JP7412975B2 - Antibacterial composition, cosmetic composition containing the antibacterial composition, and method for improving antibacterial properties of glyceryl ether compositions - Google Patents

Description

The present invention relates to an antibacterial composition and a cosmetic composition having high antibacterial properties.

Antibacterial agents and antifungal agents are usually used in cosmetics for purposes such as preservative purposes. Parabens have been used as such antibacterial agents, but in recent years, the number of people who have allergic reactions to parabens has increased, so it is possible to reduce the amount of parabens or replace them with parabens that are safe for the human body. There was a need for a highly effective antibacterial agent.

In recent years, it has been reported that diol compounds such as alkanediols and alkyl glyceryl ethers and mixtures thereof can be used as antibacterial agents. Patent Document 1 discloses an antibacterial agent comprising a diol compound having a residue obtained by removing one hydroxyl group from a trihydric or higher alcohol. Patent Document 2 discloses an antibacterial agent characterized by α-monoalkylglyceryl ether. Patent Document 3 discloses a cosmetic containing water, an oil-soluble component, and hexylglyceryl ether. Patent Document 4 discloses an antibacterial composition containing an alkanediol compound, a glyceryl ether compound, and a cationized β-glucan. These compositions are said to have good performance as antibacterial agents while being highly safe for the human body because they do not use parabens.

Japanese Patent Application Publication No. 2007-016018 Japanese Patent Application Publication No. 2004-043336 Japanese Patent Application Publication No. 2011-057647 Japanese Patent Application Publication No. 2014-005209

However, although these antibacterial agents are highly safe for the human body, they may not have sufficient antibacterial properties against bacteria and fungi, or they may need to be used in large amounts when used in cosmetics. , the market desired improved antibacterial performance. Therefore, an object of the present invention is to provide an antibacterial composition having high antibacterial properties.

Therefore, the present inventors conducted extensive studies and found an antibacterial composition that exhibits high antibacterial properties by combining specific compounds to exhibit a synergistic effect, leading to the present invention. That is, the present invention provides monoalkyl glyceryl ethers having a linear alkyl group having 6 to 8 carbon atoms, monoalkyl glyceryl ethers having a branched alkyl group having 6 to 8 carbon atoms, and alicyclic alkyl ethers having 6 to 8 carbon atoms. a glyceryl ether composition (A) consisting of two or more selected from the group consisting of monoalkyl glyceryl ethers having a group, and at least one cationic polymer (B), wherein the glyceryl ether composition (A) and the cationic The antibacterial composition has a content ratio of polymer (B) in a mass ratio of 60:40 to 99:1.

According to the present invention, it is possible to provide an antibacterial composition and a cosmetic composition that are highly safe for the human body and have high antibacterial properties. Furthermore, the antibacterial composition of the present invention can be used as an antibacterial agent that can reduce the amount of parabens that have conventionally been frequently used in cosmetics or replace part or all of parabens.

The glyceryl ether composition (A) used in the present invention comprises a monoalkyl glyceryl ether having a linear alkyl group having 6 to 8 carbon atoms, a monoalkyl glyceryl ether having a branched alkyl group having 6 to 8 carbon atoms, and a monoalkyl glyceryl ether having a branched alkyl group having 6 to 8 carbon atoms. It consists of two or more types selected from the group consisting of monoalkyl glyceryl ethers having 6 to 8 alicyclic alkyl groups. If the alkyl group of each monoalkyl glyceryl ether has less than 6 carbon atoms, its antibacterial properties will be lowered, making it unsuitable for actual use. On the other hand, if the number of carbon atoms exceeds 8, antibacterial properties may decrease and skin irritation may become stronger. Furthermore, since the solubility in water deteriorates, it becomes difficult to incorporate the aqueous solution into products. In the present invention, from the viewpoint of exhibiting high antibacterial properties due to a synergistic effect with the cationic polymer (B), monoalkyl glyceryl ethers having one or more types of straight chain alkyl groups having 6 to 8 carbon atoms are preferred. and monoalkylglyceryl ether having one or more C6-C8 alicyclic alkyl groups, monoalkylglyceryl ether having a C6 linear alkyl group and C6 alicyclic It is even more preferable to include a monoalkyl glyceryl ether having an alkyl group.

Note that examples of the monoalkylglyceryl ether having a straight-chain alkyl group having 6 to 8 carbon atoms include monohexylglyceryl ether, monoheptylglyceryl ether, and monooctylglyceryl ether. Examples of the monoalkylglyceryl ether having a branched alkyl group having 6 to 8 carbon atoms include monomethylpentylglyceryl ether, monomethylhexylglyceryl ether, monoethylhexylglyceryl ether, and monodimethylhexylglyceryl ether. Monoalkylglyceryl ethers having an alicyclic alkyl group having 6 to 8 carbon atoms include monocyclohexylglyceryl ether, monomethylcyclohexylglyceryl ether, monodimethylcyclohexylglyceryl ether, monoethylcyclohexylglyceryl ether, monocycloheptylglyceryl ether, and monocyclooctyl. Examples include glyceryl ether.

In the glyceryl ether composition (A) used in the present invention, a monoalkyl glyceryl ether having a linear alkyl group having 6 to 8 carbon atoms, a monoalkyl glyceryl ether having a branched alkyl group having 6 to 8 carbon atoms, and a monoalkyl glyceryl ether having a branched alkyl group having 6 to 8 carbon atoms; The content ratio of two or more types selected from the group consisting of monoalkyl glyceryl ethers having 6 to 8 alicyclic alkyl groups is not particularly limited, but from the viewpoint of improving antibacterial properties due to a synergistic effect, The content of glyceryl ether relative to the total amount of glyceryl ether composition (A) is preferably 10 to 90% by mass, more preferably 20 to 80% by mass. Further, for example, as the glyceryl ether composition (A), one or more monoalkyl glyceryl ethers having a linear alkyl group having 6 to 8 carbon atoms and a monoalkyl glyceryl ether having an alicyclic alkyl group having 6 to 8 carbon atoms may be used. When using one or more of the following, from the viewpoint of improving antibacterial properties due to a synergistic effect, the monoalkyl glyceryl ether having a straight chain alkyl group having 6 to 8 carbon atoms and the monoalkyl glyceryl ether having a straight chain alkyl group having 6 to 8 carbon atoms in the glyceryl ether composition (A) The content ratio of monoalkylglyceryl ether having an alicyclic alkyl group is preferably 10:90 to 80:20, more preferably 20:80 to 60:40, and 20:20 by mass. Even more preferably the ratio is 80 to 40:60.

The cationic polymer (B) used in the present invention is not particularly limited as long as it is a homopolymer of a monomer having a cationic group in the molecule or a copolymer of a monomer having a cationic group in the molecule and another monomer, but for example, , Polyquaternium-1, Polyquaternium-2, Polyquaternium-4, Polyquaternium-5, Polyquaternium-6, Polyquaternium-7, Polyquaternium-10, Polyquaternium-11, Polyquaternium-16, Polyquaternium-22, Polyquaternium-24, Polyquaternium-28, Polyquaternium -30, Polyquaternium-32, Polyquaternium-33, Polyquaternium-37, Polyquaternium-39, Polyquaternium-43, Polyquaternium-44, Polyquaternium-46, Polyquaternium-47, Polyquaternium-48, Polyquaternium-51, Polyquaternium-53, Polyquaternium-54 , Polyquaternium-55, Polyquaternium-56, Polyquaternium-57, Polyquaternium-59, Polyquaternium-61, Polyquaternium-63, Polyquaternium-64, Polyquaternium-65, Polyquaternium-66, Polyquaternium-67, Polyquaternium-68, Polyquaternium-69, Polyquaternium -70, Polyquaternium-72, Polyquaternium-73, Polyquaternium-76, Polyquaternium-77, Polyquaternium-84, Polyquaternium-85, Polyquaternium-86, Polyquaternium-87, Polyquaternium-90, Polyquaternium-92, Polyquaternium-94, Colohahydroxypropyl Examples include polymers of quaternary ammonium salts such as trimonium chloride, gular hydroxypropyltrimonium chloride, Caesarpinia spinosa hydroxypropyltrimonium chloride, and locust bean hydroxypropyltrimonium chloride, and one or more of these may be used. Can be used. Among these, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-22, polyquaternium-37, At least one selected from the group consisting of polyquaternium-39, polyquaternium-47, polyquaternium-51, and polyquaternium-53 is preferred, and polyquaternium-6, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-47, and polyquaternium-53. More preferably, at least one selected from the group consisting of Polyquaternium-51, Polyquaternium-51, and Polyquaternium-53, and at least one selected from the group consisting of Polyquaternium-6, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-47, and Polyquaternium-53. One kind is even more preferred, and at least one kind selected from the group consisting of polyquaternium-6 and polyquaternium-7 is particularly preferred.

Although the molecular weight of the cationic polymer (B) used in the present invention is not particularly limited, the weight average of the cationic polymer (B) is The molecular weight is preferably 10,000 to 5,000,000, more preferably 100,000 to 2,000,000. The weight average molecular weight is measured by gel permeation chromatography (GPC) and calculated in terms of styrene.

The antibacterial composition of the present invention includes a glyceryl ether composition (A) and a cationic polymer (B), and the content ratio of the glyceryl ether composition (A) and the cationic polymer (B) is a mass ratio. It is an antibacterial composition with a ratio of 60:40 to 99:1. In the present invention, by containing the glyceryl ether composition (A) and the cationic polymer (B) in a specific ratio, a specific synergistic effect can be achieved by the combination of the glyceryl ether composition (A) and the cationic polymer (B). and can exhibit high antibacterial properties. From the viewpoint of further enhancing antibacterial properties due to synergistic effects, the antibacterial composition of the present invention has a content ratio of glyceryl ether composition (A) and cationic polymer (B) of 70:30 to 70:30 by mass ratio. The ratio is preferably 95:5, more preferably 80:20 to 92:8, and even more preferably 85:15 to 91:9.

The antibacterial composition of the present invention can be used for the same purposes as known antibacterial agents, antifungal agents, disinfectants, and disinfectants, such as cosmetics, medical cleaning agents, household cleaning agents, The antibacterial composition of the present invention can be used in cleaning agents for the food industry, antibacterial agents for antibacterial processing of synthetic resins and daily necessities, water-based or non-aqueous paints, medical softeners, etc. However, the antibacterial composition of the present invention is not safe for the human body. Since it is expensive, it can be suitably used in cosmetics and other products that come into direct contact with the human body.

The method of using the antibacterial composition of the present invention is not particularly limited, and includes, for example, a method of spraying it on the object to be antibacterially treated, a method of applying it, a method of applying it to the object after impregnating it with a base cloth, etc. A method of impregnating the object with the agent, a method of immersing the object, a method of blending it at the time of molding or preparing the object, etc. can be used. Further, the antibacterial composition of the present invention may be composed only of the glyceryl ether composition (A) and the cationic polymer (B) at the time of preparation, storage, and use, which inhibits the effects of the present invention. Depending on the intended use, other components such as a solvent (for example, water, ethanol, propanol, isopropanol, etc.) may be included within the range.

The cosmetic composition of the present invention is a cosmetic composition containing the antibacterial composition described above. Examples of such cosmetic compositions include facial cleansing cream, facial cleansing foam, cleansing cream, cleansing milk, cleansing lotion, massage cream, cold cream, moisture cream, shaving cream, sunscreen cream, hair tonic, hair cream, hair liquid, and set. Lotion, hair bleach, color rinse, permanent wave liquid, hand cream, lipstick, various packs, foundation, lotion, cosmetic lotion, milky lotion, cologne, nail cosmetics, liquid chemicals for sanitary products such as wet tissues and antibacterial sheets, etc. It will be done.

The amount of the antibacterial composition in the cosmetic composition of the present invention is not particularly limited as long as it can exhibit the desired antibacterial properties, and can be adjusted as appropriate depending on the intended use. From the viewpoint of achieving both, the content of the glyceryl ether composition (A) is preferably 0.02 to 10% by mass, and preferably 0.05 to 5% by mass, based on the total mass of the cosmetic composition. is more preferable, and even more preferably 0.1 to 3% by mass. At this time, from the viewpoint of effectively achieving both antibacterial properties and safety of the cosmetic composition by specifically enhancing the antibacterial properties of the glyceryl ether composition (A), the content of the cationic polymer (B) is preferably 0.01 to 6% by mass, more preferably 0.03 to 3% by mass, and even more preferably 0.05 to 2% by mass, based on the total mass of the cosmetic composition. more preferred.

The cosmetic composition of the present invention has various properties (solubility, dispersibility, stability, Other ingredients may be included to improve and modify properties (e.g., properties, usability, applicability, permeability, moisturizing properties, safety, design properties, optical properties, aromatic properties, whitening properties, etc.), such as powder components, Liquid oil, solid oil, wax, hydrocarbon, higher fatty acid, higher alcohol, ester, silicone, anionic surfactant, cationic surfactant (excluding cationic polymer (B)), amphoteric surfactant, nonionic surfactant agents, humectants, water-soluble polymers, chelating agents, lower alcohols, polyhydric alcohols (excluding each component of glyceryl ether composition (A)), monosaccharides, oligosaccharides, polysaccharides, amino acids, organic amines, polymer emulsions , a pH adjuster, a skin nutrient, a vitamin, an antioxidant, etc., or two or more of them may be appropriately blended as needed. In addition, in the following, "POE" represents "polyoxyethylene" and "POP" represents "polyoxypropylene."

Examples of powder components include inorganic powders (such as talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, rhodochite, biotite, permiculite, magnesium carbonate, calcium carbonate, and silicic acid). Aluminum, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluoroapatite, hydroxyapatite, ceramic powder , metal soaps (e.g. zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc.); organic powders (e.g. polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene and acrylic acid copolymer resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.); Inorganic white pigments (e.g., titanium dioxide, zinc oxide, etc.); Inorganic red pigments (e.g., iron oxide ( Inorganic brown pigments (e.g., γ-iron oxide, etc.); Inorganic yellow pigments (e.g., yellow iron oxide, ocher, etc.); Inorganic black pigments (e.g., black iron oxide, titanium suboxide, etc.); inorganic purple pigments (e.g., manganese violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, Pearl pigments (e.g. titanium oxide coated mica, titanium oxide coated bismuth oxychloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, fish scale foil, etc.); Metal powder pigments (e.g. aluminum powder, copper powder, etc.); organic pigments such as zirconium, barium or aluminum lake (for example, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red No. 226, Red No. 228, Red No. 405, Organic pigments such as Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401, and Blue No. 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 No. 3, Blue No. 1, etc.); natural pigments (for example, chlorophyll, β-carotene, etc.), and the like.

Examples of liquid oils include avocado oil, camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, sasanqua oil, castor oil, and linseed oil. , safflower oil, cottonseed oil, eno oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, Japanese tung oil, Japanese tung oil, jojoba oil, germ oil, triglycerin, and the like.
Examples of solid fats and oils include cacao butter, coconut oil, hydrogenated coconut oil, palm oil, palm kernel oil, Japanese oak kernel oil, hydrogenated oil, Japanese oak oil, and hydrogenated castor oil.

Examples of the wax include beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, privet wax, spermaceti wax, montan wax, bran wax, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugar cane wax, isopropyl lanolin fatty acid, hexyl laurate, reduced lanolin, Examples include Jojoba wax, hard lanolin, shellac wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether, and the like.
Examples of the hydrocarbon oil include liquid paraffin, ozokerite, squalane, pristane, paraffin, ceresin, squalene, vaseline, and microcrystalline wax.

Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linoleic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid. (DHA) and the like.

Examples of higher alcohols include straight chain alcohols (for example, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, etc.); branched chain alcohols (for example, 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, octyldodecanol, etc.).

Examples of ester oils include isopropyl myristate, cetyl octoate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, cetyl lactate, and lactic acid. Myristyl, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl 12-hydroxystearate, glyceryl di-2-ethylhexanoate, dipentaerythritol fatty acid ester, glyceryl monoisostearate, neopentyl glycol dicaprate, diisomalate Stearyl, glyceryl di-2-heptylundecanoate, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, pentaerythritol tetra-2-ethylhexanoate, glyceryl tri-2-ethylhexanoate, trioctanoic acid Glyceryl, glyceryl triisopalmitate, trimethylolpropane triisostearate, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, glyceryl trimyristate, glyceryl tri-2-heptylundecanoate, castor oil fatty acid methyl ester, olein Acid oleyl, acetoglyceride, 2-heptylundecyl palmitate, diisobutyl adipate, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, di-2-heptylundecyl adipate, ethyl laurate, di-sebacate Examples include 2-ethylhexyl, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, and 2-ethylhexyl succinate.

Examples of silicone oils include linear polysiloxanes (e.g., dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane, etc.); cyclic polysiloxanes (e.g., octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexane, etc.); sasiloxane, etc.), silicone resins forming three-dimensional network structures, silicone rubber, and various modified polysiloxanes (amino-modified polysiloxanes, polyether-modified polysiloxanes, alkyl-modified polysiloxanes, fluorine-modified polysiloxanes, etc.). It will be done.

Examples of anionic surfactants include fatty acid soaps (e.g., sodium laurate, sodium palmitate, etc.); higher alkyl sulfate salts (e.g., sodium lauryl sulfate, potassium lauryl sulfate, etc.); alkyl ether sulfate salts (e.g., POE-triethanolamine lauryl sulfate, POE-sodium lauryl sulfate, etc.); N-acyl sarcosinate (e.g. sodium lauroyl sarcosine, etc.); Higher fatty acid amide sulfonates (e.g. sodium myristoyl-N-methyltaurate, oil fatty acid methyl taurate sodium, lauryl methyl taurate sodium, etc.); phosphate ester salts (POE-sodium oleyl ether phosphate, POE-stearyl ether phosphate, etc.); sulfosuccinates (for example, sodium di-2-ethylhexyl sulfosuccinate, monolauroyl monoethanolamide polyoxyethylene sodium sulfosuccinate, lauryl polypropylene glycol sodium sulfosuccinate, etc.); alkylbenzene sulfonates (e.g., sodium linear dodecylbenzenesulfonate, linear dodecylbenzenesulfonic acid triethanolamine, linear dodecylbenzenesulfonic acid, etc.) ); higher fatty acid ester sulfate salts (e.g. hydrogenated coconut oil fatty acid sodium glycerol sulfate, etc.); N-acylglutamates (e.g. monosodium N-lauroylglutamate, disodium N-stearoylglutamate, N-myristoyl-L-glutamic acid); monosodium, etc.); sulfated oil (e.g., funnel oil, etc.); POE-alkyl ether carboxylic acid; POE-alkyl allyl ether carboxylate; α-olefin sulfonate; higher fatty acid ester sulfonate; secondary alcohol sulfuric acid Examples include ester salts; higher fatty acid alkylolamide sulfate ester salts; sodium lauroyl monoethanolamide succinate; N-palmitoylaspartic acid ditriethanolamine; sodium caseinate and the like.

Examples of cationic surfactants include alkyltrimethylammonium salts (e.g., stearyltrimethylammonium chloride, lauryltrimethylammonium chloride, etc.); alkylpyridinium salts (e.g., cetylpyridinium chloride, etc.); distearyldimethylammonium chloride dialkyldimethylammonium salts; Alkyl quaternary ammonium salts; alkyldimethylbenzylammonium salts; alkylisoquinolinium salts; dialkylmorphonium salts; POE-alkylamines; alkylamine salts; amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride, etc. .

Examples of amphoteric surfactants include imidazoline-based amphoteric surfactants (for example, 2-undecyl-N,N,N-(hydroxyethylcarboxymethyl)-2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide), side-1-carboxyethyloxy disodium salt, etc.); betaine surfactants (for example, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine (sodium cocoamphoacetate), lauryldimethylaminoacetic acid betaine, Alkylbetaine, amidobetaine, sulfobetaine, etc.).

Examples of nonionic surfactants include sorbitan fatty acid esters (e.g., sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate). ate, diglycerol sorbitan pent-2-ethylhexylate, diglycerol sorbitan tetra-2-ethylhexylate, etc.); glycerin fatty acids (e.g. monocottonseed oil fatty acid glycerin, monoerucic acid glycerin, sesquioleate glycerin, monostearate glycerin, α , α'-oleate, glyceryl pyroglutamate, glyceryl monostearate, malic acid, etc.); Propylene glycol fatty acid esters (e.g., propylene glycol monostearate, etc.); Hydrogenated castor oil derivatives; Glycerin alkyl ether; POE-sorbitan fatty acid esters (For example, POE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan tetraoleate, etc.); POE-sorbitan fatty acid esters (for example, POE-sorbitan monolaurate, POE-sorbitan monooleate, POE- POE-glycerin fatty acid esters (e.g., POE-glycerin monostearate, POE-glycerin monoisostearate, POE-glycerin triisostearate, etc.); POE- Fatty acid esters (e.g., POE-distearate, POE-monodioleate, ethylene glycol distearate, etc.); POE-alkyl ethers (e.g., POE-lauryl ether, POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE -2-octyl dodecyl ether, POE-cholestanol ether, etc.); Pluronic types (e.g., Pluronic, etc.); POE/POP-alkyl ethers (e.g., POE/POP-cetyl ether, POE/POP-2-decyl tetra Decyl ether, POE/POP-monobutyl ether, POE/POP-hydrogenated lanolin, POE/POP-glycerin ether, etc.); Tetra-POE/Tetra-POP-ethylenediamine condensates (e.g. Tetronic, etc.); POE-castor oil hardening Castor oil derivatives (e.g. POE-castor oil, POE-hydrogenated castor oil, POE-hydrogenated castor oil monoisostearate, POE-hydrogenated castor oil triisostearate, POE-hydrogenated castor oil monopyroglutamic acid monoisostearate diester, POE - hydrogenated castor oil maleic acid, etc.); POE - beeswax/lanolin derivatives (e.g. POE - sorbitol beeswax, etc.); alkanolamide (e.g. coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide, etc.); POE -propylene glycol fatty acid ester; POE-alkylamine; POE-fatty acid amide; sucrose fatty acid ester; alkyl ethoxydimethylamine oxide; trioleyl phosphoric acid and the like.

Examples of moisturizing agents include polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carvone. Examples include acid salts, short-chain soluble collagen, diglycerin (EO) PO adducts, Izayoi rosea extract, Yarrow extract, Melilot extract, and the like.

Examples of natural water-soluble polymers include plant-based polymers (e.g., gum arabic, gum tragacanth, galactan, guar gum, carob gum, gum karaya, carrageenan, pectin, agar, quince seed (quince), algae colloid (cassou extract), starch). (rice, corn, potato, wheat), glycyrrhizic acid); Microbial polymers (e.g., xanthan gum, dextran, succinoglucan, bull run, gellan gum, etc.); Animal-based polymers (e.g., collagen, casein, albumin, gelatin, etc.) ) etc.

Examples of water-soluble polymers include starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methyl cellulose, ethyl cellulose, methyl hydroxypropyl cellulose, hydroxyethyl cellulose, sodium cellulose sulfate, hydroxypropyl Cellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder, etc.); Alginic acid polymers (e.g. sodium alginate, alginate propylene glycol ester, etc.); Vinyl polymers (e.g. polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone) , carboxyvinyl polymer, etc.); polyoxyethylene polymers (e.g., polyoxyethylene polyoxypropylene copolymers such as polyethylene glycol 20,000, polyethylene glycol 40,000, polyethylene glycol 60,000, etc.); acrylic polymers Molecules (eg, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, and the like.

Examples of the chelating agent include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, edetate disodium, edetate trisodium, edetate tetrasodium, polyphosphoric acid. Examples include sodium acid, sodium metaphosphate, phosphoric acid, ascorbic acid, succinic acid, edetate, and the like.

Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, and t-butyl alcohol.

Examples of polyhydric alcohols (excluding each component of the glyceryl ether composition (A)) include dihydric alcohols (for example, 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,5-pentanediol, 2,4-pentanediol, etc.) ; Trihydric alcohols (e.g., glycerin, trimethylolpropane, etc.); Tetrahydric alcohols (e.g., pentaerythritol, such as 1,2,5,6-hexanetetraol, etc.); Pentahydric alcohols (e.g., xylitol, etc.); Hexahydric alcohols (e.g. sorbitol, mannitol, etc.); polyhydric alcohol polymers (e.g. diethylene glycol, triethylene glycol, dipropylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, poly glycerin, etc.); Alcohol alkyl ethers (e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol Isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, Diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether , dipropylene glycol butyl ether, etc.); dihydric alcohol ether esters (e.g., ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diadibate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monophenyl ether acetate, etc.); sugar alcohols (e.g. sorbitol) , maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch-degrading sugar, maltose, xylitose, starch-degrading sugar reducing alcohol, etc.); glycolid; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl Alcohol; POP-butyl ether; POP/POE-butyl ether; tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphoric acid; POP/POE-pentane erythritol ether.

Examples of monosaccharides include tricarbons (e.g., D-glycerylaldehyde, dihydroxyacetone, etc.); tetracarbons (e.g., D-erythrose, D-erythrulose, D-threose, erythritol, etc.); pentose (e.g., , L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc.); hexoses (e.g., D-glucose, D-talose, D - Bucicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tagatose, etc.); Seven carbon sugars (e.g., aldoheptose, heprose, etc.); Octose sugars (e.g., octulose, etc.); Deoxy sugars ( For example, 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L-mannose, etc.); Amino sugars (for example, D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.) ); uronic acids (eg, D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid, etc.);

Examples of oligosaccharides include sucrose, umbelliferose, lactose, planteose, isoliqunose, α,α-trehalose, raffinose, lichnose, umbilicin, stachyose verbascose, and the like.
Examples of polysaccharides include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, gum tragacanth, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guar gum, dextran, and keratosulfate. , locust Bingham, succinoglucan, caronic acid, and the like.

Examples of amino acids include neutral amino acids (eg, threonine, cysteine, etc.); basic amino acids (eg, hydroxylysine, etc.). Further, examples of amino acid derivatives include sodium acylsarcosine (sodium lauroylsarcosine), acylglutamate, sodium acyl β-alanine, glutathione, and pyrrolidone carboxylic acid.

Examples of organic amines include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-methyl-1-propanol, etc. can be mentioned.

Examples of the polymer emulsion include acrylic resin emulsion, polyethyl acrylate emulsion, acrylic resin liquid, polyacrylalkyl ester emulsion, polyvinyl acetate resin emulsion, and natural rubber latex.

Examples of the pH adjuster include lactic acid-sodium lactate, succinic acid-sodium succinate, citric acid-sodium citrate, and sodium hydrogen carbonate. The pH of the cosmetic composition of the present invention may be adjusted as appropriate depending on the intended use, but from the viewpoint of applicability to the skin, it is preferably 2.0 to 12.0.

Examples of vitamins include vitamins A, B1, B2, B6, C, E and their derivatives, pantothenic acid and its derivatives, biotin, and the like.
Examples of the antioxidant include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, and the like.

Other ingredients that can be blended include, for example, anti-inflammatory agents (e.g., glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); skin whitening agents (e.g., saxifrage extract, arbutin, etc.); various extracts. things (e.g., sagebrush, sage, loquat, carrot, aloe, mallow, iris, grape, sagebrush, loofah, lily, saffron, nematode, ginger, hypericum, hypericum, ononis, garlic, hot pepper) , Chimpi, Touki, seaweed, etc.), activators (e.g., royal jelly, photosensors, cholesterol derivatives, etc.); blood circulation promoters (e.g., benzyl nicotinic acid ester, β-butoxyethyl nicotinic acid ester, capsaicin, zingerone, cantharis tincture) , ictamol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclanderate, cinnarizine, tolazoline, acetylcholine, verapamil, cephalanthine, γ-oryzanol, etc.); antiseborrheic agents (for example, sulfur, thianthol, etc.) ); anti-inflammatory agents (eg, tranexamic acid, thiotaurine, hypotaurine, etc.);

A method for improving the antibacterial properties of a glyceryl ether composition of the present invention includes a monoalkyl glyceryl ether having a straight chain alkyl group having 6 to 8 carbon atoms, a monoalkyl glyceryl ether having a branched alkyl group having 6 to 8 carbon atoms, At least one cationic polymer is added to a glyceryl ether composition consisting of two or more types selected from the group consisting of monoalkyl glyceryl ethers having an alicyclic alkyl group having 6 to 8 carbon atoms, and the cationic polymer is added to the glyceryl ether composition. This is a method for improving the antibacterial properties of a glyceryl ether composition, in which the polymer is added in an amount such that the ratio of the polymer contents is 60:40 to 99:1 in terms of mass ratio. In this method, as the glyceryl ether composition and cationic polymer, compounds equivalent to those that can be used in the antibacterial composition described above can be used.

In the method for improving the antibacterial properties of the glyceryl ether composition of the present invention, if the ratio of the content of the glyceryl ether composition to the cationic polymer is 60:40 to 99:1 in mass ratio, Although antibacterial properties can be improved, from the viewpoint of further enhancing the synergistic effect and particularly improving the antibacterial properties of the glyceryl ether composition, the content ratio of the glyceryl ether composition and the cationic polymer should be 70: by mass. The ratio is preferably 30 to 95:5, more preferably 80:20 to 92:8, and even more preferably 85:15 to 91:9. According to the present invention, when a glyceryl ether composition is blended into cosmetics, detergents, etc., sufficient antibacterial properties can be exhibited with a smaller blending amount. In the method of improving the antibacterial properties of the glyceryl ether composition of the present invention, the same glyceryl ether compositions and cationic polymers that can be used in the antibacterial compositions described above can be used.

EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples. In addition, in the following Examples and the like, "%" is based on mass unless otherwise specified.

<Compounds used>
Monoalkylglyceryl ether A-1: Cyclohexylglyceryl ether A-2: Ethylhexylglyceryl ether Cationic polymer B-1: Polyquaternium-6 (“ADEKA Cation Ace PD-50” manufactured by ADEKA Co., Ltd., 40% solution)

<Fungi to be tested>
E. coli: Escherichia coli (bacteria) ATCC 8739
P. aer: Pseudomonas aeruginosa (bacteria) ATCC 9027
S. aur: Staphylococcus aureus (bacteria) ATCC 6538
C. alb: Candida Albicans (mold) ATCC 10231
A. bra: Aspergillus brasiliensis (mold) ATCC 16404

<Preparation of bacterial solution>
After pre-cultivating the bacteria in SCD (soy bean casein digest) liquid medium, the test bacteria solution was prepared by adjusting the concentration of viable bacteria in the solution to a level of 10 ⁶ - 10 ⁷ cfu/mL with a 0.9% NaCl aqueous solution. Prepared. After the mold was precultured on a glucose agar medium, a test bacterial solution was prepared by adjusting the concentration of viable bacteria in the solution to a level of 10 ³ to 10 ⁴ cfu/mL with a 0.9% NaCl aqueous solution.

<Test method>
After dispensing 20 μL of each test bacterial solution into a microplate, the antibacterial composition containing each monoalkyl glyceryl ether and cationic polymer at the content ratios shown in Tables 1 and 2 was diluted with a medium. 180 μL of a mixed solution containing at a specific concentration was prepared (the content ratio and content of the cationic polymer are based on the amount of the active ingredient). Next, each mixed solution was cultured in a constant temperature bath at 33° C. for 48 hours, and then the turbidity of each mixed solution was observed and antibacterial properties were evaluated based on the following criteria. The results of each evaluation are shown in Tables 1 and 2.
Antibacterial evaluation criteria ○: No turbidity or presence of colonies or hyphae was observed in all 5 types of mixed solutions. ×: turbidity or presence of colonies or hyphae was observed in 1 or more types of mixed solutions.

<Evaluation of synergy>
Regarding the antibacterial composition used in Example 1, the FIC (Fractional Inhibitory Concentration) index was calculated according to the following formula. The FIC index is an index that evaluates the synergistic effect of antibacterial properties in a composition consisting of two or more ingredients.If the FIC index is less than 1, it indicates that the combination of ingredients used has a synergistic effect, and if it is greater than 1, it indicates that the combination of ingredients used has a synergistic effect. indicates that there is an antagonistic effect.
FIC= _A1 '/ _A1 + _A2 '/ _A2 + _B1 '/ _B1
In the formula, A ₁ is the MIC (minimum inhibitory concentration) value of A-1 alone, A ₁ ' is the concentration of A-1 in Example 1, A ₂ is the MIC value of A-2 alone, A ₂ ' represents the concentration of A-2 in Example 1, B ₁ represents the MIC value of B-1 alone, and B ₁ ' represents the concentration of B-1 in Example 1. At this time, the MIC value of each compound alone is determined by using a 0.9% NaCl aqueous solution as a test bacterial solution and adjusting the concentration of viable bacteria (C. alb: Candida Albicans (mold) ATCC 10231) in the solution to 10 ³ - 10 ⁴ The values measured by the following MIC test method using a bacterial solution adjusted to the cfu/mL level were used.

<MIC test method>
Dispense 0.020 μL of the test bacterial solution into a microplate, add 0.18 μL of the test solution containing compound A-1, A-2, or B-1 each adjusted to various concentrations using the culture medium, and stir to prepare a mixed solution. . Next, after culturing each mixed solution for one week at 25°C, we observed the turbidity of each mixed solution, and found that no turbidity or hyphae were observed for each combination of fungus and compound (of the fungi to be tested). The lowest concentration of each compound in the mixed solution (which inhibited growth) was determined and used as the MIC value for each compound alone.

As a result of the synergistic effect evaluation, the FIC index of the antibacterial composition used in Example 1 was 0.825, and the combination of monoalkyl glyceryl ethers A-1, A-2, and cationic polymer B-1 It was shown that there is a synergistic antibacterial effect.

From the above results, it was observed that the antibacterial composition containing the glyceryl ether composition (A) and the cationic polymer (B) at a specific mass ratio had an antibacterial enhancement effect and an antibacterial improvement. This shows that the antibacterial effect of the glyceryl ether composition (A) is significantly enhanced by the addition of the cationic polymer (B), and the antibacterial composition of the present invention exhibits high antibacterial properties.

Claims (7)

Monoalkylglyceryl ether having a straight chain alkyl group having 6 to 8 carbon atoms, monoalkylglyceryl ether having a branched alkyl group having 6 to 8 carbon atoms, and monoalkylglyceryl ether having an alicyclic alkyl group having 6 to 8 carbon atoms. A glyceryl ether composition (A) consisting of two or more types selected from the group consisting of ethers, and at least one cationic polymer (B), containing the glyceryl ether composition (A) and the cationic polymer (B). The ratio of amounts is from 60:40 to 99:1 in mass ratio, and the cationic polymer is polyquaternium-6, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-47, and polyquaternium-53. An antibacterial composition selected from the group consisting of : The antibacterial composition according to claim 1, wherein the glyceryl ether composition (A) contains at least one monoalkyl glyceryl ether having an alicyclic alkyl group having 6 carbon atoms. The antibacterial composition according to claim 1 or 2, wherein the cationic polymer (B) contains at least one selected from the group consisting of polyquaternium-6 and polyquaternium-7 . A cosmetic composition containing the antibacterial composition according to any one of claims 1 to 3. The cosmetic composition according to claim 4, wherein the content of the glyceryl ether composition (A) in the cosmetic composition is 0.01 to 3.0% by mass based on the total amount of the cosmetic composition. Monoalkylglyceryl ether having a straight chain alkyl group having 6 to 8 carbon atoms, monoalkylglyceryl ether having a branched alkyl group having 6 to 8 carbon atoms, and monoalkylglyceryl ether having an alicyclic alkyl group having 6 to 8 carbon atoms. A glyceryl ether composition consisting of two or more ethers selected from the group consisting of polyquaternium-6, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-47, and polyquaternium-53. At least one cationic polymer is added in an amount such that the content ratio of the glyceryl ether composition to the cationic polymer is 60:40 to 99:1 by mass, improving the antibacterial properties of a glyceryl ether composition. Method. 7. The method according to claim 6, which improves the antibacterial properties of the glyceryl ether composition in a cosmetic composition.