Method for producing Nε-long-chain acyl lysine crystals and composition containing the crystals

Abstract

An unground Nε-long chain acylidine crystal production method that includes: preparing a solution having at least one type of Nε-long chain acylidine dissolved in an acidic or basic solvent including water and / or one type selected from water-soluble organic solvents; dipping the solution into an acidic solution having a pH of at least 0.2 and less than 2.0, at a temperature of no more than 20°C; and crystallizing Nε-long chain acylidine crystals.

Description

[Technical field]

[0001] The present invention is ε The present invention relates to a method for producing long-chain acyl lysine crystals and a composition containing the crystals. [Background technology]

[0002] Powder materials that can simultaneously exhibit water- and oil-repellent properties are important in cosmetics and various industrial applications, but it has been considered difficult to obtain powder materials that can simultaneously exhibit both functions at low cost and with low environmental impact. For example, inorganic powders such as talc, mica, sericite, titanium oxide, zinc oxide, iron oxide, aluminum oxide, barium sulfate, boron nitride, silica, and synthetic mica (synthetic mica), and organic powders such as starch, cellulose, fatty acid salts, and bamboo and wood powder are used for the purpose of providing lubricity, improving hiding power, coloring, and absorbing and scattering light. Generally, highly polar functional groups are present on the powder surface, so the powder is easily wetted by highly polar solvents such as water. However, when such powders are used in cosmetics, they become wetted by sweat, etc., which causes dulling and discoloration of the makeup. In addition, they are washed away by sweat, causing makeup to break down. In industrial applications, paints and inks containing these powders have problems such as getting wet and washed away by water or rain, and not exhibiting sufficient lubricity when used as a lubricant for machines, etc. In addition, since general powders do not have good oil repellency, when they are used in cosmetics, the powder surface becomes wet with sebum, causing discoloration and dullness of cosmetics such as foundation (JP Patent Publication 2010-242026). In addition, absorbing oil causes makeup to come off. In industrial applications, when used as a lubricant, there is a problem that it absorbs machine oil and creates a highly viscous mud-like stain.

[0003] In order to solve these problems, a technology has been developed to treat the surface of a powder with fluorine-containing molecules that are insoluble in both water and oil. Powders that have been surface-treated with fluorine-containing molecules exhibit excellent water- and oil-repellency, but because they contain perfluorinated compounds and low-molecular-weight fluorine compounds as impurities, problems of accumulation in the environment and human body and toxicity have been pointed out. In addition, powders that have been surface-treated with fluorine-containing molecules have the problem of poor compatibility with the skin, and poor makeup wear and feel. Furthermore, the oil-repellency of powders that have been surface-treated with fluorine-containing molecules is extremely reduced in the presence of water, so there is a problem that they become wet with sweat and sebum when used in cosmetics.

[0004] N is an amino acid-derived raw material that does not disperse in water or dissolve in oil, and does not accumulate in the environment. ε -Lauroyl lysine crystals are attached to the powder surface, and the powder is N ε -Lauroyl lysine crystal function is being investigated. ε -It is important that the powder is completely covered with lauroyl lysine crystals. However, while the 90% particle size D90 (number-based distribution) of ordinary powders is often 20 μm or less, ε The 90% particle size D90 (number-based distribution) of lauroyl lysine crystals (Amihope LL, manufactured by Ajinomoto Co., Inc.) is 15.7 μm, and the median and average particle sizes of the volume-based distribution are 14.3 μm and 15.3 μm, respectively. ε The median diameter of the volume-based distribution of 1-octanoyl lysine crystals (Ajinomoto Co., Inc.'s "Amihope" OL) is 20 μm. These crystals contain almost no crystals with small particle sizes, so according to the DLVO theory, ordinary powders can be simply mixed to produce N ε -Lauroyl Lysine Crystal or N ε It is difficult to stably coat the powder with N-octanoyl lysine crystals. ε -Simply mix with lauroyl lysine crystals and apply N to the powder surface. ε A simple dry treatment method using N-lauroyl lysine crystals is known (WO 2011 / 025252). However, this method ε-The coverage rate of lauroyl lysine crystals was low, and as a result, sufficiently excellent water and oil repellency could not be achieved.

[0005] Also, N ε -In order to improve the coverage of lauroyl lysine crystals, N ε -Make a fine powder of lauroyl lysine crystals, mix this fine powder with the powder, and apply N ε A method of treating with N-lauroyl lysine crystals has been considered. For example, a wet grinding method (JP Patent Publication No. 09-323914, Patent No. 4826049) has been proposed. ε It is known that N-lauroyl lysine crystals are finely divided and mixed with inorganic powders. However, this method does not produce fine powders of N ε -To obtain lauroyl lysine crystals, it is necessary to grind it more than 20 times, and it is difficult to obtain fine powder N on an industrial large scale. ε It was difficult to produce crystalline N-lauroyl lysine. Even after grinding more than 20 times, the N ε The average particle size (volume-based distribution) of lauroyl lysine crystals is 3.4 μm, and the crystals are mixed with inorganic powder to dissolve the inorganic powder in N ε - Even when treated with lauroyl lysine crystals, it was not possible to achieve sufficiently excellent water repellency and oil repellency. Furthermore, this method requires the use of a large amount of organic solvents, which makes it difficult to produce at low cost, and is also environmentally hazardous.

[0006] A simpler way to ε -To obtain fine crystals of lauroyl lysine, add N ε -By dropping a base solution of lauroyl lysine into the crystallization, N ε It has been reported that N-lauroyl lysine crystals have been obtained (JP Patent Publication 08-337519). By mixing this crystal with a powder, the adhesion of the mixed powder to the skin and the feeling of use of the mixed powder can be improved. However, it was found that the water repellency and oil repellency of the mixed powder obtained by this method were not improved, and conversely, the dispersibility of the powder in water and oil increased. Furthermore, the N-lauroyl lysine crystals obtained by this method were not improved, and ... εIt has been reported that when the crystals of lauroyl lysine were measured using a laser diffraction / scattering type particle size distribution measuring device, the average particle size (volume-based distribution) was 18 μm (Comparative Production Example 2 in Japanese Patent No. 4826049). ε The reason why the water and oil repellency of powder cannot be improved even when lauroyl lysine crystals are used is that the mixed N ε -The particle size of the lauroyl lysine crystals is large. In the case of plate-shaped particles, the projected diameter measured by a microscope and the average particle size measured by a light scattering method may differ due to the measurement principle.

[0007] In addition, by crystallizing at pH 7.0, the average particle size (volume-based distribution) of N ε However, the N-lauroyl lysine crystals obtained by this method are not ε -Even when the powder was treated with lauroyl lysine crystals, it was not possible to achieve sufficiently excellent water and oil repellency. In addition, N is applied to the powder surface by wet processing. ε It is also known that lauroyl lysine can be attached (JP Patent Publication No. 4-63844, JP Patent Publication No. 61-10503). ε -Since lauroyl lysine itself is poorly soluble, it is dissolved in a strong alkali, strong acid or solvent, and the solution is gradually added to an acid or alkaline powder dispersion to form N on the powder surface in the powder dispersion. ε By filtering and drying the dispersion after crystallization, N-lauroyl lysine can be obtained on the surface. ε -Lauroyl lysine can be attached to the powder. However, this method is not suitable for the inorganic powder. ε Although a certain degree of water- and oil-repellency can be obtained even when treated with -lauroyl lysine, the degree is not sufficient. In addition, this method requires the use of a large amount of organic solvent and the repeated dissolving and drying steps, which makes it difficult to produce at low cost. Furthermore, in the case of powders such as silica and starch that dissolve in solvents, acids, and alkalis, the powder surface must be treated with N ε -Lauroyl Lysine Crystal or N εAnother problem is that it cannot be processed with -octanoyllysine crystals.

[0008] In addition, we use a special compounding machine to mix the powder and N ε -By strongly colliding the lauroyl lysine crystals, the surface of the powder is heated with N ε - It is also possible to treat with lauroyl lysine crystals. However, this method has the problem that the amount of powder that can be treated at one time is small, and it cannot be produced at low cost. In addition, there is also the problem that brittle powders such as silica are crushed, and the functions specific to the powder are reduced. Furthermore, there is also the problem that it is not possible to achieve sufficiently excellent water repellency and oil repellency. As described above, there was a need for a technology that could impart water- and oil-repellent properties to powder while improving the powder's feel and compatibility with the skin, and that could be produced inexpensively. Summary of the Invention

[0009] An object of the present invention is to provide a technology that can impart water-repellent and oil-repellent properties to powder while improving the soft feel of the powder, and that can be produced inexpensively.

[0010] As a result of intensive research in view of the above problems, the present inventors have discovered that a specific method can be used to ε The present invention was completed based on the discovery that the above problems can be solved by producing a long-chain acyl lysine crystal. [1] N with 90% particle size D90 of 2.8μm or less based on number distribution ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. [2] The median diameter or average particle diameter of the volume-based distribution is 2.8 μm or less. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. [3] Bulk density is 0.34 g / mL or less ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. [4] One or more water-soluble organic solvents and / or an acidic or basic solvent containing water are mixed with one or more N ε -Prepare a solution in which long-chain acyl lysine is dissolved, dropwise add said solution to an acidic solution having a pH of 0.2 or more and less than 2.0 at a temperature of 20°C or less, and ε -Non-milled N including crystallizing long-chain acyl lysine crystals ε - A method for producing long-chain acyl lysine crystals. [5] [4] The N according to any one of [1] to [3], which is obtained by the production method of [4] ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. [6] N in the crystal ε [1] to [5], which contains octanoyl lysine at a mass fraction of 99% or less. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. [7] [1] to [3], [5], or [6] according to any one of the above items ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -A composition comprising lauroyl lysine mixed crystals in an amount of 0.01 to 99.9% by mass. [8] [1] to [3], [5], or [6] according to any one of the above items ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε A composition for industrial use comprising lauroyl lysine mixed crystals in an amount of 0.01 to 99.9% by mass. [9] [1] to [3], [5], or [6] according to any one of the above items ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A cosmetic or topical preparation containing lauroyl lysine mixed crystals in a mass ratio of 0.01 to 99.9.

[10] [1] to [3], [5], or [6] according to any one of the above items ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε A cleansing composition comprising lauroyl lysine mixed crystals in an amount of 0.01 to 99.9% by mass.

[11] Powder and N according to any one of [1] to [3], [5] and [6]. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A processed powder obtained by mixing lauroyl lysine mixed crystals.

[12] The treated powder according to

[11] , wherein the powder includes a crystalline or amorphous powder of a resin powder, a silicon-containing powder, a metal oxide, a carbon-containing powder, a fluorine-containing powder, a metal salt, a boron-containing powder, or a composite powder.

[13] N coating on the surface of the treated powder ε - Lauroyl lysine crystals with a particle size of 1.8 μm or less ε -The treated powder according to

[11] or

[12] , wherein the proportion of lauroyl lysine crystals is 90% or more.

[14] N coating on the surface of the treated powder ε -octanoyl lysine and N ε The treated powder according to

[11] or

[12] , wherein the proportion of crystals having a particle size of 2.8 μm or less among the lauroyl lysine mixed crystals is 90% or more.

[15] The powder is a powder of N according to any one of [1] to [3], [5] and [6]. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε-Lauroyl lysine mixed crystals are mixed at 5 mass ratios, and 40% or more of the powder surface area is N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The method for preparing the treated powder according to any one of

[11] to

[14] , comprising coating the powder with lauroyl lysine mixed crystals.

[16] The method according to

[15] , wherein the mixing step comprises mixing by dry mixing without the need for a solvent.

[17] The method according to

[15] or

[16] , wherein the mixing step comprises mixing for 60 minutes or less using a mixer.

[18] The treated powder according to any one of

[11] to

[14] , which has water repellency.

[19] The treated powder according to any one of

[11] to

[14] and

[18] , which has oil repellency.

[20] The treated powder according to any one of

[11] to

[14] ,

[18] and

[19] , which has a soft focus effect. [twenty one] A composition comprising the treated powder according to any one of

[11] to

[14] and

[18] to

[20] in an amount of 0.01 to 99.99 mass %. [twenty two] The composition according to

[21] , which is a composition for industrial use, a cosmetic, an external preparation or a cleansing agent. [Brief description of the drawings]

[0011] [Figure 1] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-23, Example 3-1, Comparative Example 3-9, Comparative Example 3-16, Comparative Example 3-20, Comparative Example 3-1, and Comparative Example 3-21. [Diagram 2] FIG. 13 is a diagram showing the evaluation results of water repellency for Example 3-2, Comparative Example 3-10, Comparative Example 3-17, and Comparative Example 3-2. [Diagram 3] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-24, Example 3-3, and Comparative Example 3-3. [Figure 4] FIG. 13 is a diagram showing the evaluation results of water repellency for Examples 3-4 and 3-5. [Diagram 5] FIG. 13 is a diagram showing the evaluation results of water repellency for Examples 3-6, 3-7, and 3-8. [Figure 6] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-25 and Example 3-9. [Figure 7] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-26 and Example 3-10. [Figure 8] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-27, Example 3-11, and Comparative Example 3-13. [Figure 9] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-28, Example 3-12, Comparative Example 3-11, Comparative Example 3-19, and Comparative Example 3-5. [Figure 10] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-29, Example 3-13, Comparative Example 3-12, Comparative Example 3-18, Comparative Example 3-4, and Comparative Example 3-38. [Figure 11] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-36 and Comparative Example 3-14. [Figure 12] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-30, Example 3-15, and Comparative Example 3-6. [Figure 13] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-31, Example 3-16, Comparative Example 3-15, and Comparative Example 3-7. [Figure 14] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-32 and Example 3-17. [Figure 15] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-33 and Example 3-18. [Figure 16] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-34, Example 3-19, and Example 3-20. [Figure 17] FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-35, Example 3-21, and Comparative Example 3-8. [Figure 18]FIG. 13 is a diagram showing the evaluation results of water repellency for Comparative Example 3-37. [Figure 19] FIG. 1 is a diagram showing the evaluation results of water repellency for Comparative Example 5-1, Comparative Example 5-2, and Example 5-1. [Figure 20] FIG. 13 is a diagram showing the evaluation results of oil repellency for Comparative Example 3-23, Example 3-1, Comparative Example 3-9, Comparative Example 3-15, Comparative Example 3-1, and Comparative Example 3-20. [Figure 21] FIG. 13 is a diagram showing the evaluation results of oil repellency for Comparative Example 3-24, Example 3-3, Comparative Example 3-39, and Comparative Example 3-22. [Figure 22] FIG. 13 is a diagram showing the evaluation results of oil repellency for Comparative Example 3-35, Example 3-21, and Comparative Example 3-8. [Diagram 23] FIG. 13 is a diagram showing the evaluation results of oil repellency for Comparative Example 3-29, Example 3-15, and Comparative Example 3-14. [Figure 24] FIG. 1 is a diagram showing the evaluation results of oil repellency for Comparative Example 5-1, Comparative Example 5-2, and Example 5-1. [Diagram 25] 1 is an SEM image of the crystals of Example 2-1. [Figure 26] FIG. 13 is a diagram showing the evaluation results of water repellency and oil repellency for Examples 3-22 to 3-26. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] N of the present invention ε The method for producing long-chain acyl lysine crystals comprises adding one or more N-type acyl groups to an acidic or basic solvent containing one or more water-soluble organic solvents and / or water. ε -Prepare a solution in which long-chain acyl lysine is dissolved, dropwise add said solution to an acidic solution having a pH of 0.2 or more and less than 2.0 at a temperature of 20°C or less, and ε -Long-chain acyl lysine crystals can be obtained without pulverization by a method including crystallization. ε -Long chain acyl lysine solution is N εIt may be obtained by dissolving crystals of long-chain acyl lysine, or it is also possible to use a reaction solution obtained by reacting a fatty acid with lysine without crystallizing it. N ε The long-chain acyl group of the long-chain acyl lysine is a saturated or unsaturated fatty acyl group having 8 to 22 carbon atoms, such as octanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, octyldodecyl, oleyl, behenyl, coconut oil fatty acyl, palm kernel oil fatty acyl, and beef tallow fatty acyl. Of these, lauroyl and octanoyl are preferred in that they are widely available. Examples of the water-soluble organic solvent include acetone, methanol, ethanol, propanol, butanol, isopropanol, etc., and acetone, methanol, isopropanol, and butanol are preferred. These water-soluble organic solvents may be used alone or in combination of two or more. When a water-soluble organic solvent and water are used in combination, there is no particular limitation on the ratio thereof, and the weight ratio of the water-soluble organic solvent to water is in the range of 0 / 100 to 100 / 0, but is preferably 55 / 45 to 70 / 30. When the weight ratio of the two is less than 55 / 45 or more than 70 / 30, N ε -The solubility of long-chain acyl lysine decreases, and N ε -A large amount of solvent is required to dissolve the long-chain acyl lysine, which reduces the efficiency. 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 pyrrolidone carboxylic acid, with sulfuric acid and hydrochloric acid being preferred. The base used in the basic solvent may be either an organic base or an inorganic base, and examples thereof include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, ammonia, triethylamine, triethanolamine, monoethanolamine, pyridine, arginine, and lysine, with sodium hydroxide and potassium hydroxide being preferred. The amount of acid or base in the acidic or basic solvent is not particularly limited. ε-It is sufficient as long as the long-chain acyl lysine can be dissolved. The temperature during crystallization is not particularly limited as long as it is 20° C. or less, but in terms of obtaining crystals with a small median size and / or average particle size and / or 90% particle size D90 (number-based distribution), it is preferably 15° C. or less, more preferably 10° C. or less, and particularly preferably 8° C. or less. The lower limit of the temperature during crystallization may be any temperature as long as it is equal to or higher than the freezing point of the solvent. The acidic solution used for crystallization can be prepared using the above-mentioned acids. 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 produced crystals can be collected and dried by a commonly used method. The N thus obtained ε The -long-chain acyl lysine crystals function as a stable pearling agent in a cleansing composition, and furthermore, when the skin or hair is washed with a cleansing composition containing such crystals, the conditioning effect on the hair or skin is improved. Furthermore, when the crystals are contained in a cleansing composition, the slimy feeling during washing with the cleansing agent can be suppressed. Furthermore, when the crystals are used in a milky lotion, the moist feeling and glossiness of the lotion can be improved. Furthermore, by treating a powder with the crystals, the powder can be endowed with water-repellent and oil-repellent functions while improving the softness of the powder and the glossiness during application. The crystals are preferably N ε -Lauroyl Lysine Crystals, or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals are N ε -octanoyl lysine and N ε -lauroyl lysine may be a mixture of single crystals of each of them, ε -octanoyl lysine and N ε -lauroyl lysine. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals εIt is preferable that the composition contains N-octanoyl lysine at a mass ratio of 99% or less. ε The content of -octanoyllysine is more preferably 5 to 75%, further preferably 15 to 45%, and most preferably 20 to 30%.

[0013] N of the present invention ε -Lauroyl Lysine Crystals, and N ε -octanoyl lysine and N ε The N-lauroyl lysine mixed crystals have a 90% particle size D90 of 2.8 μm or less in the number-based distribution. The crystals of the present invention function as a stable pearling agent in a cleansing composition, and when the skin or hair is washed with a cleansing composition containing such crystals, the 90% particle size D90 of N-lauroyl lysine mixed crystals is 3 μm or more. ε -Compared to lauroyl lysine crystals, the conditioning effect on hair and skin is improved. In addition, when the crystals of the present invention are contained in a cleansing composition, they can suppress the slimy feeling of the cleansing agent when washing. In addition, when the crystals of the present invention are used in an emulsion, they can improve the moist feeling and gloss of the emulsion. In addition, by treating a powder with the crystals of the present invention, it is possible to impart water repellency and oil repellency to the powder while improving the softness of the powder and the gloss when applied. The 90% particle size D90 is preferably from 0.01 to 2.8 μm, more preferably from 0.05 to 1 μm, and even more preferably from 0.1 to 0.7 μm. N of the present invention ε -Lauroyl Lysine Crystals, and N ε -octanoyl lysine and N ε The -lauroyl lysine mixed crystals further have a median size or average particle size of volume-based distribution of 2.8 μm or less. The median size or average particle size is preferably 0.01 to 2.8 μm, more preferably 0.05 to 2.0 μm, and even more preferably 0.07 to 1.5 μm.

[0014] In another embodiment, the present invention ε -Lauroyl Lysine Crystals, and N ε -octanoyl lysine and N εThe bulk density of the N-lauroyl lysine mixed crystal is 0.34 g / mL or less. The crystal of the present invention functions as a stable pearling agent in a cleansing composition, and when the skin or hair is washed with a cleansing composition containing such crystal, the bulk density of the N-lauroyl lysine mixed crystal is 0.35 g / mL or more. ε -Compared to lauroyl lysine crystals, the conditioning effect on hair and skin is improved. In addition, when the crystals of the present invention are contained in a cleansing composition, they can suppress the slimy feeling of the cleansing agent when washing. In addition, when the crystals of the present invention are used in an emulsion, they can improve the moist feeling and gloss of the emulsion. In addition, by treating a powder with the crystals of the present invention, it is possible to impart water repellency and oil repellency to the powder while improving the softness of the powder and the gloss when applied. The bulk density is preferably 0.01 to 0.32 g / mL, more preferably 0.05 to 0.30 g / mL, and further preferably 0.1 to 0.25 g / mL.

[0015] N of the present invention ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The median size, average particle size, and 90% particle size D90 of the lauroyl lysine mixed crystals can be determined by measuring the particle size distribution based on the number or volume using a laser diffraction / scattering type particle size distribution measuring device. The median size means the particle size at the point where the distribution curve of the cumulative % of the passing portion intersects with the horizontal axis of 50%, and the 90% particle size D90 means the particle size at the point where the distribution curve of the cumulative % of the passing portion intersects with the horizontal axis of 90%. The average particle size means the arithmetic mean particle size of the distribution. The "number-based distribution" refers to a particle size distribution in which the number of particles is counted and the calculation is based on the number when calculating the frequency of each particle size in the particle size distribution, and the "volume-based distribution" refers to a particle size distribution in which the volume of particles assumed to be spherical is counted and the calculation is based on the value when calculating the frequency of each particle size in the particle size distribution.

[0016] The present invention relates to the above-mentioned ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N εThe present invention provides a composition containing 0.01 to 99.9% by mass of lauroyl lysine mixed crystals. The composition of the present invention can be used as a composition for industrial use. For example, it can be blended into ink for printing or writing, pencil lead, etc., in order to improve the color development, adhesion, and durability of pigments. Furthermore, it can be blended into paints from the viewpoint of preventing oxidation of pigments, improving water repellency, and improving dispersibility, and it can also be blended into 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 topical agent. The cosmetic or topical agent can be prepared in any form that can be applied to a desired site (e.g., skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method. Examples of the cosmetic or topical agent for the skin, lips, eyelashes, and nails include sunscreens such as sunscreens, body powders, and sprays; makeup cosmetics such as foundations, primers, body colors, bronzers, face powders, nail polishes, cheek colors, makeup bases, and concealers; lip cosmetics such as lip colors, lip liners, and lipsticks; eye makeup cosmetics such as eyeliners, eye shadows, eyebrows, and mascaras; leave-on cosmetics such as emulsions, lotions, creams, gels, and serums; and face masks. Examples of the cosmetic or topical agent for hair include hair styling agents, hair emulsions, hair treatments, hair conditioners, and hair lotions. Examples of the cosmetic or topical agent for the scalp include hair growth agents. Preferable cosmetic preparations include, for example, makeup cosmetic preparations, eye make-up cosmetic preparations, lip cosmetic preparations, and leave-on cosmetic preparations. Preferable external preparations include, for example, ointments, creams, mousses, and gels. The composition of the present invention can be used as a cleaning 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 achieved. More preferred examples include cleaning compositions such as face wash, body soap, soap, cleansing balm, cleansing oil, and other skin cleaning agents, shampoo, and other hair cleaning agents, dishwashing detergents, vegetable washing detergents, and machine washing detergents.

[0017] The treated powder of the present invention is a powder and the above-mentioned N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The powder is not particularly limited as long as it is used for industrial purposes or cosmetics (pigments, coloring matter, resins, pearls), and examples thereof include resin powders such as nylon beads, silicone beads, and polyethylene beads; Metal oxides such as 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 dioxide, pigment grade titanium dioxide, zirconium oxide, aluminum oxide, cerium oxide, fine particle titanium dioxide, ultrafine particle titanium dioxide, fine particle zinc oxide, fine particle iron oxide; Silicates (Al / Ca / Na silicate, Na / Mg silicate, sericite, mica, talc, kaolin, bentonite, aluminum silicate, magnesium silicate, cubic sodium aluminosilicate, silicon carbide, silicon oxides such as hydrous silica and anhydrous silicic acid (foliated silica, nonporous silica, porous silica, semiporous silica, etc.); Nylon powder, metallic fatty acid soaps such as magnesium myristate, cellulose, cellulose particles, starch, flour, wood powder, carbon black, black smoke, ultramarine, Prussian blue, carmine, and other carbon-containing powders; Metal salts such as barium sulfate, plate barium sulfate, butterfly barium sulfate, calcium carbonate, and magnesium carbonate; Fluorine-containing powders such as synthetic phlogopite (synthetic mica) and synthetic ferric phlogopite; Boron-containing powders such as boron nitride; Pearl powder, colored pearl pigments, titanium dioxide and other composite powders; Examples include waxes, pigments, lakes, and the like. Furthermore, the powder may be surface-treated with silicone, a fluorine compound, a silane coupling agent, a silane, an organic titanate, a fatty acid, a metal soap, an oil, an amino acid, etc. Crystalline or amorphous powders such as resin powders, silicon-containing powders, metal oxides, carbon-containing powders, fluorine-containing powders, metal salts, boron-containing powders, and composite powders are preferred from the viewpoint of improving water repellency and oil repellency after treatment. The above powder and N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The mixing of the mixed crystals of lauroyl lysine can be carried out by mixing in a mixer for 1 minute or more. The mixing time is preferably 1 minute or more, more preferably 10 minutes or more. From the viewpoint of low-cost production without reducing productivity, the mixing time is preferably 60 minutes or less. As the mixer, a high-speed stirring mixer such as a Henschel mixer, a household mixer, or a high-shear mixer, a container rotation type mixer or a container rotation type mixer with a stirrer such as a W-type mixer, a CV-type mixer, a V-type mixer, or a rocking mixer, a mechanical stirring type mixer of a ribbon stirring type, a double-shaft paddle type, a double-shaft planetary stirring type, or a conical screw type, an airflow stirring type mixer, a Julia mixer, a Nauta mixer, or a compression, shear, or impact type mixer such as a Nobilta, etc. can be used, and a high-speed stirring type mixer is preferable from the viewpoint of low-cost production and versatility. The mixing also includes the powder and the N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The pulverization may be carried out by pulverizing the mixed crystals of N-lauroyl lysine. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N εThe lauroyl lysine mixed crystals can be crushed for 1 minute or more using a coarse crusher, a medium crusher, a grinder, etc. The crushing time is preferably 1 minute or more, more preferably 10 minutes or more. From the viewpoint of low-cost production without reducing productivity, the mixing time is preferably 60 minutes or less. As the coarse crusher, for example, a jaw crusher can be used, as the medium crusher, for example, a cutter mill, a crusher, etc., and as the grinder, for example, a roller mill, a jet mill, a hammer mill, a pin mill, a rotary mill, an attritor, a bead mill, an atomizer, etc. can be used, but are not limited thereto. From the viewpoint of low-cost production and versatility, a jet mill, a pin mill, a rotary mill, an atomizer, a bead mill, etc. are preferred. The above powder and N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε In the mixing process of the -lauroyl lysine mixed crystals, a solvent having a boiling point of 130° C. or less may be used in an amount of 10% by mass or less based on the entire mixture, but it is preferable not to use such a solvent.

[0018] The treated powder is N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals are contained in an amount of 0.01 to 99.9 mass%, preferably 0.1 to 80 mass%, more preferably 1 to 15 mass%. N ε -N coating the surface of the treated powder treated with lauroyl lysine crystals ε Among the lauroyl lysine crystals, 90% or more of the crystals have a particle size of 1.8 μm or less, preferably 1.5 μm or less, and more preferably 1.2 μm or less. Also, N ε -octanoyl lysine and N ε -N coating the surface of the treated powder treated with lauroyl lysine mixed crystals ε -octanoyl lysine and N εAmong the lauroyl lysine mixed crystals, 90% or more of the crystals have a particle size of 2.8 μm or less, preferably 2.5 μm or less, and more preferably 1.8 μm or less. As described above, the present invention ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The powder treated with the N-lauroyl lysine mixed crystals has water repellency. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The powder treated with the N-lauroyl lysine mixed crystals has oil repellency. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -The powder treated with lauroyl lysine mixed crystals has a soft focus effect.

[0019] The treated powder is ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals are mixed at a mass ratio of 5, and 40% or more, preferably 50% of the powder surface area is N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The coated area ratio can be determined by image analysis using software such as ImageJ. The mixing can be carried out by mixing in a mixer for 1 minute or more. The mixing time is preferably 1 minute or more, more preferably 10 minutes or more. From the viewpoint of low-cost production without reducing productivity, the mixing time is preferably 60 minutes or less. As the mixer, a high-speed stirring mixer such as a Henschel mixer, a household mixer, or a high-shear mixer, a container rotation type mixer or a container rotation type mixer with a stirrer such as a W-type mixer, a CV-type mixer, a V-type mixer, or a rocking mixer, a mechanical stirring type mixer of a ribbon stirring type, a double-shaft paddle type, a double-shaft planetary stirring type, or a conical screw type, an airflow stirring type mixer, a Julia mixer, a Nauta mixer, or a compression, shear, or impact type mixer such as a Nobilta, etc. can be used, and a high-speed stirring type mixer is preferable from the viewpoint of low-cost production and versatility. The mixing also includes the powder and the N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The pulverization may be carried out by pulverizing the mixed crystals of N-lauroyl lysine. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The lauroyl lysine mixed crystals can be crushed for 1 minute or more using a coarse crusher, a medium crusher, a grinder, etc. The crushing time is preferably 1 minute or more, more preferably 10 minutes or more. From the viewpoint of low-cost production without reducing productivity, the mixing time is preferably 60 minutes or less. As the coarse crusher, for example, a jaw crusher can be used, as the medium crusher, for example, a cutter mill, a crusher, etc., and as the grinder, for example, a roller mill, a jet mill, a hammer mill, a pin mill, a rotary mill, an attritor, a bead mill, an atomizer, etc. can be used, but are not limited thereto. From the viewpoint of low-cost production and versatility, a jet mill, a pin mill, a rotary mill, an atomizer, a bead mill, etc. are preferred. The mixing may be performed using a solvent having a boiling point of 130°C or less at a mass ratio of 10% or less based on the total powder to be treated. However, it is preferable to perform the mixing by dry mixing, which does not require a solvent, in that this allows for easy and low-cost production while reducing the environmental impact.

[0020] The present invention provides a composition containing the above treated powder in 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 into ink for printing or writing, pencil lead, etc., in order to improve the color development, adhesion, and durability of the pigment. Furthermore, it can be blended into paint from the viewpoint of preventing oxidation of the pigment, improving water repellency, and improving dispersibility, and it can also be blended into 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 topical agent. The cosmetic or topical agent can be prepared in any form that can be applied to a desired site (e.g., skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method. Examples of the cosmetic or topical agent for the skin, lips, eyelashes, and nails include sunscreens such as sunscreens, body powders, and sprays; makeup cosmetics such as foundations, primers, body colors, bronzers, face powders, nail polishes, cheek colors, makeup bases, and concealers; lip cosmetics such as lip colors, lip liners, and lipsticks; eye makeup cosmetics such as eyeliners, eye shadows, eyebrows, and mascaras; leave-on cosmetics such as emulsions, lotions, creams, gels, and serums; and face masks. Examples of the cosmetic or topical agent for hair include hair styling agents, hair emulsions, hair treatments, hair conditioners, and hair lotions. Examples of the cosmetic or topical agent for the scalp include hair growth agents. Preferable cosmetic preparations include, for example, makeup cosmetic preparations, eye make-up cosmetic preparations, lip cosmetic preparations, and leave-on cosmetic preparations. Preferable external preparations include, for example, ointments, creams, mousses, and gels. The composition of the present invention can be used as a cleaning 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 achieved. More preferred examples include cleaning compositions such as face wash, body soap, soap, cleansing balm, cleansing oil, and other skin cleaning agents, shampoo, and other hair cleaning agents, dishwashing detergents, vegetable washing detergents, and machine washing detergents. The crystals or treated powders of the present invention can be blended with preservatives such as caprylyl glycol, glyceryl caprylate, phenoxyethanol, chlorphenesin, pentylene glycol, hexylene glycol, methylparaben, and propylparaben; antioxidants such as tocopherol, vitamin C, and BHT; chelating agents such as sodium ethylenediaminetetraacetate; binders such as ethyl cellulose and hydroxypropyl cellulose; thickeners such as xanthan gum, carbomer, and polyacrylate crosspolymer; oil gelling agents such as dibutyl ethylhexanoyl glutamide, dibutyl elauroyl glutamide, dextrin palmitate, and polyamide-3; moisturizing agents such as glycerin and 1,3-butylene glycol; emulsifiers such as polyoxyethylene or polysorbate emulsifiers, fatty acid polyglyceryl, and sorbitan fatty acid esters; and oils such as ester oils and hydrocarbon oils, as long as these effects are not impaired. EXAMPLES

[0021] Particle size distribution and particle size measurement method: A laser diffraction / scattering type particle size distribution analyzer (HORIBA, Partica LA-950) was used to measure particle size distribution using cumulative volume values. The results were analyzed using software provided with the device to determine the particle sizes of the number-based distribution and the volume-based distribution. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N εThe mixed crystals of -lauroyl lysine were added to 5g of isopropyl alcohol, and were dispersed by exposing to ultrasonic waves for 30 minutes while stirring using an ultrasonic device with an output of 300 watts. An appropriate amount of this dispersion was added to 500mL of isopropyl alcohol according to the device's procedure, and a dispersion sample of an appropriate concentration was prepared while checking the transparency. This sample was circulated at a flow rate of 10mL / min and exposed to ultrasonic waves for 30 minutes to disperse it into primary particles, and after degassing, the N in the sample was measured using a flow cell. ε The particle size distribution and various particle sizes of the lauroyl lysine crystals were determined.

[0022] How to measure bulk density: N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - The lauroyl lysine mixed crystals were mixed in a mixer for more than 2 minutes and crushed. The bulk density of the obtained crystals was measured using a powder rheometer FT-4 (Freeman Technology). TM Specifically, a certain amount of N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -The lauroyl lysine mixed crystals were weighed into a holder and conditioned according to the usage procedure. The volume and N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε The bulk density was measured from the mass of the lauroyl lysine mixed crystals according to the following formula. Bulk density = mass after conditioning / volume after conditioning (g / mL)

[0023] [Fine powder by pulverization method N ε - Preparation of Lauroyl Lysine Crystals] (Comparative Example 1-1) The following procedure is used to grind N200 with a 90% particle size D90 (number-based distribution) of 15.7 μm in the absence of alcohol. ε -Crushed lauroyl lysine crystals. N εAfter adding 16 parts by weight of water to 100 parts by weight of α-lauroyl lysine crystals and mixing, the mixture was fed to a dry bead mill (Ashizawa Finetech Co., Ltd., model SDA-120) at a rate of 0.5 kg / h and pulverized. Partially stabilized zirconia (PSZ) beads (diameter 1.5 mm) were used as the beads, and the bead filling rate was 70% (v / v) relative to the volume. The powder obtained after pulverization was dried and crushed in a mixer to obtain the desired fine powder N. ε The bulk density and particle sizes of the obtained crystals are shown in Table 1.

[0024] (Comparative Example 1-2) The following procedure is used to grind N with a 90% particle size D90 (number-based distribution) of 15.7 μm in the presence of a solvent. ε -Crushed lauroyl lysine crystals. N ε After adding 1 part by weight of ethanol to 100 parts by weight of α-lauroyl lysine crystals and mixing, the mixture was fed to a dry bead mill (Ashizawa Finetech Co., Ltd., model SDA-120) at a rate of 0.5 kg / h and pulverized. Partially stabilized zirconia (PSZ) beads (diameter 1.5 mm) were used as the beads, and the bead filling rate was 70% (v / v) relative to the volume. The powder obtained after pulverization was dried and crushed in a high-speed mixer to obtain the desired fine powder N. ε The bulk density and particle sizes of the obtained crystals are shown in Table 1.

[0025] (Comparative Example 1-3) The following procedure is used to produce N 15.7μm with a 90% particle size D90 (number-based distribution) using a wet grinding method in the presence of alcohol. ε -Crushed lauroyl lysine crystals. According to the embodiment of JP-A-09-323914, ε -Lauroyl lysine was pulverized. The powder obtained after pulverization was dried and crushed in a high-speed mixer to obtain the desired fine powder N ε The bulk density and particle sizes of the obtained crystals are shown in Table 1.

[0026] (Comparative Examples 1-4) The following procedure is used to grind N2O3 with a 90% particle size D90 (number-based distribution) of 15.7 μm using a dry grinding method in the absence of alcohol and water. ε -Crushed lauroyl lysine crystals. According to Comparative Example 4 of Japanese Patent No. 4826049, ε -Lauroyl lysine is ground into fine powder ε The bulk density and particle sizes of the obtained crystals are shown in Table 1.

[0027] Fine powder N obtained in Comparative Examples 1-1 to 1-4 ε The particle size and physical properties of the lauroyl lysine crystals are summarized in Table 1. [Table 1]

[0028] [Fine powder by crystallization method N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - Preparation of lauroyl lysine mixed crystals]: (Example 2-1) 5.7 g of sodium hydroxide was dissolved in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, and then the solution was heated to about 50°C. ε 36.4 g of lauroyl lysine crystals were added and dissolved at the same temperature. After that, a 0.1 mol / L hydrochloric acid solution (600 mL) was cooled to below 10°C, and N was added while maintaining the pH at 0.7 to 1.3. ε -The lauroyl lysine solution was added dropwise over 75 minutes. After the dropwise addition was completed, the pH was adjusted to 7.0 with sodium hydroxide, and the precipitated crystals were filtered and dried under reduced pressure to obtain 36.0 g of white crystals. The resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0029] (Example 2-2) 5.7 g of sodium hydroxide was dissolved in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, and then the solution was heated to about 50°C. ε 36.4 g of lauroyl lysine crystals were added and dissolved at the same temperature. After that, a 0.085 mol / L aqueous hydrochloric acid solution (150 mL) was cooled to below 0°C and N was added while maintaining the pH at 0.8 to 1.1. ε -The lauroyl lysine solution was added dropwise over 25 minutes. After the dropwise addition was completed, the pH was adjusted to 7.0 with sodium hydroxide, and the precipitated crystals were filtered and dried under reduced pressure to obtain 36.0 g of white crystals. The resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0030] (Example 2-3) Commercially available N ε -Commercially available N instead of lauroyl lysine crystals ε -octanoyl lysine crystals and N ε The same procedure as in Example 2-2 was repeated except that lauroyl lysine crystals were used in a ratio of 1:1. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystal (1:1) was obtained. The bulk density and particle sizes of the obtained mixture are shown in Table 2-2.

[0031] (Examples 2-4) Commercially available N ε -Commercially available N instead of lauroyl lysine crystals ε -octanoyl lysine crystals and N ε The same procedure as in Example 2-2 was repeated except that lauroyl lysine crystals were used in a ratio of 1:3. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystal (1:3) was obtained. The bulk density and particle sizes of the obtained mixture are shown in Table 2-2.

[0032] (Examples 2-5) Commercially available N ε -Commercially available N instead of lauroyl lysine crystals ε -octanoyl lysine crystals and N ε The same procedure as in Example 2-2 was repeated except that lauroyl lysine crystals were used in a ratio of 1:9. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystal (1:9) was obtained. The bulk density and particle sizes of the obtained mixture are shown in Table 2-2.

[0033] (Examples 2-6) Commercially available N ε -Commercially available N instead of lauroyl lysine crystals ε -octanoyl lysine crystals and N ε - Lauroyl lysine crystals were used in a ratio of 3:1, but N was obtained according to the method of Example 2-2. ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals (3:1) were obtained. The bulk density and particle sizes of the obtained mixture are shown in Table 2-2.

[0034] (Comparative Example 2-1) According to Production Example 1 described in JP-A-8-337519, ε 30 g of lauroyl lysine was dissolved in 150 ml of 10% aqueous sodium hydroxide solution. The obtained N ε The solution of -lauroyl lysine was added dropwise to 200 mL of 2 mol / L aqueous hydrochloric acid at room temperature while stirring, maintaining the pH at 2 to 5. After the entire amount had been added dropwise, the pH was adjusted to 7.0 with sodium hydroxide, and the precipitated crystals were filtered and dried to obtain 29.6 g of white crystals. The resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0035] (Comparative Example 2-2) According to Example 2 of Japanese Patent No. 4826049, 5.7 g of sodium hydroxide was dissolved in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, and the solution was heated to about 50°C and then cooled with N ε -Lauroyl lysine (36.4 g) was added and dissolved at the same temperature. Thereafter, the solution was cooled to 25° C., and 38.0 g of 17.5% hydrochloric acid was added dropwise at the same temperature over about 4 hours while maintaining the pH at 7 to 12 and stirring. After the entire amount was added dropwise, 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 resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0036] (Comparative Example 2-3) 5.7 g of sodium hydroxide was dissolved in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, and then the solution was heated to approximately 50°C and then heated under N ε -Lauroyl lysine (36.4 g) was added and dissolved at the same temperature. After that, the reaction mixture was added to a 1.01 mol / L aqueous hydrochloric acid solution (150 mL) that was kept at 25°C without controlling the pH of the reaction mixture. ε -The lauroyl lysine solution was added dropwise over 25 minutes. After the dropwise addition was completed, the pH was adjusted to 7.0 with sodium hydroxide, and the precipitated crystals were filtered and dried under reduced pressure to obtain 35.8 g of white crystals. The resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0037] (Comparative Example 2-4) 5.7 g of sodium hydroxide was dissolved in a mixed solution of 97.4 g of methanol and 62.7 g of water at room temperature, and then the solution was heated to approximately 50°C and then heated under N ε -Lauroyl lysine (36.4 g) was added and dissolved at the same temperature. After that, the reaction mixture was added to a 1.01 mol / L aqueous hydrochloric acid solution (150 mL) that was kept at 5°C without controlling the pH of the reaction mixture. ε -The lauroyl lysine solution was added dropwise over 25 minutes. After the dropwise addition was completed, the pH was adjusted to 7.0 with sodium hydroxide, and the precipitated crystals were filtered and dried under reduced pressure to obtain 34.9 g of white crystals. The resulting white crystals were dried and crushed in a high-speed mixer to obtain the desired fine powder N ε -Lauroyl lysine crystals were obtained. The bulk density and particle sizes of the obtained crystals are shown in Table 2-1.

[0038] The N obtained in Examples 2-1 to 2-6, Reference Example 2-1, and Comparative Examples 2-1 to 2-4 ε -Lauroyl Lysine Crystal, N ε -Octanoyl Lysine Crystal, N ε -octanoyl lysine and N ε The particle size and physical properties of the -lauroyl lysine mixed crystals are shown in Tables 2-1 and 2-2. [Table 2-1] [Table 2-2]

[0039] Example 3 Various powders were treated in the proportions and by the 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 Figures 1 to 19, and the evaluation results of oil repellency are shown in Figures 20 to 24.

[0040] Water repellency rating: 5 g of solvent was weighed into a vial, and 30 mg of untreated powder or various treated powders were added to the surface of the solvent from a height of 3 cm within 2 seconds. After leaving it to stand for 60 minutes after addition, the amount of powder floating on the solvent was determined visually and by image analysis using ImageJ. The more powder floating on the solvent, the more the surface of the powder is N-contacted. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε-It can be determined that the powder surface is efficiently coated with lauroyl lysine mixed crystals, making it less likely to be wetted by solvents and increasing water repellency. The solvents used to evaluate the water repellency of various powders were prepared according to the properties of the powder surface as shown in Table 3. [Table 3]

[0041] Oil repellency rating: Oils similar to the composition of sebum were mixed uniformly in the ratios shown in Table 4 to prepare liquid artificial sebum. 5 g of this artificial sebum was weighed into a vial, and 30 mg of untreated powder or various treated powders were added to the surface of the liquid sebum from a height of 3 cm within 2 seconds. After leaving it to stand for a certain period of time after addition, the amount of powder floating on the liquid sebum was determined visually and by image analysis using ImageJ. The more the amount of powder floating on the liquid sebum, the more N the powder surface. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - It can be determined that the powder surface is efficiently coated with lauroyl lysine mixed crystals, making it less likely to become wet with liquid sebum, and thus improving oil repellency. [Table 4] [Table 5-1] [Table 5-2] [Table 5-3] [Table 5-4]

[0042] How to process powders by simple mixing: Various powders and N were mixed in a Henschel mixer (FM 10C / I manufactured by Nippon Coke and Engineering Co., Ltd.). ε -Lauroyl Lysine Crystal or N ε-octanoyl lysine and N ε The mixed crystals of -lauroyl lysine were added and mixed at room temperature. In addition, 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.

[0043] How to process powders using wet processing methods: N ε 5 g of 1.5% aqueous alkali solution was dissolved in the resulting solution, and 100 g of each type of powder was added and suspended in the resulting solution (powder content: 20% by weight), and the mixture was stirred for 30 minutes. Next, hydrochloric acid was added to neutralize the mixture to pH 7.0, and the mixture was further stirred for 30 minutes. After that, the mixture was repeatedly filtered and washed with water, and then dried at 80°C for 30 hours. The dried product was crushed to obtain N ε Various powders coated with lauroyl lysine were obtained.

[0044] How to process powders by mixing in a compounding machine: Using the hybridization system NHS-1-2L (manufactured by Nara Machinery), 200 g of powder was subjected to hybridization with a median diameter of 20 μm. ε -5 g of lauroyl lysine crystals were added, and the mixture was mixed for 3 minutes at a rotor speed of 100 m / s.

[0045] Microscopic observation of the treatment state: After gold and platinum were deposited on the crystal obtained in Example 2-1, the crystal was observed with a scanning electron microscope (JEOL JCM-6000 PLUS) and images of the surface condition were recorded. The recorded images are shown in FIG.

[0046] N coating on the surface of the treated powder ε -Calculation of lauroyl lysine crystal particle size: The treated powder of Example 3-19 was vapor-deposited with gold and platinum, and then observed with a scanning electron microscope (JEOL JCM-6000 PLUS). The obtained images showed plate-like N attached to the powder surface. ε -The particle size of 500 crystals of lauroyl lysine was measured. ε - Lauroyl lysine crystals with a particle size of 1.8 μm or less εThe number of lauroyl lysine crystals was 483 (96.6%).

[0047] N coating on the surface of the treated powder ε -octanoyl lysine and N ε -Calculation of lauroyl lysine mixed crystal particle size: The treated powder of Example 3-24 was vapor-deposited with gold and platinum, and then observed with a scanning electron microscope (JEOL JCM-6000 PLUS). The particle sizes of 500 plate-like crystals attached to the powder surface were measured from the obtained images. Of the total crystals, the number of plate-like crystals with a particle size of 1.8 μm or less was 461 (92.2%), and the number of plate-like crystals with a particle size of 2.8 μm or less was 489 (97.8%).

[0048] N ε -Calculation of the coverage rate of the treated powder surface by lauroyl lysine crystals: The treated powder of Example 3-19 was vapor-deposited with gold and platinum, and then observed under a scanning electron microscope (JEOL JCM-6000 PLUS). 2 Plate-shaped N ε The area where no lauroyl lysine crystals were attached was identified and its area was calculated using ImageJ. The same process was performed on 20 powder particles, and the area of ​​1 cm 2 On average, this is 0.67 cm. 2 (67%) is N ε -It was found to be coated with lauroyl lysine.

[0049] Example 4 Various powders were mixed in the ratios shown in Table 6 using the powder processing method of simple mixing. The resulting mixed powder had good water and oil repellency, a soft feel, and excellent adhesion to the skin. [Table 6]

[0050] (Example 5-1) Various powders were mixed in the ratios shown in Table 7 using the powder processing method of simple mixing. The resulting mixed powder had good water and oil repellency, a soft feel, and excellent adhesion to the skin. [Table 7]

[0051] (Comparative Example 5-1) Various powders were mixed in the ratios shown in Table 8 using the powder processing method of simple mixing. The resulting mixed powder did not have sufficient water and oil repellency, and was not soft to the touch or adherent to the skin. [Table 8]

[0052] (Comparative Example 5-2) Various powders were mixed in the ratios shown in Table 9 using the powder processing method of simple mixing. The resulting mixed powder had almost no water and oil repellency, and was not soft to the touch or adherent to the skin. [Table 9]

[0053] Example 6 The various powders were mixed for 10 minutes using an impact mill (Atomizer, manufactured by Dalton Co., Ltd.) in the ratios shown in Table 10. The resulting mixed powder had good water and oil repellency and a soft feel. Furthermore, the pigments had excellent uniform color development. [Table 10]

[0054] Example 7 Various powders were mixed in the ratios shown in Table 11 using the powder processing method of simple mixing. The water repellency and oil repellency of the resulting mixed powders were calculated as follows. Water repellency = 100 x (amount of powder floating on top of the solvent after 60 minutes / amount of powder floating on top of the solvent at 0 minutes) Oil repellency = 100 x (amount of powder floating on top of the solvent after 5 minutes / amount of powder floating on top of the solvent at 0 minutes) Based on the values ​​obtained from the above formula, the water repellency and oil repellency of the mixed powders were evaluated according to the following evaluation criteria, and the results are shown in Table 11. <Evaluation of water repellency> 1) Water repellency value is 60% or more: Very good (A) 2) Water repellency value is greater than 30% and less than 60%: slightly favorable (B) 3) Water repellency value is greater than 10% and less than 30%: Not very desirable (C) 4) Water repellency value is less than 10%: Not suitable at all (D) <Evaluation of oil repellency> 1) Oil repellency value of 50% or more: Very good (A) 2) Oil repellency value is greater than 20% and less than 50%: slightly favorable (B) 3) Oil repellency value is greater than 5% and less than 20%: Not very desirable (C) 4) Oil repellency value is less than 5%: Not suitable at all (D) In addition, four expert panelists evaluated the softness of the various mixtures and the gloss when applied according to the following criteria. <Evaluation of softness when applied> 1) The texture is very soft and pleasant when applied... 4 points 2) The texture when applied is a little soft, which is good... 3 points 3) The texture when applied is a little hard and not very good... 2 points 4) The texture is hard when applied, and not good at all... 1 point <Gloss when applied> 1) After application, a very nice, natural shine is obtained... 4 points 2) A slight shine is obtained after application... 3 points 3) Not much shine after application... 2 points 4) No shine at all after application... 1 point The evaluation was based on the average scores of four expert panelists and was judged as follows. The results are shown in Table 11. Average rating of 3.5 or more: Very favorable (A) Average rating: 2.5 or more but less than 3.5: Somewhat favorable (B) Average rating between 1.5 and 2.5: Not very favorable (C) Average rating less than 1.5: Not desirable at all (D) [Table 11]

[0055] (Example 8-1 and Comparative Example 8-1) Using the components shown in Table 12, cleansing compositions were prepared as follows. Component A was dispersed in component B at room temperature. Component C was then added and stirred at room temperature to obtain a homogeneous solution. Component D was then added and stirred using a homodisper until homogeneous. Component E was added to adjust the pH to 5.4, and then component F was added and mixed homogeneously to obtain a cleansing composition. The resulting cleansing composition was stored for one month under cycled temperature conditions of -5°C to 40°C (the temperature inside the cabinet was kept at -5°C for 12 hours, raised from -5°C to 40°C over 3 hours, kept at 40°C for 12 hours, then cooled from 40°C to -5°C over a further 3 hours, and kept at -5°C for 12 hours. The temperature was repeatedly changed in this cycle). The degree of pearlization of the composition before and after storage was visually confirmed. The composition of Example 8-1 maintained the same pearl effect as immediately after preparation, whereas the composition of Comparative Example 8-1 was barely able to maintain the pearl effect. In addition, four expert panelists evaluated the conditioning effects on hair and skin after use of the cleansing compositions of Example 8-1 and Comparative Example 8-1. All panelists rated the composition of Example 8-1 as having a greater conditioning effect on hair and skin than the composition of Comparative Example 8-1. [Table 12]

[0056] (Example 9-1 and Comparative Example 9-1) Using the components shown in Table 13, cleansing compositions were prepared as follows. Component A was dispersed in component B at room temperature. Component E was dissolved by stirring at room temperature. Component C and component D were dissolved by stirring 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. Component E was added and stirred and mixed, and the mixture was cooled to 50°C, and component F was added. The mixture was cooled to room temperature to obtain a cleansing composition. Four expert panelists evaluated the effectiveness of the cleansing compositions of Example 9-1 and Comparative Example 9-1 in reducing the slimy feeling of the surfactant during use. As a result, all panelists rated the composition of Example 9-1 as being more effective in reducing the slimy feeling of the surfactant during use than the composition of Comparative Example 9-1. [Table 13]

[0057] Evaluation of the soft focus effect of powder: 50 mg of the powder was evenly applied to a black paper, and the light scattering ability of the powder was measured using a GONIOPHOTOMETER GP-700 (manufactured by Murakami Color Research Laboratory). Light was irradiated onto the powder surface at -45°, and the ratio of the intensities of the light scattered at 45° and 0° (45° intensity / 0° intensity) was calculated. The closer this ratio is to 1, the higher the soft focus effect of the powder can be evaluated. In addition, N ε -The improvement rate of the soft focus effect of powder by treatment with lauroyl lysine crystals was compared. [Table 14] From the results in Table 14, N ε It can be seen that the soft focus effect of the plate-shaped powder is improved by treating it with lauroyl lysine crystals.

[0058] (Example 10-1 and Comparative Example 10-1) Using the components shown in Table 15, lip cosmetics were prepared as follows. Component A was heated and dissolved at 105±5°C, and component B was added to component A and heated and dissolved at 90°C. Component C was then added and mixed by heating at 90°C, after which the mixture was dispersed using a three-roll mill, and then component D was added. Component E was added and mixed by heating at 90°C, after which the mixture was degassed. The mixture was filled into a mold at a filling temperature of 90°C, cooled, and then loaded into a container. The lip cosmetic of Example 10-1 exhibited better color development, less color unevenness, and better color uniformity than Comparative Example 10-1. Furthermore, it did not cause sweating and was stable. [Table 15]

[0059] (Example 11-1 and Comparative Example 11-1) Using the components shown in Table 16, a leave-on cosmetic composition was prepared as follows. After components A and B were heated to 80°C and dissolved, component A was added to component B with stirring. The mixture was emulsified using a homomixer (3000 rpm, 3 minutes, 80°C) and cooled to room temperature to obtain a leave-on cosmetic preparation. The leave-on cosmetic of Example 11-1 had better stability and preservative properties than Comparative Example 11-1. Furthermore, it provided an excellent moist feeling after application, and the application further improved the gloss. [Table 16]

[0060] (Example 12-1 and Comparative Example 12-1) Using the components shown in Table 17, eye make-up cosmetics were prepared as follows. After mixing component A for 10 minutes, component B was added to component A and mixed for an additional 20 minutes. Component C was mixed for 10 minutes using a mixer (FM 10C / I manufactured by Nippon Coke & Engineering Co., Ltd.), then added to the mixture of components A and B and mixed for an additional 5 minutes. The resulting mixture was filled into a container and compressed using a press to obtain the desired eye makeup cosmetic. Four expert panelists evaluated the pearly feel, gloss, payoff and color development after application of the eye makeup cosmetics of Example 12-1 and Comparative Example 12-1. All panelists rated the eye makeup cosmetic of Example 12-1 as having better pearly feel, gloss, payoff and color development after application than the eye makeup cosmetic of Comparative Example 12-1. The eye makeup cosmetic of Example 12-1 is excellent in usability because it can be produced using a small amount of oil. In Example 12-1, the gloss of the pearl powder and colored pearl pigment did not decrease, and rather was improved. [Table 17]

[0061] (Example 13-1 and Comparative Example 13-1) Using the components shown in Table 18, makeup cosmetics were prepared as follows. After mixing component B for 10 minutes, component C was added to component B, and component B was dispersed in component C using a disperser. Component A was gradually added to components B and C, and emulsified uniformly using a homomixer. After emulsification, component D was added and further mixed, then cooled to room temperature to obtain the desired makeup cosmetic. The makeup of Example 13-1 was superior to that of Comparative Example 13-1 in emulsion stability, improved gloss after application, and reduced unevenness of pigments. Furthermore, it had improved makeup staying power and preservative properties, and provided an excellent moist feeling after application. [Table 18]

[0062] Example 14 A foundation was prepared using the ingredients shown in Table 19 as follows. Component B was mixed uniformly. Component A was mixed in a mixer for 1 minute, then component B was added to component A and mixed for an additional 30 seconds. 12g of the dispersion solvent water / ethanol (mixture ratio water:ethanol = 80:20) was added to 8g of the resulting mixture and dispersed while mixing. 13g of the resulting dispersion was weighed out and placed in a container, and while pressing, tissue paper was used from above to fully absorb the dispersion solvent water / ethanol. The compressed composition in the container was dried overnight at 80°C to obtain the desired foundation. The foundation of Example 14 had excellent adhesion after application and a natural finish. Furthermore, the product itself had good moldability and beautiful color. Furthermore, the causes of makeup breakdown, such as unevenness, shine, creasing, dullness, and disappearance due to changes over time of the makeup film, were reduced. [Table 19]

[0063] Example 15 A pencil composition was prepared using the ingredients shown in Table 20 as follows. Compositions in Table 20 Component A was mixed for 5 minutes in a mixer (FM 10C / I manufactured by Nippon Coke & Engineering Co., Ltd.), then component B was added to component A and mixed for another 10 minutes. Component C was melted at 100°C, added to component A + component B, and mixed for 10 minutes. Component D was added to the resulting mixture, kneaded with a three-roll mill, filled into a container while heating, and baked to solidify. The pencil obtained in Example 15 had a high gloss and a lead that was not easily broken. Furthermore, it had excellent color development. [Table 20]

Claims

1. An N ε -lauroyl lysine crystal or a mixed crystal of N ε -octanoyl lysine and N ε -lauroyl lysine obtained by preparing a solution in which (i) N ε -lauroyl lysine or (ii) N ε -octanoyl lysine and N ε -lauroyl lysine are dissolved in an acidic or basic solvent containing one or more selected from water-soluble organic solvents and / or water, and then dropping the solution into an acidic solution having a pH of 0.2 or more and lower than pH 2.0 at a temperature of 20°C or less to cause crystallization, The 90% particle diameter D90 of the number-based distribution is 2.8 μm or less. ε - Lauroyl lysine crystals, or a particle size distribution based on number of particles having a 90% particle size D90 of 2.8 μm or less, ε -octanoyl lysine and N ε - Lauroyl lysine mixed crystals.

2. 2. The N powder according to claim 1, wherein the median diameter or average particle diameter of the volume-based distribution is 2.8 μm or less. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - Lauroyl lysine mixed crystals.

3. An N ε -lauroyl lysine crystal or a mixed crystal of N ε -octanoyl lysine and N ε -lauroyl lysine obtained by preparing a solution in which (i) N ε -lauroyl lysine or (ii) N ε -octanoyl lysine and N ε -lauroyl lysine are dissolved in an acidic or basic solvent containing one or more selected from water-soluble organic solvents and / or water, and then dropping the solution into an acidic solution having a pH of 0.2 or more and lower than pH 2.0 at a temperature of 20°C or less to cause crystallization, Bulk density is 0.34 g / mL or less. ε - Lauroyl lysine crystals, or N having a bulk density of 0.34 g / mL or less ε -octanoyl lysine and N ε - Lauroyl lysine mixed crystals.

4. One or more water-soluble organic solvents and / or an acidic or basic solvent containing water are added to one or more N ε - preparing a solution in which a long-chain acyl lysine is dissolved, and dropping said solution into an acidic solution having a pH of 0.2 or more and less than pH 2.0 at a temperature of 20°C or less to obtain a lysine having an acyl group of (i) lauroyl or (ii) octanoyl and lauroyl, ε -Non-milled N-acyl-lysine crystals including crystallization ε - a method for producing long-chain acyl lysine crystals, comprising the steps of: (1) the 90% particle size D90 of the number-based distribution of N ε -long-chain acyl lysine crystals is 2.8 μm or less, or (2) the bulk density of the N ε -long-chain acyl lysine crystals is 0.34 g / mL or less.

5. N in the crystal ε The N-octanoyl lysine composition according to any one of claims 1 to 3, which contains 99% by mass or less of octanoyl lysine. ε -octanoyl lysine and N ε - Lauroyl lysine mixed crystals.

6. The N according to any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A composition comprising 0.01 to 99.9% by weight of lauroyl lysine mixed crystals.

7. The N according to any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A composition for industrial use comprising 0.01 to 99.9% by weight of lauroyl lysine mixed crystals.

8. The N according to any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A cosmetic or topical preparation containing lauroyl lysine mixed crystals in an amount of 0.01 to 99.9% by mass.

9. The N according to any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A cleansing composition comprising lauroyl lysine mixed crystals in an amount of 0.01 to 99.9% by mass.

10. Powder and the N according to any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - A treated powder obtained by mixing lauroyl lysine mixed crystals.

11. The treated powder according to claim 10, wherein the powder comprises a crystalline or amorphous powder of a resin powder, a silicon-containing powder, a metal oxide, a carbon-containing powder, a fluorine-containing powder, a metal salt, a boron-containing powder, or a composite powder.

12. The N coating on the surface of the treated powder ε - Lauroyl lysine crystals having a particle size of 1.8 μm or less ε The treated powder according to claim 10 or 11, wherein the proportion of lauroyl lysine crystals is 90% or more.

13. The N coating on the surface of the treated powder ε -octanoyl lysine and N ε The treated powder according to claim 10 or 11, wherein the proportion of crystals having a particle size of 2.8 μm or less among the lauroyl lysine mixed crystals is 90% or more.

14. The powder is a powder of any one of claims 1 to 3 and 5. ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε -Lauroyl lysine mixed crystals are mixed at a mass ratio of 5, and 40% or more of the powder surface area is N ε -Lauroyl Lysine Crystal or N ε -octanoyl lysine and N ε - coating with lauroyl lysine mixed crystals.

15. 15. The method of claim 14, wherein said mixing comprises mixing by dry blending without the need for a solvent.

16. 16. The method of claim 14 or 15, wherein the mixing comprises mixing with a mixer for up to 60 minutes.

17. The treated powder according to any one of claims 10 to 13, which has water repellency.

18. The treated powder according to any one of claims 10 to 13 and 17, which has oil repellency.

19. The treated powder according to any one of claims 10 to 13, 17 and 18, which has a soft focus effect.

20. A composition comprising the treated powder according to any one of claims 10 to 13 and 17 to 19 in an amount of 0.01 to 99.99 mass percent.

21. The composition according to claim 20, which is a composition for industrial use, a cosmetic preparation, an external preparation or a cleansing agent.

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