JP3515874B2 - Lipstick composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a lipstick composition,
It relates to the improvement of the color transfer prevention effect and the like.

[0002]

2. Description of the Related Art Oil-based lipsticks, which have been the mainstream of lipsticks,
It is mainly composed of various oils, waxes and coloring materials. Such oil-based lipsticks have good luster when applied to the lips because they contain a large amount of oily components.However, they have stickiness and color against non-contact materials such as coffee cups and clothing. It had the disadvantage that it was transferred and discolored over time, resulting in poor makeup durability.

[0003] Various studies have hitherto been made to solve this drawback and improve the durability of makeup. As an example, JP-A-5-178722 discloses an oily solid cosmetic composition containing one or more polyoxyalkylene-modified organopolysiloxanes, which is excellent in long-lasting cosmetics.
Japanese Patent Application Laid-Open No. Hei 6-296630 discloses a suspension-resistant cosmetic composition containing a volatile solvent, a silicone resin, a wax, a powder, and an oil component. Japanese Patent Application Laid-Open No. 6-298623 discloses a durability containing a specific alkylmethylpolysiloxane. Lip care cosmetic composition having excellent abrasion resistance, JP-A-7-17831 discloses a nonionic surfactant obtained by addition polymerization of ethylene oxide, a liquid oil containing a perfluoroalkyl group, a liquid oil, and a semisolid. Oil-based cosmetics containing fats or solid fats and pigments and having excellent cosmetic durability.
No. 22 discloses a highly durable oily cosmetic containing a polyoxyalkylene-modified silicone, a liquid oil containing a perfluoroalkyl group, a liquid oil, a semi-solid fat or a solid fat, and a pigment.

[0004]

However, although these lipstick compositions have a certain degree of function, they are not only easy to apply and feel good, but also have good gloss on the lips.
In addition, there has not yet been obtained a colorless transfer to a non-contact material and a satisfactory cosmetic durability. SUMMARY OF THE INVENTION The present invention has been made in view of the above-mentioned problems of the prior art, and has an object to smoothly spread and have no stickiness when applied to the lips, to have a good luster on the lips, and to color a coffee cup or clothing. An object of the present invention is to provide a lipstick composition which does not transfer and has a long lasting makeup.

[0005]

Means for Solving the Problems As a result of intensive studies by the present inventors to achieve the above object, a specific siliconized polysaccharide compound, a fluorine-modified silicone and a volatile oil component are blended in a specific quantitative range. By doing so, it has been found that a lipstick composition having good coatability, feeling of use, and luster, and having extremely little color transfer and having excellent makeup durability can be obtained.
The present invention has been completed. That is, the lipstick composition according to the present invention comprises 1 to 50% by weight of a siliconized polysaccharide compound having a structure represented by the following general formula 7,

At least one fluorine-modified silicone selected from the group consisting of a fluorine-modified dimethylpolysiloxane represented by the following general formula (8) and a fluorine-modified methylphenylpolysiloxane represented by the following general formula (9) is used in an amount of 2 to 50% by weight. ,
The volatile silicone oil represented by the following general formula (10) or (11), and one or more volatile oils selected from volatile hydrocarbon oils having a boiling point in the range of 60 to 260 ° C. at normal pressure are converted into the silicone. It is characterized in that it is blended in an amount of at least 1/4 times the total amount of the modified polysaccharide compound and the fluorine-modified silicone.

[0007]

Embedded image (In the chemical formula 7, Glu is a sugar residue of the polysaccharide compound, and X is carbamo.
Yl group, —CH ₂ CH (OH) —, carbonyl group,
Y is a divalent linking group selected from the group consisting of
Oxygen atom, nitrogen atom, sulfur atom, phenylene group,
Having a carbonyloxy or oxycarbonyl group
And a hydroxy group, an alkoxy group and an
Total carbon which can have a substituent selected from a kill group
Means a divalent alkylene group having 2 to 8, ^{R 1} is C 1 -C
To 8 monovalent organic groups, R ² , R ³ , and R ⁴ each represent a monovalent organic group having 1 to 8 carbon atoms or a siloxy group represented by —OSiR ⁵ R ⁶ R ⁷ . Here, R ⁵ , R ⁶ and R ⁷ are each a monovalent organic group having 1 to 8 carbon atoms, and a is 0, 1 or 2
Means In addition, a monovalent organic group having 1 to 8 carbon atoms means
Alkyl group, cycloalkyl group, aryl group, aralkyl
Selected from alkenyl, alkenyl and fluorinated alkyl groups
It means a group having a prime number of 1 to 8. Further, the average number of bonds (degree of substitution) of the silicone compound per unit sugar constituting the polysaccharide compound is 0.5 to 2.5. )

[0008]

Embedded image (In formula 8, Rf ¹ is a perfluoroalkyl group having 1 to 12 carbon atoms, b ¹ is an integer of 0 to 5, y ¹ and z ¹ are average numbers, and y ¹
Represents a number of ^{1 to} 150, and z ¹ represents a number of 0 to 500. )

Embedded image (Wherein, Rf ² is a perfluoroalkyl group having 1 to 12 carbon atoms, b ² is an integer of 0 to 5, x ² , y ² , and z ² are average numbers, x ² is 1 to 150, y ² is 1~150, z ² is 0-1
The number 50 is shown. )

[0009]

Embedded image (In Chemical Formula 10, m represents an integer of 0 to ^3. )

Embedded image (In the formula 11, n represents an integer of 3 to 8.) In the present invention, it is preferable that the siliconized polysaccharide compound is represented by the following general formula 12.

[0010]

Embedded image (In the chemical formula 12, Glu, Y, R ¹ , R ² , R ³ , R ⁴ and a are the same as those in the chemical formula 7.) In the present invention, Glu is preferably a glucose residue of pullulan. It is. When a = 0, R ² ,
It is preferred that R ³ and R ⁴ are methyl groups. Also,
Y is - (CH _{2) 3} - it is preferable that a group represented by.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The siliconized polysaccharide compound used in the present invention is represented by the above formula (7). In the chemical formula 7, Glu represents a saccharide residue of a polysaccharide compound. As such a polysaccharide compound, various known polysaccharide compounds can be used. For example, cellulose, hemicellulose, gum arabic, tragacanth gum, tamarind gum, pectin , Starch, mannan, guar gum, locust bean gum, quince seed gum, alginic acid, carrageenan, agar, xanthan gum, dextran, pullulan,
In addition to chitin, chitosan, hyaluronic acid, chondroitin sulfate, derivatives of these polysaccharide compounds, for example, carboxymethylation, sulfation, phosphorylation, methylation, ethylation, addition of alkylene oxide such as ethylene oxide and propylene oxide, acylation And polysaccharide compound derivatives that have undergone cationization, low molecular weight, and the like. Of these, preferably ethyl cellulose or pullulan,
Particularly preferred is pullulan. In the present invention, the average molecular weight of the polysaccharide compound varies depending on the type of the polysaccharide compound, but is usually preferably about 1,000 to 5,000,000.

These polysaccharide compounds contain at least one or more reactive functional groups such as a hydroxyl group and a carboxyl group depending on the kind. The divalent linking group represented by X is a linking group derived from A formed by reacting a reactive functional group of the polysaccharide compound with a silicone compound represented by the following general formula (13). A conventionally known method can be used for the reaction between the silicone compound and the polysaccharide compound.

[0013]

Embedded image In the above formula 13, Y, R ¹ , R ² , R ³ , R ⁴ and a are the same as those in the above formula 7. A is a functional group capable of reacting with the reactive functional group of the polysaccharide compound, and examples thereof include an isocyanate group, an epoxy group, a vinyl group, an acryloyl group, a methacryloyl group, an amino group, an imino group, a hydroxyl group, a carboxyl group, and a mercapto group. And the like.

X is exemplified by a carbamoyl group, --CH
₂ CH (OH)-, a carbonyl group, an amino group, an ether group and the like, and from the viewpoint of reactivity, a compound of the above formula 13 in which A is an isocyanate group (O = C = N-);
A carbamoyl group (—CONH—) formed by reacting a hydroxyl group of a polysaccharide compound is preferable. In this case, the sugar residue of the polysaccharide compound means the remaining portion of the polysaccharide compound excluding the hydrogen atom of the hydroxyl group that has reacted with the isocyanate group. In the case of other reactions as well, the sugar residue of the polysaccharide compound means the same.

The divalent aliphatic group represented by Y includes an alkylene group, an alkylene group having an oxygen atom, a nitrogen atom, a sulfur atom or the like in the main chain, and an alkylene group having an arylene group such as a phenylene group in the main chain. Examples of the group include an alkylene group having a carbonyloxy group or an oxycarbonyl group in the main chain. These divalent aliphatic groups can have a substituent such as a hydroxy group, an alkoxy group, or an alkyl group, and the terminal atom of the aliphatic group is a hetero atom such as an oxygen atom, a nitrogen atom, or a sulfur atom. Is also good. To illustrate the _{Y, - (CH 2) 2} -, - (CH 2) 3 -, - (CH
_{2) 4 -, - (CH} 2) 6 -, - (CH 2) 8 -, - [CH 2
_{CH (CH 3)] -,} - (CH 2) 2 O (CH 2) 3 -, -
_{CH 2 CH (OH) -CH 2} - and others as mentioned, preferably - a propylene group represented by - (CH _{2) 3.}

In the above formula 7, R ¹ , R ² , R ³ , R ⁴ ,
Examples of the monovalent organic group having 1 to 8 carbon atoms found in R ⁵ , R ⁶ and R ⁷ include alkyl groups such as methyl group, ethyl group, propyl group and butyl group, and cycloalkyl groups such as cyclopentyl group and cyclohexyl group. And an aralkyl group such as a benzyl group, an alkenyl group such as a vinyl group and an allyl group, and an alkyl fluoride group such as a 3,3,3-trifluoropropyl group.

Further, R ² , R ³ and R ⁴ each represent —OSi
It may be a siloxy group represented by R ⁵ R ⁶ R ⁷ . Examples of such a siloxy group include a trimethylsiloxy group, an ethyldimethylsiloxy group, a phenyldimethylsiloxy group, a vinyldimethylsiloxy group, and a 3,3,3-trifluoropropyldimethylsiloxy group. In addition,
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , and R ⁷ may be the same or different. However, in the siliconized polysaccharide compound of the present invention, when a = 0, R ² , R ³ it is particularly preferred R ⁴ is a methyl group. Particularly preferred as the siliconized polysaccharide compound used in the present invention is a siliconized pullulan represented by the following formula (14). In addition, during Chemical Formula 14,
PL represents the glucose residue of pullulan.

[0018]

Embedded image In the siliconized polysaccharide compound of the present invention, the bonding ratio of the silicone compound to the reactive functional group of the polysaccharide compound is not necessarily required to be 100%. It must be connected. If the bonding ratio of the silicone compound to the polysaccharide compound is too low, the effect of preventing color transfer will not be sufficiently exhibited, and it may be difficult to incorporate the compound into the composition according to the present invention. In particular,
In general, it is preferable that the average number of bonds (degree of substitution) of the silicone compound per unit sugar constituting the polysaccharide compound is 0.5 to 2.5, though it varies depending on the type. In addition,
In the present invention, the degree of substitution is calculated from the Si content (% by weight) in the compound.

In the lipstick composition of the present invention, the compounding amount of the silicone-containing polysaccharide compound is usually 1 to 50% by weight, preferably 3 to 50% by weight.
It is 30% by weight, particularly preferably 5 to 20% by weight. If the amount of the silicone-containing polysaccharide compound is too small, the effect of preventing color transfer is not sufficiently exhibited. If the amount is too large, stickiness may occur or spreadability may be poor to deteriorate coatability.

Next, the fluorine-modified silicone used in the present invention will be described. In the present invention, the fluorine-modified silicone is phase-separated from the siliconized polysaccharide compound film after volatilization of the volatile oil as described later, and gives gloss on the lips by covering the siliconized polysaccharide compound. In addition, since the fluorine-modified silicone has water resistance and oil resistance properties, the effect of the silicone-modified polysaccharide compound to prevent color transfer can be further enhanced. As such a fluorine-modified silicone, one selected from a fluorine-modified dimethylpolysiloxane represented by the above formula 8 or a fluorine-modified methylphenylpolysiloxane represented by the above formula 9
Species or two or more species can be used.

Rf ¹ and Rf ² in Chemical Formulas 8 and 9 are each a perfluoroalkyl group having 1 to 12 carbon atoms and may be linear or branched. For example, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, tidecafluorohexyl, heptafluorooctyl, 2-pentafluoroethyl dodecafluorohexyl,-
C ₁₀ F _21, and the like -C ₁₂ F _25.

The perfluoroalkyl group is long, and
Y ¹ / (y ¹ + z ¹ ) and y ² / (x ²
When the value of (+ y ² + z ² ) is large, the proportion of the fluorine group in the molecule is increased and the water resistance and oil resistance are increased, but the solubility in other oil components is reduced. In the chemical formula 9, x ² / (x ²
When the value of (+ y ² + z ² ) is large, the content of the phenyl group increases, the solubility in other hydrocarbon oils increases, and the gloss increases. Therefore, x, y, z, and Rf are selected in consideration of the degree of water resistance and oil resistance required for the product, the solubility with other oil components used in the product, and the like. A substance that dissolves in the volatile oil but does not dissolve in the siliconized polysaccharide compound is used.

The compounding amount of the fluorine-modified silicone in the present invention is 2 to 50% by weight, preferably 3 to 30% by weight, more preferably 5 to 20% by weight. If it is less than 2%, the contribution of the lipstick to the effect of preventing gloss and color transfer is insufficient, and if it is more than 50%, stickiness may appear and the feeling of use may deteriorate, or a problem may occur in product stability. Next, the volatile oil component, which is another essential component of the present invention, will be described.

The volatile silicone oil represented by the above formula (1) or (2) used in the present invention is a linear or cyclic dimethylpolysiloxane, which has volatility at room temperature. To give examples of these products, K
F96A-0.65, KF96A-1, KF96A-
1.5, KF994, KF995, KF9937 (Shin-Etsu Chemical Co., Ltd.), SH200-1cs, SH200
-1.5cs, SH200-2cs (Toray Dow Corning Silicone), TSF404, TSF405,
TSF4045 (Toshiba silicone).

The boiling point at normal pressure used in the present invention is 6
The volatile hydrocarbon oil in the range of 0 to 260 ° C. may be linear or branched, for example, Isopar (registered trademark) A, C, D, E, G, H, K , L,
M (Exxon), Shersol (registered trademark)
71 (Shell), Saltroll (registered trademark) 100,
130 and 220 (Philipp Corporation), Isosol (registered trademark) 400 (Nippon Petrochemical), Parly
(Registered trademark) 4 (Nippon Oil & Fat), IP Solvent (registered trademark) 1620, IP Solvent 2028 (above, Idemitsu Petrochemical),
Isohexadecane, tetraisobutane 90 (Bayer), Permethyl (registered trademark) 99A, 101A and 102A (all from Prespers) and the like. These are volatile at room temperature.

In the present invention, one or more selected from these volatile silicone oils and volatile hydrocarbon oils can be used as the volatile oil component. In the present invention, the volatile oil component is blended to make the silicone-modified polysaccharide compound and the fluorine-modified silicone uniformly compatible in the product. For this reason, the amount of the volatile oil component in the lipstick composition is preferably at least 1/4 times, more preferably at least 1/2, the total amount of the siliconized polysaccharide compound and the fluorine-modified silicone. If the amount of the volatile oil component is too small, the siliconized polysaccharide compound or fluorine-modified silicone cannot be dissolved, which may make it difficult to commercialize the product or cause a problem in product stability. In addition, the use of a lipstick can be improved by blending a volatile oil component, and the volatile oil component volatilizes to firmly form a film of a siliconized polysaccharide compound, thereby preventing color transfer and cosmetics. The holding effect can be excellent. In order to obtain such an effect, it is preferable that a volatile oil component is blended in the composition in an amount of 2% by weight or more, particularly 5% by weight or more. The upper limit of the volatile oil content is not particularly limited and is usually 97
Although it can be blended in an amount of not more than 70% by weight,
Or less, particularly preferably 50% by weight or less. When the volatile oil content increases, the amount of the other components is relatively restricted, which may cause a problem in the formulation of the formulation or may fail to achieve the desired effect.

As described above, the silicone-modified polysaccharide compound and the fluorine-modified silicone used in the present invention are insoluble in each other, but in the lipstick composition of the present invention, they are uniformly dissolved and blended by the volatile oil component. The product stability is good over time. Further, the present lipstick composition has a property that it spreads well, is easy to apply, and has no stickiness. And after applying this to the lips,
The volatile oil is volatilized, and the siliconized polysaccharide compound forms a thin and strong film on the lips while embedding the coloring material, so that it is difficult to transfer color to a coffee cup or clothes,
The effect is that the discoloration is extremely small and the makeup lasts well. Furthermore, since the fluorine-modified silicone oil has low compatibility with the siliconized polysaccharide compound, the volatile oil component is phase-separated on the siliconized polysaccharide compound film after volatilization, and covers the siliconized polysaccharide compound film, so that it is good for lipstick. At the same time as imparting luster, the effect of preventing color transfer by the siliconized polysaccharide compound film is enhanced. Even when the fluorine-modified silicone undergoes phase separation, the coloring material remains firmly held in the siliconized polysaccharide compound film, and therefore, no color transfer occurs due to the phase separation of the fluorine-modified silicone.

As described above, the lipstick composition of the present invention, by properly blending the above-mentioned essential components, exhibits an effect of being excellent in applicability, feeling of use, luster, good color transfer and good holding. Can be.

In the lipstick composition of the present invention, in addition to the above essential components, if necessary, components commonly used in cosmetics can be blended as long as the effects of the present invention are not impaired. For example, carnauba wax, candelilla wax, bees wax, ceresin, microcrystalline wax,
Waxes such as solid paraffin, hydrocarbon oils such as squalane, liquid paraffin, petrolatum, higher fatty acids such as myristic acid, palmitic acid, stearic acid, 12-hydroxystearic acid, and behenic acid, cetyl alcohol, stearyl alcohol, oleyl alcohol , Higher alcohols such as batyl alcohol, cetyl-2-ethylhexanoate, 2-ethylhexyl palmitate, 2-octyldodecyl myristate, neopentyl glycol-2
-Ethylhexanoate, trioctanoic acid glyceride,
Pentaerythritol tetraoctanoate, glyceride triisostearate, glyceride diisostearate,
Isopropyl myristate, myristyl myristate,
Esters such as trioleic acid glyceride, olive oil, avocado oil, jojoba oil, sunflower oil, safflower oil, camellia oil, shea butter, macadamia nut oil, mink oil, lanolin, liquid lanolin, lanolin acetate, castor oil and other fats and oils, Mokurou , Waxes such as Chinese molle, dimethylpolysiloxane, methylphenylpolysiloxane, high polymerization degree gum-like dimethylpolysiloxane, polyether-modified silicone, amino-modified silicone, and silicone-based oils such as high polymerization degree gum-like amino-modified silicone , Fluorinated oils such as perfluoropolyether and perfluorocarbon, ethylene glycol, diethylene glycol, 1,3-butylene glycol, glycerin, hexamethylene glycol, isoprene glycol, polyethylene glycol, propylene glycol , Dipropylene glycol,
Diglycerin, polyglycerin, hyaluronic acid, acetylhyaluronic acid, chondroitin sulfate sodium, chitin,
In addition to humectants such as chitosan, ultraviolet absorbers, various surfactants, thickeners, gelling agents, metal soaps, antioxidants, preservatives, drugs, pigments, dyes, pearlescent agents, organic powders, inorganic powders, Perfume, ion-exchanged water and the like can be added.

The lipstick composition of the present invention is produced by heating, stirring, mixing and cooling the blended components containing the above essential components. The dosage form of the lipstick composition of the present invention is arbitrary, and for example, can be solid (such as a stick), semi-solid, or liquid,
Naturally, by using ion-exchanged water, a water-soluble component and a suitable surfactant and making full use of an emulsifying technique, a water-in-oil type or oil-in-water type lipstick can be used as long as the effects of the present invention are not lost. It is also possible. Hereinafter, the present invention will be described with reference to specific examples, but the present invention is not limited thereto. In addition, all mixing amounts are shown by weight% unless otherwise specified.

Production Example 1 Pullulan having a molecular weight of about 200,000 (trade name: Pullulan PF20,
10 g of N-methylpyrrolidone 30
The solution was dissolved in 0 ml, 1 g of triethylamine was added as a catalyst, and 70 g of tristrimethylsiloxysilylpropyl isocyanate was added dropwise.
The reaction solution was poured into water, and the resulting precipitate was washed with methanol and dried, and 58 g of tristrimethylsiloxysilylpropylcarbamate pullulan represented by the above general formula (6) was obtained.
Got. In addition, the substitution degree of the silicone compound per unit glucose of this product was 1.7.

Production Example 2 10 g of ethyl cellulose having a molecular weight of about 50,000 (trade name: Ethyl cellulose N-7, manufactured by Hercules) was dissolved in 1,000 ml of dimethylformamide, 5 g of triethylamine was added as a catalyst, and 50 g of tristrimethylsiloxysilylpropyl glycidyl ether was added. Was dropped. 11
After reacting at 0 ° C. for 8 hours, the reaction solution was poured into water, and the resulting precipitate was washed with water and methanol, dried and dried to form a siliconized ethyl cellulose 18 represented by the following general formula 15.
g was obtained. In addition, the substitution degree of the silicone compound per unit glucose of this product was 0.6.

Embedded image (In the chemical formula 15, EC represents a glucose residue of ethyl cellulose.)

Test Example 1 Formulation of Siliconized Polysaccharide Compound
Amount A lipstick composition was prepared by changing the amount of the silicone-containing polysaccharide compound as shown in Table 1 below, and subjected to a use test by 10 specialized panels. Evaluation items were ease of application, stickiness, gloss (after 5 minutes to 3 hours after application), and color transfer to a coffee cup or the like (after 5 minutes and 3 hours after application). The evaluation criteria are as follows. <Evaluation Criteria> ☆: All 10 persons judged good. ◎: 8 to 9 persons judged good. ：: 6 to 7 persons judged good. Δ: 4 to 5 persons judged good. X: 0 to 3 persons were judged to be good.

[0034]

[Table 1] ──────────────────────────────────── Component Sample No. 1 2 3 4 5 6 7 8 (1) Siliconized polysaccharide Compound 0 1 3 10 15 20 30 50 (Production Example 1) (2) Fluorine-modified silicone * 10 10 10 10 10 10 10 10 (3) Tecamethylcyclopentasiloxane 73 72 70 63 58 53 43 23 (4) Celesin 10 10 10 10 10 10 10 10 (5) Candelilla wax 2 2 2 2 2 2 2 2 (6) glyceryl diisostearate 2 2 2 2 2 2 2 2 (7) Red pigment lysole hine BCA 3 3 3 3 3 3 3 3易 Ease of application ◎ ◎ ◎ ◎ ◎ ◎ ○ △ Sticky ◎ ◎ ◎ ◎ ◎ ○ △ △ Luster ○ ○ ◎ ◎ ◎ ◎ ○ ○ Color transfer (after 5 minutes) × △ ○ ◎ ◎ ◎ ◎ ◎ (after 3 hours) × △ △ ○ ◎ ◎ ☆ ☆ ───── ─────────────────────── ─────── * In formula 8, Rf ¹ is a heptadecafluorooctyl ^{group, b 1 = 2, y 1} = 11, z 1 = 75 of the fluorine-modified dimethylpolysiloxane (Preparation Method) Each component 85 ° C. After heating and stirring and mixing, the mixture was filled in an airtight lipstick container and cooled to obtain a lipstick composition.

As is evident from Table 1, when the amount of the siliconized polysaccharide compound is too small, the color transfer to the contacted object is remarkable.
On the other hand, if the amount of the siliconized polysaccharide compound is too large, the spread becomes poor and stickiness occurs, which is not preferable. From the above, the compounding amount of the silicone-containing polysaccharide compound is 1 to 50% by weight, preferably 3 to 30% by weight, particularly preferably 5 to 20% by weight in the composition.

Test Example 2 Content of Fluorine-Modified Silicone Next, the case where the content of the fluorine-modified silicone was changed was examined. That is, a lipstick composition was prepared and evaluated in the same manner as in Test Example 1 using the formulation shown in Table 2 below.

[Table 2] ────────────────────────────────────        Component Sample No.                            9 10 11 12 13 14 15 ──────────────────────────────────── (1) Siliconized polysaccharide compound 15 15 15 15 15 15 15     (Production Example 1) (2) Fluorine-modified silicone * 0 2 5 10 20 30 50 (3) Tecamethylcyclopentasiloxane 68 66 63 58 48 38 18 (4) Cerecin 10 10 10 10 10 10 10 (5) Candelilla Row 2 2 2 2 2 2 2 (6) glyceryl diisostearate 2 2 2 2 2 2 2 (7) Red pigment litholium BCA 3 3 3 3 3 3 3 ────────────────────────────────────   Ease of application ◎ ◎ ◎ ◎ ◎ ○ ○   Sticky ◎ ◎ ◎ ◎ ◎ ○ △   Gloss △ ○ ○ ◎ ☆ ☆ ☆   Color transfer (after 5 minutes) △ △ ○ ◎ ◎ ○ ○         (After 3 hours) ○ ○ ◎ ◎ ◎ ◎ ○ ────────────────────────────────────         * Same as used in Test Example 1

As is evident from Table 2, if the amount of the fluorine-modified silicone is too small, the luster is inferior, and the effect of preventing color transfer is not sufficiently exhibited. On the other hand, if the amount of the fluorine-modified silicone is too large, the spread becomes poor and stickiness occurs, which is not preferable. In addition, an excessive amount of the fluorine-modified silicone may plasticize the silicone-containing polysaccharide compound film, and may instead cause color transfer. From the above, the blending amount of the fluorine-modified silicone is 2 to 50% by weight, preferably 3 to 30% by weight, particularly preferably 5 to 20% by weight in the composition.

Test Example 3 Amount of Volatile Oil Content Next, the case where the amount of the volatile oil component was changed was examined. That is, a lipstick composition was prepared in the same manner as in Test Example 1 using the formulation shown in Table 3 below, and the product stability was evaluated. The evaluation method was evaluated by visual observation of the appearance immediately after preparation and after standing at room temperature for one month, according to the following criteria. <Evaluation criteria> A: No change. Δ: Slight separation of oil and the like is observed. X: Separation of oil etc. is remarkable.

[0039]

[Table 3] ────────────────────────────────────        Component Sample No.                            16 17 18 19 20 21 22 ──────────────────────────────────── (1) Siliconized polysaccharide compound 10 10 10 10 10 10 10 10     (Production Example 1) (2) Fluorine-modified silicone * 10 10 10 10 10 10 10 (3) Tecamethylcyclopentasiloxane 0 2 5 10 20 30 50 (4) Cerecin 10 10 10 10 10 10 10 (5) Candelilla Row 2 2 2 2 2 2 2 (6) glyceryl diisostearate 65 63 60 55 45 35 15 (7) Red pigment litholium BCA 3 3 3 3 3 3 3 ────────────────────────────────────   (3) / [(1) + (2)] 0 0.1 0.25 0.5 1 1.5 2.5 ────────────────────────────────────   Stability (immediately after production) × △ ○ ○ ○ ○ ○         (After one month) × × △ ○ ○ ○ ○ ────────────────────────────────────         * Same as used in Test Example 1

As is evident from Table 3, if the volatile oil content is too small relative to the total amount of the silicone-containing polysaccharide compound and the fluorine-modified silicone, the oil cannot be uniformly dissolved and the product stability is low. Therefore, the amount of the volatile oil is preferably at least 1/4 or more, more preferably 1/2 or more times the total amount of the siliconized polysaccharide compound and the fluorine-modified silicone.

Test Example 4 Lipsticks were prepared in the same manner as in Test Example 1 using the formulations shown in Table 4 below.
It had an effect of preventing gloss transfer and good stability.

[Table 4] Component Sample No. 23 24 25 26 27 28 29 ──────────────────────────────────── (1) Siliconized polysaccharide compound 15-15 15 15 15 15 (Production Example 1) (1 ') Siliconized polysaccharide compound-15-----(Production Example 2) ────────────────── ────────────────── (2) Fluorine-modified silicone * 10 10-10 10 5-(2 ') Fluorine-modified silicone **--10--5 10 ── ────────────────────────────────── (3) Tecamethylcyclopentasiloxane 58 58 58--38 48 ( 3 ') Dimethylpolysiloxane (6CS / 25 ℃)---58-20-(3 ") Isosol 400----58-10────────────────── ────────────────── (4) Ceresin 10 10 10 10 10 10 10 (5) Candelilla wax 2 2 2 2 2 2 2 (6) Glyceryl stearate 2 2 2 2 2 2 2 (7) Red pigment lysolepan BCA 3 3 3 3 3 3 3 ──────────────────────────易 Ease of application ◎ ◎ ◎ ◎ ◎ ◎ ◎ Sticky ◎ ◎ ◎ ◎ ◎ ◎ ◎ Luster ◎ ◎ ◎ ◎ ◎ ◎ ◎ Color transfer (after 5 minutes) ◎ ◎ ◎ ◎ ◎ ◎ ◎ ◎ (after 3 hours) ◎ ○ ◎ ◎ ◎ ◎ ◎ ──────────────────────────────────── * Same as that used in Test Example 1 ** In the above Chemical Formula 9, Rf ² is a heptadecafluorooctyl group, b ² = 2, x ² = 2, y ² = 2, and z ² = 6. Polysiloxane

[0042]

EXAMPLES Example 1 Lipstick (1) 15.0% by weight of solid paraffin (2) Celesin 5.0 (3) Siliconized polysaccharide compound (Production Example 1) 25.0 (4) Decamethylcyclopentasiloxane 20.0 (5) Octamethylcyclotetrasiloxane 8.0 (6) Fluorine-modified silicone * 10.0 (7) Polyether-modified silicone ** 5.0 (8) Trioctanoic acid glyceride 3.0 (9) Red 201 No. 1.5 (10) Red No. 202 1.5 (11) Titanium dioxide 1.0 (12) Titanium dioxide coated mica 5.0 (13) Perfume qs * In the above formula 8, Rf ¹ is a nonafluorobutyl group, b ¹ = 2, y ¹ = 25, z ¹ = 200 Fluorine-modified dimethylpolysiloxane ** Trade name KF6008 (Shin-Etsu Chemical Co., Ltd.) (Production method) Heat-dissolve (1) to (8) and (13),
(9) to (12) are well dispersed after mixing. Thereafter, the mixture was sufficiently degassed, filled in a predetermined mold, and cooled to obtain a target lipstick.

Example 2 Solid lipstick (1) 4.0% by weight of ceresin (2) Candelilla wax 8.0 (3) Carnauba wax 2.0 (4) Siliconized polysaccharide compound (Production Example 1) 10.0 ( 5) Decamethylcyclopentasiloxane 54.95 (6) Fluorine-modified silicone * 3.0 (7) Methylphenylpolysiloxane (15 CS / 25 ° C) 2.0 (8) POE (25) POP (20) tetradecyl ether 1.0 (9) Deionized water 5.0 (10) Glycerin 2.0 (11) Propylene glycol 1.0 (12) Titanium dioxide 4.5 (13) Red No. 201 0.5 (14) Red 202 2.0 (15) red 223 No. 0.05 (16) ultraviolet absorber q.s. (17) antioxidant suitable amount (18) in perfume Appropriate amount * the reduction 9, Rf ² is represented by -C ₁₂ F ₂₅ Fluorinated methylphenylpolysiloxane (b ² = 2, x ² = 40, y ² = 20, ² z = 100) (Production method) (13) to (15) are well mixed with stirring, and (1)
(8) and (16) to (18) are added to the heat-melted product and mixed well to obtain an oil phase. Separately, (9)-(1
1) is heated and dissolved to obtain an aqueous phase. The aqueous phase was added to the oil phase, and the mixture was emulsified with a homomixer, then poured into a mold and rapidly cooled to obtain a target lipstick.

Example 3 Liquid lipstick (1) Siliconized polysaccharide compound (Production Example 2) 40.0% by weight (2) Decamethylcyclopentasiloxane 10.0 (3) Octamethylcyclotetrasiloxane 16.0 (4) Fluorine-modified silicone * 20.0 (5) Glyceryl trioctanoate 3.0 (6) Spherical silicone rubber powder 5.0 (7) Red No. 201 1.5 (8) Red 202 No. 1.5 (9) Titanium dioxide 3 0.0 (10) Appropriate amount of perfume * Fluorine-modified dimethylpolysiloxane in which Rf ¹ is a heptadecafluorooctyl group, b ¹ = 2, y ¹ = 11, and z ¹ = 75 (Formulation) (1) to (5) and (10) are heated and dissolved,
(6) to (9) were mixed with stirring and mixed well,
The desired liquid lipstick was obtained by filling in a container.

The lipstick compositions of Examples 1 to 3 are smooth and easy to apply when applied to the lips, have a non-sticky feel, have a good luster on the lips, and have a coffee cup or clothing. It was excellent in long-lasting makeup without color transfer.

[0046]

As described above, according to the present invention, by blending a specific siliconized polysaccharide compound, a fluorine-modified silicone and a volatile oil in a specific quantitative range,
It is possible to obtain a lipstick composition which is excellent in spreadability, gloss and use feeling, has very little color transfer, and is excellent in long-lasting makeup.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hideki Takahashi 1050 Nippa-cho, Kohoku-ku, Yokohama, Kanagawa Prefecture Inside Shiseido First Research Center (72) Inventor, Yoshimasa Miura Nippa-cho, Kohoku-ku, Yokohama, Kanagawa No. 1050 Shiseido Co., Ltd. First Research Center (56) References JP-A-10-29921 (JP, A) JP-A-10-29910 (JP, A) JP-A-9-295916 (JP, A) JP-A-8-295614 (JP, A) JP-A-7-330545 (JP, A) JP-A-7-277927 (JP, A) JP-A-7-41414 (JP, A) JP-A-2-295912 (JP JP, A) JP-A-8-134103 (JP, A) JP-A-6-145201 (JP, A) JP-A-6-157246 (JP, A) JP-A-8-208989 (JP, A) JP Hei 7-70204 (JP, A) (58) Survey (Int.Cl. ^7, DB name) A61K 7/00 - 7/50 CA (STN ) REGISTRY (STN)

Claims (5)

(57) [Claims] 1 to 50% by weight of a siliconized polysaccharide compound having the structure of the following general formula 1 and a fluorine-modified dimethylpolysiloxane of the following general formula 2 and a fluorine-modified dimethylpolysiloxane of the following general formula 3 2 to 50% by weight of at least one fluorine-modified silicone selected from methylphenylpolysiloxane, a volatile silicone oil represented by the following general formula 4 or 5, and a boiling point at normal pressure of 60 to 260 ° C. Wherein one or more volatile oils selected from volatile hydrocarbon oils in the range of 1 to 4 times or more of the total amount of the siliconized polysaccharide compound and the fluorine-modified silicone are blended. Lipstick composition. Embedded image (In the formula 1, Glu is a sugar residue of the polysaccharide compound, and X is carbamo.
Yl group, —CH ₂ CH (OH) —, carbonyl group,
Y is a divalent linking group selected from the group consisting of
Oxygen atom, nitrogen atom, sulfur atom, phenylene group,
Having a carbonyloxy or oxycarbonyl group
And a hydroxy group, an alkoxy group and an
Total carbon which can have a substituent selected from a kill group
Means a divalent alkylene group having 2 to 8, ^{R 1} is C 1 -C
To 8 monovalent organic groups, R ² , R ³ , and R ⁴ each represent a monovalent organic group having 1 to 8 carbon atoms or a siloxy group represented by —OSiR ⁵ R ⁶ R ⁷ . Here, R ⁵ , R ⁶ and R ⁷ are each a monovalent organic group having 1 to 8 carbon atoms, and a is 0, 1 or 2
Means In addition, a monovalent organic group having 1 to 8 carbon atoms means
Alkyl group, cycloalkyl group, aryl group, aralkyl
Selected from alkenyl, alkenyl and fluorinated alkyl groups
It means a group having a prime number of 1 to 8. Further, the average number of bonds (degree of substitution) of the silicone compound per unit sugar constituting the polysaccharide compound is 0.5 to 2.5. ) (In Formula 2, Rf ¹ is a perfluoroalkyl group having 1 to 12 carbon atoms, b ¹ is an integer of 0 to 5, y ¹ and z ¹ are average numbers,
y ¹ is 1 to 150, ^{z 1} is a number of 0-500. ) (Wherein, Rf ² is a perfluoroalkyl group having 1 to 12 carbon atoms, b ² is an integer of 0 to 5, x ² , y ² , and z ² are average numbers, x ² is 1 to 150, y ² is 1~150, ^{z 2} 0
１５０150 is shown. ) (In the chemical formula 4, m represents an integer of 0 to 3.) (In the chemical formula 5, n represents an integer of 3 to 8.) 2. The lipstick composition according to claim 1, wherein the siliconized polysaccharide compound is represented by the following general formula (6). Embedded image (In the chemical formula 6, Glu, Y, R ¹ , R ² , R ³ , R ⁴ and a are the same as those in the chemical formula 1.) 3. The lipstick composition according to claim 1, wherein Glu is a glucose residue of pullulan. 4. The lipstick composition according to claim 1, wherein a = 0 and R ² , R ³ and R ⁴ are methyl groups. 5. The lipstick composition according to claim 1, wherein Y is a group represented by — (CH ₂ ) ₃ —.