Copolymer and cosmetic composition containing said copolymer

Abstract

The present specification discloses: a copolymer which is obtained by reacting a diglycerol fatty acid ester represented by general formula (1) with isophorone diisocyanate and which has a weight average molecular weight of 3,500-100,000; and a cosmetic composition containing said copolymer. (In the formula, R1 represents an alkyl group having 8-24 carbon atoms or an alkenyl group having 8-24 carbon atoms, X1 to X3 each independently represent a hydrogen atom or a group represented by -C(=O)R2, and R2 represents an alkyl group having 8-24 carbon atoms or an alkenyl group having 8-24 carbon atoms. However, at least one of X1 to X3 is a hydrogen atom.)

Description

Copolymer and cosmetic composition containing said copolymer

[0001] The present invention relates to a copolymer that improves various properties of various products, such as application ease, adhesion, glossiness, and usability, and that can be suitably used particularly as a raw material for cosmetics, and to a cosmetic composition containing the copolymer.

[0002] Taking advantage of the flexibility, elasticity, strength, stability, and safety of polyurethane particles and coatings, polyurethanes with various structures have been developed and are used in products such as cosmetics and coatings. For example, Patent Document 1 describes a cosmetic containing organic microspherical powder that contains a specific spherical polyurethane fine powder and has excellent slipperiness and feel on the skin. Patent Document 2 proposes an aerosol composition useful as an aerosol-type gommage cosmetic, consisting of an aqueous concentrate containing a urethane resin and liquefied gas. Patent Document 3 proposes the use of a polyurethane salt composed of a polylactic acid polyol, a diol, and a diisocyanate as an auxiliary agent in the formulation of cosmetics and pharmaceuticals.

[0003] Furthermore, Patent Document 4 describes an oil-based composition that allows for easy adjustment of product viscosity and provides a good feel and thickening effect to the product. The oil-based composition includes at least one urethane polymer selected from the group consisting of a (PPG-12 / SMDI) copolymer and a (polyglyceryl-2 diisostearate / IPDI) copolymer, silica particles, and one or more oil components selected from ester oils, hydrocarbon oils, and silicone oils. While this oil-based composition can provide a good feel and thickening effect to a product, the silica particles required to provide these properties can make it difficult to apply depending on the form of the final product. Furthermore, there is a risk of adverse effects on the glossiness and usability of cosmetics. Furthermore, the resulting feel and other characteristics still do not meet the standards desired by users. Therefore, there is a need in the market for a raw material that can be more simply configured and improve various properties of various products, such as application, adhesion, glossiness, and usability.

[0004] Japanese Patent Application Laid-Open No. 5-262622 Japanese Patent Application Laid-Open No. 2003-137730 Japanese Patent Application Laid-Open No. 7-509741 International Publication No. 2021 / 182500

[0005] Therefore, an object of the present invention is to provide a copolymer that can improve various properties of various products, such as the application property, adhesion, glossiness, and usability, and that can be suitably used particularly as a raw material for cosmetics, and a cosmetic composition containing the copolymer.

[0006] The present inventors have conducted extensive research and found that a specific copolymer is excellent in all aspects of application, adhesion, gloss, and usability, and is particularly suitable for use in cosmetics, leading to the completion of the present invention. Specifically, the present invention relates to a copolymer obtained by reacting a diglycerin fatty acid ester represented by the following general formula (1) with isophorone diisocyanate, and having a weight-average molecular weight of 3,500 to 100,000:

[0007]

[0008] In the formula, R 1 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms; X 1 ~X 3 are each independently a hydrogen atom or —C(═O)R 2 R represents a group represented by 2 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. 1 ~X 3 At least one of the groups is a hydrogen atom.

[0009] The copolymer of the present invention can be used as a raw material for various products, and can simultaneously improve various properties of the products, such as application property, adhesion, glossiness, and usability, and can be particularly suitably used as a raw material for cosmetics.

[0010] The diglycerin fatty acid ester used in the production of the copolymer of the present invention is a diglycerin fatty acid ester represented by the following general formula (1).

[0011]

[0012] In general formula (1), R 1represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. Examples of such groups include linear alkyl groups having 8 to 24 carbon atoms, branched alkyl groups having 8 to 24 carbon atoms, linear alkenyl groups having 8 to 24 carbon atoms, and branched alkenyl groups having 8 to 24 carbon atoms. Examples of the alkyl group include octyl, 2-ethylhexyl, secondary octyl, nonyl, secondary nonyl, decyl, secondary decyl, undecyl, secondary undecyl, dodecyl, secondary dodecyl, tetradecyl, secondary tetradecyl, hexadecyl, secondary hexadecyl, stearyl, eicosyl, docosyl, tetracosyl, 2-butyloctyl, 2-butyldecyl, 2-hexyloctyl, 2-hexyldecyl, 2-octyldecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-decyltetradecyl, isostearyl, etc. Examples of the alkenyl group include those in which a methylene group at any position in the above alkyl groups is replaced with —CH═CH—.

[0013] Among these, from the viewpoint of the application property and adhesion of the resulting copolymer and cosmetic composition, R 1 is preferably an alkyl group having 10 to 22 carbon atoms or an alkenyl group having 10 to 22 carbon atoms, more preferably an alkyl group having 12 to 20 carbon atoms or an alkenyl group having 12 to 20 carbon atoms, even more preferably a linear or branched alkyl group having 12 to 18 carbon atoms, and particularly preferably a branched alkyl group having 12 to 18 carbon atoms. For example, R 1 can be an isostearyl group.

[0014] In general formula (1), X 1 ~X 3 are each independently a hydrogen atom or —C(═O)R 2 where X represents a group represented by the formula: 1 ~X 3 Among these, from the viewpoint of the application property and adhesion of the obtained copolymer and cosmetic composition, at least one of X is a hydrogen atom. 1 ~X 3 Two of them are hydrogen atoms and one is -C(=O)R 2Preferably, X is a group represented by 1 and X 2 is a hydrogen atom, and X 3 -C(=O)R 2 It is more preferable that the group is a group represented by the following formula:

[0015] R 2 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. Examples of such groups include linear alkyl groups having 8 to 24 carbon atoms, branched alkyl groups having 8 to 24 carbon atoms, linear alkenyl groups having 8 to 24 carbon atoms, and branched alkenyl groups having 8 to 24 carbon atoms. R 2 Specific alkyl or alkenyl groups of the above R 1 Among these, from the viewpoint of the application property and adhesion of the resulting copolymer and cosmetic composition, R 2 is preferably an alkyl group having 10 to 22 carbon atoms or an alkenyl group having 10 to 22 carbon atoms, more preferably an alkyl group having 12 to 20 carbon atoms or an alkenyl group having 12 to 20 carbon atoms, even more preferably a linear or branched alkyl group having 12 to 18 carbon atoms, and particularly preferably a branched alkyl group having 12 to 18 carbon atoms. 1 ~X 3 Two or more of the following are -C(=O)R 2 When R is a group represented by 2 may be the same group or different groups. For example, R 2 In one embodiment of the copolymer of the present invention, X in general formula (1) may be an isostearyl group. 1 and X 2 is a hydrogen atom, and X 3 -C(=O)R 2 and R 1 and R 2 can be prepared using diglycerin fatty acid esters in which all of the above are isostearyl groups.

[0016] The diglycerol fatty acid ester used in producing the copolymer of the present invention is not particularly limited as long as it is represented by the following general formula (1), and may be a petroleum-derived diglycerol fatty acid ester or a diglycerol fatty acid ester derived from a natural material. Examples of diglycerol fatty acid esters derived from natural materials include diglycerol fatty acid esters derived from plant materials, which are produced using specific glycerol fatty acid esters obtained by extracting and / or refining vegetable oils. In the present invention, producing a copolymer using a diglycerol fatty acid ester derived from a plant material and represented by general formula (1) is preferred because it enables the production of a copolymer with a high natural origin index. Specifically, in the present invention, using a diglycerol fatty acid ester derived from a plant material and represented by general formula (1) as the natural origin raw material, it is preferred to produce a copolymer with a natural origin index of 50% or more, more preferably a copolymer with a natural origin index of 70% or more, and even more preferably a copolymer with a natural origin index of 80% or more. In the present invention, the natural origin index of the copolymer is a value calculated in accordance with ISO 16128.

[0017] The copolymer of the present invention is obtained by reacting the above-mentioned diglycerin fatty acid ester with isophorone diisocyanate, and has a weight-average molecular weight of 3,500 to 100,000. From the viewpoints of the application property, glossiness, and usability of the resulting cosmetic composition, the weight-average molecular weight of the copolymer is preferably 4,000 to 85,000, more preferably 5,000 to 40,000, even more preferably 5,500 to 25,000, and particularly preferably 6,000 to 21,000. In the present invention, the weight-average molecular weight of the copolymer can be adjusted by adjusting the ratio of raw materials used in the reaction of the diglycerin fatty acid ester with isophorone diisocyanate and the reaction conditions (temperature, pressure, time, catalyst, additives, etc.). In the present invention, the weight-average molecular weight of the copolymer is measured by gel permeation chromatography (GPC) and calculated in terms of styrene.

[0018] The GPC measurement conditions are as follows: [GPC measurement conditions] Apparatus: HLC-8220GPC (manufactured by Tosoh Corporation) Column: TSKgel SuperMultiporeHZ-N (manufactured by Tosoh Corporation) Column temperature: 40°C Sample concentration: 0.5% by mass Developing solvent: tetrahydrofuran Detector: RI detector Reference material: TSKgel standard polystyrene (manufactured by Tosoh Corporation)

[0019] The copolymer of the present invention has a structure resulting from a reaction between the -OH structural unit of the diglycerol fatty acid ester and the isocyanate group of isophorone diisocyanate, but since one or more -OH structural units in the diglycerol fatty acid ester react with the isocyanate group of isophorone diisocyanate in any desired manner to form a urethane bond, the structure of the copolymer will vary greatly depending on the specific structure of the diglycerol fatty acid ester used and the ratio of each raw material used. For this reason, it is impossible or even impractical to uniquely describe the structure of the copolymer of the present invention by a general formula.

[0020] Examples of methods for producing the copolymer of the present invention include a method of reacting a diglycerol fatty acid ester with isophorone diisocyanate until no reactive isocyanate groups remain, and a method of reacting a diglycerol fatty acid ester with isophorone diisocyanate to produce a prepolymer, and then reacting the prepolymer with a chain extender. When a chain extender is used, the type of chain extender is not particularly limited, and for example, one or more types selected from the group consisting of water, ethylenediamine, and propylenediamine can be used.

[0021] In the method for producing the copolymer of the present invention, a solvent may be used as needed, such as ethanol, propanol, butanol, hexane, toluene, xylene, methyl ethyl ketone, ethyl acetate, butyl acetate, water, etc.

[0022] In the method for producing the copolymer of the present invention, a catalyst may be used to promote the reaction between the diglycerol fatty acid ester and isophorone diisocyanate. Examples of the catalyst 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, alcoholates, and carbonates of alkali metals and alkaline earth metals such as sodium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, and sodium carbonate; metal oxides such as 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 soaps such as sodium acetate, potassium acetate, sodium propionate, potassium propionate, sodium octylate, potassium octylate, sodium laurate, and potassium laurate. The amount of these catalysts to be added is not particularly limited, but may be about 0.001 to 1% by mass based on the total mass of the diglycerin fatty acid ester and isophorone diisocyanate used.

[0023] In the method for producing the copolymer of the present invention, other raw materials capable of reacting with the diglycerol fatty acid ester or isophorone diisocyanate may be used as long as the effects of the present invention are not impaired, but from the viewpoint of the effects of the present invention, it is preferable to use either a method in which a reactive raw material consisting of a diglycerol fatty acid ester and isophorone diisocyanate is reacted until all reactive isocyanate groups are exhausted, or a method in which a reactive raw material consisting of a diglycerol fatty acid ester and isophorone diisocyanate is reacted to produce a prepolymer, and then the prepolymer is reacted with a chain extender. In this specification, the term "reactive raw material" refers to the raw material used in the polymerization reaction in the method for producing the copolymer of the present invention.

[0024] In the method for producing the copolymer of the present invention, the conditions are not particularly limited as long as they allow the diglycerol fatty acid ester and isophorone diisocyanate to react with each other, and the reaction may be carried out by adding the entire amount of each raw material at once or by adding the raw materials in several portions. For example, a method may be used in which the reaction raw materials containing the diglycerol fatty acid ester or isophorone diisocyanate are added to the reaction system at once or in several portions, respectively, and mixed at a temperature of 30 to 160°C, preferably 60 to 160°C, under pressurized, reduced, or normal pressure, and the mixture is maintained for 30 minutes to 10 hours until the reaction is complete.

[0025] The fields in which the copolymer of the present invention can be used are not particularly limited, and it can be used in various products such as paints, inks, adhesives, fuels, lubricants, and cosmetics. In this case, the paints, adhesives, fuels, lubricants, cosmetics, and other products may contain known materials depending on the mode of use and purpose. Among these, the copolymer of the present invention is preferably used as a raw material for cosmetics because of its excellent coatability and adhesion.

[0026] When the copolymer of the present invention is used in a cosmetic, the type of cosmetic is not particularly limited, and examples thereof include lotion, cosmetic liquid, emulsion, cream, facial cleanser, cleansing milk, cleansing lotion, skin mist, hair tonic, hair liquid, setting lotion, hair bleach, color rinse, permanent wave liquid, mascara, lipstick, lip gloss, pack, foundation, eau de cologne, shampoo, rinse, treatment, hair wax, hair oil, hair milk, hair manicure, eyeliner, sunscreen, deodorant, perfume, cleansing oil, and cosmetic oil.

[0027] When the copolymer of the present invention is used in a cosmetic, the amount of the copolymer blended into the cosmetic is not particularly limited and can be adjusted depending on the type and purpose of the cosmetic to be blended, but may be, for example, 0.01 to 90% by mass relative to the total amount of the cosmetic. In this case, when the copolymer of the present invention is blended into the cosmetic particularly for the purpose of imparting properties such as ease of application, glossiness, and ease of use, the amount blended is preferably 0.01 to 25% by mass, more preferably 0.05 to 20% by mass, even more preferably 0.1 to 15% by mass, and particularly preferably 0.5 to 10% by mass, relative to the total amount of the cosmetic. Such cosmetics are not particularly limited, but examples thereof include lotions, lotions, emulsions, creams, facial cleansing foams, cleansing milks, cleansing lotions, skin mists, hair tonics, hair liquids, setting lotions, hair bleaches, color rinses, permanent wave solutions, masks, foundations, colognes, shampoos, rinses, treatments, hair waxes, hair oils, hair milks, hair manicures, eyeliners, sunscreens, deodorants, perfumes, cleansing oils, and cosmetic oils. Furthermore, when the copolymer of the present invention is blended into cosmetics, particularly for the purpose of imparting a good adhesion, it is blended in an amount of preferably 5 to 90% by mass, more preferably 10 to 85% by mass, even more preferably 20 to 80% by mass, and particularly preferably 25 to 80% by mass, based on the total amount of the cosmetics. Such cosmetics are not particularly limited, but examples thereof include mascara, lipstick, and lip gloss.

[0028] Furthermore, the method for adding the copolymer of the present invention to a cosmetic is not particularly limited, and any known method can be used, such as adding the copolymer of the present invention to a blend containing some or all of the other components of the cosmetic at room temperature or in a temperature-controlled environment, and stirring, etc., as necessary. Because the copolymer of the present invention has the structure described above, when added to a cosmetic, it can simultaneously improve various properties.

[0029] The cosmetic composition of the present invention is a cosmetic composition containing the copolymer described above. Examples of such cosmetic compositions include lotions, cosmetic liquids, emulsions, creams, facial cleansing foams, cleansing milks, cleansing lotions, skin mists, hair tonics, hair liquids, setting lotions, hair bleaches, color rinses, permanent wave liquids, mascara, lipsticks, lip glosses, face masks, foundations, colognes, shampoos, rinses, treatments, hair waxes, hair oils, hair milks, hair manicures, eyeliners, sunscreens, deodorants, perfumes, cleansing oils, and cosmetic oils. The properties of the cosmetic of the present invention can also be appropriately adjusted depending on the intended use and product form, and may be in the form of, for example, a liquid, emulsion, gel, cream, solid powder, foam, mist, or the like.

[0030] The content of the copolymer in the cosmetic composition of the present invention is not particularly limited and can be adjusted depending on the purpose and application, but may be, for example, 0.01 to 90% by mass relative to the total amount of the cosmetic composition. In this case, when the copolymer of the present invention is contained in a cosmetic composition particularly for the purpose of imparting properties such as coatability, glossiness, and ease of use, the content of the copolymer in the cosmetic composition is preferably 0.01 to 25% by mass, more preferably 0.05 to 20% by mass, even more preferably 0.1 to 15% by mass, and particularly preferably 0.5 to 10% by mass, relative to the total amount of the cosmetic composition. Examples of the cosmetic composition include lotions, cosmetic liquids, emulsions, creams, facial cleansing foams, cleansing milks, cleansing lotions, skin mists, hair tonics, hair liquids, setting lotions, hair bleaches, color rinses, permanent wave solutions, packs, foundations, colognes, shampoos, rinses, treatments, hair waxes, hair oils, hair milks, hair manicures, eyeliners, sunscreens, deodorants, perfumes, cleansing oils, and cosmetic oils. Furthermore, when the copolymer of the present invention is contained in a cosmetic composition for the purpose of imparting a particularly good adhesion feel, the content of the copolymer in the cosmetic composition is preferably 5 to 90% by mass, more preferably 10 to 85% by mass, even more preferably 20 to 80% by mass, and particularly preferably 25 to 80% by mass, based on the total amount of the cosmetic composition. Examples of the cosmetic composition include mascara, lipstick, and lip gloss.

[0031] In addition to the copolymer described above, the cosmetic composition of the present invention may contain components commonly used in cosmetic compositions to improve or modify various properties (solubility, dispersibility, stability, usability, application, penetration, moisture retention, safety, design properties, optical properties, fragrance, whitening properties, etc.) during storage, during use, and after use, depending on the mode or purpose of use. Examples of such components include cationic surfactants, anionic surfactants, amphoteric surfactants, nonionic surfactants, hydrocarbon oils, silicone oils, ester oils, higher alcohols, polyhydric alcohols, sugars and their derivatives, pH adjusters, dyes / pigments, fragrances, ultraviolet absorbers, solvents, etc., and one or more of these may be optionally blended.

[0032] Examples of cationic surfactants include 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, and stearoxypropyldimethylamine, and one or more of these can be used. The concentration of the cationic surfactant can be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, based on the total amount of the cosmetic composition.

[0033] Examples of anionic surfactants include alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate ester salts, alkenyl ether sulfates, alkenyl sulfates, olefin sulfonates, alkanesulfonates, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylate salts, α-sulfonic acid salts, N-acylamino acid surfactants, phosphate mono- or diester surfactants, sulfosuccinate esters, N-alkyloylmethyl taurine salts, and derivatives thereof. Specific examples of counter ions of the anionic group include sodium ions, potassium ions, triethanolamine, and the like, and one or more of these can be used. The concentration of the anionic surfactant can be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, relative to the total amount of the cosmetic composition.

[0034] Examples of amphoteric surfactants include betaine-type amphoteric surfactants such as 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, and 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, and one or more of these may be used. The concentration of the amphoteric surfactant may be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, relative to the total amount of the cosmetic composition.

[0035] Examples of nonionic surfactants include 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, and POE hexastearate. Examples of the glycerin monoester include POE sorbitol, 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, and POE methyl glucoside dioleate, and these may be used alone or in combination. The concentration of the nonionic surfactant can be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, relative to the total amount of the cosmetic composition.

[0036] Examples of hydrocarbon oils include liquid paraffin, squalane, pristane, ozokerite, paraffin, ceresin, petrolatum, polyisobutene, polyisoprene, isodecane, isododecane, isohexadecane, normal pentane, isopentane, normal hexane, isohexane, kerosene, decalin, tetralin, microcrystalline wax, etc., and one or more of these can be used. The concentration of the hydrocarbon oil can be, for example, 0.1% by mass to 50% by mass, and preferably 0.5% by mass to 30% by mass, relative to the total amount of the cosmetic composition.

[0037] Examples of silicone oils include chain silicone oils such as dimethylpolysiloxane, dimethiconol, diphenylpolysiloxane, diphenylsiloxyphenyltrimethicone, and octamethyltrisiloxane; cyclic silicone oils such as decamethylcyclotetrasiloxane, dodecamethylcyclotetrasiloxane, octamethylcyclotetrasiloxane, cyclopentasiloxane, dodecamethylcyclopentasiloxane, octamethylcyclopentasiloxane, decamethylcyclohexasiloxane, dodecamethylcyclohexasiloxane, and octamethylcyclohexasiloxane; and modified silicone oils such as alkyl-modified dimethylpolysiloxane, polyether-modified dimethylpolysiloxane, carbinol-modified polysiloxane, fatty acid-modified polysiloxane, higher alcohol-modified polysiloxane, amino-modified polysiloxane, and fluorine-modified polysiloxane. One or more of these can be used. The concentration of the silicone oil can be, for example, 0.1% by mass to 50% by mass, and preferably 0.5% by mass to 30% by mass, relative to the total amount of the cosmetic composition.

[0038] Examples of ester oils include ethyl acetate, butyl acetate, hexyl acetate, decyl acetate, butyl propionate, cetyl octanoate, hexyldecyl dimethyloctanoate, isononyl isononanoate, isononyl isononanoate, isotridecyl isononanoate, ethyl laurate, hexyl laurate, myristyl myristate, isopropyl myristate, isopropyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl palmitate, 2-heptylundecyl palmitate, decyl oleate, oleyl oleate, octyldodecyl oleate, isocetyl stearate, glycerin stearate, butyl stearate, ethylhexyl hydroxystearate, ethylene glycol stearate, and oxystearate. Examples of the oil include synthetic ester oils such as octyl phosphate, diethyl phthalate, triethyl citrate, 2-ethylhexyl succinate, diisopropyl sebacate, di-2-ethylhexyl sebacate, cetyl lactate, myristyl lactate, diisobutyl adipate, 2-hexyldecyl adipate, di-2-heptylundecyl adipate, cetyl ethylhexanoate, triethylhexanoin, polyglyceryl-2 triisostearate, neopentyl glycol dioctanoate, neopentyl glycol dicaprate, and pentaerythrityl tetraisostearate; and animal and vegetable ester oils such as lanolin, mink oil, cacao butter, coconut oil, palm kernel oil, camellia oil, sesame oil, castor oil, and olive oil. One or more of these may be used. The concentration of the ester oil can be, for example, 0.1% by mass to 50% by mass, and preferably 0.5% by mass to 30% by mass, relative to the total amount of the cosmetic composition.

[0039] Examples of higher alcohols include cetyl alcohol, isostearyl alcohol, lauryl alcohol, hexadecyl alcohol, octyldodecanol, etc., and one or more of these may be used. The concentration of the higher alcohol is, for example, preferably 0.1% by mass to 30% by mass, and more preferably 0.5% by mass to 20% by mass, relative to the total amount of the cosmetic composition.

[0040] Examples of polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, highly polymerized polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, isoprene glycol, 1,3-butylene glycol, glycerin, diglycerin, polyglycerin, etc., and one or more of these may be used. The concentration of the polyhydric alcohol may be, for example, 0.1% by mass to 30% by mass, and preferably 0.5% by mass to 20% by mass, relative to the total amount of the cosmetic composition.

[0041] Examples of sugars and derivatives thereof include xylose, D-glucose, sucrose, trehalose, fructose, maltose, mannose, cyclodextrin, β-glucan, chitin, chitosan, pectin, arabinogalactan, dextrin, dextran, glucosyl ethyl methacrylate polymers or copolymers, and one or more of these can be used. The concentration of the sugars and derivatives thereof can be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, relative to the total amount of the cosmetic composition.

[0042] Examples of pH adjusters include citric acid, glycolic acid, succinic acid, tartaric acid, lactic acid, malic acid, levulinic acid, acetic acid, butyric acid, valeric acid, oxalic acid, maleic acid, fumaric acid, mandelic acid, phosphoric acid, pyrophosphoric acid, hydrochloric acid, sulfuric acid, and nitric acid, and one or more of these can be used. The pH adjuster is preferably added so that the pH of the cosmetic composition of the present invention, for example, is 3.0 to 13.0.

[0043] Examples of dyes and pigments include various legal dyes, acid dyes, basic dyes, oxidation dye intermediates, couplers, autoxidation dyes, nitro dyes, disperse dyes, inorganic pigments, metal powder pigments, and surface-treated products thereof, and one or more of these can be used. The concentration of the dye or pigment can be, for example, 0.001% by mass to 10% by mass, and preferably 0.01% by mass to 5% by mass, relative to the total amount of the cosmetic composition.

[0044] Examples of fragrances include acetyl cedrene, allyl amyl glycolate, β-ionone, isobutylquinoline, iris oil, irone, indole, undecanal, undecenal, γ-undecalactone, estragole, eugenol, oakmoss, opoponax resinoid, orange oil, eugenol, aurantiol, galacsolid, carvacrol, camphor, carrot seed oil, clove oil, methyl cinnamate, geraniol, and geranyl. Nitrile, isobornyl acetate, geranyl acetate, dimethylbenzylcarbinyl acetate, styrallyl acetate, cedryl acetate, terpinel acetate, vetiveryl acetate, benzyl acetate, linalyl acetate, isopentyl salicylate, benzyl salicylate, sandalwood oil, santalol, cyclamen aldehyde, cyclopentadecanolide, methyl dihydrojasmonate, dihydromyrcenol, jasmine absolute, jasmine lactone, citral, citronellol, Citronellal, cinnamon bark oil, styrax resinoid, cedarwood oil, cedrene, cedrol, celery seed oil, thyme oil, damascone, damascenone, thymol, tuberose absolute, terpineol, gamma-terpinene, triprol, vanilla absolute, vanillin, basil oil, patchouli oil, hydroxycitronellal, alpha-pinene, piperitone, balsam of Peru, vetiver oil, vetiverol, peppermint oil, pepper oil, heliotrope Examples of fragrances include tropine, bergamot oil, benzyl benzoate, borneol, myrresinoid, musk ketone, methylnonylacetaldehyde, γ-methylionone, menthol, L-menthol, L-menthone, eucalyptus oil, β-ionone, lime oil, lavender oil, D-limonene, linalool, lyral, lilial, lemon oil, rose absolute, rose oxide, rose oil, and rosemary oil, and one or more of these can be used. The concentration of the fragrance can be, for example, 0.001% to 5% by mass, and preferably 0.01% to 3% by mass, relative to the total amount of the cosmetic composition.

[0045] Examples of ultraviolet absorbers include 2,4-dihydroxybenzophenone, 5,5'-methylenebis(2-hydroxy-4-methoxybenzophenone), 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl)benzotriazole, 2-(2-hydroxy-3,5-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-5-chlorobenzotriazole, 2-(2-hydroxy-3,5-di cumylphenyl)benzotriazole, 2,2'-methylenebis(4-tert-octyl-6-benzotriazolylphenol), polyethylene glycol ester of 2-(2-hydroxy-3-tert-butyl-5-carboxyphenyl)benzotriazole, 2-[2-hydroxy-3-(2-acryloyloxyethyl)-5-methylphenyl]benzotriazole, 2-[2-hydroxy-3-(2-methacryloyloxyethyl)-5-butylphenyl]benzotriazole, 2-[2-hydroxy-3-(2-methacryloyloxyethyl)-5-tert-butylphenyl]benzotriazole, 2-[2-hydroxy-3-(2-methacryloyloxyethyl)-5-tert-octylphenyl]benzotriazole, 2-[2-hydroxy-3-(2-methacryloyloxyethyl)-5-tert-butylphenyl]-5-chlorobenzotriazole, 2-[2-hydroxy-5-(2-methacryloyloxyethyl)phenyl]benzotriazole, 2-[2-hydroxy-3-tert-butyl-5-(2-methacryloyloxyethyl)phenyl]benzotriazole, 2-[2-hydroxy-3-tert-amyl-5-(2-methacryloyloxyethyl)phenyl] Benzotriazole, 2-[2-hydroxy-3-tert-butyl-5-(3-methacryloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-[2-hydroxy-4-(2-methacryloyloxymethyl)phenyl]benzotriazole, 2-[2-hydroxy-4-(3-methacryloyloxy-2-hydroxypropyl)phenyl]benzotriazole, 2-[2-hydroxy-4-(3-methacryloyloxypropyl)phenyl]benzotriazole, phenyl salicylate, resorcinol monobenzoate, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, octyl (3,5-di-tert-butyl-4-hydroxy)benzoate, dodecyl (3,5-di-tert-butyl-4-hydroxy)benzoate, tetradecyl (3,5-di-tert-butyl-4-hydroxy)benzoate, hexadecyl (3,5-di-tert-butyl-4-hydroxy)benzoate, octadecyl (3,5-di-tert-butyl-4-hydroxy)benzoate, behenyl (3,5-di-tert Examples of ultraviolet absorbers include 2-butyl-4-hydroxybenzoate, 2-ethyl-2'-ethoxyoxanilide, 2-ethoxy-4'-dodecyloxanilide, ethyl-α-cyano-β,β-diphenylacrylate, methyl-2-cyano-3-methyl-3-(p-methoxyphenyl)acrylate, ethylhexyl methoxycinnamate, bisethylhexyloxyphenol methoxyphenyl triazine, diethylaminohydroxybenzoylhexylbenzoate, and various metal salts or metal chelates, and one or more of these can be used. The concentration of the ultraviolet absorber can be, for example, 0.001% to 10% by mass, and preferably 0.01% to 5% by mass, based on the total amount of the cosmetic composition.

[0046] Examples of the solvent include ethanol, isopropyl alcohol, butanol, isobutyl alcohol, acetone, ethyl acetate, ethylene glycol monoethyl ether, water, etc., and one or more of these can be used. The concentration of the solvent can be, for example, 10% by mass to 99% by mass, and preferably 20% by mass to 95% by mass, based on the total amount of the cosmetic composition.

[0047] The viscosity of the cosmetic composition of the present invention at 25°C is not particularly limited and can be adjusted appropriately depending on the intended use and product form, but from the viewpoint of making the most of the application, adhesion, gloss, and usability provided by the copolymer described above, the viscosity of the cosmetic composition at 25°C is preferably 10 to 1,000,000 mPa·s, and more preferably 100 to 100,000 mPa·s. In the present invention, the viscosity of the cosmetic composition at 25°C is measured in accordance with JIS K 7117.

[0048] The present invention will be described in detail below with reference to examples and comparative examples, but the present invention is not limited thereto. In the following examples, percentages are by mass unless otherwise specified.

[0049] Example 1 In a glass reactor equipped with a stirrer, a cooling tube, and a nitrogen inlet tube, polyglyceryl-2 diisostearate derived from a plant material (in the general formula (1), R 1 is an isostearyl group, and X 1 and X 2 is a hydrogen atom, and X 3 -C(=O)R 2 is a group represented by R 2 450 g (0.60 mol) of a diglycerol fatty acid ester (in which NCO is an isostearyl group) and 60.3 g (0.27 mol) of isophorone diisocyanate were charged and reacted at 120°C for 1 hour. The reaction was terminated after confirming the absence of NCO absorption by infrared absorption spectroscopy, thereby producing Copolymer 1 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight average molecular weight of the resulting Copolymer 1, as measured by gel permeation chromatography (GPC) and calculated in terms of styrene, was 4,300.

[0050] Example 2 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 67 g (0.30 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated upon confirming the absence of NCO absorption by infrared absorption spectroscopy, thereby producing copolymer 2 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting copolymer 2, as calculated in terms of styrene, was 5,100 as measured by gel permeation chromatography (GPC).

[0051] Example 3 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 73.7 g (0.33 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing Copolymer 3 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting Copolymer 3, as calculated in terms of styrene, was 6,400 as measured by gel permeation chromatography (GPC).

[0052] Example 4 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 86.9 g (0.39 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated upon confirming the absence of NCO absorption by infrared absorption spectroscopy, thereby producing copolymer 4 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting copolymer 4, as calculated in terms of styrene, was 9,200 as measured by gel permeation chromatography (GPC).

[0053] Example 5 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 100.3 g (0.45 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing Copolymer 5 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting Copolymer 5, as calculated in terms of styrene, was 20,000 as measured by gel permeation chromatography (GPC).

[0054] Example 6 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 113.6 g (0.51 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing copolymer 6 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting copolymer 6, as calculated in terms of styrene, was 83,000 as measured by gel permeation chromatography (GPC).

[0055] Comparative Example 1 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 46.8 g (0.21 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing Copolymer 7 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting Copolymer 7, as calculated in terms of styrene, was 2,900 as measured by gel permeation chromatography (GPC).

[0056] Comparative Example 2 A glass reaction vessel equipped with a stirrer, a condenser, and a nitrogen inlet tube was charged with 450 g (0.60 mol) of plant-derived polyglyceryl-2 diisostearate and 116.3 g (0.52 mol) of isophorone diisocyanate, and the mixture was reacted at 120°C for 1 hour. The reaction was terminated after confirming that there was no NCO absorption by infrared absorption spectroscopy, thereby producing copolymer 8 consisting of a (polyglyceryl-2 diisostearate / IPDI) copolymer. The weight-average molecular weight of the resulting copolymer 8, as calculated in terms of styrene, was 130,000 as measured by gel permeation chromatography (GPC).

[0057] The copolymers obtained in Examples 1 to 6 and Comparative Examples 1 and 2 were each diluted 50% with liquid paraffin (Hicol K-230, manufactured by Kaneda Co., Ltd.) to prepare solutions. An appropriate amount was taken on a finger and applied to the back of the hand. Three panelists individually evaluated the applicability, adhesion, glossiness of the applied surface, and usability after application based on the following evaluation criteria. If three panelists rated the sample as ○, it was rated as ⊚ (Excellent); if two panelists rated it as ○, it was rated ○ (Good); and if less than two panelists rated it as ○, it was rated × (Poor). The evaluation results are shown in Table 1. In the following evaluation criteria, ○ means "pass" and × means "fail."

[0058] [Evaluation criteria for application] ○: Smooth and easy to apply to skin ×: Feels sticky or is hard and difficult to apply to skin [Evaluation criteria for adhesion] ○: Excellent adhesion to skin and no sticky feeling ×: Weak adhesion or sticky feeling [Evaluation criteria for gloss] ○: A clear gloss feeling is felt on the applied surface ×: No gloss feeling or almost no gloss feeling is felt on the applied surface [Evaluation criteria for usability] ○: Not washed away with running water (15°C) but easily removed with hot water (40°C) ×: Easily washed away with running water (15°C) or not washed away even with hot water (40°C)

[0059]

[0060] As can be seen from the above results, the copolymer of the present invention is excellent in all aspects of spreadability, adhesion, glossiness, and usability. Therefore, the copolymer of the present invention can be widely used for the purpose of improving the properties of products such as paints, inks, adhesives, fuels, lubricants, and cosmetics, and in particular, when blended in cosmetics, it can impart spreadability, adhesion, glossiness, and usability to the cosmetic composition.

[0061] Formulation examples of cosmetic compositions containing copolymers 1 to 6 produced in Examples 1 to 6 as cosmetics containing the copolymers of the present invention are shown in the following Tables 2 to 33. The values ​​in each table represent the content (mass%) of each component in each cosmetic composition.

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] The invention disclosed in this specification is as follows: [A] A copolymer obtained by reacting a diglycerin fatty acid ester represented by the following general formula (1) with isophorone diisocyanate, and having a weight average molecular weight of 3,500 to 100,000: (In the formula, R 1 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms; X 1 ~X 3 are each independently a hydrogen atom or —C(═O)R 2 R represents a group represented by 2 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. 1 ~X 3 At least one of the groups represented by the formula (1) is a hydrogen atom. 1 and X 2 are hydrogen atoms, and X 3 -C(=O)R 2 R represents a group represented by 2 [C] The copolymer of [A], containing a diglycerin fatty acid ester, wherein R is an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. [C] The copolymer of [A] or [B], wherein the diglycerin fatty acid ester is a diglycerin fatty acid ester derived from a plant material. [D] The copolymer of any of [A] to [C], wherein the weight-average molecular weight is 5,000 to 40,000. [E] A cosmetic composition containing any of the copolymers of [A] to [D]. [F] The cosmetic composition of [E], wherein the content of the copolymer is 0.01 to 90% by mass.

Claims

1. A copolymer obtained by reacting a diglycerin fatty acid ester represented by the following general formula (1) with isophorone diisocyanate, and having a weight average molecular weight of 3,500 to 100,000. (In the formula, R 1 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms; X 1 ~X 3 are each independently a hydrogen atom or —C(═O)R 2 R represents a group represented by 2 represents an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms. 1 ~X 3 At least one of the is a hydrogen atom.) 2. The diglycerin fatty acid ester is represented by the general formula (1), wherein X 1 and X 2 are hydrogen atoms, and X 3 -C(=O)R 2 R represents a group represented by 2 2. The copolymer of claim 1, comprising a diglycerin fatty acid ester, wherein is an alkyl group having 8 to 24 carbon atoms or an alkenyl group having 8 to 24 carbon atoms.

3. The copolymer according to claim 1, wherein the diglycerin fatty acid ester is derived from a plant material.

4. The copolymer of claim 1, wherein the weight average molecular weight is 5,000 to 40,000.

5. A cosmetic composition containing the copolymer according to any one of claims 1 to 4.

6. The cosmetic composition according to claim 5, wherein the content of the copolymer is 0.01 to 90% by mass.

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