TWI519318B - A powder dispersant containing a polysilicate phosphoric acid triester, a surface coating powder and a cosmetic - Google Patents

Description

Powder dispersant containing polyphosphonium phosphate triester, surface coated powder and cosmetic

The present invention relates to a powder dispersant containing a novel polyphosphoric acid triester, a surface-coated powder, and a cosmetic. More specifically, it relates to a cosmetic containing polyphosphoric acid triester, a powder coated with a novel polyphosphoric acid triester for surface coating, a cosmetic containing the same, and a powder containing polyphosphoric acid triester A bulk dispersant, a powder dispersion, and a cosmetic containing the same.

Previously, modified organic (poly) alkane was formulated in the cosmetic. For example, there are organic (poly) alkoxynes such as an amine group modification, an epoxy modification, a carboxylic acid modification, and a phosphate modification.

Among these, as for the phosphate-modified organic (poly) alkane, for example, Patent Document 1 describes that at least one ruthenium atom of an organic (poly) alkane is subjected to the following formula.

[Chemical 1]

Wherein R ¹ represents a linear or branched alkyl group having 2 to 20 carbon atoms, and R ² represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by a hydroxyl group, and R ³ and R ⁴ The same or different, respectively, represents a linear or branched alkyl group having 1 to 22 carbon atoms, p represents a number in 0 to 20, and a, b, and c represent the number of bases in parentheses bonded to a phosphorus atom, respectively. a+b+c=3, a is 1 or 2, b and c are 0 or 1; wherein, when p=0, the carbon number of R ² is 9-20] The ester is modified with an organic (poly) alkane.

Further, in Patent Document 2, although it is described as a surface treatment agent for a cosmetic powder, at least one of the phosphate-modified organic (poly) alkane and the organic (poly) alkane is used. Atomic atomic

[Chemical 2]

[R ¹ and R ² represent a C 2-20 alkylene group, R ³ represents a C1-20 alkyl group which may be substituted by -OH, R ⁴ represents a C1-22 alkyl group, and M represents H or a monovalent cation. p and q represent the numbers from 0 to 200, a, b and c represent the number of bases in parentheses bonded to the phosphorus atom, a+b+c=3, a and c are 1 or 2, and b is 0. Or the phosphate-modified phosphate shown in 1] is modified with an organic (poly) alkane.

Further, Patent Document 3 describes that at least one ruthenium atom of an organic (poly) alkane is subjected to the following formula.

[{-CH ₂ CH ₂ -R ² -(OR ¹ ) _p -O} ₃ P=O] _1/3

[wherein, among the trivalent groups in the square brackets, 3p of R ^{1 are the} same or different, and represent a straight or branched alkyl group having 2 to 20 carbon atoms, and 3 R ^{2 are the} same or different, indicating that the hydroxyl group can be Substituting a linear or branched alkyl group having 7 to 20 carbon atoms, 3 p are the same or different, representing a number from 0 to 20; further, all three terminal carbon atoms are bonded to the same or 2 or 3 A modified phosphotriester of the group shown by a ruthenium atom of a different molecular (poly) siloxane molecule is modified with an organic (poly) alkane.

However, in the above-mentioned Patent Documents 1 and 2, it is not described that the triester body obtained by binding three poly(poly)oxyalkylene oxides, which are used in the present invention, to phosphoric acid, is formulated in a cosmetic. In the above Patent Document 3, a triester body in which three organic (poly) alkane are bonded to phosphoric acid is described, but an organic (poly) alkane and a phosphoric acid are via -CH ₂ CH ₂ - R ² -(OR ¹ ) _p - groups are bonded, and the group is a long chain having 9 or more carbon atoms.

Further, in Patent Document 3, a phosphate triester is modified by an organic (poly) alkane by using the following formula

{CH ₂ =CH-R ² -(OR ¹ ) _p -O} ₃ P=O

[wherein 3p of R ^{1 are the} same or different and represent a straight or branched alkyl group having 2 to 20 carbon atoms, and 3 R ^{2 are the} same or different, and represent a straight chain having a carbon number of 7 to 20 which may be substituted by a hydroxyl group. Or a branched alkyl group, three p identical or different, indicating a number from 0 to 20, and a reaction of a phosphotriester having at least one hydrogen atom bonded to a helium atom. However, this method is difficult to synthesize in the case where the CH ₂ CH ₂ -R ² -(OR ¹ ) _p - group is short in the case of the present invention.

Therefore, a phosphoric acid triester having a shorter -CH ₂ CH ₂ -R ² -(OR ¹ ) _p - group is modified with an organic (poly) azide (also known as polyphosphoric acid triester) as a cosmetic Whether the substrate is useful or not is completely unknown.

In addition, powders such as an inorganic powder, an organic powder, and a pigment powder are blended for the purpose of a makeup effect or a touch feeling. These powders contain inorganic compounds and organic compounds, and are hydrophilic and lipophilic, so that they are not only easily soluble in water but also soluble in oil. Therefore, the cosmetic formulated with such a powder is easily wetted by water, secretions such as sweat and sebum, and impairs the original color tone of the cosmetic material, or damages the uniformity of the cosmetic film due to sweating or facial activity, etc. The so-called "dressing off" phenomenon.

Therefore, as a technique for preventing makeup removal caused by sweat or sebum, techniques such as treatment of a powder surface with various surface treatment agents or addition of a dispersant have been studied.

As a technique of adding a dispersing agent, a technique for using a powder dispersing agent for modifying a polyfluorene oxygen as a component for blending a large amount of cosmetics into an oil component has been developed.

For example, (A) a copolymer of a polyorganosiloxane monomer and (B) a monomer having a polylactone-containing group, a hydroxyl group or an anionic group (Patent Document 4), a polyether modified polyfluorene oxide (Patent Document 5), polyglycerol-modified polyfluorene (Patent Document 6), both-end polyfluorinated polyethylene glycol (Patent Document 7), and a branched polymer having a polyoxyalkylene group and a mercaptoalkyl group A siloxane compound (Patent Document 8) or the like.

As a technique for coating the surface of the powder with various surface treatment agents, for example, a decane coupling agent such as dimethoxane, hydromethyl polyoxyalkylene or perfluoroalkyl dimethyl methoxy decane may be mentioned. a polyfluorinated acid, a perfluoroalkyl diethanolamine salt, a fluorine compound such as a perfluoroalkyl phosphate, a fatty acid metal soap such as zinc stearate, or a deuterated amino acid derived from a mercapto glutamic acid The compound, lecithin or a metal salt thereof, a phosphate ester modified organic (poly) alkane or the like (for example, Patent Documents 2, 9 to 17, etc.).

With the development of these, it is possible to improve the quality and the feeling of use. However, since it is not sufficiently satisfactory, a more excellent polyoxynitride powder dispersant or a polyfluorene-based surface coating treatment agent is expected. Development.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. Hei 9-048855

[Patent Document 2] Japanese Patent Laid-Open No. Hei 9-136815

[Patent Document 3] Japanese Patent Laid-Open No. Hei 9-157397

[Patent Document 4] Japanese Patent Laid-Open No. Hei 11-263706

[Patent Document 5] Japanese Patent Laid-Open Publication No. 2001-58926

[Patent Document 6] Japanese Patent Laid-Open Publication No. 2004-169015

[Patent Document 7] Japanese Patent Laid-Open Publication No. 2005-154736

[Patent Document 8] Japanese Patent Laid-Open Publication No. 2007-269689

[Patent Document 9] Japanese Patent Laid-Open No. Hei 5-339518

[Patent Document 10] Japanese Patent Laid-Open Publication No. 2003-55142

[Patent Document 11] Japanese Patent Laid-Open Publication No. 2009-263213

[Patent Document 12] Japanese Patent Laid-Open No. 62-250074

[Patent Document 13] Japanese Patent Laid-Open No. Hei 10-167931

[Patent Document 14] Japanese Patent Laid-Open No. Hei 10-203926

[Patent Document 15] Japanese Patent Laid-Open No. Hei 11-335227

[Patent Document 16] Japanese Re-issued Patent No. 2006-106728

[Patent Document 17] Japanese Patent Laid-Open Publication No. 2008-247834

An object of the present invention is to develop a polyphosphonium oxyphosphate triester having a shorter -CH ₂ CH ₂ -R ² -(OR ¹ ) _p - group than the polyphosphonium phosphate triester described in Patent Document 3, and This is used as a dispersing agent or a surface treating agent for a powder such as a cosmetic or a cosmetic powder.

As a result of intensive studies to solve the above problems, the inventors of the present invention found that the poly-oxo-oxygen of -CH ₂ CH ₂ -R ² -(OR ¹ ) _p - group which is not synthesized in Patent Document 3 is short. The phosphate triester compound is used as a base material for cosmetics, and has excellent repairing effect, smooth feeling of use, or long-lasting effect of makeup. Further, it has been found that if it is used as a surface treatment agent for powder, it can be expressed in a small amount of treatment. It has a high water repellency and dispersibility, and is excellent in powder treatment efficiency. It has also been found to be highly dispersible when used in a dispersion of oil such as a metal oxide, and further formulated with the polyfluorene. In the cosmetic of the oxyphosphoric acid triester compound, the uniformity of the cosmetic film or the long-lasting effect of the makeup is excellent, and the present invention has been completed.

That is, the present invention relates to:

(1) A cosmetic containing formula (I)

[Chemical 3]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents 1 or more of the polyphosphoric acid triesters represented by any one of 5 to 40);

(2) The cosmetic according to the above (1), which contains the formula (I) in an amount of 60 to 100% by mass.

[Chemical 4]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents One or more of the polyphosphoric acid triesters represented by any one of 5 to 40, and 0 to 35 mass% of the formula (II)

[Chemical 5]

(in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass

[Chemical 6]

(in the formula, R ₁ , R and n are the same as defined in the above formula (I)), one or more polyphosphonium phosphates; and

(3) The cosmetic of (1) or (2) above, which further contains an oil agent.

Again, the invention relates to:

(4) A powder obtained by formula (I)

[Chemistry 7]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents One or more of the polyphosphoric acid triesters represented by any one of 5 to 40) are subjected to surface coating treatment;

(5) The powder according to the above (4), which is contained in the formula (I) containing 60% by mass to 100% by mass.

[化8]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents One or more of the polyphosphoric acid triesters represented by any one of 5 to 40, and 0 to 35 mass% of the formula (II)

[Chemistry 9]

(in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass

[化10]

One or two or more kinds of polyphosphonium oxyphosphates of the polyphosphoric acid monoesters represented by the formula (wherein R ₁ , R and n are the same as defined in the above formula (I)) are subjected to surface coating treatment;

(6) The surface-coated powder according to the above (4) or (5), which contains not only the above polyphosphonium phosphate but also an organic titanate as a surface treating agent;

(7) The powder of the above (6), wherein the mass ratio of the polyphosphoryl phosphate and the organic titanate is 1:9 to 9:1;

(8) The powder according to the above (6) or (7), wherein the organic titanate is isopropyl triisostearyl titanate;

(9) The surface-coated powder according to any one of (4) to (8) above, wherein the powder is at least one selected from the group consisting of titanium oxide, zinc oxide, and iron oxide;

(10) The surface-coated powder according to any one of (4) to (9) above, wherein the coating amount of the polyphosphonium phosphate is 0.01 to 5% by mass of the surface-coated powder;

(11) A cosmetic comprising the surface-coated powder according to any one of (4) to (10) above.

Further, the present invention relates to:

(12) A powder dispersant containing formula (I)

[11]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents 1 or more of the polyphosphoric acid triesters represented by any one of 5 to 40);

(13) The powder dispersant according to (12) above, which contains the formula (I) in an amount of 60% by mass to 100% by mass.

[化12]

(wherein R ₁ each independently represents an alkyl group having 1 to 4 carbon atoms, and R represents a divalent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one selected from the group consisting of -O- and -CO-, and n represents One or more of the polyphosphoric acid triesters represented by any one of 5 to 40, and 0 to 35 mass% of the formula (II)

[Chemistry 13]

(in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass

[Chemistry 14]

(in the formula, R ₁ , R and n are the same as defined in the above formula (I)), one or more polyphosphonium phosphates;

(14) A powder dispersion containing the powder dispersant, powder and oil agent as described in (12) or (13) above;

(15) A cosmetic comprising the powder dispersion of the above (14).

The details of the present invention will be described below.

1 polyphosphoric acid triester

The polyphosphoric acid triester used in the present invention is of formula (I)

[化15]

Said.

Wherein, each R ₁ each independently represent an alkyl group having 1 to 4 carbon atoms of, R represents an -O- and -CO- selected in at least one of a carbon number of 2 to 7 of the divalent hydrocarbyl group, n represents 5 Any integer from ~40.

Examples of the "alkyl group having 1 to 4 carbon atoms" in R ₁ include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, an isobutyl group, and a t-butyl group. . As R ₁ , among these, a methyl group is preferable.

As the "two-valent hydrocarbon group having 2 to 7 carbon atoms which may have at least one carbon-number of 2 to 7 selected from -O- and -CO-", the "2-valent hydrocarbon group having 2 to 7 carbon atoms" in R may be exemplified as Base chain, propyl chain, methyl ethyl group, butyl chain, 1,2-dimethylethyl group, pentyl chain, 1-methyl butyl chain, 2-methyl butyl chain, Hexyl chain, heptyl chain, and the like.

The "two-valent hydrocarbon group having 2 to 7 carbon atoms selected from at least one of -O- and -CO-" may have one or two or more -O- or -CO-, and examples thereof include: - CH ₂ -O-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -O-(CH ₂ ) ₂ -, -(CH ₂ ) ₃ -O-(CH ₂ ) ₂ -, -(CH ₂ ) ₄ -O-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -O(CH ₂ ) ₂ -O-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -O-(CH ₂ ) ₄ -, - (CH ₂ ) ₂ -O-(CH ₂ ) ₅ -, -(CH ₂ ) ₃ -O-CH ₂ -, -CH ₂ -CO-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CO- (CH ₂ ) ₂ -, -(CH ₂ ) ₃ -CO-(CH ₂ ) ₂ -, -(CH ₂ ) ₄ -CO-(CH ₂ ) ₂ -, -(CH ₂ ) ₂ -CO-(CH _{2) 4 -, - (CH} 2) 2 -CO- (CH 2) 5 -, - (CH 2) 3 -CO-CH 2 - and the like.

The "two-valent hydrocarbon group having 2 to 7 carbon atoms which may be selected from at least one of -O- and -CO-" is preferably -(CH ₂ ) ₃ O(CH ₂ ) ₂ - .

Specifically, examples of the polyphosphoric acid triester include the following. Where n is any integer from 5 to 40.

[Chemistry 16]

These may be used alone or in combination of two or more.

2 Polymethophosphoric acid triester manufacturing method

The polyphosphoric acid triester of the present invention can be produced, for example, by the method shown by the following reaction formula.

[化17]

(wherein R ₁ , R and n are the same as defined in formula (I))

The single-end methanol modified polyfluorene oxygen represented by the formula (IV) and the phosphonium chloride represented by the formula (V) are reacted in a solvent in the presence of a base.

As a solvent used for carrying out the above reaction, a polar solvent such as tetrahydrofuran, dimethyl hydrazine, N,N-dimethylformamide, acetone, diethyl ether or acetonitrile can be used.

As the base, alkylamines such as diethylamine and triethylamine, heterocyclic amines such as piperazine and imidazole, and quaternary ammonium salts such as benzyltriethylammonium chloride and methyltrioctylammonium chloride can be used. Salts, organic metals such as n-butyl lithium and lithium diisopropylamide.

The reaction temperature is usually about 25 ° C to 50 ° C, and the reaction time varies depending on the length of the polyoxyl chain, but it is usually about 2 hours to 20 hours.

By the above reaction, a polyphosphonium phosphate triester represented by the formula (I) can be obtained, but as a by-product, a polyphosphonium phosphate diester represented by the formula (II) and a polyfluorene represented by the formula (III) are produced. Oxyphosphate monoester or the like. It is also possible to use as a polyphosphonium phosphate mixture in the presence of such by-products, and it is also possible to purify the product by a usual method, thereby substantially using only the polyphosphonium phosphate triester represented by the formula (I).

3 Cosmetics containing polyphosphoric acid triester

The cosmetic of the present invention contains one or more of the polyphosphoric acid triesters represented by the above formula (I) and, if necessary, the formula (II)

[化18]

(in the formula, _one or more of polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and/or formula (III)

[Chemistry 19]

(In the formula, one or more of the polyphosphazene monophosphates represented by R ₁ , R and n are the same as defined in the above formula (I)).

The compounding ratio of the polyphosphonium phosphate triester represented by the formula (I), the polyphosphonium phosphate diester represented by the formula (II) and the polyphosphazyl phosphate monoester represented by the formula (III) is as long as the formula (I) The effect of the polyphosphoric acid triester to exhibit a base material as a cosmetic is not particularly limited, and it is preferably 60 to 100% by mass of the polyphosphoric acid triester represented by the formula (I), and the formula (II) The polyphosphonium phosphate diester shown is 0 to 35% by mass, and the polyphosphonium phosphate monoester represented by the formula (III) is 0 to 5% by mass.

The proportion of the polyphosphoric acid phosphate as a whole in the cosmetic is from 1 to 50% by mass, preferably from 5 to 30% by mass.

In the cosmetic, the ingredients that can be formulated can be appropriately formulated according to the type.

For example, adjustable: oil, surfactant, alcohol, water, moisturizer, gelling agent and tackifier, powder, UV absorber, preservative, antibacterial, antioxidant, skin care ingredients (whitening) Agents, cell activating agents, anti-inflammatory agents, blood circulation promoters, skin astringents, anti-lipids, etc.), vitamins, amino acids, nucleic acids, hormones, and the like.

Among these, it is preferably used together with an oil agent, and it is not particularly limited as long as it is an oil agent which can dissolve the above-mentioned polyphosphonium phosphate. By blending polyphosphoric acid phosphate, it is possible to improve the compatibility of a polar oil such as an ester oil with a nonpolar oil such as a polyoxygenated oil, and to uniformly dissolve the entire oil agent.

The blending amount of the oil agent is not particularly limited, but is preferably 1 to 30% by mass, and more preferably 5 to 20% by mass.

Examples of the oil agent include solid oil, semi-solid oil, and liquid oil, and examples thereof include natural animal and vegetable oils and semi-synthetic oils, hydrocarbon oils, ester oils, glycerin oils, polyoxygenated oils, higher alcohols, and higher fatty acids. , organic solvents, etc.

Examples of the solid oil include natural waxes such as carnauba wax, candid wax, cotton wax, shellac wax, and hardened oil, and mineral waxes such as ground wax, pure ground wax, paraffin wax, and microcrystalline wax, and polyethylene wax. Synthetic waxes such as Fischer-Tropsch wax and ethylene-propylene copolymer, higher alcohols such as behenyl alcohol, cetyl alcohol, stearyl alcohol, cholesterol, and phytosterol, and higher fatty acids such as stearic acid and behenic acid.

In the liquid oil, as natural animal and vegetable oils and semi-synthetic oils, specific examples thereof include avocado oil, linseed oil, almond oil, insect wax, sage oil, olive oil, citron oil, liver oil, apricot kernel oil, and wheat. Germ oil, sesame oil, rice germ oil, rice bran oil, camellia oil, safflower oil, Chinese tung oil, ceylon cinnamon oil, sea turtle oil, soybean oil, tea seed oil, pile oil, evening primrose oil, corn oil, rapeseed oil, Japanese tung oil, wax, germ oil, peach oil, palm oil, palm kernel oil, castor oil, sunflower oil, grape seed oil, jojoba oil, Australian walnut oil, cottonseed oil, coconut oil, three coconut oil fatty acid glycerin Ester, peanut oil, lanolin, liquid lanolin, reduced lanolin, lanolin alcohol, lanolin acetate, lanolin fatty acid isopropyl ester, POE lanolin alcohol ether, POE lanolin alcohol acetate, lanolin fatty acid polyethylene Glycol ester, POE hydrogenated lanolin ether, egg butter, and the like.

Examples of the hydrocarbon oil include squalane, squalene, mobile paraffin, decane, and polyisobutylene.

Examples of the ester oil include diisobutyl adipate, 2-hexyl decyl adipate, di-2-heptyl undecyl adipate, and N-alkyl ethylene diisostearate. Alcohol ester, isocetyl isostearate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, ethylene glycol di-2-ethylhexanoate, di-2 -ethylhexanoic acid neopentyl glycol ester, tris-2-ethylhexanoic acid trimethylolpropane ester, tetrakis-2-ethylhexanoic acid pentaerythritol ester, cetyl octanoate, octyl dodecyl phthalate , oleyl oleate, octyl dodecyl oleate, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, amyl acetate, Ethyl acetate, butyl acetate, isocetyl stearate, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, lactate Alkyl ester, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, cholesterol ester 12-hydroxystearate, dipentaerythritol Fatty acid ester, isopropyl myristate, 2-octyldodecyl myristate, nutmeg 2-hexyl decyl ester, tetradecyl myristate, hexyl decyl dimethyl octoate, ethyl laurate, hexyl laurate, N-laurel-L-glutamic acid-2-octyl ten Dialkyl ester, diisostearyl malate, and the like.

Examples of the glyceride oil include acetamyl glyceride, triisooctanoic acid glyceride, triisostearic acid glyceryl ester, triisopalmitic acid glyceride, tris-2-ethyl glyceride, and glyceryl monostearate. Ester, di-2-heptyl undecanoic acid glyceride, trimyristyl glyceride, and the like.

Examples of the polyoxygenated oil include dimethyl polyoxyalkylene, methylphenyl polyoxyalkylene, methylhydrogenpolyoxyalkylene, octamethylcyclotetraoxane, and decamethylcyclopentanyloxy. Alkane, dodecamethylcyclohexaoxane, tetramethyltetrahydrocyclotetraoxane, alkyl modified polyoxane, and the like.

Examples of the higher alcohol include oleyl alcohol, lauryl alcohol, stearyl alcohol, isostearyl alcohol, and 2-octyldodecanol.

Examples of the higher fatty acid include oleic acid, palmitic acid, myristic acid, stearic acid, and isostearic acid.

Examples of the organic solvent include hydrocarbons such as n-hexane and cyclohexane; aromatic compounds such as benzene, toluene, and xylene; and non-aromatic compounds such as ethyl acetate and butyl acetate; chloroform, dichloromethane, and dichloroethane. Chlorine-based compound such as alkane An ether compound such as an alkane or tetrahydrofuran; 2-propanol, benzyl alcohol, phenoxyethanol, carbitol, celecoxime, polybutene, spindle oil, and the like.

The surfactant is not particularly limited as long as it is generally used for cosmetics, and any of them can be used. Examples of the surfactant include an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant. These may be used alone or in combination of two or more.

Specific examples of the anionic surfactant include a fatty acid soap such as sodium stearate or triethanolamine palmitate, a carboxylate of an alkyl ether carboxylic acid and a salt thereof, a condensation of an amino acid with a fatty acid, and an alkylsulfonic acid. , alkenyl sulfonate, sulfonate of fatty acid ester, sulfonate of fatty acid decylamine, sulfonate of alkyl sulfonate and formaldehyde condensate thereof, alkyl sulfate salt, secondary higher alcohol sulfate , alkyl and allyl ether sulfate salt, fatty acid ester sulfate salt, fatty acid alkyl alcohol decyl amine sulfate salt, polyoxyethylene alkyl sulfate salt, Turkish red oil and other sulfate salts, alkyl Phosphate, ether phosphate, alkyl allyl ether phosphate, guanamine phosphate, N-decylamino acid active agent, and the like.

As a cationic surfactant, a long-chain alkyltrimethylammonium salt, a long-chain alkyldimethylammonium salt, a long-chain alkyldimethylbenzylammonium salt, or a di-oxyethylene alkylammonium salt Examples of the alkyl quaternary ammonium salt or the aromatic quaternary ammonium salt such as a salt, a dioxyethylene alkyl ether dimethyl ammonium salt or a polyoxypropylene methyl diethyl ammonium salt include an alkyl pyridinium salt. An imidazoline salt such as a pyridinium salt or an alkyldihydroxyethyl imidazoline salt or a lower alkyl ester of an N-fluorenyl basic amino acid, and examples thereof include an alkylamine salt, a polyamine, and an amino alcohol fatty acid. An amine salt such as a derivative.

Examples of the nonionic surfactant include sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, propylene glycol fatty acid ester, polyethylene glycol fatty acid ester, sucrose fatty acid ester, and polyoxygen. Vinyl alkyl ether, polyoxypropylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene Glycerol fatty acid ester, polyoxyethylene propylene glycol fatty acid ester, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyoxyethylene hydrogenated castor oil fatty acid ester, polyoxyethylene plant stanol ether, polyoxyethylene planting Alcohol ether, polyoxyethylene dihydrocholesterol ether, polyoxyethylene cholesterol ether, polyoxyalkylene alkyl modified organic polyoxyalkylene, polyoxyalkylene alkyl-alkyl co-modified organic polyoxyalkylene, alkanol Amines, sugar ethers, glycosides, and the like.

Examples of the amphoteric surfactant include a carbonyl betaine type such as alkyldimethylaminoacetate betaine, fatty acid guanamine dimethylaminoacetate betaine, and alkyl dihydroxyethylaminoacetate betaine. Amphoteric surfactant, sulfobetaine type amphoteric surfactant such as alkyl sulfobetaine, N-fatty acid thiol-N-carboxymethyl-N-hydroxyethylethylenediamine salt, N-fatty acid thiol- Amidoxime type (imidazoline type) amphoteric surfactant such as N-carboxymethoxyethyl-N-carboxymethylethylenediamine di-salt, N-[3-alkoxy-2-hydroxypropyl] fine An amino acid type amphoteric surfactant such as an amine salt, an alkyl iminodicarboxylate type amphoteric surfactant or the like.

Specific examples of the alcohol include lower alcohols such as ethanol and isopropyl alcohol, glycerin, diglycerin, polyglycerin, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, and 1,3-butanediol. Polyols such as erythritol, sugar alcohols such as sorbitol, maltose, xylitol, and maltitol.

Examples of the humectant include urea, hyaluronic acid, chondroitin sulfate, and pyrrolidone carboxylate.

As a water-based tackifier and gelling agent, there are: gum arabic, tragacanth, galactan, locust bean gum, guar gum, karaya gum, carrageenan, pectin, agar, alfalfa seeds ( Marmelo, 榅桲), starch (rice, corn, potato, wheat), seaweed gum, tranplast gum, locust bean gum and other plant-based polymers, Sanxian gum, dextran, amber gluten, amylopectin Microbial polymers, animal polymers such as collagen, casein, albumin, gelatin, starch polymers such as carboxymethyl starch and methyl hydroxypropyl starch, methyl cellulose, ethyl cellulose, and hydroxyl groups. Fibers such as propylmethylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, nitrocellulose, sodium cellulose sulfate, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder, etc. Alkyd polymer such as sodium alginate or propylene glycol alginate, vinyl polymer such as polyvinyl methyl ether, carboxyvinyl polymer, alkyl modified carboxyvinyl polymer, or polyoxyethylene polymer Polyoxyethylene polyoxypropylene copolymer Polymer, acrylic acid such as sodium polyacrylate, polyethyl acrylate, polypropylene decylamine, inorganic tackifier such as bentonite, aluminum magnesium silicate, laponite, hectorite, anhydrous citric acid, etc. Ethyleneimine, cationic polymer, and the like. Further, it also includes a film forming agent such as polyvinyl alcohol or polyvinylpyrrolidone.

Examples of the oil gelling agent include metal soaps such as aluminum stearate, magnesium stearate, and zinc myristic acid, and N-lauroside-L-glutamic acid, α,γ-di-n-butylamine, and the like. Amino acid derivatives, fatty acid dextrin esters such as palmitic acid dextrin, stearic acid dextrin, 2-ethylhexanoic acid palmitate, sucrose palmitate, sucrose stearate, etc. a benzylidene derivative of sorbitol such as monobenzylidene sorbitol or dibenzylidene sorbitol, dimethylbenzyldodecyl ammonium microcrystalline kaolinite clay, dimethyldi(octadecyl) Organically modified clay minerals such as ammonium microcrystalline kaolinite clay.

The powder may be any shape (spherical shape, needle shape, plate shape, etc.), particle diameter (smoke shape, fine particles, pigment grade, etc.), particle structure (porous, non-porous, etc.), and any of them may be used. For example, an inorganic powder, an organic powder, a surfactant metal salt powder, a colored pigment, a pearl pigment, a metal powder pigment, a natural pigment, etc. are mentioned.

Specific examples include the following.

Inorganic powder: titanium oxide, zirconium oxide, zinc oxide, antimony oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, synthetic mica, gold Mica, red mica, biotite, lithium mica, citric acid, anhydrous citric acid, aluminum citrate, magnesium citrate, aluminum magnesium citrate, calcium citrate, barium strontium citrate, barium strontium citrate, metal tungstate, hydroxyphosphorus Gray stone, vermiculite, aluminum hydroxide (HIGILITE), bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, aluminum oxide, aluminum hydroxide, boron nitride, and the like.

Organic powder: polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane, benzoguanamine powder, polymethylbenzoguanamine powder, tetrafluoro Ethylene powder, polymethyl methacrylate powder, cellulose, silk powder, nylon powder, 12 nylon, 6 nylon, crosslinked polyoxynized fine powder having a structure of crosslinked dimethyl polyfluorene, cross-linking Type polyfluorene-reticular polyoxyl block copolymer, fine powder of polymethylsesquioxane, styrene-acrylic acid copolymer, divinylbenzene-styrene copolymer, vinyl resin, urea resin, phenol Resin, fluororesin, enamel resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, microcrystalline fiber powder, starch powder, lauric acid lysine, and the like.

Surfactant metal salt powder (metal soap): zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, cetyl zinc phosphate, cetyl wax Calcium phosphate, sodium cetyl zinc phosphate, and the like.

Colored pigments: inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as iron oxide yellow and loess; inorganic black pigments such as iron oxide black and carbon black; Inorganic purple pigments such as manganese violet and cobalt violet; inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide, and cobalt titanate; inorganic blue pigments such as iron blue and ultramarine; and pigmentation of tar pigments. A resin obtained by subjecting a natural pigment to a lake, and a synthetic resin powder obtained by combining the powders.

Pearl pigment: titanium oxide coated mica, titanium oxide coated mica, bismuth oxychloride, titanium oxide coated ruthenium oxychloride, titanium oxide coated talc, alumidine base, titanium oxide coated glass powder, titanium oxide coated colored mica, and the like.

Metal powder pigment: aluminum powder, copper powder, stainless steel powder, and the like.

Tar color: red 3, red 104, red 106, red 201, red 202, red 204, red 205, red 220, red 226, red 227, red 228, red 230 , red 401, red 505, yellow 4, yellow 5, yellow 202, yellow 203, yellow 204, yellow 401, blue 1, blue 2, blue 201, blue 404, green 3, green 201, green 204, green 205, orange 201, orange 203, orange 204, orange 206, orange 207, etc.

Natural pigments: blush acid, lacquer acid, safflower, Brazilian hematoxylin, crocin and the like.

These powders may be used as they are, or may be used in combination with an oil agent, a polyfluorene oxide, a fluorine compound or the like.

The powder may be used singly or in combination of two or more kinds as needed.

Examples of the ultraviolet absorber include a benzoic acid-based ultraviolet absorber such as an aminobenzoic acid, an o-amine benzoic acid-based ultraviolet absorber such as methyl ortho-benzoate, and a salicylic acid-based ultraviolet absorber such as methyl salicylate. , a cinnamic acid-based ultraviolet absorber such as octyl methoxycinnamate, a benzophenone-based ultraviolet absorber such as 2,4-dihydroxybenzophenone, or a urinary acid-based ultraviolet absorber such as urinary acid ethyl ester. .

Examples of the preservative and antibacterial agent include p-hydroxybenzoic acid ester, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, salicylic acid, phenolic acid, sorbic acid, and p-chloro-m-cresol. , hexachlorophenol, chlorodimethylammonium chloride, chlorinated dichlorobenzidine, trichlorocarbon bismuth benzene, photoreceptor, isopropylmethylphenol, and the like.

Examples of the antioxidant include tocopherol, butylhydroxyanisole, and dibutylhydroxytoluene. Examples of the pH adjuster include lactic acid, lactate, citric acid, citrate, glycolic acid, and succinic acid. , tartaric acid, malic acid, potassium carbonate, sodium hydrogencarbonate, ammonium hydrogencarbonate, etc., as a chelating agent, may be mentioned: alanine, sodium edetate, sodium polyphosphate, sodium metaphosphate, phosphate, hydroxyethane diphosphine Examples of the cooling agent include L-menthol, camphor, peppermint oil, peppermint oil, and eucalyptus oil. Examples of the anti-inflammatory agent include allantoin, glycyrrhetinic acid, and licorice. Sub-acid derivatives, tranexamic acid, chamomile blue, and the like.

Examples of the skin-care ingredients include whitening agents such as arbutin, glutathione, and saxifrage extract, cellulite such as royal jelly, photoreceptor, cholesterol derivative, and blood extract of young cow, and skin roughness improving agent. , vanillyl phthalate, benzyl nicotinic acid, β-butoxyethyl nicotinic acid, capsaicin, zingerone, canthax, fish fat, caffeine, citric acid, α-borneol, nicotine Tocopherol, nicotinic acid inositol, cyclomandelate, cinnarizine, torasolid, acetylcholine, verapamil, cepharanthine, gamma - a blood circulation promoter such as oryzanol, a skin astringent such as zinc oxide or citric acid, or an anti-lipid such as sulfur or dimethyl thiazide.

Examples of the vitamins include vitamin A such as vitamin A oil, retinol alcohol, retinyl alcohol, palmitic acid retinol, and vitamin B2 such as riboflavin, butyrate, and flavin adenine. Vitamin B6 such as pyridoxine hydrochloride or pyridoxine dioctanoate, L-ascorbic acid, L-ascorbic acid dipalmitate, L-ascorbic acid-2-sodium sulfate, dl-α-tocopherol-L-ascorbic acid Vitamin C such as dibasic phosphate dipotassium, pantothenic acid such as calcium pantothenate, D-panthenol, panthenol ether, ethyl ethionate ether, vitamin D such as ergot calcification sterol, cholecalciferol, niacin, smoke Nicotinic acid, nicotinic acid and other nicotinic acids, dl-α-tocopherol, acetic acid dl-α-tocopherol, nicotinic acid dl-α-tocopherol, succinic acid dl-α-tocopherol and other vitamins Class E, vitamin P, biotin, etc.

Examples of the amino acid include arginine, aspartic acid, cystine, cysteine, methionine, serine, leucine, isoleucine, tryptophan, propylamine. Examples of the nucleic acid include a deoxyribonucleic acid or the like, and examples of the hormone include estradiol and ethinyl estradiol.

When the polyphosphonium phosphate triester of the present invention is used alone or a mixture of polyphosphonium phosphate containing the same is used as a cosmetic, it may be prepared by a conventional method using other components as needed, for example, in the form of a liquid or an emulsion. Various forms such as a cream, a cream, a solid, a gel, and a paste are used. Further, the cosmetic of the present invention is an oil-based, water-in-oil emulsion or oil-in-water emulsion, and the dosage form thereof is not particularly limited, and specific examples thereof include an emulsion, a cream, a cosmetic liquid, a cosmetic oil, a lipstick, and a care product. Hand cream, facial cleanser and other skin care products, foundation, makeup cream, blush, eye shadow, mascara, eyeliner, eyebrow pencil, overcoat agent, lipstick, lip gloss and other cosmetics, hair care, hair, It is applied in the form of various cosmetic materials such as shampoo, conditioner, conditioner, hair conditioner, and the like for scalp or hair.

4 Powder coated with polyphosphoric acid triester for surface coating

The surface treatment agent used for the surface-coated powder of the present invention contains one or more of the polyphosphoric acid triesters represented by the above formula (I) and, if necessary, the formula (II)

[Chemistry 20]

(in the formula, _one or more of polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and/or formula (III)

[Chem. 21]

One or two or more kinds of polyphosphonium phosphates of the polyphosphoric acid monoesters represented by the formula (wherein R ₁ , R and n are the same as defined in the above formula (I)).

The ratio of the polyphosphonium phosphate triester represented by the formula (I), the polyphosphonium phosphate diester represented by the formula (II) and the polyphosphazene phosphate monoester represented by the formula (III) is as long as the formula (I) The polyphosphoric acid triester which exhibits the effect of the surface treatment agent of the powder is not particularly limited, and is preferably a polyphosphonium phosphate triester represented by the formula (I) in an amount of from 60 to 100% by mass. The polyphosphonium phosphate diester shown is 0 to 35% by mass, and the polyphosphonium phosphate monoester represented by the formula (III) is 0 to 5% by mass.

a powder which is subjected to surface coating treatment by using the polyphosphonium phosphate triester represented by the above formula (I) or a polyphosphonium phosphate mixture containing the polyphosphonium phosphate triester represented by the formula (I). The shape (spherical shape, needle shape, plate shape, etc.) or particle diameter (smoke, fine particles, pigment grade, etc.), particle structure (porous, non-porous, etc.) is not limited, and any of them may be used. For example, an inorganic powder, an organic powder, a surfactant metal salt powder, a colored pigment, a pearl pigment, a metal powder pigment, a natural pigment, etc. are mentioned.

Specific examples include the following.

Inorganic powder: titanium oxide, zirconium oxide, zinc oxide, antimony oxide, magnesium oxide, barium sulfate, calcium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, talc, mica, kaolin, sericite, muscovite, synthetic mica, gold Mica, red mica, biotite, lithium mica, citric acid, anhydrous citric acid, aluminum citrate, magnesium citrate, aluminum magnesium citrate, calcium citrate, barium strontium citrate, barium strontium citrate, metal tungstate, hydroxyphosphorus Gray stone, vermiculite, aluminum hydroxide, bentonite, montmorillonite, hectorite, zeolite, ceramic powder, dicalcium phosphate, aluminum oxide, aluminum hydroxide, boron nitride, and the like.

Organic powder: polyamide powder, polyester powder, polyethylene powder, polypropylene powder, polystyrene powder, polyurethane, benzoguanamine powder, polymethylbenzoguanamine powder, tetrafluoro Ethylene powder, polymethyl methacrylate powder, cellulose, silk powder, nylon powder, 12 nylon, 6 nylon, crosslinked polyoxynized fine powder having a structure of crosslinked dimethyl polyfluorene, cross-linking Type polyfluorene-reticular polyoxyl block copolymer, fine powder of polymethylsesquioxane, styrene-acrylic acid copolymer, divinylbenzene-styrene copolymer, vinyl resin, urea resin, phenol Resin, fluororesin, enamel resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, microcrystalline fiber powder, starch powder, lauric acid lysine, and the like.

Surfactant metal salt powder (metal soap): zinc stearate, aluminum stearate, calcium stearate, magnesium stearate, zinc myristate, magnesium myristate, cetyl zinc phosphate, cetyl wax Calcium phosphate, sodium cetyl zinc phosphate, and the like.

Colored pigments: inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; inorganic brown pigments such as γ-iron oxide, inorganic yellow pigments such as iron oxide yellow and loess; inorganic black pigments such as iron oxide black and carbon black; Inorganic purple pigments such as manganese violet and cobalt violet; inorganic green pigments such as chromium hydroxide, chromium oxide, cobalt oxide, and cobalt titanate; inorganic blue pigments such as iron blue and ultramarine; and pigmentation of tar pigments. A resin obtained by subjecting a natural pigment to a lake, and a synthetic resin powder obtained by combining the powders.

Pearl pigment: titanium oxide coated mica, titanium oxide coated mica, bismuth oxychloride, titanium oxide coated ruthenium oxychloride, titanium oxide coated talc, alumidine base, titanium oxide coated glass powder, titanium oxide coated colored mica, and the like.

Metal powder pigment: aluminum powder, copper powder, stainless steel powder, and the like.

Tar color: red 3, red 104, red 106, red 201, red 202, red 204, red 205, red 220, red 226, red 227, red 228, red 230 , red 401, red 505, yellow 4, yellow 5, yellow 202, yellow 203, yellow 204, yellow 401, blue 1, blue 2, blue 201, blue 404, green 3, green 201, green 204, green 205, orange 201, orange 203, orange 204, orange 206, orange 207, etc.

Natural pigments: blush acid, lacquer acid, safflower, Brazilian hematoxylin, crocin and the like.

These powders may be used as they are, or may be used in combination with an oil agent, a polyfluorene oxide, a fluorine compound or the like.

The above powder may be appropriately selected depending on the purpose or use, and among them, a metal oxide such as titanium oxide, zinc oxide or iron oxide is preferred.

In the present invention, the method of treating the powder by surface-coating the polyphosphonium phosphate containing the polyphosphoric acid triester represented by the above formula (I) is not particularly limited, and generally known ones can be used. Approach. Specific examples thereof include a method of directly mixing with a powder (dry treatment method), a method using a solvent such as ethanol, isopropanol, n-hexane, benzene or toluene (wet method), a gas phase method, a mechanochemical method, or the like.

For example, a mixture of a solvent such as hexane and a polyphosphonium phosphate containing the polyphosphoric acid triester represented by the above formula (I) may be added to a mixer such as a Henschel mixer to dissolve the powder. Make it evenly dispersed. Then, the solution is heated to about 100 ° C while stirring, and the solvent is distilled off under reduced pressure, and the mixture is cooled to room temperature, and then pulverized by a pulverizer such as a pulverizer to obtain a powder covering the surface. Thereafter, the calcination treatment can also be carried out at a temperature of 125 ° C or higher.

Further, in the present invention, the powder may be coated with a polyphosphonium phosphate containing a polyphosphoric acid triester represented by the above formula (I), and a polyoxonium compound, a fluorine compound, an oil agent, a fat or oil, The treatment of a commonly known surface treatment agent such as a higher alcohol, wax, polymer, or resin.

One or two or more of these other surface treatment agents may be selected, and in particular, when the organic titanate surface treatment agent is simultaneously treated, the dispersibility of the surface coating powder to the oil agent is improved, which is preferable.

Examples of the organic titanate include alkyl titanates such as a long-chain carboxylic acid type, a pyrophosphoric acid type, a phosphorous acid type, and an amino acid type having an alkoxy group. The alkoxy group of the organic titanate preferably has an alkyl group having 1 to 4 carbon atoms from the viewpoint of reactivity with the powder, and these may be linear or branched, and examples thereof include, for example, Methoxy, ethoxy, propoxy, butoxy, and the like.

In the organic titanate, when a long-chain carboxylic acid type alkyl titanate having an alkyl group having 8 to 22 carbon atoms is selected, it is preferable from the viewpoint of dispersibility, and the following formula (VI) can be exemplified. )

(R ₂ O)-Ti-(OCOR ₃ ) ₃ (VI)

(wherein R ₂ represents an alkyl group having 1 to 4 carbon atoms, and R ₃ represents an alkyl group having 8 to 22 carbon atoms, and the alkyl group may be a straight chain or a branched).

Specific examples thereof include isopropyl triisostearyl titanate, isopropyl triisotetradecyl titanate, isopropyl trioctyl decyl titanate, and methyl triisostearate titanium. Ethyl ester, methyl triisotetradecyl titanate, ethyl triisostearyl phthalocyanate, ethyl triisotetradecyl titanate, etc., one or more of these may be used. . Among these, when isopropyl triisostearyl titanate is selected, the dispersibility of the surface-coated powder in the oil agent is good, and therefore it is particularly preferable.

Further, when a plurality of types of surface treatment agents are simultaneously subjected to coating treatment, if a solvent capable of uniformly dissolving a plurality of kinds of surface treatment agents is selected and dried by a wet method, the surface of the powder can be uniformly coated. It is better to handle.

The surface of the surface-treated powder system powder of the present invention is coated with a polyphosphonium phosphate containing a polyphosphonium phosphate triester represented by the above formula (I), and the amount thereof is not particularly limited, and is preferably a powder. 0.01 to 5 mass%. When it is in this range, the surface coating powder which is excellent in water resistance and the adhesion to the skin can be obtained.

In the case where the coating treatment is carried out simultaneously with a plurality of surface treatment agents such as organic titanate, the total amount of the surface treatment agent is preferably from 0.01 to 10% by mass. In this case, the mass of the polyphosphonium phosphate containing the polyphosphonium phosphate triester represented by the above formula (I) and the other surface treatment agent are preferably in the range of 1:9 to 9:1, and further, 1: In the range of 3 to 3:1, a surface-coated powder which is particularly excellent in dispersibility of an oil agent can be obtained.

In the case where the surface-coated powder of the present invention is used as a cosmetic, it is produced by combining one or two or more kinds of the above-mentioned surface-coated powders with a known cosmetic component in accordance with a conventional method. The blending amount of the surface-coated powder in the cosmetic of the present invention is not particularly limited, and varies from 1 to 90% by mass, preferably from 5 to 40%, depending on the dosage form or the object of the cosmetic. %.

In the cosmetic, the ingredients that can be formulated can be appropriately formulated according to the type.

For example, it can be adjusted: oil agent, surfactant, alcohol, water, humectant, gelling agent and tackifier, powders other than the above surface coating treatment, ultraviolet absorber, preservative, antibacterial agent, anti-drug Oxidizing agents, skin-care ingredients (whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, anti-lipids, etc.), vitamins, amino acids, nucleic acids, hormones, and the like. Specifically, the same as those listed in the item "3 Cosmetics containing polyphosphoric acid triester" can be cited.

In the case where the surface-coated powder of the present invention is used as a cosmetic, it can be carried out in various forms and objects in the same manner as described in the section "3 Cosmetics containing polyphosphoric acid triester".

5 Powder dispersant containing polyphosphoric acid triester

The powder dispersing agent of the present invention contains one or more of the polyphosphoric acid triesters represented by the above formula (I) and, if necessary, the formula (II)

[化22]

(in the formula, _one or more of polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and/or formula (III)

[化23]

(In the formula, one or more of the polyphosphazene monophosphates represented by R ₁ , R and n are the same as defined in the above formula (I)).

The compounding ratio of the polyphosphonium phosphate triester represented by the formula (I), the polyphosphonium phosphate diester represented by the formula (II) and the polyphosphazyl phosphate monoester represented by the formula (III) is as long as the formula (I) The polyphosphoric acid triester is not particularly limited as long as it exhibits an effect as a dispersing agent for the cosmetic, and it is preferably 60 to 100% by mass of the polyphosphoric acid triester represented by the formula (I), and the formula (II) The polyphosphonium phosphate diester shown is 0 to 35% by mass, and the polyphosphonium phosphate monoester represented by the formula (III) is 0 to 5% by mass.

The powder dispersion containing the above powder dispersant is an oil dispersion composition containing the following components.

(A) a powder dispersant containing the polyphosphonium phosphate triester represented by the above formula (I) (B) powder and (C) oil agent

The amount of the polyphosphonium phosphate containing polyphosphonium phosphate in the powder dispersion of the present invention is not particularly limited, and in the case where other powder dispersant is not contained, it is preferably in terms of mass ratio. The powder 1 is 0.1 to 0.5.

Further, in the powder dispersion of the present invention, it is preferable to further contain a powder dispersing agent other than the powder dispersing agent of the present invention, and it is also different depending on the oil agent to be a dispersing medium (except for the present invention) The powder dispersing agent can be exemplified by polyoxyalkylene modified polyfluorene oxide, amine modified polyoxynium oxide, alkyl modified polyfluorene oxide, polyglycerol modified polyfluorene, and the like. Polyxyloxy resin such as trimethylsulfonyloxynonanoic acid, acrylic acid-polyfluorene graft polymer, polyhydroxystearic acid, lecithin, polyoxyethylene alkyl ether, sorbitan fatty acid ester, poly Nonionic surfactants such as oxyethylene alkyl phosphates and fatty acid polyglycerides.

The powder used in the powder dispersion of the present invention has a shape (spherical shape, needle shape, plate shape, etc.) or particle diameter (smoke, fine particles, pigment grade, etc.), particle structure (porous, nonporous) Etc.) Any one can be used. For example, an inorganic powder, an organic powder, a surfactant metal salt powder, a colored pigment, a pearl pigment, a metal powder pigment, a natural pigment, etc. are mentioned.

Specific examples thereof are the same as those of the surface-coated powder. The powder may be appropriately selected depending on the purpose or use, and among them, a metal oxide such as titanium oxide, zinc oxide or iron oxide is preferred.

Further, the amount of the powder in the powder dispersion of the present invention is not particularly limited, but is preferably from 1 to 50% by mass, and more preferably from 5 to 40% by mass.

The oil agent used as the powder dispersion of the present invention can be used as long as it is a liquid oil at room temperature.

Specific examples include the following.

Polyoxygenated oil: dimethyl polyoxyalkylene, methylphenyl polyoxyalkylene, methyl hydrogen polyoxyalkylene, methyl polytrimethyloxane, dimethyloxane-methylbenzene Low viscosity to high viscosity organic polyoxane such as oxyalkylene copolymer; octamethylcyclotetraoxane, decamethylcyclopentaoxane, dodecamethylcyclohexaoxane, tetramethyltetra Hydrocyclotetraoxane, tetramethyltetraphenylcyclotetraoxane, tetramethyltetrakis(trifluoropropyl)cyclotetraoxane, pentamethylpenta(trifluoropropyl)cyclopentaoxane Such as a cyclic oxane or the like.

Fluorine-based oil agent: perfluoropolyether, perfluorodecalin, perfluorooctane, and the like.

Hydrocarbon oil: linear, branched, and further volatile hydrocarbon oil. Specific examples thereof include α-olefin oligomers, light isoparaffin waxes, light mobile isoparaffins, squalane, synthetic squalane, phytosqualane, squalene, mobile paraffin, and mobile isoparaffin , polybutene, isododecane, and the like.

Ester oil: diisobutyl adipate, 2-hexyl decyl adipate, di-2-heptyl undecyl adipate, N-alkyl glycol monoisostearate, different Isocetyl stearate, trimethylolpropane triisostearate, isodecyl isononanoate, isotridecyl isononanoate, ethylene glycol di-2-ethylhexanoate, Cetyl 2-ethylhexanoate, trimethylolpropane tri-2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, cetyl octanoate, oleyl oleate, octyl oleate Dodecyl ester, decyl oleate, neopentyl glycol dicaprate, triethyl citrate, 2-ethylhexyl succinate, amyl acetate, ethyl acetate, butyl acetate, stearic acid Acid isocetyl ester, butyl stearate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, tetradecyl lactate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, isopropyl myristate, octyldodecyl myristate, myristic acid 2 -hexyl decyl ester, tetradecyl myristate, hexyl decyl dimethyl octoate, ethyl laurate , hexyl laurate, N-laurel-L-glutamic acid-2-octyldodecyl ester, diisostearyl malate, and the like.

Glyceryl ester oil: glyceryl acetate, triisooctanoic acid glyceride, glyceryl triisostearate, glyceryl triisopalmitate, glyceryl monostearate, glyceryl di-2-heptyl undecanoate, three flesh Glyceric acid glyceride, myristyl isostearic acid diglyceride, and the like.

Higher fatty acids: undecylenic acid, oleic acid, linoleic acid, linoleic acid, arachidonic acid, eicosapentaenoic acid, docosahexenoic acid (DHA, Docosahexaenoic) Acid), isostearic acid, lactic acid, and the like.

Higher alcohols: oleyl alcohol, isostearyl alcohol, hexyl decyl alcohol, octyldodecanol, 2-decyltetradecyl alcohol, monooleyl glyceryl ether (squalyl alcohol), and the like.

Natural animal and vegetable oils and semi-synthetic oils: avocado oil, almond oil, olive oil, liver oil, apricot kernel oil, wheat germ oil, sesame oil, rice germ oil, rice bran oil, camellia oil, safflower oil, Chinese tung oil, sea turtle Oil, soybean oil, tea seed oil, pile oil, evening primrose oil, corn oil, rapeseed oil, Japanese tung oil, germ oil, peach kernel oil, castor oil, castor oil fatty acid methyl ester, sunflower oil, grape seed oil, lotus Bay oil, Australian walnut oil, oyster sauce, meadowfoam, cottonseed oil, tri-coconut fatty acid glyceride, peanut oil, liquid lanolin, lanolin acetate, lanolin fatty acid polyethylene glycol ester, egg yolk Oil, etc.

Organic solvent: hydrocarbon such as n-hexane or cyclohexane; aromatic compound such as benzene, toluene or xylene; non-aromatic compound such as ethyl acetate or butyl acetate; chlorine system such as chloroform, dichloromethane or dichloroethane. Compound, two An ether compound such as an alkane or tetrahydrofuran, 2-propanol, benzyl alcohol, phenoxyethanol, carbitol, celecoxime, spindle oil or the like.

The blending amount of the oil agent in the powder dispersion of the present invention is not particularly limited, but is preferably 1 to 50% by mass, and more preferably 5 to 40% by mass.

Further, the powder dispersion of the present invention can be produced by a known method. For example, it is possible to dissolve or disperse the powder dispersant in the above-mentioned oil agent, add a powder thereto, and mix it by a dispersion machine such as a ball mill, a bead mill, a sand mill, or a paint shaker, etc., and it is easy to obtain. Further, the obtained powder dispersion can be directly formulated into a cosmetic or the like.

The powder dispersion of the present invention can be used for various purposes, and can be formulated into skin care products, color cosmetics products, hair products, antiperspirant products, ultraviolet protection products, and the like, and all the cosmetics which are especially applied to the skin or hair. In addition to cosmetics, it can also be applied to inks, paints, pigments for plastics, and the like.

Depending on the type of the cosmetic material and the dosage form, the powder dispersion may be adjusted to 0.1 to 99% by mass, more preferably 2 to 80% by mass, based on the total amount of the cosmetic material. If it is less than 0.1% by mass, there is a case where the effect of blending into the cosmetic is not sufficiently exhibited. In addition, one or two or more types of these powder dispersions can be appropriately selected depending on the purpose or use.

In the cosmetic, the ingredients that can be formulated can be appropriately formulated according to the type.

For example, it can be adjusted: oil agent, surfactant, alcohol, water, humectant, gelling agent and tackifier, powders other than the above surface coating treatment, ultraviolet absorber, preservative, antibacterial agent, anti-drug Oxidizing agents, skin-care ingredients (whitening agents, cell activators, anti-inflammatory agents, blood circulation promoters, skin astringents, anti-lipids, etc.), vitamins, amino acids, nucleic acids, hormones, and the like. Specific examples thereof are the same as those mentioned in the section "3 Cosmetics containing polyphosphoric acid triester".

In the case where the powder dispersion of the present invention is used as a cosmetic, it can be carried out in various forms and objects in the same manner as those described in the section "3 Cosmetics containing polyphosphoric acid triester".

[Examples]

The examples are shown below, but the invention is not limited to the examples. Further, in the following examples, % means mass%.

1 Production example of polyphosphoric acid triester [Manufacturing Example 1]

Methanol-modified polyfluorene (Formula 2) 265 g and tetrahydrofuran 136 g were mixed and cooled to -40 °C. After 200 ml of lithium diisopropylamide (LDA, Lithium diisopropylamide) (1 mol/THF (Tetrahydrofuran) solution) was added dropwise and reacted for 90 minutes, 7.8 g of phosphonium chloride (formula 1) was added and reacted for 1 hour. After the temperature was raised to 25 ° C and further matured for 2 hours, 42 g of concentrated hydrochloric acid was added to complete the reaction. The solvent was washed with methanol and the solvent was distilled off, whereby a mixture containing polyphosphoric acid triester was obtained. The composition ratio of the obtained mixture was measured by 31 P-NMR (Nuclear magnetic resonance), the formula (I) as a triester body was 92%, and the formula (II) as a diester body was 1%, including other The by-product of polyphosphoric acid was 7%.

[Chem. 24]

[Manufacturing Example 2]

Methanol-modified polyoxynium (Formula 3) 302 g and tetrahydrofuran 150 g were mixed and cooled to -40 °C. After 74 ml of n-butyllithium (1.6 mol/hexane solution) was added dropwise and reacted for 90 minutes, 5.4 g of phosphonium chloride (formula 1) was added and reacted for 1 hour. After the temperature was raised to 25 ° C and further matured for 2 hours, 10 g of water was added to complete the reaction. The solvent was washed with methanol and the solvent was distilled off, whereby a mixture containing polyphosphoric acid triester was obtained. The composition ratio of the obtained mixture was measured by 31 P-NMR, and the formula (I) as a triester was 83%, and the formula (II) as a diester was 17%.

[化25]

[Manufacturing Example 3]

Methanol-modified polyoxo (Formula 2) 291 g, tetrahydrofuran 87 g, and triethylamine 19 g were mixed and cooled to -40 °C. A mixed solution of phosphorus chlorochloride (formula 1) 8.6 g and tetrahydrofuran 18 g was added dropwise over about 30 minutes. After aging at -40 ° C for 5 hours and aging at 25 ° C for 12 hours, it was washed with methanol and the solvent was distilled off, whereby a mixture containing polyphosphoric acid triester was obtained. The composition ratio of the obtained mixture was measured by 31 P-NMR, and the formula (I) as a triester was 64%, the formula (II) as a diester was 18%, and the by-product containing other polyphosphoric acid was 18%.

[Chem. 26]

[Manufacturing Example 4]

6.1 g of phosphonium chloride (formula 1) was dissolved in 93 g of tetrahydrofuran at 25 °C. A mixed solution of methanol-modified polyoxo (formula 4) 300 g and triethylamine 8.1 g was added dropwise to the solution over a period of about 2 hours. After aging for 15 hours, 0.7 g of water and 4.1 g of triethylamine were added and the reaction was terminated. After washing with methanol, the solvent was distilled off, whereby a mixture containing polyphosphoric acid triester was obtained. The composition ratio of the obtained mixture was measured by 31 P-NMR, and the formula (I) as a triester was 11%, the formula (II) as a diester was 66%, and the formula (III) as a monoester was 3 %, containing by-products of other polyphosphoric acid is 20%.

[化27]

2 Formulations of cosmetics containing polyphosphonium phosphate

The mixture containing the polyphosphoric acid triester manufactured in the above Production Example was used in the following formulation. Therefore, in the following examples, for example, the "product of Production Example 1" means the production of the mixture containing the polyphosphoric acid triester obtained in Example 1.

[Examples 1 to 4, Comparative Examples 1 to 5] Hair Oil

The hair oil of the formulation shown in Table 1 was prepared by the following method, and the moist feeling of the hair, the degree of non-stickiness, and the smoothness of the hair were evaluated by the following methods. The results are shown in Table 1.

[Table 1]

(Production method) A. Mix the ingredients 1~10 evenly. B. Fill A in the container. (evaluation method) sensory evaluation of hair bundle

The hair bundles of Japanese women with damaged hair were immersed in each hair oil and dried for 24 hours, and the hair bundles were evaluated. 20 people in the cosmetics evaluation expert group evaluated the "wet feeling of hair", "degree of non-stickiness", and "smoothness of hair" in seven stages according to the following evaluation criteria, and then used the average score of the entire group. The determination is made based on the following criteria.

[evaluation benchmark]

[Judgement criteria]

(result)

According to the above-described evaluation results of the hair bundle, the hair oils of Examples 1 to 4 were hair conditioners having a moist feeling of hair, a degree of non-stickiness, and excellent smoothness of hair. The hair oil of Comparative Examples 1 to 3 was formulated with a dimethylpolyoxane having a short polyether chain length, so that the moist feeling of the hair or the smoothness of the hair was poor, and the hair oil of Comparative Examples 4 and 5 was compared. Since the dimethylpolysiloxane having a long polyether chain length is blended, although the moist feeling of the hair is excellent, there is a sticky feeling, and the smoothness of the hair is poor.

[Examples 5 to 8, Comparative Examples 6 to 9] O/W (oil-in-water) type hair conditioner

[Table 2]

(Production method) A. The components 1 to 12 were uniformly dissolved at 80 °C. B. The components 13-15 were uniformly dissolved at 80 °C. C. A was added to B and emulsified at 80 °C. D. Cool C and add ingredient 16. E. Defoam D and fill into the container. (evaluation method)

20 people in the cosmetics evaluation expert group used the hair conditioners of Examples 5 to 8 and Comparative Examples 6 to 9 to test the "wet feeling of hair", "degree of no stickiness", and "hair" according to the above evaluation criteria. Each item of the "smoothness" was evaluated in seven stages, and the average score of the entire group was used, and the judgment was made based on the above criteria.

(result)

The conditioners of Examples 5 to 8 are hair conditioners which have a moist feeling of hair, a degree of no stickiness, and an excellent smoothness of hair. The conditioners of Comparative Examples 6 and 8 were formulated with a dimethylpolyoxane having a short polyether chain length, so that in Comparative Example 6 in which the amount of the mixture was small, the moist feeling of the hair or the smoothness of the hair was poor. Moreover, even if the hair conditioner of Comparative Example 8 having a large amount of blending is used, the hair has no moist feeling, a sticky feeling, and a poor smoothness of the hair. Further, since the hair conditioners of Comparative Examples 7 and 9 were prepared with a dimethylpolysiloxane having a long polyoxynoxy chain length, the hair was excellent in moist feeling, but it was sticky and the hair was less smooth.

[Example 9] Emulsified lotion

(Note 8) Phytocompo-PP (manufactured by Nippon Seiki Co., Ltd.)

(Production method)

(1) The components 1 to 6 were heated to 75 ° C and uniformly mixed and dissolved.

(2) The components 7, 8 were heated to 75 ° C and uniformly mixed and dissolved.

(3) Add (2) to (1) to emulsify it.

(4) Cooling (3) and adding component 9 to obtain an emulsified lotion.

(result)

The emulsified lotion of Example 9 is an emulsified lotion which is excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 10] Emulsion

(Production method)

(1) Components 1 to 7 were uniformly mixed at 80 °C.

(2) The components 8 to 14 were uniformly mixed at 80 °C.

(3) Add (2) to (1) and emulsify it.

(4) The emulsion is obtained while being cooled while stirring (3).

(result)

The emulsion of Example 10 was an emulsion excellent in "wet feeling", "degree of non-stickiness", and "smoothness".

[Example 11] O/W type cream

(Production method)

(1) Components 1 to 6 were uniformly mixed at 80 °C.

(2) The components 7 to 12 were uniformly mixed at 80 °C.

(3) Add (2) to (1) and emulsify it.

(4) The mixture is cooled while being stirred (3) to obtain a cream.

(result)

The O/W type cream of the eleventh embodiment is an O/W type cream which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 12] W/O (water-in-oil) type cream

(Production method)

(1) The components 1 to 7 were heated to 75 ° C and uniformly mixed and dissolved.

(2) The components 8, 11 were heated to 75 ° C and uniformly mixed and dissolved.

(3) Add (2) to (1) and emulsify it.

(4) Cooling (3) and adding ingredients 9, 10 to obtain a W/O type cream.

(result)

The W/O type cream of Example 12 is a W/O type cream which is excellent in "wet feeling", "degree of non-stickiness", and "smoothness".

[Example 13] Cleansing Oil

(Production method)

(1) The components 1 to 7 are uniformly mixed at room temperature to obtain a cleansing oil.

(result)

The cleansing oil of Example 13 is a cleansing oil which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 14] Cleaning cream

(Production method)

(1) Components 1 to 7 were uniformly mixed at 80 °C.

(2) The components 8 to 13 were uniformly mixed at 80 °C.

(3) Add (1) to (2) and emulsify it.

(4) Agitating (3) while cooling to obtain a cleaning cream.

(result)

The cleaning cream of Example 14 is a cleaning cream excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 15] Styling water

(Note 9) BY11-007 (manufactured by Toray Dow Corning Co., Ltd.)

(Production method)

(1) The components 1 to 9 are uniformly mixed at room temperature to obtain shaped water.

(result)

The setting water of Example 15 is a molding water excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 16] Wax

(Production method)

(1) The components 1 to 3 were uniformly mixed at 80 °C.

(2) The components 4 to 8 were uniformly mixed at 80 °C.

(3) Add (2) to (1) and emulsify it.

(4) After adding the components 9 to 15 in (3), the mixture is cooled while stirring to obtain a wax.

(result)

The hair wax of Example 16 was a wax having excellent "wet feeling", "no stickiness", and "smoothness".

[Example 17] O/W type mascara

(Note 10) YODOSOL 32A707 (45% solid content) (manufactured by NSC Japan)

(Production method)

(1) The components 1 to 3 were uniformly mixed at 80 °C.

(2) The components 4 to 8 are treated by a roller.

(3) The components 9 to 14 were uniformly mixed at 80 °C.

(4) After mixing (1) and (2), (3) is added and emulsified.

(5) Cooling (4) to obtain O/W type mascara.

(result)

The O/W type mascara of Example 17 is an O/W type mascara which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 18] Cream lip gloss

(Note 11) ANTARON V-220 (manufactured by ISP)

(Note 12) AEROSIL 200 (made by Japan Aerotech Co., Ltd.)

(Production method)

(1) The components 1 to 9 were dissolved and mixed at 100 °C.

(2) Adding components 10 to 18 to (1) and uniformly mixing and dispersing them.

(3) Inject (2) into the tube and cool to obtain a creamy lip gloss.

(result)

The creamy lip gloss of Example 18 is a creamy lip gloss which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 19] Lipstick

(Production method)

(1) Components 1 to 7 were uniformly dissolved and mixed at 100 °C.

(2) Add components 8 to 13 in (1) and mix them uniformly.

(3) Inject (2) into the container and cool to obtain a lipstick.

(result)

The lipstick of Example 19 was a lipstick which was excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 20] Oily eye shadow

(Note 13) Rheoreal TT (manufactured by Chiba Powder Co., Ltd.)

(Note 14) 5% treatment with dimethyl polyoxane

(Production method)

(1) The components 1 to 9 were dissolved and mixed at 100 °C.

(2) Adding components 10 to 18 to (1) and uniformly mixing and dispersing them.

(3) (2) is injected into a container to be cooled and solidified to obtain an oily eye shadow.

(result)

The oily eyeshadow of Example 20 is an oily eye shadow which is excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 21] Solid powdery foundation

(Production method)

(1) Components 1 to 9 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 10 to 13 are uniformly mixed and dissolved.

(3) Add (2) and 14 while stirring with a Henschel mixer (1) and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) (4) was filled in a metal container and compression-molded to obtain a solid powdery foundation.

(result)

The solid powdery foundation of Example 21 was a solid powdery foundation excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 22] solid powder eye shadow

(Production method)

(1) Components 1 to 9 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 10 to 13 are uniformly mixed and dissolved.

(3) Add (2) and 14 while stirring with a Henschel mixer (1) and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) (4) was filled in a metal container and compression-molded to obtain a solid powdery eye shadow.

(result)

The solid powdery eye shadow of Example 22 was a solid powdery eye shadow which was excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 23] solid powdery blush

(Production method)

(1) Components 1 to 7 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 8 to 11 were heated to 65 ° C and uniformly mixed and dissolved.

(3) Add (2) and 12 while stirring (1) with a Henschel mixer and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) (4) was filled in a metal container and compression-molded to obtain a solid powdery blush.

(result)

The solid powdery blush of Example 23 was a solid powdery blush which was excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 24] Stick concealer

(Production method)

(1) The components 1 to 8 were mixed and dissolved at 100 °C.

(2) The components 9 to 14 were uniformly mixed in (1) at 90 °C.

(3) The (2) was processed by a three-roll mill.

(4) The (3) defoaming was dissolved and filled in a vessel at 85 ° C, and then cooled at 4 ° C to obtain a stick concealer.

(result)

The stick concealer of Example 24 is a stick concealer which is excellent in "wet feeling", "no stickiness", and "smoothness".

[Example 25] W/O type sunscreen

(Note 15) ABIL EM-90 (manufactured by EVONIC GOLDSCHMIDT GMBH)

(Production method)

(1) After the components 3 and 4 were heated and dissolved, the components 1 and 2 were added and uniformly dispersed by a roller.

(2) After dissolving the components 5 to 10 at 70 ° C, (1) was added at 60 ° C and uniformly mixed and dissolved.

(3) After the components 11 to 13 were mixed and dissolved, they were added to (2) at 60 ° C and emulsified.

(4) Adding components 14 and 15 to (3) and uniformly mixing them to obtain a W/O type sunscreen.

(result)

The W/O type sunscreen of Example 25 is a W/O type sunscreen which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 26] W/O type foundation

(Note 16) KF-6026 (manufactured by Shin-Etsu Chemical Co., Ltd.)

(Note 17) KF-6015 (manufactured by Shin-Etsu Chemical Co., Ltd.)

(Production method)

(1) The components 1 to 3 are uniformly mixed.

(2) The components 4 to 11 were uniformly dispersed by a roller.

(3) Add (2) to (1) and mix them uniformly.

(4) Adding components 12 to 16 to (3) and emulsifying them to obtain a W/O type foundation.

(result)

The W/O type foundation of Example 26 was a W/O type foundation which was excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 27] O/W type foundation

(Production method)

(1) The components 1 to 8 were uniformly dispersed by a roller.

(2) The components 9 to 12 are uniformly mixed.

(3) Add (1) to (2) and mix them uniformly.

(4) The components 13 to 20 were mixed and dissolved at 80 °C.

(5) (4) was added to (3) at 80 ° C and emulsified.

(6) Cooling (5) and adding component 21 to obtain an O/W type foundation.

(result)

The O/W type foundation of Example 27 was an O/W type foundation which was excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 28] oily solid foundation

(Production method)

(1) The components 7 to 14 were heated and dissolved at 90 °C.

(2) Adding components 1 to 6 to (1) and uniformly dispersing them by a roll.

(3) Component 15 was added to (2), dissolved at 80 ° C, and then filled into a metal container to obtain an oily solid foundation.

(result)

The oily solid foundation of Example 28 was an oily solid foundation excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 29] Makeup milk

(Production method)

(1) The components 1 to 4 were uniformly dissolved at 80 °C.

(2) The components 5 to 12 were uniformly dissolved at 80 °C.

(3) Add (1) to (2) and emulsify it.

(4) Adding component 13 to (3) and cooling to obtain makeup pre-milk.

(result)

The makeup lotion of Example 29 is a makeup lotion which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 30] Body milk

(Production method)

(1) The components 1 to 7 were uniformly dissolved at 80 °C.

(2) The components 8 to 16 were uniformly dissolved at 80 °C.

(3) Add (1) to (2) and emulsify it.

(4) The body lotion is obtained by stirring (3) with stirring.

(result)

The body lotion of Example 30 is a body lotion which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 31] Cleansing milk

(Note 18) IP Solvent 1620 (made by Idemitsu Kosan Co., Ltd.)

(Production method)

(1) The components 1 to 4 are uniformly mixed.

(2) Adding components 5 to 8 to (1) at 60 ° C and emulsifying them.

(3) The makeup remover is obtained by cooling while stirring (2).

(result)

The cleansing milk of Example 31 is a cleansing lotion which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 32] Waterproof mascara

(Production method)

(1) The components 1 to 5 were heated to 110 °C.

(2) Add components 6 to 10 to (1) and mix them.

(3) Add components 11 to 13 to (2) and mix them.

(4) A pair of roller pairs (3) are used to obtain a waterproof mascara.

(result)

The waterproof mascara of Example 32 is a waterproof mascara which is excellent in "wet feeling", "no stickiness" and "smoothness".

[Example 33] oily eyeliner

(Production method)

(1) The components 1 to 5 were heated to 100 ° C and uniformly mixed.

(2) Heat the ingredients 6 to 9 to 80 ° C and mix them evenly.

(3) Add (2) to (1) and mix them uniformly.

(4) The oily eyeliner is obtained by treating the pair of rollers (3).

(result)

The oily eyeliner of Example 33 is an oily eyeliner excellent in "wet feeling", "no stickiness", and "smoothness".

3 Production Example of Powder Surface-Coated by Polyphosphoric Acid Phosphate

The surface-coated powder was prepared by the following method using the product containing the polyphosphoric acid triester manufactured by the production example of the above 1. Other powders were also prepared in the same manner.

[Manufacturing Example 5] Examples of titanium oxide

To a solution of 49.0 g of titanium oxide, a solution in which 1.0 g of the product of Production Example 1 as a surface treatment agent and 70 g of n-hexane were dissolved was added, and the mixture was highly dispersed by a coating shaker for 30 minutes. Thereafter, the obtained slurry was air-dried, calcined at 125 ° C for 1 hour, and pulverized by a pulverizer to obtain titanium oxide surface-treated with 2.0% of the product of Production Example 1.

[Manufacturing Example 6] Examples of iron oxide or iron oxide

In the same manner as above, a mixture of 2.5 g of the product of Production Example 2 and 70 g of n-hexane dissolved in a surface treatment agent was added to 47.5 g of iron oxide or iron oxide, and the mixture was highly dispersed by a paint shaker for 30 minutes. Thereafter, the obtained slurry was air-dried, calcined at 125 ° C for 1 hour, and pulverized by a pulverizer to obtain a powder obtained by subjecting the powder to surface treatment with 5.0% of the product of Production Example 2.

[Manufacturing Example 7] Examples of talc, mica or sericite

In the same manner as above, a mixture of 0.5 g of the product of Production Example 1 and 70 g of n-hexane dissolved as a surface treatment agent was added to 49.5 g of talc, mica or sericite, and the mixture was highly dispersed by a coating shaker for 30 minutes. . Thereafter, the obtained slurry was air-dried, calcined at 125 ° C for 1 hour, and pulverized by a pulverizer to obtain a powder obtained by subjecting the powder to surface treatment with 1.0% of the product of Production Example 1.

[Manufacturing Example 8] Example of composite processing

To 750 g of isopropyl alcohol, 45 g of the product of Production Example 2 as a surface treatment agent and 15 g of isopropyl triisostearyl titanate were added and dissolved, and then put into 20 L of Henschel. In the mixer. 2940 g of titanium oxide (TIPAQUE CR-50, manufactured by Ishihara Sangyo Co., Ltd.) was added thereto, and uniformly dispersed at 70 °C. Then, the mixture was heated to 120 ° C, and the solvent was distilled off under reduced pressure while stirring for about 2 hours. After the powder was dried, it was cooled to room temperature, taken out from the mixer, and pulverized by an atomizer. It was calcined in a thermostat at 130 ° C for 6 hours to obtain a titanium oxide surface-treated with 1.5% of the product of Production Example 2 and 0.5% of isopropyl triisostearyl titanate.

[Manufacturing Example 9] Example of composite processing

To 5050 g of isopropyl alcohol, 50 g of the product of Production Example 2 as a surface treatment agent and 50 g of isopropyl triisostearyl titanate were added and dissolved, and then put into 20 L of Henschel. In the mixer. 4900 g of titanium oxide (TIPAQUE CR-50, manufactured by Ishihara Sangyo Co., Ltd.) was added thereto, and uniformly dispersed at 70 °C. Then, the mixture was heated to 120 ° C, and the solvent was distilled off under reduced pressure while stirring for about 2 hours. After the powder was dried, it was cooled to room temperature, taken out from the mixer, and pulverized by a nebulizer. It was calcined in a thermostat at 130 ° C for 6 hours to obtain a titanium oxide surface-treated with 1.0% of the product of Production Example 2 and 1.0% of isopropyltriisostearyl titanate.

[Manufacturing Example 10] Example of Compound Processing

To 750 g of isopropyl alcohol, 15 g of the product of Production Example 2 as a surface treatment agent and 45 g of isopropyl triisostearyl titanate were added and dissolved, and then put into 20 L of Henschel. In the mixer. 2940 g of titanium oxide (TIPAQUE CR-50, manufactured by Ishihara Sangyo Co., Ltd.) was added thereto, and uniformly dispersed at 70 °C. Then, the mixture was heated to 120 ° C, and the solvent was distilled off under reduced pressure while stirring for about 2 hours. After the powder was dried, it was cooled to room temperature, taken out from the mixer, and pulverized by a nebulizer. It was calcined in a thermostat at 130 ° C for 6 hours to obtain a titanium oxide surface-treated with 0.5% of the product of Production Example 2 and 1.5% of isopropyl triisostearyl titanate.

[Manufacturing Comparative Example 1]

To 49.0 g of titanium oxide, a solution in which 1.0 g of isopropyl triisostearyl titanate as a surface treatment agent and 50 g of isopropyl alcohol were dissolved was added, and the mixture was highly dispersed by a paint shaker for 30 minutes. Thereafter, the obtained slurry was air-dried, calcined at 125 ° C for 1 hour, and pulverized by a pulverizer to obtain oxidation of the surface of the powder by using 2.0% of isopropyl triisostearyl titanate. titanium.

(Evaluation of Dispersibility of Surface-Coated Powder (Composite Treatment))

The dispersibility of the surface-coated titanium oxides of Production Examples 8 to 10 and Comparative Example 1 was evaluated. As the dispersing solvent, (1) decamethylcyclopentaoxane, (2) tri-2-ethylhexanoic acid glyceride, (3) decamethylcyclopentaoxane, p-methoxy 2-ethylhexyl cinnamate and isotridecyl isononanoate are mixed at a ratio of 22:6:2 by mass (hereinafter referred to as a mixed solvent). 1 g of surface-coated titanium oxide was added to a standard bottle, 30 ml of the above-mentioned dispersion solvent was added thereto, and the lid was placed thereon, and the mixture was covered by an ultrasonic machine (BRANSONIC 1510J-DTH 42 kHz) for 30 minutes. Thereafter, the mixture was transferred to a settling tube having a bottom area of 1 cm ² and a height of 30 cm, and allowed to stand at room temperature, and the volume of the dispersion layer was visually evaluated after 6 days. At this time, the reading value of the scale of the settling tube (the height of the dispersion layer) was used as a criterion for determination. The results are shown in Table 3.

(judgment basis)

◎: The height of the dispersion layer is 25 cm or more

○: The height of the dispersion layer is 20 cm or more and less than 25 cm.

Δ: the height of the dispersion layer is 10 cm or more and less than 20 cm

×: the height of the dispersion layer is less than 10 cm

[table 3]

4 Formulation example of a cosmetic containing a powder coated with polyphosphonium phosphate for surface coating treatment

The surface-coated powder produced by the above production examples was used in the following formulation.

In the following examples, for example, "manufacturing Example 1 (2.0%) treated titanium oxide" means a product obtained in Production Example 1 in an amount of 2.0% by mass (containing a mixture of polyphosphoric acid triesters) A surface-treated powder coated with titanium oxide.

[Examples 34 to 39 and Comparative Examples 10 to 12]

W/O type foundation

[Table 4]

(Production method)

(1) The components 1 to 17 are treated by a roller.

(2) The components 18 to 21 are treated by a roller.

(3) The (1), (2) and the components 22 and 23 are uniformly mixed by a disperser.

(4) Slowly add ingredients 24 to 28 in (3) and emulsify them.

(5) Defoaming (4) and filling it into a container to obtain a W/O type foundation.

(Evaluation)

For the W/O type foundations of Examples 34 to 39 and Comparative Examples 10 to 12, 20 people in the cosmetics evaluation expert group used "smoothness of makeup film", "lasting effect of makeup", and "smoothness" according to the following evaluation criteria. Each of the items is evaluated in seven stages, and the average score of the entire group is used and judged based on the following criteria.

[evaluation benchmark]

[Judgement criteria]

(result)

The W/O type foundations of Examples 34 to 39 are a W/O type foundation which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use. The W/O type foundation of Comparative Example 10 has a small amount of treatment of the methyl hydrogen polyoxymethane in the titanium oxide, so that the uniformity of the cosmetic film, the long-lasting effect of the makeup, and the feeling of smoothness are poor, and even if it is oxidized Comparative Example 11 in which the amount of treatment in titanium was large was also inferior in the uniformity of the cosmetic film, the long-lasting effect of the makeup, and the feeling of being smooth. Further, the W/O type foundation of Comparative Example 12 was also inferior in the uniformity of the makeup film, the makeup lasting effect, and the smooth feeling of use.

[Example 40] O/W type liquid foundation

(Production method)

(1) The components 1 to 8 were uniformly dispersed by a roller.

(2) The components 9 to 12 are uniformly mixed.

(3) Add (1) to (2) and mix them uniformly.

(4) The components 13 to 19 were mixed and dissolved at 80 °C.

(5) (4) was added to (3) at 80 ° C and emulsified.

(6) Cooling (5) and adding component 20 to obtain an O/W type foundation.

(result)

The O/W type foundation of Example 40 was an O/W type foundation which was excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 41] oily solid foundation

(Production method)

(1) The components 7 to 13 were heated and dissolved at 90 °C.

(2) Adding components 1 to 6 to (1) and uniformly dispersing them by a roll.

(3) After adding component 14 to (2) and dissolving at 80 ° C, it was filled in a metal container to obtain an oily solid foundation.

(result)

The oily solid foundation of Example 41 was an oily solid foundation excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 42] Rod-shaped oily solid concealer

(Production method)

(1) The components 1 to 7 were mixed and dissolved at 100 °C.

(2) The components 8 to 13 were uniformly mixed in (1) at 90 °C.

(3) The (2) was processed by a three-roll mill.

(4) After defoaming (3) and dissolving and filling into a vessel at 85 ° C, it was cooled at 4 ° C to obtain a stick concealer.

(result)

The rod-like oily solid concealer of Example 42 is a stick-like oily solid concealer which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 43] Solid powdery foundation

(Production method)

(1) Components 1 to 10 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 11 to 13 are uniformly mixed and dissolved.

(3) Add (2) and 14 while stirring with a Henschel mixer (1) and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) (4) was filled in a metal container and compression-molded to obtain a solid powdery foundation.

(result)

The solid powdery foundation of Example 43 was a solid powdery foundation excellent in uniformity of a cosmetic film, a makeup lasting effect, and a smooth feeling of use.

[Example 44] solid powder eye shadow

(Production method)

(1) Components 1 to 9 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 10 to 12 are uniformly mixed and dissolved.

(3) Add (2) and 13 while stirring (1) with a Henschel mixer and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) The (4) was filled in a metal container and compression-molded to obtain a solid powdery eye shadow.

(result)

The solid powdery eye shadow of Example 44 was a solid powdery eye shadow which was excellent in uniformity of a cosmetic film, a makeup lasting effect, and a smooth feeling of use.

[Example 45] Solid powdered blush

(Production method)

(1) Components 1 to 7 were uniformly dispersed at 75 ° C using a Henschel mixer (manufactured by Mitsui Miike Co., Ltd.).

(2) The components 8 to 10 were heated to 65 ° C and uniformly mixed and dissolved.

(3) Add (2) and 11 while stirring with a Henschel mixer (1) and uniformly disperse them.

(4) The (3) is pulverized by a pulverizer.

(5) (4) was filled in a metal container and compression-molded to obtain a solid powdery blush.

(result)

The solid powdery blush of Example 45 is a solid powdery blush which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 46] Powdered powder

(Production method)

(1) The components 1 to 4 are uniformly mixed.

(2) Add ingredients 5 to 8 while stirring with a Henschel mixer (1) and mix them evenly.

(3) The powder was obtained by pulverizing (2) with a pulverizer.

(result)

The powdery honey powder of Example 46 was a powdery honey powder which was excellent in uniformity of a cosmetic film, a makeup lasting effect, and a smooth feeling of use.

[Example 47] Lipstick

(Production method)

(1) Components 1 to 7 were uniformly dissolved and mixed at 100 °C.

(2) Add components 8 to 14 in (1) and mix them uniformly.

(3) Inject (2) into a container and allow it to cool to obtain a lipstick.

(result)

The lipstick of Example 47 was a lipstick which was uniform in the uniformity of the makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 48] O/W type mascara

(Note 5) YODOSOL 32A707 (45% solid content) (manufactured by NSC Japan)

(Production method)

(1) The components 1 to 3 were uniformly mixed at 80 °C.

(2) The components 4 to 8 are treated by a roller.

(3) The components 9 to 14 were uniformly mixed at 80 °C.

(4) After mixing (1) and (2), (3) is added and emulsified.

(5) Cooling (4) to obtain O/W type mascara.

(result)

The O/W type mascara of Example 48 is an O/W type mascara which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 49] Waterproof mascara

(Note 6) IP Solvent 1620 (made by Idemitsu Kosan Co., Ltd.)

(Production method)

(1) The components 1 to 5 were heated to 110 °C.

(2) Add components 6 to 10 to (1) and mix them.

(3) Add components 11 to 13 to (2) and mix them.

(4) The (3) was treated with a three-roll mill to obtain a waterproof mascara.

(result)

The waterproof mascara of Example 49 is a waterproof mascara which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

[Example 50] Oily eyeliner

(Production method)

(1) The components 1 to 5 were heated to 100 ° C and uniformly mixed.

(2) Heat the ingredients 6 to 9 to 80 ° C and mix them evenly.

(3) Add (2) to (1) and mix them uniformly.

(4) The oily eyeliner is obtained by treating the pair of rollers (3).

(result)

The oily eyeliner of Example 50 is an oily eyeliner excellent in uniformity of a cosmetic film, a makeup lasting effect, and a smooth feeling of use.

[Example 51] W/O type sunscreen

(Note 7) ABIL EM-90 (manufactured by EVONIC GOLDSCHMIDT GMBH)

(Production method)

(1) After the components 3 and 4 were heated and dissolved, the components 1 and 2 were added and uniformly dispersed by a three-roll mill.

(2) After dissolving the components 5 to 10 at 70 ° C, (1) was added at 60 ° C and uniformly mixed and dissolved.

(3) After the components 11 to 13 were mixed and dissolved, they were added to (2) at 60 ° C and emulsified.

(4) The components 14 and 15 were added to (3) and uniformly mixed to obtain a W/O type sunscreen.

(result)

The W/O type sunscreen of Example 51 is a W/O type sunscreen which is excellent in uniformity of a makeup film, a makeup lasting effect, and a smooth feeling of use.

5 Production Example of Powder Dispersion Containing Polyphosphonium Phosphate [Examples 52 to 60 and Comparative Example 13]

The product containing the polyphosphoric acid triester manufactured by the production examples 1 to 4 of the above 1 was prepared together with the components shown in Table 5, and the powder dispersion was prepared and evaluated by the method shown below. The comparative examples were also evaluated in the same manner. The results are shown in Table 5.

In the following examples, for example, the "product of Production Example 1" means the production of the product obtained in Example 1 (containing a mixture of polyphosphoric acid triester). The same applies to the subsequent embodiments.

(Simple evaluation of the dispersion of the settlement tube)

[table 5]

(evaluation method)

The dispersion containing the components 1 to 9 was dispersed by an ultrasonic machine (BRANSONIC 1510J-DTH 42 kHz) for 1 hour, and then added to a sedimentation tube having a bottom area of 1 cm ² and a height of 30 cm, and visually evaluated for 3 days. Settling volume. Further, the sedimentation volume means the sum of the volume of the dispersion layer and the sedimentation layer, and is determined based on the read value of the scale of the settling tube.

The judgment criteria are as follows.

◎: (settling volume is) 20 cm or more.

○: (Settling volume is) 15 cm or more and less than 20 cm.

Δ: (settling volume is) less than 5 cm above 5 cm.

×: (settling volume is) less than 5 cm.

[Examples 61 to 6610 to 15 and Comparative Examples 14 and 15]

The product containing the polyphosphoric acid triester manufactured by the above Production Examples 1 to 4 was prepared together with the components shown in Table 6 to prepare a powder dispersion, which was evaluated by the method shown below. The comparative examples were also evaluated in the same manner. The results are shown in Table 6.

(coating film evaluation)

[Table 6]

(evaluation method)

The components 1 to 11 were mixed and treated three times with a 1 HP three-roll mill.

The obtained dispersion was applied onto a glass plate by a rubber knife (6 μm), and uniformity was evaluated by visual observation.

The judgment criteria are as follows.

◎: There was no unevenness in the coating film, and the whiteness was high.

○: There was no unevenness in the coating film, but the whiteness was slightly lower.

Δ: The coating film was uneven, and the whiteness was slightly lower.

×: The coating film was uneven, and the whiteness was low.

6 Formulation of a cosmetic containing a powder dispersion containing polyphosphonium phosphate

[Examples 67 to 70 and Comparative Examples 16, 17] W/O type foundation

A W/O type foundation having the composition shown in Table 7 was prepared, and the uniformity of the cosmetic film and the long-lasting effect of the makeup were evaluated.

[Table 7]

(Production method)

(1) The components 1 to 14 are treated by a roller.

(2) The components 15 to 17 are treated by a roller.

(3) The (1), (2) and the components 18 to 20 are uniformly mixed by a disperser.

(4) Slowly add ingredients 21 to 25 in (3) and emulsify them.

(5) Defoam and fill (4) into the container.

(Evaluation)

For the W/O type foundations of Examples 67 to 70 and Comparative Examples 16 and 17, 20 of the cosmetics evaluation expert groups performed the items of "uniformity of the cosmetic film" and "lasting effect of makeup" according to the following evaluation criteria. The evaluation of the stages is further determined by the average score of the entire group based on the following criteria.

[evaluation benchmark]

[Judgement criteria]

The W/O type foundations of Examples 67 to 70 were W/O type foundations which were excellent in powder dispersibility, uniform in cosmetic film, and excellent in makeup lasting effect. In the W/O type foundation of Comparative Examples 16 and 17, the ratio of the previous polyoxygen dispersant/powder was 0.1, but the powder dispersibility was inferior, so that it was not excellent in the uniformity of the cosmetic film and the makeup lasting effect.

[Example 71] W/O type foundation

(Production method)

(1) Components 1 to 9 were uniformly mixed by a three-roll mill to prepare a dispersion containing polyfluorene-modified phosphoric acid triester.

(2) The components 10 to 13 are uniformly mixed.

(3) Add (1) to (2) and mix them uniformly.

(4) The components 14 to 20 were mixed and dissolved at 80 °C.

(5) (4) was added to (3) at 80 ° C and emulsified.

(6) Cooling (5) and adding component 21 to obtain an O/W type foundation.

The O/W type foundation of Example 71 was an O/W type foundation which was excellent in "uniformity of a cosmetic film" and "lasting effect of makeup".

[Example 72] oily solid foundation

(Production method)

(1) The components 7 to 14 were heated and dissolved at 90 °C.

(2) A dispersion containing polyfluorene-modified phosphoric acid triester was prepared by adding the components 1 to 6 to (1) and uniformly mixing them by a three-roll mill.

(3) After adding the component 15 to (2) and dissolving at 80 ° C, it was filled in a metal container to obtain an oily solid foundation.

The oily solid foundation of Example 72 was an oily solid foundation excellent in "uniformity of a cosmetic film" and "lasting effect of makeup".

[Example 73] Rod-shaped oily solid concealer

(Production method)

(1) The components 1 to 8 were mixed and dissolved at 100 °C.

(2) Add components 9 to 15 in (1) at 90 ° C and mix them uniformly.

(3) A dispersion containing polyfluorene-modified phosphoric acid triester was prepared by treating (2) with a three-roll mill.

(4) After defoaming (3) and dissolving and filling into a vessel at 85 ° C, it was cooled at 4 ° C to obtain a stick concealer.

The rod-like oily solid concealer of Example 73 is a stick-like oily solid concealer which is excellent in "uniformity of a cosmetic film" and "lasting effect of makeup".

[Example 74] W/O type sunscreen

(Note 3) ABIL EM-90 (manufactured by EVONIC GOLDSCHMIDT GMBH)

(Production method)

(1) After the components 3 and 4 were heated and dissolved, the components 1 and 2 were added and uniformly mixed by a roll to prepare a dispersion containing the polyfluorene-modified phosphoric acid triester.

(2) After dissolving the components 5 to 10 at 70 ° C, (1) was added at 60 ° C and uniformly mixed and dissolved.

(3) After the components 11 to 13 were mixed and dissolved, they were added to (2) at 60 ° C and emulsified.

(4) Adding components 14 and 15 to (3) and uniformly mixing them to obtain a W/O type sunscreen.

The W/O type sunscreen of Example 74 is a W/O type sunscreen which is excellent in "uniformity of a cosmetic film" and "lasting effect of makeup".

[Example 75] W/O type foundation

(Note 4) KF-6015 (manufactured by Shin-Etsu Chemical Co., Ltd.)

(method of law)

(1) The components 1 to 3 are uniformly mixed.

(2) The components 4 to 10 were uniformly dispersed by a roller.

(3) Add (2) to (1) and mix them uniformly.

(4) After adding the components 11 to 14 to (3) and emulsifying them, the component 15 is added to obtain a W/O type foundation.

The W/O type foundation of Example 75 was a W/O type foundation which was excellent in "uniformity of a cosmetic film" and "lasting effect of makeup".

[Industrial availability]

Since the polyphosphonium phosphate triester of the present invention has a large amount of polyfluorene oxide chain, it also exhibits water repellency and dispersibility in a small amount of treatment, and has a phosphate group, especially since the metal oxide is firmly bonded to the surface of the powder, Excellent adhesion. Therefore, the cosmetic formulated with the polyphosphoric acid triester of the present invention is excellent in the repairing effect, the smooth feeling of use, and the long-lasting effect of makeup. Further, the cosmetic film of the cosmetic powder coated with the polyphosphonium phosphate triester coated with the present invention is excellent in uniformity and long-lasting makeup effect.

Further, the polyphosphonium phosphate triester of the present invention exhibits a high dispersibility even when it is used in an oil dispersion of a powder of a metal oxide or the like, and is further formulated with the makeup of the polyphosphonium phosphate triester of the present invention. The uniformity of the cosmetic film and the long-lasting effect of the makeup are excellent.

Claims (15)

A cosmetic containing formula (I) as a polyphosphonium phosphate: (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or more of polyphosphoric acid triesters. A cosmetic containing polyphosphonium phosphate containing: (60) as a polyphosphonium phosphate of 60 to 100% by mass: (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or more of polyphosphoric acid triesters, and 0 to 35 mass% of formula (II): (in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass : (In the formula, one or more of the polyphosphazene monophosphates represented by R ₁ , R and n are the same as defined in the above formula (I)). The cosmetic of claim 1 or 2 further comprising an oil. A powder by the formula (I) as a polyphosphonium phosphate: (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or two or more kinds of polyphosphoric acid triesters are subjected to surface coating treatment. A powder which is subjected to surface coating treatment by polyphosphonium phosphate containing: (60) as a polyphosphonium phosphate of 60% by mass to 100% by mass: (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or more of polyphosphoric acid triesters, and 0 to 35 mass% of formula (II): (in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass : (In the formula, one or more of the polyphosphazene monophosphates represented by R ₁ , R and n are the same as defined in the above formula (I)). The surface-coated powder of claim 4 or 5, which further comprises an organic titanate as a surface treating agent in addition to the above polyphosphoric acid phosphate. The powder of claim 6, wherein the mass ratio of the polyphosphoric acid phosphate to the organic titanate is 1:9 to 9:1. The powder of claim 6, wherein the organic titanate is isopropyl triisostearyl titanate. A surface-treated powder according to claim 4 or 5, wherein the powder is at least one selected from the group consisting of titanium oxide, zinc oxide, and iron oxide. The surface-coated powder according to claim 4 or 5, wherein the polyphosphonium phosphate is coated in an amount of 0.01 to 5% by mass based on the surface-coated powder. A cosmetic containing the surface-coated powder of any one of claims 4 to 10. A powder dispersant containing the formula (I) as a polyphosphonium phosphate: (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or more of polyphosphoric acid triesters. A powder dispersant comprising polyphosphonium phosphate, the polyphosphonium phosphate comprising: (60) as a polyphosphonium phosphate of 60% by mass to 100% by mass (wherein each R ₁ independently represents an alkyl group having 1 to 4 carbon atoms, R represents a divalent hydrocarbon group having 2 to 7 carbon atoms of -O-, and n represents an integer of 5 to 40) One or more of polyphosphoric acid triesters, and 0 to 35 mass% of formula (II): (in the formula, _one or more of the polyphosphonium phosphate diesters represented by R ₁ , R and n are the same as defined in the above formula (I)), and the formula (III) of 0 to 5% by mass : (In the formula, one or more of the polyphosphazene monophosphates represented by R ₁ , R and n are the same as defined in the above formula (I)). A powder dispersion comprising the powder dispersant, powder and oil of claim 12 or 13. A cosmetic comprising the powder dispersion of claim 14.