Humectants containing oil and components for external skin application that include them.

Abstract

DEPCT64 A humectant containing oil and other components for external use on the skin. In addition, a specific characteristic of this invention is that it contains an esterification product. Component A and component B, or the esterification product containing component A and component B. And the components C and the esterification products have a pH value of 0-160. Milligrams of KOH / gram and the mass ratio of fatty acid residues obtained from component B and fatty acid residues. Fats obtained from component C in fatty acid residues which make up the esterification products. Elements A, B, and C are equal to 99.9:0.1-45:55 elements. A: Polyhydric alcohols that are dipentaerythritol, erythritol, or sorbitan; B: Components. One or more fatty acids, or equal to two, selected from straight-chain saturated fatty acids with a certain number of carbon atoms. 6-10 atoms, C composition: 1 or more fatty acids, or equal to 2 types selected from fatty acids. Containing 6-28 carbon atoms (excluding element B). -----------------------------------------------------------

Description

Oil-based moisturizer and topical skin composition containing the same

[0001] The present invention relates to an esterified product composed of a specific polyhydric alcohol and a fatty acid, an oil-based moisturizer composed of the esterified product, and a topical skin composition containing the oil-based moisturizer.

[0002] In the field of cosmetics, water-soluble moisturizers such as polyethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol, and hyaluronic acid have been commonly used as moisturizers for preventing skin dryness and imparting moisture to the skin (see Patent Document 1). In addition, many water-soluble moisturizers such as various natural extracts and extracts have been developed. However, after these water-soluble moisturizers are applied to the skin, they may flow off the skin due to sweating or being washed away by water, and as a result, skin moisturization may not be maintained.

[0003] On the other hand, as oil-based moisturizers, although there are few examples, oil agents such as petrolatum are known. Oil agents can suppress moisture evaporation from the skin surface by occluding the skin. Therefore, particularly petrolatum is widely used as a base for topical skin compositions for treating, preventing or improving symptoms caused by skin dryness, specifically mainly as a base for ointments (see Patent Document 2).

[0004] Certainly, petrolatum, which is oily, has the merit of being difficult to flow off by sweating or being washed away by water. However, due to the nature of petrolatum itself, it has a sticky feeling when applied to the skin and poor skin affinity, so it may feel uncomfortable when used. Furthermore, if the petrolatum applied to the skin is wiped off by contact with clothes or the like, its occluding effect cannot be exerted, and as a result, skin moisturization may not be maintained.

[0005] As an evaluation method for the moisturizing effect, evaluation methods based on the amount of transepidermal water loss (for example, see Patent Document 3) or the amount of stratum corneum moisture (for example, see Patent Documents 4 and 5) have been common. In fact, many patent documents have been issued that evaluate the moisturizing effect by the amount of stratum corneum moisture.

[0006] Furthermore, in Patent Document 6, the moisturizing effect of the beauty serum is evaluated by sensory evaluation, specifically whether the subject feels moisturized after applying it to the surface of their skin. In other words, the moisturizing effect is evaluated solely by sensory evaluation, and the water content of the stratum corneum is not investigated. Therefore, it is unclear whether the application of the beauty serum actually improved the skin's moisturizing function.

[0007] JP-A-11-209223 Patent No. 4385170 Patent No. 5954935 Patent No. 5572263 Patent No. 5917043 Patent No. 4377879

[0008] For moisturizers incorporated into topical skin compositions such as cosmetics, there is a growing demand for the development of products with superior moisturizing effects.

[0009] The object of the present invention is to provide an oily humectant with excellent skin moisturizing effect, and a topical skin composition containing the same. More specifically, the object is to provide an oily humectant comprising an ester compound that has a skin moisturizing function when applied to the skin, and a topical skin composition containing the same.

[0010] In view of the circumstances described above, the present inventors diligently researched the moisturizing functions of various oily substances. As a result, they investigated the effect of oily substances on the moisturizing function of the skin by applying the oily substance to the skin surface, waiting for a predetermined time, and then measuring the moisture content of the stratum corneum of the skin after removing the oily substance from the skin surface. They discovered that certain esterified compounds have a high moisturizing effect on the skin, and thus completed the present invention. Specifically, the present invention provides the following.

[0011] [1] An oily humectant comprising an ester of component A and component B or an ester of component A, component B and component C, wherein the hydroxyl value of the ester is 0 to 160 mg KOH / g, and the mass ratio of fatty acid residues derived from component B and fatty acid residues derived from component C in the fatty acid residues constituting the ester of component A, component B and component C is 99.9:0.1 to 45:55. Component A: A polyhydric alcohol which is dipentaerythritol, erythritol, or sorbitan. Component B: One or more fatty acids selected from straight-chain saturated fatty acids having 6 to 10 carbon atoms. Component C: One or more fatty acids selected from fatty acids having 6 to 28 carbon atoms (excluding component B). [2] The oily humectant according to [1], wherein component A is dipentaerythritol. [3] A composition for external use on the skin, characterized by comprising the oily humectant according to [1] or [2]. [4] The external skin composition according to [3], wherein the external skin composition is a cosmetic, a facial cleanser, a body wash, or a topical pharmaceutical. [5] A method for moisturizing the skin, characterized by applying the external skin composition containing the oily moisturizer according to [1] or [2] to the surface of the skin. [6] Use for moisturizing an ester of component A and component B having a hydroxyl value of 0 to 160 mg KOH / g, or an ester of component A, component B and component C having a hydroxyl value of 0 to 160 mg KOH / g and a mass ratio of fatty acid residues derived from component B and fatty acid residues derived from component C in the constituent fatty acid residues of 99.9:0.1 to 45:55. Component A: A polyhydric alcohol which is dipentaerythritol, erythritol, or sorbitan. Component B: One or more fatty acids selected from straight-chain saturated fatty acids having 6 to 10 carbon atoms. Component C: One or more fatty acids selected from fatty acids having 6 to 28 carbon atoms (excluding component B). [7] Use for preparing a topical skin composition of an esterified product of component A and component B having a hydroxyl value of 0 to 160 mg KOH / g, or an esterified product of component A, component B, and component C having a hydroxyl value of 0 to 160 mg KOH / g and a mass ratio of fatty acid residues derived from component B to fatty acid residues derived from component C in the constituent fatty acid residues of 99.9:0.1 to 45:55.Component A: A polyhydric alcohol, which is dipentaerythritol, erythritol, or sorbitan. Component B: One or more fatty acids selected from straight-chain saturated fatty acids with 6 to 10 carbon atoms. Component C: One or more fatty acids selected from fatty acids with 6 to 28 carbon atoms (excluding component B).

[0012] According to the present invention, an oily humectant comprising a specific esterified compound and having a moisturizing effect when applied to the skin, and a topical skin composition containing the oily humectant can be obtained.

[0013] Embodiments of the present invention will be described in detail below. In the present invention and this specification, "oil-based humectant" means an agent that is insoluble in water at room temperature and atmospheric pressure (for example, 20°C, 101.3 kPa) and has a moisturizing effect. Here, solubility in water means that when mixed with water, it becomes uniform without forming layers or becoming cloudy. In other words, when an oil-based humectant is mixed with water, it separates from water molecules to form layers or becomes cloudy due to emulsification.

[0014] In the present invention and this specification, the term "moisturizing effect" means the effect of improving the moisturizing function of the skin, and more specifically, the effect of retaining or increasing the moisture content of the stratum corneum. The oily moisturizer according to the present invention is preferably one that maintains the effect of retaining or increasing the moisture content of the stratum corneum for a certain period of time, not only when applied to the skin, but also when a portion or most of the external skin composition has been removed from the skin surface after application.

[0015] The water content of the stratum corneum can be determined by its electrical conductivity (μS). The electrical conductivity (μS) of the stratum corneum depends on its water content; the higher the water content, the higher the electrical conductivity (μS). The electrical conductivity (μS) of the stratum corneum can be measured by a constant-pressure sensor probe contact high-frequency conductance exchange method. Specifically, the electrical conductivity (μS) of the stratum corneum can be measured using a stratum corneum water content measuring device based on this measurement method, for example, IBS's stratum corneum water content measuring device "SKICON-200".

[0016] The hydroxyl value (mgKOH / g) of esterified compounds can be measured by the hydroxyl value (pyridine-acetic anhydride method) described in section 2.3.6.2-1996 of the "Standard Test Methods for Analysis of Fats and Oils, 2013 Edition," published by the Japan Oil Chemists' Society.

[0017] Specifically, it is the amount of potassium hydroxide in milligrams required to neutralize the acetic acid bonded to the hydroxyl group when 1 g of the sample is acetylated. The hydroxyl value of the esterified product is measured by neutralization titration. More specifically, the acetylation reagent is added to the sample and heated in a glycerin bath for 1 hour. Then, 1 mL of water is added to convert the unreacted acetic anhydride to acetic acid, and phenolphthalein solution is added as an indicator. The mixture is then titrated with potassium hydroxide ethanol solution. The hydroxyl value is calculated from the amount of potassium hydroxide ethanol solution required to confirm the color development of phenolphthalein. The acetylation reagent is a solution prepared by adding pyridine to 25 g of acetic anhydride to make a total volume of 100 mL.

[0018] <Oily Moisturizing Agent> The oily moisturizing agent according to the present invention consists of an esterified product of component A and component B, or an esterified product of component A, component B, and component C, wherein the hydroxyl value of the esterified product is 0 to 160 mgKOH / g. Among the esterified products, the esterified product of component A, component B, and component C has a mass ratio of fatty acid residues derived from component B and fatty acid residues derived from component C in the fatty acid residues constituting the esterified product of 99.9:0.1 to 45:55. Component A: A polyhydric alcohol, which is dipentaerythritol, erythritol, or sorbitan. Component B: One or more fatty acids selected from straight-chain saturated fatty acids having 6 to 10 carbon atoms. Component C: One or more fatty acids selected from fatty acids having 6 to 28 carbon atoms (excluding component B).

[0019] The polyhydric alcohol component A is dipentaerythritol, erythritol, or sorbitan. Dipentaerythritol can be obtained from pentaerythritol by a condensation reaction or the like, and is commercially available. Sorbitan can also be obtained from sorbitol by an intramolecular condensation reaction or the like, and is commercially available. Examples of commercially available dipentaerythritol include Dipentaerythritol (90% GRADE) sold by Lee Changrong Chemical Co., Ltd., examples of commercially available erythritol include Erythritol sold by Bussan Food Science Co., Ltd., and examples of commercially available sorbitan include Sorbitan M-70 sold by Sanko Chemical Industry Co., Ltd. Dipentaerythritol is preferred as the polyhydric alcohol component A because it provides a higher moisturizing effect.

[0020] The fatty acid of component B is a straight-chain saturated fatty acid having 6 to 10 carbon atoms. Specifically, examples of straight-chain saturated fatty acids having 6 to 10 carbon atoms include caproic acid (n-hexanoic acid: 6 carbon atoms), n-heptanoic acid (7 carbon atoms), caprylic acid (n-octanoic acid: 8 carbon atoms), pelargonic acid (n-nonanoic acid: 9 carbon atoms), and capric acid (n-decanoic acid: 10 carbon atoms). One or two selected from caprylic acid and capric acid are preferred, with caprylic acid being more preferred.

[0021] The fatty acid of component C is a fatty acid having 8 to 22 carbon atoms, preferably 8 to 18 carbon atoms. Furthermore, the fatty acid may be a straight-chain saturated fatty acid, a branched saturated fatty acid, a straight-chain unsaturated fatty acid, or a branched unsaturated fatty acid. It may also be a hydroxyl group-containing fatty acid. Among these, straight-chain saturated fatty acids or branched saturated fatty acids are preferred, with straight-chain saturated fatty acids being more preferred. In addition to monounsaturated fatty acids, polyunsaturated fatty acids can also be used. One or more of these fatty acids can be used as component C. However, straight-chain saturated fatty acids having 6 to 10 carbon atoms (component B) are excluded.

[0022] Examples of straight-chain saturated fatty acids with 11 to 28 carbon atoms include n-undecanoic acid (11 carbon atoms), lauric acid (n-dodecanoic acid: 12 carbon atoms), myristic acid (14 carbon atoms), palmitic acid (16 carbon atoms), and stearic acid (18 carbon atoms), behenic acid (22 carbon atoms), montanic acid (28 carbon atoms), etc.

[0023] Examples of straight-chain unsaturated fatty acids with 6 to 28 carbon atoms include palmitoleic acid (16 carbon atoms), oleic acid (18 carbon atoms), linoleic acid (18 carbon atoms), linolenic acid (18 carbon atoms), and erucic acid (22 carbon atoms).

[0024] Branched saturated fatty acids with 6 to 28 carbon atoms include, specifically, 2-ethylhexanoic acid (8 carbon atoms, also called isocaprylic acid), 3,5,5-trimethylhexanoic acid (9 carbon atoms, also called isononanoic acid), 2-butyloctanoic acid (10 carbon atoms), isoundecanoic acid (11 carbon atoms), 2-butyloctanoic acid (12 carbon atoms, also called isolauric acid or indodecanoic acid), isotridecanoic acid (13 carbon atoms), isopalmitic acid (16 carbon atoms), isostearic acid (18 carbon atoms, with three different branching states), and octyldodecanoic acid (20 carbon atoms).

[0025] Examples of hydroxyl group-containing fatty acids with 6 to 28 carbon atoms include 12-hydroxystearic acid (18 carbon atoms) and ricinoleic acid (18 carbon atoms).

[0026] Dibasic acids are examples of polyunsaturated fatty acids with 6 to 28 carbon atoms. Specifically, these include suberic acid (octanedioic acid: 8 carbon atoms), azelaic acid (nonanedioic acid: 9 carbon atoms), sebacic acid (decandioic acid: 10 carbon atoms), undecandioic acid (11 carbon atoms), dodecandioic acid (12 carbon atoms), tridecandioic acid (13 carbon atoms), tetradecandioic acid (14 carbon atoms), pentadecandioic acid (15 carbon atoms), hexadecanedioic acid (16 carbon atoms), heptadecanedioic acid (17 carbon atoms), octadecandioic acid (18 carbon atoms), nonadecanedioic acid (19 carbon atoms), eicosanedioic acid (20 carbon atoms), isoeicosanedioic acid (20 carbon atoms), and octacosanedioic acid (28 carbon atoms).

[0027] The saturated fatty acid in component B and the fatty acid in component C may be chemically synthesized products or extracted from natural sources. Furthermore, commercially available products can be used for both component B and component C.

[0028] When the esterified oily humectant according to the present invention is an esterified product of component A, component B, and component C, the amount of fatty acid residues derived from component C in the fatty acid residues constituting the esterified product should be such that it does not impair the skin moisturizing effect obtained by introducing fatty acid residues derived from component B into the hydroxyl groups in the polyhydric alcohol of component A through an esterification reaction. The mass ratio of fatty acid residues derived from component B to fatty acid residues derived from component C in the fatty acid residues constituting the esterified product (hereinafter sometimes referred to as the "mass ratio of constituent fatty acid residues of component B and component C") is in the range of 99.9:0.1 to 45:55, preferably 99.9:0.1 to 50:50, and more preferably 99.9:0.1 to 80:20.

[0029] The mass ratio of component B and component C fatty acid residues in the constituent fatty acids of the esterified product can be measured, for example, as follows: Prepare a derivative by methyl esterifying the fatty acid residues in the esterified product sample using the 2.4.1.1-2013 methyl esterification method (sulfuric acid-methanol method) (published by the Japan Oil Chemists' Society, "Standard Test Methods for Analysis of Fats and Oils, 2013 Edition") or an equivalent method. For the preparation of this methyl esterified derivative, methyl esterification methods such as the 2.4.1.2-2013 boron trifluoride-methanol method and the 2.4.1.3-2013 sodium methoxide method from the same standard test methods for analysis of fats and oils may also be used as reference.

[0030] The obtained derivative can be separated and measured using the method described in 2.4.2.3-2013 Fatty Acid Composition (Capillary Gas Chromatography) (published by the Japan Oil Chemists' Society, "Standard Test Methods for Analysis of Fats and Oils, 2013 Edition") or an equivalent method to determine the mass ratio of component B and component C of the constituent fatty acids in the esterified product. For example, when saturated and unsaturated fatty acids with 18 carbon atoms are mixed, if you want to know the individual components rather than the total mass ratio of saturated and unsaturated fatty acids with 18 carbon atoms, the 2.4.2.3-2013 Fatty Acid Composition (Capillary Gas Chromatography) method can be used to separate stearic acid, oleic acid, linoleic acid, linolenic acid, etc.

[0031] More specifically, a derivative is prepared by dissolving the esterified sample in a derivatization reagent and heat-treating it to methylate the fatty acid residues in the esterified product. The obtained derivatives are separated and quantified according to the type of fatty acid methyl ester using a gas chromatograph equipped with FID. The composition of fatty acid residues in the esterified product is determined based on the percentage (%) of the peak area of ​​the fatty acid methyl ester obtained from each fatty acid residue relative to the total peak area on the chromatograph. By preparing methylated derivatives of fatty acid raw materials for which the mass ratio of constituent fatty acid residues of component B and component C is known in advance, and analyzing these derivatives with a gas chromatograph, the mass ratio of constituent fatty acid residues of component B and component C in the esterified product can be confirmed more accurately.

[0032] The oily moisturizer according to the present invention comprises an esterified product in which at least a portion of the hydroxyl groups in the polyhydric alcohol of component A are replaced by fatty acid residues derived from the fatty acid of component B by an esterification reaction, and the hydroxyl value is 0 to 160 mgKOH / g, or an esterified product in which fatty acid residues derived from the fatty acid of component B and fatty acid residues derived from the fatty acid of component C are replaced, and the mass ratio of fatty acid residues derived from component B to fatty acid residues derived from component C is 99.9:0.1 to 45:55, and the hydroxyl value is 0 to 160 mgKOH / g. By setting the hydroxyl value of the esterified product within a specific range, the esterified product can be made to have a skin moisturizing effect.

[0033] The oily humectant according to the present invention can provide a moisturizing effect if the hydroxyl value of the esterified compound constituting it is between 0 and 160 mg KOH / g. By changing the hydroxyl value of the esterified compound constituting the oily humectant according to the present invention, the viscosity and feel of the esterified compound can be adjusted to a desired state. Therefore, the oily humectant according to the present invention can be appropriately selected from esterified compounds with different hydroxyl values ​​depending on the application and formulation considerations.

[0034] The viscosity and feel of the esterified oily humectant according to the present invention are also affected by the type and composition of fatty acid residues in the esterified product. Therefore, by adjusting the types of fatty acids in component B and component C, and the esterification efficiency with the polyhydric alcohol of component A, it is possible to obtain an esterified product with a desired viscosity and feel. For example, by limiting the fatty acid of component B to at least one of caprylic acid and capric acid, the viscosity of the esterified product can be further reduced. Esterified products with low viscosity feel less sticky and have a smooth feel when applied to the skin. Therefore, a topical skin composition containing an esterified product of the fatty acid of component B as an oily humectant has good skin compatibility and a superior feel.

[0035] The inclusion of fatty acid residues derived from the fatty acid of component C in the esterified product improves the feel and various physical properties when the esterified product is applied to the skin surface. In other words, by appropriately adjusting the type and relative abundance (esterification rate) of fatty acid residues derived from the fatty acid of component C in the esterified product, it is possible to obtain an esterified product that has a moisturizing effect while possessing the desired feel and physical properties, making it extremely useful as an oily moisturizer.

[0036] The esterified oily humectant according to the present invention is an esterified product obtained by using component A and component B, or component A, component B and component C, as reaction raw materials, and carrying out an esterification reaction such that the hydroxyl value is within a specific range.

[0037] The esterified product of component A, dipentaerythritol, may contain fatty acid esters with a degree of esterification of 1 to 6. The composition ratio of dipentaerythritol fatty acid esters with a degree of esterification of 1 to 6 is not particularly limited as long as the hydroxyl value of the esterified product is 0 to 160 mgKOH / g. This composition ratio can be adjusted by appropriately adjusting the charging ratio of the raw materials and the reaction conditions of the esterification reaction.

[0038] The esterified product of erythritol as component A may contain fatty acid esters with a degree of esterification of 1 to 4. The composition ratio of erythritol fatty acid esters with a degree of esterification of 1 to 4 is not particularly limited as long as the hydroxyl value of the esterified product is 0 to 160 mgKOH / g. This composition ratio can be adjusted by appropriately adjusting the charging ratio of the raw materials and the reaction conditions of the esterification reaction.

[0039] The esterified product of sorbitan as component A may contain fatty acid esters with a degree of esterification of 1 to 4. The composition ratio of sorbitan fatty acid esters with a degree of esterification of 1 to 4 is not particularly limited as long as the hydroxyl value of the esterified product is 0 to 160 mgKOH / g. This composition ratio can be adjusted by appropriately adjusting the charging ratio of the raw materials and the reaction conditions of the esterification reaction.

[0040] The esterification reaction to obtain the esterified product of component A and component B, which is an oily humectant according to the present invention, can be carried out, for example, by charging 1 mole of component A with the number of moles of component B necessary to achieve the desired hydroxyl value, or a larger number of moles, and reacting them at a temperature of 180 to 240°C, either without a catalyst or in the presence of a catalyst. As the catalyst, a catalyst known in the field of organic chemistry, such as an acid, alkali, or other catalyst used in the esterification reaction of alcohols and fatty acids, can be used. The reaction may be carried out in a solvent that does not adversely affect the esterification reaction, or without a solvent. As the solvent, a solvent known in the field of organic chemistry, such as one used in the esterification reaction of alcohols and fatty acids, can be used. The reaction time can usually be 10 to 20 hours. However, the reaction time may be less than 10 hours or more than 20 hours, as it is affected by the raw materials used (linear or branched), the presence or absence of a catalyst, the esterification temperature, or the excess amount of acid. After the reaction is complete, if a catalyst was used, it may be removed by filtration or adsorption treatment. Esterified products can be obtained from the reactants of an esterification reaction by conventional methods such as distillation to remove excess unreacted raw materials or by purification under alkaline conditions. Furthermore, if it is desired to improve the color of the esterified product, it can be decolorized using conventional methods.

[0041] Here, by adjusting the amounts of component A and component B used and calculating to achieve the desired hydroxyl value, an esterified product with a hydroxyl value close to the desired value can be obtained.

[0042] For example, when producing an esterified product in which component A is dipentaerythritol and the hydroxyl value is 0 mgKOH / g, that is, when producing a full fatty acid ester of dipentaerythritol (in which fatty acids are esterified to all hydroxyl groups of dipentaerythritol), it can be produced by charging more than 6 moles of component B for every 1 mole of component A.

[0043] Also, when producing an esterified product in which component A is erythritol or sorbitan and the hydroxyl value is 0 mgKOH / g, that is, when producing a full ester of fatty acid of erythritol or sorbitan (in which all fatty acids of erythritol or sorbitan are esterified), it can be produced by charging more than 4 moles of component B per 1 mole of component A.

[0044] Also, when producing an esterified product in which component A is dipentaerythritol and the hydroxyl value is greater than 0 mgKOH / g, that is, when producing a partial ester of fatty acid of dipentaerythritol (in which fatty acids are esterified to a part of the hydroxyl groups of dipentaerythritol), it can be produced by charging less than 6 moles of component B per 1 mole of component A and completing the reaction.

[0045] Also, when producing an esterified product in which component A is erythritol or sorbitan and the hydroxyl value is greater than 0 mgKOH / g, that is, when producing a partial ester of fatty acid of erythritol or sorbitan (in which fatty acids are esterified to a part of the hydroxyl groups of erythritol or sorbitan), it can be produced by charging less than 4 moles of component B per 1 mole of component A and completing the reaction.

[0046] Also, in the production of a partial ester having a target hydroxyl value, regardless of whether component A is dipentaerythritol, erythritol, or sorbitan, by charging an amount more than the required amount of component B and stopping the reaction halfway while observing the transition of the acid value during the reaction, an esterified product near the target hydroxyl value can be obtained. In addition, regardless of whether component A is dipentaerythritol, erythritol, or sorbitan, if the hydroxyl value of the obtained esterified product deviates from the target hydroxyl value, by setting the charging ratio considering the degree of deviation, an esterified product having the target hydroxyl value can be finally obtained.

[0047] In the production of an esterified product of component A, component B, and component C, which is an oil-based moisturizer according to the present invention, the esterification reaction for obtaining an esterified product having a target hydroxyl value can be carried out, for example, by charging 1 mol of component A with the number of moles of component B and component C necessary to achieve the target hydroxyl value, or a larger number of moles, and reacting at a temperature of 180 to 240°C in the absence or presence of a catalyst. For the purification after the reaction is completed, it may be carried out in the same manner as the method described above.

[0048] Here, by adjusting the charged amounts of component A, component B, and component C and calculating so as to achieve the target hydroxyl value, an esterified product near the target hydroxyl value can be obtained. For example, when component A is dipentaerythritol and an esterified product having a hydroxyl value of 0 mgKOH / g is to be produced, that is, when a full ester of fatty acid of dipentaerythritol (in which all hydroxyl groups of dipentaerythritol are esterified with fatty acid) is to be produced, it can be produced by charging more than 6 moles of component B and component C per 1 mole of component A.

[0049] Also, when component A is erythritol or sorbitan and an esterified product having a hydroxyl value of 0 mgKOH / g is to be produced, that is, when a full ester of fatty acid of erythritol or sorbitan (in which all fatty acids of erythritol or sorbitan are esterified) is to be produced, it can be produced by charging more than 4 moles of component B and component C per 1 mole of component A.

[0050] Also, when component A is dipentaerythritol and an esterified product having a hydroxyl value greater than 0 mgKOH / g is to be produced, that is, when a partial ester of fatty acid of dipentaerythritol (in which a part of the hydroxyl groups of dipentaerythritol are esterified with fatty acid) is to be produced, it can be produced by charging less than 6 moles of component B and component C per 1 mole of component A and completing the reaction.

[0051] Furthermore, when producing an esterified product in which component A is erythritol or sorbitan and the hydroxyl value is greater than 0 mgKOH / g, that is, when producing a partial ester of the fatty acid of erythritol or sorbitan (where a fatty acid is esterified to some of the hydroxyl groups of erythritol or sorbitan), it can be produced by charging less than 4 moles of components B and C for 1 mole of component A and completing the reaction.

[0052] Furthermore, regardless of whether component A is dipentaerythritol, erythritol, or sorbitan, in the production of a partial ester having the desired hydroxyl value, an esterified product with a hydroxyl value close to the desired value can also be obtained by charging a larger amount than the required amounts of components B and C, and stopping the reaction midway while observing the changes in the acid value during the reaction.

[0053] Furthermore, regardless of whether component A is dipentaerythritol, erythritol, or sorbitan, if the hydroxyl value of the resulting esterified product deviates from the desired hydroxyl value, the esterified product with the desired hydroxyl value can be obtained by adjusting the mixing ratio to account for the degree of the deviation.

[0054] Furthermore, if the total amount of component B and component C added is greater than the number of moles of component B and component C required to achieve the desired hydroxyl value, and the reactivity of component C is lower than that of component B, the reaction of component B may proceed first, causing the mass ratio of constituent fatty acid residues of component B and component C in the resulting esterified product to deviate from the mass ratio of constituent fatty acid residues added. In such cases, the mass ratio of constituent fatty acid residues of component B and component C can be adjusted by taking this deviation into account beforehand and adjusting the mass ratio of the amounts of each component added, or by performing a two-step reaction in which the fatty acids of component C, which have lower reactivity, are added and reacted first, followed by the addition and reaction of component B.

[0055] One embodiment of the esterified oily humectant according to the present invention is an esterified product of component A and component B, wherein component A is dipentaerythritol, erythritol, or sorbitan, and component B is one or more fatty acids selected from linear saturated fatty acids having 6 to 10 carbon atoms, and has a hydroxyl value of 0 to 160 mgKOH / g. Preferably, it is an esterified product of dipentaerythritol (component A) having a hydroxyl value of 0 to 160 mgKOH / g and one or more fatty acids (component B) selected from linear saturated fatty acids having 6 to 10 carbon atoms, and more preferably, it is an esterified product of dipentaerythritol (component A) having a hydroxyl value of 0 to 160 mgKOH / g and one or more fatty acids (component B) selected from caprylic acid and capric acid.

[0056] One embodiment of the esterified oily humectant according to the present invention is an esterified product of component A, component B, and component C, wherein component A is dipentaerythritol, erythritol, or sorbitan, component B is one or more fatty acids selected from straight-chain saturated fatty acids having 6 to 10 carbon atoms, and component C is one or more fatty acids selected from fatty acids having 6 to 28 carbon atoms (excluding component B), the mass ratio of the constituent fatty acid residues of component B and component C in the fatty acid residues constituting the esterified product is 99.9:0.1 to 45:55, and the hydroxyl value is 0 to 160 mgKOH / g. Preferably, the esterified product is of dipentaerythritol (component A), one or more fatty acids selected from linear saturated fatty acids having 8 to 10 carbon atoms (component B), and one or more fatty acids selected from fatty acids having 8 to 18 carbon atoms (component C), wherein the hydroxyl value is 0 to 160 mg KOH / g and the mass ratio of constituent fatty acid residues of component B to component C is 99.9:0.1 to 45:55. More preferably, the esterified product is of dipentaerythritol (component A), one or more fatty acids selected from caprylic acid and capric acid (component B), and one or more fatty acids selected from fatty acids having 8 to 18 carbon atoms (component C), wherein the hydroxyl value is 0 to 160 mg KOH / g and the mass ratio of constituent fatty acid residues of component B to component C is 99.9:0.1 to 45:55.

[0057] The oily humectant according to the present invention preferably has a moisturizing effect that increases the electrical conductivity (μS) of the stratum corneum of the skin after application of the oily humectant to at least 50 μS or more than the electrical conductivity (μS) of the stratum corneum before application, more preferably at least 60 μS or more, and even more preferably at least 70 μS or more.

[0058] When investigating the moisturizing effect of an oily humectant, the electrical conductivity (μS) of the stratum corneum is measured in an environment where room temperature and humidity are within a certain range, for example, in an environment controlled to 18-22°C and 40-55% RH. More specifically, for example, an oily humectant is uniformly applied to a skin surface whose stratum corneum electrical conductivity (μS) has been measured in advance. After leaving the oily humectant on for a certain period, for example 30-90 minutes, the oily humectant is removed from the skin surface. After a certain period, for example 5-60 minutes, the electrical conductivity (μS) of the stratum corneum to which the oily humectant was applied is measured. The moisturizing effect value is calculated using the obtained values ​​of electrical conductivity (μS) of the stratum corneum before and after application of the oily humectant, and the moisturizing effect is evaluated. It is preferable to evaluate the moisturizing effect of an oily humectant during a time when the skin is prone to dryness.

[0059] By mixing the esterified oily humectant according to the present invention with other components, a topical skin composition can be applied to the body surface of an animal for moisturizing purposes. Even if the esterified is solid at room temperature, it can be dissolved in a liquid oil and used as a liquid oil.

[0060] The other components are not particularly limited as long as they do not excessively impair the moisturizing effect of the esterified product, and can be appropriately selected and used from among various additives permitted to be included in cosmetics, cleansers, topical pharmaceuticals, etc. Examples of such other components include oily components (excluding the oily moisturizer according to the present invention), aqueous components, polymer emulsions, anionic surfactants, cationic surfactants, amphoteric surfactants, lipophilic nonionic surfactants, hydrophilic nonionic surfactants, natural surfactants, humectants (excluding the oily moisturizer according to the present invention), thickeners, preservatives, powder components, pigments, pH adjusters, antioxidants, UV absorbers, fragrances, dyes, metal ion chelating agents, and purified water. Specifically, these are the same components that can be included in the topical skin composition described later.

[0061] The oily humectant according to the present invention can be used as a raw material for various topical skin compositions. By incorporating the oily humectant into various topical skin compositions, a skin moisturizing effect can be imparted to the topical skin compositions.

[0062] <Skin Topical Composition> Next, the skin topical composition according to the present invention will be described. The skin topical composition according to the present invention contains the oily humectant according to the present invention, and the oily humectant itself can also be used as a skin topical composition.

[0063] Herein, in the present invention and this specification, "external skin composition" means all external compositions applied externally to the body surface such as skin, nails, and hair, including cosmetics, cleansers, quasi-drugs, and topical pharmaceuticals. The external skin composition according to the present invention is preferably an external skin composition whose purpose of use is to moisturize the body surface tissue of animals such as humans, such as the skin, and more preferably a moisturizing cosmetic, moisturizing cleanser, moisturizing quasi-drug, or moisturizing topical pharmaceutical used for moisturizing the skin.

[0064] The topical skin composition according to the present invention contains an oily humectant according to the present invention, and by applying it to the skin, it can improve the skin's moisturizing function and moisturize the skin. In particular, the oily humectant according to the present invention can maintain a high moisture content in the stratum corneum of the skin and maintain a moisturized state even after it has been wiped off after being applied to the skin. For this reason, the topical skin composition according to the present invention containing this oily humectant can maintain its moisturizing effect for a certain period of time, not only when applied to the skin, but also even when some or most of the topical skin composition has been removed from the skin surface by sebum, sweat, friction, washing, etc., after application to the skin.

[0065] The topical skin composition according to the present invention is used by adhering it to the body surface of an animal. The body surface to which the topical skin composition is applied is not particularly limited and includes, for example, skin, nails, and hair. The manner in which the topical skin composition is applied to the body surface is not particularly limited and may be applied by coating the body surface or by spraying it.

[0066] The subjects to whom the topical skin composition according to the present invention is used, i.e., subjects requiring skin moisturization, are not particularly limited, but are preferably animals. These animals may be humans or other animals. Because the oily humectant according to the present invention provides a high moisturizing effect, it is preferable to use the topical skin composition according to the present invention on animals that require moisturizing of their skin and hair, such as animals living in dry environments or animals that require treatment, prevention, or improvement of symptoms caused by dry skin. Symptoms caused by dry skin include dry skin such as redness, eczema, and cracking, xerotic dermatitis, atopic dermatitis, and senile pruritus. For example, by applying a cosmetic containing the oily humectant according to the present invention, or an ointment containing the oily humectant according to the present invention as a base material, to the skin surface, it is expected that the decrease in the moisture content of the stratum corneum of the skin will be suppressed and symptoms caused by dry skin will be improved compared to when a cosmetic or ointment without the oily humectant according to the present invention is applied.

[0067] There are no particular restrictions on the use or dosage form of the topical skin composition according to the present invention; it may be a cosmetic, a cleanser, a quasi-drug, or a topical pharmaceutical. Furthermore, the topical skin composition according to the present invention may have any appearance, such as transparent (e.g., solubilized or dissolved), translucent (e.g., dispersed in a fine particle state), cloudy (e.g., dispersed or emulsified), or two-layer separated (e.g., separated into two layers). For example, the topical skin composition according to the present invention can be a wide variety of topical skin compositions that conventionally used oily components. Examples of cosmetics include, specifically, skincare cosmetics such as emulsions, serums, creams, lotions, cosmetic oils, emollient creams, and hand creams; hair cosmetics such as rinses, hair conditioners, hair waxes, and hair creams; lip cosmetics such as lipsticks and lip glosses; eye makeup cosmetics such as powder foundations, emulsified foundations, blushes, makeup bases, eyebrow cosmetics, nail cosmetics, and solvent-based nail care products; and sunscreen cosmetics such as sun oils and emulsified sunscreens. Examples of cleansing agents include, specifically, cleansing oils, cleansing creams, facial cleansers, body washes, and hair washes such as shampoos. Examples of topical pharmaceuticals include, specifically, topical preparations such as creams, ointments, and lotions, and adhesive preparations such as poultices and plasters. There are no particular restrictions on the manufacturing method of these external skin compositions, and they can be manufactured by known methods.

[0068] The topical skin composition according to the present invention can be manufactured by using the oily humectant according to the present invention as a raw material. The oily humectant according to the present invention can be easily formulated, like many oily raw materials. Since the oily humectant according to the present invention is oily, when used as a raw material for a topical skin composition, the topical skin composition according to the present invention can be efficiently manufactured by mixing it with oily components from other raw materials. The oily humectant according to the present invention can also be used to manufacture a topical skin composition by dispersing it in an aqueous medium by emulsification or by solubilizing it in an aqueous medium, without mixing it with oily components from other raw materials.

[0069] The amount of the oily humectant according to the present invention in the topical skin composition according to the present invention is not particularly limited, as long as it is an amount that can exert a moisturizing effect on the skin by the oily humectant. The amount of the oily humectant according to the present invention can be appropriately determined considering other components, the type of topical skin composition and its manner of use (whether it is applied to the skin and not intentionally removed from the skin surface, or whether it is removed from the skin surface within a certain period after application), etc. For example, the amount of the oily humectant according to the present invention in the topical skin composition according to the present invention can be appropriately determined within the range of 0.001 to 99.9% by mass of the total mass of the topical skin composition.

[0070] The topical skin composition according to the present invention may contain, as necessary, various components commonly used in topical skin compositions, provided that they do not impair the effects of the present invention. Such components vary depending on the use and dosage form of the topical skin composition, but examples include oily components (excluding the oily humectant according to the present invention), aqueous components, polymer emulsions, anionic surfactants, cationic surfactants, amphoteric surfactants, lipophilic nonionic surfactants, hydrophilic nonionic surfactants, natural surfactants, humectants (excluding the oily humectant according to the present invention), thickeners, preservatives, powder components, pigments, pH adjusters, antioxidants, UV absorbers, fragrances, dyes, metal ion chelating agents, and purified water.

[0071] Examples of the oily components include hydrocarbons such as liquid paraffin, heavy liquid isoparaffin, solid paraffin, α-olefin oligomer, squalane, petrolatum, polyisobutylene, polybutene, montan wax, ceresin wax, microcrystalline wax, polyethylene wax, and Fischer-Tropsch wax; oils and fats such as olive oil, castor oil, jojoba oil, mink oil, and macadamia nut oil; waxes such as beeswax, candelilla wax, gay wax, carnauba wax, and Japanese wax; and cetyl 2-ethylhexanoate. Isopropyl myristate, isopropyl palmitate, octyldodecyl myristate, polyglyceryl diisostearate, polyglyceryl triisostearate, diglyceryl triisostearate, polyglyceryl tetraisostearate, diglyceryl tetraisostearate, trioctanoin, diisostearyl malate, neopentyl glycol dioctanoate, propylene glycol didecanoate, cholesterol fatty acid ester, glyceryl tristearate, glycerin fatty acid ester eicosanedioic acid condensate, palmitate Esters such as chistrin, dextrin myristate, and dextrin fatty acid esters; fatty acids such as stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, and oleic acid; higher alcohols such as stearyl alcohol, cetyl alcohol, lauryl alcohol, oleyl alcohol, isostearyl alcohol, behenyl alcohol, octyldodecanol, and isohexadecyl alcohol; low-molecular-weight dimethylpolysiloxane, high-molecular-weight dimethylpolysiloxane, methylphenylpolysiloxane, decamethyl Silicones such as clopentasiloxane, octamethylcyclotetrasiloxane, polyether-modified polysiloxane, polyoxyalkylene / alkylmethylpolysiloxane / methylpolysiloxane copolymer, and alkoxy-modified polysiloxane; fluorinated oils such as perfluorodecane, perfluorooctane, and perfluoropolyether; amino acid ester oils such as N-acyl glutamic acid such as stearoyl glutamic acid and N-lauroyl-L-glutamic acid di(cholesteryl or phytosteryl / behenyl / octyldodecyl);Examples include lanolin, liquid lanolin, lanolin acetate, liquid lanolin acetate, isopropyl lanolin fatty acid, and lanolin alcohol, as well as other lanolin derivatives. These oily components may be used individually or in combination of two or more.

[0072] Examples of the aqueous components include lower alcohols such as ethyl alcohol and butyl alcohol; glycols such as propylene glycol, 1,3-butylene glycol, dipropylene glycol, and polyethylene glycol; glycerols such as glycerin, diglycerin, and polyglycerin; and plant extracts such as aloe vera, witch hazel, witch hazel, cucumber, tomato, apple, lemon, lavender, and rose. These aqueous components may be used individually or in combination of two or more.

[0073] Examples of the polymer emulsions include alkyl acrylate polymer emulsions, alkyl methacrylate polymer emulsions, alkyl acrylate copolymer emulsions, alkyl methacrylate copolymer emulsions, acrylic acid / alkyl acrylate copolymer emulsions, methacrylate / alkyl methacrylate copolymer emulsions, alkyl acrylate / styrene copolymer emulsions, alkyl methacrylate / styrene copolymer emulsions, vinyl acetate polymer emulsions, polyvinyl acetate emulsions, vinyl acetate-containing copolymer emulsions, vinylpyrrolidone / styrene copolymer emulsions, and silicone-containing copolymer emulsions. These polymer emulsions may be used individually or in combination of two or more types.

[0074] Examples of the anionic surfactants include soap base, fatty acid soaps such as sodium laurate and sodium palmitate, higher alkyl sulfate salts such as sodium lauryl sulfate and potassium lauryl sulfate, alkyl ether sulfate salts such as polyoxyethylene (POE)-lauryl sulfate triethanolamine and POE-lauryl sulfate sodium; N-acyl sarcosinates such as sodium lauroyl sarcosinate; higher fatty acid amide sulfonates such as sodium N-myristoyl-N-methyl taurate, sodium coconut oil fatty acid methyl taulide, and sodium lauryl methyl taulide; phosphate salts such as sodium POE-oleyl ether phosphate and POE-stearyl ether phosphate; sodium di-2-ethylhexyl sulfosuccinate, monolauroyl monoethanolamide polyoxyethylene sulfosuccinate sodium, and lauryl polypropylene glycol sulfosuccinate Examples include sulfosuccinates such as sodium acid; alkylbenzene sulfonates such as sodium linear dodecylbenzenesulfonate, linear dodecylbenzenesulfonate triethanolamine, and linear dodecylbenzenesulfonate; N-acyl glutamates such as monosodium N-lauroyl glutamate, disodium N-stearoyl glutamate, and monosodium N-myristoyl-L-glutamate; higher fatty acid ester sulfates such as sodium hydrogenated coconut oil fatty acid glycerin sulfate; sulfurized oils such as belladonna oil; POE-alkyl ether carboxylic acid, POE-alkyl allyl ether carboxylic acid salt, α-olefin sulfonate, higher fatty acid ester sulfonate, secondary alcohol sulfate, higher fatty acid alkylolamide sulfate, sodium lauroyl monoethanolamide succinate, N-palmitoyl aspartate ditriethanolamine, and sodium caseinate. These anionic surfactants may be used individually or in combination of two or more.

[0075] Examples of the cationic surfactants include alkyltrimethylammonium salts such as stearyltrimethylammonium chloride and lauryltrimethylammonium chloride; dialkyldimethylammonium salts such as distearyldimethylammonium chloride; alkylpyridinium salts such as poly(N,N'-dimethyl-3,5-methylenepiperidinium) chloride and cetylpyridinium chloride; alkylquaternary ammonium salts, alkyldimethylbenzylammonium salts, alkylisoquinolinium salts, dialkylmorpholinium salts, POE-alkylamines, alkylamine salts, polyamine fatty acid derivatives, amyl alcohol fatty acid derivatives, benzalkonium chloride, and benzethonium chloride. These cationic surfactants may be used individually or in combination of two or more.

[0076] Examples of the amphoteric surfactants include imidazoline-based amphoteric surfactants such as 2-undecyl-N,N,N-(hydroxyethylcarboxymethyl)-2-imidazoline sodium and 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt; and betaine-based surfactants such as 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, alkyl betaine, amide betaine, and sulfobetaine. These amphoteric surfactants may be used individually or in combination of two or more.

[0077] Examples of the aforementioned lipophilic nonionic surfactants include sucrose fatty acid esters; glycerin fatty acids such as monocottonseed oil fatty acid glycerin, monoerucate glycerin, sesquioleate glycerin, monostearate glycerin, α,α'-oleate pyroglutamate glycerin, and monostearate glycerin; polyglycerin fatty acid esters such as monoisostearate diglyceryl and diisostearate diglyceryl; propylene glycol fatty acid esters such as monostearate propylene glycol; sorbitan fatty acid esters such as sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, penta-2-ethylhexyl sorbitan diglycerol sorbitan, and tetra-2-ethylhexyl sorbitan diglycerol sorbitan; hydrogenated castor oil derivatives, and glycerin alkyl ethers. These lipophilic nonionic surfactants may be used individually or in combination of two or more types.

[0078] Examples of the hydrophilic nonionic surfactants include POE-sorbitan fatty acid esters such as POE-sorbitan monooleate, POE-sorbitan monostearate, and POE-sorbitan tetraoleate; POE-sorbitan fatty acid esters such as POE-sorbitan monolaurate, POE-sorbitan monooleate, POE-sorbitan pentaoleate, and POE-sorbitan monostearate; POE-glycerin monostearate, POE-glycerin monoisostearate, and POE-glycerin POE-glycerol fatty acid esters such as phosphate triisostearate; POE-fatty acid esters such as POE-monoleate, POE-distearate, POE-dioleate, and POE-stearate; POE-alkyl ethers such as POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, and POE-cholestanol ether; Pluronic type ethers such as Pluronic; POE-POP-cetyl ether, POE- POE / POP alkyl ethers such as POP-2-decyltetradecyl ether, POE / POP-monobutyl ether, POE / POP-hydrogenated lanolin, and POE / POP-glycerin ether; tetraPOE / tetraPOP-ethylenediamine polymers such as Tetronic; POE-castor oil, POE-hydrogenated castor oil, POE-hydrogenated castor oil monoisostearate, POE-hydrogenated castor oil triisostearate, POE-hydrogenated castor oil monopyroglutamic acid monoisostearate diester, and POE-hydrogenated castor oil Examples include POE-castor oil hydrogenated castor oil derivatives such as oil maleic acid; POE-beeswax / lanolin derivatives such as POE-sorbitol beeswax; alkanolamides such as coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, and fatty acid isopropanolamide; POE-propylene glycol fatty acid esters, POE-alkylamines, POE-fatty acid amides, sucrose fatty acid esters, POE-nonylphenylformaldehyde polymers, alkylethoxydimethylamine oxide, and trioleyl phosphate. These hydrophilic nonionic surfactants may be used individually or in combination of two or more.Note that POP stands for polyoxypropylene.

[0079] Examples of the aforementioned natural surfactants include lecithins such as soybean phospholipids, hydrogenated soybean phospholipids, egg yolk phospholipids, and hydrogenated egg yolk phospholipids; and soybean saponins. These natural surfactants may be used individually or in combination of two or more.

[0080] Examples of the aforementioned humectants include polyethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, carotenoid acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, urea, bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin ethylene oxide (EO) adduct, diglycerin propylene oxide (PO) adduct, Rosa rugosa extract, Achillea millefolium extract, and Melilotus extract. These humectants may be used individually or in combination of two or more.

[0081] Examples of the thickening agents include gum arabic, carrageenan, karaya gum, tragacanth gum, carob gum, quince seed (marmelo), casein, dextrin, gelatin, sodium pectinate, sodium alginate, methylcellulose, ethylcellulose, carboxymethylcellulose (CMC), hydroxyethylcellulose, hydroxypropylcellulose, polyvinyl alcohol (PVA), polyvinyl methyl ether (PVM), polyvinylpyrrolidone (PVP), sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, dialkyldimethylammonium sulfate cellulose, xanthan gum, aluminum magnesium silicate, bentonite, hectorite, quaternary ammonium salt type cation-modified bentonite, quaternary ammonium salt type cation-modified hectorite, and decaglycerin fatty acid ester eicosanedioic acid condensate. These thickening agents may be used individually or in combination of two or more.

[0082] Examples of the aforementioned preservatives include methylparaben, ethylparaben, and butylparaben. These preservatives may be used individually or in combination of two or more.

[0083] Examples of the aforementioned powder components include inorganic powders such as talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, rose mica, biotite, thiamite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, tungstate metal salts, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, metal soaps (zinc myristate, calcium palmitate, aluminum stearate), and boron nitride; and organic powders such as polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene-acrylic acid copolymer resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, and cellulose powder. These powder components may be used individually or in combination of two or more types.

[0084] Examples of the aforementioned pigments include inorganic white pigments such as titanium dioxide and zinc oxide (including fine particle type titanium dioxide and zinc oxide used as ultraviolet scattering agents, or surface-coated inorganic white pigments in which the surface of these is coated with fatty acid soaps such as aluminum stearate and zinc palmitate, fatty acids such as stearic acid, myristic acid, palmitic acid, and fatty acid esters such as palmitate dextrin); inorganic red pigments such as iron oxide (red iron oxide) and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as yellow iron oxide and ochre; inorganic black pigments such as black iron oxide, carbon black, and lower-grade titanium oxide; inorganic purple pigments such as mango violet and cobalt violet; inorganic green pigments such as chromium oxide, chromium hydroxide, and cobalt titanate; and inorganic blue pigments such as ultramarine and Prussian blue. Examples of pigments include: system pigments; titanium oxide coated mica, titanium oxide coated bismuth oxychloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, and pearl pigments such as fish scale foil; metal powder pigments such as aluminum powder and copper powder; organic pigments such as Red 201, Red 202, Red 204, Red 205, Red 220, Red 226, Red 228, Red 405, Orange 203, Orange 204, Yellow 205, Yellow 401, and Blue 404; zirconium such as Red 3, Red 104, Red 106, Red 227, Red 230, Red 401, Red 505, Orange 205, Yellow 4, Yellow 5, Yellow 202, Yellow 203, Green 3, and Blue 1; and organic pigments such as barium or aluminum lake. These pigments may be used individually or in combination of two or more types.

[0085] Examples of the pH adjusting agents include EDTA, disodium EDTA, citric acid, sodium citrate, sodium hydroxide, potassium hydroxide, and triethanolamine. These pH adjusting agents may be used individually or in combination of two or more.

[0086] Examples of the antioxidants include vitamin C and its derivatives and salts thereof, tocopherols and their derivatives and salts thereof, dibutylhydroxytoluene, butylhydroxyanisole, and gallic acid esters. These antioxidants may be used individually or in combination of two or more.

[0087] Examples of the aforementioned ultraviolet absorbers include benzoic acid-based ultraviolet absorbers such as para-aminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N,N-dipropoxy PABA ethyl ester, N,N-diethoxy PABA ethyl ester, N,N-dimethyl PABA ethyl ester, N,N-dimethyl PABA butyl ester, and N,N-dimethyl PABA octyl ester; anthranilic acid-based ultraviolet absorbers such as homomenthyl-N-acetylanthranilate; amyl salicylate, menthyl salicylate, homomenthyl Salicylic acid-based UV absorbers such as salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, and p-isopropanolphenyl salicylate; octyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropyl cinnamate, methyl-2,4-diisopropyl cinnamate, propyl-p-methoxy cinnamate, isopropyl-p-methoxy cinnamate, isoamyl-p-methoxy cinnamate, octyl-p-methyl Cinnamic acid-based UV absorbers such as toxicinnameate (2-ethylhexyl-p-methoxycinnamate), 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, and glyceryl mono-2-ethylhexanoyl-diparamethoxycinnamate; 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4' Benzophenone-based UV absorbers such as -dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, and 4-hydroxy-3-carboxybenzophenone;Examples include 3-(4'-methylbenzylidene)-d,l-camphor, 3-benzylidene-d,l-camphor, urocanic acid, ethyl urocanic acid, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, dibenzarazine, dianisioylmethane, 4-methoxy-4'-t-butyldibenzoylmethane, 5-(3,3-dimethyl-2-norbornylidene)-3-pentan-2-one, and 2,4,6-trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)1,3,5-triazine, 4-tert-butyl-4'-methoxydibenzoylmethane, etc. These UV absorbers may be used individually or in combination of two or more types.

[0088] Examples of the aforementioned pigments include chlorophyll and β-carotene. These pigments may be used individually or in combination of two or more.

[0089] Examples of the aforementioned fragrances include plant-derived fragrances such as rose oil, jasmine oil, and lavender oil, and synthetic fragrances such as limonene, citral, linalool, and eugenol. These fragrances may be used individually or in combination of two or more.

[0090] Examples of the metal ion sequestering agents include disodium edetate, edetate salts, and hydroxyethanediphosphonic acid. These metal ion sequestering agents may be used individually or in combination of two or more.

[0091] One aspect of the present invention is a method for moisturizing the skin, comprising applying an effective amount of a topical skin composition containing an oily moisturizer according to the present invention to the skin surface of an object requiring moisturizing. The effective amount can be appropriately adjusted depending on the object to which the topical skin composition is applied and the environment in which the object exists, but for example, 1 cm of one application site. ２The dosage per application is 0.1 mg to 20 mg, preferably 0.2 mg to 10 mg. It can be applied 1 to 10 times per day, preferably 1 to 5 times. The application period can be adjusted depending on the condition of the subject. It can be used continuously, but applications ranging from one day to several months, for example, from one day to six months, are exemplified. It may also be used as a single application, or if multiple applications are made, they may be applied on consecutive days, and the application period may include non-application days.

[0092] The moisturizing effect of a topical skin composition can be evaluated by applying the composition to the skin according to its intended use and evaluating the change in stratum corneum moisture content. Stratum corneum moisture content is evaluated by measuring the electrical conductivity of the stratum corneum using commercially available equipment. The moisturizing effect of the topical skin composition is evaluated by calculating the change in stratum corneum moisture content before and after the test.

[0093] The test conditions, such as the method of use, application time, test time, and test period for the topical skin composition, should be determined according to the manner in which the topical skin composition is used. Furthermore, if the topical skin composition, dirt, dust, etc., remain on the surface, it may affect electrical conductivity and prevent accurate evaluation of stratum corneum moisture content; therefore, these should be washed or removed before measuring the electrical conductivity of the stratum corneum. It is preferable to evaluate the moisturizing effect of the topical skin composition during periods when the skin is prone to dryness.

[0094] To explain in more detail, the moisturizing effect of a topical skin composition after a single application can be evaluated as follows: First, the electrical conductivity (stratum corneum moisture content) of the stratum corneum of the skin is measured before applying the topical skin composition. Next, the topical skin composition is applied to the skin for a certain period of time according to its intended use, and then the topical skin composition is removed from the skin surface by washing or wiping. After a certain period of time has elapsed since removal, the electrical conductivity (stratum corneum moisture content) of the stratum corneum to which the topical skin composition was applied is measured. The moisturizing effect value is calculated using the obtained values ​​of electrical conductivity (stratum corneum moisture content) of the stratum corneum before and after application of the topical skin composition, and the moisturizing effect is evaluated. It is preferable to evaluate the moisturizing effect of a topical skin composition during periods when the skin is prone to dryness.

[0095] Furthermore, the moisturizing effect of a topical skin composition during continuous application can be evaluated, for example, as follows: First, before starting the continuous application test of the topical skin composition, the electrical conductivity of the stratum corneum of the skin (stratum corneum moisture content before the start of the continuous application test) is measured. Next, the topical skin composition is applied to the skin at least once a day according to its intended use, and daily life is continued for several days. On the day after the end of the continuous application test period, the area where the topical skin composition was applied is washed to remove any remaining topical skin composition, dirt, and dust, and then the electrical conductivity of the stratum corneum (stratum corneum moisture content at the end of the continuous application test) is measured. The moisturizing effect value is calculated using the obtained values ​​of electrical conductivity (stratum corneum moisture content) of the stratum corneum before and after the continuous application test, and the moisturizing effect is evaluated. It is preferable to evaluate the moisturizing effect of a topical skin composition during a time when the skin is prone to dryness.

[0096] As an example of applications of the external skin composition containing the oily moisturizer according to the present invention, a specific embodiment is shown below, including an ointment base, cosmetic oil, oil-in-water emulsion cosmetic, sunscreen, water-in-oil emulsion cosmetic, powder cosmetic, hair cosmetic, emulsion-type eye makeup cosmetic, water-based cosmetic, solvent-based nail care product, cleansing agent composition, pack cosmetic, and oily solid lip cosmetic.

[0097] [Ointment Base] In addition to the oily humectant according to the present invention, the ointment base may optionally contain other oily components, oily thickeners, antioxidants, and preservatives. The content of the oily humectant according to the present invention in the ointment base is preferably 0.1 to 99% by mass, and the content of the oily thickener is preferably 0.1 to 20% by mass.

[0098] Table 1 shows an example of an ointment-based formulation using the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily humectant according to the present invention. Note that "O.D.O," a product of Nisshin Oillio Group, can be used as tri(caprylic / capric acid) glyceryl, and "Leopal KL," a product of Chiba Flour Milling Co., Ltd., can be used as palmitate dextrin.

[0099] The ointment base of this formulation example 1 can be manufactured by heating and mixing ingredients 1 to 7 until uniformly dissolved, pouring the mixture into a wide-mouthed jar container, and allowing it to cool.

[0100]

[0101] [Cosmetic Oil] In addition to the oily humectant according to the present invention, the cosmetic oil may optionally contain other oily components, antioxidants, and preservatives. The content of the oily humectant according to the present invention in the cosmetic oil is preferably 0.1 to 100% by mass.

[0102] Table 2 shows an example of a cosmetic oil formulation using the esterified product produced in Example 1, described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizer according to the present invention.

[0103] The cosmetic oil in this formulation example 2 can be manufactured by dissolving ingredients 1 to 9 and mixing them uniformly.

[0104]

[0105] [Oil-in-Water Emulsified Cosmetics] In addition to the oily humectant according to the present invention, oil-in-water emulsion cosmetics may contain a surfactant, an aqueous humectant such as glycerin, a water-soluble polymer, and water. The content of the oily humectant according to the present invention in the oil-in-water emulsion cosmetic is preferably 0.1 to 60% by mass, the content of the surfactant is preferably 0.01 to 10% by mass, the content of the aqueous humectant is preferably 1 to 40% by mass, the content of the water-soluble polymer is preferably 0.001 to 5% by mass, and the content of water is preferably 20 to 95% by mass.

[0106] Table 3 shows an example of a formulation of an oil-in-water emulsion moisturizing cream using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizer according to the present invention. Note that "Cosmoll 168ARV," a product manufactured by Nisshin Oillio Group, can be used as the dipentaerythritol fatty acid ester.

[0107] The oil-in-water emulsion moisturizing cream of this formulation example 3 can be manufactured by the following steps A to C. A: Heat and dissolve components 1 to 9 and mix them uniformly. B: Heat and mix components 10 to 15 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A at 80°C and emulsify, then cool and add component 16.

[0108]

[0109] Table 4 shows an example of a formulation of an oil-in-water emulsion hand cream using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizer according to the present invention.

[0110] The oil-in-water emulsion hand cream of this formulation example 4 can be manufactured by the following steps A to C: A: Heat and dissolve components 1 to 8 and mix them uniformly. B: Heat and mix components 9 to 13 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A at 80°C, emulsify, and cool.

[0111]

[0112] Table 5 shows an example of a formulation of an oil-in-water emulsion cleansing cream using, for example, the esterified product produced in Example 1 described later, i.e., the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizer according to the present invention.

[0113] The oil-in-water emulsion cleansing cream of this formulation example 5 can be manufactured by the following steps A to C. A: Heat and dissolve components 1 to 8 and mix them uniformly. B: Heat and mix components 9 to 15 uniformly. C: At 80°C, add the mixture obtained in step B to the mixture obtained in step A and emulsify, then cool to obtain the oil-in-water emulsion cleansing cream.

[0114]

[0115] [Sunscreen] The sunscreen preferably contains a metal oxide powder having an ultraviolet shielding effect in addition to the oily humectant according to the present invention, and may further contain an organic ultraviolet absorber. It is more preferable that the average particle size of the metal oxide powder having an ultraviolet shielding effect is 10 to 100 nm, as this suppresses white cast when applied to the skin. The content of the oily humectant according to the present invention in the sunscreen is preferably 0.1 to 60% by mass.

[0116] Table 6 shows examples of formulations for a multilayer water-in-oil emulsion sunscreen using, for example, the esterified product produced in Example 1 described later, i.e., caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), and the esterified product produced in Example 11 described later, i.e., caprylic acid ester of sorbitan (hydroxyl value 2 mg KOH / g), as oily humectants according to the present invention. Furthermore, as stearic acid-treated fine particle titanium dioxide, "TIPAQUE TTO-S2" manufactured by Ishihara Sangyo Co., Ltd. can be used; as silicone-treated zinc oxide, "FINEX 25" manufactured by Sakai Chemical Industry Co., Ltd., treated with 5% methylhydrogenpolysiloxane can be used; and as cetyl dimethicone copolyol, "ABIL EM-90" manufactured by Evonik can be used.

[0117] The multilayer water-in-oil emulsion sunscreen of this formulation example 6 can be manufactured by the following steps A to D: A: Mix components 1 to 13 uniformly. B: Mix components 14 to 17 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the emulsion obtained in step C into a resin bottle containing a stainless steel ball.

[0118]

[0119] Table 7 shows an example of a formulation of a cream-type oil-in-water sunscreen using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizing agent according to the present invention. Furthermore, as the stearic acid-treated fine particle titanium dioxide, the product "TIPAQUE TTO-S2" manufactured by Ishihara Sangyo Co., Ltd. can be used.

[0120] The cream-type oil-in-water sunscreen of this formulation example 7 can be manufactured by the following steps A to E. A: Heat components 1 to 10 to 70°C and mix uniformly. B: Heat components 12 to 16 to 70°C and mix uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: After the emulsion obtained in step C is cooled to room temperature, component 11 is added and mixed. E: Fill the mixture obtained in step D into a container.

[0121]

[0122] Table 8 shows an example formulation of a water-in-oil sun care cream using, for example, the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily moisturizing agent according to the present invention. Shin-Etsu Chemical Co., Ltd.'s product "KF-6017" can be used as the polyether-modified silicone, and Shin-Etsu Chemical Co., Ltd.'s product "KF-9021" can be used as the trimethylsiloxysilicate solution.

[0123] The water-in-oil sun care cream of this formulation example 8 can be manufactured by the following steps A to C: A: Mix components 1 to 8 uniformly at room temperature. B: Mix components 9 to 12 uniformly at room temperature. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify and mix.

[0124]

[0125] Table 9 shows an example of a stick-type oily concealer formulation using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily humectant according to the present invention. For the stearic acid-treated titanium dioxide, a powder obtained by treating 3% by mass of Ishihara Sangyo Co., Ltd.'s product "TIPAQUE CR-50" with stearic acid can be used, and for the dipentaerythritol fatty acid ester, Nisshin Oillio Group's product "Cosmoll 168ARV" can be used.

[0126] The stick-type oily concealer of this formulation example 9 can be manufactured by the following steps A to D: A: Heat components 6 to 14 to 70°C and mix uniformly. B: Add components 1 to 5 and component 15 to the mixture obtained in step A and mix uniformly. C: Heat and dissolve the mixture obtained in step B again and degas it. D: Fill the processed product obtained in step C into a stick container and cool to room temperature.

[0127]

[0128] [Water-in-oil emulsion cosmetic] A water-in-oil emulsion cosmetic can be prepared by adding a surfactant and an aqueous component in addition to the oily humectant according to the present invention. The content of the oily humectant according to the present invention in the water-in-oil emulsion cosmetic is preferably 0.1 to 60% by mass, the content of the surfactant is preferably 0.1 to 10% by mass, and the content of the aqueous component is preferably 5 to 70% by mass.

[0129] Table 10 shows an example of a water-in-oil foundation formulation using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily humectant according to the present invention. Furthermore, "KF-6017" manufactured by Shin-Etsu Chemical Co., Ltd. can be used as the polyether-modified silicone, and "Benton 38" manufactured by ELEMENTIS can be used as the organically modified clay mineral.

[0130] The water-in-oil foundation of this formulation example 10 can be manufactured by the following steps A to C. A: Components 10 to 17 are heated and mixed, cooled to 40°C, and then components 1 to 9 and component 18 are added and dispersed in a homomixer. B: Components 19 to 24 are uniformly mixed and dissolved. C: The mixture obtained in step B is added to the dispersion obtained in step A and emulsified.

[0131]

[0132] Table 11 shows an example of a water-in-oil hand cream formulation using, for example, the esterified product produced in Example 1 described later, i.e., caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizing agent according to the present invention. Furthermore, Evonik's product "ABIL EM-90" can be used as the alkyl-containing polyoxyalkylene-modified organopolysiloxane.

[0133] The water-in-oil hand cream of this formulation example 11 can be manufactured by the following steps A to C. A: Mix ingredients 1 to 6 and disperse ingredient 7 therein using a disperser mixer. B: Mix ingredients 8 to 11 uniformly. C: Add the mixture obtained in step B to the dispersion obtained in step A and emulsify.

[0134]

[0135] Table 12 shows an example of a water-in-oil eyeshadow formulation using, for example, the esterified product produced in Example 2 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 67 mg KOH / g), as an oily humectant according to the present invention. Shin-Etsu Chemical Co., Ltd.'s product "KF-6017" can be used as the polyether-modified silicone, and Shin-Etsu Chemical Co., Ltd.'s product "KF-7312F" can be used as the trimethylsiloxysilicate solution.

[0136] The water-in-oil eyeshadow of this formulation example 12 can be manufactured by the following steps A to C. A: Mix components 1 to 7 and disperse component 8 therein using a disperser mixer. B: Mix components 9 to 13 uniformly. C: Add the mixture obtained in step B to the dispersion obtained in step A and emulsify.

[0137]

[0138] Table 13 shows an example of a water-in-oil mascara formulation using, for example, the esterified product produced in Example 2 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 67 mg KOH / g), as an oily humectant according to the present invention. Furthermore, "Benton 38" manufactured by ELEMENTIS Corporation can be used as the organically modified clay mineral, and "KF-7312J" manufactured by Shin-Etsu Chemical Co., Ltd. can be used as the organic silicone resin.

[0139] The water-in-oil mascara of this formulation example 13 can be manufactured by the following steps A to C: A: Mix components 6 to 12 uniformly. B: Mix components 1 to 5 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify.

[0140]

[0141] [Powdered Cosmetics] Powdered cosmetics contain powders such as extender pigments and coloring pigments in addition to the oily humectant according to the present invention. Preferably, the content of the oily humectant according to the present invention in the powdered cosmetics is 0.1 to 30% by mass, and the content of the powders is 70 to 95% by mass.

[0142] Table 14 shows an example of a solid powder foundation formulation using the esterified product produced in Example 2 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 67 mg KOH / g), as an oily humectant according to the present invention.

[0143] The solid powder foundation of this formulation example 14 can be manufactured by the following steps A to D: A: Heat components 8 to 12 to 50°C and mix. B: Mix and disperse components 1 to 7. C: Add the mixture obtained in step A to the mixed dispersion obtained in step B and mix. D: Grind the mixture obtained in step C and compress and mold it into a dish.

[0144]

[0145] Table 15 shows an example of a formulation of a solid powder face powder using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily humectant according to the present invention. Note that "Cosmoll 168ARV," a product manufactured by Nisshin Oillio Group, can be used as the dipentaerythritol fatty acid ester.

[0146] The solid powdered white powder of this formulation example 15 can be manufactured by the following steps A to C. A: Mix and disperse components 1 to 4. B: Add components 5 to 9 to the mixed dispersion obtained in step A and mix uniformly. C: Grind the mixture obtained in step B and compress and mold it into a dish.

[0147]

[0148] Table 16 shows an example of a formulation of a solid powder cake foundation (using water) using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 0 mg KOH / g), as an oily humectant according to the present invention. For silicone-treated talc, talc treated with 5% by mass of methylhydrogenpolysiloxane can be used, and for fluorine-treated sericite, sericite treated with 5% by mass of perfluoroalkyl phosphate diethanolamine salt can be used.

[0149] The solid powder cake foundation (using water) of this formulation example 16 can be manufactured by the following steps A to D. A: Mix and disperse components 1 to 8. B: Heat components 9 to 13 to 50°C and mix. C: Add the mixture obtained in step B and component 14 to the mixed dispersion obtained in step A and mix uniformly. D: Grind the mixture obtained in step C and compress and mold it into a dish.

[0150]

[0151] Table 17 shows an example of a powdered blush formulation using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily moisturizer according to the present invention.

[0152] The powdered blush of this formulation example 17 can be manufactured by the following steps A to C: A: Mix and disperse components 1 to 6 uniformly. B: Add component 7 to the mixed dispersion obtained in step A and mix uniformly. C: Grind the mixture obtained in step B and fill it into a container.

[0153]

[0154] Table 18 shows an example of a powdered eye color formulation using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily moisturizing agent according to the present invention.

[0155] The powdered eye color of this formulation example 18 can be manufactured by the following steps A to C. A: Mix and disperse components 1 to 6 uniformly. B: Add component 7 to the mixed dispersion obtained in step A and mix uniformly. C: Grind the mixture obtained in step B and fill it into a container.

[0156]

[0157] Table 19 shows an example of a formulation of a powdered body powder using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily moisturizer according to the present invention.

[0158] The powdered body powder of this formulation example 19 can be manufactured by the following steps A to C: A: Mix and disperse components 1 to 4 uniformly. B: Add component 5 to the mixed dispersion obtained in step A and mix uniformly. C: Grind the mixture obtained in step B and fill it into a container.

[0159]

[0160] [Hair Cosmetic] The hair cosmetic contains a cationic surfactant in addition to the oily humectant according to the present invention. The hair cosmetic can be further prepared by adding higher alcohols, water, humectants, etc.

[0161] Table 20 shows an example of a hair cream formulation using the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily moisturizing agent according to the present invention. For example, Shin-Etsu Chemical's "KF96A (6cs)" can be used as dimethylpolysiloxane, Clariant Japan's "GENAMIN STAC" as stearyltrimethylammonium chloride, and Nippon Emulsion Co., Ltd.'s "EMALEX 503" as polyoxyethylene oleyl ether.

[0162] The hair cream of this formulation example 20 can be manufactured by the following steps A to C. A: Mix and dissolve ingredients 1 to 6 uniformly. B: Mix and dissolve ingredients 7 to 11 and ingredient 13 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A at 80°C, emulsify, then add ingredient 12 and cool.

[0163]

[0164] Table 21 shows an example of a hair conditioner formulation using the esterified product produced in Example 2 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 67 mg KOH / g), as an oily humectant according to the present invention.

[0165] The hair conditioner of this formulation example 21 can be manufactured by the following steps A to C: A: Dissolve and mix ingredients 1 to 6 uniformly. B: Dissolve and mix ingredients 7 to 11 uniformly. C: Emulsify the mixture obtained in step B at 80°C while adding the mixture obtained in step A, then add ingredient 12 and mix.

[0166]

[0167] Table 22 shows an example of a hair rinse (for rinsing) formulation using, for example, the esterified product produced in Example 2 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 67 mg KOH / g), as an oily humectant according to the present invention. As a highly polymerized methylpolysiloxane emulsion, product "BY22-073" manufactured by Toray Dow Corning can be used.

[0168] This hair rinse (for rinsing) of formulation example 22 can be manufactured by the following steps A to C. A: Dissolve and mix components 1 to 4 uniformly. B: Dissolve and mix components 5 to 9 uniformly. C: Emulsify the mixture obtained in step B at 80°C while adding the mixture obtained in step A, then add component 10 and mix.

[0169]

[0170] Table 23 shows an example of a cuticle protection gel formulation using, for example, the esterified product produced in Example 16 described later, i.e., erythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid in the constituent fatty acid residues is 80:20, and the hydroxyl value is 9 mg KOH / g), as an oily moisturizer according to the present invention.

[0171] The cuticle protection gel of this formulation example 23 can be manufactured by the following steps A to D: A: Mix components 1 to 5 uniformly. B: Mix components 6 to 11 uniformly. C: Add the mixture obtained in step A to the mixture obtained in step B and mix and disperse. D: Add component 12 to the mixture obtained in step C and mix uniformly.

[0172]

[0173] [Emulsified Eye Makeup Cosmetics] The emulsion-type eye makeup cosmetic contains an oily humectant according to the present invention, in addition to a film-forming polymer emulsion. The emulsion-type eye makeup cosmetic can be prepared by adding a surfactant, pigment, higher alcohol, water, humectant, etc., in addition to the oily humectant and film-forming polymer emulsion according to the present invention. The content of the oily humectant according to the present invention in the emulsion-type eye makeup cosmetic is preferably 0.1 to 80% by mass of the total amount of the emulsion-type eye makeup cosmetic. Furthermore, in the emulsion-type eye makeup cosmetic, the solid content in the film-forming polymer emulsion is preferably 0.1 to 30% by mass of the total amount of the emulsion-type eye makeup cosmetic.

[0174] Table 24 shows examples of formulations for oil-in-water emulsion mascaras using, for example, the esterified product produced in Example 11 described later, i.e., sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), and the esterified product produced in Example 16 described later, i.e., erythritol (caprylic acid / capric acid) ester (the composition ratio of caprylic acid and capric acid of constituent fatty acid residues is 80:20, hydroxyl value 9 mg KOH / g).

[0175] The oil-in-water emulsion mascara of this formulation example 24 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 9, add components 10 to 12 and mix uniformly. B: Mix components 13 to 21 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the mixture obtained in step C into a container.

[0176]

[0177] Table 25 shows an example of a water-in-oil emulsion mascara formulation using, for example, the esterified product produced in Example 16 described later, i.e., erythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid in the constituent fatty acid residues is 80:20, and the hydroxyl value is 9 mg KOH / g), as an oily humectant according to the present invention.

[0178] The water-in-oil emulsion mascara of this formulation example 25 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 5 and mix them uniformly. B: Mix components 6 to 11 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the mixture obtained in step C into a container.

[0179]

[0180] Table 26 shows an example of a formulation for an oil-in-water emulsion eyeliner using the esterified product produced in Example 6 described later, namely, the (caprylic / capric acid) ester of dipentaerythritol (with a composition ratio of caprylic acid and capric acid of constituent fatty acid residues of 80:20 and a hydroxyl value of 150 mg KOH / g), as an oily humectant according to the present invention.

[0181] The oil-in-water emulsion eyeliner of this formulation example 26 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 4, add components 5 and 6 and mix uniformly. B: Mix components 7 to 13 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the mixture obtained in step C into a container.

[0182]

[0183] Table 27 shows an example of a formulation of an oil-in-water emulsion eyeshadow using, for example, the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily humectant according to the present invention.

[0184] The oil-in-water emulsion eyeshadow of this formulation example 27 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 6, add components 7 and 8 and mix uniformly. B: Mix components 9 to 16 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the mixture obtained in step C into a container.

[0185]

[0186] Table 28 shows an example of an oil-in-water emulsion eyebrow formulation using, for example, the esterified product produced in Example 11 described later, namely sorbitan caprylic acid ester (hydroxyl value 2 mg KOH / g), as an oily humectant according to the present invention.

[0187] The oil-in-water emulsion eyebrow product of this formulation example 28 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 6, add component 7 and mix uniformly. B: Mix components 8 to 13 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A and emulsify. D: Fill the mixture obtained in step C into a container.

[0188]

[0189] [Water-based cosmetic] The water-based cosmetic contains, in addition to the oily humectant according to the present invention, ethanol, a nonionic surfactant, an alkyl-modified carboxyvinyl polymer, and water. The content of the oily humectant according to the present invention in the water-based cosmetic is preferably 0.01 to 40% by mass of the total amount of the water-based cosmetic.

[0190] Table 29 shows an example of a lotion formulation using the esterified product produced in Example 6 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid in the constituent fatty acid residues is 80:20, and the hydroxyl value is 150 mg KOH / g), as an oily moisturizer according to the present invention.

[0191] The lotion of this formulation example 29 can be manufactured by the following steps A to C: A: Mix and dissolve ingredients 1 to 3 uniformly. B: Mix and dissolve ingredients 4 to 8 uniformly. C: Add the mixture obtained in step A to the mixture obtained in step B while stirring, and fill into a container.

[0192]

[0193] Table 30 shows an example of a serum formulation using the esterified product produced in Example 6 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (with a composition ratio of caprylic and capric acid of constituent fatty acid residues of 80:20 and a hydroxyl value of 150 mg KOH / g), as an oily moisturizer according to the present invention.

[0194] The serum of this formulation example 30 can be manufactured by the following steps A to C: A: Mix and dissolve ingredients 1 to 5 uniformly. B: Mix and dissolve ingredients 6 to 11 uniformly. C: Add the mixture obtained in step A to the mixture obtained in step B while stirring, and fill into a container.

[0195]

[0196] Table 31 shows an example of a gel-type eye color formulation using the esterified product produced in Example 6 described later, namely, the (caprylic / capric acid) ester of dipentaerythritol (with a composition ratio of caprylic acid and capric acid of constituent fatty acid residues of 80:20 and a hydroxyl value of 150 mg KOH / g), as an oily humectant according to the present invention.

[0197] The gel-type eye color of this formulation example 31 can be manufactured by the following steps A to C. A: Mix and dissolve components 1 to 7 uniformly. B: Mix and dissolve components 8 to 11 uniformly. C: Add the mixture obtained in step A to the mixture obtained in step B while stirring.

[0198]

[0199] [Solvent-based nail care product] The solvent-based nail care product contains, in addition to the oily humectant according to the present invention, a film-forming agent and a non-aromatic solvent. The content of the oily humectant according to the present invention in the solvent-based nail care product is preferably 0.01 to 40% by mass of the total amount of the solvent-based nail care product.

[0200] Table 32 shows an example of a nail polish formulation using the esterified product produced in Example 5 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid of constituent fatty acid residues is 80:20, and the hydroxyl value is 0 mg KOH / g), as an oily humectant according to the present invention. Furthermore, "Acrybase MH7057" manufactured by Fujikura Chemical Co., Ltd. can be used as the alkyl acrylate / styrene copolymer, "Benton 27" manufactured by ELEMENTIS Inc. can be used as the organically modified clay mineral, and "AEROSIL 300" manufactured by Nippon Aerosil Co., Ltd. can be used as the anhydrous silicic acid.

[0201] The nail polish of this formulation example 32 can be manufactured by the following steps A to C: A: Mix components 7 to 9, add component 10, and mix uniformly. B: Add components 1 to 6 to the mixture obtained in step A and mix uniformly. C: Add components 11 to 15 to the mixture obtained in step B and mix uniformly, then fill into a container.

[0202]

[0203] Table 33 shows an example of a topcoat formulation using the esterified product produced in Example 5 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid of constituent fatty acid residues is 80:20, and the hydroxyl value is 0 mg KOH / g), as an oily humectant according to the present invention. Fujikura Chemicals' product "Acrybase MH7057" can be used as the alkyl acrylate / styrene copolymer.

[0204] The top coat of this formulation example 33 can be manufactured by the following steps A and B: A: Mix components 5 to 8 uniformly, then add components 1 to 4 and mix uniformly. B: Fill the mixture obtained in step A into a container.

[0205]

[0206] Table 34 shows an example of a base coat formulation using the esterified product produced in Example 5 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid in the constituent fatty acid residues is 80:20, and the hydroxyl value is 0 mg KOH / g), as an oily humectant according to the present invention. As the alkyl acrylate / styrene copolymer, Fujikura Chemical Co., Ltd.'s product "Acrybase MH7057" can be used.

[0207] The base coat of this formulation example 34 can be manufactured by the following steps A and B: A: Mix components 4 to 7 uniformly, then add components 1 to 3 and mix uniformly. B: Fill the mixture obtained in step A into a container.

[0208]

[0209] [Detergent Composition] The detergent composition contains, in addition to the oily humectant according to the present invention, one or more selected from anionic surfactants, amphoteric surfactants, and nonionic surfactants. The content of the oily humectant according to the present invention in the detergent composition is preferably 0.01 to 30% by mass of the total amount of the detergent composition. The total content of one or more selected from anionic surfactants, amphoteric surfactants, and nonionic surfactants in the detergent composition is preferably 0.01 to 40% by mass of the total amount of the detergent composition.

[0210] Table 35 shows an example of a shampoo formulation using the esterified product produced in Example 5 described later, namely, the (caprylic / capric acid) ester of dipentaerythritol (with a composition ratio of caprylic acid and capric acid of constituent fatty acid residues of 80:20 and a hydroxyl value of 0 mg KOH / g), as an oily humectant according to the present invention.

[0211] The shampoo of this formulation example 35 can be manufactured by uniformly mixing ingredients 1 to 9.

[0212]

[0213] Table 36 shows an example of a body soap formulation using the esterified product produced in Example 5 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid of constituent fatty acid residues is 80:20, and the hydroxyl value is 0 mg KOH / g), as an oily moisturizer according to the present invention.

[0214] This body soap, formulation example 36, can be manufactured by uniformly mixing ingredients 1 to 10.

[0215]

[0216] Table 37 shows an example of a facial cleansing cream formulation using, for example, the esterified product produced in Example 5 described later, i.e., dipentaerythritol (caprylic / capric acid) ester (the composition ratio of caprylic and capric acid of constituent fatty acid residues is 80:20, and the hydroxyl value is 0 mg KOH / g), as an oily moisturizing agent according to the present invention. Furthermore, as the highly polymerized dimethylpolysiloxane, Shin-Etsu Chemical Co., Ltd.'s product "KF-96H-6000cs" can be used.

[0217] The facial cleansing cream of this formulation example 37 can be manufactured by the following steps A to C. A: Heat and dissolve components 1 to 7 to 70°C. B: Heat components 8 to 12 to 70°C. C: At 70°C, gradually add the mixture obtained in step A to the mixture obtained in step B while stirring, and after the saponification reaction is complete, cool while stirring.

[0218]

[0219] Table 38 shows an example of a gel-type facial cleanser formulation using the esterified product produced in Example 1, described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizing agent according to the present invention.

[0220] The gel-type facial cleanser of this formulation example 38 can be manufactured by the following steps A and B: A: Mix components 1 to 3 uniformly. B: Add components 4 to 9 to the mixture obtained in step A and mix uniformly.

[0221]

[0222] Table 39 shows examples of cleansing oil formulations using, for example, the esterified product produced in Example 1, i.e., caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), the esterified product produced in Example 11, i.e., caprylic acid ester of sorbitan (hydroxyl value 2 mg KOH / g), and the esterified product produced in Example 15, i.e., caprylic acid ester of erythritol (hydroxyl value 0 mg KOH / g), as oily moisturizing agents according to the present invention.

[0223] The cleansing oil of this formulation example 39 can be manufactured by uniformly mixing ingredients 1 to 9.

[0224]

[0225] [Pack Cosmetic] In addition to the oily humectant according to the present invention, the pack cosmetic may contain an aqueous humectant such as glycerin, a water-soluble polymer, and water. The content of the oily humectant according to the present invention in the pack cosmetic is preferably 0.1 to 60% by mass, the content of the aqueous humectant is preferably 1 to 40% by mass, the content of the water-soluble polymer is preferably 0.001 to 20% by mass, and the content of water is preferably 20 to 95% by mass.

[0226] Table 40 shows an example of a paste-type peel-off pack formulation using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily humectant according to the present invention. Note that Kuraray's product "Kuraray Poval PVA217" can be used as the polyvinyl alcohol.

[0227] The paste-type peel-off pack of this formulation example 40 can be manufactured by the following steps A to C: A: Mix components 1 to 5 uniformly. B: Mix components 6 to 9 uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A, heat and stir at 50°C, cool, and then add component 10.

[0228]

[0229] Table 41 shows an example of a cream pack formulation using the esterified product produced in Example 1, described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizing agent according to the present invention.

[0230] The cream pack of this formulation example 41 can be manufactured by the following steps A to C. A: Heat and dissolve components 1 to 6 at 80°C and mix uniformly. B: Heat and dissolve components 7 to 12 at 80°C and mix uniformly. C: Add the mixture obtained in step B to the mixture obtained in step A at 80°C, emulsify, cool, and add component 13.

[0231]

[0232] Table 42 shows an example of a sheet pack formulation using the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily moisturizing agent according to the present invention. Note that "Saracos PG-180," a product of Nisshin Oillio Group, can be used as polyglyceryl-10 monooleate, and "Saracos DG-180," a product of Nisshin Oillio Group, can be used as polyglyceryl-2 monooleate.

[0233] The sheet-like pack of this formulation example 42 can be manufactured by the following steps A to D: A: Heat and dissolve components 1 to 3 and mix them uniformly. B: Heat and mix components 4 to 9 uniformly. C: Add the mixture obtained in step A to the mixture obtained in step B, emulsify, and cool to obtain the liquid portion for the sheet-like pack. D: Impregnate a nonwoven fabric with the liquid portion obtained in step C to obtain the sheet-like pack.

[0234]

[0235] [Oil-based solid lip cosmetic] In addition to the oil-based humectant according to the present invention, the oil-based solid lip cosmetic may optionally contain a wax component with a melting point of 70°C or higher, other oil-based components, organic pigments, inorganic pigments, antioxidants, and preservatives. The content of the oil-based humectant according to the present invention in the cosmetic oil is preferably 0.1 to 95% by mass.

[0236] Table 43 shows an example of a formulation of an oily solid lip cosmetic using, for example, the esterified product produced in Example 1 described later, namely, the caprylic acid ester of dipentaerythritol (hydroxyl value 0 mg KOH / g), as an oily humectant according to the present invention. Note that "Cosmol 168ARV" manufactured by Nisshin Oillio Group can be used as the dipentaerythrityl fatty acid ester, "Saracos WO-6" manufactured by Nisshin Oillio Group can be used as the dipentaerythrityl tripolyhydroxystearate, and "Cosmol 43V" manufactured by Nisshin Oillio Group can be used as the polyglyceryl-2 triisostearate.

[0237] The oily solid lip cosmetic of this formulation example 43 can be manufactured by the following steps A to D. A: Heat components 5 to 16 to 90°C and mix uniformly. B: Add components 1 to 4 and component 17 to the mixture obtained in step A and mix uniformly. C: Heat and dissolve the mixture obtained in step B again and degas it. D: Fill the processed product obtained in step C into a stick container and cool to room temperature.

[0238]

[0239] The present invention will be described in more detail below based on embodiments, but the present invention is not limited in any way to these descriptions. In the following, unless otherwise specified, "%" means mass percent.

[0240] [Examples 1-18, Comparative Examples 1-9] Production of Esterified Products Esterified products were produced by using alcohol and fatty acids as reaction raw materials, and by adjusting the molar ratio of alcohol to fatty acid to carry out an esterification reaction. Specifically, first, the alcohol and fatty acid listed in Tables 46 and 47 were placed in a four-necked flask, heated to 180-240°C under a nitrogen stream, and the esterification reaction was carried out for about 10-20 hours while removing the generated water from the system. After the reaction was completed, excess acid was removed as needed to obtain the desired esterified product. More specifically, the esterified product of Example 5 was produced by the method shown in Production Example 1 described later. The esterified product of Example 2 was produced by the method shown in Production Example 2 described later.

[0241] Tables 46 and 47 show the reaction raw materials, hydroxyl value, properties (appearance) at 35°C, evaluation results of moisturizing effect, and evaluation results of usability of the obtained esterified products. Furthermore, for esterified products produced using two types of fatty acids as raw materials, the composition of constituent fatty acid residues of the obtained esterified products was measured, and the mass ratio of each constituent fatty acid residue was calculated. These values ​​are shown in Tables 46 and 47.

[0242] [Production Example 1] Production of Esterified Products Dipentaerythritol, caprylic acid, and capric acid were used as reaction raw materials. The molar ratios of dipentaerythritol, caprylic acid, and capric acid were adjusted so that the hydroxyl value of the resulting esterified product was 0 mg KOH / g and the mass ratio of caprylic acid to capric acid in the resulting esterified product was 8:2. Specifically, 1198.6 g (8.3 mol) of caprylic acid, 299.6 g (1.7 mol) of capric acid, and 254.3 g (1.0 mol) of dipentaerythritol were placed in a four-necked flask and heated to 230-240°C under a nitrogen stream. The esterification reaction was carried out for approximately 15 hours while removing the water produced from the system. After the reaction was completed, excess acid was removed to obtain 940 g of the target esterified product. The acid value of the obtained esterified product was 0.1 and the hydroxyl value was 0 mg KOH / g. Furthermore, the mass ratio of the constituent fatty acid residues of the obtained esterified product was caprylic acid:capric acid = 79:21.

[0243] [Production Example 2] Production of Esterified Products Dipentaerythritol and caprylic acid were used as reaction raw materials, and the molar ratio of dipentaerythritol to caprylic acid was adjusted so that the hydroxyl value of the resulting esterified product was approximately 70 mg KOH / g. Specifically, 692.2 g (4.8 mol) of caprylic acid and 254.3 g (1.0 mol) of dipentaerythritol were placed in a four-necked flask and heated to 230-240°C under a nitrogen stream. The esterification reaction was carried out for approximately 25 hours while removing the water produced from the system. The reaction was terminated when it was confirmed that the acid value of the reactants had fallen below 1, and 817 g of the target esterified product was obtained. The obtained esterified product had an acid value of 0.1 and a hydroxyl value of 67 mg KOH / g.

[0244] [Comparative Example 10] Production of Dipentaerythritol Fatty Acid Ester Dipentaerythritol and caprylic acid were used as reaction raw materials, and the molar ratio of dipentaerythritol to caprylic acid was adjusted so that the hydroxyl value of the resulting esterified product was approximately 170 mg KOH / g. However, the reaction separated into two phases, and the desired esterified product could not be produced. Therefore, various evaluations of the dipentaerythritol fatty acid ester with a hydroxyl value of approximately 170 mg KOH / g could not be performed.

[0245] <Measurement of the composition of constituent fatty acid residues of esterified products> In the following examples, the mass ratio of each constituent fatty acid residue of the esterified product was measured by first preparing a derivative by methyl esterifying the fatty acid residues in the esterified product using a method corresponding to 2.4.1.1-2013 Methyl esterification method (sulfuric acid-methanol method) (published by the Japan Oil Chemists' Society, "Standard Test Methods for Analysis of Fats and Oils, 2013 Edition"), and then separating the obtained derivative using a method corresponding to 2.4.2.3-2013 Fatty acid composition (capillary gas chromatography method) (published by the Japan Oil Chemists' Society, "Standard Test Methods for Analysis of Fats and Oils, 2013 Edition").

[0246] Specifically, first, one drop of the esterified product was placed in a test tube and dissolved in 2 mL of sulfuric acid-methanol solution [a solution prepared by mixing 2 mL of sulfuric acid with 230 mL of methanol]. Next, the test tube was heated, and a derivative was prepared by methyl esterifying the fatty acid residue in the esterified product via a transesterification reaction.

[0247] These methyl ester derivatives were dissolved in 2 mL of hexane and injected into a column of a gas chromatograph equipped with FID. Each methyl ester derivative was then separated and detected under the following GC analysis conditions.

[0248] <GC Analysis Conditions> • Column: DB-1ht (Agilent Technologies) • Injection Volume: 1 μL • Carrier Gas: Helium • Column Temperature: 50–370°C (15°C / min heating)

[0249] The chromatographic peaks were identified by comparing their retention times with those obtained by analyzing a standard substance under the same measurement conditions as the test sample. The composition of fatty acid residues in the esterified product was calculated based on the percentage of peak area of ​​the methyl ester derivative peaks derived from each fatty acid residue on the chromatograph.

[0250] <Skin Stratum Corneum Moisture Content Measurement Test> In this invention, the moisturizing effect of the esterified product, that is, the effect of improving the moisturizing function of the skin, was evaluated based on the change in the stratum corneum moisture content of the skin before and after application of the esterified product. The stratum corneum moisture content was measured using a stratum corneum moisture content measuring device (device name: SKICON-200) from IBS Corporation. The stratum corneum moisture content measuring device is a general-purpose instrument used to measure the moisture state of the stratum corneum, and is a device that measures the electrical conductivity (μS) of the stratum corneum. The higher the skin moisture content, the higher the electrical conductivity of the stratum corneum. Therefore, the electrical conductivity (μS) measured by the stratum corneum moisture content measuring device was defined as the stratum corneum moisture content.

[0251] <Evaluation Test of Moisturizing Effect of Esterified Substances After Single Application> The moisturizing effect of the test samples on the skin was evaluated based on the change in the stratum corneum moisture content of the skin after directly applying the test samples to cleansed skin and wiping it off with a cotton swab soaked in hexane. The skin stratum corneum moisture content measurement test was conducted on multiple panelists during the autumn to spring period, when skin tends to dry out. In addition, to eliminate the influence of room temperature and humidity on the measurement results, the test was conducted in a room where the room temperature was adjusted to 18-22°C and the humidity to 40-55% RH.

[0252] Specifically, first, a human forearm was washed with soap, and then the skin of the forearm was allowed to acclimate to the measurement environment by being placed in a room with the temperature and humidity adjusted to the aforementioned range for 30 minutes, thus preparing the initial conditions for measurement. Next, a 3 cm x 3 cm square on the washed forearm was designated as the measurement site, and the stratum corneum moisture content of the skin in that area was measured and used as the blank value (stratum corneum moisture content before the start of the test). After that, 40 μL of the test sample to be evaluated was uniformly applied to the square measurement site on the forearm. 60 minutes after application, the test sample was wiped off with a cotton swab soaked in hexane, and 30 minutes after wiping, the stratum corneum moisture content of the skin in the wiped area (stratum corneum moisture content at the end of the test) was measured. In addition, in order to consider and subtract changes in skin condition during the measurement time when evaluating the moisturizing effect of the test sample, the stratum corneum moisture content of the unapplied area was also measured before the start of the test and at the end of the test, and the change in stratum corneum moisture content of the unapplied area was calculated.

[0253] The moisturizing effect value (μS) was calculated from the measured stratum corneum moisture content of the skin based on the following formula. The moisturizing effect value (μS) for each test sample was the average of the moisturizing effect values ​​(μS) of the five panelists.

[0254] (Equation 1) [Moisturizing effect value (μS)] = [Stratum corneum moisture content of the coated area at the end of the test (μS)] - [Stratum corneum moisture content of the blank (μS)] - [Change in stratum corneum moisture content of the uncoated area (μS)] (Equation 2) [Change in stratum corneum moisture content of the uncoated area (μS)] = [Stratum corneum moisture content of the uncoated area at the end of the test (μS)] - [Stratum corneum moisture content of the uncoated area before the start of the test (μS)]

[0255] Based on the moisturizing effect value (μS) of each test sample, the moisturizing effect of each test sample was evaluated according to the criteria in Table 44. Test samples with moisturizing evaluations of a1, b1, and c1 were judged to have a moisturizing effect and be useful as moisturizers, while test samples with evaluations of d1 and e1 were judged to lack sufficient moisturizing effect and not be useful as moisturizers.

[0256]

[0257] <Evaluation of Moisture-Retaining Effects During Single Application> For each esterified compound, five panelists conducted the <Evaluation Test of Moisture-Retaining Effects During Single Application of Esterified Compounds> described above to evaluate its moisturizing properties. However, since the skin's epidermal temperature during the test was approximately 30-35°C, evaluation samples that were solid at 35°C could not be properly applied to the skin. Therefore, for esterified compounds that were solid at 35°C, they were mixed with cetyl 2-ethylhexanoate (product name "Sarakos 816T", manufactured by Nisshin Oillio Group Co., Ltd.) in a 1:1 mass ratio, and the resulting liquid at 35°C was used as the test sample for evaluation.

[0258] <Evaluation of User Experience> For topical skin compositions, excellent user experience is also important in actual use. Sensory evaluations were conducted for each esterified compound, specifically regarding "non-stickiness" and "adhesion."

[0259] Four expert panelists evaluated the "non-stickiness" and "adhesion" of each test sample when applied uniformly to the forearm, using a five-point scale (5 points: good, 4 points: fairly good, 3 points: average, 2 points: slightly bad, 1 point: bad). The usability score for each test sample was the average of the scores given by the four panelists.

[0260] Based on the "non-stickiness" evaluation score of each test sample, the usability of each test sample was evaluated according to the criteria in Table 45.

[0261]

[0262] Based on the "adhesion" evaluation score of each test sample, the usability of each test sample was evaluated according to the criteria in Table 46.

[0263]

[0264]

[0265]

[0266] [Comparative Examples 11-23] The moisturizing effect was investigated by performing the above-mentioned <Moisturizing Evaluation during Single Application> on various commercially available oils and glycerin. The properties (appearance) and evaluation results of the various commercially available oils and glycerin at 35°C are shown in Table 49.

[0267] Glycerin in Comparative Example 23 is a typical aqueous humectant and is commonly used as a humectant. In the case of glycerin, in the <Hydrating Evaluation for Single Application> described above, a cotton swab soaked in water was used to remove the glycerin applied to the skin, instead of hexane. The evaluation conditions were the same as in the <Hydrating Evaluation for Single Application> described above, except that the solvent used for removal was changed from hexane to water.

[0268]

[0269] From the results in Tables 47-49, it was found that the esterified products of Examples 1-18, that is, esterified products with a hydroxyl value of 0-160 mgKOH / g obtained by using dipentaerythritol, erythritol, or sorbitan as the reaction raw material for the esterification reaction, and by using one or more fatty acids selected from fatty acids with 6-28 carbon atoms as the fatty acid, are oily substances with a high moisturizing effect value of 50 μS or more, and are very useful as oily humectants. On the other hand, the esterified products of Comparative Examples 2 to 5, 8, and 9, which do not use dipentaerythritol, erythritol, or sorbitan as raw materials, the esterified product of Comparative Example 1, which uses erythritol or dipentaerythritol as a raw material but in which the mass ratio of fatty acid residues derived from component B to fatty acid residues derived from component C in the esterified product of component A, component B, and component C is outside the range of 99.9:0.1 to 45:55, and the esterified products of Comparative Examples 6 and 7, which use erythritol as a raw material but do not use component B as a raw material, had a moisturizing effect value of less than 50 μS, and did not show sufficient moisturizing effect as a humectant. The oils of Comparative Examples 11 to 22 are oils that have been conventionally used as raw materials for external skin compositions, but it was confirmed that the esterified products of Examples 1 to 18, which are oily humectants according to the present invention, exhibit a higher moisturizing effect than the oils of Comparative Examples 11 to 22.

[0270] The esterified products of Examples 1 to 18 were able to maintain a high stratum corneum moisture content even after being removed from the skin. From this, it can be inferred that they exert their moisturizing effect through a mechanism different from conventional oily moisturizers, which exert their moisturizing effect by suppressing moisture evaporation from the skin by forming an oily film on the skin surface.

[0271] Although glycerin in Comparative Example 23 is generally considered to have good moisturizing properties and is widely used as an aqueous moisturizer, the moisturizing effect value of glycerin in this moisturizing evaluation was 8 μS, and sufficient moisturizing effect was not confirmed. For reference, when the stratum corneum moisture content was measured on skin with glycerin applied to the skin surface 60 minutes after application and before removal with water, the increase in electrical conductivity corresponding to the moisturizing effect value was a very high value of 477 μS, confirming that glycerin is said to be useful as a moisturizer. However, considering that glycerin is highly hygroscopic and that this value decreases significantly after glycerin is removed from the skin, it is presumed that this moisturizing effect value before glycerin removal is the result of measuring the sum of the moisture content in the stratum corneum and the moisture content contained in glycerin.

[0272] [Examples 19-23, Comparative Examples 24-29] The moisturizing effect of emulsions containing the esterified compounds of Examples 2, 5, 13, 14, and 16, the esterified compound of Comparative Example 1, and the oils of Comparative Examples 12, 15, 18, and 20 was investigated in single-application tests (tests in which the emulsion was applied to the skin surface only once).

[0273] Specifically, emulsions with the formulations shown in Tables 51 and 52 were first manufactured by the following steps A to C. For the glyceryl stearate, "LASEMUL92AE" from Industrial Quimica Lasem (IQL) was used; for PEG-100 stearate, "LASEMUL4000" from IQL was used; and for the (acrylates / alkyl acrylate (C10-30)) crosspolymer, "Pemulen TR-1" from Lubrizol was used. A: Components 1-2 were heated and mixed at 70°C. B: Components 3-10 were uniformly heated and mixed at 70°C. C: The mixture obtained in step B was added to the mixture obtained in step A, and the mixture was emulsified in an emulsifier (tabletop disper mixer) at 2000 rpm, 70°C, and for 5 minutes to obtain an emulsion.

[0274] <Evaluation Test of Moisturizing Effect of Single Application of Emulsion> Moisturizing effects of the emulsions in Examples 19-23 and Comparative Examples 24-29 were evaluated by 10 panelists. Specifically, the moisturizing effect of the emulsions containing esterified compounds was evaluated by applying the emulsion containing an esterified compound or oil to cleansed skin, washing it with running water, and then measuring the moisture content of the stratum corneum of the skin.

[0275] The skin stratum corneum moisture content measurement test was conducted during the autumn and spring months, when skin tends to be dry. In addition, to eliminate the influence of room temperature and humidity on the measurement results, the test was conducted in a room where the room temperature was adjusted to 18-22°C and the humidity to 40-55%.

[0276] The moisture content of the stratum corneum of the skin was measured as follows. First, as in the <Evaluation Test of Moisturizing Effect of Single Application of Esterified Substances> described above, the measurement area was cleaned, acclimatized to the environment, a blank value was measured, and the unapplied area was measured. Then, 40 mg of the emulsion was uniformly applied to a square measurement area on the forearm. Five hours after application, the applied area was washed with running water (2 L / min) for 20 seconds, excess water was wiped off, and the moisture content of the stratum corneum (μS) was measured 30 minutes later. Next, as in the <Evaluation Test of Moisturizing Effect of Single Application of Esterified Substances> described above, the average value of the moisturizing effect values ​​of five panelists, obtained using Equations 1 and 2, was taken as the moisturizing effect value (μS) of each emulsion.

[0277] (Equation 1) [Moisturizing effect value (μS)] = [Stratum corneum moisture content of the coated area at the end of the test (μS)] - [Stratum corneum moisture content of the blank (μS)] - [Change in stratum corneum moisture content of the uncoated area (μS)] (Equation 2) [Change in stratum corneum moisture content of the uncoated area (μS)] = [Stratum corneum moisture content of the uncoated area at the end of the test (μS)] - [Stratum corneum moisture content of the uncoated area before the start of the test (μS)]

[0278] Based on the moisturizing effect value (μS) of each emulsion, the moisturizing effect of each emulsion was evaluated according to the criteria in Table 50. Emulsions with moisturizing evaluations of a4, b4, and c4 were judged to be useful as emulsions with moisturizing effect, while emulsions with d4 and e4 were judged to have no moisturizing effect and not be useful as emulsions with moisturizing effect. The evaluation results for each emulsion are shown in Tables 51 and 52.

[0279]

[0280]

[0281]

[0282] Tables 51 and 52 show that the emulsion containing the esterified oily humectant according to the present invention provides a higher moisturizing effect than the esterified emulsion of Comparative Example 1 or the emulsions of Comparative Examples 24-29 containing commercially available oils, even when applied once to the skin surface and then removed. Furthermore, it was confirmed that the moisturizing effect of the emulsion was higher when the oily humectant according to the present invention was included, even when compared to an emulsion without an oil (Comparative Example 29).

[0283] According to the present invention, it is possible to provide an oily humectant with excellent skin moisturizing effect, and a topical skin composition containing the same.

Claims

DEPCT641. An oil-based humectant product characterized as an esterification product containing components A and B, or an esterification product containing components A, B, and C, with a pH of 0-160 mg KOH / g, and a mass ratio of fatty acid residues obtained from component B and fatty acid residues obtained from component C in the fatty acid residues that make up the esterification product containing components A and B. Composition B and composition C are equal to 99.9:0.1-45:

55. Composition A: Polyhydric alcohol as dipentaryrytritol, erythritol, or sorbitan. Composition B: One or more fatty acids, or equal to two, selected from 6-10 carbon-chain saturated fatty acids. Composition C: One or more fatty acids, or equal to two, selected from 6-28 carbon-chain fatty acids (excluding composition B).

2. A humectant containing the oil specified in claim 1, in which composition A is dipentaryrytritol. 3.

1. A topical skin preparation characterized by the inclusion of an oil-based humectant specified in Patent 1 or 24.

2. A topical skin preparation specified in Patent 3, which is a cosmetic, facial cleanser, body cleanser, or topical pharmaceutical product.

3. A method of moisturizing the skin characterized by the application of a topical skin preparation containing an oil-based humectant specified in Patent 1 or 26.

4. The use of an esterification product containing components A, B, and C to maintain moisture, where the esterification product containing components A and B has a pH of 0-160 mg KOH / g or a pH of 0-160 mg KOH / g, and the mass ratio of fatty acid residues obtained from component B and fatty acid residues obtained from component C in the fatty acid residue is 99.9:0.1-45:55 Component A: Polyhydric alcohol as dipentary erythritol, erythritol, or sorbitan. Component B: One or more, or equal to two, fatty acids selected from straight-chain saturated fatty acids with 6-10 carbon atoms. Component C: One or more, or equal to two, fatty acids selected from fatty acids with 6-28 carbon atoms (excluding component B).

7. Use to create formulations for external skin application of esterification products containing components A and B and components C, which are esterification products containing components A and B with a pH of 0-160 mg KOH / g or with a pH of 0-160 mg KOH / g, including a mass ratio of fatty acid residues obtained from component B and fatty acid residues obtained from component C in the fatty acid residue composition equal to 99.9:0.1-45:55 Component A: Polyhydric alcohol as dipentaryrytriol, erythritol, or sorbitan. Component B: One or more fatty acids, or two or more, selected from straight-chain saturated fatty acids with 6-10 carbon atoms. Component C: One or more fatty acids, or two or more, selected from fatty acids with 6-28 carbon atoms (excluding component B). -----------------------------------------------------------;.