JPH10330639A - Colored pigment, its production and cosmetic using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a colored pigment capable of suitably using as a coloring agent for cosmetics by stably fixing a xanthene based pigment in a vividly colored state onto a specific powdery carrier substance. SOLUTION: This colored pigment is obtained by converting a lactone type xanthene-based pigment of formula I (X is H, Br, I or Cl; Y is H or Cl) to a quinoid type xanthene based pigment of formula II and fixing the quinoid type xanthene-based pigment to a particulate water-containing silicic acid mineral or barium sulfate. A method for producing the colored pigment includes e.g. a method bringing powdery water-containing silicic acid salt mineral or barium sulfate into contact with an aqueous solution containing ammonium salt or alkali metal salt of pigment of formula I. Furthermore, a bright makeup cosmetic stabilized in color tone can be provided by formulating 100 pts.wt. basic composition of the cosmetic with 0.01-50 pts.wt. of the colored pigment.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel colored pigment,
The present invention relates to a production method thereof and a cosmetic containing the colored pigment. More specifically, the present invention relates to a colored pigment comprising a xanthene dye fixed to a specific carrier, a method for producing the same, and a makeup cosmetic containing the colored pigment.

[0002]

2. Description of the Related Art Hitherto, xanthene dyes are known as dyes for foods, medicines and cosmetics. The xanthene dye has a tautomer due to “acid” ⇔ “alkali”. That is, specifically taking red No. 223 known as a xanthene dye as an example, this is a lactone type 2,4,5,7-tetrabromo represented by the following structural formula (A) in an acidic region. -3,6-
Fluoranediol, a substance called Red No. 223 (tetrabromofluorescein). But,
Red No. 223 changes to a quinoid type in the alkaline region, and disodium salt of 9-ortho-carboxyphenyl-6-hydroxy-2,4,5,7-tetrabromo-3-isoxanthone, that is, Red No. 230 (1)
It changes into a substance called (eosin YS). Conversely, (1) of Red No. 230 which had a quinoid type (B) structure in the alkaline region,
It changes to lactone type (A) red No. 223.

Embedded image When it has a lactone type (A) structure, it is insoluble in water, but when it has a quinoid type (B) structure, it becomes soluble in water and has a vivid red color. Will be different. As described above, since the xanthene-based dye has a property that the color tone changes depending on the pH range and is not stable, it has not been easy to stabilize the color tone until now.

On the other hand, powdered hydrated silicate minerals (for example, mica, talc, kaolin, etc.) or barium sulfate are used for color adjustment as a diluent for coloring materials, and are also useful for cosmetics (extensibility, extensibility, etc.). It is used to adjust adhesion. However, a colored pigment obtained by stably fixing a xanthene-based dye to the hydrated silicate mineral or barium sulfate in a state of exhibiting a vivid color tone with high saturation has not been found so far.

[0004]

SUMMARY OF THE INVENTION Under such circumstances, the present invention provides a colored pigment comprising a xanthene dye which is stably immobilized in a vividly colored state, and which is a cosmetic pigment. It is intended to be used as a component.

[0005]

Means for Solving the Problems The present inventors have made intensive studies on stably fixing a xanthene dye in a state of exhibiting a vivid color tone, and as a result, have found that a xanthene dye having a lactone type structure has been obtained. The following general formula (III)

Embedded image (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), or converted to a quinoid-type ammonium salt represented by the following general formula ( IV)

Embedded image Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, Y is a hydrogen atom or a chlorine atom, and Z is a sodium atom or a potassium atom. By converting it into a salt and bringing it into contact with a specific carrier substance in the presence of a water-soluble aluminum salt, the xanthene dye easily adheres to the carrier substance in a quinoid structure and is stable in a state of exhibiting a vivid color tone. The present invention has been completed based on this finding.

That is, the present invention provides a compound represented by the general formula (I)

Embedded image (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom) represented by the general formula (II)

Embedded image (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), which is a quinoid-type xanthene dye represented by the following formula: The present invention provides a makeup cosmetic comprising 0.01 to 50 parts by weight of a colored pigment fixed to a mineral or barium sulfate and 100 to 50 parts by weight of a basic composition of the cosmetic. is there.

According to the present invention, the colored pigment is
Powdered hydrated silicate mineral or barium sulfate is prepared by adding a water-soluble aluminum salt to a compound represented by the general formula

Embedded image (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), containing an aqueous solution containing an ammonium salt or an alkali metal salt of a lactone-type xanthene dye. It can be manufactured by contact.

[0008]

DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, a powdery hydrated silicate mineral or barium sulfate is used as a carrier substance for fixing a xanthene dye.

The hydrated silicate mineral in the form of powder is a viscous mineral mainly containing silicon and aluminum and containing magnesium, iron, alkali metals (Li, Na, K) and the like. 15 μm “talc powder”, “kaolin powder” having an average particle size of 0.3 to 5 μm, “mica (aka mica) powder” having an average particle size of 4 to 6 μm, synthetic mica powder, average particle size 3-7μ
m "Serisite (sericite) powder" and "sintered sericite (sintered mica) powder"
And the like.

As barium sulfate, for example, “barium arsenate powder” having an average particle diameter of 4 to 10 μm obtained by pulverizing natural barite and separating it in air or water depending on the difference in specific gravity, or "Precipitating barium sulfate powder" having an average particle diameter of 0.1 to 15 μm, which is obtained by allowing sodium sulfate to act on an aqueous solution of barium sulfide or by allowing sulfuric acid to act on an aqueous solution of barium chloride;
Alternatively, when barium sulfate is precipitated, “plate-like barium sulfate powder” having a plate-like diameter of 5 to 10 μm and a thickness of 0.1 to 0.4 μm, which is precipitated so as to form plate-like crystals, or a spherical crystal is used. 0.1 μm fine “spherical particulate barium sulfate powder”.

In the present invention, the above-mentioned powdery carrier substances may be used alone or in combination of two or more.

On the other hand, typical examples of the lactone type xanthene dye represented by the general formula (I) used in the present invention include 3,6-fluoranediol [yellow 2
No. 01 / fluorescein], 4,5-dibromo-3,6
-Fluorandiol [Dai No. 201 / dibromofluorescein], 4,5-diiodo-3,6-fluoranediol [Daiiro No. 206 / diiodofluorescein], 2,4,5,7-tetrabromo-3 , 6-Fluoranediol [Red 223 / tetrabromofluorescein], 2,4,5,7-tetrachloro-3,6-fluoranediol [Red 216 / tetrachlorofluorescein], 2,4,5,7 -Tetrabromo-12,1
3,14,15-tetrachloro-3,6-fluoranediol [Red No. 218 / tetrachlorotetrabromofluorescein] and the like.

In the present invention, one of these xanthene dyes having a lactone structure may be used alone, or two or more of them may be used in combination to obtain a colored pigment having a desired color tone.

These lactone-type xanthene dyes are converted into a quinoid-type xanthene dye represented by the above general formula (III) by treating with an aqueous ammonia solution. By treating with an aqueous solution of a bicarbonate, it is converted into a quinoid-type xanthene dye represented by the general formula (IV).

The aqueous ammonia used to convert the lactone-type xanthene dye into a quinoid-type structure is a commercially available concentrated aqueous ammonia (28%).
And examples of the alkali metal carbonate and bicarbonate include sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate.

At this time, if a hydroxide of an alkali metal such as sodium hydroxide or potassium hydroxide which exhibits strong alkalinity is used, the compound represented by the general formula (V):

Embedded image (Wherein X is a hydrogen atom, bromine atom, iodine atom or chlorine atom, Y is a hydrogen atom or chlorine atom, and M is an alkali metal), a dialkali metal salt of a xanthene dye represented by the formula It is not preferable because the substituent at the 3-position of the fluorescein skeleton cannot be immobilized on the powdery carrier substance as it is as the hydroxyl group (-OH).

The colored pigment of the present invention is obtained by immobilizing the quinoid type xanthene dye represented by the general formula (II) on the above-mentioned powdery carrier substance. The lactone-type xanthene dye represented by (I) is treated with an aqueous ammonia solution to obtain a quinoid-type ammonium salt represented by the general formula (III), or an alkali metal carbonate and hydrogencarbonate. By treating with an aqueous solution, a quinoid-type alkali metal salt (carboxyl metal salt: —COO ⁻ Z ⁺ ) represented by the above general formula (IV) is obtained. By contacting in the presence of a salt, a desired colored pigment can be efficiently produced.

In this case, the xanthene dye cannot be immobilized on the powdery carrier substance as it is in the lactone type represented by the general formula (I). Further, even if the powdery carrier substance is simply brought into contact with the quinoid-converted xanthene dye without using the water-soluble aluminum salt, the powdery carrier substance is not immobilized on the powdery carrier substance. The lactone-type xanthene dye is treated with an aqueous ammonia solution or an aqueous solution of an alkali metal carbonate or bicarbonate, and further contacted in the presence of a water-soluble aluminum salt to stabilize the xanthene dye as a quinoid structure, It is fixed and immobilized on the surface of the powdery carrier material.

The phenomenon that the xanthene dye stabilizes in the quinoid type structure and is fixed and fixed on the surface of the powdery carrier substance is as follows. First, the lactone type xanthene dye is aqueous ammonia or an alkali metal carbonate or bicarbonate. By treatment with an aqueous solution of the general formula (III)
Alternatively, the quinoid structure represented by the general formula (IV) is obtained, and the presence of an aluminum ion derived from a water-soluble aluminum salt causes the presence of the general formula (III)
Ammonium ion (N
H ₄ ⁺ ) or an alkali metal ion (Z ⁺ ) in the molecular structure represented by the general formula (IV) is replaced with an aluminum ion, and at the same time, a xanthene-based structure in which the aluminum ion is used to form a quinoid-type structure It is presumed to be caused by the adsorption of the pigment and the powdery carrier substance.

Examples of the water-soluble aluminum salt used in the present invention include aluminum sulfate, aluminum chloride, aluminum acetate, aluminum potassium sulfate, sodium aluminum sulfate, and ammonium ammonium sulfate. These water-soluble aluminum salts may be used alone or in combination of two or more.

As a specific method of stabilizing and fixing a xanthene dye to the powdery carrier substance in a quinoid type structure, first, an aqueous ammonia solution or an aqueous solution of an alkali metal carbonate or bicarbonate is added to a general formula ( The lactone type xanthene dye represented by I) is added and dissolved. Then, after dispersing the powdery carrier substance into the dye solution while stirring, a method of adding a water-soluble aluminum salt or the like can be used.

Here, the concentration of the aqueous ammonia solution or the aqueous solution of the alkali metal carbonate or bicarbonate used to dissolve the lactone-type xanthene dye is 0.0
The amount is preferably 1.0 to 10.0 times (W / V%) 1.0 to 10.0 times the molar amount of a lactone-type xanthene dye (in the case of ammonia water, as NH ₃ ).
Preferably, a molar amount of 2.0 to 7.0 times is used.

The lactone type xanthene dye is used in an appropriate amount of 0.1 to 15% by weight, preferably 1 to 10% by weight, based on the powdery carrier substance. The concentration of the xanthene dye in the dye solution is 0.05 to 1.00%.
(W / V%), preferably 0.1 to 0.5% (W / V
%).

Next, the amount of the water-soluble aluminum salt used is as follows:
In the case of a water-soluble aluminum salt having one aluminum atom per 1 mol: an appropriate amount is 1.0 to 1.5 mol per 1 mol of the lactone type xanthene dye. In the case of a water-soluble aluminum salt having two aluminum atoms per mole: lactone type xanthene dye 1
An appropriate amount is 0.5 to 0.7 mole based on the mole. The water-soluble aluminum salt may be gradually added as it is, but is preferably added in the form of an aqueous solution.
When this is used as an aqueous solution, 0.1 to 5.0%
(W / V%) is prepared and used.

The fixing treatment is performed at room temperature to about 70 ° C. for 3 hours.
It may be performed for about 0 minutes to 3 hours. Further, the pH of the dye solution during the fixing treatment is preferably kept in a range of 4.0 to 7.0, and in order to adjust the pH of the dye solution to this range,
The water-soluble aluminum salt as an acidic substance or the aqueous ammonia solution or an aqueous solution of an alkali metal carbonate or hydrogencarbonate as an alkaline substance may be appropriately added.

In this manner, the quinoid-type xanthene dye is easily fixed to the carrier substance of the powdered hydrated silicate mineral or barium sulfate in a state where the quinoid type xanthene dye exhibits a vivid color tone, and is stabilized. After the fixation, the carrier on which the dye is fixed and immobilized is removed by a known means such as filtration or centrifugation, dried, and, if necessary, crushed (crushed) to obtain a desired finely powdered colored pigment. Is obtained.

The lactone type xanthene dyes and the dyes obtained by converting the lactone type into quinoids are also used as coloring agents for foods, pharmaceuticals, cosmetics, and the like. In particular, the colored pigment of the present invention in which a quinoid-type xanthene dye is fixed to the carrier substance is dark (lightness V in Munsell value is 7 or less) and vivid (saturation C is 10 in Munsell value). that's all)
In addition, the color tone is stable and can be used very suitably as a coloring agent for cosmetics.

The makeup cosmetic of the present invention contains the above-mentioned colored pigment as a coloring agent, and the amount thereof is 0.01 to 100 parts by weight based on the basic composition of the cosmetic.
It is selected in the range of 50 parts by weight. The optimum amount of the colored pigment is selected within the above range according to the type of the cosmetic.

The basic composition in the makeup cosmetic of the present invention is not particularly limited, and is a basic composition conventionally used in various makeup cosmetics, for example, eye shadow, blusher, foundation, lipstick, nail polish and the like. Can be mentioned. The makeup cosmetic of the present invention may optionally contain other coloring agents such as inorganic pigments and organic pigments. The method for preparing the makeup cosmetic of the present invention is not particularly limited, and a method conventionally used for preparing a makeup cosmetic can be used.

[0030]

The colored pigment of the present invention is obtained by stabilizing and fixing a xanthene dye to a specific powdery carrier substance in a state of exhibiting a vivid color tone, and the color density is the lightness of the Munsell value. V is 7 or less, and its vividness is 10 or more as measured by the Munsell value saturation C, and its color tone is stable. Therefore, it is extremely suitably used as a coloring agent for cosmetics. And has excellent extensibility to the skin, and can express a transparent and vivid color tone. Further, the makeup cosmetic of the present invention contains the colored pigment, and has good adhesiveness to the skin and a good feeling of use such as spreading and familiarity, such as eye shadow, blush, Foundation,
It is suitably used as a lipstick, a beautiful nail material and the like.

[0031]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. The physical properties of the obtained pigment were determined as follows. (1) Appearance By visual observation. (2) Hue H, lightness V, saturation C 380 to 78 using a spectrophotometer using an integrating sphere [Spectrophotometer "Ubest50" manufactured by JASCO Corporation].
A reflection spectrum is measured in a wavelength region of 0 nm, and a C light source (daylight including a blue sky) is measured from the measured spectrum using a color calculation program [TSV-433 type color calculation program manufactured by JASCO Corporation]. The Munsell value according to a color system based on a 2-degree visual field determined by the International Commission on Illumination (CIE) was determined as a standard light source. The hue (H) of the Munsell value is represented by “R” for the “red” hue area, “P” for the “purple” hue area, “B” for the “blue” hue area, and “yellow” for the hue area. The hue area is represented by “Y”.

Example 1 80 ml of 0.5% ammonia aqueous solution in 800 ml of purified water
, And 2 g of 3,6-fluoranediol [Yellow No. 201 / fluorescein] is dissolved therein, and barium sulfate powder [manufactured by Sakai Chemical Industry Co., Ltd .: plate-like barium sulfate “plate-like” is stirred at room temperature. Barium sulfate H ", purity 98%,
Particle size 5-10 μm × 0.2 μm, median diameter 7.416
μm], disperse by adding 20 g, and add 1% while stirring.
342 ml of an aqueous solution of (W / V%) aluminum potassium sulfate dodecahydrate was added dropwise over 1 hour, and the mixture was further stirred at room temperature for 2 hours. At this time, the pH of the dye solution was 6. Then, the yellow barium sulfate powder is filtered off,
It was dried at 55 ° C. and pulverized in a mortar to obtain 21.6 g of a fine powdery pigment having a yellow appearance. The filtrate was slightly yellow and transparent, and had a pH of 6. In addition, despite drying at 55 ° C., the fixed xanthene-based dye did not fade and exhibited a bright yellow color, confirming that the obtained pigment was excellent in heat resistance. FIG. 1 shows the spectral reflection spectrum of the yellow pigment thus obtained. The hue H obtained from this spectrum is 6.3 YR (reddish yellow), the lightness V is 7.3, the chroma C is 10.2, and it is a yellow pigment having a high chroma and a vivid color tone. It was confirmed that there was.

Example 2 A 0.5% aqueous ammonia solution (60 ml) in 800 ml of purified water
And 2 g of 4,5-dibromo-3,6-fluoranediol [Daiiro No. 201 / dibromofluorescein] is dissolved therein.
Barium sulfate powder [manufactured by Sakai Chemical Industry Co., Ltd .: plate-shaped barium sulfate “plate-shaped barium sulfate H”,
Purity 98%, particle size 5-10 μm × 0.2 μm, median diameter 7.416 μm], 20 g was added and dispersed, and 1% (W / V%) aluminum potassium sulfate ·
271 ml of an aqueous solution of dodecahydrate was added dropwise over 1 hour,
The mixture was further stirred at 50 ° C. for 2 hours. At this time, the pH of the dye solution was 5. Thereafter, the orange barium sulfate powder was filtered off, dried at 55 ° C., and crushed in a mortar to obtain 21.7 g of a fine powdery pigment having an orange appearance. The filtrate was slightly yellow and transparent, and had a pH of 5. In addition, despite drying at 55 ° C., the fixed xanthene dye did not fade and exhibited a bright orange color, confirming that the obtained pigment had excellent heat resistance. FIG. 2 shows the spectral reflection spectrum of the orange pigment thus obtained.
The hue H obtained from this spectrum is 4.3Y
R (orange), lightness V were 7.3, and chroma C was 10.3, and it was confirmed that this was an orange pigment having a high chroma and a vivid color tone.

Example 3 In place of 2 g of 4,5-dibromo-3,6-fluoranediol [Daiiro No. 201 / dibromofluorescein] in Example 2, 2,4,5,7-tetrabromo-3, Using 2 g of 6-fluoranediol [Red No. 223 / tetrabromofluorescein], 1% (W /
V%) 21.5 g of a fine powdery pigment having a red appearance was obtained in the same manner as in Example 2 except that an aqueous solution of potassium aluminum sulfate dodecahydrate was used in an amount of 204 ml. At this time, the pH of the dye solution was 5, and the filtrate was slightly red and transparent, and its pH was 5. FIG. 3 shows the spectral reflection spectrum of the red pigment thus obtained. The hue H obtained from this spectrum is 5.3R
(Red), lightness V is 5.4, chroma C is 11.5,
It was confirmed that the pigment was a red pigment having a high saturation and a vivid color tone.

Example 4 In place of 2 g of 4,5-dibromo-3,6-fluoranediol [Orange No. 201 / dibromofluorescein] in Example 2, 2,4,5,7-tetrabromo-12,12 was used. Using 2 g of 13,14,15-tetrachloro-3,6-fluoranediol [Red No. 218 / tetrachloro-tetrabromofluorescein], 1% (W
/ V%) 21.4 g of a fine powdery pigment having a red appearance was obtained in the same manner as in Example 2 except that 169 ml of an aqueous solution of potassium aluminum sulfate sulfate dodecahydrate was used. At this time, the pH of the dye solution was 5, and the filtrate was slightly red and transparent, and its pH was 5. FIG. 4 shows the spectral reflection spectrum of the red pigment thus obtained. The hue H determined from this spectrum is 9.0 RP
(Purple red), lightness V was 5.7, and chroma C was 12.0, and it was confirmed that the pigment was a red pigment having a high chroma and a vivid color tone.

Example 5 In place of 2 g of 4,5-dibromo-3,6-fluoranediol [Daiiro No. 201 / dibromofluorescein] in Example 2, 2,4,5,7-tetrabromo-3, 2 g of 6-fluoranediol [Red No. 223 / tetrabromofluorescein] was used, and instead of 20 g of barium sulfate powder, 20 g of mica powder [Tokai Pigment Co., Ltd .: “Mica M” average particle diameter of 20 μm] was used. Further, 21.6 g of a fine powdery pigment having a red appearance was obtained in the same manner as in Example 2 except that an aqueous solution of 1% (W / V%) aluminum potassium sulfate dodecahydrate was used in an amount of 204 ml. Was. The pH of the dye solution at this time is 5
The filtrate was slightly red and transparent, and its pH was 5.
FIG. 5 shows the spectral reflection spectrum of the red pigment thus obtained. The hue H obtained from this spectrum is 4.1R (red), the lightness V is 5.7, and the saturation C is 1
0.4, which was confirmed to be a red pigment having a high chroma and a vivid color tone.

Example 6 Instead of 60 ml of the 0.5% aqueous ammonia solution in Example 2, 120 ml of a 2% aqueous sodium carbonate solution was used, and a 1% (W / V%) aqueous solution of aluminum potassium sulfate dodecahydrate was used. Except for using 270 ml, 21.1 g of a fine powdery pigment having an orange appearance was obtained in the same manner as in Example 2. The pH of the dye solution at this time is 6
The filtrate was slightly yellow and transparent, and its pH was 6.
FIG. 6 shows the spectral reflection spectrum of the orange pigment thus obtained. The hue H obtained from this spectrum is 9.5R (orange near the “red R” on the Munsell hue circle), the lightness V is 6.3, the chroma C is 11.7, and the chroma is It was confirmed that this was an orange pigment having a high vivid color tone.

Example 7 In place of 60 ml of the 0.5% ammonia aqueous solution in Example 2, 100 ml of a 1% aqueous sodium hydrogencarbonate solution was used, and a 1% (W / V%) aqueous solution of potassium aluminum sulfate dodecahydrate was further added. In the same manner as in Example 2 except that 270 ml of the pigment was used, 21.3 g of a fine powdery pigment having an orange appearance was obtained. At this time, the pH of the dye solution was 6, the filtrate was slightly yellow and transparent, and the pH was 6. FIG. 7 shows the spectral reflection spectrum of the orange pigment thus obtained. The hue H obtained from this spectrum is 0.2YR (“Red R” on the Munsell hue circle).
Orange), lightness V is 6.4, and saturation C is 11.3.
It was confirmed that the pigment was an orange pigment having a high color saturation and a vivid color tone.

[Dye Elution Test] A dye elution test was performed on the colored pigment obtained according to the present invention. First, 0.5 g of the colored pigment obtained in each of the above Examples was placed in a test tube, and
0 ml of purified water was added to each, shaken for 1 hour in a constant temperature shaking water bath adjusted to 50 ° C., allowed to stand, and the coloring state of the supernatant was visually observed to confirm the elution of the dye. As a result, no coloring matter was eluted from the colored pigment obtained in each of the above Examples.

Comparative Example The color of a colored powder prepared by mixing and dispersing a xanthene dye in a white powder according to a conventional method and the color of the colored pigment obtained by the present invention were compared and evaluated.

Comparative Example 1 Barium sulfate powder 2 similar to that used in the examples
To 0 g, 2 g of 2,4,5,7-tetrabromo-3,6-fluoranediol [Red No. 223 / tetrabromofluorescein] was added and mixed to obtain a red powder. FIG. 8 shows the spectral reflection spectrum of this red powder. The hue H obtained from this spectrum was 6.5R (red), the lightness V was 7.4, and the chroma C was 7.9.

The colored pigment of the present invention, which is obtained by converting the same xanthene dye to the quinoid type and fixing the same to the barium sulfate powder with respect to the red powder obtained in Comparative Example 1,
It was obtained in Example 3 above, and shows the spectral reflection spectrum of FIG. 3, and the Munsell value obtained from this spectrum is: Hue H: 5.3R (red), Lightness V:
5.4, chroma C: 11.5. Compared with the red powder of Comparative Example 1, it was confirmed that the red pigment according to the present invention had a clearly high chroma and a vivid color tone. Was done.

Comparative Example 2 Barium sulfate powder 2 similar to that used in the examples
In 0 g, 2,4,5,7-tetrabromo-12,13,
2 g of 14,15-tetrachloro-3,6-fluoranediol [Red No. 218 / tetrachloro-tetrabromofluorescein] was added and mixed to obtain a red powder. FIG. 9 shows the spectral reflection spectrum of this red powder. Also,
Hue H obtained from this spectrum was 9.7 RP (purple red), lightness V was 8.2, and chroma C was 4.1.

The colored pigment of the present invention, which is obtained by converting the same xanthene dye to the quinoid type and fixing the same to the barium sulfate powder with respect to the red powder obtained in Comparative Example 2,
It was obtained in Example 4, which shows the spectral reflection spectrum of FIG. 4, and the Munsell value obtained from this spectrum was: hue H: 9.0 RP (purple red), lightness V: 5. 7. Saturation C: 12.0. Compared with the red powder of Comparative Example 2, the red pigment according to the present invention has a distinctly deeper brightness, and has a vivid color tone with much higher saturation. It was confirmed that.

[Production of Cosmetic] Example 8 Production of Lipstick (A) Component Colored pigment of Example 3 20 parts by weight Castor oil 25 parts by weight (B) Component Candelilla wax 9 parts by weight Solid paraffin 8 parts by weight Beeswax 5 Parts by weight Carnauba wax 5 parts by weight Lanolin 11 parts by weight Isopropyl myristate 10 parts by weight The above-mentioned component (A) is kneaded with a three-roller, and this is added to the dissolved mixture of the (B) component and mixed again with the three-roller. After kneading, the mixture was redissolved, poured into a mold, and cooled to obtain a lipstick. The colored pigment of the present invention also had good dispersibility, and the color tone, adhesion, elongation, and touch of the obtained lipstick were extremely good.

Example 9 Production of Lipstick (A) Component Colored pigment of Example 4 20 parts by weight Castor oil 25 parts by weight Component (B) Candelilla wax 9 parts by weight Solid paraffin 8 parts by weight Beeswax 5 parts by weight Carnauba wax 5 parts by weight Lanolin 11 parts by weight Isopropyl myristate 10 parts by weight The above component (A) was kneaded with a three-roller, added to the dissolution mixture of the component (B), kneaded again with the three-roller, and then re-dissolved. Then, the mixture was poured into a mold and cooled to obtain a lipstick. The colored pigment of the present invention also had good dispersibility, and the color tone, adhesion, elongation, and touch of the obtained lipstick were extremely good.

Example 10 Production of Blusher (A) Component Colored pigment of Example 5 7 parts by weight Talc 75 parts by weight Kaolin 10 parts by weight Zinc myristate 5 parts by weight Component (B) Liquid paraffin 3 parts by weight The above (A) Stir the ingredients well with a blender and mix,
The component (B) was sprayed there, further stirred and mixed by a blender, processed by a pulverizer, and then pressed into a mold to obtain a blusher. The color, adhesion, elongation, touch, and water resistance (sweat resistance) of the obtained blusher were extremely good.

[Brief description of the drawings]

FIG. 1 is a spectral reflection spectrum diagram of a yellow pigment obtained in Example 1.

FIG. 2 is a spectral reflection spectrum of the orange pigment obtained in Example 2.

FIG. 3 is a spectral reflection spectrum diagram of a red pigment obtained in Example 3.

FIG. 4 is a spectral reflection spectrum diagram of a red pigment obtained in Example 4.

FIG. 5 is a spectral reflection spectrum diagram of a red pigment obtained in Example 5.

FIG. 6 is a spectral reflection spectrum diagram of the orange powder obtained in Example 6.

FIG. 7 is a spectral reflection spectrum diagram of the orange powder obtained in Example 7.

FIG. 8 is a spectral reflection spectrum diagram of the red powder obtained in Comparative Example 1.

FIG. 9 is a spectral reflection spectrum diagram of the red powder obtained in Comparative Example 2.

Continuation of the front page (72) Inventor Yuko Noda 5396-2, Kamiogino, Atsugi-shi, Kanagawa Den Materials Co., Ltd.

Claims (3)

[Claims] 1. A compound of the general formula (I) (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), a lactone-type xanthene dye represented by the general formula (II): (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), which is a quinoid-type xanthene dye represented by the following formula: Colored pigment fixed to mineral or barium sulfate. 2. A hydrated silicate mineral or barium sulfate in the form of a powder in the presence of a water-soluble aluminum salt is represented by the general formula (I): (Wherein X is a hydrogen atom, a bromine atom, an iodine atom or a chlorine atom, and Y is a hydrogen atom or a chlorine atom), containing an aqueous solution containing an ammonium salt or an alkali metal salt of a lactone-type xanthene dye. A method for producing a colored pigment, which is brought into contact with the pigment. 3. A makeup cosmetic comprising 0.01 to 50 parts by weight of the colored pigment according to claim 1 based on 100 parts by weight of the basic composition of the cosmetic.