JP3465031B2 - Coated pigments and cosmetics - Google Patents

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a resin particle having an ultraviolet absorbing property, which is formed from a resin having an ultraviolet absorbing structure, an extender pigment or a pearl pigment whose surface is at least partially coated with the resin particle, and The present invention relates to cosmetics containing such a coated pigment and having low skin irritation.

[0002]

BACKGROUND OF THE INVENTION Sun rays contain ultraviolet rays that cause erythema (sunburn) on human skin and cause spots, freckles, etc. Cosmetics containing absorbents are used.

Ultraviolet absorbers include inorganic pigments such as titanium dioxide, zinc oxide and iron oxide which shield ultraviolet rays, and organic ultraviolet absorbers which absorb ultraviolet rays. The above-mentioned inorganic pigment hides the skin and blocks ultraviolet rays. When such an inorganic pigment is applied to the skin, it is whitened or colored, and therefore cannot be incorporated in a large amount in cosmetics.

On the other hand, the organic ultraviolet absorber absorbs ultraviolet rays without hiding the skin, so that the problem of whitening or coloring does not occur. For these reasons, in recent years, organic UV absorbers have been increasingly used as the UV absorber.

However, many organic UV absorbers are irritating to the skin, and if they are used as they are in a mixture with other cosmetic base materials, they may irritate the skin.

Therefore, in order to prevent such an organic ultraviolet absorber from coming into direct contact with the skin, it has been proposed to disperse the ultraviolet absorber inside the resin particles and use it. There is. For example, Japanese Patent Publication No. 62-51931, JP-A No. 62-198612, and the like disclose resin particles containing such an organic ultraviolet absorber.

By thus binding the organic UV absorber in the resin particles, it becomes difficult for the UV absorber to come into direct contact with the skin, and irritation is reduced as compared with cosmetics containing the UV absorber directly. Therefore, if the resin particles in which the UV absorber is bound inside as described above is used, the skin irritation due to the UV absorber should be eliminated, but even if such resin particles are actually used, the UV absorber still remains The skin may be irritated.

That is, the organic ultraviolet absorber is restricted only by the physical engaging force in the pores existing in the particles formed from the resin, apart from the resin structure forming the particles, If an oily base or the like of cosmetics enters inside, the oily base moves out of the particles. Then, when actually measured, several% of the used organic ultraviolet absorber may be eluted when the amount is large. The ultraviolet absorbent thus eluted was the cause of skin irritation.

[0009]

OBJECT OF THE INVENTION It is an object of the present invention to provide ultraviolet absorbing resin particles which are not irritating to the skin.

A further object of the present invention is to provide an extender pigment or pearl pigment whose surface is at least partially coated with the above UV-absorbing resin particles having no skin irritation.

Another object of the present invention is to provide a hypoallergenic cosmetic containing the above-mentioned non-skin irritating coated pigment.

[0012]

[0013]

[0014]

SUMMARY OF THE INVENTION In the coated particles of the present invention, a surface of an extender pigment or a pearl pigment has a repeating unit derived from a reactive benzotriazole compound represented by the following formula [I], and a (meth) acrylic compound It is characterized by being coated with 5 to 95% of ultraviolet absorbing resin particles formed of a resin having a repeating unit derived from ## STR1 ## and / or a repeating unit derived from a styrene compound.

[Chemical 4]

Further, in the cosmetic of the present invention, the surface of the extender pigment or pearl pigment has a repeating unit derived from the reactive benzotriazole compound represented by the above formula [I], and a (meth) acrylic compound. UV-absorbing resin particles formed from a resin having a repeating unit derived from and / or a repeating unit derived from a styrenic compound , characterized in that it contains a coated pigment coated in an amount of 5 to 95%. There is.

The ultraviolet absorbing resin particles of the present invention are benzotriazole compounds represented by the above formula [I].
(2'-hydroxy-5'-methacryloxyethylphenyl) -2
It is formed of a resin having a repeating unit derived from H-benzotriazole. Thus, the resin forming the particles of the present invention has a repeating unit having an ultraviolet absorbing function in its molecular structure. Therefore, even if the particles come into contact with the oily cosmetic base, the ultraviolet absorbent component does not flow out, and the skin irritation is extremely low. Further, the coated pigment having at least a part of the surface coated with these particles has no skin irritation and exhibits a good ultraviolet absorbing action, and the gloss of the pigment can be adjusted by changing the surface coverage of the pigment. . Such a coated pigment is obtained by, for example, drying an aqueous dispersion containing ultraviolet absorbing resin particles and a pigment by a spray drying method, or in the presence of a pigment to be coated, the above monomer in an aqueous medium. It can be easily produced by polymerizing. Furthermore, cosmetics containing such a coated pigment have less skin irritation, have a good ultraviolet absorbing action, have good paste of makeup, and have no unnatural luster in makeup.

[0017]

DETAILED DESCRIPTION OF THE INVENTION Next, the ultraviolet absorbing resin particles, the coated pigment, and the cosmetic material of the present invention will be specifically described.

The ultraviolet absorbing resin particles of the present invention are a copolymer of a specific reactive benzotriazole compound and a (meth) acrylic compound and / or styrene compound.

This reactive benzotriazole compound can be represented by the following formula [I].

[0020]

[Chemical 5]

[I] This reactive benzotriazole compound is derived from the benzotriazole structure possessed by 2- (2'-hydroxy-5'-methacryloxyethylphenyl) -2H-benzotriazole. It has an ultraviolet absorbing function and a polymerization activity derived from a methacryloyl group.

Therefore, this compound has an excellent action of absorbing ultraviolet rays and exhibits good reactivity with acrylic compounds and styrene compounds. It is an acrylic compound and / or a styrene compound that reacts with the reactive benzotriazole compound represented by the above formula [I] to form the ultraviolet absorbing resin particles of the present invention.

Here, examples of the acrylic compound used for forming the particles include (meth) acrylic acid ester-based monomers, and examples of the styrene compound include substituted or unsubstituted styrene-based monomers. Mention may be made of monomers. Further, other monomers copolymerizable with these monomers can be copolymerized.

Examples of the (meth) acrylic acid ester-based monomer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth). ) Acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-propyl (meth) acrylate, chloro
-2-hydroxyethyl (meth) acrylate, diethylene glycol mono (meth) acrylate, methoxyethyl (meth) acrylate, glycidyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate and isoboronor (meth) ) Acrylate etc. can be mentioned.

Further, examples of the substituted or unsubstituted styrene-based monomer include styrene, methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene,
Alkyl styrenes such as diethyl styrene, triethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene and octyl styrene;
Mention may be made of halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, styrene iodide and chloromethylstyrene; and nitrostyrene, acetylstyrene and methoxystyrene.

The acrylic compound and the styrene compound may be copolymerized individually with the benzotriazole compound, or may be copolymerized by combining both.

Examples of other monomers that can be copolymerized with the benzotriazole compound together with the acrylic acid monomer or the styrene monomer as described above include vinyl monomers and unsaturated carboxylic acid monomers.

Specific examples of the vinyl monomers include vinyl pyridine, vinyl pyrrolidone, vinyl carbazole, vinyl acetate and acrylonitrile; conjugated diene monomers such as butadiene, isoprene and chloroprene; halogens such as vinyl chloride and vinyl bromide. Examples thereof include vinylidene halide and vinylidene halide such as vinylidene chloride.

Further, specific examples of the unsaturated carboxylic acid monomer include (meth) acrylic acid, α-ethyl (meth) acrylic acid, crotonic acid, α-methylcrotonic acid,
Addition-polymerizable unsaturated aliphatic monocarboxylic acids such as α-ethyl crotonic acid, isocrotonic acid, tiglic acid and ungeric acid; addition of maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid and hydromuconic acid Mention may be made of polymerizable unsaturated aliphatic dicarboxylic acids.

If desired, the (meth) acrylic acid ester copolymer may be copolymerized with a bifunctional or polyfunctional monomer. Examples of bifunctional or polyfunctional monomers include ethylene glycol di (meth) acrylate, triethylene glycol (meth) acrylate, tetraethylene glycol (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate. ) Acrylate, 1,1,1-trihydroxymethylethane triacrylate, 1,1,1-trishydroxymethylmethylethane triacrylate, 1,1,1-trishydroxymethylpropane triacrylate and vinylbenzene can be mentioned. .

In the ultraviolet absorbing resin particles of the present invention,
The benzotriazole-based compound is an acrylic compound and / or a styrene-based compound 1 that forms the particles.
It is usually used in an amount of 1 to 40 parts by weight, preferably 10 to 30 parts by weight, based on 00 parts by weight.

When the ultraviolet absorbing resin particles of the present invention are acrylic resins, a copolymer of a (meth) acrylic acid ester-based monomer and the above benzotriazole-based compound is preferable, but the present invention is not limited to this. ) Acrylic ester-based monomer is usually 20 to 100 parts by weight, preferably 40 to 100 parts by weight, styrene-based monomer is usually 0 to 80 parts by weight, preferably 0 to 60 parts by weight, bifunctional or polyfunctional. 0 to 20 parts by weight of monomer,
A copolymer obtained by (co) polymerizing preferably 0 to 15 parts by weight, a vinyl monomer in an amount of usually 0 to 50 parts by weight, and an unsaturated carboxylic acid monomer in an amount of usually 0 to 50 parts by weight can be used. Have sex.

Further, when the ultraviolet absorbing resin particles of the present invention are styrenic resins, a copolymer of a styrenic monomer and the above-mentioned benzotriazole compound is preferable, but not limited to this, the styrenic monomer is usually used. 20-100
Parts by weight, preferably 40 to 100 parts by weight, (meth) acrylic acid ester-based monomer, usually 0 to 80 parts by weight,
Preferably 0 to 60 parts by weight, difunctional or polyfunctional monomer, usually 0 to 20 parts by weight, preferably 0 to 15 parts by weight, vinyl monomer, usually 0 to 50 parts by weight, unsaturated carboxylic acid monomer There is a possibility that a copolymer obtained by (co) polymerizing the compound may be used in an amount of 0 to 50 parts by weight.

Further, when the ultraviolet absorbing resin particles of the present invention are a copolymer of an acrylic compound, a styrene compound and a benzotriazole compound, the (meth) acrylic acid ester monomer is usually 20 to 80. Parts by weight,
Preferably 40 to 60 parts by weight, the styrenic monomer is
Usually, it is possible to use a copolymer which is copolymerized in an amount of 20 to 80 parts by weight, preferably 40 to 60 parts by weight, and further, as the copolymer, a bifunctional or polyfunctional monomer is usually used. Is 0 to 20 parts by weight, preferably 0 to 1
There is a possibility that a copolymer obtained by (co) polymerizing 5 parts by weight, usually 0 to 50 parts by weight of a vinyl monomer and 0 to 50 parts by weight of an unsaturated carboxylic acid monomer can be used. ing.

The reactive benzotriazole compound represented by the above formula [I] is a repeating unit represented by the following formula [IA] in the resin forming the ultraviolet absorbing resin particles of the present invention. Is considered to form.

[0036]

[Chemical 6]

[IA] The repeating unit formed by the acrylic compound and the styrene compound is well known.

The ultraviolet absorbing resin particles of the present invention have an average particle diameter of usually 0.06 to 20 μm, preferably 0.0.
It is in the range of 7 to 8 μm. Particles having an average particle diameter within the above range can satisfactorily coat the surface of an extender pigment or a pearl pigment to impart ultraviolet absorptivity to the extender pigment or the pearl pigment. By adjusting the ratio, it becomes possible to adjust the gloss of the pigment.

In the ultraviolet absorbing resin particles of the present invention, the resin itself constituting the particles has an ultraviolet absorbing property, and since this resin is insoluble in the oily base material of cosmetics, etc. When added to cosmetics, the UV absorber, which has conventionally been the cause of skin irritation, does not elute, and the safety is extremely high. Further, the benzotriazole-based compound copolymerized with this resin has excellent ultraviolet absorption.

The above-mentioned UV absorbing resin particles can be blended with a resin film and used as a UV absorbing agent and a tack preventive agent for the resin film. The UV absorbing resin particles are particularly preferable. It is highly useful as an ultraviolet absorber incorporated in cosmetics. In particular, by coating an extender pigment or a pearl pigment with the ultraviolet absorbing resin particles, it is possible to impart an ultraviolet absorbing action to the extender pigment or the pearl pigment and to adjust the gloss of the extender pigment or the pearl pigment. In addition, the powder characteristics (for example, fluidity) of this extender pigment or pearl pigment can be improved.

The coated pigment of the present invention is an extender pigment or pearl pigment whose surface is incompletely coated with the above-mentioned ultraviolet absorbing resin particles. Here, the extender pigment is a pigment for adjusting the fluidity and optical properties of the cosmetic by being mixed with the cosmetic, and specific examples of the extender pigment include talc, kaolin, and calcium carbonate. , Magnesium carbonate, magnesium silicate and silicic anhydride.

The pearl pigment is a pigment used to impart a pearly luster to cosmetics, and specific examples of the pearl pigment include fish scale foil, bismuth oxychloride, titanium mica and mica. be able to.

In the coated pigment of the present invention, at least a part of the surface of the extender pigment or the pearl pigment as described above is coated with the above-mentioned ultraviolet absorbing resin particles. That is, in the coated pigment of the present invention, the above-mentioned ultraviolet absorbing resin particles adhere to the surface of the pigment and cover at least a part of the surface of the pigment in a state where the particle shape of the ultraviolet absorbing resin is maintained substantially. By thus coating the surface of the extender pigment or pearl pigment with the above-mentioned ultraviolet absorbing resin particles, it is possible to impart an ultraviolet absorbing action to the extender pigment or pearl pigment, and at the same time, to extend the extender pigment or pearl pigment. It is possible to adjust the powder characteristics (eg, fluidity) and gloss of the above. Therefore, the surface coverage of the extender pigment or pearl pigment with the ultraviolet absorbing resin particles can be appropriately set in consideration of the characteristics of the extender pigment or pearl pigment to be obtained. However, if the coating rate of the pigment surface is less than 5%, it may not be possible to impart an effective ultraviolet absorbing performance to this coated pigment, so normally 5% or more of the surface of the pigment is coated.

Further, as the coverage of the UV absorbing resin particles on the surface of the extender pigment or pearl pigment is increased to 30%, 50%, 70% or more, the ultraviolet absorbing performance is improved and the extender pigment is improved. Alternatively, the properties inherently possessed by the pearl pigment become latent, and the properties essentially possessed by the resin particles (aggregate of resins) become apparent. For example, in the case of pearl pigments, as the coverage of resin particles increases, the pearly luster gradually decreases, but powder properties such as fluidity and ultraviolet absorption properties tend to improve. Further, in the case of the extender pigment, as the coverage increases, the gloss, which is not preferable as the extender pigment, decreases, and the powder properties such as fluidity and the ultraviolet absorbing properties tend to improve.

Particularly on the surface of the extender pigment or pearl pigment
By coating 0 to 95%, preferably 45 to 90% of the ultraviolet absorbing resin particles with the above-mentioned ultraviolet absorbing resin particles, the extender pigment and the pearl pigment are maintained while maintaining the characteristics essentially possessed by the extender pigment and the pearl pigment. Can be endowed with good powder characteristics and ultraviolet absorption characteristics. Further, in the case of an extender pigment, the unnatural luster is eliminated, and the above-mentioned coverage is particularly preferable. In the present invention , with the coating pigment having a coverage of more than 95%, the characteristics of the coated extender pigment or the pearl pigment do not appear, and the ultraviolet absorption characteristics and the powder characteristics of the ultraviolet absorbing resin particles are simply revealed. Therefore, if the coating amount exceeds 95%, it is meaningless to use an extender pigment or a pearl pigment.
Further, it is preferably 90% or less.

In the coated pigment of the present invention, at least a part of the surface of the extender pigment or the pearl pigment is coated with the specific ultraviolet absorbing resin particles, and the surface of the coated pigment of the present invention is the present invention. The ultraviolet-absorbing resin particles of No. 1 exist in a state where the shape is maintained as it is. If a resin film is simply formed on the surface of the extender pigment or the pearl pigment, the gloss of the extender pigment or the pearl pigment is increased, and the powder characteristics are hardly improved. By coating with an extender pigment or pearl pigment while maintaining the shape,
The gloss of the extender pigment or the pearl pigment can be adjusted according to the coverage. Further, the powder characteristics of the extender pigment or the pearl pigment are also improved. And since the resin forming the particles themselves has excellent ultraviolet absorption properties, the coating pigment of the present invention becomes excellent in ultraviolet absorption properties by coating with the ultraviolet absorption resin particles. At the same time, the ultraviolet absorbing component is not eluted by the cosmetic oily base or the like.

The coated pigment of the present invention is prepared by dispersing a benzotriazole compound and an acrylic compound and / or a styrene compound in an aqueous medium in which an extender pigment or a pearl pigment is dispersed, as described below. It can be produced by reacting these polymerizable components in the presence of a pigment.

To produce the coated particles of the present invention, first,
The extender pigment or pearl pigment to be coated is dispersed in an aqueous medium. Here, water is usually used as the aqueous medium, but a water-soluble organic solvent such as alcohol may be mixed with the aqueous medium.

Then, the benzotriazole compound represented by the above formula [I] and the acrylic compound and / or the styrene compound are dispersed in the aqueous medium in the form of fine oil droplets. When the resin-forming component as described above is dispersed in the form of oil droplets in an aqueous medium in which an extender pigment or a pearl pigment is dispersed, it can be dispersed without using an emulsifier. An emulsifier or the like can also be used. Therefore, particles can be formed from the monomer dispersed in the form of oil droplets by emulsion polymerization, soap-free emulsion polymerization, suspension polymerization or seed polymerization. Examples of emulsifiers used, for example, in emulsion polymerization are alkylbenzene sulfonates such as sodium dodecylbenzene sulfonate; polyethylene glycol alkyl ethers such as polyethylene glycol nonyl phenyl ether; and vinyl, acryloyl and allyl. Examples thereof include reactive emulsifiers having a reactive group such as a group, and examples of the dispersion stabilizer include water-soluble polymer compounds such as polyvinyl alcohol and polyacrylate. The emulsifier, dispersion stabilizer and the like are usually used in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the monomer.

To disperse the monomer in the aqueous medium, a dispersing device such as a homomixer is usually used. further,
In this aqueous medium, a reaction initiator is usually dispersed and polymerized. Examples of the reaction initiator that can be used here include azo compounds such as azobisisobutyronitrile, organic peroxides such as benzoyl peroxide and lauryl peroxide, and persulfates such as potassium persulfate and ammonium persulfate. Mention may be made of salt. Such a reaction initiator is usually used in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the monomer.

When polymerizing the monomers dispersed in the aqueous medium as described above, it is preferable to purge the inside of the reaction vessel with an inert gas such as nitrogen gas. After purging the inside of the reaction vessel with an inert gas in this way, the polymerization reaction proceeds by heating the temperature of the reaction solution to 60 to 80 ° C. The resin particles formed by polymerizing the monomer adhere to the surface of the extender pigment or the pearl pigment coexisting in the aqueous medium.

Under the above reaction conditions, the reaction time required for producing the particles is usually 3 to 6 hours. Thus, in the presence of the extender pigment or the pearl pigment, the surface of the extender pigment or the pearl pigment can be formed by polymerizing oil-droplet-shaped monomers in an aqueous medium to form particles. A coated pigment coated with resin particles can be produced.

Extending pigment or pearl pigment 10
Adjusting the amount of the monomer so that the amount of the ultraviolet absorbing resin particles produced with respect to 0 part by weight is 110 parts by weight or less, preferably 100 parts by weight or less, more preferably 98 to 5 parts by weight. Thus, the surface of the extender pigment or pearl pigment can be discontinuously coated with the ultraviolet absorbing resin particles as described above.

By performing the above reaction in the presence of both the extender pigment and the pearl pigment, two types of coated pigments in which the surfaces of the extender pigment and the pearl pigment are incompletely coated with the ultraviolet absorbing resin particles Can be obtained.

As described above, the surface of the extender pigment or the pearl pigment is incompletely coated with the ultraviolet absorbing resin particles, and the coated pigment produced by filtering, centrifuging or the like is separated, and further the emulsifier and the dispersion stabilizer are added. The coated pigment of the present invention can be obtained by washing to remove the above.

The coated pigment thus produced can be provided as a dispersion in an aqueous medium, or can be separated from the aqueous medium and dried, and then the dried product can be crushed and provided as a powder. it can.

Further, the coated pigment of the present invention can also be produced by drying a dispersion liquid in which the above-mentioned ultraviolet absorbing resin particles and the extender pigment and / or the pearl pigment are dispersed by using a spray dryer. The spray drier sprays the dispersion by atomizing it into a drying chamber such as a hot gas chamber or a hot cylinder with hot air or the like,
It is an apparatus for instantaneously evaporating volatile components (for example, water) in the dispersion liquid and drying. Here, the temperature of the hot air that blows the dispersion liquid to the drying chamber is usually set to a temperature equal to or higher than the boiling point of the dispersion medium, but when an aqueous medium is used, the temperature of the hot air is within the range of 120 to 200 ° C. It is preferable to set to. The drying conditions are set such that the temperature of the gas exhausted after being blown with the hot air as described above falls within the range of 60 to 100 ° C. That is, the temperature difference between the hot air supplied to the dryer and the exhaust gas is 50 to 100.
It is preferable to set the spray-drying conditions so that the temperature is about ° C.

As described above, for the coated particles of the present invention, the ultraviolet absorbing resin particles of the present invention are produced in the presence of an extender pigment or a pearl pigment, and water in the dispersion liquid is removed by a method such as spray drying. Further, in the above reaction, resin particles are produced without the presence of an extender pigment or a pearl pigment in the above reaction, and the obtained pigment is dispersed in the dispersion liquid. To disperse the extender pigment or the pearl pigment, and then to dry the dispersion liquid in which the resin particles and the pigment are dispersed by evaporating volatile components by a method such as spray drying. Can also be manufactured by.

The ultraviolet absorbing resin particles produced without the presence of the extender pigment or the pearl pigment in this way are more uniform than the ultraviolet absorbing resin particles produced in the coexistence of the extender pigment or the pearl pigment, and thus the In the invention, it is preferable to produce the coated pigment by this method.

In the coated inorganic particles thus prepared by the spray drying method, the above-mentioned specific resin particles are adhered around the extender pigment or pearl pigment, and the spherical organic fine powder adhered on the outer periphery is The spherical shape is maintained almost as it is.

The coated pigment thus obtained has a form in which the outer periphery of the extender pigment or pearl pigment is covered with resin particles. In such a coated pigment of the present invention, the coverage of the pigment surface can be changed by adjusting the amount of resin particles and the amount of resin particles.

The coated pigment of the present invention can be used in the same manner as the extender pigment or the pearl pigment which has been used conventionally. Examples of cosmetics containing the extender pigment and / or pearl pigment coated as described above include makeup cosmetics such as foundation, powder white powder, solid white powder, blusher, and eye shadow.

Specifically, the coated pigment of the present invention includes paraffin, sercine, petrolatum, liquid paraffin, castor oil, sorghum, lanolin, beeswax, carnauba wax, candelilla wax, vegetable oil, vegetable oil ester, fatty acid, higher alcohol and squalane. Oils and waxes; anionic surfactants such as sodium alkylsulfate, cationic surfactants such as alkyltrimethylammonium chloride, amphoteric surfactants such as alkyldimethylammonium betaine, and poly Surfactants such as nonionic surfactants such as oxyethylene alkyl ethers; resins; dispersion stabilizers;
Dyes, fragrances, preservatives, alkylene glycols, other coloring pigments, inorganic powders, organic powders, triethanolamine, solvents and the like can be mixed with commonly used cosmetic raw materials to obtain desired cosmetics.

In such cosmetics, the coated pigment of the present invention can be used in the same amount as that of the extender pigment or pearl pigment which is usually used. Specifically, it is used in an amount of 1 to 95% by weight in the total amount of the cosmetic ingredients. 1
If the amount is less than wt%, the characteristics of the coated pigment of the present invention may not be exhibited, and considering the amounts of other components constituting the cosmetic, the upper limit of the amount of the coated pigment of the present invention to be blended is 9
It is about 5% by weight.

[0065]

The ultraviolet absorbing resin particles of the present invention are benzotriazole compounds represented by the above formula [I].
-(2'-hydroxy-5'-methacryloxyethylphenyl)-
It is formed of a resin having a repeating unit derived from 2H-benzotriazole. Thus, the resin forming the particles of the present invention has a repeating unit having an ultraviolet absorbing function in its molecular structure. Therefore, even if the particles come into contact with the oily cosmetic base, the ultraviolet absorbent component does not flow out, and the skin irritation is extremely low. Further, the coated pigment having at least a part of the surface coated with these particles,
It has no skin irritation and exhibits a good ultraviolet absorbing action, and the gloss of the pigment can be adjusted by changing the surface coverage of the pigment. Such a coated pigment, for example, by dispersing the ultraviolet absorbing resin particles and the pigment in an aqueous medium, and drying it with a spray dryer, or in the presence of the pigment to be coated in an aqueous medium. It can be easily produced by polymerizing the above monomers. Further, cosmetics containing such a coated pigment have less skin irritation, have a good ultraviolet absorbing action, have good paste of makeup, and have no unnatural luster in makeup.

[0066]

【Example】

[0067]

[Production Example 1] 500 ml of purified water in a round bottom separable flask
Then, 1 g of an emulsifier (Adeka Soap SE-10N, manufactured by Asahi Denka Co., Ltd.) was added thereto and thoroughly mixed and dispersed.

100 g of methyl methacrylate (MMA)
Then, 20 g of 2- (2'-hydroxy-5'-methacryloxyethylphenyl) -2H-benzotriazole and 1 g of azobisisobutyronitrile (AIBN) were added to the purified water in the flask to homogenize. It was emulsified with a mixer.

After the emulsification, the emulsified liquid in the flask was sealed with nitrogen gas for 30 minutes, and then the mixture was stirred at a temperature of 73 ° C. for 5 minutes.
The polymerization reaction was carried out for a time. After 5 hours, the reaction solution was cooled to room temperature.

The average particle size of the obtained particles was 1.0 μm. 1 part by weight of the obtained particles was mixed with a benzotriazole-based compound-insoluble polyacrylate resin-insoluble ester oil, silicone oil, squalane oil 999.
Apply ultrasonic waves to the parts for 3 minutes to disperse,
After allowing to stand for a period of time, the supernatant was separated and the particles contained therein were separated by centrifugation at 2000 rpm for 20 minutes. Measure the absorbance of the obtained oil,
The amount of the UV absorber eluted from the calibration curve prepared in advance using 2- (2'-hydroxy-5'-methacryloxyethylphenyl) -2H-benzotriazole was determined, and the amount of the eluted UV absorber was used. It was expressed as a relative value to the ultraviolet absorber (total inclusion amount).

The results are shown in Table 1.

[0072]

[Production Example 2] In Production Example 1, the emulsifier ADEKA SOAP S
Instead of E-10N, sodium dodecylbenzene sulfonate and polyvinyl alcohol (Poval-420,
1 (manufactured by Kuraray): 1, except using (weight) mixture in a similar manner were prepared Ru average particle diameter 1.5μm der ultraviolet-absorbing resin particles.

Regarding the obtained ultraviolet absorbing resin particles,
The elution amount of the ultraviolet absorber was measured in the same manner as in Production Example 1.

[0074]

Comparative Example 1 Methyl methacrylate (MMA) 100
g, 4-tert-butyl-4′-methoxydibenzoylmethane (ultraviolet absorber) 20 g and azobisisobutyronitrile (AIBN) 1 g, separately, into a round-bottom separable flask with 500 ml of purified water. 1 g of an emulsifier (Adeka soap SE-10N, manufactured by Asahi Denka Co., Ltd.) was added and thoroughly mixed to disperse.

After the emulsification, the emulsified liquid in the flask was sealed with nitrogen gas for 30 minutes, and then the mixture was stirred at a temperature of 73 ° C. for 5 minutes.
The polymerization reaction was carried out for a time. After 5 hours, the reaction solution was cooled to room temperature.

The average particle diameter of the obtained resin particles is 1.0 μm.
Met. UV absorber is soluble in the obtained resin particles,
In addition, 999 parts by weight of ester oil, silicone oil, and squalane oil in which the polyacrylate resin is insoluble are dispersed by applying ultrasonic waves for 3 minutes, and the mixture is allowed to stand at 40 ° C. for 24 hours, and then the supernatant liquid is collected. The particles contained in were separated by centrifugation at 2000 rpm for 20 minutes. The absorbance of the obtained oil was measured, and 4-tert-butyl-4'- was previously prepared.
The amount of the ultraviolet absorber eluted from the calibration curve prepared using methoxydibenzoylmethane was determined, and the amount of the eluted ultraviolet absorber was expressed as a relative value to the used ultraviolet absorber (total inclusion amount).

The results are shown in Table 1.

[0078]

[Table 1]

As is clear from Table 1 above, in the ultraviolet-absorbing resin particles of the present invention, the resin forming the particles themselves has an ultraviolet-absorbing property, so that the elution of the ultraviolet-absorbing agent is extremely small, and therefore, In the cosmetic containing the ultraviolet-absorbing resin particles of the present invention, skin roughness due to elution of the ultraviolet-absorbing agent does not occur. In Table 1 above, Production Example 1 and
The ultraviolet absorber eluted from the particles of Production Example 2 was considered to be unreacted 2- (2'-hydroxy-5'-methacryloxyethylphenyl) -2H-benzotriazole attached to the particles, and was washed. It is possible to prevent almost complete elution with, for example.

[0080]

Example 1 Natural mica 2 was added to 100 parts by weight of an aqueous dispersion in which the ultraviolet absorbing resin particles produced in Production Example 1 were dispersed.
A dispersion was prepared by adding 00 parts by weight and 200 parts by weight of ion-exchanged water and stirring them well.

The dispersion liquid thus prepared was mixed with hot air at a temperature of 1
The pigment was dried using a spray dryer set at 80 ° C. and an exhaust air temperature of 80 ° C. to obtain a coated pigment in which the surface of natural mica was incompletely coated with resin particles.

This coated mica was compounded according to the following Formulation 1 to prepare a powder foundation. Prescription 1 component Content rate (parts by weight) Coated mica ... 30.0 Talc ... 45.0 Titanium dioxide ...・ ・ ・ 8.0 Coloring pigment ・ ・ ・ ・ ・ ・ ・ ・ 2.4 Butyl paraoxybenzoate ・ ・ ・ ・ ・ ・ 0.2 POE Sorbitan monooleate ・ 1.0 Squalane ・ ・ ・・ ・ ・ ・ ・ ・ ・ 1.0 Diisostearyl malate ・ ・ ・ ・ 5.0 Fragrance ・ ・ ・ ・ ・ ・ ・ 0.4 Magnesium stearate ・ ・ ・ ・ 2.0 The powder foundation produced as described above had a more calm luster than the foundation prepared in the same manner using uncoated mica, and the makeup was also good.

[0083]

Example 2 A coated talc was produced in the same manner as in Example 1 . This coated talc and the coated mica obtained in Example 1 were blended according to the following Formulation 2 to produce a powder foundation. The powder foundation produced as described above had a more calm luster than the powder foundation prepared similarly using uncoated talc and mica, and also had good makeup paste.

─────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-6-73368 (JP, A) JP-A-2-91109 (JP, A) JP-A-60-38411 (JP, A) (58) Field (Int.Cl. ⁷ , DB name) A61K ^7/ 00-7/50 C09K 3/00 CA (STN) REGISTRY (STN)

Claims (3)

(57) [Claims] 1. A surface of an extender pigment or a pearl pigment has a repeating unit derived from a reactive benzotriazole compound represented by the following formula [I], a repeating unit derived from a (meth) acrylic compound, and A coated pigment characterized by being coated with 5 to 95% of ultraviolet absorbing resin particles formed of a resin having a repeating unit derived from a styrene compound. [Chemical 1] 2. An extender pigment surface or a pearl pigment surface 40
The coated pigment according to claim 1, wherein ˜95% is coated with the resin particles. 3. The surface of the extender pigment or pearl pigment has a repeating unit derived from a reactive benzotriazole compound represented by the following formula [I], a repeating unit derived from a (meth) acrylic compound, and A cosmetic composition comprising a UV-absorbing resin particle formed of a resin having a repeating unit derived from a styrene compound and / or containing a coating pigment in an amount of 5 to 95% . [Chemical 2]