JP3519530B2 - Oily cosmetics - Google Patents

Description

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane, which is excellent in usability, finish and cosmetic durability. The present invention relates to obtaining an oil-based solid cosmetic with very little color transfer to clothes and the like. [0002] Conventionally, oily cosmetics such as lipstick, eyeliner, eye shadow, oily foundation, etc., have difficulty in satisfying good usability and long-lasting makeup at the same time, and emphasize emphasis on usability and finish. Has a drawback that it has poor makeup durability and easily adheres to clothes or bleeds. Many studies have been made to solve these disadvantages. For example, in lipsticks, dyes are blended to improve cosmetic durability by dyeing on the lips, and a lot of solid oily bases such as wax are blended,
The one that strengthened the coating and reduced the color transfer, the one that blended volatile oil and film-forming agent, formed a film on the skin surface by volatilization of the volatile solvent after application, and improved the cosmetic durability In addition, the addition of polyoxyalkylene-modified organopolysiloxane, etc., absorbs a small amount of moisture on the lips and moisture in the air over time, increases the viscosity of the coating, and reduces color transfer. Have been. [0003] However, those containing a dye are easy to dry in the coated portion with the passage of time, and those containing a large amount of solid oily base such as wax have a large spreadability and poor usability. In addition, a composition containing a volatile oil agent and a film forming agent loses luster over time after application, and the applied portion dries. In addition, there is a problem in stability over time since redness is caused by volatilization of the volatile solvent. Polyoxyalkylene-modified organopolysiloxane (polyether-modified silicone)
Has good compatibility with silicone oils, but has disadvantages such as poor compatibility with triglycerides and ester oils commonly used in oily cosmetics and the inability to stably blend them. Therefore, there has been a demand for an oil-based cosmetic which has excellent usability, finish, and long-lasting makeup, and has little color transfer over time. [0004] Under such circumstances, the present inventors have conducted intensive studies and as a result, by blending a long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane into an oil-based cosmetic, it has been found that the coating can be carried out. Although it has a good feeling of use at the time, it is easy to spread, but after applying it, it absorbs moisture in the air or the skin and thickens it. The invention has been completed. That is, the present invention provides an oil-based cosmetic comprising a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane. The long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane used in the present invention may be any organopolysiloxane co-modified with a long-chain alkyl group-containing group and a polyoxyalkylene group. Can also be used, and are preferably those represented by the following general formula (1) or (3). [0006] (Wherein 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, wherein R ² represents the following general formula (2)-(C ₂ H ₄₎ O) _x- (C ₃ H ₆ O) _y -R ³ (2) wherein R ³ is an alkyl group having 1 to 4 carbon atoms or a hydrogen atom, 1 is 10 to 200, and m is 1-25, and n is 1-100, with the condition that n ≧ m and 3n <l in the average molecule, and h is 7-17
And a, and the molecular weight of R ² is 250 to 2000, where x and y are the weight ratio of oxyethylene groups and oxypropylene groups 100: 0 to 20: are selected to be 80. [0008] Wherein R ⁴ represents an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group or a fluorine-substituted alkyl group, and R ⁵ represents the 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) —, and 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, and 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 each 1.0 ≦
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 comprises an organohydrogenpolysiloxane represented by the following general formula (6), a polyoxyalkylene compound represented by the following general formula (7), The compound can be easily synthesized in one step by subjecting the alkylene compound represented by the formula (8) to an 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 to 10 alkyl groups, aryl groups, aralkyl groups or fluorine-substituted alkyl groups, R ⁷
Is a hydrogen atom or 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 respectively 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 mixing ratio of the polyoxyalkylene compound of formula (8) and the alkylene compound of formula (8) is 0.5 to 2.0, preferably 0.8 to 1.2 in terms of the molar ratio of the SiH group to the terminal unsaturated group. . 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 can be a catalytic amount, and is particularly 50 ppm or less, preferably 20 ppm or less in terms of platinum or rhodium. 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 conditions for the addition reaction are not particularly limited, but the reaction is preferably performed 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, such as Abil EM-90 and Abil B9806 (both manufactured by Goldschmidt) represented by the general formula (1). Or a silicone compound of the general formula (3) (as described in JP-A-04-326324 and JP-A-07-217666), and if necessary, one or more kinds can be used. . In the present invention, the blending amount of the long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane 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 is not limited to animal oils, vegetable oils, mineral oils, and synthetic oils, and includes hydrocarbons. ,
Examples include oils and fats, waxes, esters, fatty acids, higher alcohols, silicone oils, fluorinated oils, and lipophilic surfactants. For example, liquid paraffin, squalane, polybutene, petrolatum, paraffin wax, ceresin wax, microcrystalline wax, synthetic hydrocarbon wax, jojoba oil, mocro, 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) and the like can be used. Can be used. The oil-based cosmetic of the present invention contains, in addition to the above components,
Powders generally used in cosmetics, surfactants, antioxidants, polymer compounds, fragrances, preservatives, ultraviolet absorbers, humectants, cosmetic ingredients, and the like can be appropriately blended as long as the effects of the present invention are not impaired. it can. The oily cosmetic of the present invention includes lipstick, eyeshadow, eyeliner, foundation, cream and the like, and can be produced by heating, mixing, stirring and the like. The effect of the oil-based cosmetic of the present invention is more remarkably exhibited in a system containing substantially no water. EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. Production Example 1 In a long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane reactor, the following average composition formula (9) was used. 183 parts by weight of an organohydrogensiloxane represented by the following formula, 182 parts by weight of a polyoxyalkylene represented by the following average composition formula (10): CH ₂ ＣＨCHCH ₂ O (C ₂ H ₄₀ ) ₉ H (10) 434 parts by weight of an oleyl alcohol derivative represented by the following average composition formula (11) CH ₂ ＣＨCHCH ₂ O (C ₃ H ₆ O) ₃ C ₁₈ H ₃₅ . 0.1 parts 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 distill off the solvent, followed by filtration to obtain an organopolysiloxane represented by the following reaction formula (12). Embedded image 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 ＣC (CH ₃ ) CH 241 parts by weight of a polyoxyalkylene represented by ₂ CH ₂ O (C ₂ H ₄₀ ) ₉ H... (13), and the following average composition formula (14): CH ₂ ＣＨCHCH ₂ O (C ₃ H ₆ O) ₃ C ₁₄ H ₂₉ ... 343 parts by weight of a myristyl alcohol derivative represented by the following formula:
And 160 parts by weight of ethanol, and 0.1 part by weight of an ethanol solution containing 2% by weight of chloroplatinic acid was added thereto, and the mixture was reacted under reflux of the solvent for 6 hours. The reaction product was heated under reduced pressure to distill off the solvent, followed by filtration, and the following reaction formula (15)
An organopolysiloxane represented by the following formula was obtained. Embedded image 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 [0028] was prepared lipstick compositions shown in Examples 1 to 8 and Comparative Examples 1 and 2 <Lipstick> Table 1, was performed pigment dispersibility in the molten state, usability, finished, the makeup evaluation . Table 1 also shows the results. [Table 1] (Preparation method) The component A was heated and melted at 110 to 120 ° C, and the component B was added thereto, mixed uniformly, poured into a molding die, and cooled and solidified to produce a lipstick. (Test Method and Evaluation Method) a) Pigment Dispersibility The pigment dispersibility in a molten state before flowing into the mold of each sample was visually evaluated. b) Lightness of spreadability (usability) Each sample was applied to the lips, and the lightness of spreadability was evaluated. 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 of color transfer (make-up) Each sample was applied to the lips and the panel was allowed to live a normal life. Two hours later, the lips were pressed with a tissue and the difficulty of the lipstick color transfer was evaluated. . e) Good color retention (cosmetic durability) Each sample was applied to the lips, the panel was allowed to live a normal life, and the cosmetic durability after half a day was evaluated. For each of the evaluation items, the following seven levels (0 to 6) were absolutely evaluated by a sensory panel of 10 persons, and the average score was further divided into four levels. (1) Absolute evaluation 6: Very good 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad 0: Very bad (2) 4-grade evaluation 5 or more: ◎ 4 or more and less than 5: ○ 3 points or more and less than 4 points: Δ Less than 3 points: × As is clear from the results in Table 1, the lipsticks of Examples 1 to 8 which are products of the present invention are compared with the lipsticks of Comparative Examples 1 and 2. Thus, it can be seen that the pigment has much more excellent properties in all aspects of pigment dispersibility, usability, finish, and cosmetic durability. Example 9: Oily foundation (component) (%) (1) Celesin wax 6.0 (2) Paraffin wax 5.0 (3) Vaseline 5.0 (4) Squalane remaining amount (5) Dimethyl polysiloxane 15.0 (6) Silicone compound of Production Example 1 5.0 (7) Titanium oxide (hydrophobic treatment ^* ) 10.0 (8) Sericite (hydrophobic treatment ^* ) 15.0 (9) Bengala (hydrophobic treatment) Treatment ^* ) 1.5 (10) Yellow iron oxide (hydrophobic treatment ^* ) 2.5 (11) Black iron oxide (hydrophobic treatment ^* ) 0.5 (12) Antioxidant appropriate amount (13) Flavor appropriate amount ^* methyl Hydrogen polysiloxane treatment (Preparation method) Components (1) to (6) were dissolved by heating, and (7) to (13) were added thereto, uniformly mixed, and degassed. This was filled in a metal dish and cooled and solidified to produce an oily foundation. Example 10: Eye shadow (component) (%) (1) Mica 25.0 (2) Remaining amount of talc (3) Nylon powder 5.0 (4) Titanium mica 20.0 (5) Black iron oxide 0.5 (6) Ultramarine blue 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) Suitable amount of ultraviolet absorber (13) Suitable amount of fragrance (Preparation method) Components (1) to (7) were stirred and mixed, and dissolved by heating and dissolving (8) to (13). The product is added, mixed, pulverized, and then compression-molded into a metal plate. [0038] (Preparation 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, usability and finish, and also excellent in cosmetic durability. The oil-based cosmetic of the present invention is excellent in pigment dispersibility, feeling in use, finish, and cosmetic durability by blending a specific long-chain alkyl-containing polyoxyalkylene-modified organopolysiloxane. is there.

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Shigeyoshi Momose 48-18 Sakaemachi, Kita-ku, Tokyo Inside Kose Research Institute Co., Ltd. (56) References JP-A-7-316018 (JP, A) JP-A-5 JP-A-194172 (JP, A) JP-A-4-313125 (JP, A) JP-A-5-139949 (JP, A) JP-A-6-293623 (JP, A) JP-A-5-139930 (JP, A) JP-A-7-61907 (JP, A) JP-A-5-70335 (JP, A) JP-A-5-70336 (JP, A) JP-A-5-70337 (JP, A) 105614 (JP, A) JP-A-8-198740 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A61K ^7/ 00-7/50

Claims (1)

(57) [Claims] (Claim 1) Formula (3) [Wherein, R ⁴ represents an alkyl group having 1 to 10 carbon atoms, an aryl group, an aralkyl group or a fluorine-substituted alkyl group, and R ⁵ represents the 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) —, and 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, and 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 each 1.0 ≦
a ≦ 2.5, 0.001 ≦ b ≦ 1.5, 0.001 ≦ c ≦
An oil-based cosmetic containing a silicone compound represented by the formula (1) and containing substantially no water.