JPH06305933A - Oily solid cosmetic - Google Patents

Abstract

PURPOSE:To provide an oily solid cosmetic containing a specific alkylglyceryl ether-modified silicone as an essential ingredient, excellent in cosmetic retainability, good in both touch and finish, and useful as a lip stick, a make-up cosmetic such as a foundation, etc. CONSTITUTION:An oily solid cosmetic containing one kind or more of alkyl glyceryl ether-modified silicones. The alkylglyceryl ether is especially preferably an alkylglyceryl ether-modified silicone of formula I [at least one of R<1>-R<12> is alkylglyceryl ether of formula II (Q is 3-20C divalent hydrocarbon; R<13>, R<14> are H, 1-32C hydrocarbon), and the others are H, 1-32C hydrocarbon, phenyl; p-r are such numbers that the content of the group of the formula II is 1-50wt.%]. The addition of a solid, semi-solid or liquid oily raw material (e.g. vegetable wax, lanolin wax, petrolatum) in addition of the silicone is preferable.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oily solid cosmetic composition which is excellent in feeling of use, finish and makeup retention.

[0002]

2. Description of the Related Art Conventionally, oily makeup cosmetics such as lipsticks, eye shadows, eyeliners and oily foundations have the drawback that after applying to the skin, the makeup lasts poorly and is liable to adhere to clothes or bleed. Had.

In order to eliminate this drawback and improve makeup retention, various studies have been made in the past. As an example, a volatile oil agent is blended, and after application, the oil agent is volatilized so that the coloring material and the wax remain on the coated surface, and an attempt to improve the durability of the makeup; and a polymer such as a polymer in the volatile oil agent. There has been an attempt to improve the durability of makeup by blending a film-forming agent dissolved therein and applying and drying it to form a polymer film on the skin surface.

However, the cosmetics which are intended to improve the makeup lasting by using the volatile oil agent have a drawback that the gloss after application is deteriorated with time, which is a problem especially in lipstick. Further, since the volatile oily agent volatilizes over time, thinning of the lipstick occurs and there is a problem in terms of stability of the product over time.

[0005]

SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide an oily solid cosmetic composition which does not have the above-mentioned drawbacks, is excellent in makeup retention, and has a good feeling in use and a good finish.

[0006]

Means for Solving the Problems As a result of intensive studies in view of the above situation, the present inventor has found that a solid cosmetic containing an alkyl glyceryl ether-modified silicone is excellent in makeup lasting and has good feeling and finish. The inventors have found that it is good and completed the present invention.

That is, the present invention is one or more of alkyl glyceryl ether modified silicones (hereinafter,
An oily solid cosmetic containing (A) component is provided.

The (A) component alkyl glyceryl ether-modified silicone of the present invention is blended as an oil component. Therefore, the alkyl glyceryl ether-modified silicone (A) has a degree of alkyl glyceryl ether modification such that it becomes an oil, that is,
An alkylglyceryl ether having a low degree of modification is preferable.

Specific examples of the preferred alkyl glyceryl ether-modified silicone include those represented by the following general formula (1).

[0010]

[Chemical 2]

(In the formula, Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, and R ¹³ and R ¹⁴ are the same or different and each is a hydrogen atom or a linear or branched carbon atom having 1 to 32 carbon atoms. An alkyl glyceryl ether group represented by the formula (1) represents a hydrogen group), the rest each represent a hydrogen atom, a linear or branched hydrocarbon group having 1 to 32 carbon atoms or a phenyl group, and p, q
And r represent the number such that the content of the alkyl glyceryl ether group represented by the general formula (2) in the molecule becomes 1 to 50% by weight.

Specific examples of the more preferable ones include those represented by the following general formulas (3) to (6).

[0013]

[Chemical 3]

[In the formula, R ^{1 to} R ⁹ , Q, R ¹³ , R ¹⁴ and p
And q have the same meaning as described above. However, a plurality of R ¹³ and R ¹⁴ existing in the same molecule may be different from each other.]

In the above general formulas (1), (3) to (6), the divalent hydrocarbon group represented by Q and having 3 to 20 carbon atoms is trimethylene, tetramethylene, pentamethylene, hexamethylene or hepta. Methylene, octamethylene, nonamethylene, decamethylene, undecamethylene,
Linear alkylene groups such as dodecamethylene, tetradecamethylene, hexadecamethylene and octadecamethylene; branched chains such as propylene, 2-methyltrimethylene, 2-methyltetramethylene, 2-methylpentamethylene, 3-methylpentamethylene Examples thereof include alkylene groups.

In the definition of R ^{1 to} R ¹⁴ , the number of carbon atoms is 1 to 3.
As the linear or branched hydrocarbon group of 2, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl,
Linear alkyl groups such as octadecyl, eicosyl, doeicosyl, tetraeicosyl, hexaeicosyl, octaeicosyl, triacontyl; isopropyl, sec-
Branched chain alkyl groups such as butyl, tert-butyl, neopentyl, 1-ethylpropyl, 1-heptyldecyl and the like can be mentioned. In the present invention, R ^{1 to} R ¹² are preferably linear or branched hydrocarbon groups having 1 to 25 carbon atoms (provided that a part of them may be hydrogen atoms), and particularly 1 to 1 carbon atoms.
22 straight or branched chain hydrocarbon groups (provided that some may be hydrogen atoms) are preferred. Further, R ¹³ and R ¹⁴ are preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom.

Further, p, q, and r are numbers such that the content of the alkyl glyceryl ether group (2) is 1 to 50% by weight, but the organopolysiloxane as a raw material is easily available, and is easily produced. From the viewpoint of operability and the like, the range of 0 to 2000 is preferable. Further, in the general formulas (3) to (6), p is particularly preferably in the range of 1 to 500, more preferably in the range of 10 to 30. Furthermore, general formula (3)-
In (6), q is particularly preferably in the range of 1 to 50, and more preferably in the range of 1 to 30.

The alkyl glyceryl ether-modified silicone as the component (A) in the present invention has a content of the alkyl glyceryl ether group (2) in the molecule of 1 to 50% by weight in order to obtain good finish and cosmetic durability. If it deviates from this range, the above effects cannot be obtained, which is not preferable.

The alkyl glyceryl ether-modified silicone as the component (A) is an alkenyl glyceryl ether corresponding to an organohydrogenpolysiloxane having at least one silicon-hydrogen bond according to the method described in JP-A-4-134013. Can be produced by reacting

The alkyl glyceryl ether-modified silicone as the component (A) in the present invention may be used alone or in combination of two or more, and the amount thereof is 0.1 to 10% based on the total composition.
It is preferably in the range of 50% by weight, particularly 1 to 15% by weight. If the blending amount is less than 0.1% by weight, the effect of holding makeup and the like are not sufficient, and if it exceeds 50% by weight, the feel is deteriorated, which is not preferable.

The oily solid cosmetic composition of the present invention is preferably a non-aqueous cosmetic composition containing the above-mentioned essential component alkyl glyceryl ether-modified silicone and containing substantially no water.

Further, the oily solid cosmetic of the present invention contains one or more solid (semi-solid or liquid) oily raw materials other than the above-mentioned component (A) (hereinafter referred to as the component (B)). be able to. Among the oily raw materials (B), solid or semi-solid ones include, for example, mokuro, hardened beef tallow, carnauba wax, candelilla wax, rice wax, beeswax, ceresin wax, microcrystalline wax, paraffin wax, polyethylene wax, Hardened jojoba oil, lanolin, petrolatum and mixtures thereof and the like can be mentioned. The blending amount of these may be appropriately determined depending on the cosmetic, but is usually 1 to 90% by weight, preferably 5 to 70% by weight in the total composition.

Examples of the liquid oily raw material include hydrocarbons such as liquid paraffin, liquid isoparaffin (liquid polyisobutylene) and squalane; natural animal and vegetable oils such as olive oil and jojoba oil; silicone oil such as dimethylpolysiloxane; isopropyl. Examples thereof include synthetic ester oils such as myristate, and mixtures thereof. The blending amount of these liquid oily raw materials may be appropriately determined depending on the purpose, but is usually 1 to 90% by weight, preferably 5 to 10% by weight in the total composition.
It is 70% by weight.

Further, the oily solid cosmetic of the present invention may be blended with known pigments usually used in cosmetics.
Specifically, for example, extender pigments such as talc, sericite, mica, kaolin, silica, nylon powder, polyethylene powder and cellulose powder; carbon black, titanium oxide, iron oxide, zinc oxide, ultramarine blue, navy blue,
Colorants such as chromium oxide, organic tar dyes and lakes;
In addition, composite pigments such as mica tatin and iron oxide coated mica can be blended. Further, those cosmetic pigments whose surface is treated with silicone, higher fatty acid, higher alcohol, fatty acid ester, metal soap, amino acid or alkyl phosphate can be used.
These pigments are used in the oily solid cosmetic of the present invention in an amount of 0 to 95% by weight, preferably 5 to 70% by weight.

In the oily solid cosmetic of the present invention, in addition to the above components, other oily raw materials, surfactants, medicinal components, preservatives, other than the above, depending on the purpose, as long as the effects of the present invention are not impaired, Antioxidants, moisturizers, UV absorbers, fragrances and the like can be added.

The oily solid cosmetic composition of the present invention can be produced by heating, mixing, stirring, etc. the above components according to a conventional method, such as lipstick, foundation, eye shadow,
It can be a makeup cosmetic product such as an eyeliner.

[0027]

The alkyl glyceryl ether-modified silicone compounded in the oily solid cosmetic composition of the present invention is liquid in the absence of water, but has a viscosity when a small amount (1 to 20% by weight) of water is added. To rise. Therefore, the oily solid cosmetic of the present invention has a low viscosity at the time of preparation, so that the spread of the cosmetic is light and the pigment can be applied thinly and evenly on the skin, resulting in excellent finish and usability. ing. In addition, after application, water is supplied into the coating film from the skin or breath, and the alkylglyceryl ether-modified silicone in the coating film becomes highly viscous, which increases the viscosity of the coating film and removes makeup. It gets harder. Further, in the presence of water, the adhesion between the alkyl glyceryl ether-modified silicone and the skin or the lips is improved, and as a result, the durability of makeup is improved. Therefore, the oily solid cosmetic composition of the present invention is excellent in the feeling of use and finish and has a long lasting makeup.

[0028]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

Reference Example 1 A 100 ml two-necked flask equipped with a cooling tube and a magnetic stirrer was charged with the following formula.

[0030]

[Chemical 4]

Organohydrogensiloxane represented by 15 g (4.4 mmol), 10-undecenyl glyceryl ether 8.1 g (33 mmol), 1 part of potassium acetate
0.65 g (0.66 mmol) of a 0% ethanol solution and 50 g of isopropyl alcohol were charged, and 0.17 g (6.
6 × 10 ⁻³ mmol) was added and the temperature was raised by heating. The temperature of the contents was kept at 40 ° C. and stirred for 2.5 hours. After distilling off the solvent and treating with activated carbon, the unreacted 10
-Undecenyl glyceryl ether was distilled off to obtain a brown highly viscous material. The obtained product was confirmed to be compound (1-a) represented by the following formula by IR and ¹ H-NMR spectrum. Average molecular weight 5800 ( ¹ H-NMR
Calculated), the content of alkyl glyceryl ether group is 17
weight%.

[0032]

[Chemical 5]

IR (liquid film, cm ^-1 ) 3420 (-OH) 2968, 2932, 2860 (C-H) 1264 (Si-CH ₃ ) 1096, 1026, 842 (Si-O-Si) ¹ H-NMR (Δppm, in CDCl ₃ , CHCl ₃ standard (7.28pp
m)] 0.00 (s, about _{390H) Si-C H 3 0.35-0.50} (m, 8H) Si-C H 2 1.08-1.39 (br, 64H) -C H 2 - 1.39-1.62 (br, 8H) C H ₂ -CH ₂ -O 1.96-2.29 (br, 4H) CH ₂ -O H 2.43-2.68 (br, 4H) CH-O H 3.38-3.50 (m, 16H) C H ₂ -O 3.50-3.70 (m , 8H) C H ₂ -OH 3.70-3.86 (m, 4H) C H -OH

Reference Example 2 A 100 ml two-necked flask equipped with a cooling tube and a magnetic stirrer was charged with the following formula.

[0035]

[Chemical 6]

15 g (4.4 mmol) of an organohydrogensiloxane represented by, 4.3 g (33 mmol) of allyl glyceryl ether, 0.65 g (0.66 mmol) of a 10% potassium acetate solution in ethanol and 50 g of isopropyl alcohol were charged. 2% isopropyl alcohol solution of chloroplatinic acid 0.17g (6.6 × 10 ^-3 mm
ol) was added and heated to raise the temperature. The temperature of the contents was kept at 40 ° C, and the mixture was stirred for 2.5 hours. After distilling off the solvent and treating with activated carbon, the unreacted allyl glyceryl ether was distilled off under reduced pressure by distillation under reduced pressure to obtain a viscous material. The obtained product was analyzed by IR and ¹ H-NMR spectrum to obtain the following formula (1-
It was confirmed to be the compound represented by b). Average molecular weight 4000 (calculated by ¹ H-NMR), alkyl glyceryl ether content 20% by weight.

[0037]

[Chemical 7]

IR (liquid film, cm ^-1 ) 3400 (-OH) 2965, 2925, 2860 (C-H) 1262 (Si-CH ₃ ) 1096, 1022, 844 (Si-O-Si) ¹ H-NMR (Δppm, in CDCl ₃ , CHCl ₃ standard (7.28pp
m)] 0.01 (s, about _{273H) Si-C H 3 0.38-0.58} (m, 10H) Si-C H 2 - 1.10-1.41 (br, 8H) -C H 2 - 1.44-1.86 (m, 10H) C H ₂ -CH ₂ -O 3.30-3.55 (m, 20H) C H ₂ -O 3.55-3.77 (m, 10H) C H ₂ -OH 3.77-3.90 (m, 5H) C H -OH

Example 1 Lipstick Lipsticks were produced by heating the components shown in Table 1 below to 80 ° C. and mixing them uniformly, pouring them into a molding die and cooling and solidifying. About the obtained lipstick, Table 1 was prepared by 10 panelists.
Sensory evaluation was performed on the test items according to the following evaluation criteria. The results are shown in Table 1.

Evaluation Criteria ⊚: Eight or more out of 10 evaluated as good. ◯: 6 or more out of 10 evaluated as good. Δ: 4 or more out of 10 evaluated as good. X: 3 out of 10 evaluated as good.

[0041]

[Table 1]

As is clear from Table 1, the lipstick of the present invention was excellent in finish, color transfer and color fading resistance, and further bleeding resistance.

Example 2 A lipstick was produced in the same manner as in Example 1, except that the alkyl glyceryl ether-modified silicone obtained in Reference Example 2 was used in place of the alkyl glyceryl ether-modified silicone of Inventive Product 1 of Example 1. The lipstick of the present invention (Product 2 of the present invention) was excellent in finish, color transfer and color fading resistance, and further bleeding resistance.

Example 3 Oily foundation Of the components shown in Table 2, the wax and oil components were dissolved at 90 ° C., the pigment part and the fragrance were added thereto, and the mixture was degassed. This was poured into a mold, cooled and molded, and then filled in a container to obtain an oily foundation. The makeup retention of these foundations was evaluated according to the evaluation criteria of Example 1. The results are shown in Table 2.

[0045]

[Table 2]

As is clear from Table 2, the oil-based foundation of the present invention was clearly superior to the comparative product in terms of makeup retention (prevention of makeup deterioration).

Example 4 Solid Powder Eye Shadow Among the components shown in Table 3, the powder part was stirred and mixed with a blender,
The oil phase part which was heated and dissolved was sprayed onto this and further stirred.
Then, it was crushed and compression molded with a molding machine to obtain a solid powder eye shadow. The makeup retention of these powder eye shadows was evaluated according to the evaluation criteria of Example 1. The results are shown in Table 3.

[0048]

[Table 3]

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[Procedure amendment]

[Submission date] May 14, 1993

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] 0024

[Correction method] Change

[Correction content]

Further, the oily solid cosmetic of the present invention may be blended with known pigments usually used in cosmetics.
Specifically, for example, extender pigments such as talc, sericite, mica, kaolin, silica, nylon powder, polyethylene powder and cellulose powder; carbon black, titanium oxide, iron oxide, zinc oxide, ultramarine blue, navy blue,
Colorants such as chromium oxide, organic tar dyes and lakes;
In addition, composite pigments such as mica titanium and iron oxide coated mica may be blended. Further, those cosmetic pigments whose surface is treated with silicone, higher fatty acid, higher alcohol, fatty acid ester, metal soap, amino acid or alkyl phosphate can be used.
These pigments are used in the oily solid cosmetic of the present invention in an amount of 0 to 95% by weight, preferably 5 to 70% by weight.

Claims (3)

[Claims] 1. An oily solid cosmetic containing one or more alkyl glyceryl ether-modified silicones. 2. The oily solid cosmetic composition according to claim 1, wherein the alkyl glyceryl ether-modified silicone is represented by the following general formula (1). [Chemical 1] (In the formula, Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, and R ¹³ and R ¹⁴ are the same or different and each represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 32 carbon atoms. Represents the alkyl glyceryl ether group, and the rest each represent a hydrogen atom, a linear or branched hydrocarbon group having 1 to 32 carbon atoms or a phenyl group, and p, q and r are general in the molecule. The content of the alkyl glyceryl ether group represented by the formula (2) is 1 to 50% by weight.] 3. The oily solid cosmetic composition according to claim 1, further comprising a solid, semi-solid or liquid oily raw material other than the alkyl glyceryl ether modified silicone.