JP3486052B2 - Coated powder and cosmetic containing the same - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a powder whose surface is coated with a modified silicone and a cosmetic containing the same,
More specifically, the present invention relates to a coated powder having good adhesion to the skin, a smooth feel, excellent usability, and high hydrophobicity, and a cosmetic containing the same.

[0002]

2. Description of the Related Art Various powders are blended in cosmetics. Depending on the purpose of improving adhesion to skin, water repellency, dispersibility, etc., powder surface Is subjected to a hydrophobic treatment. Many methods are known as the hydrophobic treatment, for example, a method using an oil agent, that is, a method of heat-treating the oil agent on the surface of the powder and a method of baking the oil agent are known. The surface treatment agent used for hydrophobizing the powder surface includes fluorine compounds, methylhydrogenpolysiloxane, methylhydrogensiloxane / dimethylsiloxane copolymer, acryl / silicone graft copolymer, alumina, silica and the like. It is known and used singly or in combination of two or more depending on the purpose.

[0003]

However, the treated powder obtained by the above-mentioned hydrophobic treatment method has a stronger squeaky feeling and bulkiness than the untreated powder when applied onto the skin. However, there was a problem that it felt like powder, and the usability was not favorable. Further, there is a problem in that the hydrophobic treatment lowers the affinity between the powder and the skin and deteriorates the adhesion to the skin. Therefore, there has been a demand for a surface-treated powder having sufficient hydrophobicity and capable of obtaining a cosmetic having a good adhesive property, a feeling of use and a long-lasting makeup when blended into a cosmetic.

[0004]

As a result of intensive investigations conducted by the present inventors in such a situation, the use of a powder surface-treated with a poly (N-acylalkyleneimine) -modified silicone results in the adhesion to the skin and the The present invention has been completed based on the finding that a cosmetic having an excellent feeling in use, a high hydrophobicity, and a good durability can be obtained.

That is, the present invention provides a skin cosmetic containing a coating powder whose surface is coated with a poly (N-acylalkyleneimine) -modified silicone.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The poly (N-acylalkyleneimine) -modified silicone used in the present invention has the formula (1) in the molecule.

[0007]

[Chemical 3]

(In the formula, R ¹ is a hydrogen atom and has 1 to 22 carbon atoms.
Or any of an alkyl group, a cycloalkyl group, an aralkyl group and an aryl group, and n is 2 or 3. ) Has a segment of poly (N-acylalkyleneimine) consisting of a repeating unit represented by the formula (1) and a segment of organopolysiloxane, wherein at least one of the silicon atoms at the terminal or side chain of the segment of organopolysiloxane is hetero. A segment of poly (N-acylalkyleneimine) composed of the repeating unit represented by the formula (1) is bonded via an alkylene group containing an atom .
In such a poly (N-acylalkyleneimine) -modified silicone, the weight ratio of the poly (N-acylalkyleneimine) segment to the organopolysiloxane segment is 1/50 to 20/1, preferably 1/40 to 2 / 1
And a molecular weight of 500 to 500,000, preferably 1,
Those of 000 to 300,000 are preferable for obtaining stable cosmetics.

Further, in the formula (1), examples of the cycloalkyl group represented by R ¹ include those having 3 to 6 carbon atoms; examples of the aralkyl group include phenylalkyl and naphthylalkyl; and examples of the aryl group. Examples thereof include phenyl, naphthyl, alkyl-substituted phenyl and the like. Examples of the alkylene group containing a hetero atom bonded to at least one silicon atom in the segment of the organopolysiloxane include a C2-20 alkylene group containing 1 to 3 nitrogen atoms, oxygen atoms or sulfur atoms. As a specific example, the formula (2)

[0010]

[Chemical 3]

Examples include groups represented by:

Preferred examples of such poly (N-acylalkyleneimine) -modified silicone include poly (N-
Formylethyleneimine modified silicone, poly (N-
Acetylethyleneimine) modified silicone, poly (N-
Propionylethyleneimine) modified silicone, poly (N-n-octanoylethyleneimine) modified silicone, poly (N-n-dodecanoylethyleneimine) modified silicone, poly (N-formylpropyleneimine) modified silicone, poly (N- Acetylpropylene imine)
Examples thereof include modified silicone, poly (N-propionylpropyleneimine) modified silicone, poly (Nn-octanoylpropyleneimine) modified silicone, and poly (Nn-dodecanoylpropyleneimine) modified silicone.

The above poly (N-acylalkyleneimine)
The modified silicone is a known method (Japanese Patent Laid-Open No. 2-27682).
4, JP-A-4-85334 and JP-A-4-8.
5335, JP-A-5-112423, JP-A-7-133352, etc.),
For example, it is synthesized by the following method. First, the segment of the poly (N-acylalkyleneimine) composed of the repeating unit represented by the formula (1) has the formula (3):

[0014]

[Chemical 5]

(In the formula, R ² is a hydrogen atom and has 1 to 22 carbon atoms.
Represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, and n is 2 or 3. ) Is obtained by ring-opening polymerization of the cyclic imino ether compound. The cyclic imino ether compound represented by the formula (3) is 2-oxazolines or 2-oxazines as exemplified below. That is, 2-oxazoline, 2-methyl-2-oxazoline, 2-ethyl-
2-oxazoline, 2-propyl-2-oxazoline,
2-butyl-2-oxazoline, 2-pentyl-2-oxazoline, 2-heptyl-2-oxazoline, 2-octyl-2-oxazoline, 2-nonyl-2-oxazoline, 2-decyl-2-oxazoline, 2- Undecyl-2-oxazoline, 2-dodecyl-2-oxazoline, 2-tridecyl-2-oxazoline, 2-tetradecyl-2-oxazoline, 2-pentadecyl-2-oxazoline, 2-hexadecyl-2-oxazoline, 2-
Heptadecyl-2-oxazoline, 2-octadecyl-
2-oxazoline, 2-nonadecyl-2-oxazoline, 2-eicosyl-2-oxazoline, 2-heneicosyl-2-oxazoline, 2-docosyl-2-oxazoline, 2-benzyl-2-oxazoline, 2-phenyl-2- Oxazoline, 2-naphthyl-2-oxazoline, 2-anthryl-2-oxazoline, 2-pyrenyl-2-oxazoline, 2-perylenyl-2-oxazoline, 2-cyclohexyl-2-oxazoline, 2-oxazine, 2-methyl- Oxazine, 2-ethyl-2-oxazine, 2-propyl-2-oxazine, 2-butyl-2-oxazine, 2-pentyl-2-oxazine, 2
-Hexyl-2-oxazine, 2-heptyl-2-oxazine, 2-octyl-2-oxazine, 2-nonyl-
2-oxazine, 2-decyl-2-oxazine, 2-undecyl-2-oxazine, 2-dodecyl-2-oxazine, 2-tridecyl-2-oxazine, 2-tetradecyl-2-oxazine, 2-pentadecyl-2- Oxazine, 2-hexadecyl-2-oxazine, 2-heptadecyl-2-oxazine, 2-octadecyl-2-oxazine, 2-nonadecyl-2-oxazine, 2-eicosyl-2-oxazine, 2-heneicosyl-2-oxazine, 2-docosyl-2-oxazine, 2-benzyl-2-oxazine, 2-phenyl-2-oxazine, 2
-Naphthyl-2-oxazine, 2-anthryl-2-oxazine, 2-pyrenyl-2-oxazine, 2-perylenyl-2-oxazine, 2-cyclohexyl-2-oxazine and the like can be mentioned.

These cyclic imino ethers are, for example, L
iebigs Ann. Chem. , P996 to p10
09 (1974). These compounds may be used alone as a monomer for ring-opening polymerization, or may be used in combination of two or more kinds.

Examples of the polymerization initiator for ring-opening polymerization of the above cyclic imino ether include toluene sulfonic acid alkyl ester, sulfuric acid dialkyl ester, trifluoromethane sulfonic acid alkyl ester and alkyl halide, but are not limited thereto. Absent. These initiators can be used alone or as a mixture.

A molecular chain of poly (N-acylalkyleneimine) can be obtained by ring-opening polymerization of the cyclic iminoether compound represented by the above formula (3) using these initiators. The chain may be a homopolymer chain or a copolymer chain, and the copolymer chain may be a random copolymer chain or a block copolymer chain.

The above poly (N-acylalkyleneimine)
The molecular weight of the molecular chain is preferably 150 or more and 50,000 or less, more preferably 500 or more and 10,000 or less. When the molecular weight is less than 150, the property of poly (N-acylalkyleneimine) is lost, and 5
If it is more than 10,000, the production becomes difficult, which is not preferable.

The modified silicone used in the present invention is a polymerization active species produced by ring-opening polymerization of a cyclic iminoether compound represented by the formula (3), and an organopolysiloxane having a functional group capable of reacting with the polymerization active species. Can be obtained by reacting.

As the functional group capable of reacting with the above-mentioned polymerization active species, primary, secondary or tertiary amino group, mercapto group, hydroxyl group, carboxylate group and the like can be mentioned. Among them, amino group or mercapto group is preferable. is there. The organopolysiloxane containing an amino group or a mercapto group in the molecule preferably has a molecular weight of 300 or more and 400,000 or less, more preferably 800 or more and 250,000 or less, and even if it is linear, it may be branched. May be included. If the molecular weight of the organopolysiloxane is less than 300, it is not preferable for obtaining a stable emulsion, and
If it is more than 400,000, it becomes gelled and is difficult to react, which is not preferable. The contained amino group or mercapto group may be introduced into any part of the main chain and the side chain.

The reaction between the organopolysiloxane having an amino group or a mercapto group and the reactive end of poly (N-acylalkyleneimine) obtained by the cationic polymerization of cyclic iminoether can be carried out as follows. .

The initiator is used in combination with a polar solvent, preferably a single solvent such as acetonitrile, valeronitrile, dimethylformamide, dimethylacetamide, chloroform, methylene chloride, ethylene chloride, ethyl acetate, methyl acetate, or other solvent as necessary. Dissolved in a mixed solvent of 40 to 1
The temperature is raised to 50 ° C, preferably 60 to 100 ° C. The cyclic iminoether represented by the above general formula (3) is added thereto all at once, or when the reaction is vigorous, it is dropped to carry out polymerization. The progress of polymerization can be traced by quantifying the residual amount of the cyclic iminoether, which is a monomer, with an analytical instrument such as gas chromatography. Even if the cyclic imino ether is consumed and the polymerization is completed, the active species at the growing terminal remains reactive. Without isolating the polymer
Subsequently, this polymer solution is mixed with an organopolysiloxane containing an amino group or a mercapto group in the molecule, and reacted at 5 to 100 ° C, preferably 20 to 60 ° C. The mixing ratio can be appropriately selected as desired, but the reaction is carried out at a ratio of 0.1 to 1.3 molar equivalents of poly (N-acylalkyleneimine) to 1 mol of the amino group or mercapto group in the organopolysiloxane. Is preferred. When the amount is less than 0.1 molar equivalent, the modification ratio is small, so that the property of the poly (N-acylalkyleneimine) intended in the present invention is hard to be imparted, and more than 1.3 molar equivalent is unnecessary.

By the reaction as described above, a block copolymer or graft polymer having poly (N-acylalkyleneimine) segments attached to polydimethylsiloxane can be obtained. The poly (N-acylalkyleneimine) -modified silicone may be used alone or in combination of two or more.

In the present invention, the powder coated with the poly (N-acylalkyleneimine) -modified silicone is not particularly limited as long as it is a powder usually used in cosmetics, and it may be an inorganic powder, an organic powder or a pearl. Agents are used.
Specifically, talc, mica, kaolin, titanium oxide,
Aluminum silicate, anhydrous silicic acid, zinc oxide, calcium carbonate, magnesium carbonate, red iron oxide, yellow iron oxide, black iron oxide, ultramarine blue, titanium mica, sericite, aluminum oxide, zirconium oxide, bismuth oxychloride, iron oxide mica, etc. Can be mentioned. Examples of the organic powder include polyethylene, polystyrene, cellulose, nylon, acrylic resin, polytetrafluoroethylene, silk powder and the like, and these can be used alone or in combination of two or more kinds. The average particle size of the powder is not particularly limited, as the optimum particle size differs depending on the purpose of blending in the cosmetic. For example, in the case of plate-like powders such as mica, talc, and sericite, which are extender pigments, 1
.About.50 .mu.m, preferably 3 to 30 .mu.m, particularly preferably 5 to 25 .mu.m. Also, nylon powder, PMMA,
Spherical powder such as silica is 0.1 to 4 in terms of smoothness.
0 μm, preferably 0.2 to 30 μm, particularly preferably 0.2 to 25 μm. Furthermore, in the case of coloring titanium oxide, zinc oxide, iron oxide or the like, 0.01 to 1 is used.
It is 0 μm, preferably 0.02 to 7 μm, and particularly preferably 0.03 to 5 μm.

In the present invention, the method of coating the powder with the poly (N-acylalkyleneimine) modified silicone is not particularly limited. Generally, the powder may be treated with a poly (N-acylalkyleneimine) -modified silicone, and specifically, a solution in which the poly (N-acylalkyleneimine) -modified silicone is dissolved and the powder are mixed and filtered. Alternatively, a method of mixing under reduced pressure at room temperature or heating and then distilling off the solvent is desirable. Any solvent can be used as long as it can dissolve poly (N-acylalkyleneimine) -modified silicone, and for example, lower alcohols, ethers, esters and the like are used. Among them, ethanol, isopropyl alcohol, ethyl acetate and the like are preferable.

The treatment amount of the poly (N-acylalkyleneimine) -modified silicone varies depending on its kind, but is usually 0.1 to 50% by weight of the powder, particularly 1 to 2%.
0 wt% is desirable. The mixing temperature is 20 ° C to 90 ° C.
The degree is desirable. In addition, the amount of solvent is preferably 0.3 to 30 times, and more preferably 0.5 to 10 times the weight of the powder.
Mixing time varies depending on the throughput and type of powder, but is usually 1
~ 15 hours are preferred.

The coated powder prepared in this manner has the surface of the powder coated with poly (N-acylalkyleneimine) -modified silicone, and the poly (N-acylalkyleneimine) present on the surface of the powder. ) Part of the modified silicone may be chemically bonded to the constituent components of the raw material powder.

The cosmetic powder can be blended in the cosmetic according to a conventional method. Examples of such cosmetics include makeup cosmetics such as foundation, powder, makeup base, white powder, blusher, eye shadow, eyebrow, lipstick, skin care cosmetics such as lotion and emulsion, cream, UV protection cosmetics, body emulsion. , Body powder, baby powder, and other body cosmetics.

[0030]

The cosmetics containing the coated powder of the present invention are
It has a good feel when applied to the skin and has a good affinity with the skin, and therefore has excellent adhesion to the skin.

[0031]

The present invention will be further described with reference to examples, but the present invention is not limited thereto. In the synthesis examples, the weight average molecular weight is determined by gel permeation liquid chromatography using chloroform as a developing solvent, and the value is a polystyrene conversion value.

Synthesis Example 1 (Synthesis of Poly (N-acetylethyleneimine) Modified Silicone) 13.03 g (0.070 mol) of methyl-p-toluenesulfonate (methyltosylate), 2-methyl-2
A mixture of 70 g (0.82 mol) of oxazoline, 10 ml of acetonitrile and 30 ml of chloroform was refluxed for 6 hours to synthesize a terminal reactive polymer (molecular weight 1,000) of poly (N-acetylethyleneimine). To this reaction solution, 3-aminopropyl-substituted polydimethylsiloxane at both ends (manufactured by Chisso Corporation, FM3311, molecular weight 1,000)
A solution prepared by dissolving 31.8 g in 50 ml of chloroform was added and reacted at 55 ° C. for 24 hours. The solvent was distilled off under reduced pressure to obtain a block copolymer (molecular weight 3,000) having poly (N-acetylethyleneimine) chains attached to both ends of polydimethylsiloxane. The copolymer was a light yellow, brittle solid (yield 110.2 g,
Yield 96%).

Synthesis Example 2 (Synthesis of Poly (N-n-dodecanoylpropyleneimine) Modified Silicone) 1.45 g (7.8 × 10 ⁻³ mol) of methyl tosylate,
7.8 g of 2-n-undecyl-2-oxazine (0.0
33 mol) and 1 ml of a mixture of 10 ml of dimethylacetamide.
The temperature was kept at 00 ° C. for 24 hours to synthesize poly (N-n-dodecanoylpropyleneimine) (molecular weight 1,000). To this reaction solution was added 3-aminopropyl-substituted polydimethylsiloxane at both ends (manufactured by Chisso Corporation, FM3325, molecular weight 1).
A solution prepared by dissolving 38.9 g of 10,000) in 50 ml of chloroform was added, and the mixture was refluxed for 72 hours. Then, it was reprecipitated with methanol, and the residue was dried under reduced pressure. The obtained polymer was a yellow viscous liquid and had a molecular weight of 12,000 (yield 45.7 g, yield 95%).

Synthesis Example 3 (Synthesis of Poly (N-acetylethyleneimine) Modified Silicone) 3.26 g (0.018 mol) of methyl tosylate, 2-
A mixture of 70 g (0.82 mol) of methyl-2-oxazoline, 10 ml of acetonitrile and 40 ml of chloroform was added to 6 parts.
After refluxing for an hour, poly (N-acetylethyleneimine) (molecular weight 4,000) was synthesized. Add 3 to the side chain in this reaction solution.
-Polydimethylsiloxane substituted with aminopropyl group (KF865, manufactured by Shin-Etsu Silicone Co., Ltd., amine equivalent 4,4)
00, molecular weight 2,000) 63.6 g of chloroform 1
A solution dissolved in 50 ml was added and reacted at 55 ° C. for 24 hours. By distilling off the solvent under reduced pressure, a graft polymer (molecular weight 6,000) having a poly (N-acetylethyleneimine) chain attached to polydimethylsiloxane and a molecular weight 2,
A mixture of 000 silicones was produced. This polymer was a pale yellow fragile solid (yield 134.1 g, yield 98%).

Synthesis Example 4 Synthesis of (N-acetylethyleneimine). (Nn-octanoylethyleneimine) Random Copolymer Modified Silicone 1.86 g (0.01 mol) of methyl tosylate, 2-n
-Heptyl-2-oxazoline 10 g (0.059 mol), 2-methyl-2-oxazoline 10 g (0.11)
A mixture of 74 mol) and 20 ml of chloroform was refluxed for 6 hours to synthesize a (N-acetylethyleneimine). (N-n-octanoylethyleneimine) random copolymer (molecular weight 2,000). Chloroform 150 was added to 43.34 g of polydimethylsiloxane having a side chain substituted with 2-aminoethylaminopropyl group (manufactured by Shin-Etsu Silicone Co., Ltd., KF857, amine equivalent 830, viscosity 70 cs (25 ° C.)).
The above random copolymer solution was added to a solution dissolved in g and refluxed for 10 hours. The solvent was distilled off under reduced pressure to give a poly (N-acylethyleneimine) -grafted copolymer (molecular weight: 1900).
0) was obtained. The copolymer was a pale yellow viscous liquid (yield 64.5 g, yield 99%).

Synthesis Example 5 (Synthesis of poly (N-formylpropyleneimine) -modified silicone) Methyl tosylate 13.03 g (0.070 mol), 2
A mixture of 70 g (0.82 mol) of oxazine, 10 ml of acetonitrile and 30 ml of chloroform was refluxed for 6 hours,
An end-reactive polymer (molecular weight 1,000) of poly (N-formyl propylene imine) was synthesized. Polydimethylsiloxane having a 3-mercaptopropyl group in its side chain was added to this reaction solution (X-22-98 manufactured by Shin-Etsu Silicone Co., Ltd.).
0, sulfur content 1.7%, viscosity 150cs (25 ℃))
Add a solution of 50 g in 100 ml of chloroform,
The reaction was carried out at 30 ° C for 3 hours and then at 60 ° C for 24 hours. By distilling off the solvent under reduced pressure, a graft polymer (molecular weight 6,200) in which poly (N-formylpropyleneimine) chain was attached to polydimethylsiloxane was obtained. The copolymer was a pale yellow viscous liquid (yield 129.0).
g, yield 97%).

Synthesis Example 6 (Synthesis of amino-modified silicone containing a tertiary amino group in its side chain (precursor of Synthesis Example 7)) 6.00 g (0.031 mol) of N, N-dimethylaminopropylmethyldimethoxysilane 1.46 g of water (0.
After heating the mixture (081 mol) at 60 ° C for 5 hours, the produced methanol and water are removed under reduced pressure at 60 ° C and 2 to 5 mmHg. After the temperature was raised to 80 ° C., 228 g (0.769 mol) of octamethylcyclotetrasiloxane, 1.92 g (1.18 × 10 ⁻² mol) of hexamethyldisiloxane and 0.90 g of polymerization catalyst (tetramethylammonium hydroxide 0) Containing 12 g (1.32 × 10 ⁻³ mol) of tetramethylammonium hydroxide pentahydrate dissolved in octamethylcyclotetrasiloxane and toluene, reacted at 80 ° C. for 12 hours, and vacuum dried at 80 ° C./2 mmHg. The content of tetramethylammonium hydroxide was determined by the hydrochloric acid titration method), and the mixture was heated for 72 hours in a nitrogen atmosphere. 1
The oligomer was removed at 20 ° C. under a vacuum of 2 to 5 mmHg to synthesize an amino-modified silicone containing a tertiary amino group in the side chain represented by the following formula. The product was a colorless and transparent oil (225 g). The weight average molecular weight is 22,
It was 000. The amine equivalent was 7,200 as determined by the hydrochloric acid titration method.

[0038]

[Chemical 6]

Synthesis Example 7 (Synthesis of Poly (N-propionylethyleneimine) Modified Silicone) 2.36 g (0.0153 mol) of diethyl sulfate and 30.3 g (0.306 mol) of 2-ethyl-2-oxazoline.
Was dissolved in 43 ml of chloroform and heated under reflux in a nitrogen atmosphere for 5 hours to give poly (N-propionylethyleneimine).
A terminal reactive polymer (molecular weight of 2,000) was synthesized. A solution of 100 g of the tertiary amino-modified silicone synthesized in Synthesis Example 6 (0.0139 mol as an amino group) in 270 ml of chloroform was added thereto all at once, and the mixture was heated under reflux for 16 hours. The reaction mixture was concentrated under reduced pressure, and a graft copolymer having a N-propionylethyleneimine chain attached to a polydimethylsiloxane represented by the following formula (molecular weight 28,90
0) was obtained. The polymer was a pale yellow rubbery solid (yield 129 g, yield 97%).

[0040]

[Chemical 7]

Synthesis Example 8 (Synthesis of Poly (N-propionylethyleneimine) Modified Silicone) 3.55 g (0.0230 mol) of diethyl sulfate and 27.4 g (0.276 mol) of 2-ethyl-2-oxazoline.
Was dissolved in 60 g of dehydrated ethyl acetate, and the solution was placed under a nitrogen atmosphere.
The mixture was heated under reflux for a period of time to synthesize a poly (N-propionylethyleneimine) terminal reactive polymer (molecular weight 1,200). Here, side chain primary aminopropyl-modified polydimethylsiloxane (molecular weight 110,000, amine equivalent 2
0,800) 400 g (0.0192 mol in terms of amino group) in 50% ethyl acetate solution was added all at once, and the mixture was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure to obtain a graft copolymer having a N-propionylethyleneimine chain on polydimethylsiloxane (molecular weight: 115,000). This copolymer was a pale yellow rubbery solid (yield 4
27 g, yield 99%).

Synthesis Example 9 (Synthesis of Poly (N-propionylethyleneimine) Modified Silicone) 3.77 g (0.0244 mol) of diethyl sulfate and 48.4 g (0.488 mol) of 2-ethyl-2-oxazoline.
Was dissolved in 107 g of dehydrated chloroform and heated under reflux for 5 hours under a nitrogen atmosphere to synthesize a poly (N-propionylethyleneimine) end-reactive polymer (molecular weight 2,000). A 50% ethyl acetate solution of 400 g (0.0407 mol in terms of amino group) of side chain primary aminopropyl-modified polydimethylsiloxane (molecular weight 110,000, amine equivalent 9,840) (0.0407 mol) was added all at once for 13 hours. Heated to reflux. The reaction mixture was concentrated under reduced pressure to obtain a graft copolymer having a N-acetylethyleneimine chain attached to polydimethylsiloxane (molecular weight: 137,000).
The obtained copolymer was a pale yellow rubbery solid (yield 444 g,
The yield was 98%).

Examples 1 to 5 10 g of the compounds obtained in Synthesis Examples 1 to 5 were placed in a round bottom flask.
Then, 600 g of isopropyl alcohol was further added, mixed and dissolved. Thereafter, 150 g of sericite having an average particle size of 7 μm was added thereto, and the mixture was further stirred at 60 ° C. for 4 hours. Thereafter, isopropyl alcohol was distilled off under reduced pressure at 50 ° C. to 60 ° C., dried and pulverized to obtain the desired coated powder (average particle size 7 μm).

Comparative Example 1 Untreated sericite 150 similar to that used in Example 1
g and 10 g of methyl hydrogen siloxane / dimethyl siloxane copolymer with an air blender (air temperature 5
0 ° C.) and mixed. Next, heat treatment is performed at 80 ° C. for 1 hour, then the temperature is raised to 105 ° C., and heat treatment is further performed for 1 hour.
A dimethylsiloxane copolymer-coated sericite was obtained.

Tactile Evaluation and Hydrophobicity Evaluation Ten panelists specialized in the surface treatment of Examples 1 to 5 and Comparative Example 1 and untreated sericite alone were evaluated by 10 panelists in 5 stages of 1 to 5 below. Get evaluated,
The average value is shown. Further, the hydrophobicity was evaluated by the contact angle of water when a powder was tabletted and water droplets were dripped on the tablet, and evaluated in the following 5 grades.

Feeling evaluation (spreading, squeaking, graininess, powderiness) 1: Poor feeling. 2: The feeling is a little bad. 3: Normal. 4: Feels a little good. 5: Feels good.

Hydrophobic 1: Water was absorbed in the powder. 2: 0 to less than 30 degrees 3: 30-less than 90 degrees 4: 90 to less than 120 degrees 5: 120-180 degrees

[0048]

[Table 1]

As is clear from the above, the coated sericites of Examples 1 to 5 were excellent in feeling in use and hydrophobicity.

Example 6 (Powder Foundation) A powder foundation having the following composition was produced by the following production method.

[0051]

[Table 2] (Composition) (wt%) (1) Poly (N-acylalkyleneimine) -modified silicone (Synthesis Example 1) Coated powder (the following powder was treated in the same manner as in Example 1) Site 20.0 Zinc oxide 8.0 Titanium oxide 10.0 Mica balance Kaolin 5.0 Bengala 0.8 Yellow iron oxide 2.5 Black iron oxide 0.1 (2) Liquid paraffin 8.0 (3) Beeswax 2. 0 (4) Preservative 0.2 (5) Perfume Proper amount 100.0

(Manufacturing Method) The component (1) was mixed and pulverized through a pulverizer. This was transferred to a high-speed blender, and components (2) to (5) which had been heated and mixed to make uniform were added and further mixed to make uniform. Then, this was processed with a crusher, passed through a sieve, and compression-molded in a metal plate to obtain a desired powder foundation.

Examples 8 to 10 (powder foundation) The compounds obtained in Synthesis Examples 7 to 9 were used to coat an untreated powder similar to the component (1) of Example 6 in the same manner as in Example 1. Processed. The obtained coated powder was used as the component (1) of Example 6.
A powder foundation was produced in the same manner as in Example 6 except that the powder foundation was used instead of.

Comparative Example 2 A coating treatment was carried out in the same manner as in Comparative Example 1 except that the untreated powder similar to the component (1) of Example 6 was used in place of the untreated sericite in Comparative Example 1. Example 6 except that the resulting coated powder was used in place of component (1) of Example 6
A powder foundation was produced in the same manner as in.

(Evaluation of Feeling / Evaluation of Makeup Persistence) The texture of powder foundations of Examples 6 to 10 and Comparative Example 2 was evaluated by 10 professional panelists in 5 grades from 1 to 5 as shown below. Each of the four grades was evaluated and the average value was shown.

Feeling evaluation (spreading, sticking, familiarity, lack of powderiness, lack of bulkiness) 1: Feeling is bad. 2: The feeling is a little bad. 3: Normal. 4: Feels a little good. 5: Feels good.

Makeup lasting 1: The makeup is broken. 2: The makeup is a little worn. 3: Almost no makeup is damaged. 4: Does not lose makeup.

[0058]

[Table 1]

As is clear from the above, the powder foundations of Examples 6 to 10 were excellent in the feeling of spreading, sticking, familiarity and the like and the durability of makeup.

Example 11 (two-layer liquid foundation)

[Table 4] (Composition) (% by weight) (1) Poly (N-acylalkyleneimine) -modified silicone (Synthesis example 1) Coated powder (the following powder was treated in the same manner as in Example 1) Oxidation Titanium 4.5 Sericite 4.5 Iron oxide (red, yellow, black) 1.5 (2) Octamethylcyclotetrasiloxane 20.0 (3) Dimethylpolysiloxane (10 cSt) 10.0 (4) Dimethylsiloxane Methyl polyoxyethylene siloxane copolymer 1.0 (5) Glycerin 2.0 (6) Ethanol 15.0 (7) Purified water balance (8) Octyl methoxycinnamate 2.0 (9) Fragrance micrometer 100.0

(Manufacturing Method) Components (2) to (4) and (8)
After dissolving (9) and (9) at room temperature, the component (1) was dispersed with a disper. Next, the components (5) to (7) were added with stirring and emulsified to obtain the intended two-layer liquid foundation. The above-mentioned two-layer type liquid foundation was excellent in feeling such as spreadability and familiarity, was excellent in adhesion to the skin, and was excellent in durability of makeup.

Example 12 (lotion) A lotion having the following composition was produced by the following production method.

[Table 5] (Composition) (% by weight) (1) Purified water 74.0 (2) Ethanol 15.0 (3) Glycerin 10.0 (4) Poly (N-acylalkyleneimine) modified silicone 1.0 ( Synthesis Example 2) Coated powder ( processed with zinc oxide powder by the same method as in Example 1 ) 100.0 in total

(Manufacturing method) Components (2) and (3) were added to component (1), the mixture was stirred with an anchor mixer, component (4) was added, and the mixture was further mixed with a disper to obtain a lotion. .

This lotion gave a smooth feeling of use and had a long lasting makeup.

Example 13 (two-layer type skin care emulsion) A two-layer type skin care emulsion having the following composition was produced by the following method.

(Table 6) (Composition) (% by weight) (1) Octamethyltetrasiloxane 25.0 (2) Dimethylpolysiloxane (10 cSt) 5.0 (3) Dimethylsiloxane / methylpolyoxyethylenesiloxane copolymer 1.0 (4) Squalane 5.0 (5) Glycerin 7.0 (6) Ethanol 15.0 (7) Purified Water Balance (8) Poly (N-acylalkyleneimine) Modified Silicone 7.0 (Synthesis Example 3) Coated Powder Body ( treated with porous silica powder in the same manner as in Example 1 ) 100.0

(Production Method) Components (1) to (4) were dissolved at room temperature, and then component (8) was dispersed with a disper.
The mixture of components (5) to (7) was added to this while stirring and emulsified to obtain a two-layer type skin care emulsion.

This two-layer type skin care emulsion gave a refreshing feeling of use, had good skin familiarity and good makeup retention.

Example 14 (two-layer type sunscreen emulsion) A two-layer type sunscreen emulsion having the following composition was produced by the following production method.

[Table 7] (Composition) (% by weight) (1) Octamethyltetrasiloxane 25.0 (2) Dimethylpolysiloxane (6cSt) 5.0 (3) Dimethylsiloxane / methylpolyoxyethylenesiloxane copolymer 1.0 (4) Squalane 5.0 (5) Glycerin 7.0 (6) Ethanol 15.0 (7) Purified water Balance (8) Octyl methoxycinnamate 2.0 (9) Poly (N-acylalkyleneimine) modified silicone 3.5 (synthesis example 4) coated powder (example 1 in the same manner as in fine particles of titanium oxide (MT-500SA, manufactured by Tayca Corporation) those that have been treated with) total 100.0

(Manufacturing Method) After dissolving the components (1) to (4) and (8) at room temperature, the component (9) was dispersed with a disper. The mixture of components (5) to (7) was added to this with stirring and emulsified to obtain a two-layer sunscreen emulsion.

This two-layer type sunscreen emulsion spreads,
It was well-known, had a refreshing feel, and had good makeup lasting.

Example 15 (dual-use powder foundation) A dual-use powder foundation having the following composition was produced by the following production method.

[Table 8] (Composition) (% by weight) (1) Poly (N-acylalkyleneimine) -modified silicone (Synthesis Example 5) Coated powder (the following powder was treated in the same manner as in Example 1) Oxidation Titanium 10.0 Mica Titanium 3.5 Sericite 20.0 Mica Balance Kaolin 5.0 Talc 4.0 Aluminum Oxide 10.0 Barium Sulfate 5.0 Bengala 0.8 Yellow Iron Oxide 2.5 Black Iron Oxide 0.1 (2) Liquid paraffin 4.0 (3) Squalane 2.0 (4) Methylphenyl polysiloxane (100 cSt) 4.0 (5) Preservative 0.2 (6) Perfume proper amount meter 100.0

(Manufacturing Method) The component (1) was mixed and pulverized through a pulverizer. This was transferred to a high-speed blender, and components (2) to (6) which had been heated and mixed to make uniform were added and further mixed to make uniform. Then, this was processed with a crusher, the particle size was made uniform through a sieve, and then compression-molded in a gold plate to obtain a dual-use powder foundation.

This dual-purpose powder foundation gave a refreshing feeling of use, was excellent in feeling of spreading, familiarity, and the like, and had good makeup retention.

[0074]

[0075]

[0076]

Example 17 (blusher) A blusher having the following composition was produced by the following production method.

[Table 10] (Composition) (wt%) (1) Poly (N-acylalkyleneimine) -modified silicone (Synthesis Example 7) Coated powder (the following powder was treated in the same manner as in Example 1) Oxidation Titanium 10.0 Mica 13.0 Kaolin Balance Red No. 202 2.5 Iron oxide (red, yellow, black) 5.0 (2) Dimethylpolysiloxane (10 cSt) 10.0 (3) Liquid paraffin 2.0 (4 ) Preservative 0.1 (5) Fragrance Suitable amount 100.0

(Manufacturing Method) The component (1) was mixed and pulverized through a pulverizer. This was transferred to a high-speed blender, and components (2) to (5) which had been heated and mixed to make uniform were added and further mixed to make uniform. Then, this was processed with a crusher, and after making a particle size uniform through a sieve, it was compression-molded in a gold plate to obtain a blusher.

The blusher had good spreadability, familiarity with the skin, and long lasting makeup.

Example 18 (makeup base cream) A makeup base cream having the following composition was produced by the following production method. (Composition) (% by weight) (1) Decamethylcyclopentasiloxane 30.0 (2) Aristo wax 4.0 (3) Sorbitan diisostearate 2.0 (4) Dimethyl polysiloxane (6cSt) 15.0 ( 5) Octyl methoxycinnamate 1.0 (6) Poly (N-acylalkyleneimine) modified silicone (Synthesis Example 8) Coated powder (the following powder was treated in the same manner as in Example 1) Sericite 5 0.0 Nylon powder 3.0 Iron oxide (red, yellow, black) 0.1 (7) 1,3-butylene glycol 5.0 (8) Preservative 0.1 (9) Purified water Balance (10) Fragrance Trace amount 100.0 in total

(Manufacturing Method) The components (1) to (5) were heated and dissolved, then the component (6) was added, and the components were uniformly mixed with a homogenizer. Furthermore, the component (7) which was previously heated and dissolved at 40 ° C.
The mixture of (10) was added and emulsified. Then, it cooled to room temperature and obtained the makeup base cream.

This makeup base cream had good spreadability, good familiarity, and good makeup retention.

─────────────────────────────────────────────────── ─── Continued Front Page (51) Int.Cl. ⁷ Identification Code FI C09C 1/00 C09C 1/00 1/02 1/02 1/04 1/04 1/24 1/24 1/28 1/28 1/32 1/32 1/36 1/36 1/40 1/40 1/42 1/42 3/12 3/12 (56) Reference JP-A-7-242518 (JP, A) JP-A-7 -133352 (JP, A) JP 5-112423 (JP, A) JP 5-25025 (JP, A) JP 7-258040 (JP, A) JP 7-173395 (JP, A) ) JP-A-3-287509 (JP, A) JP-A-8-104512 (JP, A) JP-A-62-187770 (JP, A) JP-A-6-9898 (JP, A) JP-A-6- 32991 (JP, A) JP-A-7-187674 (JP, A) JP-A-8-48910 (JP, A) JP-A-8-104606 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) A61K 7/02 A61K 7/031 A61K 7/42 C08G 77/388 C08 G 77/452 C09C 1/00 C09C 1/02 C09C 1/04 C09C 1/24 C09C 1/28 C09C 1/32 C09C 1/36 C09C 1/40 C09C 1/42 C09C 3/12

Claims (2)

(57) [Claims] 1. A compound represented by the formula (1) : (In the formula, R ¹ is a hydrogen atom or an alkyl having 1 to 22 carbon atoms.
Group, cycloalkyl group, aralkyl group, aryl group
The difference is n, and n is 2 or 3. ) Represented by
Poly (N-acylalkyleneimine) composed of return units
Segment and organopolysiloxane segment
The end of the segment of organopolysiloxane or
Is a compound of the formula (2) : Via an alkylene group containing a hetero atom represented by
A poly (N consisting of the repeating unit represented by the formula (1)
-Acylalkyleneimine)
And the segment of the poly (N-acylalkyleneimine)
And the organopolysiloxane segment weight ratio
1/50 to 20/1 with a molecular weight of 500 to 500,000
A skin cosmetic containing a coating powder whose surface is coated with a poly (N-acylalkyleneimine) -modified silicone of 0 . 2. The powder whose surface is coated is talc, mica, kaolin, titanium oxide, aluminum silicate, silicic acid anhydride, zinc oxide, calcium carbonate, magnesium carbonate, red iron oxide, yellow iron oxide, black iron oxide, ultramarine blue. , Mica titanium, sericite, aluminum oxide, zirconium oxide, bismuth oxychloride, iron oxide mica, polyethylene,
Polystyrene, cellulose, nylon, acrylic resin,
Polytetrafluoroethylene or claim 1 Symbol placement of skin cosmetics is silk powder.