N ε -Method for producing long-chain acyl lysine crystals and composition containing the same

Abstract

Non-crushed N ε A method for producing a long-chain acyl-lysine crystal, comprising: preparing a solution containing one or more N- ε The solution is added dropwise to an acidic solution having a pH of 0.2 or more and a pH of less than 2.0 at a temperature below 20°C, so that N ε ‑Long-chain acyl-lysine crystals.

Description

Technical Field

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

[0002] Powder raw materials that can play the performance of water repellency and oil repellency at the same time are very important in cosmetics and various industrial applications. However, it has always been considered difficult to obtain cheap powder raw materials that can play these functions at the same time and have a small environmental load. For example, inorganic powders such as talc, mica, sericite, titanium oxide, zinc oxide, iron oxide, aluminum oxide, barium sulfate, boron nitride, silicon dioxide, synthetic phlogopite (synthetic mica) and organic powders such as starch, cellulose, fatty acid salts, bamboo or wood powders are used to impart lubricity, improve hiding power, coloring, light absorption or scattering purposes. In general, due to the presence of high polarity functional groups on the powder surface, the powder is easily wetted by high polarity solvents such as water. However, when such powder is used in cosmetics, it is wetted by sweat, etc., thereby becoming the cause of the dullness and discoloration of makeup. In addition, it can also be caused to remove makeup due to sweating. In industrial applications, the coating or ink containing these powders can also be wetted by water or rain and lost, and when used as a lubricant for machinery, there is a problem that cannot give full play to lubricity. In addition, general powders are not good in oil repellency, so if used in cosmetics, the surface of the powder will be wetted by sebum, etc., causing discoloration or dullness of cosmetics such as foundation (Japanese Patent Publication No. 2010-242026). In addition, it can also cause makeup removal due to oil absorption. In industrial applications, when used as a lubricant, there is also the problem of absorbing machine oil and generating high-viscosity mud and other dirt.

[0003] In order to solve such a problem, a technology for treating the surface of powders with fluorinated molecules that are neither soluble in water nor soluble in oil has been developed. The powders surface-treated with fluorinated molecules show excellent performance in water repellency and oil repellency, but due to the presence of perfluorinated compounds or low molecular weight fluorinated compounds as impurities, the problems of accumulation and toxicity in the environment or human body have been pointed out. In addition, the powders surface-treated with fluorinated molecules have poor skin affinity, and there are problems of makeup persistence and poor sense of use. In addition, the powders surface-treated with fluorinated molecules have extremely reduced oil repellency in the presence of water, so when used in cosmetics, there is a problem of wetting (getting wet) in sweat and sebum.

[0004] Regarding N as a raw material derived from amino acids which is neither dispersed in water nor dissolved in oil and does not accumulate in the environment ε -Lauroyl lysine crystals adhere to the powder surface, giving the powder N ε-The function of lauroyl lysine crystal technology is being studied. It is important that the surface of the powder is N ε -Lauroyl lysine crystals are completely covered. However, the 90% particle size D90 (number-based distribution) of general powders is mostly less than 20 μm, while the commercially available N ε - The 90% particle size D90 (number-based distribution) of lauroyl lysine crystals ("AMIHOPE LL" manufactured by Ajinomoto Co., Ltd.) was 15.7 μm, and the median particle size and average particle size of the volume-based distribution were 14.3 μm and 15.3 μm, respectively. ε - The median particle size of the volume-based distribution of octanoyl lysine crystals ("AMIHOPE OL" manufactured by Ajinomoto Co., Ltd.) is 20 μm. These crystals contain almost no crystals with small particle sizes, so according to the DLVO theory, it is difficult for general powders to be N-type by simple mixing. ε -Lauroyl lysine crystals or N ε -octanoyl lysine crystals are stably coated. For example, it is known that the powder is mixed with N ε -Lauroyl lysine crystals are simply mixed with N ε - A simple dry treatment method for treating the surface of a powder with lauroyl lysine crystals (International Publication No. 2011 / 025252). However, in this method, N ε - The coverage rate of the lauroyl lysine crystals was poor, and as a result, sufficiently excellent water repellency and oil repellency could not be achieved.

[0005] In addition, N ε -lauroyl lysine crystal coverage is improved to produce N ε - a fine powder of lauroyl lysine crystals, the fine powder is simply mixed with the powder, and N ε - a method for treating the surface of a powder with lauroyl lysine crystals. For example, it is known that N is treated by a wet pulverization method (Japanese Patent Laid-Open No. 09-323914, Japanese Patent No. 4826049). ε -Lauroyl lysine crystals are finely divided and mixed with inorganic powder. However, the N ε -Lauroyl lysine crystals need to be crushed more than 20 times, and industrial large-scale micro powder N ε -The production of lauroyl lysine crystals is difficult. In addition, even if crushed more than 20 times, the obtained N ε -lauroyl lysine crystals also had an average particle size (volume-based distribution) of 3.4 μm. The crystals were mixed with inorganic powder and precipitated with N ε-Lauroyl lysine crystals are used to treat inorganic powders, but sufficient and excellent water repellency and oil repellency cannot be achieved. In addition, this method requires the use of a large amount of organic solvent, which is a problem that it cannot be produced at a low cost and has a high environmental load.

[0006] It has been reported that in order to obtain N in a simpler way ε -Lauroyl lysine fine crystals are prepared by dropping N into a solution of hydrochloric acid or the like maintained at a pH of 2 to 5. ε -lauroyl lysine was crystallized from an alkaline solution to obtain N with an average projected diameter of 0.5 μm. ε - Crystals of lauroyl lysine (Japanese Patent Publication No. 08-337519). By mixing the crystals with powder, the adhesion of the mixed powder to the skin and the feeling of use of the mixed powder can be improved. However, it is known that the water repellency and oil repellency of the mixed powder obtained by this method are not improved, but the dispersibility of the powder in water and oil is increased. In addition, it is also reported that the N obtained by this method is measured by a laser diffraction / scattering type particle size distribution measuring device. ε In the case of the crystals of -lauroyl lysine, the average particle size (volume-based distribution) is 18 μm (Comparative Example 2 of Japanese Patent No. 4826049). ε -Lauroyl lysine crystals cannot improve the water and oil repellency of the powder. The reason can be cited as follows: ε -Lauroyl lysine crystals have a large particle size. In the case of plate-like particles, the projected particle size measured by a microscope and the average particle size measured by a light scattering method or the like may differ in the measurement principle.

[0007] In addition, by crystallization at pH 7.0, N ε -Lauroyl lysine crystals (Japanese Patent No. 4826049). However, even if the N ε - Even if the powder is treated with lauroyl lysine crystals, it is still impossible to achieve sufficiently excellent water repellency and oil repellency.

[0008] In addition, it is also known that N ε -Lauroyl lysine adheres to the powder surface (Japanese Patent Publication No. 4-63844, Japanese Patent Publication No. 61-10503). ε -Lauroyl lysine itself is insoluble, so it can be dissolved in a strong base or acid or solvent, and the solution is slowly added to the acidic or alkaline powder dispersion to make N ε-lauroyl lysine neutralizes the surface of the powder crystallized in the powder dispersion. By filtering and drying the dispersion after crystallization, a powder with N attached to the surface can be obtained. ε -lauroyl lysine. However, even if this method is used with N ε -Lauroyl lysine is used to treat inorganic powders, and although certain water repellency and oil repellency can be obtained, the degree is still insufficient. In addition, in the case of this method, a large amount of organic solvents need to be used, or the dissolution and drying processes need to be repeated, which has the problem of being unable to be produced cheaply (low cost). In addition, in the case of powders such as silicon dioxide and starch that can be completely dissolved in solvents or acids or alkalis, there is also the problem of being unable to be produced with N ε -Lauroyl lysine crystals or N ε -The topic of treating the surface of the powder of octanoyl lysine crystals.

[0009] In addition, we also considered using a special composite processing machine to combine the powder with N ε -Lauroyl lysine crystals were strongly collided and mechanical shear force was used to ε -Lauroyl lysine crystals are used to treat the surface of the powder. However, in the case of this method, the amount of powder that can be treated at one time is small, and there is a problem that it cannot be produced cheaply. In addition, there is also a problem that brittle powders such as silicon dioxide are crushed and the unique functions of the powder are reduced. In addition, there is also a problem that it is impossible to achieve sufficient excellent water repellency and oil repellency. As mentioned above, it is necessary to give the powder the functions of water repellency and oil repellency while improving the feel of use and skin affinity of the powder, and a technology that can be produced cheaply. Summary of the invention

[0010] An object of the present invention is to obtain a technology that can improve the soft touch of powder and impart water repellency and oil repellency to powder, and can be produced at low cost.

[0011] The present inventors have conducted intensive research on the above-mentioned subject and have found for the first time that by producing N ε -Long-chain acyl lysine crystals can solve the above-mentioned problems, thereby completing the present invention. That is, the present invention is the following invention;

[0012] [1]N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε - mixed crystals of lauroyl lysine, wherein the 90% particle size D90 of the number-based distribution is 2.8 μm or less;

[0013] [2] According to [1] ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and Nε - mixed crystals of lauroyl lysine, wherein the median or average particle size of the volume-based distribution is 2.8 μm or less;

[0014] [3]N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε - mixed crystals of lauroyl lysine, wherein the bulk density is 0.34 g / mL or less;

[0015] [4] Non-crushed (i.e. not crushed) N ε - A method for producing a long-chain acyl lysine crystal, comprising: preparing a solution containing one or more N- ε -long-chain acyl lysine, and adding the solution dropwise to an acidic solution having a pH of 0.2 or more and less than 2.0 at a temperature below 20°C to make N ε - Crystallization (precipitation) of long-chain acyl lysine crystals;

[0016] [5] N according to any one of [1] to [3] ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε - Mixed crystals of lauroyl lysine, wherein the crystals or mixed crystals are obtained by the production method described in [4];

[0017] [6] N according to any one of [1] to [5] ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε - a mixed crystal of lauroyl lysine, wherein the crystal contains N ε - Capryloyl lysine;

[0018] [7] A composition comprising 0.01 to 99.9 mass % of N described in any one of [1] to [3], [5] and [6]. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine;

[0019] [8] A composition for industrial use, comprising 0.01 to 99.9% by mass of N described in any one of [1] to [3], [5] and [6]. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε-Mixed crystals of lauroyl lysine;

[0020] [9] A cosmetic or external preparation containing 0.01 to 99.9% by mass of N described in any one of [1] to [3], [5] and [6]. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine;

[0021]

[10] A cleaning composition comprising 0.01 to 99.9% by mass of N described in any one of [1] to [3], [5] and [6]. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine;

[0022]

[11] A treated powder, wherein the treated powder is prepared by mixing the powder and N described in any one of [1] to [3], [5] and [6] with the treated powder. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε - obtained by mixing mixed crystals of lauroyl lysine;

[0023]

[12] The treated powder according to

[11] , 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;

[0024]

[13] The treated powder according to

[11] or

[12] , wherein the N coating the surface of the treated powder ε - In the lauroyl lysine crystals, N ε - The ratio of lauroyl lysine crystals is more than 90%;

[0025]

[14] The treated powder according to

[11] or

[12] , wherein the N coating the surface of the treated powder ε -Octanoyl lysine and N ε - In the mixed crystals of lauroyl lysine, the proportion of crystals with a particle size of 2.8 μm or less is 90% or more;

[0026]

[15] The method for preparing a treated powder according to any one of

[11] to

[14] , comprising: mixing 5 mass % of N according to any one of [1] to [3], [5] and [6] with the powder. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε-Mixed crystals of lauroyl lysine, more than 40% of the powder surface area is N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε - Coating with mixed crystals of lauroyl lysine;

[0027]

[16] The preparation method according to

[15] , wherein the mixing comprises: mixing by dry mixing without a solvent;

[0028]

[17] The preparation method according to

[15] or

[16] , wherein the mixing comprises: mixing by a mixer for 60 minutes or less;

[0029]

[18] The treated powder according to any one of

[11] to

[14] , wherein the powder is water repellent;

[0030]

[19] The treated powder according to any one of

[11] to

[14] and

[18] , wherein the powder has oil repellency;

[0031]

[20] The treated powder according to any one of

[11] to

[14] ,

[18] and

[19] , wherein the powder has a soft focus effect;

[0032]

[21] A composition comprising 0.01 to 99.99% by mass of the treated powder described in any one of

[11] to

[14] and

[18] to

[20] ;

[0033]

[22] The composition according to

[21] , wherein the composition is an industrial composition, a cosmetic, an external preparation, or a cleaning product.

[0034] Brief description of the attached figure

[0035] Figure 1 It is a graph 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;

[0036] Figure 2 It is a graph showing the evaluation results of water repellency for Example 3-2, Comparative Example 3-10, Comparative Example 3-17 and Comparative Example 3-2;

[0037] Figure 3 It is a graph showing the evaluation results of water repellency for Comparative Example 3-24, Example 3-3, and Comparative Example 3-3;

[0038] Figure 4It is a graph showing the evaluation results of water repellency for Example 3-4 and Example 3-5;

[0039] Figure 5 It is a graph showing the evaluation results of water repellency for Example 3-6, Example 3-7 and Example 3-8;

[0040] Figure 6 It is a graph showing the evaluation results of water repellency of Comparative Example 3-25 and Example 3-9;

[0041] Figure 7 It is a graph showing the evaluation results of water repellency of Comparative Example 3-26 and Example 3-10;

[0042] Figure 8 It is a graph showing the evaluation results of water repellency for Comparative Example 3-27, Example 3-11, and Comparative Example 3-13;

[0043] Fig. 9 It is a graph 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;

[0044] Fig.10 It is a graph 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;

[0045] Fig.11 It is a graph showing the evaluation results of water repellency of Comparative Example 3-36 and Comparative Example 3-14;

[0046] Fig.12 It is a graph showing the evaluation results of water repellency for Comparative Example 3-30, Example 3-15, and Comparative Example 3-6;

[0047] Fig.13 It is a graph showing the evaluation results of water repellency for Comparative Example 3-31, Example 3-16, Comparative Example 3-15, and Comparative Example 3-7;

[0048] Fig.14 It is a graph showing the evaluation results of water repellency of Comparative Example 3-32 and Example 3-17;

[0049] Fig.15 It is a graph showing the evaluation results of water repellency of Comparative Example 3-33 and Example 3-18;

[0050] Fig.16 It is a graph showing the evaluation results of water repellency for Comparative Example 3-34, Example 3-19, and Example 3-20;

[0051] Fig.17 It is a graph showing the evaluation results of water repellency for Comparative Example 3-35, Example 3-21, and Comparative Example 3-8;

[0052] Fig.18 This is a graph showing the evaluation results of water repellency for Comparative Example 3-37;

[0053] Fig.19 It is a graph showing the evaluation results of water repellency of Comparative Example 5-1, Comparative Example 5-2 and Example 5-1;

[0054] Fig. 20 It is a graph 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;

[0055] Fig.21 It is a graph showing the evaluation results of oil repellency for Comparative Example 3-24, Example 3-3, Comparative Example 3-39 and Comparative Example 3-22;

[0056] Fig. 22 It is a graph showing the evaluation results of oil repellency for Comparative Example 3-35, Example 3-21, and Comparative Example 3-8;

[0057] Fig.23 It is a graph showing the evaluation results of oil repellency for Comparative Example 3-29, Example 3-15, and Comparative Example 3-14;

[0058] Fig.24 It is a graph showing the evaluation results of oil repellency of Comparative Example 5-1, Comparative Example 5-2 and Example 5-1;

[0059] Fig.25 is a SEM image of the crystal of Example 2-1;

[0060] Fig.26 This is a diagram showing the evaluation results of water repellency and oil repellency for Examples 3-22 to 3-26. DETAILED DESCRIPTION

[0061] About N of the present invention ε - A method for producing long-chain acyl lysine crystals, which can be obtained in a non-crushing manner by a method comprising the following steps: preparing a solution containing one or more N- ε -long-chain acyl lysine, and adding the solution dropwise to an acidic solution having a pH of 0.2 or more and a pH of less than 2.0 at a temperature of 20°C or less to make N ε -Long-chain acyl lysine crystals were precipitated.ε -Long-chain acyl lysine solution can be N ε - The long-chain acyl lysine can be obtained by dissolving the crystals, or a solution obtained by reacting a fatty acid and lysine without crystallizing the reaction solution can be used.

[0062] N ε The long-chain acyl group of the -long-chain acyl lysine is a saturated or unsaturated fatty acid acyl group having 8 to 22 carbon atoms, and examples thereof include octanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, octyldodecyl, oleyl, behenyl, coconut oil fatty acid acyl, palm kernel oil fatty acid acyl, and tallow fatty acid acyl. From the viewpoint of general availability, lauroyl and octanoyl are preferred.

[0063] Examples of the water-soluble organic solvent include acetone, methanol, ethanol, propanol, butanol, isopropanol, and the like, preferably acetone, methanol, isopropanol, and butanol. These water-soluble organic solvents may be used alone or in combination of two or more.

[0064] When a water-soluble organic solvent and water are used together, 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, preferably 55 / 45 to 70 / 30. When the weight ratio of the two is less than 55 / 45 or greater than 70 / 30, N ε -The solubility of long-chain acyl-lysine decreases, making N ε -The dissolution of long-chain acyl-lysine requires a large amount of solvent, which reduces the efficiency.

[0065] The acid used for the acidic solvent may be any of an organic acid and an inorganic acid, and examples thereof include sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, citric acid, lactic acid, glutamic acid, and pyrrolidonecarboxylic acid, among which sulfuric acid and hydrochloric acid are preferred.

[0066] The base used for the alkaline solvent may be any of an organic base and an inorganic base, and examples thereof include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, ammonia, triethylamine, triethanolamine, monoethanolamine, pyridine, arginine, lysine, etc., preferably sodium hydroxide and potassium hydroxide.

[0067] The amount of acid or base in the acidic solvent or alkaline solvent is not particularly limited, as long as it can dissolve N ε -long chain acyl lysine.

[0068] The temperature during crystallization is not particularly limited as long as it is 20° C. or less. From the perspective of obtaining crystals with a small median particle 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. In addition, the lower limit of the temperature during crystallization is as long as it is above the solidification point of the solvent.

[0069] The acidic solution used in the crystallization can be prepared from the above-mentioned acid. The pH of the acidic solution is 0.2 or more and less than 2.0, preferably 0.7 to 1.3, and more preferably 0.8 to 1.1.

[0070] The generated crystals can be collected and dried by commonly used methods.

[0071] The N obtained in this way ε -Long-chain acyl lysine crystals act as stable pearlescent agents in cleaning compositions, and when cleaning skin or hair with a cleaning composition containing such crystals, the conditioning effect of hair or skin is improved. In addition, when the crystals are contained in a cleaning composition, the slimy feeling of the cleaning product during cleaning can be suppressed. In addition, when the crystals are used in an emulsion, the moist feeling and gloss of the emulsion can be improved. In addition, by treating the powder with the crystals, the powder can be given water-repellent and oil-repellent functions while improving the softness of the touch of the powder and the gloss during coating. The crystals are preferably N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine. ε -Octanoyl lysine and N ε -The mixed crystals of lauroyl lysine can be N ε -Octanoyl lysine and N ε - a mixture of single crystals of lauroyl lysine, or N ε -Octanoyl lysine and N ε -lauroyl lysine eutectic. In addition, preferably in N ε -Octanoyl lysine and N ε The mixed crystals of lauroyl lysine contain N ε -Octanoyl lysine. ε The content of -octanoyl lysine is more preferably 5 to 75%, further preferably 15 to 45%, most preferably 20 to 30%.

[0072] For the present invention, N ε -Lauroyl lysine crystals, and N ε -Octanoyl lysine and N εThe mixed crystals of -lauroyl lysine have a 90% particle size D90 of 2.8 μm or less in the number-based distribution. The crystals of the present invention act as a stable pearlescent agent in a cleaning composition, and when the cleaning composition containing such crystals is used to clean the skin or hair, the 90% particle size D90 is greater than that of N-lauroyl lysine. ε Compared with the crystals of -lauroyl lysine, the hair or skin care effect is improved. In addition, when the crystals of the present invention are contained in a cleaning product composition, the slimy feeling of the cleaning product during cleaning can be suppressed. In addition, when the crystals of the present invention are used in an emulsion, the moist feeling and gloss of the emulsion can be improved. In addition, by treating the powder with the crystals of the present invention, the softness of the touch of the powder and the gloss during coating can be improved, while giving the powder the functions of water repellency and oil repellency.

[0073] The 90% particle size D90 is preferably from 0.01 to 2.8 μm, more preferably from 0.05 to 1 μm, further preferably from 0.1 to 0.7 μm.

[0074] In addition, for the N ε -Lauroyl lysine crystals, and N ε -Octanoyl lysine and N ε The mixed crystals of -lauroyl lysine have a median particle size or average particle size based on volume distribution of 2.8 μm or less, preferably 0.01 to 2.8 μm, more preferably 0.05 to 2.0 μm, and further preferably 0.07 to 1.5 μm.

[0075] In other aspects, N of the present invention ε -Lauroyl lysine crystals, and N ε -Octanoyl lysine and N ε The bulk density of the mixed crystals of -lauroyl lysine is 0.34 g / mL or less. The crystals of the present invention act as a stable pearlescent agent in a cleaning composition, and when a cleaning composition containing such crystals is used to clean skin or hair, it is comparable to N-lauroyl lysine having a bulk density of 0.35 g / mL or more. ε Compared with the crystals of -lauroyl lysine, the hair or skin care effect is improved. In addition, when the crystals of the present invention are contained in a cleaning product composition, the slimy feeling of the cleaning product during cleaning can be suppressed. In addition, when the crystals of the present invention are used in an emulsion, the moist feeling and gloss of the emulsion can be improved. In addition, by treating the powder with the crystals of the present invention, the softness of the touch of the powder and the gloss during coating can be improved, while giving the powder the functions of water repellency and oil repellency.

[0076] The bulk density is preferably from 0.01 to 0.32 g / mL, more preferably from 0.05 to 0.30 g / mL, further preferably from 0.1 to 0.25 g / mL.

[0077] The N of the present invention ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -The median particle size, average particle size and 90% particle size D90 of the mixed crystals of lauroyl lysine can be obtained 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 particle size refers to the particle size at the point where the distribution curve of the passing material cumulative percentage intersects with the 50% horizontal axis, and the 90% particle size D90 refers to the particle size at the point where the distribution curve of the passing material cumulative percentage intersects with the 90% horizontal axis. The average particle size refers to the arithmetic mean particle size of the distribution. "Number-based distribution" means that when calculating the frequency of each particle size of the particle size distribution, the number of particles is counted and the particle size distribution is calculated based on the number, and "volume-based distribution" means that when calculating the frequency of each particle size of the particle size distribution, the volume of particles assumed to be spherical is counted and the particle size distribution is calculated based on the value.

[0078] The present invention provides a composition comprising 0.01 to 99.9 mass % of the above-mentioned N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε - mixed crystals of lauroyl lysine. The composition of the present invention can be used as a composition for industrial use. For example, it can be incorporated into ink for printing or writing, pencil cores, etc. in order to improve the color development, adhesion and durability of the pigment. In addition, from the viewpoint of improving the anti-oxidation, water repellency and dispersibility of the pigment, it can be incorporated into coatings, tires or paper. In addition, it can also be used as a lubricant for machinery.

[0079] The composition of the present invention can also be used as a cosmetic or external preparation. The cosmetic or external preparation can be made into a preparation of any form applicable to, for example, a desired part (e.g., skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method. As cosmetics or external preparations for skin, lips, eyelashes, and nails, sunscreen products such as sunscreen, body powder, and spray can be cited, makeup cosmetics such as foundation, primer, body makeup, bronzer, face powder, nail care, blush, makeup base, and concealer, lip gloss, lip liner, lipstick, and other lip cosmetics, eyeliner, eye shadow, eyebrow pencil, mascara, and other eye makeup cosmetics, emulsion, lotion, cream, gel, beauty essence, and leave-on cosmetics, and facial mask. Examples of cosmetics or external preparations for hair include hair grooming agents, hair emulsions, hair treatments, hair conditioners, and hair lotions. Examples of cosmetics or external preparations for scalp include hair growth enhancers. Preferred cosmetics include color cosmetics, eye cosmetics, lip cosmetics, and leave-on cosmetics. Preferred external preparations include ointments, creams, mousse agents, and gels.

[0080] The composition of the present invention can be used as a cleaning composition. As a cleaning composition, as long as it is a cleaning composition containing a surfactant, it is not particularly limited, and the effect of the present invention can be exerted. As a more preferred example, skin cleaning products such as face wash, shower gel, soap, cleansing balm, cleansing oil, hair cleaning products such as shampoo, cleaning products for dishwashing, cleaning products for vegetable washing, cleaning products for machine cleaning, etc. can be cited.

[0081] The processing powder of the present invention can be obtained by combining "powder" and "N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine" are obtained by mixing. The powder is not particularly limited as long as it is a powder for industrial use or cosmetics (pigment, colorant, resin, pearlescent agent), and examples thereof include resin powders such as nylon beads, silicone beads, and polyethylene beads;

[0082] 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 oxide, pigment-grade titanium oxide, zirconium oxide, aluminum oxide, cerium oxide, microparticle titanium oxide, ultramicroparticle titanium oxide, microparticle zinc oxide, and microparticle iron oxide;

[0083] Silicon powders such as silicate (silicic acid (Al / Ca / Na), silicate (Na / Mg), sericite, mica, talc, kaolin, bentonite, aluminum silicate, magnesium silicate, cubic sodium aluminosilicate, silicon carbide, hydrous silicon dioxide and anhydrous silica (silicic anhydride) (bladed silica, non-porous silica, porous silica, porous silica, semi-porous silica, etc.);

[0084] Nylon powder, metal fatty acid soaps such as magnesium myristic acid, cellulose, cellulose particles, starch, wheat flour, wood powder, carbon black, black smoke, ultramarine, dark blue, carmine and other carbon-containing powders;

[0085] Metal salts of barium sulfate, plate-like barium sulfate, butterfly-like barium sulfate, calcium carbonate, magnesium carbonate, etc.;

[0086] Fluorine-containing powders of synthetic phlogopite (synthetic mica), synthetic phlogopite iron, etc.;

[0087] Boron-containing powders such as boron nitride;

[0088] Composite powders of pearlescent powder, colored pearlescent pigment, mica titanium, etc.;

[0089] Wax, pigment, lake, etc.

[0090] Furthermore, for powder, surface treatments such as organosilicon treatment, fluorine compound treatment, silane coupling agent treatment, silane treatment, organic titanate (salt) treatment, fatty acid treatment, metal soap treatment, oil treatment, amino acid treatment can be implemented. It should be noted that from the perspective of improving the water repellency and oil repellency after treatment, preferably a crystal or amorphous powder of resin powder, silicon-containing powder, metal oxide, carbon-containing powder, fluorine-containing powder, metal salt, boron-containing powder, composite powder.

[0091] The above-mentioned "powder" and "N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε-The mixing of the "mixed crystals of lauroyl lysine" can be implemented by mixing in a mixer for more than 1 minute. The mixing time is preferably more than 1 minute, and more preferably more than 10 minutes. From the viewpoint of not reducing the production efficiency and being able to produce inexpensively, the mixing time is preferably less than 60 minutes. As the mixer, a high-speed stirring mixer such as a Henschel mixer, a household mixer, a high-shear mixer, a W-type mixer, a CV-type mixer, a V-type mixer, a rocking mixer, or a container rotating mixer with a stirrer, a ribbon stirring type, a multi-shaft paddle type, a double-shaft planetary stirring type, a conical screw type mechanical stirring mixer, an air flow stirring mixer, a Julia mixer (Julia Mixer), a Nauta mixer (Nauta Mixer), a NOBILTA (dry particle composite equipment) and the like compression / shear / collision type mixer, etc., can be used. From the viewpoint of inexpensive production and versatility, a high-speed stirring mixer is preferred.

[0092] The mixing can also be carried out by mixing the "above-mentioned powder" and the "above-mentioned N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε The pulverization can be carried out by crushing the "above-mentioned powder" and the "above-mentioned N-lauroyl lysine mixed crystals" with a coarse crusher, a medium crusher or a pulverizer. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε The "mixed crystals of -lauroyl lysine" are crushed for more than 1 minute. The crushing time is preferably more than 1 minute, and more preferably more than 10 minutes. From the viewpoint of not reducing production efficiency and being able to produce inexpensively, the mixing time is preferably less than 60 minutes. As a coarse crusher, for example, a jaw crusher can be used; as a medium crusher, for example, a cutter mill, a grinder, etc. can be used; as a grinder, for example, a roller mill, a jet mill, a hammer mill, a pin mill, a tumbling mill, an attritor, a bead mill, an atomizer, etc. can be used, but it is not limited to these. From the viewpoint of inexpensive production and versatility, a jet mill, a pin mill, a drum mill, a sprayer, a bead mill, etc. are preferred.

[0093] In the "above powder" and "above N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N εIn the mixing process of the "mixed crystals of 1,2-lauroyl lysine", a solvent having a boiling point of 130°C or lower may be used in a range of 10% by mass or less based on the entire mixture, but it is preferably not used.

[0094] The treated powder contains N in an amount of 0.01 to 99.9 mass %, preferably 0.1 to 80 mass %, more preferably 1 to 15 mass %. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

[0095] Covered with N ε -lauroyl lysine crystals are treated with N ε In 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.

[0096] In addition, the coating is N ε -Octanoyl lysine and N ε -lauroyl lysine mixed crystals treated with N ε -Octanoyl lysine and N ε In the mixed crystals of -lauroyl lysine, 90% or more of the crystals have a particle size of 2.8 μm or less, preferably 2.5 μm or less, more preferably 1.8 μm or less.

[0097] As described above, using the N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε The powder treated with the mixed crystal of -lauroyl lysine has water repellency. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -lauroyl lysine mixed crystals treated powder has oil repellency. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε - The powder treated with mixed crystals of lauroyl lysine has a soft focus effect.

[0098] The treated powder can be prepared by a method comprising the following steps: mixing the N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε - mixed crystals of lauroyl lysine, wherein at least 40%, preferably 50%, of the powder surface area is Nε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Lauroyl lysine mixed crystal coating. The coating area ratio can be obtained by image analysis using software such as ImageJ.

[0099] The mixing can be implemented by mixing in a mixer for more than 1 minute. The mixing time is preferably more than 1 minute, and more preferably more than 10 minutes. From the viewpoint of not reducing production efficiency and being able to produce cheaply, the mixing time is preferably less than 60 minutes. As a mixer, a high-speed stirring mixer such as a Henschel mixer, a household mixer, a high-shear mixer, a W-type mixer, a CV-type mixer, a V-type mixer, a rock mixer, etc., a container rotating mixer or a container rotating mixer with a stirrer, a ribbon stirring mixer, a multi-axis paddle type, a double-axis planetary stirring mixer, a conical screw type mechanical stirring mixer, an air flow stirring mixer, a Julia mixer (Julia mixer), a Nota mixer, a NOBILTA (dry particle composite equipment) and the like compression / shear / collision type mixer, etc., from the viewpoint of cheap production and versatility, a high-speed stirring mixer is preferably used.

[0100] The mixing can also be carried out by mixing the "above-mentioned powder" and the "above-mentioned N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine" are pulverized. The pulverization can be carried out by using a coarse crusher, a medium crusher or a pulverizer to crush the "above-mentioned powder" and the "above-mentioned N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε The "mixed crystals of -lauroyl lysine" are crushed for more than 1 minute. The crushing time is preferably more than 1 minute, and more preferably more than 10 minutes. From the viewpoint of not reducing the production efficiency and being able to produce cheaply, the mixing time is preferably less than 60 minutes. As a coarse crusher, for example, a jaw crusher can be used; as a medium crusher, for example, a cutter, a grinder, etc. can be used; as a grinder, for example, a roller mill, a jet mill, a hammer mill, a nail disc grinder, a drum mill, an ultrafine grinder, a bead mill, a sprayer, etc. can be used, but it is not limited to these. From the viewpoint of cheap production and versatility, a jet mill, a nail disc grinder, a drum mill, a sprayer, a bead mill, etc. are preferred.

[0101] For the mixing, a solvent with a boiling point of 130°C or less may be used at a mass ratio of 10% or less relative to the entire treated powder. However, dry mixing without a solvent is preferred from the perspective of reducing environmental load and facilitating low-cost production.

[0102] The present invention provides a composition, wherein the treated powder is contained in an amount of 0.01 to 99.9% by mass. The composition of the present invention can be used as a composition for industrial use. For example, it can be incorporated into ink for printing or writing, a lead of a pencil, etc., in order to improve the color development, adhesion and durability of the pigment. In addition, from the viewpoint of improving the anti-oxidation, water repellency and dispersibility of the pigment, it can be incorporated into a coating, or into a tire or paper. In addition, it can also be used as a lubricant for machinery.

[0103] The composition of the present invention can also be used as a cosmetic or topical agent. The cosmetic or topical agent can be made into a preparation of any form applicable to, for example, a desired part (e.g., skin, hair, scalp, lips, eyes, eyelashes, eyelids, nails) according to a conventional method. As cosmetics or topical agents for skin, lips, eyelashes, and nails, sunscreen products such as sunscreen, talcum powder, and spray can be cited, makeup cosmetics such as foundation, primer, body makeup, bronzer, face powder, nail care, blush, makeup base, concealer, lip gloss, lip liner, lipstick and other lip cosmetics, eyeliner, eye shadow, eyebrow pencil, mascara and other eye makeup cosmetics, emulsion, lotion, cream, gel, beauty essence and other resident cosmetics, facial mask. As cosmetics or topical agents for hair, for example, hair modifiers, hair lotions, conditioners, hair conditioners, and hair liquids can be cited. As cosmetics or topical agents for the scalp, for example, hair growth agents can be cited. Preferred cosmetics include makeup cosmetics, eye makeup cosmetics, lip makeup cosmetics, and leave-on cosmetics. Preferred external preparations include ointments, creams, hair fixatives, and gels.

[0104] The composition of the present invention can be used as a cleaning composition. As a cleaning composition, there is no particular limitation as long as it contains a surfactant, and the effect of the present invention can be exerted. As more preferred examples, skin cleaning products such as face wash, shower gel, soap, skin cleansing cream, and face cleansing oil, hair cleaning products such as shampoo, cleaning products for dishwashing, cleaning products for vegetable washing, and cleaning products for machine cleaning can be cited.

[0105] The crystal or treated powder of the present invention may be formulated with the following ingredients as long as these effects are not impaired: preservatives such as caprylyl glycol, glyceryl caprylate, phenoxyethanol, chlorphenesin, pentylene glycol, hexylene glycol, methylparaben, propylparaben; antioxidants such as tocopherol, vitamin C, BHT, etc.; chelating agents such as sodium edetate; binders such as ethyl cellulose and hydroxypropyl cellulose; thickeners such as xanthan gum, carbomer, and polyacrylate cross-linked polymers; oil gelling agents such as dibutyl ethylhexanoyl glutamine, dibutyl lauroyl glutamine, dextrin palmitate, and polyamide-3; humectants such as glycerin and 1,3-butylene glycol; emulsifiers such as polyoxyethylene or polysorbate (Tween) emulsifiers, polyglycerol fatty acid esters, and sorbitan fatty acid esters; and oils such as ester oils and hydrocarbon oils.

[0106] Example

[0107] Method for determination of particle size distribution and particle size:

[0108] The particle size distribution was measured using a laser diffraction / scattering particle size distribution measuring device (HORIBA, Partica LA-950) using volume cumulative values. The results were analyzed using the software included with the device to obtain various particle sizes based on number distribution and volume distribution. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -The mixed crystals of lauroyl lysine were added to 5 g of isopropanol and exposed to ultrasonic waves for 30 minutes while stirring using an ultrasonic device with a power of 300 watts to break and disperse. An appropriate amount of the dispersion was added to 500 mL of isopropanol according to the steps of the device, and a dispersed sample of appropriate concentration was prepared while confirming the transparency. The sample was dispersed into primary particles while applying ultrasonic waves for 30 minutes while circulating at a flow rate of 10 mL / min. After degassing, the N in the sample was determined using a flow cell. ε - Particle size distribution and various particle sizes of lauroyl lysine crystals.

[0109] Method for determining bulk density:

[0110] N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε The mixed crystals of -lauroyl lysine were stirred in a mixer for more than 2 minutes to break them up. TM Specifically, a certain amount of N ε-Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -Lauroyl lysine mixed crystals are placed in the holder and conditioned according to the usage steps. ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -The mass of the mixed crystals of lauroyl lysine is determined by the following formula for bulk density;

[0111] Bulk density = adjusted mass / adjusted volume (g / mL).

[0112] [Fine powder N based on pulverization method ε -Preparation of Lauroyl Lysine Crystals]

[0113] (Comparative Example 1-1)

[0114] According to the following operation, N-2000 particles with a 90% particle size D90 (number-based distribution) of 15.7 μm were pulverized by dry pulverization in the absence of alcohol. ε -Lauroyl lysine crystals. ε -Lauroyl lysine crystals were mixed with 16 parts by weight of water, and the mixture was fed to a dry bead mill (manufactured by 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 beads, and the filling rate of the beads was set to 70% (v / v) relative to the volume. The powder obtained after pulverization was dried and crushed with a mixer to obtain the target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 1.

[0115] (Comparative Example 1-2)

[0116] According to the following operation, N-2000 particles with a 90% particle size D90 (number-based distribution) of 15.7 μm were pulverized by dry pulverization in the presence of a solvent. ε -Lauroyl lysine crystals. ε-Lauroyl lysine crystals were mixed with 1 part by weight of ethanol and then fed to a dry bead mill (manufactured by Ashizawa Finetech Co., Ltd., model SDA-120) at a rate of 0.5 kg / h for pulverization. Partially stabilized zirconia (PSZ) beads (diameter 1.5 mm) were used as beads, and the filling rate of the beads was set to 70% (v / v) relative to the volume. The powder obtained after pulverization was dried and crushed with a high-speed mixer to obtain the target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 1.

[0117] (Comparative Examples 1-3)

[0118] According to the following operation, N-2000 with a 90% particle size D90 (number-based distribution) of 15.7 μm was pulverized by wet pulverization in the presence of alcohol. ε -Lauroyl lysine crystals. ε - Pulverization of lauroyl lysine. The powder obtained after pulverization is dried and crushed with a high-speed mixer to obtain the target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 1.

[0119] (Comparative Examples 1-4)

[0120] According to the following operation, N-2000 nanoparticles with a 90% particle size D90 (number-based distribution) of 15.7 μm were pulverized by dry pulverization in the absence of alcohol or water. ε -Lauroyl lysine crystals. ε -Lauroyl lysine was crushed to obtain fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 1.

[0121] The 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.

[0122] [Table 1]

[0123] Table 1: Micro powder N ε - Particle size and physical properties of lauryl phthalolysine crystals

[0124]

[0125] [Micro powder N based on crystallization method ε -Lauroyl lysine crystals or N ε-Octanoyl lysine and N ε -Preparation of mixed crystals of lauroyl lysine]:

[0126] (Example 2-1)

[0127] 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 36.4 g of commercially available N ε -lauroyl lysine crystals were dissolved at the same temperature. Then, while maintaining the pH at 0.7 to 1.3, N was added dropwise over 75 minutes to a 0.1 mol / L aqueous hydrochloric acid solution (600 mL) cooled to below 10°C. ε -lauroyl lysine solution. After the addition was completed, 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 target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0128] (Example 2-2)

[0129] 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 36.4 g of commercially available N ε -lauroyl lysine crystals were dissolved at the same temperature. Then, while maintaining the pH at 0.8 to 1.1, N was added dropwise over 25 minutes to a 0.085 mol / L aqueous hydrochloric acid solution (150 mL) cooled to below 0°C. ε -lauroyl lysine solution. After the addition was completed, 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 target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0130] (Example 2-3)

[0131] In addition to using commercially available N ε -Octanoyl lysine crystals and N ε -Lauroyl lysine crystals replace the commercially available N ε -lauroyl lysine crystals, N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine (1:1). The bulk density and various particle sizes of the obtained mixture are shown in Table 2-2.

[0132] (Example 2-4)

[0133] In addition to using commercially available N ε -Octanoyl lysine crystals and N ε -Lauroyl lysine crystals replace the commercially available N ε -lauroyl lysine crystals, N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine (1:3). The bulk density and various particle sizes of the obtained mixture are shown in Table 2-2.

[0134] (Example 2-5)

[0135] In addition to using commercially available N ε -Octanoyl lysine crystals and N ε -Lauroyl lysine crystals replace the commercially available N ε -lauroyl lysine crystals, N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine (1:9). The bulk density and various particle sizes of the obtained mixture are shown in Table 2-2.

[0136] (Example 2-6)

[0137] In addition to using commercially available N ε -Octanoyl lysine crystals and N ε -Lauroyl lysine crystals replace the commercially available N ε -lauroyl lysine crystals, N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine (3:1). The bulk density and various particle sizes of the obtained mixture are shown in Table 2-2.

[0138] (Comparative Example 2-1)

[0139] According to the manufacturing example 1 described in Japanese Patent Application Laid-Open No. 8-337519, 30 g of N ε -lauroyl lysine was dissolved in 150 mL of 10% sodium hydroxide aqueous solution. The pH was maintained at 2-5 and the obtained N ε The solution of -lauroyl lysine was added dropwise to 200 mL of 2 mol / L hydrochloric acid aqueous solution while stirring at room temperature. After all the addition, 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 obtained white crystals were dried and crushed with a high-speed mixer to obtain the target fine powder Nε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0140] (Comparative Example 2-2)

[0141] According to the manufacturing example 2 described in 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 then 36.4 g of N was added after heating to about 50°C. ε -lauroyl lysine and dissolve it at the same temperature. Then, the solution was cooled to 25°C, the pH was maintained at 7-12, and 38.0 g of 17.5% hydrochloric acid was added dropwise while stirring at the same temperature for about 4 hours. After all the additions were made, 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 target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0142] (Comparative Example 2-3)

[0143] 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 36.4 g of N ε -lauroyl lysine was dissolved at the same temperature. Then, without controlling the pH of the reaction system, N was added dropwise over 25 minutes to a 1.01 mol / L aqueous hydrochloric acid solution (150 mL) continuously controlled at 25°C. ε -lauroyl lysine solution. After the addition was completed, 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 target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0144] (Comparative Example 2-4)

[0145] 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 36.4 g of N ε -lauroyl lysine was dissolved at the same temperature. Then, without controlling the pH of the reaction system, N was added dropwise over 25 minutes to a 1.01 mol / L aqueous hydrochloric acid solution (150 mL) continuously controlled at 5°C. εAfter the 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 obtained white crystals were dried and crushed with a high-speed mixer to obtain the target fine powder N ε -Lauroyl lysine crystals. The bulk density and various particle sizes of the obtained crystals are shown in Table 2-1.

[0146] 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 crystals, N ε -Octanoyl lysine crystals, N ε -Octanoyl lysine and N ε The particle size and physical properties of the mixed crystals of -lauroyl lysine are shown in Tables 2-1 and 2-2.

[0147] [Table 2-1]

[0148] Table 2-1: Micro powder N ε -Particle size and physical properties of lauroyl lysine crystals

[0149]

[0150] [Table 2-2]

[0151] Table 2-2: N ε -Octanoyl lysine and N ε - Particle size and physical properties of mixed crystals of lauroyl lysine

[0152]

[0153] (Example 3)

[0154] Various powders were treated according to 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. Figures 1 to 19 The evaluation results of water repellency are shown in FIG. Figures 20-24 The evaluation results of oil repellency are shown in FIG.

[0155] Evaluation of water repellency:

[0156] Weigh 5 g of solvent into a vial, and add 30 mg of untreated powder or various treated powders to the surface of the solvent from a height of 3 cm within 2 seconds. After standing for 60 minutes after addition, the amount of powder floating on the solvent was determined by visual observation and image analysis based on ImageJ. The more powder floating on the solvent, the more effectively the powder surface was covered by N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε-Lauroyl lysine mixed crystals are coated, and the powder surface is less wettable by the solvent, and the water repellency is higher.

[0157] Solvents for evaluating the water repellency of various powders were prepared as shown in Table 3 according to the properties of the powder surfaces.

[0158] [Table 3]

[0159] Table 3: Solvents used to evaluate the water repellency of various powders

[0160]

[0161] Evaluation of oil repellency:

[0162] The oils of the composition similar to sebum were uniformly mixed in the proportions shown in Table 4 to prepare liquid simulated sebum. 5 g of the simulated sebum was weighed into a tube bottle, 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 the addition was allowed to stand for a certain period of time, the amount of powder floating on the liquid sebum was determined by visual observation and image analysis based on ImageJ. The more powder floating on the liquid sebum, the more effectively the powder surface was covered by N ε -Lauroyl lysine crystals or N ε -Octanoyl lysine and N ε -The mixed crystals of lauroyl lysine are coated, making the powder surface less wettable by liquid sebum and more oil-repellent.

[0163] [Table 4]

[0164] Table 4

[0165] Oils quality% Caprylic / capric triglyceride 33.3 Octyldodecyl myristate 33.3 Oleic acid 20 Squalane 13.4 .

[0166] [Table 5-1]

[0167]

[0168] [Table 5-2]

[0169] Table 5-2: N for various powders ε - Details of the treatment method of lauroyl lysine crystals

[0170]

[0171] [Table 5-3]

[0172] Table 5-3: N for various powders ε - Details of the treatment method of lauroyl lysine crystals

[0173]

[0174] [Table 5-4]

[0175]

[0176] Treatment methods for powders based on simple mixing:

[0177] "Various powders" and "N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine" and stirred and mixed at room temperature. In addition, when the temperature in the mixer gradually rises due to the mixing operation, the maximum temperature in the mixer is controlled to be lower than 80°C.

[0178] Powder processing method based on wet processing method:

[0179] 5g of N ε -Lauroyl lysine was dissolved in a 1.5% alkaline aqueous solution, and 100 g of various powders were added to the resulting solution to suspend it (powder content 20% by weight), and stirred for 30 minutes. Next, hydrochloric acid was added to neutralize it to pH 7.0, and stirring was continued for 30 minutes. Then, it was filtered, repeatedly washed with water, and dried at 80°C for 30 hours. By crushing the dried body, N ε -Various powders coated with lauroyl lysine.

[0180] Processing method of mixed powders based on the use of composite processing machinery:

[0181] Using a hybridization system NHS-1-2L (manufactured by Nara Machinery), 5 g of N with a median particle size of 20 μm was added to 200 g of the powder. ε -lauroyl lysine crystals were mixed at a rotor peripheral speed of 100 m / s for 3 minutes.

[0182] Microscope observation of processing status:

[0183] After gold and platinum were deposited on the crystal obtained in Example 2-1, the surface was observed using a scanning electron microscope (JEOL JCM-6000PLUS) and an image of the surface state was recorded. The recorded image is shown in Fig.25 .

[0184] N coating on the powder surface ε - Calculation of particle size of lauroyl lysine crystals:

[0185] The treated powder of Example 3-19 was deposited with gold and platinum and then observed using a scanning electron microscope (JEOL JCM-6000PLUS). Based on the obtained image, 500 plate-like N ε - Particle size of lauroyl lysine crystals. N ε - In the lauroyl lysine crystals, N ε - The number of lauroyl lysine crystals was 483 (96.6%).

[0186] N coating on the powder surface ε -Octanoyl lysine and N ε -Calculation of particle size of mixed crystals of lauroyl lysine:

[0187] After the treated powder of Example 3-24 was evaporated with gold and platinum, it was observed with a scanning electron microscope (JEOL JCM-6000PLUS). The particle size of 500 plate-like crystals attached to the surface of the powder was measured based on the obtained image. Among all the crystals, the number of plate-like crystals with a particle size of less than 1.8 μm was 461 (92.2%), and the number of plate-like crystals with a particle size of less than 2.8 μm was 489 (97.8%).

[0188] Using N ε -Calculation of the coverage of the treated powder surface of lauroyl lysine crystals:

[0189] The treated powder of Example 3-19 was deposited with gold and platinum and then observed using a scanning electron microscope (JEOL JCM-6000PLUS). 2 The obtained powder image shows that the plate-like N ε -Lauroyl lysine crystals, and their area was calculated using ImageJ. The same process was performed on 20 powders. The results showed that 2 Powder image, average 0.67cm 2 (67%) by N ε -Lauroyl lysine coating.

[0190] (Example 4)

[0191] Various powders were mixed by a treatment method based on simple mixing of powders at the ratios shown in Table 6. The obtained mixed powder had good water repellency and oil repellency, had a soft touch, and was excellent in the sense of close fit to the skin.

[0192] [Table 6]

[0193] Table 6

[0194]

[0195] (Example 5-1)

[0196] Various powders were mixed by a treatment method based on simple mixing of powders at the ratios shown in Table 7. The obtained mixed powder had good water repellency and oil repellency, had a soft touch, and was excellent in the sense of close fit to the skin.

[0197] [Table 7]

[0198] Table 7

[0199]

[0200] (Comparative Example 5-1)

[0201] Various powders were mixed by a treatment method based on simple mixing of powders at the ratios shown in Table 8. The obtained mixed powders did not have sufficient water repellency and oil repellency, and also did not have sufficient soft touch and adhesion to the skin.

[0202] [Table 8]

[0203] Table 8

[0204]

[0205] (Comparative Example 5-2)

[0206] Various powders were mixed by a treatment method based on simply mixed powders at the ratios shown in Table 9. The obtained mixed powders had almost no water repellency and oil repellency, and also had insufficient soft touch and adhesion to the skin.

[0207] [Table 9]

[0208] Table 9

[0209]

[0210] (Example 6)

[0211] The various powders were mixed for 10 minutes using a collision type mill (Atomizer manufactured by Dalton Co., Ltd.) in the proportions shown in Table 10. The obtained mixed powder had good water repellency and oil repellency and a soft touch. Furthermore, the uniform color development of the pigment was also excellent.

[0212] [Table 10]

[0213] Table 10

[0214]

[0215] (Example 7)

[0216] Various powders were mixed by a treatment method based on simple mixed powders according to the ratios shown in Table 11. The water repellency and oil repellency of the obtained mixed powders were calculated as follows;

[0217] Water repellency = 100 × (amount of powder floating on the solvent after 60 minutes / amount of powder floating on the solvent at 0 minutes)

[0218] Oil repellency = 100 x (amount of powder floating on the solvent after 5 minutes / amount of powder floating on the solvent at 0 minutes).

[0219] The water repellency and oil repellency of the mixed powder were compared based on the values ​​obtained by the above formula and evaluated according to the following evaluation criteria.

[0220] <Evaluation of water repellency>

[0221] 1) Water repellency value is 60% or more: Very good (A)

[0222] 2) Water repellency value is higher than 30% and lower than 60%: slightly better (B)

[0223] 3) Water repellency value is higher than 10% and lower than 30%: Not good (C)

[0224] 4) The value of water repellency is less than 10%: completely bad (D).

[0225] <Evaluation of the degree of oil repellency>

[0226] 1) Oil repellency value is 50% or more: Very good (A)

[0227] 2) Oil repellency value is higher than 20% and lower than 50%: slightly better (B)

[0228] 3) Oil repellency value is higher than 5% and lower than 20%: Not good (C)

[0229] 4) The value of oil repellency is less than 5%: completely bad (D).

[0230] In addition, four professional evaluators evaluated the softness of the touch and the gloss during coating of each mixture according to the following criteria.

[0231] <Evaluation of Softness during Coating>

[0232] 1) The touch when applied is very soft, good... 4 points

[0233] 2) The touch is slightly soft when applied, good... 3 points

[0234] 3) The touch is a bit hard when applied, not very good... 2 points

[0235] 4) The touch when applied is hard and not good at all…1 point.

[0236] <Gloss during coating>

[0237] 1) After coating, a very good natural gloss is obtained...4 points

[0238] 2) Slightly glossy after coating...3 points

[0239] 3) After coating, the gloss is not very good...2 points

[0240] 4) No gloss was obtained after coating... 1 point.

[0241] The results are shown in Table 11.

[0242] Evaluation average score 3.5 or above: Very good (A)

[0243] Average evaluation score of 2.5 or above and below 3.5: Moderately good (B)

[0244] The average evaluation score is above 1.5 and below 2.5: Not very good (C)

[0245] Average rating score below 1.5: Not good at all (D).

[0246] [Table 11]

[0247]

[0248] (Example 8-1 and Comparative Example 8-1)

[0249] Using the components shown in Table 12, a cleaning composition was prepared as follows.

[0250] Component A is dispersed in component B at room temperature. Component C is then added and stirred at room temperature to form a uniform solution. Component D is then added and stirred with a homogenizer until uniform. Component E is added to adjust the pH to 5.4, and then component F is added and mixed uniformly to obtain a cleaning composition.

[0251] The obtained cleaning composition was stored for 1 month under a circulating temperature of -5°C to 40°C (for the temperature inside the warehouse, it was kept at -5°C for 12 hours, raised from -5°C to 40°C in 3 hours, kept at 40°C for 12 hours, cooled from 40°C to -5°C in 3 hours, and kept at -5°C for 12 hours. The temperature was changed repeatedly in this cycle.). The degree of pearlization of the composition before and after storage was confirmed by visual observation. The composition of Example 8-1 maintained the same degree of pearlescent effect as that immediately after preparation, while the composition of Comparative Example 8-1 almost failed to maintain the pearlescent effect.

[0252] In addition, four professional evaluators evaluated the hair and skin care effects of the cleaning compositions of Example 8-1 and Comparative Example 8-1 after use. As a result, all evaluators evaluated that the composition of Example 8-1 had higher hair and skin care effects than the composition of Comparative Example 8-1.

[0253] [Table 12]

[0254] Table 12 Cleaning product composition

[0255]

[0256] (Example 9-1 and Comparative Example 9-1)

[0257] A cleaning composition was prepared as follows using the components shown in Table 13. 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 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 cleaning composition.

[0258] Four professional evaluators evaluated the effect of the cleaning compositions of Example 9-1 and Comparative Example 9-1 in reducing the sticky feeling of the surfactant during use. As a result, all evaluators evaluated that the composition of Example 9-1 was more effective in reducing the sticky feeling of the surfactant during use than the composition of Comparative Example 9-1.

[0259] [Table 13]

[0260] Table 13 Cleaning product composition

[0261]

[0262] Evaluation of the soft focus effect of powder:

[0263] 50 mg of powder was evenly coated on black paper, and the light scattering properties of the powder were measured using a goniophotometer (GP-700) (Murakami Color Research Laboratory). The powder surface was irradiated with light at -45°, and the ratio of the intensity of light scattered at 45° and 0° (intensity at 45° / intensity at 0°) was calculated. The closer the ratio is to 1, the higher the soft focus effect of the powder can be evaluated. In addition, the light scattering performance of the powder was measured based on the N ε - The improvement rate of the soft focus effect of powders treated with lauroyl lysine crystals was compared.

[0264] [Table 14]

[0265] Table 14: Evaluation of the improvement of soft focus effect of powder

[0266]

[0267] From the results in Table 14, we can see that by using N ε -Lauroyl lysine crystal treatment improves the soft focus effect of the plate-like powder.

[0268] (Example 10-1 and Comparative Example 10-1)

[0269] Using the components shown in Table 15, lip cosmetics were prepared as follows.

[0270] 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. Furthermore, component C was added and heated and mixed at 90°C, and then dispersed on a three-roll mill, and component D was added. Component E was added and heated and mixed at 90°C, and then degassed. The mixture was filled into a mold at a filling temperature of 90°C, and then cooled and filled into a container.

[0271] 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 bleeding and the stability was also good.

[0272] [Table 15]

[0273] Table 15: Lip cosmetics

[0274]

[0275] (Example 11-1 and Comparative Example 11-1)

[0276] A leave-on cosmetic was prepared as follows using the components shown in Table 16. Component A and component B were heated and dissolved at 80°C, and then component A was added to component B while 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.

[0277] The leave-on cosmetic of Example 11-1 had better stability and antiseptic properties than Comparative Example 11-1. Furthermore, the moist feeling after application was excellent, and the glossiness was further improved by application.

[0278] [Table 16]

[0279] Table 16: Leave-on cosmetics

[0280]

[0281] (Example 12-1 and Comparative Example 12-1)

[0282] Using the components shown in Table 17, eye makeup cosmetics were prepared as follows.

[0283] After mixing component A for 10 minutes, component B was added to component A and mixed for 20 minutes. Component C was mixed for 10 minutes using a mixer (FM 10C / I manufactured by Nippon Coking Industry Co., Ltd.), then added to the mixture of component A + component B and mixed for 5 minutes. The resulting mixture was filled into a container and compressed using a press to obtain the target eye makeup cosmetics.

[0284] Four professional evaluators evaluated the pearly feeling, gloss, adhesion and color development of the eye makeup cosmetics of Example 12-1 and Comparative Example 12-1 after application. As a result, all the evaluators evaluated that the eye makeup cosmetics of Example 12-1 had a higher pearly feeling, gloss, adhesion and color development after application than the eye makeup cosmetics of Comparative Example 12-1. The eye makeup cosmetics of Example 12-1 can be prepared with a smaller amount of oil, so the feeling of use is excellent. In Example 12-1, the gloss of the pearlescent powder and the colored pearlescent pigment is not reduced, but the gloss is improved.

[0285] [Table 17]

[0286] Table 17: Eye makeup cosmetics

[0287]

[0288] (Example 13-1 and Comparative Example 13-1)

[0289] Color cosmetics were prepared as follows using the components shown in Table 18. 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 slowly added to component B + component C, and uniformly emulsified using a homomixer. After emulsification, component D was added and further mixed, and cooled to room temperature to obtain the target color cosmetics.

[0290] The color cosmetics of Example 13-1 have excellent emulsion stability, can improve gloss after application, and can improve uneven pigmentation compared to Comparative Example 13-1. Furthermore, the color cosmetics of Example 13-1 have improved makeup durability and good antiseptic properties, and have excellent moist feeling after application.

[0291] [Table 18]

[0292] Table 18: Makeup cosmetics

[0293]

[0294] (Example 14)

[0295] A foundation is prepared as follows using the ingredients shown in Table 19. Mix component B evenly. After mixing component A for 1 minute using a mixer, add component B to component A and mix for 30 seconds. Add 12 g of water / ethanol (mixing ratio of water:ethanol = 80:20) as a dispersion solvent to 8 g of the obtained mixture, and disperse while mixing. Weigh 13 g of the obtained dispersion into a container, and while pressing, fully absorb the water / ethanol as a dispersion solvent from above with tissue paper. Dry the compressed composition in the container at 80°C overnight to obtain the target foundation.

[0296] The foundation of Example 14 has excellent adhesion after application and excellent natural makeup effect. Furthermore, the product itself has good formability and beautiful color. Furthermore, the makeup film has fewer causes of makeup removal such as unevenness, oiliness, wrinkling, dullness, and disappearance due to changes over time.

[0297] [Table 19]

[0298] Table 19: Foundation

[0299]

[0300] (Example 15)

[0301] Using the components shown in Table 20, a composition for pencils was prepared as follows.

[0302] After mixing component A of the composition of Table 20 for 5 minutes using a mixer (FM 10C / I manufactured by Nippon Coke Industry Co., Ltd.), component B was added to component A and mixed for 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 resulting mixture, kneaded using a three-roll mill, and then filled into a container while heating, and calcined to solidify.

[0303] The pencil obtained in Example 15 had a lead that was not easily broken and had high glossiness. Furthermore, it had excellent color development properties.

[0304] [Table 20]

[0305] Table 20: Composition for pencils

[0306]

Claims

1. N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, wherein The 90% particle size D90 of the number-based distribution is 2.8 μm or less.

2. The N according to claim 1 ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, wherein The median particle size or average particle size of the volume-based distribution is 2.8 μm or less. 3.N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, wherein The bulk density is below 0.34 g / mL.

4. Non-crushed N ε - A method for producing long-chain acyl lysine crystals, wherein: include: Prepare to dissolve one or more N in an acidic or alkaline solvent containing one or more selected from water-soluble organic solvents and / or water. ε -long-chain acyl lysine, and adding the solution dropwise to an acidic solution having a pH of 0.2 or more and less than 2.0 at a temperature below 20°C to make N ε -Long chain acyl lysine crystals, N ε -Long-chain acyl lysine crystals are the N- ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

5. N according to any one of claims 1 to 3 ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, wherein The crystal or the mixed crystal is obtained by the production method according to claim 4.

6. N according to any one of claims 1 to 3 ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, wherein The crystal contains N at a ratio of 99 mass % or less. ε -Capryloyl lysine.

7. A composition, wherein The N according to any one of claims 1 to 3, 5 and 6 is contained in an amount of 0.01 to 99.9 mass %. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

8. A composition for industrial use, wherein: The N according to any one of claims 1 to 3, 5 and 6 is contained in an amount of 0.01 to 99.9 mass %. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

9. Cosmetics or external preparations, wherein: The N according to any one of claims 1 to 3, 5 and 6 is contained in an amount of 0.01 to 99.9 mass %. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

10. A cleaning composition, wherein: The N according to any one of claims 1 to 3, 5 and 6 is contained in an amount of 0.01 to 99.9 mass %. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine.

11. Processing of powders, wherein: The treated powder is prepared by mixing the powder and the N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -The mixed crystals of lauroyl lysine are obtained by mixing.

12. The treated powder according to claim 11, wherein: The powder includes: resin powder, silicon-containing powder, metal oxide, carbon-containing powder, fluorine-containing powder, metal salt, boron-containing powder, composite powder, crystalline or amorphous powder.

13. The treated powder according to claim 11 or 12, wherein: N coating on the powder surface ε - In the lauroyl lysine crystals, N ε - The ratio of lauroyl lysine crystals is 90% or more.

14. The treated powder according to claim 11 or 12, wherein: N coating on the powder surface ε -Octanoyl lysine and N ε In the mixed crystals of -lauroyl lysine, the proportion of crystals having a particle size of 2.8 μm or less is 90% or more.

15. The method for preparing a treated powder according to any one of claims 11 to 14, wherein: include: The N according to any one of claims 1 to 3, 5 and 6 is mixed in a powder at 5% by mass. ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Mixed crystals of lauroyl lysine, more than 40% of the powder surface area is N ε -Lauroyl lysine crystals, or N ε -Octanoyl lysine and N ε -Lauroyl lysine mixed crystals coated.

16. The preparation method according to claim 15, wherein: The mixing includes mixing by dry mixing without a solvent.

17. The preparation method according to claim 15 or 16, wherein: The mixing includes: mixing by a mixer for less than 60 minutes.

18. The treated powder according to claim 11 or 12, wherein: The treated powder is water repellent.

19. The treated powder according to claim 11 or 12, wherein: The treated powder has oil repellency.

20. The treated powder according to claim 11 or 12, wherein: The treated powder has a soft focus effect.

21. A composition, wherein The treated powder according to any one of claims 11 to 14 and 18 to 20 is contained in an amount of 0.01 to 99.99 mass %.

22. The composition according to claim 21, wherein The composition is an industrial composition, a cosmetic, an external agent or a cleaning product.

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