Cosmetic composition and method for producing same

Abstract

Provided is a cosmetic composition having excellent emulsifiability and little residual feeling. In addition, provided is a method for producing said cosmetic composition.　A cosmetic composition containing a polyglycerol monofatty acid ester (A) and an oil agent (B), wherein in the polyglycerol monofatty acid ester (A), the number of carbon atoms in the fatty acid is 4-25, the peak intensity ratio represented by formula (X) is 0.20 or more, and the peak intensity ratio represented by formula (Y) is 0.46 or less.　Formula (X): P2 / P1 Formula (Y): P3 / P1 P1: The total of peak intensities, obtained by performing mass spectrometry on the polyglycerol monofatty acid ester (A) by using a time‑of‑flight mass spectrometer, of a monoester form, a monoester dehydration product, a diester form, a diester dehydration product, a triester form, and a triester dehydration product of a polyglycerol fatty acid ester, and of a polyglycerol and a polyglycerol dehydration product. P2: The peak intensity, obtained by performing mass spectrometry on the polyglycerol monofatty acid ester (A) by using the time‑of‑flight mass spectrometer, of the monoester form of the polyglycerol fatty acid ester. P3: The total of peak intensities, obtained by performing mass spectrometry on the polyglycerol monofatty acid ester (A) by using the time‑of‑flight mass spectrometer, of the polyglycerol and the polyglycerol dehydration product.

Description

Cosmetic composition and method for producing the same

[0001] This disclosure relates to cosmetic compositions and methods for producing the same.

[0002] Polyglycerin monofatty acid esters exhibit various properties depending on the combination of polyglycerin with fatty acids having different degrees of polymerization and chain lengths, and have been used as surfactants in a wide range of applications such as food additives, detergent compositions, and cosmetics (cosmetic compositions). Methods for producing such polyglycerin fatty acid esters include esterification reactions of polyglycerin and fatty acids, transesterification reactions of polyglycerin and fatty acid esters, and addition polymerization reactions of glycidol and fatty acids (Patent Documents 1 to 6).

[0003] However, the polyglycerol monofatty acid esters known to date contain many by-products other than the monoester (e.g., dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester), and the purity of the monoester was not considered high.

[0004] JP 8-109153, JP 9-117258, JP 9-216813, JP 9-272893, JP 2006-111539, International Publication No. 2004 / 048304

[0005] Therefore, cosmetic compositions containing polyglycerin monofatty acid esters described in Patent Documents 1 to 6 had the problem of insufficient "emulsification" required for cosmetics and leaving a "lingering feeling." Accordingly, the object of this disclosure is to provide a cosmetic composition that has excellent emulsification properties and leaves little lingering feeling. It is also to provide a method for producing the above cosmetic composition.

[0006] As a result of diligent research, the inventors of this disclosure have found that the above problems can be solved by incorporating a specific polyglycerin monofatty acid ester into a cosmetic composition. The invention described herein was completed based on these findings.

[0007] In other words, the present disclosure provides a cosmetic composition comprising a polyglycerin monofatty acid ester (A) and an oil (B), wherein the polyglycerin monofatty acid ester (A) has 4 to 25 carbon atoms in the fatty acid, has a peak intensity ratio represented by the following formula (X) of 0.20 or more, and has a peak intensity ratio represented by the following formula (Y) of 0.46 or less. Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester (A), as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of polyglycerin and dehydrated polyglycerin obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer.

[0008] In polyglycerol monofatty acid ester (A), the number of carbon atoms in the fatty acid is preferably 8 to 22.

[0009] The HLB value of polyglycerol monofatty acid ester (A) is preferably 5 to 17.

[0010] In polyglycerol monofatty acid ester (A), the average degree of polymerization of glycerol is preferably 2 to 22.

[0011] The polyglycerin monofatty acid ester (A) preferably contains at least one selected from the group consisting of polyglycerin monofatty acid ester (A1) in which the average degree of polymerization of glycerin is 3 or more and less than 5, polyglycerin monofatty acid ester (A2) in which the average degree of polymerization of glycerin is 5 or more and less than 8, and polyglycerin monofatty acid ester (A3) in which the average degree of polymerization of glycerin is 8 or more and less than 12.

[0012] The oil agent (B) preferably contains at least one selected from the group consisting of hydrocarbon oils, ester oils, and triglycerides.

[0013] The content of the polyglyceryl monofatty acid ester (A) with respect to the above cosmetic composition (100% by mass) is preferably 2 to 70% by mass.

[0014] The content of the oil agent (B) is preferably 30 to 98% by mass.

[0015] The polyglyceryl monofatty acid ester (A) is preferably a reaction product of glycidol and a fatty acid, an esterified product of polyglycerol and a fatty acid, or a transesterified product of polyglycerol and a fatty acid ester.

[0016] In the polyglyceryl monofatty acid ester (A), the above fatty acid is preferably a linear fatty acid or a branched-chain fatty acid.

[0017] In the polyglyceryl monofatty acid ester (A), the above fatty acid is preferably a saturated fatty acid or an unsaturated fatty acid.

[0018] The above cosmetic composition is preferably for oily cosmetic use.

[0019] The above cosmetic composition is preferably for cleansing use.

[0020] The cosmetic composition of the present disclosure has excellent emulsifying properties and little residue feeling.

[0021] It is a chart of HPLC analysis of the polyglyceryl monocapric acid ester of Example 1. It is a chart of the corrected molecular weight and the corresponding peak intensity in the polyglyceryl monocapric acid ester of Example 1. The hollow bar graph shows the monoester form.

[0022] [Cosmetic Composition] The cosmetic composition of the present disclosure comprises a polyglycerin monofatty acid ester (A) and an oil (B), wherein the polyglycerin monofatty acid ester (A) has 4 to 25 carbon atoms in the fatty acid, the peak intensity ratio represented by the following formula (X) is 0.20 or more, and the peak intensity ratio represented by the following formula (Y) is 0.46 or less. Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester (A), as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of polyglycerin and dehydrated polyglycerin obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer.

[0023] <Polyglycerin monofatty acid ester (A)> The polyglycerin monofatty acid ester (A) used in the cosmetic composition of this disclosure has 4 to 25 carbon atoms in its fatty acid, a peak intensity ratio represented by the following formula (X) of 0.20 or more, and a peak intensity ratio represented by the following formula (Y) of 0.46 or less. Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester (A), as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of polyglycerin and dehydrated polyglycerin obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer.

[0024] In the above cosmetic composition, one polyglycerin monofatty acid ester (A) may be used alone, or two or more may be used in combination. The above cosmetic composition may contain at least one selected from the group consisting of polyglycerin monofatty acid ester (A) having an average degree of polymerization of glycerin of 3 or more and less than 5, polyglycerin monofatty acid ester (A2) having an average degree of polymerization of glycerin of 5 or more and less than 8, and polyglycerin monofatty acid ester (A3) having an average degree of polymerization of glycerin of 8 or more and less than 12. The embodiments of polyglycerin monofatty acid ester (A) will be described below, but polyglycerin monofatty acid esters (A1) to (A3) may also have similar embodiments except for the average degree of polymerization of glycerin.

[0025] The polyglycerol monofatty acid ester (A) contains at least polyglycerol monofatty acid ester. In addition to the polyglycerol monofatty acid ester, it may also contain polyglycerol polyfatty acid esters such as polyglycerol difatty acid ester and polyglycerol trifatty acid ester. Further, it may contain polyglycerol and the like which are raw materials of the polyglycerol monofatty acid ester. Moreover, it may contain the dehydrates thereof described later.

[0026] The above polyglycerol monofatty acid ester is represented by, for example, the following formula (1). RC(=O)-[C ３ H ６ O ２ ｎ -OH・・・(1)

[0027] In formula (1), R represents an aliphatic hydrocarbon group having 3 to 24 carbon atoms. Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, or an alkyl group having a hydroxy group. The number of carbon atoms of the aliphatic hydrocarbon group corresponds to the number of carbon atoms of the "fatty acid" described later minus 1. n is the average degree of polymerization of glycerin and represents, for example, 2 to 22.

[0028] C within the parentheses in the above formula (1) ３ H ６ O ２ contains at least one structure selected from the group consisting of the following formulas (2), (3), and (4). -O-CH ２ -CH(OH)-CH ２ -・・・(2) -O-CH(CH ２ OH)-CH ２ -・・・(3) -O-CH ２ -CH(CH ２ OH)-・・・(4)

[0029] ​In this specification, polyglycerin monofatty acid esters may be simply referred to as "monoesters." Polyglycerin difatty acid esters are formed when two hydroxyl groups of polyglycerin are linked to the carboxyl groups of fatty acids by ester bonding. Such polyglycerin monofatty acid esters may be simply referred to as "diesters." Polyglycerin trifatty acid esters are formed when three hydroxyl groups of polyglycerin are linked to the carboxyl groups of fatty acids by ester bonding. Such polyglycerin monofatty acid esters may be simply referred to as "triesters." In addition, polyglycerin polyfatty acid esters other than polyglycerin difatty acid esters and polyglycerin trifatty acid esters may also be referred to as "tetraesters," "pentaesters," "hexaesters," etc., in the same manner as above. Furthermore, these polyglycerin polyfatty acid esters may be referred to as "polyesters."

[0030] In polyglycerin monofatty acid esters (A), some of the polyglycerin may be dehydrated during the manufacturing process. In polyglycerin monofatty acid esters, those in which some of the polyglycerin has been dehydrated may be called dehydrated polyglycerin monofatty acid esters, or dehydrated monoesters of polyglycerin fatty acid esters, or simply dehydrated monoesters. Similarly, polyglycerin polyfatty acid esters such as polyglycerin difatty acid esters and polyglycerin trifatty acid esters may be called dehydrated polyglycerin difatty acid esters or dehydrated diesters, or dehydrated polyglycerin polyfatty acid esters or dehydrated polyesters such as dehydrated polyglycerin trifatty acid esters or dehydrated triesteres. These dehydrated products may have a cyclic structure.

[0031] Polyglycerin monofatty acid ester (A) may be obtained by (1) an addition polymerization reaction of glycidol to a fatty acid, (2) an esterification reaction of polyglycerin and a fatty acid, or (3) a transesterification reaction of polyglycerin and a fatty acid ester. The polyglycerin monofatty acid ester obtained by reaction (1) above can be rephrased as a reaction product of glycidol and a fatty acid. The polyglycerin monofatty acid ester obtained by reaction (2) above can be rephrased as an esterified product of polyglycerin and a fatty acid. The polyglycerin monofatty acid ester obtained by reaction (3) above can be rephrased as a transesterified product of polyglycerin and a fatty acid ester. Among these, the reaction product of glycidol and a fatty acid as described in (1) above is preferred because it has a higher proportion of monoesters in polyglycerin monofatty acid ester (A).

[0032] (Time-of-Flight Mass Spectrometer (TOF-MS)) The time-of-flight mass spectrometer (TOF-MS) and its measurement conditions for polyglycerol monofatty acid ester (A) are not particularly limited, but for example, they can be measured using the following apparatus and conditions. • Instrument: Xevo G2-XSQTof (Waters Co., Ltd.) • Infusion method: Infusion (5 μL / min) • Measurement mode: Neg • Cone gas: 50 L / h • Desolvation gas: 1000 L / h • Source temperature: 120°C • Desolvation temperature: 500°C • Capillary: 2.0 kV • Sampling cone: 40 • Source offset: 80 • Sample concentration: 25 ppm (methanol) • MS range: 50-3000

[0033] In polyglycerol monofatty acid ester (A), the peak intensity ratio represented by formula (X) is calculated by P2 / P1. The peak intensity ratio represented by formula (Y) is calculated by P3 / P1. P1 is the sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerol monofatty acid ester, as well as polyglycerol and dehydrated polyglycerol, obtained by mass spectrometry of polyglycerol monofatty acid ester (A) using a time-of-flight mass spectrometer. P2 is the peak intensity of the monoester of polyglycerol fatty acid ester obtained by mass spectrometry of polyglycerol monofatty acid ester (A) using a time-of-flight mass spectrometer. P3 is the sum of the peak intensities of polyglycerol and dehydrated polyglycerol obtained by mass spectrometry of polyglycerol monofatty acid ester (A) using a time-of-flight mass spectrometer.

[0034] The peak intensities of each component used in P1 to P3 above are derived from the peak intensities obtained when mass spectrometry of polyglycerol monofatty acid ester (A) is performed using the time-of-flight mass spectrometer described above.

[0035] When mass spectrometry is performed on polyglycerol monofatty acid ester (A) using the above-described time-of-flight mass spectrometer, in addition to the peak corresponding to the molecular weight of the monoester (i.e., polyglycerol monofatty acid ester), peaks corresponding to the molecular weight of impurities such as dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester may be observed. Furthermore, peaks corresponding to the molecular weight of other polyglycerol polyfatty acid esters and their dehydrated products such as tetraester, dehydrated tetraester, pentaester, and dehydrated pentaester may be observed as impurities. In addition, peaks corresponding to the molecular weight of polyglycerol and dehydrated polyglycerol, which are raw materials or by-products of polyglycerol monofatty acid ester (A), may be observed as impurities.

[0036] Polyglycerol monofatty acid esters and impurities can be identified by the molecular weight measured when the polyglycerol monofatty acid ester (A) is subjected to mass spectrometry using the above-mentioned time-of-flight mass spectrometer.

[0037] The following outlines the calculation methods for formulas (X), (Y), and P1-3 described above. The specific methods are described in the examples. (a) Mass spectrometry of polyglycerol monofatty acid ester (A) is performed using a time-of-flight mass spectrometer to obtain the molecular weight and peak intensity derived from each component described in P1-3. The decimal part of each molecular weight value is rounded down to an integer, and the corresponding peak intensity values ​​are added together. The rounding down of the molecular weights to an integer as described above is intended to correspond with the corrected molecular weight in (c) described below. (b) The theoretical molecular weight of each component described in P1-3 is calculated. (c) The theoretical molecular weight in (b) is corrected considering (i) to (iv) below to define the corrected molecular weight. (i) The molecular weight measured and detected by the time-of-flight mass spectrometer is derived from the molecule that has been deprotonated by ionization. (ii) For (i), the molecular weight of the peak top of the intensity may shift by 1 for larger molecules. (iii) Since some of the components described on pages 1 to 3 have the same molecular weight, it is necessary to appropriately select and calculate them. (iv) Considering the number of esterifications of the polyglycerin fatty acid ester and the degree of polymerization of glycerin, it is necessary to exclude any dehydration degree that cannot exist. (d) The intensity obtained in (a) is matched to the corrected molecular weight of each component of the polyglycerin mono fatty acid ester (A) calculated in (c), and these are summed up to obtain the respective peak intensities of "monoester," "dehydrated monoester," "diester," "dehydrated diester," "tryester," "dehydrated tryester," "polyglycerin," and "dehydrated polyglycerin" described on pages 1 to 3. The peak intensities of each of the above components were calculated as follows. - The peak intensities for monoesters, diesters, triesters, and polyglycerins are the sum of the peak intensities when the degree of polymerization of glycerin is 1 to 20. - The peak intensities for dehydrated monoesters, diesters, triesters, and polyglycerins are the sum of the peak intensities when the degree of polymerization of glycerin is 1 to 20 and when the degree of dehydration is 1 to 3 (1 to 3 water molecules have been removed).Using the peak intensities of each component of polyglycerol monofatty acid ester (A) calculated in (e) and (d), the above formulas (X) and (Y) are calculated.

[0038] P1 above is the sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester (A), as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2 above is the peak intensity of the monoester of polyglycerin mono fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. Therefore, the peak intensity ratio expressed by formula (X) = P2 / P1 can be said to be an indicator of the content of polyglycerin mono fatty acid ester (monoester of polyglycerin fatty acid ester) contained in polyglycerin mono fatty acid ester (A). In other words, a large value of formula (X) means that the purity of polyglycerin mono fatty acid ester in polyglycerin mono fatty acid ester (A) is high. P3 above is the sum of the peak intensities of polyglycerin and polyglycerin dehydrate obtained by mass spectrometry of polyglycerin monofatty acid ester (A) using a time-of-flight mass spectrometer. Therefore, the peak intensity ratio expressed by equation (Y) = P3 / P1 can be said to be an indicator of the content of polyglycerin and polyglycerin dehydrate contained in polyglycerin monofatty acid ester (A). In other words, a small value of equation (Y) means that the content of polyglycerin and polyglycerin dehydrate in polyglycerin monofatty acid ester (A) is small, and relatively the content of the monoester of polyglycerin fatty acid ester is large (high purity).

[0039] The peak intensity ratio represented by the above formula (X) is not particularly limited as long as it is 0.20 or higher, but is more preferably 0.21 or higher, more preferably 0.23 or higher, more preferably 0.24 or higher, more preferably 0.25 or higher, more preferably 0.26 or higher, more preferably 0.28 or higher, more preferably 0.3 or higher, more preferably 0.31 or higher, more preferably 0.33 or higher, more preferably 0.35 or higher, more preferably 0.37 or higher, more preferably 0.40 or higher, more preferably 0.44 or higher, more preferably 0.48 or higher, and more preferably 0.52 or higher. Also, the peak intensity ratio represented by the above formula (X) is not particularly limited, but is for example 1 or less, preferably 0.9 or less, more preferably 0.8 or less, more preferably 0.75 or less, more preferably 0.7 or less, more preferably 0.65 or less, and more preferably 0.6 or less.

[0040] The peak intensity ratio represented by the above formula (Y) is not particularly limited as long as it is 0.46 or less, but is preferably 0.45 or less, more preferably 0.44 or less, more preferably 0.42 or less, more preferably 0.39 or less, more preferably 0.37 or less, more preferably 0.35 or less, more preferably 0.33 or less, more preferably 0.32 or less, and more preferably 0.30 or less. Also, the peak intensity ratio represented by the above formula (Y) is not particularly limited, but for example, is 0.01 or more, preferably 0.05 or more, and more preferably 0.10 or more.

[0041] In polyglycerol monofatty acid ester (A), the average degree of polymerization of glycerol is not particularly limited, but is preferably 2 to 40. The average degree of polymerization of glycerol may be 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more. Alternatively, the average degree of polymerization of glycerol may be 35 or less, 30 or less, 25 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, 8 or less, 6 or less, or 4 or less. The average degree of polymerization of glycerol may also be 3 to 20, or 4 to 10.

[0042] In polyglycerol monofatty acid ester (A), the average degree of polymerization of glycerol may further be 3 or more but less than 5, 5 or more but less than 8, or 8 or more but less than 12. In this case, polyglycerol monofatty acid ester (A) can be rephrased as polyglycerol monofatty acid ester (A1), polyglycerol monofatty acid ester (A2), and polyglycerol monofatty acid ester (A3), respectively.

[0043] In polyglycerin monofatty acid ester (A), the method for determining the average degree of polymerization of glycerin is not particularly limited. For example, in the case of polyglycerin monofatty acid ester (A) obtained by reaction (1) described in the "Method for Producing Polyglycerin Monofatty Acid Ester (A)" below, it can be determined by the number of moles of glycidol added to 1 mole of fatty acid. For example, if the average degree of polymerization of glycerin is n, then when n moles of glycidol are added to 1 mole of fatty acid, the average degree of polymerization of glycerin in the resulting polyglycerin monofatty acid ester (A) is n. Also, for example, in the case of polyglycerin monofatty acid ester (A) obtained by reactions (2) and (3) below, it is the same as the average degree of polymerization of glycerin in the polyglycerin used. For example, in polyglycerin monofatty acid ester (A) obtained by an esterification reaction between polyglycerin with an average degree of polymerization of m and a fatty acid, the average degree of polymerization of glycerin is m.

[0044] Another method for determining the average degree of polymerization of glycerin is the method using hydroxyl value. Hydroxyl value refers to the number of mg of potassium hydroxide required to neutralize the acetic acid bonded to the hydroxyl groups when 1 g of the sample is acetylated (see JIS K 0070-1992). The amount of hydroxyl groups in the polyglycerin chain of polyglycerin monofatty acid ester (A) can be calculated from the hydroxyl value, and its average degree of polymerization can be determined.

[0045] In polyglycerol monofatty acid ester (A), the hydroxyl value is not particularly limited, but is preferably 317 to 754 KOH / g. The hydroxyl value of polyglycerol monofatty acid ester (A) may be 317 KOH / g or more, 389 KOH / g or more, 413 KOH / g or more, 475 KOH / g or more, 483 KOH / g or more, or 539 KOH / g or more. Alternatively, the hydroxyl value of polyglycerol monofatty acid ester (A) may be 754 KOH / g or less, 751 KOH / g or less, 745 KOH / g or less, 741 KOH / g or less, 734 KOH / g or less, 725 KOH / g or less, 713 KOH / g or less, 698 KOH / g or less, or 677 KOH / g or less.

[0046] In polyglycerol monofatty acid ester (A), the above fatty acid is not particularly limited, but for example, a fatty acid having 4 to 25 carbon atoms is preferred. The above fatty acid may be a saturated fatty acid or an unsaturated fatty acid. It may also be a straight-chain fatty acid or a branched-chain fatty acid (a fatty acid with a side chain). Furthermore, it may be a substituted fatty acid in which some of the hydrogen atoms bonded to the carbon chain are replaced by hydroxyl groups. Here, fatty acid refers to a fatty acid as a component of polyglycerol monofatty acid ester.

[0047] The number of carbon atoms in the above fatty acid is not particularly limited, but may be 6 or more, 8 or more, 10 or more, 12 or more, 14 or more, 15 or more, 16 or more, or 18 or more. Also, the number of carbon atoms in the above fatty acid is not particularly limited, but may be 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, or 8 or less. The number of carbon atoms in the above fatty acid may also be 4 to 14 or 15 to 25, or 8 to 14 or 16 to 18.

[0048] The above fatty acids are not particularly limited, but for example, caproic acid (C) ６ (saturated fatty acids), caprylic acid (C ８ (saturated fatty acids), pelargonic acid (C ９ (saturated fatty acids), 2-ethylhexanoic acid (C ８ (branched-chain fatty acids), capric acid (C １０ (saturated fatty acids), lauric acid (C １２ (saturated fatty acids), isotridecanoic acid (C１３ (branched-chain fatty acids), myristic acid (C １４ (saturated fatty acids), pentadecyl acid (C １５ (saturated fatty acids), palmitic acid (C １６ (saturated fatty acids), palmitoleic acid (C １６ (unsaturated fatty acids), stearic acid (C １８ (saturated fatty acids), isostearic acid (C １８ (branched-chain fatty acids), oleic acid (C １８ (unsaturated fatty acids), linoleic acid (C １８ (unsaturated fatty acids), ricinoleic acid (C １８ (unsaturated fatty acids), hydroxystearic acid (C １８ (substituted fatty acids), arachidic acid (C ２０ (saturated fatty acids), behenic acid (C ２２ , saturated fatty acids), erucic acid (C ２２ (unsaturated fatty acids), nervonic acid (C ２４ Examples include unsaturated fatty acids.

[0049] When the number of carbon atoms in the above fatty acid is 4 to 14 (particularly 8 to 14), the peak intensity ratio represented by formula (X) above is not particularly limited as long as it is 0.20 or higher, but is more preferably 0.23 or higher, more preferably 0.25 or higher, more preferably 0.30 or higher, more preferably 0.33 or higher, more preferably 0.35 or higher, and more preferably 0.40 or higher.

[0050] When the number of carbon atoms in the above fatty acid is 4 to 14 (particularly 8 to 14), the peak intensity ratio represented by formula (Y) is not particularly limited as long as it is 0.46 or less, but is preferably 0.45 or less, more preferably 0.42 or less, more preferably 0.39 or less, and more preferably 0.37 or less. Also, the peak intensity ratio represented by formula (Y) is not particularly limited, but for example, is 0.01 or more, preferably 0.05 or more, and more preferably 0.10 or more.

[0051] When the number of carbon atoms in the above fatty acid is 4 to 14 (particularly 8 to 14), the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, even more preferably 4 to 10, and particularly preferably 6 to 10.

[0052] When the number of carbon atoms in the above fatty acid is 15 to 25 (particularly 16 to 18), the peak intensity ratio represented by the above formula (X) is not particularly limited as long as it is 0.20 or higher, but is more preferably 0.23 or higher, more preferably 0.24 or higher, more preferably 0.25 or higher, more preferably 0.28 or higher, more preferably 0.30 or higher, more preferably 0.31 or higher, more preferably 0.33 or higher, and more preferably 0.35 or higher.

[0053] When the number of carbon atoms in the above fatty acid is 15 to 25 (particularly 16 to 18), the peak intensity ratio represented by formula (Y) is not particularly limited as long as it is 0.46 or less, but is preferably 0.44 or less, more preferably 0.37 or less, more preferably 0.32 or less, more preferably 0.30 or less, and more preferably 0.28 or less. Also, the peak intensity ratio represented by formula (Y) is not particularly limited, but for example, is 0.01 or more, preferably 0.05 or more, and more preferably 0.10 or more.

[0054] When the number of carbon atoms in the above fatty acid is 15 to 25 (particularly 16 to 18), the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0055] When the above fatty acid is a straight-chain fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the peak intensity ratio represented by formula (X) is not particularly limited as long as it is 0.20 or higher, but is more preferably 0.24 or higher, more preferably 0.28 or higher, and more preferably 0.30 or higher. In this case, the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0056] When the above fatty acid is a straight-chain fatty acid with 15 to 25 carbon atoms (particularly 16 to 18), the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0057] When the above fatty acid is a branched-chain fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the peak intensity ratio represented by formula (X) is not particularly limited as long as it is 0.20 or higher, but is preferably 0.25 or higher, more preferably 0.30 or higher, and more preferably 0.33 or higher. In this case, the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0058] When the above fatty acid is a branched-chain fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the peak intensity ratio represented by formula (Y) is not particularly limited as long as it is 0.46 or less, but is preferably 0.40 or less, more preferably 0.37 or less, and more preferably 0.35 or less. Furthermore, the peak intensity ratio represented by formula (Y) is not particularly limited, but is, for example, 0.01 or more, preferably 0.05 or more, and more preferably 0.10 or more.

[0059] When the above fatty acid is a branched-chain fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0060] When the above fatty acid is an unsaturated fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the peak intensity ratio represented by formula (X) is not particularly limited as long as it is 0.20 or higher, but is more preferably 0.23 or higher, more preferably 0.25 or higher, more preferably 0.30 or higher, and more preferably 0.33 or higher. In this case, the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0061] When the above fatty acid is an unsaturated fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the peak intensity ratio represented by formula (Y) is not particularly limited as long as it is 0.46 or less, but is preferably 0.44 or less, more preferably 0.32 or less, more preferably 0.30 or less, and more preferably 0.28 or less. Also, the peak intensity ratio represented by formula (Y) is not particularly limited, but is, for example, 0.01 or more, preferably 0.05 or more, and more preferably 0.1 or more.

[0062] When the above fatty acid is an unsaturated fatty acid having 15 to 25 carbon atoms (particularly 16 to 18), the average degree of polymerization of glycerin is not particularly limited, but is preferably 2 to 40, more preferably 3 to 20, and even more preferably 4 to 10.

[0063] In polyglycerol monofatty acid ester (A), the area ratio of the peaks corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester of the polyglycerol fatty acid ester, as well as polyglycerol and dehydrated polyglycerol, in the following HPLC (high-performance liquid chromatography) analysis is not particularly limited, but is preferably 50% or more, more preferably 60% or more, even more preferably 80% or more, and particularly preferably 90% or more.

[0064] In polyglycerol monofatty acid ester (A), the area ratio of the peaks corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester of the polyglycerol fatty acid ester in the following HPLC (high-performance liquid chromatography) analysis is preferably, for example, 5% or more, more preferably 10% or more, and even more preferably 20% or more. Furthermore, the area ratio of the peaks corresponding to polyglycerol and dehydrated polyglycerol is, for example, 1% or more, 5% or more, 10% or more, or 20% or more, and is preferably, for example, 80% or less, more preferably 70% or less, and even more preferably 60% or less.

[0065] (HPLC Analysis) The HPLC analysis method for polyglycerol monofatty acid ester (A) is not particularly limited, but for example, it can be measured using the following apparatus and conditions: • Apparatus: LC-2030C 3D (Shimadzu Corporation) • Column: Two Wakosil 5C18 Φ4.6 mm × 250 mm (W) columns connected in series • Detector: RID-20A (Shimadzu Corporation) • Oven temperature: 40°C • Sample: 10% methanol solution • Sample injection volume: 10 μl • Mobile phase flow rate: 0.75 ml / min

[0066] The "peaks corresponding to monoesters, dehydrated monoesters, polyesters, and dehydrated polyesters of polyglycerin fatty acid esters, as well as polyglycerin and dehydrated polyglycerin" mentioned above refer, for example, to the peaks whose peak tops are located between a retention time of 6.0 and 20.0 minutes on the HPLC chart in the HPLC analysis method shown above. Therefore, the area ratio of the above peaks is the sum of the peak area ratios between a retention time of 6.0 and 20.0 minutes on the HPLC chart. The "peaks corresponding to monoesters, dehydrated monoesters, polyesters, and dehydrated polyesters of polyglycerin fatty acid esters" mentioned above refer, for example, to the peaks whose peak tops are located between a retention time of 8.2 and 20.0 minutes on the HPLC chart in the HPLC analysis method shown above. Therefore, the area ratio of the above peaks is the sum of the peak area ratios between a retention time of 8.2 and 20.0 minutes on the HPLC chart. The "peaks corresponding to polyglycerin and dehydrated polyglycerin" mentioned above refer, for example, to the peaks whose peak tops are located between retention times of 6.0 and 8.2 minutes in the HPLC analysis method shown above. Therefore, the area ratio of the above peaks is the sum of the peak area ratios between retention times of 6.0 and 8.2 minutes in the HPLC chart.

[0067] The content of polyglycerin monofatty acid ester (A) in the above cosmetic composition (100% by mass) is not particularly limited, but is preferably 2% by mass or more, more preferably 4% by mass or more, even more preferably 8% by mass or more, even more preferably 10% by mass or more, and particularly preferably 14% by mass or more. Also, is preferably 80% by mass or less, more preferably 70% by mass or less, even more preferably 60% by mass or less, even more preferably 50% by mass or less, even more preferably 40% by mass or less, and particularly preferably 30% by mass or less. When the above cosmetic composition contains two or more types of polyglycerin monofatty acid ester (A), the above content refers to the total amount of polyglycerin monofatty acid ester (A). When the content of polyglycerin monofatty acid ester (A) is within the above range, the cosmetic composition tends to have excellent emulsifying properties and less residue.

[0068] The above cosmetic composition may contain polyglycerin fatty acid esters (XA) other than polyglycerin monofatty acid ester (A). When the above cosmetic composition contains polyglycerin fatty acid ester (XA), the content of polyglycerin fatty acid ester (XA) relative to polyglycerin monofatty acid ester (A) (100 parts by mass) is not particularly limited, but is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, and particularly preferably 5 parts by mass or less.

[0069] Method for producing polyglycerin monofatty acid ester (A) Polyglycerin monofatty acid ester (A) may be obtained by any of the following reactions: (1) an addition polymerization reaction of glycidol to a fatty acid, (2) an esterification reaction of polyglycerin and a fatty acid, and (3) a transesterification reaction of polyglycerin and a fatty acid ester. Among these, the polyglycerin monofatty acid ester (A) obtained by reaction (1) above is preferred because it has a higher proportion of monoester. In other words, it is preferable that polyglycerin monofatty acid ester (A) be obtained by a production method that includes an addition polymerization reaction step of a fatty acid and glycidol.

[0070] The reaction described in (1) above can be carried out with or without a catalyst, but from the viewpoint of improving the proportion of monoesters, it is preferable to carry it out with a catalyst (especially an acidic catalyst). In particular, if the average degree of polymerization of glycerin in the polyglycerin monofatty acid ester (A) to be obtained exceeds 5, it is preferable to carry out the reaction described in (1) above with a catalyst. This is because there is a strong tendency for the proportion of monoesters in the obtained polyglycerin monofatty acid ester (A) to be higher. Conversely, if the average degree of polymerization of glycerin in the polyglycerin monofatty acid ester (A) to be obtained is 5 or less, it is preferable to carry out the reaction described in (1) above with a catalyst, but there is no significant difference in the proportion of monoesters even if it is carried out without a catalyst.

[0071] The above-mentioned acidic catalyst is not particularly limited, but it is preferable to use organic acids commonly used in cosmetics as catalysts. Examples include ascorbic acid; carboxylic acids such as acetic acid, formic acid, citric acid, succinic acid, and adipic acid; and phosphoric acid-based acidic catalysts. Organic acids with a large acid dissociation constant are preferred as the above-mentioned acidic catalyst. Among these, phosphoric acid-based acidic catalysts are preferred from the viewpoint of the purity of the polyglycerol monofatty acid ester (A).

[0072] Examples of the above-mentioned phosphoric acid catalysts include phosphoric acids or esters of phosphoric acids, such as phosphoric acids like phosphoric acid, phosphoric anhydride, polyphosphate, orthophosphate, metaphosphate, pyrophosphate, triphosphate, and tetraphosphate, as well as acidic phosphoric acid esters such as methyl acid phosphate, ethyl acid phosphate, isopropyl acid phosphate, butyl acid phosphate, and 2-ethylhexyl acid phosphate. Among these, phosphoric acid is preferred.

[0073] The catalyst may be used individually or in combination of two or more types. The amount of catalyst added is 0.001 to 10 parts by mass, preferably 0.01 to 5 parts by mass, per 100 parts by mass of fatty acid. It is preferable that the proportion of monoester is higher when the amount of catalyst added is within the above range.

[0074] When producing polyglycerol monofatty acid ester (A) by the reaction described in (1) above, the reaction may be carried out, for example, by continuously or intermittently supplying an acidic catalyst to the fatty acid (1-1) while continuously or intermittently supplying glycidol, or by continuously or intermittently supplying glycidol to a mixture of the fatty acid and the acidic catalyst (1-2). Furthermore, as an embodiment carried out in the absence of a catalyst, the reaction may be carried out by continuously or intermittently supplying glycidol to the fatty acid (1-3).

[0075] Regarding (1-1) above, to explain in detail, it means that an addition polymerization reaction is carried out by placing a fatty acid in a reaction vessel and continuously or intermittently supplying glycidol to the reaction vessel while also continuously or intermittently supplying an acidic catalyst to the reaction vessel. In other words, it means that glycidol and the acidic catalyst are supplied to the fatty acid continuously or intermittently at least for a certain period of time. For example, the method of supply is dropwise. Regarding (1-2) above, to explain in detail, it means that an addition polymerization reaction is carried out by placing a fatty acid and an acidic catalyst in a reaction vessel and mixing them as necessary, and continuously or intermittently supplying glycidol to the reaction vessel. For example, the method of supply is dropwise. Regarding (1-3) above, to explain in detail, it means that an addition polymerization reaction is carried out by placing a fatty acid in a reaction vessel and continuously or intermittently supplying glycidol to the reaction vessel. In other words, it means that glycidol is supplied to the fatty acid continuously or intermittently at least for a certain period of time.

[0076] In the reaction described in (1) above, the formation of polyglycerol may proceed in the reaction system (for example, in the reaction vessel) in addition to the formation of polyglycerol monofatty acid ester. However, by adding glycidol dropwise, either continuously or intermittently, the concentration of glycidol in the system can be kept low, so the formation of polyglycerol monofatty acid ester tends to be more dominant than the formation of polyglycerol.

[0077] The acidic catalyst may be mixed with the fatty acid before the addition reaction with glycidol, or it may be supplied to the fatty acid continuously or intermittently along with glycidol as needed during the reaction. However, from the viewpoint of increasing the purity of the resulting polyglycerol monofatty acid ester (A), it is preferable to supply the acidic catalyst to the fatty acid continuously or intermittently along with glycidol during the reaction. In other words, the reaction in (1) above is preferably carried out by the operation described in (1-1) above. This is because the acidic catalyst promotes or facilitates the formation of polyglycerol as well as polyglycerol, and it is thought that by supplying the acidic catalyst to the fatty acid continuously or intermittently along with glycidol, the formation of polyglycerol monofatty acid ester becomes particularly dominant over the formation of polyglycerol. Similarly, when the acidic catalyst supplied along with glycidol is supplied to the fatty acid all at once, the formation of polyglycerol tends to be dominant over the formation of polyglycerol monofatty acid ester. Therefore, from this viewpoint as well, it is preferable to carry out the reaction by the operation described in (1-1) above.

[0078] In the reaction described in (1) above, the reactants may be aged after the operations described in (1-1) to (1-3) above, if necessary. The reaction temperature in the reaction described in (1) above is not particularly limited, but is preferably 50 to 180°C, more preferably 70 to 160°C, even more preferably 100 to 140°C, and most preferably 110 to 135°C. When the reaction temperature is within the above range, side reactions such as the decomposition of glycidol tend to be less likely to occur. The above reaction is preferably carried out under a nitrogen gas atmosphere, and may be pressurized if necessary.

[0079] The reactions described in (2) and (3) above can be carried out, for example, in or without a catalyst (alkaline catalyst or acid catalyst), at atmospheric pressure or under reduced pressure. The amounts of polyglycerin and fatty acid or polyglycerin and fatty acid ester charged are not particularly limited and can be selected and used as appropriate. The reaction temperature is not particularly limited, but is preferably 20 to 180°C, more preferably 30 to 160°C, and even more preferably 40 to 140°C.

[0080] The obtained polyglycerol monofatty acid ester may be purified as needed. The purification method can be carried out using known methods and is not particularly limited. Examples of purification methods include adsorption treatment with activated carbon or activated clay; treatment under reduced pressure using steam, nitrogen, etc. as a carrier gas; washing with acid or alkali; and molecular distillation. Impurities can also be removed using liquid-liquid partitioning, adsorbents, resins, molecular sieves, loose reverse osmosis membranes, ultrafiltration membranes, etc.

[0081] <Oil (B)> Oil (B) is not particularly limited as long as it is used as a cosmetic. Preferred oils for oil (B) include hydrocarbon oils, ester oils, triglycerides, silicone oils, animal and vegetable oils, and ether oils, more preferably hydrocarbon oils, ester oils, triglycerides, and ether oils, and even more preferably hydrocarbon oils and ester oils. Oil (B) can be used alone or in combination of two or more types.

[0082] Hydrocarbon oils are not particularly limited, but examples include squalane, squalene, liquid paraffin, isododecane, hydrogenated polyisobutene, isohexadecane, isoparaffin (light isoparaffin), tetradecene, hydrogenated polydecene, undecane, and tridecane.

[0083] Ester oils are not particularly limited as long as they are oils having ester bonds in their molecules, but examples include isopropyl palmitate, isopropyl myristate, ethylhexyl palmitate, cetyl palmitate, isocetyl myristate, butyl stearate, stearyl stearate, dioctyl adipate, diisopropyl adipate, dibutyl adipate, ethyl isostearate, isostearyl isostearate, octyldodecyl myristate, isocetyl stearate, cetyl ricinoleate, octyldodecyl ricinoleate, and dicaprate. Examples include opentyl glycol, propylheptyl caprylate, caprylyl caprylate, caprylyl caprate, hexyldecyl isostearate, octyldodecyl lactate, diisostearyl malate, diglyceryl triisostearate, isotridecyl isononanoate, octyldodecyl isostearate, ethylhexyl stearate, hexyl laurate, dioctyl sebacate, dilauryl thiodipropionate, isononyl isononanoate, isotridecyl isononanoate, triethyl citrate, cetyl ethylhexanoate, and dicaprylyl carbonate.

[0084] Triglycerides are not particularly limited as long as they are acylglycerols in which three molecules of fatty acids are ester-bonded to glycerol, but examples include triethylhexanoin, trimiristine, triisostearin, tricaprine, tri(caprylic / capric acid) glyceryl, tri(caprylic / capric acid / myristic acid / stearic acid) glyceryl, and (caprylic / capric acid / succinic acid) triglyceryl.

[0085] The silicone oil is not particularly limited, but examples include dimethicone, cyclomethicone, phenyldimethicone, phenyltrimethicone, cyclopentasiloxane, and diphenylsiloxyphenyltrimethicone.

[0086] While not limited to animal or vegetable oils, examples include olive fruit oil (olive oil), coconut oil (coconut oil), argania spinosa kernel oil, almond oil, jojoba oil, avocado oil, sunflower seed oil (sunflower oil), grape seed oil, palm oil, peanut oil, rosehip oil, castor oil, wheat germ oil, soybean oil, safflower oil, camellia oil, rice germ oil, and corn germ oil.

[0087] Ether oils are not particularly limited, but examples include dialkyl ethers such as dihexyl ether, dicaprylyl ether, and cetyl-1,3-dimethylbutyl ether.

[0088] The content of oil agent (B) relative to the above cosmetic composition (100% by mass) is not particularly limited, but is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, even more preferably 50% by mass or more, even more preferably 60% by mass or more, and particularly preferably 70% by mass or more. Alternatively, it is preferably 98% by mass or less, more preferably 96% by mass or less, even more preferably 92% by mass or less, even more preferably 90% by mass or less, and particularly preferably 86% by mass or less. If the above cosmetic composition contains two or more types of oil agents (B), the above content refers to the total amount of oil agents (B). When the content of oil agent (B) is within the above range, the cosmetic composition tends to have excellent emulsifying properties and less residue.

[0089] The above cosmetic composition may contain other components (hereinafter sometimes referred to as "other components") besides polyglycerin monofatty acid ester (A) and oil (B), depending on its use and purpose, as long as it does not impair the effects of the invention disclosed herein. Examples of other components include water, polyhydric alcohols, surfactants, pH adjusters, chelating agents, antioxidants, preservatives, fragrances, amino acids, sugars, polysaccharides, organic salts, inorganic salts, bactericides, blood flow promoters, anti-inflammatory agents, UV absorbers, UV scattering agents, vitamins, pigments, aqueous gelling agents, oily gelling agents, powders, colorants, cooling agents, thickeners, plant extracts, neutralizing agents, and humectants.

[0090] Examples of polyhydric alcohols, though not particularly limited, include glycerin, propylene glycol, 1,3-butylene glycol, dipropylene glycol, propanediol, pentylene glycol, sorbitol, mannitol, xylitol, erythritol, pentaerythritol, arabitol, 1,2-hexanediol, 1,2-octanediol, polyglycerin (e.g., diglycerin, triglycerin, etc.), ethylhexylglycerin, caprylyl glycol, 1,10-decanediol, and isopentyldiol.

[0091] The cosmetic composition of this disclosure preferably uses a polyglycerin monofatty acid ester (A) having an HLB (Hydrophile-Lypophile Balance) value of 5 to 17 (preferably 10 to 15). When two or more polyglycerin monofatty acid esters (A) are used, the above HLB value may be a weighted average value, or it may be a value that each of the two or more polyglycerin monofatty acid esters (A) satisfies. Furthermore, by combining a polyglycerin monofatty acid ester (A) with a relatively low HLB value (hereinafter referred to as polyglycerin monofatty acid ester (A10)) and a polyglycerin monofatty acid ester (A) with a relatively high HLB value (hereinafter referred to as polyglycerin monofatty acid ester (A20)), the HLB value can be set to 5 to 17 (particularly 10 to 15), resulting in the cosmetic composition of this disclosure having particularly excellent emulsifying properties and a particularly low residue.

[0092] The HLB value of polyglycerin monofatty acid ester (A10) is not particularly limited, but is preferably 9 or more and less than 11, more preferably 9.5 to 10.8, and even more preferably 10 to 10.6. The HLB value of polyglycerin monofatty acid ester (A20) is not particularly limited, but is preferably 11 to 16, more preferably 11.2 to 15.5, and even more preferably 11.5 to 15. Therefore, in the cosmetic composition of this disclosure, it is preferable to adjust the blending amounts of polyglycerin monofatty acid ester (A10) and polyglycerin monofatty acid ester (A20) so that the combined HLB value (weighted average HLB value) is 10 to 15 (preferably 10.2 to 13, more preferably 10.4 to 12.5, and even more preferably 10.6 to 12), taking into account the respective HLB values.

[0093] In the cosmetic composition of this disclosure, the amount of polyglycerin monofatty acid ester (A10) relative to polyglycerin monofatty acid ester (A) (100% by mass) is not particularly limited, but for example it may be 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more. Alternatively, for example it may be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, or 10% by mass or less. Furthermore, in the cosmetic composition of this disclosure, the amount of polyglycerin monofatty acid ester (A20) blended with polyglycerin monofatty acid ester (A) (100% by mass) is not particularly limited, but for example, it may be 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more. Alternatively, for example, it may be 90% by mass or less, 80% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, or 10% by mass or less. By setting the polyglycerin monofatty acid ester (A10) and / or polyglycerin monofatty acid ester (A20) within the above ranges, the HLB value (weighted average HLB value) after combining these polyglycerin monofatty acid esters can be within the above ranges.

[0094] In this specification, the HLB value can be calculated by determining the organic value (OV) and inorganic value (IV) from the organic conceptual diagram and using the following formula: HLB = IV / OV × 10 = IOB (Inorganic Organic Balance) × 10

[0095] In the above cosmetic composition, the viscosity at 25°C is not particularly limited, but is preferably 20 to 10,000 mPa·s, more preferably 50 to 8,000 mPa·s, even more preferably 100 to 6,000 mPa·s, and particularly preferably 200 to 4,000 mPa·s. The method for measuring viscosity is not particularly limited, but can be measured, for example, by the method described in the examples below.

[0096] The above cosmetic composition can be prepared by mixing the above components by a conventional method. A specific method for producing the above cosmetic composition is to mix a polyglycerin monofatty acid ester (A), in which the fatty acid has 4 to 25 carbon atoms, has a peak intensity ratio represented by the following formula (X) of 0.20 or more, and a peak intensity ratio represented by the following formula (Y) of 0.46 or less, with an oil (B) to obtain a cosmetic composition containing the polyglycerin monofatty acid ester (A) and the oil (B). Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester (A), as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of polyglycerin and dehydrated polyglycerin obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer.

[0097] In the method for producing the above cosmetic composition, other components may be mixed simultaneously with or after the mixing of the polyglycerin monofatty acid ester (A) and the oil (B).

[0098] The above cosmetic composition may also be a transparent cosmetic composition.

[0099] The above cosmetic composition can be suitably used as various cosmetic compositions. That is, this disclosure also provides cosmetic compositions containing the above cosmetic composition. The above cosmetic composition may be used as a cosmetic composition on its own, or it may be used as a cosmetic composition further containing the above optional components.

[0100] The specific product or form of the above cosmetic composition is not particularly limited, but it is preferably used as an oily cosmetic, an emulsified cosmetic, or a bicontinuous cosmetic, and more preferably as an oily cosmetic. Examples include cleansing cosmetics such as cleansing milk, cleansing lotion, cleansing oil, cleansing balm, hot cleansing balm, cleansing gel, hot cleansing gel, cleansing gel pack, cleansing cream, and cleansing foam; massage cosmetics such as massage oil, massage oil gel, massage scrub gel, and hot massage gel; hair cream, hair oil, hair liquid, and bath additives.

[0101] Each embodiment disclosed herein can be combined with any other features disclosed herein. Each configuration and combination thereof in each embodiment is an example, and can be added, omitted, replaced, and otherwise modified as appropriate without departing from the spirit of this disclosure. Furthermore, each invention relating to this disclosure is not limited by the embodiments or the following examples, but is limited only by the claims.

[0102] The embodiments of this disclosure will be described in more detail below based on the examples. In these examples, it should be noted that, considering that the polyglycerol monofatty acid esters obtained by synthesis in each manufacturing example may contain components other than polyglycerol monofatty acid esters, they may be referred to as "polyglycerol monofatty acid ester products."

[0103] (Mass spectrometry using time-of-flight mass spectrometer (TOF-MS)) In the manufacturing example, the polyglycerin monofatty acid ester product was subjected to mass spectrometry using the following equipment and conditions: • Equipment: Xevo G2-XSQTof (Waters Co., Ltd.) • Infusion method: Infusion (5 μL / min) • Measurement mode: Neg • Cone gas: 50 L / h • Desolvation gas: 1000 L / h • Source temperature: 120°C • Desolvation temperature: 500°C • Capillary: 2.0 kV • Sampling cone: 40 • Source offset: 80 • Sample concentration: 25 ppm (methanol) • MS range: 50-3000

[0104] (Measurement of HLB value) In the examples and comparative examples, the HLB (Hydrophile-Lypophile Balance) value of the polyglycerin monofatty acid ester product was calculated by determining the organic value (Organic Value = OV) and inorganic value (Inorganic Value = IV) from the organic conceptual diagram and then using the following formula: HLB = IV / OV × 10 = IOB (Inorganic Organic Balance) × 10

[0105] (HPLC Analysis) In the manufacturing example, the polyglycerin monofatty acid ester product was subjected to HPLC analysis using the following equipment and conditions: • Equipment: LC-2030C 3D (Shimadzu Corporation) • Column: Two Wakosil 5C18 Φ4.6 mm × 250 mm (W) columns connected in series • Detector: RID-20A (Shimadzu Corporation) • Oven temperature: 40°C • Sample: 10% methanol solution • Sample injection volume: 10 μl • Mobile phase flow rate: 0.75 ml / min

[0106] (Production Example 1) 0.81 mol (139.7 g) of capric acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.86 mol (360.4 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monocaprate ester product with an average degree of polymerization of glycerin of 6 was obtained.

[0107] HPLC analysis of the obtained polyglycerin monocaprate ester products revealed that the area ratio of peaks present between retention times of 6.0 and 20.0 minutes on the HPLC chart corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 93.0%. Furthermore, the area ratio of peaks present between retention times of 8.2 and 20 minutes on the HPLC chart corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester was 47.9%. Additionally, the area ratio of peaks present between retention times of 6.0 and 8.2 minutes on the HPLC chart corresponding to polyglycerin and dehydrated polyglycerin was 45.1%. Figure 1 shows the HPLC analysis chart. In the figure, the peaks corresponding to monoesters, dehydrated monoesters, polyesters, and dehydrated polyesters are labeled "PGL esters, etc.," while the peaks corresponding to polyglycerin and dehydrated polyglycerin are labeled "PGL, etc."

[0108] Furthermore, the obtained polyglycerin product was subjected to mass spectrometry using the time-of-flight mass spectrometer (TOF-MS) described above. The peak intensity ratio (P2 / P1) was calculated according to the following formula (X) and was found to be 0.325. The peak intensity ratio (P3 / P1) was also calculated according to the following formula (Y) and was found to be 0.287.

[0109] Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of the polyglycerin monofatty acid ester product, as well as polyglycerin and dehydrated polyglycerin, obtained by mass spectrometry using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of the polyglycerin fatty acid ester obtained by mass spectrometry using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of the polyglycerin and dehydrated polyglycerin obtained by mass spectrometry using a time-of-flight mass spectrometer.

[0110] Furthermore, the HLB value of the obtained polyglycerol monocaprate ester was 15.4.

[0111] [Method for Calculating Peak Intensity Ratio] The method for calculating the peak intensity ratio is described in detail below in (a) to (e). (a) The molecular weight and peak intensity derived from each component contained in the polyglycerin monofatty acid ester product were obtained by measurement using a time-of-flight mass spectrometer. The decimal part of each molecular weight value was rounded down to an integer, and the corresponding peak intensity values ​​were added together to obtain the peak intensity of the integerized molecular weight. For example, if the measured values ​​obtained were a peak intensity of 31 for a molecular weight of "50.0012", a peak intensity of 5 for a molecular weight of "50.0041", and a peak intensity of 15 for a molecular weight of "50.0241", then the sum of the peak intensities of molecular weights between 50 and 51 (31 + 5 + 15 + ...) is the peak intensity of the integerized molecular weight of "50". The molecular weight range was set to 50 to 2999. This molecular weight range was determined considering the number of carbon atoms in the fatty acid and the degree of polymerization of glycerin in the polyglycerin monofatty acid ester product of this disclosure. In other words, this was determined based on the idea that there are almost no polyglycerol fatty acid esters that may be contained in the above-mentioned products that fall outside the above-mentioned molecular weight range.

[0112] The following describes (a) in Production Example 1. By measuring using a time-of-flight mass spectrometer, the molecular weight and peak intensity derived from each component in the polyglycerin monocaprate ester product obtained in Production Example 1 were obtained. Tables 1 to 6 show the results obtained by rounding down the decimal part of each molecular weight value to an integer and summing the corresponding peak intensity values.

[0113]

[0114] (b) Calculate the theoretical molecular weight of monoesters, dehydrated monoesters, diesters, dehydrated diesters, triesters, and dehydrated triesters of polyglycerin fatty acid esters, as well as polyglycerin and dehydrated polyglycerin. Note that the theoretical molecular weights for monoesters, diesters, triesters, and polyglycerin are those when the degree of polymerization of glycerin is 1 to 20. Furthermore, the theoretical molecular weights for dehydrated monoesters, dehydrated diesters, dehydrated triesters, and dehydrated polyglycerin are those when the degree of polymerization of glycerin is 1 to 20, and those when the degree of dehydration is 1 to 3 (1 to 3 water molecules have been removed).

[0115] The following describes (b) in Production Example 1. In Production Example 1, the theoretical molecular weight of the monoester of the polyglycerin monocaprate ester product is listed in the "Monoester" column of Table 7. The theoretical molecular weight of the dehydrated monoester is listed in the "Dehydrated Monoester (Dehydration Degree = 1)", "Dehydrated Monoester (Dehydration Degree = 2)", and "Dehydrated Monoester (Dehydration Degree = 3)" columns of Table 7. The same applies to other constituent components such as diesters.

[0116]

[0117] (c) In order to correspond to each molecular weight derived from the time-of-flight mass spectrometer obtained in (a), the theoretical molecular weight in (b) was corrected by the following method and referred to as the "corrected molecular weight". • Correction method: The molecular weight of the component measured and detected by the time-of-flight mass spectrometer is the deprotonated molecule [M-H] due to ionization. － Therefore, the molecular weights obtained in (a) are basically obtained by subtracting 1 from the molecular weight obtained by rounding down the theoretical molecular weight in (b) to an integer. However, as the molecular weight increases, the molecular weight at the peak of the intensity may shift by 1 due to errors in molecular weight calculation and rounding down the measured molecular weight to an integer. Therefore, for those with a theoretical molecular weight of 700 or more in (b), the peak intensities corresponding to three points—the molecular weight obtained by rounding down the theoretical molecular weight in (b) to an integer (M1), the molecular weight obtained by subtracting 1 from M1 (M2), and the molecular weight obtained by subtracting 2 from M1 (M3)—were compared, and the molecular weight with the largest peak intensity among them was defined as the "corrected molecular weight." Furthermore, for those with a theoretical molecular weight of less than 700 in (b), the molecular weight obtained by rounding down the theoretical molecular weight in (b) to an integer and subtracting 1 was defined as the "corrected molecular weight."

[0118] - Adjustment after correction: The corrected molecular weight obtained by the above method may be the same even for different structures, depending on the degree of dehydration of the polyglycerol chain, the degree of polymerization of the polyglycerol chain, and the number of bonds to fatty acids (esterification number) of the polyglycerol chain. Due to molecular design considerations, the content of polyglycerol fatty acid esters with a high esterification number and a high degree of dehydration will be low. Therefore, for molecules with the same corrected molecular weight, all molecules except the one with the highest ranking according to the following criteria will not be included in the peak intensity calculation.

[0119] ・Priority criteria 1. Number of esterifications: fewer > more 2. Degree of dehydration: less > more 3. If the superiority of the comparison differs in criteria 1 and 2 above, the superiority is judged in the order of 1 > 2. For example, in a comparison of specific components (A) and (B), if 1. component (B) has fewer esterifications and 2. component (A) has a lower degree of glycerin dehydration, then 1. component (B) with fewer esterifications takes precedence because 1 > 2 in the above criteria.

[0120] Furthermore, considering the number of esterifications in the polyglycerol fatty acid ester and the degree of polymerization of glycerol, peak intensity is not included if the resulting dehydration degree is impossible. For example, in order for one water molecule to be removed from a polyglycerol fatty acid ester (dehydration degree of 1), the polyglycerol fatty acid ester must have two or more hydroxyl groups. Therefore, there are no polyglycerol fatty acid esters with only one hydroxyl group that have a dehydration degree of 1 to 3.

[0121] The following describes (c) in Production Example 1. For each component of the polyglycerin monocaprate ester product calculated in Table 7, if the theoretical molecular weight in (b) is less than 700, the "corrected molecular weight" was obtained by subtracting 1 from the molecular weight obtained by rounding down the theoretical molecular weight to an integer. For example, the monoester (glycerin degree of polymerization = 4) has a theoretical molecular weight of 468.58, and its corrected molecular weight is 467.

[0122] For substances in (b) with a theoretical molecular weight of 700 or more, the peak intensities corresponding to three points were compared: the molecular weight obtained by rounding down the theoretical molecular weight in (b) to an integer (M1), the molecular weight obtained by subtracting 1 from M1 (M2), and the molecular weight obtained by subtracting 2 from M1 (M3). The molecular weight with the highest intensity among these was defined as the "corrected molecular weight." For example, the theoretical molecular weight of polyglycerin (glycerin degree of polymerization = 11, degree of dehydration = 3) is 778.83, so the molecular weight (M1) is 778, the molecular weight (M2) is 777, and the molecular weight (M3) is 776. The peak intensity corresponding to molecular weight (M1) is 6780, the peak intensity corresponding to molecular weight (M2) is 8510, and the peak intensity corresponding to molecular weight (M3) is 6740 (see Table 2). Therefore, the peak intensity with the highest intensity, 8510, i.e., 777 = molecular weight (M2), is the "corrected molecular weight."

[0123] Furthermore, for example, the theoretical molecular weight of the triester (glycerin degree of polymerization = 4) is 777.8, and the molecular weight (M1) is 777, the molecular weight (M2) is 776, and the molecular weight (M3) is 775. The peak intensity corresponding to molecular weight (M1) is 8510, the peak intensity corresponding to molecular weight (M2) is 6740, and the peak intensity corresponding to molecular weight (M3) is 7840 (see Table 2). Therefore, the peak intensity with the highest value, 8510, i.e., 777 = molecular weight (M1), can be the "corrected molecular weight". However, since the corrected molecular weight is the same as that of the polyglycerin (glycerin degree of polymerization = 11, dehydration degree = 3) mentioned above, in accordance with the "priority order" described above, the corrected molecular weight of polyglycerin (glycerin degree of polymerization = 11, dehydration degree = 3) becomes "777", and the triester (glycerin degree of polymerization = 4) is not included in the peak intensity.

[0124] Furthermore, the monoester compound (glycerol degree of polymerization = 1) has two hydroxyl groups, and is therefore included in the peak intensity when the degree of dehydration is 1, but is not included in the peak intensity when the degree of dehydration is 2 or 3 because it does not exist. The diester compound (glycerol degree of polymerization = 1) has only one hydroxyl group, so it does not exist when the degree of dehydration is 1 to 3, and is not included in the peak intensity. Taking the above into consideration, the corrected molecular weight of each component is summarized in Table 8. "-" indicates a component that is not included in the peak intensity.

[0125]

[0126] The corrected molecular weights of each component of the polyglycerin mono fatty acid ester product calculated in (d) and (c) are matched with the intensities obtained in (a), and these are summed up to obtain the peak intensities of "monoester," "dehydrated monoester," "diester," "dehydrated diester," "tryester," "dehydrated tryester," "polyglycerin," and "dehydrated polyglycerin" as defined in P1 to P3.

[0127] The following describes (d) in Production Example 1. Table 9 shows the correspondence between the corrected molecular weight of each component of the polyglycerin monocaprate product calculated in (b) and the intensity obtained in (a). Based on Table 9, the peak intensities of "monoester," "dehydrated monoester," "diester," "dehydrated diester," "tryester," "dehydrated tryester," "polyglycerin," and "dehydrated polyglycerin" as defined in P1 will be explained.

[0128] Figure 2 is a chart showing the corrected molecular weight and the corresponding peak intensity percentage (%) for the polyglycerin monocaprate ester product of Production Example 1. The hollow bar graph represents the monoester.

[0129]

[0130] The peak intensity for "monoester" is the sum of the values ​​for the monoesters in Table 9 where the degree of polymerization of glycerin is between 1 and 20, and is 1,324,420. The peak intensity for "diester" is the sum of the values ​​for the diesters in Table 9 where the degree of polymerization of glycerin is between 1 and 20, and is 244,000. The peak intensity for "tryester" is the sum of the values ​​for the triesters in Table 9 where the degree of polymerization of glycerin is between 1 and 20, and is 122,900. The peak intensity for "polyglycerin" is the sum of the values ​​for the polyglycerins in Table 9 where the degree of polymerization of glycerin is between 1 and 20, and is 320,400.

[0131] The peak intensity for "dehydrated monoester" is the sum of the cases in Table 9 where the degree of polymerization of glycerin is 1 to 20 and the degree of dehydration is 1 to 3, and is 555300 (= 207830 + 188370 + 159100). The peak intensity for "dehydrated diester" is the sum of the cases in Table 9 where the degree of polymerization of glycerin is 1 to 20 and the degree of dehydration is 1 to 3, and is 533110 (= 201130 + 169410 + 162570). The peak intensity for "dehydrated triester" is the sum of the cases in Table 9 where the degree of polymerization of glycerin is 1 to 20 and the degree of dehydration is 1 to 3, and is 128630 (= 42650 + 43130 + 42850). The peak intensity for "dehydrated polyglycerin" is the sum of the values ​​for the dehydrated polyglycerin products in Table 9 where the degree of polymerization of glycerin is 1 to 20 and the degree of dehydration is 1 to 3, which is 848470 (= 445710 + 258400 + 144360).

[0132] The above formulas (X) and (Y) are calculated using the peak intensities of each component of the polyglycerin monofatty acid ester product calculated in (e) and (d).

[0133] The following explains (e) in Manufacturing Example 1. Equation (X) = P2 / P1 = 1324420 / 4077230 = 0.325 Equation (Y) = P3 / P1 = (320400 + 848470) / 4077230 = 0.287

[0134] (Production Example 2) 0.55 mol (94.3 g) of capric acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 5.48 mol (405.67 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monocaprate ester product with an average degree of polymerization of glycerin of 10 was obtained.

[0135] HPLC analysis of the obtained polyglycerin monocaprate ester products revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 93.8%.

[0136] Furthermore, the obtained polyglycerin monocaprate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.353. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.322.

[0137] Furthermore, the HLB value of the obtained polyglycerol monocaprate ester was 16.8.

[0138] (Production Example 3) 0.53 mol (106.4 g) of lauric acid was placed in a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 5.31 mol (393.6 g) of glycidol was added dropwise over 10 hours. During the addition of glycidol, 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise. Then, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Next, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monolaurate ester product with an average degree of polymerization of glycerin of 10 was obtained.

[0139] HPLC analysis of the obtained polyglycerin monolaurate ester product revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 98.9%.

[0140] Furthermore, the obtained polyglycerin monolaurate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.429. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.348.

[0141] Furthermore, the HLB value of the obtained polyglycerin monolaurate ester was 16.0.

[0142] (Production Example 4) 0.74 mol (169.7 g) of myristic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.46 mol (330.3 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monomyristate ester product with an average degree of polymerization of glycerin of 6 was obtained.

[0143] HPLC analysis of the obtained polyglycerin monomyristate ester product revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 96.2%.

[0144] Furthermore, the obtained polyglycerin monomyristate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.446. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.267.

[0145] Furthermore, the HLB value of the obtained polyglycerol monomyristate ester was 13.4.

[0146] (Production Example 5) 0.52 mol (117.8 g) of myristic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 5.16 mol (382.18 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monomyristate ester product with an average degree of polymerization of glycerin of 10 was obtained.

[0147] HPLC analysis of the obtained polyglycerin monomyristate ester product revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 97.4%.

[0148] Furthermore, the obtained polyglycerin monomyristate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.391. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.314.

[0149] Furthermore, the HLB value of the obtained polyglycerol monomyristate ester was 15.2.

[0150] (Production Example 6) 0.69 mol (195.1 g) of stearic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.12 mol (304.9 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monostearate ester product with an average degree of polymerization of glycerin of 6 was obtained.

[0151] The obtained polyglycerin monostearate ester product could not be dissolved in the measurement solvent (10% methanol solution), and therefore HPLC analysis could not be performed. However, considering the trends of polyglycerin monofatty acid ester products in the manufacturing method and other manufacturing examples, it is estimated that the area percentage of peaks present in the HPLC chart between retention times of 6.0 and 20.0 minutes, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, is at least 80%.

[0152] Furthermore, the obtained polyglycerin monostearate product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.256. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.457.

[0153] Furthermore, the HLB value of the obtained polyglycerin monostearate ester was 11.9.

[0154] (Production Example 7) 0.49 mol (138.7 g) of stearic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.88 mol (361.3 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monostearate ester product with an average degree of polymerization of glycerin of 10 was obtained.

[0155] The obtained polyglycerin monostearate ester product could not be dissolved in the measurement solvent (10% methanol solution), and therefore HPLC analysis could not be performed. However, considering the trends of polyglycerin monofatty acid ester products in the manufacturing method and other manufacturing examples, it is estimated that the area percentage of peaks present in the HPLC chart between retention times of 6.0 and 20.0 minutes, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, is at least 80%.

[0156] Furthermore, the obtained polyglycerin monostearate product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.410. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.414.

[0157] Furthermore, the HLB value of the obtained polyglycerin monostearate ester was 14.0.

[0158] (Production Example 8) 0.86 mol (244.0 g) of oleic acid was placed in a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, 3.46 mol (256.0 g) of glycidol was added dropwise over 20 hours while maintaining the reaction temperature at 120°C. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monooleate ester product with an average degree of polymerization of glycerin of 4 was obtained.

[0159] HPLC analysis of the obtained polyglycerin monooleate ester products revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 95.5%.

[0160] Furthermore, the obtained polyglycerin monooleate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.502. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.316.

[0161] Furthermore, the HLB value of the obtained polyglycerol monooleate ester was 10.4.

[0162] (Production Example 9) 0.69 mol (194.3 g) of oleic acid was placed in a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.13 mol (305.7 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monooleate ester product with an average degree of polymerization of glycerin of 6 was obtained.

[0163] HPLC analysis of the obtained polyglycerin monooleate ester products revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 95.8%.

[0164] Furthermore, the obtained polyglycerin monooleate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.558. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.382.

[0165] Furthermore, the HLB value of the obtained polyglycerol monooleate ester was 12.0.

[0166] (Production Example 10) 0.49 mol (138.0 g) of oleic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, while maintaining the reaction temperature at 120°C, 4.89 mol (362.0 g) of glycidol was added dropwise over 10 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monooleate ester product with an average degree of polymerization of glycerin of 10 was obtained.

[0167] HPLC analysis of the obtained polyglycerin monooleate ester products revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 98.6%.

[0168] Furthermore, the obtained polyglycerin monooleate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.274. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.435.

[0169] Furthermore, the HLB value of the obtained polyglycerol monooleate ester was 14.0.

[0170] (Production Example 11) 0.86 mol (244.9 g) of isostearic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 120°C. Then, 3.44 mol (255.1 g) of glycidol was added dropwise over 20 hours while maintaining the reaction temperature at 120°C. Next, the mixture was aged for 3 hours while maintaining the temperature at 120°C. Then, the temperature was raised to 130°C and the reaction was continued until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monoisostearate ester product with an average degree of polymerization of glycerin of 4 was obtained.

[0171] HPLC analysis of the obtained polyglycerin monoisostearate ester product revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 97.6%.

[0172] Furthermore, the obtained polyglycerin monoisostearate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.507. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.307.

[0173] Furthermore, the HLB value of the obtained polyglycerin monoisostearate ester was 10.5.

[0174] (Production Example 12) 0.69 mol (195.1 g) of isostearic acid was added to a 1-liter four-necked flask equipped with a nitrogen inlet tube, stirrer, condenser, temperature controller, and dropping cylinder, and heated to 150°C. Then, while maintaining the reaction temperature at 150°C, 4.12 mol (304.9 g) of glycidol was added dropwise over 12 hours, and 0.004 mol (0.4 g) of 42.5% phosphoric acid was added dropwise during the addition of glycidol. The reaction was then continued while maintaining the temperature at 150°C until the oxirane concentration in the system was less than 0.1%. After cooling, the reaction product was removed, and approximately 500 g of polyglycerin monoisostearate ester product with an average degree of polymerization of glycerin of 6 was obtained.

[0175] HPLC analysis of the obtained polyglycerin monoisostearate ester product revealed that the area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 97.1%.

[0176] Furthermore, the obtained polyglycerin monoisostearate ester product was subjected to mass spectrometry in the same manner as in Production Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), which was 0.523. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), which was 0.293.

[0177] Furthermore, the HLB value of the obtained polyglycerin monoisostearate ester was 12.1.

[0178] (Comparative Product 1) HPLC analysis was performed on SY Glister MO-7S (polyglycerin monooleate ester with an average degree of polymerization of glycerin of 10, manufactured by Sakamoto Pharmaceutical Co., Ltd.). The area ratio of peaks located between retention times of 6.0 and 20.0 minutes on the HPLC chart, corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester, as well as polyglycerin and dehydrated polyglycerin, was 95.5%. Mass spectrometry was performed in the same manner as in Manufacturing Example 1, and the peak intensity ratio (P2 / P1) was calculated according to the above formula (X), resulting in a value of 0.167. The peak intensity ratio (P3 / P1) was calculated according to the above formula (Y), resulting in a value of 0.447.

[0179] Furthermore, the HLB value for SY Glister MO-7S was 14.0.

[0180] Cosmetic compositions for Examples 1-1 to 1-8, Examples 2-1 to 2-28, and Comparative Examples 1-1 to 1-2 were prepared by mixing polyglycerin monofatty acid ester (A) and oil (B) in the proportions shown in Tables 10 to 12. The numerical values ​​for each component in Tables 10 to 12 represent parts by mass.

[0181] Each component in Tables 10-12 is explained below.• Polyglycerin mono fatty acid ester (A) MO04: Polyglycerin monooleate ester product obtained in Production Example 8 with an average degree of polymerization of 4. HLB value: 10.4 MO06: Polyglycerin monooleate ester product obtained in Production Example 9 with an average degree of polymerization of 6. HLB value: 12.0 MO10: Polyglycerin monooleate ester product obtained in Production Example 10 with an average degree of polymerization of 10. HLB value: 14.0 MIS04: Polyglycerin monoisostearate ester product obtained in Production Example 11 with an average degree of polymerization of 4. HLB value: 10.5 MC06: Polyglycerin monocaprate ester product obtained in Production Example 1 with an average degree of polymerization of 6. HLB value: 15.4 MIS06: Polyglycerin monoisostearate ester product obtained in Production Example 12 with an average degree of polymerization of 6. HLB value is 12.1 Other polyglycerin mono fatty acid esters MO-7S: Polyglycerin monooleate ester with an average degree of polymerization of glycerin of 10, manufactured by Sakamoto Pharmaceutical Co., Ltd. HLB value is 14.0 Oils (B) Moresco White P-70: Hydrocarbon oil (liquid paraffin), manufactured by MORESCO Corporation Saracos 816T: Ester oil (cetyl ethylhexanoate), manufactured by Nisshin Oillio Group Ltd. Saracos P-8: Ester oil (ethylhexyl palmitate), manufactured by Nisshin Oillio Group Ltd. Saracos 99: Ester oil (isononyl isononanoate), manufactured by Nisshin Oillio Group Ltd. O.D.O: Tri(caprylic / capric acid) glyceryl, manufactured by Nisshin Oillio Group Ltd. T.I. O: Triethylhexanoin, manufactured by Nisshin Oillio Group Ltd. Saracos 334: Tri(caprylic / capric / myristic / stearic acid) glyceryl, manufactured by Nisshin Oillio Group Ltd. CORN Germ OIL REFINED: Corn germ oil, manufactured by Vantage Specialties Spain, S.L.U. Rice Germ Oil: Rice germ oil, manufactured by Koei Kogyo Co., Ltd. CROPURE OL: Olive fruit oil, manufactured by Croda Japan Co., Ltd. Saracos TG-810S: (Caprylic / capric / succinic acid) triglyceryl, manufactured by Nisshin Oillio Group Ltd.

[0182] [Evaluation] For Examples 1-1 to 1-8, Examples 2-1 to 2-28, and Comparative Examples 1-1 to 1-2, the components were weighed into glass beakers according to the compositions listed in Tables 10 to 12, heated and mixed at approximately 80°C, and then cooled to near room temperature to prepare the cosmetic compositions. Lipstick (product name: Lipstick Y, manufactured by Chifure Holdings Co., Ltd.) was applied to the arms of five expert panel members, and 0.5 g each of the cosmetic compositions from the examples and comparative examples was applied on top of the lipstick and allowed to blend in, after which it was washed off with water. Points were assigned to the following items, and the average values ​​of the five people are listed as evaluation results in Tables 10 to 12. ・Visibility: Visibility was evaluated according to the following criteria. 1: Watery 2: Slightly viscous 3: Viscous 4: Moderately viscous 5: Viscosity equivalent to honey ・Blending: Blending was evaluated according to the following criteria. 1: Slightly difficult to blend 2: Blends well 3: Blends fairly well 4: Blends well 5: Blends very well Emulsification: Emulsification was evaluated according to the following criteria: 1: Water does not penetrate 2: Only a little water penetrates 3: Water penetrates 4: Emulsifies uniformly 5: Emulsifies uniformly immediately Residual feeling: Residual feeling was evaluated according to the following criteria: 1: Sticky 2: Leaves a residue 3: Leaves a slight residue 4: Leaves almost no residue 5: Leaves a dry feeling

[0183] • Viscosity Measurement: The viscosity (mPa·s) of the cosmetic composition at 25°C was measured using a Type B viscometer (product name: BMII, manufactured by Toki Sangyo Co., Ltd.). The results are listed in Tables 10-12 under Viscosity (mPa·s).

[0184] - Appearance Evaluation / Measurement of Transmittance (%) at 660 nm A UV-Vis spectrophotometer (product name: UV-1800, manufactured by Shimadzu Corporation) was used to measure the transmittance (%) at 660 nm and evaluate it as follows. The measurement temperature was 25°C. The evaluation results are recorded in "Transparency" in Tables 10-12. The measurement results are also recorded in "Transmittance (%)". ◎: 95% or more ○: 90% or more and less than 95% △: 60% or more and less than 90% ×: Less than 60%

[0185]

[0186] In summary, the composition of the present disclosure and its variations are described below. [1] A cosmetic composition comprising a polyglycerin monofatty acid ester (A) and an oil (B), wherein the polyglycerin monofatty acid ester (A) has 4 to 25 carbon atoms in the fatty acid, the peak intensity ratio represented by the following formula (X) is 0.20 or more, and the peak intensity ratio represented by the following formula (Y) is 0.46 or less. Equation (X) = P2 / P1 Equation (Y) = P3 / P1 P1: The sum of the peak intensities of the monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P2: The peak intensity of the monoester of polyglycerin fatty acid ester obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. P3: The sum of the peak intensities of the polyglycerin and dehydrated polyglycerin obtained by mass spectrometry of polyglycerin mono fatty acid ester (A) using a time-of-flight mass spectrometer. [2] A cosmetic composition according to [1], wherein the polyglycerin monofatty acid ester (A) comprises at least one selected from the group consisting of a polyglycerin monofatty acid ester (A1) having an average degree of polymerization of glycerin of 3 or more and less than 5, a polyglycerin monofatty acid ester (A2) having an average degree of polymerization of glycerin of 5 or more and less than 8, and a polyglycerin monofatty acid ester (A3) having an average degree of polymerization of glycerin of 8 or more and less than 12. [3] A cosmetic composition according to [1] or [2], wherein the polyglycerin monofatty acid ester (A) has a carbon number of 6 or more, 8 or more, 10 or more, 12 or more, 14 or more, 15 or more, 16 or more, or 18 or more; and / or 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, or 8 or less. [4] The cosmetic composition according to any one of [1] to [3], wherein the polyglycerin monofatty acid ester (A) has 4 to 14, 15 to 25, 8 to 14, or 16 to 18 carbon atoms in the fatty acid.[5] A cosmetic composition according to any one of [1] to [4], wherein the polyglycerin monofatty acid ester (A) has a peak intensity ratio represented by the above formula (X) of 0.21 or more, 0.23 or more, 0.24 or more, 0.25 or more, 0.26 or more, 0.28 or more, 0.3 or more, 0.31 or more, 0.33 or more, 0.35 or more, 0.37 or more, 0.40 or more, 0.44 or more, 0.48 or more, or 0.52 or more; and / or 1 or less, 0.9 or less, 0.8 or less, 0.75 or less, 0.7 or less, 0.65 or less, or 0.6 or less. [6] A cosmetic composition according to any one of [1] to [5], wherein the polyglycerin monofatty acid ester (A) has a peak intensity ratio represented by the above formula (Y) that is 0.45 or less, 0.44 or less, 0.42 or less, 0.39 or less, 0.37 or less, 0.35 or less, 0.33 or less, 0.32 or less, or 0.30 or less; and / or 0.01 or more, 0.05 or more, or 0.10 or more. [7] A cosmetic composition according to any one of [1] to [6], wherein the polyglycerin monofatty acid ester (A) has an average degree of polymerization of glycerin that is 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more; and / or 40 or less, 35 or less, 30 or less, 25 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, 8 or less, 6 or less, or 4 or less. [8] A cosmetic composition according to any one of [1] to [7], wherein the average degree of polymerization of glycerin in the polyglycerin monofatty acid ester (A) is 2 to 40, 3 to 20, or 4 to 10. [9] A cosmetic composition according to any one of [1] to [8], wherein the fatty acid in the polyglycerin monofatty acid ester (A) is a straight-chain fatty acid or a branched-chain fatty acid.

[10] A cosmetic composition according to any one of [1] to [9], wherein the fatty acid in the polyglycerin monofatty acid ester (A) is a saturated fatty acid or an unsaturated fatty acid.

[11] A cosmetic composition according to any one of [1] to [9], wherein the fatty acid in the polyglycerin monofatty acid ester (A) is caproic acid (C). ６ (saturated fatty acids), caprylic acid (C ８ (saturated fatty acids), pelargonic acid (C ９ (saturated fatty acids), 2-ethylhexanoic acid (C ８(branched-chain fatty acids), capric acid (C １０ (saturated fatty acids), lauric acid (C １２ (saturated fatty acids), isotridecanoic acid (C １３ (branched-chain fatty acids), myristic acid (C １４ (saturated fatty acids), pentadecyl acid (C １５ (saturated fatty acids), palmitic acid (C １６ (saturated fatty acids), palmitoleic acid (C １６ (unsaturated fatty acids), stearic acid (C １８ (saturated fatty acids), isostearic acid (C １８ (branched-chain fatty acids), oleic acid (C １８ (unsaturated fatty acids), linoleic acid (C １８ (unsaturated fatty acids), ricinoleic acid (C １８ (unsaturated fatty acids), hydroxystearic acid (C １８ (substituted fatty acids), arachidic acid (C ２０ (saturated fatty acids), behenic acid (C ２２ , saturated fatty acids), erucic acid (C ２２ , unsaturated fatty acids), and nervonic acid (C ２４A cosmetic composition according to any one of [1] to

[10] , wherein at least one selected from the group consisting of (unsaturated fatty acids).

[12] A cosmetic composition according to any one of [1] to

[11] , wherein in polyglycerin monofatty acid ester (A), the area ratio of the peaks corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester of the polyglycerin fatty acid ester, as well as polyglycerin and dehydrated polyglycerin, in HPLC analysis, is 50% or more, 60% or more, 80% or more, or 90% or more.

[13] A cosmetic composition according to any one of [1] to

[12] , wherein in polyglycerin monofatty acid ester (A), the area ratio of the peaks corresponding to the monoester, dehydrated monoester, polyester, and dehydrated polyester of the polyglycerin fatty acid ester, in HPLC (high-performance liquid chromatography) analysis, is 5% or more, 10% or more, or 20% or more.

[14] The cosmetic composition according to any one of [1] to

[13] , wherein in the polyglycerin monofatty acid ester (A), the area ratio of the peaks corresponding to polyglycerin and polyglycerin dehydrated product in HPLC (high-performance liquid chromatography) analysis is 80% or less, 70% or less, or 60% or less.

[15] The cosmetic composition according to any one of [1] to

[14] , wherein the polyglycerin monofatty acid ester (A) is a reaction product of glycidol and a fatty acid, an esterified product of polyglycerin and a fatty acid, or a transesterified product of polyglycerin and a fatty acid ester.

[16] The cosmetic composition according to any one of [1] to

[15] , wherein the oil (B) comprises at least one selected from the group consisting of hydrocarbon oils, ester oils, triglycerides, silicone oils, animal and vegetable oils, and ether oils.

[17] The cosmetic composition according to any one of [1] to

[16] , wherein the content of polyglycerin mono fatty acid ester (A) in the above cosmetic composition (100% by mass) is 2% by mass or more, 4% by mass or more, 8% by mass or more, 10% by mass or more, or 14% by mass or more.

[18] The cosmetic composition according to any one of [1] to

[17] , wherein the content of polyglycerin mono fatty acid ester (A) in the cosmetic composition (100% by mass) is 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, or 30% by mass or less.

[19] The cosmetic composition according to any one of [1] to

[18] , wherein the content of oil (B) in the cosmetic composition (100% by mass) is 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, or 70% by mass or more.

[20] The cosmetic composition according to any one of [1] to

[19] , wherein the content of oil (B) in the cosmetic composition (100% by mass) is 98% by mass or less, 96% by mass or less, 92% by mass or less, 90% by mass or less, or 86% by mass or less.

[21] A cosmetic composition according to any one of [1] to

[20] , wherein the HLB value of the polyglycerin mono fatty acid ester (A) is 5 to 17 or 10 to 15.

[22] A cosmetic composition according to any one of [1] to

[21] , wherein the cosmetic composition is transparent.

[23] A cosmetic composition according to any one of [1] to

[22] , which is for use as an oily cosmetic, an emulsified cosmetic, or a bicontinuous cosmetic.

[24] A cosmetic composition according to any one of [1] to

[23] , which is for use as a cleansing product such as a cleansing milk, cleansing lotion, cleansing oil, cleansing balm, hot cleansing balm, cleansing gel, hot cleansing gel, cleansing gel pack, cleansing cream, or cleansing foam; for use as a massage product such as a massage oil, massage oil gel, massage scrub gel, or hot massage gel; for use as a hair cream, hair oil, hair liquid, or bath additive.

Claims

A cosmetic composition comprising a polyglycerin monofatty acid ester (A) and an oil (B), In polyglycerol monofatty acid ester (A), Fatty acids have 4 to 25 carbon atoms. The peak intensity ratio represented by the following formula (X) is 0.20 or higher, and A cosmetic composition having a peak intensity ratio of 0.46 or less, represented by the following formula (Y). Formula (X)=P2 / P1 Formula (Y)=P3 / P1 P1: Mass spectrometry was performed on polyglycerol mono fatty acid ester (A) using a time-of-flight mass spectrometer, and the sum of the peak intensities of the obtained polyglycerol fatty acid ester monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester, as well as polyglycerol and dehydrated polyglycerol. P2: Mass spectrometry was performed on polyglycerol mono fatty acid ester (A) using a time-of-flight mass spectrometer, and the peak intensity of the obtained polyglycerol monoester was determined. P3: For polyglycerol monofatty acid ester (A), mass spectrometry was performed using a time-of-flight mass spectrometer, and the sum of the peak intensities of the obtained polyglycerol and polyglycerol dehydrated products was obtained. The cosmetic composition according to claim 1, wherein the polyglycerin monofatty acid ester (A) has 8 to 22 carbon atoms in the fatty acid. The cosmetic composition according to claim 1 or 2, wherein the HLB value of the polyglycerin monofatty acid ester (A) is 5 to 17. The cosmetic composition according to claim 1 or 2, wherein the average degree of polymerization of glycerin in the polyglycerin monofatty acid ester (A) is 2 to 22. The cosmetic composition according to claim 1 or 2, wherein the polyglycerin monofatty acid ester (A) comprises at least one selected from the group consisting of polyglycerin monofatty acid ester (A1) having an average degree of polymerization of glycerin of 3 or more and less than 5, polyglycerin monofatty acid ester (A2) having an average degree of polymerization of glycerin of 5 or more and less than 8, and polyglycerin monofatty acid ester (A3) having an average degree of polymerization of glycerin of 8 or more and less than 12. 　 The cosmetic composition according to claim 1 or 2, wherein the oil (B) comprises at least one selected from the group consisting of hydrocarbon oils, ester oils, and triglycerides. 　 The cosmetic composition according to claim 1 or 2, wherein the content of polyglycerin mono fatty acid ester (A) relative to the cosmetic composition (100% by mass) is 2 to 70% by mass. 　 The cosmetic composition according to claim 1 or 2, wherein the content of the oil agent (B) relative to the cosmetic composition (100% by mass) is 30 to 98% by mass. The cosmetic composition according to claim 1 or 2, wherein polyglycerin monofatty acid ester (A) is a reaction product of glycidol and a fatty acid, an esterified product of polyglycerin and a fatty acid, or a transesterified product of polyglycerin and a fatty acid ester. 　 The cosmetic composition according to claim 1 or 2, wherein the fatty acid is a straight-chain fatty acid or a branched-chain fatty acid. 　 The cosmetic composition according to claim 1 or 2, wherein the fatty acid is a saturated fatty acid or an unsaturated fatty acid. 　 A cosmetic composition according to claim 1 or 2, for use as an oil-based cosmetic. 　 A cosmetic composition according to claim 1 or 2, for cleansing purposes. 　 A polyglycerol monofatty acid ester (A) has 4 to 25 carbon atoms in the fatty acid, a peak intensity ratio represented by the following formula (X) of 0.20 or higher, and a peak intensity ratio represented by the following formula (Y) of 0.46 or lower, Mix with oil (B), A method for producing a cosmetic composition comprising a polyglycerol monofatty acid ester (A) and an oil (B). Formula (X)=P2 / P1 Formula (Y)=P3 / P1 P1: Mass spectrometry was performed on polyglycerol mono fatty acid ester (A) using a time-of-flight mass spectrometer, and the sum of the peak intensities of the obtained polyglycerol fatty acid ester monoester, dehydrated monoester, diester, dehydrated diester, triester, and dehydrated triester, as well as polyglycerol and dehydrated polyglycerol. P2: Mass spectrometry was performed on polyglycerol mono fatty acid ester (A) using a time-of-flight mass spectrometer, and the peak intensity of the obtained polyglycerol monoester was determined. P3: For polyglycerol monofatty acid ester (A), mass spectrometry was performed using a time-of-flight mass spectrometer, and the sum of the peak intensities of the obtained polyglycerol and polyglycerol dehydrated products was obtained.

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