JPH0648916A - Cosmetic - Google Patents

Abstract

PURPOSE:To obtain a cosmetic smoothly spreadable on the skin, exhibiting excellent smoothness and having excellent emulsion stability by using a silicone in combination with a nonionic amphiphatic compound capable of keeping a lamellar liquid crystal structure over a wide temperature range. CONSTITUTION:The cosmetic applicable to the skin, hair, etc., is produced by using (A) a nonionic amphiphatic compound having >=1 long-chain branched alkyl or alkenyl and >=3 OH groups in one molecule and capable of keeping a lamellar liquid crystal structure at least at 25 deg.C and keeping the structure at a temperature exceeding 50 deg.C in combination with (B) one or more kinds of silicone compounds selected from dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, fatty acid polysiloxane, cyclic silicone, etc. The amounts of the components A and B in the cosmetic are preferably 0.01-80wt.% and 0.01-30wt.%, respectively. The component A is e.g. 1mol addition product of sorbitol and isostearyl glycidyl ether.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cosmetic composition, more specifically, it has excellent moisturizing properties, spreads well when applied to the skin, hair, etc., has excellent smoothness when dried and wet, and has excellent emulsion stability. Regarding good cosmetics.

[0002]

2. Description of the Related Art Generally, various moisturizers are used in cosmetics. However, conventional moisturizers do not provide a sufficient moisturizing effect when the compounding amount is small, and the moisturizing agent is used in a large amount to obtain the effect. When compounded, there were problems such as impairing the stability of the system.

Further, conventionally, various oil agents have been blended in hair cosmetics for the purpose of imparting flexibility and wettability to the hair, protecting the hair, improving the feel and giving an emollient effect. Among these oil agents, silicones typified by dimethylpolysiloxane are superior in smoothness and lubricity as compared with higher alcohols, glycerides, liquid paraffins, esters, etc., and give a smooth feel and gloss to hair. Is known and is used in many hair cosmetics. However, silicones are inferior in moisturizing effect and are smooth but lacking in moisturizing effect.
Further, since it is hydrophobic, it has a drawback that it has a strong squeaky feeling when the hair is moistened. Also, in skin cosmetics, silicones are generally used for the purpose of imparting a smooth feel without stickiness. However, silicones generally have poor compatibility with other cosmetic oils and poor emulsification / dispersion properties of the system.Therefore, if a large amount of silicone is added to effectively exhibit the properties of silicone oil, emulsification / dispersion in the system There is also a problem that the property deteriorates and the separation phenomenon occurs over time.

On the other hand, emulsion type cosmetics are widely used because of their composition, they can provide appropriate oil and water to the skin and hair. Then, by changing the type and amount of the oil component, various emulsions having different physical properties and feeling of use can be obtained. However, since the emulsion is a thermodynamically unstable system, it is difficult to stabilize it, and many studies and attempts have been made so far. One of the countermeasures is the addition of an emulsification aid having a surfactant. Such emulsification aids include cationic surfactants, anionic surfactants, amphoteric surfactants and nonionic surfactants, but they have a wide range of oil components that can be mixed and are applicable to various cosmetics. Nonionic surfactants are most preferable because they are possible.

Nonionic emulsification aids include higher alcohols and long-chain branched alkyltriols (Japanese Patent Publication No. 38-50).
50, JP-A-63-258804), long-chain alkyl polyglycerol ether (JP-A-52-63).
75, 63-23737), ethylene oxide adducts of higher alcohols (JP-A-62-965).
No. 85) and polyol ethers derived from higher fatty acids (Japanese Patent Publication No. 61-56016) and the like are known. However, these compounds do not form a lamellar liquid crystal by themselves, have a strong oily feeling when applied to the skin or hair, or have a narrow liquid crystal formation temperature range even when combined with other components, and thus stabilize the cosmetic composition. There was a problem that I could not keep it.

[0006]

Therefore, the object of the present invention is to provide excellent moisturizing properties, good spreadability when applied to skin, hair, etc., excellent smoothness in dry and wet conditions, and good stability. The purpose is to provide cosmetics.

[0007]

Under such circumstances, the inventors of the present invention have conducted diligent research to solve the above-mentioned problems, and as a result, found that a nonionic amphipathic compound having a lamellar liquid crystal structure in a wide temperature range was obtained. It has been found that, when used in combination with silicones, it is possible to obtain a cosmetic which spreads well when applied, gives a refreshing feeling without stickiness, has excellent moisturizing properties, and has good stability, and to complete the present invention. I arrived.

That is, the present invention relates to a cosmetic containing the following components (A) and (B). (A) having at least one long-chain branched alkyl or alkenyl group and at least three hydroxyl groups in one molecule, 2
Nonionic amphipathic compound (B) dimethyl polysiloxane, methylphenyl polysiloxane, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic having a lamellar liquid crystal structure at a temperature above 5 ° C. and 50 ° C. One or more silicones selected from the group consisting of alcohol-modified polysiloxane, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone and alkyl-modified silicone.

The nonionic amphipathic compound of the component (A) used in the present invention has a lamellar liquid crystal structure at least at 25 ° C., and further retains a lamellar liquid crystal structure at a temperature of more than 50 ° C. It is necessary. Here, the confirmation of the lamella-like liquid crystal structure is performed, for example, by The Journal of Cell Biology (The Journal).
of Cell Biology), Volume 12, Volume 2
07-209 and surface, Vol. 11, No. 10, 57.
The method described on pages 9 to 590 can be performed using X-ray diffraction and a differential scanning calorimeter (DSC). Examples of compounds having such properties are shown below (A-
1), (A-2) and (A-3).

(A-1) Glycerylated polyols represented by the following general formula (1). A _a (G) (1) [wherein G represents a residue obtained by removing a hydroxyl groups from a polyol selected from pentaerythritol, sorbitol, maltitol, glucose, fructose and alkyl glycosides, and A is

[0011]

[Chemical 1]

(Wherein R ¹ represents a branched alkyl group or alkenyl group having 10 to 36 carbon atoms), and a represents a number of 1 or more and does not exceed the total number of the hydroxyl groups of the polyol].

(A-2) A methyl branched fatty acid ester represented by the following general formula (2).

[0014]

[Chemical 2]

[Wherein b ₁ and b ₂ are each 0 to 20]
Represents the integer, and the sum of b ₁ and b ₂ is 6 to 20]

(A-3) Branched fatty acid glyceroglycolipid represented by the following general formula (3)

[0017]

[Chemical 3]

General formula (1) showing the component (A-1)
Among them, the alkyl glycoside represented by G is methyl
Glucoside, ethyl glucoside, propyl glucoside,
Octyl glucoside, methyl maltoside, ethyl malto
Examples include sid. Also, R ¹Has 16 carbons
.About.36, particularly 18 to 24 branched alkyl groups are preferred.
Such branched alkyl group R¹The following general formula (4)
Or (5)

[0019]

[Chemical 4]

A group represented by the formula (wherein c _{1 to} c ₄ have the same meanings as described above) is preferred. Preferred examples of these branched alkyl groups include methylpentadecyl group, methylhexadecyl group, methylheptadecyl (isostearyl) group, methyloctadecyl group, methylbehenyl group, ethylhexadecyl group, ethyloctadecyl group, ethylhebenyl group, Butyl dodecyl group, butyl hexadecyl group,
Butyloctadecyl group, hexyldecyl group, peptylundecyl group, octyldodecyl group, decyldodecyl group,
Examples thereof include a decyltetradecyl group, a dodecylhexadecyl group, and a tetradecyloctadecyl group. Further, in the general formula (1), a is preferably 1 or 2.

Such glycerylated polyols (1)
Is produced, for example, by reacting a polyol with a corresponding branched alkyl glycidyl ether in the presence of a basic catalyst according to the following formula.

[0022]

[Chemical 5]

[Wherein R ¹ has the same meaning as described above]

The reaction molar ratio between the polyol and the branched alkyl glycidyl ether (6) in this reaction can be appropriately selected depending on the degree of etherification of the desired glycerylated polyol. For example, in order to obtain a desired glycerylated polyol having a high content of 1 mol adduct, it is usually necessary to use the polyol in excess at a ratio of 1.2: 1.0 to 10.0: 1.0. Considering the production amount of 1 mol adduct and the recovery of polyol, 1.5:
A ratio of 1.0 to 5.0: 1.0 is preferable. Further, in order to obtain a desired product having a high content of 2 mol adduct of glycerylated polyol, it is usually 0.3: 1.0 to 1.1: 1.
If the branched alkyl glycidyl ether is used in excess at a ratio of 0, considering the production amount of the 2 mol adduct,
A ratio of 0.4: 1.0 to 0.8: 1.0 is preferable.

The reaction is usually carried out without a solvent, but it is preferable to use an organic solvent for the purpose of assisting the mixing of the polyol and the branched alkyl glycidyl ether. Examples of the organic solvent include dimethyl sulfoxide, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, etc.
It is preferable to use 0 times the amount.

As the catalyst, an acid or basic catalyst generally known as an epoxy group reaction catalyst can be used. When an acid catalyst is used, a side reaction is
It is not preferable because a decomposition reaction of the ether bond or a dehydration reaction of the hydroxyl group of the generated glycerylated polyols occurs.
It is preferable to use a basic catalyst. The basic catalyst used is not particularly limited, but sodium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, sodium hydride and the like can be mentioned from the viewpoint of reactivity and economy. These basic catalysts are contained in an amount of 0.01 to 20.0% by weight, particularly 0.1 to 10.
It is preferably used in the range of 0% by weight.

The reaction is carried out at 50 to 200 ° C., preferably 80
It is carried out at ˜150 ° C. If the reaction temperature is less than 50 ° C, the reaction rate is slow, and if it exceeds 200 ° C, the product is colored, which is not preferable.

In this reaction, when water is present in the reaction system, the epoxy group of the branched alkyl glycidyl ether reacts with water to form glyceryl ether as a by-product.
It is preferable to dissolve or disperse the polyol in an organic solvent, heat it to blow dry nitrogen gas, or heat and dehydrate it under reduced pressure to remove water, and then add a branched alkyl glycidyl ether to react.

After completion of the reaction, an organic acid such as acetic acid or citric acid or an inorganic acid such as sulfuric acid, hydrochloric acid or phosphoric acid is added to neutralize the catalyst, and then the organic solvent used in the reaction is removed. In order to avoid thermal decomposition of the reaction product, the organic solvent is preferably removed under reduced pressure, usually at a temperature of 120 ° C or lower.

The glycerylated polyols (1) used in the present invention are usually 1 mol adduct of 1 molecule of a branched alkyl glycidyl ether (6) added to 1 molecule of a polyol,
Branched alkyl glycidyl ether (3) with 3 molecules or more per 1 molecule of polyol in addition to 2 mol addition product with 2 molecules added
It is obtained as a mixture of polymorphic adducts in which is added. Glycerylated polyols (1) thus obtained
Is usually used as a mixture of these 1-mole adducts, 2-mole adducts, or poly-mole adducts. However, if there is a problem due to performance or formulation reasons, etc., such as silica gel column or solvent extraction. It can be purified using a known purification method. The glycerylated polyols (1) of the present invention may contain unreacted glycosides in addition to the desired 1-mol adduct, 2-mol adduct, or polymorph adduct. Such an unreacted glycoside can be used as it is contained if there is no problem in practical use. If there is a problem, an organic solvent such as ethyl acetate, methyl ethyl ketone, methyl isobutyl ketone, chloroform or the like is used. The layer can be removed by a method using an extraction solvent system or a known purification method such as Smith thin film distillation.

Further, in the general formula (2) representing the methyl branched fatty acid ester, the sum of b ₁ and b ₂ is 6 to 20, but preferably 10 from the viewpoint of performance as a cosmetic material.
-16, particularly preferably 14. The branched methyl group is particularly preferably located near the center of the alkyl main chain.

The methyl branched fatty acid ester (2) is produced according to the following reaction formula.

[0033]

[Chemical 6]

[In the formula, b ₁ and b ₂ have the same meanings as described above, and R ³ represents an alkyl group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms] The target compound (2) is produced by reacting the lower alkyl ester of fatty acid (7) with pentaerythritol (8).

The lower alkyl ester (7) of methyl-branched fatty acid used in this reaction can be obtained by esterifying the corresponding carboxylic acid by a conventional method. Among the corresponding carboxylic acids here, those obtained industrially are usually
A mixture having a uniform distribution of the total number of carbon atoms in the alkyl group and the positions of the branched methyl groups. For example, isostearic acid having a methyl branch obtained as a by-product during the production of oleic acid dimer has a total number of carbon atoms of 18 (b ₁ And the sum of b ₂ is 14%), and the balance is those having a total carbon number of 14, 16, or 20, and the branched methyl group is located almost at the center of the alkyl main chain. [Journal of the American Oil Chemistry
Society (J. Amer. Oil Chem. So
c. ) Vol. 51, 522 (1974)].

In this reaction, the ratio of the lower alkyl ester of methyl-branched fatty acid (7) and pentaerythritol (8) used is (7) / (8) = 1/1 to 1 in molar ratio.
It is preferably 0/1.

The solvent used in this reaction is not particularly limited, but is a lower alkyl ester of methyl-branched fatty acid (7).
And pentaerythritol (8) are preferably dissolved, and dimethylformamide and the like are preferably used.

As a reaction catalyst, an alkali catalyst is usually used, and sodium methylate or the like is preferably used. The catalyst amount is not particularly limited, but it is preferably used in the range of 0.1 to 20 mol% with respect to the lower alkyl ester (7) of methyl branched fatty acid. The reaction temperature of this reaction is selected from the range of 60 to 150 ° C.

Isolation of compound (2) from the reaction mixture is
It can be carried out by a conventional method, for example, distilling off the solvent, recrystallization, chromatography or the like, or a combination thereof.

Further, the branched fatty acid glyceroglycolipids are shown.
In the general formula (3), R²C ₁And c₂Cosmetics
From the viewpoint of performance as a material, the above b₁And b₂Same as
It is preferable that the sum of shit is 10-16, especially 14,
c₃And c_FourFrom the same viewpoint, the sum is 6 to 14,
It is preferably 8 to 12.

The branched fatty acid glyceroglycolipid (3) is produced, for example, according to the following reaction formula.

[0042]

[Chemical 7]

[In the formula, X ¹ represents a halogen atom, M represents a hydrogen atom or a cation group, and R ² has the same meaning as described above.]

That is, fatty acid (1
Compound (3) is obtained by reacting 0).

The compound (9) used in this reaction can be easily produced by a known method, for example, a reaction of a monosaccharide or oligosaccharide with glycerol monohalohydrin, glycerol dihalohydrin or epihalohydrin.

The compound (10) can be produced, for example, by reacting a fatty acid with an alkali metal hydroxide such as sodium hydroxide or an amine in the presence of a suitable solvent. Examples of the cation group represented by M in the compound (10) include alkali metal, ammonium group, alkylammonium group, trialkanolamine and the like.

To carry out the present method, for example, the compound (9) and the compound (10) may be reacted at a temperature of 30 to 150 ° C, preferably 70 to 120 ° C. The amount of the compound (10) used here is usually 0.3 to 3.0 times, and particularly preferably 1.0 to 3.0 times the mol of the compound (9).
It is 2.0 times the molar amount. When M of the compound (10) is a hydrogen atom, the reaction is carried out in the presence of an alkaline substance. Examples of the alkaline substance include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal alcoholates and alkylamine hydroxides.

In carrying out this reaction, a polar solvent can be used for the purpose of promoting mixing of the compound (9) and the compound (10) and allowing the reaction to proceed smoothly. The polar solvent used here is at least one selected from dimethylformamide, dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, pyridine, water and the like. The amount of polar solvent used may be selected appropriately. Further, in carrying out this reaction, a phase transfer catalyst can be used for the purpose of promoting this reaction, if necessary. The amount of the phase transfer catalyst used here may be appropriately selected, but is usually 0.1 to 10 mol% with respect to the compound (10). The phase transfer catalyst used here includes, for example, tetraethylammonium bromide, tetrapropylammonium bromide,
Tetrabutylammonium bromide, tetraheptylammonium bromide, tetrahexylammonium bromide, N, N, N-trimethyl-N-octylammonium chloride, N, N, N-trimethyl-N-
Decyl ammonium chloride, N, N, N-trimethyl-N-dodecyl ammonium chloride, N, N, N
-Trimethyl-N-hexadecyl ammonium chloride, N, N, N-trimethyl-N-octadecyl ammonium chloride, N, N-dimethyl-N, N-dihexadecyl ammonium chloride, N, N-dimethyl-
Mention may be made of tetraalkylammonium chlorides such as N, N-dioctadecyl ammonium chloride.

In addition to the desired glyceroglycolipid (3), the reaction product of the above reaction usually contains an inorganic salt as a by-product, unreacted compound (9) or (10), and the like. There is. Therefore, although the reaction product can be used as it is depending on the purpose of use, when a higher purity product is required, for example, partition chromatography, adsorption chromatography, solvent fractionation method, recrystallization method, etc. It may be appropriately purified by a known method before use.

Thus obtained (A-1) and (A-2)
And (A-3) is a thermotropic liquid crystal which retains the lamellar liquid crystal structure in a wide temperature range as described above, and has good properties as a cosmetic material such as being dispersed almost uniformly as lamellar liquid crystal when mixed with water. Have.

The component (A) can be used alone or in combination of two or more kinds, and is usually 0.0
It is preferable to add 1 to 80% by weight, particularly 0.1 to 60% by weight.

The silicones as the component (B) used in the present invention include, for example, the following (B-1) to (B-1).
(B-11) may be mentioned. (B-1) Dimethyl polysiloxane represented by the following formula (11)

[0053]

[Chemical 8]

(In the formula, d represents a number of 3 to 20,000.) (B-2) Methylphenyl polysiloxane represented by the following formula (12-1) or (12-2).

[0055]

[Chemical 9]

(Where e ₁ is a number from ₁ to 20000, e
₂ and e ₃ are numbers whose sum is 1 to 500. ) (B-3) Amino-modified silicone represented by the following formula (13-1) or (13-2)

[0057]

[Chemical 10]

Of these, particularly preferred amino-modified silicones are represented by the following general formula.

[0059]

[Chemical 11]

(In the formula, R ⁶ , f ₁ and f ₂ have the above-mentioned meanings.) A typical amino-modified silicone of the present invention is represented by the following general formula and has an average molecular weight of about 3,000 to 100,000, which is called CTFA dictionary (Cosmetic Ingre, USA) under the name of Amodimethicone.
dient Dictionary) 3rd edition.

[0061]

[Chemical 12]

(In the formula, f ₁ and f ₂ have the above-mentioned meanings.) The above amino-modified silicone is preferably used as an aqueous emulsion, and the aqueous emulsion is, for example, JP-B-56-38609. In accordance with the method described in Japanese Patent Publication No. JP-A-2003-187, a cyclic diorganopolysiloxane and an organodialkoxysilane having an aminoalkyl group and a hydroxyl group, a hydroxyalkyl group, an oxyalkylene group or a polyoxyalkylene group are added to a quaternary ammonium salt system. It is obtained by emulsion polymerization in the presence of a surfactant and water.

When the above amino-modified silicone is used as an aqueous emulsion, the amount of amino-modified silicone contained in the aqueous emulsion is usually 20 to 60% by weight, preferably 30 to 50% by weight. .

Commercially available preferred amino-modified silicone aqueous emulsions include SM 8702C (manufactured by Toray Silicone Co., Ltd.) and DC 929 (manufactured by Dow Corning Co., Ltd.).

(B-4) Fatty acid-modified polysiloxane represented by the following formula (14)

[0066]

[Chemical 13]

[Wherein g ₁ , g ₂ and g ₃ are 1 to 350
, G ₄ is a number from 0 to 10, R ¹² is C _n1 H
_2n1 + ₁ indicating the (n 1 = 9~21). ] (B-5) Alcohol-modified silicone represented by the following formula (15-1) or (15-2)

[0068]

[Chemical 14]

[Wherein, h ₁ and h ₂ are each _{1 to} 500
(Preferably 1 to 200) and R ¹³ is C _n2 H.
_2n2 shows the (n ₂ = 0~4). (B-6) Aliphatic alcohol-modified polysiloxane represented by the following formula (16)

[0070]

[Chemical 15]

Here, R ¹⁴ represents a methyl group or a phenyl group, i ₁ represents an integer of ₁ to 3000, i ₂ and i ₃ represent integers such that i ₂ + i ₃ = 1 to 500, and R ¹⁵
Represents an alkyl group having 1 to 28 carbon atoms (preferably 12 to 22 carbon atoms), and i ₄ represents an integer of 0 to 6. (B-7) The following formulas (17-1), (17-2), (17)
-3) or polyether modified silicone represented by (17-4)

[0072]

[Chemical 16]

(B-8) Epoxy-modified silicone represented by the following formula (18)

[0074]

[Chemical 17]

[Wherein k ₁ is ₁ to 500 (preferably 1
To 250), k ₂ is 1 to 50 (preferably 1 to 3)
0) and R ¹⁷ represents an alkylene group having 1 to 3 carbon atoms. (B-9) Fluorine-modified silicone represented by the following formula (19)

[0076]

[Chemical 18]

[In the formula, 1 is 1 to 400 (preferably 1 to
250). ] (B-10) Cyclic silicone represented by the following formula (20)

[0078]

[Chemical 19]

(In the formula, m represents a number of 3 to 8 and R ¹⁸ represents an alkyl group having 1 to 3 carbon atoms.) (B-11) The following formula (21-1) or (21-2) Alkyl-modified silicone represented by

[0080]

[Chemical 20]

[Wherein, o ₁ and o ₂ are each _{1 to} 500
(Preferably 1 to 200), and R ¹⁹ has 2 carbon atoms.
To 18 alkyl groups, R ²⁰ is C _n3 H _2n3 (n ₃ = 0 to
4) and R ²¹ represents an alkyl group having 10 to 16 carbon atoms. ]

In these silicones, rinse,
In the case of a rinse-type hair cosmetic such as a conditioner, the above (B-1) [wherein, in the formula (11), d can be selected from 3 to 20,000 depending on the purpose of the feeling of finish, but a light finish As the type of 100-100
0 is preferable], (B-3), (B-6), (B-
Those of 7) and (B-10) are preferable. In the case of non-sooting type hair cosmetics such as hair creams, styling lotions, and styling mousses, the above (B-1) [for the purpose of reducing oily feeling,
In Formula (11), d is preferably 2000 to 8000], (B-2), (B-3), (B-7) and (B-
Those of 10) are preferable.

The total amount of the component (B) silicones is 0.01 to 30% by weight, especially 0.1 to 30% by weight in the cosmetic of the present invention.
20% by weight is preferred.

Further, in order to further enhance the effect of the present invention, a surfactant can be used in combination. As such a surfactant, any of a nonionic surfactant, a cationic surfactant, an anionic surfactant and an amphoteric surfactant can be used, and particularly for skin cosmetics, a nonionic surfactant is used. For skin and hair cleansing agents, anionic surfactants, nonionic surfactants and amphoteric surfactants are used, and for hair cosmetics such as hair rinses and hair styling agents, cationic surfactants are used. preferable. As the nonionic surfactant, for example, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid monoglyceride, sucrose fatty acid ester,
Examples thereof include higher fatty acid alkanolamides, and typical examples of the cationic surfactant include quaternary ammonium salts. Any quaternary ammonium salt can be preferably used as long as it is usually used in cosmetics, and in particular, a branched chain represented by the following general formulas (22) and (23) described in JP-A-61-267505. It is preferable to contain one or more quaternary ammonium salts.

[0085]

[Chemical 21]

[0086]

[Chemical formula 22]

Examples of the anionic surfactant include straight chain or branched chain alkylbenzene sulfonate, alkyl or alkenyl sulfate, alkyl or alkenyl ether sulfate added with ethylene oxide and / or propylene oxide, olefin sulfonate, Alkane sulfonates, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylates to which ethylene oxide and / or propylene oxide is added, α-sulfo fatty acid salt esters, amino acid type surfactants, phosphate ester type surfactants , Sulfosuccinic acid type surfactants, taurine type surfactants, amide ether sulfate type surfactants and the like, and amphoteric surfactants include sulfonic acid type amphoteric surfactants, betaine type amphoteric surfactants and the like. . These surfactants are added in an amount of 0.01 to 30 in the total composition.
%, Preferably 0.1 to 10% by weight.

Furthermore, in the cosmetic of the present invention, if necessary, a component usually used in cosmetics, pharmaceuticals, foods, etc., for example, higher alcohols having a linear or branched alkyl group or alkenyl group; Hydrocarbons such as liquid paraffin, petrolatum and solid paraffin; lanolin derivatives such as liquid lanolin and lanolin fatty acids; phospholipids such as lecithin; sterols and derivatives thereof such as cholesterol; collagen degrading peptide derivatives; perfluoropolyether; higher alcohols Higher fatty acid esters, higher fatty acids, oils and fats such as long-chain amidoamine having an alkyl group or an alkenyl group; animal and vegetable oils and fats such as mink oil and olive oil; antidandruff agents, fungicides, vitamins and other medicinal agents; parabens Antiseptics such as classifiers; Thickeners such as water-soluble polymers; Colorants such as dyes and pigments; Ultraviolet Absorbents; propylene glycol,
Moisturizers such as glycerin, carbitol, 3-methyl-1,3-butanediol, sugars; astringents; fragrances; pigments;
Others, Encyclopedia of Conditioning Rinse Ingredients [ENCYCLOP
EDIA OF CONDITIONING RINS
E INGREDIENTS (MICELLE PRE
SS, 1987)] and Encyclopedia of Shampoo Ingredients [ENCYCLOP
EDIA OF SHAMPOO INGREDIEN
TS (MICELLE PRESS, 1985)],
The components listed in the latest cosmetics science (Yakuji Nipposha, 1988) can be appropriately blended within a range not impairing the effects of the present invention.

The cosmetics of the present invention can be produced according to a usual method, for example, basic cosmetics such as oil-in-water type, water-in-oil type emulsified cosmetics, oil-based cosmetics, and make-up cosmetics such as lipsticks and foundations. Skin cleanser; Body treatment; Hair cosmetics such as shampoo, hair rinse, hair treatment, hair cream, styling lotion, styling mousse, conditioning mousse, hair spray, hair liquid, styling gel; skin cream, skin milk, skin lotion It can be applied to skin care cosmetics such as; bath agents and the like.

[0090]

The cosmetic composition of the present invention has an excellent moisturizing action due to the synergistic action of the components (A) and (B), has a low oily feeling and spreads easily, and particularly when applied to hair, when it is wet. It has the characteristics of less squeaking and good smoothness,
Furthermore, the emulsion stability is also good.

[0091]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.

Synthesis Example 1 Pentaerythritol 82 g, dimethyl sulfoxide 2
00 g and 1 g of sodium hydroxide were put into a 500 ml flask, heated and dissolved at 105 ° C., dry nitrogen gas was blown thereinto, and about 20 g of water and dimethyl sulfoxide were distilled out to remove water in the reaction system. After 39 g of isostearyl glycidyl ether was added dropwise to this over 1 hour, 1
The reaction was carried out at 05 ° C. for 4 hours with stirring. After the reaction,
Acetic acid (1.5 g) was added to the reaction mixture to neutralize the catalyst, dimethyl sulfoxide was completely distilled off at 80 ° C. under reduced pressure, and 99% ethanol was added to the residue to separate unreacted pentaerythritol by filtration. did. Ethanol was distilled off from the obtained filtrate under reduced pressure, and water was added to the residue 500 times.
ml and ethyl acetate (500 ml) were added and the mixture was extracted with ethyl acetate. The solvent was distilled off from the ethyl acetate-soluble fraction to obtain 63 g of a pale yellow adduct of pentaerythritol isostearyl glycidyl ether. When this crude product is separated and purified using silica gel column chromatography with an elution solvent of acetone: hexane = 2: 1,
The desired pentaerythritol-isostearyl glycidyl ether 1 mol adduct was eluted, and the elution fractions were collected and the solvent was distilled off to obtain the desired pentaerythritol isostearyl glycidyl ether 1 mol adduct 16 g ( Yield 30%) was obtained. Hydroxyl value 482 (calculated value 486) NMR (CDCl ₃ ): δ (ppm) 3.95 (1H, m, -OCH ₂ -C H OH-CH ₂ O-), 3.67 (6H, s, -C (C H ₂ OH) ₃ ),
3.46 (8H, m, -OCH _2- ), 1.30 ~ 1.59 (29H, b, -CH ₂ -,-CH-), 0.8
8 (6H, m, -CH ₃ ) IR (liquid film) cm ^-1 : ν _OH (-OH) 3200 to 3400 ν _OH (stretch) (-CH-,-CH ₂ -,-CH ₃ ) 2850,2920 ν _OH (Variation angle) (-CH-,-CH ₂ -,-CH ₃ ) 1375,1460 ν _CO (-CO-) 1110,1035,1010

Synthesis Example 2 91 g of sorbitol, 100 g of N-methylpyrrolidone and 1 g of sodium hydroxide were placed in a 300 ml flask and
The mixture was heated to 00 ° C. to dissolve it, and dry nitrogen gas was blown into it to distill about 10 g of water and N-methylpyrrolidone to remove water in the reaction system. After 33 g of isostearyl glycidyl ether was added dropwise thereto over 2 hours, the reaction was carried out at 110 ° C. for 4 hours with stirring. After completion of the reaction, acetic acid (1.5 g) was added to the reaction mixture to neutralize the catalyst, and N-
Methylpyrrolidone was completely distilled off at 80 ° C., 500 g of acetone was added to the residue, and the precipitated unreacted sorbitol was filtered off. Acetone was distilled off from the obtained filtrate under reduced pressure to obtain 42 g of a crude purified product of an adduct of sorbitol / isostearyl glycidyl ether. When this crude product was separated and purified using silica gel column chromatography with an elution solvent of chloroform: methanol = 5: 1, the target 1 mol adduct of sorbitol / isostearyl glycidyl ether was eluted and the elution fraction was obtained. 20 g of 1 mol adduct of the desired sorbitol isostearyl glycidyl ether is collected by collecting the components and distilling off the solvent.
(Yield 39%) was obtained. Hydroxyl value 664 (calculated value 663) NMR (CDCl ₃ ): δ (ppm) 3.95 to 3.94 (15H, m, -O-CH _2- , O-CH-), 1.34 to 1.58 (29H, b,
-CH ₂ -,-CH-), 0.86 (6H, m, -CH ₃ ) IR (liquid film) cm ^-1 : ν _OH (-OH) 3200 to 3400 ν _OH (stretch) (-CH-,-CH ₂ -,-CH ₃ ) 2840,2910 ν _OH (Bend) (-CH-,-CH ₂ -,-CH ₃ ) 1370,1455 ν _CO (-CO-) 1030 ~ 1110

Synthesis Example 3 Methyl glucoside 97 g, dimethyl sulfoxide 200
g and 1 g of sodium hydroxide were placed in a 500 ml flask and heated to 105 ° C. to dissolve them, and dry nitrogen gas was blown thereinto to distill about 20 g of water and dimethyl sulfoxide to remove water in the reaction system. 33 g of isostearyl glycidyl ether was added dropwise to the flask over 4 hours and then reacted at 105 ° C. for 5 hours with stirring.
After the reaction was completed, 1.5 g of acetic acid was added to the reaction mixture to neutralize the catalyst, and dimethylsulfoxide was added under reduced pressure at 80 ° C.
Completely removed by distillation at 99 ° C., 99% ethanol was added to the residue, and the precipitated unreacted methyl glucoside was filtered off.
Ethanol was distilled off from the obtained filtrate under reduced pressure, 500 ml of water and 500 ml of ethyl acetate were added to the residue for extraction with ethyl acetate, and the solvent was distilled off from the ethyl acetate-soluble fraction to give pale yellow methyl glucoside / iso. 49 g of a crude product of an adduct of stearyl glycidyl ether was obtained. When this crude product was separated and purified using silica gel column chromatography, the target 1 mol adduct of methyl glucoside / isostearyl glycidyl ether was eluted with an elution solvent of acetone: hexane = 4: 1. Collect the eluate fractions and evaporate the solvent to remove the target methyl glucoside
1-Mole Adduct of Isostearyl Glycidyl Ether 16
g was obtained. Hydroxyl value 436 (calculated value 432) NMR (CDCl ₃ ): δ (ppm) 4.75 (1H, d, -OC H -OCH ₃ ), 3.95 (1H, m, -OCH ₂ -C H OH-CH ₂ O- ),
3.77 to 3.35 (12H, m, -OC H ₂ -,-OC H- ), 3.24 (3H, s, -OCH ₃ ), 1.
30 to 1.59 (29H, b, -C H ₂ -,-C H- ), 0.85 (6H, m, -C H ₃ ) IR (liquid film) cm ^-1 : ν _OH (-OH) 3200 to 3400 ν _OH (stretch) (-CH-,-CH ₂ -,-CH ₃ ) 2840,2915 ν _OH (bend) (-CH-,-CH ₂ -,-CH ₃ ) 1375,1460 ν _CO (-CO- ) 1110,1035,1005

Synthesis Example 4 69 g of maltitol, 400 g of N-methylpyrrolidone and 2 g of sodium hydroxide were placed in a 300 ml flask, and 1
It was heated to 10 ° C. to dissolve it, and dry nitrogen gas was blown into the solution to distill about 10 g of water and N-methylpyrrolidone to remove water in the reaction system. 38 g of 2-decyl tetradecyl glycidyl ether was added dropwise to the reaction solution over 2 hours, and then reacted at 110 ° C. for 4 hours while stirring. After completion of the reaction, 5 g of phosphoric acid was added to the reaction mixture to neutralize the catalyst, and then N-methylpyrrolidone was completely distilled off at 80 ° C. under reduced pressure, and 500 g of acetone was added to the residue for precipitation. Unreacted maltitol was filtered off. Acetone was distilled off from the obtained filtrate under reduced pressure to obtain 83 g of a crudely purified adduct of maltitol 2-decyltetradecylglycidyl ether. When this crude product is separated and purified by silica gel column chromatography, the target 1 mol adduct of maltitol 2-decyltetradecyl glycidyl ether is eluted with an eluting solvent of chloroform: methanol = 2: 1. Then, the eluted fractions were collected and the solvent was distilled off to obtain 20 g of a 1 mol adduct of maltitol 2-decyltetradecyl glycidyl ether. Hydroxyl value 663 (calculated value 670) NMR (CDCl ₃ ): δ (ppm) 4.90 (1H, d, -OC H -OCH ₃ ), 3.96 (1H, m, -OCH ₂ -C H OH-CH ₂ O- ),
3.78 ~ 3.42 (20H, m, -OC H ₂ -,-OC H- ), 1.30 ~ 1.59 (41H, b, -C
H ₂ -,-C H- ), 0.81 (6H, m, -C H ₃ ) IR (liquid film) cm ^-1 : ν _OH (-OH) 3200 to 3400 ν _OH (stretch) (-CH-,- CH ₂ -,-CH ₃ ) 2830,2910 ν _OH (Bending angle) (-CH-,-CH ₂ -,-CH ₃ ) 1370,1450 ν _CO (-CO-) 1030,1110

Synthesis Example 5 Methyl isostearate 29.9 was placed in a 1 liter reaction vessel equipped with a distillation condenser equipped with a thermometer, a stirrer and a pressure reducing device.
g (0.1 mol), pentaerythritol 68 g (0.
5 mol), 1.9 g of 28% sodium methylate / methanol solution and 450 ml of dimethylformamide were charged,
2.5 at 100 ° C and 100 to 120 mmHg vacuum
The reaction was carried out over time. During this reaction, about 100 ml of dimethylformamide was distilled from the reaction system. After cooling the contents of the reaction, about 400 ml of water was added and the layers were separated. After extraction by adding ether to the lower layer, the ether layer was added to the initially separated upper layer, and each layer was washed with 200 ml of water three times. After removing the ether under reduced pressure, crude pentaerythritol monoisostearate having a purity of 77% was obtained (yield 70
%). This was purified by silica gel chromatography (ethyl acetate / ethanol) until a single spot was obtained by thin layer chromatography, and 21 g of pentaerythritol monoisostearate (yield 50%) was obtained (purity 94%). IR (liquid ^{film) cm -1: 3450 (OH)} , 2840~2950 (CH), 1720 (C = O), 1640 (CH), 1040 (CO) 1 H-NMR (CDCl 3) δppm:

[0097]

[Chemical formula 23]

4.1 [(c), 2H], 3.6 [(b), 6H], 3.3 [(a), 3H], 2.
4 [(d), 2H], 1.1-1.7 [(e), 27H], 0.9 [(f), 6H]

Synthesis Example 6 (1) Glucose 160 g (0.88 mol) and 3-chloro-1,2-propanediol 956 g (8.
8 mol) and Dowex 50WX8 (H
40 g of a mold, 50 to 100 mesh) was added, and the temperature was raised to 60 ° C. with stirring and the reaction was performed for 16 hours. After the reaction,
3 unreacted under reduced pressure by filtration with a glass filter
-Chloro-1,2-propanediol was distilled off. The obtained residue was washed with 500 g of acetone three times in total, and then dried under reduced pressure to give 3-chloro-2-hydroxy-1-O-.
79 g of glucosyl propane was obtained (33% yield). (2) 83 g (0.3 mol) of 3-chloro-2-hydroxy-1-O-glucosylpropane obtained in (1) in the reactor
47 g (0.15 mol) of sodium isostearate, 1.0 g of tetrabutylammonium bromide and 200 ml of dimethylformamide were added, and the mixture was heated to 100 ° C. with stirring and reacted for 8 hours. After completion of the reaction, dimethylformamide was distilled off under reduced pressure. To the obtained residue, 300 g of water and 600 g of ethyl acetate were added, shaken vigorously, and allowed to stand to recover an ethyl acetate layer, and ethyl acetate was distilled off under reduced pressure to obtain a crude product. The crude product was further purified by silica gel chromatography (chloroform / methanol = 10: 1) to give 3-O-isostearoyl-
14 g of 1-O-glucosylglycerol was obtained (isolation yield 26%).

[0100]

[Chemical formula 24]

¹ H-NMR (CDCl ₃ ) δ (ppm, TMS standard): 0.79 to 1.03 (t, 6H), 1.11 to 1.45 (broad, 25H), 1.56 (broad,
2H), 2.33 (broad, 2H), 3.23 ~ 4.39 (m, 11H), 4.88 (broad, 1
H) IR (liquid film) cm ^-1 : 3400,2950 to 2860,1740,1650,1470,1390 to 950 mass spectrometry (FAB ionization method) m / z: 521 (M + H) ⁺

Synthesis Example 7 Pentaerythritol 82 g, dimethyl sulfoxide 2
00 g and 1 g of sodium hydroxide were put into a 500 ml flask, heated and dissolved at 105 ° C., dry nitrogen gas was blown thereinto, and about 20 g of water and dimethyl sulfoxide were distilled out to remove water in the reaction system. After 39 g of isostearyl glycidyl ether was added dropwise to this over 1 hour, 1
The reaction was carried out at 05 ° C. for 4 hours with stirring. After the reaction,
Acetic acid (1.5 g) was added to the reaction mixture to neutralize the catalyst, dimethyl sulfoxide was completely distilled off at 80 ° C. under reduced pressure, and 99% ethanol was added to the residue to separate unreacted pentaerythritol by filtration. did. Ethanol was distilled off from the obtained filtrate under reduced pressure, and water was added to the residue 500 times.
ml and ethyl acetate (500 ml) were added and the mixture was extracted with ethyl acetate. The solvent was distilled off from the ethyl acetate-soluble fraction to obtain 63 g of a pale yellow pentaerythritol-isostearyl glycidyl ether adduct. When gel permeation chromatography was performed on this crude product,
1 mole of isostearyl glycidyl ether added to pentaerythritol, 2 moles of diether body, 3 moles of triether body, and 4
It was confirmed that the mixture was a mixture of mole-added tetraethers, and the composition ratios of the monoethers, diethers, triethers and tetraethers were 77%, 19% and 3% from the peak area ratios, respectively. % And 1%. Hydroxyl value 438 IR (liquid film) cm ^-1 : ν _OH (-OH) 3200 to 3400 ν _OH (stretching) (-CH-,-CH ₂ -,-CH ₃ ) 2850,2920 ν _OH (bending angle) ( -CH-,-CH ₂ -,-CH ₃ ) 1375,1460 ν _CH (-CO-) 1110,1035,1010

Test Example 1 With respect to the nonionic amphipathic compound obtained in Synthesis Example,
The properties at room temperature (25 ° C) and 55 ° C and the dissolved state in water (concentration 5% by weight) were examined. The results are shown in Table 1. (Evaluation method) The properties at 25 ° C and 55 ° C were examined by a polarizing plate, a polarizing microscope, X-ray diffraction, DSC and the like. The dissolved state in the water system is the same as the property after collecting 1 g of the sample in a 30 ml sample bottle, adding ion-exchanged water to the sample concentration of 5% by weight, and then repeatedly heating and stirring to uniformly mix. The dissolved state was investigated by the method of.

[0104]

[Table 1]

Example 1 A hair oil having the composition shown in Table 2 was produced, and its performance and storage stability were investigated. The results are shown in Table 2. (Manufacturing method) Each component is heated to 70 ° C to dissolve it and stirred
After mixing, the mixture was cooled to room temperature with stirring to obtain hair oil. (Evaluation method) Performance evaluation 20 g of hair of a Japanese woman treated with cold perm
(A length of 15 cm) was bundled, this hair bundle was washed with a commercial shampoo containing an anion activator as a main component, and towel-dried. 0.02 g of the hair oil shown in Table 2 was uniformly applied, and this wet hair bundle was subjected to a sensory evaluation of its spreadability, familiarity, lack of moisturizing feel and oiliness, and dry brushability. The evaluation criteria are shown as ⊚ for excellent evaluation, ◯ for good evaluation, Δ for normal evaluation, and × for inferior evaluation.

Storage stability The sample was placed in a 100 ml transparent glass container, and after storage, the appearance was observed with the naked eye. The evaluation was based on the following criteria. ◯: The whole is uniform and no abnormality such as dispersion or aggregation is observed. X: It is non-uniform and separation, aggregation, etc. are recognized.

[0107]

[Table 2]

Example 2 Hair Treatment Composition:

[Table 3] (1) 2-dodecylhexadecyltrimethyl ammonium chloride 1.5 (% by weight) (2) Stearyl trimethyl ammonium chloride 1.0 (3) Dimethylpolysiloxane [wherein d = 1000] 1 .5 (4) cetostearyl alcohol 3.0 (5) 1 mol of pentaerythritol glyceryl isostearyl glycidyl ether adduct (Synthesis example 1) 3.0 (6) liquid paraffin 3.0 (7) hydroxyethyl cellulose (1 % Aqueous solution viscosity 8000cp) 0.5 (8) Polyoxyethylene oleyl ether (EO = 5) 0.5 (9) Methylparaben 0.2 (10) Perfume 0.4 (11) Water balance

Example 3 Conditioning Mousse Composition:

[Table 4] (1) Di2-hexadecyldimethylammonium chloride 0.5 (% by weight) (2) Methylphenyl polysiloxane [in the formula (12-2), e ₂ = 190, e ₃ = 10] 1. 0 (3) Isotridecyl myristate 1.0 (4) 3-Methyl-1,3-butanediol 1.0 (5) Liquid paraffin 2.5 (6) 1 mol adduct of methyl glucoside / isostearyl glycidyl ether ( Synthesis Example 3) 3.0 (7) 95% ethanol 5.0 (8) Methylparaben 0.1 (9) Perfume 0.1 (10) Water balance

Example 4 Hair Cream Composition:

[Table 5] (1) Di2-hexadecyldimethylammonium chloride 2.0 (wt%) (2) Cetyltrimethylammonium chloride 1.0 (3) Pentaerythritol monoisostearate (Synthesis example 5) 3.0 ( 4) cetyl alcohol 5.0 (5) amino-modified silicone [(13-1) _{^{wherein, R 4 = CH 3, f}} 1 = 2, f 2 = 1, f 3 = 4, R 5 = CH 3, R ^{_{6 = - (CH 2) 3}} OCH 2 CH (OH) CH 2 N (C 2 H 5) 2, R 7 = OH ] 2.0 (6) Liquid paraffin 3.0 (7) perfume 0.4 (8 ) Water balance

Example 5 Cream composition:

Oil phase components: (1) Maltitol 2-decyl tetradecyl 1 mol adduct of glycidyl ether (Synthesis Example 4) 3.0 (wt%) (2) Polyether-modified silicone [(17-1 ) In the formula, j ₁ = 25, j ₂ = 4, R ¹⁶ : j ₃ = 3, j ₄ = 10, j ₅ = 0, B = H] 0.5 (3) cetanol 2.0 (4) stearin Acid 3.0 (5) Trimethylol isoheptadecane 3.0 (6) Lipid (cholesteryl ester of isostearic acid) 8.0 (7) Monolauryl glycerin 2.0 (8) Polyoxyethylene (20) sorbitan monolauric acid Ester 2.0 Water phase component: (9) Methylparaben 0.2 (10) Perfume 0.1 (11) Water balance

Example 6 Emulsion composition:

Table 7 Oil phase components: (1) 3-O-isostearoyl-1-O-glucosylglycerol (Synthesis example 6) 3.0 (wt%) (2) cetanol 0.5 (3) petrolatum 1.0 (4) Polyoxyethylene (10) monooleic acid ester 2.0 (5) Stearic acid 2.0 (6) Dimethylpolysiloxane [in the formula (11), d = 1000] 1.0 Aqueous phase component: (7 ) Methylparaben 0.2 (8) Perfume 0.1 (9) Water balance

Example 7 Hair Treatment Composition:

Table 1 (1) 2-dodecylhexadecyl trimethyl ammonium chloride 1.5 (wt%) (2) stearyl trimethyl ammonium chloride 1.0 (3) dimethyl polysiloxane [d = 1000] 1 in the formula (11) 1 .5 (4) cetostearyl alcohol 3.0 (5) Pentaerythritol glyceryl isostearyl glycidyl ether 1 mol to 4 mol Mixture of adducts (Synthesis example 7) 3.0 (6) Liquid paraffin 3.0 (7) ) Hydroxyethyl cellulose (1% aqueous solution viscosity 8000 cp) 0.5 (8) Polyoxyethylene oleyl ether (EO = 5) 0.5 (9) Methylparaben 0.2 (10) Perfume 0.4 (11) Water balance

Claims (2)

[Claims] 1. A cosmetic comprising the following components (A) and (B). (A) having at least one long-chain branched alkyl or alkenyl group and at least three hydroxyl groups in one molecule, 2
Nonionic amphipathic compound (B) dimethyl polysiloxane, methylphenyl polysiloxane, amino-modified silicone, fatty acid-modified polysiloxane, alcohol-modified silicone, aliphatic having a lamellar liquid crystal structure at a temperature above 5 ° C. and 50 ° C. One or more silicones selected from the group consisting of alcohol-modified polysiloxane, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone and alkyl-modified silicone. 2. The component (A) is 0.01 to 80% by weight,
The cosmetic according to claim 1, which contains the component (B) in an amount of 0.01 to 30% by weight.