JP5211722B2 - Polypentamethylene sebacamide resin fine particles and cosmetics containing the same - Google Patents

Description

  The present invention relates to fine particles comprising polypentamethylene sebacamide resin and cosmetics using the same.

  Fine particles derived from polyamide resin have been used as a raw material for various cosmetics for a long time since they have good slipperiness with the skin. Various studies have also been made on the production method. Polyamide resin fine particles that have been put to practical use so far include polycaprolactam (nylon 6) and polylauryl lactam (nylon 12). In recent years, environmentally friendly materials have been demanded in various chemical products industries, but for cosmetics and paints, it has been a problem because it is difficult to collect after use. Under these circumstances, polypentamethylene sebacamide (nylon 510) is composed of 1,5-pentanediamine that can be synthesized from lysine and 60% sebacic acid that can be synthesized from castor oil. From the viewpoint of carbon neutrality. It can be said that it is an extremely remarkable polyamide resin.

  In addition, most of the conventional polyamide fine particles have a smooth or porous particle surface. In addition, since the surface form has irregularities but is spherical, there was no fine particle having an appropriate roughness on the skin surface in actual use.

  Patent Document 1 describes a method of precipitating polyamide resin fine particles by dissolving a synthetic linear polyamide resin in a solvent at a high temperature and then cooling the solution. As a specific example, a method of obtaining particles by dissolving polyhexamethylene adipamide (nylon 66) or polyhexamethylene sebacamide (nylon 610) in a glycol solvent and then cooling is described. .

  Patent Document 2 describes a method for producing amorphous nylon resin fine particles by dissolving an amorphous nylon resin in a mixed solvent of ethylene glycol and morpholine or dimethylacetamide and then cooling.

  Furthermore, Patent Document 3 discloses a method in which a crystalline polyamide resin is dissolved in a solvent at a high temperature and then cooled to induce phase separation, and a crystalline polyamide powder of independent monospherical particles is obtained by precipitation, separation, and filtration. Have been described.

  In Patent Document 4, a polyamide resin as a raw material is dissolved in a solvent that does not exhibit solubility below the boiling point under high temperature and high pressure, and the polyamide resin is precipitated by lowering the temperature or pressure to obtain polyamide resin fine particles. A method is described.

  Patent Document 5 describes a method for precipitating polyamide resin fine particles from a uniform solution obtained by mixing a non-solvent of a polyamide resin and water in an aromatic alcohol solution of a polyamide resin.

  Patent Document 6 describes a method for producing a spherical powder of a polyhydric alcohol-soluble substance. Examples of the alcohol-soluble substance include nylon resin. Nylon 6 resin is dissolved in ethylene glycol at a high temperature, A method of cooling precipitation is described.

  Patent Document 7 describes a method of depositing polyamide resin fine particles by using a two-component composition comprising a polyamide resin and another component polymer and adding a solvent which is a poor solvent to the polyamide resin. ing.

  Patent Document 8 describes an example of cosmetics using fine particles made of nylon 12 resin, and it is known to use nylon fine particles for cosmetics.

  However, although the method described in Patent Document 1 shows a method for producing fine particles made of nylon 66 or nylon 610, there is no description on the surface form of the fine particles obtained thereby, and the particle diameter and surface form are controlled. There is no mention of the possibilities or conditions to do. Moreover, it is not described about the use for cosmetics.

  The particles obtained by the method described in Patent Document 2 are particles made of amorphous nylon, and examples of producing particles made of nylon 6 resin and nylon 12 resin are also described in the examples. However, there is no description of the possibility or conditions for controlling the surface morphology and particle size.

  Polyamide fine particles obtained by the method described in Patent Document 3 have a smooth surface, and the surface morphology cannot be controlled. If an attempt is made to adjust the polymerization reaction conditions for production, fine particles having an appropriate roughness feeling such as an increase in particle diameter or significant aggregation of particles cannot be obtained. Moreover, it is not described about the use for cosmetics.

  The method for producing polyamide particles described in Patent Document 4 is a method for producing polyamide resin fine particles while polymerizing laurolactam or caprolactam in a fluid medium such as xylene. The fine particles obtained by this method have uneven surfaces. In this case, the fine particles are spherical, and fine particles having anisotropy that leads to an appropriate rough feeling cannot be obtained.

  According to the method described in Patent Document 5, a method for producing fine particles made of polyamide 6 is shown. However, the fine particles obtained by this method have a uniform spherical shape, and fine particles having a rough feeling cannot be obtained. Moreover, it is not described about the use for cosmetics.

  According to the method described in Patent Document 6, although the obtained nylon 6 resin fine particles have a concavo-convex surface, only fine particles having a uniform shape can be obtained, and therefore, fine particles having an appropriate roughness cannot be obtained. Moreover, it is not described about the use for cosmetics.

  According to the method described in Patent Document 7, a method for producing polyamide resin fine particles in which the particle diameter can be easily controlled is described. However, the fine particles having a moderate roughness can be obtained while only obtaining porous particles. I can't. Moreover, it is not described about the use for cosmetics.

The cosmetic described in Patent Document 8 is an example of a cosmetic using fine particles made of nylon 12 resin having a smooth surface, and an example of a cosmetic using nylon 510 resin fine particles having a moderate roughness is described. Absent.
US Pat. No. 2,639,278 JP-A-5-32795 JP-A-8-12765 JP-A-9-316206 JP 2002-143680 A JP-A-3-157430 JP 2000-136249 A JP-A-9-263523

The present inventors have discovered that obtaining a poly pentamethylene sebacamide resin particles having an appropriate roughness in the skin contact, also for its object to obtain a cosmetic with the poly pentamethylene sebacamide resin particles.

As a result of diligent research to solve the above-mentioned problems, the present inventors have precipitated from a solvent using a polypentamethylene sebacamide resin raw material, so that fine particles having spherical and anisotropic shapes have an uneven surface. It has been found that polypentamethylene sebacamide resin fine particles having an appropriate rough feeling can be obtained by mixing and the present invention has been achieved. That is, the present invention
(1) Polypentamethylene sebacamide resin fine particles, wherein the average deviation of the dynamic friction coefficient is 0.0038 to 0.0090,
(2) The polypentamethylene sebacamide resin fine particles according to (1), wherein the average particle size is 5 to 40 μm,
(3) The method for producing polypentamethylene sebacamide resin fine particles according to (1) or (2), wherein the polypentamethylene sebacamide resin is dissolved in a solvent and precipitated.
(4) The method for producing polypentamethylene sebacamide resin fine particles according to (3), wherein the polypentamethylene sebacamide resin is dissolved in a solvent, cooled and precipitated.
(5) The method for producing polypentamethylene sebacamide resin fine particles according to (3), wherein polypentamethylene sebacamide resin is dissolved in a solvent and precipitated by adding a poor solvent;
(6) The method for producing polypentamethylene sebamide resin fine particles according to any one of (3) to (5), wherein the solvent is alcohol or a mixture of alcohol and water,
(7) The alcohol is 1 -butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1- Butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, 2,2,2-trifluoroethanol, glycerin, ethylene glycol, diethylene glycol, 2-butene-1,4-diol, 1,2-propanediol 1,4-butanediol, 1,2-di (hydroxymethyl) benzene, 1,3-di (hydroxymethyl) benzene, 1,4-di (hydroxymethyl) benzene, cyclohexanol, o-cresol, m- Cresol, p-cresol, chlorophenol, triethylene glycol, and propylene glycol The method for producing polypentamethylene sebamide resin fine particles according to (6), which is at least one selected from coal,
(8) A cosmetic comprising the polypentamethylene sebamide resin fine particles according to (1) or (2),
(9) The cosmetic product according to (8), wherein the cosmetic product is a foundation, a cheek red, an eye shadow, a cleansing agent, a face-wash cream, a sunscreen cream, an antiperspirant, a pre-shave lotion, and a mascara.

  The polypentamethylene sebacamide resin fine particles of the present invention are obtained from plant-derived raw materials, and the average deviation of the friction coefficient is 0.0038 to 0.009. Cosmetics obtained using these particles are conventional nylons. Compared to resin fine particles, it has a moderate roughness in skin contact and can be used not only in foundations, cheeks, eye shadows, sunscreen creams, antiperspirants, pre-shave lotions, but also in face washing and cleansing.

  The polypentamethylene sebacamide resin used in the present invention is a polyamide resin composed of 1,5-pentanediamine and sebacic acid, and specifically a nylon 510 resin.

  In addition, as long as the mol% occupying in all the structural units is 5 mol% or less, the following polyamide units may be copolymerized.

  Polyamide units obtained from lactams such as undecaractam, dodecaractam, ε-caprolactam, 2-aminoacetic acid, 3-aminopropionic acid, 4-aminobutanoic acid, 5-aminopentanoic acid, 7-aminoheptanoic acid, 8-amino Polyamide units obtained from amino acids such as octanoic acid, 9-aminononanoic acid, 10-aminodecanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, tetramethylenediamine, hexamethylenediamine, 2-methyl-1,5-diminopentane , 3-methyl-1,5-diaminopentane, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamidecamethylenediamine, undecamethylenediamine, dodecamethylenediamine, o-xylylenediamine, m-ki Diamines such as lylenediamine, p-xylylenediamine, 1,2-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane and succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, 1,7 -Heptanedicarboxylic acid, 1,9-nonanedicarboxylic acid, 1,11-undecanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4- Examples thereof include polyamide units obtained from dicarboxylic acids such as cyclohexanedicarboxylic acid, or any combination of these polyamide units.

  Although there is no restriction | limiting in particular in the relative viscosity of the polypentamethylene sebacamide resin used by this invention, in order to maintain uniformity with the particle size of the polypentamethylene sebacamide resin fine particle obtained, it is 2.0-4. 0.0 is preferred. More preferably, it is 2.2-3.5, More preferably, it is 2.4-3.3. The relative viscosity mentioned here refers to a value measured with an Ubbelohde viscometer at 25 ° C. using a solution of 1 g of polypentamethylene sebacamide in 100 mL of 98% sulfuric acid.

  In the present invention, an average deviation of the coefficient of dynamic friction is adopted in evaluating the rough feeling on the skin required as a cosmetic. When this evaluation method is converted into actual use of cosmetics, a range of 0.0038 to 0.0090 is desirable, preferably 0.0040 to 0.0060, and more preferably 0.0042 in order to obtain a moderate roughness. ~ 0.0050.

  Here, the average deviation of the coefficient of dynamic friction was measured using a Kato Tech Co., Ltd. KES-SE-STP friction tester, and 0.01 g of fine particles were applied so as to be smooth to an area of 2 cm × 10 cm on the sample stage. It is a value measured by setting the moving speed to be 1 mm / min.

The average particle diameter of the polyamide resin particles of the present invention is in the range of 5~40μm terms of sense of touch with the skin obtained cosmetically preferably 5 to 30 [mu] m, more preferably 5～25Myu m desirable. The average particle child size here refers to a 50% median diameter measured by a laser diffraction scattering method. By setting the average particle size within this range, it is preferable because a product having an excellent usability as a cosmetic product can be obtained.

  Next, a method for producing the polypentamethylene sebacamide resin fine particles of the present invention will be described below.

The polypentamethylene sebacamide resin is immersed in a solvent, and the polypentamethylene sebacamide resin is dissolved while heating and stirring at about 80 to 300 ° C. The dissolution temperature is preferably 100 to 280 ° C, more preferably 120 to 250 ° C. If the temperature is too low, the polypentamethylene sebacamide resin will not dissolve sufficiently, or even if dissolved, the particle size will be non-uniform during precipitation, or the particles will tend to form in a significantly fused form. Show. On the other hand, if the temperature is too high, the polypentamethylene sebacamide resin is decomposed and colored yellow or the particle diameter tends to be non-uniform. At this time, it is preferable to carry out in an atmosphere of an inert gas such as nitrogen, argon or carbon dioxide gas so that the polypentamethylene sebacamide resin is not oxidized and deteriorated. The concentration of the polypentamethylene sebacamide resin when dissolved is preferably 5 to 50% by weight, more preferably 10 to 40% by weight, and particularly 10 to 30% by weight. If the concentration is too low, the particles become too fine and the resulting fine particles tend to agglomerate secondary. On the other hand, when the concentration is too high, the particle diameter tends to be too large, or the particles tend to show a shape in which the particles are significantly fused during precipitation. The polypentamethylene sebacamide resin is dissolved and then precipitated.
As a method of precipitation, it is naturally cooled at room temperature, the whole container is cooled in a place controlled at a constant temperature, or water, air, or inert gas is applied around the container. By cooling in 1 to 60 minutes, the dissolved polypentamethylene sebacamide resin is precipitated as spherical particles. When slowly cooled, particles having a large particle diameter can be obtained, but care must be taken because the particles may be fused significantly. On the other hand, when cooled rapidly, particles having a small particle diameter can be obtained, but care must be taken because the particles may be considerably fused. The solution cooling program varies depending on the target particle size, the container to be used, the concentration of the polypentamethylene sebacamide resin solution, and the like, and therefore needs to be appropriately adjusted.

For example, in the case of polypentamethylene sebacamide resin fine particles having an average particle diameter exceeding 40 μm, “the polypentamethylene sebacamide solution concentration is preferably 5% by weight, and the cooling rate is preferably 0.1 ° C./min or less”. obtained by cooling in the conditions, when the average particle child size poly pentamethylene sebacamide resin fine particles below 5 [mu] m, the poly pentamethylene sebacamide solution concentration preferably 5 to 10 wt%, the cooling rate It can be obtained by cooling at 100 ° C./min or more. The poly case of precipitating a pentamethylene Se preferred average particle a son diameter 5.0~40.0μm conditions sebacamide resin fine particles, preferably 5 to 30 weight poly pentamethylene sebacamide solution concentrations of the present invention %, And the cooling rate is 0.1 ° C./min to 100 ° C./min.

  The precipitated polypentamethylene sebacamide resin fine particles are separated as a cake by centrifugation, and the resulting cake is vacuum-dried to obtain pure polypentamethylene sebacamide resin fine particles.

The alcohol used in the present invention is a compound having one or more hydroxy groups in one molecule. Specifically , 1 -butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1- Butanol, 2-methyl-2-butanol, 3-methyl-2-butanol, 2,2,2-trifluoroethanol, glycerin, ethylene glycol, diethylene glycol, 2-butene-1,4-diol, 1,2-propanediol 1,4-butanediol, 1,2-di (hydroxymethyl) benzene, 1,3-di (hydroxymethyl) benzene, 1,4-di (hydroxymethyl) benzene, cyclohexanol, o-cresol, m- Cresol, p-cresol, chlorophenol, triethylene glycol, propylene glycol, etc. And a mixture of one or more of these. Among these, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, propylene glycol, o-cresol, m-cresol, and p-cresol are preferably used.

  When the polypentamethylene sebacamide resin is dissolved in alcohol or a mixture of alcohol and water, a small amount of an alkali compound may be added to promote dissolution. Specific examples include alkali metal, alkaline earth metal hydroxides, carbonates, hydrogen carbonates, and organic acid salts. More specifically, sodium hydroxide, calcium hydroxide, magnesium hydroxide, water, and the like. Potassium oxide, lithium hydroxide, sodium carbonate, calcium carbonate, magnesium carbonate, potassium carbonate, lithium carbonate, sodium bicarbonate, calcium bicarbonate, magnesium bicarbonate, potassium bicarbonate, lithium bicarbonate, sodium acetate, calcium acetate, magnesium acetate , Potassium acetate, lithium acetate and the like. Particularly preferred is calcium carbonate. The amount used is 0.001 to 10% by weight, preferably 0.01 to 5% by weight, more preferably 0.1 to 2% by weight, based on 100% by weight of the polypentamethylene sebacamide resin used.

  Moreover, when using the alkali compound as described above, it is preferable to neutralize the polypentamethylene sebacamide resin fine particles before separating them, and the neutralization can be achieved by adding an acidic compound. Specific examples include mineral acids, organic acids, and more specifically, hydrochloric acid, sulfuric acid, nitric acid, sulfurous acid, nitrous acid, hypochlorous acid, hypobromous acid, phosphoric acid, polyphosphoric acid, phosphorous acid, and the following. Examples include phosphorous acid, formic acid, acetic acid, propionic acid, butyric acid, and caproic acid. Particularly preferred is sulfuric acid. The amount used is an amount necessary to neutralize the alkali compound used previously.

  Moreover, regarding the precipitation method of the polypentamethylene sebacamide resin fine particles described above, there is a method using a poor solvent in addition to cooling. In this case, an aromatic alcohol is preferable as a solvent for the polypentamethylene sebacamide resin, and specifically, o-cresol, m-cresol, p-cresol, and chlorophenol are preferable. The polypentamethylene sebacamide resin concentration in the solution is 0.1 to 30% by weight, preferably 0.2 to 25% by weight. On the other hand, as the poor solvent, those in which the aromatic alcohol solvent and water are at least partially compatible are preferable, and linear alcohols, ketones and the like are preferable. It is also important to be compatible with water. For example, methanol, ethanol, propanol, acetone and the like are preferable. Further, the total weight of the poor solvent and water is preferably larger than the weight of the aromatic alcohol solution of the polypentamethylene sebacamide resin. The ratio of the poor solvent to water is preferably 2 to 90% by weight of water.

  In order to add a homogeneous solution in which a poor solvent and water are mixed to an aromatic alcohol solution of polypentamethylene sebacamide resin, the poor solvent is added to the aromatic alcohol solution of polypentamethylene sebacamide resin. Add water, then add water, mix poor solvent and water, then add polypentamethylene sebacamide resin aromatic alcohol solution, add water to polypentamethylene sebacamide resin aromatic alcohol solution An example is a method of adding a poor solvent after mixing. Any method may be used as long as the uniformity of the solution is maintained, but an addition order in which an aromatic alcohol solution of polypentamethylene sebacamide resin is added after mixing a poor solvent and water is preferable. The proportion in which the three components of the aromatic alcohol solution of the polypentamethylene sebacamide resin of the present invention, the poor solvent, and water are compatible is important.

  With the obtained uniform solution, polypentamethylene sebamide resin fine particles can be deposited after a certain period of time. The time for forming a uniform solution is, for example, about 0.1 second to 120 minutes. Even temporarily, it is important that the three components form a uniform solution. If necessary, appropriate stirring may be added.

  The temperature at which the polypentamethylene sebacamide resin fine particles are precipitated from the three-component solution is preferably 10 to 60 ° C. Depending on the temperature, the solvent composition range in which the three-component solution becomes uniform may be widened. When the temperature is lower than 10 ° C., the region where the three-component solution is uniform may be narrowed. When the temperature is higher than 60 ° C., the vapor pressure of the solvent is increased, which is not preferable.

  The precipitated polypentamethylene sebacamide resin fine particles can be isolated from the solution by a usual method such as decantation, centrifugation, or filtration. For example, a liquid in which polypentamethylene sebacamide resin fine particles are suspended may be further diluted with methanol and centrifuged. Alternatively, the centrifugation may be repeated after washing with methanol several times. Next, pure polypentamethylene sebamide resin fine particles are obtained by subjecting to hot air drying or vacuum drying.

Poly pentamethylene sebacamide resin fine particles obtained in the present invention, the shape is spherical shape, since the uniform particle size, is useful as a base material for cosmetics. Specific cosmetics include foundations, cheeks, eye shadows, cleansing agents, facial cleansing creams, sunscreen creams, antiperspirants, pre-shave lotions, after-shave lotions, funny, lotions, packs, massage creams, emulsions, moisturizing creams, Essence, Lipstick, Eyeliner, Nail Enamel, Soap, Bathing Agent, Shampoo, Rinse, Hair Treatment, Sun Oil, Depigmenting / Hair Removal Cream, Insect Repellent, Insect Repellent, Hair Liquid, Pomade, Hair Color Agent, Cologne, Shampoo, It is useful for rinsing and hair styling agents, but is particularly useful for foundations, cheeks, eye shadows, cleansing agents, facial creams, sunscreen creams, antiperspirants, and pre-shave lotions.

  In addition, many of the polyamide resin fine particles known so far have a relatively smooth surface and low oil absorption, but like some of the polyamide resin fine particles, the polypentamethylene sebacamide resin fine particles of the present invention The surface is uneven and the oil absorption is high. Therefore, it is superior in dispersibility in an aqueous solvent as compared with conventional polyamide resin fine particles.

  Therefore, when the polypentamethylene sebacamide resin fine particles of the present invention are used in cosmetics such as foundations, a refreshing feel while keeping a moist feeling, a refreshing feeling, a smooth feeling, a smooth feeling, a feeling of fitting ( There is an advantage of giving a feeling like familiarity. In addition, the water absorption property of the polypentamethylene sebacamide resin and the high oil absorption property of the particles of the present invention prevent the cosmetic from collapsing and make the makeup last a long lasting effect, and it is uniform based on slipperiness and good dispersibility. Effects such as smooth finish, soft focus (easy to blur the wrinkles), and natural finish. In addition, it has the advantage of excellent dispersibility when dispersed in oils, and has the potential to create cosmetics with a new feel that has never been seen before.

  EXAMPLES Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.

  Characteristic evaluation of the polypentamethylene sebacamide resin fine particles obtained in the following examples and comparative examples was performed as follows.

  Morphological observation with a scanning electron microscope: Observation was performed using JSM-6360LV manufactured by JEOL Datum.

Average particle size: Using Microtrac Inc. 9.0 L (MT3000), as a dispersion medium of ethanol - were determined using the Le, average particle child size 50% median diameter (cumulative median diameter) (unit: [mu] m) and did.

  Average deviation of dynamic friction coefficient: Using Kato Tech Co., Ltd. KES-SE-STP friction tester, 0.01 g of fine particles were applied to an area of 2 cm × 10 cm on the sample stage so as to be smooth, and the moving speed of the sample stage was 1 mm / It was set and evaluated to be min.

[Production of polyamide resin]
[Reference Example 1] Production of polypentamethylene sebacamide resin 35.0 g of 1,5-pentanediamine in 30 wt% aqueous solution (content of 1,5-pentanediamine of 0.103 mol), 20.8 g of sebacic acid (0.103 mol) Was placed in a test tube, placed in an autoclave, sealed, and purged with nitrogen. The jacket temperature was set to 285 ° C. and heating was started. After the can internal pressure reached 17.5 kg / cm ² , the can internal pressure was maintained at 17.5 kg / cm ² for 3 hours. Thereafter, the jacket temperature was set to 295 ° C., and the internal pressure of the can was released to normal pressure over 2 hours. Thereafter, the heating was stopped when the temperature inside the can reached 270 ° C. After allowing to cool to room temperature, the test tube was removed from the autoclave to obtain a polypentamethylene sebamide resin. The molten polymer was discharged into a water bath and pelletized with a strand cutter. The obtained pellets were vacuum-dried at 80 ° C. for 12 hours. The relative viscosity was 2.70 measured at 25 ° C. using an Ostwald viscometer in a 98% concentrated sulfuric acid solution of 1% by weight of polyamide resin.

[Reference Example 2] Production of polycaproamide resin A 30 L stainless steel autoclave was charged with 10 kg of ε-caprolactam, 43 g of benzoic acid, and 200 g of ion-exchanged water, and after nitrogen substitution, sealed and heated and stirred at 250 ° C. for 10 hours. Thus, a polycaproamide resin was prepared. The obtained polycaproamide resin was drawn into a strand from the lower part of the autoclave and cut into pellets. The pellets were extracted in boiling water for 15 hours and then vacuum dried at 80 ° C. for 24 hours. The relative viscosity ηr of the obtained polycaproamide resin was 2.35.

[Production of polyamide resin fine particles]
<Example 1> Production of polypentamethylene sebacamide resin fine particles (A-1) To 100 g of the polypentamethylene sebacamide resin produced in Reference Example 1, 525 g of propylene glycol was added, and 180% in a nitrogen atmosphere. Stir at ° C. After stirring for 30 minutes, the polypentamethylene sebacamide resin was dissolved, so the solution was poured into a stainless steel vat kept at 166 ° C. and left at that temperature for 30 minutes. Since the polypentamethylene sebacamide particles were precipitated, the precipitate was centrifuged to remove propylene glycol, and a polypentamethylene sebacamide resin fine particle cake was obtained. The cake was taken out, spread on a bat and dried in a vacuum dryer at 80 ° C. for 24 hours.

  Scanning electron micrographs of the obtained fine particles are shown in FIG. 1 and FIG. It can be seen that spherical and anisotropic fine particles are mixed, and the surface has fine irregularities. With these forms, a desired rough feeling can be obtained.

  The average particle diameter of the fine particles was 20.9 μm, and the average deviation (roughness) of the dynamic friction coefficient was 0.0051.

<Example 2> Production of polypentamethylene sebacamide resin fine particles (A-2) 10 g of polypentamethylene sebacamide resin produced in Reference Example 1 was dissolved in 190 g of m-cresol, and 1000 g of methanol and 200 g of water were dissolved in this solution. Were mixed and stirred, and after about 2 minutes, polypentamethylene sebacamide resin fine particles were precipitated. Further, the mixture was allowed to stand for 24 hours to complete the precipitation. Thereafter, the mixture was centrifuged and washed with methanol and acetone to separate the polypentamethylene sebacamide resin fine particles into a cake. The cake was taken out, spread on a bat and dried in a vacuum dryer at 80 ° C. for 24 hours.

  The obtained polypentamethylene sebacamide resin fine particles are mixed with fine particles having a true spherical shape and anisotropy in the same manner as in Example 1, and there are fine irregularities on the surface. A feeling of roughness can be obtained.

  The average particle diameter of the fine particles was 20.1 μm, and the average deviation (roughness) of the dynamic friction coefficient was 0.0053.

<Comparative example 1> Manufacture of polycaproamide resin fine particles (B) To 100 g of the polycaproamide resin manufactured in Reference Example 2, 525 g of ethylene glycol was added and stirred at 180 ° C under a nitrogen atmosphere. Since the polycaproamide resin dissolved after stirring for 30 minutes, the solution was poured into a stainless steel vat kept at 166 ° C. and left at that temperature for 30 minutes. Since the polycaproamide resin fine particles were precipitated, the precipitate was centrifuged to remove ethylene glycol to obtain a cake of polycaproamide resin fine particles. The cake was taken out, spread on a bat and dried in a vacuum dryer at 80 ° C. for 24 hours.

  Scanning electron micrographs of the obtained fine particles are shown in FIG. 3 and FIG. Although the surface morphology was very uneven, the particles were almost spherical.

  The average particle diameter of the fine particles was 13.1 μm, and the average deviation (roughness) of the dynamic friction coefficient was 0.0037.

<Comparative Example 2> Production of polylauramide resin fine particles (C-1) 190 g of anhydrous laurolactam, 1000 mL of liquid paraffin, and 3.8 g of potassium stearate were placed in a four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser. After the inside was replaced with dry nitrogen, it was heated to 160 ° C., and laurolactam was dissolved in liquid paraffin. While maintaining the solution at 160 ° C., 7.6 g of caprolactam potassium salt and 1.12 g of phosphorus trichloride were added and stirred for 2 hours. After cooling the solution to room temperature, the solution was filtered, and the resulting polylauramide resin fine particles were isolated. The particles were washed with n-butanol, further washed with water, and dried in a vacuum dryer overnight. 150g of the particles are obtained, the relative viscosity of the particles 2.91, an average particle child size was 10.1.

  Further, scanning electron micrographs of the obtained polylauramide resin fine particles are shown in FIG. 5 and FIG. It can be seen that the surface form is extremely smooth and is a spherical fine particle. The average deviation (roughness) of the dynamic friction coefficient in the fine particles was 0.0025.

<Comparative Example 3> Production of polylauramide resin fine particles (C-2) 190 g of anhydrous laurolactam, 980 mL of liquid paraffin, and 3.8 g of potassium stearate were placed in a four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser. After the inside was replaced with dry nitrogen, it was heated to 160 ° C., and laurolactam was dissolved in liquid paraffin. While maintaining the solution at 160 ° C., 8.6 g of caprolactam potassium salt and 1.12 g of phosphorus trichloride were added and stirred for 2 hours. After cooling the solution to room temperature, the solution was filtered, and the resulting polylauramide resin fine particles were isolated. The particles were washed with n-butanol, further washed with water, and dried in a vacuum dryer overnight. 150g of the particles are obtained, the relative viscosity of the particles 3.95, an average particle child size was 5.1 .mu.m.

  Further, scanning electron micrographs of the obtained polylauramide resin fine particles are shown in FIG. 7 and FIG. It can be seen that the surface form is extremely smooth and is a spherical fine particle. The average deviation (roughness) of the dynamic friction coefficient in the fine particles was 0.0034.

<Examples 3-6, Comparative Examples 4-9> Application to Cosmetics Using the polyamide resin fine particles obtained in Examples 1-2 and Comparative Examples 1-3, milky white liquid for test and white UV were as follows. Lotion was manufactured.

Milky white [Prescription]
Among the following raw materials, vegetable emulsified wax, jojoba oil, xanthan gum and silk powder were purchased from Natural Laboratories. Other raw materials were purchased as reagents.
Vegetable emulsified wax (Arachides-20 and stearyl alcohol mixture): 20 g
Jojoba oil: 20g
Xanthan gum: 20g
Distilled water: 400mL
Polyamide resin fine particles of Examples and Comparative Examples: 10 g
Silk powder: 10g

[Production method]
Jojoba oil and emulsified wax are heated to 50-60 ° C. with stirring to completely dissolve (liquid A). Distilled water, polyamide resin fine particles, and silk powder are heated to 50 to 60 ° C. with stirring and stirred for 2 minutes (Liquid B). Mix half of the B liquid with the A liquid at a temperature of 50-60 ° C. and stir well. To this mixture, xanthan gum is added little by little with stirring, and the remaining half of solution B is added with stirring. The mixture was stirred well and stirred uniformly so that no lumps were formed.

White UV lotion [Prescription]
Of the following raw materials, plant placenta, fine titanium oxide, and talc were purchased from Natural Laboratories. Other raw materials were purchased as reagents.
Plant placenta (manufactured by Natural Laboratories): 14 drops fine particle titanium oxide (average particle size 0.03 μm): 10 g
Polyamide resin fine particles of Examples, Comparative Examples and Reference Examples: 10 g
Talc: 2.5g
Glycerin: 10mL
Distilled water: 190 mL

[Production method]
Distilled water, placenta, and glycerin were added to a mixture of titanium oxide, polyamide resin fine particles, and talc and stirred well. Since it separated into two layers when allowed to stand, the container was vigorously shaken before use and used uniformly.

  An appropriate amount of the above-mentioned milky white solution was applied to the back of the hand, and a refreshing feel while maintaining a moist feeling, an excellent refreshing feeling, a smooth feeling, a smooth feeling, and a fit feeling (familiarity) were investigated. For each touch, good: 5 points, slightly good: 4 points, normal: 3 points, slightly bad: 2 points, bad: 1 point, and the evaluation results of 20 people were averaged. The same investigation was conducted on the white UV lotion. Table 1 shows the evaluation results of the milky white liquid, and Table 2 shows the evaluation results of the white UV lotion.

  From Examples 3 to 6 and Comparative Examples 4 to 9, it can be seen that cosmetics using the polypentamethylene sebacamide particles of the present invention are excellent in touch when in contact with the skin.

2 is a scanning electron micrograph of polypentamethylene sebamide resin fine particles obtained in Example 1. FIG. (500 times) It is the scanning electron micrograph which expanded a part of FIG. (2000 times) 2 is a scanning electron micrograph of polycaproamide resin fine particles obtained in Comparative Example 1. FIG. (500 times) It is the scanning electron micrograph which expanded a part of FIG. (5000 times) 2 is a scanning electron micrograph of polylauramide resin fine particles obtained in Comparative Example 2. FIG. (1000 times) 6 is an enlarged scanning electron micrograph of part of FIG. 5. (10,000 times) 4 is a scanning electron micrograph of polylauramide resin fine particles obtained in Comparative Example 3. FIG. (1000 times) It is the scanning electron micrograph which expanded a part of FIG. (10,000 times)

Claims (9)

Polypentamethylene sebacamide resin fine particles having an average deviation of a dynamic friction coefficient of 0.0038 to 0.0090. 2. The polypentamethylene sebacamide resin fine particles according to claim 1, having an average particle diameter of 5 to 40 μm. The method for producing polypentamethylene sebacamide resin fine particles according to claim 1 or 2, wherein the polypentamethylene sebacamide resin is dissolved in a solvent and precipitated. 4. The method for producing polypentamethylene sebacamide resin fine particles according to claim 3, wherein the polypentamethylene sebacamide resin is dissolved in a solvent and cooled to be precipitated. The method for producing polypentamethylene sebacamide resin fine particles according to claim 3, wherein the polypentamethylene sebacamide resin is dissolved in a solvent and precipitated by adding a poor solvent. The method for producing fine polypentamethylene sebacamide resin particles according to any one of claims 3 to 5, wherein the solvent is alcohol or a mixture of alcohol and water. Alcohol is 1 -butanol, 2-butanol, 2-methyl-1-propanol, 2-methyl-2-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 2 -Methyl-2-butanol, 3-methyl-2-butanol, 2,2,2-trifluoroethanol, glycerin, ethylene glycol, diethylene glycol, 2-butene-1,4-diol, 1,2-propanediol, 1, 4-butanediol, 1,2-di (hydroxymethyl) benzene, 1,3-di (hydroxymethyl) benzene, 1,4-di (hydroxymethyl) benzene, cyclohexanol, o-cresol, m-cresol, p -Cresol, chlorophenol, triethylene glycol, and propylene glycol The method for producing fine polypentamethylene sebamide resin particles according to claim 6, which is at least one selected from the group consisting of: Cosmetics containing the polypentamethylene sebacamide resin fine particles according to claim 1 or 2. The cosmetic according to claim 8, wherein the cosmetic is any one selected from a foundation, a blusher, an eye shadow, a cleansing agent, a face washing cream, a sunscreen cream, an antiperspirant, a pre-shave lotion, and a mascara.

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