WO2007132710A1 - Agent bactéricide/conservateur - Google Patents

Agent bactéricide/conservateur Download PDF

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Publication number
WO2007132710A1
WO2007132710A1 PCT/JP2007/059590 JP2007059590W WO2007132710A1 WO 2007132710 A1 WO2007132710 A1 WO 2007132710A1 JP 2007059590 W JP2007059590 W JP 2007059590W WO 2007132710 A1 WO2007132710 A1 WO 2007132710A1
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WO
WIPO (PCT)
Prior art keywords
mass
preservative
bactericidal
rutin
parts
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Application number
PCT/JP2007/059590
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English (en)
Japanese (ja)
Inventor
Makoto Takeuchi
Noriko Mori
Hiromi Tatsukawa
Original Assignee
Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo filed Critical Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
Priority to JP2008515499A priority Critical patent/JP5145214B2/ja
Publication of WO2007132710A1 publication Critical patent/WO2007132710A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Definitions

  • the present invention relates to a novel disinfectant / preservative and its use.
  • preparations for external use on skin such as cosmetics are required to be prepared so as not to contain microorganisms as much as possible.
  • preservatives are usually used because it is impossible to prevent microbial contamination and growth during use.
  • a bactericidal agent will be used depending on the dosage form of the external preparation for skin, it may not be physically sterilized during the production, and in such a case, a bactericidal agent will be used.
  • Raw materials applied to the external preparation for skin as a bactericidal agent or preservative include, for example, organic acids such as benzoic acid and dehydroacetic acid, alcohols such as phenylethanol and phenoxyisopropyl alcohol, hydroxybenzoic acid There are phenols such as esters and chlortaresol, ammonium salts such as benzalkonium chloride and benzethonium chloride, and chlorhexidine, propylene glycol, photosensitizer 101 and photosensitizer 201.
  • Photosensitive Element 101 and Photosensitive Element 201 exhibit remarkable sterilization and antiseptic properties at low concentrations, so that sterilization against acne bacteria is possible in addition to general cosmetics such as basic cosmetics, finished cosmetics, and hair cosmetics. For example, it is widely used as an active ingredient in quasi-drugs such as acne agents that use growth-inhibiting ability.
  • quasi-drugs such as acne agents that use growth-inhibiting ability.
  • force cyanine dyes such as Photosensitive Element 101 and Photosensitive Element 201 have low light resistance compared to the above-mentioned other sterilizing / preserving agents due to the chemical structure. When exposed to ambient light such as natural light or artificial light in a dissolved state, it decomposes in a short time.
  • the problem to be solved by the present invention is to provide a sterilizing / preservative that does not easily decompose the sterilizing / preserving component even when exposed to ambient light such as natural light or artificial light. It is in [0006] Further, the problem to be solved by the present invention is to provide the use of such a bactericidal / preservative, in particular, a skin external preparation such as cosmetics.
  • the present invention provides a bactericidal / preservative comprising a cyanine dye represented by the general formula 1 or 2 as a bactericidal / preservative component and rutin or a sugar derivative thereof as a component for enhancing the light resistance of the cyanine dye.
  • a bactericidal / preservative comprising a cyanine dye represented by the general formula 1 or 2 as a bactericidal / preservative component and rutin or a sugar derivative thereof as a component for enhancing the light resistance of the cyanine dye.
  • the problem is solved by providing an agent.
  • R to R are the same or different aliphatic hydrocarbon groups.
  • aliphatic hydrocarbon groups may have a substituent.
  • I 3 represents an appropriate anion.
  • the present invention solves the above-mentioned problems by providing a skin external preparation containing such a bactericidal / preservative.
  • the sterilizing 'preservative according to the present invention is sterilized even when exposed to ambient light such as natural light and artificial light.
  • topical skin preparations such as cosmetics using such antibacterial / preservatives can be used for growth of microorganisms mixed during preparation or use even in the form of solutions, emulsions, gels, and the like.
  • quasi-drugs containing the cyanine dyes represented by the general formula 1 or 2 as an active ingredient have the advantage that the bactericidal ability and the like are not easily reduced for a long time.
  • the present invention comprises a cyanine dye represented by the general formula 1 or 2 as a sterilizing / preserving component, and rutin or a sugar derivative thereof as a component that enhances the light resistance of the cyanine dye. Containing sterilization / preservative and its use.
  • R to R are the same or different aliphatic hydrocarbon groups.
  • aliphatic hydrocarbon group a linear or branched group having up to 20 carbon atoms, usually having up to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an isopropenyl group, 1 propenyl group, 2-propenyl group, 2-propynyl group, butyl group, isobutyl group, see butyl group, tert_butyl group, 2-butyr group, 1,3_butadienyl group, pentyl group, isopentyl Group, neopentyl group, tert_pentyl group, 1-methylpentyl group, 2-methylpentyl group, hexyl group, 2_pentenyl group, 2_pentene_4_ynyl group, isohexyl group, 5_methylhexyl Group, heptyl group, octyl group, non
  • one or more of its hydrogen atoms are in a hydroxy group or within the range not departing from the object of the present invention.
  • methoxy group, trifluoromethoxy group, ethoxy group, propoxy Group isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert butoxy group, pentyloxy group, phenoxy group, benzyloxy group and the like, which may be substituted.
  • cyanine dyes represented by the general formulas 1 and 2 those having two or more similar cyclic groups in the molecule, and those having a cyclic group strength S each having an aliphatic hydrocarbon group In terms of ease of preparation, their aliphatic hydrocarbon groups are conveniently the same as each other.
  • X— or X— represents an appropriate anion, and each anion
  • inorganic ions such as fluorine ion, chlorine ion, bromine ion, iodine ion, perchlorate ion, perbromate ion, periodate ion, nitrate ion, sulfate ion, phosphate ion, borate ion, etc.
  • iodine ions are particularly preferable because they have sterilizing and antiseptic properties.
  • cyanine dyes include those represented by chemical formulas 1 to 10. None of these cause substantial damage to the human body. Prominent bactericidal activity against microorganisms to be excluded in topical skin preparations, for example, microorganisms of the genus Alpergillus, Escherichia, Candida, Corynebacterium, Syudomonas, Staphylococcus, and Noctilus Demonstrate.
  • the cyanine dyes represented by the chemical formulas 1 to 10 those represented by the chemical formulas 2 and 7 have particularly high bactericidal and antiseptic properties and are moderately soluble in various solvents commonly used for external preparations for skin. It is particularly preferable since it has the properties.
  • the cyanine dyes represented by Chemical Formulas 2 and 7 have specifications that are compatible with topical skin preparations such as cosmetics and quasi-drugs, respectively, as “Pionin” (Photosensitive Element 201) and “Platonin” (Photosensitive Element). No. 101) is sold under the product name.
  • rutin as used in the present invention is a kind of flavonol glycoside represented by the chemical formula 11.
  • (Taercetin _3-rutinoside) for example, natural ones derived from plants such as laceae, legumes and citrus can be easily obtained.
  • the rutin sugar derivative referred to in the present invention means one in which a sugar residue is bonded to one or more of the hydroxy groups in the chemical formula 11, and in particular, the same patent application in terms of availability.
  • rutin is known to have a high purity product with pale yellow needles
  • a high-purity product but also a relatively low-purity product of natural origin prepared from a plant of the family Taceae, Legumes, Citrus, Synthetic products or semi-synthetic products, and also specific to rutin sugar derivatives and preparation methods such as those described above, which are obtained by enzymatic treatment of these in the presence of a partially degraded starch, such as unreacted rutin and starch. It may be a composition in which impurities such as partially decomposed products are naturally integrated.
  • the sterilizing “preservative” is a sterilizing “preservative” containing one or more cyanine dyes as described above, and rutin and Z or a sugar derivative thereof.
  • the content of rutin and / or its sugar derivative in such a sterilizing / preservative depends on the type and use of the individual skin external preparations to which the sterilizing 'preservative is applied, but is generally expressed in terms of solids as a general formula 1 or More than 0.01 parts by weight, preferably 0.1 to 1,000 parts by weight, more preferably 1 to 500 parts by weight, per 1 part by weight of the cyanine dye represented by 2.
  • the amount of rutin and / or a sugar derivative thereof is less than 0.01 parts by mass relative to 1 part by mass of the cyanine dye represented by the general formula 1 or 2, the light resistance of the cyanine dye cannot be substantially increased, and 1 Even if the amount exceeds 000 parts by mass, the effect of increasing light resistance has peaked, and the yellow color inherent to rutin or its sugar derivatives has become conspicuous, and this may impair commercial value depending on the application. Usually, it is adjusted in the range of 0.01 to 1,000 parts by mass.
  • the sterilizing / preserving agent of the present invention exhibits a remarkable sterilizing / preserving ability in any of liquid, solid and semi-solid.
  • the solvent is not particularly limited as long as the cyanine dye represented by the general formula 1 or 2 and rutin or a sugar derivative thereof are substantially dissolved, and is commonly used in skin external preparations such as cosmetics.
  • Dermatologically acceptable for example, water, ethanol, propanol monoole, isopropanol, glycerin, ethylene glycolanol, propylene glycolanol, butylene glycol, 1,2_pentanediol, 1,2-hexane Alcohols such as diol, 1,2-heptanediol, 1,2-octanediol and low molecular weight polyols are listed, and these are used in combination as necessary.
  • polyoxyethylene alkyl ether polyoxyethylene lauryl ether, polyoxyethylene myristyl ether
  • polyoxyethylene can be used as a solubilizer.
  • surfactants such as ethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene oleyl cetyl ether, polyoxyethylene beenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene noyl phenyl ether , Heat and stir.
  • concentration of cyanine dye in the solution-like disinfectant 'preservative according to the present invention should be set as appropriate, when it is made into a product as a disinfectant / preservative, up to 20% by weight of cyanine dye is usually 0.01. Add or subtract 10% by mass.
  • the use of the sterilizing / preservative according to the present invention will be described.
  • the sterilizing / preservative according to the present invention has a remarkable sterilizing / preserving action without causing substantial damage to the human body. Because it is hard to be attenuated even in an environment exposed to ambient light, such as natural light and artificial light, and sterilized 'preservative ability', sterilization 'preservatives are required, especially in cosmetics and pharmaceutical departments It is extremely useful in the field of external preparations for skin including external products.
  • Skin external preparations to which the sterilizing / preservative according to the present invention can be applied include, for example, face wash sarcophagus, face wash cream, face wash foam, cleansing cream, cleansing jewel, coronole cream, lotion, massage cream, milky lotion, beauty Basic and whitening cosmetics such as liquids, moisturizing creams, vanishing creams, hyzenic creams, packs, powder foundations, cake foundations, amphibious foundations, stick foundations, cream foundations, liquid foundations, white powders, makeup bases, lipsticks, eye shadows Finishing cosmetics such as eyeliner, mascara, hairbrow, scarlet, nail enamel, body cream, body lotion, massage cream, body powder, etc.
  • external preparations and other external preparations for skin are mentioned, and the disinfectant / preservative according to the present invention disinfects microorganisms in such external preparations for skin and effectively suppresses the growth of microorganisms.
  • Such an external preparation for skin is used together with the bactericidal / preservative according to the present invention, for example, water, acetone, toluene, ethyl methyl ketone, isobutyl methyl ketone, cyclohexane, butanol, isoamyl acetate, ethyl acetate.
  • Solvents such as butyl acetate, avocado oil, almond oil, olive oil, cacao oil, sesame oil, safflower oil, soybean oil, camellia oil, versic oil, castor oil, mink oil, cottonseed oil, molasses, palm oil, egg yolk oil Fats and oils such as sperm oil, sperm whale oil, beeswax, whale wax, lanolin, jojoba oil, carnauba wax, canderia wax, montan wax, liquid paraffin, petrolatum, paraffin, ozokerite, stiilene, microcrystalline wax, Polyethylene powder, screen, scalar , Hydrocarbons such as pristane, fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, 12-hydroxystearic acid, tonole oil, lanolin fatty acid, ethanol, isopropanol, lauryl alcohol, cetanol Nore, stearyl alcohol,
  • UV absorber lactic acid, tartaric acid, succinic acid, citrate, boric acid, allantoin, allantoin hydroxyaluminum, zinc chloride, calamine, zinc sulfate, zinc p-phenol sulfonate, potassium aluminum sulfate, resorcinol, resorcinol, ferric chloride , Edeto disodium, sodium Tae phosphate, sodium polyphosphate, sequestering agents, such as sodium metaphosphate, chondroitin sodium sulfate, 1, 3 - butylene glycol, sodium lactate, maltitol, humectants such as xylitol,
  • amino acids, vitamins, hormones, fragrances, colorants, antifungal agents, antibiotics, antiperspirants, deodorants, skin bleaches, organic bases, aerosol propellants that are widely used in cosmetics It can be prepared by appropriately blending organic chemicals, inorganic chemicals, insect repellents, wound healing agents, antih
  • the amount of the bactericidal / preservative of this invention in such a topical skin preparation depends on the intended use of the topical skin preparation, but in the case of cosmetics, the concentration of cyanine pigment is 0.002% by mass, In the case of quasi-drugs, the dosage is adjusted up to 0.005% by mass.
  • the sterilizing and preservative referred to in this invention is not limited to an independent form in which the cyanine dye represented by the general formula 1 or 2 and rutin or a sugar derivative thereof are mixed in advance.
  • a form of skin external preparation in which cyanine pigment and rutin or its sugar derivative are individually added to an application target such as an external preparation for skin, and both are formulated so as to have the desired effect there.
  • the sterilizing / preserving agent according to the present invention is a sterilizing / preserving component within the range not departing from the object of the present invention, as well as other cyanine dyes represented by the general formulas 1 and 2, and other commonly used in the field.
  • Disinfection 'Preservatives for example, organic acids such as benzoic acid and dehydroacetic acid, alcohols such as phenylethanol, phenoxyisopropyl pill alcohol, phenols such as hydroxybenzoic acid ester and chronolecresol, benzalkonium chloride, benzethonium chloride Ammonium salts such as chlorohexidine, propylene glycol, etc., or a combination of one or more of them.
  • Photosensitizer 101 which is a cyanine dye represented by Chemical Formula 7, or Chemical Formula 2 Test solution 1 to 10 containing or not containing noretine, ⁇ -darcosylrutin, hesperidin or ⁇ -darcosyl hesperidin together with any of photosensitizer 201, which is a cyanine dye represented by Each was prepared.
  • install a fluorescent lamp (rated power 15 W, wavelength 380 to 700 nm) so that the light intensity on the surface of the quartz tube is 2.7 mW / cm 2 at a wavelength of 413 nm.
  • test solution was sampled over time, and artificial light from a fluorescent lamp was irradiated for 40 hours. Incidentally, the characteristic yellow color becomes conspicuous in solutions of rutin, hesperidin and their sugar derivatives when the concentration force exceeds 1% by mass.
  • rutin rutin, hesperidin and their sugar derivatives when the concentration force exceeds 1% by mass.
  • methanol / water mixture volume ratio 85:15
  • the remaining cyanine dye was quantified by applying high performance liquid chromatography using as an eluent.
  • test solutions 1, 2, 6 and 7 combined with either rutin or ⁇ -darcosylrutin showed no errors due to analysis even when irradiated with artificial light for 40 hours. Within the range, the cyanine dye was hardly decomposed. In contrast, the control test solutions 5 and 10 containing no rutin or a sugar derivative thereof were similarly irradiated with light, and the amount of cyanine dye was reduced to less than one-fourth of the initial value after 20 hours. After 40 hours, the degradation of cyanine dye progressed beyond detection.
  • Control solutions 3, 4, 8, and 9 to which hesperidin and sarcosine hesperidin were added were able to detect very little cyanine dye after 40 hours, but increased the light resistance of cyanine dye. From the viewpoint, both were far from the test solution containing rutin and hyaldarcosilrutin.
  • rutin and hesperidin show clearly different behaviors regarding the light resistance of Photosensitive Element 201 and Photosensitive Element 101, which are representative cyanine dyes represented by the general formulas 1 and 2. It was. As is well known, rutin and hesperidin are both analogs having a benzopyran skeleton and a lutinose residue bonded to the benzopyran skeleton. is there. Nevertheless, it was a surprising fact that they behave so differently.
  • the concentrations of rutin and its sugar derivatives ⁇ -darcosylrutin, unimaltosylrutin and unimaltotriosylrutin were set to 0.001.
  • the test was performed in the range of mass% in the same manner as described above, when 40 hours had passed, 70% or more of the cyanine dye remained without being decomposed.
  • cyanine dyes and rutin represented by Chemical Formula 1, Chemical Formulas 3 to 6 and Chemical Formulas 8 to 10 Hirudarukosylrutin, Hiichi Martosyl Rutin and Himaltotriosyl
  • the light resistance was remarkably increased and decomposed by the coexistence of rutin or one darcosylrutin. It turned out to be difficult.
  • the bactericidal / preservative ability of cyanine dyes represented by chemical formulas 1 to 10 did not decrease even in the presence of rutin or its sugar derivative.
  • Polyoxyethylene cetyl ether ( ⁇ 20) was added as a solubilizer to an appropriate amount of 1,2-pentanediol to a concentration of 10% by mass, and Photosensitizer 201 (produced by Hayashibara Biochemical Research Institute, The product name “Pionin”) and Hi-Dalcocilrutin (sold by Hayashibara Biochemical Laboratories Co., Ltd., trade name “Hi-G-Rutin”) are dissolved to a concentration of 1 and 3% by mass, respectively. The sterilization-like preservative was obtained.
  • a—Gnolecosyl Noretin has a remarkable anti-oxidant ability, and even if it is exposed to ambient light such as natural light and artificial light, the bactericidal / preservative ability of this example is difficult to decrease. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.
  • a solution-like disinfectant / preservative according to the present invention was obtained in the same manner as in Example 1 except that 1,3-butylene glycol was used in place of 1,2-pentanediol.
  • a—Gnolecosyl Noretin has a remarkable antioxidative ability, and even if it is exposed to ambient light such as natural light and artificial light, the bactericidal / preservative of this example is difficult to decrease. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.
  • Example except that high purity rutin (manufactured by Tokiwa Plant Chemical Laboratory Co., Ltd., purity of 95% or more) was blended to a concentration of 1% by mass instead of a-gnolecosyl noretin
  • Sterilization and antiseptics of this example which have remarkable antioxidant ability by rutin and are not easily reduced even when exposed to ambient light such as natural light and artificial light. It is extremely useful for topical skin preparations.
  • Photosensitive Element 101 (trade name “Platonin”, manufactured by Hayashibara Biochemical Laboratories, Inc.) is blended to a concentration of 0.04% by mass, and the concentration of Hirudarukosyl rutin is 20
  • a solution-like sterilizing / preserving agent according to the present invention was obtained in the same manner as in Example 1 except that the mass% was changed.
  • a—Gnolecosyl Noretin has a remarkable anti-oxidant ability, and even if exposed to ambient light such as natural light and artificial light, the bactericidal / preservative of this example is unlikely to deteriorate. It is extremely useful in skin external preparations such as cosmetics and quasi drugs.
  • the disinfectant 'preservative obtained by the method of Example 1 was blended to a concentration of 0.005% by mass in accordance with a conventional method. Got water.
  • Oleic acid ester (20EO) 2.0 parts by mass
  • the skin lotion of the present example which has excellent skin cleansing power and does not irritate the skin, hardly grows microorganisms even when used for a long period of time.
  • this invention was formulated by blending the disinfectant / preservative obtained by the method of Example 2 to a concentration of 0.008% by mass according to a conventional method.
  • the emollient cream was obtained.
  • the emollient cream of this example which is excellent in moisture retention and spreadability of the skin and does not irritate the skin, hardly grows microorganisms even when used for a long period of time.
  • the present invention was formulated by blending the disinfectant preservative obtained by the method of Example 3 to a concentration of 0.004% by mass in accordance with a conventional method with the basic formula of the following peel-off type pack agent. A pack agent was obtained.
  • the pack of this example which has excellent skin cleansing power and moisturizes the skin, hardly grows microorganisms even when stored for a long period of time.
  • the disinfectant obtained by the method of Example 1 was blended in a concentration of 0.004% by mass according to a conventional method. -I got Chillon.
  • Titanium oxide 8.0 parts by mass
  • the shampoo according to the present invention is obtained by blending the disinfectant / preservative obtained by the method of Example 4 to a concentration of 0.007% by mass with the basic formulation of the transparent shampoo shown below according to a conventional method. It was.
  • the transparent shampoo of this example which has excellent detergency and does not irritate the skin, hardly grows microorganisms even when used for a long time.
  • Example 2 For the basic formula of the acne agent shown below, the same ⁇ -darcosyl rutin as used in Example 1 was blended to a concentration of 0.0015% by mass according to a conventional method. An agent was obtained.
  • Cyanine dye represented by chemical formula 2 0.005 parts by mass Concentrated glycerin 0.5 parts by mass
  • the acne agent of this example which effectively prevents acne and significantly improves and alleviates various symptoms associated with acne, exhibits a stable pharmacological action over a long period of time.
  • the disinfectant / preservative according to the present invention is extremely useful in external preparations for skin such as cosmetics and quasi-drugs, especially in external preparations exposed to ambient light such as natural light and artificial light during preparation or use. . In fields other than the topical skin preparation, it can be advantageously applied to a wide variety of articles requiring a disinfectant.

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  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un agent bactéricide/conservateur dont l'ingrédient bactéricide/conservateur se dégrade difficilement même lorsqu'il est exposé à une lumière environnante, telles une lumière artificielle et une lumière naturelle, ainsi que l'utilisation de l'agent bactéricide/conservateur. L'invention porte sur un agent bactéricide/conservateur qui comprend un colorant de cyanine spécifique servant d'ingrédient bactéricide/conservateur et une rutine ou dérivé du sucre correspondant en tant qu'ingrédient destiné à améliorer la résistance à la lumière du colorant de cyanine. L'invention a également trait à un agent destiné à une application externe sur la peau qui contient l'agent bactéricide/conservateur.
PCT/JP2007/059590 2006-05-11 2007-05-09 Agent bactéricide/conservateur WO2007132710A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2008515499A JP5145214B2 (ja) 2006-05-11 2007-05-09 殺菌・防腐剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-132213 2006-05-11
JP2006132213 2006-05-11

Publications (1)

Publication Number Publication Date
WO2007132710A1 true WO2007132710A1 (fr) 2007-11-22

Family

ID=38693805

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/059590 WO2007132710A1 (fr) 2006-05-11 2007-05-09 Agent bactéricide/conservateur

Country Status (3)

Country Link
JP (1) JP5145214B2 (fr)
TW (1) TWI427071B (fr)
WO (1) WO2007132710A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0327293A (ja) * 1989-03-08 1991-02-05 Hayashibara Biochem Lab Inc α―グリコシル　ルチンの製造方法とその用途
JPH04363395A (ja) * 1991-06-10 1992-12-16 T Hasegawa Co Ltd 水溶性香料組成物の劣化防止方法
JPH08119849A (ja) * 1994-10-20 1996-05-14 Kose Corp 皮膚外用剤
JPH10203954A (ja) * 1997-01-20 1998-08-04 Noevir Co Ltd 抗菌性低刺激化粧料
JP2003160465A (ja) * 2001-11-29 2003-06-03 Shiseido Co Ltd 経皮吸収促進用プレトリートメント剤及びそのプレトリートメント剤を用いた化粧方法
JP2003192530A (ja) * 2001-12-28 2003-07-09 Mitani Sangyo Co Ltd 野蚕シルク繊維

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02215706A (ja) * 1989-02-16 1990-08-28 Nippon Kanko Shikiso Kenkyusho:Kk 抗微生物用組成物および化粧料
JPH07233046A (ja) * 1993-12-28 1995-09-05 Kose Corp 外用剤

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0327293A (ja) * 1989-03-08 1991-02-05 Hayashibara Biochem Lab Inc α―グリコシル　ルチンの製造方法とその用途
JPH04363395A (ja) * 1991-06-10 1992-12-16 T Hasegawa Co Ltd 水溶性香料組成物の劣化防止方法
JPH08119849A (ja) * 1994-10-20 1996-05-14 Kose Corp 皮膚外用剤
JPH10203954A (ja) * 1997-01-20 1998-08-04 Noevir Co Ltd 抗菌性低刺激化粧料
JP2003160465A (ja) * 2001-11-29 2003-06-03 Shiseido Co Ltd 経皮吸収促進用プレトリートメント剤及びそのプレトリートメント剤を用いた化粧方法
JP2003192530A (ja) * 2001-12-28 2003-07-09 Mitani Sangyo Co Ltd 野蚕シルク繊維

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MORI K.: "Simultaneous Determination of Photosensitizers in Quasi-Drugs and Cosmetics", ANNUAL REPORT OF TOKYO METROPOLITAN INSTITUTE OF PUBLIC HEALTH, vol. 56, 2005, pages 111 - 115, XP003018894 *

Also Published As

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JP5145214B2 (ja) 2013-02-13
JPWO2007132710A1 (ja) 2009-09-24
TW200812988A (en) 2008-03-16
TWI427071B (zh) 2014-02-21

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