JP5393197B2 - Lip cosmetics - Google Patents

Description

  The present invention relates to a lip cosmetic containing a novel cycloalkyl group-containing acrylic copolymer. More specifically, the present invention is excellent in color retention and secondary adhesion prevention over time, and has a glossy feeling and a burden feeling. The present invention relates to a lip cosmetic excellent in smoothness and smooth use.

Conventionally, as a technique for embodying a lip cosmetic that is excellent in water resistance, oil resistance, makeup holding effect and secondary adhesion prevention effect, there are several techniques that combine an organic silicone resin and a volatile oil. For example, a technology in which an organic silicone resin having a specific structure and average molecular weight and a volatile oil are blended (see, for example, Patent Document 1), a volatile oil, a water-repellent polymer such as a silicone resin dissolved therein, a wax, and a volatile oil A technique of blending a compatible non-volatile oil (for example, see Patent Document 2) has been studied.
These technologies are cosmetics that contain organic silicone resin dissolved in volatile oil, and the coating of organic silicone resin is formed by volatilization of volatile oil after application. Although a cosmetic having an excellent secondary adhesion preventing effect can be obtained, since the film is hard and the cosmetic film lacks flexibility, the skin and lips are hard to feel, and the coating film is not glossy.
For example, a compound having a high molecular weight and an organosilicone resin having a specific structure and a volatile oil as in Patent Document 1 can provide a high makeup-holding effect and secondary adhesion prevention effect, I felt a sense of burden.
Further, as in Patent Document 2, by adding a volatile oil, a water-repellent polymer such as a silicone resin dissolved therein, and a non-volatile oil compatible with the wax and the volatile oil, in addition to the secondary adhesion preventing effect The technology to obtain a lipstick composition with a smooth feeling of use and excellent lip water retention has been studied, but the gloss of the cosmetic film is impaired by the incorporation of the wax, and the oil resistance is slightly impaired by the incorporation of the non-volatile oil. Therefore, when it is used as a lipstick, if it is overcoated with gloss, it may mix and the decorative film may collapse, resulting in poor makeup and secondary adhesion.
An acrylic resin typified by polymethylmethacrylate is widely used in cosmetics because it has high smoothness and forms a hard and glossy film. However, acrylic resins are highly polar and dissolve in organic solvents such as acetone, toluene, butyl acetate, and chloroform, but are insoluble in paraffinic solvents such as light liquid isoparaffin and isododecane. For this reason, it has been used dissolved in beauty nails, but it has been used as an aqueous dispersion or solvent dispersion in other cosmetics (see, for example, Patent Document 3).

JP-A-9-124430 JP-A-9-143034 JP 2001-294515 A

  Therefore, it was desired to develop a new film-forming agent that can provide a lip cosmetic that has excellent color retention over time and secondary adhesion prevention effects, and is excellent in glossiness, no burden, and smooth use feeling. .

As a result of intensive studies to solve the above problems, the present inventor has developed a novel acrylic copolymer and solved the above problems by blending it with a volatile oil and a coloring agent in a lip cosmetic. I found it. The newly developed component (A) cycloalkyl group-containing acrylic copolymer of the present invention is an acrylic resin and has flexibility, so when used in lip cosmetics, there is a sense of burden on the movement of the lips. In addition, because it forms a film with excellent water resistance and oil resistance, it has excellent color retention and secondary adhesion prevention effects. In addition, by dissolving in a paraffin solvent or the like commonly used in cosmetics, it is possible to develop a variety of formulation types, and the transparency of the acrylic resin makes the color of the colorant and the brightness of the pearls dirty. It has become possible to develop colors vividly.
The inventor has the following components (A), (B) and (C);
(A) An acrylic copolymer obtained by polymerizing a monomer containing the following component (a1) and component (a2) and / or (a3), wherein the component (a1) The blending amount is 50 to 90% by mass, the blending amount of the components (a2) and / or (a3) is 10 to 50% by mass, and at least 30% by mass is dissolved in light liquid isoparaffin at 25 ° C. A cycloalkyl group-containing acrylic copolymer;
(A1) acrylate and / or methacrylate containing a cycloalkyl group;
(A2) acrylate and / or methacrylate containing a linear or branched alkyl group having 8 to 12 carbon atoms;
(A3) Organopolysiloxane macromonomer containing a radical polymerizable group at one end (B) Volatile oil agent (C) By blending a colorant, water resistance, oil resistance, color retention over time and secondary The inventors have found that a lip cosmetic excellent in the adhesion preventing effect, excellent in glossiness, no burden, and smooth in use can be obtained, and has completed the present invention.

That is, the present invention provides the following components (A), (B) and (C);
(A) An acrylic copolymer obtained by polymerizing a monomer containing the following component (a1) and component (a2) and / or (a3), wherein the component (a1) The blending amount is 50 to 90% by mass, the blending amount of the components (a2) and / or (a3) is 10 to 50% by mass, and at least 30% by mass is dissolved in light liquid isoparaffin at 25 ° C. A cycloalkyl group-containing acrylic copolymer;
(A1) acrylate and / or methacrylate containing a cycloalkyl group;
(A2) acrylate and / or methacrylate containing a linear or branched alkyl group having 8 to 12 carbon atoms;
(A3) an organopolysiloxane macromonomer containing a radical polymerizable group at one end;
(B) It relates to a lip cosmetic containing a volatile oil (C) colorant.

The lip cosmetic of the present invention is excellent in color retention over time and secondary adhesion preventing effect, and is excellent in a feeling of gloss, a feeling of burden, and a smooth feeling of use.

The component (A) cycloalkyl group-containing acrylic copolymer used in the lip cosmetic of the present invention is a component that produces color retention with time, secondary adhesion prevention effect, and no burden, component (a1 Acrylate and / or methacrylate containing a cycloalkyl group; and component (a2) an acrylate and / or methacrylate containing a linear or branched alkyl group having 8 to 12 carbon atoms; and / or (a3) at one end An acrylic copolymer obtained by polymerizing a monomer containing an organopolysiloxane macromonomer containing a radical polymerizable group, wherein the compounding amount of component (a1) is 50 to 90% by mass in the total amount of constituent monomers (Hereinafter, simply referred to as “%”), the blending amount of component (a2) and / or (a3) is 10 to 50%, and light liquid isoparaffin is 25 ° C. The copolymer is not particularly limited as long as it is a copolymer that dissolves at least 30%. For example, the component (a1), the component (a2), the component (a3), and an optional component as necessary, or the component (a1) and the component Polymerizing (a2) and optional components as necessary, or component (a1), component (a3) and optional components as necessary in the presence of an organic solvent in the absence of water. More specifically, an acrylic copolymer obtained by polymerizing component (a2) 10 to 50% with respect to component (a1) 50 to 90%, or component (a1) 50 A total of 10 components (a2) and (a3) with respect to acrylic copolymer obtained by polymerizing component (a3) 10-50% with respect to -90% and component (a1) 50-90% Acrylic copolymer obtained by polymerizing ~ 50% is suitable. Can be exemplified.
In the present invention, light liquid isoparaffin is a mixture of hydrocarbons mainly composed of isoparaffin. Among them, the one used as a standard for solubility at 25% at 25 ° C. is petroleum oil as defined in JIS K2254. The initial distillation temperature according to the product distillation test method is 166 ° C., the distillation end point is 202 ° C., and the kinematic viscosity at 37.8 ° C. is 1.28 mm ² / s.

  Among the constituent monomers of the component (A) cycloalkyl group-containing acrylic copolymer of the present invention, the cycloalkyl group-containing acrylate and / or methacrylate of the component (a1) is a lipophilic polymerizable monomer and is transparent with water resistance. It forms a skeleton having a hard film-forming ability. Specific examples include cyclohexyl acrylate, cyclohexyl methacrylate, dicyclopentanyl acrylate, dicyclopentanyl methacrylate, tricyclodecyl acrylate, tricyclodecyl methacrylate, tricyclodecanyl acrylate, tricyclodecanyl methacrylate, and the like. These can be used alone or in combination of two or more. Among these, cyclohexyl methacrylate is particularly preferable because it has a good radical polymerizability, a high yield, and a copolymer having a suitable glass transition point for forming a hard film.

  Among the constituent monomers of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention, the acrylate and / or methacrylate containing a linear or branched alkyl group having 8 to 12 carbon atoms of the component (a2) is An oleophilic polymerizable monomer that forms a skeleton that imparts flexibility and adhesion to the film and enhances solubility in light liquid isoparaffin. Specific examples include octyl acrylate, octyl methacrylate, and 2-ethylhexyl. Examples thereof include acrylate, 2-ethylhexyl methacrylate, isononyl acrylate, isononyl methacrylate, lauryl acrylate, lauryl methacrylate, and the like. These may be used alone or in combination of two or more. Among these, 2-ethylhexyl methacrylate and lauryl methacrylate are preferable, and 2-ethylhexyl methacrylate is particularly preferable because it can improve solubility.

Among the constituent monomers of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention, the organopolysiloxane macromonomer of the present invention containing a radical polymerizable group at one end of the component (a3) is an acrylic. An ester compound in which an organopolysiloxane is linked to an acid or methacrylic acid via a divalent hydrocarbon group can be exemplified, and specific examples include an organopolysiloxane macromonomer represented by the following formula (1). .
These can be used individually by 1 type or in mixture of 2 or more types. The organopolysiloxane macromonomer containing a radically polymerizable group at one end of the component (a3) imparts water resistance to the film and improves the solubility in light liquid isoparaffin.

(In the formula, m is 1 to 10, preferably 1 to 4, n is an integer of 0 to 200, R ₁ represents hydrogen or a methyl group, and R _{2 to} R ₈ are alkyl groups having 1 to 5 carbon atoms. Is shown.)
More specifically, a dimethylpolysiloxane macromonomer represented by the general formula (2) can be exemplified.

(In the formula, n represents an integer of 0 to 200, R1 represents hydrogen or a methyl group, and R2 represents an alkyl group having 1 to 5 carbon atoms.)
Here, R1 is hydrogen or a methyl group, R2 is an alkyl group having 1 to 5 carbon atoms, and n representing a repeating unit of a dimethylpolysiloxane group is 0 to 200, sufficient water resistance is obtained, and further transparent It is preferable because a uniform film can be obtained. n is more preferably 5 to 150 in terms of obtaining water resistance and a uniform film.

  The cycloalkyl group-containing acrylic copolymer of component (A) of the present invention comprises component (a1), component (a2) and / or component (a3) as constituent monomers, but component (a1) 50 to The cycloalkyl group-containing acrylic copolymer obtained by polymerizing 10 to 50% of component (a2) with respect to 90% forms a relatively hard film while having flexibility, and component (a1) 50 to 50%. The acrylic copolymer obtained by polymerizing 10 to 50% of the component (a3) with respect to 90% forms a particularly water-resistant film, and the component (a2) with respect to 50 to 90% of the component (a1). ) And (a3) are polymerized at a total of 10 to 50%, and a cycloalkyl group-containing acrylic copolymer is formed with a particularly hard and water-resistant film.

  In addition, the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention is a monomer other than the above components (a1) to (a3) as long as it does not impair the effects of the present invention. It can contain as. The polymerizable monomer other than the components (a1) to (a3) is not particularly limited, but styrene, substituted styrene, vinyl acetate, acrylic acid, methacrylic acid, other acrylic esters and methacrylates, maleic anhydride, Maleic acid ester, fumaric acid ester, vinyl chloride, vinylidene chloride, ethylene, propylene, butadiene, acrylonitrile, fluorinated olefin, acrylamide, methacrylamide, methylacrylamide, methylmethacrylamide, dimethylmethacrylamide, N-isopropylacrylamide, N-vinyl Pyrrolidone, N-vinylacetamide, t-butyl acrylate, t-butyl methacrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, dimethylaminoethyl methacrylate Rate, dimethylaminoethyl methacrylamide, and 2-acrylamido-2-dimethylamino-propane sulfonate and the like.

  As the blending ratio of the constituent monomer components (a1) to (a3) of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention and any polymer monomer, the blending amount of the component (a1) is as follows: It is 50 to 90% of the total amount of constituent monomers, and preferably 50 to 80%. If it is less than 50%, a film having sufficient hardness cannot be obtained, and if it exceeds 90%, the solubility in light liquid isoparaffin deteriorates. The compounding amount of the component (a2) is 10 to 50% of the total amount of the constituent monomers, and preferably 15 to 45%. If it is less than 10%, the solubility in light liquid isoparaffin becomes poor, and if it exceeds 50%, a film with sufficient hardness cannot be obtained, and there are drawbacks such as stickiness, tackiness, and film non-uniformity. Arise. The compounding amount of the component (a3) is 10 to 50% of the total amount of the constituent monomers, and preferably 15 to 45%. If it is less than 10%, the solubility in light liquid isoparaffin deteriorates, and if it exceeds 50%, a film with sufficient hardness cannot be obtained, resulting in defects such as stickiness, tackiness, and film non-uniformity. . Moreover, about the case where a component (a2) and a component (a3) are used together, the total of the compounding quantity is 10 to 50%, and 15 to 45% is preferable. When the total amount of component (a2) and component (a3) exceeds 50%, a film with sufficient hardness cannot be obtained, and there are defects such as stickiness, tackiness, and film non-uniformity. If the total blending amount is less than 10%, the solubility in light liquid isoparaffin is deteriorated. The blending amount of the optional component may be within a range of 30% or less of the total amount of the constituent monomers, preferably 20% or less, for example, 0.01 to 10%.

The weight average molecular weight of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention is not particularly limited, but is preferably in the range of 1.0 × 10 ^{4 to} 2.0 × 10 ⁵ . The weight average molecular weight is measured by liquid gel permeation chromatography (GPC) using tetrahydrofuran as an eluent and using a calibration curve prepared with a linear polystyrene standard and a refractive index detector. When the weight average molecular weight of the cycloalkyl group-containing acrylic copolymer of component (A) is less than 1.0 × 10 ⁴ , the film-forming property is slightly inferior, and when it is greater than 2.0 × 10 ⁵ , The melt viscosity is increased, and the uniformity of the film is somewhat inferior.

  The cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention uses the above components (a1) to (a3) and other optional polymer monomers as constituent monomers as necessary, It can be obtained by random polymerization by a known polymerization method in the presence (in the absence of water). Although not particularly limited, organic peroxides such as benzoyl peroxide and lauroyl peroxide, α, α′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile), 2, Polymerization may be performed in the presence of a radical polymerization initiator such as an azo compound such as 2′-azobis (2-methylbutyronitrile), a persulfuric acid polymerization initiator such as potassium persulfate and ammonium persulfate, and a solution. A polymerization method, a suspension polymerization method, a bulk polymerization method, a precipitation polymerization method and the like can be used. Among these, the solution polymerization method is particularly preferable because it is easy to adjust the molecular weight of the obtained acrylic copolymer to the optimum range.

  Examples of the organic solvent used in the polymerization of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention include aromatic hydrocarbons such as benzene, toluene and xylene, ketones such as methyl ethyl ketone and methyl isobutyl ketone, and acetic acid. Examples thereof include esters such as ethyl and butyl acetate, and alcohols such as isopropanol, ethanol and methanol, and these can be used alone or in combination. Moreover, it can also superpose | polymerize in paraffinic solvents, such as a light liquid isoparaffin, isododecane, and isohexadecane.

  The polymerization reaction temperature of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention is not particularly limited as long as it is a temperature range in which a normal radical polymerization initiator can be used, but is usually 40 to 120 ° C. Implemented in a range. While the reaction temperature varies depending on the radical polymerization initiator to be used, the type of monomer, and the reaction temperature, it is usually carried out for 2 to 24 hours. If the polymerization time is too short, the amount of residual monomer is large and the yield is lowered, which is not preferable.

  Production examples of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention are shown below. Note that these do not limit the present invention.

(Production Example 1)
[Cycloalkyl group-containing acrylic copolymer (1)]
A four-necked separable flask (hereinafter simply referred to as “flask”) equipped with a reflux condenser, a thermometer, a nitrogen inlet tube and a stirrer was added 22.5 g of cyclohexyl methacrylate, 7.5 g of 2-ethylhexyl methacrylate and toluene. 70 g was added, and nitrogen gas was introduced to make the atmosphere sufficiently nitrogen, and then heated to 100 ° C., and 0.15 g of α, α′-azobisisobutyronitrile (hereinafter referred to as AIBN) was added. The mixture was refluxed for 3 hours for polymerization. Methanol was injected into the resulting reaction product to precipitate an acrylic copolymer, and the precipitate was filtered off and dried under vacuum to obtain 27.4 g of a solid content of cycloalkyl group-containing acrylic copolymer. The weight average molecular weight in terms of polystyrene was 5.0 × 10 ⁴ .

(Production Example 2)
[Cycloalkyl group-containing acrylic copolymer (2)]
Add 15 g of cyclohexyl methacrylate, 15 g of 2-ethylhexyl methacrylate and 70 g of toluene to the above flask, introduce nitrogen gas to make a sufficient nitrogen atmosphere, warm to 100 ° C., add 0.15 g of AIBN and reflux for 3 hours. And polymerized. Methanol was injected into the obtained reaction product to precipitate an acrylic copolymer, and the precipitate was filtered off and dried under vacuum to obtain 25.5 g of a cycloalkyl group-containing acrylic copolymer solid content. The weight average molecular weight in terms of polystyrene was 3.7 × 10 ⁴ .

(Production Example 3)
[Cycloalkyl group-containing acrylic copolymer (3)]
21 g of cyclohexyl methacrylate, 9 g of 2-ethylhexyl methacrylate and 70 g of toluene were added to the flask, and after introducing nitrogen gas to make a nitrogen atmosphere sufficiently, the mixture was heated to 100 ° C. and 0.15 g of AIBN was added. The mixture was refluxed for a period of time for polymerization. Methanol was injected into the obtained reaction product to precipitate an acrylic copolymer, and the precipitate was filtered off and dried under vacuum to obtain 23.8 g of a cycloalkyl group-containing acrylic copolymer solid. The weight average molecular weight in terms of polystyrene was 4.7 × 10 ⁴ .

(Production Example 4)
[Cycloalkyl group-containing acrylic copolymer (4)]
Add 22.5 g of cyclohexyl methacrylate, 7.5 g of methacryl-modified dimethylpolysiloxane macromonomer of the following formula (3) and 70 g of toluene to the above flask, introduce nitrogen gas into a nitrogen atmosphere, and heat up to 80 ° C. Warm, 0.15 g of AIBN was added and refluxed for 5 hours for polymerization. Methanol was injected into the obtained reaction product to precipitate an acrylic copolymer, and the precipitate was filtered and dried under vacuum to obtain 13.4 g of a solid content of cycloalkyl group-containing acrylic copolymer. The weight average molecular weight in terms of polystyrene was 5.2 × 10 ⁴ .

(Production Example 5)
[Cycloalkyl group-containing acrylic copolymer (5)]
After adding 22.5 g of cyclohexyl methacrylate, 7.5 g of methacryl-modified dimethylpolysiloxane macromonomer of the following formula (4) and 70 g of toluene to the flask and introducing nitrogen gas to make a nitrogen atmosphere sufficiently, the temperature reaches 100 ° C. The mixture was warmed, 0.15 g of AIBN was added, and the mixture was refluxed for 3 hours for polymerization. Toluene was distilled off from the obtained reaction product by evaporation, followed by vacuum drying to obtain 26.6 g of a cycloalkyl group-containing acrylic copolymer solid content. The weight average molecular weight in terms of polystyrene was 6.7 × 10 ⁴ .

(Production Example 6)
[Cycloalkyl group-containing acrylic copolymer (6)]
Add 22.5 g of cyclohexyl methacrylate, 7.5 g of methacryl-modified dimethylpolysiloxane macromonomer of the following formula (5) and 70 g of toluene to the above flask, introduce nitrogen gas into a nitrogen atmosphere, and heat up to 80 ° C. Warm, 0.15 g of AIBN was added and refluxed for 5 hours for polymerization. Methanol was injected into the obtained reaction product to precipitate an acrylic copolymer, and the precipitate was filtered off and dried under vacuum to obtain 29.1 g of a solid content of cycloalkyl group-containing acrylic copolymer.

(Production Example 7)
[Cycloalkyl group-containing acrylic copolymer (7)]
To the flask, 21 g of cyclohexyl methacrylate, 4.5 g of 2-ethylhexyl methacrylate, 4.5 g of methacryl-modified dimethylpolysiloxane macromonomer of the above formula (4) and 70 g of toluene were added, and nitrogen gas was introduced to make a nitrogen atmosphere sufficiently. Thereafter, the mixture was heated to 80 ° C., 0.15 g of AIBN was added, and the mixture was refluxed for 5 hours for polymerization. Methanol was injected into the obtained reaction product to precipitate an acrylic copolymer, and the precipitate was filtered and dried under vacuum to obtain 11.0 g of a cycloalkyl group-containing acrylic copolymer solid content. The weight average molecular weight in terms of polystyrene was 6.2 × 10 ⁴ .

(Production Example 8)
50% cyclohexyl methacrylate and 50% methacryl-modified dimethylpolysiloxane macromonomer of formula (4) above, 50% cyclohexyl methacrylate and 50% lauryl methacrylate, 75% cyclohexyl methacrylate and 25% lauryl methacrylate, 60% cyclohexyl methacrylate and 2-ethylhexyl methacrylate When each 40% methacryl-modified dimethylpolysiloxane macromonomer combination was used as a raw material and synthesized according to the above synthesis method, a cycloalkyl group-containing acrylic copolymer could be obtained.

  The cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention is dissolved in a paraffin solvent when reacted, or an oil agent such as other hydrocarbon, ester, triglyceride or the like as necessary. It is also possible to dilute with or to replace the solvent with another oil. The acrylic copolymer composition containing such an oil-soluble cycloalkyl group is also included in the component (A) of the present invention. Moreover, the solvent of the solution can be removed and the acrylic copolymer can be taken out as a solid, and the acrylic copolymer obtained can be used as an acrylic copolymer solution by dissolving in light liquid isoparaffin. You can also. Two or more of the above acrylic copolymers and their solutions can be used in combination.

  The solubility of the cycloalkyl group-containing acrylic copolymer of the component (A) of the present invention is such that the initial distillation temperature according to the petroleum product distillation test method specified in JIS K2254 is 166 ° C. When it has a distillation property of 202 ° C. and a kinematic viscosity at 37.8 ° C. of 1.28 mm 2 / s), it must be dissolved at least 30% at 25 ° C. If this solubility is shown, it is possible to form a film that is uniform, transparent, and has high coating strength.

The t-butyl group-containing acrylic copolymer of the component (A) of the present invention is used as a film-forming agent for lip cosmetics, so that it retains color retention over time, prevents secondary adhesion, and has no burden. The blending amount is preferably 0.1 to 30%, preferably 1 to 25%, more preferably 2 to 20% as a solid content. When blended in this range, it is particularly excellent in terms of color retention over time, secondary adhesion prevention effect, and lack of burden.
In the case where the t-butyl group-containing acrylic copolymer of component (A) is blended in the lip cosmetic, it is preferably used by dissolving it in the volatile oil of component (B). More preferably, it is used by dissolving in isoparaffin. In that case, it is preferable to use it as a solution concentration of about 15 to 40%, and in the case of a high concentration, about 50%.

  The component (B) volatile oil used in the lip cosmetic of the present invention is volatilized from the cosmetic film to form a film of the dissolved cycloalkyl group-containing acrylic copolymer of the component (A). If it is what produces a secondary adhesion prevention effect and is normally used for cosmetics, it will not be restrict | limited. Moreover, even if it does not dissolve the cycloalkyl group-containing acrylic copolymer of component (A), it may be used for the purpose of feeling adjustment during coating. Specific examples include light liquid isoparaffin, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, dodecamethylcyclohexasiloxane, methyltrimethicone, dimethylpolysiloxane, decamethyltetrasiloxane, and ethyltrisiloxane. As commercial products, as light liquid isoparaffin, Isopar H (manufactured by Esso Chemical Co., Ltd.), isododecane (manufactured by Bayer), isohexadecane (manufactured by Unikema), IP solvent 1620MU, IP solvent 2028MU, IP solvent 2835 (above, Idemitsu Kosan Co., Ltd.) TFS405 (manufactured by Toshiba Silicone), SH245, DC345 (manufactured by Dow Corning Toray), KF-995 (manufactured by Shin-Etsu Chemical Co., Ltd.), and silicone trimethylone as methyltrimethicone. -1.5 (made by Shin-Etsu Chemical Co., Ltd.), KF-96L-2CS (made by Shin-Etsu Chemical Co., Ltd.) as methylpolysiloxane, KF-96L-1.5CS (made by Shin-Etsu Chemical Co., Ltd.) as decamethyltetrasiloxane SIL as ethyltrisiloxane OFT ETS (manufactured by Momentive Performance Materials, Inc.), and the like. Among these, light liquid isoparaffin is preferable in that it has good solubility with the cycloalkyl group-containing acrylic copolymer of component (A) and produces a secondary adhesion preventing effect.

Although the compounding quantity of the volatile oil agent of the component (B) to the lip cosmetic of this invention is not specifically limited, 10 to 90% is preferable and especially 15 to 85% is more preferable. When it mix | blends in this range, it will become the thing especially excellent in the point of makeup lasting, secondary adhesion prevention effect, and a usability | use_condition.

The colorant of component (C) used in the lip cosmetic of the present invention colors the lip cosmetic, imparts color to the lips, and gives a cosmetic film with good color development without fogging. If it is a colorant to be used, it is particularly suitable for spherical, plate-like, spindle-like, needle-like shapes, fumes, fine particles, particle sizes such as pigment grades, or porous, non-porous particle structures, etc. Without being limited, inorganic color pigments, organic color pigments, dyes, glitter pigments, metals, and the like can be used. Specific powders include white inorganic pigments such as titanium oxide, zinc oxide, cerium oxide, and barium sulfate, colored inorganic pigments such as iron oxide, carbon black, chromium oxide, chromium hydroxide, bitumen, ultramarine, and bengara, mica Titanium, bismuth oxychloride, organic pigment-treated mica titanium, titanium dioxide-coated mica, titanium dioxide-coated synthetic phlogopite, titanium dioxide-coated bismuth oxychloride, iron oxide mica titanium, bituminized mica titanium, carmine-treated mica titanium, fish scale foil, dioxide Luminous pigments such as titanium coated glass powder, polyethylene terephthalate / aluminum / epoxy laminated powder, polyethylene terephthalate / polyolefin laminated film powder, polyethylene terephthalate / polymethyl methacrylate laminated film powder, etc., red 201, red 202, Red 205 Organic pigment powders such as red 226, red 228, orange 203, orange 204, blue 404, yellow 401, red 3, red 104, red 106, orange 205, yellow 4 , Yellow 5, green 3, blue 1, etc. zirconium, barium or aluminum lake or other organic pigment powders or metal powders such as aluminum powder, gold powder, silver powder, fine titanium oxide coated mica titanium, fine zinc oxide Examples thereof include composite powders such as coated mica titanium, barium sulfate-coated mica titanium, titanium oxide-containing silicon dioxide, and zinc oxide-containing silicon dioxide. These are one or more of fluorine compounds, silicone compounds, metal soaps, lecithins, hydrogenated lecithins, collagens, hydrocarbons, higher fatty acids, higher alcohols, esters, waxes, waxes, surfactants, etc. Surface treatment may be performed using

The compounding quantity of the component (C) used for the lip cosmetic of this invention is 0.01-25%, and 0.1-20% is preferable. Within this range, satisfactory results can be obtained in terms of providing a decorative film with good color without fogging, color retention, and secondary adhesion prevention effects.

The lip cosmetic of the present invention further imparts a plastic effect to the cycloalkyl group-containing acrylic copolymer of component (A) by further containing component (D) a non-volatile hydrocarbon oil that is liquid at 25 ° C. This is preferable in terms of producing a long-lasting color and a feeling of no burden. Among these, the non-volatile hydrocarbon oil whose viscosity in 98.9 degreeC is 200 mm < ² > / s is preferable. For example, heavy liquid isoparaffin, polybutene, and polyisobutene can be mentioned. Among them, heavy liquid isoparaffin, polybutene, and polyisobutene are preferable. Examples of commercially available products include Pearl Ream 18, Pearl Ream 24, Pearl Ream 46 (above, manufactured by Nippon Oil & Fats Co., Ltd.), Polybutene 100R, Polybutene 300R, Polybutene 2000H (above, manufactured by Idemitsu Kosan Co., Ltd.), and the like. Moreover, these can use 1 type (s) or 2 or more types as needed.

  The compounding quantity of a component (D) is 0.5 to 50%, Preferably it is 1 to 10%. If it is in this range, a satisfactory product can be obtained in terms of color durability and no sense of burden.

  In the lip cosmetic of the present invention, in addition to the above components (A), (B), (C) and (D), it is usually added to cosmetics as long as the effects of the present invention are not impaired. As components, oily components other than components (A), (B) and (D), powders such as extender pigments other than component (C), surfactants, water, polyhydric alcohols, lower alcohols, water-soluble Aqueous components such as polymers, moisturizers, saccharides, UV absorbers, antioxidants, anti-fading agents, preservatives, medicinal ingredients, stabilizers, fragrances, and the like may be appropriately blended for imparting various effects. it can.

  Moreover, as an oil agent used for this invention, it can use without a restriction | limiting especially if it is an oil component normally used for cosmetics other than component (B), (D), such as animal oil, vegetable oil, synthetic oil, etc. Regardless of the origin and properties of solid oil, semi-solid oil, liquid oil, volatile oil, etc., hydrocarbons, fats, waxes, hardened oils, ester oils, fatty acids, higher alcohols, silicone oils Fluorinated oils, lanolin derivatives, oily gelling agents and the like can be used. Specifically, hydrocarbons such as liquid paraffin, α-olefin oligomer, squalane, petrolatum, ceresin wax, polyethylene wax, Fischer-Tropsch wax, paraffin wax, microcrystalline wax, ozokerite wax, ethylene propylene copolymer, olive oil, Castor oil, mink oil, macadamia nut oil, oils such as molasses, wax such as beeswax, carnauba wax, candelilla wax, gay wax, montan wax, rosin acid pentaerythritol ester, dipentaerythritol fatty acid ester, Cholesterol fatty acid ester, N-lauroyl-L-glutamate di (cholesteryl, behenyl, octyldodecyl), isopropyl myristate, isopropyl palmitate, 2- Esters such as cetyl ylhexanoate, octyldodecyl myristate, glyceryl trioctanoate, polyglyceryl diisostearate, polyglyceryl triisostearate, diisostearyl malate, neopentyl glycol dioctanoate, jojoba oil, stearic acid, lauric acid, myristic acid, Fatty acids such as behenic acid, isostearic acid, oleic acid, higher alcohols such as stearyl alcohol, cetyl alcohol, lauryl alcohol, oleyl alcohol, isostearyl alcohol, behenyl alcohol, low polymerization dimethylpolysiloxane, high polymerization dimethylpolysiloxane, Silicone such as methylphenyl polysiloxane, alkoxy-modified polysiloxane, cross-linked organopolysiloxane, fluorine-modified polysiloxane , Fluorinated oils such as perfluorodecane, perfluorooctane, and perfluoropolyether, and lanolin derivatives such as lanolin, lanolin acetate, lanolin fatty acid isopropyl, lanolin alcohol, and the like. Stearic acid, dextrin palmitate, dextrin palmitate / 2-ethylhexanoate dextrin, dextrin stearate, dextrin palmitate / dextrin stearate, dextrin oleate, dextrin isopalmitate, dextrin fatty acid esters of dextrin isostearate, sucrose stearate, Examples thereof include sucrose fatty acid ester of sucrose acetate stearate, aluminum isostearate, calcium stearate and the like.

  As a powder component, if it is a powder used as a powder generally used in cosmetics, a spherical shape, a plate shape, a needle-like shape, a haze shape, a fine particle, a particle size such as a pigment class, a porous material, It is not particularly limited by the particle structure such as non-porous, and examples thereof include inorganic powders and organic powders. Specifically, white body powders such as talc, hydroxyapatite, boron nitride, clay minerals such as kaolin, bentonite, smectite, hectorite, montmorillonite, and their organically modified products, polyamide resins, polyethylene resins Polyester resin, fluorine resin, cellulose resin, polystyrene resin, copolymer resin such as styrene-acryl copolymer resin, organic polymer resin powder such as polypropylene resin, silicone resin, urethane resin, zinc stearate, Examples thereof include organic low molecular weight powders such as N-acyl lysine, natural organic powders such as silk powder and cellulose powder. These powders may be used singly or in combination of two or more, and may be used in combination. These powders are one or two of fluorine compounds, silicone compounds, metal soaps, lecithins, hydrogenated lecithins, collagens, hydrocarbons, higher fatty acids, higher alcohols, esters, waxes, waxes, surfactants, etc. Surface treatment may be performed using the above.

  As the surfactant, any surfactant that is generally used in cosmetics can be used. Nonionic surfactants, anionic surfactants, cationic surfactants, amphoteric surfactants, etc. Is mentioned. For example, glycerin fatty acid ester alkylene glycol adduct, polyglycerin fatty acid ester alkylene glycol adduct, sorbitan fatty acid ester and its alkylene glycol adduct, sucrose fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyalkylene alkyl co-modified organopolysiloxane , Polyoxyalkylene-modified organopolysiloxane, lecithin and the like.

  Furthermore, the aqueous component can be used for the purpose of imparting a moisture effect, and may be any component that is soluble in water and water. In addition to water, for example, alcohols such as ethyl alcohol, propylene glycol, 1 , 3-butylene glycol, dipropylene glycol, polyethylene glycol and other glycols, glycerol, diglycerin, polyglycerol and other glycerols, aloe vera, witch hazel, hamamelis, cucumber, lemon, lavender, rose and other plant extracts It is done.

  Examples of water-soluble polymers include guar gum, sodium chondroitin sulfate, sodium hyaluronate, gum arabic, sodium alginate, carrageenan and other semi-synthetic compounds such as methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, carboxyvinyl polymer, Synthetic compounds such as alkyl-added carboxyvinyl polymer, polyvinyl alcohol, polyvinyl pyrrolidone, and sodium polyacrylate, as well as proteins, mucopolysaccharides, collagen, elastin, keratin and the like.

  Examples of antioxidants include α-tocopherol and ascorbic acid. Examples of cosmetic ingredients include vitamins, anti-inflammatory agents and herbal medicines. Examples of preservatives include paraoxybenzoic acid esters, phenoxyethanol, and 1,2-pentanediol. Can be mentioned.

Examples of the ultraviolet absorber include benzophenone, PABA, cinnamic acid, salicylic acid, 4-tert-butyl-4'-methoxydibenzoylmethane, oxybenzone, and the like.

  The lip cosmetic of the present invention is not particularly limited, and examples thereof include solid, semi-solid, and liquid lipsticks, lip glosses, lip treatments, lip balms, lip bases for bases, and lipsticks. An overcoat etc. are mentioned. The dosage form is not particularly limited, but is preferably an oily type or a water-in-oil type in which the outer phase is oily in terms of color retention and gloss.

Hereinafter, the present invention will be described in detail with reference to examples. Note that these do not limit the present invention.
Examples 1 to 8 and Comparative Examples 1 to 5: Oily liquid lipsticks Oily liquid lipsticks having the composition shown in Table 1 were prepared by the following production method. Color retention over time, b. Secondary adhesion prevention effect, c. Shiny feeling, d. No sense of burden, e. The smooth usability was evaluated, and the results are also shown in Table 1.

* 1: Cycloalkyl group-containing acrylic copolymer of Production Example 1 (1)
* 2: Cycloalkyl group-containing acrylic copolymer of Production Example 2 (2)
* 3: Cycloalkyl group-containing acrylic copolymer of Production Example 3 (3)
* 4: Acrylic polymer produced by the following production method,
After adding 30 g of cyclohexyl methacrylate and 70 g of toluene to a four-necked separable flask equipped with a reflux condenser, a thermometer, a nitrogen inlet tube and a stirrer, nitrogen gas was introduced to make a sufficient nitrogen atmosphere, and then 100 ° C. Then, α, α′-azobisisobutyronitrile (AIBN) 0.15 g was added and refluxed for 3 hours for polymerization. Methanol was injected into the obtained reaction product to precipitate an acrylic polymer, and the precipitate was filtered off and dried under vacuum to obtain 29.9 g of a poly (cyclohexyl methacrylate) solid content.
* 5: Silicon KF-7312 (manufactured by Shin-Etsu Chemical Co., Ltd.), 50% decamethylcyclopentasiloxane solution * 6: Nissetsu U-3700A (manufactured by Nippon Carbide Industries Co., Ltd.), 50% light fluid isoparaffin solution * 7: IP solvent 2028 (Made by Idemitsu Kosan Co., Ltd.)
* 8: AEROSIL300 (Nippon Aerosil Co., Ltd.)
* 9: BENTONE 38 (made by Elementis)
* 10: Polybutene 2000H (made by Idemitsu Kosan Co., Ltd.)
(Production method)
A: Components (1) to (8) are uniformly dissolved.
B: Components (9) to (15) are added to A and uniformly mixed and dispersed.
C: B is defoamed and then filled into a container with an application body.

(Evaluation method)
Each sample was tested for use by 20 specialist panels. For each panel, immediately after application for C, D, E, for B, observe no color transfer when tissue is turned off 10 minutes after application, and for A, 6 hours after application, The following absolute evaluation criteria were evaluated and graded, and the average value was calculated from the total score of all the panels of each sample, and judged according to the following 4-grade criteria. In the table, the determination result and the average value of the score are shown in parentheses.
<Sensory evaluation items>
A. Color retention over time. Secondary adhesion prevention effect c. Sense of gloss. There is no burden. Smooth feel <absolute evaluation criteria>
(Score): (Evaluation)
6 points: Very good 5 points: Good 4 points: Slightly good 3 points: Normal 2 points: Slightly bad 1 point: Defects <4 step criteria>
(Judgment): (Average score)
◎: More than 5 points ○: More than 3 points 5 points or less △: More than 2 points 3 points or less ×: 2 points or less

As is clear from the results of the table, the oily liquid lipsticks of Examples 1 to 8 of the present invention have a color retention over time, a secondary adhesion preventing effect, and a glossy feeling compared to the oily liquid lipsticks of Comparative Examples 1 to 5. It was excellent in the sense of lack of burden and smooth use. In particular, Example 6 in which the olefin polymer of component (D) and / or polyolefin was blended was excellent in terms of color durability and no sense of burden. On the other hand, Comparative Example 1 in which the cycloalkyl group-containing acrylic copolymer of the component (A) is not blended does not form a film, so that the color persistence is poor and the secondary adhesion preventing effect is not observed. In Comparative Example 2 in which the volatile oil of component (B) is not blended, the decorative film cannot form a sufficient film, and a satisfactory film can be obtained in terms of secondary adhesion prevention effect and lack of burden. There wasn't. Further, in Comparative Example 3 in which an acrylic polymer was used instead of the cycloalkyl group-containing acrylic copolymer of component (A), the uniformity of the decorative film was lacking. Therefore, in terms of gloss, component (A) In Comparative Example 4 in which trimethylsiloxysilicic acid was used instead of, a dispersion of an alkyl acrylate / styrene copolymer instead of the component (A) was used because the decorative film lacked flexibility and there was no burden. In Comparative Example 5 in which the decorative film was used, the decorative film lacked in flexibility and uniformity, and satisfactory results were not obtained in terms of glossiness and lack of burden.

Example 9: Oily stick-like lipstick (component) (%)
(1) Polyethylene wax * 11 6
(2) Candelilla wax 6
(3) Cetyl tri-2-ethylhexanoate 30
(4) Cycloalkyl group-containing acrylic copolymer * 2 1
(5) Isododecane * 12 Residual amount (6) Trimethylsiloxysilicate solution * 5 1
(7) Decamethylcyclopentasiloxane 5
(8) PEG-9 polydimethylsiloxyethyl dimethicone 1
(9) Silylated silicic acid * 13 2
(10) Bengala-coated mica titanium * 14 5
(11) Red No. 202 0.1
(12) Yellow No. 4 0.1
(13) Refined avocado oil 0.1
(14) Fragrance 0.5
* 11: PERFORMALENE 500 (manufactured by New Phase Technology)
* 12: Isododecane (manufactured by Bayer)
* 13: AEROSIL R972 (Nippon Aerosil Co., Ltd.)
* 14: Dimethylpolysiloxane 3% treatment (manufacturing method)
A: The component (4) and the component (5) are uniformly dissolved.
B: A, components (1) to (3) and components (6) to (8) are uniformly dissolved by heating at 95 ° C.
C: Components (9) to (14) are added to B and mixed and dispersed uniformly.
D: After defoaming C, fill the container.
The oily stick-like lipstick thus obtained was evaluated in the same manner as in Examples 1 to 8, and was excellent in color retention over time, secondary adhesion prevention effect, glossiness, no feeling of burden, and smooth use feeling. It was.

Example 10: Oily paste lip gloss (component) (%)
(1) Dextrin palmitate 3
(2) Heavy liquid isoparaffin * 15 30
(3) Cycloalkyl group-containing acrylic copolymer solution * 16 50
(4) Isododecane * 11 remaining amount (5) Titanium oxide coated glass powder * 17 5
(6) Honey 0.01
* 15: Pearl Dream 18 (Nippon Yushi Co., Ltd.)
* 16: 30% light fluid isoparaffin solution of the cycloalkyl group-containing acrylic copolymer (3) of Production Example 3 * 17: Metashine 1080RC-R (manufactured by Nippon Sheet Glass Co., Ltd.)
(Production method)
A: Components (1) to (4) are uniformly dissolved by heating at 95 ° C.
B: Components (5) to (6) are added to A and mixed and dispersed uniformly.
C: After defoaming B, fill the tube container.
The oily paste-like lip gloss thus obtained was evaluated in the same manner as in Examples 1 to 8. As a result, the color persisted over time, the effect of preventing secondary adhesion, a feeling of gloss, no feeling of burden, and a smooth feeling of use. It was excellent.

Example 11: Oily solid lip balm (component) (%)
(1) Ceresin wax 18
(2) Vaseline 30
(3) Glyceryl 2-ethylhexanoate 5
(4) Polyglyceryl triisostearate 10
(5) Cycloalkyl group-containing acrylic copolymer * 18 1
(6) Acrylic copolymer containing cycloalkyl group * 19 1
(7) Isohexadecane * 20 Residual amount (8) Ethanol 0.5
(9) Polyethylene terephthalate / aluminum / epoxy laminated powder 1
(10) Titanium oxide * 21 0.1
(11) Tocopherol acetate 0.1
* 18: Cycloalkyl group-containing acrylic copolymer of Production Example 4 (4)
* 19: Cycloalkyl group-containing acrylic copolymer of Production Example 5 (5)
* 20: Isohexadecane (manufactured by Unikema)
* 21: 5% perfluoropolyether treatment (production method)
A: Components (1) to (7) are uniformly dissolved by heating at 95 ° C.
B: Components (8) to (11) are added to A and mixed and dispersed uniformly.
C: B is defoamed and then filled into a jar.
The oily solid lip balm thus obtained was evaluated in the same manner as in Examples 1 to 8. As a result, the color persisted over time, the effect of preventing secondary adhesion, a glossy feeling, no feeling of burden, and a smooth feeling of use. It was excellent.

Example 12: Water-in-oil pasty lipstick (component) (%)
(1) Dextrin palmitate 2
(2) α-olefin oligomer Remaining amount (3) Decamethylcyclopentasiloxane 5
(4) Polyoxyethylene / methylpolysiloxane copolymer 1
(5) Sorbitan sesquioleate 5
(6) Cycloalkyl group-containing acrylic copolymer * 22 0.5
(7) Isododecane * 12 1
(8) Purified water 20
(9) Red No. 226 0.3
(10) Titanium oxide * 21 0.1
* 22: Cycloalkyl group-containing acrylic copolymer of Production Example 6 (6)
(Production method)
A: Components (1) to (7) are uniformly dissolved by heating at 95 ° C.
B: Component (8) is added to A and emulsified. Thereafter, components (9) to (10) are added and mixed uniformly.
C: After defoaming B, fill the tube container.
The water-in-oil pasty lipstick thus obtained was evaluated in the same manner as in Examples 1 to 8. As a result, the color persisted over time, the effect of preventing secondary adhesion, a feeling of gloss, no feeling of burden, and smooth use. It was excellent in feeling.

Example 13: Water-in-oil paste lipstick base (component) (%)
(1) Dextrin palmitate 5
(2) α-olefin oligomer remaining amount (3) sorbitan sesquioleate 5
(4) Cycloalkyl group-containing acrylic copolymer * 23 0.5
(5) Isododecane * 12 1
(6) Purified water 10
(7) Red No. 218 0.05
(8) Nylon fiber 0.1
* 23: Cycloalkyl group-containing acrylic copolymer of Production Example 7 (7)
(Production method)
A: Components (1) to (5) are uniformly dissolved by heating at 95 ° C.
B: Components (6) to (8) are added to A and emulsified.
C: After defoaming B, fill the tube container.
The water-in-oil pasty lipstick base thus obtained was evaluated in the same manner as in Examples 1 to 8, and was excellent in color retention over time, lack of burden, and smooth use feeling. .

Claims (9)

The following components (A), (B) and (C)
(A) An acrylic random copolymer obtained by polymerizing a monomer containing the following component (a1) and components (a2) and / or (a3), wherein the component (a1) The blending amount of the component (a2) and / or (a3) is 10 to 50% by weight, and at least 30% by weight is dissolved in light liquid isoparaffin at 25 ° C. A cycloalkyl group-containing acrylic random copolymer;
(A1) acrylate and / or methacrylate containing a cycloalkyl group;
(A2) acrylate and / or methacrylate containing a linear or branched alkyl group having 8 to 12 carbon atoms;
(A3) A lip cosmetic comprising an organopolysiloxane macromonomer containing a radically polymerizable group at one end, (B) a volatile oil agent (C) and a colorant. The lip cosmetic according to claim 1, wherein the cycloalkyl group-containing acrylic random copolymer of component (A) is obtained by polymerizing component (a1) and component (a2). The lip cosmetic according to claim 1, wherein the cycloalkyl group-containing acrylic random copolymer of component (A) is obtained by polymerizing component (a1) and component (a3). The lip of claim 1, wherein the cycloalkyl group-containing acrylic random copolymer of component (A) is obtained by polymerizing component (a1), component (a2) and component (a3). Cosmetics. The constituent monomer component (a3) of the cycloalkyl group-containing acrylic random copolymer of the component (A) is a dimethylpolysiloxane macromonomer represented by the following general formula (1): Lip cosmetics according to either 3 or 4.

(In the formula, m is 1 to 10, preferably 1 to 4, n is an integer of 0 to 200, R1 represents hydrogen or a methyl group, and R2 to R8 represent an alkyl group having 1 to 5 carbon atoms. ) The lip cosmetic according to any one of claims 1 to 5, wherein the constituent monomer component (a1) of the cycloalkyl group-containing acrylic random copolymer of the component (A) is cyclohexyl methacrylate. The cycloalkyl group-containing acrylic random copolymer of the component (A) has a weight average molecular weight in terms of polystyrene measured by liquid gel permeation chromatography of 1.0 × 10 ^{4 to} 2.0 × 10 ^5. The lip cosmetic according to any one of claims 1 to 6. The lip cosmetic according to any one of claims 1 to 7, wherein the volatile oil of component (B) is light liquid isoparaffin. Furthermore, lip cosmetics in any one of Claims 1-8 which contain liquid non-volatile hydrocarbon oil at 25 degreeC as a component (D).