JP3130969B2 - Skin cosmetics - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a skin cosmetic, and more particularly, to a skin cosmetic for protecting the skin from roughening due to water work or the like, and mainly from roughening.

[0002]

2. Description of the Related Art Conventionally, hand creams have been widely used to protect skin from rough skin due to water work or the like.
The hand cream replenishes sebum lost by water work and the like, and imparts flexibility to the skin by adding a moisturizer and water.

[0003]

However, since the hand cream is easily washed away by washing with water, the effect of protecting the skin is not always satisfactory. In fact, some housewives suffer from hand washing due to repeated water work such as cooking and washing. Many people are suffering from. Dentists who frequently wash their hands cannot use hand creams because they must not adhere to treatment tools or patients, so their hands are worn away. In severe cases, unpleasant skin irritation often occurs. Also, many barbers complain of inflammation caused by hair dyes and perm solutions in addition to rough skin caused by hand washing. As a technique of a skin protective agent for a person engaged in such a terrible occupation, Japanese Patent Publication No. Sho 4
There is a composition described in Japanese Patent Application Laid-Open No. 8-1503, which is a composition obtained by combining a relatively high-viscosity trimethylsilyl-terminal-blocked diorganosiloxane and a silicone resin, so that it has a sticky feeling when applied to the skin. It is strong and has disadvantages such as remarkable adhesion to a contact object. Also, as a skin cosmetic that effectively protects the skin from water work and has a refreshing feeling of use, a technique using a high molecular weight dimethylpolysiloxane or a high molecular weight methylphenylpolysiloxane is known. (Japanese
-183515). However, even in this case, it was not sufficiently satisfactory in terms of water repellency and prevention of adhesion to a contact object. In view of such circumstances, the present inventors have found that the skin is effectively protected from water work, in particular, the protective effect is not lost even after repeated washing with water, and it has a refreshing feeling of use, and has a refreshing feeling on contact. As a result of diligent research aimed at obtaining a skin cosmetic with less adhesion, if a specific amino- or ammonia-modified high-molecular silicone is used, it will spread well and give a long-lasting feel when applied to the skin. The present inventors have found that a good water-repellent film which protects the skin over time and is not easily washed away even by washing with water is formed, and based on this finding, the present invention has been completed.

[0004]

That is, the present invention provides a compound represented by the following general formula 1:

Embedded image [In the formula, R ¹ represents a methyl group or a part thereof is a phenyl group, and R ² represents the same as R ³ or a methyl group or a hydroxyl group. R ³ is wherein R ⁴ Z {R ⁴ represents a divalent alkylene group having carbon atoms of 3 to 6, Z is _{^{-NR 5 2, -N + R 5}} 3
_{^{A -, -NR 5 (CH 2}} ) a NR 5 2, -NR 5 (CH 2) a N +
R ⁵ ₃ A ^- and _{^{-NR 5 (CH 2) a N}} (R 5) C = O
(R ⁶ ) (R ⁵ represents hydrogen or an alkyl group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, A represents Cl, Br or I;
Is an integer from 2 to 6. 1) selected from the group consisting of
Represents a valence group. Represents a substituent having an amino group or an ammonium group represented by｝, m and n are each a positive integer, m + n is an integer of 3,000 to 20,000, and n / m is 1/500 to 1 / 10,000. ]
Skin cosmetics other than makeup cosmetics , characterized in that they contain one or more amino- or ammonium-modified high molecular silicones represented by the formula:

The polymer silicone represented by the general formula 1 of the present invention has m + n of 3,000 to 20,000,
Preferably, it is 4,000 to 10,000. 3,0
If it is less than 00, it is oily and has insufficient skin protection effect.
If it exceeds 000, it does not dissolve in other cosmetic raw materials such as silicone oil and cannot be blended in cosmetics. Also,
n / m is 1/500 to 1 / 10,000, preferably 1/500 to 1/2000. If it exceeds 1/500, the content of amino groups or ammonium groups in the silicone increases, and a crosslinking reaction or the like occurs during production,
It is also not preferable from the viewpoint of raw material odor. 1 / 10,000
If it is less than 30, the interaction with the skin becomes weak, the skin protection effect becomes poor, and the water repellency becomes poor. The amino-modified or ammonium-modified high molecular silicone of the present invention can be produced by the same production method as general amino-modified or ammonium-modified silicone. For example, it can be produced by polycondensing γ-aminopropylmethyldiethoxysilane, cyclic dimethylpolysiloxane and hexamethyldisiloxane in the presence of an alkali catalyst.
The amino-modified or ammonium-modified high molecular silicone used in the present invention is in the form of a soft rubber, and even when used in a large amount, an extremely excellent skin cosmetic can be obtained without stickiness. The amount of the amino-modified or ammonium-modified polymer silicone in the present invention is 2 to 2 in the total amount of the cosmetic.
It is 50% by weight, preferably 2 to 30% by weight. If it is less than 2% by weight, a sufficient effect cannot be obtained, and if it exceeds 50% by weight, it is difficult to dissolve in other raw materials.

When the silicone of the present invention is blended in cosmetics, it may be dissolved in a volatile oil such as a low-boiling cyclic silicone oil or a low-boiling chain silicone oil having a volatile property, or a low-boiling isoparaffin hydrocarbon. Is preferred.
Examples of the low boiling point cyclic silicone oil include octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and the like. Examples of low boiling chain silicone oils include:
Dimethyl polysiloxane (viscosity 0.65 to 5 cSt / 2
5 ° C.). The low-boiling isoparaffinic hydrocarbon preferably has 1 to 30 carbon atoms.

[0007] In addition to the above essential components, the skin cosmetic composition of the present invention may contain olive oil, coconut oil, safflower oil, castor oil within a quantitative and qualitative range that does not impair the effects of the present invention depending on the purpose. Oils, fats such as cottonseed oil, waxes such as lanolin, jojoba oil, carnauba wax, hydrocarbon oils such as liquid paraffin, squalane, petrolatum, volatile isoparaffin, fatty acids, alcohols, cetyl octanoate, isopropyl myristate, etc. Silicone oils such as ester oils, dimethylpolysiloxane and methylphenylpolysiloxane, silicone resins, water-soluble polyhydric alcohols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, glycerin, sorbitol, polyethylene glycol, hyaluronic acid, chondroitin Sulfuric acid, pyrrolidone cal For example, moisturizers such as phosphates, ultraviolet absorbers, ultraviolet scattering agents, thickeners such as carboxyvinyl polymer, antioxidants, preservatives, anti-inflammatory agents, drugs such as vitamins and hormones, and general cosmetics such as fragrances. It is possible to mix other components.

Further, it is needless to say that a water-in-oil or oil-in-water type emulsified composition is used as long as water repellency is not lost by blending purified water, a water-soluble component and an appropriate emulsifier and making full use of emulsification technology. It is also possible to make things.
In addition, at the time of emulsification, an emulsifier is dissolved in a water-soluble polyhydric alcohol, an oil containing an amino-modified or ammonium-modified high molecular silicone is added and emulsified to form an emulsified composition, and the composition is diluted with water. It can also make emulsions. Emulsifiers used in this case include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene cholesteryl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glyceryl fatty acid ester, polyoxyethylene hardened castor oil, and polyethylene. Nonionic activators such as glycol fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, and polyether-modified silicones; stearyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, behenyltrimethylammonium chloride, and cetylpyridinium chloride Cationic activator, sodium cetyl sulfate, polyoxyethylene lauryl ether sodium sulfate Beam, sodium lauryl sulfate,
Anionic activators such as coconut oil fatty acid potassium and coconut oil fatty acid sodium methyltaurine. Examples of the water-soluble polyhydric alcohol include ethylel glycol, propylene glycol, 1,3-butylene glycol, 1,
4-butylene glycol, dipropylene glycol, glycerin, diglycerin, triglycerin, tetraglycerin, glucose, maltose, maltitol, sucrose, fructose, xylitol, sorbitol, maltotriose, threitol, erythritol, starch,
Degraded sugar-reduced alcohol, hyaluronic acid, etc., and one or more of these are used.

[0009]

The present invention will be described in more detail with reference to the following examples. The present invention is not limited by these. All amounts are by weight. Example 1 (Lotion) (1) Liquid paraffin 2.0% (2) Cetyl octoate 10.0 (3) Decamethylcyclopentasiloxane 60.0 (4) Amino-modified polymer silicone 20.0 (General formula 1) And R ¹ and R ² are methyl groups, and R ³ is — (CH ₂ ) ₃ N (CH ₃ ) ₂ m = 5,000, n = 5. (5) Methylphenylpolysiloxane 8.0 (n = 100) (1) to (5) were stirred and dissolved at 70 to 80 ° C., and cooled to obtain a lotion. Example 1 had a refreshing feeling of use and good water repellency, and had an effect of protecting the skin for a long time. In addition, even when the hand to which Example 1 was applied was touched with metal or the like, no component was attached.

Example 2 (Lotion) (1) Dimethylpolysiloxane (5cSt) 65.0% (2) Glyceryl triisostearate 5.0 (3) Amino-modified high molecular silicone 5.0 (R in general formula 1) ¹ and R ² are methyl groups, R ³ is — (CH ₂ ) ₃ N (CH ₃ ) (CH ₂ ) ₂ N (CH ₃ ) ₂ , m = 10,000, n = 5) (4) Olive oil 0 (1) to (4) were stirred and dissolved at 50 to 60 ° C., and cooled to obtain a lotion. Example 2 had a refreshing feel and good water repellency.

Comparative Example 1 (Lotion) (1) Liquid paraffin 2.0% (2) Cetyl octoate 10.0 (3) Decamethylcyclopentasiloxane 60.0 (4) Dimethylpolysiloxane (5 cSt / 25 ° C.) 20.0 (5) Methylphenylpolysiloxane 8.0 (n = 100) (1) to (5) were stirred and dissolved at 70 to 80 ° C., and cooled to obtain a lotion.

Comparative Example 2 (Lotion) (1) Dimethyl polysiloxane (5 cSt) 65.0% (2) Glyceryl triisostearate 5.0 (3) High molecular weight dimethyl polysiloxane 5.0 (Polymerization degree n = 7) (4) Olive oil 25.0 (1) to (4) were stirred and dissolved at 50 to 60 ° C., and cooled to obtain a lotion.

The following evaluations were performed on Examples 1 and 2 and Comparative Examples 1 and 2. A water drop is placed 30 minutes after applying the sample to the forearm, and the contact angle is measured. Further, after washing the forearm portion coated with the sample once with soap, a water drop is again placed and the contact angle is measured (measurement is performed at each of five places and an average value is obtained). Table 1 shows the results.

[0014]

[Table 1] ３０ 30 minutes after application After washing with soap ───────────── ───────────── Example 1 107 ゜ 103 ゜ Comparative Example 1 102 ゜ 62 ゜ Example 2 91 ゜ 87 ゜ Comparative Example 2 82 ゜ 51 ゜ ─────────ロ ー The lotion of the example has better water repellency than the comparative example,
Also, it had good water repellency even after washing with soap.

Example 3 (Cream) (1) Liquid paraffin 20.0% (2) Solid paraffin 5.0 (3) Microcrystalline wax 4.0 (4) Ammonium-modified high molecular silicone 30.0 (general formula 1) 10% of R ¹ is a phenyl group, the rest is a methyl group, R ² is a methyl group, R ³ is — (CH ₂ ) ₃ N ⁺ (CH ₃ ) ₃ Cl ⁻ , m = 10,000, n = 2) (5) Isopropyl myristate 6.0 (6) Volatile isoparaffin 35.0 (1) to (6) were stirred and dissolved at 70 to 80 ° C., and cooled to obtain a cream. Example 3 has a refreshing feeling,
It had the effect of protecting the skin for a long time. In addition, even when holding the cup or the like with the hand to which Example 3 was applied, no adhesion of the components was observed. Further, Example 3 is excellent in water resistance,
Even after washing 5 times with soap, it had good water repellency.

Example 4 (Moisture Lotion) (1) Squalane 10.0% (2) Isopropyl myristate 20.0 (3) Amino-modified high molecular silicone 5.0 (In the general formula 1, R ¹ is a methyl group, R ² hydroxyl, R ³ is _{- (CH 2) 3 n (} CH 3) 2, m = 3,000, n = 6) (4) decamethylcyclopentasiloxane 35.0 (5) sorbitan monooleate 5.0 (6) Purified water 22.0 (7) Dipropylene glycol 3.0 (1) to (5) were stirred and dissolved at 70 to 80 ° C., and (7) dissolved in (6) was added thereto. I got a moisturizing lotion.

Example 5 (Lotion) (1) Light liquid isoparaffin 15.0% (2) Amino-modified high molecular silicone 3.0 (In the general formula 1, R ¹ and R ² are methyl groups, and R ³ is-(CH ₂ ) ₃ N (CH ₃ ) ₂ , m = 8,000, n = 10) (3) Dimethyl polysiloxane (10 cSt) 5.0 (4) Olive oil 5.0 (5) 1,3-butylene glycol 0 (6) Polyoxyethylene (60 mol) 3.0 Hardened castor oil ester (7) Purified water 59.0 (8) Appropriate amount of fragrance (2) to (4) and (8) are dissolved in (1) ,
The solution (6) was dissolved in the solution (5) and emulsified. The emulsion was added to the solution (7) and dissolved to obtain a lotion.

[0018]

The skin cosmetic composition of the present invention has good spreadability, protects the skin for a long time with a refreshing feel when applied to the skin, and is not easily washed away even by washing with water. Furthermore, it is a skin cosmetic that has little adhesion to a target object even when touched by the hand or the like to which it is applied.

────────────────────────────────────────────────── (5) References JP-A-5-32527 (JP, A) JP-A-5-32532 (JP, A) JP-A-3-153620 (JP, A) Patent 2525193 (JP, A) B2) (58) Field surveyed (Int. Cl. ⁷ , DB name) A61K ^7/ 00-7/50

Claims (8)

(57) [Claims] 1. A compound of the general formula: [In the formula, R ¹ represents a methyl group or a part thereof is a phenyl group, and R ² represents the same as R ³ or a methyl group or a hydroxyl group. R ³ is wherein R ⁴ Z {R ⁴ represents a divalent alkylene group having carbon atoms of 3 to 6, Z is _{^{-NR 5 2, -N + R 5}} 3
_{^{A -, -NR 5 (CH 2}} ) a NR 5 2, -NR 5 (CH 2) a N +
R ⁵ ₃ A ^- and _{^{-NR 5 (CH 2) a N}} (R 5) C = O
(R ⁶ ) (R ⁵ represents hydrogen or an alkyl group having 1 to 4 carbon atoms, R ⁶ represents an alkyl group having 1 to 4 carbon atoms, A represents Cl, Br or I;
Is an integer from 2 to 6. 1) selected from the group consisting of
Represents a valence group. Represents a substituent having an amino group or an ammonium group represented by｝, m and n are each a positive integer, m + n is an integer of 3,000 to 20,000, and n / m is 1/500 to 1 / 10,000. ]
Skin cosmetics other than makeup cosmetics , characterized in that they contain one or more amino- or ammonium-modified high molecular silicones represented by the formula: 2. A manufacturer comprising a mixture of the amino-modified or ammonium-modified polymer silicone according to claim 1 dissolved in a low-boiling cyclic silicone.
Skin cosmetics other than cosmetics for cosmetics . 3. A manufacturer comprising a mixture of the amino-modified or ammonium-modified high molecular silicone according to claim 1 dissolved in a low boiling chain silicone.
Skin cosmetics other than cosmetics for cosmetics . 4. A skin cosmetic other than a cosmetic for make-up , characterized by blending the amino-modified or ammonium-modified polymer silicone of claim 1 dissolved in a low-boiling isoparaffinic hydrocarbon. 5. A make-up preparation characterized by emulsifying the amino-modified or ammonium-modified polymer silicone solution according to claim 2 with an emulsifier .
Emulsion type skin cosmetics other than cosmetics. 6. The method according to claim 5, wherein the emulsifier is a nonionic activator.
The emulsion type skin cosmetic according to the above. 7. The emulsion-type skin cosmetic according to claim 5, wherein the emulsifier is a cation or an anionic surfactant. 8. The emulsion-type skin according to claim 5, wherein, during the emulsification, an amino-modified or ammonium-modified polymer silicone solution is added to a solution obtained by dissolving an emulsifier in a water-soluble polyhydric alcohol to emulsify. Cosmetics.