JP2001199937A - Cosmetic oil, cosmetics and external preparation using the same - Google Patents

Abstract

(57) [Summary] [Problem] To provide cosmetics and external preparations which are excellent in safety, stability, water holding property, gloss and good feeling of use and which contain dimer acid esters. SOLUTION: A dimer acid ester excellent in safety, stability, water holding property and luster, and a cosmetic excellent in safety, stability, water holding property, luster and feeling of use by blending the dimer acid ester. And an external preparation.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a dimer acid ester obtainable by esterifying dimer acid with an alcohol containing at least sterol, and a cosmetic and external preparation containing the dimer acid ester. More specifically, a dimer acid ester excellent in safety, stability, water hydration, gloss, and feel, and a cosmetic and external use excellent in safety, stability, water hydration, gloss, and use feeling containing this ester Agent.

[0002]

2. Description of the Related Art Conventionally, various esters have been used in cosmetics and external preparations, but they have not always been satisfactory in safety, stability, water retention, luster, feel and the like.

Examples of conventionally used synthetic esters include, for example, cetyl isooctylate, isodecyl isononanoate, isopropyl palmitate, octyldodecyl myristate, octyl stearate, isostearyl isostearate, glyceryl isooctylate, glyceryl isostearate, and oleic acid. Octyl dodecyl, ethyl linoleate, ethyl cinnamate, octyl salicylate, propyl paraoxybenzoate, dioctyl phthalate and the like can be mentioned. These oils are hydrated,
It is not always satisfactory in terms of gloss, familiarity with skin and hair, and feeling of use. As dimer-acid esters as raw materials for cosmetics, diisopropyl dimer dilinoleate, dioctyl dimer dilinoleate, diisostearyl dimer dilinoleate, ditridecyl dimer dilinoleate, and dioctyl dodecyl dimer dilinoleate include CTFA (The Cosmetic, Toiletry and Fragrance A).
ssociation published by International Cosmetic Ingredient Dictionary (Internationa
l Cosmetic Ingredient Dictionary and Handbook), but these are also insufficient in terms of water holding property, gloss, and feeling of use.

[0004]

As described above, various esters have been used as oily raw materials for cosmetics and external preparations, but they are not always satisfactory, and furthermore, safety and stability are high. What has good hydration, gloss, and usability has been desired. The present invention provides a dimer acid ester having excellent safety, stability, water holding property, and luster as a raw material of cosmetics and external preparations, and a cosmetic composition obtained by blending them and making full use of their excellent characteristics. For external preparations.

[0005]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention. That is, according to the present invention, it is possible to obtain a safe, stable, water-retaining, and glossy oil agent by esterifying dimer acid with an alcohol containing at least sterol, and further contain those dimer acid esters. This makes it possible to obtain cosmetics and external preparations with good safety, stability, water hydration, luster, and feeling of use.

[0006] Dimer acid is a known dibasic acid obtained by an intermolecular polymerization reaction of unsaturated fatty acids, and its industrial production process is almost standardized in the industry. For example, it is obtained by dimerizing an unsaturated fatty acid having 11 to 22 carbon atoms or a lower alcohol ester thereof with a clay catalyst.
The industrially obtained dimer acid is mainly composed of a dibasic acid having about 36 carbon atoms, but contains an arbitrary amount of trimer acid and monomeric acid depending on the degree of purification. Generally, those having a dimer acid content exceeding 70% by weight and those having a dimer acid content increased to 90% or more by molecular distillation are distributed. Further, a double bond having a double bond remaining after the dimerization reaction and having been further hydrogenated to improve the oxidation stability is also on the market. In the present invention, any of such currently available dimer acids can be used.

[0007]

Embodiments of the present invention will be described below. The dimer acid ester of the present invention can be obtained, for example, by the following method. That is, the desired dimer acid ester is obtained by esterification of dimer acid with an alcohol containing at least sterol. The esterification method is not particularly limited, but can be synthesized by a generally used method. For example, using paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, boron trifluoride, hydrogen fluoride or the like as a catalyst or without a catalyst, using benzene, toluene, hexane, heptane or the like as a solvent or using no solvent The reaction may be performed at a temperature of 50 to 260 ° C. or,
The dimer acid ester of the present invention can also be obtained by a transesterification reaction between a dimer acid lower alcohol ester and an alcohol containing at least sterol. In this case, an alkali catalyst such as sodium hydroxide, potassium hydroxide or potassium carbonate, or a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium butoxide can be used as a catalyst.

In the esterification reaction and transesterification reaction, the average esterification degree of the resulting ester can be arbitrarily changed between monoester and diester by changing the charge ratio of dimer acid or lower alcohol ester of dimer acid to alcohol. It is possible to adjust. Further, the monoester can be further treated with an alkali such as sodium hydroxide, potassium hydroxide, potassium carbonate or the like to obtain an alkali metal salt, and further can be converted to another metal salt by a usual metathesis method.

The dimer acid is esterified with sterol and one alcohol selected from linear alcohols having 1 to 34 carbon atoms, branched alcohols having 3 to 34 carbon atoms, and unsaturated alcohols having 6 to 34 carbon atoms. In this case, as the alcohol component, a sterol and a linear alcohol having 1 to 34 carbon atoms and / or a branched alcohol having 3 to 34 carbon atoms and / or an unsaturated alcohol having 6 to 34 carbon atoms can be mixed and used. . In addition, since sterols generally have a lower reaction rate than other alcohols, if it is desired to obtain an ester in which each carboxyl group of dimer acid is uniformly esterified with sterols and other alcohols in a high yield, the dimer acid must be prepared in advance. After reacting only a sterol with an acid or dimer acid lower alcohol ester to obtain a monoester, from a linear alcohol having 1 to 34 carbon atoms or a branched alcohol having 3 to 34 carbon atoms or an unsaturated alcohol having 6 to 34 carbon atoms It is desirable to further react the selected alcohol.

Examples of the sterol used here include cholesterol, dihydrocholesterol, desmosterol, lanosterol, dihydrolanosterol, agnosterol, latosterol, sitosterol, campesterol, stigmasterol, brassicasterol, ergosterol and the like. Sterols contained in soybeans and rapeseed are sitosterols, campesterols, stigmasterols, brassicasterols, ergosterols, and the like, and sterols obtained as a mixture of these sterols are generally called phytosterols, and are used in the present invention. Can use phytosterols of various origins. Further, phytosterol may be used after hydrogenation.

Examples of the straight-chain alcohol having 1 to 34 carbon atoms include methanol, ethanol, propanol,
Butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, docosanol, tetracosanol And the like. Examples of the branched alcohol having 3 to 34 carbon atoms include isopropyl alcohol, isobutyl alcohol, isopentyl alcohol, isohexanol, isoheptanol, isooctanol, dimethyloctanol, isononanol, isodecanol, isoundecanol, isododecanol, and isotridecanol. Knol, isotetradecanol, isopentadecanol, isohexadecanol,
Isoheptadecanol, isooctadecanol, isononadecanol, isoeicosanol, 2-ethylhexanol, 2-butyloctanol, 2-hexyldecanol, 2-octyldodecanol, 2-decyltetradecanol, 2-dodecyl Hexadecanol, 2-tetradecyloctadecanol, 2-hexadecyloctadecanol, isostearyl alcohol obtained from a by-product of dimer acid, isostearyl alcohol obtained by reducing isostearic acid by the Garbet method, and aldol condensation method Examples include isostearyl alcohol obtained by reducing isostearic acid and long-chain branched alcohols (12 to 34) obtained from lanolin. 6-34 carbon atoms
Examples of the unsaturated alcohols include undecenol, laurorenol, myristorenol, palmitolenol, oleyl alcohol, elaidyl alcohol, linoleyl alcohol, linolenyl alcohol, erucyl alcohol, brassyl alcohol, arachidyl alcohol and the like. .

The obtained ester may be a diester or a monoester depending on the purpose, or a mixed ester of two or more alcohols. The dimer acid ester thus obtained can be used for appropriate applications as it is, but can be further purified by an ordinary method and used for various applications if necessary.

According to the invention, the molecular weight is between about 700 and 1,
Ester having a relatively high molecular weight of about 500 can be obtained, but they can provide an oil agent which is less irritating to the skin and has high durability. Further, a lubricating oil having good oxidation stability, high water hydration and a high refractive index can be obtained. Also, safety containing this dimer acid ester,
It is possible to provide cosmetics and external preparations that are excellent in stability, water holding property and gloss and have a good use feeling.

The blending amount of the dimer acid ester in the cosmetic of the present invention is not particularly limited, but is about 0.1 to 50% by weight, particularly preferably 0.5 to 30% by weight. In addition, the cosmetic of the present invention, if necessary, water and additives added to the usual cosmetics, such as fats and oils, emulsifiers, alcohols,
Moisturizer, thickener, antioxidant, antiseptic, bactericide, chelating agent, pH adjuster, ultraviolet absorber, whitening agent, solvent, exfoliant / dissolving agent, antipruritic, anti-inflammatory, antiperspirant, refreshing Agents, reducing agents, antihistamines, astringents, stimulants, hair growth agents,
Polymer powder, hydroxy acids, vitamins and their derivatives, sugars and their derivatives, organic acids, enzymes, nucleic acids, hormones, clay minerals, fragrances, pigments, and the like can be blended.

Examples of these additional components include, but are not limited to, cetanol, myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol, stearyl alcohol, aralkyl alcohol, jojoba alcohol, chimyl alcohol, butyl alcohol, hexyldecanol. , Higher alcohols such as isostearyl alcohol and 2-octyldodecanol; lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, behenic acid, undecylenic acid, 12-hydroxystearic acid, palmitoleic acid, oleic acid, linoleic acid Higher fatty acids such as acids, linoleic acid, erucic acid, docosahexaenoic acid, eicosapentaenoic acid, isohexadecanoic acid, anteisopentadecanoic acid, and long-chain branched fatty acids Metallic soaps such as aluminum salts, calcium salts, magnesium salts, zinc salts and potassium salts, and nitrogen-containing derivatives such as amides; liquid paraffin, squalane, squalene, petrolatum, solid paraffin, ceresin, microcrystalline wax, etc. Hydrocarbons; safflower oil, olive oil, castor oil, avocado oil, sesame oil, tea oil, evening primrose oil, wheat germ oil, macadamia nut oil, hazelnut oil, kukui nut oil,
Vegetable oils such as rosehip oil, meadowfoam oil, persic oil, tea tree oil, peppermint oil, hydrogenated castor oil and the like;
Vegetable fats such as cocoa butter, shea butter, wood wax, coconut oil, palm oil, palm kernel oil; animal fats such as beef tallow, milk fat, horse fat, egg yolk oil, mink oil, turtle oil; carnauba wax, candelilla Vegetable waxes such as wax, jojoba oil, hydrogenated jojoba oil; animal waxes such as beeswax, spermaceti, lanolin, orange luffy oil; liquid lanolin, reduced lanolin, adsorptive purified lanolin, lanolin acetate, lanolin acetate liquid Lanolin such as hydroxylanolin, polyoxyethylene lanolin, lanolin fatty acid, hard lanolin fatty acid, lanolin alcohol, lanolin alcohol acetate, acetic acid (cetyl lanolyl) ester; phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, sphingomyelin, phosphatidic acid, Such as lysolecithin Phospholipid derivatives such as hydrogenated soybean phospholipid and hydrogenated egg yolk phospholipid; sterols such as cholesterol, dihydrocholesterol, lanosterol, dihydrolanosterol, phytosterol; cholesteryl acetate, cholesteryl nonanoate, cholesteryl stearate, isostearin Acid cholesteryl, cholesteryl oleate, N-lauroyl-
L-glutamic acid di (cholesteryl behenyl octyldodecyl), N-lauroyl-L-glutamic acid di (cholesteryl octyldodecyl), N-lauroyl-L-glutamic acid di (phytosteryl-2-octyldodecyl), 12-hydroxystearic acid Cholesteryl, macadamia nut oil cholesteryl, macadamia nut oil phytosteryl, phytosteryl isostearate, soft lanolin fatty acid cholesteryl, hard lanolin fatty acid cholesteryl, long chain branched fatty acid cholesteryl, sterol esters such as cholesteryl long chain α-hydroxy fatty acid cholesteryl; ethyl oleate, avocado Oil fatty acid ethyl, isopropyl palmitate, octyl palmitate, isopropyl isostearate, isotridecyl isononanoate, la Lower alcohol fatty acid esters such as isopropyl phosphate fatty acid; higher alcohol fatty acid esters such as octyl dodecyl myristate, cetyl octoate, oleyl oleate, octyl dodecyl oleate, octyldodecyl lanolin fatty acid, hexyldecyl dimethyloctanoate and dioctyl succinate Higher alcohol oxyesters such as cetyl lactate and diisostearyl malate; polyhydric alcohol fatty acid esters such as glyceride trioleate, glyceride triisostearate, glyceride tri (caprylic / capric acid) and propylene glycol dioleate; Silicon resin, methylpolysiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, highly polymerized methylpolysiloxane, dimethylpolysiloxane, methylphenol Silicone derivatives such as phenylpolysiloxane, methylhydrogenpolysiloxane, organically modified polysiloxane, cyclic dimethylsiloxane, crosslinked methylpolysiloxane, and crosslinked methylphenylpolysiloxane; and perfluoropolyether.

Examples of the emulsifier include fatty acid salts, alkyl sulfate salts, alkylbenzene sulfonate salts, polyoxyethylene alkyl sulfate salts, polyoxyethylene fatty amine sulfate salts, acyl N-methyltaurine salts, alkyl ether phosphate salts, N Anionic surfactants such as acyl amino acid salts; polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether,
Nonionic surfactants such as polyoxyethylene alkyl ether sorbitan fatty acid partial ester, polyhydric alcohol fatty acid partial ester, polyglycerin fatty acid ester, polyoxyethylene fatty acid ester, alkyldimethylamine oxide, and alkylpolyglycoside; alkyltrimethylammonium chloride, short Cationic surfactants such as linear polyoxyethylene alkylamines and salts or quaternary salts thereof, and benzalkonium chloride; alkyldimethylaminoacetic acid betaine, alkylamidodimethylaminoacetic acid betaine, 2-alkyl-N-carboxy-N-
Amphoteric surfactants such as hydroxyimidazolinium betaine; polymeric surfactants such as polyvinyl alcohol, sodium alginate, starch derivatives, tragacanth rubber, and acrylic acid / methacrylic acid copolymer; and the like.

As humectants, propylene glycol,
Glycerin, polyhydric alcohols such as 1,3-butanediol, sodium hyaluronate, citrate, urea, lactic acid bacteria culture, yeast extract, eggshell membrane protein, bovine submandibular gland mucin, hypotaurine, sesame lignan glycoside, Betaine,
Chondroitin sulfate, ceramide (types 1, 2, 3,
4, 5, 6), hydroxyceramide, pseudo-ceramide, glycosphingolipid, glutathione, polyethylene glycol, sorbitol, carbitol, sodium lactate, 2,
-Sodium pyrrolidone-5-carboxylate, albumin, trimethylglycine; collagen, elastin, collagen-degrading peptide, elastin-degrading peptide, keratin-degrading peptide, conchiolin-degrading peptide, silk-proteolytic peptide, soybean-proteolytic peptide, wheat proteolytic peptide, casein Protein peptides such as degraded peptides and derivatives thereof; amino acids such as arginine, serine, glycine, threonine, glutamic acid, cysteine, methionine, leucine, tryptophan; placental extract, aerastin, collagen, aloe extract, hamamelis water, loofah water And animal / plant extracts such as chamomile extract, licorice extract and comfrey extract.

As thickeners, guar gum, quince seed gum, xanthan gum, carrageenan, alginic acid,
Examples include high molecular compounds such as sodium carboxymethylcellulose, carboxyvinyl polymer, polyvinylpyrrolidone, amphoteric methacrylate copolymer, cationized cellulose, polyacrylate copolymer, and nitrocellulose.

Examples of the antioxidant include BHT, BHA, propyl gallate, tocopherol and the like.

Examples of the preservative include phenols, benzoic acid and salts thereof, halogenated bisphenols, acid amides, quaternary ammonium salts and the like.

[0021] As disinfectants, trichlorocarbanide,
Examples include zinc pyrithione, benzalkonium chloride, benzethonium chloride, chlorhexidine, halocarban, hinokitiol, phenol, isopropylphenol, and photosensitizers.

Examples of the chelating agent include edetate, sodium oxalate and the like.

Examples of the pH adjuster include citric acid, succinic acid, hydrochloric acid, ethanolamine, diethanolamine, triethanolamine, aqueous ammonia, sodium hydroxide, calcium chloride and the like.

Examples of the ultraviolet absorber include benzophenone derivatives, paraaminobenzoic acid derivatives, paramethoxycinnamic acid derivatives, salicylic acid derivatives, urocanic acid, ethyl urocanate, 4-tert-butyl-4'-methoxydibenzoylmethane, 2- (2 '-Hydroxy-5'-methylphenyl) benzotriazole, methyl anthranilate, rutin and derivatives thereof can be exemplified.

As whitening agents, kojic acid, arbutin,
Ascorbic acid, ascorbic acid glucoside, glutathione, ellagic acid, placenta extract, oryzanol, rucinol and the like can be exemplified.

Examples of the solvent include lower alcohols such as ethanol, propanol, 1,3-butanediol, diethylene glycol and dipropylene glycol; acetone, ethylene glycol monoethyl ether, toluene and the like.

Salicylic acid,
Examples thereof include sulfur, resorcin, selenium sulfide, and pyridoxine.

Examples of the antipruritic include diphenhydramine hydrochloride, chlorferamine maleate, camphor and the like.

Examples of the anti-inflammatory agent include glycyrrhizic acid and its derivatives, guaiazulene, hydrocortisone acetate, prednisone and the like.

Examples of the antiperspirant include chlorohydroxyaluminum, aluminum chloride, zinc oxide and zinc paraphenolsulfonate.

Examples of the cooling agent include menthol, methyl salicylate and the like.

Examples of the reducing agent include thioglycolic acid, cysteine and the like.

Examples of the antihistamine include diphedamine hydrochloride, chlorpheniramine maleate, glycyrrhetinic acid derivatives and the like.

Examples of astringents include citric acid, tartaric acid, lactic acid, potassium aluminum sulphate, tannic acid and the like.

Examples of the stimulant include tincture tincture, tincture tincture, tincture tincture, benzyl nicotinate and the like.

Examples of the hair-growing agents include assembly extract, cepharanthin, vitamin E and its derivatives, γ-oryzanol, pepper tincture, ginger tincture, cantharistin tincture, benzyl nicotinate, allantoin, photosensitizer 301, photosensitizer 401 and the like. Can be exemplified.

Polymer powders include starch, nylon powder, polyethylene powder, polymethyl methacrylate,
Polyethylene terephthalate / polymethyl methacrylate laminated powder can be exemplified.

Examples of α-hydroxy acids and derivatives thereof include lactic acid, glycolic acid, fruit acid, hydroxycapric acid, long-chain α-hydroxy fatty acid, and long-chain α-hydroxy fatty acid cholesteryl.

Examples of the vitamins and their derivatives include vitamins such as vitamin A, vitamin B group, vitamin D, vitamin E, pantothenic acid, and biotin; ascorbyl stearate, ascorbyl palmitate, ascorbyl dipalmitate, and tetraisopalmitin. Vitamin derivatives such as ascorbyl acid, magnesium ascorbyl phosphate, sodium ascorbate, tocopherol nicotinate, tocopherol acetate, tocopherol linoleate, and tocopherol ferulate can be exemplified.

Examples of saccharides and derivatives thereof include cyclodextrin, β-glucan, chitin, chitosan, glucose, trehalose, pectin, arabinogalactan,
Sugars such as gelatin, dextrin and dextran and derivatives thereof can be exemplified.

Examples of the organic acids include abietic acid and tartaric acid.

Examples of the enzymes include lysozyme chloride, keratinase, papain, pancreatin, protease and the like.

Examples of the nucleic acids include disodium adenosine triphosphate.

As hormones, estradiol,
Estrone, ethinylestradiol, cortisone,
Hydrocortisone, prednisone and the like can be exemplified.

As the clay minerals, montmorillonite,
Sericite, kaolinite, kaolin and the like can be exemplified.

Examples of the fragrance include limonene, linanol, citral, β-ionone, benzylbenzoate, indole, eugenol, auran thiol, geraniol, laral, damascon, benzyl acetate, jasmine lactone, galact solid, essential oil and the like. it can.

As the pigment, mica, talc, kaolin, calcium carbonate, red iron oxide, yellow iron oxide, black iron oxide,
Ultramarine, navy blue, carbon black, titanium dioxide, zinc oxide, titanium mica, fish scale foil, boron nitride, photochromic pigments, synthetic fluorophlogopite, inorganic pigments such as fine particle composite powder; β-carotene, calsamine, rutin, cochineal,
Examples include natural pigments such as chlorophyll; organic synthetic pigments such as dyes, lakes, and organic pigments.

[0048] In addition, components used in known components such as cosmetics, pharmaceuticals, foods, and the like can be appropriately compounded as long as the effects of the present invention are not impaired.

The cosmetic of the present invention can be produced according to a usual method, and includes basic cosmetics, makeup cosmetics,
Hair cosmetics, aromatic cosmetics, body cosmetics and the like are included.

The basic cosmetics include, for example, cleansing foam, cleansing gel, powder, facial cleansing powder,
Facial cleansing such as cleansing cream, cleansing milk, cleansing lotion, cleansing oil, cleansing mask, etc .; lotion such as softening lotion, astringent lotion, washing lotion, multi-layer type lotion; emollient lotion, moisture lotion, milky lotion,
Nourishing Lotion, Nourishing Milk, Skin Moisture, Moisture Emulsion, Massage Lotion, Cleansing Lotion, Protect Emulsion, Sun Protect, Sun Protector, UV Care Milk, Sunscreen, Makeup Lotion, Horny Smoother, Elbow Lotion, Hair Milk, Hand Lotion , Body lotion, etc .; emollient cream, nourishing cream, nourishing cream, burnishing cream, moisture cream, night cream, massage cream, cleansing cream, makeup cream, base cream, pre-made cream, sunscreen cream, suntan cream, hair Remover, hair cream, deodorant cream, shaving Creams such as reams and keratin softening creams; gels such as cleansing gels and moisture gels: soaps such as toilet soaps, transparent soaps, medicinal soaps, liquid soaps, shaving soaps, synthetic toilet soaps; peel-off packs, powder packs, washing packs, oils pack,
Pack masks such as cleansing masks; essences such as moisturizing essences, whitening essences, and ultraviolet essences can be exemplified.

Examples of make-up cosmetics include white powders and powders, foundations, lipsticks, blushers, eyeliners, mascaras, eye shadows, eyebrows, eyebrows, nail enamels, enamel removers, nail treatments, and the like.

Hair cosmetics include shampoos such as oil shampoos, cream shampoos, conditioning shampoos, dandruff shampoos and rinsing shampoos; rinsing; hair restorer; hair foam, hair mousse, hair spray, hair mist, hair gel, water grease, Set lotion, curler lotion,
Examples include hair liquids, pomades, tics, hair creams, hair blows, split ends coats, hair oils, agents for permanent waving, hair dyes, hair bleach and the like.

[0053] Aroma cosmetics include perfume, perfume,
Examples thereof include parfum, eau de parfum, eau de toilette, eau de cologne, condensed perfume, aromatic powder, perfume soap, body lotion, bath oil and the like.

Examples of body cosmetics include body cleansing agents such as body shampoos; deodorant cosmetics such as deodorant lotions, deodorant powders, deodorant sprays, and deodorant sticks; decolorants, depilatory / depilatory agents; bath agents; An insect repeller and the like can be exemplified.

Further, the dosage form is an oil-in-water (O / W) type,
Water-in-oil (W / O) type, W / O / W type, O / W / O type emulsion type cosmetics, oily cosmetics, solid cosmetics, liquid cosmetics, kneaded cosmetics, sticky cosmetics Cosmetics, volatile oil cosmetics, powder cosmetics, jelly cosmetics, gel cosmetics, paste cosmetics, emulsion polymer cosmetics, sheet cosmetics, mist cosmetics, spray cosmetics And the like.

The external preparation is applied directly to the skin in the form of an ointment, patch, lotion, liniment, liquid coating or the like. The blending amount of the dimer acid ester in the external preparation of the present invention is not particularly limited, but is about 0.1 to 50% by weight, and particularly preferably 0.5 to 30% by weight. As ingredients to be added to ointments, patches, lotions, liniments, liquid coatings, etc., all additives usually used in these preparations can be used.

[0057]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.

Synthesis Example 1 (Synthesis of dicholesteryl dimer acid) Dimer acid (EMPOL106 manufactured by Cognis Japan KK) was placed in a 1 L reactor equipped with a stirrer, a thermometer, and a gas inlet tube.
1) 174 g (0.30 mol), cholesterol 233
g (0.60 mol), heptane 260 g and paratoluenesulfonic acid 1.2 g are added, and the mixture is heated to 104 ° C. under a nitrogen stream and reacted for 20 hours. After cooling, 160 g of heptane was added, and the unreacted carboxylic acid was removed with an aqueous sodium hydroxide solution, followed by washing with water to recover the solvent, heptane, to obtain 337 g of the desired dicholesteryl dimerate. The resulting ester is a waxy solid at room temperature, having an acid value of 1.7 and a hydroxyl value of 8.
5, saponification value was 71.5.

Synthesis Example 2 (Synthesis of phytosteryl dimer acid / isostearyl dimer acid) Dimer acid (EMPOL106 manufactured by Cognis Japan KK) was placed in a 1 L reactor equipped with a stirrer, a thermometer, and a gas inlet tube.
1) 174 g (0.30 mol), phytosterol 12
8 g (0.31 mol), heptane 260 g and paratoluenesulfonic acid 1.2 g are added, and the mixture is heated to 104 ° C. in a nitrogen stream and reacted for 11 hours. Then, 85 g of isostearyl alcohol (manufactured by Higher Alcohol Industry Co., Ltd.)
(0.31 mol) and react for 15 hours. After cooling, 160 g of heptane was added, and the unreacted carboxylic acid was removed with an aqueous sodium hydroxide solution, and the solution was washed with water to recover heptane as a solvent. Thus, 369 g of the target phytosteryl dimerate / isostearyl was obtained. The obtained ester was a viscous liquid at room temperature, and had an acid value of 0.6, a hydroxyl value of 14.4 and a saponification value of 86.4.

Synthesis Example 3 (Synthesis of phytosteryl dimerate / behenyl) In place of cholesterol in Synthesis Example 1, 124 g (0.30 mol) of phytosterol and 97 g of behenyl alcohol
(0.30 mol) to obtain 346 g of the desired phytosteryl dimerate / behenyl. The resulting ester is a waxy solid at room temperature, acid value 0.7,
The hydroxyl value was 8.7 and the saponification value was 75.4.

Synthesis Example 4 (Synthesis of Cholesteryl Dimer Acid Part) Instead of 233 g of cholesterol of Synthesis Example 1, 117 g (0.30 mol) of cholesterol was reacted in the same manner, washed with water, recovered with heptane, and treated with the desired dimer acid part. 253 g of cholesteryl were obtained. The obtained ester was a viscous liquid at room temperature, and had an acid value of 67.0, a hydroxyl value of 7.1 and a saponification value of 113.1.

Test Example 1 The water content of the dimer acid esters obtained in Synthesis Examples 1 to 4 was measured. Water content is 50% of each oil agent in liquid paraffin
The water was kneaded well with a pestle while dripping water onto the mortar, and the weight of water kneaded until water could not be kneaded was shown as a percentage of the diluent. As a result, as shown in Table 1, all showed high water content.

Test Example 2 The refractive index of the dimer acid esters obtained in Synthesis Examples 1 to 4 was measured. Refractive index is measured using a refractometer Model3 (ATAGO)
Was measured under the condition of 50 ° C. Table 1 shows the results. The dimer acid ester of the present invention exhibited a refractive index almost equal to or higher than that of liquid lanolin, which is known as a glossy oil agent, and exhibited very glossy characteristics.

[0064]

【table 1】

Example 1 An ointment was prepared by mixing phytosteryl dimerate / isostearyl dimer obtained in Synthesis Example 2 as follows. -------------------------------------------------- --------------- Component weight% ------------------------------- ----------------------------------- Liquid paraffin 30.0 Phytosteryl dimer / isostearyl of Synthesis Example 2 10.0 Dimethylsiloxane 10.0 Cetostearyl alcohol 5.0 Cetrimide 0.5 Chlorocresol 0.1 Purified water Residue ------------------------ ------------------------------------------- Liquid paraffin, synthetic example 2 Heat phytosteryl / isostearyl dimer, dimethylsiloxane, and cetostearyl alcohol to 70 ° C. and mix until uniform. The above-mentioned oil phase was added to the solution of cetrimide and chlorocresol dissolved in purified water at 70 ° C. while stirring to homogenize, and then cooled to room temperature to prepare an ointment.

Comparative Example 1 Tristearic acid glyceride 10 was used instead of phytosteryl dimerate / isostearyl 10% by weight in Example 1.
An ointment was prepared in the same manner as in Example 1 except that the weight% was used.

Example 2 The cholesteryl dimerate obtained in Synthesis Example 1 was blended as follows to prepare an emollient cream. -------------------------------------------------- ------------------ Component% by weight ---------------------------- ---------------------------------------- Dicholesteryl dimerate of Synthesis Example 1 7. 0 Stearic acid 3.0 Vaseline 6.0 Cetyl alcohol 5.0 POE (20) Cetyl alcohol ether 2.0 Propylene glycol monostearate 3.0 Dipropylene glycol 3.0 Glycerin 3.0 Triethanolamine 1.0 Preservative, antioxidant Appropriate amount Purified water Residue ---------------------------------------- ---------------------------- Dipropylene glycol, glycerin, triethanolamine and preservative are dissolved in purified water and heated to 70 ° C. Warm (aqueous phase). The other components are mixed and dissolved at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase while stirring, followed by stirring, and then uniformly emulsified by an emulsifier and cooled to room temperature to prepare an emollient cream.

Comparative Example 2 An emollient cream was prepared in the same manner as in Example 2, except that 7% by weight of glyceryl tri-2-ethylhexanoate was used instead of 7% by weight of cholesteryl dimerate of Example 2.

Example 3 The phytosteryl dimerate / isostearyl dimer obtained in Synthesis Example 2 was mixed as follows to prepare an emulsion. -------------------------------------------------- ----------------- Component% by weight ----------------------------- -------------------------------------- 2. Phytosteryl dimer / isostearyl of Synthesis Example 2 0 Stearic acid 2.0 Vaseline 3.0 Cetyl alcohol 1.0 Sorbitan monooleate 2.0 Polyethylene glycol 1500 3.0 1,3-butylene glycol 5.0 Triethanolamine 1.0 Perfume, preservatives Appropriate amount Purification Water residue ------------------------------------------------ ------------------- Add polyethylene glycol 1500, 1,3-butylene glycol, triethanolamine and preservative to purified water and heat to 70 ° C to dissolve (aqueous phase ). The other components are mixed and dissolved by heating to 70 ° C. (oil phase). The oil phase is gradually added to this aqueous phase while stirring to carry out preliminary emulsification. Further, the emulsion was uniformly emulsified by an emulsifier and cooled to room temperature to prepare an emulsion.

Comparative Example 3 An emulsion was prepared in the same manner as in Example 3 except that 3% by weight of glyceryl tri-2-ethylhexanoate was used instead of 3% by weight of phytosteryl dimer / isostearyl dimer in Example 3. .

Example 4 A liquid cream shampoo was prepared by mixing the partial cholesteryl dimer acid obtained in Synthesis Example 4 as follows. -------------------------------------------------- ----------------- Component% by weight ----------------------------- -------------------------------------- Dimer acid partial cholesteryl 2.0 poly of Synthesis Example 4 Oxyethylene (3) sodium lauryl sulfate (30%) 30.0 Sodium lauryl sulfate (30%) 15.0 Lauroyl diethanolamide 3.0 Polyethylene glycol distearate 2.0 Perfume, preservative Appropriate amount Sequestering agent, pH Adjusting agent Appropriate amount Purified water Residue -------------------------------------------- ----------------------- Heat purified water to 70 ℃, add other ingredients and dissolve uniformly, then cool to prepare liquid cream shampoo did.

Comparative Example 4 A liquid cream shampoo was prepared in the same manner as in Example 4, except that 2% by weight of cetyl 2-ethylhexanoate was used instead of 2% by weight of partially cholesteryl dimer acid in Example 4.

Example 5 A hair conditioner was prepared by mixing phytosteryl dimerate / behenyl obtained in Synthesis Example 3 as follows. -------------------------------------------------- ------------------ Component% by weight ---------------------------- ---------------------------------------- Phytosteryl dimerate / Behenyl of Synthesis Example 3 2 3.0 Stearyltrimethylammonium chloride 3.0 Glyceryl monostearate 0.5 Cetyl alcohol 3.0 Glycerin 3.0 Perfume and preservatives Appropriate amount Purified water residue ----------------- -------------------------------------------------- -Heat and dissolve stearyltrimethylammonium chloride and preservative in purified water at 70 ° C. Separately, a mixture obtained by stirring and mixing the phytosteryl / behenyl dimer, glyceryl monostearate, cetyl alcohol, glycerin, and fragrance of Synthesis Example 3 at 70 ° C. was added thereto, and the mixture was sufficiently stirred and mixed, and then cooled. A hair conditioner was prepared.

Comparative Example 5 A hair conditioner was prepared in the same manner as in Example 5 except that 2% by weight of tallow fatty acid glyceride was used instead of 2% by weight of phytosteryl dimer / behenyl in Example 5.

Example 6 A lipstick was prepared by mixing the phytosteryl dimerate / isostearyl dimerate obtained in Synthesis Example 2 as follows. -------------------------------------------------- ----------------- Component% by weight ----------------------------- -------------------------------------- Phytosteryl dimerate / isostearyl of Synthesis Example 2 20. 0 Dimer diol diisostearate 46.0 Glyceryl triisooctanoate 10.0 Carnauba wax 3.0 Candelilla wax 6.0 Seresin 5.0 Titanium dioxide 6.0 Red 201 No. 1.0 Red 202 No. 2.0 Iron oxide black 1 0.0 Perfume, antioxidant appropriate amount ------------------------------- --------------------------- Titanium dioxide, Red No. 201, Red No. 202, iron oxide black as part of dimer diol diisostearate Knead with a roller and mix evenly. After mixing and heating and dissolving the other components, the previously kneaded pigment / dye dispersion is added and uniformly dispersed with a homomixer. After dispersion and degassing, the mixture is poured into a mold and rapidly cooled to form a stick.

Comparative Example 6 A lipstick was prepared in the same manner as in Example 6, except that 20% by weight of diisostearyl malate was used instead of 20% by weight of phytosteryl dimerate / isostearyl dimer of Example 6.

Test Example 3 Ointments, emollient creams prepared in Examples 1 to 5,
Emulsion, shampoo, hair conditioner, and the ointments of Comparative Examples 1 to 5, emollient cream, emulsion, shampoo, to see the stability of the hair conditioner,
The stability at 40 ° C. was investigated. Table 2 shows the results.

As shown in Table 2, the stability of the ointments, emollient creams, emulsions, shampoos and hair conditioners prepared in Examples 1 to 5 was as follows: Ointments, emollient creams, emulsions, shampoos and hair conditioners of Comparative Examples 1 to 5 Was better than In the column of evaluation in Table 2, "O": stable after 30 days after preparation. "△": 10 to 29 days after preparation, phase separation or precipitation occurred. "X": phase separation or precipitate occurred within 10 days after preparation.

[0079]

[Table 2]

Test Example 4 Female panelists actually used the ointment of Example 1 and Comparative Example 1 and the cosmetics prepared in Examples 2, 3 and Comparative Examples 2 and 3 to evaluate practical use. Table 3 shows the results.
Shown in In this case, the evaluation criteria for the feeling of use and the durability of the feeling of use are as follows. [Usability] "］": extremely good, "、": good, "△": slightly poor, "x": poor [Continuity] After 5 hours of use, the use feeling was evaluated according to the following criteria. "◎": extremely good, "○": good, "△": slightly bad, "x": bad

From Table 3, it can be seen that the ointment and the cosmetic of the present invention are very excellent in use feeling and sustainability.

[0082]

[Table 3]

Test Example 5 The shampoo and the hair conditioner prepared in Examples 4 and 5 and Comparative Examples 4 and 5 were actually used by female panelists, and practical evaluation was performed. The evaluation was made on the following evaluation criteria for three items of moist feeling, gloss, and cohesiveness of the hair after use. The results are shown in Table 4. [Moist feeling] A: Very moist. ○: Moist. Δ: Neither can be said. ×: Not moist. [Glossy] A: Very glossy. ：: There is luster. Δ: Neither can be said. X: There is no luster. [Cohesiveness] A: Very cohesive. ：: united. Δ: Neither can be said. ×: Not organized.

From Table 4, it can be seen that the shampoo and hair conditioner of the present invention are excellent in usability.

[0085]

[Table 4]

Test Example 6 A female panelist actually used the lipsticks prepared in Example 6 and Comparative Example 6, and was evaluated for practical use and stability.
Practical evaluations include moist feeling during and after use, adhesion,
The following evaluation criteria were used for the four items of extensibility and gloss applied. The results are shown in Table 5. [Moist feeling] A: Very moist. ○: Moist. Δ: Neither can be said. ×: Not moist. [Adhesiveness] A: Very good. ：: Good stickiness. Δ: Neither good nor bad. ×: Bad. [Extensibility] A: Very good elongation. ：: Good elongation. Δ: Neither good nor bad. X: Elongation is poor. [Coating gloss] A: Very glossy. ：: Good gloss. X: There is no luster. [Oxidation stability] Left in an oven at 40 ° C for 3 months,
The change in odor was evaluated. ：: almost no change. X: There was a clear smell. [Sweating test] ：: No sweating was observed for 2 months or more. Δ: No sweat was observed for 2 weeks or more. ×: Sweating was observed within 2 weeks.

From Table 5, it can be seen that the lipstick according to the present invention is excellent in use feeling, oxidative stability and no sweating.

[0088]

[Table 5]

[0089]

The dimer acid ester according to the present invention comprises:
It is excellent in safety, stability, water holding property and luster, and it is possible to obtain cosmetics and external preparations containing the same which are excellent in safety, stability, water holding property and luster and have good usability.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (reference) A61K 47/14 A61K 47/14 F term (reference) 4C076 AA07 DD34 DD37 DD47 DD70 EE27 4C083 AA122 AB232 AB242 AC012 AC022 AC072 AC122 AC182 AC242 AC371 AC372 AC392 AC402 AC422 AC442 AC542 AC642 AC692 AC782 AC792 AC812 AD042 AD152 AD491 AD492 CC01 CC05 CC13 CC33 CC38 DD22 DD23 EE01 EE06 EE07 EE09 FF01 4H006 AA02 AB12

Claims (5)

[Claims] 1. A dimer acid ester obtainable by esterifying dimer acid with sterol. 2. A dimer acid comprising sterol and one carbon atom
A dimer acid ester obtainable by esterification with one kind of alcohol selected from a straight-chain alcohol having from 34 to 34, a branched alcohol having from 3 to 34 carbon atoms, and an unsaturated alcohol having from 6 to 34 carbon atoms. 3. The dimer acid ester according to claim 1, wherein the dimer acid ester is a disterol ester of dimer acid. 4. The dimer acid ester according to claim 1, wherein the dimer acid ester is a monosterol ester of dimer acid and / or a metal salt of a monosterol ester. 5. A cosmetic or external preparation comprising the dimer acid ester according to any one of claims 1 to 4.