WO2019078557A1 - Novel cosmetic coloring material and use thereof - Google Patents

Abstract

The present invention relates to a novel coloring material comprising: a polyamide- and/or polyurethane-based particulate material; and a water-soluble dye. The novel coloring material according to the present invention allows the application of a water-soluble dye to an anhydrous formulation, thereby expanding the limited scope of use of a dye, exhibits excellent reflectance and has fluorescent characteristics, thereby widening the spectrum of a cosmetic coloring material which has had limited use in the cosmetic field.

Description

Novel cosmetic coloring materials and uses thereof

The present invention relates to a novel cosmetic colorant and a use thereof.

Make-up cosmetics such as lip cosmetics such as lipstick and gloss which apply lips, cheeks (ball lotion) or eyeshadow are cosmetic products that exhibit important cosmetic effects to the degree of changing the impression of the user's appearance, It is one of the important factors in selection. Recently, a makeup cosmetic with a clear color and a clear impression has been demanded. For example, a lipstick showing a high luminance of fluorescence has been attracting attention.

The makeup cosmetics are generally blended with a oily base material and a coloring material (coloring agent). Among them, a coloring material is responsible for coloring when applied to lips or skin.

Organic synthetic dyes (also called tar dyes) and inorganic pigments are included in cosmetics, and organic synthetic dyes are classified as dyes and organic pigments. Among the organic synthetic dyes, there are oil-dispersible dyes which are dispersed in water-soluble dyes and oils, and organic pigments are lake dyes in which water-soluble or poorly soluble dyes are insolubilized.

Until now, the kinds of cosmetic pigment which can be used in a water-free formulation are very few, and it has been difficult to realize various colors in cosmetics for lips such as lipsticks and lip gloss. In addition, water-soluble dyes have further limitations in their application to water-free formulations.

In this regard, Korean Patent Laid-Open Publication No. 2017-0103966 discloses a makeup cosmetic capable of fluorescence coloring, but it has a limitation that it can not be applied to water-soluble dyes, but can improve the color of the oil-dispersible dyes.

Accordingly, there is a continuing need to develop a coloring material capable of broadening the spectrum of color expression that can not be expressed by conventional dyes, and a manufacturing method thereof, by using a limited variety of cosmetic colorants that can pass all the global regulations.

In order to overcome the limitations of color in the present cosmetic colorant, especially in anhydrous formulations, the present invention provides a new colorant based on water-soluble dyestuffs which can be used in cosmetic formulations without a formulation such as lipstick or lip gloss. The present invention also provides a cosmetic composition comprising the novel colorant and a cosmetic composition for lips comprising the same.

In order to achieve the object of the present invention, the present invention provides a color material and a cosmetic composition comprising the color material.

Specifically, the present invention relates to a curable composition comprising: at least one powder selected from the group consisting of a polyurethane powder and a polyamide powder having a weight average molecular weight of 200,000 or more; And a water-soluble dye of the following structural formula (1).

[Structural formula 1]

In the above structural formula 1, R ₁ is yet oxygen (O) or _{N (C 2 H 5) 2} , and if R ₁ is oxygen and n is 1, R ₁ is N (C ₂ H _{5) 2} in case n is 0, ; R ₂ and R ₃ are each independently hydrogen, bromine (Br) or iodine (I); R ₄ is COO ^- or SO ₃ ^- and; M is 0 when R ₅ is hydrogen, chlorine or SO ₃ ^- and m is 0 when R ₅ is hydrogen or chlorine, m is 1 when R ₅ is SO ₃ ^- , R ₆ is hydrogen or chlorine, X is aluminum, Calcium, sodium or potassium.

The present invention also provides a cosmetic composition comprising the colorant.

The present invention also provides a cosmetic composition for lips comprising the above-mentioned colorant.

The water-soluble dyes of the present invention; And a polyurethane or polyamide-based powder exhibit a new color tone exhibiting a fluorescence color feeling and a reflectance of 100 or more and a very high chroma and lightness. When the color material of the present invention is used, Soluble dye can be used in a water-free formulation, and thus a cosmetic composition having a color that can not be realized with a conventional oil-soluble dye or lake pigment can be provided.

FIG. 1 is a photograph showing the difference in color between a colorant prepared according to an embodiment of the present invention and a conventional water-soluble dye.

FIGS. 2A, 2B, 2C, and 2D are graphs showing the fluorescence analysis results of the colorant prepared according to one embodiment of the present invention and the conventional water-soluble dye.

FIGS. 3A, 3B, 3C, and 3 D are graphs showing the results of analyzing the reflectance characteristics of a colorant prepared according to an embodiment of the present invention and a conventional water-soluble dye.

4 is a graph showing the results of analyzing the reflectance characteristics of the comparative color material prepared in one example of the present invention.

5A and 5B are photographs showing the color difference of the lipstick manufactured using the coloring material and the rake pigment according to an embodiment of the present invention.

The inventors of the present invention have made continuous efforts to prepare a coloring material that can be used in anhydrous form based on a water-soluble dye in order to overcome the limit of dyes usable in anhydrous formulations. As a result, it has been found that polyurethane powder and / It has been confirmed that the use of a colorant containing both a polyamide powder having a molecular weight of 200,000 or more and a water-soluble dye has excellent dispersibility in a water-free formulation, Thereby completing the invention. When the colorant of the present invention is used, a water-soluble dye that has not been used in conventional anhydrous formulations can be used in a water-free formulation, and fluorescence characteristics not obtained with conventional dyes can be obtained. It is possible to improve the color of the make-up cosmetics and widen the range of colors that can be realized.

Hereinafter, the present invention will be described in more detail.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, unless further departing from the scope of the invention as defined by the following claims. It is not. It is to be understood that the scope of the present invention includes all modifications, equivalents, and alternatives falling within the scope and spirit of the present invention.

The present invention relates to a polyurethane powder and / or a polyamide powder having a weight average molecular weight of 200,000 or more; And water-soluble dyes.

The present invention can provide a cosmetic material which can use a water-soluble dye even in a water-free formulation through the color material to express an extended spectrum color that could not be obtained in a water-free formulation until now, have.

The coloring material of the present invention may have a reflectance of 100 or more. The reflectivity is a value obtained by measuring the degree to which the color material reflects light according to the wavelength. When the reflectance exceeds 100, it means that more light is reflected than the reaction amount light. Therefore, a coloring material having a reflectance of 100 or more is more suitable for use in cosmetics in that it can express a clearer color. In one embodiment of the present invention, it was confirmed that the color material of the present invention had a reflectance exceeding 100 at a wavelength of 600 nm to 620 nm.

Further, the coloring material of the present invention may be one having a characteristic of developing fluorescence.

The dye of the present invention may be in the form of a polyurethane powder and / or a polyamide powder having a weight average molecular weight of 200,000 or more and a water-soluble dye combined with each other, Or may be in the form of a dye coated. The cosmetic composition comprising the colorant of the present invention having a water-soluble dye bonded to the surface of the powder can have a higher reflectivity and fluorescence-generating property as compared with the case of simply containing the powder and the water-soluble dye, The cosmetic material of the present invention has an effect that the coloring material is well dispersed.

In the present invention, a water-soluble dye means a dye having a property of dissolving in a water-soluble solvent in a dye that can be used in a cosmetic, and means a dye having a hydrolysis-decomposing property among the dyes specified to be usable in cosmetics in Korea.

Preferably, the water-soluble dye of the present invention may have the following structural formula (1). The compound of formula 1 may be a salt compound.

[Structural formula 1]

In the above structural formula 1, R ₁ is yet oxygen (O) or _{N (C 2 H 5) 2} , and if R ₁ is oxygen and n is 1, R ₁ is N (C ₂ H _{5) 2} in case n is 0, ; R ₂ and R ₃ are each independently hydrogen, bromine (Br) or iodine (I); R ₄ is COO ^- or SO ₃ ^- and; M is 0 when R ₅ is hydrogen, chlorine or SO ₃ ^- , R ₅ is hydrogen or chlorine, and m is 1 when R ₅ is SO ₃ ^- ; R ₆ is hydrogen or chlorine, and X is aluminum, calcium, sodium or potassium.

In the above structural formula 1, when R ₁ is oxygen (O), R ₄ is COO ^- and R ₅ may be hydrogen or chlorine. In this case, one of two R < ₁ > s in formula 1 may represent the ionic form of O < ^- >.

In the above formula 1, when R ₁ is N (C ₂ H ₅ ) ₂ , R ₄ and R ₅ may be SO ₃ ^- . In this case, one of the two R ₁ in the structural formula 1 may represent a ₂ ⁺ ion form N (C ₂ H _5). In the coloring material of the present invention, the water-soluble dye having the structure of the structural formula 1 may be bonded to the polyurethane powder and / or the polyamide powder to form a new coloring material. The coloring material may be a color And it is possible to provide a coloring material exhibiting a color having excellent brightness and saturation when incorporated in cosmetics as compared with conventional lake-based coloring matter. Particularly, since it has excellent dispersibility even in a water-free formulation, it can be effectively used for a water-free formulation such as lipstick among cosmetic compositions, and it is significant in that it broadens spectrum of color that can be exerted in conventional anhydrous formulations.

The water-soluble dyes are preferably selected from the group consisting of (1) of Red No. 104, (2) of Red No. 104, (1) of Red No. 103, (2) of Red No. 230, (2) of Yellow No. 202.

(1) of the above Red No. 104 is 9- (3,4,5,6-tetrachloro-2-carboxyphenyl) -6-hydroxy-2,5,4,5,7-tetrabromo- 3-one, which can be represented by the following formula (1).

(2) of the above Red No. 104 is 9- (3,4,5,6-tetrachloro-2-carboxyphenyl) -6-hydroxy-2,5,4,5,7-tetrabromo- 3-one, which can be represented by the following formula (2).

(1) of Red No. 103 is a disodium salt of 9- (2-carboxyphenyl) -6-hydroxy-2,4,7-tetrabromo-3H-xanthene- 3 < / RTI >

(2) of the above Red No. 230 is a dipotassium salt of 9- (2-carboxyphenyl) -6-hydroxy-2,5,4,5,7-tetrabromo-3H- 4 < / RTI >

The above-mentioned Equivalent No. 207 is a disodium salt of 9- (2-carboxyphenyl) -6-hydroxy-4,5-diiodo-3H-xanthene-3-one.

The Red No. 106 is a monosodium salt of 2 - [[N, N-diethyl-6- (diethylamino) -3H-xanthene-3-imino] -9-yl] -5-sulfobenzenesulfonate And can be represented by the following formula (6). The Red No. 106 is also referred to as Acid Red No. 52.

(1) of Yellow No. 202 is a disodium salt of 9- (2-carboxyphenyl) -6-hydroxy-3H-xanthene-3-one represented by the following formula (7).

(2) of Yellow No. 202 is a dipotassium salt of 9-olo-carboxyphenyl-6-hydroxy-3-isoxanthone represented by the following general formula (8).

The water-soluble dye of the present invention can have the characteristic of a coloring material that combines with a polyurethane powder and / or a polyamide powder to exhibit fluorescence even though it is a water-soluble dye, by including the structure of the structural formula 1 as a common property.

In the present invention, powder means an object in which solid particles or solid fine particles are gathered, and may be used in combination with powders or powders commonly used in the technical field of the present invention.

In the present invention, the polyurethane powder includes all the polyurethane powder, and may be a polymer of isocyanate group / OH group.

More specifically, hexamethylene diisocyanate (HDI) / trimethylol hexyllactone crosspolymer (hexamethylene diisocyanate (HDI) / trimethylol hexyllactone crosspolymer); And a powder selected from the group consisting of hexamethylene diisocyanate (HDI) / polypropylene glycol (PPG) / polycaprolactone crosspolymer (hexamethylene diisocyanate (HDI) / polypropylene glycol (PPG) / Polycaprolactone crosspolymer) But is not limited thereto.

In consideration of the physical properties and ease of use of the composition to be added, the polyurethane powder may further contain an organic / inorganic particle such as silica or polymethylsilsesquioxane within a range that does not affect the properties of the polyurethane powder .

The polyurethane powder is also commercially available, for example, D-400 (Toshiki), EPU-2X (hexamethylene diisocyanate / trimethylolhexyl lactone crosspolymer and polymethyl methacrylate, Silica, SUNJIN BEAUTY SCIENCE) or KSP-101 (manufactured by SHINETSU), but is not limited thereto.

The polyurethane powder may have a weight average molecular weight of 5,000 to 300,000, preferably 7,000 to 100,000. When the particle size is satisfied, it is possible to provide a color material having a reflectance of 100 or more, a high brightness and a high saturation, and a fluorescence-emitting property.

Further, the average particle size of the polyurethane powder may be 5 탆 to 30 탆, and preferably 10 탆 to 20 탆. When the particle size is satisfied, it is possible to provide a coloring material having a reflectance of 100 or more and having fluorescence expression characteristics.

In the present invention, the polyamide powder may have a weight average molecular weight of 200,000 or more. When the molecular weight is less than 200,000, the water-soluble dye of the present invention is not excellent in reflectivity when it is reacted with the water-soluble dye of the present invention. In addition, the polyamide powder of the present invention has a low absorption capacity through a high molecular weight of 200,000 or more, so that the effect of increasing the composition is lowered, and when it is included in the cosmetic composition, the glossiness of the cosmetic composition is improved. Moreover, since a high molecular weight coloring material can be used, it is easy to control the production of cosmetics and facilitates the manufacturing process including dispersion.

The polyamide powder may be nylon powder, and may be at least one selected from the group consisting of nylon-6, nylon-11, nylon-12, nylon-66 and copolymers thereof. If so, it is not limited to the type of nylon. The copolymer may be, for example, a copolymer of nylon-6 and 12, but is not limited thereto.

The coloring material of the present invention is preferably a water-soluble dye as described above; And polyurethane powder. The colorant of the present invention including a water-soluble dye and a polyurethane powder has a very high reflectance, and thus can have a better expression characteristic when contained in a cosmetic, and at the same time, a colorant having fluorescence properties can be provided.

The coloring material of the present invention is preferably a water-soluble dye as described above; And a polyamide powder having a weight average molecular weight of 200,000 or more. The coloring material of the present invention comprising a water-soluble dye and a polyamide powder having a weight-average molecular weight of 200,000 or more together can lower the effect of increasing the composition with a low water-absorbing ability and can provide a coloring material that improves the glossiness when it is contained in cosmetics Is excellent.

The content of the powder in the coloring material of the present invention is preferably 80 to 99.99% by weight, more preferably 90 to 99.9% by weight, and most preferably 95 to 99.9% by weight based on the total weight. If the content of the powder exceeds 99.99% by weight, the strength of the coloring material is relatively lowered. If the content of the powder is less than 80% by weight, it is difficult to use the coloring material in the makeup cosmetic composition of the anhydrous form, .

The content of the water-soluble dye in the colorant of the present invention is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight, and most preferably 0.1 to 5% by weight based on the total weight of the colorant. When the content of the dye is less than 0.01% by weight, the coloring power is deteriorated and it is difficult to use an appropriate amount in the preparation of a makeup cosmetic composition. When the content exceeds 20% by weight, it is difficult to use it in the anhydrous formulations. .

The coloring material of the present invention has excellent characteristics in that it broadens the color spectrum that can be used in the cosmetic composition, and the present invention relates to a cosmetic composition comprising the coloring material.

Preferably, the cosmetic composition may be a cosmetic composition of a non-aqueous formulation. In addition, the cosmetic composition may be a cosmetic composition for makeup or lips in that it contains a colorant. In the case of the cosmetic composition containing the colorant of the present invention, the colorant of the present invention is excellent in reflectivity and exhibits fluorescence color, so that the lightness and chroma of the cosmetic composition are higher than those in the case of using a conventional lake pigment . Thus, the cosmetic composition comprising the colorant of the present invention may exhibit excellent color expression in eye, mouth or other tonal make-up products.

In the cosmetic composition of the present invention, the coloring material may be contained in an amount of 0.1 to 50 wt%, and the content of the coloring material may be varied depending on the specific use of the cosmetic composition. For example, when the cosmetic composition is a lip composition, the colorant of the present invention may be contained in an amount of 5 to 50% by weight, or 15 to 35% by weight.

The cosmetic composition of the present invention may contain, in addition to the above components, a cosmetic composition which is usually contained in a cosmetic composition such as a preservative, a moisturizer, a softener, a surfactant, an organic and inorganic pigment, an organic powder, an ultraviolet absorber, an antiseptic, , a pH adjusting agent, an alcohol, a coloring matter, a flavoring agent, a blood circulation promoting agent, a cooling agent, and a wax, but is not limited thereto.

In particular, when the cosmetic composition of the present invention is a lip cosmetic composition, it may further include at least one selected from the group consisting of waxes, oils, pigments, and other additives.

Examples of the wax include, but are not limited to, candelilla wax, carnauba wax, ceresin, paraffin, cocoa butter, polyethylene, microcrystalline wax, ozokerite, wax and synthetic wax. In the lip composition of the present invention, the wax may be contained in an amount of 3 to 20% by weight, but is not limited thereto.

Examples of the oil component include a mineral oil such as mineral oil; Animal oils such as squalane and lanolin; Vegetable oils such as sunflower seed oil, avocado oil, jojoba oil, olive oil and castor oil; Diisopropyl myristate, isopropyl palmitate, cetyl hexyl hexanoate, cetyl myristate, polybutene, polyisobutene, hydrogenated polyisobutene, various polyols, tri-2 - synthetic oil such as ethylhexyl acid glycerin, triglyceride oil, octyldodecanol and diisostearyl malate, but not limited thereto.

On the other hand, in the present invention, as the other components usable in the cosmetic composition, particularly the lip cosmetic composition, it is possible to use a conditioning agent, oily ingredient, moisturizing agent, antioxidant, ultraviolet absorber, preservative, It may be blended.

The cosmetic composition, particularly the lip cosmetic composition, having such a composition can be subjected to a treatment such as heating, mixing, stirring, etc. by a usual production method to produce a lip cosmetic composition for the production of lipstick, lip gloss, lip balm or lip pencil.

The present invention also relates to a curable composition comprising: at least one powder selected from the group consisting of a polyurethane powder and a polyamide powder having a weight average molecular weight of 200,000 or more; And a water-soluble dye to prepare a coloring material; And a method of producing the lip cosmetic product by adding the color material to the cosmetic composition.

At least one powder selected from the group consisting of a polyurethane powder of the present invention and a polyamide powder having a weight average molecular weight of 200,000 or more; And water-soluble dyes are excellent in dispersibility even in the anhydrous form, and in particular, make it possible to produce cosmetics having excellent fluorescence properties which can not be obtained with conventional dyes, and which have good color and excellent expression.

In the method of manufacturing a lip cosmetic product according to the present invention, when the polyamide powder is 200,000 or more, the absorption capacity is low, thereby lowering the effect of increasing the composition, thereby improving luster in cosmetic products for lips. In addition, it is easy to disperse to improve the efficiency of cosmetic production.

Hereinafter, the present invention will be described in detail with reference to Production Examples and Experimental Examples. The following Examples and Experiments are illustrative of the present invention and are not intended to limit the scope of the present invention.

[ Manufacturing example  One] Color  Produce

Manufacturing example  1-1. Powder  Used Color  Produce

The dye was dissolved in water-soluble dyes using purified water and ethanol as a solvent. Nylon-12 (ANYBES, average particle size of 6-9 탆, molecular weight: 300,000, manufactured by SH Energy Chemical Co., Ltd., Table 1) as a polyamide powder; (TOSHIKI; Plastic Powder D-400, average particle size: 12-18 占 퐉; molecular weight: 10,000 or more, Table 1); (SUNSIL-130; average particle size: 7 탆, Table 2) was added to the mixture and the mixture was stirred for 10 minutes at 1000 rpm using a Disper mixer. The blending ratios of the water-soluble dyestuffs (1) of Red No. 104 or (1) of Red No. 103 are as shown in Table 1. Then, the solvent was evaporated to obtain a coloring material.

Component (% by weight)	Example 1	Example 2	Example 3	Example 4	Example 5	Example 6	Example 7	Example 8	Example 9
HS di / trimethylolhexyl lactone cross polymer, silica	-	-	99.0	99.0	9.9	29.7	49.5	69.3	89.1
Nylon-12	99.0	99.0	-	-	89.1	69.3	49.5	29.7	9.9
(1) of Red No. 104,	1.0	-	1.0	-	1.0	1.0	1.0	1.0	1.0
Red No. 103 (1)	-	1.0	-	1.0	-	-	-	-	-
sum	100	100	100	100	100	100	100	100	100

Component (% by weight)	Comparative Example 1	Comparative Example 2	Comparative Example 3	Comparative Example 4
Silica	-	-	99.0	99.0
(1) of Red No. 104,	100.0	-	1.0	-
Red No. 103 (1)	-	100.0	-	1.0
sum	100	100	100	100

Manufacturing example  1-2. Red 227  Included Color  Produce

A coloring material containing a red color No. 227 dye was prepared by using nylon-12, a polyurethane-based powder or silica in the same manner as in Example 1-1 except that the red color No. 227 was used as a water-soluble dye.

[Red No. 227]

ingredient	Comparative Example 5	Comparative Example 6	Comparative Example 7
HS di / trimethylolhexyl lactone cross polymer, silica	99.0	-	-
Nylon-12	-	99.0	-
Silica			99.0
Red 227	1.0	1.0	1.0
sum	100	100	100

[ Experimental Example  1] New Color  Identify characteristics

(1) of Red No. 104 (1) of Comparative Example 1) and the coloring material of Example 1 (polyamide powder of a molecular weight of 300,000 + red No. 104 of (1) of the red color 103 (1)) and the colorant of Example 3 (the colorant of the polyurethane powder + red color No. 104) (1) of a polyamide powder with a molecular weight of 300,000 + (1) of red 103) and the color material of Example 4 (polyurethane powder + red 103 (1)).

As shown in Fig. 1, the coloring materials of Examples 1 to 4 of the present invention and the conventional water-soluble dyes of Comparative Example 1 or 2 exhibited a large color difference even with naked eyes. In particular, only the coloring materials of Examples 1 to 4 of the present invention Is observed.

The fluorescence of each color material of Comparative Examples 1 and 2 and Examples 3 and 4 was analyzed using a time-resolved fluorescence spectrophotometer. Excitation was performed at 500 nm for each treatment, and the intensity of light was measured in the visible light region.

As a result, as shown in Figs. 2A to 2D, when the light of 500 nm was given, it was confirmed in a graph that the colorant of Example 3 and the colorant of Example 4 showed emission. On the other hand, in Comparative Example 1 and Comparative Example 2, no light other than the quasi-light was observed. Therefore, it can be seen that Examples 3 and 4 have the characteristics of a fluorescent coloring material emitting light energy by receiving light energy, unlike Comparative Example 1 (1) of Red No. 104 (1) or Comparative Example 2 (Red No. 103, (1)

[Experimental Example 2] Analysis of reflectance of dye

It is possible to prove the fluorescent color feeling of the colorant through the result of measuring the reflectance of light according to the wavelength. Therefore, the dyes of Examples 1 to 9 and Comparative Examples 1 to 4 were measured for the reflectance of light according to wavelength using a MINOLTA CM512M3 colorimeter Were measured. Specifically, the reflectance was measured at around 600 nm or 620 nm and is shown in Table 4 below.

	Example 1	Example 2	Example 3	Example 4	Example 5	Example 6	Example 7	Example 8	Example 9
Reflectivity	152 (620 nm)	129 (600 nm)	176 (620 nm)	131 (600 nm)	155 (620 nm)	159 (620 nm)	165 (620 nm)	169 (620 nm)	173 (620 nm)

	Comparative Example 1	Comparative Example 2	Comparative Example 3	Comparative Example 4	Comparative Example 5	Comparative Example 6	Comparative Example 7
Reflectivity	28 (620 nm)	15 (600 nm)	85 (620 nm)	70 (600 nm)	44 (620 nm)	42 (620 nm)	42 (620 nm)

As a result, as shown in Figs. 3A to 3D, the conventional water-soluble dyestuffs not modified with the powders of Comparative Examples 1 and 2 had a reflectance of less than 100 in all sections, and the colorants of Comparative Example 3 or 4 including silica also had reflectivity Is less than 100, it is confirmed that it does not have desired reflectivity characteristics in the present invention. However, the color materials of Examples 1 to 9 exhibit a reflectance of 100 or more at around 620 nm and 600 nm, meaning that they reflect more light than the received amount of light, which means they are all fluorescent color materials. In particular, it was confirmed that the colorant of Example 3 or 4 modified with a polyurethane-based powder can produce a colorant having a better reflectivity than the case of using a polyamide colorant under the same conditions. This shows the same tendency when lipsticks were produced using the coloring material of the present invention.

Further, as shown in Table 5 or FIG. 4, it was found that the colorant containing red No. 227 had a reflectance of less than 100 even though it was modified in the same manner, As a result, it is found that the dye of the present invention can be obtained by modifying the powder of the present invention to exhibit the characteristics of the fluorescent coloring material only for a dye having a partial structure satisfying the structural formula 1 of the present invention.

[ Manufacturing example  2] Anhydrous form of  Cosmetics Manufacturing

As a result of confirming that the color materials 1 to 4 had properties as a fluorescent coloring material, lipsticks were prepared using the coloring materials of Examples 3 and 4 in order to confirm whether or not the coloring material could be used for a water-free formulation. Lipsticks were prepared by using Lake pigment Red28 Lake and Red22 Lake for each of water-soluble dye red No. 104 (1) and red No. 103 (1) in order to compare color development characteristics in a water-free formulation.

The wax and oil components shown in Table 6 were heated to dissolve the wax, and they were mixed and stirred at 1000 rpm for 10 minutes using a Disper mixer. Thereafter, each dye was added thereto and further stirred for 10 minutes at 1000 rpm with a Disper mixer. Then, it was degassed and poured into a lipstick mold to cool the lipstick. As the polyurethane powder (HS di / trimethylolhexyl lactone cross polymer, silica), powders having the same conditions as in Production Example 1-1 were used.

Component (% by weight)	Comparative Example 8	Comparative Example 9	Example 10	Example 11
Synthetic wax, an ethylene / propylene copolymer	5.0	5.0	5.0	5.0
Ceresin	6.5	6.5	6.5	6.5
Polyglyceryl-2 triisostearate	Balance
Triethanolhexanone	45.0	45.0	45.0	45.0
(1) of Red No. 104 (Red28 Lake)	0.3	-	-	-
Red No. 103 (1) (Red 22 Lake)	-	0.3	-	-
Colorant of Example 3	-		30.0	-
The colorant of Example 4	-	-	-	30.0
HS di / trimethylolhexyl lactone cross polymer, silica	30.0	30.0	-	-
sum	100

As shown in Figs. 5A and 5B, when conventional rake dyes were used for a water-free formulation as in Comparative Examples 8 and 9, and when the coloring materials of Examples 3 and 4 of the present invention were used (Production Examples 1 and 2) In the case of Comparative Examples 8 and 9, in the case of Comparative Examples 8 and 9, in each of Examples 10 and 11, even though the cosmetic composition contained HS as the polyurethane powder and silica as the polyurethane powder, The difference between lipstick and color was remarkable. This means that the color rendering property of the surface-modified coloring material of the present invention is not caused by simple mixing of the polyamide or polyurethane powder and the dye.

[ Manufacturing example  3] Cosmetics  Preparation of composition

The kinds and ratios of the dyes used in the preparation of the various cosmetic dyes were changed, and the makeup cosmetic dyes were prepared by the same five methods. In the same manner as in the above method, a comparative example (a conventional rake dye, and a new coloring material of the present invention modified with a polyurethane powder according to Example 1-1) Quot; modified ") was prepared, and the brightness and saturation of the composition were compared under five conditions. The following table is the value of the Munsell colorimetric system and is the value measured with the MINOLTA CM512M3 colorimeter.

Samples (content by weight% based on 100 g total)	Value		Chroma
	Unmodified	Modification	Unmodified	Modification
Sample 1 (Unmodified: (1) Rake 0.3 weight% of Red No. 103; Modification: (1) Red Color No. 103 No. 1 (wt)	5.66	6.84	12.48	15.93
Sample 2 (Unmodified: (1) Rake 0.9% by weight of Red No. 103; Modification: (3) Red Color No. 103 (3)	5.03	5.73	13.22	14.72
Sample 3 (Unmodified: (1) Rake 0.1% by weight of Red No. 104; Modification: (1) Use of 10 g of 1% (wt)	4.65	6.24	13.58	17.68
Sample 4 (Unmodified: (1) Rake 0.6% by weight of Red No. 104; (Modification: 30 g of 2% (wt)	4.32	5.46	13.03	17.54
Sample 5 (unmodified: (1) rake 1.5% by weight of Red No. 104; (1) 30% of the colorant containing 5% (wt) of Red No. 104)	3.97	4.41	12.57	14.04

The coloring amounts used in Samples 1 to 5 of Table 7 are all the same, and as shown in Table 7, the lightness and chroma of the cosmetic composition containing the novel cosmetic coloring material according to the present invention include the conventional lake coloring matter Compared with the case of the case of the case of the test. Therefore, in the case of the cosmetic composition containing the colorant of the present invention, a cosmetic composition having a clear and excellent coloring property can be provided.

Claims (9)

1. At least one powder selected from the group consisting of polyurethane powder and polyamide powder having a weight average molecular weight of 200,000 or more; And

   A colorant comprising a water-soluble dye of the following structural formula 1:

   [Structural formula 1]

   

   In the above formula 1,

   R ₁ is oxygen (O) or N (C ₂ H ₅ ) ₂ , n is 1 when R ₁ is oxygen, and n is 0 when R ₁ is N (C ₂ H ₅ ) ₂ ;

   R ₂ and R ₃ are each independently hydrogen, bromine (Br) or iodine (I);

   R ₄ is COO ^- or SO ₃ ^- and;

   M is 0 when R ₅ is hydrogen, chlorine or SO ₃ ^- , and R ₅ is hydrogen or chlorine, m is 1 when R ₅ is SO ₃ ^-

   R < ₆ > is hydrogen or chlorine; X is aluminum, calcium, sodium or potassium.
2. The method according to claim 1,

   The polyurethane may be selected from the group consisting of hexamethylene diisocyanate (HDI) / trimethylol hexyllactone crosspolymer (hexamethylene diisocyanate (HDI) / trimethylol hexyllactone crosspolymer); And at least one member selected from the group consisting of hexamethylene diisocyanate (HDI) / polypropylene glycol (PPG) / polycaprolactone crosspolymer (hexamethylene diisocyanate (HDI) / polypropylene glycol (PPG) / Polycaprolactone crosspolymer).
3. The method according to claim 1,

   Wherein the polyamide is at least one selected from the group consisting of nylon-6, nylon-11, nylon-12, nylon-66 and copolymers thereof.
4. The method according to claim 1,

   The water-soluble dyes include the dyes of (1) of Red No. 104, (2) of Red No. 104, (1) of Red No. 103, (2), Red No. 207, Red No. 106, (2). ≪ / RTI >
5. The method according to claim 1,

   Wherein the color material has a reflectivity of more than 100.
6. The method according to claim 1,

   Polyurethane powder; And

   (1) of Red No. 104, (2) of Red No. 104, (1) of Red No. 103, (2) of Red No. 230, No. 207 of Red No. 106, No. 1 of Yellow No. 202, And at least one water-soluble dye selected from the group consisting of water-soluble dyes.
7. A cosmetic composition comprising the colorant according to any one of claims 1 to 6.
8. 8. The method of claim 7,

   Wherein the cosmetic composition is a water-free formulation.
9. A cosmetic composition for lips comprising the colorant according to any one of claims 1 to 6.

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