JP6286138B2 - Fructooligosaccharide fatty acid ester and cosmetics - Google Patents

Description

  The technology of the present disclosure relates to a fructooligosaccharide fatty acid ester and a cosmetic containing the fructooligosaccharide fatty acid ester.

  In skin care cosmetics, in addition to the purpose of keeping the user's body clean and keeping the skin healthy, the touch when the user applies it to the skin and the feel when stretched on the skin, the so-called feeling of use, is also regarded as important. Yes. In the design of cosmetics, various components such as a moisturizing component, an emollient component, and a thickening agent for function expression are blended to achieve both a function and a feeling of use. However, when priority is given to the function, stickiness, creaking, and the like are likely to remain, and when priority is given to the touch, problems such as having to suppress active ingredients that express the function may occur.

  In makeup cosmetics, the aim is to beautify users, increase their appeal, and change their appearance, and the durability of the cosmetic film and the feeling of use are very important elements, as with skin care cosmetics. . In the design of cosmetics, various components such as powder components, oil components, moisturizers, surfactants and the like are blended for function expression, aiming to achieve both function and feeling of use. However, if priority is given to the function, the user may not be satisfied with the feeling of use due to stickiness, poor stretch, bulkiness, slimy feeling, etc. If priority is given to the touch, problems such as reduced functionality and storage stability may occur. There was a thing.

  For example, oily skin care cosmetics and makeup cosmetics mainly contain oils such as liquid oils, semi-solid oils, or solid oils, and coloring materials for coloring cosmetics. Yes. However, conventional cosmetics have the drawback of feeling sticky and oily. Therefore, in order to obtain a good feeling of use, powders such as three-dimensional cross-linked organopolysiloxane, silica and resin powder are blended. (For example, refer to Patent Document 1 and Patent Document 2).

JP-A-1-79106 JP-A-2005-247808

  By the way, if 3D cross-linked organopolysiloxane is blended in cosmetics in order to improve stability, freshness, and makeup sustainability, the soft touch is lost and the spread becomes worse. there were. On the other hand, even cosmetics containing powders such as silica and resin powder have not yet solved the stickiness of oily components in cosmetics.

  An object of the technology of the present disclosure is to provide a fructooligosaccharide fatty acid ester having no stickiness and adhesiveness, and a cosmetic.

In one embodiment of the fructooligosaccharide fatty acid ester in the present disclosure, the fructooligosaccharide and the fatty acid represented by the general formula R ₁ COOH are ester-bonded. The fructooligosaccharide has an average molecular weight of 300 or more and 10,000 or less. The fatty acid hydrocarbon group R ₁ is an alkyl group or an alkenyl group, and the hydrocarbon group R ₁ includes a straight chain hydrocarbon group having 7 to 11 carbon atoms and a branched chain having 7 to 17 carbon atoms. At least one of a hydrocarbon group and an unsaturated hydrocarbon group having 7 to 17 carbon atoms is included. The substitution rate of the fatty acid per molecule of the fructooligosaccharide is 95% or more and 100% or less, and is liquid at 25 ° C.

One aspect of the cosmetic according to the present disclosure includes an oil agent in a range of 0.1 wt% to 99.8 wt%, and the oil agent is a fructooligosaccharide fatty acid ester.
One aspect of the cosmetics according to the present disclosure is at least one of a first fructooligosaccharide fatty acid ester as an oil agent, a dextrin fatty acid ester as a gelling agent or a film forming agent, and a second fructooligosaccharide fatty acid ester as a gelling agent. Including. In the first fructooligosaccharide fatty acid ester, fructooligosaccharide and a fatty acid represented by the general formula R ₁ COOH are ester-bonded, the average molecular weight of the fructooligosaccharide is 300 or more and 10,000 or less, and the hydrocarbon group R _{1 of the} fatty acid. Is an alkyl group or an alkenyl group, and the hydrocarbon group R ₁ includes a straight chain hydrocarbon group having 7 to 11 carbon atoms, a branched hydrocarbon group having 7 to 17 carbon atoms, and a carbon number At least one of 7 to 17 unsaturated hydrocarbon groups is included. The substitution rate of the fatty acid per molecule of the fructo-oligosaccharide is 65% or more and 100% or less and is liquid at 25 ° C. The dextrin fatty acid ester and the second fructooligosaccharide fatty acid ester are solid or resinous at 25 ° C.

In another aspect of the cosmetic according to the present disclosure, the substitution rate of the fatty acid per molecule of the first fructooligosaccharide is 95% or more and 100% or less.
According to the above aspect, since it is an oil agent composed of an ester of fructooligosaccharide and a fatty acid, for example, it has more affinity for skin, hair, eyelashes, etc. than an ester of alcohol or glycerin and a fatty acid. The amount of high sugar used increases the adhesion to the skin. Moreover, since fructose oligosaccharides are used as constituent materials for esters, the molecular weight ratio of sugar chains in fructo-oligosaccharide fatty acid esters is larger than when monosaccharides or disaccharides are used, resulting in higher adhesion to the skin. It is done.

  Here, in the case of an oil agent using a material having a lower affinity for the skin than fructo-oligosaccharide, the adhesion to the skin is increased by increasing the ratio of the hydroxyl group, which is a hydrophilic group having a high affinity for the skin, in the molecule. Has been enhanced. However, although the adhesion of the oil agent is enhanced by the hydroxyl group, it gives the user a sticky feeling derived from the hydroxyl group. In this respect, in the above aspect, it is possible to ensure adhesion to the skin with fructooligosaccharides, so that the residual amount of hydroxyl groups per molecule of fructooligosaccharides can be reduced, that is, the fatty acid substitution rate can be increased. it can. As a result, according to the said aspect, the stickiness of fructo-oligosaccharide fatty acid ester which is an oil agent can be suppressed by making the substitution rate of a fatty acid 95% or more high.

  In another aspect of the cosmetic according to the present disclosure, the first fructooligosaccharide fatty acid ester is included in a range of 0.5 wt% to 90 wt%, and the dextrin fatty acid ester and the second fructooligosaccharide fatty acid ester are The total amount is included in the range of 0.5 wt% to 30 wt%.

  According to another aspect of the cosmetic in the present disclosure, the cosmetic is imparted with high adhesion to the skin and low stickiness, which are characteristics of the first fructooligosaccharide fatty acid ester. In addition, the dextrin fatty acid ester and the second fructo-oligosaccharide fatty acid ester prevent the cosmetic from being applied to the skin while preventing the cosmetic from dripping from the application target.

It is a graph which shows the relationship between the average molecular weight of the fructooligosaccharide in the fructooligosaccharide fatty acid ester which is liquid at 25 degreeC, the carbon number of a fatty acid, and a substitution rate.

  One embodiment of a fructooligosaccharide fatty acid ester and a cosmetic will be described with reference to FIG. Below, the structure of fructo-oligosaccharide fatty acid ester, the state of fructooligosaccharide fatty acid ester, the manufacturing method of fructooligosaccharide fatty acid ester, and the structure of cosmetics are demonstrated in order.

[Configuration of fructooligosaccharide fatty acid ester]
Fructooligosaccharide fatty acid ester is an ester of fructooligosaccharide and fatty acid, and has a structure represented by the following chemical formula 1.

  In the above chemical formula 1, n represents the number of fructose residues constituting the fructo-oligosaccharide, and A represents a fatty acid residue or hydrogen that forms an ester bond with the hydroxyl group of the fructose residue. When the fructooligosaccharide polymer constituting the fructooligosaccharide fatty acid contains glucose, B is a glucose residue represented by the following chemical formula 2, and when the fructooligosaccharide polymer does not contain glucose, B is: A fatty acid residue or hydrogen similar to A is shown.

  The fructo-oligosaccharide is an oligosaccharide having fructose as a main component, and the average molecular weight (hereinafter also referred to as molecular weight) of the fructo-oligosaccharide is preferably 300 or more and 10,000 or less. The average molecular weight indicates the number average molecular weight. That is, “n + 2” which is the degree of polymerization of fructooligosaccharide is preferably 2 or more and 61 or less, and more preferably 3 or more. The fructooligosaccharide binding mode may be β-2,1 bond or β-2,6 bond. Fructooligosaccharides whose binding mode is β-2,1 bond include inulin, asparagosin, asphodelan, tritican, critezan, bacmondow and the like and fructooligosaccharides generated from these polysaccharides. Fructooligosaccharides whose binding mode is β-2,6-linkage include fructo-oligosaccharides generated from Flean, Levan, Ceracan, etc., and these polysaccharides. Furthermore, fructooligosaccharides include fructooligosaccharides obtained by polymerizing fructose contained in sucrose by a transfer reaction using an enzyme or the like using sucrose as a raw material.

The fatty acid is represented by the general formula R ₁ COOH, and the hydrocarbon group R ₁ constituting the fatty acid has a straight chain alkyl group having 7 to 11 carbon atoms, or has 7 to 17 carbon atoms. At least one of a branched alkyl group and an alkenyl group is used. As the fatty acid, for example, at least one of caprylic acid, capric acid, lauric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, and oleic acid is used.

  Each fructose residue other than both ends constituting the fructooligosaccharide has three hydroxyl groups, and each of the three hydroxyl groups is one for each of the carbon at the 3rd position, the carbon at the 4th position, and the carbon at the 6th position. Are connected. Since each fructose residue can form an ester bond with a maximum of three fatty acids, the maximum value of the degree of substitution of fatty acids per fructose residue is three. In contrast, each of the sugars at both ends constituting the fructo-oligosaccharide has four hydroxyl groups, so the maximum value of the degree of substitution of fatty acids per monosaccharide is 4.

The substitution rate per fructose molecule (hereinafter also referred to as the substitution rate) is preferably 65% or more and 100% or less, more preferably 95% or more and 100% or less, and it binds to one molecule of fructo-oligosaccharide. More preferably, all the hydroxyl groups are substituted, that is, the substitution rate is 100%. When the substitution rate is less than 65%, the fructo-oligosaccharide fatty acid ester is resinous or solid at 25 ° C. When the ratio is 95% or more and 100% or less, the number of hydroxyl groups remaining in one molecule of fructooligosaccharide is smaller than when the substitution rate is 65% or more and less than 95%. Therefore, when the fructooligosaccharide fatty acid ester is applied to the skin, the sticky feeling given to the user is suppressed. The substitution rate of fatty acid per molecule of fructo-oligosaccharide constituting the fructooligosaccharide fatty acid ester can be calculated by the following formula using the ester value and the hydroxyl value.
Substitution rate (%) = ester value / (ester value + hydroxyl value) × 100
Examples of fructooligosaccharide fatty acid esters include caprylic fructooligosaccharide, capric fructooligosaccharide, (capryl / capric acid) fructooligosaccharide, lauric fructooligosaccharide, 2-ethylhexanoic acid fructooligosaccharide, isononanoic acid fructooligosaccharide, and isostearic acid fructooligosaccharide. , (Lauric acid / isononanoic acid) fructooligosaccharides.

  When the fructooligosaccharide fatty acid ester is caprylic fructooligosaccharide, A in the above chemical formula 1 is a capryloyl group represented by the following chemical formula 3 or hydrogen.

  The fructooligosaccharide fatty acid ester is liquid at 25 ° C., and whether or not the fructooligosaccharide fatty acid ester is liquid at 25 ° C. is determined by the following method. That is, first, an A line as a marked line is attached to a glass bottomed cylindrical body having an inner diameter of 30 mm and a height of 120 mm at a position where the height from the bottom is 55 mm, and the height from the bottom. Is marked with a B line as a marked line. Then, the fructooligosaccharide fatty acid ester heated to 25 ° C. is supplied up to the A line to the standing cylindrical body. Next, the cylindrical body to which the fructooligosaccharide fatty acid ester is supplied is brought down on the horizontal base in a state where the outer peripheral surface of the cylindrical body is in contact with the horizontal base throughout the height direction.

  When a part of the fructooligosaccharide fatty acid ester in the cylindrical body exceeds the B line within 90 seconds from the time when the cylindrical body is tilted, the fructooligosaccharide fatty acid ester is liquid. On the other hand, when the whole fructo-oligosaccharide fatty acid ester does not exceed the B line within 90 seconds, the fructo-oligosaccharide fatty acid ester is resinous or solid.

[State of fructooligosaccharide fatty acid ester]
The state of fructooligosaccharide fatty acid ester is determined by the average molecular weight of fructooligosaccharide used for the synthesis of fructooligosaccharide fatty acid ester, the number of carbon atoms of fatty acid, and the substitution rate of fatty acid per fructooligosaccharide molecule. That is, in the fructooligosaccharide fatty acid ester, as the average molecular weight of the fructooligosaccharide increases, the viscosity of the fructooligosaccharide fatty acid ester increases. As the carbon number of the fatty acid increases, the viscosity of the fructooligosaccharide fatty acid ester increases. Such a tendency is common whether the fatty acid is linear or branched, and when the fatty acid is a linear saturated fatty acid and has 14 carbon atoms, the fructo-oligosaccharide fatty acid ester. Is a solid regardless of other conditions. In the fructooligosaccharide fatty acid ester, the viscosity of the fructooligosaccharide fatty acid ester increases as the substitution rate per molecule of the fructooligosaccharide decreases.

  As shown in FIG. 1, when the fatty acid constituting the fructooligosaccharide fatty acid ester is a linear saturated fatty acid, the molecular weight of the fructooligosaccharide, the carbon number of the fatty acid, and the substitution rate per molecule of fructooligosaccharide are as follows: The fructooligosaccharide fatty acid ester is in a liquid state at 25 ° C.

  As shown in FIG. 1 (a), 300 ≦ molecular weight M <1500, 8 ≦ carbon number C ≦ 10, 65% ≦ substitution rate T ≦ 100%, and carbon number C = 12, and The range defined by 75% ≦ substitution rate T ≦ 100% is the condition that the fructooligosaccharide fatty acid ester is liquid at 25 ° C.

  As shown in FIG. 1B, 1500 ≦ molecular weight M <3000, carbon number C = 8 and 65% ≦ substitution rate T ≦ 100%, carbon number C = 10 and 75% ≦ substitution. The range defined by the rate T ≦ 100% and the carbon number C = 12, and 85% ≦ substitution rate T ≦ 100% is the condition that the fructooligosaccharide fatty acid ester is liquid at 25 ° C.

  As shown in FIG. 1C, 3000 ≦ molecular weight M <6000, carbon number C = 8, 65% ≦ substitution rate T ≦ 100%, carbon number C = 10, and 80% ≦ substitution. The range defined by the rate T ≦ 100%, the carbon number C = 12, and the 87% ≦ substitution rate T ≦ 100% is the condition that the fructooligosaccharide fatty acid ester is liquid at 25 ° C.

  As shown in FIG. 1D, 6000 ≦ molecular weight M ≦ 10000, carbon number C = 8, 2.2 ≦ substitution rate T ≦ 100%, carbon number C = 10, and 90% ≦ The range defined by the substitution rate T ≦ 100% and the carbon number C = 12, and 93% ≦ substitution rate T ≦ 100% is the condition that the fructooligosaccharide fatty acid ester is liquid at 25 ° C.

For example, the fructooligosaccharide fatty acid esters listed below are liquid at 25 ° C.
・ Caprylic fructo-oligosaccharide, molecular weight 700, substitution rate 95%
・ Lauric acid fructooligosaccharide, molecular weight 700, substitution rate 98%
・ Lauric acid fructooligosaccharide, molecular weight 2000, substitution rate 87%
・ Caprylic acid fructooligosaccharide, molecular weight 8000, substitution rate 85%
When the fatty acid constituting the fructooligosaccharide fatty acid ester is a branched chain saturated fatty acid, the fructooligosaccharide molecular weight, the number of carbon atoms of the fatty acid, and the substitution rate per fructooligosaccharide molecule are included in the following ranges. The sugar fatty acid ester is liquid at 25 ° C.
・ Molecular weight of fructooligosaccharide M 300 ≦ M ≦ 10000
-Carbon number of fatty acid C 8 ≤ C ≤ 18
・ Fatty acid substitution rate T 65% ≦ T ≦ 100%
For example, the fructooligosaccharide fatty acid esters listed below are liquid at 25 ° C.
-Isononanoic acid fructooligosaccharide, molecular weight 700, substitution rate 75%
-Isopalmitic acid fructooligosaccharide, molecular weight 700, substitution rate 85%
・ Isostearic acid fructooligosaccharide, molecular weight 2000, substitution rate 80%
・ 2-ethylhexanoic acid fructooligosaccharide, molecular weight 8000, substitution rate 77%
When the fatty acid constituting the fructooligosaccharide fatty acid ester is a linear unsaturated fatty acid, the molecular weight of the fructooligosaccharide, the number of carbon atoms of the fatty acid, and the substitution rate per fructooligosaccharide molecule are included in the following ranges. For example, fructooligosaccharide fatty acid ester is liquid at 25 ° C.
・ Molecular weight of fructooligosaccharide M 300 ≦ M ≦ 10000
-Carbon number of fatty acid C 8 ≤ C ≤ 18
・ Fatty acid substitution rate T 65% ≦ T ≦ 100%
For example, the fructooligosaccharide fatty acid esters listed below are liquid at 25 ° C.
・ Oleic acid fructooligosaccharide fatty acid ester, molecular weight 8000, substitution rate 75%
-Palmitoleic acid fructooligosaccharide fatty acid ester, molecular weight 2000, substitution rate 90%
On the other hand, when the fatty acid constituting the fructooligosaccharide fatty acid ester is a linear fatty acid, the molecular weight of fructooligosaccharide, the number of carbon atoms of the fatty acid, and the substitution rate per molecule of fructooligosaccharide are included in the following ranges: Fructooligosaccharide fatty acid ester is solid at 25 ° C.

  For example, the condition that the fructooligosaccharide fatty acid ester is in a solid state is that when the molecular weight M is 300 ≦ molecular weight M <1500, the carbon number C = 12, and 65% ≦ substitution rate T <75%. The same condition is that when the molecular weight M is 1500 ≦ molecular weight M <3000, the carbon number C = 10 and 65% ≦ substitution rate T <75%, and the carbon number C = 12, and 65% ≦ The substitution rate T <85%. The same condition is that when the molecular weight M is 3000 ≦ molecular weight M <6000, the carbon number C = 10 and 65% ≦ substitution rate T <80%, and the carbon number C = 12, and 65% ≦ The substitution rate T <87%. The same condition is that when the molecular weight M is 6000 ≦ molecular weight M ≦ 10000, the carbon number C = 8 and 65% ≦ substitution rate T <2.2, the carbon number C = 10 and 65% ≦ substitution. Rate T <90%, carbon number C = 12, and 65% ≦ substitution rate T <93%.

In addition, for example, the fructooligosaccharide fatty acid esters listed below are solid at 25 ° C.
・ Lauric acid fructooligosaccharide, molecular weight 700, substitution rate 67%
・ Capric acid fructooligosaccharide, molecular weight 4000, substitution rate 75%
・ Caprylic acid fructooligosaccharide, molecular weight 8000, substitution rate 70%
・ Lauric acid fructooligosaccharide, molecular weight 8000, substitution rate 87%
When there is only one type of fatty acid constituting the fructooligosaccharide fatty acid ester, it is liquid at 25 ° C. regardless of the molecular weight of the fructooligosaccharide, the number of carbon atoms of the fatty acid, and the substitution rate per fructooligosaccharide molecule. Any combination of the three conditions may be used.

  Further, even when the fatty acid constituting the fructooligosaccharide fatty acid ester is a mixture of two or more fatty acids, regardless of the molecular weight of the fructooligosaccharide, the carbon number of the fatty acid, and the substitution rate per fructooligosaccharide molecule, As long as it is liquid, any combination of the three conditions may be used. For example, a combination of two types of straight chain fatty acids having different carbon numbers of fatty acids, a combination of straight chain fatty acids and branched fatty acids, a combination of branched fatty acids and unsaturated fatty acids, and a combination of two types of branched fatty acids having different carbon numbers. Etc.

[Method for producing fructooligosaccharide fatty acid ester]
As a method of synthesizing fructooligosaccharide fatty acid ester by reacting fructooligosaccharide and fatty acid, for example, the following method is used. That is, a method in which a fatty acid, a fatty acid chloride, or a fatty acid anhydride reacts with fructooligosaccharide in the presence of a basic catalyst is used.

[Composition of cosmetics]
The cosmetic comprises the above-mentioned fructooligosaccharide fatty acid ester, or a fructo-oligosaccharide fatty acid ester as the first fructooligosaccharide fatty acid ester, a dextrin fatty acid ester that is a gelling agent or a film forming agent, and a gelling agent. And at least one fructooligosaccharide fatty acid ester as a second fructooligosaccharide fatty acid ester.

Dextrin fatty acid ester is an ester of dextrin and fatty acid.
Dextrin is a polymer of α-glucose, and the average molecular weight of dextrin is preferably 500 or more and 20000 or less. As the dextrin, a hydrolyzate of starch is used. As the starch, for example, starch produced from corn, wheat, rice, sweet potato, potato, tapioca, sago, mung beans, peas, or the like is used. Alternatively, starch produced from other than the listed plants is used as the starch. As the starch, for example, processed starch such as acetylated starch can be used as long as the modified starch has a low modification rate to the extent that it does not affect the esterification reaction with fatty acid.

  As a method for producing dextrin, known methods such as an enzyme treatment method, an acid treatment method, an alkali treatment method, and a heat treatment method are used. In an enzyme treatment method, for example, an enzyme such as α-amylase, multi-dextrin is produced as an enzyme-modified dextrin, and in an acid treatment method, a treatment method using an inorganic acid or an organic acid, Generated. In the heat treatment method, starch is roasted in the absence of acid or in the presence of acid to produce roasted dextrin. In the heat treatment method, starch is roasted in the presence of acid-free or alkali to produce British gum.

The fatty acid is represented by the general formula R ₂ COOH, and the hydrocarbon group R ₂ constituting the fatty acid has a linear alkyl group and alkenyl group having 7 to 21 carbon atoms, or 7 to 21 carbon atoms. At least one of the following branched alkyl and alkenyl groups is used. The fatty acid includes at least one of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, and oleic acid. Used.

  Each glucose residue constituting the dextrin also has three hydroxyl groups, and each of the three hydroxyl groups is bonded to each of the carbon at the 2-position, the carbon at the 3-position, and the carbon at the 6-position. Since each glucose residue can form an ester bond with a maximum of three fatty acids, the maximum value of the average substitution degree of fatty acids per glucose residue (hereinafter also referred to as substitution degree) is 3. The degree of substitution per glucose residue is preferably 1.0 or more and 3.0 or less. When the substitution degree is less than 1.0, the dextrin fatty acid ester is hardly dissolved in the oil, and when the dextrin fatty acid ester is mixed with the oil, the undissolved residue or precipitation of the dextrin fatty acid ester occurs.

  Examples of dextrin fatty acid esters include caprylic dextrin, myristic dextrin, dextrin palmitate, dextrin stearate, dextrin (palmitic acid / ethylhexanoic acid), dextrin (palmitic acid / isostearic acid), and dextrin isostearate. It is done.

  Dextrin fatty acid ester is resinous or solid at 25 ° C and has the function of gelling a liquid oil, or when applied to the skin, it makes it difficult to break up makeup by creating a film on the skin. It has a function to do.

As a method for synthesizing a dextrin fatty acid ester by reacting dextrin with a fatty acid, the same method as that for the fructo-oligosaccharide fatty acid ester described above is used.
The fructooligosaccharide fatty acid ester as a gelling agent is an ester of fructooligosaccharide and a fatty acid, and the average molecular weight of the fructooligosaccharide is preferably 300 or more and 10,000 or less.

The fatty acid is represented by the general formula R ₃ COOH, and for the hydrocarbon group R ₃ constituting the fatty acid, at least one linear alkyl group having 7 to 21 carbon atoms is used. As the fatty acid, at least one of caprylic acid, capric acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, and behenic acid is used.

  The substitution rate of fatty acid per molecule of fructooligosaccharide constituting the fructooligosaccharide fatty acid ester is preferably 65% or more and 100% or less. When the substitution rate is less than 65%, the compatibility with the oil decreases, and when the fructooligosaccharide fatty acid ester is mixed with the oil, the undissolved residue or precipitation of the fructooligosaccharide fatty acid ester occurs.

  Examples of fructooligosaccharide fatty acid esters include caprylic fructooligosaccharide, myristic fructooligosaccharide, palmitic fructooligosaccharide, stearic fructooligosaccharide, behenic fructooligosaccharide, (palmitic acid / stearic acid) fructooligosaccharide, and stearic acid / Behenic acid) fructooligosaccharides.

Fructooligosaccharide fatty acid ester is solid at 25 ° C. and has a function of gelling a liquid oil agent.
As a method of synthesizing fructooligosaccharide fatty acid ester by reacting fructooligosaccharide and fatty acid, the same method as that of fructooligosaccharide fatty acid ester as an oil agent described above is used.

  In cosmetics, it is preferable that fructooligosaccharide fatty acid ester as an oil agent is contained in the range of 0.1 mass% or more and 99.8 mass% (hereinafter, wt%) or less. When the amount of fructooligosaccharide fatty acid ester contained as an oil agent is less than 0.1%, the above-mentioned non-sticky feel due to fructooligosaccharide fatty acid ester is not felt by the user, and adhesion to the skin Also lower. Alternatively, when the cosmetic contains at least one of a dextrin fatty acid ester as a gelling agent or film-forming agent and a fructooligosaccharide fatty acid ester as a gelling agent, the fructooligosaccharide fatty acid ester as an oil agent is 0. It is preferably contained in the range of 5 wt% or more and 90 wt% or less.

  In cosmetics, it is preferable that dextrin fatty acid ester as a gelling agent or film forming agent and fructooligosaccharide fatty acid ester as a gelling agent are contained in a total amount of 0.5 wt% or more and 30 wt% or less. When the total amount is less than 0.5%, the viscosity given to the cosmetic becomes so small that the powder contained in the cosmetic cannot sufficiently adhere to the skin, and the cosmetic drips from the skin. It becomes easy to fall. On the other hand, when the total amount exceeds 30%, the viscosity of the cosmetic is increased to such an extent that the sticky feel of the fructooligosaccharide fatty acid ester as an oil agent is not felt by the user, or the viscosity of the cosmetic. However, it becomes so high that it is difficult for the user to spread the paint on the skin.

  Cosmetics include fructooligosaccharide fatty acid esters as oil agents, dextrin fatty acid esters as gelling agents or film forming agents, and fructooligosaccharide fatty acid esters that are oil agents in addition to fructooligosaccharide fatty acid esters as gelling agents. The following substances may be included as long as the effect is obtained. That is, cosmetics include, for example, oils, surfactants, alcohols, water, humectants, emollients, gelling agents and thickeners, powders, ultraviolet absorbers, ultraviolet scattering agents, antiseptics, antibacterial agents. , Antioxidants, skin cleansing ingredients (whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, antiseborrheic agents, etc.), vitamins, amino acids, nucleic acids, hormones, etc. Good.

  The oil agent is not particularly limited and includes solid oil, semi-solid oil, liquid oil, natural animal and vegetable oils and semi-synthetic oil, hydrocarbon oil, ester oil, glyceride oil, silicone oil, higher alcohol, higher fatty acid, Examples include organic solvents.

  Solid oils include natural waxes such as carnauba wax, candelilla wax, cotton wax, shellac wax, hydrogenated oil, mineral waxes such as ozokerite, ceresin, paraffin wax, microcrystalline wax, petrolatum, polyethylene wax, Fischer-Tropsch wax, ethylene Examples include synthetic waxes such as propylene copolymers, higher alcohols such as behenyl alcohol, cetyl alcohol, stearyl alcohol, cholesterol and phytosterol, higher fatty acids such as stearic acid and behenic acid, and the like.

  Liquid oils, including natural animal and vegetable oils and semi-synthetic oils, specifically avocado oil, linseed oil, almond oil, ibotarou, eno oil, olive oil, kaya oil, liver oil, kyounin oil, wheat germ oil, sesame oil, rice germ oil , Rice bran oil, sasanqua oil, safflower oil, cinnamon oil, cinnamon oil, turtle oil, soybean oil, tea seed oil, camellia oil, evening primrose oil, corn oil, rapeseed oil, Japanese kiri oil, nukarou, germ oil, persic oil , Palm oil, palm kernel oil, castor oil, sunflower oil, grape oil, jojoba oil, macadamia nut oil, cottonseed oil, palm oil, tricoconut oil fatty acid glyceride, peanut oil, lanolin, liquid lanolin, reduced lanolin, lanolin alcohol, lanolin acetate, Lanolin Fatty Acid Isopropyl, Polyoxyethylene Lanolin Alcohol Ether, Polyoxyethylene Ethanol Phosphorus alcohol acetate, lanolin fatty acid polyethylene glycol, polyoxyethylene hydrogenated lanolin alcohol ether, yolk oil, and the like.

Examples of the hydrocarbon oil include squalane, squalene, liquid paraffin, pristane, polyisobutylene and the like.
Ester oils include isononyl isononanoate, isotridecyl isononanoate, diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, N-alkylglycol monoisostearate, isocetyl isostearate, triisostearate tris Methylolpropane, cetyl 2-ethylhexanoate, ethylene glycol di-2-ethylhexanoate, neopentyl glycol di-2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, penta-2-ethylhexanoate Erythritol, cetyl octanoate, octyldodecyl gum ester, oleyl oleate, octyldodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate , 2-ethylhexyl succinate, amyl acetate, ethyl acetate, butyl acetate, isocetyl stearate, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, isopropyl palmitate, 2-palmitate Ethylhexyl, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, cholesteryl 12-hydroxystearylate, dipentaerythritol fatty acid ester, isopropyl myristate, 2-octyldecyl myristate, 2-hexyldecyl myristate, myristic acid Myristyl, hexyldecyl dimethyloctanoate, ethyl laurate, hexyl laurate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, malic acid Isostearyl and the like.

  As glyceride oil, acetoglyceride, (caprylic acid / caproic acid) glyceride, triisostearic acid glyceride, triisopalmitic acid glyceride, tri-2-ethylhexanoic acid glyceride, monostearic acid glyceride, di-2-heptylundecanoic acid glyceride And trimyristic acid glyceride.

  Silicone oils include caprylyl methicone, phenyltrimethicone, dimethylpolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, tetramethyltetrahydro. Examples include gencyclotetrasiloxane and alkyl-modified silicone.

Examples of the higher alcohol include oleyl alcohol, lauryl alcohol, stearyl alcohol, isostearyl alcohol, and 2-octyldodecanol.
Examples of higher fatty acids include oleic acid, palmitic acid, myristic acid, stearic acid, and isostearic acid.

  The surfactant is not particularly limited as long as it is usually used in cosmetics, and any surfactant can be used. Examples of the surfactant include an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant. These may be used alone or in combination of two or more as required. be able to.

  Specific examples of anionic surfactants include fatty acid soaps such as sodium stearate and triethanolamine palmitate, alkyl ether carboxylic acids and salts thereof, carboxylates such as condensation of amino acids and fatty acids, alkyl sulfonic acids, and alkene sulfones. Acid salts, sulfonates of fatty acid esters, sulfonates of fatty acid amides, sulfonates of alkyl sulfonates and their formalin condensates, alkyl sulfate esters, secondary higher alcohol sulfates, alkyl and allyl ether sulfates Ester salts, fatty acid ester sulfates, fatty acid alkylolamide sulfates, polyoxyethylene alkyl sulfates, sulfate salts such as funnel oil, alkyl phosphates, ether phosphates, alkyl allyl ether phosphates A Dorin salts, such as N- acylamino acid-based active agents.

  Cationic surfactants include long chain alkyltrimethylammonium salts, dilong chain alkyldimethylammonium salts, long chain alkyldimethylbenzylammonium salts, dipolyoxyethylene alkylmethylammonium salts, dipolyoxyethylene alkyl ether dimethylammonium salts, poly Alkyl quaternary ammonium salts such as oxypropylene methyl diethyl ammonium salt and aromatic quaternary ammonium salts, pyridinium salts such as alkyl pyridinium salts, imidazoline salts such as alkyl dihydroxyethyl imidazoline salts, N-acyl basic amino acid lower alkyl esters And amine salts such as alkylamine salts, polyamines, amino alcohol fatty acid derivatives and the like.

  Nonionic surfactants include sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, polyoxy Ethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene castor oil, polyoxyethylene cured Castor oil, polyoxyethylene hydrogenated castor oil fatty acid ester, polyoxyethylene N-phytostanol ether, polyoxyethylene phytosterol ether, polyoxyethylene cholestanol ether, polyoxyethylene cholesteryl ether, polyoxyalkylene-modified organopolysiloxane, polyoxyalkylene-alkyl co-modified organopolysiloxane, alkanolamide, alkylglycoside, fructo-oligo Examples thereof include sugar fatty acid esters, inulin fatty acid esters, dextrin fatty acid esters and the like.

  Examples of amphoteric surfactants include carbobetaine-type amphoteric surfactants such as alkyldimethylaminoacetic acid betaine, fatty acid amidopropyldimethylaminoacetic acid betaine, alkyldihydroxyethylaminoacetic acid betaine, and sulfobetaine-type amphoteric surfactants such as alkylsulfobetaine, N -Amidoamine type (imidazoline type) amphoteric surfactants such as fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine salt, N-fatty acid acyl-N-carboxymethoxyethyl-N-carboxymethylethylenediamine di-salt, N- [ Amino acid type amphoteric surfactants such as 3-alkyloxy-2-hydroxypropyl] arginine salt, and alkyliminodicarboxylate type amphoteric surfactants.

  Specific examples of alcohols include lower alcohols such as ethanol and isopropanol, glycerin, diglycerin, polyglycerin, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-butylene glycol, and erythritol. Examples thereof include sugar alcohols such as monohydric alcohol, sorbitol, maltose, xylitol and maltitol.

Examples of the humectant include urea, hyaluronic acid, chondroitin sulfate, pyrrolidone carboxylate and the like.
Examples of emollients include natural animal and vegetable oils, fatty acid esters, lanolin and derivatives thereof, higher alcohols, hydrocarbon oils, phospholipids and fatty acids.

  Water-based thickeners and gelling agents include gum arabic, gum tragacanth, galactan, carob gum, guar gum, caraya gum, carrageenan, pectin, agar, quince seed (malmello), starch (rice, corn, potato, wheat), alge colloid, tolanto gum Plant polymers such as locust bean gum, microbial polymers such as xanthan gum, dextran, succinoglucan, pullulan, animal polymers such as collagen, casein, albumin, gelatin, carboxymethyl starch, methylhydroxypropyl starch, etc. Starch-based polymers, methylcellulose, ethylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, nito Cellulose, cellulose sulfate sodium, sodium carboxymethyl cellulose, crystalline cellulose, cellulose-based cellulose polymer, alginic acid-based polymers such as sodium alginate, propylene glycol alginate, polyvinyl methyl ether, carboxyvinyl polymer, alkyl-modified carboxyvinyl polymer, etc. Vinyl polymer, polyoxyethylene polymer, polyoxyethylene polyoxypropylene copolymer polymer, acrylic polymer such as sodium polyacrylate, polyethyl acrylate, polyacrylamide, bentonite, magnesium aluminum silicate, laponite Inorganic thickeners such as hectorite and silicic anhydride, polyethyleneimine, and cationic polymers. Also included are film forming agents such as polyvinyl alcohol and polyvinyl pyrrolidone.

  Examples of oil gelling agents include metal soaps such as aluminum stearate, magnesium stearate, zinc myristate, amino acid derivatives such as N-lauroyl-L-glutamic acid, α, γ-di-n-butylamine, and palmitic acid sucrose esters. And fatty acid sucrose esters such as stearic acid sucrose ester, benzylidene derivatives of sorbitol such as monobenzylidene sorbitol and dibenzylidene sorbitol, and organically modified clay minerals such as dimethylbenzyl dodecyl ammonium montmorillonite clay and dimethyl dioctadecyl ammonium montmorillonite clay.

  Examples of powders include inorganic powders, organic powders, metal soap powders, colored pigments, pearl pigments, metal powders, tar dyes, natural dyes, etc., and their particle shapes (spherical, needle-like, plate-like, etc.) Regardless of particle diameter (smoke, fine particles, pigment grade, etc.) and particle structure (porous, nonporous, etc.), any of them can be used.

  Specific inorganic powders include titanium oxide, zirconium oxide, zinc oxide, cerium oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite , Synthetic mica, phlogopite, saucite, biotite, lithia mica, silicic acid, anhydrous silicic acid, aluminum silicate, magnesium silicate, magnesium aluminum silicate, calcium silicate, barium silicate, strontium silicate, tungstic acid Metal salt, hydroxyapatite, vermiculite, hydrite, bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, alumina, aluminum hydroxide, boron nitride, boron nitride, silica, sodium chloride Potassium, and the like.

  Organic powders include polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane, benzoguanamine powder, polymethylbenzoguanamine powder, tetrafluoroethylene powder, polymethylmethacrylate powder, cellulose powder, silk powder, nylon powder ( 12 nylon, 6 nylon), styrene / acrylic acid copolymer powder, divinylbenzene / styrene copolymer powder, vinyl resin powder, urea resin powder, phenol resin powder, fluororesin powder, silicon resin powder, acrylic resin powder, melamine Resin powder, epoxy resin powder, polycarbonate resin powder, microcrystalline fiber powder powder, comedemp , Lauroyl lysine, hydrophobized starch, surface-treated starch and the like.

  Examples of metal soap powder (surfactant metal salt powder) include zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, zinc cetyl phosphate, calcium cetyl phosphate, and sodium zinc cetyl phosphate. Each powder is mentioned.

  Examples of colored pigments include inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate, inorganic brown pigments such as γ-iron oxide, inorganic yellow pigments such as yellow iron oxide and loess, black iron oxide, carbon black, etc. Lake inorganic black pigments, inorganic purple pigments such as manganese violet and cobalt violet, inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide and cobalt titanate, inorganic blue pigments such as bitumen and ultramarine blue, and tar dyes And those obtained by lacquering natural pigments and composite powders obtained by combining these powders.

  Examples of the pearl pigment include titanium oxide-coated mica, titanium oxide-coated mica, bismuth oxychloride, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, fish scale foil, titanium oxide-coated colored mica, and the metal powder is aluminum. Examples thereof include powder, copper powder, and stainless steel powder.

  The tar pigments are red No. 3, red No. 104, red No. 106, red No. 201, red No. 202, red No. 204, red No. 205, red No. 220, red No. 226, red No. 227, red No. 228 and red 230. No., red 401, red 505, yellow 4, yellow 5, yellow 202, yellow 203, yellow 204, yellow 401, blue 1, blue 2, blue 201, blue 404, Green No. 3, Green No. 201, Green No. 204, Green No. 205, Orange No. 201, Orange No. 203, Orange No. 204, Orange No. 206, Orange No. 207 and the like, and natural pigments include carminic acid, lacaic acid, Examples include calsamine, bradylin, and crocin.

  The above powder may be used as it is, or the powder may be combined and subjected to surface treatment with an oil agent, silicone, fluorine compound, or the like. The said powder can be used 1 type or in combination of 2 or more type as needed.

  As UV absorbers, benzoic acid UV absorbers such as paraaminobenzoic acid, anthranilic acid UV absorbers such as methyl anthranilate, salicylic acid UV absorbers such as methyl salicylate, and cinnamic acids such as octyl paramethoxycinnamate And benzophenone ultraviolet absorbers such as 2,4-dihydroxybenzophenone, and urocanic acid ultraviolet absorbers such as ethyl urocanate.

Examples of the ultraviolet scattering agent include zinc oxide and titanium oxide.
Preservatives and antibacterials include paraoxybenzoates, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, salicylic acid, carboxylic acid, parachlormetacresol, hexachlorophene, benzalkonium chloride, chlorhexidine chloride, trichlorocarba Nilide, photosensitizer, isopropylmethylphenol and the like can be mentioned.

  Tocopherol, butylhydroxyanisole, dibutylhydroxytoluene and the like as antioxidants, and lactic acid, lactate, citric acid, citrate, glycolic acid, succinic acid, tartaric acid, malic acid, potassium carbonate, sodium bicarbonate as pH adjusters , Ammonium bicarbonate, etc., as a chelating agent alanine, sodium edetate, sodium polyphosphate, sodium metaphosphate, phosphate, hydroxyethane diphosphone, etc., as a refreshing agent, L-menthol, camphor, light cargo oil, peppermint oil Examples of anti-inflammatory agents such as eucalyptus oil include allantoin, glycyrrhetinic acid salt, glycyrrhetin derivatives, tranexamic acid, azulene and the like.

  As skin beautifying ingredients, whitening agents such as arbutin, glutathione, and yukinoshita extract, royal jelly, photosensitizer, cholesterol derivatives, cell activators such as calf blood extract, skin roughening agent, nonyl acid wallenyl amide, nicotinic acid benzyl ester, Nicotinic acid β-butoxyethyl ester, capsaicin, gingerone, cantalis tincture, ictamol, caffeine, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandrate, cinnarizine, trazoline, acetylcholine, verapamil, cephalanthin , Blood circulation promoters such as γ-oryzanol, skin astringents such as zinc oxide and tannic acid, and antiseborrheic agents such as sulfur and thianthol.

  Vitamins such as vitamin A oil, retinol, retinol acetate, retinol palmitate, vitamin B2 such as riboflavin, riboflavin butyrate, flavin adenine nucleotide, vitamin B6 such as pyridoxine hydrochloride, pyridoxine dioctanoate Vitamin C such as L-ascorbic acid, L-ascorbic acid dipalmitate, L-ascorbic acid-2-sodium sulfate, dl-α-tocopherol-L-ascorbic acid diester dipotassium, calcium pantothenate, D -Pantothenic alcohols, pantothenyl ethyl ether, pantothenic acids such as acetyl pantothenyl ethyl ether, vitamin Ds such as ergocalciferol, cholecalciferol, nicotinic acid, benzyl nicotinate, Nicotinic acids such as succinic acid amide, dl-α-tocopherol, dl-α-tocopherol acetate, dl-α-tocopherol nicotinate, vitamin E such as dl-α-tocopherol succinate, vitamin P, biotin, etc. .

  Amino acids include arginine, aspartic acid, cystine, cysteine, methionine, serine, leucine, isoleucine, tryptophan, alanine, glycine, proline and the like, nucleic acids such as deoxyribonucleic acid, and hormones such as estradiol and ethinylestradiol.

Examples of phospholipids include lecithin, hydrogenated lecithin, phosphatidylcholines such as dipalmitoyl phosphatidylcholine, and the like.
Examples of ceramides include N-acylated phytosphingosine, N-acylated sphingoid and the like.

[Production example]
[Production Example 1]
76 g of dimethylformamide and 76 g (0.96 mol) of pyridine were added to 32.4 g (0.2 mol in terms of fructose residue) of Bacmondow extract powder (manufactured by Ichimaru Falcos), and the mixture was heated to 60 ° C. The solute was dissolved by heating and stirring the solution. To the solution, 175 g (0.8 mol, 4 times the amount of fructose residue) of lauric acid chloride was added dropwise over 60 minutes, and the solution was stirred for 60 minutes after the addition.

  The reaction solution of fructo-oligosaccharide and fatty acid was added to 200 ml of a mixture of methanol and water in a ratio of 9 to 1, stirred, allowed to stand, and the upper layer was removed by decantation. The operation of adding the reaction solution to a mixture of methanol and water and performing decantation was repeated three times, and then the solution was dried under reduced pressure at 100 ° C., whereby 130 g of fructooligosaccharide that was liquid at 25 ° C. A lauric acid ester (Sample 1) was obtained. When the fatty acid substitution rate in the fructooligosaccharide lauric acid ester was calculated using the ester value and the hydroxyl value, it was found that the substitution rate was 97%.

[Production Example 2]
As fructooligosaccharide, the same operation as in Production Example 1 was performed except that 27 g of chicory-derived fructooligosaccharide having an average molecular weight of about 600 (Roughty Rose P-95, manufactured by Beneo Co., Ltd.) was used and 120 g of caprylic acid chloride was used as the fatty acid. went. As a result, 92 g of fructooligosaccharide capric acid ester (sample 2) derived from chicory that is liquid at 25 ° C. was obtained. When the fatty acid substitution rate in the fructooligosaccharide capric acid ester was calculated using the ester value and the hydroxyl value, it was found that the substitution rate was 100%.

[Production Example 3]
The same procedure as in Production Example 3 was performed, except that 34 g of fructooligosaccharide having an average molecular weight of about 2600, 60 g of capric acid chloride, and 160 g of isopalmitic acid chloride were used. As a result, 150 g of fructooligosaccharide (capric acid / isopalmitic acid) ester (sample 3) which was liquid at 25 ° C. was obtained. When the substitution rate of the fatty acid in the fructooligosaccharide (capric acid / isopalmitic acid) ester was calculated using the ester value and the hydroxyl value, it was found to be 100%.

[Production Example 4]
The same operation as in Production Example 1 was performed except that 34 g of Mayoligo P (manufactured by Meiji Co., Ltd.) was used as the fructooligosaccharide and 100 g of isononanoic acid chloride was used as the fatty acid. As a result, 34 g of fructooligosaccharide isononanoic acid ester (sample 4) that was liquid at 25 ° C. was obtained. When the substitution rate of the fatty acid in the fructooligosaccharide isononanoic acid ester was calculated using the ester value and the hydroxyl value, it was found to be 75%.

[Production Example 5]
Inulin was dissolved by adding 100 g of 3-methylpyridine to 22 g of inulin derived from chicory having an average molecular weight of about 2400 and stirring at 50 ° C. 140 g of isostearic acid chloride was added dropwise to the inulin solution over 20 minutes, and the solution was stirred for 2 hours after the addition. The reaction solution of fructooligosaccharide and fatty acid was added to a 300 ml solution in which methanol and water were mixed 1: 1, stirred, allowed to stand, and the upper layer was removed by decantation. The operation of adding the reaction solution to a mixed solution of methanol and water and performing decantation was repeated three times, and then the solution was dried under reduced pressure at 100 ° C., whereby 110 g of inulin isostearin liquid at 25 ° C. An acid ester (sample 5) was obtained. When the substitution rate of fatty acid in inulin isostearate was calculated from the ester value and the hydroxyl value, it was found to be 85%.

[Example]
[Example 1 Fructooligosaccharide fatty acid ester]
About the above-mentioned sample 1 to sample 5, 20 people's monitor evaluated the non-stickiness when it applied to skin which is two items, and adhesiveness. Evaluation was made into five grades of good (5 points), good (4 points), normal (3 points), slightly bad (2 points), and bad (1 point), and the average score of each item was calculated.

  As shown in Table 1, in samples 1 to 3, it was recognized that the monitor was the least sticky and the adhesion to the skin was the highest. In contrast, Sample 3 and Sample 4 were found to be sticky on the monitor as compared to Sample 1 to Sample 3, although the adhesion to the skin was good. That is, as shown in Table 1, it is recognized that the higher the substitution rate of fatty acids per molecule of fructo-oligosaccharide, the less the stickiness and the better the adhesion, especially when the substitution rate is 95% or more. It was.

[Example 2 O / W cream]
Using the sample 2 described above, an O / W cream was prepared by the following method and the formulation shown below. When preparing the O / W cream, first, the components (1) to (11), which are oil phase components, were mixed and heated to 90 ° C. to prepare a mixed solution. And it mixed and emulsified with the component (15) from the component (12) which is the water phase component which mixed with the liquid mixture previously, and melt | dissolved by heating. Next, the premixed component (16) and component (17) were added and mixed uniformly.

Ingredient wt%
(1) Sample 2 5.0
(2) Squalane 7.0
(3) Jojoba oil 3.0
(4) Ethylhexyl palmitate 5.0
(5) Stearic acid 0.5
(6) Behenyl alcohol 2.2
(7) Glyceryl stearate (SE) 1.1
(8) Sorbitan sesquiisostearate 0.5
(9) Polyglyceryl stearate-10 1.2
(10) Dimethicone 0.1
(11) Tocopherol 0.1
(12) Butylene glycol 8.0
(13) Glycerin 8.0
(14) 1 wt% sodium hydroxide aqueous solution 9.0
(15) Water 31.3
(16) 1 wt% carboxyvinyl polymer aqueous solution 16.0
(17) 2 wt% xanthan gum aqueous solution 2.0
[Example 3 Lipstick]
Using the sample 3 described above, a lipstick was prepared by the following method and the formulation shown below. When making the lipstick, the components (1) to (10) were mixed and dissolved by heating the mixture to 90 ° C. And the solid lipstick was obtained by cooling a liquid mixture.

Ingredient wt%
(1) Sample 4 30.0
(2) Diisostearyl malate 2.0
(3) Tri (caprylic / capric) glyceryl 26.0
(4) Diphenyl dimethicone 3.0
(5) Hexa (hydroxystearic acid / stearic acid / rosin acid)
Dipentaerythrityl 15.0
(6) Candelilla wax 3.0
(7) Polyethylene wax 2.0
(8) Microcrystalline wax 4.0
(9) Ceresin 7.0
(10) Color material base 8.0
Example 4 Eye Shadow
Using the sample 1 described above, an eye shadow was prepared by the following method and the formulation shown below. When preparing an eye shadow, the component (1) to the component (4) were mixed to prepare a mixed solution 1. On the other hand, a mixture 2 was prepared by previously mixing the components (5) to (9). After the mixture 2 was added to the mixture 1 and mixed, a solid eye shadow was obtained by compression molding.

Ingredient wt%
(1) Sample 1 6.0
(2) Isotridecyl isononanoate 1.0
(3) Diphenyl dimethicone 1.0
(4) Sorbitan sesquioleate 2.0
(5) Talc 45.0
(6) Mica 15.0
(7) Sericite 5.0
(8) Pigment 15.0
(9) Pearl pigment 10.0
[Example 5 beauty oil]
Using the sample 1 and sample 2 described above, beauty oil was prepared by the following method and the formulation shown below. When preparing the beauty oil, components (1) to (3) were mixed uniformly.

Ingredient wt%
(1) Sample 1 38.0
(2) Sample 2 60.0
(3) Ascorbyl tetrahexyldecanoate 2.0
In the cosmetic oil of Example 5, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.1 wt% to 99.8 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.1 wt%, the stickiness due to the fructooligosaccharide fatty acid ester and the good adhesion to the skin cannot be obtained. On the other hand, when the content of fructooligosaccharide fatty acid ester exceeds 99.8 wt%, the blending amount of, for example, ascorbyl tetrahexyldecanoate, which is a cosmetic ingredient, is decreased by the amount of blending of fructooligosaccharide fatty acid ester.

  In addition, according to Example 2 to Example 5, there is less stickiness compared to the case where a fructooligosaccharide fatty acid ester having a substitution rate of fatty acid per molecule of fructooligosaccharide of less than 95% is used as the component (1). It was recognized that it was excellent in performance.

[Example 6 Fructooligosaccharide fatty acid ester composition]
Composition 1 to Composition 5 were prepared by mixing the above-mentioned Sample 1 to Sample 5, liquid paraffin as an oil agent, and dextrin palmitate as one of dextrin fatty acid esters as a gelling agent at the following ratios. . Moreover, the comparative example 1 which does not contain a sample and the comparative example 2 which does not contain a palmitic acid dextrin were created as a comparative example. Then, the following items when each composition and each comparative example were applied to the skin were evaluated by a monitor of 20 people, and the average value of each item was calculated.

[Composition 1 to Composition 5]
-Sample 1 to sample 5 30 wt%
・ Liquid paraffin 66wt%
・ Dextrin palmitate 4wt%
[Comparative Example 1]
・ Liquid paraffin 96wt%
・ Dextrin palmitate 4wt%
[Comparative Example 2]
・ Sample 1 30wt%
・ Liquid paraffin 70wt%
The items evaluated were not dripping from the finger when applied to the skin or when applied to the skin, and ease of application (A) as ease of spreading on the skin, use as a feel when applied These are three items: good feeling (B) and adhesion to the skin (C) as a touch that soaks into the skin. Evaluation for each item was made into five grades: good (5 points), slightly good (4 points), normal (3 points), slightly bad (2 points), and bad (1 point). And, when the average score of each item exceeds 4.5 points, “◎” indicates that it is very good, and the case where it exceeds 3.5 points and is 4.5 points or less is good. It was shown as “◯”. The case where the average score was more than 1 point and 3.5 points or less was indicated as “Δ” indicating a little failure, and the case where the average score was 1 point or less was indicated as “X” indicating a failure.

  The results of evaluation of Composition 1 to Composition 5, Comparative Example 1 and Comparative Example 2 are shown in Table 2 below.

  As shown in Table 2, it was confirmed that Comparative Example 1 not containing a sample was gel-like due to the function of dextrin palmitate, so that the ease of application (A) was good. According to the composition 1 to the composition 5 including any one of the samples 1 to 5, the usability (B) and the adhesion to the skin (C) are enhanced as compared with the comparative example 1. Was recognized. Moreover, compared with the comparative example 2 which does not contain dextrin palmitate, the composition 1 to the composition 5 containing dextrin palmitate are easy to apply (A), feeling of use (B), and adhesion to the skin ( It was observed that all of C) was enhanced.

[Example 7: Liquid lipstick]
A liquid lipstick containing any one of Sample 2, Sample 3 and Sample 5 described above and dextrin isostearate as a film forming agent or stearic acid fructooligosaccharide as a gelling agent was prepared. Further, as Comparative Example 3, a liquid lipstick containing diisostearyl malate as an oil and dextrin isostearate as a film forming agent was prepared. It should be noted that both the examples and the comparative examples are oil agents such as components (8) and (9) shown in Table 3 and powders such as components (10) shown in Table 3 ( 13) the pigment.

  About the liquid lipstick of an Example and the liquid lipstick of a comparative example, the following four items were evaluated by the method similar to Example 2 mentioned above. That is, the adhesion to the lips (A) and the non-stickiness (B) indicating no stickiness when the upper and lower lips were put together were evaluated. In addition, it is evaluated that there is no feeling of tightness over time indicating that the lips do not feel tight over time (C), and that there is no peeling due to sticking of liquid lipstick, for example, a cup, etc. (D) did.

  The liquid lipstick was prepared by the following method. That is, by mixing any of the components (5) to (7) that are gelling agents with the component (8) that is an oil agent, and heating the mixture to 90 ° C., the components (5) to ( Any one of 7) was dissolved. Then, any one of the components (1) to (4) as an oil agent, the component (9) as an oil agent, the components (10) to (12) as a powder, and a pre-mixed with the solution Then, component (13), which was a pulverized powder, was added and mixed uniformly.

  The evaluation results for the liquid lipstick of the example and the liquid lipstick of the comparative example are shown in Table 3 below.

  As shown in Table 3, according to the liquid lipstick of the example using fructooligosaccharide fatty acid ester as the oil agent, the stickiness of the liquid lipstick is higher than that of the liquid lipstick of the comparative example using diisostearyl malate as the oil agent. It was found to be suppressed. In addition, among the examples, it was recognized that the effect of suppressing stickiness was highest for liquid lipstick 1 and liquid lipstick 2, and lowest for liquid lipstick 3. Furthermore, according to the liquid lipstick of the example, it was confirmed that the adhesion to the lips, and thus the difficulty of peeling off of the liquid lipstick, was enhanced as compared with the liquid lipstick of the comparative example.

  In the liquid lipstick, it is preferable that fructooligosaccharide fatty acid ester is contained in a range of 0.5 mass% to 90 mass%. When the content of the fructo-oligosaccharide fatty acid ester is less than 0.5 wt%, it is difficult to obtain a feeling of close contact with the lips, and thus adhesion to the lips. On the other hand, when the content exceeds 90 wt%, even if isodecane, which is a volatile oil, volatilizes, the content of the fructooligosaccharide fatty acid ester is large, so that the adhesion of the components remaining on the lips is increased. As a result, it becomes difficult to obtain stability over time.

  In the liquid lipstick, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester as a gelling agent or film forming agent is preferably 0.5 wt% or more and 20 wt% or less. When the total amount of the gelling agent is less than 0.5 wt%, the liquid lipstick is insufficiently gelled, so that the state applied to the lips is not easily maintained. On the other hand, when the total amount of the gelling agent exceeds 20 wt%, the viscosity of the liquid lipstick becomes high, so that irregularities are easily formed on the liquid lipstick film formed on the lips.

Example 8 Lip Gloss
Using the sample 2 described above, a lip gloss was prepared by the following method and the formulation shown below. When preparing the lip gloss, first, component (2), component (3), and a part of component (1) are mixed and heated to 90 ° C., and components (1) and (2) that are oil agents are mixed. Ingredient (3) was dissolved. And the remainder of component (1), component (4), and component (5) were added and mixed with respect to the liquid mixture of component (1) to component (3).

Ingredient wt%
(1) Sample 2 70.0
(2) Dextrin myristate 10.0
(3) Isonyl isononanoate 7.0
(4) Hydrogenated polyisobutene 12.0
(5) Color material 1.0
According to the lip gloss of Example 8, it was confirmed that stickiness was suppressed as compared with the case where diisostearyl malate was used as the oil agent. In addition, since dextrin fatty acid ester is used as a gelling agent, compared to the case of using fructooligosaccharide fatty acid ester as a gelling agent, it is possible to suppress the lip gloss from becoming cloudy and to increase the transparency. As a result, it was confirmed that the gloss when applied to the lipstick was also enhanced.

  In lip gloss, it is preferable that fructooligosaccharide fatty acid ester as an oil agent is contained in a range of 0.5% to 90%. When the content of fructooligosaccharide fatty acid ester is less than 0.5 wt%, the stickiness of fructooligosaccharide fatty acid ester is superior to the stickiness of fructooligosaccharide fatty acid ester, etc. It is done.

  Here, since fructooligosaccharide fatty acid ester also has a function of imparting gloss to lip gloss, it is possible to suppress stickiness while maintaining the gloss of lip gloss by using fructooligosaccharide fatty acid ester instead of hydrogenated polyisobutene. it can. However, since the effect of imparting gloss to lip gloss is higher with hydrogenated polyisobutene than with fructooligosaccharide fatty acid ester, fructooligosaccharide fatty acid ester can be suppressed to 90 wt% or less in order to maintain the gloss of lip gloss. preferable.

  That is, when the content of fructo-oligosaccharide fatty acid ester exceeds 90 wt%, the amount of hydrogenated polyisobutene that is an oil agent is reduced by that amount, and it is difficult to obtain gloss due to hydrogenated polyisobutene.

  In lip gloss, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester as a gelling agent is preferably 0.5 wt% or more and 20 wt% or less. When the total amount of the gelling agent is less than 0.5 wt%, the viscosity of the lip gloss is lowered to such an extent that the gelling agent drops off from the lips. On the other hand, when the total amount of the gelling agent exceeds 20 wt%, Due to the high gloss viscosity, it is difficult for the user to apply to the lips.

[Example 9 oil-based cleansing oil gel]
Using sample 3 described above, an oily cleansing oil gel was prepared by the following method and the formulation shown below. When preparing an oil-based cleansing oil gel, first, the components (2) to (5) were mixed, and the mixture was dissolved by heating to 90 ° C. And a component (1), a component (6), and a component (7) were added to the liquid mixture, and these were mixed uniformly. Next, the component (8) was added to the mixed solution of the component (1) to the component (7) little by little with stirring, and the mixed solution of the component (1) to the component (8) was cooled to room temperature with stirring.

Ingredient wt%
(1) Sample 3 2.0
(2) (palmitic acid / ethylhexanoic acid) dextrin 3.0
(3) Isotridecyl isononanoate 8.0
(4) Cetyl ethylhexanoate 51.0
(5) Ethylhexyl palmitate 10.0
(6) Polyglyceryl-10 dioleate-10 14.0
(7) Polyglyceryl-2 sesquicaprylate 6.0
(8) Water 6.0
According to the oil-based cleansing oil gel of Example 9, compared to the case where mineral oil is used as the oil agent, when applied to the skin by the user, it has a non-sticky feel, that is, a moist feel and good sliding. Allowed to be given to the user. Moreover, since the viscosity was provided by the ester (palmitic acid / ethylhexanoic acid) which is a gelatinizer, it was also recognized that the usability was good as compared with the configuration not including the gelator.

  Since oil-based cleansing oil gel is required to have a function of removing cosmetics, surfactants for peeling cosmetics from the skin, and for dissolving cosmetics in reacting surfactants with cosmetics It is necessary that an oil is included. For example, in the above formulation examples, component (6) and component (7) are surfactants, and components (3) to (5) are oil agents.

  In addition, with an oil-based cleansing oil gel, when the user moves his / her finger on the skin with the oil-based cleansing oil gel applied to the skin, the moist feel and slip as described above are given to the user. It is preferable to give a good feel.

  In this respect, the oil-based cleansing oil gel preferably contains fructooligosaccharide fatty acid ester as an oil agent in a range of 0.5 wt% to 90 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, it is difficult to obtain a touch due to the fructooligosaccharide fatty acid ester. On the other hand, when the content exceeds 90 wt%, the amount of the oil agent that dissolves the surfactant and the cosmetic is reduced by that amount, and the detergency of the oil-based cleansing oil gel tends to be lowered.

  Moreover, in the oil-based cleansing oil gel, it is preferable that the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester as a gelling agent is contained in the range of 0.5 wt% to 30 wt%. By including the gelling agent in such a range, when the oily cleansing oil gel is applied to the skin, the oily cleansing oil gel can be prevented from dripping from the skin. On the other hand, when the total amount of the gelling agent exceeds 30 wt%, the viscosity of the oil-based cleansing oil gel becomes high enough to make it difficult to apply the oil-based cleansing oil gel to the skin.

[Example 10 Lipstick]
Using the sample 4 described above, a lipstick was prepared by the following method and the formulation shown below. When preparing a lipstick, first, component (2) to component (8) are mixed, the mixture is dissolved by heating to 90 ° C., and then component (1), component (9), and component (10) are prepared. Was added. And the liquid mixture which mixed the component (10) uniformly from the component (1) was created, and solid lipstick was obtained by cooling a liquid mixture.

Ingredient wt%
(1) Sample 4 30.0
(2) Dextrin isostearate 10.0
(3) Inulin stearate 7.0
(4) Tri (capryl / capric acid) glyceryl 10.0
(5) Jojoba oil 10.0
(6) Neopentyl glycol dicaprate 10.0
(7) Candelilla Row 9.0
(8) Carnauba wax 4.0
(9) Color material base 8.0
(10) Pearl agent 2.0
It was recognized that the lipstick of Example 10 is not sticky, that is, gives a light touch to the user as compared with the case of using diisostearyl malate as an oil agent. In addition, the lipstick of Example 10 was found to give a moist feel when applied to the lips because the adhesion to the lips was enhanced.

  In lipstick, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.5 wt% to 80 wt%. When the fructo-oligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the lips are difficult to obtain.

  The lipstick contains, for example, waxes such as the above component (7) and component (8), so that the lipstick is kept solid, and the higher the hardness of the lipstick, the more easily the shape of the lipstick is maintained. In order to disperse powders, for example, pigments such as the above component (9) and component (10), in the lipstick, for example, the component (4) to the component (6), etc. Thus, it is preferable that the oil agent with high compatibility with a wax is contained.

  Here, the present inventors have found that fructooligosaccharide fatty acid ester has a function of increasing the hardness of a mixed oil when added to a mixed oil of a wax and an oil agent having high compatibility with the wax. It was. Therefore, by using fructooligosaccharide fatty acid ester as an oil agent, it is possible to maintain the hardness of lipstick while increasing the gloss of lipstick by reducing the amount of wax that lowers the gloss of lipstick compared to fructooligosaccharide fatty acid ester. . However, since the effect of increasing the hardness of the lipstick is higher in the wax than in the fructooligosaccharide fatty acid ester, the fructooligosaccharide fatty acid ester is preferably suppressed to 80 wt% or less in order to maintain the hardness of the lipstick.

  When the fructooligosaccharide fatty acid ester exceeds 80 wt%, it is necessary to reduce the amount of at least one of the wax for maintaining the shape of the lipstick or the oil agent having high compatibility with the wax. Therefore, it is difficult to maintain the shape of the lipstick, and the dispersibility of the pigment is lowered, so that the color development property of the lipstick is lowered. Even if the amount of the wax and the oil agent is not reduced, the amount of the pigment for coloring the lipstick has to be reduced, so that the color of the lipstick is lowered.

  In lipstick, it is preferable that the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester as a gelling agent is contained in the range of 0.5 wt% or more and 30 wt% or less. When the total amount of the gelling agent is within the above range, the viscosity of the lipstick is increased by the gelling agent, so that it easily adheres to the lips. In addition, since the pigment is more uniformly dispersed in the lipstick by the function of dispersing the pigment contained in the gelling agent, the gloss and color development of the lipstick are enhanced. On the other hand, when the total amount of the gelling agent exceeds 30 wt%, the viscosity of the lipstick becomes so high that the user feels stickiness.

[Example 11 powder foundation]
Using the sample 5 described above, a powder foundation was prepared by the following method and the formulation shown below. When preparing the powder foundation, first, the component (2) to the component (4) were mixed, and the mixture was dissolved by heating to 90 ° C. Then, the component (1), the component (5), and the component (6) previously mixed and pulverized to the component (12) were added to the mixture and cooled, and then the solid mixture was pulverized with a mill. By applying pressure to the powder obtained by the mill using a press, a pellet-shaped powder foundation was obtained.

Ingredient wt%
(1) Sample 5 1.0
(2) Squalane 3.0
(3) Vaseline 1.0
(4) (palmitic acid / stearic acid) dextrin 1.0
(5) (Dimethicone / Vinyl Dimethicone) Crosspolymer 4.0
(6) Starch aluminum octenyl succinate 9.0
(7) Sericite 28.8
(8) Barium sulfate 6.0
(9) Silicone-treated pigment 10.7
(10) Silicone-treated talc 30.0
(11) Boron nitride 4.0
(12) Zinc myristate 1.5
It was recognized that the powder foundation of Example 11 did not make the user feel sticky when applied to the skin even though the adhesion to the skin was enhanced compared to the case where squalane was used as the oil. It was. Moreover, according to the powder foundation of Example 7, compared with the case where Squalane is also used, when the powder foundation is applied to the skin, the user feels a rich touch that is a comfortable weight. It was also recognized.

  In the powder foundation, it is preferable that fructooligosaccharide fatty acid ester as an oil agent is contained in a range of 0.5 wt% to 10 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. On the other hand, when the content of the fructooligosaccharide fatty acid ester exceeds 10 wt%, the powder foundation is not a solid powder but a liquid with a high viscosity, so that the components (6) to (12 ) It is difficult to give the user a smooth feel.

  In the powder foundation, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably 0.5 wt% or more and 5 wt% or less. When the total amount of the gelling agent is less than 0.5 wt%, the powder foundation is less likely to adhere to the skin as compared with the case where it is 0.5 wt% or more. When the total amount of the gelling agent exceeds 5 wt%, the powder foundation tends to give the user a sticky feeling when applied to the skin, compared to the case where the gelling agent is 5 wt% or less. .

[Example 12: Oily foundation]
Using the above sample 5, an oily foundation was prepared by the following method and the formulation shown below. When preparing the oily foundation, first, the components (2) to (4) were mixed, and the mixture was dissolved by heating to 90 ° C. And after adding component (1) and component (5) to component (8) to the mixture and cooling, the solid mixture was pulverized by a mill. After the pulverized mixture was heated to 80 ° C., the mixture was filled in a container to obtain an oily foundation.

Ingredient wt%
(1) Sample 5 20.0
(2) Inulin stearate 1.5
(3) Dextrin palmitate 4.5
(4) Diphenylsiloxyphenyl trimethicone 31.0
(5) Kaolin 10.7
(6) (Vinyl dimethicone / methicone silsesquioxane) cross polymer 10.0
(7) Titanium oxide 20.0
(8) Iron oxide, red, yellow, black 2.3
The oily foundation of Example 12 feels sticky to the user when applied to the skin, although the adhesion to the skin is enhanced compared to the case where diphenylsiloxyphenyl trimethicone is used as the oil agent. It was admitted not to let it. In addition, according to the oily foundation of Example 8, it was also recognized that the user was given a rich feel as compared with the case of using diphenylsiloxyphenyl trimethicone.

  In the oily foundation, it is preferable that fructooligosaccharide fatty acid ester as an oil agent is contained in a range of 0.5 wt% to 80 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, it becomes difficult to obtain the non-stickiness obtained from the fructooligosaccharide fatty acid ester and the feeling of adhesion to the skin. When the content of the fructooligosaccharide fatty acid ester exceeds 80 wt%, the components (5) to (8) which are powders are not blended in an amount sufficient to cause color development.

  In the oily foundation, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably included in the range of 1.0 wt% to 30 wt%. When the total amount of the gelling agent is less than 1.0 wt%, the oily foundation hardly adheres to the skin. When the total amount of the gelling agent exceeds 30 wt%, the viscosity of the oily foundation becomes so high that it becomes difficult to use.

[Example 13 O / W emulsified foundation]
Using the sample 4 described above, an O / W emulsified foundation was prepared by the following method and the formulation shown below. When preparing an O / W emulsified foundation, first, the components (1) to (11) that are oil phase components are mixed and heated to 90 ° C., and the components (12 ) To component (16) and a part of component (17) which is an aqueous phase component were added and emulsified. Subsequently, the remainder of (17) and (18) to (21) previously mixed were added to the emulsion and mixed uniformly.

Ingredient wt%
(1) Sample 4 8.0
(2) Dextrin palmitate 1.0
(3) Dextrin isostearate 0.5
(4) Stearic acid 1.0
(5) Glyceryl stearate 0.5
(6) Behenyl alcohol 1.0
(7) Polysorbate 80 0.8
(8) Sorbitan sesquiisostearate 0.5
(9) Squalane 3.0
(10) Tri (capryl / capric acid) glyceryl 5.3
(11) Jojoba oil 3.0
(12) Butylene glycol 15.0
(13) Glycerin 3.0
(14) Sodium hydroxide 0.1
(15) Carboxyvinyl polymer 0.1
(16) Xanthan gum 0.02
(17) Water 43.28
(18) Hydrogenated lecithin 1.6
(19) Titanium oxide 6.0
(20) Iron oxide 1.3
(21) Mica 5.0
According to the O / W emulsified foundation of Example 13, it was confirmed that the adhesion to the skin was enhanced while suppressing stickiness as compared with the case where mineral oil was used as the oil agent.

  In addition, it is preferable that fructooligosaccharide fatty acid ester is contained in 0.5 to 50 wt% in the O / W emulsion type foundation. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. When the content of fructo-oligosaccharide fatty acid ester exceeds 50 wt%, the proportion of oil is increased by decreasing the amount of water as much as the amount of oil is increased. The viscosity becomes so high that it is difficult to apply to the skin.

  In the O / W emulsified foundation, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably included in the range of 0.5 wt% to 20 wt%. When the total amount of the gelling agent is less than 0.5 wt%, the O / W emulsified foundation hardly adheres to the skin. When the total amount of the gelling agent exceeds 20 wt%, the viscosity of the O / W emulsified foundation becomes high enough to be difficult to apply to the skin.

[Example 14 W / O emulsified foundation]
Using the sample 1 described above, a W / O emulsified foundation was prepared by the following method and the formulation shown below. When preparing a W / O emulsified foundation, first, the components (1) to (3), a part of the component (4), and the component (5) are mixed and mixed by heating to dissolve. A liquid was created. The components (10) to (12) dissolved in advance by heating were added to the mixed solution, and the solution was emulsified by stirring with a homomixer. After the emulsion was cooled, the remainder of component (4) mixed in advance and component (6) to component (9) were added to the emulsion.

Ingredient wt%
(1) Sample 1 2.0
(2) (palmitic acid / ethylhexanoic acid) dextrin 2.0
(3) Isotridecyl isononanoate 3.0
(4) Cyclomethicone 15.0
(5) Dimethicone copolyol 2.0
(6) Silicone-treated mica 10.0
(7) Silicone-treated titanium oxide 8.0
(8) Silicone-treated iron oxide 2.3
(9) Polymethyl methacrylate 8.0
(10) Sodium chloride 1.0
(11) Butylene glycol 7.0
(12) Water 39.7
According to the W / O emulsified foundation of Example 14, it was confirmed that the adhesion to the skin was enhanced while suppressing stickiness as compared with the case where diisostearyl malate was used as the oil agent.

  In the W / O emulsification type foundation, it is preferable that fructooligosaccharide fatty acid ester as an oil agent is contained in a range of 0.5 wt% to 50 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. When the content of fructooligosaccharide fatty acid ester exceeds 50 wt%, the blending amount of water is reduced by the amount of fructooligosaccharide fatty acid ester blending, so the viscosity of the W / O emulsified foundation is difficult to use. It becomes so high. In addition, the component (1), component (3), which is an oil phase component, and the proportion of the component (9) to the component (9), which is a powder, with respect to the component (4) are reduced, so that the W / O emulsion foundation The amount of powder per coating amount is reduced.

  In the W / O emulsified foundation, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably included in the range of 0.5 wt% to 20 wt%. When the total amount of the gelling agent is less than 0.5 wt%, the W / O emulsified foundation hardly adheres to the skin. When the total amount of the gelling agent exceeds 20 wt%, the viscosity of the W / O emulsified foundation becomes high enough to make it difficult to use.

[Example 15 cream eyeliner]
Using the sample 1 described above, a cream eyeliner was prepared by the following method and the formulation shown below. When preparing the cream eyeliner, first, the components (2) to (5) were mixed, and the mixture was dissolved by heating to 90 ° C. And the component (1) and the component (6) and the component (7) which were mixed beforehand and grind | pulverized were added with respect to the liquid mixture, and it mixed uniformly.

Ingredient wt%
(1) Sample 1 8.0
(2) Dextrin palmitate 8.0
(3) Dextrin isostearate 3.0
(4) Hydrogenated rosin acid pentaerythrityl octyldodecyl isostearate 6.0
(5) Dodecane 27.0
(6) Black iron oxide 27.0
(7) Mica 21.0
According to the cream eyeliner of Example 15, it was confirmed that the adhesion to the skin was enhanced as compared with the case where diisostearyl malate was used as the oil agent. Furthermore, according to the cream eyeliner of Example 15, it was recognized that the ease of drawing when the user drew a line on the edge of the bag was enhanced due to high adhesion.

  In addition, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.5 wt% or more and 50 wt% or less in the cream eyeliner. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained from the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. When the content of the fructooligosaccharide fatty acid ester exceeds 50 wt%, the ratio of the component (6) and the component (7) that are powders to the component (1) and the component (5) that are oil phase components is small. , The adhesion to the skin is deteriorated, that is, the coloring component is hardly attached.

  In the cream eyeliner, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester as gelling agents is preferably included in the range of 0.5 wt% to 20 wt%. When the total amount of the gelling agent is less than 0.5 wt%, the cream eyeliner becomes difficult to adhere to the skin. When the total amount of the gelling agent exceeds 20 wt%, the viscosity of the cream eyeliner becomes so high that it becomes difficult to use.

Example 16 Mascara
Using sample 2 described above, a mascara was prepared by the following method and the formulation shown below. When preparing the mascara, first, the component (1) to the component (10) were heated and dissolved uniformly to prepare the mixed solution 1. And after adding the component (11) to the component (13) to the mixed solution 1, the mixed solution 1 was stirred with a disper. Mascara was obtained by cooling the liquid mixture 1 to room temperature.

Ingredient wt%
(1) Sample 2 1.0
(2) Dextrin palmitate 10.0
(3) Polyethylene 5.0
(4) Microcrystalline wax 1.0
(5) Candelilla wax 1.0
(6) Isododecane 47.95
(7) Dextrin isostearate 6.0
(8) Tocopherol 0.05
(9) Trimethylsiloxysilicic acid 8.0
(10) Quotanium-18 bentonite 5.0
(11) Iron oxide 5.0
(12) Talc 6.0
(13) Nylon-12 4.0
According to the mascara of Example 16, as compared with the case where diisostearyl malate is used as the oil agent, the mascara hardness can be increased while reducing the amount of wax, so that the component (13) which is a fiber is easily dispersed. It was recognized that In addition, since the dispersibility of the fiber is high, when the user applies mascara to the cocoons, the cocoons are not easily attached to each other by the mascara, and as a result, the adjacent cocoons are separated from each other, and the mascara It was recognized that it was easy to spread along the eyelashes and it was difficult to form a lump. That is, it was recognized that the finish was improved.

  In mascara, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.5 wt% to 50 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. When the content of fructooligosaccharide fatty acid ester exceeds 50 wt%, the blending amount of fructooligosaccharide fatty acid ester increases, so the blending amount of isododecane, which is a volatile oil agent, and the blending amount of other components decrease. Therefore, it becomes difficult for the mascara to dry, and the eyelashes tend to stick to each other.

  In mascara, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester, which are gelling agents, is preferably included in the range of 0.5 wt% to 20 wt%. When the total amount of the gelling agent is less than 0.5 wt%, the mascara is difficult to adhere to the eyelashes. When the total amount of the gelling agent exceeds 20 wt%, the viscosity of the mascara becomes so high that it becomes difficult to use.

Example 17 Eye Shadow
Using the sample 5 described above, an eye shadow was prepared by the following method and the formulation shown below. When preparing an eye shadow, first, component (6) to component (13) are mixed and pulverized in a mill, while component (1) to component (5) are mixed and the mixture is heated to 90 ° C. Dissolved by. And the powder of the component (6) to the component (13) was added to the mixed solution, and the component (14) was added to the mixed solution and mixed uniformly. Next, these mixed liquids were dried at 70 ° C. for 4 hours or more, and then the solids were pulverized by a mill. Finally, the powder obtained by the mill was pressed with a press to obtain a pellet-shaped eye shadow.

Ingredient wt%
(1) Sample 5 2.0
(2) Squalane 4.0
(3) Vaseline 1.8
(4) Dextrin isostearate 2.0
(5) Dextrin myristate 0.2
(6) Starch aluminum octenyl succinate 10.0
(7) Mica 20.0
(8) Talc 20.0
(9) Pearl agent 20.0
(10) Colored mica 10.0
(11) Polymethyl methacrylate 7.0
(12) Titanium oxide 2.0
(13) Iron oxide 1.0
(14) Isoparaffin 40.0
According to the eye shadow of Example 17, compared to the case of using diisostearyl malate as an oil agent, the adhesion to the skin is enhanced and the peeling from the skin is suppressed, that is, the makeup is good. Was recognized.

  In addition, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.5 wt% or more and 50 wt% or less in eye shadow. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, the non-stickiness obtained by the fructooligosaccharide fatty acid ester and the adhesion to the skin are difficult to obtain. When the content of fructooligosaccharide fatty acid ester exceeds 50 wt%, the amount of fructooligosaccharide fatty acid ester is increased, so that the amount of isoparaffin, which is a volatile oil agent, and other components, especially powder Since the blending amount of the component (6) to the component (13) is reduced, the eye shadow is difficult to dry. As a result, the eye shadow applied to the skin is easily rubbed and removed from the skin, or it is easy to bleed on the skin.

  In the eye shadow, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably included in the range of 0.5 wt% or more and 20 wt% or less. When the total amount of the gelling agent is less than 0.5 wt%, the eye shadow is difficult to adhere to the skin. When the total amount of the gelling agent exceeds 20 wt%, the eye shadow becomes hard enough to be difficult to use.

Example 18 Sunscreen Balm
Using the sample 2 described above, a sunscreen balm was prepared by the following method and the formulation shown below. When preparing a sunscreen balm, first, a mixture of component (2) to component (4) is dissolved by heating to 90 ° C., and then component (1) and component (5) to component (8) are combined. In addition to the mixture, it was mixed uniformly. And in the state which heated the liquid mixture at 75 degreeC, the component (11) from the component (9) mixed previously was added, and these were emulsified using the homomixer.

Ingredient wt%
(1) Sample 2 5.0
(2) Dextrin palmitate 2.0
(3) Inulin stearate 8.0
(4) Squalane 7.0
(5) (Vinyl dimethicone / methicone silsesquioxane) cross polymer 2.0
(6) Zinc oxide 10.0
(7) PEG-10 dimethicone 1.5
(8) Cyclopentasiloxane 24.0
(9) 1,3-butylene glycol 4.0
(10) Glycerin 5.5
(11) Water 31.0
According to the sunscreen balm of Example 18, compared to the case of using diisostearyl malate as an oil agent, the adhesion to the skin was enhanced, and when applied to the skin, there was no stickiness and was smooth. It was allowed to give the user a feel.

  In the sunscreen balm, the fructooligosaccharide fatty acid ester is preferably contained in the range of 0.5 wt% to 90 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, it becomes difficult to obtain the non-stickiness obtained from the fructooligosaccharide fatty acid ester and the feeling of adhesion to the skin. If the content of fructooligosaccharide fatty acid ester exceeds 90 wt%, the amount of fructooligosaccharide fatty acid ester is increased and the amount of zinc oxide, which is a UV scattering agent, is reduced. Sex is reduced. Even when an ultraviolet ray inhibitor is contained as a component, the blending amount of the ultraviolet ray inhibitor is reduced for the same reason, so that the sunscreen balm has a reduced protection against ultraviolet rays. In addition, titanium oxide can be used as the ultraviolet scattering agent.

  In the sunscreen balm, the total amount of dextrin fatty acid ester and fructooligosaccharide fatty acid ester which are gelling agents is preferably included in the range of 0.5 wt% to 20 wt%. When the total amount of the gelling agent is less than 0.5 wt%, the sunscreen balm is difficult to adhere to the skin. When the total amount of the gelling agent exceeds 20 wt%, the viscosity of the sunscreen balm becomes so high that it is difficult to use.

[Example 19 beauty oil]
Using the sample 1 described above, a beauty oil was prepared by the following method and the formulation shown below. When preparing the beauty oil, components (1) to (3) were mixed uniformly.

Ingredient wt%
(1) Sample 1 10.0
(2) Squalane 88.0
(3) Ascorbyl tetrahexyldecanoate 2.0
According to the beauty oil of Example 19, it was confirmed that the adhesion to the skin was improved while stickiness was suppressed as compared with the case of using mineral oil.

  In the cosmetic oil, it is preferable that fructooligosaccharide fatty acid ester is contained in the range of 0.5 wt% to 90 wt%. When the content of the fructooligosaccharide fatty acid ester is less than 0.5 wt%, it becomes difficult to obtain the non-stickiness obtained from the fructooligosaccharide fatty acid ester and the feeling of adhesion to the skin. When the content of fructooligosaccharide fatty acid ester exceeds 90 wt%, the amount of ascorbyl tetrahexyl decanoate, which is a cosmetic component, decreases as the blending amount of fructooligosaccharide fatty acid ester increases.

[About each example]
If the fructo-oligosaccharide fatty acid ester as an oil agent used in each example satisfies the following conditions and is liquid at 25 ° C., use a substance other than the sample described in each example. Also good. That is, as the fatty acid that forms an ester bond with fructo-oligosaccharide, one or more of the fatty acids described above can be selected. Moreover, as long as each fructooligosaccharide fatty acid ester is mix | blended in cosmetics in the quantity described in each Example, it is possible to acquire the effect equivalent to the above-mentioned.
・ Molecular weight of fructooligosaccharide M 300 ≦ M ≦ 10000
・ C number of fatty acid C linear saturation 8 ≦ C ≦ 12
Branch chain saturation 8 ≦ C ≦ 18
Unsaturated 8 ≦ C ≦ 18
・ Fatty acid substitution rate T 65% ≦ T ≦ 100%
In addition, when the substitution rate of the fatty acid per molecule of fructo-oligosaccharide is 95% or more and 100% or less, each implementation is compared with the case where the substitution rate is 65% or more and less than 95% by the number of hydroxyl groups. The stickiness of the cosmetics in the example can be suppressed.

Moreover, in each Example, 2 or more types of fructo-oligosaccharide fatty acid ester containing a mutually different fatty acid may be used for the fructo-oligosaccharide fatty acid ester as an oil agent.
Furthermore, in each Example, even if it is a dextrin fatty acid ester as a gelatinizer or a film formation agent, the fatty acid which forms an ester bond with dextrin can select 1 or more of the fatty acids mentioned above. Two or more dextrin fatty acid esters containing different fatty acids may be used as the dextrin fatty acid ester. Moreover, in each Example, even if it is a fructo-oligosaccharide fatty acid ester as a gelatinizer, the fatty acid which forms an ester bond with a fructo-oligosaccharide can select 1 or more of the fatty acids mentioned above. Two or more fructooligosaccharide fatty acid esters containing different fatty acids may be used for the fructooligosaccharide fatty acid ester.

  Of the dextrin fatty acid esters that are gel agents used in each embodiment, at least one of Leopard KL2, Leopard KS2, and Leopard TL2 can be used as dextrin palmitate, and Leopard can be used as dextrin myristate. MKL2 can be used (Leopard is a registered trademark). Leopard TT2 can be used for dextrin (palmitic acid / ethylhexanoic acid) which is also a gelling agent, and Unifilma HVY can be used for dextrin isostearate which is a film forming agent (Unifilma is a registered trademark). . In addition, among fructooligosaccharide fatty acid esters which are gelling agents, at least one of Leopard ISK2 and Leopard ISL2 can be used for inulin stearate. These gelling agents are all manufactured by Chiba Flour Milling Co., Ltd.

As described above, according to one embodiment of the fructooligosaccharide fatty acid ester and the cosmetic, the effects listed below can be obtained.
(1) Since sugars having high affinity for the skin are used and fructose oligosaccharides are used as constituent materials for esters, the molecular weight of sugar chains is larger than when monosaccharides or disaccharides are used. Adhesion to the skin is improved. In addition, by setting the fatty acid substitution rate to a high substitution rate of 95% or more, stickiness of the fructooligosaccharide fatty acid ester, which is an oil agent, can be suppressed while maintaining adhesion to the skin.

  (2) The cosmetics are given high adhesion to the skin and low stickiness, which are the characteristics of fructooligosaccharide fatty acid esters, which are oil agents. In addition, in the cosmetic, the gelling agent can prevent the cosmetic from being difficult to spread on the skin while suppressing the cosmetic from dripping from the application target.

Claims (5)

A fructo-oligosaccharide composed of only a plurality of fructose or only a plurality of fructose and one glucose ;
An ester bond with a fatty acid represented by the general formula R ₁ COOH;
The average molecular weight of fructooligosaccharide is 10,000 or less 6 00 or more,
The fatty acid hydrocarbon group R ₁ is an alkyl group or an alkenyl group, and the hydrocarbon group R ₁ is a linear saturated hydrocarbon group having 7 to 11 carbon atoms, 7 to 17 carbon atoms. At least one of the following branched hydrocarbon groups and an unsaturated hydrocarbon group having 7 to 17 carbon atoms,
The substitution rate of the fatty acid per molecule of the fructooligosaccharide is 95% or more and 100% or less,
Fructooligosaccharide fatty acid ester that is liquid at 25 ° C.   The substitution rate of the fatty acid per molecule of the fructooligosaccharide is 97% or more and 100% or less.
  The fructo-oligosaccharide fatty acid ester according to claim 1. Containing 0.1 to 99.8% by weight of the oil agent,
Cosmetics which are the fructooligosaccharide fatty acid ester of Claim 1 or 2 . A first fructooligosaccharide fatty acid ester as an oil agent;
Dextrin fatty acid ester as a gelling agent or film-forming agent, and at least one of a second fructooligosaccharide fatty acid ester as a gelling agent,
The first fructooligosaccharide fatty acid ester is
A fructo-oligosaccharide composed of only a plurality of fructose or only a plurality of fructose and one glucose ;
An ester bond with a fatty acid represented by the general formula R ₁ COOH;
The average molecular weight of fructooligosaccharide is 10,000 or less 6 00 or more,
The fatty acid hydrocarbon group R ₁ is an alkyl group or an alkenyl group, and the hydrocarbon group R ₁ is a linear saturated hydrocarbon group having 7 to 11 carbon atoms, 7 to 17 carbon atoms. At least one of the following branched hydrocarbon groups and an unsaturated hydrocarbon group having 7 to 17 carbon atoms,
The substitution rate of the fatty acid of the first fructooligosaccharide per molecule is 100% or less 95% or more,
It is liquid at 25 ° C,
The dextrin fatty acid ester and the second fructo-oligosaccharide fatty acid ester are solid or resinous at 25 ° C. The first fructooligosaccharide fatty acid ester is contained in a range of 0.5 wt% to 90 wt%,
The cosmetic according to claim 4 , wherein the dextrin fatty acid ester and the second fructooligosaccharide fatty acid ester are contained in a total amount of 0.5 wt% to 30 wt%.

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