Urethane polymer, method for producing urethane polymer, and cosmetic containing urethane polymer

Abstract

The present invention provides: a urethane polymer that is obtained by reacting castor oil with isophorone diisocyanate and that has a weight average molecular weight of 10,000-150,000; a method for producing the urethane polymer; and a cosmetic containing the urethane polymer.

Description

Urethane polymer, method for producing the urethane polymer, and cosmetic containing the urethane polymer

[0001] The present invention relates to a urethane polymer that has excellent properties and can be particularly suitably used in cosmetics, a method for producing the urethane polymer, and cosmetics containing the urethane polymer.

[0002] It is known that various urethane polymers are used in cosmetics, detergents, and the like to obtain compositions with desired properties (see, for example, Patent Documents 1 and 2). Another known example of such a urethane polymer is a reaction product of castor oil and isophorone diisocyanate (see, for example, Patent Document 3).

[0003] JP 2017-031426 A JP 2022-119195 A U.S. Pat. No. 5,707,612

[0004] As described in Patent Document 3, a urethane polymer formed from a reaction product of castor oil and isophorone diisocyanate is known under the product name POLYDERM PPI-CO, has a molecular weight of approximately 2082, and is said to improve adhesion, durability, moisture retention, and gloss when incorporated into skin or hair cosmetics. However, even when this urethane polymer is used, the properties may not be sufficient when incorporated into cosmetics, and there has been a demand in the market for a urethane polymer that is more excellent in various properties and can be used in cosmetics. Therefore, an object of the present invention is to provide a urethane polymer that has excellent properties and is particularly suitable for use in cosmetics.

[0005] The present inventors have therefore conducted extensive research and have arrived at the present invention, which relates to a urethane polymer obtained by reacting castor oil with isophorone diisocyanate and having a weight-average molecular weight of 10,000 to 150,000.

[0006] The present invention can provide a urethane polymer that has excellent properties and is particularly suitable for use in cosmetics.

[0007] The urethane polymer of the present invention is obtained by reacting castor oil with isophorone diisocyanate and has a weight-average molecular weight of 10,000 to 150,000. Such a urethane polymer can be produced by reacting the raw materials, castor oil and isophorone diisocyanate, in a specific ratio. The castor oil used in producing the urethane polymer of the present invention has a CAS number of 8001-79-4 and is a type of vegetable oil generally extracted from castor seeds. It is a mixture primarily composed of triesters of glycerin with fatty acids such as ricinoleic acid, linoleic acid, oleic acid, palmitic acid, and stearic acid. Note that, in the present invention, castor oil does not include modified castor oils such as hydrogenated castor oil or various castor oil derivatives obtained by chemically treating castor oil. In the present invention, castor oil extracted from castor bean seeds or commercially available castor oil may be used, and examples of such commercially available products include the refined castor oil series manufactured by Ito Oil Mills, Ltd.

[0008] The hydroxyl value of the castor oil used in producing the urethane polymer of the present invention is not particularly limited and can be adjusted as appropriate. However, from the viewpoint of the various properties of the resulting urethane polymer, it is preferable to use a castor oil having a hydroxyl value of 140 to 180 mgKOH / g, more preferably a castor oil having a hydroxyl value of 150 to 170 mgKOH / g, and even more preferably a castor oil having a hydroxyl value of 155 to 165 mgKOH / g. The acid value of the castor oil used is also not particularly limited and can be adjusted as appropriate. However, from the viewpoint of the various properties of the resulting urethane polymer, it is preferable to use a castor oil having an acid value of 5.0 mgKOH / g or less, more preferably a castor oil having an acid value of 3.0 mgKOH / g or less, and even more preferably a castor oil having an acid value of 1.5 mgKOH / g or less. In this case, the lower limit of the acid value of the castor oil is not particularly limited and can be adjusted as appropriate; for example, it may be 0.0 mgKOH / g.

[0009] The isophorone diisocyanate used in producing the urethane polymer of the present invention has a CAS number of 4098-71-9 and is a compound having two isocyanate groups in the molecule. By using isophorone diisocyanate as the isocyanate compound, the urethane polymer of the present invention has various excellent properties compared to urethane polymers obtained using other diisocyanate compounds, and can be a urethane polymer that is particularly suitable for use in cosmetics.

[0010] The urethane polymer of the present invention has a weight-average molecular weight of 10,000 to 150,000. The urethane polymer of the present invention can be obtained by reacting the above-mentioned castor oil and isophorone diisocyanate in a specific ratio. With such a weight-average molecular weight, the urethane polymer of the present invention has excellent properties and is particularly suitable for use as a cosmetic material. Furthermore, with a weight-average molecular weight of 150,000 or less, the urethane polymer of the present invention exhibits ease of production and handleability suitable for use as a cosmetic material. To achieve even more excellent properties, the weight-average molecular weight of the urethane polymer of the present invention is preferably 15,000 to 140,000, more preferably 40,000 to 130,000, even more preferably 60,000 to 120,000, and particularly preferably 90,000 to 120,000. In the present invention, the weight-average molecular weight of the urethane polymer is the weight-average molecular weight measured by gel permeation chromatography (GPC) and calculated in terms of styrene.

[0011] The viscosity of the urethane polymer of the present invention is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of the various properties of the resulting urethane polymer, for example, the viscosity at 25°C measured using a Brookfield viscometer is preferably 10,000 to 5,000,000 mPa·s, more preferably 50,000 to 4,000,000 mPa·s, even more preferably 200,000 to 3,000,000 mPa·s, and particularly preferably 600,000 to 2,500,000 mPa·s. Furthermore, from the viewpoint of various properties of the resulting urethane polymer, the viscosity at 60°C measured using a Brookfield viscometer is preferably 5,000 to 1,500,000 mPa·s, more preferably 8,000 to 1,200,000 mPa·s, even more preferably 20,000 to 1,000,000 mPa·s, and particularly preferably 50,000 to 900,000 mPa·s.

[0012] The urethane polymer of the present invention is a polymer obtained by reacting castor oil with isophorone diisocyanate, and is believed to be primarily composed of a urethane polymer obtained by the reaction of the hydroxyl groups present in the ricinoleic acid residues constituting the fatty acid esters, the main component of castor oil, with the isocyanate groups of isophorone diisocyanate to form urethane bonds. However, the specific structure of the urethane polymer is not only different depending on the equivalent ratio of the castor oil and isophorone diisocyanate used, but also on the castor oil itself, which is used as a raw material, is a mixture of glycerides (fatty acid esters) of various fatty acids and glycerin, so that it is impossible or even practical to uniquely describe the structure of the urethane polymer of the present invention by a general formula.

[0013] The urethane polymer of the present invention can be produced by reacting castor oil with isophorone diisocyanate so as to have a weight-average molecular weight of 10,000 to 150,000. There are no particular limitations on the production method, but the polymer can be produced, for example, by reacting castor oil with isophorone diisocyanate in the presence of a catalyst and a solvent as necessary, in amounts such that the ratio of the number of hydroxyl groups in the castor oil used to the number of isocyanate groups in the isophorone diisocyanate used (OH:NCO) is 1:0.40 to 1:0.90. In the present invention, from the viewpoint of easily obtaining a urethane polymer having more excellent properties and suitable for use in cosmetics in particular, the urethane polymer is preferably produced by reacting castor oil and isophorone diisocyanate in amounts such that the ratio of the number of hydroxyl groups in the castor oil to the number of isocyanate groups in the isophorone diisocyanate (OH:NCO) is 1:0.44 to 1:0.80, more preferably 1:0.48 to 1:0.72, even more preferably 1:0.52 to 1:0.68, even more preferably 1:0.56 to 1:0.64, and particularly preferably 1:0.59 to 1:0.63. Note that the urethane polymer produced may contain unreacted castor oil used as a raw material.

[0014] In addition to isophorone diisocyanate, the urethane polymer of the present invention can use other polyisocyanate compounds such as hexamethylene diisocyanate and dicyclohexylmethane-4,4'-diisocyanate as raw materials, provided that the effects of the present invention are not impaired. However, the amount of other polyisocyanate compounds per mole of isophorone diisocyanate is preferably 0.1 moles or less, more preferably 0.05 moles or less, and even more preferably no other polyisocyanate compounds are used. Furthermore, the urethane polymer of the present invention can use polyhydric alcohol compounds other than castor oil (e.g., polyalkylene glycol, glycerin, etc.) as raw materials, provided that the effects of the present invention are not impaired. However, the amount of polyhydric alcohol compounds per 100 parts by mass of castor oil is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably no polyhydric alcohol compounds other than castor oil are used. Therefore, it is most preferable that the urethane polymer of the present invention is obtained by reacting only isophorone diisocyanate and castor oil.

[0015] The catalyst that can be used when reacting castor oil with isophorone diisocyanate is not particularly limited, and known catalysts can be used depending on the purpose. Examples of such catalysts include strong acids such as sulfuric acid and toluenesulfonic acid; metal halides such as titanium tetrachloride, hafnium chloride, zirconium chloride, aluminum chloride, gallium chloride, indium chloride, iron chloride, tin chloride, and boron fluoride; hydroxides of alkali metals or alkaline earth metals such as sodium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, and sodium carbonate; Examples thereof include metal oxides such as alcoholates, carbonates, aluminum oxide, calcium oxide, barium oxide, and sodium oxide; organometallic compounds such as tetraisopropyl titanate, dibutyltin dichloride, dibutyltin oxide, and dibutyltin bis(2-ethylhexylthioglycolate); and fatty acid metal salts such as sodium acetate, potassium acetate, sodium propionate, potassium propionate, sodium octylate, potassium octylate, sodium laurate, and potassium laurate, and these may be used alone or in combination. When a catalyst is used in the reaction of castor oil and isophorone diisocyanate, the amount of the catalyst used is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of efficiently carrying out the reaction, the amount of the catalyst used is preferably 0.001 to 30 parts by mass, more preferably 0.005 to 20 parts by mass, even more preferably 0.01 to 15 parts by mass, and particularly preferably 0.05 to 10 parts by mass, when the total amount of castor oil and isophorone diisocyanate used is taken as 100 parts by mass.

[0016] The solvent that can be used when reacting castor oil with isophorone diisocyanate is not particularly limited, and any known solvent that does not react with castor oil or isophorone diisocyanate can be used. Examples of such solvents include pentane, hexane, heptane, octane, decane, dodecane, benzene, toluene, xylene, ethylbenzene, dodecylbenzene, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diphenyl ether, dibenzyl ether, diallyl ether, tetrahydrofuran, dioxane, N-methyl-2-pyrrolidone, ethyl butyrate, butyl butyrate, ethyl acetate, butyl acetate, dimethylformamide, N,N-dimethylacetamide, acetonitrile, propionitrile, and benzonitrile. One or more of these can be used. When a solvent is used in the reaction of castor oil and isophorone diisocyanate, the amount of the solvent used is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of efficiently carrying out the reaction, the amount of the solvent used is preferably 1 to 1,000 parts by mass, more preferably 10 to 500 parts by mass, and even more preferably 20 to 200 parts by mass, when the total amount of castor oil and isophorone diisocyanate used is taken as 100 parts by mass.

[0017] The temperature when reacting castor oil with isophorone diisocyanate is not particularly limited as long as it is a temperature at which the reaction between castor oil and isophorone diisocyanate proceeds, and can be adjusted appropriately depending on the purpose, but can be, for example, 60 to 160° C. From the viewpoint of easily obtaining a urethane polymer that is more excellent in various properties and that can be suitably used in cosmetics in particular, it is preferably 80 to 140° C., more preferably 100 to 130° C., and even more preferably 110 to 120° C. In this case, the reaction time when reacting castor oil with isophorone diisocyanate is not particularly limited and can be adjusted appropriately depending on the purpose, but from the viewpoint of easily obtaining a urethane polymer that can be suitably used in cosmetics in particular, it is preferably 30 minutes to 48 hours, more preferably 1 hour to 24 hours, even more preferably 2 hours to 15 hours, and particularly preferably 3 hours to 10 hours.

[0018] When reacting castor oil with isophorone diisocyanate, the reaction may be carried out under normal pressure, reduced pressure, or pressurized conditions, and the pressure can be adjusted appropriately. When reacting castor oil with isophorone diisocyanate under reduced pressure, the pressure is not particularly limited and can be adjusted appropriately depending on the purpose, but the reaction can be carried out under a pressure of 0.01 Pa to 80,000 Pa, for example. When reacting castor oil with isophorone diisocyanate under a pressurized condition, the pressure is not particularly limited and can be adjusted appropriately depending on the purpose, but the reaction can be carried out under a pressure of 0.001 MPa to 10 MPa, based on atmospheric pressure, for example.

[0019] The form and embodiment of use of the urethane polymer of the present invention are not particularly limited, and it can be incorporated into, for example, cosmetics, detergents, paints, pharmaceuticals, foods, etc., but from the viewpoint of the effects of the present invention, it is preferable to use the urethane polymer in cosmetics. Furthermore, the content of the urethane polymer in compositions such as cosmetics, detergents, paints, pharmaceuticals, and foods containing the urethane polymer of the present invention is not particularly limited, and can be, for example, 0.001 to 90.0 mass% relative to the total amount of the composition, preferably 0.01 to 80.0 mass%, more preferably 0.05 to 70.0 mass%, and even more preferably 0.10 to 60.0 mass% relative to the total amount of the composition.

[0020] The cosmetic of the present invention is a cosmetic containing the above-mentioned urethane polymer. In the present invention, by containing a urethane polymer obtained by reacting castor oil with isophorone diisocyanate and having a weight-average molecular weight of 10,000 to 150,000, the cosmetic can have excellent properties. The content of the above-mentioned urethane polymer in the cosmetic of the present invention is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of optimally exhibiting the properties of the urethane polymer and providing a cosmetic with even more excellent properties, the content of the urethane polymer in the cosmetic is preferably 0.1 to 90.0 mass%, more preferably 0.5 to 80.0 mass%, even more preferably 1.0 to 70.0 mass%, and particularly preferably 2.0 to 60.0 mass%, relative to the total amount of the cosmetic.

[0021] Cosmetics containing the urethane polymer of the present invention can be blended with various components to improve or modify various properties (solubility, dispersibility, stability, usability, application, penetration, moisture retention, safety, design, optical properties, fragrance, whitening properties, etc.) during storage, during use, and after use, depending on the intended use. Examples of such components include higher alcohols, powder components, colorants, higher fatty acids, humectants, water-soluble polymers, sequestering agents, water, oily components, lower alcohols, polyhydric alcohols, monosaccharides, oligosaccharides, polysaccharides, amino acids and derivatives thereof, organic amines, pH adjusters, vitamins, ultraviolet absorbers, antioxidants, thickeners, surfactants, and other possible components (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, antiseborrheic agents, anti-inflammatory agents, various extracts, plant and seaweed extracts, etc.), and one or more of these can be blended as desired.

[0022] Examples of higher alcohols include straight-chain higher alcohols such as lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, and cetostearyl alcohol; and branched-chain higher alcohols such as monostearyl glycerin ether (batyl alcohol), 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, and octyldodecanol, and these may be used alone or in combination.

[0023] Examples of powder components include inorganic powders (e.g., talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, lepidolite, biotite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate, calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, zinc myristate, calcium palmitate, aluminum stearate, boron nitride, etc.); and organic powders (e.g., polyamide resin powder, polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene-acrylic acid copolymer resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.), and these may be used alone or in combination.

[0024] Examples of colorants include inorganic white pigments (e.g., titanium dioxide, zinc oxide, etc.); inorganic red pigments (e.g., iron oxide, iron titanate, etc.); inorganic brown pigments (e.g., γ-iron oxide, etc.); inorganic yellow pigments (e.g., yellow iron oxide, ochre, etc.); inorganic black pigments (e.g., black iron oxide, low-order titanium oxide, etc.); inorganic purple pigments (e.g., manganese violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, Prussian blue, etc.); inorganic pearl pigments (e.g., titanium oxide-coated mica, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, colored titanium oxide-coated mica, bismuth oxychloride, fish scale foil, etc.); organic synthetic pigments such as zirconium lake, barium lake, aluminum lake, etc. (for example, Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 226, Red No. 227, Red No. 228, Red No. 230, Red No. 401, Red No. 405, Red No. 505, Orange No. 203, Orange No. 204, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Yellow No. 205, Yellow No. 401, Blue No. 1, Blue No. 404, Green No. 3, etc.); natural pigments (for example, chlorophyll, β-carotene, etc.), and these may be used alone or in combination.

[0025] Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA). One or more of these may be used.

[0026] Examples of moisturizing agents include polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO)PO adduct, Rosa robur extract, yarrow extract, melilot extract, and the like, and one or more of these can be used.

[0027] Examples of natural water-soluble polymers include plant-derived polymers (e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (marmelo), algae colloid (cassow extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial-derived polymers (e.g., xanthan gum, dextran, succinoglucan, pullulan, gellan gum); and animal-derived polymers (e.g., collagen, casein, albumin, gelatin), and the like, and one or more of these may be used.

[0028] Examples of water-soluble polymers include starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methyl cellulose, ethyl cellulose, methylhydroxypropyl cellulose, hydroxyethyl cellulose, sodium cellulose sulfate, hydroxypropyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, crystalline cellulose, cellulose powder, etc.); alginic acid-based polymers (e.g., sodium alginate, propylene glycol alginate, etc.); vinyl-based polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene-based polymers (e.g., polyoxyethylene polyoxypropylene copolymers made from polyethylene glycol 20,000, 40,000 or 60,000); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, etc., and one or more of these can be used.

[0029] Examples of sequestering agents include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, and trisodium ethylenediaminehydroxyethyltriacetate, and one or more of these may be used.

[0030] Examples of oily components include ester oils, hydrocarbon oils, and silicone oils, and one or more of these can be used. Among these, examples of ester oils include isopropyl myristate, cetyl octanoate, isononyl isononanoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, glyceryl di-2-ethylhexanoate, dipentaerythritol fatty acid esters, glyceryl monoisostearate, neopentyl glycol dicaprate, diisostearyl malate, glyceryl di-2-heptylundecanoate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, tetra-2 2-ethylhexanoate, pentaerythritol tri-2-ethylhexanoate, glyceryl trioctanoate, glyceryl tripalmitate (tripalmitin), glyceryl trimyristate (trimyristin), glyceryl triisostearate (triisostearin), glyceryl tri-2-heptylundecanoate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, castor oil fatty acid methyl ester, oleyl oleate, acetoglyceride, diisobutyl adipate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, ethyl laurate, diisopropyl sebacate, triethylhexanoin, tri(caprylic acid / capric acid)glyceryl, and the like, and one or more of these can be used. Also usable are oils and fats such as avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, camellia oil, castor oil, linseed oil, safflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, Chinese tung oil, Japanese tung oil, jojoba oil, germ oil, triglycerides, cacao butter, coconut oil, hydrogenated coconut oil, palm oil, palm kernel oil, Japan wax kernel oil, hydrogenated oil, Japan wax, and hydrogenated castor oil, including ester oils.

[0031] Examples of hydrocarbon oils include liquid paraffin, ozokerite, squalane, pristane, paraffin, polyisobutene, hydrogenated polyisobutene, isododecane, ceresin, squalene, petrolatum, and microcrystalline wax, and one or more of these can be used.

[0032] Examples of silicone oils include chain polysiloxanes (e.g., dimethicone, diphenyldimethicone, diphenylpolysiloxane, etc.), cyclic polysiloxanes (e.g., octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, etc.), silicone resins that form a three-dimensional network structure, silicone rubber, and various modified polysiloxanes (amino-modified polysiloxanes, polyether-modified polysiloxanes, alkyl-modified polysiloxanes, fluorine-modified polysiloxanes, etc.), and these can be used alone or in combination of two or more.

[0033] Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, and t-butyl alcohol, and one or more of these can be used.

[0034] Examples of polyhydric alcohols include dihydric alcohols (e.g., ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,2-hexanediol, etc.); trihydric alcohols (e.g., glycerin, trimethylolpropane, etc.); tetrahydric alcohols (e.g., pentaerythritol such as 1,2,6-hexanetriol, etc.); pentahydric alcohols (e.g., xylitol, etc.); hexahydric alcohols (e.g., sorbitol, mannitol, etc.); polyhydric alcohol polymers (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, polyglycerin, etc.); alkyl ethers of dihydric alcohols (e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol glycol mono 2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol butyl ether, etc.);Ether esters of dihydric alcohols (e.g., ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate, sugar alcohols (for example, sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch-decomposed sugars, maltose, xylitose, starch-decomposed sugar reduced alcohols, etc.); glysolid; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl alcohol; POP-butyl ether; POP·POE-butyl ether; tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphate; POP·POE-pentaneerythritol ether; polyglycerin, and the like, and one or more of these may be used;

[0035] Examples of monosaccharides include trioses (e.g., D-glyceryl aldehyde, dihydroxyacetone, etc.); tetraoses (e.g., D-erythrose, D-erythrulose, D-threose, erythritol, etc.); pentoses (e.g., L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc.); hexoses (e.g., D-glucose, D-talose, D-psicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tag heptoses (e.g., aldoheptose, heptose, etc.); octose (e.g., octulose, etc.); deoxysugars (e.g., 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L-mannose, etc.); aminosugars (e.g., D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.); uronic acids (e.g., D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid, etc.), and one or more of these can be used.

[0036] Examples of oligosaccharides include sucrose, umbelliferose, lactose, planteose, isolichinoses, α,α-trehalose, raffinose, lychinoses, umbilicin, stachyose, verbascoses, etc., and one or more of these can be used.

[0037] Examples of polysaccharides include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guar gum, dextran, keratosulfate, locust bean gum, succinoglucan, and caronic acid, and one or more of these can be used.

[0038] Examples of the amino acid include neutral amino acids (e.g., threonine, cysteine, etc.) and basic amino acids (e.g., hydroxylysine, etc.). Examples of the amino acid derivative include sodium acyl sarcosine (sodium lauroyl sarcosine), acyl glutamate, sodium acyl β-alanine, glutathione, pyrrolidone carboxylic acid, etc., and one or more of these can be used.

[0039] Examples of organic amines include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol, and these can be used alone or in combination of two or more.

[0040] Examples of pH adjusters include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate, and one or more of these can be used.

[0041] Examples of vitamins include vitamins A, B1, B2, B6, C, E and derivatives thereof, pantothenic acid and derivatives thereof, biotin, etc., and one or more of these can be used.

[0042] As the ultraviolet absorber, inorganic ultraviolet absorbers and surface-treated products thereof, and organic ultraviolet absorbers can be used, for example, salicylic acid and its sodium salt, salicylic acid derivatives such as amyl salicylate, menthyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, and p-isopropanol phenyl salicylate; octyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropyl cinnamate, methyl-2,4-diisopropyl cinnamate, propyl-p-methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate, 2-ethylhexyl-p-methoxycinnamate (ethylhexyl methoxycinnamate), Cinnamic acid derivatives such as para-aminobenzoic acid, para-aminobenzoic acid monoglycerin ester, N,N-dipropoxypara-aminobenzoic acid ethyl ester, N,N-diethoxypara-aminobenzoic acid ethyl ester, N,N-dimethylpara-aminobenzoic acid ethyl ester, N,N-dimethylpara-aminobenzoic acid butyl ester, N,N-dimethylpara-aminobenzoic acid ethyl ester, and diethylaminohydroxybenzoylhexyl benzoate; anthranilic acid derivatives such as homomenthyl-N-acetylanthranilate;2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone (oxybenzone-3), 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate benzophenone derivatives such as benzophenone, 2-hydroxy-4-n-octoxybenzophenone, and 4-hydroxy-3-carboxybenzophenone; 3-(4'-methylbenzylidene)-d,l-camphor, 3-benzylidene-d,l-camphor; 2-phenyl-5-methylbenzoxazole; 2,2'-hydroxy-5-methylphenylbenzotriazole; 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole; 2-(2'-hydroxy-5'-methylphenylbenzotriazole; dibenzalazine; dianisoylmethacrylate dibenzoylmethane derivatives such as 4-t-butylmethoxydibenzoylmethane; urocanic acid derivatives such as urocanic acid and ethyl urocanate; diphenylacrylate derivatives such as 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (octocrylene); 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 1-(3,4-dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione, dimethoxybenzylidene dibenzoate Examples of such compounds include hydantoin derivatives such as 2-ethylhexyl xoimidazolidinepropionate; silicone-based ultraviolet absorbers such as dimethicodiethylbenzalmalonate (polysilicone-15); phenylbenzimidazolazole sulfonic acid, terephthalylidene dicamphorsulfonic acid, drometrizole trisiloxane, methyl anthranilate, bisethylhexyloxyphenol methoxyphenyl triazine, octyl triazone, rutin and its derivatives, and oryzanol and its derivatives, and these compounds may be used alone or in combination.

[0043] Examples of antioxidants include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, and gallic acid esters, and one or more of these can be used.

[0044] Examples of thickeners include xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, karaya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, β-glucan, β-glucan derivatives, gellan gum, dextran, α-glucose and α-glucose derivatives, cellulose or derivatives thereof, keratin and collagen or derivatives thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharides, carbomer, dimethyldiallylammonium chloride-acrylamide copolymer, dimethyldiallylammonium chloride hectorite, acrylamide-acrylic acid-dimethyldiallylammonium chloride copolymer, dibutylethylhexanoyl glutamide, and the like. One or more of these may be used.

[0045] Examples of surfactants include cationic surfactants (e.g., lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, alkyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyltrimethylammonium saccharin, cetyltrimethylammonium saccharin, behenyltrimethylammonium methylsulfate, behenyldimethylamine, behenic acid diethylaminoethylamide, behenic acid dimethylaminopropylamide, behenic acid dimethylaminoethylamide, stearyldimethylamine, palmitoxypropyldimethylamine, stearoxypropyldimethylamine, etc.); anionic surfactants (e.g., alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate ester salts, alkenyl ether sulfates, alkenyl sulfates, olefins, etc.); amine sulfonates, alkanesulfonates, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylates, α-sulfonic acid salts, N-acyl amino acid surfactants, phosphate mono- or diester surfactants, sulfosuccinate esters, N-alkyloylmethyl taurine salts, and derivatives thereof); amphoteric surfactants (for example, coconut oil fatty acid amidopropyl dimethyl acetate betaine, lauryl dimethyl amino acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxymethyl imidazolinium betaine, lauryl hydroxysulfobetaine, lauroyl amidoethyl hydroxyethyl carboxymethyl betaine, betaine-type amphoteric surfactants such as metal salts of hydroxypropyl phosphate, amino acid-type amphoteric surfactants such as metal salts of β-laurylaminopropionic acid, sulfate ester-type amphoteric surfactants, and sulfonic acid-type amphoteric surfactants);Nonionic surfactants (e.g., POE cetyl ether (ceteth), POE stearyl ether (steareth), POE behenyl ether, POE oleyl ether (oleth), POE lauryl ether (laureth), POE octyldodecyl ether, POE hexyldecyl ether, POE isostearyl ether, POE nonylphenyl ether, POE octylphenyl ether, POE polyoxypropylene cetyl ether, POE polyoxypropylene decyltetradecyl ether, POE sorbitan monooleate, POE sorbitan monostearate, POE sorbitan monopalmitate, POE sorbitan monolaurate, POE sorbitan trioleate, POE glycerin monostearate, POE glycerin monomyristate, POE sorbit tetraoleate, POE isostearate ... lubit, POE sorbitol monolaurate, POE sorbitol beeswax, polyethylene glycol monooleate, polyethylene glycol monostearate, polyethylene glycol monolaurate, lipophilic glycerin monooleate, lipophilic glycerin monostearate, self-emulsifying glycerin monostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan monopalmitate, sorbitan monolaurate, sucrose fatty acid esters, decaglyceryl monolaurate, decaglyceryl monostearate, decaglyceryl monooleate, decaglyceryl monomyristate, alkyl glucoside, POE methyl glucoside, POE methyl glucoside dioleate, etc., and one or more of these may be used;

[0046] Other ingredients that can be added include, for example, preservatives (1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, hexylglycerin, cyclohexylglycerin, ethylhexylglycerin, methylparaben, ethylparaben, butylparaben, phenoxyethanol, etc.); anti-inflammatory agents (for example, glycyrrhizinic acid derivatives, glycyrrhetinic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (for example, saxifrage extract, arbutin, etc.); various extracts (for example, Phellodendron bark, Coptis chinensis, Lithospermum root, Peony root, Swertia japonica, Birch, Sage, Loquat, Carrot, Aloe, Mallow, Iris, Grape, Job's tears, Loofah, Lily, Saffron, Cnidium rhizome, Angelica juncea, St. John's wort,

[0049] Examples of the active ingredient include: water hyacinth, ononis, garlic, chili pepper, tangerine peel, angelica acutiloba, seaweed, etc.); activators (for example, royal jelly, photosensitizers, cholesterol derivatives, etc.); blood circulation promoters (for example, nicotinic acid benzyl ester, nicotinic acid β-butoxyethyl ester, capsaicin, zingerone, cantharides tincture, ichthammol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthine, γ-oryzanol, etc.); antiseborrheic agents (for example, sulfur, thianthol, etc.); and anti-inflammatory agents (for example, tranexamic acid, thiotaurine, hypotaurine, etc.), and one or more of these can be used.

[0047] When higher alcohols, powder components, colorants, higher fatty acids, moisturizers, water-soluble polymers, sequestering agents, lower alcohols, water, polyhydric alcohols, monosaccharides, oligosaccharides, polysaccharides, amino acids and derivatives thereof, organic amines, pH adjusters, vitamins, ultraviolet absorbers, antioxidants, thickeners, surfactants, and other ingredients that can be added to a cosmetic containing the urethane polymer of the present invention (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, antiseborrheic agents, anti-inflammatory agents, various extracts, plant and seaweed extracts, etc.), the content of each ingredient is not particularly limited and may be adjusted depending on the embodiment and purpose. For example, each ingredient may be added in an amount of 0.001 to 50.0% by mass relative to the total amount of the cosmetic.

[0048] From the viewpoint of efficiently achieving an SPF-boosting effect in the resulting cosmetic composition containing the urethane polymer of the present invention, it is preferable that the cosmetic composition further contains an ultraviolet absorber. In this case, from the viewpoint of easily achieving an SPF-boosting effect when used in combination with the urethane polymer, the ultraviolet absorber preferably contains one or more types selected from the group consisting of salicylic acid derivatives, cinnamic acid derivatives, benzoic acid derivatives, diphenyl acrylate derivatives, and benzophenone derivatives, more preferably contains one or more types selected from the group consisting of salicylic acid derivatives, cinnamic acid derivatives, and diphenyl acrylate derivatives, and even more preferably contains one or more types selected from the group consisting of ethylhexyl salicylate, ethylhexyl methoxycinnamate, and octocrylene.

[0049] When a cosmetic containing the urethane polymer of the present invention contains an ultraviolet absorber, the content of the ultraviolet absorber is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of easily obtaining an SPF boost effect by using the cosmetic in combination with the urethane polymer, the content of the ultraviolet absorber in the cosmetic is preferably 0.01 to 40% by mass, more preferably 0.1 to 30% by mass, and even more preferably 1.0 to 25% by mass, relative to the total amount of the cosmetic.

[0050] When the cosmetic preparation containing the urethane polymer of the present invention also contains an ultraviolet absorber, the content of the urethane polymer is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of easily obtaining an SPF boost effect by using the cosmetic preparation in combination with the ultraviolet absorber, the content of the urethane polymer in the cosmetic preparation is preferably 1.0 to 90.0% by mass, more preferably 2.0 to 80.0% by mass, even more preferably 3.0 to 70.0% by mass, and particularly preferably 5.0 to 60.0% by mass, relative to the total amount of the cosmetic preparation.

[0051] When a cosmetic preparation containing the urethane polymer of the present invention also contains an ultraviolet absorber, the content ratio of the urethane polymer to the ultraviolet absorber in the cosmetic preparation is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of easily obtaining an SPF boost effect when the urethane polymer and the ultraviolet absorber are used in combination, the content ratio of the urethane polymer to the ultraviolet absorber in the cosmetic preparation (urethane polymer: ultraviolet absorber) is preferably 1:0.05 to 1:20, more preferably 1:0.1 to 1:10, and even more preferably 1:0.2 to 1:5, by mass.

[0052] When a cosmetic containing the urethane polymer of the present invention contains an ultraviolet absorber, from the viewpoint of more efficiently exerting the SPF boost effect, it preferably further contains one or more oily components selected from the group consisting of silicone oils, ester oils, and hydrocarbon oils, more preferably one or more oily components selected from the group consisting of ester oils and hydrocarbon oils, and even more preferably one or more ester oils. In this case, the silicone oils, ester oils, and hydrocarbon oils that can be used are those described above.

[0053] When a cosmetic containing the urethane polymer of the present invention contains an ultraviolet absorber and an oily component, the content of the oily component is not particularly limited and can be adjusted appropriately depending on the purpose, but from the viewpoint of more efficiently exerting the SPF boost effect, the content of the oily component is preferably 1 to 80 mass %, more preferably 2 to 70 mass %, and even more preferably 5 to 60 mass %, relative to the total amount of the cosmetic.

[0054] Cosmetics containing the urethane polymer of the present invention preferably further contain a colorant, from the viewpoint of the resulting cosmetic efficiently exhibiting colorant capture properties and discoloration prevention properties. In this case, the colorant is not particularly limited, and known inorganic pigments, organic synthetic dyes, natural dyes, etc. used in cosmetics can be used, for example, the colorants described above can be used. Among these, from the viewpoint of easily achieving the effects of colorant capture properties and discoloration prevention when used in combination with the urethane polymer of the present invention, it is preferable to contain one or more colorants selected from the group consisting of inorganic pigments and organic synthetic dyes, and it is more preferable to contain one or more organic synthetic dyes.

[0055] When a cosmetic containing the urethane polymer of the present invention contains a colorant, the content of the colorant is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of easily obtaining the effects of colorant capture and discoloration prevention when used in combination with the urethane polymer, the content of the colorant in the cosmetic is preferably 0.001 to 20% by mass, more preferably 0.005 to 10% by mass, and even more preferably 0.01 to 5% by mass, relative to the total amount of the cosmetic.

[0056] When a cosmetic containing the urethane polymer of the present invention contains a colorant, the content ratio of the urethane polymer to the colorant in the cosmetic is not particularly limited and can be adjusted appropriately depending on the purpose. However, from the viewpoint of easily obtaining the effects of colorant capture and discoloration prevention when the urethane polymer and colorant are used in combination, the content ratio of the urethane polymer to the colorant in the cosmetic (urethane polymer:colorant) is preferably 1:0.0001 to 1:1, more preferably 1:0.0005 to 1:0.5, and even more preferably 1:0.001 to 1:0.1, by mass.

[0057] When a cosmetic containing the urethane polymer of the present invention contains a colorant, it is preferable that it further contains one or more oily components selected from the group consisting of silicone oil, ester oil, and hydrocarbon oil, from the viewpoint of more efficiently exhibiting colorant capture and discoloration prevention properties. Among these, it is more preferable to contain silicone oil as the oily component, from the viewpoint of more easily achieving the effects of colorant capture and discoloration prevention when used in combination with the urethane polymer and the colorant, and it is even more preferable to contain silicone oil and one or more oils selected from the group consisting of ester oil and hydrocarbon oil. In this case, the silicone oil, ester oil, and hydrocarbon oil can each be those described above.

[0058] When a cosmetic containing the urethane polymer of the present invention contains a colorant and an oily component, the content of the oily component is not particularly limited and can be adjusted appropriately depending on the purpose, but from the viewpoint of more efficiently exhibiting colorant capture properties and discoloration prevention properties, the content of the oily component is preferably 1 to 95 mass %, more preferably 2 to 90 mass %, and even more preferably 5 to 85 mass %, based on the total amount of the cosmetic.

[0059] The specific product or form of the cosmetic containing the urethane polymer of the present invention is not particularly limited, and examples include hair cosmetics, skin cosmetics, makeup cosmetics, fragrance cosmetics, body cosmetics, and topical skin preparations. Among these, when the cosmetic containing the urethane polymer of the present invention contains an ultraviolet absorber, it is preferably a sunscreen cosmetic such as a sunscreen cream, sunscreen emulsion, or sunscreen lotion, or a foundation, from the viewpoint of more efficiently exerting the SPF boost effect. Furthermore, when the cosmetic containing the urethane polymer of the present invention contains a colorant, it is preferably a lipstick, lip gloss, eye gloss, nail gloss, mascara, or eye shadow, from the viewpoint of more efficiently exerting the colorant capture ability and discoloration prevention ability.

[0060] The present disclosure includes the following aspects.

[0061] [1] A urethane polymer obtained by reacting castor oil with isophorone diisocyanate, and having a weight average molecular weight of 10,000 to 150,000.

[0062] [2] The urethane polymer according to [1], which is used in cosmetics.

[0063] [3] A cosmetic containing the urethane polymer described in [1].

[0064] [4] A cosmetic comprising the urethane polymer according to [1] and an ultraviolet absorber.

[0065] [5] A cosmetic comprising the urethane polymer according to [1] and a colorant.

[0066] The method for producing a urethane polymer according to [1], comprising reacting the castor oil and the isophorone diisocyanate in amounts such that the ratio (OH:NCO) of the number of hydroxyl groups in the castor oil to the number of isocyanate groups in the isophorone diisocyanate is 1:0.40 to 1:0.90.

[0067] A method for improving the SPF boost effect of a cosmetic, comprising blending an ultraviolet absorber and the urethane polymer according to [1] into the cosmetic.

[0068] A method for improving the colorant capture ability and discoloration prevention ability of a cosmetic, comprising blending a colorant and the urethane polymer according to [1] into the cosmetic.

[0069] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples and may be changed within the scope of the present invention. In the following examples, percentages are by mass unless otherwise specified.

[0070] <Method for measuring weight-average molecular weight> The weight-average molecular weight of the urethane polymers produced in the examples was measured by gel permeation chromatography (GPC) and calculated in terms of styrene. The detailed method for measuring this is as follows: GPC apparatus: HLC-8320GPC (manufactured by Tosoh Corporation) Column: TSKgel (registered trademark) SuperMultiporeHZ-N (manufactured by Tosoh Corporation) Detector: RI detector (built into HLC-8320GPC) Flow rate: 0.3 ml / min Sample concentration: 0.5% by mass (THF solution) Injection volume: 5 μl Column temperature: 40° C. Standard sample: TSKgel standard polystyrene (weight-average molecular weights: 98,900, 37,200, 13,700, 9,490, 5,430, 3,120, 1,010, 589; all manufactured by Tosoh Corporation).

[0071] Example 1 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 250 g of castor oil (Castor Oil LAV manufactured by Ito Oil Mills, Ltd., hydroxyl group equivalent: 161 mg KOH / g) and 40 g (0.18 mol) of isophorone diisocyanate, and the mixture was reacted at 110 to 120°C for 5 hours. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing urethane polymer 1. The weight average molecular weight of the resulting urethane polymer 1, as measured by gel permeation chromatography (GPC) and calculated in terms of styrene, was 17,500.

[0072] Example 2 Urethane polymer 2 was produced in the same manner as in Example 1, except that the amount of isophorone diisocyanate used was 46 g (0.21 mol). The weight average molecular weight of the resulting urethane polymer 2, as measured by gel permeation chromatography (GPC) and calculated as a styrene equivalent, was 77,800.

[0073] Example 3 Urethane polymer 3 was produced in the same manner as in Example 1, except that the amount of isophorone diisocyanate used was 48 g (0.22 mol). The weight average molecular weight of the resulting urethane polymer 3, as measured by gel permeation chromatography (GPC) and calculated as a styrene equivalent, was 107,600.

[0074] Example 4 Urethane polymer 4 was produced in the same manner as in Example 1, except that the amount of isophorone diisocyanate used was 50 g (0.23 mol). The weight average molecular weight of the resulting urethane polymer 4, as measured by gel permeation chromatography (GPC) and calculated in terms of styrene, was 111,800.

[0075] Comparative Example 1 Urethane polymer 5 was produced in the same manner as in Example 1, except that the amount of isophorone diisocyanate used was 26 g (0.12 mol). The weight average molecular weight of the resulting urethane polymer 5 was measured by gel permeation chromatography (GPC) and calculated as a styrene equivalent, to be 1,200.

[0076] <Evaluation of SPF Boost Effect> Cosmetics containing the urethane polymer of the present invention were produced using the urethane polymers 1 to 5 produced in Examples 1 to 4 and Comparative Example 1, as shown in Tables 1 to 3, and the SPF boost effect was evaluated in accordance with ISO 24443:2021 and ISO 24444:2019. Specifically, in accordance with the in vitro measurement method of ISO 24443:2021, test pieces were prepared by applying each cosmetic to a test substrate (Helioplate SB6 manufactured by HelioScreen), and after drying, transmittance was measured at nine points using an SPF analyzer (UV-2000S manufactured by Labsphere), and the SPF (initial SPF) was calculated from the average value. Furthermore, a coating film of each cosmetic was formed on a separate test substrate in the same manner, and the test specimen was then immersed in a water bath heated to 30°C for 30 minutes while stirring the water bath with a paddle blade. The test specimen was then removed, drained, and dried in a thermostatic chamber at 40°C for 30 minutes, after which the SPF (SPF after water immersion) was calculated in the same manner as above. Furthermore, for the calculated initial SPF value and SPF after water immersion, a relative SPF value was calculated, where the initial SPF value of the cosmetic of Comparative Example 3, which did not contain a urethane polymer, was set at 100. The calculation results are also shown in Tables 1 to 3. In this evaluation, a relative SPF value of more than 100 indicates that the SPF has been enhanced (SPF boosted) by the incorporation of the urethane polymer, and a post-water immersion SPF of more than 100 indicates excellent water resistance and SPF boost effect.

[0077]

[0078]

[0079]

[0080] <Colorant Capture Ability Evaluation 1> Using the urethane polymers 1 to 5 produced in Examples 1 to 4 and Comparative Example 1, cosmetics (total amount 10 g) containing the urethane polymer of the present invention were produced as shown in Tables 4 to 9, and the colorant capture ability of each cosmetic was evaluated. Specifically, the components were mixed to produce a cosmetic, which was then stirred at 80°C for 5 minutes and allowed to cool to room temperature. After standing, each cosmetic separated into an upper layer primarily composed of an oily component, a middle layer primarily composed of a urethane polymer, and a lower layer primarily composed of water, and it is believed that the colorant was present in one of these layers. The appearance of each cosmetic after standing was visually observed and the colorant capture ability of each cosmetic was evaluated based on the Colorant Capture Ability Evaluation Criteria 1 described below. The evaluation results are shown in Tables 4 to 9. In this evaluation, if the evaluation result is ○, in a cosmetic containing a colorant, even if it contains silicone oil, ester oil, or the like, it is possible to prevent the colorant from dispersing throughout the cosmetic. This indicates that, for example, in a lipstick or the like containing an oily component as its main component, by preventing the colorant from dispersing in the surface layer after application, even when the surface of the applied area comes into contact with a mask or the like, the effect of not causing color transfer to the mask or the like can be achieved.

[0081] Colorant Capture Evaluation Criteria 1: ○: All of the colorant is dispersed only in the middle and lower layers. ×: The colorant is also dispersed in the upper layer.

[0082] <Discoloration Resistance Evaluation 1> Separately from the evaluation of colorant capture ability, cosmetics (total amount 10 g) containing the urethane polymer of the present invention were prepared as shown in Tables 4 to 9, and discoloration resistance was evaluated. Specifically, the components were mixed to prepare the cosmetics, stirred at 80°C for 5 minutes, and then air-cooled to room temperature. After that, approximately 0.25 ml of the middle layer (a layer believed to be mainly composed of urethane polymer) of each cosmetic was extracted using a dropper and dispensed onto white art paper, and allowed to stand at room temperature for 5 minutes. After standing, the color of the cosmetics was visually observed and the discoloration resistance of each cosmetic was evaluated based on the discoloration resistance evaluation criteria 1 described below. The evaluation results are shown in Tables 4 to 9. In this evaluation, an evaluation result of ○ or △ indicates that the colorant could be prevented from discoloring for a long period of time, even after application of the cosmetics, and a desirable color could be maintained.

[0083] Discoloration prevention evaluation criteria 1 ○: No discoloration, and the same color as the manufactured cosmetic was retained △: Discoloration was slightly strong reddish ×: Discoloration was dark reddish

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] <Colorant Capture Ability Evaluation 2> Using the urethane polymer 3 produced in Example 3, cosmetics (total amount 10 g) containing the urethane polymer of the present invention were produced as shown in Tables 10 to 12, and the colorant capture ability of each cosmetic was evaluated. Specifically, the components were mixed to produce a cosmetic, which was then stirred at 80°C for 5 minutes and allowed to cool to room temperature. After standing, each cosmetic separated into an upper layer primarily composed of diphenyl dimethicone and triisostearin, a middle layer primarily composed of the urethane polymer, and a lower layer primarily composed of water, and it is believed that the colorant was present in one of these layers. The appearance of each cosmetic after standing was visually observed, and the colorant capture ability of each cosmetic was evaluated based on the colorant capture ability evaluation criteria 2 described below. The evaluation results are shown in Tables 10 to 12. In this evaluation, if the evaluation result is ○, in a cosmetic containing a colorant, even if it contains silicone oil, ester oil, or the like, it is possible to prevent the colorant from dispersing throughout the cosmetic. This indicates that, for example, in a lipstick or the like containing an oily component as its main component, by preventing the colorant from dispersing in the surface layer after application, even when the surface of the applied area comes into contact with a mask or the like, the effect of not causing color transfer to the mask or the like can be achieved.

[0091] Colorant Capture Evaluation Criteria 2: ○: All of the colorant is dispersed only in the middle and lower layers. ×: The colorant is also dispersed in the upper layer.

[0092] <Discoloration Resistance Evaluation 2> Separately from the evaluation of colorant capture ability, cosmetics (total amount 10 g) containing the urethane polymer of the present invention were prepared as shown in Tables 10 to 12, and their discoloration resistance was evaluated. Specifically, the components were mixed to prepare the cosmetics, stirred at 80°C for 5 minutes, and then air-cooled to room temperature. After that, approximately 0.25 ml of the middle layer (the layer believed to be mainly composed of the urethane polymer) of each cosmetic was extracted using a dropper and dispensed onto white art paper, and allowed to stand at room temperature for 5 minutes. After standing, the color of the cosmetics was visually observed and the discoloration resistance of each cosmetic was evaluated based on the discoloration resistance evaluation criteria 2 described below. The evaluation results are shown in Tables 10 to 12. In this evaluation, an evaluation result of ○ indicates that the colorant can be prevented from discoloring for a long period of time, even after application of the cosmetics, and a desirable color can be maintained.

[0093] Discoloration prevention evaluation criteria 2 ○: No discoloration, and the same color as the manufactured cosmetic was retained ×: Discoloration occurred

[0094]

[0095]

[0096]

[0097] From the above results, it can be seen that the urethane polymer of the present invention has excellent properties such as SPF boost effect, colorant capture ability, and discoloration prevention ability, and is therefore a urethane polymer that can be suitably used in cosmetics.

[0098] Formulation examples of cosmetics containing the urethane polymers of the present invention, including urethane polymers 1 to 4 produced in Examples 1 to 4, are shown in the following Tables 13 to 39. The values ​​in each table represent the content (mass %) of each component in each cosmetic.

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

Claims

1. A urethane polymer obtained by reacting castor oil with isophorone diisocyanate and having a weight average molecular weight of 10,000 to 150,000.

2. The urethane polymer according to claim 1, which is used in cosmetics.

3. A cosmetic containing the urethane polymer according to claim 1.

4. A cosmetic comprising the urethane polymer of claim 1 and an ultraviolet absorber.

5. A cosmetic comprising the urethane polymer of claim 1 and a colorant.

6. A method for producing a urethane polymer according to claim 1, comprising reacting the castor oil and the isophorone diisocyanate in amounts such that the ratio (OH:NCO) of the number of hydroxyl groups in the castor oil to the number of isocyanate groups in the isophorone diisocyanate is 1:0.40 to 1:0.

90.

7. A method for improving the SPF boost effect of a cosmetic, comprising blending an ultraviolet absorber and the urethane polymer of claim 1 into the cosmetic.

8. A method for improving the colorant capture and discoloration prevention properties of a cosmetic, comprising blending a colorant and the urethane polymer of claim 1 into the cosmetic.

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