JP4297773B2 - Polyether composition for cosmetics - Google Patents

Description

  The present invention relates to a polyether composition for cosmetics. More particularly, the present invention relates to a polyether composition for cosmetics used in foundations, lipsticks, nail makeup enamels and the like.

Polyether compounds using ethylene oxide or propylene oxide as raw materials have been widely applied as cosmetic raw materials. For example, polyoxyethylene-type polyethers have excellent emulsifying power and solubilizing power, so that they are emulsifiers for creams or emulsions. As a solubilizer, fragrances or chemicals for lotions are used. The ethylene oxide / propylene oxide block copolymer type is widely used as a cosmetic raw material because it has a large molecular weight and less skin irritation compared to other surfactants (see Non-Patent Document 1). . It has also been proposed to use polyoxyalkylene compounds obtained by addition polymerization of ethylene oxide and propylene oxide with monovalent or polyhydric alcohols in hair cosmetics (hairdressing). (See Patent Document-1)
"New Cosmetics" (Takeo Nagai: Nanzando Publishing) JP-A-3-261713

  In recent years, since cosmetics are desired to have good tactile sensation, oils such as vegetable oils, mineral oils, silicone compounds, and inorganic powders have been added. However, since conventional polyether compounds have poor compatibility with oils, the tactile feel of cosmetics is easily impaired. In addition, since there is a problem with the dispersibility of the inorganic powder in oil, a step of surface-treating the inorganic powder with a silicone-based coupling agent in advance is necessary to disperse the inorganic powder.

As a result of diligent studies to solve the above problems, the present inventors have found that a specific polyether composition has excellent oil compatibility (compatibility with oil) and inorganic powder dispersibility, and reached the present invention. did.
That is, the present invention provides the polyether (E1) represented by the general formula (1) and / or Etherified product (E2c) obtained from (E1) and (poly) halide It is a polyether composition for cosmetics characterized by comprising.
Formula _{^{R 1 - {(OCH 2 CH}} 2 CH 2 CH 2) m (OA) n -OH} q (1)
[Wherein, R ¹ is a residue obtained by removing OH from a C1-C24 q-valent alcohol, A is a 1,2-propylene group , q is an integer of 1-6, m and n are 1- It is an integer of 600, and the portion of (OCH ₂ CH ₂ CH ₂ CH ₂ ) _m (OA) _n represents a random bond or a block bond. ]

  The polyether composition for cosmetics of the present invention is an inorganic powder that has an effect of imparting a smooth feel to cosmetics by exhibiting excellent oil compatibility that could not be achieved by conventional techniques, and has not been surface-treated. Therefore, the cosmetic manufacturing process can be simplified or the cost can be reduced.

In the general formula (1) representing the polyether (E1) in the present invention, R ¹ is at least one, preferably all hydroxyl groups are removed from a C1-C24 q-valent alcohol (q is 1-6). Residues such as linear, branched or alicyclic 1-6 valent alcohol residues, 1-6 valent phenol residues, and 1-6 valent araliphatic alcohol residues. It is done.

Examples of the monohydric alcohol [R ¹ OH] that forms a residue obtained by removing a hydroxyl group from a monohydric alcohol include linear or branched saturated aliphatic monools having 1 to 24 carbon atoms (methanol, ethanol, n- and i). -Propanol, butanol, pentanol, hexanol, heptanol, octanol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol , Eicosyl alcohol, heneicosyl alcohol, docosyl alcohol, tricosyl alcohol, tetracosyl alcohol, etc.); cis- or trans- unsaturated aliphatic hydrocarbon group having 3 to 24 carbon atoms Alkenyl group or alkynyl group) (1-, 2- and iso-propenyl alcohol, butenyl alcohol, pentynyl alcohol, hexenyl alcohol, peptenyl alcohol, nonenyl alcohol, decenyl alcohol, undecenyl alcohol, Dodecenyl alcohol, tridecenyl alcohol, tetradecenyl alcohol, pentadecenyl alcohol, hexadecenyl alcohol, heptadecenyl alcohol, octadecenyl alcohol, nonadecenyl alcohol, eicosenyl Alcohol, henecosenyl alcohol, dococenyl alcohol, tricocenyl alcohol and tetracocenyl alcohol); and alicyclic monools having 4 to 24 carbon atoms (such as cyclopentanol and cyclohexanol). It is.

Examples of the dihydric alcohol [R ¹ (OH) ₂ ] that forms a dihydric alcohol residue include aliphatic diols having 2 to 24 carbon atoms (for example, ethylene glycol, propylene glycol, 1,3-, 1,4). -And 1,2-butanediol, neopentyl glycol, 1,6-hexanediol, 1,2- and 1,8-octanediol, isobutylene glycol, 3-methyl-1,5-pentanediol, 2,2, 4-trimethyl-1,3-pentanediol, 2,2-dimethyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol and 2,5-dimethylhexane-2,5- Alkylene glycols such as diols; alicyclic diols having 4 to 18 carbon atoms (for example, 1,4-cyclohexanediol and 1,4-cyclohexanedi) Cycloalkylene glycol) such as ethanol; hydrogenated bisphenols (e.g., hydrogenated bisphenol A and hydrogenated bisphenol F); and heterocyclic diols (for example, 1,4,3,6- sorbide) and the like.

Examples of the trivalent to hexavalent alcohol [R ¹ (OH) ₃ to ₆ ] forming the residue of the trivalent to hexavalent alcohol include trivalent alcohols having 3 to 24 carbon atoms (for example, glycerin, 1, 2, 3). -Butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butane Triol, 2,3,4-pentanetriol, 2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, pentamethyl Glycerin, 1,2,4-butanetriol, 1,2,4-pentanetriol, alkanetriols such as trimethylolethane and trimethylolpropane), 4 having 5 to 24 carbon atoms Hexavalent polyhydric alcohols (eg, pentaerythritol, sorbitol, mannitol, 1,5-, 3,6- and 1,4-sorbitan and alkane polyols such as diglycerin; their intramolecular or intermolecular dehydrates; and Sugars such as sucrose, glucose, mannose, fructose and methyl glucoside and derivatives thereof).

Examples of phenols [R ¹ OH] that form a residue obtained by removing a hydroxyl group from monovalent phenols include monohydric phenols having 6 to 24 carbon atoms, such as phenol, alkylphenol (o, m, or p-methylphenol). M, p-dimethylphenol, 2,6-dimethylphenol, o, m or p-ethylphenol, pn-butylphenol, p-octylphenol and p-nonylphenol), monostyrylphenol and monobenzylphenol, etc. It is done.
Examples of phenols [R ¹ (OH) ₂ ] that form residues of 2 to 6 valent phenols include 2 to 6 valent phenols having 6 to 24 carbon atoms. These phenols include monocyclic polyhydric phenols [for example, dihydric phenols (catechol, resorcin, hydroquinone, etc.), trioxybenzene, tetraoxybenzene, hexaoxybenzene, etc.], bisphenols (for example, bisphenol A, bisphenol). F) and the like.

1-6 monovalent The aromatic aliphatic alcohols to form the residue of araliphatic alcohols _{^{[R 1 (OH) 1 ~}} 6], aralkyl alcohol having 7 to 24 carbon atoms (benzyl alcohol, phenethyl alcohol, etc.), carbon Examples thereof include substituted aralkyl alcohols of formula 8 to 24 (o, m or p-methylbenzyl alcohol, pn-butylphenethyl alcohol, etc.).

  Among these, from the viewpoint of inorganic powder dispersibility, a residue of a linear, branched or alicyclic 1-6 valent aliphatic alcohol having 2 to 20 carbon atoms, particularly 2 to 18 carbon atoms, particularly 1 A residue of a trivalent (particularly monovalent or divalent) aliphatic or alicyclic alcohol is preferred.

  A in General formula (1) is a C2-C12 alkylene group except a 1, 4- butylene group. Examples of the alkylene group having 2 to 24 carbon atoms include ethylene group, 1,2- and 1,3-propylene group, 1,2- and 2,3-butylene group and isobutylene group, 1,6-hexylene group, Examples include 1,2-undecylene group and 1,2-dodecylene group. Two or more of these may be used in combination. Among these, an alkylene group having 2 to 8 carbon atoms is preferable, and an ethylene group and a 1,2-propylene group are more preferable from the viewpoint of inorganic powder dispersibility.

M and n in General formula (1) are 1-600, preferable m is 3-100, and preferable n is 5-150. The ratio of m to n (m / n) is preferably 5/95 to 95/5, particularly 30/70 to 70/30, from the viewpoint of oil compatibility.
(OCH ₂ CH ₂ CH ₂ CH ₂ ) and (OA) may be random bonds, block bonds, or a combination thereof. It is preferable that at least a portion has a random bond portion in view of excellent fluidity at a low temperature, and more preferably 80% by mass or more of (OCH ₂ CH ₂ CH ₂ CH ₂ ) is random addition.

  (E1) has a number average molecular weight of preferably 500 to 30,000, more preferably 1,000 to 10,000, and particularly preferably 1,500 to 6,000. If it is 500 or more, the inorganic powder dispersibility becomes better, and if it is 30,000 or less, it is difficult to achieve high viscosity, which is convenient in terms of handling. The number average molecular weight (hereinafter abbreviated as Mn) is measured by a hydroxyl value measurement.

The HLB (hydrophilic-hydrophobic balance) of (E1) is preferably 10 or less, more preferably 1 to 8, and particularly preferably 2 to 6. Within this range, it is excellent from the viewpoint of oil compatibility. HLB is a value calculated by the Oda method based on an organic conceptual diagram, and this calculation method is described in, for example, “Emulsification / Solubilization Technology” [Showa 51, Engineering Book Co., Ltd.]. The organic and inorganic values for deriving HLB are described in “Organic Conceptual Diagram-Fundamentals and Applications” [Sankyo Publishing Co., Ltd., 1984]. Value).

(E1) is tetrahydrofuran (hereinafter referred to as THF) in an alcohol having 1 to 24 carbon atoms represented by R ¹ (OH) q in the presence of a catalyst, preferably at a temperature of 30 to 120 ° C., preferably at a pressure of 0 to 0.6 MPa. And a C2-C12 alkylene oxide other than THF (hereinafter abbreviated as AO) can be produced by random addition, block addition, or a combination thereof.

As the above-mentioned catalyst, conventionally known catalysts can be used. However, in the addition reaction containing THF (a single addition reaction of THF or a random copolymerization addition reaction of THF and AO) and the addition reaction of only AO, preferred types of catalyst are used. Different.
As a catalyst for the addition reaction containing THF, Lewis acids such as BF ₃ , BaCl ₃ , AlCl ₃ , FeCl ₃ and SnCl _3, and complexes thereof [for example, BF ₃ ether complex, BF ₃ tetrahydrofuran complex (BF ₃ · THF) ; Protic acids such as H ₂ SO ₄ and HClO ₄ ; Perchlorates of alkali metals such as KClO ₄ and NaClO ₄ ; Peroxides of alkaline earth metals such as Ca (ClO ₄ ) ₂ and Mg (ClO ₄ ) ₂ Examples include chlorates; perchlorates of metals other than the above such as Al (ClO ₄ ) _{3 and the} like, and BF ₃ ether complexes and BF ₃ · THF are preferred.
In addition to the above-mentioned catalyst, the catalyst for the addition reaction using only AO is an alkali catalyst, for example, a hydroxide [KOH, NaOH, CsOH, Ca (OH) ₂ or other alkali metal or alkaline earth metal water. Oxides, etc.]; oxides (oxides of alkali metals or alkaline earth metals such as K ₂ O, CaO, BaO); alkali metals (Na, K, etc.) and hydrides thereof (NaH, KH, etc.); Examples include amines such as triethylamine and trimethylamine, and preferred are KOH, NaOH, CsOH, BF ₃ ether complex and BF ₃ · THF.

  As AO, in formula (1), A is an alkylene group having 2 to 12 carbon atoms, ethylene oxide (hereinafter referred to as EO), propylene oxide (hereinafter referred to as PO), 1,2-butylene oxide, 2, Examples include 3-butylene oxide, isobutylene oxide, 1,2-undecylene oxide, and the like. Of these, EO, PO, 1,2-butylene oxide, and 1,2-undecylene oxide are preferable, and EO and PO are particularly preferable. These may be used in combination.

Examples of the derivative (E2) of (E1) in the present invention include those obtained by reacting at least one, preferably all of the terminal hydroxyl groups of (E1).
As (E2), esterified product (E2a) obtained from (E1) and a carboxylic acid having 1 to 18 carbon atoms or an ester-forming compound thereof, urethanized product (E2b) obtained from (E1) and polyisocyanate, (E1) ) And (poly) halides, etherified compounds (E2c), cyanoethylated compounds obtained from (E1) and acrylonitrile, (E1) sulfates, (E1) phosphates, and (E1) aminated compounds, etc. Is mentioned. Of these, (E2a), (E2b), (E2c) and combinations thereof are preferred.

(A) for producing (E2a) includes a carboxylic acid having 1 to 18 carbon atoms and an ester-forming compound thereof [for example, a carboxylic anhydride of the carboxylic acid, an alkyl having 1 to 4 carbon atoms of the carboxylic acid. Carboxylic acid alkyl ester having a group, carboxylic acid halide of the carboxylic acid, etc.].
Specific examples of (a) include the following.
(A-1); C1-C18 aliphatic monocarboxylic acid Formic acid, acetic acid, propionic acid, thiopropionic acid, butanoic acid, hexanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid and the like;
(A-2); C2-C18 aliphatic divalent carboxylic acid Oxalic acid, malonic acid, succinic acid, propanedicarboxylic acid, thiodipropionic acid, etc.

(A-3): C4-C18 aliphatic polyvalent (3 to 4 or more) carboxylic acid propanetricarboxylic acid, methylcyclohexanetricarboxylic acid, cyclohexentricarboxylic acid, methylcyclohexentricarboxylic acid, cyclohexanetetracarboxylic acid, etc. (A-4); aromatic monocarboxylic acid having 7 to 18 carbon atoms benzoic acid, phenylacetic acid and naphthalenecarboxylic acid (a-5); aromatic dicarboxylic acid having 8 to 18 carbon atoms phthalic acid, isophthalic acid, Terephthalic acid, naphthalene dicarboxylic acid, xylylene dicarboxylic acid, tetrahydrophthalic acid, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, highmic acid, tetrabromophthalic acid, tetrachlorophthalic acid and the like (a-6); 18 aromatic polyvalent (3-4 valence or higher) Boronic acid benzenetricarboxylic acid, benzenetetracarboxylic acid, naphthalenetetracarboxylic acid and the like (a-7); (a-2), (a-3), (a-5) and (a-6) acid anhydrides ( a-8); methyl, ethyl, propyl and butyl esters of (a-1) to (a-6) (a-9); acid halogens (chlorine, bromine, etc.) of (a-1) to (a-6) )monster

Of these, preferred are (a-2), (a-5) and (a-7), more preferred are (anhydrous) oxalic acid, (anhydrous) malonic acid, (anhydrous) succinic acid, (Anhydrous) glutaric acid, (anhydrous) thiodipropionic acid, (anhydrous) tetrahydrophthalic acid, methyltetrahydro (anhydrous) phthalic acid, hexahydro (anhydrous) phthalic acid, (anhydrous) hymic acid, (anhydrous) norbornene dicarboxylic acid, ( Anhydrous) phthalic acid, (anhydrous) isophthalic acid and terephthalic acid, particularly preferred are (anhydrous) oxalic acid, (anhydrous) malonic acid, (anhydrous) succinic acid, (anhydrous) propanedicarboxylic acid and (anhydrous) thio Dipropionic acid.
(E2a) using these has a low viscosity and is easy to handle.

The reaction conditions of (E1) and (a) are not particularly limited, and can be performed under known esterification reaction conditions. For example, in the case of a one-step synthesis method, an esterification catalyst, preferably an acid catalyst (for example, paratoluenesulfonic acid, sulfuric acid, etc.) is used, preferably 50 to 150 ° C., more preferably 70 to 130 ° C. for 8 to 20 hours. It can be synthesized by reaction. The equivalent ratio [(E1) / (a)] of the functional groups of (E1) and (a) is preferably 0.5 to 2.0, more preferably 0.9 to 1.5. When it is 0.9 or more, a large amount of unreacted polycarboxylic acid does not remain and treatment such as water washing becomes unnecessary. Moreover, since the lubricity of a product will become further better if it is 2.0 or less, it is preferable.
Moreover, solvents, such as toluene and benzene, can be used for reaction as needed. The esterification reaction can be carried out at normal pressure, reduced pressure, or increased pressure, but the reduced pressure is preferable because the reaction time becomes shorter. The degree of reduced pressure is preferably 30 mmHg or less, particularly preferably 10 mmHg or less, at the final stage of the reaction. The progress of the esterification reaction can be determined by the amount of water distilled from the reaction system, the amount of lower alcohol, the acid value of the reaction system, the viscosity, or the Mn of the product.

As polyisocyanate (b) for producing (E2b), polyisocyanates having 2 to 6 or more valences are used, and those conventionally used for polyurethane production are exemplified, and the following (b-1) ) To (b-6).
(b-1) an aromatic polyisocyanate having 6 to 20 carbon atoms (excluding the carbon number in the NCO group);
1,3- and / or 1,4-phenylene diisocyanate, 2,4-, 2,6-tolylene diisocyanate (TDI), crude TDI, 2,4′-, 4,4′-diphenylmethane diisocyanate (MDI), Crude MDI, 4,4′-diisocyanatobiphenyl, 3,3′-dimethyl-4,4′-diisocyanatobiphenyl, 3,3′-dimethyl-4,4′-diisocyanatodiphenylmethane, 1,5 -Naphthylene diisocyanate, 4,4 ', 4 "-triphenylmethane triisocyanate, m- and p-isocyanatophenylsulfonyl isocyanate, polyaryl polyisocyanate (PAPI) and the like;

(b-2) an aliphatic polyisocyanate having 2 to 18 carbon atoms;
Ethylene diisocyanate, hexamethylene diisocyanate (HDI), tetramethylene diisocyanate, dodecane methylene diisocyanate, 1,6,11-undecane triisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, 2,6-diisocyanatomethyl carbonate Proate, bis (2-isocyanatoethyl) fumarate, bis (2-isocyanatoethyl) carbonate, 2-isocyanatoethyl-2,6-diisocyanatohexanoate, trimethylhexamethylene diisocyanate (TMDI), dimer acid Diisocyanate (DDI) and the like;
(b-3) an alicyclic polyisocyanate having 4 to 15 carbon atoms;
Isophorone diisocyanate (IPDI), dicyclohexyl diisocyanate, dicyclohexylmethane diisocyanate (H-MDI), cyclohexylene diisocyanate, hydrogenated tolylene diisocyanate (HTDI), bis (2-isocyanatoethyl) -4-cyclohexene-1,2-dicarboxyl Rate, 2,5- and / or 2,6-norbornane diisocyanate, etc .;
(b-4) an araliphatic polyisocyanate having 8 to 15 carbon atoms;
m- and / or p-xylylene diisocyanate (XDI), α, α, α ′, α′-tetramethylxylylene diisocyanate (TMXDI) and the like;

(b-5) Modified product of the above polyisocyanate;
Examples of modified products include urethane groups, carbodiimide groups, allophanate groups, urea groups, burette groups, uretdione groups, uretonimine groups, isocyanurate groups, oxazolidone group-containing modified products. / Or polymer polyol) adduct body [molar ratio of NCO / OH is preferably 1.01 to 10/1, more preferably 1.1 to 5/1. For example, 1 mol of trimethylolpropane and the diisocyanate 3 described above Molar adducts, pentaerythritol and 4 moles of the above diisocyanates, etc .;

(B-6) diisocyanate polymer;
Isocyanurates of polyisocyanates (trimers, pentamers), burettes of diisocyanates (trimers, pentamers) and the like;
Etc. These may be used in combination of two or more.
Among these, preferred are (b-1) and (b-2), and more preferred are 1,3- and / or 1,4-phenylene diisocyanate, TDI, crude TDI, MDI, ethylene diisocyanate, tetramethylene. Diisocyanate and HDI.

The reaction conditions of (E1) and (b) are not particularly limited, and can be carried out under known urethanization reaction conditions. For example, it can be synthesized by using a urethanization catalyst, preferably a transition metal catalyst (for example, dibutyltin dilaurate) and reacting at 50 to 150 ° C., more preferably at 70 to 130 ° C. for 8 to 20 hours. . The equivalent ratio [(E1) / (b)] of the functional groups of (E1) and (b) is preferably 0.5 to 2.0, more preferably 0.9 to 1.5. When it is 0.5 to 2.0, the lubricity of (E2) is further improved, which is preferable.
Moreover, the solvent similar to the above can be used for reaction as needed. The urethanization reaction can be carried out at normal pressure or under pressure. The progress of the urethanization reaction can be judged by the isocyanate group content, viscosity, Mn of the product, etc. of the reaction system.

(Poly) halides (c) for producing (E2c) are monohalogenated alkyl (c1) having 1 to 24 carbon atoms and polyhalogenated alkyl having 2 to 4 or more carbon atoms having 1 to 4 carbon atoms. (C2) is mentioned, and specifically, the following compounds are mentioned.
(C1) C1-C24 monohalogenated alkyl chloromethane, chloroethane, chloro n-hexane, chloro n-dodecane, etc.
(C2) C1-C4 polyhalogenated alkyl dichloromethane, dichloroethane, bromochloromethane, dibromomethane, dibromoethane, trichloroethylene, 1,3-dichloropropane, 1,3-trichloropropane, 1,2,2 dibromobutane, etc.
Of these, (c2) is preferred among (c), more preferably dichloromethane and dichloroethane, and (E2) using these is easy to handle because of its low viscosity.

  The reaction conditions of (E1) and (c) are not particularly limited and can be synthesized under known etherification reaction conditions. For example, an alkaline compound, preferably an inorganic alkaline compound (for example, sodium hydroxide, potassium hydroxide) is added in an amount of 0.9 to 1.5 equivalents to (c), preferably 50 to 150 ° C., more preferably 70. It can be synthesized at ~ 130 ° C for 6 to 24 hours. The equivalent ratio [(E1) / (c)] of the functional groups of (E1) and (c) is preferably 0.5 to 2.0, more preferably 0.9 to 1.5. If it is 0.5 or more and 2.0 or less, the lubricity of the product is further improved, which is preferable. Also. If necessary, the same solvent as described above can be used for the reaction. The etherification reaction can be carried out at normal pressure or under pressure. The progress of the etherification reaction can be judged by the alkali number, viscosity, Mn of the product, etc. of the reaction system.

  In the cosmetic polyether composition of the present invention, the mass ratio when (E1) and (E2) are used in combination is preferably 99/1 to 1/99, more preferably 90/10 to 10/90.

  The cosmetic polyether composition of the present invention is usually liquid, pasty or solid, and is preferably liquid from the viewpoint of ease of handling.

The cosmetic of the present invention contains the above-described polyether composition and oil and / or inorganic powder, and preferably contains oil and inorganic powder.
Examples of the cosmetics of the present invention include skin care cosmetics such as facial creams, massage creams, hand creams, and nutritional creams, makeup cosmetics such as foundations, makeup creams, lipsticks, and nail enamels, and hair care cosmetics such as hair mousse and hair treatments. .

The cosmetic of the present invention has a good tactile sensation because the polyether composition is excellent in oil compatibility.
Examples of oils that can be used in the cosmetics of the present invention include fats and oils [olive oil, camellia oil, macadamia nut oil, castor oil, etc.], waxes [carnauba wax, candelilla wax, jojoba oil, beeswax etc.], hydrocarbons [liquid paraffin, petrolatum, ceresin, Squalane etc.], higher fatty acids [lauric acid, myristic acid, palmitic acid, stearic acid etc.], higher alcohols [cetyl alcohol, stearyl alcohol, isostearyl alcohol etc.], esters [isopropyl myristate, 2-octyldodecyl myristate, 2-ethylhexanoic acid cetylmalate diisostearyl and the like] and silicone oils [methylpolysiloxane, methylphenylpolysiloxane and the like].

The cosmetic of the present invention is excellent in the tactile sensation, elongation, and lubricity of the cosmetic because the polyether composition is excellent in inorganic powder dispersibility.

Examples of inorganic powders that can be used in the cosmetics of the present invention include metal oxides (silica, diatomaceous earth, alumina, zinc oxide, titanium oxide, calcium oxide, magnesium oxide, iron oxide, tin oxide, antimony oxide, etc.), metal hydroxides ( Calcium hydroxide, magnesium hydroxide, aluminum hydroxide and basic magnesium carbonate), metal carbonates (calcium carbonate, magnesium carbonate, zinc carbonate, barium carbonate, dawsonite, hydrotalcite, etc.), metal sulfates (calcium sulfate, Barium sulfate and gypsum fibers), metal silicates (calcium silicate, talc, kaolin, clay, mica, montmorillonite, bentonite, activated clay, sepiolite, imogolite, sericite, glass fiber, glass beads, silica-based balloon, etc.) Metal nitride (Al nitride) Nium, boron nitride, silicon nitride, etc.), carbons (carbon black, graphite, carbon fiber, carbon balun, charcoal powder, fullerene, etc.), and other inorganic materials (metal powders such as gold, silver, copper and tin, titanium) Potassium oxide, lead zirconate titanate, aluminum borate, molybdenum sulfide, silicon carbide, stainless steel fiber, zinc borate, slag fiber, Teflon powder, wood powder, pulp, rubber powder, and aramid fiber).
These may be used alone or in combination of two or more.

The inorganic powder may be treated with a surface treatment agent as necessary.
As the surface treatment agent, a known treatment agent can be used. For example, a silane coupling agent [γ-chloropropyltrimethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, vinyl tris (β-methoxyethoxy) silane, γ-methacryloxypropyltrimethoxysilane and β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane etc.], titanate coupling agent [isopropyl triisostearoyl titanium etc.], aluminate coupling agent [acetoalkoxyaluminum di Isopropylate, etc.], fatty acids [stearic acid, oleic acid, linoleic acid, linolenic acid, eleostearic acid, etc.], fats and oils [coconut oil, rice dregs oil, soybean oil, flaxseed oil, dehydrated castor oil, safflower oil and tung oil Etc.], polyethylene glycol Type nonionic surfactant [higher alcohol EO adduct, fatty acid EO adduct, higher alkylamine EO adduct, polypropylene glycol EO adduct, etc.], polyhydric alcohol type nonionic surfactant [glycerin fatty acid ester, penta Eryslit fatty acid ester, sorbit or sorbitan fatty acid ester, polyhydric alcohol alkyl ether and alkanolamine aliphatic amide, etc.], wax [maleated polypropylene and maleated polyethylene, etc.], carboxylic acid coupling agent [carboxylated polybutadiene And carboxylated polyisoprene etc.], and phosphoric acid coupling agents [monooctyl phosphate, mono (2,6-dimethyl-7-octenyl) phosphate, mono (6-mercaptohexyl) phosphate Ester and mono (2-methacryloxypropyl) phosphate, etc.].
The surface treatment can be performed by mixing the inorganic powder and the surface treatment agent at room temperature or 30 to 200 ° C. while mixing them under normal pressure or reduced pressure. The mass ratio of the inorganic powder to the surface treatment agent is 1 to 100 parts by mass of the surface treatment agent with respect to 100 parts by mass of the inorganic powder.

The shape of the inorganic powder may be any of a spherical shape, a granular shape, a star shape, or an irregular granular shape.
The weight average particle diameter of the inorganic powder is usually 1 nm to 10 μm, preferably 10 nm to 1 μm.

The cosmetic product of the present invention may further contain other components as necessary.
For example, for skin cosmetics, surfactants, moisturizers, UV absorbers, alcohols, chelating agents, pH adjusters, preservatives, other thickeners, pigments and fragrances commonly used as skin cosmetic ingredients Can be used.
For hair cosmetics, surfactants, anionic polymers, silicones, other thickeners, UV absorbers, pearlizing agents, antioxidants, preservatives, pigments, and fragrances that are commonly used as hair cosmetic ingredients Can be used.

The content of the polyether composition of the present invention based on the mass of the cosmetic product of the present invention varies depending on the intended use of cosmetics, properties (liquid, solid), etc., but is usually 0.1 to 60% (in the following,% is mass) %), Preferably 0.2-30%, oil content 0.01-70%, preferably 0.01-40%, inorganic powder usually 0.1-70%, preferably 0.1 ~ 40%.
Examples of the formulation of the cosmetic of the present invention include the following foundation lotions.
8-20% of the polyether composition of the present invention
Stearic acid and its glycerin ester 2-8%
Liquid paraffin (oil) 10-40%
Triethanolamine 1-3%
Propylene glycol 5-10%
Titanium oxide (inorganic powder) 3-9%
Bentonite (inorganic powder) 3-15%
Preservative Appropriate amount of perfume Appropriate amount of purified water 100%

<Example>
EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. In addition, below, a part shows a mass part. In the following, Examples 2 and 4 are reference examples.

Example 1
A glass autoclave was charged with 186 parts (1.0 mole) of lauryl alcohol, 468 parts (6.5 moles) of tetrahydrofuran (THF) and 7.9 parts of BF ₃ · THF, and 580 parts of PO (10.0 parts) from a pressure-resistant dropping funnel. Mol) was added dropwise at 35 to 50 ° C. over 10 hours. Thereafter, it was aged at 50 ° C. for 5 hours and cooled. Further, after adding 4.8 parts of 48% NaOH aqueous solution, an adsorption treatment agent [manufactured by Kyowa Chemical Industry Co., Ltd .; Kyoward 600 and Kyoward 1000. The same shall apply hereinafter. ], Filtered, and dehydrated under reduced pressure at 130 ° C. and 30 mmHg or less to obtain 1,230 parts (E1-1) of a lauryl alcohol THF 6.5 mol / PO 10.0 mol random adduct.

Example 2
617 parts (0.5 mol) of (E1-1) obtained in Example 1 and 25 parts (0.25 mol) of succinic anhydride were reacted at 120 ° C. for 12 hours while bubbling nitrogen through the liquid. Polyether (E2-1) was obtained. (E2-1) was liquid at room temperature, and the acid value (measured according to JIS K 1557) was 3.0.

Example 3
A glass autoclave was charged with 130 parts (1.0 mol) of 2-ethylhexyl alcohol, 504 parts (7.0 mol) of THF, and 7.9 parts of BF ₃ · THF, and 580 parts (10.0 mol) of PO from a pressure-resistant dropping funnel. Was added dropwise at 35 to 50 ° C. over 10 hours. Thereafter, it was aged at 50 ° C. for 5 hours and cooled. Thereafter, the same treatment as in Example 1 was performed to obtain 1,100 parts (E1-2) of 2-ethylhexyl alcohol THF 7.0 mol / PO 10.0 mol random adduct.

Example 4
A glass autoclave was charged with 62 parts (1.0 mol) of ethylene glycol, 1008 parts (14.0 mol) of THF, and 7.9 parts of BF ₃ .THF, and 880 parts (20.0 mol) of EO was added from a pressure-resistant dropping funnel. It dripped over 10 hours at -50 degreeC. Thereafter, it was aged at 50 ° C. for 5 hours and cooled. Thereafter, the same treatment as in Example 1 was performed to obtain 1,760 parts (E1-3) of an ethylene glycol THF 14.0 mol / EO 21.0 mol random adduct.

Comparative Example 1
200 parts (1.0 mol) of lauryl alcohol and 3.3 parts of KOH were charged into a glass autoclave, and 836 parts (19.0 mol) of EO was added dropwise from a pressure-resistant dropping funnel at 105 ° C. over 33 hours. Thereafter, it was aged at 130 ° C. for 10 hours and cooled. Furthermore, it processed with the adsorption processing agent, filtered, and dehydrated under reduced pressure at 130 degreeC and 30 mmHg or less, and obtained 1,036 parts of EO 19.0 mol adducts of lauryl alcohol.

The oil compatibility of the polyether compositions obtained in the above examples and comparative examples was evaluated.
Evaluation test method;
In a 200 ml glass beaker, 10 parts of the polyether composition and 70 parts of mineral oil (spindle oil) were placed, stirred at room temperature with a glass rod having a diameter of 5 mm at a speed of about 200 rpm / min for 5 minutes, and then mixed. It was allowed to stand for minutes and the appearance was visually observed. The results are shown in Table 1.
○: Transparent and uniform
Δ: cloudiness
×: Two-layer separation

  The polyether composition for cosmetics of the present invention is a skin care cosmetic such as a face-wash cream, massage cream, hand cream, and nutrition cream, a makeup cosmetic such as a foundation, makeup cream, lipstick, and nail enamel, and a hair care cosmetic such as hair mousse and hair treatment. Can be used for etc.

Claims (3)

Polyether (E1) represented by the general formula (1) and / or Etherified product (E2c) obtained from (E1) and (poly) halide A polyether composition for cosmetics, comprising:
Formula _{^{R 1 - {(OCH 2 CH}} 2 CH 2 CH 2) m (OA) n -OH} q (1)
[Wherein, R ¹ is a residue obtained by removing OH from a C1-C24 q-valent alcohol, A is a 1,2-propylene group , q is an integer of 1-6, m and n are 1- It is an integer of 600, and the portion of (OCH ₂ CH ₂ CH ₂ CH ₂ ) _m (OA) _n represents a random bond or a block bond. ] The polyether composition for cosmetics according to claim 1, wherein (E1) has an HLB of 10 or less and a number average molecular weight of 500 to 30,000. A cosmetic comprising the polyether composition according to claim 1 or 2 and an oil and / or inorganic powder.