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WO2018101370A1 - Composition riche en acyl-aminoacides - Google Patents

Composition riche en acyl-aminoacides Download PDF

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Publication number
WO2018101370A1
WO2018101370A1 PCT/JP2017/042924 JP2017042924W WO2018101370A1 WO 2018101370 A1 WO2018101370 A1 WO 2018101370A1 JP 2017042924 W JP2017042924 W JP 2017042924W WO 2018101370 A1 WO2018101370 A1 WO 2018101370A1
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Prior art keywords
composition
composition according
group
weight
general formula
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PCT/JP2017/042924
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English (en)
Japanese (ja)
Inventor
絵子 水津
奈々 原矢
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味の素株式会社
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to a composition having high antibacterial properties and high shelf-life containing a high concentration of acylamino acid, acetophenone derivative and polyhydric alcohol, and a cosmetic comprising the composition.
  • the present invention also relates to a preservative method for cosmetics, which comprises adding the composition.
  • Patent Documents 1 and 2 As a technique for preserving cosmetics by devising combinations of materials, methods for preserving cosmetics using acetophenone derivatives and polyhydric alcohols (particularly diols) have been proposed (Patent Documents 1 and 2).
  • acetophenone derivatives have been reported to make the emulsion droplets fine in the emulsion composition, stabilize the emulsion system, and improve the functionality of cosmetics. Further, it was not discussed from the viewpoint of coloring stability (Patent Documents 1 and 2).
  • there is a problem that low molecular diols have a great influence on the feeling of use and prescription, and it is not preferable to increase the blending amount so much, and in some cases, the requirement for low irritation may not be satisfied.
  • acylamino acids are known as low-stimulation and high-safety materials.
  • acylproline or a salt thereof has been reported to exhibit a moisturizing effect with excellent hygroscopicity and moisture retention, and to provide a cosmetic with an excellent feeling of use while suppressing the smell of antibacterial agents where odor is a problem.
  • Patent Documents 2 and 3 Acylglycine or a salt thereof can be used as a detergent composition with low irritation and no sliminess (Patent Document 4), and in particular, undecylenoylglycine has anti-acne and anti-dandruff activity (Patent Document 5).
  • octanoylglycine is used as an anti-acne, antiperspirant, deodorant and the like, and has been disclosed to exhibit an antibacterial effect, but it has also been reported to cause squeaky feeling in cosmetics (Patent Document) 6).
  • Patent Document 6 acylproline and acylglycine are far from being materials that satisfy all the required conditions in the above-described technology for preserving cosmetics.
  • the present invention contains a high concentration of acylproline and / or acylglycine and an acetophenone derivative, has a high antiseptic effect without adding a preservative such as paraben, has sufficient storage stability, and has a good feeling of use. It is to provide a feasible composition.
  • a composition containing an acetophenone derivative at a high concentration in advance is not suitable for long-term storage at a wide range of temperatures.
  • proline and / or acylglycine and polyhydric alcohol When combined with proline and / or acylglycine and polyhydric alcohol, it has a high antiseptic effect over a wide pH range against bacteria and fungi, especially mold, and precipitates, freezes, separates, becomes turbid, colored even after long-term storage at low and high temperatures
  • the present invention has been completed by finding that it has a sufficient storage stability without causing a problem in performance change, has a low irritation, and has a good feeling of use without stickiness or creaking.
  • a composition comprising the following (A), (B) and (C): (A) Acylproline represented by the general formula (I) and a salt thereof:
  • acyl group represented by R 1 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 4 to 18 carbon atoms
  • acyl group represented by R 2 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 6 to 12 carbon atoms
  • R 3 and R 4 each independently represents hydrogen, a hydroxy group or —OCH 3
  • C Polyhydric alcohol.
  • Composition [3] The composition according to any one of [1] or [2], wherein (A) is at least one selected from the group consisting of decanoylproline and octanoylglycine.
  • the acylproline represented by the general formula (I) is at least one selected from the group consisting of octanoylproline, decanoylproline, undecylenoylproline and lauroylproline [1] ] Or the composition in any one of [2].
  • the acylglycine represented by the general formula (II) is at least one selected from the group consisting of octanoyl glycine, undecylenoyl glycine and decanoyl glycine [1] or [ 2].
  • (A) is at least one selected from the group consisting of decanoyl proline, octanoyl glycine and undecylenoyl glycine.
  • (B) The compound represented by the general formula (III) is
  • Composition [18] The composition according to any one of [1] to [17], which has a pH of 5.5 to 6.5. [19] The composition according to any one of [1] to [18], which is liquid.
  • composition according to any one of [1] to [19], which is an antibacterial or antiseptic composition is an antibacterial or antiseptic composition.
  • a cosmetic comprising the composition according to any one of [1] to [20].
  • a method for preserving a cosmetic comprising the step of adding the composition according to any one of [1] to [20] to the cosmetic, wherein the composition is 0.1% relative to the total weight of the cosmetic.
  • composition of the present invention contains a high concentration of an acetophenone derivative and an acylamino acid, a desired amount can be easily added to various cosmetics. According to the present invention, it is possible to provide a cosmetic having excellent storage stability by preventing the growth of not only bacteria but also fungi at a wide pH. Furthermore, according to this invention, the cosmetics which have a desired external appearance and excellent in the usability
  • FIG. 1 shows the influence on the color stability depending on the type and amount of polyhydric alcohol as the transmittance after storage at 70 ° C. for 3 weeks.
  • the vertical axis represents the transmittance (%) at 430 nm.
  • FIG. 2 shows the effect of the type and amount of polyhydric alcohol on the color stability in terms of transmittance after storage at 70 ° C. for 3 weeks.
  • the vertical axis represents the transmittance (%) at 430 nm.
  • FIG. 3 shows the cytotoxic expression concentration of the present composition and a wetting agent having an antiseptic function.
  • R 1 —CO— is an acyl group derived from a saturated or unsaturated fatty acid having 4 to 18 carbon atoms, that is, an acyl residue of the saturated or unsaturated fatty acid.
  • the long-chain acyl group represented by R 1 —CO— is an acyl group derived from an acid having a single composition, as well as a natural mixture such as coconut oil fatty acid, castor oil fatty acid, olive oil fatty acid, and palm oil fatty acid. It may be an acyl group derived from a fatty acid or a fatty acid obtained by synthesis (including a branched fatty acid). One of these may be used, or two or more selected from the above group may be mixed and used.
  • the acyl group represented by R 1 —CO— is preferably an acyl group derived from a saturated or unsaturated fatty acid having 6 to 14 carbon atoms, more preferably from a saturated or unsaturated fatty acid having 8 to 12 carbon atoms.
  • the acyl group is more preferably derived, more preferably an acyl group derived from a saturated or unsaturated fatty acid having 8 to 10 carbon atoms, and particularly preferably a decanoyl group.
  • the acylproline represented by the general formula (I) is preferably octanoylproline, decanoylproline, undecylenoylproline, or lauroylproline, and more preferably decanoylproline.
  • R 1 represents a hydrocarbon group having 3 to 17 carbon atoms.
  • the “hydrocarbon group” include a chain hydrocarbon group such as an alkyl group and an alkynyl group, but a chain hydrocarbon group is preferable, and any linear or branched chain can be used. . Of these, an alkyl group is more preferable.
  • the “hydrocarbon group” preferably has 5 to 13 carbon atoms, more preferably 7 to 11, and still more preferably 7 to 9.
  • Examples of the salt of the compound represented by the general formula (I) include pharmacologically acceptable salts, alkali metal salts such as lithium salt, sodium salt and potassium salt; alkalis such as calcium salt and magnesium salt. Examples include earth metal salts; ammonium salts; and basic organic salts. Of these, from the viewpoint of solubility, sodium salts, potassium salts, and ammonium salts are preferable, sodium salts and potassium salts are more preferable, and sodium salts are still more preferable.
  • the compound represented by the formula (I) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • acylproline in the present invention is not particularly limited, and can be easily produced by combining known methods.
  • acylproline can be prepared by the Schotten-Baumann method by simultaneously dropping acid chloride and a base such as sodium hydroxide on proline.
  • the proline may be L, D, or a mixture thereof, but is preferably L.
  • the acyl group represented by R 2 —CO— is an acyl group derived from a saturated or unsaturated fatty acid having 6 to 12 carbon atoms, that is, an acyl residue of the saturated or unsaturated fatty acid. Examples include hexanoyl group, heptanoyl group, octanoyl group, 2-ethylhexanoyl group, tert-octanoyl group, nonanoyl group, isononanoyl group, decanoyl group, isodecanoyl group, undecylenoyl group, undecanoyl group and lauroyl group.
  • the long-chain acyl group represented by R 2 —CO— is obtained by natural mixed fatty acids such as coconut oil fatty acid and palm kernel oil fatty acid, or by synthesis, in addition to an acyl group derived from an acid having a single composition. It may be an acyl group derived from a fatty acid (including a branched fatty acid). One of these may be used, or two or more selected from the above group may be mixed and used.
  • the acyl group represented by R 2 —CO— is preferably an acyl group derived from a saturated or unsaturated fatty acid having 8 to 11 carbon atoms, more preferably an octanoyl group or an undecylenoyl group.
  • the acyl glycine represented by the general formula (II) is preferably octanoyl glycine, undecylenoyl glycine, and decanoyl glycine, and is preferably octanoyl glycine and undecylenoyl glycine.
  • R 2 represents a hydrocarbon group having 5 to 11 carbon atoms.
  • the “hydrocarbon group” include chain hydrocarbon groups such as an alkyl group and an alkynyl group.
  • a chain hydrocarbon group is preferable, and a straight chain or branched chain group can be used, and an alkyl group is more preferable. Further, 7 to 10 carbon atoms are more preferable.
  • Examples of the salt of the compound represented by the general formula (II) include pharmacologically acceptable salts, alkali metal salts such as lithium salt, sodium salt and potassium salt; alkalis such as calcium salt and magnesium salt. Examples include earth metal salts; ammonium salts; and basic organic salts. Of these, from the viewpoint of solubility, sodium salts, potassium salts, and ammonium salts are preferable, sodium salts and potassium salts are more preferable, and sodium salts are still more preferable.
  • the compound represented by the formula (II) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • acylglycine in the present invention is not particularly limited, and can be easily produced by combining known methods.
  • acylglycine can be prepared by the Schotten-Baumann method by simultaneously dropping acid chloride and a base such as sodium hydroxide into glycine.
  • (A) in the composition of this invention can be used 1 type or in mixture of 2 or more types among acylproline and its salt, and acylglycine and its salt.
  • acylproline or a salt thereof is preferable.
  • acylglycine or a salt thereof is usually 0.01 to 50 parts by weight, preferably 0.1 to 20 parts by weight, 0.1 to 10 parts by weight is more preferable.
  • the content of (A) in the composition of the present invention is usually 10% by weight or more, preferably 13% by weight or more, more preferably 15% by weight or more with respect to the total weight of the composition.
  • the content of (A) is usually 40% by weight or less, preferably 35% by weight or less, and more preferably 30% by weight or less.
  • [(B) Acetophenone derivative] (B) in the present invention is a compound represented by the following general formula (III) or a salt thereof:
  • R 3 and R 4 each independently represent hydrogen, a hydroxy group, or —OCH 3 .
  • the compound represented by the general formula (III) is a compound in which R 3 and R 4 are bonded to the ortho, meta, and / or para position with respect to the acetyl group, (III-a) Acetophenone
  • Examples of the salt of the compound represented by the general formula (III) include pharmacologically acceptable salts, alkali metal salts such as lithium salt, sodium salt and potassium salt; alkalis such as calcium salt and magnesium salt. Examples include earth metal salts; ammonium salts; and basic organic salts. Among these, from the viewpoint of versatility, sodium salt, potassium salt, and ammonium salt are preferable, sodium salt and potassium salt are more preferable, and sodium salt is more preferable.
  • the compound represented by the formula (III) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • the compound represented by the general formula (III) or a salt thereof may be any of chemical synthesis methods, natural products derived from animals and plants, those obtained by fermentation methods or gene recombination methods.
  • the content of (B) in the composition of the present invention is usually 5% by weight or more, preferably 8% by weight or more, preferably 10% by weight or more based on the total weight of the composition from the viewpoints of antiseptic effect and storage stability. More preferably, it is more than wt%.
  • the content of (B) is usually 20% by weight or less, preferably 18% by weight or less, and more preferably 15% by weight or less.
  • (A) is usually 0.1 to 25 parts by weight and 0.2 to 15 parts by weight with respect to 1 part by weight of (B). Part by weight, preferably 1 to 14 parts by weight.
  • the total weight of (A) and (B) is usually 10% or more, preferably 15% or more, more preferably 20%, based on the total weight of the composition. Above, more preferably 25% or more, particularly preferably 28% or more.
  • the upper limit is not particularly limited, but is usually 80% or less, preferably 60% or less.
  • a polyhydric alcohol is a compound which has 2 or more of hydroxyl groups in 1 molecule.
  • glycerin, diglycerin, polyglycerin, propylene glycol (1,2-propanediol), butylene glycol, pentylene glycol, methylpropanediol, 1,2-pentanediol, 1,5-pentanediol, dipropylene glycol examples include xylene glycol, 1,2-hexanediol, 1,6-hexanediol, neopentyl glycol, isoprene glycol, cyclohexyl glycerin, low-polymerized polyethylene glycol, maltitol, erythritol, mannitol, xylitol, and sorbitol.
  • polyhydric alcohols having 2 to 20 carbon atoms are preferred, and polyhydric alcohols having 3 to 12 carbon atoms are more preferred from the viewpoint of long-term storage stability, availability, and compatibility with component (B).
  • 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, dipropylene glycol, 1,2-pentanediol, 1,2-hexanediol, 1,6 -Hexanediol is preferable, 1,2-pentanediol, dipropylene glycol, 1,3-propanediol, 1,2-hexanediol and 1,6-hexanediol are more preferable.
  • polyhydric alcohols can be used alone or in combination of two or more.
  • any of commercially available products, chemical synthesis methods, natural products derived from animals and plants, those obtained by fermentation methods or gene recombination methods may be used.
  • the content of (C) in the composition of the present invention is usually 10% by weight or more, preferably 20% by weight or more, with respect to the total weight of the composition, from the viewpoint of antiseptic effect and storage stability. More preferably, it is more than wt%.
  • the content of (C) is usually 60% by weight or less, preferably 45% by weight or less, and more preferably 35% by weight or less.
  • (A) is usually 10 to 40% by weight, (B) is 5 to 20% by weight, and (C) is 10 to 60% by weight, (A) is preferably 13 to 35% by weight, (B) is preferably 8 to 18% by weight, and (C) is preferably 20 to 45% by weight, and (A) is preferably 15 to 30% by weight. More preferably, 10% to 15% by weight of (B), and 25 to 35% by weight of (C) are blended.
  • the weight ratio ((A) + (C) of the sum of (A) and (C) to (B) )) / (B) usually exceeds 2.8.
  • the weight ratio is preferably 2.9 or more, more preferably 3.3 or more, and particularly preferably 3.9 or more. If it is the range of this numerical value, the composition excellent in long-term storage stability can be provided.
  • the upper limit is ((A) + (C)) / (B) of 17 or less, preferably 6 or less. Within this range, a clear solution can be provided without causing precipitation.
  • the composition of the present invention preferably contains a chelating agent as the component (D).
  • chelating agents include etidronic acid, pentetic acid, EDTA and salts thereof from the viewpoint of long-term storage stability and availability. Of these, etidronic acid, pentetic acid and salts thereof are preferable, pentetic acid or a salt thereof is more preferable from the viewpoint of long-term storage stability, and pentasodium acid pentasodium is particularly preferable from the viewpoint of ease of blending.
  • the content of (D) in the composition of the present invention is usually 0.01% by weight or more and 0.2% by weight or more with respect to the total weight of the composition from the viewpoint of the antiseptic effect and storage stability. Is preferred. Moreover, it is 0.5 weight% or less normally, and 0.4 weight% or less is preferable.
  • the total weight of the composition of the present invention is usually (A) 10 to 40% by weight, (B) 5 to 20% by weight, (C) 10 to 60% by weight, (D) 0.01 to 0.5 wt% is blended, (A) 13 to 35 wt%, (B) 8 to 18 wt%, (C) 20 to 45 wt%, (D) 0.2 to 0.4% by weight is preferably blended, (A) 15-30% by weight, (B) 10-15% by weight, (C) 25-35% by weight, (D) 0.2-0. More preferably, 4% by weight is blended.
  • any of hard water and soft water may be used.
  • water any of hard water and soft water may be used.
  • well water natural water, ground water, tap water, ion exchange water, purified water, distilled water, ultrapure water and the like can be used.
  • the pH of the composition of the present invention is preferably from pH 5.5 to pH 6.5 from the viewpoint of long-term storage stability and ease of production. If the pH is less than 5.5, the acetophenone derivative may be released from the aqueous phase and separated, and if the pH is more than 6.5, coloring may occur and long-term storage stability may be deteriorated.
  • a dilute acid aqueous solution or a dilute alkaline aqueous solution may be used, but dilute hydrochloric acid or citric acid aqueous solution because of its good operability and ease of incorporation into cosmetics.
  • dilute sulfuric acid, sodium hydroxide aqueous solution and potassium hydroxide aqueous solution are preferably used.
  • composition of the present invention can be used as an antibacterial composition (antibacterial agent), an antiseptic composition (preservative) or an auxiliary agent thereof.
  • Antibacterial agents, preservatives or their adjuvants can be produced by a known method by adding the additives described later, even with the composition of the present invention alone.
  • antibacterial means not to increase bacteria for a long time, and means to suppress the growth of bacteria on the surface of a composition such as cosmetics.
  • preservation means preventing invasion, growth, and proliferation of microorganisms so that no spoilage or fermentation occurs. Therefore, the “preservative effect” means an effect of suppressing the growth of fungi such as fungi and bacteria to prevent the cosmetic material from deteriorating and enhancing its preservability.
  • composition of the present invention is not particularly limited, and can take any form such as liquid, emulsion, paste, gel, solid, and powder. Of these, liquid, emulsion, paste, and gel are preferable.
  • a cosmetic comprising the composition of the present invention is also included in the present invention.
  • the cosmetic may contain only the composition of the present invention, or a component that may be usually added to the cosmetic is effective for the present invention. You may mix
  • Specific ingredients that may be added to cosmetics include oils, surfactants, powders, amino acids, polyamino acids and salts thereof, lower alcohols, animal and plant extracts, nucleic acids, vitamins, enzymes, anti-inflammatory agents, Examples include bactericides, antiseptics, antioxidants, moisturizers, thickeners, viscosity modifiers, ultraviolet absorbers, antiperspirants, pigments, dyes, fragrances, pH adjusters, pearlizing agents, wetting agents, and the like. These are merely examples, and other components may be added as a matter of course.
  • Oils include fatty acids such as isostearic acid, undecylenic acid, oleic acid; myristyl myristate, hexyl laurate, decyl oleate, isopropyl myristate, hexyldecyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, monostearic acid Esters such as ethylene glycol, cetyl octoate, octyl oxystearate, alkyl benzoate; hydrocarbons such as liquid paraffin, polyisobutene, petrolatum, squalane; waxes such as lanolin, reduced lanolin, carnauba wax; silicone oil, mink oil, Fats and oils such as cocoa oil, coconut oil, palm kernel oil, camellia oil, sesame oil, castor oil, olive oil, jojoba oil; ethylene / ⁇ -olefin / co-oligomer
  • silicone oils include methylpolysiloxane, highly polymerized methylpolysiloxane, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer, and poly (oxyethylene, oxypropylene) / methyl.
  • Ether-modified silicone such as polysiloxane copolymer; stearoxymethyl polysiloxane; methyl hydrogen polysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, tetrahydrotetramethylcyclotetrasiloxane, methylcyclopolysiloxane and dodecamethylcyclohexyl Cyclic silicones such as sasiloxane; amino-modified silicones such as methylphenylpolysiloxane and aminoethylaminopropylsiloxane / dimethylsiloxane copolymer Corn: Low molecular silicone compounds such as stearoxytrimethylsilane and trimethylsiloxysilicic acid; silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polys
  • the surfactant examples include N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts, N-long chain fatty acid acyl-N-methyl taurine salts, alkyls.
  • Anionic surfactants such as sulfates and their alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak base salts, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids; Ether type surfactants such as glycerin ether and its alkylene oxide adduct, ether ester type surfactants such as alkylene oxide adduct of glycerin ester, alkylene oxide adduct of sorbitan ester, polyoxyalkylene fatty acid ester, glycerin ester Ester type surfactants such as fatty acid polyglycerin ester, sorbitan ester, sucrose fatty acid ester, alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and its ethylene oxide adduct, and nonionic surfactants
  • the powder examples include resin powders such as nylon beads and silicone beads, nylon powder, metal fatty acid soap, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, cobalt oxide, carbon black, ultramarine, bitumen, Zinc oxide, titanium oxide, zirconium oxide, silicon oxide, aluminum oxide, cerium oxide, titanium mica, boron nitride, barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate, silicon carbide, dye, lake, sericite, mica , Talc, kaolin, plate-like barium sulfate, butterfly-like barium sulfate, fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, acyl lysine, acyl glutamic acid, acyl arginine, acyl glycine, and the like, and further silicone treatment, Fluorine compound Management, silane coupling agent treatment, silane treatment, organic titanate process, acylated lysine treatment, fatty acid treatment,
  • amino acids examples include glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, isoleucine, leucine, and valine.
  • polyamino acids and salts thereof examples include polyglutamic acid and polyaspartic acid.
  • lower alcohols examples include ethanol and propanol.
  • nucleic acids disodium 5′-inosinate, disodium 5′-uridylate, etc .
  • vitamins vitamins A, C, etc. and derivatives thereof; as enzymes Is papain, protease, etc .
  • anti-inflammatory agent is potassium glycyrrhizinate, etc .
  • bactericidal agent is triclosan, trichlorocarban, octopirox, zinc pyrithione, etc .
  • antiseptic is methyl paraben, butyl paraben, etc .
  • Dibutylhydroxytoluene and the like urea and panthenol as the humectant; hydroxypropyl starch phosphate and the like as the thickener; polyoxyalkylene sorbitan ester and polyoxyethylene glycol distearate as the viscosity modifier , Ethanol, etc .
  • UV As the collecting
  • Examples of the cosmetics of the present invention include face wash, lotion, milky lotion, cream, gel, cosmetic liquid, pack, mask, soap, body shampoo, white powder, foundation, lipstick, teak, eyeliner, mascara, eye shadow, Skin cosmetics such as eyebrows, and hair cosmetics such as shampoos, rinses, hair conditioners, hair styling agents, hair treatments and the like. It can be any cosmetics, but it can be used for face wash, lotion, milk, cream, gel, beauty essence, pack, mask, body shampoo and other skin cosmetics, shampoo, rinse, hair conditioner, hair treatment, etc. It is preferable to use a cosmetic for hair. Moreover, it is more preferable to use a cosmetic for skin that requires moisturizing.
  • composition of the present invention and the method for producing the cosmetic are not particularly limited, and in addition to the essential components (A), (B) and (C), in addition to (D), the cosmetic composition as necessary.
  • Various components (such as the above-mentioned other components, water, etc.) necessary for producing can be appropriately selected and blended, and can be produced by a conventional method.
  • the blending amount of the composition of the present invention to be blended with the cosmetic is: It is preferably 0.1% to 10% by weight, more preferably 0.3% to 6% by weight, and particularly preferably 0.5% to 4% by weight based on the total weight of the cosmetic.
  • the antiseptic method for cosmetics comprising the step of adding the above (A), (B), (C) and (D) to the cosmetics is also the second aspect of the present invention.
  • the order of adding (A), (B), (C) and (D) may be added first or simultaneously.
  • Each definition is as described above.
  • the addition amount of (A), (B), (C) and (D) is usually 0.
  • the total amount of (A), (B), (C) and (D) is 0. 1 to 10% by weight, preferably 0.5 to 8% by weight, more preferably 1 to 5% by weight.
  • the present invention also includes a preservative enhancer of the acetophenone derivative represented by the above general formula (III) or a salt thereof, characterized by containing (A).
  • (A) is usually 0.1 to 25 parts by weight, preferably 0.2 to 15 parts by weight, more preferably 1 to 14 parts per 1 part by weight of (B). It mix
  • % means “% by weight”.
  • Octanoyl glycine was synthesized by a method similar to Synthesis Example 1 using glycine (Ajinomoto Co.) and octanoyl chloride (Tokyo Kasei Co., Ltd.). That is, glycine (manufactured by Ajinomoto Co., Inc.) was dissolved in water, and octanoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) and a 25% aqueous sodium hydroxide solution were added while adjusting the pH to 12. 75% sulfuric acid was added for neutralization, and the aqueous layer was removed. Water and ethyl acetate were further added to remove the aqueous layer. Ethyl acetate was distilled off under reduced pressure to obtain octanoylglycine.
  • glycine manufactured by Ajinomoto Co., Inc.
  • octanoyl chloride manufactured by Tokyo Chemical Industry Co., Ltd.
  • Criteria after storage at 50 ° C. and 70 ° C . Transparency of appearance, precipitation A Turbidity and precipitation are not observed after storage. B: After storage, it becomes slightly turbid and precipitation is observed. C Clear turbidity and precipitation are observed after storage.
  • Each compounding amount in this Preparation Example is expressed in weight (g).
  • the weight (g) is omitted, and only the numerical value indicating the blending amount is displayed.
  • “n.d.” in the table indicates that evaluation was not performed.
  • 1,2-pentanediol or dipropylene glycol is blended as a polyhydric alcohol, and when ((A) + (C)) / (B) is greater than 2.8, the composition has a low temperature and a high temperature. It was found that long-term storage stability was excellent in both environments.
  • FIG. 1 Effect of polyhydric alcohol type and addition amount (14.5% and 29.8%)).
  • Antiseptic test 1 of cream to which high composition was added (1) Preparation of cream formulation The aqueous phase component (a) listed in Table 4 was heated, dissolved by stirring, dissolved in advance, and adjusted to pH 6.6 with 3% aqueous sodium hydroxide or citric acid solution. The mixed component of component (b) + (c) + (d) + (e) was added and emulsified. After cooling, the pH of the cream was confirmed while stirring. The prepared composition was subjected to an antiseptic test and a storage stability test. A sample to which the composition of the example was not added was used as a comparative example.
  • test bacterial solution (1) Bacteria Pre-culture at 32.5 ° C. for 20 hours on SCD agar medium. The pre-cultured bacteria were scraped with a platinum loop and suspended in sterilized physiological saline to prepare about 10 8 cells / mL. (2) Yeast Pre-culture at 22.5 ° C. for 48 hours in a Sabouraud-glucose agar medium. The pre-cultured bacteria were scraped with a platinum loop and suspended in sterilized physiological saline to prepare about 10 8 cells / mL. (3) Mold Pre-culture on a Sabouraud-glucose agar medium at 22.5 ° C for 6-10 days. The pre-cultured bacteria were scraped with a platinum loop and suspended in sterile physiological saline supplemented with 0.05% polysorbate 80 to prepare about 10 8 cells / mL.
  • test bacteria For each type of test bacteria, take 20 g of a sample in a sterile vial and inoculate 0.15 mL of the test bacteria solution. Each sample was stored at 22.5 ° C., and the number of viable bacteria was measured on the 7, 14, 21, and 28 days.
  • Aspergillus oryzae As for Aspergillus oryzae, the number of viable bacteria decreases to 0.1% or less compared to the number of bacteria inoculated by 7 days after inoculation, and then the level is the same or until the end of the 28-day test. The viable count was less than that.
  • ⁇ As for Aspergillus oryzae, the number of viable bacteria decreases to 1% or less compared to the number of bacteria inoculated by 7 days after inoculation, and then the number of viable bacteria equal to or less than that level until the end of the 28-day test Stayed in number.
  • ⁇ As for Aspergillus oryzae, the number of viable bacteria is reduced to 10% or less compared to the number of bacteria inoculated by 7 days after inoculation, and then the number of viable bacteria equal to or less than that level until the end of the 28-day test. Stayed in number.
  • X The criterion of ⁇ is not satisfied.
  • specimens containing Examples 1 and 2 (compositions containing Preparation Examples 1-1 and 1-2, respectively) showed good antibacterial activity against bacteria and fungi.
  • Viscosity change rate (%) ⁇ (viscosity after 3 months) ⁇ (initial viscosity) ⁇ ⁇ (initial viscosity) ⁇ 100 When the viscosity was reduced, the absolute value was used for determination.
  • Viscosity variation judgment criteria Judgment was made based on the viscosity change rate as follows: A: Less than 10% B: 10% or more and less than 30% C: 30% or more.
  • test method (1) Preparation of test bacterial solution E. Coli, P. aeruginosa, S. aureus Each test bacterium is cultured on an SCD agar slant medium at 37 ° C. for 20 hours. This 1 platinum ear is transplanted to Mueller Hinton bouillon and cultured at 37 ° C. for 20 hours. The culture solution was diluted with Mueller Hinton bouillon and adjusted to about 10 6 cells / mL, respectively. C. albicans After culturing the test bacteria on a potato dextrose agar medium at 25 ° C. for 48 hours, the test bacteria were scraped with a platinum loop and suspended in sterilized physiological saline to prepare about 10 6 cells / mL. A.
  • test bacteria are cultured on a potato dextrose agar slant medium at 25 ° C. for 7 to 14 days.
  • Tween 80 0.05% physiological saline is poured onto the slope, and the spores are scraped off with platinum ears. This solution was filtered through a sterilized gauze folded in four, and then diluted with 0.05 Tween 80 0.05% physiological saline to prepare a solution of about 10 6 cells / mL.
  • test bacteria prepared in (1) above are collected with a disposable loop (diameter 1 mm), streaked to about 1 cm in length on an agar medium supplemented with an antibacterial agent, and then each specified temperature and time.
  • SI which is a synergistic index of antibacterial effect, was calculated by an industrially accepted method using a ratio determined by the following formula. When the calculated SI is greater than 1, a synergistic effect is observed when the SI is equal to the antagonism 1 or when the additive SI is less than 1. The lower the SI, the greater the synergy exhibited by the mixture.
  • Staphylococcus aureus Staphylococcus aureus
  • Candida albicans Candida albicans
  • Aspergillus brasiliensis Agaricus
  • Judgment As for products stored at 50 ° C., after taking out from the storage for every one month for 3 months, the product is allowed to cool to room temperature, and with regard to the appearance transparency, coloring, and generation (precipitation) of orientation, Judgment was made based on the same criteria.
  • Each compounding amount in this Preparation Example is expressed in weight (g).
  • the weight (g) is omitted, and only the numerical value indicating the blending amount is displayed.
  • Each compounding amount in this Preparation Example is expressed in weight (g).
  • the weight (g) is omitted, and only the numerical value indicating the blending amount is displayed.
  • “n.d.” in the table indicates that evaluation was not performed.
  • Test cell line HaCaT cells were added and cultured in a 96-well plate and used for the experiment.
  • HaCaT cells were cultured in DMEM (Dulbecco's Modified Eagle Medium) (containing 10% serum) at 37 ° C., 5% CO 2 and saturated water vapor.
  • the confluent cells were seeded in a 96-well plate (5 ⁇ 10 4 cells / well) and cultured for 1 day.
  • Preparation Example 1-1 was confirmed to be less irritating than other typical wetting agents having antiseptic functions as shown in FIG.
  • composition containing a high concentration of acylamino acid and acetophenone derivative which has a high antiseptic effect, is excellent in storage stability, and can be easily incorporated into cosmetics.
  • the present invention relates to a composition having high antibacterial properties and high preservability containing a high concentration of an acylamino acid, a hydroxamic acid derivative and a polyhydric alcohol, and a cosmetic comprising the composition.
  • the present invention also relates to a preservative method for cosmetics, which comprises adding the composition.
  • Patent Document 1 ′ As a technique for preserving cosmetics by devising combinations of materials, a method for preserving cosmetics using alkylhydroxamic acid and alcohol (particularly diols) has been proposed (Patent Document 1 ′). However, this method does not have a sufficient antiseptic effect on Aspergillus brasiliensis ⁇ ⁇ . Furthermore, there is a problem that low molecular diols have a great influence on the feeling of use and prescription, and it is not preferable to increase the blending amount so much, and in some cases, the requirement for low irritation may not be satisfied.
  • acylamino acids are known as low-stimulation and high-safety materials.
  • acylproline or a salt thereof has been reported to exhibit a moisturizing effect with excellent hygroscopicity and moisture retention, and to provide a cosmetic with an excellent feeling of use while suppressing the smell of antibacterial agents where odor is a problem.
  • Patent Documents 2 ′ and 3 ′ acylglycine or a salt thereof can be used as a detergent composition that is hypoallergenic and has no sliminess (Patent Document 4 '), and in particular, undecylenoylglycine has anti-acne and anti-dandruff activities (Patent Document 5).
  • Patent Literature Patent Document 1 ′
  • Patent Document 2 Patent Document 2 '
  • Patent Document 3 Patent Document 3
  • Patent Document 4 JP-A-5-156287
  • Patent Document 5 Patent Document 5'
  • EP0983055 Patent Document 6 '
  • the present invention has a high antiseptic effect without adding a preservative such as paraben containing a hydroxamic acid derivative in a high concentration of acylproline and / or acylglycine, has sufficient storage stability, and has a good feeling of use. It is providing the composition which provides.
  • a composition comprising the following (A ′), (B ′) and (C ′):
  • a ′ Acylproline represented by the general formula (I) and a salt thereof:
  • acyl group represented by R 1 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 4 to 18 carbon atoms
  • acyl group represented by R 2 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 6 to 12 carbon atoms
  • R 3 represents an alkyl group having 5 to 11 carbon atoms, an alkenyl group having 5 to 11 carbon atoms, an alkynyl group having 5 to 11 carbon atoms, or an alkoxy group having 5 to 11 carbon atoms
  • C ' Polyhydric alcohol.
  • the acyl group represented by R 1 —CO— is an acyl group derived from a saturated or unsaturated fatty acid having 6 to 14 carbon atoms.
  • Composition [3] (A ′) The composition according to [1] or [2], wherein the acylproline represented by the general formula (I) is decanoylproline.
  • (B ′) The compound represented by the general formula (III ′) is at least one selected from the group consisting of octanohydroxamic acid, heptanohydroxamic acid and hexanohydroxamic acid. [1] The composition according to any one of [5]. [7] The method according to any one of [1] to [6], wherein (C ′) is at least one selected from the group consisting of glycerin, diglycerin, methylpropanediol, dipropylene glycol, and pentylene glycol. Composition.
  • content of (B ′) in the composition is 1.5 to 20% by weight.
  • content of (C ′) in the composition is 4 to 45% by weight.
  • a method for preserving cosmetics comprising the steps of adding the following (A ′), (B ′) and (C ′) to a cosmetic, wherein (A ′) relative to the total weight of the cosmetic:
  • a method comprising adding 0.1 to 10% by weight of the total amount of (B ′) and (C ′) to the cosmetic:
  • (A ′) Acylproline represented by the general formula (I) and a salt thereof:
  • acyl group represented by R 1 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 4 to 18 carbon atoms
  • acyl group represented by R 2 —CO— represents an acyl group derived from a saturated or unsaturated fatty acid having 6 to 12 carbon atoms
  • R 3 represents an alkyl group having 5 to 11 carbon atoms, an alkenyl group having 5 to 11 carbon atoms, an alkynyl group having 5 to 11 carbon atoms, or an alkoxy group having 5 to 11 carbon atoms
  • C ' Polyhydric alcohol.
  • the composition of the present invention contains a high concentration of alkylhydroxamic acid or acylamino acid, a desired amount can be easily added to various cosmetics. According to the present invention, it is possible to provide a cosmetic having excellent storage stability by preventing the growth of not only bacteria but also fungi at a wide pH. Furthermore, according to this invention, the cosmetics which have a desired external appearance and excellent in the usability
  • R 1 —CO— is an acyl group derived from a saturated or unsaturated fatty acid having 4 to 18 carbon atoms, that is, an acyl residue of the saturated or unsaturated fatty acid.
  • the long-chain acyl group represented by R 1 —CO— is an acyl group derived from an acid having a single composition, as well as a natural mixture such as coconut oil fatty acid, castor oil fatty acid, olive oil fatty acid, and palm oil fatty acid. It may be an acyl group derived from a fatty acid or a fatty acid obtained by synthesis (including a branched fatty acid). One of these may be used, or two or more selected from the above group may be mixed and used.
  • the acyl group represented by R 1 —CO— is preferably an acyl group derived from a saturated or unsaturated fatty acid having 6 to 14 carbon atoms, more preferably from a saturated or unsaturated fatty acid having 8 to 12 carbon atoms.
  • the acyl group is more preferably derived, more preferably an acyl group derived from a saturated or unsaturated fatty acid having 8 to 10 carbon atoms, and particularly preferably a decanoyl group.
  • the acylproline represented by the general formula (I) is preferably octanoylproline, decanoylproline, undecylenoylproline, or lauroylproline, and more preferably decanoylproline.
  • R 1 represents a hydrocarbon group having 3 to 17 carbon atoms.
  • the “hydrocarbon group” include a chain hydrocarbon group such as an alkyl group and an alkynyl group, but a chain hydrocarbon group is preferable, and any linear or branched chain can be used. . Of these, an alkyl group is more preferable.
  • the “hydrocarbon group” preferably has 5 to 13 carbon atoms, more preferably 7 to 11, and still more preferably 7 to 9.
  • Examples of the salt of the compound represented by the general formula (I) include pharmacologically acceptable salts, alkali metal salts such as lithium salt, sodium salt and potassium salt; alkalis such as calcium salt and magnesium salt. Examples include earth metal salts; ammonium salts; and basic organic salts. Of these, from the viewpoint of solubility, sodium salts, potassium salts, and ammonium salts are preferable, sodium salts and potassium salts are more preferable, and sodium salts are still more preferable.
  • the compound represented by the formula (I) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • acylproline in the present invention is not particularly limited, and can be easily produced by combining known methods.
  • acylproline can be prepared by the Schotten-Baumann method by simultaneously dropping acid chloride and a base such as sodium hydroxide on proline.
  • the proline may be L, D, or a mixture thereof, but is preferably L.
  • acylglycine [(A'-2) acylglycine]
  • the acylglycine in the present invention is represented by the general formula (II).
  • the acyl group represented by R 2 —CO— is an acyl group derived from a saturated or unsaturated fatty acid having 6 to 12 carbon atoms, that is, an acyl residue of the saturated or unsaturated fatty acid. Examples include hexanoyl group, heptanoyl group, octanoyl group, 2-ethylhexanoyl group, tert-octanoyl group, nonanoyl group, isononanoyl group, decanoyl group, isodecanoyl group, undecylenoyl group, undecanoyl group and lauroyl group.
  • the long-chain acyl group represented by R 2 —CO— is obtained by natural mixed fatty acids such as coconut oil fatty acid and palm kernel oil fatty acid, or by synthesis, in addition to an acyl group derived from an acid having a single composition. It may be an acyl group derived from a fatty acid (including a branched fatty acid). One of these may be used, or two or more selected from the above group may be mixed and used.
  • the acyl group represented by R 2 —CO— is preferably an acyl group derived from a saturated or unsaturated fatty acid having 8 to 11 carbon atoms, more preferably an octanoyl group or an undecylenoyl group.
  • the acyl glycine represented by the general formula (II) is preferably octanoyl glycine, undecylenoyl glycine, and decanoyl glycine, and is preferably octanoyl glycine and undecylenoyl glycine.
  • R 2 represents a hydrocarbon group having 5 to 11 carbon atoms.
  • the “hydrocarbon group” include chain hydrocarbon groups such as an alkyl group and an alkynyl group.
  • a chain hydrocarbon group is preferable, and a straight chain or branched chain group can be used, and an alkyl group is more preferable.
  • the “hydrocarbon group” preferably has 7 to 10 carbon atoms.
  • Examples of the salt of the compound represented by the general formula (II) include pharmacologically acceptable salts, alkali metal salts such as lithium salt, sodium salt and potassium salt; alkalis such as calcium salt and magnesium salt. Examples include earth metal salts; ammonium salts; and basic organic salts. Of these, from the viewpoint of solubility, sodium salts, potassium salts, and ammonium salts are preferable, sodium salts and potassium salts are more preferable, and sodium salts are still more preferable.
  • the compound represented by the formula (II) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • acylglycine in the present invention is not particularly limited, and can be easily produced by combining known methods.
  • acylglycine can be prepared by the Schotten-Baumann method by simultaneously dropping acid chloride and a base such as sodium hydroxide into glycine.
  • (A ′) in the composition of the present invention can be used by mixing one kind or two or more kinds from the group consisting of acylproline and a salt thereof, and acylglycine and a salt thereof.
  • acylproline or a salt thereof is preferable.
  • acylglycine or a salt thereof is usually 0.01 to 50 parts by weight, preferably 0.1 to 20 parts by weight, 0.1 to 10 parts by weight is more preferable.
  • the content of (A ′) in the composition of the present invention is usually 10% by weight or more, preferably 13% by weight or more, more preferably 15% by weight or more with respect to the total weight of the composition.
  • the content of (A ′) is usually 40% by weight or less, preferably 35% by weight or less, more preferably 30% by weight or less.
  • [(B ′) Hydroxamic acid] (B ′) in the present invention is a compound represented by the following general formula (III) or a salt thereof:
  • R 3 represents an alkyl group having 5 to 11 carbon atoms, an alkenyl group having 5 to 11 carbon atoms, an alkynyl group having 5 to 11 carbon atoms, or an alkoxy group having 5 to 11 carbon atoms. Represents a group.
  • alkyl group having 5 to 11 carbon atoms may be either a straight chain or branched chain.
  • an alkyl group having 6 to 10 carbon atoms is preferable, and an alkyl group having 8 carbon atoms is more preferable.
  • alkenyl group having 5 to 11 carbon atoms may be either a straight chain or a branched chain, for example, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, Examples include 3-hexenyl, 5-hexenyl, 1-heptenyl, 1-octenyl, 1-nonenyl, 1-decenyl, 1-undecenyl and the like. Among them, an alkenyl group having 6 to 10 carbon atoms is preferable, and an alkenyl group having 8 carbon atoms is more preferable.
  • alkynyl group having 5 to 11 carbon atoms may be either a straight chain or branched chain.
  • 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 4-methyl-3-pentynyl examples include 1-hexynyl, 3-hexynyl, 5-hexynyl, 1-heptynyl, 1-octynyl, 1-noninyl, 1-decynyl, 1-undecynyl and the like.
  • an alkynyl group having 6 to 10 carbon atoms is preferable, and an alkynyl group having 8 carbon atoms is more preferable.
  • alkoxy group having 5 to 11 carbon atoms examples include pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy and undecyloxy. Among these, an alkoxy group having 6 to 10 carbon atoms is preferable, and an alkoxy group having 8 carbon atoms is more preferable.
  • octanohydroxamic acid As the compound represented by the general formula (III ′), octanohydroxamic acid, heptanohydroxamic acid and hexanohydroxamic acid are preferable, and octanohydroxamic acid is more preferable.
  • Examples of the salt of the compound represented by the general formula (III ′) include pharmacologically acceptable salts, alkali metal salts such as lithium salts, sodium salts, potassium salts; calcium salts, magnesium salts, etc. Examples include alkaline earth metal salts; ammonium salts; and basic organic salts. Among these, from the viewpoint of versatility, sodium salt, potassium salt, and ammonium salt are preferable, sodium salt and potassium salt are more preferable, and sodium salt is more preferable.
  • the compound represented by the formula (III ′) may be a hydrate, a non-hydrate, a non-solvate or a solvate.
  • any of a chemical synthesis method, a natural product derived from an animal or a plant, a fermentation method or a gene recombination method may be used.
  • it can be synthesized by reacting a corresponding alkylhydroxylamine with an active carbonyl compound such as an active ester or acid chloride.
  • the content of (B ′) in the composition of the present invention is usually preferably 1.5% by weight or more and 2% by weight or more from the viewpoint of use of the composition in cosmetics.
  • the content of (B ′) is usually 20% by weight or less, preferably 10% by weight or less, more preferably 8% by weight or less, and further preferably 6% by weight or less.
  • (B ′) is 1 part by weight
  • (A ′) is usually 0.1 to 50 parts by weight, preferably 0.2 to 25 parts by weight, More preferred is ⁇ 20 parts by weight, and particularly preferred is 1 to 14 parts by weight.
  • the total weight of (A ′) and (B ′) is usually 8% by weight or more, preferably 10% by weight or more, based on the total weight of the composition. Preferably it is 15 weight% or more, More preferably, it is 18 weight% or more, Most preferably, it is 20 weight% or more, Usually, it is 80 weight% or less, and 60 weight% or less is preferable.
  • a polyhydric alcohol means the compound which has 2 or more of hydroxyl groups in 1 molecule.
  • caprylyl glycol and 1,3-propanediol are excluded.
  • glycerin, diglycerin, methylpropanediol, dipropylene glycol, propylene glycol (1,2-propanediol), and pentylene glycol are preferred from the viewpoint of long-term storage stability and availability.
  • Glycerin, methylpropanediol (2-methyl-1,3-propanediol), dipropylene glycol, pentylene glycol (1,2-pentanediol) are more preferred from the viewpoint of low viscosity reduction when blended into cosmetics.
  • Glycerin is more preferable from the viewpoint of versatility and low irritation.
  • These polyhydric alcohols can be used singly or in combination of two or more.
  • any of commercially available products, chemical synthesis methods, natural products derived from animals and plants, those obtained by fermentation methods or gene recombination methods may be used.
  • the content of (C ′) in the composition of the present invention is usually 4% by weight or more, preferably 5% by weight or more, and preferably 6% by weight or more based on the total weight of the composition from the viewpoint of storage stability. Is more preferable, and 8% by weight or more is more preferable.
  • the content of (C ′) is usually 45% by weight or less, preferably 40% by weight or less.
  • (A ′) is usually 10 to 40% by weight, (B ′) is 1.5 to 20% by weight, and (C ′) based on the total weight of the composition of the present invention. 4 to 45% by weight, (A ′) 13 to 35% by weight, (B ′) 1.5 to 10% by weight, and (C ′) 6 to 40% by weight. More preferably, (A ′) is blended in an amount of 15 to 30% by weight, (B ′) in an amount of 2 to 8% by weight, and (C ′) in an amount of 6 to 40% by weight.
  • the weight ratio of (A ′) and (C ′) to (B ′) (( A ′) + (C ′)) / (B ′) usually exceeds 7.
  • the weight ratio is preferably 7.5 or more, more preferably 7.7 or more, and particularly preferably 8.0 or more. If it is the range of this numerical value, the composition excellent in long-term storage stability can be provided.
  • the upper limit is ((A ′) + (C ′)) / (B ′) of 50 or less, preferably 40 or less.
  • water As the component (D ′), either hard water or soft water may be used.
  • water natural water, ground water, tap water, ion exchange water, purified water, distilled water, ultrapure water, or the like can be used. .
  • the content of (D ′) in the composition of the present invention is usually 20% by weight or more, preferably 30% by weight or more, and 42% by weight with respect to the total weight of the composition. % Or more is more preferable. Further, the content of (D ′) is usually 80% by weight or less, and preferably 64% by weight or less.
  • the pH of the composition of the present invention is preferably 4.5 or more from the viewpoint of long-term storage stability and ease of production. Moreover, pH 8 or less is preferable.
  • composition of the present invention can be used as an antibacterial composition (antibacterial agent), an antiseptic composition (preservative) or an auxiliary agent thereof.
  • Antibacterial agents, preservatives, or their adjuvants can be produced by a known method by adding the additives described later, even with the composition of the present invention alone.
  • antibacterial means not to increase bacteria for a long time, and means to suppress the growth of bacteria on the surface of a composition such as cosmetics.
  • preservation means preventing invasion, growth, and proliferation of microorganisms so that no spoilage or fermentation occurs. Therefore, the “preservative effect” means an effect of suppressing the growth of fungi such as fungi and bacteria to prevent the cosmetic material from deteriorating and enhancing its preservability.
  • composition of the present invention is not particularly limited, and can take any form such as liquid, emulsion, paste, gel, solid, and powder. Of these, liquid, emulsion, paste, and gel are preferable.
  • a cosmetic comprising the composition of the present invention is also included in the present invention.
  • the cosmetic may contain only the composition of the present invention, or a component that may be usually added to the cosmetic is effective for the present invention. You may mix
  • oil agents, chelating agents, surfactants, powders, amino acids, polyamino acids and salts thereof, lower alcohols, animal and plant extracts, nucleic acids, vitamins, enzymes, anti-inflammatory agents, bactericides, antiseptics, antiseptics Examples include oxidants, humectants, thickeners, viscosity modifiers, ultraviolet absorbers, antiperspirants, pigments, dyes, fragrances, pH adjusters, pearlizing agents, wetting agents, and the like. These are merely examples, and other components may be added as a matter of course.
  • Oils include fatty acids such as isostearic acid, undecylenic acid, oleic acid; myristyl myristate, hexyl laurate, decyl oleate, isopropyl myristate, hexyldecyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, monostearic acid Esters such as ethylene glycol, cetyl octoate, octyl oxystearate, alkyl benzoate; hydrocarbons such as liquid paraffin, polyisobutene, petrolatum, squalane; waxes such as lanolin, reduced lanolin and carnauba wax; silicone oils; mink oil; Fats and oils such as cocoa oil, coconut oil, palm kernel oil, camellia oil, sesame oil, castor oil, olive oil, jojoba oil; ethylene / ⁇ -olefin / co-oligomer
  • silicone oils include methylpolysiloxane, highly polymerized methylpolysiloxane, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer, and poly (oxyethylene, oxypropylene) / methyl.
  • Ether-modified silicone such as polysiloxane copolymer; stearoxymethyl polysiloxane; methyl hydrogen polysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, tetrahydrotetramethylcyclotetrasiloxane, methylcyclopolysiloxane and dodecamethylcyclohexyl Cyclic silicones such as sasiloxane; amino-modified silicones such as methylphenylpolysiloxane and aminoethylaminopropylsiloxane / dimethylsiloxane copolymer Corn: Low molecular silicone compounds such as stearoxytrimethylsilane and trimethylsiloxysilicic acid; silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polys
  • the chelating agent is not particularly limited, but preferably triethylenetetramine, 2-thenoyltrifluoroacetone, thioglycolic acid, tartaric acid, succinic acid, 8-quinolinol, pyridine-2,6-dicarboxylic acid, pyridine, 1, 10-phenanthroline, lactic acid, 8-hydroxyquinoline-5-sulfonic acid, glycine, 2,2′-pyridylethylenediamine, aurintricarboxylic acid, xylenol orange, 5-sulfosalicylic acid, salicylic acid, pyrocatechol-3,5-disulfonate, 4,5-dihydroxybenzene-1,3-disulfonic acid, 1,2-diaminocyclohexane-N, N, N ′, N′-tetraacetic acid, citric acid, oxalate, nitrilotriacetic acid, ethylenediamine-N,
  • the surfactant examples include N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts, N-long chain fatty acid acyl-N-methyl taurine salts, alkyls.
  • Anionic surfactants such as sulfates and their alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak base salts, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids; Ether type surfactants such as glycerin ether and its alkylene oxide adduct, ether ester type surfactants such as alkylene oxide adduct of glycerin ester, alkylene oxide adduct of sorbitan ester, polyoxyalkylene fatty acid ester, glycerin ester Ester type surfactants such as fatty acid polyglycerin ester, sorbitan ester, sucrose fatty acid ester, alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and its ethylene oxide adduct, and nonionic surfactants
  • the powder examples include resin powders such as nylon beads and silicone beads, nylon powder, metal fatty acid soap, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, cobalt oxide, carbon black, ultramarine, bitumen, Zinc oxide, titanium oxide, zirconium oxide, silicon oxide, aluminum oxide, cerium oxide, titanium mica, boron nitride, barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate, silicon carbide, dye, lake, sericite, mica , Talc, kaolin, plate-like barium sulfate, butterfly-like barium sulfate, fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, acyl lysine, acyl glutamic acid, acyl arginine, acyl glycine, and the like, and further silicone treatment, Fluorine compound Management, silane coupling agent treatment, silane treatment, organic titanate process, acylated lysine treatment, fatty acid treatment,
  • amino acids examples include glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, isoleucine, leucine, and valine.
  • polyamino acids and salts thereof examples include polyglutamic acid and polyaspartic acid.
  • lower alcohols examples include ethanol and propanol.
  • nucleic acids disodium 5′-inosinate, disodium 5′-uridylate, etc .
  • vitamins vitamins A, C, etc. and derivatives thereof
  • anti-inflammatory agent is potassium glycyrrhizinate, etc .
  • bactericidal agent is triclosan, trichlorocarban, octopirox, zinc pyrithione, etc .
  • antiseptic is methyl paraben, butyl paraben, etc .
  • pigments Tar dyes, inorganic dyes, Natural base-derived pigments, etc .; fragrances; pH adjusting agents such as citric acid, trisodium citrate, sodium carbonate, phosphoric acid, etc .; Pearling agents such as ethylene glycol distearate, etc .; Wetting agents such as betaine Is mentioned.
  • Examples of the cosmetics of the present invention include face wash, lotion, milky lotion, cream, gel, cosmetic liquid, pack, mask, soap, body shampoo, white powder, foundation, lipstick, teak, eyeliner, mascara, eye shadow, Skin cosmetics such as eyebrows, and hair cosmetics such as shampoos, rinses, hair conditioners, hair styling agents, hair treatments and the like. It can be any cosmetics, but it can be used for face wash, lotion, milk, cream, gel, beauty essence, pack, mask, body shampoo and other skin cosmetics, shampoo, rinse, hair conditioner, hair treatment, etc. It is preferable to use a cosmetic for hair. Moreover, it is more preferable to use a cosmetic for skin that requires moisturizing.
  • compositions and cosmetics of the present invention are not particularly limited, and in addition to the essential components (A ′), (B ′) and (C ′), a cosmetic composition is produced as necessary.
  • Various components necessary for the above can be appropriately selected and blended, and can be produced by conventional methods.
  • the blending amount of the composition of the present invention to be blended with the cosmetic is: It is preferably 0.1% to 10% by weight, more preferably 0.3% to 6% by weight, and particularly preferably 0.5% to 4% by weight based on the total weight of the cosmetic.
  • the antiseptic method for cosmetics including the step of adding (A ′), (B ′) and (C ′) to the cosmetic is also the second aspect of the present invention.
  • the order of adding (A ′), (B ′) and (C ′) may be added first or simultaneously.
  • Each definition is as described above.
  • the added amount of (A ′), (B ′) and (C ′) is usually 0.1% of the total amount of (A ′), (B ′) and (C ′) with respect to the total weight of the cosmetic. -10% by weight, preferably 0.2-7.0% by weight, more preferably 0.5-6.0% by weight.
  • the present invention also includes a preservative enhancer of hydroxamic acid represented by the above general formula (III ′) or a salt thereof (B ′), which contains the above (A ′).
  • (B ′) is usually 0.1 to 50 parts by weight, preferably 0.2 to 25 parts by weight, and more preferably 0 to 1 part by weight of (B ′). 8 to 20 parts by weight, particularly preferably 1 to 14 parts by weight.
  • Other definitions are as described above.
  • % means “% by weight”.
  • Octanoyl glycine was synthesized by a method similar to Synthesis Example 1 using glycine (Ajinomoto Co.) and octanoyl chloride (Tokyo Kasei Co., Ltd.). That is, glycine (manufactured by Ajinomoto Co., Inc.) was dissolved in water, and octanoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) and a 25% aqueous sodium hydroxide solution were added while adjusting the pH to 12. 75% sulfuric acid was added for neutralization, and the aqueous layer was removed. Water and ethyl acetate were further added to remove the aqueous layer. Ethyl acetate was distilled off under reduced pressure to obtain octanoylglycine.
  • glycine manufactured by Ajinomoto Co., Inc.
  • octanoyl chloride manufactured by Tokyo Chemical Industry Co., Ltd.
  • the uniformity of the obtained sample was visually determined based on the following criteria.
  • (Criteria) ⁇ A transparent and uniform composition can be obtained. ⁇ It is an opaque viscous liquid as a whole, but it is uniformly mixed. X Insoluble matter, precipitation, etc. are seen, and it is a non-uniform solution.
  • Example 2A Long-term storage stability test at low temperature and high temperature
  • the composition was filled in a transparent glass bottle having a capacity of 10 mL, and the container was covered and allowed to stand at -5 ° C, 25 ° C and 50 ° C.
  • -5 °C low temperature storage
  • the composition of the composition uniformity (presence / absence of separation), presence / absence of freezing, presence / absence of precipitation) of the composition immediately after removal from the storage for every 3 months for 12 months
  • the determination was made visually based on the following criteria. With regard to 50 ° C.
  • a lotion containing no composition of the examples a lotion containing 1.0% by weight of decanoylproline, and a lotion containing 0.12% by weight of octanohydroxamic acid were prepared in the same manner, and the control was performed.
  • Reference Examples 1 to 3 were used for the following evaluations. The numerical values in the table indicate% by weight.
  • Anti-mold test (1) to the lotion 1mL prepared as, Aspergillus niger as initial number of bacteria of 10 5 cells per 1mL (Aspergillus brasiliensis (Ab)) is added to bacterial solution.
  • (2) Store the formulation of (1) at 25 ° C. for 7 days.
  • the stickiness and squeakiness within 1 minute after application are scored according to the following criteria. The average score was obtained and the feeling of use was evaluated.
  • the composition of the present invention has a high antiseptic effect and excellent storage stability, and further contains a high concentration of alkylhydroxamic acid and acylamino acid, so that a desired amount can be easily blended in various cosmetics, etc. Ideal for manufacturing.

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Abstract

La présente invention concerne une composition qui présente d'excellentes propriétés antiseptiques et une stabilité en stockage élevée et qui contient : un dérivé d'acétophénone et un polyol dans un acyl-aminoacide fortement concentré ; ou un dérivé d'acide hydroxamique et un polyol dans un acyl-aminoacide fortement concentré.
PCT/JP2017/042924 2016-11-30 2017-11-29 Composition riche en acyl-aminoacides WO2018101370A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003226636A (ja) * 2002-01-31 2003-08-12 Noevir Co Ltd 弱酸性洗浄料
WO2009070736A1 (fr) * 2007-11-29 2009-06-04 Inolex Investment Corporation Conservateurs pour compositions cosmétiques, de toilette et pharmaceutiques
WO2014007290A1 (fr) * 2012-07-03 2014-01-09 味の素株式会社 Hydratant et produit cosmétique le comprenant
JP2014172908A (ja) * 2013-03-08 2014-09-22 Symrise Ag 抗菌組成物
WO2016195038A1 (fr) * 2015-06-02 2016-12-08 味の素株式会社 Composition cosmétique contenant de l'acylproline
JP2016222669A (ja) * 2015-06-02 2016-12-28 味の素株式会社 化粧料組成物
JP2017190330A (ja) * 2016-04-12 2017-10-19 ミョンジン ニューテック カンパニー リミッテド ラウリルピリジニウムクロリドを含むウェットティッシュ原緞における拡散性が増加したウェットティッシュ組成物及びそのウェットティッシュ

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003226636A (ja) * 2002-01-31 2003-08-12 Noevir Co Ltd 弱酸性洗浄料
WO2009070736A1 (fr) * 2007-11-29 2009-06-04 Inolex Investment Corporation Conservateurs pour compositions cosmétiques, de toilette et pharmaceutiques
WO2014007290A1 (fr) * 2012-07-03 2014-01-09 味の素株式会社 Hydratant et produit cosmétique le comprenant
JP2014172908A (ja) * 2013-03-08 2014-09-22 Symrise Ag 抗菌組成物
WO2016195038A1 (fr) * 2015-06-02 2016-12-08 味の素株式会社 Composition cosmétique contenant de l'acylproline
JP2016222669A (ja) * 2015-06-02 2016-12-28 味の素株式会社 化粧料組成物
JP2017190330A (ja) * 2016-04-12 2017-10-19 ミョンジン ニューテック カンパニー リミッテド ラウリルピリジニウムクロリドを含むウェットティッシュ原緞における拡散性が増加したウェットティッシュ組成物及びそのウェットティッシュ

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