Oil agent composition for cosmetic and cosmetic containing said oil agent composition for cosmetic

Abstract

The present invention relates to an oil agent composition for a cosmetic containing an alkylene oxide adduct (A) represented by formula (1).　(1): R-[O(PO)b / (EO)a-H]n, wherein in formula (1), R is a residue obtained by removing all hydroxyl groups from a compound having n hydroxyl groups; n is 4 or 6; EO and PO represent an ethyleneoxy group and a propyleneoxy group, respectively; a and b are an average number of moles added of ethyleneoxy group and propyleneoxy group, respectively; and 10≤a×n≤20 and 90≤b×n≤120.]

Description

Cosmetic oil composition and cosmetic containing said cosmetic oil composition

[0001] The present invention relates to a cosmetic oil composition and a cosmetic containing the cosmetic oil composition.

[0002] Traditionally, naturally occurring lanolin has been used in many cosmetics due to its excellent affinity to skin, water-holding properties, and moisturizing properties. However, due to concerns about infectious diseases such as mad cow disease and animal welfare concerns, lanolin has been replaced by synthetic products and plant-derived water-holding oils. Known examples of lanolin substitutes include dipentaerythritol esters, which have high adhesion to skin, excellent water-holding properties, moisturizing properties, and waterproof film-forming ability, as well as pigment dispersibility and stability over time, and cosmetics containing such esters (Patent Document 1). Dimer diol derivatives, which have excellent water-holding properties, moisturizing properties, and pigment dispersibility and are highly safe, and cosmetics containing such esters are also known (Patent Document 2).

[0003] Patent No. 5395325 Public Information Patent No. 3889657

[0004] However, both lanolin and lanolin substitutes become cloudy and opaque when hydrated, which limits the appearance of cosmetics.The present invention aims to provide a cosmetic oil composition that has excellent water-holding properties, is colorless and transparent in appearance after hydration, and has excellent solubility of UV absorbers and dispersibility of pigments, as well as cosmetics containing the cosmetic oil composition that provide excellent moist feeling and non-stickiness to skin and hair.

[0005] The present inventors have conducted extensive research to solve the above problems and have arrived at the present invention. That is, the present invention relates to a cosmetic oil composition containing an alkylene oxide adduct (A) represented by the following formula (1): R—[O(PO) ｂ / (EO) ａ -H] ｎ...(1) [in formula (1), R is a residue obtained by removing all hydroxyl groups from a compound having n hydroxyl groups, n is 4 or 6, EO and PO are ethyleneoxy and propyleneoxy groups, respectively, a and b are the average numbers of moles of ethyleneoxy and propyleneoxy groups added, respectively, and 10≦a×n≦20, 90≦b×n≦120], and a cosmetic comprising the cosmetic oil composition.

[0006] The cosmetic oil composition of the present invention has excellent water-holding properties, is colorless and transparent in appearance after water-holding, and has excellent UV solubility and pigment dispersibility. Furthermore, cosmetics containing the cosmetic oil composition of the present invention provide excellent moist feeling and non-stickiness to skin and hair.

[0007] The present invention will be described in detail below. In this specification, the names of compounds may be described using the display names or alternative display names listed in the "List of Cosmetics Display Names" compiled by the Japan Cosmetic Industry Association.

[0008] The cosmetic oil composition of the present invention contains an alkylene oxide adduct (A) represented by the following formula (1): R—[O(PO) ｂ / (EO) ａ -H] ｎ ... (1) In formula (1), R is a residue obtained by removing all hydroxyl groups from a compound having n hydroxyl groups, n is 4 or 6, EO and PO are ethyleneoxy and propyleneoxy groups, respectively, a and b are the average numbers of moles of ethyleneoxy and propyleneoxy groups added, respectively, and 10≦a×n≦20, 90≦b×n≦120.

[0009] The alkylene oxide adduct (A) represented by the formula (1) is a compound having a structure in which ethylene oxide and propylene oxide are added to all hydroxyl groups of a compound having n hydroxyl groups. In formula (1), n ​​is 4 or 6, preferably 4. Examples of compounds having four hydroxyl groups include diglycerin, erythritol, pentaerythritol, sorbitan, and methyl glucoside. Examples of compounds having six hydroxyl groups include sorbitol. Of these, diglycerin, pentaerythritol, and sorbitol are preferred from the perspective of the feel when used in cosmetics. In the cosmetic oil composition of the present invention, the compound having n hydroxyl groups is preferably at least one selected from the group consisting of diglycerin, pentaerythritol, and sorbitol, and more preferably diglycerin or pentaerythritol.

[0010] In the formula (1), a and b are the average number of moles of ethyleneoxy groups and propyleneoxy groups added, respectively, and each is independently a value of 0 or greater. The average number of moles of ethyleneoxy groups added (a) is preferably 2.5 or greater and 5 or less, and more preferably 3 or greater and 4 or less. If a is less than 2.5, the moist feeling of the skin when using the cosmetic preparation may deteriorate, and if it exceeds 5, the non-stickiness of the skin when using the cosmetic preparation may deteriorate. The average number of moles of propyleneoxy groups added (b) is preferably 22.5 or greater and 30 or less, more preferably 22.75 or greater and 30 or less, and even more preferably 22.75 or greater and 25 or less. If b is less than 22.5, the water holding ability of the cosmetic oil composition may deteriorate, and if it exceeds 30, the water holding ability of the cosmetic oil composition may also deteriorate. The ratio (b / a) of the average number of moles of propyleneoxy groups added to the average number of moles of ethyleneoxy groups added is from 4.5 to 12, preferably from 5 to 11.5, and more preferably from 6 to 11. If b / a is less than 4.5, the cosmetic oil composition will be water-soluble and will not have water-holding ability.

[0011] In the formula (1), the value (a×n) obtained by multiplying the average number of moles of ethyleneoxy groups added (a) by n is from 10 to 20, and preferably from 12 to 16. If a×n is less than 10, the moist feeling of the skin when using the cosmetic may deteriorate, and if it exceeds 20, the non-stickiness of the skin when using the cosmetic may deteriorate. Furthermore, in the formula (1), the value (b×n) obtained by multiplying the average number of moles of propyleneoxy groups added (b) by n is from 90 to 120, preferably from 91 to 120, and more preferably from 91 to 100. If b×n is less than 90, the water holding ability of the cosmetic oil composition may deteriorate, and if it exceeds 120, the water holding ability of the cosmetic oil composition may also deteriorate.

[0012] The bonding form (polymerization form) of the ethyleneoxy group and the propyleneoxy group is not particularly limited, and examples thereof include block polymerization and random polymerization. From the viewpoint of achieving both water holding ability and non-stickiness, block polymerization is preferred. In the formula (1), "(PO) ｂ / (EO) ａ " indicates that the positions of EO and PO (the order of ethylene oxide and 1,2-propylene oxide added to a compound having n hydroxyl groups) are not particularly limited. That is, in the cosmetic oil composition of the present invention, the alkylene oxide adduct (A) represented by the formula (1) does not necessarily have to be one obtained by adding 1,2-propylene oxide first and then ethylene oxide when carrying out a reaction of adding ethylene oxide and 1,2-propylene oxide to a compound having n hydroxyl groups, but may be one obtained by adding ethylene oxide first and then 1,2-propylene oxide, or may be one obtained by co-addition (random polymerization) of ethylene oxide and 1,2-propylene oxide.

[0013] The a and b are the number average molecular weight (Mn) of the alkylene oxide adduct (A) calculated using the hydroxyl value (mgKOH / g) of the alkylene oxide adduct (A), and the number average molecular weight (Mn) of the alkylene oxide adduct (A) calculated using the proton nuclear magnetic resonance ( １The hydroxyl value of the alkylene oxide adduct (A) can be calculated from the ratio of ethyleneoxy groups to propyleneoxy groups determined by measuring 1H-NMR. The hydroxyl value of the alkylene oxide adduct (A) can be calculated based on the amounts of the compound having n hydroxyl groups (unreacted compound) and the alkylene oxide adduct of the compound having n hydroxyl groups. For example, it can be measured by Method A described in JIS K1557-1, Plastics - Polyurethane Raw Material Polyol Test Methods, Part 1: Determination of Hydroxyl Value.

[0014] The number average molecular weight (Mn) of the alkylene oxide adduct (A) can be calculated by the following formula 1 using the hydroxyl value (mg KOH / g) of the alkylene oxide adduct (A) measured by Method A described in JIS K1557-1, Plastics - Polyurethane Raw Material Polyol Test Methods, Part 1: Determination of Hydroxyl Value: Number average molecular weight (Mn) of alkylene oxide adduct (A) = (4 × 56,100) / hydroxyl value of alkylene oxide adduct (A) [mg KOH / g] (Formula 1)

[0015] In the alkylene oxide adduct (A), the ratio of the average number of moles of propyleneoxy groups to the average number of moles of ethyleneoxy groups is determined by dissolving 10 mg of the alkylene oxide adduct (A) in 0.5 ml of deuterated chloroform under the following conditions: １ H-NMR measurement is performed, and the ratio of the integral values ​​of the peak observed between 0.6 and 1.4 ppm to the integral value of the peak observed between 3.0 and 4.0 ppm in the obtained NMR chart can be calculated. １ H-NMR measurement conditions] Apparatus: BRUKER AVANCE III 400HD (frequency: 400 MHz, manufactured by BRUKER OPTICS) Sample temperature: 25°C Number of accumulations: 16

[0016] １In the NMR chart obtained by H-NMR measurement, the peak observed between 0.6 and 1.4 ppm is a peak derived from three hydrogen atoms bonded to the methyl group of the propyleneoxy group, and the peak observed between 3.0 and 4.0 ppm is a peak derived from a total of four hydrogen atoms bonded to the ethylene group of the ethyleneoxy group, two hydrogen atoms bonded to the methylene group of the propyleneoxy group, and one hydrogen atom bonded to the methine group of the propyleneoxy group. Therefore, the ratio (b / a) of the total number of moles of ethyleneoxy groups to the total number of moles of propyleneoxy groups contained in the alkylene oxide adduct (A) can be calculated from the ratio of the integral values ​​of the two peaks using the following (Equation 2):

[0017] (b / a)=(4 / 3)×{S １ / (S ２ -S １ )} (Formula 2) [In Formula 2, S １ is the integral value of the peak observed between 0.6 and 1.4 ppm, and S ２ is the integral value of the peak observed between 3.0 and 4.0 ppm.]

[0018] The alkylene oxide adduct (A) can be produced by adding ethylene oxide and 1,2-propylene oxide to a compound having n hydroxyl groups in the presence of a catalyst so that the value (a×n) obtained by multiplying the average number of moles of ethyleneoxy groups added (a) by n and the value (b×n) obtained by multiplying the average number of moles of propyleneoxy groups added (b) by n fall within the above-mentioned ranges (hereinafter, this reaction will be referred to as an alkylene oxide addition reaction). More specifically, the alkylene oxide addition reaction can be carried out by a known method, such as a method in which ethylene oxide and 1,2-propylene oxide are added dropwise to a mixture of a compound having n hydroxyl groups and a catalyst. Among these, a reaction product obtained by adding ethylene oxide and propylene oxide to pentaerythritol is preferred, a reaction product obtained by adding 10 to 20 moles of ethylene oxide and 90 to 120 moles of 1,2-propylene oxide to 1 mole of pentaerythritol is more preferred, and a reaction product obtained by adding 10 to 20 moles of ethylene oxide and 90 to 100 moles of 1,2-propylene oxide to 1 mole of pentaerythritol is particularly preferred.

[0019] From the viewpoint of the reaction activity of the catalyst, it is preferable to perform a dehydration treatment on a mixture of the compound having n hydroxyl groups and the catalyst before carrying out the alkylene oxide addition reaction. The dehydration treatment is preferably carried out by mixing the compound having n hydroxyl groups and the catalyst in a reaction vessel (e.g., a stainless steel autoclave equipped with a stirrer and a temperature control function), adjusting the temperature inside the reaction vessel to 80 to 300°C (preferably 80 to 120°C) under normal pressure or reduced pressure (preferably under reduced pressure, more preferably under reduced pressure after replacing the atmosphere in the reaction vessel with nitrogen), and performing the dehydration treatment for 1 to 4 hours.

[0020] The catalyst may be an acid catalyst or an alkali catalyst, and is preferably an alkali catalyst. The catalyst may be used alone or in combination of two or more kinds.

[0021] Examples of acidic catalysts include perhalogen acids and / or their salts, sulfuric acid and / or its salts, phosphoric acid and / or its salts, nitric acid and / or its salts, and perfluoroalkylsulfonic acid metal salts. Examples of halogens in perhalogen acids and / or their salts include chlorine, bromine, and iodine, with chlorine being preferred from the viewpoint of reactivity. Examples of perhalogen salts, sulfate salts, phosphate salts, and nitrate salts include sodium salts, potassium salts, magnesium salts, and ammonium salts, respectively. Examples of perfluoroalkylsulfonic acid metal salts include trifluoromethanesulfonic acid metal salts and pentafluoroethanesulfonic acid metal salts. The metal that forms a salt with perfluoroalkylsulfonic acid is not particularly limited, but is preferably a divalent or trivalent metal from the viewpoint of reactivity. Examples of divalent or trivalent metals include magnesium, calcium, scandium, barium, zinc, cobalt, nickel, copper, aluminum, cadmium, titanium, hafnium, chromium, molybdenum, manganese, iron, palladium, and rare earth metal atoms, and preferred are magnesium, zinc, aluminum, titanium, iron, and scandium.

[0022] Examples of the alkali catalyst include hydroxides of alkali metals (lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, etc.), hydroxides of alkaline earth metals (magnesium hydroxide, calcium hydroxide, barium hydroxide, etc.), tertiary amines (triethylamine, trimethylamine, etc.), and quaternary ammonium salts (tetramethylammonium hydroxide, etc.), of which potassium hydroxide, sodium hydroxide, and cesium hydroxide are preferred, and potassium hydroxide is more preferred.

[0023] The amount of the acid catalyst or alkali catalyst used is preferably 0.0001 to 1% by weight, more preferably 0.001 to 0.5% by weight, based on the total weight of the compound having n hydroxyl groups, ethylene oxide, and 1,2-propylene oxide, from the viewpoints of the reaction rate of the alkylene oxide addition reaction and the viscosity of the resulting alkylene oxide adduct (A).

[0024] Furthermore, from the viewpoint of facilitating stirring of the mixture of the compound having n hydroxyl groups and the catalyst before the alkylene oxide addition reaction and stirring during the alkylene oxide addition reaction, the alkylene oxide addition reaction may be carried out by further adding a solvent to the mixture of the compound having n hydroxyl groups and the catalyst. The compound having n hydroxyl groups, the catalyst, and the solvent may be mixed in a reaction vessel, or a mixture may be premixed and placed in a reaction vessel to carry out the reaction. Examples of the solvent include toluene, xylene, benzene, dimethyl sulfoxide, diglyme, triglyme, 1,4-dioxane, cyclohexane, hexane, diethyl ether, dimethylformamide, carbon tetrachloride, N-methylpyrrolidone, 1,2-dimethoxyethane, 1,2-dichloroethane, chloroform, and dialkyl polypropylene glycol. The solvent may be used alone or in combination of two or more.

[0025] As the solvent, toluene and xylene are preferred from the viewpoints of miscibility with the compound having n hydroxyl groups and the catalyst and ease of distillation. When the alkylene oxide adduct (A) is produced using a solvent, the solvent may be distilled off before use in the cosmetic oil composition, or may be used without being distilled off. As a method for distilling off the solvent, a known method such as distilling the solvent under reduced pressure using an evaporator can be used.

[0026] From the viewpoint of reaction rate and the like, the amount of the solvent used in the alkylene oxide addition reaction is preferably 99% by weight or less, and more preferably 90% by weight or less, based on the total weight of the compound having n hydroxyl groups, the catalyst, ethylene oxide, and 1,2-propylene oxide.

[0027] The reaction temperature in the alkylene oxide addition reaction may be 100 to 200°C, preferably 105 to 150°C, and more preferably 110 to 145°C, from the viewpoint of the reaction rate of the alkylene oxide addition reaction.

[0028] When the alkylene oxide addition reaction is carried out in the presence of an alkali catalyst, a step of adsorbing and removing the alkali catalyst in the reaction mixture with an adsorbent may be carried out after the alkylene oxide addition reaction. Preferred adsorbents include magnesium silicate [e.g., Kyoward 600 (manufactured by Kyowa Chemical Industry Co., Ltd.) (Kyoward is a registered trademark of Kyowa Chemical Industry Co., Ltd.)] and aluminum silicate [e.g., Kyoward 700 (manufactured by Kyowa Chemical Industry Co., Ltd.)].

[0029] From the viewpoints of the efficiency of adsorption and removal and shortening the time required for the adsorption and removal process, the weight of the adsorbent used is preferably 3.0% by weight or less, and more preferably 2.0% by weight or less, based on the total weight of the compound having n hydroxyl groups, catalyst, ethylene oxide, and 1,2-propylene oxide used in the alkylene oxide addition reaction.

[0030] The cosmetic oil composition of the present invention may be the alkylene oxide adduct (A) itself, or may contain, in addition to the alkylene oxide adduct (A), a known oil composition other than the alkylene oxide adduct (A). When a known oil composition other than the alkylene oxide adduct (A) is contained, the content thereof is preferably 1 to 50 wt %, and more preferably 1 to 25 wt %, based on the weight of the cosmetic oil composition.

[0031] The cosmetic of the present invention contains the cosmetic oil composition. The cosmetic of the present invention may contain known optional components in addition to the cosmetic oil composition, as long as the effects of the present invention are not impaired. Examples of optional components include known cosmetic raw material components used as cosmetic raw materials, such as water, oils, silicone compounds, alcohols, gelling agents, anionic surfactants, nonionic surfactants other than the alkylene oxide adduct (A), amphoteric surfactants, cationic surfactants, inorganic pigments, polymeric compounds, chelating agents, pH adjusters, cooling agents, whitening agents, moisturizers, UV absorbers, conditioning agents, fragrances, colorants, and preservatives. The optional components may be used alone or in combination of two or more.

[0032] Examples of oils include fats and oils (almond oil, olive oil, soybean oil, hardened oil, camellia oil, rapeseed oil, castor oil, coconut oil, beef tallow, lard, etc.), waxes (lanolin, beeswax, jojoba oil, candelilla wax, etc.), higher fatty acids (lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, undecylenic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid (DHA), isostearic acid, 12-hydroxystearic acid, etc.), esters of fatty acids and alcohols (caprylic / capric triglyceride, ethylhexyl palmitate, etc.), and hydrocarbons (ceresin, paraffin, mineral oil, petrolatum, squalane, liquid paraffin, etc.). One type of oil may be used alone, or two or more types may be used in combination.

[0033] Examples of silicone compounds include methylphenylpolysiloxane, methylpolysiloxane, octamethylcyclotetrasiloxane, dimethylsiloxane / methyl(polyoxyethylene)siloxane copolymer, decamethylcyclopentanesiloxane, dimethylsiloxanemethyl(polyoxyethylene / polyoxypropylene)siloxane copolymer, methylhydrogenpolysiloxane, dodecamethylcyclohexanesiloxane, methylpolycyclosiloxane, dimethylsiloxane / methylstearyloxysiloxane copolymer, methylpolysiloxane emulsion, octamethyltrisiloxane, cyclic silicone resin, highly polymerized methylpolysiloxane, tetradecamethylhexanesiloxane, and trimethylsiloxysilicate. One type of silicone compound may be used alone, or two or more types may be used in combination.

[0034] Examples of alcohols include monohydric alcohols (methanol, ethanol, isopropyl alcohol, n-butyl alcohol, lauryl alcohol, myristyl alcohol, palmityl alcohol (cetanol), cetyl alcohol, stearyl alcohol, behenyl alcohol, hexadecyl alcohol, oleyl alcohol, isostearyl alcohol, hexyldodecanol, octyldodecanol, cetearyl alcohol, 2-decyltetradecynol, cholesterol, phytosterol, polyoxyethylene cholesteryl ether, monostearyl glycerin ether (batyl alcohol), monooleyl glyceryl ether (selachyl alcohol), and medufoam seed oil), dihydric to hexahydric polyhydric alcohols (ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, 1,3-butanediol (1,3-butylene glycol), 1,2-pentanediol, hexylene glycol, glycerin, diglycerin, and sorbitol), and cholesterol. The alcohols may be used alone or in combination of two or more.

[0035] Examples of gelling agents include guar gum, starch, carboxymethyl cellulose, acetyl methyl cellulose, polyvinyl alcohol, disteardimonium hectorite, sucrose palmitate, dextrin stearate, monobenzylidene sorbitol, and N-lauroyl-L-glutamic acid, etc. One type of gelling agent may be used alone, or two or more types may be used in combination.

[0036] Examples of anionic surfactants include hydrocarbon ether carboxylic acids having 8 to 24 carbon atoms or salts thereof [such as sodium (poly)oxyethylene lauryl ether acetate and disodium (poly)oxyethylene lauryl sulfosuccinate], hydrocarbon sulfate ester salts having 8 to 24 carbon atoms [sodium lauryl sulfate, sodium (poly)oxyethylene lauryl sulfate, (poly)oxyethylene lauryl triethanolamine sulfate, and sodium (poly)oxyethylene coconut oil fatty acid monoethanolamide sulfate], hydrocarbon sulfonates having 8 to 24 carbon atoms [sodium dodecylbenzenesulfonate], and Examples of anionic surfactants include hydrocarbon phosphate salts of 8 to 24 [such as sodium lauryl phosphate and sodium (poly)oxyethylene lauryl ether phosphate], fatty acid salts [such as sodium laurate and triethanolamine laurate], and acylated amino acid salts [sodium coconut oil fatty acid methyl taurate, sodium coconut oil fatty acid sarcosine, triethanolamine coconut oil fatty acid sarcosine, triethanolamine N-coconut oil fatty acid acyl-L-glutamate, sodium N-coconut oil fatty acid acyl-L-glutamate, disodium cocoyl glutamate, and sodium lauroylmethyl-β-alanine]. One type of anionic surfactant may be used alone, or two or more types may be used in combination.

[0037] Examples of nonionic surfactants other than the alkylene oxide adduct (A) include aliphatic alcohol (8 to 24 carbon atoms) alkylene oxide (2 to 8 carbon atoms) adducts, (poly)oxyalkylene (2 to 8 carbon atoms) higher fatty acid (8 to 24 carbon atoms) esters [polyethylene glycol monostearate (steareth-20, etc.) and polyethylene glycol distearate, etc.], polyhydric (dihydric to decahydric or higher) alcohol fatty acid (8 to 24 carbon atoms) esters [polyglyceryl-6 polyricinoleate, polyglyceryl-2 isostearate, glycerin monostearate, ethylene glycol monostearate, sorbitan monolaurate, etc.], (poly)oxyalkylene (2 to 8 carbon atoms) polyhydric (dihydric to decahydric or higher) alcohol higher fatty acid (8 to 24 carbon atoms) esters [polyoxyethylene sorbitan monolaurate, etc.], and polyoxyethylene dioleic acid methyl glucoside, etc.], fatty acid alkanolamides [1:1 type coconut oil fatty acid diethanolamide and 1:1 type lauric acid diethanolamide, etc.], (poly)oxyalkylene (2 to 8 carbon atoms) alkyl (1 to 22 carbon atoms) phenyl ethers, (poly)oxyalkylene (2 to 8 carbon atoms) alkyl (8 to 24 carbon atoms) amino ethers, and alkyl (8 to 24 carbon atoms) dialkyl (1 to 6 carbon atoms) amine oxides [lauryl dimethylamine oxide, etc.], etc., which do not contain a triad consisting of an oxypropylene unit in the oxyalkylene chain, or compounds in which the ratio of the number of isotactic triads in the oxypropylene chain contained in the oxyalkylene chain is less than 26% relative to the total number of isotactic triads, heterotactic triads, and syndiotactic triads. Nonionic surfactants other than the alkylene oxide adduct (A) may be used alone or in combination of two or more types.

[0038] Examples of amphoteric surfactants include betaine-type amphoteric surfactants [coconut oil fatty acid amidopropyl betaine, coconut oil fatty acid amidopropyl dimethylaminoacetic acid betaine, lauryl dimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine, lauryl hydroxysulfobetaine, and lauroyl amidoethyl hydroxyethyl carboxymethyl betaine hydroxypropyl sodium phosphate] and amino acid-type amphoteric surfactants [sodium β-laurylaminopropionate]. One type of amphoteric surfactant may be used alone, or two or more types may be used in combination.

[0039] Examples of cationic surfactants include tetraalkyl (C1 to C18) ammonium salts [behentrimonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, etc.] and alkyl (C1 to C4) sulfate higher fatty acid aminoalkyl (C2 to C4) trialkyl (C1 to C4) ammonium salts [lanolin fatty acid aminopropylethyldimethylammonium ethyl sulfate, etc.]. One type of cationic surfactant may be used alone, or two or more types may be used in combination.

[0040] Examples of inorganic pigments include mica, talc, calcium carbonate, red iron oxide, yellow iron oxide, black iron oxide, carbon black, and titanium oxide. One type of inorganic pigment may be used alone, or two or more types may be used in combination.

[0041] Examples of polymer compounds include natural polymers (locust bean gum, carrageenan, galactan, gum arabic, xanthan gum, gelatin, collagen, etc.), semi-synthetic polymers (methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, cationized cellulose, soluble starch, propylene glycol alginate, etc.), and synthetic polymers (polyvinylpyrrolidone, carboxyvinyl polymer, polyacrylic acid ester copolymer, amphoteric methacrylic acid ester copolymer, cationized polyurethane polymer, highly polymerized polyethylene glycol, polyoxyethylene polyoxypropylene block polymer, etc.). One type of polymer compound may be used alone, or two or more types may be used in combination.

[0042] Examples of the chelating agent include ethylenediaminetetraacetic acid, polyphosphoric acid, pyrophosphoric acid, gluconic acid, ascorbic acid, and salts thereof. One type of chelating agent may be used alone, or two or more types may be used in combination.

[0043] Examples of pH adjusters include potassium carbonate, sodium bicarbonate, ammonium bicarbonate, lactic acid, succinic acid, citric acid, etc. The pH adjusters may be used alone or in combination of two or more.

[0044] Examples of the cooling agent include L-menthol and camphor, etc. The cooling agent may be used alone or in combination of two or more kinds.

[0045] Examples of whitening agents include arbutin, kojic acid, glutathione, hydroquinone, hydroquinone derivatives, resorcinol, resorcinol derivatives, and glabrene. One type of whitening agent may be used alone, or two or more types may be used in combination.

[0046] Examples of moisturizing agents include sodium lactate, sodium pyrrolidone carboxylate, sodium hyaluronate, chondroitin sulfate, etc. One type of moisturizing agent may be used alone, or two or more types may be used in combination.

[0047] Examples of ultraviolet absorbers include benzophenone derivatives [t-butyl methoxydibenzoylmethane, diethylaminohydroxybenzoyl hexyl benzoate, etc.], para-aminobenzoic acid derivatives [ethylhexyl dimethyl PABA, etc.], methoxycinnamic acid derivatives [ethylhexyl methoxycinnamate, etc.], salicylic acid derivatives [ethylhexyl salicylate, etc.], urocanic acid derivatives, and octocrylene. One type of ultraviolet absorber may be used alone, or two or more types may be used in combination.

[0048] Examples of conditioning agents include cationized cellulose with a Mw of 500 to 5,000,000, cationized guar gum (guar gum trimonium chloride, etc.), sodium polyacrylate, protein derivatives, ceramides, pseudoceramides, fatty acids having 16 to 40 carbon atoms, panthenol, etc. One type of conditioning agent may be used alone, or two or more types may be used in combination.

[0049] Examples of fragrances include d-limonene, β-caryophyllene, cis-3-hexenol, linalool, farnesol, β-phenylethyl alcohol, 2,6-nonadienal, citral, α-hexyl cinnamic aldehyde, β-ionone, 1-carvone, cyclopentadecanone, linalyl acetate, benzyl benzoate, γ-undecalactone, eugenol, rose oxide, indole, phenylacetaldehyde dimethyl acetal, aurantiol, cinnamic aldehyde, methyl ionone musk, anise essential oil, cinnamon essential oil, and jasmine essential oil. One type of fragrance may be used alone, or two or more types may be used in combination.

[0050] Examples of coloring agents include Blue No. 1, Blue No. 2, Green No. 3, and Red No. 1, and all of the coloring agents that can be used in cosmetics can be used. Only one type of coloring agent can be used alone, or two or more types can be used in combination.

[0051] Examples of preservatives include phenoxyethanol, o-cymen-5-ol, methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, etc. One type of preservative may be used alone, or two or more types may be used in combination.

[0052] The types and contents of known optional components are not particularly limited and can be adjusted depending on the intended use of the cosmetic oil composition. The preferred contents of the optional components are as follows: The contents of oils, silicone compounds, alcohols, anionic surfactants, nonionic surfactants other than the alkylene oxide adduct (A), amphoteric surfactants, cationic surfactants, inorganic pigments, polymeric compounds, and moisturizers are each preferably 50% by weight or less, more preferably 10% by weight or less, based on the total weight of the cosmetic. The contents of gelling agents, chelating agents, whitening agents, and conditioning agents are each preferably 50% by weight or less, more preferably 10% by weight or less, based on the total weight of the cosmetic. The contents of pH adjusters, cooling agents, UV absorbers, fragrances, colorants, and preservatives are each preferably 10% by weight or less, more preferably 5% by weight or less, based on the total weight of the cosmetic.

[0053] When the cosmetic of the present invention contains water, the content of water is appropriately selected depending on the type of cosmetic, but is preferably 10 to 98 wt %, and more preferably 20 to 95 wt %, based on the total weight of the cosmetic.

[0054] The cosmetic of the present invention can be prepared by uniformly mixing the cosmetic oil composition of the present invention with known optional components, if necessary, using a homodisper, etc. Examples of stirring blades that can be used for mixing include paddle-type stirring blades and spiral-type stirring blades.

[0055] In this specification, the term "cosmetics" refers to cleansers for hair or skin (such as shampoos, facial cleansers, cream facial cleansers, body soaps, solid soaps, cleansing oils, and liquid soaps), hair care cosmetics (such as hair rinses, conditioners, non-cationic conditioners, hair treatments, hair oils, hair milks, and styling agents (such as hair gels and hair sprays)), skin care cosmetics (such as skin lotions, lotions, cosmetic oils, emulsions, creams, hand creams, all-in-one gels, and shaving agents), makeup cosmetics (such as emulsion-type foundations, solid foundations, makeup bases, BB creams, CC creams, powders, lipsticks, blushers, eyeliners, eye shadows, eyebrow makeup products, and mascaras), hair cosmetics (such as hair waxes, hair gels, hair sprays, and hair colorants), sunscreen cosmetics (such as cream-type, gel-type, and roll-on-type cosmetics), wipe-off cosmetics (such as face masks, makeup remover sheets, sweat wipes, and hair wipes), fragrance products, and antiperspirants. The cosmetic of the present invention is preferably a shampoo, cream, hair treatment, cosmetic oil, or sunscreen cosmetic. The formulation of the cosmetic of the present invention is not particularly limited, and examples include powder, solid, solid powder, stick, liquid (such as a homogeneous liquid or emulsion), cream, sheet, and gel. When the cosmetic is an emulsion cosmetic, it may be in the form of either an oil-in-water emulsion or a water-in-oil emulsion.

[0056] This specification describes the following: <1> A cosmetic oil composition containing an alkylene oxide adduct (A) represented by the following formula (1): R—[O(PO) ｂ / (EO) ａ -H] ｎ... (1) [In formula (1), R represents a residue obtained by removing all hydroxyl groups from a compound having n hydroxyl groups, n is 4 or 6, EO and PO represent an ethyleneoxy group and a propyleneoxy group, respectively, a and b represent the average number of moles of ethyleneoxy groups and propyleneoxy groups added, respectively, and 10≦a×n≦20, 90≦b×n≦120] <2> The cosmetic oil composition according to above <1>, wherein the compound having n hydroxyl groups is at least one selected from the group consisting of diglycerin, pentaerythritol, and sorbitol. <3> A cosmetic comprising the cosmetic oil composition according to above <1> or <2>.

[0057] The present invention will be further explained below with reference to examples and comparative examples, but the present invention is not limited to these.

[0058] Production Example 1: Preparation of Alkylene Oxide Adduct (A-1) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 522.0 g (9.0 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 535.6 g of Intermediate 1. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 53.6 g (0.01 mol) of Intermediate 1, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 4.9 g (0.11 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 58.4 g of alkylene oxide adduct (A-1). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0059] Production Example 2: Preparation of Alkylene Oxide Adduct (A-2) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 529.0 g (9.1 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 542.6 g of Intermediate 2. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 54.3 g (0.01 mol) of Intermediate 2, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 6.2 g (0.14 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 60.5 g of alkylene oxide adduct (A-2). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0060] Production Example 3: Preparation of Alkylene Oxide Adduct (A-3) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 533.6 g (9.2 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 547.2 g of Intermediate 3. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 54.7 g (0.01 mol) of Intermediate 3, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 5.3 g (0.13 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 60.0 g of alkylene oxide adduct (A-3). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0061] Production Example 4: Preparation of Alkylene Oxide Adduct (A-4) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 522.0 g (9.0 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 535.6 g of Intermediate 4. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 53.6 g (0.01 mol) of Intermediate 4, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 6.6 g (0.15 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 60.2 g of alkylene oxide adduct (A-4). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0062] Production Example 5: Preparation of Alkylene Oxide Adduct (A-5) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 696.0 g (12.0 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 709.6 g of Intermediate 5. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 71.0 g (0.01 mol) of Intermediate 5, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 8.9 g (0.2 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 79.8 g of alkylene oxide adduct (A-5). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0063] Production Example 6: Preparation of Alkylene Oxide Adduct (A-6) In a stainless steel autoclave equipped with a stirrer and temperature control, 16.6 g (0.1 mol) of diglycerin (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 638.0 g (11.0 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 654.6 g of Intermediate 6. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 65.5 g (0.01 mol) of Intermediate 6, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 4.4 g (0.1 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 69.9 g of alkylene oxide adduct (A-6). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0064] Production Example 7: Preparation of Alkylene Oxide Adduct (A-7) In a stainless steel autoclave equipped with a stirrer and temperature control, 18.2 g (0.1 mol) of sorbitol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 551.0 g (9.5 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 569.2 g of Intermediate 7. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 56.9 g (0.01 mol) of Intermediate 7, and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 5.3 g (0.12 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 62.2 g of alkylene oxide adduct (A-7). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0065] Production Example 8: Preparation of Alkylene Oxide Adduct (A'-1) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed. The atmosphere inside the autoclave was replaced with nitrogen, and dehydration was carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 261.0 g (4.5 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 274.6 g of Intermediate 1'. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 27.5 g (0.01 mol) of Intermediate 1', and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 4.4 g (0.1 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 31.9 g of alkylene oxide adduct (A'-1). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0066] Production Example 9: Preparation of Alkylene Oxide Adduct (A'-2) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed. The atmosphere inside the autoclave was replaced with nitrogen, and dehydration was carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The autoclave was then heated to 120°C, and 87.0 g (1.5 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 100.6 g of Intermediate 2'. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 50.5 g (0.05 mol) of Intermediate 2', and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out for 1 hour at 120°C under reduced pressure (2.7 kPa). The temperature inside the autoclave was then raised to 120°C, and 11.0 g (0.25 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 61.5 g of alkylene oxide adduct (A'-2). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0067] Production Example 10: Preparation of Alkylene Oxide Adduct (A'-3) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed. The atmosphere inside the autoclave was replaced with nitrogen, and dehydration was carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 70.0 g (1.2 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 83.6 g of Intermediate 3'. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 41.5 g (0.05 mol) of Intermediate 3', and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 17.6 g (0.4 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 59.1 g of alkylene oxide adduct (A'-3). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0068] Production Example 11: Preparation of Alkylene Oxide Adduct (A'-4) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed. The atmosphere inside the autoclave was replaced with nitrogen, and dehydration was carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 580.8 g (10.0 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 594.4 g of Intermediate 4'. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 59.4 g (0.01 mol) of Intermediate 4', and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 19.8 g (0.45 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 79.2 g of alkylene oxide adduct (A'-4). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0069] Production Example 12: Preparation of Alkylene Oxide Adduct (A'-5) In a stainless steel autoclave equipped with a stirrer and temperature control, 13.6 g (0.1 mol) of pentaerythritol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.8 g of potassium hydroxide (FUJIFILM Wako Pure Chemical Industries, Ltd.) were mixed. The atmosphere inside the autoclave was replaced with nitrogen, and dehydration was carried out at 120°C under reduced pressure (2.7 kPa) for 1 hour. The autoclave was then heated to 120°C, and 726.0 g (12.5 mol) of 1,2-propylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 739.6 g of Intermediate 5'. The time from the start of the dropwise addition of 1,2-propylene oxide to the end of the reaction was 12 hours. A stainless steel autoclave equipped with a stirrer and temperature control was charged with 73.9 g (0.01 mol) of Intermediate 5', and the atmosphere inside the autoclave was replaced with nitrogen. Dehydration was then carried out under reduced pressure (2.7 kPa) at 120°C for 1 hour. The temperature inside the autoclave was then raised to 120°C, and 8.8 g (0.2 mol) of ethylene oxide was added dropwise while adjusting the gauge pressure of the autoclave to maintain it in the range of 50 to 200 kPa, yielding 82.7 g of alkylene oxide adduct (A'-5). The time from the start of the dropwise addition of ethylene oxide to the end of the reaction was 12 hours.

[0070] Examples 1 to 7 and Comparative Examples 1 to 5 The alkylene oxide adducts (A-1) to (A-7) obtained in Production Examples 1 to 7 were directly used as Cosmetic Oil Compositions 1 to 7 (Examples 1 to 7), and the alkylene oxide adducts (A'-1) to (A'-5) obtained in Production Examples 8 to 12 were directly used as Cosmetic Oil Compositions 1' to 5' (Comparative Examples 1 to 5). For each cosmetic oil composition, the average number of moles of ethyleneoxy groups added (a), the average number of moles of propyleneoxy groups added (b), and the ratio of the average number of moles of propyleneoxy groups to the average number of moles of ethyleneoxy groups (b / a) are shown in Table 1.

[0071]

[0072] <Water Holding Test> A water holding test was conducted for the cosmetic oil compositions of Examples 1 to 7 and Comparative Examples 1 to 5 by the following method, and the water holding rate and appearance were evaluated. 5 g of the cosmetic oil composition was placed in a 60 ml plastic cup, and 0.2 to 0.5 g of ion-exchanged water was added and mixed. The end point was the point at which water began to drain from the cosmetic oil composition. The drained liquid was removed, and the weight (g) of water held by the cosmetic oil composition at the end point was measured. This value was divided by the weight (5 g) of the cosmetic oil composition and multiplied by 100 to calculate the water holding rate (%). The same test was conducted three times in total. The appearance of the cosmetic oil composition at the end point was also visually confirmed, and the presence or absence of turbidity was evaluated. In the appearance evaluation, compositions without turbidity were rated as colorless and transparent. Furthermore, for cosmetic oil compositions 6' to 8' of Comparative Examples 6 to 8, the following commercially available products (lanolin and lanolin substitutes) were used, and a water holding test was conducted in the same manner as in Example 1, etc., to evaluate the water holding rate and appearance. For Examples 1 to 7 and Comparative Examples 1 to 8, the water holding rates and their average values ​​calculated in the first to third tests, as well as the evaluation results of appearance, are shown in Table 2.

[0073]

[0074] The following cosmetic oil compositions 6' to 8' listed in Table 2 were used: Cosmetic oil composition 6': Lanolin ("Anhydrate Lanolin" manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Cosmetic oil composition 7': Dipentaerythrityl hexa(hydroxystearate / stearate / rosinate) ("Cosmol 168ARV" manufactured by The Nisshin Oillio Group, Ltd.) Cosmetic oil composition 8': Glyceryl (ethylhexanoate / stearate / adipate) ("Nomcoat LAH" manufactured by The Nisshin Oillio Group, Ltd.)

[0075] <Solubility of UV absorbers> To 100 g of each of cosmetic oil compositions 1 to 7 and cosmetic oil compositions 9' to 11', the UV absorbers listed in Table 3 were added in the maximum amounts listed in Table 3 and mixed. Thereafter, it was visually confirmed whether they had dissolved, and the solubility was evaluated according to the following criteria. Note that solid UV absorbers were heated to 85°C and dissolved, and mixed with the cosmetic oil composition, and then when they were returned to room temperature, it was visually confirmed whether they had dissolved. The results are shown in Table 3. <Evaluation criteria> ◯: Completely dissolved △: Partially undissolved and some residue remains ×: Insoluble

[0076]

[0077] The cosmetic oil compositions 9' to 11' shown in Table 3 were as follows: Cosmetic oil composition 9': mineral oil ("Carnation" manufactured by Sonneborn LLC) Cosmetic oil composition 10': cetyl ethylhexanoate ("Koyo COC" manufactured by Koyo Fine Chemical Co., Ltd.) Cosmetic oil composition 11': cyclopentasiloxane ("KF-96A-10cs" manufactured by Shin-Etsu Chemical Co., Ltd.) Uvinul MC80N: UVB screening material (liquid), ethylhexyl methoxycinnamate Escalol 587 UV Filters: UVB screening material (liquid), ethylhexyl salicylate Escalol 507 UV Filters: UVB screening material (liquid), ethylhexyl dimethyl PABA Escalol 597: UVA / UVB screening material (liquid), octocrylene; Escalol 517: UVA screening material (solid), t-butyl methoxydibenzoylmethane; Uvinul A plus Granular: UVA screening material (solid), diethylaminohydroxybenzoyl hexyl benzoate

[0078] <Pigment Dispersibility> The cosmetic oil compositions of Examples 1 to 7 and cosmetic oil compositions 6' to 8' of Comparative Examples 6 to 8 were evaluated for pigment dispersibility by the following method. A mixture of the cosmetic oil composition and ethylhexyl palmitate (trade name "Salacos P-8", manufactured by The Nisshin Oillio Group, Ltd.) in a 1:1 weight ratio was gradually added to 20 g of titanium oxide and mixed. The amount of cosmetic oil composition added when all the titanium oxide was wet (when the powder had solidified into one mass) (wet point) and the amount of cosmetic oil composition added when the titanium oxide began to flow (pour point) were determined, and each was converted to a numerical value per 100 g of titanium oxide. The results are shown in Table 4. The smaller the difference between the wetting point and the pour point, the better the pigment dispersibility of the cosmetic oil composition.

[0079]

[0080] Cosmetic oil compositions 6' to 8' listed in Table 4 are the same as cosmetic oil compositions 6' to 8' listed in Table 2, respectively.

[0081] <Examples 8 to 14 and Comparative Examples 9 to 17: Shampoo> Cosmetic oil compositions 1 to 7 and cosmetic oil compositions 1' to 8', along with other optional ingredients listed in Table 5, were placed in a paddle mixer in the weight ratios listed in Table 5 and mixed at 25°C and a rotation speed of 60 rpm to prepare cosmetics (shampoos) of the present invention according to Examples 8 to 14 and comparative shampoos according to Comparative Examples 9 to 17. The resulting shampoos according to Examples 8 to 14 and Comparative Examples 9 to 17 were evaluated for moist feeling and non-stickiness of the scalp after use by the methods described below, and the results are shown in Table 5.

[0082] <Scalp Moisture: Shampoo> Ten male and female panelists thoroughly wet their scalps with 40°C hot water at room temperature of 25°C and humidity of 60%, and then washed with 5g of shampoo. After rinsing with 40°C hot water, the scalp was towel-dried and evaluated for moistness. The moistness of the scalp was evaluated on a 5-point scale from 1 to 5, with higher scores indicating a more moist scalp. The total scores of the 20 panelists are shown in Table 5.

[0083] <Non-sticky scalp: Shampoo> Five male and five female panelists thoroughly wetted their scalps with 40°C hot water and then washed them with 5g of shampoo. After rinsing with 40°C hot water, the scalp was towel-dried and evaluated for non-stickiness. Non-stickiness of the scalp was evaluated on a 5-point scale from 1 to 5, with higher scores indicating less stickiness. The total scores of the 10 panelists are shown in Table 5.

[0084]

[0085] Cosmetic oil compositions 6' to 8' listed in Table 5 are the same as cosmetic oil compositions 6' to 8' listed in Table 2. The optional components listed in Table 5 were as follows: 25 wt% disodium cocoyl glutamate: "Amisoft CS-22" manufactured by Ajinomoto Co., Inc. 34 wt% aqueous solution of coconut oil fatty acid amidopropyl betaine: "Revon HC-30W" manufactured by Sanyo Chemical Industries, Ltd.

[0086] <Examples 15 to 22 and Comparative Examples 18 to 26: Creams> Cosmetic oil compositions 1 to 7 and cosmetic oil compositions 1' to 8', along with other optional ingredients listed in Table 6, were placed in a disper mixer in the weight ratios listed in Table 6 and mixed at 80°C and a rotation speed of 60 rpm to produce cosmetics (creams) of the present invention according to Examples 15 to 22 and comparative creams according to Comparative Examples 18 to 26. The obtained creams according to Examples 15 to 22 and Comparative Examples 18 to 26 were evaluated for moist feeling and non-stickiness of the skin after use by the methods described below, and the results are shown in Table 6.

[0087] <Skin Moisture: Cream> Ten male and female panelists washed their forearms with a simple cleanser, rinsed with 40°C hot water, towel-dried, and then allowed to acclimate for 15 minutes at room temperature of 25°C and humidity of 60%. Then, 1 g of cream was applied to the forearms, and the stratum corneum moisture content was measured 2 minutes later. This value was used as the initial value. Ten minutes later, the stratum corneum moisture content was measured again. The initial value was set to 100%, and the stratum corneum moisture retention rate (%) after 10 minutes was calculated using the following formula. A higher stratum corneum moisture retention rate indicates better skin moisturization (moisture retention). A Corneometer (manufactured by Courage+Khazaka) was used to measure the stratum corneum moisture content. The average stratum corneum moisture retention rate for the 20 panelists is shown in Table 6. Stratum corneum moisture retention rate (%) = (stratum corneum moisture content after 10 minutes × 100) / initial value

[0088] <Non-stickiness of skin: Cream> Five male and five female panelists washed their forearms with a simple cleanser, rinsed them with 40°C hot water, towel-dried them, and then acclimatized them for 15 minutes at room temperature of 25°C and humidity of 60%. Then, 1 g of cream was applied to the forearms and evaluated for non-stickiness. If there was almost no feeling of cream remaining on the fingers, it was evaluated as non-sticky. Non-stickiness of skin was evaluated on a 5-point scale from 1 to 5, with higher scores indicating less stickiness. The total scores of the 10 panelists are shown in Table 6.

[0089]

[0090] Cosmetic oil compositions 6' to 8' listed in Table 6 are the same as cosmetic oil compositions 6' to 8' listed in Table 2. The optional components listed in Table 6 used were as follows: Polyglyceryl-6 polyricinoleate: "NIKKOL Hexaglyn PR-15" manufactured by Nikko Chemicals Co., Ltd. Polyglyceryl-2 isostearate: "NIKKOL DGMIS" manufactured by Nikko Chemicals Co., Ltd. Glycerin: "Purified Glycerin" manufactured by Kao Corporation BG (1,3-butylene glycol): "High Sugarcane BG" manufactured by Kokyu Alcohol Kogyo Co., Ltd. Caprylic / capric triglycerin: "O.D.O" manufactured by Nisshin Oillio Group, Ltd.

[0091] Examples 23 to 28 and Comparative Example 27: Hair Treatment Cosmetic oil compositions 1 to 7 and cosmetic oil composition 6' were heated to 80°C and mixed uniformly with component A so as to achieve the weight ratios shown in Table 7, yielding solution A. Component B was also heated to 80°C and mixed uniformly so as to achieve the weight ratios shown in Table 7, yielding solution B. Solution A and solution B were placed in a homomixer and mixed at 25°C and a rotation speed of 4000 rpm, and the pH was adjusted to 5 with lactic acid to produce cosmetics (hair treatments) of the present invention according to Examples 23 to 28 and a comparative hair treatment according to Comparative Example 27. The resulting hair treatments according to Examples 23 to 28 and Comparative Example 27 were evaluated for moist feeling and non-stickiness of hair after use using the methods described below, and the results are shown in Table 7.

[0092] <Hair Moisture: Hair Treatment> Five male and five female panelists applied 1 g of each hair treatment to hair at room temperature of 25°C and humidity of 60%, and evaluated the hair moisturization. The hair moisturization was evaluated on a five-point scale from 1 to 5, with higher scores indicating higher hair moisturization. The total scores of the 10 panelists are shown in Table 7.

[0093] <Hair non-stickiness: Hair treatment> Five male and five female panelists applied 1 g of each hair treatment to hair at room temperature of 25°C and humidity of 60%, and evaluated the non-stickiness of hair. The non-stickiness of hair was rated on a 5-point scale from 1 to 5, with higher scores indicating less stickiness of hair. The total scores of the 10 panelists are shown in Table 7.

[0094]

[0095] Cosmetic oil composition 6' shown in Table 7 is the same as cosmetic oil composition 6' shown in Table 2. As optional components shown in Table 7, the following were used.・Behentrimonium chloride: "Econol TM-22" manufactured by Sanyo Chemical Industries, Ltd. ・Cetyl alcohol: "Deodorized Cetanol" manufactured by Kokyu Alcohol Kogyo Co., Ltd. ・Myristyl alcohol: "Kalcol 4098" manufactured by Kao Corporation ・Ethylhexyl palmitate: "Salacos P-8" manufactured by Nisshin Oillio Group, Ltd. ・Isostearyl alcohol: "Isostearyl Alcohol EX" manufactured by Kokyu Alcohol Kogyo Co., Ltd. ・Squalane: "Olive Squalane" manufactured by Kokyu Alcohol Kogyo Co., Ltd. ・Steareth-20: "BS-20" manufactured by Nikko Chemicals Co., Ltd. ・Guar gum trimonium chloride: "JAGUAR C-13S" manufactured by Sansho Co., Ltd. ・Glycerin: "Purified glycerin" manufactured by Kao Corporation ・PG (propylene glycol): "propylene glycol" reagent manufactured by Nacalai Tesque, Inc. Phenoxyethanol: "Newpol EFP" manufactured by Sanyo Chemical Industries, Ltd. Lactic acid: "Lactic acid" reagent manufactured by Nacalai Tesque, Inc.

[0096] According to the present invention, it is possible to provide a cosmetic oil composition that has excellent water-holding ability, is colorless and transparent in appearance after water-holding, and has excellent solubility of ultraviolet absorbers and dispersibility of pigments, as well as a cosmetic containing the cosmetic oil composition that is excellent in moisturizing and non-sticky feeling on skin and hair. Cosmetics containing the cosmetic oil composition of the present invention have high water-holding ability and provide a moisturizing and non-sticky feeling on skin, and are therefore suitable for cosmetic oils, shampoos, creams, hair treatments, and the like. Furthermore, because the cosmetic oil composition of the present invention has excellent solubility of ultraviolet absorbers and excellent dispersibility of pigments, it is also suitable for sunscreen cosmetics, etc.

Claims

1. A cosmetic oil composition containing an alkylene oxide adduct (A) represented by the following formula (1): R—[O(PO) ｂ / (EO) ａ -H] ｎ ...(1) [In formula (1), R represents a residue obtained by removing all hydroxyl groups from a compound having n hydroxyl groups, n is 4 or 6, EO and PO represent an ethyleneoxy group and a propyleneoxy group, respectively, a and b represent the average number of moles of ethyleneoxy groups and propyleneoxy groups added, respectively, and 10≦a×n≦20, 90≦b×n≦120] 2. The cosmetic oil composition according to claim 1, wherein the compound having n hydroxyl groups is at least one selected from the group consisting of diglycerin, pentaerythritol and sorbitol.

3. A cosmetic comprising the cosmetic oil composition according to claim 1 or 2.

Images