JP2008056600A - Eye makeup cosmetic - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an eye makeup cosmetic excellent in smooth usability and close adhesion, especially excellent in glossy feeling, transparent feeling and flexibility of cosmetic film, and lasting property of these cosmetic effects. <P>SOLUTION: This eye makeup cosmetic excellent in smooth usability and close adhesion, especially excellent in glossy feeling, transparent feeling and flexibility of the cosmetic film, and lasting property of these cosmetic effects is provided by blending the components of (a) a compound obtained by esterifying the carboxy groups at both terminals of an oligomer ester of a dimer acid with a dimer diol with isostearyl alcohol, (b) a film-forming component and (c) silicic anhydride. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to an eye makeup cosmetic comprising a specific ester compound, a film-forming component, and silicic acid anhydride. Specifically, it is excellent in usability and adhesion, and in particular, the gloss and transparency of the cosmetic film, the flexibility, The present invention relates to eye makeup cosmetics that are excellent in the sustainability of these cosmetic effects.

Eye makeup cosmetics are cosmetics that can be applied to the eyes and eyelids to add color and change the texture, thereby making the eyes clearer and creating a more attractive appearance. It is what
Conventionally, in these eye makeup cosmetics, studies have been made to improve the adhesion and adhesion of the cosmetic film, improve the cosmetic effect and the long-lasting makeup, or increase the smooth usability during application.
Eyes and eyelids are parts that move more than other parts of the face, such as the forehead and cheeks, so eye makeup cosmetics have their makeup film formed quickly and have high adhesion and blink. Even so, the decorative film does not collapse, and it is necessary for the decorative film to be caused, and for no secondary adhesion. Therefore, volatile substances have been blended to improve quick drying, and waxes and resins have been blended to improve the adhesion of the decorative film, and the film has been strengthened to prevent the decorative film from collapsing. However, when the quick drying property is enhanced to strengthen the film, there is a problem that the feeling of use is lowered by feeling dry and losing the flexibility of the decorative film. Therefore, research to increase flexibility has been made. For example, a technique containing a non-aqueous polymer dispersion in which a polymer is dispersed in volatile silicone and a hollow powder (for example, see Patent Document 1), a technique containing a specific silylated peptide-silane compound copolymer composition (For example, refer to Patent Document 2).

  On the other hand, research has been done to change the texture by adding color using powder, fibers, etc., but if the film is solidified by improving quick drying, the decorative film loses transparency, powder and In some cases, the effect of the color and texture of the fiber is impaired. Further, the glossiness is also reduced due to the disappearance of the transparency of the decorative film. Therefore, studies have been made to improve the transparency and gloss. For example, a technique containing a specific acrylic-silicone graft copolymer and a rosin acid resin (see, for example, Patent Document 3), a technique containing a fatty acid ester of inulin and / or hydrolyzed inulin, a wax, and a candelilla resin ( (For example, see Patent Document 4)

  Furthermore, by using polydimerlinoleic acid dimer dilinoleyl which is a specific oil agent, a technique (for example, Patent Document 5) that gives gloss to a decorative film and improves adhesion and makeup durability, dimer acid and An ester obtained by esterifying an oligomer ester with a divalent or higher alcohol with a monovalent alcohol or / and a monovalent carboxylic acid, or an oligomer ester with a dimer diol and a divalent or higher carboxylic acid is converted into a monovalent alcohol. Alternatively, there is a technique (for example, Patent Document 6) relating to an ester esterified with a monovalent carboxylic acid.

JP 2004-315420 A JP 2005-263694 A JP 2000-119139 A JP 2005-306854 A JP 2002-128629 A JP 2004-256515 A

However, with the conventional technique, the flexibility of the decorative film and the glossy feeling can be improved, but those capable of having both are not developed. Also, in lipsticks, techniques that make use of the gloss of liquid oil are well studied, but in eye makeup cosmetics, non-volatile liquid oils cause makeup collapse and deterioration of usability, Not much research has been done.
Accordingly, there has been a demand for eye makeup cosmetics that are excellent in smooth usability and adhesion at the time of application, and particularly excellent in the glossiness, transparency, flexibility, and durability of these cosmetic effects.

Under such circumstances, the present inventors have conducted extensive studies to solve the above problems, and as a result, esterified carboxyl groups at both ends of oligomeric esters of dimer acid and dimer diol, which are specific ester compounds, with isostearyl alcohol. By blending the prepared compound with a film-forming component and silicic acid anhydride, it is excellent in smooth usability and adhesion at the time of application, especially the gloss and transparency of the cosmetic film, flexibility, and sustainability of these cosmetic effects. The present inventors have found that an eye makeup cosmetic excellent in quality can be obtained, and have completed the present invention.
That is, the present invention comprises the following components (a) and (b):
(A) Compound R ³ OCO—R ¹ — (— COO—R ² —OCO— in which the carboxyl groups at both ends of the oligomeric ester of dimer acid and dimer diol represented by the following chemical formula (1) are esterified with isostearyl alcohol R ^1- ) _n -COOR ³ (1)
(In the formula, R ¹ represents a dimer acid residue, R ² represents a dimer diol residue, R ³ represents an isostearyl alcohol residue, and n represents a number of 4 to 6.)
(B) A film-forming component (c) A cosmetic material containing silicic acid anhydride is provided.

  The cosmetic of the present invention relates to an eye makeup cosmetic that is excellent in usability and adhesion, and particularly excellent in glossiness, transparency, flexibility, and sustainability of these cosmetic effects.

Hereinafter, the present invention will be described in detail.
The compound obtained by esterifying the carboxyl groups at both ends of the oligomeric ester of the dimer acid and dimer diol of the component (a) used in the present invention with isostearyl alcohol (hereinafter sometimes simply referred to as “ester compound”), It can be represented by the following general formula (1).
R ³ OCO—R ¹ — (— COO—R ² —OCO—R ¹ —) _n —COOR ³ (1)
(In the formula, R ¹ represents a dimer acid residue, R ² represents a dimer diol residue, R ³ represents an isostearyl alcohol residue, and n represents a number of 4 to 6.)

The ester compound of component (a) used in the present invention is a compound obtained by esterifying carboxyl groups present at both ends of an oligomer ester obtained from dimer acid and dimer diol with isostearyl alcohol.
Dimer acid, which is a starting material, is obtained by an intermolecular polymerization reaction of unsaturated fatty acid, but is obtained by dimerizing unsaturated fatty acid having 11 to 22 carbon atoms, and mainly a dibasic acid having about 36 carbon atoms. It is an ingredient. The CAS number corresponds to 61788-89-4. Further, in the dimerization reaction, hydrogenated dimer acid obtained by hydrogenating double bonds is preferable. Examples of commercially available products include PRIPOL 1006, 1009, 1015, and 1025 (manufactured by Unikema).
The dimer diol is mainly composed of a diol having about 36 carbon atoms in which the dimer acid and / or lower alcohol ester thereof is hydrogenated in the presence of a catalyst and the carboxylic acid portion of the dimer acid is an alcohol. Examples of commercially available products include PRIPOL 2033 (manufactured by Unikema).
Isostearyl alcohol includes those obtained by reducing fatty acids obtained from dimer acid by-products, those obtained by garvet method, those obtained by aldol condensation method, etc. Can also be used. Examples of commercially available products include Speziol C18 ISOC (manufactured by Cognis).

Although the manufacturing method of the ester compound of a component (a) is not specifically limited, For example, after esterifying dimer acid and dimer diol and obtaining oligomer ester, it obtains by esterifying a carboxyl group with isostearyl alcohol further. Can do. It can also be obtained by esterifying dimer acid, dimer diol and isostearyl alcohol at once.
In the production of component (a), when an oligomer ester is obtained as an intermediate, the oligomer ester of dimer acid and dimer diol, which is an intermediate, can be obtained by changing the respective charging ratios, The average molecular weight can be adjusted. The range of the charging ratio is preferably 0.4 to 0.9 molar equivalent of dimer diol with respect to 1 molar equivalent of dimer acid. Furthermore, when esterifying with isostearyl alcohol, it is preferable that it is 0.8-1.5 mol with respect to the remaining carboxyl group.

  The conditions for the esterification reaction in obtaining the ester compound of component (a) are not particularly limited, and are carried out by a commonly used method. For example, paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, boron trifluoride diethyl ether complex or the like is used as a catalyst, and heptane, hexane, cyclohexane, toluene, xylene or the like is used as a solvent at 50 to 260 ° C. be able to. Alternatively, esterification can be carried out at 100 to 260 ° C. even without solvent and without catalyst.

  The ester compound of component (a) preferably has a viscosity at 25 ° C. of 10,000 to 20,000 mPa · s. Examples of such ester compounds include LUSPLAN DA-DD-IS (manufactured by Nippon Seika Co., Ltd.). The viscosity was measured using a cone plate viscometer (ROTO visco1 manufactured by Haake Co.) under the conditions of a shear rate of 100 (1 / s), a cone diameter of 35 mm, and an angle of 2 °.

  The blending amount of the component (a) is not particularly limited, but is preferably 0.05 to 20% by mass (hereinafter simply referred to as “%”), and in particular, in mascara, eyeliner, and eyebrow, 0.05 to 5% is more preferable, and in the eye color, 0.1 to 15% is more preferable. When it mix | blends in this range, it will become especially excellent in the glossiness, transparency, a softness | flexibility, and the sustainability of these cosmetic effects.

The film-forming component of component (b) used in the present invention is not particularly limited as long as it is a resin or polymer that forms a film when a cosmetic is applied, and even if natural, semi-synthetic, or synthetic, Either oil-soluble or water-soluble can be used.
Specifically, as an oil-soluble film forming component, terpenic acid-based resins such as rosinic acid pentaerythritol, trimethylsiloxysilicic acid, and candelilla resin (here, candelilla resin is an organic solvent made of candelilla wax) The resin content obtained by fractional extraction is preferably 65% or more, more preferably 85% or more.), Alkyl dimethicone acrylate copolymer, polyvinyl acetate type Resins, polyvinyl isobutyl ether, polyisobutylene and the like can be mentioned, and one or more of these can be used.
Examples of the water-soluble film-forming component include polyvinyl alcohol, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymer, etc., and one or more of these can be used.
Further, the film forming component can be used by dispersing in an aqueous solvent. Examples of film forming components include alkyl acrylate (co) polymers, alkyl methacrylate (co) polymers, alkyl acrylate / alkyl methacrylate copolymers, vinyl acetate polymers, alkyl acrylate / styrene copolymers. , Alkyl methacrylate / styrene copolymer, vinyl pyrrolidone / styrene copolymer, organopolysiloxane polymer, and the like. As a polymer emulsion in which one or more of these are dispersed in an aqueous solvent, for example, , Alkyl acrylate (co) polymer emulsion, alkyl methacrylate (co) polymer emulsion, acrylic acid / alkyl acrylate copolymer emulsion, acrylic acid / alkyl methacrylate copolymer emulsion, methacrylic acid / alkyl acrylate copolymer Polymer emulsion, methacryl・ Alkyl methacrylate copolymer emulsion, alkyl acrylate / styrene copolymer emulsion, alkyl methacrylate / styrene copolymer emulsion, vinyl acetate polymer emulsion, vinyl acetate-containing copolymer emulsion, vinyl pyrrolidone / styrene copolymer An emulsion, an organopolysiloxane polymer emulsion, etc. are mentioned, These 1 type (s) or 2 or more types can be used. Here, the aqueous solvent refers to a solvent that contains water as a main component and may contain a polyhydric alcohol or the like.
Among these film-forming components, terpenic acid resin, trimethylsiloxysilicic acid, alkyl dimethicone acrylate copolymer, candelilla resin, and polyisobutylene are water-soluble film-forming components as oil-soluble film-forming components. As a film-forming component used by dispersing vinylpyrrolidone / vinyl acetate copolymer in an aqueous solvent, alkyl acrylate copolymer, alkyl methacrylate copolymer, alkyl acrylate / alkyl methacrylate copolymer , Vinyl acetate polymer, alkyl acrylate / styrene copolymer, alkyl methacrylate / styrene copolymer, and vinylpyrrolidone / styrene copolymer are preferred because of their excellent usability and adhesion, and excellent cosmetic effect. .

As commercial products of component (b) used in the present invention, ester gum HP (manufactured by Arakawa Chemical Industries) as terpenic acid-based resin, and silicon KF-7312J or silicon KF-9021 (or more as trimethylsiloxysilicic acid) Shin-Etsu Chemical Co., Ltd.), Candelilla Resin E-1 (Nippon Natural Products Co.), alkyl acrylate dimethicone copolymer KP-545 (Shin-Etsu Chemical Co., Ltd.), polyisobutylene Vista NEX LMMH-LC (manufactured by Exxon Chemical Co., Ltd.), ACURYN33A (manufactured by Rohm and Haas Co.) as an alkyl acrylate copolymer emulsion, Yodosol GH800 (manufactured by NSC Japan), and vinylibran GV-5651 as a vinyl acetate polymer emulsion (Manufactured by Nissin Chemical Industry Co., Ltd.), Examples of the vinyl pyrrolidone / vinyl acetate copolymer include PVP / VAE-735 (manufactured by ISP).
Any of these components may be used alone or in combination of two or more as required.
Although the compounding quantity of a component (b) is not specifically limited, 0.5-25% is preferable and especially 1-20% is more preferable. The film-forming component can be used by being dispersed or dissolved in a solvent. In this case, the solid content of the film-forming component is set as a preferable blending amount. When it mix | blends in this range, a makeup | decoration lasting will be favorable and it will become what is excellent in a glossiness and usability.

  The silicic anhydride of the component (c) used in the present invention is not particularly limited, and any of amorphous, hydrophobized, or crystalline structures can be used, and the usability and stability over time are good. It is to make. Commercially available products include Cylysia 550, Cylicia 770, Cyrossphere C-1504 (above, manufactured by Fuji Silysia Chemical Co., Ltd.), AEROSIL200, AEROSIL300, AEROSILR972 (above, manufactured by Nippon Aerosil Co., Ltd.), NipSeal E-220 (produced by Nippon Silica Kogyo Co., Ltd.) ) Etc. can be illustrated. In particular, in oily eye makeup cosmetics, fumed silica having a primary particle size of 50 nm or less is preferred. For example, commercially available products include AEROSIL 200, AEROSIL 300, AEROSIL 380S (above, Nippon Aerosil). AEROSIL R-972, AEROSIL R-974, AEROSIL R-976S (manufactured by Nippon Aerosil Co., Ltd.) and the like may be mentioned. Moreover, these silicic anhydrides can use 1 type (s) or 2 or more types as needed.

  Although the compounding quantity of a component (c) is not specifically limited, Preferably it is 0.1 to 8%, More preferably, it is 0.5 to 5%. If it is this range, what was excellent in usability and stability with time will be obtained.

  In the eye makeup cosmetic of the present invention, various components other than the essential components, for example, an oily component, a powder component, a fiber, a surfactant, and an aqueous solution, as long as the effects of the present invention are not impaired. Ingredients, ultraviolet absorbers, water-soluble polymers, humectants, anti-fading agents, antioxidants, antifoaming agents, cosmetic ingredients, preservatives, fragrances and the like can be appropriately blended to impart various effects.

  Moreover, in this invention, hardness and the feel at the time of application | coating can be adjusted by mix | blending an oil agent other than a component (a) and a component (b). The oil agent used here can be used without particular limitation as long as it is an oil component usually used in cosmetics. The origin of animal oil, vegetable oil, synthetic oil, etc., solid oil, semi-solid oil, liquid oil, volatile oil Hydrocarbons, fats and oils, waxes, hardened oils, ester oils, fatty acids, higher alcohols, silicone oils, fluorine oils, lanolin derivatives, oily gelling agents, etc. Can be used. Specifically, liquid paraffin, heavy liquid isoparaffin, α-olefin oligomer, squalane, petrolatum, polybutene, ceresin wax, polyethylene wax, Fischer-Tropsch wax, paraffin wax, microcrystalline wax, ozokerite wax, ethylene propylene copolymer, etc. Hydrocarbons, olive oil, castor oil, mink oil, macadamia nut oil, oils such as owl, wax such as beeswax, carnauba wax, candelilla wax, gay wax, montan wax, cetyl isooctanoate, isopropyl myristate , Isopropyl palmitate, octyldodecyl myristate, neopentyl glycol dioctanoate, cholesterol fatty acid ester, glycerin fatty acid ester, jojoba Esters such as stearic acid, lauric acid, myristic acid, behenic acid, isostearic acid, oleic acid and other fatty acids, stearyl alcohol, cetyl alcohol, lauryl alcohol, oleyl alcohol, isostearyl alcohol, higher alcohols such as behenyl alcohol, Low-polymerization dimethylpolysiloxane, high-polymerization dimethylpolysiloxane, methylphenylpolysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, polyether-modified polysiloxane, polyoxyalkylene / alkylmethylpolysiloxane / methylpolysiloxane Polymers, alkoxy-modified polysiloxanes, cross-linked organopolysiloxanes, silicones such as fluorine-modified polysiloxanes, perfluorodecane, perfluoro Fluorine oils such as looctane and perfluoropolyether, lanolin derivatives such as lanolin, lanolin acetate, lanolin fatty acid isopropyl, lanolin alcohol and the like, and oily gelling agents include 12-hydroxystearic acid, dextrin palmitate, palmitic acid Acid / 2-ethylhexanoic acid dextrin, dextrin stearate, dextrin palmitate / dextrin stearate, dextrin oleate, dextrin isopalmitate, dextrin fatty acid esters of dextrin isostearate, sucrose stearate, sucrose fatty acid stearate acetate Examples thereof include esters, aluminum isostearate, and calcium stearate.

  As powder, other than component (b) and component (c), spherical, plate-like, needle-like shapes, fumes, fine particles, pigment grades, etc., or porous, non-porous particles, etc. It is not particularly limited by the structure and the like, and inorganic powders, glitter powders, organic powders, pigment powders, metal powders, composite powders, 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 and ultramarine, talc and white cloud. Mother, phlogopite, phlogopite, biotite, synthetic mica, sericite (sericite), synthetic sericite, kaolin, silicon carbide, smectite, aluminum oxide, magnesium oxide, zirconium oxide, antimony oxide, siliceous earth, silicic acid Aluminum, magnesium magnesium metasilicate, calcium silicate, barium silicate, magnesium silicate, calcium carbonate, magnesium carbonate, hydroxyapatite, boron nitride, etc., white powder, titanium dioxide coated mica, titanium dioxide coated bismuth oxychloride, oxidation Iron mica titanium, bitumen treated mica titanium, karmi Bright powder such as treated mica titanium, bismuth oxychloride, fish scale foil, polyamide resin, polyethylene resin, polyacrylic resin, polyester resin, fluorine resin, cellulose resin, polystyrene resin, styrene-acrylic co Copolymer resin powder such as polymer resin, organic polymer resin powder such as polypropylene resin, silicone resin and urethane resin, organic low molecular weight powder such as N-acyl lysine, natural organic powder such as starch, silk powder and cellulose powder Body, organic pigment powder such as red 201, red 202, red 205, red 226, red 228, orange 203, orange 204, blue 404, yellow 401, red 3, red 104 No., red No. 106, orange No. 205, yellow No. 4, yellow No. 5, green No. 3, blue No. 1, etc. zirconium, barium or aluminum Organic pigment powder such as minium lake or metal powder such as aluminum powder, gold powder, silver powder, fine particle titanium oxide coated mica titanium, fine particle zinc oxide coated mica titanium, barium sulfate coated mica titanium, titanium oxide containing silicon dioxide, zinc oxide Organic modifications such as composite powders such as silicon dioxide, laminating agents such as polyethylene terephthalate / aluminum / epoxy laminated powder, polyethylene terephthalate / aluminum laminated powder, polyethylene terephthalate / polyolefin laminated film powder, polyethylene terephthalate / polymethyl methacrylate laminated film powder A clay mineral etc. can be illustrated. These powders can be used singly or in combination of two or more of them. These powders are one or two of fluorine compound, silicone compound, metal soap, lecithin, hydrogenated lecithin, collagen, hydrocarbon, higher fatty acid, higher alcohol, ester, wax, wax, surfactant and the like. Surface treatment may be performed using seeds or more.

  The fiber is not particularly limited, but, for example, synthetic fibers such as nylon and polypropylene, artificial fibers such as rayon, natural fibers such as cellulose, semi-synthetic fibers such as acetate silk, polyethylene terephthalate and nylon form a layer and interfere light Interference fibers having These fibers can be used singly or in combination of two or more, and are subjected to surface treatment by a known method using a fluorine compound, silicone oil, powder, oil agent, gelling agent, emulsion polymer, surfactant or the like. It may be what you did.

  As the surfactant, any surfactant can be used as long as it is used in cosmetics, such as a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, etc. Is mentioned. For example, inorganic and organic salts of fatty acids such as stearic acid and lauric acid, glycerin fatty acid esters and their alkylene glycol adducts, polyglycerin fatty acid esters and their alkylene glycol adducts, sorbitan fatty acid esters and their alkylene glycol adducts, polyoxy Examples include ethylene hydrogenated castor oil, polyoxyalkylene alkyl co-modified organopolysiloxane, polyether-modified organopolysiloxane, and lecithin.

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, polyglycerin and other glycerols, aloe vera, witch hazel, hamamelis, cucumber, lemon, lavender, rose and other plant extracts It is done.
As the water-soluble polymer, other than the component (b), natural type such as guar gum, sodium chondroitin sulfate, sodium hyaluronate, gum arabic, sodium alginate, carrageenan, semi-synthetic type such as methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, etc. And synthetic compounds such as carboxyvinyl polymer, alkyl-added carboxyvinyl polymer, and sodium polyacrylate.
Examples of the UV absorber include UV absorbers such as benzophenone, PABA, cinnamic acid, and salicylic acid, 4-tert-butyl-4′-methoxydibenzoylmethane, oxybenzone, and the like. Examples include protein, mucopolysaccharide, collagen, elastin, keratin and the like.
Examples of the antioxidant include α-tocopherol and ascorbic acid, examples of the beauty component include vitamins, anti-inflammatory agents and herbal medicines, and examples of the antiseptic include paraoxybenzoate ester and phenoxyethanol.

  The dosage form of the eye makeup cosmetic of the present invention is not particularly limited, but can be an oil-in-water type and an oil-in-water emulsion type, a water-in-oil type and a water-in-oil emulsion type, an oily type, etc. It can take the form of cream, gel or liquid. Examples of eye makeup cosmetics by use include mascara, eyeliner, eyebrow, and eye color.

  For example, in the case of an oil-in-water emulsion type, the eye makeup cosmetic of the present invention adds component (a) and component (b) to the oil phase, adds component (c) to the water phase, and mixes the water phase and oil phase. Can be produced by emulsification. When component (b) is water-soluble or polymer emulsion, it is added to the aqueous phase. In the case of an oily type, it can be obtained by heating and mixing the components (a) to (c).

  Next, the present invention will be described in more detail with reference to examples. The present invention is not limited at all by these.

(Synthesis Example 1)
"Dimer acid dimer diol oligomer ester isostearyl alcohol ester compound"
Hydrogenated dimer acid (PRIPOL 1006: manufactured by Unikema) 200 g (0.348 mol) and dimer diol (PRIPOL 2033: manufactured by Unikema) 132 g (0.243 mol) were charged into a reactor and heated to 210-220 ° C. in a nitrogen stream. Then, the esterification reaction was carried out for 5 hours while distilling off the generated water to obtain 323 g of an intermediate dimer acid dimer diol oligomer ester (dimer acid: dimer diol = 1: 0.7). Furthermore, 307 g of the oligomer ester and 59 g (0.217 mol) of isostearyl alcohol (Speziol C18 ISOC: manufactured by Cognis) were charged into a reactor, heated to 210 to 220 ° C. in a nitrogen stream, and the generated water was distilled off. Then, the esterification reaction was performed for 10 hours to obtain 351 g of the target ester compound. The obtained ester compound had a hue Gardner 2, an acid value of 5.2, a saponification value of 111, a viscosity of 15,000 mPa · s, and a refractive index of 1.48.

(Examples 1-7 and Comparative Examples 1-6) Oil-in-water emulsified mascara (high viscosity cream)
An oil-in-water emulsified mascara was produced by the formulation shown in Table 1 and the production method shown below. About each obtained mascara, the smooth usability and adhesiveness at the time of application | coating, the transparent feeling and glossiness of a decorative film, its sustainability, a softness | flexibility, and its sustainability were evaluated and further determined by sensory evaluation. The results are also shown in Table 1.

* 1: Ester compound of Synthesis Example 1 * 2: Polybutene 100R (manufactured by Idemitsu Kosan Co., Ltd.)
* 3: Candelilla resin E-1 (manufactured by Nippon Natural Products)
* 4: Esther gum HP (Arakawa Chemical Industries)
* 5: Iodosol GH800 (NSC Japan)
* 6: Silicia 550 (Fuji Silysia Chemical)
(Production method)
A: After components (1) to (9) are heated and dissolved at 110 to 120 ° C., component (10) is added and mixed uniformly.
B: Components (11) to (17) are mixed uniformly and heated to 80 to 90 ° C.
C: B was added to A to emulsify, defoamed, cooled, and then filled into a container to obtain an oil-in-water emulsified mascara.

2. Sensory evaluation (evaluation method)
Each sample is evaluated by 10 panelists based on 10 sensory test panels, and each panel is evaluated in 7 levels by absolute evaluation. Judged by. For evaluation items (c) and (d), a sample was applied to a candy and the panel was allowed to live a normal life, and the condition after 6 hours was evaluated.
(Evaluation item)
(B) Usability and adhesion (b) Transparency and gloss of cosmetic film (c) Persistence of transparency and gloss (d) Flexibility and persistence (absolute evaluation)
(Score): (Evaluation)
6: Very good 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad 0: Very bad (judgment criteria)
(Average score) (Judgment)
More than 5 points: Very good: ◎
3 points to 5 points or less: Good: ○
More than 1 point and 3 points or less: Somewhat bad: △
1 point or less: Defect: ×

As is apparent from Table 1, the oil-in-water emulsified mascara of the present invention is light and smooth, has excellent usability, and also has an excellent feeling of adhesion, excellent transparency and gloss of the cosmetic film, and transparency and gloss. The feeling persisted, and the cosmetic film had excellent flexibility and durability.
On the other hand, in Comparative Example 1 in which the component (a) was not blended, an excellent product was not obtained particularly in terms of transparency and glossiness of the decorative film and its sustainability.
Further, in Comparative Example 2 using polybutene which is an oil agent with a high refractive index instead of the component (a), although the decorative film is transparent and glossy immediately after application, the decorative film is not uniformly formed. Over time, the transparency and glossiness disappeared.
In Comparative Example 3 in which component (b) was not blended, an excellent product was not obtained particularly in terms of usability and adhesion, and transparency and glossiness.
Furthermore, in Comparative Example 4 in which the amount of solid oil was increased in place of component (b), the adhesion was slightly improved, but the glossiness and its durability were not improved.
Further, in Comparative Example 5 in which the component (c) was not blended, an excellent product was not obtained particularly in terms of usability, adhesion, flexibility, and sustainability.
Further, in Comparative Example 6 using talc, which is an oil-absorbing powder, instead of component (c), the usability was somewhat improved, but the flexibility and its durability were not improved.

Example 8: Oily mascara (highly viscous gel)
(Ingredient) (%)
(1) Beeswax 3
(2) Light liquid isoparaffin 65
(3) Carnauba wax 3
(4) Ester compound * 1 3
(5) Trimethylsiloxysilicic acid * 7 2
(6) Rosin acid pentaerythlit * 4 3
(7) Black iron oxide 1
(8) Remaining amount of talc (9) Silicic acid anhydride * 8 2
* 7: Silicon KF-9021 (Decamethylcyclopentasiloxane 50% solution) (Shin-Etsu Chemical Co., Ltd.)
* 8: Cyros Sphere C-1504 (Fuji Silysia Chemical)
(Production method)
A: Components (1) to (6) are dissolved by heating at 110 ° C.
B: Components (7) to (9) are added to A and mixed uniformly.
C: B is filled into a container to obtain a product.
The oil-based mascara obtained as described above is light and smooth, has excellent usability, and also has a good feeling of adhesion, excellent transparency and glossiness of the cosmetic film, and maintains the transparency and glossiness. It was excellent in the flexibility and durability of the decorative film.

Example 9: Hydrous oil type mascara (high viscosity gel)
(Ingredient) (%)
(1) Inulin stearate 2
(2) Carnauba wax 0.5
(3) Beeswax 4
(4) Ceresin 1.5
(5) Polyethylene wax 0.5
(6) Ester compound * 1 3
(7) Candelilla resin * 3 9
(8) Rosin acid pentaerythlit * 4 4
(9) Light liquid isoparaffin remaining amount (10) Organically modified clay mineral * 9 1.6
(11) Fumed silicic acid anhydride * 10 2.5
(12) Black iron oxide 5
(13) Talc 6
(14) Purified water 6
(15) 1,3-butylene glycol 5
(16) Alkyl acrylate copolymer emulsion (solid content 50%) * 11 9
(17) Vinyl acetate polymer emulsion (solid content 45%) * 125
(18) Polyvinyl alcohol * 13 2
(19) Polypropylene fiber * 14 3
(20) Fluorine compound-treated nylon fiber * 15 3
(21) Methyl paraoxybenzoate 0.2
* 9: BENTONE38V BC (manufactured by ELEMENTIS)
* 10: AEROSIL 300 (Nippon Aerosil Co., Ltd.)
* 11: YODOSOL GH810 (NSC Japan)
* 12: Vinibrand GV-5651 (Nissin Chemical Industry)
* 13: Gohsenol EG-05 (Nippon Gosei Co., Ltd.)
* 14: P.I. P fiber 5.6D-2MM (manufactured by Chubu Pile)
* 15: Perfluoropolymethylisopropyl 5% treatment (6D (denier), 2 mm)
(Production method)
A: Components (1) to (9) are dissolved by heating at 110 ° C.
B: Components (10) to (13) are added to A and mixed uniformly.
C: Components (14) to (21) are mixed uniformly.
D: C is added to B and mixed uniformly.
E: D is filled into a container to obtain a product.
The oil-containing mascara obtained as described above is light and smooth and has excellent usability, and also has a good feeling of adhesion, excellent transparency and glossiness of the cosmetic film, and sustains the transparency and glossiness. However, it was excellent in the flexibility and sustainability of the decorative film.

Example 10: Oily eye color (solid)
(Ingredient) (%)
(1) Rosin acid pentaerythlit * 4 3
(2) Dextrin palmitate 5
(3) Glyceryl trioctanoate 10
(4) Polyglyceryl triisostearate 15
(5) Cetyl octanoate Residual amount (6) Ester compound * 1 10
(7) Haze-like silicic acid * 16 1
(8) Silicone resin powder * 17 10
(9) Iron oxide 5
(10) Titanium oxide coated glass powder * 185
(11) Polyethylene terephthalate / polymethyl methacrylate laminated film powder 5
(12) Oil-soluble rosemary extract 1
* 16: AEROSIL 200 (Nippon Aerosil Co., Ltd.)
* 17: Tospearl 2000B (GE Toshiba Silicone)
* 18: Metashine 1080RC-Y (manufactured by Nippon Sheet Glass Co., Ltd.)
(Production method)
A. Components (1) to (6) are heated and dissolved at 110 ° C., and (7) to (12) are added and mixed uniformly.
B. After filling the container, cool to make the product.
The oily eye color obtained as described above is light and smooth, has excellent usability, has excellent adhesion, has excellent transparency and glossiness of the cosmetic film, and maintains transparency and glossiness. However, it was excellent in the flexibility and sustainability of the decorative film.

Example 11: Oily eyeliner (liquid)
(Ingredient) (%)
(1) Polyisobutylene 5
(2) Light liquid isoparaffin remaining amount (3) dextrin palmitate 5
(4) Polyethylene wax 10
(5) Ceresin 5
(6) Ester compound * 1 2
(7) Haze-like silicic acid * 10 3
(8) Carmine 2
(9) Ultramarine 2
(10) Silicone-treated talc * 19 20
(11) Fragrance 0.05
* 19: 5% (dimethicone / methicone) copolymer treatment (production method)
A. Components (1) to (6) are dissolved by heating at 90 ° C., and (7) to (11) are added and mixed uniformly.
B. Fill the container to make the product.
The oil-type eyeliner obtained as described above has a light, smooth and excellent usability, and also has an excellent feeling of adhesion, excellent transparency and glossiness of the cosmetic film, and maintains the transparency and glossiness. However, it was excellent in the flexibility and sustainability of the decorative film.

Example 12: Water-in-oil emulsified eye color (cream)
(Ingredient) (%)
(1) Silicone-treated talc * 20 5
(2) Silicone-treated titanium oxide * 20 2
(3) Silicone-treated iron oxide * 20 3
(4) Blue No. 404 0.5
(5) Red No. 226 0.2
(6) Hydrophobic-treated fumed silicic acid * 21 0.2
(7) Neopentyl glycol dioctanoate 5
(8) Organically modified clay mineral * 9 1
(9) Decamethylpentasiloxane 25
(10) Ester compound * 1 3
(11) Alkyl acrylate / dimethicone copolymer * 22 5
(12) Cetyl dimethicone copolyol * 23 2.7
(13) Oil-soluble Arnica extract 0.1
(14) Nylon powder 1.5
(15) 1,3-butylene glycol 0.5
(16) Ethyl alcohol 7
(17) Methyl paraoxybenzoate 0.05
(18) Purified water remaining amount (19) Sodium chloride 0.5
(20) Fragrance 0.5
* 20: Treatment with 3% dimethylpolysiloxane * 21: AEROSIL R972 (manufactured by Nippon Aerosil Co., Ltd.)
* 22: Silicon KP-545 (Decamethylcyclopentasiloxane 30% solution) (Shin-Etsu Chemical Co., Ltd.)
* 23: ABIL EM90 (Gold Schmidt)
(Production method)
A. Ingredients (1) to (13) are mixed uniformly.
B. Components (14) to (20) are mixed uniformly.
C. B is injected into A and emulsified.
D. Fill the container with C to make a product.
The water-in-oil eye color obtained as described above is light and smooth, has excellent usability, has excellent adhesion, and has excellent transparency and glossiness of the cosmetic film, as well as transparency and glossiness. It was excellent in the flexibility of the decorative film and its sustainability.

Example 13: Oil-in-water emulsified eye color (cream)
(Ingredient) (%)
(1) Stearic acid 1
(2) Cetanol 1
(3) Glyceryl monostearate 0.5
(4) Ethylene glycol monostearate (40 EO) 0.5
(5) Candelilla resin * 3 8
(6) Ester compound * 1 5
(7) Ultramarine 1
(8) Red No. 202 1
(9) Purified water remaining amount (10) 1,3-butylene glycol 5
(11) Sodium hydroxide 0.2
(12) Hydrolyzed conchiolin solution 0.1
(13) Methyl paraoxybenzoate 0.1
(14) Alkyl acrylate copolymer emulsion (solid content 50%) * 11 10
(15) Vinylpyrrolidone / vinyl acetate copolymer * 24 3
(16) Ethyl alcohol 3
(17) Haze-like silicic acid * 10 2
(18) Mica titanium 10
(19) Fragrance 0.5
* 24: PVP / VAE-735 (made by ISP)
(Production method)
A. Components (1) to (6) are dissolved by heating at 70 ° C., and (7) and (8) are added and mixed uniformly.
B. Ingredients (9) to (19) are mixed uniformly and heated to 70 ° C.
C. Add B to A and emulsify.
D. Fill the container to make the product.
The oil-in-water emulsified eye color obtained as described above has a light, smooth and excellent usability, and also has an excellent feeling of adhesion, excellent transparency and gloss of the cosmetic film, and transparency and gloss. It was excellent in the flexibility of the decorative film and its sustainability.

Example 14: Oil-in-water emulsified eyebrow (liquid)
(Ingredient) (%)
(1) Stearic acid 3
(2) Cetanol 2
(3) Glyceryl monostearate 0.5
(4) Ester compound * 1 0.5
(5) Candelilla resin * 3 10
(6) Sucrose fatty acid ester 1.5
(7) Black iron oxide 1
(8) Silicic anhydride * 8 1
(9) Purified water remaining amount (10) 1,3-butylene glycol 5
(11) Sodium hydroxide 0.2
(12) Royal jelly extract 0.1
(13) Methyl paraoxybenzoate 0.1
(14) Alkyl acrylate copolymer emulsion (solid content 50%) * 25 10
* 25: YODOSOL GH-800 (NSC Japan)
(Manufacturing method)
A. Components (1) to (6) are dissolved by heating at 110 ° C., and (7) is added and mixed uniformly.
B. Ingredients (8) to (14) are uniformly mixed and heated to 70 ° C.
C. Add B to A and emulsify.
D. Fill the container to make the product.
The oil-in-water emulsified eyebrow obtained as described above has a light, smooth and excellent usability, and also has an excellent feeling of adhesion, excellent transparency and glossiness of the cosmetic film, and also has a transparency and glossiness. It lasted and was excellent in the flexibility of the decorative film and its sustainability.

Claims (6)

The following components (a) to (c);
(A) Compound R ³ OCO—R ¹ — (— COO—R ² —OCO) obtained by esterifying carboxyl groups at both ends of the oligomeric ester of dimer acid and dimer diol represented by the following general formula (1) with isostearyl alcohol -R ^1- ) _n -COOR ³ (1)
(In the formula, R ¹ represents a dimer acid residue, R ² represents a dimer diol residue, R ³ represents an isostearyl alcohol residue, and n represents a number of 4 to 6.)
(B) An eye makeup cosmetic comprising a film-forming component (c) and silicic anhydride.   The eye makeup cosmetic according to claim 1, wherein the blending amount of the film-forming component of component (b) is 0.5 to 25% by mass.   The film forming component of component (b) is a terpenic acid resin, trimethylsiloxysilicic acid, alkyl dimethicone acrylate copolymer, candelilla resin, polyisobutylene, vinylpyrrolidone / vinyl acetate copolymer or The eye makeup cosmetic according to claim 1 or 2, wherein there are two or more kinds.   The film forming component of component (b) is an alkyl acrylate copolymer, an alkyl methacrylate copolymer, an alkyl acrylate / alkyl methacrylate copolymer, a vinyl acetate polymer, an alkyl acrylate / styrene copolymer, a meta 2. One or more selected from an alkyl acrylate / styrene copolymer and a vinylpyrrolidone / styrene copolymer, and the film-forming component dispersed in an aqueous solvent and used. Or eye makeup cosmetics of 2.   5. The eye makeup cosmetic according to any one of claims 1 to 4, wherein the amount of silicic anhydride as the component (c) is 0.1 to 8% by mass.   The eye makeup cosmetic according to any one of claims 1 to 5, wherein the eye makeup cosmetic is used for vase.