lysine crystalline 1: except for using 9 ratio of, N epsilon according to the method of Example 2-2 - Octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals (1: 9) were obtained.
  • Table 2-2 shows the bulk density and various particle diameters of the obtained mixture.
  • Example 2-6 Commercially available N epsilon - lauroyl lysine commercial N epsilon instead of crystal - octanoyl lysine crystals and N epsilon - lauroyl lysine crystals 3: according to the method of Example 2-2 except for using a ratio of 1 N epsilon - octa A mixed crystal of noyl lysine and N ⁇ -lauroyl lysine (3: 1) was obtained. The bulk density and various particle diameters of the obtained mixture are shown in Table 2-2.
  • the pH was adjusted to 7.0 with hydrochloric acid, and the precipitated crystals were filtered and dried to obtain 35.0 g of white crystals.
  • the obtained white crystals were dried and crushed with a high-speed mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 2-1 shows the bulk density and various particle diameters of the obtained crystals.
  • the pH was adjusted to 7.0 with sodium hydroxide, the precipitated crystals were filtered, and dried under reduced pressure to obtain 35.8 g of white crystals.
  • the obtained white crystals were dried and crushed with a high-speed mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 2-1 shows the bulk density and various particle diameters of the obtained crystals.
  • the pH was adjusted to 7.0 with sodium hydroxide, the precipitated crystals were filtered, and dried under reduced pressure to obtain 34.9 g of white crystals.
  • the obtained white crystals were dried and crushed with a high-speed mixer to obtain the desired fine powder N ⁇ -lauroyl lysine crystals.
  • Table 2-1 shows the bulk density and various particle diameters of the obtained crystals.
  • the particle size and physical properties of the lysine and N ⁇ -lauroyl lysine mixed crystals are shown in Tables 2-1 and 2-2.
  • Example 3 Various powders were treated by the ratios and methods shown in Tables 5-1 to 5-4, and the water repellency and oil repellency of the treated powders were evaluated. The evaluation results of water repellency are shown in FIGS. 1 to 19, and the evaluation results of oil repellency are shown in FIGS. 20 to 24.
  • Oils similar to the composition of sebum were uniformly mixed at the ratio shown in Table 4 to prepare a liquid pseudo-sebum. 5 g of this pseudo-sebum was measured in a vial, and 30 mg of untreated powder or various treated powders was added to the surface of the liquid sebum within 2 seconds from a height of 3 cm. After allowing to stand for a certain period of time after the addition, the amount of powder floating on the liquid sebum was grasped visually and by image analysis by ImageJ.
  • Powder processing method by simple mixing Various powders and N ⁇ -lauroyl lysine crystals or N ⁇ - octanoyl lysine and N ⁇ -lauroyl lysine mixed crystals were added to a Henschel mixer (FM 10C / I manufactured by Nippon Coke Industries, Ltd.) and mixed by stirring at room temperature. Further, when the temperature inside the mixer gradually increased due to the mixing operation, the maximum temperature inside the mixer was controlled to be lower than 80 ° C.
  • a Henschel mixer FM 10C / I manufactured by Nippon Coke Industries, Ltd.
  • Powder treatment method by wet treatment method 5 g of N ⁇ -lauroyl lysine was dissolved in a 1.5% alkaline aqueous solution, 100 g of various powders was added to the obtained solution and suspended (powder content 20% by weight), and the mixture was stirred for 30 minutes. Then, hydrochloric acid was added to neutralize the pH to 7.0, and stirring was continued for another 30 minutes. Then, after repeating filtration and washing with water, it was dried at 80 ° C. for 30 hours. By crushing this dried product, various powders on which a N ⁇ -lauroyl lysine film was formed were obtained.
  • Powder processing method by mixing with a compound processing machine Using a hybridization system NHS-1-2L (manufactured by Nara Machinery Co., Ltd.), 5 g of N ⁇ -lauroyl lysine crystals having a median diameter of 20 ⁇ m was added to 200 g of powder, and mixed treatment was performed at a rotor peripheral speed of 100 m / s for 3 minutes. went.
  • NHS-1-2L manufactured by Nara Machinery Co., Ltd.
  • Example 2-1 Microscopic observation of the processed state: After depositing gold and platinum on the crystals obtained in Example 2-1 the crystals were observed with a scanning electron microscope (JEOL JCM-6000 PLUS), and an image of the surface state was recorded. The recorded image is shown in FIG.
  • Example 3-24 covers the treated powder surface epsilon - octanoyl lysine and N epsilon - calculation of the particle size of lauroyl lysine mixed crystal:
  • the treated powder of Example 3-24 was deposited with gold and platinum, and then observed with a scanning electron microscope (JEOL JCM-6000 PLUS). From the obtained image, the particle diameters of 500 plate-like crystals adhering to the powder surface were measured. Of all the crystals, the number of plate-like crystals with a particle size of 1.8 ⁇ m or less was 461 (92.2%), and the number of plate-like crystals with a particle size of 2.8 ⁇ m or less was 489 (97.8%). It was.
  • Example 4 The various powders were mixed at the ratios shown in Table 6 by the powder treatment method by simple mixing.
  • the obtained mixed powder had good water repellency and oil repellency, had a soft feel, and had an excellent adhesion to the skin.
  • Example 5-1 Various powders were mixed at the ratios shown in Table 7 by a powder treatment method by simple mixing.
  • the obtained mixed powder had good water repellency and oil repellency, had a soft feel, and had an excellent adhesion to the skin.
  • Example 6 The various powders were mixed at the ratios shown in Table 10 for 10 minutes using an impact type crusher (atomizer manufactured by Dalton Corporation). The obtained mixed powder had good water repellency and oil repellency, and had a soft feel. Furthermore, the uniform color development of the pigment was also excellent.
  • Example 7 Various powders were mixed at the ratios shown in Table 11 by a powder treatment method by simple mixing.
  • the water repellency and oil repellency of the obtained mixed powder were calculated from the following, respectively.
  • Water repellency 100 x (amount of powder floating on the solvent after 60 minutes / amount of powder floating on the solvent at 0 minutes)
  • Oil repellency 100 x (amount of powder floating on the solvent after 5 minutes / 0 minutes)
  • evaluation was performed according to the following evaluation criteria, and the water repellency and oil repellency of the mixed powder were compared. The results are shown in Table 11.
  • Example 8-1 and Comparative Example 8-1) A cleaning composition was prepared using the components shown in Table 12 as follows. Component A was dispersed in component B at room temperature. Further, component C was added and stirred at room temperature to prepare a uniform solution. Further, component D was added, and the mixture was stirred using a homodisper until uniform. After adding component E to adjust the pH to 5.4, component F was added and mixed uniformly to obtain a cleaning composition. The resulting cleaning composition was heated to a cycle temperature of -5 ° C to 40 ° C (keeping the temperature inside the chamber at -5 ° C for 12 hours and increasing from -5 ° C to 40 ° C over 3 hours to 40 ° C for 12 hours. After keeping, the mixture was further cooled from 40 ° C.
  • Example 8-1 maintained the same pearl effect as immediately after preparation, whereas the composition of Comparative Example 8-1 could hardly maintain the pearl effect.
  • all the panelists were found to be of Example 8-1. It was evaluated that the composition had a higher conditioning effect on hair and skin as compared with the composition of Comparative Example 8-1.
  • Example 9-1 and Comparative Example 9-1) A cleaning composition was prepared using the components shown in Table 13 as follows. Component A was dispersed in component B at room temperature. Further, the component E was stirred and dissolved at room temperature. Further, component C and component D were each stirred and dissolved at 60 ° C. Component C and component D were added to component B in which component A was dispersed, and the mixture was stirred and mixed at 60 ° C. Further, component E was added, stirred and mixed, cooled to 50 ° C., and component F was added. The mixture was cooled to room temperature to obtain a cleaning composition.
  • Example 9-1 As a result of evaluating the effect of reducing the slimy feeling of the surfactant when using the cleaning composition of Example 9-1 and Comparative Example 9-1 by four specialized panelists, all the panelists were evaluated as Example 9-1. Was evaluated to have a higher effect of reducing the slimy feeling of the surfactant at the time of use as compared with the composition of Comparative Example 9-1.
  • Example 10-1 and Comparative Example 10-1 Lip cosmetics were prepared using the ingredients shown in Table 15 as follows. Component A was heated and dissolved at 105 ⁇ 5 ° C., component B was added to component A and dissolved by heating at 90 ° C. Further, component C was added, heated and mixed at 90 ° C., dispersed in three rolls, and then component D was added. After adding component E and heating and mixing at 90 ° C., defoaming was performed. It was filled in a sink at a filling temperature of 90 ° C., cooled, and then loaded into a container. The lip cosmetic of Example 10-1 had better color development, less color unevenness, and better color uniformity than Comparative Example 10-1. Furthermore, there was no sweating and the stability was good.
  • Example 11-1 and Comparative Example 11-1) A leave-on cosmetic was prepared using the ingredients shown in Table 16 as follows. After each of component A and component B was heated to 80 ° C. to dissolve them, component A was added to component B with stirring. It was emulsified with a homomixer and cooled to room temperature (3000 rpm, 3 minutes, 80 ° C.) to obtain a leave-on cosmetic.
  • the leave-on cosmetics of Example 11-1 had better stability and antiseptic properties than Comparative Example 11-1. Furthermore, it has an excellent moist feeling after application, and the gloss is further improved by application.
  • Example 12-1 and Comparative Example 12-1 An eye makeup cosmetic was prepared using the ingredients shown in Table 17 as follows. After mixing the A component for 10 minutes, the B component was added to the A component and mixed for another 20 minutes. The C component was mixed for 10 minutes using a mixer (FM 10C / I manufactured by Nippon Coke Industries, Ltd.), added to the mixture of A component + B component, and further mixed for 5 minutes. The obtained mixture was filled in a container and compressed using a press to obtain the desired eye makeup cosmetic. As a result of evaluating the pearly feeling, gloss, gloss and color development after application of the eye makeup cosmetics of Example 12-1 and Comparative Example 12-1 by four specialized panelists, all the panelists were evaluated as Example 12-1. The eye make-up cosmetics of No.
  • Example 12-1 were evaluated to have higher pearly feeling, gloss, gloss and color development after application than the eye make-up cosmetics of Comparative Example 12-1. Since the eye makeup cosmetic of Example 12-1 can be produced using a small amount of oil, it is excellent in usability. In Example 12-1, the gloss of the pearl powder and the colored pearl pigment did not decrease, but rather the gloss was improved.
  • Example 13-1 and Comparative Example 13-1) A make-up cosmetic was prepared using the ingredients shown in Table 18 as follows. After mixing the B component for 10 minutes, the C component was added to the B component, and the B component was dispersed in the C component using a disperser of the disperser. Component A was gradually added to component B + component C, and the mixture was uniformly emulsified using a homomixer. After the completion of emulsification, component D was added and further mixed, and the mixture was cooled to room temperature to obtain the desired make-up cosmetics. Compared with Comparative Example 13-1, the make-up makeup of Example 13-1 was excellent in emulsification stability, could improve gloss after application, and could improve pigment unevenness. Further, it has good makeup retention and antiseptic properties, and has an excellent moist feeling after application.
  • Example 14 A foundation was prepared using the ingredients shown in Table 19 as follows.
  • the B component was uniformly mixed. After mixing the component A with a mixer for 1 minute, the component B was added to the component A and mixed for another 30 seconds.
  • 13 g of the obtained dispersion was measured in a container, and while pressing, water / ethanol as a dispersion solvent was sufficiently absorbed from above using tissue paper.
  • the composition compressed in the container was dried at 80 ° C. overnight to obtain the desired foundation.
  • the foundation of Example 14 had an excellent adhesion after application and was excellent in a natural finish. Furthermore, the product itself had good moldability and a beautiful color. Furthermore, the causes of makeup disintegration such as unevenness, shine, wrinkles, dullness, and disappearance due to changes in the makeup film over time were reduced.
  • Example 15 A pencil composition was prepared using the components shown in Table 20 as follows.
  • the composition A component in Table 20 was mixed in a mixer (FM 10C / I manufactured by Nippon Coke Industries Co., Ltd.) for 5 minutes, then the B component was added to the A component and mixed for another 10 minutes.
  • Component C was dissolved at 100 ° C., added to component A + component B, and mixed for 10 minutes.
  • Component D was added to the obtained mixture, kneaded with three rolls, filled in a container while heating, and fired and solidified.
  • the pencil obtained in Example 15 had a core that was hard to break and had a high gloss. Furthermore, it was excellent in color development.

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KR1020227002566A KR20220027995A (ko) 2019-06-27 2020-06-23 Nε-장쇄 아실 라이신 결정의 제조 방법 및 그 결정을 함유하는 조성물
CN202080046815.7A CN114026062B (zh) 2019-06-27 2020-06-23 Nε-长链酰基赖氨酸晶体的制造方法及包含该晶体的组合物
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US17/646,027 US12221403B2 (en) 2019-06-27 2021-12-27 Nε-long chain acyl lysine crystal production method and composition containing said crystals
US19/005,604 US20250136541A1 (en) 2019-06-27 2024-12-30 Nepsilon-long chain acyl lysine crystal production method and composition containing said crystals
JP2025028747A JP2025071320A (ja) 2019-06-27 2025-02-26 Ｎε－長鎖アシルリジン結晶の製造方法及びその結晶を含有する組成物

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