JP5096829B2 - Makeup remover - Google Patents

Description

The present invention relates to a makeup remover containing a diester of a dicarboxylic acid represented by Chemical Formula 1 and a polyoxyethylene monoalkyl ether represented by Chemical Formula 2.
(Chemical formula 1)
HO-CO-R1-CO-OH
(Wherein R1 represents a linear, branched or cyclic hydrocarbon group having 2 to 10 carbon atoms)
(Chemical formula 2)
R2- (OCH2CH2) n-OH
(Wherein R2 is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n represents an integer of 2 to 11)

  With makeup cosmetics such as foundations, lipsticks, eye makeup, and nail enamel, with the advancement of materials and formulation technology, products with good makeup that are resistant to moisture and sebum are increasing. In connection with this, the performance improvement of the makeup remover for removing these makeup cosmetics is desired. In order to remove makeup cosmetics around the face such as foundation, lipstick, and eye makeup, cleansing agents that generally include an oil agent for removing makeup and a surfactant for washing it off are widely used. These oils include hydrocarbons such as liquid paraffin and squalane, natural fats such as jojoba oil, olive oil, macadamia nut oil, isotridecyl isononanoate, isononyl isononanoate, isopropyl myristate, diethyl sebacate, cetyl isooctanoate, octyl palmitate, Although ester oils such as glyceryl tri-2-ethylhexanoate, tricapryl / glyceryl caprate, and silicone oils such as methylphenylpolysiloxane and methylpolysiloxane are used, the makeup removing ability is not always satisfactory. . Further, since a large amount of oil is used as a cleansing agent, there is a problem that the feeling of use is poor, such as stickiness. For this reason, it has been desired to develop an oil agent that is excellent in makeup removing ability and has a good feeling in use. In addition, solvents such as acetates, acetone, and alcohols are used to remove nail enamel, but if these solvents are used, the oil on the nails and surrounding skin is removed, and the nails and surrounding skin are whitened. This causes problems such as nail damage and rough skin. Therefore, a nail enamel remover that replaces these problems has been desired.

On the other hand, diesters of polyoxyethylene monoalkyl ether and dicarboxylic acid have both hydrophilic and lipophilic functions, and are known to have excellent usability and feel as oils for cosmetics or skin external preparations. .
JP 2001-206812 A JP 2001-240526 A Japanese Patent Application No. 2006-315081

  The problem to be solved by the present invention is an oil agent having excellent make-up removal ability and excellent use feeling, and a cleansing agent and nail excellent in make-up removal ability and use feeling containing the oil agent. The object is to provide a makeup remover such as an enamel remover.

As a result of intensive studies to solve the above problems, the present inventors have found that a diester of a dicarboxylic acid represented by Chemical Formula 1 and a polyoxyethylene monoalkyl ether represented by Chemical Formula 2 has an excellent makeup removing ability. The present invention was completed. That is, the present invention provides a makeup remover that has both excellent makeup removing ability and excellent feeling of use, containing the diester.
(Chemical formula 1)
HO-CO-R1-CO-OH
(Wherein R1 represents a linear, branched or cyclic hydrocarbon group having 2 to 10 carbon atoms)
(Chemical formula 2)
R2- (OCH2CH2) n-OH
(Wherein R2 is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n represents an integer of 2 to 11)

  The makeup remover such as the cleansing agent and nail enamel remover of the present invention is excellent in makeup removal ability and has a good feeling in use.

In order to express the excellent function of the present invention, it is essential to use a diester of a dicarboxylic acid represented by Chemical Formula 1 and a polyoxyethylene monoalkyl ether represented by Chemical Formula 2.
(Chemical formula 1)
HO-CO-R1-CO-OH
(Wherein R1 represents a linear, branched or cyclic hydrocarbon group having 2 to 10 carbon atoms)
(Chemical formula 2)
R2- (OCH2CH2) n-OH
(Wherein R2 is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n represents an integer of 2 to 11)

  As the dicarboxylic acid represented by Chemical Formula 1 constituting the diester, R1 is a dicarboxylic acid representing a linear, branched or cyclic hydrocarbon group having 2 to 10 carbon atoms. Specifically, saturated linear dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid; 2,2,4-trimethyladipic acid, 2,4 Saturated branched dicarboxylic acids such as 1,4-trimethyladipic acid; cyclic such as 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid And the like. Of these, succinic acid, adipic acid, azelaic acid, sebacic acid, and dodecanedioic acid are preferred as the saturated linear dicarboxylic acid from the viewpoints of availability, economy, makeup removal, and the like, and as cyclic dicarboxylic acid Is preferably 1,4-cyclohexanedicarboxylic acid, phthalic acid, or terephthalic acid. Of these, cyclic dicarboxylic acids are preferred, and 1,4-cyclohexanedicarboxylic acid is most preferred.

  On the other hand, as a polyoxyethylene monoalkyl ether represented by Chemical Formula 2 constituting a diester, R2 is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n is an integer of 2 to 11 It is. Examples of straight, branched or cyclic hydrocarbon groups having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, and n-hexyl group. Cyclohexyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, n-dodecyl group, and the like. From the reactivity during esterification, performance of diester, economy, etc., methyl group, ethyl Group is preferred, and ethyl group is particularly preferred. Furthermore, n is preferably 2 or 3 from the viewpoints of economy, reactivity, etc., and the polyoxyethylene monoalkyl ether represented by Chemical Formula 1 is preferably diethylene glycol monoethyl ether or triethylene glycol monoethyl ether. Most preferred is monoethyl ether.

  Although the manufacturing method of the diester used for this invention is not specifically limited, The esterification reaction is 150-260 degreeC by the following manufacturing methods, ie, the raw material dicarboxylic acid or dicarboxylic acid anhydride, and polyoxyethylene monoalkyl ether without a solvent. If it makes it, it can manufacture economically advantageous. The charging ratio of the dicarboxylic acid and the polyoxyethylene monoalkyl ether during the esterification reaction is preferably 1.6 to 6, more preferably 2 to 4 in molar ratio from the ester production rate and economical viewpoint. is there. Esterification can also be performed using a catalyst and a solvent. When a catalyst such as an acid catalyst is used, a general acid catalyst such as p-toluenesulfonic acid, sulfuric acid, hydrochloric acid, methanesulfonic acid, boron trifluoride diethyl ether complex, titanium alcoholate, or solid acid catalyst can be used. . When using a solvent, commonly used solvents such as toluene and heptane can be used. After completion of the esterification reaction, the target diester can be obtained by purification without purification or by a conventional purification method such as distillation under reduced pressure, washing with water, steam deodorization, or activated carbon treatment. During production, in addition to diesters, monoesters and unreacted polyoxyethylene monoalkyl ethers may remain in the diesters. Even if the monoester or unreacted polyoxyethylene monoalkyl ether remains, there is no problem in use, but the purity of the diester is 80% by weight or more, preferably 90% by weight or more, more preferably 95% by weight or more. It is desirable to be.

  The diester thus obtained is excellent in makeup removing ability and feeling of use as an oil agent of a makeup removing agent. The diester can be used as it is as an oil agent for a makeup remover, but can also be used as a mixture with an antioxidant, an oily base for cosmetics or other external preparations for skin, a moisturizer, a touch improver, etc. . As the antioxidant, tocopherol derivatives such as tocopherol (vitamin E) and tocopherol acetate; BHT, BHA; gallic acid derivatives such as propyl gallate; vitamin C (ascorbic acid) and / or a derivative thereof can be used. When the antioxidant is contained, the content of the antioxidant is preferably 0.0001 to 0.1% by weight.

  The makeup remover of the present invention specifically includes cleansing foams, cleansing creams, cleansing milks, cleansing lotions, cleansing gels, cleansing oils, cleansing masks, facial cleansing agents, and nail enamel removers. . As the dosage form, liquid type, oily type, oil-in-water (O / W) type, water-in-oil (W / O) type, emulsified type such as W / O / W type, O / W / O type, stick type Volatile oil type, powder type, jelly type, gel type, paste type, sheet type, mist type, spray type and the like are preferable. Moreover, the makeup remover of the present invention can be produced according to a usual method.

  The blending amount of the diester to the makeup remover of the present invention is not particularly limited, but in either case of cleansing agent or nail enamel remover, the diester is preferably about 0.1 to 99% by weight, more preferably 0.5. ~ 90% by weight.

  The make-up remover of the present invention contains additives that are generally blended into the make-up remover as necessary, such as oil bases, moisturizers, feel improvers, surfactants, polymers, thickeners, Gelling agents, solvents, propellants, antioxidants, antiseptics, antibacterial agents, chelating agents, pH adjusting agents, acids, alkalis, fragrances, dyes, colorants, dyes, pigments, water and the like can be blended.

  Examples of these additive components include cetanol, myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol, stearyl alcohol, aralkyl alcohol, behenyl alcohol, jojoba alcohol, chimyl alcohol, seraalkyl alcohol, batyl. Higher alcohols such as alcohol, hexyldecanol, isostearyl alcohol, 2-octyldodecanol, dimer diol; aralkyl alcohols and derivatives such as benzyl alcohol; lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, behenic acid, undecylen Acid, 12-hydroxystearic acid, palmitooleic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, docosahexaenoic acid, ethyl Higher fatty acids such as cosapentaenoic acid, isohexadecanoic acid, anteisohenicosanoic acid, long-chain branched fatty acid, dimer acid, hydrogenated dimer acid, and their aluminum salts, calcium salts, magnesium salts, zinc salts, potassium, sodium salts, etc. Metal soaps, and nitrogen-containing derivatives such as amides; liquid paraffin (mineral oil), heavy liquid isoparaffin, light liquid isoparaffin, α-olefin oligomer, polyisobutene, hydrogenated polyisobutene, polybutene, squalane, olive-derived squalane, squalene , Hydrocarbons such as petroleum jelly and solid paraffin; candelilla wax, carnauba wax, rice wax, wax, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax , Petrolatum, Fischer-Tropsch wax, polyethylene wax, ethylene / propylene copolymer and other waxes; palm oil, palm oil, palm kernel oil, 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, rosehip oil, meadow foam oil, persic oil, tea tree oil, mint oil, corn oil, rapeseed oil, sunflower oil, wheat germ oil, linseed oil, cottonseed oil, soybean oil Vegetable oils such as peanut oil, rice bran oil, cacao butter, shea butter, hydrogenated palm oil, hydrogenated castor oil, jojoba oil, hydrogenated jojoba oil; beef tallow, milk fat, horse fat, egg yolk oil, mink oil, turtle Animal fats and oils such as oil; animal oils such as whale wax, lanolin and orange luffy oil Liquid lanolin, reduced lanolin, adsorption purified lanolin, lanolin acetate, acetic acid liquid lanolin, hydroxy lanolin, polyoxyethylene lanolin, lanolin fatty acid, hard lanolin fatty acid, lanolin alcohol, lanolin alcohol acetate, acetic acid (cetyl lanolyl) ester, etc. Lanolins: phospholipids such as lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, sphingomyelin, phosphatidic acid, lysolecithin, etc .; hydrogenated soybean phospholipid, partially hydrogenated soybean phospholipid , Phospholipid derivatives such as hydrogenated egg yolk phospholipid, partially hydrogenated egg yolk phospholipid; cholesterol, dihydrocholesterol, lanosterol, dihi Sterols such as loranosterol, phytosterol, cholic acid; sapogenins; saponins; cholesteryl acetate, cholesteryl nonanoate, cholesteryl stearate, cholesteryl isostearate, cholesteryl oleate, di-N-lauroyl-L-glutamate (cholesteryl / behenyl / Octyldodecyl), N-lauroyl-L-glutamate di (cholesteryl / octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl / behenyl / octyldodecyl), N-lauroyl-L-glutamate di (phytosteryl / octyldodecyl) Acyl sarcosine alkyl esters such as N-lauroyl sarcosine isopropyl, cholesteryl 12-hydroxystearate, macadamia nut oil fatty acid cholesteryl, Steroid esters such as macadamia nut oil fatty acid phytosteryl, isostearate phytosteryl, soft lanolin fatty acid cholesteryl, hard lanolin fatty acid cholesteryl, long chain branched fatty acid cholesteryl, long chain α-hydroxy fatty acid cholesteryl; phospholipid / cholesterol complex, phospholipid / phytosterol complex Lipid complexes such as octyldodecyl myristate, hexyldecyl myristate, octyldodecyl isostearate, cetyl palmitate, octyldodecyl palmitate, cetyl octanoate, hexyldecyl octanoate, isotridecyl isononanoate, isononanoyl isononanoate, isononanoic acid Octyl, isotridecyl isononanoate, isodecyl neopentanoate, isotridecyl neopentanoate, neopentanoic acid Stearyl, octyldodecyl neodecanoate, oleyl oleate, octyldodecyl oleate, octyldodecyl ricinoleate, lanolin fatty acid octyldodecyl, hexyldecyl dimethyloctanoate, octyldodecyl erucate, isostearic acid hydrogenated castor oil, ethyl oleate, avocado oil fatty acid Ethyl, isopropyl myristate, isopropyl palmitate, octyl palmitate, isopropyl isostearate, lanolin fatty acid isopropyl, diethyl sebacate, diisopropyl sebacate, dioctyl sebacate, diisopropyl adipate, dibutyloctyl sebacate, diisobutyl adipate, dioctyl succinate , Monoalcohol carboxylic acid esters such as triethyl citrate; cetyl lactate, dii malate Oxyacid esters such as sostearyl, monoisostearic acid hydrogenated castor oil; glyceryl trioctanoate, glyceryl trioleate, glyceryl triisostearate, glyceryl diisostearate, tri (caprylic acid / capric acid) glyceryl, tri (caprylic acid / caprin) Acid / myristic acid / stearic acid) glyceryl, hydrogenated rosin triglyceride (hydrogenated ester gum), rosin triglyceride (ester gum), glyceryl behenate, trimethylolpropane trioctanoate, trimethylolpropane triisostearate, dioctanoic acid Neopentyl glycol, neopentyl glycol dicaprate, 2-butyl-2-ethyl-1,3-propanediol dioctanoate, propylene glycol dioleate Pentaerythrityl tetraoctanoate, hydrogenated rosin pentaerythrityl, ditrimethylolpropane triethylhexanoate, ditrimethylolpropane (isostearic acid / sebacic acid), pentaerythrityl triethylhexanoate, (hydroxystearic acid / stearic acid / rosin acid) Dipentaerythrityl, diglyceryl diisostearate, polyglyceryl tetraisostearate, polyglyceryl-10 nonaisostearate, deca (erucic acid / isostearic acid / ricinoleic acid) polyglyceryl-8, (hexyldecanoic acid / sebacic acid) diglyceryl oligoester, glycol distearate ( Ethylene glycol distearate), 3-methyl-1,5-pentanediol dineopentanoate, 2, dineopentanoic acid 2, Polyhydric alcohol fatty acid esters such as diethyl-1,5-pentanediol; diisopropyl dimerlinoleate, diisostearyl dimerdilinoleate, dimerdilinoleate di (isostearyl / phytosteryl), dimerdilinoleic acid (phytosteryl) / Behenyl), dimer dilinoleic acid (phytosteryl / isostearyl / cetyl / stearyl / behenyl), dimer dilinoleic acid dimer dilinoleyl, diisostearic dimer dilinoleyl, dimer dilinoleyl hydrogenated rosin condensate, dimer dilinol Dimer acid or dimer diol derivative such as acid-hardened castor oil, hydroxyalkyl dimer linoleyl ether; coconut oil fatty acid monoethanolamide (cocamide MEA), coconut oil fatty acid diethanola Amide (cocamide DEA), lauric acid monoethanolamide (lauramide MEA), lauric acid diethanolamide (lauramide DEA), lauric acid monoisopropanolamide (lauramide MIPA), palmitic acid monoethanolamide (partamide MEA), palmitic acid diethanolamide ( Fatty acid alkanolamides such as partamide DEA) and palm oil fatty acid methylethanolamide (cocamidomethyl MEA); dimethicone (dimethylpolysiloxane), highly polymerized dimethicone (highly polymerized dimethylpolysiloxane), cyclomethicone (cyclic dimethylsiloxane, decamethylcyclopenta) Siloxane), phenyltrimethicone, diphenyldimethicone, phenyldimethicone, stearoxypropyldimethylamine, (aminoethylamino) (Ropylemethicone / dimethicone) copolymer, dimethiconol, dimethiconol crosspolymer, silicone resin, silicone rubber, amino-modified silicone such as aminopropyl dimethicone and amodimethicone, cation-modified silicone, polyether-modified silicone such as dimethicone copolyol, polyglycerin-modified silicone, sugar Modified silicone, carboxylic acid modified silicone, phosphoric acid modified silicone, sulfuric acid modified silicone, alkyl modified silicone, fatty acid modified silicone, alkyl ether modified silicone, amino acid modified silicone, peptide modified silicone, fluorine modified silicone, cation modified and polyether modified silicone, Amino- and polyether-modified silicones, alkyl- and polyether-modified silicones, Silicones such as hexane-polyoxyalkylene copolymer; perfluorodecane, perfluorooctane, fluorine-based oils such as perfluoropolyether may be mentioned as preferred.

  As the humectant / feel improver, glycerin, 1,3-butylene glycol, propylene glycol, 3-methyl-1,3-butanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, Polyols such as trimethylolpropane, pentaerythritol, hexylene glycol, diglycerin, polyglycerin, diethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, ethylene glycol / propylene glycol copolymer and polymers thereof; diethylene glycol monoethyl ether (Ethoxydiglycol), ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol dibutyl ether, etc. (Eicosandioic acid / tetradecandioic acid) water-soluble esters such as polyglyceryl-10 and tetradecandioic acid polyglyceryl-10; sugar alcohols such as sorbitol, xylitol, erythritol, mannitol, maltitol; glucose, fructose, galactose Mannose, threose, xylose, arabinose, fucose, ribose, deoxyribose, maltose, trehalose, lactose, raffinose, gluconic acid, glucuronic acid, cyclodextrins (α-, β-, γ-cyclodextrin, and maltosylation, Modified cyclodextrins such as hydroxyalkylation), β-glucan, chitin, chitosan, heparin and derivatives, pectin, arabinogalactan, dextrin, dextran, glycogen Sugars such as ethyl glucoside, glucosyl ethyl methacrylate polymer or copolymer, and derivatives thereof; hyaluronic acid, sodium hyaluronate; chondroitin sulfate sodium; mucoitin sulfate, caroline sulfate, kerato sulfate, dermatan sulfate; white jellyfish extract, white jellyfish Fucoidan; Tuberose polysaccharide, naturally-occurring polysaccharide; Organic acids such as citric acid, tartaric acid and lactic acid and salts thereof; Urea; 2-pyrrolidone-5-carboxylic acid and salts thereof such as sodium; Betaine (trimethylglycine) , Proline, hydroxyproline, arginine, lysine, serine, glycine, alanine, phenylalanine, tyrosine, β-alanine, threonine, glutamic acid, glutamine, asparagine, aspartic acid, cysteine, cystine, methio , Leucine, isoleucine, valine, tryptophan, histidine, taurine and other amino acids and their salts; collagen, fish-derived collagen, atelocollagen, gelatin, elastin, collagen-degrading peptide, hydrolyzed collagen, hydroxypropylammonium hydrolyzed collagen, elastin Degraded peptide, keratin degrading peptide, hydrolyzed keratin, conchiolin degrading peptide, hydrolyzed conchiolin, silk proteolytic peptide, hydrolyzed silk, lauroyl hydrolyzed silk sodium, soy proteolytic peptide, wheat proteolytic peptide, hydrolyzed wheat protein, casein Protein peptides such as degraded peptides and acylated peptides and their derivatives; palmitoyl oligopeptide, palmitoyl pentapeptide, palmitoyl tetrapep Acylated peptides such as tide; silylated peptides; lactic acid bacteria culture solution, yeast extract, eggshell membrane protein, bovine submandibular gland mucin, hypotaurine, sesame lignan glycoside, glutathione, albumin, whey; choline chloride, phosphorylcholine; Animal and plant extract components such as placenta extract, aerostin, collagen, aloe extract, hamamelis water, loofah water, chamomile extract, licorice extract, comfrey extract, silk extract, Izayoi rose extract, yarrow extract, eucalyptus extract, and melilot extract Preferred are ceramides such as natural ceramides (types 1, 2, 3, 4, 5, 6), hydroxyceramide, pseudoceramide, glycosphingolipid, ceramide, and sugar-ceramide-containing extract.

Preferred examples of the surfactant include an anionic surfactant, a nonionic surfactant, a cationic surfactant, an amphoteric surfactant, and a polymer surfactant. There is no restriction | limiting in particular in HLB of surfactant, It can use from about 1 low thing to about 20 high thing, It is also preferable to combine a low thing and a high thing of HLB. Examples of preferable surfactants include fatty acid salts such as potassium laurate and potassium myristate; alkyl sulfates such as sodium lauryl sulfate, triethanolamine lauryl sulfate, and ammonium lauryl sulfate; laureth Polyoxyethylene alkyl sulfates such as sodium sulfate and laureth sulfate triethanolamine; cocoyl methyl taurine sodium, cocoyl methyl taurine potassium, lauroyl methyl taurine sodium, myristoyl methyl taurine sodium, lauroyl methyl alanine sodium, lauroyl sarcosine sodium, lauroyl sarcosine triethanol Acyl N-methyl amino acid salts such as amines and sodium methylalanine lauroylglutamate; Cocoyl Glue Acyl amino acid salts such as sodium minate, triethanolamine cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, sodium stearoyl glutamate, ditriethanolamine palmitoyl aspartate, cocoylalanine triethanolamine; polyoxyethylene alkyl ethers such as sodium laureth acetate Acetic acid salt; Succinic acid ester salt such as sodium lauroyl monoethanolamide succinate; Fatty acid alkanolamide ether carboxylate; Acyl lactate; Polyoxyethylene fatty amine sulfate; Fatty acid alkanolamide sulfate; Hardened coconut oil fatty acid sodium glyceryl sulfate Fatty acid glyceride sulfate such as alkylbenzene polyoxyethylene sulfate; α-olefin Olefin sulfonates such as sodium sulfonate; alkylsulfosuccinates such as disodium lauryl sulfosuccinate and dioctyl sodium sulfosuccinate; disodium laureth sulfosuccinate, monolauroyl monoethanolamide polyoxyethylene sodium sulfosuccinate, lauryl polypropylene glycol sulfosuccinic acid Alkyl ether sulfosuccinates such as sodium; alkylbenzene sulfonates such as sodium tetradecylbenzenesulfonate and tetraethanolamine tetraethanol; alkylnaphthalenesulfonates; alkanesulfonates; α-sulfo fatty acid methyl ester salts; Acyl isethionate; alkyl glycidyl ether sulfonate; alkyl sulfoacetate; laurethrin Alkyl ether phosphates such as sodium, sodium dilaureth phosphate, sodium trilaureth phosphate, sodium monooles phosphate; alkyl phosphate salts such as potassium lauryl phosphate; sodium caseinate; alkyl aryl ether phosphate; fatty acid amide ether phosphorus Phospholipids such as phosphatidylglycerol, phosphatidylinositol, and phosphatidic acid; silicone anionic surfactants such as carboxylic acid-modified silicone, phosphate-modified silicone, and sulfate-modified silicone; and nonionic surfactants, laureth (Polyoxyethylene lauryl ether), ceteth (polyoxyethylene cetyl ether), steareth (polyoxyethylene stearyl ether), behenez (polyoxyethylene) Nbehenyl ethers), isosteares (polyoxyethylene isostearyl ethers), octyldecesses (polyoxyethylene octyldodecyl ethers) and other polyoxyethylene alkyl ethers with various polyoxyethylene addition numbers; polyoxyethylene alkylphenyl ethers; Polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil monoisostearate, polyoxyethylene hydrogenated castor oil triisostearate, polyoxyethylene hydrogenated castor oil monopyroglutamic acid monoisostearate diester, poly Castor oil such as oxyethylene hydrogenated castor oil maleic acid and hydrogenated castor oil derivatives; polyoxyethylene phytosterol; polyoxyethylene cholesterol; polyoxy Polyoxyethylene lanolin; polyoxyethylene reduced lanolin; polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene 2-decyltetradecyl ether, polyoxyethylene polyoxypropylene monobutyl ether, polyoxyethylene lanolin; Oxyethylene / polyoxypropylene hydrogenated lanolin, polyoxyethylene / polyoxypropylene alkyl ethers such as polyoxyethylene / polyoxypropylene glycerin ether; polyoxyethylene / polyoxypropylene glycol; (poly) such as PPG-9 diglyceryl Glycerin polyoxypropylene glycol; glyceryl stearate, glyceryl isostearate, glyceryl palmitate, myristate group Glyceryl fatty acid partial esters such as ceryl, glyceryl oleate, glyceryl coconut fatty acid, mono-cotton oil fatty acid glycerin, glyceryl monoerucate, glyceryl sesquioleate, α, α'-oleic acid pyroglutamic acid glycerin, monostearic acid glycerin malic acid; Polyglyceryl stearate-2, 3, 4, 5, 6, 8, 10, polyglyceryl distearate-6, 10, polyglyceryl tristearate, polyglyceryl decastearate-10, polyglyceryl isostearate -2, 3, 4, 5, 6, 8, 10, diglycostyl diisostearate (diglyceryl diisostearate), 3, 10, polyglyceryl-2 triisostearate, polyglyceryl tetraisostearate Ril-2, polyglyceryl-10 decaisostearate, polyglyceryl-2 oleate, 3,4, 5,6, 8,8, dioleate polyglyceryl-6, trioleate polyglyceryl-2, dekaoleic acid Polyglyceryl fatty acid esters such as polyglyceryl-10; ethylene glycol monofatty acid esters such as ethylene glycol monostearate; propylene glycol monofatty acid esters such as propylene glycol monostearate; pentaerythritol partial fatty acid esters; sorbitol partial fatty acid esters; maltitol moieties Fatty acid ester; maltitol ether; sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monos Sorbitan fatty acid esters such as allate, sorbitan sesquioleate, sorbitan trioleate, diglycerol sorbitan penta-2-ethylhexylate, diglycerol sorbitan tetra-2-ethylhexylate; sucrose fatty acid ester, methyl glucoside fatty acid ester, trehalose undecylenate, etc. Partial derivatives of sugar derivatives; alkyl glucosides such as caprylyl glucoside; alkyl polyglycosides; lanolin alcohols; reduced lanolin; polyoxyethylene distearate, polyethylene glycol diisostearate, polyoxyethylene monooleate, polyoxyethylene di- Polyoxyethylene fatty acid mono- and diesters such as oleate; polyoxyethylene propylene glycol fatty acid ester; polyoxyethylene Polyoxyethylene glycerin fatty acid esters such as polyoxyethylene monooleate such as polyglycerin monostearate, polyoxyethylene glycerin monoisostearate, polyoxyethylene glycerin triisostearate; polyoxyethylene sorbitan monooleate, polyoxy Polyoxyethylene sorbitan fatty acid esters such as ethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan tetraoleate; polyoxyethylene sorbitol monolaurate, polyoxyethylene sorbitol monooleate, polyoxyethylene sorbitol penta Polyoxyethylene sorbitol fatty acid esters such as oleate and polyoxyethylene sorbitol monostearate Polyoxyethylene methyl glucoside fatty acid ester; Polyoxyethylene alkyl ether fatty acid ester; Polyoxyethylene animal and vegetable oils such as polyoxyethylene sorbitol beeswax; Alkyl such as isostearyl glyceryl ether, chimyl alcohol, ceralkyl alcohol, batyl alcohol Glyceryl ethers; polyhydric alcohol alkyl ethers; polyoxyethylene alkylamines; tetrapolyoxyethylene / tetrapolyoxypropylene-ethylenediamine condensates; natural surfactants such as saponins and sophorolipids; polyoxyethylene fatty acid amides; coconut oil Fatty acid monoethanolamide (cocamide MEA), coconut oil fatty acid diethanolamide (cocamide DEA), lauric acid monoethanolamide (laura) De MEA), lauric acid diethanolamide (lauramide DEA), lauric acid monoisopropanolamide (lauramide MIPA), palmitic acid monoethanolamide (partamide MEA), palmitic acid diethanolamide (partamide DEA), palm oil fatty acid methyl ethanolamide (cocamidomethyl) Fatty acid alkanolamides such as MEA); alkyldimethylamine oxides such as lauramine oxide, cocamamine oxide, stearamine oxide, and behenamine oxide; alkylethoxydimethylamine oxide; polyoxyethylene alkyl mercaptan; poly such as dimethicone copolyol Silicone such as ether-modified silicone, polysiloxane-oxyalkylene copolymer, polyglycerin-modified silicone, sugar-modified silicone Nonionic surfactants, etc .; for cationic surfactants, alkyltrimethylammonium chlorides such as behentrimonium chloride, steartrimonium chloride, cetrimonium chloride, lauryltrimonium chloride; alkyls such as stearyltrimonium bromide Trialkylammonium bromide; dialkyldimethylammonium chloride such as distearyldimonium chloride and dicocodimonium chloride; fatty acid amidoamines and salts thereof such as stearamidepropyldimethylamine and stearamideethyldiethylamine; alkyl ether amines such as stearoxypropyldimethylamine; Salt or quaternary salt thereof; ethyl sulfate long chain branched fatty acid (12-31) aminopropylethyldimethylammonium, ethyl lanolin sulfate Fatty acid amide-type quaternary ammonium salts such as aminopropylethyldimethylammonium fatty acid; polyoxyethylene alkylamine and its salts or quaternary salts; alkylamine salts; fatty acid amidoguanidinium salts; alkyl etheraminemonium salts; Benzalkonium salts; benzethonium salts; pyridinium salts such as cetylpyridinium chloride; imidazolinium salts; alkylisoquinolinium salts; dialkyl morpholinium salts; polyamine fatty acid derivatives; Silicone-based cationic surfactants such as amino-modified silicone, cation-modified silicone, cation-modified and polyether-modified silicone, amino-modified and polyether-modified silicone;
In amphoteric surfactants, N-alkyl-N, N-dimethylamino acid betaines such as lauryl betaine (lauryldimethylaminoacetic acid betaine); fatty acid amide alkyl-N, N-dimethylamino acids such as cocamidopropyl betaine and lauramidopropyl betaine Betaines; imidazoline-type betaines such as sodium cocoamphoacetate and sodium lauroamphoacetate; alkylsulfobetaines such as alkyldimethyltaurine; sulfate-type betaines such as alkyldimethylaminoethanol sulfate; phosphate-type betaines such as alkyldimethylaminoethanol phosphate; Sphingophospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, sphingomyelin, lysolecithin, hydrogenated soybean phospholipid, partially hydrogenated Phospholipids such as soybean phospholipid, hydrogenated egg yolk phospholipid, partially hydrogenated egg yolk phospholipid, and hydroxylated lecithin; silicone-based amphoteric surfactants; polymer surfactants such as polyvinyl alcohol, sodium alginate, starch derivatives, Preferred are tragacanth gum, acrylic acid / alkyl methacrylate copolymer; and various silicone surfactants.

  Polymers, thickeners and gelling agents include guar gum, locust bean gum, queens seed, carrageenan, galactan, arabic gum, tara gum, tamarind, far selelain, karaya gum, troarooi, cara gum, tragacanth gum, pectin, pectic acid and sodium Salt such as salt, salt such as alginic acid and sodium salt, mannan; starch such as rice, corn, potato, wheat; xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid and its salt, xanthan gum, pullulan, gellan gum, chitin , Chitosan, agar, gypsum extract, chondroitin sulfate, casein, collagen, gelatin, albumin; methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropi Cellulose, carboxymethylcellulose and salts thereof such as sodium, methylhydroxypropylcellulose, cellulose sodium sulfate, cellulose dialkyldimethylammonium sulfate, crystalline cellulose, cellulose such as cellulose powder and derivatives thereof; soluble starch, carboxymethyl starch, methylhydroxypropyl starch, Starch-based polymers such as methyl starch, starch derivatives such as hydroxypropyltrimonium chloride, octenyl succinate corn starch and aluminum; alginic acid derivatives such as sodium alginate, propylene glycol alginate; Vinyl pydridone-vinyl alcohol copolymer, polyvinyl methyl ether Polyethylene glycol, polypropylene glycol, polyoxyethylene / polyoxypropylene copolymer; amphoteric methacrylic acid such as (methacryloyloxyethylcarboxybetaine / alkyl methacrylate) copolymer, (acrylates / stearyl acrylate / ethylamine methacrylate oxide) copolymer, etc. Ester copolymer; (Dimethicone / vinyl dimethicone) crosspolymer, (alkyl acrylate / diacetone acrylamide) copolymer, (alkyl acrylate / diacetone acrylamide) copolymer AMP; Polyvinyl acetate partial saponification product, maleic acid copolymer; Vinylpyrrolidone / dialkylaminoalkyl methacrylate copolymer; acrylic resin alkanolamine; polyester, water-dispersible polyester; Kurylamide; Polyacrylic acid ester copolymer such as polyethyl acrylate, carboxyvinyl polymer, polyacrylic acid and its sodium salt, acrylic acid / methacrylic acid ester copolymer; acrylic acid / alkyl methacrylate Polymer: Cationized cellulose such as polyquaternium-10, diallyldimethylammonium chloride / acrylamide copolymer such as polyquaternium-7, acrylic acid / diallyldimethylammonium chloride copolymer such as polyquaternium-22, and acrylic acid such as polyquaternium-39・ Diallyldimethylammonium chloride / acrylamide copolymer, acrylic acid / cationized methacrylic acid ester copolymer, acrylic acid / cationized methacrylic acid amide copolymer, polyquaternium Acrylic acid / methyl acrylate / methacrylamidopropyltrimethylammonium chloride copolymer such as 47, methacrylic acid choline ester polymer; cationized polysaccharides such as cationized oligosaccharide, cationized dextran, guar hydroxypropyltrimonium chloride; Polyethyleneimine; Cationic polymer; Polymer of 2-methacryloyloxyethyl phosphorylcholine such as polyquaternium-51 and copolymer with butyl methacrylate copolymer; Acrylic resin emulsion, polyethyl acrylate emulsion, polyacrylalkyl ester emulsion, Polymer emulsions such as polyvinyl acetate resin emulsion, natural rubber latex, synthetic latex; nitrocellulose; polyurethanes and various copolymers; various silicones Various silicone-based copolymers such as acrylic-silicone graft copolymers; various fluoropolymers; 12-hydroxystearic acid and its salts; dextrin fatty acid esters such as dextrin palmitate and dextrin myristate; silicic anhydride, Smoke-like silica (ultrafine silicic anhydride), aluminum magnesium silicate, magnesium magnesium silicate, metal soap, dialkyl phosphate metal salt, bentonite, hectorite, organically modified clay mineral, sucrose fatty acid ester, fructooligosaccharide fatty acid ester It is mentioned as preferable.

  Solvents and propellants include ethanol, 2-propanol (isopropyl alcohol), butanol, isobutyl alcohol and other lower alcohols; propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, isopentyl diol and other glycols Diethylene glycol monoethyl ether (ethoxydiglycol), ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, triethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether Glycol ethers such as ethylene glycol monoethyl ether Glycol ether esters such as acetate, diethylene glycol monoethyl ether acetate, propylene glycol monoethyl ether acetate; Glycol esters such as diethoxyethyl succinate, ethylene glycol disuccinate; benzyl alcohol, benzyloxyethanol, propylene carbonate, dialkyl carbonate , Acetone, ethyl acetate, butyl acetate, N-methylpyrrolidone; toluene; fluorocarbon, next-generation flon; propellants such as LPG, dimethyl ether, carbon dioxide, and the like are preferable.

  Antioxidants include tocopherol derivatives such as tocopherol (vitamin E) and tocopherol acetate; BHT, BHA; gallic acid derivatives such as propyl gallate; vitamin C (ascorbic acid) and / or derivatives thereof; erythorbic acid and derivatives thereof; Preferred are sulfites such as sodium sulfite; bisulfites such as sodium bisulfite; thiosulfates such as sodium thiosulfate; metabisulfites; thiotaurine, hypotaurine; thioglycerol, thiourea, thioglycolic acid, cysteine hydrochloride As mentioned.

  Preservatives and antibacterial agents include hydroxybenzoic acid such as methylparaben, ethylparaben, propylparaben, and butylparaben and salts or esters thereof; salicylic acid; sodium benzoate; phenoxyethanol; 1,2-pentanediol, 1,2-hexane 1,2-diols such as diols; isothiazolinone derivatives such as methylchloroisothiazolinone and methylisothiazolinone; imidazolinium urea; dehydroacetic acid and its salts; phenols; halogenated bisphenols such as triclosan, acid amides , Quaternary ammonium salts; trichlorocarbanide, zinc pyrithione, benzalkonium chloride, benzethonium chloride, sorbic acid, chlorhexidine, chlorhexidine gluconate, halocarban, hexachlorophene, Kichioru; phenol, isopropyl phenol, cresol, thymol, p-chlorophenol, phenylphenol, other phenols such as phenylphenol sodium; phenylethyl alcohol, photosensitive Motorui, be mentioned as antibacterial zeolite, silver ion.

  Examples of chelating agents include edetate (ethylenediaminetetraacetate) such as EDTA, EDTA2Na, EDTA3Na, and EDTA4Na; hydroxyethylethylenediaminetriacetate such as HEDTA3Na; pentetate (diethylenetriaminepentaacetate); phytic acid; Phosphonic acid and its sodium salt; sodium oxalate; polypolyamino acids such as polyaspartic acid and polyglutamic acid; sodium polyphosphate, sodium metaphosphate, phosphoric acid; sodium citrate, citric acid, alanine, dihydroxyethylglycine Gluconic acid, ascorbic acid, succinic acid, and tartaric acid are preferable.

  pH adjusters / acids / alkalis include citric acid, sodium citrate, lactic acid, sodium lactate, glycolic acid, succinic acid, acetic acid, sodium acetate, malic acid, tartaric acid, fumaric acid, phosphoric acid, hydrochloric acid, sulfuric acid, monoethanol Amine, diethanolamine, triethanolamine, isopropanolamine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol, arginine, hydroxylation Sodium, potassium hydroxide, aqueous ammonia, guanidine carbonate, and ammonium carbonate are preferable.

  As perfumes, acetyl cedrene, amylcinnamaldehyde, allyl amyl glycolate, β-ionone, iso-Esuper, isobutyl quinoline, Iris oil, Iron, indole, ylang ylang oil, undecanal, undecenal, γ-undecalactone, Estragole, eugenol, oak moss, opoponax resinoid, orange oil, eugenol, auranthiol, galac solid, carvacrol, L-carvone, camphor, cannon, carrot seed oil, clove oil, methyl cinnamate, geraniol, geranyl nitrile , Isobornyl acetate, geranyl acetate, dimethylbenzyl carvinyl acetate, styrylyl acetate, cedolyl acetate, terpinel acetate, pt-butylcyclohexyl acetate, vetiberyl acetate, benzyl acetate, vinegar Linalyl, isopentyl salicylate, benzyl salicylate, sandalwood oil, santalol, cyclamenaldehyde, cyclopentadecanolide, methyl dihydrojasmonate, dihydromilsenol, jasmine absolute, jasmine lactone, cis-jasmon, citral, citronenol, citronellal, Cinnamon bark oil, 1,8-cineole, cinnamaldehyde, stylax resinoid, cedarwood oil, cedrene, cedrol, celery seed oil, thyme oil, damascon, damassenone, thymol, tuberose absolute, decanal, decalactone, terpineol, γ-terpinene, Tripral, Nellore, Nonanal, 2,6-Nonadienol, Nonalactone, Patchouli alcohol, Vanilla absolute , Vanillin, basil oil, patchouli oil, hydroxycitronellal, α-pinene, piperitone, phenethyl alcohol, phenylacetaldehyde, petitglen oil, hexylcinnamaldehyde, cis-3-hexenol, peruvian valsum, vetiver oil, vetiverol, peppermint oil, Pepper oil, heliotropin, bergamot oil, benzyl benzoate, borneol, milresinoid, musk ketone, methylnonylacetaldehyde, γ-methylyonone, menthol, L-menthol, L-menthol, eucalyptus oil, β-yonone, lime oil, lavender oil, Synthetic and natural fragrances such as D-limonene, linalool, rilal, rireal, lemon oil, rose absolute, rose oxide, rose oil, rosemary oil, various essential oils, and various blended fragrances It is mentioned as preferred.

As pigments / colorants / dyes / pigments, brown 201, black 401, purple 201, purple 401, blue 1, blue 2, blue 201, blue 202, blue 203, blue 204 , Blue 205, Blue 403, Blue 404, Green 201, Green 202, Green 204, Green 205, Green 3, Green 401, Green 402, Red 102, Red 104-1 , Red 105-1, Red 106, Red 2, Red 201, Red 202, Red 203, Red 204, Red 205, Red 206, Red 207, Red 208, Red 213 Red 214, Red 215, Red 218, Red 219, Red 220, Red 221, Red 223, Red 225, Red 226, Red 227, Red 228, Red 230 No. 1, Red 230-2, Red 231, Red 232, Red 3, Red 401, Red 404, Red 405, Red 501, Red 502, Red 503, Red 504, Red 505, red 506, orange 201, orange 203, orange 204, orange 205, orange 206, orange 207, orange 401, orange 402, orange 403, yellow 201, yellow 202- No. 1, yellow 202-2, yellow 203, yellow 204, yellow 205, yellow 4, yellow 401, yellow 402, yellow 403-1, yellow 404, yellow 405, yellow 406 Legal dyes such as Yellow No. 407 and Yellow No. 5; Other acidic dyes such as Acid Red 14; Arianor Sienna Brown, Arianor Madder Red, Arianor
Basic dyes such as Steel Blue and Arianor Straw Yellow; HC Yellow 2, HC Yellow 5, HC Red 3, 4-hydoxypropylamino-3-nitrophenol, N, N'-bis (2-hydroxyethyl) -2-nitro-p-
Nitro dyes such as phenylenediamine, HC Blue 2 and Basic Blue 26; disperse dyes; inorganic white pigments such as titanium dioxide and zinc oxide; inorganic red pigments such as iron oxide (Bengara) and iron titanate; and γ-iron oxide Inorganic brown pigments; inorganic yellow pigments such as yellow iron oxide and ocher; inorganic black pigments such as black iron oxide and low-order titanium oxide; inorganic purple pigments such as mango violet and cobalt violet; chromium oxide and chromium hydroxide Inorganic green pigments such as cobalt titanate; inorganic blue pigments such as ultramarine and bitumen; titanium oxide coated mica, titanium oxide coated bismuth oxychloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, fish scale foil Pearl powder such as aluminum powder, copper powder, metal powder pigment such as gold; surface treatment inorganic and metal powder pigment; red 01, Red 202, Red 204, Red 205, Red 220, Red 226, Red 228, Red 405, Orange 203, Orange 204, Yellow 205, Yellow 401, Blue 404 Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green Organic pigments such as zirconium, barium or aluminum lakes such as No. 3 and Blue No. 1; surface-treated organic pigments; anthraquinones such as astaxanthin and alizarin, anthocyanidins, β-carotene, catenal, capsanthin, chalcone, calsamine, quercetin, crocin, Naphthoquinones such as chlorophyll, curcumin, cochineal, shikonin, bixin, flavo Natural pigments and dyes such as amines, betacyanidine, henna, hemoglobin, lycopene, riboflavin, rutin; p-phenylenediamine, toluene-2,5-diamine, o-, m-, or p-aminophenol, m-phenylene Oxidative dye intermediates and couplers such as diamine, 5-amino-2-methylphenol, resorcin, 1-naphthol, 2,6-diaminopyridine and their salts; auto-oxidizing dyes such as indoline; Can be mentioned.

  Preferred examples of water include normal water, purified water, hard water, soft water, natural water, deep sea water, electrolytic alkaline ionized water, electrolytic acidic ionized water, ionic water, and clustered water.

  In addition to these, cosmetic raw material standards, blending ingredient standard by cosmetic varieties, Japan Cosmetic Industry Association ingredient display name list, INCI dictionary (The International Cosmetic Ingredient Dictionary and Handbook), quasi-drug raw material standards, Japanese pharmacopoeia, pharmaceutical additives Ingredients listed in standards, official food additives, etc., and Japanese and foreign patent publications and patent publications (including publications and republications) in which the international patent classification IPC belongs to the classification of A61K7 and A61K8 It is possible to contain known cosmetic ingredients, pharmaceutical ingredients, food ingredients, etc., such as the ingredients described, in known combinations, blending ratios and blending amounts.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail using an Example, this invention is not limited to these Examples.

Example 1 Synthesis of succinic acid bis (diethylene glycol monoethyl ether) ester 90.0 g (0.9 mol) of succinic anhydride and diethylene glycol monoethyl ether 362. were added to a 300 ml reactor equipped with a stirrer, a thermometer and a gas introduction tube. 1 g (2.7 mol) was charged, heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 20 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure and steam deodorization was performed to obtain 297 g (yield 94%) of the target diester. The obtained ester was a colorless to pale yellow liquid having an acid value of 3.4 and a hue Gardner of 1 or less. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage).

Example 2 Synthesis of bis (diethylene glycol monoethyl ether) ester of adipic acid In a 300 ml reactor equipped with a stirrer, a thermometer and a gas introduction tube, 75 g (0.5 mol) of adipic acid and 206.3 g of diethylene glycol monoethyl ether (1 0.5 mol), heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 27 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure and steam deodorization was performed to obtain 185 g (yield 96%) of the target diester. The obtained ester was a colorless to pale yellow liquid having an acid value of 4.0 and a hue Gardner of 1 or less. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage).

Example 3 Synthesis of 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester 602 g (3.5 mol) of 1,4-cyclohexanedicarboxylic acid in a 3 L reactor equipped with a stirrer, thermometer and gas introduction tube Then, 1503 g (11.2 mol) of diethylene glycol monoethyl ether was charged, heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 33 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure, and steam deodorization was performed to obtain 1358 g (yield 96%) of the desired 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester. The obtained ester was a colorless to pale yellow liquid having an acid value of 3.3 and a hue Gardner of 1 or less. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage).

Example 4 Synthesis of azelaic acid bis (diethylene glycol monoethyl ether) ester A 300 ml reactor equipped with a stirrer, a thermometer and a gas introduction tube was charged with 85 g (0.45 mol) of azelaic acid and 181.8 g of diethylene glycol monoethyl ether (1 .36 mol) was charged, heated to 150 to 230 ° C. while blowing nitrogen, and reacted for 24 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure and steam deodorization was performed to obtain 181 g (yield 92%) of the target diester. The obtained ester was a yellow liquid and had an acid value of 3.9 and a hue Gardner 2. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage).

Example 5 Synthesis of dodecanedioic acid bis (diethylene glycol monoethyl ether) ester 100 g (0.43 mol) of dodecanedioic acid and 174.8 g of diethylene glycol monoethyl ether in a 300 ml reactor equipped with a stirrer, thermometer and gas introduction tube (1.3 mol) was charged, heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 20 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure and steam deodorization was performed to obtain 186 g (yield 93%) of the target diester. The obtained ester was a colorless to pale yellow liquid having an acid value of 3.9 and a hue Gardner of 1 or less. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage).

Example 6 Synthesis of phthalic acid bis (diethylene glycol monoethyl ether) ester In a 300 ml reactor equipped with a stirrer, thermometer and gas introduction tube, 80 g (0.54 mol) of phthalic acid and 217.4 g of diethylene glycol monoethyl ether (1 .62 mol) was charged, heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 50 hours while distilling off water. Subsequently, unreacted diethylene glycol monoethyl ether was distilled off under reduced pressure, and steam deodorization was performed to obtain 203.1 g (yield 94%) of the target diester. The ester thus obtained was a pale yellow liquid having an acid value of 9.8 and a hue Gardner 1. The diester content was 92% from analysis by capillary gas chromatography (FID, area percentage).

Example 7 Nail enamel removal ability Nail enamel removal ability was evaluated about the diester of Examples 1-6. In addition, diethoxyethyl succinate, liquid paraffin, cetyl isooctanoate, and isonononyl isononanoate were used as comparative oil agents.
(Evaluation method)
Apply a certain amount of commercially available nail enamel on a glass plate and dry, then drop a sufficient amount to cover the coated portion of the diester of Examples 1 to 6 on the coated nail enamel and use a wipe. The nail enamel removal ability was evaluated after wiping for 1 minute. The evaluation was performed in three stages: ○: completely removed, Δ: slightly removed, ×: not removed at all.
(result)
As described below, the diester used in the present invention was excellent in the ability to remove nail enamel.

Nail enamel removal ability Commercial product A Commercial product B Commercial product C
------------------------------------
Diester of Example 1 ○ ○ ○
Diester of Example 2 ○ ○ ○
Diester of Example 3 ○ ○ ○
Diester of Example 4 ○ ○ ○
Diester of Example 5 ○ ○ ○
Diester of Example 6 ○ ○ ○
Diethoxyethyl succinate △ △ △
Liquid paraffin × × ×
Cetyl isooctanoate × × ×
Isononyl isononanoate No No No
------------------------------------
Commercial product A: Shiseido Neel Enamel N Part No. RS333
Commercial product B: Kiss Me Nail Enamel Kids EX Part No. 34
Commercial product C: Finonere enamel Part number RD388

Example 8 Prevention of Nail Whitening For the diesters of Examples 1 to 6, a nail enamel remover having the following formulation was prepared, and the effect of preventing nail whitening was evaluated. For comparison, a non-diester compound was used.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Examples 1-6 40.00
2 Tocopherol 0.05
3 Ethyl acetate Residual ---------------------------------
(Preparation method)
No. 1-3 were added and mixed uniformly with stirring.
(Evaluation method)
The produced nail enamel remover was applied to the nail, and the state of the nail after drying was visually confirmed. The evaluation was performed in three stages: ◯: no whitening was observed, Δ: whitened slightly, x: whitened.
(result)
The nail enamel remover containing no diester showed whitening of the nail, whereas the nail enamel remover containing the diester of Examples 1 to 6 showed no nail whitening, and the nail enamel remover of the present invention It was found to prevent nail whitening.
Prevention of nail bleaching Nail condition --------------------------------
Diester compounded product of Example 1
Diester blended product of Example 2 ○
Diester blend product of Example 3 ○
Diester blended product of Example 4 ○
Diester blended product of Example 5 ○
Diester blend product of Example 6 ○
Diester-free product ×
--------------------------------

Example 9 Lipstick removing ability Cleansing milk having the following formulation was prepared using the diesters of Examples 1 to 6, and the ability to remove lipstick was evaluated. For comparison, cleansing milk not containing a diester was used.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Examples 1-6 3.00
2 Neosolute-DE (Nippon Seika) 5.00
3 Stearic acid 0.50
4 Mineral oil 32.00
5 Seths-20 2.40
6 Triceteth-5 Phosphoric acid 3.60
7 Stearic acid PG (SE) 3.00
8 Propylparaben 0.10
9 Dimethicone (10cs) 10.00
10 Carbomer 0.10
11 Hydroxide K 0.04
12 EDTA-2Na 0.05
13 Phenoxyethanol 0.20
14 Methylparaben 0.10
15 Purified water Total amount of 100 --------------------------------
(Preparation method)
No. 15 is a part of No. 15. No. 10 was added and stirred well. 11 was added to obtain a viscous liquid (Part A). No. 12-14, the remaining No. 15 was heated to about 70 ° C. and dissolved (Part B). No. 1 to 9 were heated to about 70 ° C. and dissolved (part C). After stirring and emulsifying part B while stirring part C, part A was added and cooled with stirring.
(Evaluation method)
Apply a certain amount of commercially available lipstick to Bio Skin Plate (Beaulux), and after drying, apply enough amount of each cleansing milk to cover the lipstick-coated part, and evaluate the ability to remove lipstick by rubbing with your finger did. In the evaluation, a case where the time until the lipstick fell within 1 minute was indicated as ◯, a case where the lipstick was within 2 minutes, a case where it was not dropped in 2 minutes, and a case where the lipstick was not dropped in 2 minutes.
(result)
The cleansing milk containing no diester did not remove the lipstick, whereas the cleansing milks containing the diesters of Examples 1 to 6 all removed the lipstick within 2 minutes, and the cleansing milk of the present invention was capable of removing lipstick. It turned out to be excellent.

Lipstick removal ability Commercial product D
--------------------------------
Diester compounded product of Example 1
Diester blended product of Example 2 ○
Diester blend product of Example 3 ○
Diester blended product of Example 4 ○
Diester compounded product of Example 5
Diester blend product of Example 6 ○
Diester-free product ×
--------------------------------
Commercial product D: Max Factor Lip Finity Pro Part No. F453F

Example 10 Usability When using the cleansing milk prepared in Example 9 and applying it to the skin, the feel after washing with water was evaluated. The thing which did not mix | blend the diester was used as a comparison.
(Evaluation method)
The feel when applied to the skin (stickiness, familiarity with the skin) and the feel after washing with water (moist feeling, refreshing feeling) were evaluated by the sensuality of 10 panelists. Evaluation: ◎: 8-10 out of 10 answered good, ○: 6-7 out of 10 answered good, △: 4-5 out of 10 answered good, x: 10 Three or less of them were in four stages of answering good.
(result)
As described below, the cleansing milk of the present invention was superior in usability compared to a diester-free product.

When applying After washing with water Feeling of use Stickiness Skin feeling Moist feeling Refreshing --------------------------------- ----
Diester of Example 1 ○ ○ ○ ○
Diester of Example 2 ◎ ○ ◎ ○
Diester of Example 3 ◎ ○ ◎ ◎
Diester of Example 4 ◎ ○ ○ ○
Diester of Example 5 ◎ ○ ○ ○
Diester of Example 6 ◎ ○ ○ ◎
Diester-free product × ○ △ △
------------------------------------

Example 11 Nail Enamel Remover A nail enamel remover having the following formulation was prepared. This nail enamel remover was excellent in removing nail enamel and provided a moist feeling to the nails.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 5 90.00
2 CIO (Nippon Seika) 10.00
--------------------------------
(Preparation method)
No. 1-2 was added and mixed uniformly with stirring.

Example 12 Nail Enamel Remover A nail enamel remover having the following formulation was prepared. This nail enamel remover was excellent in removing nail enamel and suppressed whitening of nails.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 2 40.00
2 Butyl acetate 30.00
3 Tocopherol 0.05
4 Ethyl acetate Residual ---------------------------------
(Preparation method)
No. 1-4 were added and mixed uniformly with stirring.

Example 13 Nail Enamel Remover A nail enamel remover having the following formulation was prepared. This nail enamel remover was excellent in removing nail enamel and suppressed whitening of nails.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 50.00
2 Propylene carbonate 49.95
3 Tocopherol 0.05
--------------------------------
(Preparation method)
No. 1-4 were added and mixed uniformly with stirring.

Example 14 Cleansing oil A cleansing oil having the following formulation was prepared. This cleansing oil had a refreshing feel and was well-familiar with foundations, makeup, etc., and could be quickly removed.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 1.00
2 Laureth-4 7.00
3 Tocopherol appropriate amount
4 Propylparaben appropriate amount
5 Cetyl octoate Total amount of 100
6 Mineral oil 10.00
--------------------------------
(Preparation method)
All ingredients were heated and dissolved and mixed.

Example 15 Cleansing Gel A cleansing gel having the following formulation was prepared. Since this cleansing gel has excellent solubility, it has good effects such as a good feel of foundation and makeup, and a refreshing feel.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 5 15.00
2 Plandool-H (Nippon Seika) 2.00
3 Bellpole DC-30 (Nippon Seika) 2.00
4 LUSPLAN DD-IS (Nippon Seika) 15.00
5 PEG-25 hydrogenated castor oil 20.00
6 Glycerin 16.00
7 BG 5.00
8 Purified water Total amount of 100 --------------------------------
(Preparation method)
No. 1-No. 7 is weighed and dissolved by heating to about 80 ° C. (A). No. 8 is weighed and heated to about 80 ° C. (B). While stirring, gradually add B to A, and cool to 40 ° C. after emulsification.

Example 16 Facial cleansing foam A facial cleansing foam having the following formulation was prepared. This facial cleansing foam has good foaming and provides effects such as providing a smooth and smooth feel to the skin.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 1.00
2 Potassium palm fatty acid (34%) 44.00
3 Cocamidopropyl betaine (30%) 38.00
4 Cocamide DEA 6.00
5 PEG1000 4.00
6 Glycol distearate2.00
7 Glycerin 4.40
8 Methylparaben 0.20
9 Phenoxyethanol 0.20
10 Purified water Total amount of 100 --------------------------------
(Preparation method)
All ingredients were mixed uniformly.

Example 17 Facial Cleansing Foam A facial cleansing foam having the following formulation was prepared. This face-washing foam had good foaming, and it was possible to obtain effects such as providing a smooth and smooth feel to the skin.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 1.00
2 (coconut fatty acid / hydrogenated beef tallow fatty acid) glutamic acid Na 20.00
3 Plandool-G (Nippon Seika) 1.00
4 Lauric acid diethanolamide 2.00
5 PEG-8 5.00
6 PEG-30 10.00
7 BG 14.00
8 Propylparaben 0.10
9 Methylparaben 0.20
10 Lipidure PMB (Japanese fat) 1.00
11 Crystalline cellulose 10.00
12 Tocopherol 0.20
13 Purified water Total amount of 100 --------------------------------
(Preparation method)
No. 1-9, no. 12 was heated to about 80 ° C. and dissolved. After dissolution, no. 12-13 were added and dissolved. While stirring at about 60 ° C., no. 10-11 were added and cooled.

Example 18 Cleansing Cream A cleansing cream having the following formulation was prepared. This cleansing cream had good familiarity with makeup cosmetics and was excellent in cleansing effect.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 15.00
2 Ceresin 6.00
3 Mineral oil 35.00
4 Sorbitan sesquioleate 1.50
5 Oleic acid polyoxyethylene sorbitan 0.30
6 Paraffin 2.00
7 Butylparaben 0.10
8 Methylparaben 0.20
9 Trisodium edetate 0.02
10 Phenoxyethanol 0.20
11 Purified water Total amount of 100 --------------------------------
(Preparation method)
No. 1 to 7 were heated to about 80 ° C. and dissolved (part A). No. 8-11 were added and heated to about 80 ° C. to dissolve (Part B). The part B was gradually added to the part A with stirring and emulsified, and then cooled to about 40 ° C. with stirring.

Example 19 Cleansing Lotion A cleansing lotion having the following formulation was prepared. This cleansing lotion had good familiarity with makeup cosmetics and was excellent in cleansing effect.

Component Blending amount (% by weight)
--------------------------------
1 Diester of Example 3 4.00
2 BG 28.00
3 DPG 20.00
4 PEG / PPG-25 / 30 copolymer 2.00
5 PEG-60 hydrogenated castor oil 5.00
6 Lactic acid 0.10
7 Sodium lactate 0.10
8 Dihydrocholes-30 0.50
9 Sodium metaphosphate 0.10
10 Methylparaben 0.20
11 Purified water Total amount of 100 --------------------------------
(Preparation method)
No. 1 to 7 were heated to about 80 ° C. and dissolved (part A). No. 8-11 were added and heated to about 80 ° C. to dissolve (Part B). The part B was gradually added to the part A with stirring and emulsified, and then cooled to about 40 ° C. with stirring.

  According to the present invention, it is possible to obtain a makeup remover such as a cleansing agent and a nail enamel remover having excellent makeup removal ability and good usability.

Claims (5)

1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, diphthalic acid selected from phthalic acid, isophthalic acid, terephthalic acid , and polyoxyethylene monoester represented by Chemical formula 2 A makeup remover containing a diester with an alkyl ether.
(Chemical formula 2)
R2- (OCH2CH2) n-OH
(Wherein R2 is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n represents an integer of 2 to 11)   A nail enamel remover comprising the diester according to claim 1.   A cleansing agent comprising the diester according to claim 1. R2 is A composition according to any one of claims 1 to 3 methyl or ethyl polyoxyethylene monoalkyl ether represented by Formula 2. The composition according to any one of claims 1 to 3 , wherein the polyoxyethylene monoalkyl ether represented by Chemical Formula 2 is one or two selected from diethylene glycol monoethyl ether and triethylene glycol monoethyl ether.