JPH09136812A - Skin cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a skin cosmetic, excellent in adhesion to the skin, good in makeup durability and having a light touch. SOLUTION: This skin cosmetic is obtained by blending N-vinylpyrrolidone with a copolymer prepared by copolymerizing an organopolysiloxane compound, represented by the following formula (1) (R<1> is hydrogen atom or methyl group; R<2> is a 1-10C bivalent hydrocarbon group which may be interrupted by one or more oxygen atoms; R<3> and R<4> are each same or different 1-18C unsubstituted or substituted monovalent hydrocarbon group or R; ER is a polyroganosiloxane group) and having a radically polymerizable group at one terminal of a molecular chain at >60mol% content of N-vinylprrolidone expressed in terms of mol% and >60wt.% content thereof expressed in terms of weight ratio in the copolymer as an oil agent.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a copolymer obtained by copolymerizing N-vinylpyrrolidone and an organopolysiloxane compound having a radically polymerizable group at one end of a molecular chain at a specific ratio as an oil agent. The present invention relates to a blended skin cosmetic, and more particularly to a skin cosmetic having excellent adhesion to the skin and having a light feeling.

[0002]

2. Description of the Related Art Organopolysiloxane represented by dimethylpolysiloxane is an oil agent which has been widely used in cosmetics in recent years because of its characteristics such as light feel, excellent water repellency and high safety. Although dimethylpolysiloxane has excellent properties as an oil agent for cosmetics as described above, on the other hand, it has low solubility parameters, low surface tension, and low intermolecular force. Simple replacement of hydrogen oil, ester oil, fats and oils is difficult. In addition, even if silicone oil is blended in a mixed system with an oil agent, the compatibility is poor, and therefore the discharge phenomenon is likely to occur, which sometimes imposes prescriptive restrictions in the preparation of cosmetics.

On the other hand, polyvinylpyrrolidone obtained by polymerizing N-vinylpyrrolidone is known to be a polymer having good solubility in various solvents and oil agents and having film forming ability and complex forming ability. There is. Many copolymers are also known because they are relatively easy to copolymerize with acrylic monomers. Recently, a copolymer with an organopolysiloxane having a radically polymerizable group at one end of the molecular chain, which is called a silicone macromonomer, has been reported (JP-A-3-128909, JP-A-3-170).
No. 518, JP-A-4-36218, and JP-A-4-175.
No. 318, etc.), and these are mainly proposed as hair cosmetics, especially as a setting agent.

[0004]

Even if an organopolysiloxane is to be incorporated into a makeup cosmetic composition, the organopolysiloxane has a poor adhesion to the skin due to its nature.
In many cases, usability deteriorates, and it is unavoidable to use it in a mixed system with a conventional oil agent such as hydrocarbon oil, ester oil, and fat. As a result, as described above, these oil agents and silicone oil have poor compatibility, so that the discharge phenomenon is likely to occur, and there is a prescriptive restriction in the preparation of cosmetics. The present invention has been made in view of the above circumstances, and an object thereof is to provide an oil agent for cosmetics having intermediate properties between an oil agent such as silicone oil and conventional hydrocarbon oils, ester oils, and fats and oils. In addition, the object is to provide a skin cosmetic having excellent emollient effect and moisturizing effect, water repellency, good usability, excellent adhesion to the skin, very good makeup retention, and a light feeling. And

[0005]

Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that N-vinylpyrrolidone and an organopolysiloxane compound having a radically polymerizable group at one end of a molecular chain are required. In the copolymer obtained by copolymerizing with a radically polymerizable monomer according to the above, the copolymer obtained by copolymerizing N-vinylpyrrolidone in a specific ratio is a conventional one such as hydrocarbon oil, ester oil, fat and oil. The present invention has been completed by finding that it has an intermediate property between the oil agent and the silicone oil and has water repellency as well as an emollient effect and a moisture effect. That is, the present invention is a copolymer obtained by copolymerizing N-vinylpyrrolidone and an organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain represented by the following general formula (1): The skin cosmetic is characterized in that the copolymer has an N-vinylpyrrolidone ratio of more than 60 mol% in a molar ratio and less than 60% by weight in a molar ratio as an oil agent.

[0006]

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[Wherein R ¹ is a hydrogen atom or a methyl group;
R ² is a divalent hydrocarbon group having 1 to 10 carbon atoms, which may be interrupted by one or two or more oxygen atoms; R ³ and R ⁴ are the same or different and are unsubstituted with 1 to 18 carbon atoms. Alternatively, it is a substituted monovalent hydrocarbon group or R. R is represented by the following general formula (2).

[0008]

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(In the formula, R ⁵ , R ⁶ and R ⁷ represent the same or different C 1-18 unsubstituted or substituted monovalent hydrocarbon groups, and n represents an integer of 1-300.) Is a copolymer of N-vinylpyrrolidone, an organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain represented by the general formula (1), and another radically polymerizable monomer. The skin cosmetics containing the above-mentioned copolymer as an oil agent have excellent adhesion to the skin, have excellent makeup retention, and have a light touch.

[0010]

DETAILED DESCRIPTION OF THE INVENTION A detailed description will be given below. The N-vinylpyrrolidone used in the present invention is represented by the following chemical formula (3).

[0011]

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Specific examples of the organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain represented by the above general formula (1) used in the present invention include the following general formula ( It can be obtained by subjecting the (meth) acrylate-substituted chlorosilane compound represented by 4) to the terminal hydroxyl group-substituted organopolysiloxane represented by the general formula (5) in a dehydrochlorination reaction according to a conventional method. It is not limited to this.

[0013]

[Chemical 6]

[0014]

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Among the compounds represented by the above general formula (1), specific examples of the compounds preferably used include the compounds shown below.

[0016]

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[0017]

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[0018]

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[0019]

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[0020]

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[0021]

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The copolymer used in the present invention is a copolymer of the organopolysiloxane compound represented by the above general formula (1) and the N-vinylpyrrolidone represented by the above chemical formula (3). Further, it may be a copolymer in which a part of the organopolysiloxane compound represented by the general formula (1) is replaced with another radically polymerizable monomer and copolymerized. That is, a copolymer of the organopolysiloxane compound represented by the above general formula (1), the N-vinylpyrrolidone represented by the above formula (3) and another radical polymerizable monomer can also be used. Other radically polymerizable monomers include styrene, substituted styrene, vinyl acetate, (meth) acrylic acid, (meth) acrylic acid ester, maleic anhydride, maleic acid ester, fumaric acid, fumaric acid ester, vinyl chloride, vinylidene chloride. , Ethylene, propylene, butadiene, acrylonitrile, fluorinated olefins and the like can be exemplified, and these can be used alone or in combination of two or more. In the case of a copolymer having another radical polymerizable monomer as a copolymerization component, the ratio of the organopolysiloxane compound represented by the general formula (1) to the copolymer is 0.1% by weight or more.

In this copolymer, the above chemical formula (3)
The proportion of N-vinylpyrrolidone represented by is 60 mol%
N, in order to maintain the characteristics of silicone,
-Vinylpyrrolidone should be less than 60% by weight. When the content is 60% by weight or more, the hydrophilicity becomes too strong, and therefore when incorporated into a cosmetic, the water repellency of the cosmetic film,
The makeup lasts worse. In addition, if you want to further emphasize the feel of silicone, N-vinylpyrrolidone is 20
It is preferably less than 10% by weight, and while being excellent in adhesion to the skin, light elongation and light feel can be obtained, and pigment dispersibility is also excellent, which is particularly excellent as a raw material for cosmetics.

Further, when a large amount of methyl methacrylate or the like is blended as the radically polymerizable monomer used in the copolymer of the present invention, the resulting copolymer has characteristics of acrylic resin, film-forming property and film retention. When the strength is improved and a large amount of acrylic acid ester having a t-butyl group, 2-ethylhexyl group or the like as a part of the structure is blended, the resulting copolymer becomes an oil agent having a soft feel.

The copolymer of the compound represented by the general formula (1) and the N-vinylpyrrolidone represented by the chemical formula (3), or the copolymerization of these with a radical-polymerizable monomer is benzoyl peroxide. , Lauroyl peroxide, azobisisobutyronitrile and the like in the presence of a usual radical polymerization initiator, and any of the solution polymerization method, emulsion polymerization method, turbidity polymerization method and bulk polymerization method can be applied. Among these, the solution polymerization method is a preferable method because it is easy to adjust the molecular weight of the obtained copolymer to an optimum range. As the solvent used here,
Aromatic hydrocarbons such as benzene, toluene and xylene;
Examples thereof include one or a mixture of two or more of esters such as methyl ethyl ketone and methyl isobutyl ketone. Further, this polymerization reaction has a reaction temperature of 50 to 180 ° C.,
It is particularly preferable to carry out the treatment in the range of 60 to 120 ° C., and the reaction can be completed in about 5 to 10 hours under this temperature condition.

The copolymer of the present invention produced as described above comprises the compound represented by the general formula (1) as a copolymerization component and the N-vinylpyrrolidone represented by the chemical formula (3). When used, the structure has the units (a) and (b) shown below in the molecule.

[0027]

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[0028]

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In the present invention, the blending amount of the copolymer in the cosmetic is preferably 0.1 to 80% by weight, 1 to 5
0% by weight is particularly preferred. When these copolymers are blended into skin cosmetics as an oil agent, the adhesion of the cosmetic to the skin is improved by the action of the polar and hydrophilic parts such as pyrrolidone in the highly hydrophobic oil, and the silicone. The water-repellent and oil-repellent film is formed by the action of the portion, so that the water resistance and oil resistance are improved and the makeup lasting property becomes very good. It also has an emollient effect and a moisturizing effect. Thus, a skin cosmetic containing the N-vinylpyrrolidone of the present invention and a copolymer obtained by copolymerizing an organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain at a specific ratio as an oil agent is It has excellent adhesion to the skin, very long make-up, and a light feel.

The cosmetics of the present invention prepared by blending the copolymer include basic cosmetics for the face and limbs such as creams and emulsions; makeup cosmetics such as foundation, white powder, blusher, eyeshadow and lipstick. Is mentioned. Also,
In addition to the copolymer, a cosmetic ingredient that is usually used can be blended according to the product type or the cosmetic purpose. Examples of such cosmetic ingredients include oils, waxes, hydrocarbons, silicone oils, higher fatty acids, higher alcohols, esters, oil raw materials such as lanolin, powder raw materials such as white pigments, colored pigments, extender pigments, and metallic soaps. , Surfactants, polyhydric alcohols, lower alcohols, polymer compounds, water, antioxidants, ultraviolet absorbers, preservatives, tar dyes, cosmetic ingredients, and fragrances.

[0031]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Production Example 1 Copolymer A In a glass reactor equipped with a thermometer and a reflux condenser, 70.8 g of a compound represented by the following chemical formula, 94.3 g of N-vinylpyrrolidone, 600 g of toluene and azobisisobutyronitrile were used. Charge 5 g, stir while maintaining at 110-115 ° C., carry out copolymerization reaction for 8 hours, and after purification, about 15
0 g of a colorless solid was obtained (ratio of N-vinylpyrrolidone: 92.4 mol%, 57.1 wt%). This solid is
From a qualitative test and an infrared absorption spectrum, it was confirmed to be a copolymer having a dimethylpolysiloxane chain and a pyrrolidone group as a side chain.

[0032]

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Production Example 2 Copolymer B Using 142.6 g of a compound represented by the following chemical formula, 11.0 g of 2-ethylhexyl acrylate, 93.2 g of N-vinylpyrrolidone, 600 g of toluene and 5 g of azobisisobutyronitrile, The same operation as in Production Example 1 was carried out to obtain about 230 g of a colorless solid (proportion of N-vinylpyrrolidone: 83.8 mol%, 37.8 wt%).

[0034]

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Production Example 3 Copolymer C 198.7 g of a compound represented by the following chemical formula, 3.2 g of t-butyl acrylate, 47.2 N-vinylpyrrolidone
g, 100 g of toluene and 0.5 g of azobisisobutyronitrile, and using the same procedure as in Production Example 1, about 240
g of colorless viscous liquid was obtained (proportion of N-vinylpyrrolidone: 85.1 mol%, 18.9 wt%).

[0036]

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Production Example 4 Copolymer D 162.5 g of a compound represented by the following chemical formula, 4.6 g of 2-ethylhexyl acrylate, 5.0 g of methyl methacrylate, 38.9 g of N-vinylpyrrolidone, 300 g of toluene and azobisisobutyrate. Using 5 g of ronitrile,
The same operation as in Production Example 1 was carried out to obtain about 200 g of a colorless viscous liquid (proportion of N-vinylpyrrolidone: 70.0 mol%, 18.4 wt%).

[0038]

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Examples 1 and 2, Comparative Examples 1 to 4 Lipsticks Lipsticks were produced according to the components and proportions shown in Table 1.

[0040]

[Table 1]

(Production Method) A: Components (1) to (10) were uniformly heated and dissolved. B: A and components (11) to (13) were uniformly dispersed. After adding the components (14) to (17) to C: B, the mixture was filled in a container.

(Evaluation) Using a panel of 50 women, a use test was conducted according to the criteria and the criteria shown in Table 2 for ease of use, luster, no bleeding, and durability of makeup, and the average was evaluated.

[0043]

[Table 2]

Table 3 shows the results of evaluation of Examples 1 and 2 and Comparative Examples 1 to 4.

[0045]

[Table 3]

As is clear from the results shown in Table 3, Example 1
It can be seen that, as compared with Comparative Examples 1 to 4, lipsticks Nos. 2 to 2 have good usability, are glossy, and have a long-lasting lipstick without bleeding.

Example 3 Lipstick (prescription) (wt%) 1. Paraffin wax 5.0 2. Polyethylene wax 10.0 3. Ceresin wax 5.0 4. Vaseline 10.0 5. Diisostearyl malate 5.0 6. Diglyceryl triisostearate 5.0 7. Decamethylcyclopentasiloxane remaining amount 8. Trimethylsiloxysilicic acid 15.0 9. Copolymer A (Production Example 1) 10.0 10. Pigment 8.0 11. Silicone treated iron oxide mica titanium 5.0 12. Appropriate amount of beauty ingredients 13. Appropriate amount of UV absorber 14. Preservative appropriate amount 15. Appropriate amount of fragrance

(Production Method) A: Components (1) to (9) were uniformly heated and dissolved. B: A and components (10) to (11) were uniformly dispersed. After adding the components (12) to (15) to C: B, the mixture was filled in a container. The product of the present invention obtained as described above is excellent in usability,
Good makeup lasting, no bleeding,
It was a lipstick that didn't feel tight.

Example 4 Emulsion (prescription) (wt%) 1. N-acyl glutamic acid 0.1 2.1,3-butylene glycol 0.4 3. Glycerin monofatty acid ester 0.5 4. Cetanol 0.5 5. Gaylow 1.0 6. Macadamian nut oil 6.0 7. Liquid paraffin 3.0 8. Copolymer C (Production Example 3) 5.0 9. Sodium hydroxide 0.025 10.1, 3-butylene glycol 15.0 11. Purified water balance

(Manufacturing Method) A: Component (1) is dissolved in (2) by heating, and then components (3)-
(8) was added and the temperature was raised to 75 ° C. B: Components (9) to (11)
Was uniformly dissolved at 75 ° C. C: B was added to A, emulsified, and cooled. The product of the present invention obtained as described above was a milky lotion having a water-repellent film, yet having a moist feeling and excellent in usability and usability.

Example 5 Powder Foundation (Component) (wt%) 1. Silicone treated titanium oxide (A) * 10.0 2. Silicone treated titanium oxide (B) ** 2.0 3. Silicone treated sericite *** 35.0 4. Lecithin-treated talc residual amount 5. Lecithin-treated spherical nylon powder 5.0 6. Red iron oxide 0.4 7. Yellow iron oxide 2.0 8. Amber 0.4 9. Black iron oxide 0.1 10. Copolymer B (Production Example 2) 5.0 11. Dimethyl polysiloxane (6cs) 3.5 12. Dipentaerythritol fatty acid ester 1.5 *: 98 parts of rutile type titanium oxide hydrophobized with 2 parts of methyl hydrogen polysiloxane **: 98 parts of anatase type titanium oxide hydrophobic with 2 parts of methyl hydrogen polysiloxane Chemically treated ***: 95 parts of sericite treated with 2 parts of methyl hydrogen polysiloxane for hydrophobic treatment, and 3 parts of petrolatum for oil treatment

(Production method) A. Components (1) to (9) were mixed and ground. B. The components (10) to (12) were uniformly mixed. C. After adding B to A and making it uniform, it was further crushed and pressed into a dish. The product of the present invention obtained as described above was a powder foundation which was smooth and had excellent adhesiveness, was resistant to sweat, etc., had good makeup durability, and was excellent in usability and usability.

[0053]

As described in detail above, the copolymerization product obtained by copolymerizing the N-vinylpyrrolidone of the present invention and the organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain at a specific ratio. Skin cosmetics that combine coalesced as an oil agent have excellent adhesion to the skin and have a very long-lasting makeup.
Moreover, it is an excellent skin cosmetic with a light feel.

Claims (5)

[Claims] 1. N-vinylpyrrolidone and the following general formula (1):
A copolymer obtained by copolymerizing an organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain represented by the following formula, wherein the proportion of N-vinylpyrrolidone in the copolymer is A skin cosmetic comprising a copolymer in an amount of more than 60 mol% and less than 60 wt% in a weight ratio as an oil agent. Embedded image [Wherein R ¹ is a hydrogen atom or a methyl group; R ² is an optionally interrupted one or more oxygen atom, and has 1 to 1 carbon atoms.
Divalent hydrocarbon group 0; R ^3, R ⁴ is a monovalent hydrocarbon radical or R substituted or unsubstituted 1 to 18 carbon atoms the same or different. R is represented by the following general formula (2). Embedded image (In the formula, R ⁵ , R ⁶ and R ⁷ are the same or different and have 1 to 1 carbon atoms.
8 represents an unsubstituted or substituted monovalent hydrocarbon group, and n is 1 to
Indicates an integer of 300. ] 2. A copolymer of N-vinylpyrrolidone, an organopolysiloxane compound having a radically polymerizable group at one end of the molecular chain represented by the general formula (1), and another radically polymerizable monomer. The cosmetic according to claim 1, which is a polymer. 3. The skin cosmetic according to claim 1, wherein the weight ratio of N-vinylpyrrolidone in the copolymer is less than 20% by weight. 4. The skin cosmetic according to claim 1, 2 or 3, wherein the cosmetic is lipstick. 5. The skin cosmetic according to claim 1, 2 or 3, wherein the cosmetic is a foundation.