JP2009057350A - Antibacterial agent and antibacterial cosmetic or external preparation containing the same - Google Patents

Abstract

[PROBLEMS] To provide an excellent antibacterial agent that is excellent in safety, has little odor, has good pH stability in an aqueous solution system, and does not emit harmful substances even when hydrolyzed, and contains the antibacterial agent Providing antibacterial cosmetics or skin external preparations with excellent safety and stability.
An antibacterial agent containing a diester of a dicarboxylic acid represented by Chemical Formula 1 and a polyoxyethylene monoalkyl ether represented by Chemical Formula 2 is used.
(Chemical formula 1)
HO-CO-R1-CO-OH
(Wherein R1 represents a linear, branched or cyclic hydrocarbon group having 3 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)
[Selection figure] None

Description

The present invention relates to an antibacterial agent 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 3 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 present invention also relates to an antibacterial cosmetic or skin external preparation containing the antibacterial agent.

  In general, antibacterial agents (preservatives) are blended in cosmetics or skin external preparations for the purpose of suppressing the growth of contaminated microorganisms from the outside and improving the storage stability of the product. As antibacterial agents used for such purposes, parabens (paraoxybenzoic acid esters) and phenoxyethanol are generally used. Parabens, phenoxyethanol and the like are excellent as antiseptic means for use in cosmetics or external preparations for skin, but are not necessarily satisfactory in terms of skin irritation and skin sensitization, and phenoxyethanol. Also had the problem of a strong odor. Therefore, the demand for cosmetics or external preparations for skin that reduce the amount of parabens and phenoxyethanol or do not mix at all has increased. Under such circumstances, Patent Document 1 proposes diethoxyethyl succinate as an antibacterial component replacing parabens and phenoxyethanol. However, since diethoxyethyl succinate has poor pH stability in an aqueous solution, it is still insufficient as an antibacterial agent to be added to cosmetics or skin external preparations. Furthermore, diethoxyethyl succinate has a problem that ethyl cellosolve having a safety problem occurs when hydrolysis occurs.

On the other hand, diesters of polyoxyethylene monoalkyl ethers such as ethyl carbitol and dicarboxylic acids such as cyclohexanedicarboxylic acid have both hydrophilic and lipophilic functions and are excellent in usability as oils for cosmetics or skin external preparations. It is known to have a touch (Patent Document 2).
JP 2002-3375 A Japanese Patent Application No. 2006-315081

  The problem to be solved by the present invention is an excellent antibacterial agent that is excellent in safety, has little odor, has good pH stability in an aqueous solution system, and does not emit harmful substances even when hydrolyzed, Another object of the present invention is to provide an antibacterial cosmetic or skin external preparation excellent in safety and stability, containing the antibacterial agent.

As a result of intensive studies to solve the above problems, the present inventors have used the dicarboxylic acid represented by Chemical Formula 1 and the polyoxyethylene monoalkyl ether represented by Chemical Formula 2 to solve the above problems. The inventors have found that this can be solved and completed the present invention. That is, the present invention relates to an antibacterial agent containing a diester of a dicarboxylic acid represented by Chemical Formula 1 and a polyoxyethylene monoalkyl ether represented by Chemical Formula 2, and an antibacterial cosmetic containing the antibacterial agent or An external preparation for skin is provided.
(Chemical formula 1)
HO-CO-R1-CO-OH
(Wherein R1 represents a linear, branched or cyclic hydrocarbon group having 3 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 antibacterial agent containing the diester of the present invention is an antibacterial agent with excellent safety, low odor, good pH stability in an aqueous solution system, and no harmful substances even when hydrolyzed Since it is an agent, it can be preferably blended in cosmetics or external preparations for skin. Moreover, the antimicrobial cosmetics or skin external preparation excellent in safety | security and stability can be obtained by mix | blending the antimicrobial agent of this invention.

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 3 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 dicarboxylic acid represented by Chemical Formula 1 constituting the diester is a dicarboxylic acid in which R1 represents a linear, branched or cyclic hydrocarbon group having 3 to 10 carbon atoms. When R1 is a hydrocarbon group having 2 or less carbon atoms, that is, when the dicarboxylic acid is succinic acid or malonic acid, the pH stability of the diester aqueous solution is deteriorated. Therefore, in the present invention, R1 is a hydrocarbon group having 2 or less carbon atoms. The dicarboxylic acid which is cannot be used. Further, when R1 is a hydrocarbon group having 11 or more carbon atoms, the water solubility and antibacterial properties of the diester are lost, and therefore dicarboxylic acids in which R1 is a hydrocarbon group having 11 or more carbon atoms cannot be used. Examples of dicarboxylic acids constituting the diester used in the antibacterial agent of the present invention include saturated linear dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid; Saturated branched dicarboxylic acids such as 2,4-trimethyladipic acid and 2,4,4-trimethyladipic acid; 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, etc. And saturated cyclic dicarboxylic acids; aromatic cyclic dicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid. Among these, from the viewpoints of antibacterial property, water solubility, pH stability of aqueous solution, oxidation stability, availability, etc., as dicarboxylic acid represented by Chemical Formula 1 constituting diester, R1 has 3 to 6 carbon atoms. A dicarboxylic acid representing a saturated linear, branched or cyclic hydrocarbon group is more preferred. More specifically, preferred dicarboxylic acids are adipic acid, pimelic acid, suberic acid, and 1,4-cyclohexanedicarboxylic acid. Since antibacterial properties and pH stability of aqueous solutions of diesters are good, 1,4 -Cyclohexanedicarboxylic acid is most preferred.

  R2 of the polyoxyethylene monoalkyl ether represented by Chemical Formula 2 constituting the diester is a linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms, and n is an integer of 2 to 11. Examples of the linear, branched or cyclic hydrocarbon group having 1 to 12 carbon atoms of R2 include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, n- Examples include hexyl group, cyclohexyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, n-dodecyl group, etc., from the viewpoints of reactivity, antibacterial properties, water solubility, and availability during esterification. , A methyl group and an ethyl group are preferable, and an ethyl group is particularly preferable. On the other hand, for n in Chemical Formula 2, when n is 1, that is, when cellosolve (ethylene glycol monoalkyl ether) is used, cellosolves that have been pointed out to have safety problems when the diester is hydrolyzed are Therefore, in the present invention, those in which n is 1 in Chemical Formula 2 cannot be used from the viewpoint of safety. Moreover, when n is 12 or more, it cannot be used for this invention from the viewpoint of the reaction at the time of esterification, the difficulty of a refinement | purification, and an antimicrobial property. Therefore, n in the chemical formula 2 needs to be an integer of 2 to 11. Furthermore, n is preferably 2 or 3 from the viewpoints of availability and antibacterial properties. For these reasons, the polyoxyethylene monoalkyl ether represented by Chemical Formula 2 is preferably diethylene glycol monoethyl ether or triethylene glycol monoethyl ether, and most preferably diethylene glycol monoethyl ether.

  From the above, as the diester used in the antibacterial agent of the present invention, bis (diethylene glycol monoethyl ether), bis (triethylene glycol monoethyl ether) adipate, bis (diethylene glycol monoethyl ether) pimelate, bis suberate ( Diethylene glycol monoethyl ether), 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether), 1,4-cyclohexanedicarboxylic acid bis (triethylene glycol monoethyl ether) are preferred, adipic acid bis (diethylene glycol monoethyl ether), 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) is more preferred, and 1,4-cyclohexanedicarboxylic acid bis (diethylene) Glycol monoethyl ether) are antibacterial, pH stability of the aqueous solution, most preferable in terms of safety.

  Although the manufacturing method of the diester used for the antibacterial agent of the present invention is not particularly limited, the following manufacturing method, that is, when the raw material dicarboxylic acid and polyoxyethylene monoalkyl ether are subjected to an esterification reaction at 150 to 260 ° C. without solvent. Can be produced economically advantageously. 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 of the present invention can be obtained by purification without purification or by a conventional purification method such as vacuum distillation, washing with water, steam deodorization, activated carbon treatment or the like. During production, in addition to diesters, monoesters and unreacted polyoxyethylene monoalkyl ethers may remain in the diesters. Even if a monoester or unreacted polyoxyethylene monoalkyl ether remains, it may not be a problem depending on the use, but when used as an antibacterial agent described later, particularly as an oil for cosmetics or external preparations for skin. The purity of the diester is desirably 80% by weight or more, preferably 90% by weight or more, and more preferably 95% by weight or more.

  The diester thus obtained has excellent antibacterial properties, good safety, little odor, good pH stability in an aqueous solution system, and can produce harmful substances even when hydrolyzed. However, it can be used as an antibacterial agent as it is, but for cosmetics such as antibacterial agents other than the diester or antiseptics, antioxidants, polyols described later and polymers thereof, or the like An antibacterial agent can also be obtained by containing together a moisturizer / feel improver for external preparations for skin, an oily base for cosmetics or external preparations for skin. Antibacterial agents or preservatives other than the diester include phenoxyethanol; 1,2-pentanediol (pentylene glycol), 1,2-hexanediol, 1,2-octanediol (caprylyl glycol), etc. Alkanediols; alkyl glyceryl ethers such as 2-ethylhexyl glyceryl ether (ethyl hexyl glycerin) can be used. When blending an antibacterial agent other than the diester, the content of the antibacterial agent or preservative other than the diester is preferably 1 to 90% by weight, although it depends on the type of the antibacterial agent. 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 content of the diester in the antibacterial agent of the present invention is not particularly limited, but is generally 10 to 99.99% by weight, preferably 50 to 99.99% by weight.

  The antibacterial agent of the present invention has excellent properties such as safety, low odor, good pH stability in an aqueous solution system, and no harmful substances even when hydrolyzed. Therefore, an antibacterial cosmetic or external preparation for skin can be prepared by blending this into a cosmetic or external preparation for skin. The blending amount of the antibacterial agent of the present invention in cosmetics or external preparations for skin is preferably 0.1 to 50% by weight, more preferably 0.2 to 20% by weight, in order to exhibit sufficient antibacterial properties.

  In addition to the antibacterial agent of the present invention, antibacterial agents or preservatives other than the diester, and, if necessary, generally used in cosmetics or skin external preparations. Added components such as oil base, moisturizer, feel improver, surfactant, polymer, thickener / gelator, solvent, propellant, antioxidant, reducing agent, oxidizing agent, chelating agent, pH Conditioner, acid, alkali, powder, inorganic salt, UV absorber, whitening agent, vitamins and derivatives thereof, anti-inflammatory agent, anti-inflammatory agent, hair growth agent, blood circulation promoter, stimulant, hormone, anti-wrinkle Agent, anti-aging agent, squeeze agent, cooling sensation agent, warming sensation agent, wound healing promoter, irritation relaxation agent, analgesic agent, cell activator, plant / animal / microbe extract, antipruritic agent, keratin exfoliating / dissolving agent, antibacterial agent Sweat agent, freshener, astringent, enzyme, nucleic acid, fragrance, pigment, colorant, dye, pigment, water It can be formulated.

Examples of these additional components include antibacterial agents or preservatives other than the diesters such as parabens (hydroxybenzoate esters) such as methylparaben, ethylparaben, propylparaben, and butylparaben; phenoxyethanol; 1,2-pentanediol; 1,2-alkanediols such as 1,2-hexanediol and 1,2-octanediol; alkylglyceryl ethers such as 2-ethylhexylglyceryl ether (ethylhexylglycerin); salicylic acid; sodium benzoate; methylchloroisothiazolinone Isothiazolinone derivatives such as methyl isothiazolinone; imidazolinium urea; dehydroacetic acid and its salts; phenols; halogenated bisphenols such as triclosan, acid amides, quaternary ammonium salts; Lichlorocarbanide, zinc pyrithione, benzalkonium chloride, benzethonium chloride, sorbic acid, chlorhexidine, chlorhexidine gluconate, halocarban, hexachlorophene, hinokitiol; phenol, isopropylphenol, cresol, thymol, parachlorophenol, phenylphenol, phenylphenol Other phenols such as sodium; phenylethyl alcohol, photosensitizers, antibacterial zeolite, and silver ion are preferable, but an antibacterial agent or a preservative other than the diester is used as an antibacterial agent or a preservative for antiseptic purposes. In the case, from the viewpoint of safety of cosmetics or external preparations for skin, phenoxyethanol; 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, etc. , 2-alkanediols; the use of alkyl glyceryl ethers such as 2-ethylhexyl glyceryl ether are more preferable.

  Examples of oily bases include cetanol, myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol, stearyl alcohol, aralkyl alcohol, behenyl alcohol, jojoba alcohol, chimyl alcohol, ceralkyl alcohol, batyl alcohol, hexyldecanol, isostearyl alcohol, Higher alcohols such as 2-octyldodecanol and dimer diol; aralkyl alcohols and derivatives such as benzyl alcohol; lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, behenic acid, undecylenic acid, 12-hydroxystearic acid, Palmitooleic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, docosahexaenoic acid, eicosapentaenoic acid, isohexa Higher fatty acids such as cannic acid, anteisohenicosanoic acid, long-chain branched fatty acid, dimer acid, hydrogenated dimer acid, and metal soaps such as aluminum salts, calcium salts, magnesium salts, zinc salts, potassium, sodium salts, etc. 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, petrolatum, solid Type hydrocarbons such as candelilla wax, carnauba wax, rice wax, wax, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, petrolatum, fisher Tropsch wax, polyethylene wax, waxes such as ethylene / propylene copolymer; 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, cucumber nut oil, rosehip oil, meadow foam oil, persic oil, tea tree oil, peppermint oil, corn oil, rapeseed oil, sunflower oil, wheat germ oil, linseed oil, cottonseed oil, soybean oil, peanut oil, rice bran Vegetable oils such as oil, cacao butter, shea fat, hydrogenated coconut oil, hydrogenated castor oil, jojoba oil, hydrogenated jojoba oil; animal properties such as beef tallow, milk fat, horse fat, egg yolk oil, mink oil, turtle oil Fats and oils; animal waxes such as whale wax, lanolin, orange luffy oil; liquid lanolin, reduced lanoli Lanolins such as adsorption purified lanolin, lanolin acetate, liquid lanolin acetate, hydroxy lanolin, polyoxyethylene lanolin, lanolin fatty acid, hard lanolin fatty acid, lanolin alcohol, lanolin alcohol acetate, acetic acid (cetyl lanolyl) ester; lecithin, phosphatidylcholine, Phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, sphingophospholipids such as sphingomyelin, phospholipids such as phosphatidic acid, lysolecithin; hydrogenated soybean phospholipid, partially hydrogenated soybean phospholipid, hydrogenated egg yolk phospholipid, Phospholipid derivatives such as partially hydrogenated egg yolk phospholipids; cholesterol, dihydrocholesterol, lanosterol, dihydrolanosterol, phytoster Sterols such as oleol and 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), N Acyl sarcosine alkyl esters such as lauroyl sarcosine isopropyl, cholesteryl 12-hydroxystearate, macadamia nut oil fatty acid cholesteryl, macadamia nut oil fatty acid phyto Sterol esters such as steryl, phytosteryl isostearate, 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, etc. Lipid complex: octyldodecyl myristate, hexyl decyl myristate, octyl dodecyl isostearate, cetyl paritate, octyldodecyl palmitate, cetyl octanoate, hexyl decyl octanoate, isotridecyl isononanoate, isononyl isononanoate, isononanoate Isotridecyl acid, isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octeodecanoate Ludodecyl, oleyl oleate, octyldodecyl oleate, octyldodecyl ricinoleate, lanolin fatty acid octyldodecyl, hexyldecyl dimethyloctanoate, octyldodecyl erucate, isostearic acid hydrogenated castor oil, ethyl oleate, ethyl avocado oil, 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, triethyl citrate, etc. Monoalcohol carboxylic acid esters; cetyl lactate, diisostearyl malate, monoisostearyl Oxyacid esters such as acid hydrogenated castor oil; glyceryl trioctanoate, glyceryl trioleate, glyceryl triisostearate, glyceryl diisostearate, glyceryl tri (caprylic / capric), tri (caprylic / capric / myristin) Acid / stearic acid) glyceryl, hydrogenated rosin triglyceride (hydrogenated ester gum), rosin triglyceride (ester gum), glyceryl behenate, trimethylolpropane trioctanoate, trimethylolpropane triisostearate, neopentyl glycol dioctanoate , Neopentyl glycol dicaprate, 2-butyl-2-ethyl-1,3-propanediol dioctanoate, propylene glycol dioleate, pentaerythrtetraoctanoate Chill, hydrogenated rosin pentaerythrityl, triethylhexanoic acid ditrimethylolpropane, (isostearic acid / sebacic acid) ditrimethylolpropane, triethylhexanoic acid pentaerythrityl, (hydroxystearic acid / stearic acid / rosinic acid) dipentaerythrityl, diisostearic acid di Glyceryl, 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) , Dineopentanoic acid 3-methyl-1,5-pentanediol, dineopentanoic acid 2,4-diethyl-1,5-pentane Polyhydric alcohol fatty acid esters such as ol; dimer dilinoleate diisopropyl, dimer dilinoleate diisostearyl, dimer dilinoleate di (isostearyl / phytosteryl), dimer dilinoleate (phytosteryl / behenyl), dimer dilinoleate (Phytosteryl / isostearyl / cetyl / stearyl / behenyl), dimer dilinoleic acid dimer dilinoleyl, diisostearic dimer dilinoleyl, dimer dilinoleyl hydrogenated rosin condensate, dimer dilinoleic acid hydrogenated castor oil, hydroxyalkyl die Dimer acid or dimer diol derivative such as merlinoleyl ether; coconut oil fatty acid monoethanolamide (cocamide MEA), coconut oil fatty acid diethanolamide (cocamide DEA), Lauri Acid monoethanolamide (lauramide MEA), lauric acid diethanolamide (lauramide DEA), lauric acid monoisopropanolamide (lauramide MIPA), palmitic acid monoethanolamide (partamide MEA), palmitic acid diethanolamide (partamide polyamide) Fatty acid alkanolamides such as fatty acid methylethanolamide (cocamidomethyl MEA); dimethicone (dimethylpolysiloxane), highly polymerized dimethicone (highly polymerized dimethylpolysiloxane), cyclomethicone (cyclic dimethylsiloxane, decamethylcyclopentasiloxane), phenyltrimethicone , Diphenyldimethicone, phenyldimethicone, stearoxypropyldimethylamine, (aminoethylaminopropylmethicone / dimethicone) Polymer, 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, carvone 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-modified and poly-modified Ether-modified silicone, alkyl-modified and polyether-modified silicone, polysiloxane-oxyalkylene copolymer Silicones such as body; 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 salts thereof; collagen, fish-derived collagen, atelocollagen, gelatin, elastin, collagen-degrading peptide, hydrolyzed collagen, hydroxypropylammonium chloride-hydrolyzed collagen, elastin Degraded peptide, keratin degrading peptide, hydrolyzed keratin, conchiolin degrading peptide, hydrolyzed conchiolin, silk proteolytic peptide, hydrolyzed silk, lauroyl hydrolyzed silk sodium, soybean 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 tides; silylated peptides; lactic acid bacteria culture solution, yeast extract, eggshell membrane protein, bovine submandibular 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 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 (partamid MEA), palmitic acid diethanolamide (partamide DEA), palm oil fatty acid methylethanolamide (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 salt; Pyridinium salt such as cetylpyridinium chloride; Imidazolinium salt; Alkylisoquinolinium salt; Dialkyl morpholinium salt; Polyamine fatty acid derivatives; Aminopropyl dimethicone and amodimethicone 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 laurylbetaine (lauryldimethylaminoacetic acid betaine); fatty acid amidoalkyl-N, N-dimethylamino acids such as cocamidopropylbetaine and lauramidopropylbetaine 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 its salts such as sodium, methylhydroxypropylcellulose, sodium cellulose sulfate, cellulose dialkyldimethylammonium sulfate, crystalline cellulose, cellulose powder such as cellulose powder; 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 and propylene glycol alginate; polyvinylpyridone (PVP), polyvinyl alcohol (PVA), 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: Cationic 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, 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. Preferred examples of the reducing agent include thioglycolic acid, cysteine, cysteamine and the like. Preferred examples of the oxidizing agent include aqueous hydrogen peroxide, ammonium persulfate, sodium bromate, and percarbonate.

  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.

  Examples of powders include mica, talc, kaolin, sericite, montmorillonite, kaolinite, mica, muscovite, phlogopite, synthetic mica, red mica, biotite, permiculite, magnesium carbonate, calcium carbonate, aluminum silicate, silica Barium acid, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, zeolite, barium sulfate, calcined calcium sulfate, calcium phosphate, fluorine apatite, hydroxyapatite, ceramic powder, bentonite, smectite, clay, mud, Metal soap (e.g., zinc myristate, calcium palmitate, aluminum stearate), calcium carbonate, bengara, yellow iron oxide, black iron oxide, ultramarine, bitumen, carbon black, titanium oxide, fine particles and ultrafine Titanium oxide, zinc oxide, fine and ultrafine zinc oxide, alumina, silica, fumed silica (ultrafine silica), titanium mica, fish scale foil, boron nitride, photochromic pigment, synthetic fluorophlogopite, fine particle composite powder Body, gold, aluminum, etc., various sizes and shapes of inorganic powders, and these are treated with various surface treatment agents such as hydrogen silicone, cyclic hydrogen silicone, or other silane or titanium coupling agents Inorganic powders such as hydrophobized or hydrophilized powders; starch, cellulose, nylon powder, polyethylene powder, polymethyl methacrylate powder, polystyrene powder, copolymer resin powder of styrene and acrylic acid, polyester powder, Benzoguanamine resin powder, polyethylene terephthalate, polymethyl Organic powders and surface-treated powders of various sizes and shapes, such as methacrylate powder, polyethylene terephthalate / aluminum / epoxy powder, urethane powder, silicone powder, Teflon (registered trademark) powder, organic-inorganic composite powder Is preferable. Inorganic salts include sodium chloride-containing salts such as salt, common salt, rock salt, sea salt, natural salt; potassium chloride, aluminum chloride, calcium chloride, magnesium chloride, bittern, zinc chloride, ammonium chloride; sodium sulfate, aluminum sulfate, Aluminum sulfate / potassium sulfate (alum), aluminum sulfate / ammonium sulfate, barium sulfate, calcium sulfate, potassium sulfate, magnesium sulfate, zinc sulfate, iron sulfate, copper sulfate; sodium phosphates such as 1Na, 2Na and 3Na phosphates, phosphoric acid Potassium, calcium phosphates and magnesium phosphates are preferred.

Examples of ultraviolet absorbers include paraaminobenzoic acid, paraaminobenzoic acid monoglycerin ester, N, N-dipropoxyparaaminobenzoic acid ethyl ester, N, N-diethoxyparaaminobenzoic acid ethyl ester, and N, N-dimethylparaaminobenzoic acid ethyl ester. Benzoic acid-based ultraviolet absorbers such as esters, N, N-dimethylparaaminobenzoic acid butyl ester, N, N-dimethylparaaminobenzoic acid ethyl ester; Anthranilic acid-based ultraviolet absorbers such as homomenthyl-N-acetylanthranilate; Salicylic acid And salicylic acid-based purple such as sodium salt, amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanol phenyl salicylate Line absorber: Octyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropyl cinnamate, methyl-2,4-diisopropyl cinnamate, propyl-p- Methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate, 2-ethylhexyl p-methoxycinnamate (octyl paramethoxycinnamate), 2-ethoxyethyl-p-methoxycinnamate (sinoxate), Cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl α-cyano-β-phenylcinnamate (octocrine), glyceryl mono-2-ethylhexanoyl-diparamethoxy Nameto, cinnamic acid UV absorbers such as ferulic acid and its derivatives; 2,4-dihydroxybenzophenone, 2,2'-
Dihydroxy-4-methoxybenzophenone, 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, 2,2 ′, 4,4′-tetrahydroxybenzophenone, 2-hydroxy-4-
Methoxybenzophenone (oxybenzone-3), 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenyl -Benzophenone ultraviolet absorbers such as benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, l- Camphor, 3-benzylidene-d, l-camphor; 2-phenyl-5-methylbenzoxazole; 2,2'-hydroxy-5-methylphenylbenzotriazole; 2- (2'-hydroxy-5'-t- Octylphenyl) benzotriazole; 2- (2′-H Dioxy-5'-methylphenylbenzotriazole;dibenzalazine;dianisoylmethane; 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one; di- such as 4-t-butylmethoxydibenzoylmethane Benzoylmethane derivatives; octyl triazone; urocanic acid derivatives such as urocanic acid and ethyl urocanate; 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, 1- (3,4-dimethoxyphenyl) -4, Hydantoin derivatives such as 4-dimethyl-1,3-pentanedione, dimethoxybenzylidenedioxoimidazolidinepropionate 2-ethylhexyl, phenylbenzimidazolazole sulfonic acid, terephthalylidene dicamphulsulfonic acid, drometrizol trisiloxane, anthranyl Methyl, rutin and its derivatives, oryzanol and derivatives thereof as preferred.

  Examples of whitening agents include hydroquinone glycosides such as arbutin and α-arbutin and esters thereof; ascorbic acid phosphate salts such as ascorbic acid, sodium ascorbate phosphate and magnesium ascorbate phosphate, ascorbic acid Ascorbic acid fatty acid esters such as tetraisopalmitic acid ester, ascorbic acid alkyl ethers such as ascorbic acid ethyl ether, ascorbic acid glucosides such as ascorbic acid-2-glucoside and fatty acid esters thereof, ascorbic acid sulfate ester, tocopheryl ascorbyl phosphate Ascorbic acid derivatives such as kojic acid, ellagic acid, tranexamic acid and its derivatives, ferulic acid and its derivatives, placenta extract, glutathione, oryzanol, butylreso Shinoru, oil soluble Kamomiraekisu oil soluble licorice extract, Nishikawa willow extract, be mentioned as saxifrage extract, and the like plant extracts are preferred.

  Vitamins and their derivatives include vitamin A such as retinol, retinol acetate, retinol palmitate; thiamine hydrochloride, thiamine sulfate, riboflavin, riboflavin acetate, pyridoxine hydrochloride, pyridoxine dioctanoate, pyridoxine dipalmitate, Flavin adenine dinucleotide, cyanocobalamin, folic acid, nicotinic acid such as nicotinic acid amide / benzyl nicotinate, vitamin B group such as choline; vitamin C such as ascorbic acid and its sodium salt; vitamin D; α, Vitamin Es such as β, γ, δ-tocopherol; other vitamins such as pantothenic acid and biotin; ascorbic acid phosphates such as ascorbic acid phosphate sodium salt and ascorbic acid phosphate magnesium salt; Ascorbic acid fatty acid esters such as corobic acid tetraisopalmitic acid ester, ascorbyl stearate, ascorbyl palmitate and ascorbyl dipalmitate, ascorbic acid alkyl ether such as ascorbic acid ethyl ether, ascorbic acid glucoside such as ascorbic acid-2-glucoside and Ascorbic acid derivatives such as fatty acid esters and tocopheryl phosphate ascorbyl; vitamin derivatives such as tocopherol nicotinate, tocopherol acetate, tocopherol acetate, tocopherol linoleate, tocopherol phosphate, tocopherol phosphate etc., tocotrienol, and other various vitamin derivatives Is preferable.

  Anti-inflammatory and anti-inflammatory agents include glycyrrhizic acid and its derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, guaiazulene, allantoin, indomethacin, zinc oxide, hydrocortisone acetate, prednisone, diphedramine hydrochloride, chlorpheniramine maleate; peach leaf extract A plant extract such as a koji leaf extract is preferable. Plant growth and tinctures such as assembly extract, red pepper tincture, ginger tincture, ginger extract, cantalis tincture; capsaicin, nonyl acid valenylamide, gingeron, ictamol, tannic acid Borneol, cyclandelate, cinnarizine, trazoline, acetylcholine, verapamil, cephalanthin, γ-oryzanol, cephalanthin, vitamin E and nicotinic acid tocopherol, acetic acid tocopherol and other derivatives, γ-oryzanol, nicotinic acid, nicotinic acid amide, nicotinic acid benzyl Derivatives such as ester, inositol hexanicotinate, nicotine alcohol, allantoin, photosensitizer 301, photosensitizer 401, capronium chloride, pentadecanoic acid monoglyceride, Preferable examples include flavonol derivatives, stigmasterol or stigmasteranol, its glycosides, and minoxidil. Preferred hormones include estradiol, estrone, ethinyl estradiol, cortisone, hydrocortisone, prednisone and the like. Other remedies such as anti-wrinkle agents, anti-aging agents, squeeze agents, cooling sensations, warming sensation agents, wound healing promoters, irritation relievers, analgesics, cell activators include retinols, retinoic acids, retinoin Acid tocopheryl; derivatives such as lactic acid, glycolic acid, gluconic acid, fruit acid, salicylic acid and glycosides / esterified products thereof, α- or such as hydroxycapric acid, long chain α-hydroxy fatty acid, long chain α-hydroxy fatty acid cholesteryl β-hydroxy acids and derivatives thereof; γ-aminobutyric acid, γ-amino-β-hydroxybutyric acid; carnitine; carnosine; creatine; ceramides, sphingosines; caffeine, xanthine and the like; and coenzyme Q10, carotene, lycopene , Astaxanthin, lutein, α-lipoic acid, platinum nanocolloid, fullerenes, etc. Antioxidant / active oxygen scavengers; catechins; flavones such as quercetin; isoflavones; gallic acid and ester sugar derivatives; polyphenols such as tannin, sesamin, protoanthocyanidin, chlorogenic acid, apple polyphenol; rutin and glycosides, etc. Derivatives of hesperidin and glycosides; lignan glycosides; licorice extract-related substances such as grabrizine, glabrene, liquiritin, and isoliquiritin; lactoferrin; shogaol, gingerol; fragrance substances such as menthol, camphor, cedrol, and derivatives thereof Preferred examples include capsaicin, vanillin and the like and derivatives; insect repellents such as diethyltoluamide; and complexes of physiologically active substances and cyclodextrins.

  Plant / animal / microbe extracts include iris extract, ashitaba extract, asunalo extract, asparagus extract, avocado extract, achacha extract, almond extract, altea extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo biloba extract , Incheon extract, Fennel extract, Turmeric extract, Oolong tea extract, Peony extract, Ages extract, Echinacea leaf extract, Enmeo extract, Ogon extract, Oat extract, Auren extract, Barley extract, Panax ginseng extract, Hypericum extract, Odori extract , Dutch mustard extract, orange extract, dried sea water, seaweed extract, oyster leaf extract, oyster extract, hydrolyzed elastin, hydrolyzed wheat powder, hydrolysis Luc, Cascon extract, Chamomile extract, Oil-soluble chamomile extract, Carrot extract, Kawara mugi extract, Oat extract, Calcade extract, Licorice extract, Oil-soluble Licorice extract, Kiwi extract, Kiou extract, Cyprid extract, Quina extract, Cucumber extract, Kiri leaf extract, Guanosine, guava extract, cucumber extract, gardenia extract, kumazasa extract, clara extract, walnut extract, chestnut extract, grapefruit extract, clematis extract, black rice extract, brown sugar extract, black vinegar, chlorella extract, mulberry extract, gentian extract, Gentian pepper extract, tea Extract, yeast extract, kokuboku extract, coffee extract, burdock extract, rice extract, rice fermented extract, rice bran fermented extract, rice germ oil, comfrey extract, Lagen, Cowberry extract, Saishin extract, Psycho extract, Saitai extract, Saffron extract, Salvia extract, Salmon extract, Sasa extract, Hawthorn extract, Sansha extract, Salamander extract, Shiitake extract, Giant extract, Shikon extract, Perilla extract, Linden extract, Shimosukeso Extract, jatoba extract, peonies extract, ginger cucumber extract, ginger root extract, white birch extract, white jellyfish extract, horsetail extract, stevia extract, stevia fermented product, west river willow extract, horse chestnut extract, hawthorn extract, elderberry extract, yarrow extract , Mint extract, sage extract, mallow extract, nematode extract, essence extract, Sakuhakuhi extract, Diou extract, Dai Extract, peanut extract, thyme extract, dandelion extract, lichen extract, tea extract, clove extract, chigaya extract, chimpi extract, tea tree oil, tea tea extract, red pepper extract, red snapper extract, red snapper extract, red spruce extract, red spruce extract, tomato Extract, natto extract, carrot extract, garlic extract, wild rose extract, hibiscus extract, bacmond extract, lotus extract, parsley extract, birch extract, honey, hamamelis extract, parietalia extract, hyacinth extract, bisabolol, cypress extract, bifidobacteria extract, Loquat extract, dandelion extract, burdock extract, bukkuri extract, butcher bloom extract, grape extract, grape seed extract, propolis, loofah extract, Safflower extract, peppermint extract, body extract, button extract, hop extract, squid extract, pine extract, maroonnier extract, mizubasho extract, mukuroji extract, melissa extract, mozuku extract, peach extract, cornflower extract, eucalyptus extract, yukinoshita extract, yuzu extract, lily extract, Yokuinin extract, mugwort extract, lavender extract, green tea extract, eggshell membrane extract, apple extract, rooibos tea extract, litchi extract, lettuce extract, lemon extract, forsythia extract, forsythia extract, rose extract, rosemary extract, roman chamomile extract, royal jelly Extracts such as an extract and a bitumen extract are preferred.

  Examples of the antipruritic agent include diphenhydramine hydrochloride, chlorpheniramine maleate, camphor, substance-P inhibitor, and the like. Examples of the exfoliating / dissolving agent include salicylic acid, sulfur, resorcin, selenium sulfide, pyridoxine and the like. Examples of the antiperspirant include chlorohydroxyaluminum, aluminum chloride, zinc oxide, and zinc paraphenol sulfonate. Examples of the refreshing agent include menthol and methyl salicylate. Examples of the astringent include citric acid, tartaric acid, lactic acid, aluminum sulfate / potassium sulfate, and tannic acid. Examples of enzymes include superoxide dismutase, catalase, lysozyme chloride, lipase, papain, pancreatin, protease, and the like. Preferred nucleic acids include ribonucleic acid and salts thereof, deoxyribonucleic acid and salts thereof, and adenosine triphosphate disodium.

  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, damacenone, 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 of the antibacterial cosmetic or skin external preparation of the present invention include skin external preparations such as hair cosmetics, basic cosmetics, makeup cosmetics, aromatic cosmetics, body cosmetics, and ointments. . The cosmetic / skin external preparation of the present invention can be produced according to a usual method.

  The antibacterial cosmetic or skin external preparation of the present invention will be described in more detail. As hair cosmetics, oil shampoo, cream shampoo, conditioning shampoo, dandruff shampoo, hair color shampoo, rinse integrated shampoo Shampoos such as: rinse, treatment, hair pack, hair foam, hair mousse, hair spray, hair mist, hair wax, hair gel, water grease, set lotion, color lotion, hair tonic, hair liquid, pomade, tic, hair cream, hair blow, Split coat, hair oil, permanent wave agent, straight permanent agent, oxidative hair dye, hair bleach, hair color pretreatment, hair color after treatment, permanent pretreatment, Ma after treatments, hair manicure, and as hair growth agents are preferred.

  Basic cosmetics include soft lotion, astringent lotion, cleansing lotion, multi-layer lotion, etc .; emollient lotion, moisture lotion, milky lotion, nourishing lotion, nourishing milk, skin moisture, moisturizer -Emulsions such as emulsion, massage lotion, cleansing lotion, protect emulsion, sun protect, sun protector, UV care milk, sunscreen, makeup lotion, horny smoother, elbow lotion, hand lotion, body lotion; emollient cream, nutritional cream, nari Thing cream, burnishing cream, moisture cream, night cream, massage cream, cleansing cream, makeup cream, base cream Cream, sun makeup cream, suntan cream, hair removal cream, deodorant cream, shaving cream, keratin softening cream, etc .; gel such as moisture gel; essence such as moisturizing essence, whitening essence, UV protection essence; liposome Liposome cosmetics such as beauty essence and liposome lotion; Peel-off packs, powder packs, washing packs, oil packs, cleansing masks and other packs and masks; cleansing foams, cleansing creams, cleansing milks, cleansing lotions, cleansing gels, cleansing oils , Cleansing mask, washing powder, face washing powder, etc .; cosmetic soap, transparent soap, medicated soap, liquid soap, shaving soap, synthetic cosmetic soap Soap can be mentioned as preferred.

  Examples of makeup cosmetics that may be preferably used include white powder, dusts, foundations, lipsticks, lip gloss, blushers, eyeliner, mascara, eye shadow, eyebrow, eyebrow, nail enamel, enamel remover, and nail treatment.

  Preferred examples of the aromatic cosmetics include perfume, perfume, parfum, eau de parfum, eau de toilette, eau de cologne, perfumes, fragrance powder, perfume soap, body lotion and bath oil.

  Body cosmetics such as body shampoos; deodorant lotions, deodorant powders, deodorant sprays, deodorant sticks and other deodorant cosmetics; decoloring agents, hair removal / hair removal agents; bathing agents; insect repellents A repeller is preferred.

  Moreover, as a skin external preparation, it can be used with dosage forms, such as an ointment, a patch, a lotion agent, a liniment agent, and a liquid coating agent. It can also be used as an oral cosmetic such as toothpaste and mouthwash.

  Examples of the dosage form of the antibacterial cosmetic or skin external preparation of the present invention include an oil-in-water (O / W) type, a water-in-oil (W / O) type, a W / O / W type, and an O / W / O type. Emulsified cosmetics, oily cosmetics, solid cosmetics, liquid cosmetics, kneaded cosmetics, stick cosmetics, volatile oil cosmetics, powder cosmetics, jelly cosmetics, gel cosmetics , Paste-type cosmetics, emulsified polymer-type cosmetics, sheet-type cosmetics, mist-type cosmetics, spray-type cosmetics, and the like are preferable.

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

Example 1 Synthesis of 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester and preparation of antibacterial agent composition containing the same 1, 3 L reactor equipped with stirrer, thermometer and gas introduction pipe was charged with 1, 602 g (3.5 mol) of 4-cyclohexanedicarboxylic acid and 1503 g (11.2 mol) of diethylene glycol monoethyl ether were charged, heated to 150 ° C. to 230 ° C. while blowing nitrogen, and reacted for 33 hours while distilling off water. It was. 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). By adding 0.03% by weight of δ-d-tocopherol to the obtained 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester, stirring and mixing, antibacterial agent composition 1 (1,4- An antibacterial agent composition of 99.97% by weight of cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester and 0.03% by weight of δ-d-tocopherol was obtained.

Example 2 Synthesis of 1,4-cyclohexanedicarboxylic acid bis (triethylene glycol monoethyl ether) ester and preparation of antibacterial composition containing the same In a 300 mL reactor equipped with a stirrer, a thermometer, and a gas introduction tube While charging 55 g (0.32 mol) of 1,4-cyclohexanedicarboxylic acid and 112 g (0.64 mol) of triethylene glycol monoethyl ether, heating to 150 ° C. to 250 ° C. while blowing nitrogen, distilling off water. The reaction was performed for 30 hours, and steam deodorization was performed to obtain 140 g (yield 92%) of the desired 1,4-cyclohexanedicarboxylic acid bis (triethylene glycol monoethyl ether) ester. The ester obtained was a pale yellow liquid with an acid value of 7.7 and a hue Gardner 3. The diester content was 90% from analysis by capillary gas chromatography (FID, area percentage). By adding 0.03% by weight of δ-d-tocopherol to the obtained 1,4-cyclohexanedicarboxylic acid bis (triethylene glycol monoethyl ether) ester, stirring and mixing, antibacterial agent composition 2 (1, An antibacterial agent composition of 99.97% by weight of 4-cyclohexanedicarboxylic acid bis (triethylene glycol monoethyl ether) ester and 0.03% by weight of δ-d-tocopherol was obtained.

Example 3 Synthesis of bis (diethylene glycol monoethyl ether) ester of adipic acid and preparation of antibacterial agent composition containing the same 75 g of adipic acid (0.5 g) in a 300 mL reactor equipped with a stirrer, thermometer and gas introduction tube Mol) and 206.3 g (1.5 mol) of diethylene glycol monoethyl ether, and 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). By adding 0.03% by weight of δ-d-tocopherol to the obtained diester, stirring and mixing, antibacterial agent composition 3 (99.97% by weight of bis (diethylene glycol monoethyl ether) ester adipate, δ− An antibacterial agent composition of 0.03% by weight of d-tocopherol was obtained.

Example 4 Synthesis of glutaric acid bis (diethylene glycol monoethyl ether) ester and preparation of antibacterial agent composition containing the same In a 300 mL reactor equipped with a stirrer, a thermometer, and a gas introduction tube, 66 g (0.5 g) of glutaric acid was added. Mol) and 206.3 g (1.5 mol) of diethylene glycol monoethyl ether, and 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 175 g (yield 96%) of the target diester. The obtained ester was a colorless to pale yellow liquid having an acid value of 4.2 and a hue Gardner of 1 or less. The diester content was 99% from analysis by capillary gas chromatography (FID, area percentage). By adding 0.03% by weight of δ-d-tocopherol to the obtained diester, stirring and mixing, antibacterial agent composition 4 (99.97% by weight of bis (diethylene glycol monoethyl ether) glutarate ester, δ− An antibacterial agent composition of 0.03% by weight of d-tocopherol was obtained.

Comparative Example 1 Synthesis of succinic acid bis (diethylene glycol monoethyl ether) ester and preparation of composition containing the same 90.0 g of succinic anhydride (0. 0 g) in a 300 mL reactor equipped with a stirrer, thermometer and gas introduction pipe. 9 mol) and 362.1 g (2.7 mol) of diethylene glycol monoethyl ether were 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). By adding 0.03% by weight of δ-d-tocopherol to the obtained diester, and stirring and mixing, Comparative Composition 1 (99.97% by weight of bis (diethylene glycol monoethyl ether) succinate), δ- A composition having 0.03% by weight of d-tocopherol was obtained.

Example 5 Evaluation of aqueous solution stability The antibacterial agent compositions 1 to 4 obtained in Examples 1 to 4 of the present invention were evaluated for pH stability in a 1% aqueous solution. As comparative objects, Comparative Example Composition 1 containing succinic acid bis (diethylene glycol monoethyl ether) ester obtained in Comparative Example 1 and commercially available diethoxyethyl succinate were used.
(Evaluation methods)
Each composition and a 1% aqueous solution of diethoxyethyl succinate were prepared and stored in a thermostatic bath at 50 ° C. for 1 week, 2 weeks, and 1 month, and changes in pH were evaluated. The results are shown in Table 1.
(result)
As shown in Table 1, the antibacterial agent composition 1 of the present invention (a composition containing 1,4-cyclohexanedicarboxylic acid bis (diethylene glycol monoethyl ether) ester) and 2 (1,4-cyclohexanedicarboxylic acid bis ( The aqueous solution of the composition containing triethylene glycol monoethyl ether) ester was stable and hardly changed in pH, and was excellent as a composition for cosmetics or external preparations for skin. In addition, the aqueous solution of the antibacterial agent composition 3 (a composition containing bis (diethylene glycol monoethyl ether) ester adipate) has a slight change in pH, but is acceptable as a composition for cosmetics or skin external preparations. It was thought that there was. On the other hand, the pH of the aqueous solution of diethoxyethyl succinate and Comparative Example Composition 1 (composition containing bis (diethylene glycol monoethyl ether) succinate) was greatly reduced by storage and was inferior to the pH of the aqueous solution. It was. Further, the antibacterial agent composition 4 (a composition containing bis (diethylene glycol monoethyl ether) ester of glutaric acid) has better pH stability of the aqueous solution than diethoxyethyl succinate and Comparative Example Composition 1, but the present invention. Compared with the preferable antibacterial agent compositions 1 to 3, it was slightly inferior.

Example 6 Odor Evaluation About the antibacterial agent compositions 1 to 4 obtained in Examples 1 to 4 of the present invention, the odor evaluation was sensorially evaluated by 10 panelists. As a comparison object, phenoxyethanol was used. As a result, the antibacterial agent compositions 1 to 4 had a much lower odor level than phenoxyethanol, and were excellent as compositions for cosmetics or skin external preparations.

（結果）
表２に示した通り、本発明の抗菌組成物１〜４は、比較対象として用いたコハク酸ジエトキシエチルと同等以上の抗菌性を示した。特に、抗菌組成物３、同４は、抗菌剤として汎用されるフェノキシエタノールと同等の高い抗菌性を示した。
（実施例５〜７の結果に関する考察）
実施例５〜７の結果を総合的に評価すると、本発明の本発明の抗菌組成物１〜３は、高い抗菌性を示し、水溶液のｐＨ安定性に優れ、臭いも少ないことから、化粧品又は皮膚外用剤に用いる抗菌剤として特に有用であると判断できる。抗菌組成物４は水溶液のｐＨ安定性に若干の問題があるため、限定的な使用状況では有用と考えられる。一方、比較例組成物１、コハク酸ジエトキシエチル、フェノキシエタノールは、水溶液のｐＨ安定性若しくは臭いに難があった。 Example 7 Evaluation of antibacterial properties The antibacterial properties of the antibacterial agent compositions 1 to 4 obtained in Examples 1 to 4 of the present invention were evaluated by the following methods. As comparison objects, diethoxyethyl succinate and phenoxyethanol were used.
(Antimicrobial evaluation method)
An aqueous solution in which 0.5% peptone and 0.5% yeast extract were allowed to coexist with the antibacterial agent compositions 1 to 4 obtained in Examples 1 to 4 of the present invention, diethoxyethyl succinate, and phenoxyethanol ( 2% by weight, 1% by weight, 0.8% by weight, 0.6% by weight, 0.4% by weight, and 0.2% by weight). After inoculation with Staphylococcus), the change in the number of bacteria by the pour method was observed on day 0 and day 7. The antibacterial evaluation results are shown in Table 2.

(result)
As shown in Table 2, the antibacterial compositions 1 to 4 of the present invention exhibited an antibacterial property equivalent to or higher than that of diethoxyethyl succinate used as a comparison target. In particular, antibacterial compositions 3 and 4 showed high antibacterial properties equivalent to phenoxyethanol, which is widely used as an antibacterial agent.
(Consideration on the results of Examples 5 to 7)
When the results of Examples 5 to 7 are evaluated comprehensively, the antibacterial compositions 1 to 3 of the present invention exhibit high antibacterial properties, are excellent in pH stability of an aqueous solution, and have little odor. It can be judged that it is particularly useful as an antibacterial agent used in a skin external preparation. Since the antibacterial composition 4 has some problems in pH stability of the aqueous solution, it is considered useful in a limited use situation. On the other hand, Comparative Composition 1, Diethoxyethyl succinate and phenoxyethanol had difficulty in pH stability or odor of the aqueous solution.

Hereinafter, various cosmetics or skin external preparations formulated with the antibacterial agent of the present invention will be exemplified. These cosmetics or external preparations for skin had sufficient antibacterial properties.
Example 8 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was not sticky to the touch, gave a moist feeling and was excellent in familiarity with the skin.

Component Blending amount (% by weight)
1 Antimicrobial composition 1 of Example 1 1.20
2 Ascorbyl ethyl 1.00
3 DPG 10.00
4 Citric acid 0.05
5 Na citrate 0.40
6 EDTA-2Na 0.10
7 Purified water Amount to be 100 in total (Preparation method)
No. 1 and 3 were added and stirred and mixed uniformly (part A). Next, no. 2, 4, 5, 6 7 (part B). Part B was added to part A with stirring to make it uniform.

Example 9 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was not sticky to the touch, gave a moist feeling and was excellent in familiarity with the skin.

Component Blending amount (% by weight)
1 Antimicrobial composition 1 of Example 1 2.50
2 Ascorbyl ethyl 1.00
3 BG 7.50
4 Citric acid 0.05
5 Na citrate 0.40
6 Ethanol 8.00
7 EDTA-2Na 0.10
8 Purified water Amount to be 100 in total (preparation method)
No. 1 and 3 were added and stirred and mixed uniformly (part A). Next, no. 2, 4-7. 8 (part B). Part B was added to part A with stirring to make it uniform.

Example 10 Cosmetic liquid A cosmetic liquid having the following formulation was prepared. This essence had sufficient antibacterial properties and was excellent in odor and stability. In addition, the skin was soft and smooth, while maintaining a fresh, smooth and moist skin.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 4.00
2 Ascorbyl ethyl 1.00
3 Glycyrrhizic acid 2K 0.10
4 DPG 15.00
5 Citric acid 0.01
6 Na citrate 0.09
7 Tremoist-TP (Nippon Seika) 0.20
8 Ethanol 5.00
9 EDTA-2Na 0.02
10 Purified water Total amount of 100 (Preparation method)
No. 1, 4, and 8 were added and stirred and mixed uniformly (part A). Next, no. No. 10 in part 7 (part B). No. 2, 3, 5, 6, 9 are the remaining Nos. 10 (part C). To part A, parts B and C were added with stirring to make uniform.

Example 11 Skin Care Cream A skin care cream having the following formulation was prepared. This skin care cream had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was the cream excellent in the effect which provides a moist feeling.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Arbutin 3.00
3 Glycerin 3.00
4 Squalane 3.00
5 Jojoba oil 3.00
6 Palm kernel oil 3.10
7 Glyceryl stearate 2.30
8 PEG-60 glyceryl isostearate 1.40
9 PG (SE) stearate 1.30
10 Stearyl alcohol 3.00
11 Behenyl alcohol 2.00
12 Dimethicone 1.50
13 1,2-hexanediol 0.50
14 Citric acid 0.01
15 Na citrate 0.09
16 Purified water Amount to be 100 in total (preparation method)
No. 1-3, no. 13 to 16 were heated to about 80 ° C. and dissolved uniformly (part A). Next, no. 4 to 12 were heated to about 80 ° C. and dissolved uniformly (part B). A part A was added to part B with stirring and emulsified, and then cooled.

Example 12 Body Soap A body soap having the following formulation was prepared. The body soap has sufficient antibacterial properties and has excellent odor and stability. In addition, the skin could be given a moist and smooth feeling.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Potassium soap base solution (37%) 40.00
3 Laurylmethyl taurine Na 2.00
4 Glyceryl stearate (SE) 1.00
5 Palm kernel oil fatty acid DEA 2.00
6 PEG-8 2.00
7 Tremoist-TP (Nippon Seika) 0.05
8 Lactic acid 3.27
9 EDTA-2Na 0.05
10 Methylparaben 0.02
11 Purified water Total amount of 100 (production method)
No. 1-No. 11 was dissolved by heating at about 80 ° C. and cooled with stirring.

Example 13 Emulsion An emulsion having the following formulation was prepared. This emulsion had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was excellent in the effect which provides a moist feeling.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 5.00
2 Squalane 8.00
3 IOTG (Nippon Seika) 8.00
4 Cetyl dimethicone copolyol 1.00
5 Polyglyceryl-3 diisostearate0.80
6 Polysorbate 40 1.00
7 Glyceryl stearate 1.00
8 Tetraoleic acid Solves-60 1.00
9 Dimethicone (10cs) 4.00
10 BG 6.00
11 Hydrolyzed collagen 0.20
12 Hydrolyzed keratin 0.20
13 Carbomer 0.50
14 Hydroxide K 0.20
15 Purified water Total amount of 100 (Preparation method)
No. 15 is a part of No. 15. No. 13 was added and stirred, then 14 was added to obtain a viscous liquid (Part A). Next, no. 1, 10 and the remaining No. 15 was heated to about 70 ° C. and dissolved (Part B). No. 2 to 9 were heated to about 70 ° C. and dissolved (part C). Part B is added to Part C with stirring and emulsified, and then cooled to about 50 ° C. 11 and 12 were added and stirred until uniform.

Example 14 Cleansing milk A cleansing milk having the following formulation was prepared. This cleansing milk had sufficient antibacterial properties and was excellent in stability. Moreover, since the solubility is excellent, the foundation, makeup and the like are well removed, and an effect such as imparting a refreshing feel can be obtained.

Component Blending amount (% by weight)
1 Antimicrobial composition 1 of Example 1 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 PG stearate (SE) 3.00
8 Propylparaben 0.10
9 Dimethicone 10.00
10 Carbomer 0.10
11 Hydroxide K 0.04
12 EDTA-2Na 0.05
13 Phenoxyethanol 0.20
14 Purified water Total amount to be 100 (Preparation method)
No. 14 is a part of No. 14. No. 10 was added and stirred well. 11 was added to obtain a viscous liquid (Part A). No. 12, 13 and the remaining No. 14 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.

Example 15 Lipstick A lipstick having the following formulation was prepared. This lipstick had sufficient antibacterial properties. The lipstick was fresh and highly adhesive.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 4.00
2 Plandool-G (Nippon Seika) 27.50
3 LUSPLAN DD-DA7 (Nippon Seika) 8.00
4 YOFCO MAS (Nippon Seika) 3.00
5 Neosolute-DE (Nippon Seika) 5.00
6 CIO (Nippon Seika) 15.00
7 IOTG (Nippon Seika) 15.00
8 Cyclomethicone 5.00
9 Ceresin 9.00
10 Candelilla Row 5.00
11 Tocopherol 0.50
12 Iron oxide 1.00
13 Titanium oxide 1.00
14 Mica 1.00
(Preparation method)
No. 1 to 14 was added and mixed uniformly with stirring at about 80 ° C., and then rapidly cooled.

Example 16 Hair mist Hair mist having the following formulation was prepared. This hair mist had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was non-sticky, had a light set-up property, and was able to impart a good feel and smooth fingering to the hair.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Hydrolyzed keratin (25%) 2.00
3 cetrimonium chloride (30%) 0.60
4 Glycerin 5.00
5 Polyquaternium-6 0.80
6 Betaine 0.80
7 Ethanol 20.00
8 Purified water Amount to be 100 in total (preparation method)
Each component was stirred and mixed uniformly.

Example 17 Leave-on treatment A leave-on treatment (for hair) having the following formulation was prepared. This leave-on treatment (for hair) had sufficient antibacterial properties and was excellent in odor and stability. In addition, the hair has a moist feel and can impart softness and slipperiness to the hair.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Hydrolyzed keratin (25%) 2.00
3 Cetrimonium chloride (30%) 3.80
4 Sucraph AG-8 (Nippon Seika) 0.80
5 Glycerin 4.00
6 Polyquaternium-6 0.60
7 Polyquaternium-7 0.40
8 Ethanol 5.00
9 Purified water Amount to be 100 in total (preparation method)
No. 6, 7, 9 were dissolved by heating to about 80 ° C. (part A). No. in part A 1 to 5 was added and dissolved uniformly, and after cooling to about 40 ° C. 8 was added and stirred and mixed uniformly.

Example 18 Hair Essence A hair essence having the following formulation was prepared. This hair essence had sufficient antibacterial properties and was excellent in odor and stability. In addition, the hair has a moist feel and can impart softness and slipperiness to the hair.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 5.00
2 Pentylene glycol 2.00
3 Stearyl trimonium chloride (64%) 4.60
4 Sucraph AG-8 (Nippon Seika) 1.00
5 Zicococomonium chloride (74%) 0.80
6 Lauramide DEA 1.00
7 PEG-60 hydrogenated castor oil 0.80
8 Castor oil 0.20
9 Ethanol 10.00
10 Polyquaternium-10 0.20
11 Purified water Total amount to be 100 (Preparation method)
No. 10 and 11 were heated to about 80 ° C. and dissolved (part A). No. in part A 1 to 8 was added and dissolved uniformly and cooled to about 40 ° C. 9 was added and stirred and mixed uniformly.

Example 19 Skin Care Cream A skin care cream having the following formulation was prepared. This skin care cream had sufficient antibacterial properties and was excellent in odor and stability. Moreover, it was the cream excellent in the effect which provides a moist feeling.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Arbutin 3.00
3 IOTG (Nippon Seika) 3.00
4 Squalane 3.00
6 Palm kernel oil 2.50
7 Glyceryl stearate 1.80
8 PEG-60 glyceryl isostearate 1.10
9 PG (SE) stearate 1.00
10 Stearyl alcohol 1.20
11 Behenyl alcohol 1.70
12 Dimethicone 1.50
13 δ-Tocopherol 0.10
14 Glycerin 2.00
15 Citric acid 0.01
16 Na citrate 0.09
17 Purified water Amount to be 100 in total (preparation method)
No. 1-2, no. 14-17 was heated to about 80 ° C. and dissolved uniformly (part A). Next, no. 3 to 13 were heated to about 80 ° C. and dissolved uniformly (part B). A part A was added to part B with stirring and emulsified, and then cooled.

Example 20 Shampoo A shampoo having the following formulation was prepared. This shampoo had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 1 of Example 1 3.00
2 Laureth sulfate Na (27%) 30.00
3 Cocamidopropyl betaine 10.00
4 Lauramide MIPA 1.50
5 PPG-2 cocamide 0.20
6 Polyquaternium-10 0.20
7 Glycolic acid (50%) Appropriate amount 8 Na hydroxide (10%) Appropriate amount 9 Purified water Total amount to be 100 (Preparation method)
No. 6 and 9 were heated to about 80 ° C. and dissolved. Here, no. 1-5 were added and dissolved uniformly. Cool to room temperature. 7 and 8 were used to adjust the pH to 6.4 to 6.8.

Example 21 Cream rinse A cream rinse having the following formulation was prepared. This cream rinse had sufficient antibacterial properties and had excellent odor and stability.

Component Blending amount (% by weight)
A
Antibacterial composition 1 of Example 1 2.50
Stearic acid diethylaminoethylamide 3.00
Phosphoric acid 0.80
Cetanol 4.00
Triethylhexanoin 2.00
BG 7.50
B
Hydrolyzed wheat protein (25%) 1.50
C
Purified water Total amount to be 100 (Preparation method)
A component was heated and melt | dissolved in 80 degreeC (A part). C component was heated to 80 degreeC (C part). To part A, part C was added with stirring and emulsified. Stirring was continued, B component was added at about 50 degreeC, stirring was stopped at 40-35 degreeC, and it stood to cool.

Example 22 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 1 of Example 1 2.00
2 Ascorbyl glucoside 2.00
3 Ethanol 15.00
4 PEG-60 hydrogenated castor oil 0.20
5 Tocopherol 0.05
6 Carbomer 0.05
7 AMP 0.04
8 EDTA-3Na 0.05
9 Purified water Amount to be 100 in total (preparation method)
No. 1, 3-5 were added and dissolved uniformly (part A). No. A part of 6, 7, 9 was mixed and stirred to obtain a viscous liquid (Part B). No. 2, 8 and the remaining 9 were added and dissolved uniformly, and A part and B part were added and stirred to make uniform.

Example 23 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
Antibacterial composition 1 of Example 1 3.00
Ascorbyl ethyl 1.00
DPG 7.00
Citric acid 0.01
Na citrate 0.09
Glycyrrhizin K2 0.10
EDTA-2Na 0.05
Purified water Total amount to be 100 (Preparation method)
All ingredients were mixed and stirred until uniform.

Example 24 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
Antibacterial composition 1 of Example 1 1.40
Ascorbyl ethyl 1.00
Ethylhexanoic acid glycerin 0.20
Citric acid 0.01
Na citrate 0.09
Glycyrrhizin K2 0.10
EDTA-2Na 0.05
Purified water Total amount to be 100 (Preparation method)
All ingredients were mixed and stirred until uniform.

Example 25 Emulsion An emulsion having the following formulation was prepared. This emulsion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
A
Polyglyceryl myristate-10 2.10
Hydrogenated soybean phospholipid 0.60
Stearic acid 0.50
Behenyl alcohol 1.60
Cetyl palmitate 0.60
Hydrogenated polydecene 6.00
Cetyl ethylhexanoate 6.00
Triethylhexanoin 6.00
B
Antibacterial composition 1 of Example 1 4.00
Caprylyl glycol 0.20
Amount C of purified water totaling 100
Carbomer 0.10
Hydroxide Na 0.04
Purified water 14.86
(Preparation method)
C component was mixed and stirred to give a viscous liquid (part C). A component was heated and melt | dissolved in 80 degreeC (A part). B component was heated to 80 degreeC (B part). After part B was added to part A with stirring and emulsified, part C was added, stirring was continued, stirring was stopped at 40 to 35 ° C., and the mixture was allowed to cool.

Example 26 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 1.00
2 Ascorbyl ethyl 1.00
3 DPG 10.00
4 Citric acid 0.05
5 Na citrate 0.40
6 EDTA-2Na 0.10
7 Purified water Amount to be 100 in total (Preparation method)
No. 1 and 3 were added and stirred and mixed uniformly (part A). Next, no. 2, 4, 5, 6 7 (part B). Part B was added to part A with stirring to make it uniform.

Example 27 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 2 of Example 2 2.50
2 Ascorbyl ethyl 1.00
3 BG 7.50
4 Citric acid 0.05
5 Na citrate 0.40
6 Ethanol 8.00
7 EDTA-2Na 0.10
8 Purified water Amount to be 100 in total (preparation method)
No. 1 and 3 were added and stirred and mixed uniformly (part A). Next, no. 2, 4-7. 8 (part B). Part B was added to part A with stirring to make it uniform.

Example 28 Cosmetic liquid A cosmetic liquid having the following formulation was prepared. This beauty serum had sufficient antibacterial properties.

Component Blending amount (% by weight)
1 Antibacterial agent composition 4 of Example 4 2.00
2 Ascorbyl ethyl 1.00
3 Glycyrrhizic acid 2K 0.10
4 DPG 15.00
5 Citric acid 0.01
6 Na citrate 0.09
7 Tremoist-TP (Nippon Seika) 0.20
8 Ethanol 5.00
9 EDTA-2Na 0.02
10 Purified water Total amount of 100 (Preparation method)
No. 1, 4, and 8 were added and stirred and mixed uniformly (part A). Next, no. No. 10 is part of No. 10. 7 (part B). No. 2, 3, 5, 6, 9 are the remaining Nos. 10 (part C). To part A, parts B and C were added with stirring to make uniform.

Example 29 Skin Care Cream A skin care cream having the following formulation was prepared. This skin care cream had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 1.00
2 Arbutin 3.00
3 Glycerin 3.00
4 Squalane 3.00
5 Jojoba oil 3.00
6 Palm kernel oil 3.10
7 Glyceryl stearate 2.30
8 PEG-60 glyceryl isostearate 1.40
9 PG (SE) stearate 1.30
10 Stearyl alcohol 3.00
11 Behenyl alcohol 2.00
12 Dimethicone 1.50
13 1,2-hexanediol 0.50
14 Citric acid 0.01
15 Na citrate 0.09
16 Purified water Amount to be 100 in total (preparation method)
No. 1-3, no. 13 to 16 were heated to about 80 ° C. and dissolved uniformly (part A). Next, no. 4 to 12 were heated to about 80 ° C. and dissolved uniformly (part B). A part A was added to part B with stirring and emulsified, and then cooled.

Example 30 Body Soap A body soap having the following formulation was prepared. The body soap has sufficient antibacterial properties and has excellent odor and stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 3 of Example 3 1.20
2 Potassium soap base solution (37%) 40.00
3 Laurylmethyl taurine Na 2.00
4 Glyceryl stearate (SE) 1.00
5 Palm kernel oil fatty acid DEA 2.00
6 PEG-8 2.00
7 Tremoist-TP (Nippon Seika) 0.05
8 Lactic acid 3.27
9 EDTA-2Na 0.05
10 Methylparaben 0.02
11 Purified water Total amount of 100 (production method)
No. 1-No. 11 was dissolved by heating at about 80 ° C. and cooled with stirring.

Example 31 Emulsion An emulsion having the following formulation was prepared. This emulsion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 5.00
2 Squalane 8.00
3 IOTG (Nippon Seika) 8.00
4 Cetyl dimethicone copolyol 1.00
5 Polyglyceryl-3 diisostearate0.80
6 Polysorbate 40 1.00
7 Glyceryl stearate 1.00
8 Tetraoleic acid Solves-60 1.00
9 Dimethicone (10cs) 4.00
10 BG 6.00
11 Hydrolyzed collagen 0.20
12 Hydrolyzed keratin 0.20
13 Carbomer 0.50
14 Hydroxide K 0.20
15 Purified water Total amount of 100 (Preparation method)
No. 15 is a part of No. 15. No. 13 was added and stirred, then 14 was added to obtain a viscous liquid (Part A). Next, no. 1, 10 and the remaining No. 15 was heated to about 70 ° C. and dissolved (Part B). No. 2 to 9 were heated to about 70 ° C. and dissolved (part C). Part B is added to Part C with stirring and emulsified, and then cooled to about 50 ° C. 11 and 12 were added and stirred until uniform.

Example 32 Cleansing milk A cleansing milk having the following formulation was prepared. This cleansing milk had sufficient antibacterial properties and was excellent in stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 3 of Example 3 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 PG stearate (SE) 3.00
8 Propylparaben 0.10
9 Dimethicone 10.00
10 Carbomer 0.10
11 Hydroxide K 0.04
12 EDTA-2Na 0.05
13 Phenoxyethanol 0.20
14 Purified water Total amount to be 100 (Preparation method)
No. 14 is a part of No. 14. No. 10 was added and stirred well. 11 was added to obtain a viscous liquid (Part A). No. 12, 13 and the remaining No. 14 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.

Example 33 Lipstick A lipstick having the following formulation was prepared. This lipstick had sufficient antibacterial properties. The lipstick was fresh and highly adhesive.

Component Blending amount (% by weight)
1 Antibacterial agent composition 2 of Example 2 4.00
2 Plandool-G (Nippon Seika) 27.50
3 LUSPLAN DD-DA7 (Nippon Seika) 8.00
4 YOFCO MAS (Nippon Seika) 3.00
5 Neosolute-DE (Nippon Seika) 5.00
6 CIO (Nippon Seika) 15.00
7 IOTG (Nippon Seika) 15.00
8 Cyclomethicone 5.00
9 Ceresin 9.00
10 Candelilla Row 5.00
11 Tocopherol 0.50
12 Iron oxide 1.00
13 Titanium oxide 1.00
14 Mica 1.00
(Preparation method)
No. 1 to 14 was added and mixed uniformly with stirring at about 80 ° C., and then rapidly cooled.

Example 34 Hair mist Hair mist having the following formulation was prepared. This hair mist had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 3 of Example 3 1.50
2 Hydrolyzed keratin (25%) 2.00
3 cetrimonium chloride (30%) 0.60
4 Glycerin 5.00
5 Polyquaternium-6 0.80
6 Betaine 0.80
7 Ethanol 20.00
8 Purified water Amount to be 100 in total (preparation method)
Each component was stirred and mixed uniformly.

Example 35 Leave-on treatment A leave-on treatment (for hair) having the following formulation was prepared. This leave-on treatment (for hair) had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 3 of Example 3 1.50
2 Hydrolyzed keratin (25%) 2.00
3 Cetrimonium chloride (30%) 3.80
4 Sucraph AG-8 (Nippon Seika) 0.80
5 Glycerin 4.00
6 Polyquaternium-6 0.60
7 Polyquaternium-7 0.40
8 Ethanol 5.00
9 Purified water Amount to be 100 in total (preparation method)
No. 6, 7, 9 were dissolved by heating to about 80 ° C. (part A). No. in part A 1 to 5 was added and dissolved uniformly, and after cooling to about 40 ° C. 8 was added and stirred and mixed uniformly.

Example 36 Hair Essence A hair essence having the following formulation was prepared. This hair essence had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antimicrobial composition 3 of Example 3 3.00
2 Pentylene glycol 2.00
3 Stearyl trimonium chloride (64%) 4.60
4 Sucraph AG-8 (Nippon Seika) 1.00
5 Zicococomonium chloride (74%) 0.80
6 Lauramide DEA 1.00
7 PEG-60 hydrogenated castor oil 0.80
8 Castor oil 0.20
9 Ethanol 10.00
10 Polyquaternium-10 0.20
11 Purified water Total amount to be 100 (Preparation method)
No. 10 and 11 were heated to about 80 ° C. and dissolved (part A). No. in part A 1 to 8 was added and dissolved uniformly and cooled to about 40 ° C. 9 was added and stirred and mixed uniformly.

Example 37 Skin Care Cream A skin care cream having the following formulation was prepared. This skin care cream had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 1.00
2 Arbutin 3.00
3 IOTG (Nippon Seika) 3.00
4 Squalane 3.00
6 Palm kernel oil 2.50
7 Glyceryl stearate 1.80
8 PEG-60 glyceryl isostearate 1.10
9 PG (SE) stearate 1.00
10 Stearyl alcohol 1.20
11 Behenyl alcohol 1.70
12 Dimethicone 1.50
13 δ-Tocopherol 0.10
14 Glycerin 2.00
15 Citric acid 0.01
16 Na citrate 0.09
17 Purified water Amount to be 100 in total (preparation method)
No. 1-2, no. 14-17 was heated to about 80 ° C. and dissolved uniformly (part A). Next, no. 3 to 13 were heated to about 80 ° C. and dissolved uniformly (part B). A part A was added to part B with stirring and emulsified, and then cooled.

Example 38 Shampoo A shampoo having the following formulation was prepared. This shampoo had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 2.00
2 Laureth sulfate Na (27%) 30.00
3 Cocamidopropyl betaine 10.00
4 Lauramide MIPA 1.50
5 PPG-2 cocamide 0.20
6 Polyquaternium-10 0.20
7 Glycolic acid (50%) Appropriate amount 8 Na hydroxide (10%) Appropriate amount 9 Purified water Total amount to be 100 (Preparation method)
No. 6 and 9 were heated to about 80 ° C. and dissolved. Here, no. 1-5 were added and dissolved uniformly. Cool to room temperature. 7 and 8 were used to adjust the pH to 6.4 to 6.8.

Example 39 Cream rinse A cream rinse having the following formulation was prepared. This cream rinse had sufficient antibacterial properties and had excellent odor and stability.

Component Blending amount (% by weight)
A
Antibacterial composition 3 of Example 3 1.50
Stearic acid diethylaminoethylamide 3.00
Phosphoric acid 0.80
Cetanol 4.00
Triethylhexanoin 2.00
BG 7.50
B
Hydrolyzed wheat protein (25%) 1.50
C
Purified water Total amount to be 100 (Preparation method)
A component was heated and melt | dissolved in 80 degreeC (A part). C component was heated to 80 degreeC (C part). To part A, part C was added with stirring and emulsified. Stirring was continued, B component was added at about 50 degreeC, stirring was stopped at 40-35 degreeC, and it stood to cool.

Example 40 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
1 Antibacterial agent composition 3 of Example 3 1.00
2 Ascorbyl glucoside 2.00
3 Ethanol 15.00
4 PEG-60 hydrogenated castor oil 0.20
5 Tocopherol 0.05
6 Carbomer 0.05
7 AMP 0.04
8 EDTA-3Na 0.05
9 Purified water Amount to be 100 in total (preparation method)
No. 1, 3-5 were added and dissolved uniformly (part A). No. A part of 6, 7, 9 was mixed and stirred to obtain a viscous liquid (Part B). No. 2, 8 and the remaining 9 were added and dissolved uniformly, and A part and B part were added and stirred to make uniform.

Example 41 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
Antibacterial composition 3 of Example 3 3.00
Ascorbyl ethyl 1.00
DPG 7.00
Citric acid 0.01
Na citrate 0.09
Glycyrrhizin K2 0.10
EDTA-2Na 0.05
Purified water Total amount to be 100 (Preparation method)
All ingredients were mixed and stirred until uniform.

Example 42 Lotion Toner lotion having the following formulation was prepared. This lotion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
Antibacterial composition 3 of Example 3 1.40
Ascorbyl ethyl 1.00
Ethylhexanoic acid glycerin 0.20
Citric acid 0.01
Na citrate 0.09
Glycyrrhizin K2 0.10
EDTA-2Na 0.05
Purified water Total amount to be 100 (Preparation method)
All ingredients were mixed and stirred until uniform.

Example 43 Emulsion An emulsion having the following formulation was prepared. This emulsion had sufficient antibacterial properties and was excellent in odor and stability.

Component Blending amount (% by weight)
A
Polyglyceryl myristate-10 2.10
Hydrogenated soybean phospholipid 0.60
Stearic acid 0.50
Behenyl alcohol 1.60
Cetyl palmitate 0.60
Hydrogenated polydecene 6.00
Cetyl ethylhexanoate 6.00
Triethylhexanoin 6.00
B
Antibacterial composition 3 of Example 3 4.00
Caprylyl glycol 0.20
Amount C of purified water totaling 100
Carbomer 0.10
Hydroxide Na 0.04
Purified water 14.86
(Preparation method)
C component was mixed and stirred to give a viscous liquid (part C). A component was heated and melt | dissolved in 80 degreeC (A part). B component was heated to 80 degreeC (B part). After part B was added to part A with stirring and emulsified, part C was added, stirring was continued, stirring was stopped at 40 to 35 ° C., and the mixture was allowed to cool.

According to the present invention, it is possible to obtain an antibacterial agent having excellent properties that are excellent in safety, have little odor, have good pH stability in an aqueous solution system, and do not emit harmful substances even when hydrolyzed. Moreover, the antimicrobial cosmetics or skin external preparation excellent in safety | security and stability can be obtained by mix | blending this.

Claims (8)

An antibacterial agent 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 3 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 antibacterial agent according to claim 1, wherein R2 of the polyoxyethylene monoalkyl ether represented by Chemical formula 2 is a methyl group or an ethyl group.   The antibacterial agent according to claim 1, 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.   The antibacterial agent according to any one of claims 1 to 3, wherein R1 of the dicarboxylic acid represented by Chemical Formula 1 is a linear, branched or cyclic hydrocarbon group having 3 to 6 carbon atoms.   The antimicrobial agent according to any one of claims 1 to 3, wherein the dicarboxylic acid represented by Chemical Formula 1 is one or more selected from adipic acid, pimelic acid, suberic acid, and cyclohexanedicarboxylic acid.   The antimicrobial agent according to any one of claims 1 to 3, wherein the dicarboxylic acid represented by Chemical Formula 1 is cyclohexanedicarboxylic acid. The antibacterial cosmetics or skin external preparation containing the antibacterial agent in any one of Claims 1-6. An antibacterial cosmetic or skin external preparation containing the antibacterial agent according to any one of claims 1 to 6, and one or more selected from phenoxyethanol, 1,2-alkanediol, and alkyl glyceryl ether.