JPH09175928A - Oily cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an oily cosmetic easy in coating extension, exhibiting good touch, absorbing water to increase the strength of a cosmetic film, after coated, and thereby good in the durability of the make-up by compounding a specific polyoxyalkylene-modified organopolysiloxane. SOLUTION: This oily cosmetic is compounded with a long chain alkyl- containing polyoxyalkylene-modified organopolysiloxane preferably in an amount of 0.1-30wt.% based on the oily cosmetic. The long chain alkyl-containing polyoxyalkylene-modified organopolysiloxane is preferably a compound of formula I [R<1> is a 1-8C alkyl, H, phenyl; R<2> is a group of formula II [R<3> is an alkyl, H; (x) and (y) are each such a number that the weight ratio of C2 H4 O and C3 H6 O is 100:0 to 20:80]; (l) is 10-200; (m) is 1-25; (n) is 1-100 under such conditions that (n) is larger than (m) and that 3(n) is <1; the mol.wt. of R<2> is 250-2000], etc. The oily cosmetic can be used as a lip stick, an eye shadow, an eye liner, a foundation, a cream, etc.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention has excellent usability, finish, and makeup retention by incorporating a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane, and has very little color transfer to clothes and the like. Relating to obtaining an oily solid cosmetic.

[0002]

2. Description of the Related Art Conventionally, it has been difficult for oily cosmetics such as lipsticks, eyeliners, eye shadows and oily foundations to have good usability and makeup retention at the same time. However, it had a defect that it adhered to clothes and bleeding easily. In order to eliminate these drawbacks, many studies have been conducted conventionally. For example, in lipsticks, a dye is added to improve the durability of the makeup by dyeing on the lips, and a lot of solid oily base such as wax is added,
Those that strengthen the coating film to reduce color transfer, blend a volatile oil agent and a film-forming agent, form a film on the skin surface by volatilizing the volatile solvent after application, and improve the makeup lasting etc. In addition, it has been newly investigated to add a polyoxyalkylene-modified organopolysiloxane or the like to absorb a trace amount of moisture on the lips and moisture in the air over time, and thicken the coating film to reduce color transfer. Came.

[0003]

However, those containing a dye tend to dry the coated part over time, and those containing a large amount of a solid oily base such as wax have a heavy spreadability and are poor in usability. Further, those containing a volatile oil agent and a film-forming agent lose their luster over time after application and the applied part dries. Moreover, volatilization of the volatile solvent causes red thinning, which causes a problem in terms of stability over time. Polyoxyalkylene-modified organopolysiloxane (polyether-modified silicone)
Has a good compatibility with silicone oil, but has a drawback in that it is poorly compatible with triglyceride, ester oil and the like which are generally used in oily cosmetics and cannot be stably blended. Therefore, there has been a demand for an oily cosmetic which is excellent in usability, finish and makeup retention and has less color transfer over time.

[0004]

Under such circumstances, as a result of intensive studies by the present inventors, by incorporating a long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane into an oil-based cosmetic composition, the spreadability at the time of application is increased. It has been found that an effect of improving makeup lasting can be obtained by absorbing moisture in the air or skin after application and increasing viscosity, and increasing makeup film strength after application. Came to do. That is, the present invention provides an oily cosmetic characterized by containing a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane.

The long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane used in the present invention can be any organopolysiloxane that is co-modified with a group containing a long-chain alkyl group and a polyoxyalkylene group. Can also be used, and is preferably represented by the following general formula (1) or (3).

[0006]

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(In the formula, R ¹ may be the same or different and represents an alkyl group having 1 to 8 carbon atoms, a hydrogen atom or a phenyl group, and in the formula, R ² is represented by the following general formula (2)-(C ₂ H ₄ O) _x - a _{(C 3 H 6 O) y} -R 3 ... (2), wherein R ³ is an alkyl group or a hydrogen atom having 1 to 4 carbon atoms, l is 10 to 200, m is 1 to 25, and n is 1 to 100 provided that n ≧ m in the average molecule and 3n <l, and h is 7 to 17
And the molecular weight of R ² is 250 to 2000, where x and y are selected such that the weight ratio of oxyethylene groups to oxypropylene groups is 100: 0 to 20:80. )

[0008]

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[Wherein R ⁴ is an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group or a fluorine-substituted alkyl group, and R ⁵ is the following general formula (4) —C _m H _2m —O— (C ₂ H ₄ O) _d (C ₃ H ₆ O) _e —R ⁷ (4), an organic group represented by the formula (4), R ⁶ is represented by the following general formula (5) —C _n H _2n —O— (C ₂ H ₄ O). _{) f (C 3 H 6 O} ) g -R 8 ... (5) an organic group (R ⁷ represented by the 1 hydrogen atom or a carbon atoms
An alkyl group of 5 or an organic group represented by R ⁹ — (CO) —, R ⁸ is a monovalent hydrocarbon group having 12 to 30 carbon atoms,
R ⁹ is an alkyl group having 1 to 5 carbon atoms, d is 2 to 20
An integer of 0, e is an integer of 0 to 200, and d + e is 3 to 2
00, f is an integer of 0 to 50, g is an integer of 0 to 50, f + g is 0 to 50, and m and n are integers of 0 to 5. ), And a, b, and c are 1.0 ≦, respectively.
a ≦ 2.5, 0.001 ≦ b ≦ 1.5, 0.001 ≦ c
≦ 1.5. ]

The silicone compound of the above formula (3) used in the present invention is an organohydrogenpolysiloxane represented by the following general formula (6), a polyoxyalkylene compound represented by the following general formula (7), and the following general formula: The alkylene compound represented by (8) can be easily synthesized in one step by addition reaction in the presence of a platinum catalyst or a rhodium catalyst. ^{_{R 4 a H (b + c}} ) SiO (4-abc) / 2 ... (6) C m H (2m-1) -O- (C 2 H 4 O) d (C 3 H 6 O) e -R _{^{7 ... (7) C n H}} (2n-1) -O- (C 2 H 4 O) f (C 3 H 6 O) g -R 8 ... (8) ( where, wherein R ⁴ is C 1 -C -10 alkyl group, aryl group, aralkyl group or fluorine-substituted alkyl group, R ⁷
Is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or R ⁹
An organic group represented by — (CO) —, R ⁸ has 12 to 3 carbon atoms.
0 is a monovalent hydrocarbon group, and R ⁹ is an alkyl group having 1 to 5 carbon atoms. a, b, and c are 1.0 ≦ a ≦ 2.
5, 0.001 ≦ b ≦ 1.5, 0.001 ≦ c ≦ 1.5
It is. d is an integer of 2 to 200, e is an integer of 0 to 200, and d + e is 3 to 200, f is an integer of 0 to 50, g is an integer of 0 to 50, and f + g is 0 to 50, m and n are integers of 0-5. )

Here, the organohydrogenpolysiloxane of the above formula (6) may be linear, branched or cyclic, but is mainly linear in order to promote the addition reaction smoothly. Is preferred. The organohydrogenpolysiloxane of the above formula (6) and the above formula (7)
The polyoxyalkylene compound and the alkylene compound of formula (8) are mixed in a molar ratio of SiH groups to terminal unsaturated groups of 0.5 to 2.0, preferably 0.8 to 1.2. .

The above addition reaction is preferably carried out in the presence of a platinum catalyst or a rhodium catalyst. Specifically, chloroplatinic acid, alcohol-modified chloroplatinic acid, a chloroplatinic acid-vinylsiloxane chain or the like is preferably used. used. The amount of the catalyst used may be a catalytic amount, but in particular, the amount of platinum or rhodium is 50 ppm or less, preferably 20 ppm or less.

The above addition reaction may be carried out in an organic solvent, if necessary. Examples of the organic solvent include aliphatic alcohols such as methanol, ethanol, 2-propanol and butanol, benzene, toluene, xylene and the like. Aromatic hydrocarbons, aliphatic or alicyclic hydrocarbons such as n-pentane, n-hexane, and cyclohexane, and halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride are included. Is preferably ethanol or 2-propanol. The addition reaction conditions are not particularly limited, but it is preferable to carry out the reaction under reflux for 1 to 10 hours.

The long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane used in the present invention is commercially available, for example, Abil EM-90 represented by the general formula (1), Abil B9806 (both manufactured by Gold Schmidt). Or a silicone compound represented by the general formula (3) (described in Japanese Patent Application Laid-Open No. 04-036324 and Japanese Patent Application No. 07-217666) can be used, and if necessary, one kind or two or more kinds can be used. .

The compounding amount of the long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane in the present invention is as follows:
In terms of usability and long-lasting effect, 0.1 to
It is preferably 30.0% by weight (hereinafter simply referred to as "%"), and more preferably 0.1 to 20.0%.

The oily cosmetic of the present invention may contain an oily base in addition to the above essential components. The oily base used in the present invention is not particularly limited as long as it is a commonly used solid, semi-solid or liquid oil, and it may be any of animal oils, vegetable oils, mineral oils and synthetic oils, and hydrocarbons. ,
Examples include oils and fats, waxes, esters, fatty acids, higher alcohols, silicone oils, fluorine-based oils, lipophilic surfactants and the like. For example, liquid paraffin, squalane, polybutene, petrolatum, paraffin wax, ceresin wax, microcrystalline wax, synthetic hydrocarbon wax, jojoba oil, mokuro, beeswax, carnauba wax, candelilla wax, dimethylpolysiloxane, methyl (decamethyl) cyclopolysiloxane. , A dimethylpolysiloxane polymer having a three-dimensional crosslinked structure, trimethylsiloxysilicic acid, methacryl-modified methylpolysiloxane, poly (glyceryl) mono (di or tri) isostearate, etc. can be used, and one or more kinds can be used as necessary. Can be used.

The oily cosmetic of the present invention contains, in addition to the above components,
Cosmetics Generally used powders, surfactants, antioxidants, polymer compounds, fragrances, preservatives, ultraviolet absorbers, moisturizers, cosmetic ingredients, etc. may be appropriately added within a range that does not impair the effects of the present invention. it can.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION The oily cosmetics of the present invention include lipsticks, eye shadows, eye liners, foundations, creams and the like, which can be produced by heating, mixing, stirring and the like. Further, the oil-based cosmetic composition of the present invention exhibits the effect more remarkably in a system containing substantially no water.

[0019]

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 A long chain alkyl-containing polyoxyalkylene-modified organopolysiloxane reactor was charged with the following average composition formula (9).

[0021]

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183 parts by weight of organohydrogensiloxane represented by the following formula, 182 parts by weight of polyoxyalkylene represented by the following average composition formula (10) CH ₂ ═CHCH ₂ O (C ₂ H ₄₀ ) ₉ H (10), 434 parts by weight of the oleyl alcohol derivative represented by the following average composition formula (11) CH ₂ ═CHCH ₂ O (C ₃ H ₆ O) ₃ C ₁₈ H ₃₅ (11) and 160 parts by weight of ethanol were mixed, and mixed with this. 0.1 part by weight of an ethanol solution containing 2% by weight of chloroplatinic acid was added, and the mixture was reacted for 6 hours under reflux of the solvent. The reaction product was heated under reduced pressure to remove the solvent and then filtered to obtain an organopolyosiloxane represented by the following reaction formula (12).

[0023]

[Chemical 6]

However, R ⁸ : -C ₃ H ₆ O (C ₃ H ₆ O) ₃ C ₁₈ H ₃₅ R ⁹ : -C ₃ H ₆ O (C ₂ H ₄₀ ) ₉ H

Production Example 2 In a long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane reactor, 183 parts by weight of the organohydrogensiloxane represented by the above average composition formula (9) and the following average composition formula (13) CH ₂ = 241 parts by weight of polyoxyalkylene represented by C (CH ₃ ) CH ₂ CH ₂ O (C ₂ H ₄₀ ) ₉ H (13), the following average composition formula (14) CH ₂ ═CHCH ₂ O (C ₃ H ₆ O) ₃ C ₁₄ H ₂₉ 343 parts by weight of the myristyl alcohol derivative represented by (14),
And 160 parts by weight of ethanol were mixed, 0.1 part by weight of an ethanol solution containing 2% by weight of chloroplatinic acid was added, and the mixture was reacted for 6 hours under reflux of the solvent. The reaction product is heated under reduced pressure to remove the solvent, followed by filtration to obtain the following reaction formula (15).
An organopolyosiloxane represented by

[0026]

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However, R ¹⁰ : -C ₃ H ₆ O (C ₃ H ₆ O) ₃ C ₁₄ H ₂₉ R ¹¹ : -CH ₂ CH (CH ₃ ) CH ₂ CH ₂ O (C ₂ H ₄₀ )
₉ H

Examples 1 to 8 and Comparative Examples 1 and 2 <Lipstick> Lipsticks having the compositions shown in Table 1 were prepared, and the pigment dispersibility in the molten state, usability, finish and makeup retention were evaluated. Table 1 also shows the results.

[0029]

[Table 1]

(Manufacturing Method) The component A was heated and dissolved at 110 to 120 ° C., the component B was added thereto and mixed uniformly, and then poured into a molding die and solidified by cooling to produce a lipstick.

(Test method and evaluation method) a) Pigment dispersibility The pigment dispersibility in the molten state before being poured into the mold of each sample was visually evaluated. b) Lightness of spread (usability) Each sample was applied to the lips to evaluate the lightness of spread. c) Uniformity of the makeup film (finish) Each sample was applied to the lips, and the uniformity of the makeup film was evaluated. d) Difficulty in transfer of color (makeup lasting) Each sample was applied to the lips, and the panel was allowed to have a normal life, and after 2 hours, the lips were held with a tissue to evaluate the difficulty of transfer of the color of the lipstick. . e) Good color retention (holding makeup) Each sample was applied to the lips, and the panel was made to have a normal life, and the makeup retention after half a day was evaluated.

For each evaluation item, a sensory panel of 10 people performed the following absolute evaluation in 7 stages (0 to 6), and the average score was further divided into 4 stages for evaluation. (1) Absolute evaluation 6: Very good 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad 0: Very bad (2) Four-point rating 5 or more: ◎ 4 or more and less than 5: ○ 3 or more and less than 4 points: △ Less than 3 points: ×

As is clear from the results shown in Table 1, the lipsticks of Examples 1 to 8, which are the products of the present invention, were superior to the lipsticks of Comparative Examples 1 and 2 in pigment dispersibility, usability, finish and makeup retention. It can be seen that it has far superior properties in all respects.

Example 9: Oily foundation (component) (%) (1) Ceresin wax 6.0 (2) Paraffin wax 5.0 (3) Vaseline 5.0 (4) Squalane residual amount (5) Dimethylpolysiloxane 15.0 (6) Silicone compound of Production Example 1 5.0 (7) Titanium oxide (hydrophobicizing treatment ^* ) 10.0 (8) Sericite (hydrophobicizing treatment ^* ) 15.0 (9) Red iron oxide (hydrophobicizing) Treatment ^* ) 1.5 (10) Yellow iron oxide (hydrophobization treatment ^* ) 2.5 (11) Black iron oxide (hydrophobization treatment ^* ) 0.5 (12) Antioxidant proper amount (13) Perfume proper amount ^* Methyl Hydrogen polysiloxane treatment

(Production method) Components (1) to (6) were heated and dissolved, and (7) to (13) were added thereto, and the mixture was uniformly mixed and deaerated. This was filled in a gold plate and cooled to solidify to produce an oily foundation.

Example 10: Eye shadow (Component) (%) (1) Mica 25.0 (2) Talc balance (3) Nylon powder 5.0 (4) Mica titanium 20.0 (5) Black iron oxide 0.5 (6) Ultramarine 1.0 (7) Red No. 202 1.5 (8) Microcrystalline wax 3.0 (9) Vaseline 3.0 (10) Liquid paraffin 6.5 (11) Production Example 2 Silicone compound 2.0 (12) UV absorber proper amount (13) Perfume proper amount

(Manufacturing method) Components (1) to (7) were mixed with stirring, and the melted product of (8) to (13) heated and dissolved was added thereto, further mixed, crushed, and then compressed in a gold plate. Mold.

[0038]

(Production method) Components (1) to (3), (8),
(9) is dispersed, and (4) to (7) are further added and dispersed.

The products of the present invention obtained in Examples 9 to 11 were all excellent in pigment dispersibility, feeling of use and finish, and also excellent in makeup retention.

[0041]

The oil-based cosmetic composition of the present invention is excellent in pigment dispersibility, feeling in use, finish and makeup retention by incorporating a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Shigeyoshi Momose 48-18 Sakaemachi, Kita-ku, Tokyo Inside Kose Research Institute

Claims (4)

[Claims] 1. An oil-based cosmetic composition comprising a long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane. 2. A long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane containing 0.1 to 3 in an oily cosmetic composition.
The oily cosmetic composition according to claim 1, which is blended in an amount of 0% by weight. 3. A long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane is represented by the following general formula (1): (In the formula, R ¹ may be the same or different and has 1 to 8 carbon atoms.
An alkyl group, a hydrogen atom or a phenyl group of the formula
² the following general formula _{(2) - (C 2 H} 4 O) x - a _{(C 3 H 6 O) y} -R 3 ... (2), wherein R ³ is an alkyl group having 1 to 4 carbon atoms Is a hydrogen atom, l is 10 to 200, m is 1 to 25, and n is 1 to 100 with the proviso that n ≧ m in the average molecule and 3n <l, and h is 7 to 17
And the molecular weight of R ² is 250 to 2000, where x and y are selected such that the weight ratio of oxyethylene groups to oxypropylene groups is 100: 0 to 20:80. The oily cosmetic according to claim 1 or 2, which is a silicone compound represented by the formula (3). 4. A long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane is represented by the following general formula (3): (However, wherein R ⁴ is an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group or a fluorine-substituted alkyl group, R ⁵
Following general formula _{(4) -C m H 2m -O-} (C 2 H 4 O) d (C 3 H 6 O) e -R 7 ... organic group represented by (4), R ⁶ is represented by the following general formula _{(5) -C n H 2n -O-} (C 2 H 4 O) f (C 3 H 6 O) g -R 8 ... (5) an organic group (R ⁷ represented by the 1 hydrogen atom or a carbon atoms
An alkyl group of 5 or an organic group represented by R ⁹ — (CO) —, R ⁸ is a monovalent hydrocarbon group having 12 to 30 carbon atoms,
R ⁹ is an alkyl group having 1 to 5 carbon atoms, d is 2 to 20
An integer of 0, e is an integer of 0 to 200, and d + e is 3 to 2
00, f is an integer of 0 to 50, g is an integer of 0 to 50, f + g is 0 to 50, and m and n are integers of 0 to 5. ), And a, b, and c are 1.0 ≦, respectively.
a ≦ 2.5, 0.001 ≦ b ≦ 1.5, 0.001 ≦ c
≦ 1.5. The oily cosmetic according to claim 1 or 2, which is a silicone compound represented by the formula (3).