JPH10152416A - Composition for rough (lip stock) - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a rough composition that shows improved spread and cosmetic durability by formulating hydroxyalkylated cyclodextrin and a specific silicone cinnamic acid derivative at a specific ratio. SOLUTION: This composition contains (A) 0.1-10.0wt.% of hydroxyalkylated cyclodextrin and (B) 0.1-10.0wt.% of a silicone connamic acid derivative bearings the unit of the formula [R<1> is a 1-4C alkyl, phenyl, trimethylsiloxy; R<2> is a divalent hydrocarbon having 2 or more carbon atoms (may be contain O atoms); X is an alkoxy; n is 0-3; a is 2, 3] and another unit: O(4-m)/2 SiR<3> m (R<3> is Ru1 ; m is n) and (C), when necessary, a nonvolatile oil, an antioxidant, an ultraviolet absorber, an ultraviolet screening agent, a preservative, a humectant, dyes, pigments and the like. When the composition is made into a stock, 5.0-20.0wt.% of a shape-retaining agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention belongs to the technical field of lipstick compositions, and more specifically to the lipstick composition having improved spreadability and long-lasting makeup.

[0002]

2. Description of the Related Art Lipstick is used to apply color to the lips by applying to the lips, to give gloss and to bring out charm.
It is one of the makeup cosmetics that has the most cosmetic effect. One of the quality functions required of the lipstick is that "it can be spread smoothly and smoothly on the lips, and can be held for a necessary time". The lipstick composition generally used for lipsticks mainly contains a powder containing wax, various liquid oils, and coloring materials, and a combination of these powders provides basic lipsticks related to the above-mentioned quality functions. Maintains ease of use, gloss, moist feeling, and long lasting makeup.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a lipstick composition which further improves "expansion" and "makeup durability" related to the basic usability of the lipstick.

[0004]

Means for Solving the Problems As a result of diligent studies aimed at solving this problem, the present inventor has found that by mixing a hydroxyalkylated cyclodextrin with a specific silicone cinnamate derivative, it is possible to achieve a better result. The present inventors have found that a lipstick composition with improved "growth" and "makeup durability" can be provided, and completed the present invention.

That is, the present invention provides a lipstick composition comprising the following components (a) and (b): (A) 0.1% by weight or more and 10.0% by weight or less of the hydroxyalkylated cyclodextrin based on the whole composition. (B)

Embedded image (In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms, a phenyl group or a trimethylsiloxy group, and R ² has at least 2 carbon atoms and may contain an oxygen atom. X represents a hydrogen group, X represents an alkoxy group, and n represents 0
A represents an integer of 1 to 3, a represents 2 or 3, and O _{(4-m) / 2} SiR ³ _m (II) (wherein R ³ has 1 carbon atom) Represents an alkyl group, a phenyl group or a trimethylsiloxy group, and m represents an integer of 0 to 3). Above, 10.0
% By weight or less.

In the present invention, the term "composition for lipstick" refers to a composition used for lipstick, which is a makeup cosmetic, such as sticky, pencil, ointment and the like.
It is used regardless of the specific form of the lipstick.

[0007]

Embodiments of the present invention will be described below. The lipstick composition of the present invention is a lipstick composition comprising a hydroxyalkylated cyclodextrin. The hydroxyalkylated cyclodextrin (hereinafter, also referred to as HACD) blended in the composition for lipstick of the present invention is cyclodextrin (hereinafter, also referred to as CD) which is well known as a cyclic oligosaccharide.
Is obtained by introducing a hydroxyalkyl group into a hydroxyl group. That is, it is a cyclodextrin derivative in which a hydrophobic hydroxyalkyl group is introduced into a hydroxyl group of cyclodextrin to increase the hydrophobicity.

Cyclodextrin is an oligosaccharide in which glucose residues are cyclically linked by α-1,4 bonds,
Α-cyclodextrin consisting of 6 glucose residues,
7 β-cyclodextrins, 8 γ
-Cyclodextrins are generally known. In the present invention, one or more of these cyclodextrins can be selected and used. Also, α,
It can also be used in the form of a starch hydrolyzate containing both β and γ cyclodextrins simultaneously.

As the hydroxyalkyl group to be substituted for the hydroxyl group of cyclodextrin, a hydroxyethyl group, a hydroxypropyl group and the like are mainly used. Hydroxyalkylated cyclodextrin can be obtained by performing a hydroxyl group substitution reaction with these. Examples of the hydroxyalkylated cyclodextrin include hydroxyethylated cyclodextrin, hydroxypropylated cyclodextrin, hydroxybutylated cyclodextrin, and dihydroxypropylated cyclodextrin. In the present invention, a suitable substitution degree of a hydroxyl group to a hydroxyalkyl group is 1 to 14 per cyclodextrin.

[0010] Among these hydroxyalkylated cyclodextrins, hydroxyethylated β-cyclodextrin or hydroxypropylated β-cyclodextrin can be mentioned as a particularly preferred hydroxyalkylated cyclodextrin. That is, these preferred hydroxyalkylated cyclodextrins are relatively easy to produce, and when incorporated into the lipstick composition of the present invention, the usability of this composition is particularly improved. Since cyclodextrin is particularly poorly soluble in water, it is possible to particularly improve the cosmetic durability of the lipstick composition of the present invention containing these.

Several methods have been known for producing hydroxyalkylated cyclodextrins. Hydroxyalkylated cyclodextrins which can be added to the lipstick composition of the present invention are also prepared by using these production methods. Can be manufactured. An example of the manufacturing process will be described in a manufacturing example described later.

The amount of the hydroxyalkylated cyclodextrin in the lipstick composition of the present invention is 0.1% by weight or more and 10.0% by weight or less of the whole composition.
It is preferably from 5% by weight to 8.0% by weight. When the amount is less than 0.1% by weight of the whole composition, the effect of improving the cosmetic durability is not sufficiently exhibited, which is not preferable. When the amount is more than 10.0% by weight, the tendency to increase the spread is strongly preferred. Absent.

The lipstick composition of the present invention is a lipstick composition comprising the above-mentioned silicone cinnamate derivative.
As described above, this silicone transdermal acid derivative is a silicone transdermal acid derivative having a unit (I) and a unit (II) in one molecule.

First, the unit (I) will be described.
In the unit (I), R ¹ represents an alkyl group having 1 to 4 carbon atoms, a phenyl group or a trimethylsiloxy group, and n represents the number of substitutions of R ¹ . R ¹ is, for example, a methyl group,
Examples thereof include an ethyl group, a propyl group, an isopropyl group, a t-butyl group, a phenyl group, and a trimethylsiloxy group. However, a methyl group, a phenyl group, or a trimethylsiloxy group may be used because of availability of raw materials. preferable. When a plurality of the units (I) are present in the silicone-based cinnamic acid derivative, R ¹ and n in each unit (I) may be the same or different. The same applies to a, R ² and X described below, which may be the same or different between a plurality of units (I).

R ² has at least 2 carbon atoms,
Represents a divalent hydrocarbon group which may contain an oxygen atom, for example, an ethylene group, a trimethylene group, a 2-methyltrimethylene group, a 1-methyltrimethylene group, a 1-dimethyltrimethylene group, a tetramethylene group, Examples include 2'-oxydiethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, and cyclohexylene group. The above divalent hydrocarbon groups, for example, ethylene group, trimethylene group, 2-methyltrimethylene group, 1-methyltrimethylene group, 1-dimethyltrimethylene group, tetramethylene group, 2,2′-oxydiethylene group, etc. Is preferred. In addition, a 1-methyltrimethylene group is particularly preferable because a side reaction of a hydrosilylation reaction in synthesizing the silicone cinnamate derivative is relatively small.

Examples of the alkoxy group X include, for example, a methoxy group, an ethoxy group and an isopropoxy group. This silicone-cinnamic acid derivative, in which any alkoxy group is selected, has no remarkable difference in solubility, water resistance, oil resistance and medium-wavelength ultraviolet (UV-B) absorption wavelength with respect to the silicone-based base, but the availability of reagents Considering ease of use, X
It is preferable to select a silicone cinnamate derivative in which a methoxy group is selected. A represents the number of substitutions of X.

Next, the unit (II) will be described. In the unit (II), R ³ is an alkyl group having 1 to 4 carbon atoms,
Represents a phenyl group or a trimethylsiloxy group, and m is R ³
Represents the number of substitutions. Examples of R ³ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a t-butyl group, a phenyl group, a trimethylsiloxy group, and the like. Or a trimethylsiloxy group.

The silicone cinnamic acid derivative blended in the lipstick composition of the present invention can be synthesized as follows. That is,

Embedded image (Wherein, Y represents a monovalent hydrocarbon group having at least 2 carbon atoms, having an olefinically unsaturated bond, and possibly containing an oxygen atom. X and a are the same as those described above. Cinnamic acid ester represented by the formula:

A siloxane having R ⁴ _n SiHO _{(3-n) / 2} units and / or R ⁵ _m SiO _{(4-m) / 2} units (R ⁴ is an alkyl group having 1 to 4 carbon atoms, a phenyl group or A trimethylsiloxy group, n is an integer of 0 to 3, R ⁵ has 1 to ³ carbon atoms.
4, an alkyl group, a phenyl group or a trimethylsiloxy group, and m represents an integer of 0 to 3. ); In an organic solvent,
It can be synthesized by reacting in the presence of a catalyst.

The above-mentioned ester, that is, the ester of the general formula (III) is prepared by converting the corresponding substituted cinnamic acid derivative into an acid chloride by a conventional method, and then reacting the ester with a monohydric alcohol having an olefinically unsaturated bond in the presence of an amine. Is obtained by As the reaction solvent, a usual organic solvent can be used, and among them, an aromatic organic solvent such as toluene, benzene or xylene is preferable, and the reaction is carried out at a relatively high temperature, specifically, about the reflux temperature.

Incidentally, depending on the alcohol used in the reaction,
Y in the general formula (III) is different, but is a monovalent hydrocarbon group having at least two carbon atoms, having an olefinically unsaturated bond, and possibly containing an oxygen atom as described above. . Examples of the linear hydrocarbon group having one double bond in the group include a vinyl group, an allyl group, a 3-butenyl group, a 4-pentenyl group, a 1-propenyl group, a 2-butenyl group, and a 2-methyl- 1-propenyl group, 3-methyl-2-butenyl group, allyloxyethyl group and the like; as a branched hydrocarbon group, for example, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1- Dimethyl-2
-Propenyl group, 1-ethyl-2-propenyl group, 1-
Examples thereof include a diethyl-2-propenyl group, a 1-methyl-3-butenyl group, and a 2-methyl-3-butenyl group. Examples of the hydrocarbon group having two double bonds in the group include a 1,3-butadienyl group, a 3-methyl-1,3-butadienyl group, and a 1,3-propedienyl group.

Considering the superiority of the esterification reaction and the hydrosilylation reaction among these Ys and the stability (including light stability) of the silicone cinnamate derivative derived from these esters, the terminal The above hydrocarbon group having one double bond, ie, vinyl group, allyl group, 3
-Butenyl group, 4-pentenyl group, allyloxyethyl group, 1-methyl-2-propenyl group, 2-methyl-2-
Propenyl group, 1-dimethyl-2-propenyl group, 1-
Ethyl-2-propenyl group, 1-diethyl-2-propenyl group, 1-methyl-3-butenyl group, 2-methyl-3
It is preferred to select -butenyl group and the like as Y.

By subjecting the thus obtained ester of the general formula (III) to a hydrosilylation reaction with the above-mentioned siloxane, a silicone cinnamic acid derivative to be added to the lipstick composition of the present invention can be obtained. Is an organosilicon compound having at least one Si-H, R ⁴ _n SiHO _{(3-n) / 2} units and R ⁵
_m SiH _{(4-m) / 2} expressed as a siloxane having ₂ units. For example, triethoxysilane, di (trimethylsiloxy) methylsilane, tri (trimethylsiloxy) silane, trimethylsiloxymethylphenylsilane, trimethylsiloxyethylmethylsilane, trimethylsiloxyethylphenylsilane, 1,1,3,3,
5,5-heptamethyltrisiloxane, 1,1,1,
3,5,5-heptamethyltrisiloxane and the like can be exemplified. Among these, 1,1,1,1,1,1 and 1, from the superiority of the hydrosilylation reaction, the availability of silanes and siloxanes, and the compatibility with silicone-based materials.
3,5,5,5-heptamethyltrisiloxane is preferred. However, the present invention is not limited to this as long as the silicone cinnamic acid derivative of the present invention can be produced.

As the reaction solvent for the above-mentioned hydrosilylation reaction, ordinary organic solvents can be used.
An aromatic organic solvent such as benzene or xylene is preferable, and the reaction is carried out at a relatively high temperature, specifically, about the reflux temperature.

As a catalyst for accelerating the progress of the hydrosilylation reaction, a known rhodium complex (Wilkinson
complex), ruthenium complex, platinum complex, chloroplatinic acid, and the like. Among these catalysts, it is preferable to select a chloroplatinic acid catalyst in consideration of its availability and operational simplicity in the hydrosilylation reaction.

The amount of the silicone cinnamate derivative thus prepared in the lipstick composition of the present invention is 0.1% by weight or more and 10.0% by weight or less of the whole composition. It is preferably from 0.1% by weight to 8.0% by weight. At a loading of less than 0.1% by weight of the total composition,
Unfavorable because stretch and makeup lasting did not improve.
If it is added in excess of weight%, the hardness of the composition tends to be lower than the limit, which is not preferable.

By combining the above-mentioned hydroxyalkylated cyclodextrin and a silicone cinnamate derivative in combination, it is possible to obtain a lipstick composition in which "growth" and "cosmetic durability" on the lips of the composition are synergistically improved. Provided.

The lipstick composition of the present invention may contain, in addition to the above-mentioned essential components, other optional components generally contained in the lipstick composition. For example, non-volatile oils include, for example, liquid paraffin, squalane, castor oil, olive oil, jojoba oil, glyceryl diisostearate, trimethylolpropane tri-2-ethyl isostearate, isopropyl myristate, cetyl-2-ethylhexano Ate, glyceryl triisostearate,
Examples include 2-heptylundecyl palmitate, methylpolysiloxane, polybutene, glycerin triisostearate, diisostearyl malate, lanolin, and the like. One or more of these are arbitrarily selected.

In addition, for example, an antioxidant, an ultraviolet absorber, an ultraviolet shielding agent, a preservative, a humectant, a dye, a pigment, and the like can be added to the lipstick composition of the present invention. When the lipstick composition of the present invention relates to a stick-like lipstick, ceresin wax, carnauba wax, polyethylene wax, paraffin wax or the like is used as a shape retainer in an amount of 5.0% by weight or more and 20.0% by weight of the whole composition. % Is preferred. Specific formulations of the lipstick composition of the present invention will be specifically described in Examples described later.

[0030]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the technical scope of the present invention should not be construed as being limited by these Examples. In addition, the compounding amount is a weight% with respect to the whole composition unless otherwise specified.

[Production Example] Production of hydroxyalkylated cyclodextrin 100 g of β-cyclodextrin (Celdex N: manufactured by Nippon Shokuhin Kako) was added to a 20% aqueous sodium hydroxide solution 150
dissolved in 50 ml of propylene oxide while maintaining the temperature at 30 ° C.
Was gradually added and the reaction was continued with stirring for 20 hours. After completion of the reaction, the pH was adjusted to 6.0 with hydrochloric acid, and the adjusted solution was placed in a dialysis membrane tube, and desalted for 24 hours under flowing water. Thereafter, drying was carried out with a freeze dryer to obtain about 90 g of hydroxypropylated β-cyclodextrin. The substitution degree of the hydroxypropylated β-cyclodextrin per cyclodextrin was 5.1.

Hereinafter, the hydroxypropyl cyclodextrin to be incorporated in the lipstick composition of the present invention used in this example is the hydroxypropyl cyclodextrin produced in this production example. Further, the silicone cinnamate derivative used in the following examples was produced based on the above-mentioned production method.

The performance of the lipstick cosmetics was confirmed by the following five-grade evaluation by a 15-member expert panel for stretchability and long-lasting makeup. Evaluation Criteria (for both growth and makeup) 1: Poor 2: Slightly bad 3: Normal 4: Slightly good 5: Good The evaluation results are indicated by the following symbols based on the average value based on the above criteria of 15 expert panels.

Evaluation results ◎: 4.5 to 5.0 ○: 3.5 to less than 4.5 Δ: 2.5 to less than 3.5 ×: 1.5 to less than 2.5 XX: 1.0 to less than 1.5

The hardness is measured using a spring balance type card meter. That is, in the present embodiment, the “hardness” is a resistance value when a needle having a diameter of 3.0 mm is immersed under a load of 400 g at 37 ° C. and is represented by a value of 200 scales. Indicates that

Examples 1-4 and Comparative Examples 1-18 Lipstick compositions having the compositions shown in Table 1 below (Tables 1 and 2) were prepared. For the comparative example,
The above performance evaluation was performed.

[0037]

[Table 1]

[0038]

[Table 2]

According to Table 1, no improvement in the usability was observed when only the silicone cinnamic acid derivative was blended. Conversely, when it was blended in an excessive amount of 20% by weight of the whole composition,
The result was that it was difficult to maintain the hardness (Comparative Examples 1 to 5). In addition, even when only the hydroxyalkylated cyclodextrin was blended, no improvement in usability was observed (Comparative Examples 1, 6, 11, and 14).

On the other hand, when both are combined, the hydroxyalkylated cyclodextrin is added in an amount of 0.1 to 10% by weight of the whole composition, and the silicone-based cinnamic acid derivative is added in an amount of 0.1 to 10% by weight. And "make-up" improved synergistically. If the hydroxyalkylated cyclodextrin exceeds 10% by weight, it will not be dissolved in ion-exchanged water, and the spread will become heavy. When the amount of ion-exchanged water was increased in order to increase the solubility, the amount of oil was relatively reduced, the smoothness of the oil was reduced, and good results were not obtained (Examples 1 to 4 and Comparative Examples 1 to 4). Examples 7 to 10, 1
2, 13, 15-18).

The lipstick compositions of the present invention having various formulations are shown below. [Example 5] Emulsified stick lipstick compounding amount (% by weight) Paraffin wax 6.0 ceresin 4.0 carnauba wax 3.0 dimethylpolysiloxane (viscosity 6CS) 10.0 diisostearylmalate 27.0 lanolin 30.0 silicone-based cinnamic acid derivative 3.0 ([3-bis (trimethyl Siloxy) methylsilylpropyl] -3,4,5-trimethoxycinnamate) Synthetic sodium-magnesium silicate 1.0 Polyoxyethylene-methylpolysiloxane copolymer 1.0 Titanium dioxide 2.0 Red No. 202 0 Antioxidant appropriate amount perfume appropriate amount B. Ion-exchanged water 4.0 glycerin 1.0 hydroxyalkylated cyclodextrin 4.0 (HP-β-CD)合計 Total 100

<Production Method> A was dissolved at 90 to 100 ° C.
Dispersed with a disperser. Next, after adding B and further dispersing,
After degassing, the mixture was poured into a lipstick container and cooled to obtain an emulsified stick lipstick. This emulsified stick-like lipstick was evaluated as ◎ in both evaluations of “grow” and “make-up”.

Example 6 Emulsified Stick Lipstick Compounding Amount (% by Weight) Paraffin wax 6.0 ceresin 4.0 carnauba wax 3.0 glyceryl tri-2-ethylhexanoate 32.0 glyceryl diisostereate 20.0 lanolin 10.0 silicone-based cinnamic acid derivative 5.0 ([3-bis ( Trimethylsiloxy) methylsilyl-1-methylpropyl] -3,4,5-trimethoxycinnamate) Polyglyceryl diisostearate 2.0 Titanium dioxide 3.0 Red 202 No. 3.0 Antioxidant Suitable amount Perfume Suitable amount B. Ion-exchanged water 6.0 glycerin 3.0 hydroxyalkylated cyclodextrin 3.0 (HE-β-CD)）合計 Total 100

<Production method> A was dissolved at 90 to 100 ° C,
Dispersed with a disperser. Next, after adding B and further dispersing,
After degassing, the mixture was poured into a lipstick container and cooled to obtain an emulsified stick lipstick. This emulsified stick-like lipstick was evaluated as ◎ in both evaluations of “grow” and “make-up”.

Example 7 Emulsion Stick Lipstick Compounding Amount (% by Weight) Paraffin wax 6.0 ceresin 4.0 carnauba wax 3.0 dimethylpolysiloxane (viscosity 6CS) 15.0 diisostearyl malate 20.0 glyceryl diisostereate 30.0 silicone cinnamic acid derivative 5.0 ([3 -Bis (trimethylsiloxy) methylsilyl-1-methylpropyl] -3,4-dimethoxycinnamate Synthetic sodium-magnesium silicate 2.0 Polyoxyethylene-methylpolysiloxane copolymer 1.0 Titanium dioxide 3.0 Red No. 202 2.0 Suitable amount of antioxidant Perfume Suitable amount Ion-exchanged water 5.0 glycerin 1.0 hydroxyalkylated cyclodextrin 3.0 (HE-β-CD)合計 Total 100

<Production method> A was dissolved at 90 to 100 ° C,
Dispersed with a disperser. Next, after adding B and further dispersing,
After degassing, the mixture was poured into a lipstick container and cooled to obtain an emulsified stick lipstick. This emulsified stick-like lipstick was evaluated as ◎ in both evaluations of “grow” and “make-up”.

Example 8 Emulsion Liquid Lipstick Compounding Amount (% by Weight) Paraffin wax 10.0 ceresin 2.0 dextrin palmitic acid ester 1.0 dimethylpolysiloxane (viscosity 6CS) 15.0 liquid paraffin 37.5 lanolin 5.0 silicone-based cinnamic acid derivative 10.0 ([3-bis (trimethyl Siloxy) methylsilylpropyl] -3,4,5-methoxycinnamate) Synthetic sodium-magnesium 1.0 Polyoxyethylene-methylpolysiloxane copolymer 0.5 Titanium dioxide 1.0 Red No. 202 4.0 Antioxidant appropriate amount perfume appropriate amount B. Ion-exchanged water 8.0 glycerin 1.0 hydroxyalkylated cyclodextrin 4.0 (HP-β-CD)合計 Total 100

<Production method> A was dissolved at 90 to 100 ° C,
Dispersed with a disperser. Next, after adding B and further dispersing,
It was degassed, poured into a lipstick container, and cooled to obtain an emulsified liquid lipstick. These emulsified liquid lipsticks are "grown" and "have makeup"
Both were ◎ in the above evaluation.

[0049]

According to the present invention, there is provided a lipstick composition in which "growth" and "cosmetic durability" are synergistically improved.

Continuing from the front page (72) Inventor Miwa Soyama 1050 Nippa-cho, Kohoku-ku, Yokohama-shi, Kanagawa Prefecture Inside Shiseido Daiichi Research Center

Claims (1)

[Claims] 1. A lipstick composition comprising the following components (a) and (b): (a) hydroxyalkylated cyclodextrin in an amount of 0.1% by weight or more and 10.0% by weight of the whole composition; (B) embedded image (In the formula, R ¹ represents an alkyl group having 1 to 4 carbon atoms, a phenyl group or a trimethylsiloxy group, and R ² has at least 2 carbon atoms and may contain an oxygen atom. X represents a hydrogen group, X represents an alkoxy group, and n represents 0
A represents an integer of 1 to 3, a represents 2 or 3, and O _{(4-m) / 2} SiR ³ _m (II) (wherein R ³ has 1 carbon atom) Represents an alkyl group, a phenyl group or a trimethylsiloxy group, and m represents an integer of 0 to 3). Above, 10.0
% By weight or less.