WO2005004601A1 - Alcools secondaires utilises en tant que principes actifs antimicrobiens - Google Patents

Alcools secondaires utilises en tant que principes actifs antimicrobiens Download PDF

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Publication number
WO2005004601A1
WO2005004601A1 PCT/EP2004/051078 EP2004051078W WO2005004601A1 WO 2005004601 A1 WO2005004601 A1 WO 2005004601A1 EP 2004051078 W EP2004051078 W EP 2004051078W WO 2005004601 A1 WO2005004601 A1 WO 2005004601A1
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Prior art keywords
compound
butanol
methyl
gram
formula
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PCT/EP2004/051078
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German (de)
English (en)
Inventor
Aurelia Reckziegel
Horst Surburg
Florian Wolf
Jürgen Rabenhorst
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Symrise Gmbh & Co. Kg
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Application filed by Symrise Gmbh & Co. Kg filed Critical Symrise Gmbh & Co. Kg
Priority to EP04741770A priority Critical patent/EP1651037A1/fr
Publication of WO2005004601A1 publication Critical patent/WO2005004601A1/fr

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    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic

Definitions

  • the present invention relates to the use of certain secondary alcohols as active ingredients against Gram-positive bacteria, as are particularly responsible for (a) body odor, (b) impure skin and / or acne, and (c) bad breath and / or bad breath.
  • Some of the compounds that can be used according to the invention are new, as are the preparations in which they are used.
  • the healthy warm-blooded organism especially the healthy human skin and mucous membrane, is populated with a large number of non-pathogenic microorganisms.
  • This so-called microflora of the skin or mucous membrane is not only harmless, it represents an important protection for the defense against opportunistic or pathogenic germs.
  • other microorganisms can improve the condition of the healthy ones
  • antimicrobial agents are sought, the antibacterial spectrum (antibiogram) of which includes Gram-positive bacteria. It is already known that certain alcohols have an antimicrobial effect.
  • primary alcohols such as. B. Famesol, a primary sesquiterpene alcohol.
  • farnesol and other primary alcohols with antimicrobial properties have a sensitizing and allergenic potential, so that their use is increasingly no longer tolerated.
  • the primary object of the present invention to provide compounds which are active against Gram-positive bacteria.
  • the compounds to be specified should have a possibly slight intrinsic odor, be easy to incorporate into antibacterial preparations, be stable in the usual cosmetic formulations and also under the required application conditions, and be readily accessible, ie. H. be producible by simple chemical reactions and be well tolerated, d. H. do not cause unacceptable health effects when used-
  • R 1 to R 6 are independently hydrogen or methyl
  • A is a phenyl group optionally substituted with a further C, - to C 5 - substituted alkyl substituents, a norbornane-2-yl or a Pina ⁇ - 3-yl-Gr ⁇ ppe.
  • the alcohols to be used according to the invention are secondary alcohols which comprise an aryl radical (group A).
  • group A an aryl radical
  • WO 01/85120 A1 relates to the use of the secondary alcohol 6,10-dimethyI-5,9-undecadien-2-ol as an antimicrobial active ingredient, it also gives no indication of the usability of secondary alcohols which come under the formula I.
  • DE 100 25 124 A1 describes combinations of active ingredients which comprise a glycerol monoalkyl ether and an aryl-substituted alcohol. It is not excluded that the glycerol monoalkyl ether is combined with a secondary aryl-substituted alcohol, but the primary alcohols phenoxyethanoi, anise alcohol and 2-methyl-5-phenyl-pentan-1-ol and the tertiary alcohol phenyl-dimethylethylcarbonol are particularly preferred , It is not disclosed that aryl-substituted alcohols alone can have an effect against Gram-positive bacteria, and this applies in particular to aryl-substituted secondary alcohols.
  • EP 0 919 607 A2 discloses additives for the physical and / or microbiological stabilization of the liquid or viscous composition of a lubricant, the additive being an aromatic alcohol, which can also be secondary. However, it is not disclosed which germs the additive should be effective against; however, it is generally stated that
  • Cooling lubricant compositions are microbiologically stabilized. However, since cooling lubricants are usually only colonized by bacteria that are Gram-negative, EP 0 919 607 A2 at least gives no indication that they are used as an additive
  • the compounds of the formula I to be used according to the invention have a very excellent activity against Having Gram-positive bacteria
  • the compounds of the formula I are particularly suitable because they have at most a low intrinsic odor and can be prepared by simple chemical reactions.
  • the secondary alcohols of the formula I are active substances against Gram-positive bacteria in particular can be used in cosmetic, oral hygiene and / or dermatological preparations
  • Gram-positive bacteria are known to the person skilled in the art, which are responsible for the unpleasant body conditions according to (a) - (c).
  • Gram-positive bacteria that cause body odor are bacteria e.g. B. from the genera Corynebacterium, Staphyiococcus, Micrococcus and Brevibacterium, in particular Corynebacterium xerosis, Staphyiococcus epidermidis and Staphyiococcus hominis, Micrococcus luteus and / or Micrococcus sedentarius and Brevibacterium epidermidis.
  • Gram-positive bacteria that verusache ⁇ impure skin and / or acne are, for example, bacteria of the genus Propionibacterium, in particular Propionibacterium acnes.
  • Gram-positive bacteria that cause bad breath and / or bad breath are, for example, bacteria of the genera Actinomyces, Eubacterium, Rothia and Stomatococcus, in particular Actinomyces viscosus, Eubacterium brachy, Eubacterium nodatum, Eubacterium saburreum, Eubacterium timidum and Eubacterium denticus and Roth Stomatococcus mucilaginosus.
  • the secondary alcohols of formula (!) Harmonize with a variety of common cosmetic auxiliaries and additives.
  • the compounds of formula I can therefore be incorporated into a wide variety of dosage forms and preparations. Preparations to be applied to the skin which contain compounds of the formula I are able to determine the number of Gram-positive bacteria responsible for the respective phenomenon or the particular impairment according to the above
  • Enumeration (a) to (c) are responsible for reducing, while the microflora of the contacted skin is protected.
  • Preparations which contain the compounds of the formula I are regularly distinguished by good skin tolerance, provided that none of the other constituents contained in the preparation cause an intolerance.
  • deodorants especially those against body odor and bad breath, which contain the secondary alcohols of the formula I.
  • deodorants have good skin tolerance (including
  • group A is preferably phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 4-isobutylphenyl, 2,4-dimethylphenyl, 3,4 -Dimethyiphenyl, 2,5-dimethylphenyl, 2,4,5-trimethylphenyl, 2,4,6-trimethylphenyl,
  • At least one of the groups R 1 to R ⁇ is methyl if A is phenyl or a monoalkyl-substituted phenyl.
  • the following compounds of the formula I are particularly preferred as active substances against Gram-positive bacteria:
  • the invention also relates to methods for controlling Gram-positive bacteria, the bacteria being contacted with an antimicrobially effective amount of a compound of the formula I or a mixture of at least two different compounds of the formula I.
  • the compounds of the formula I mentioned above apply here Meanings of the substituents, the information relating to the particularly preferred compounds of the formula I of course also continuing to apply.
  • the invention also relates to a method for controlling (a) body odor caused by Gram-positive bacteria (b) impure skin and / or acne caused by Gram-positive bacteria and / or (c) bad breath caused by Gram-positive bacteria and / or bad breath, the Gram-positive bacteria being contacted with an antimicrobially effective amount of a compound of the formula I or a mixture of at least two different compounds of the formula I.
  • a method for controlling (a) body odor caused by Gram-positive bacteria (b) impure skin and / or acne caused by Gram-positive bacteria and / or (c) bad breath caused by Gram-positive bacteria and / or bad breath, the Gram-positive bacteria being contacted with an antimicrobially effective amount of a compound of the formula I or a mixture of at least two different compounds of the formula I.
  • the compound of the formula I is usually applied flat to the area of the skin (including the mucous membrane)
  • control encompasses both the treatment of existing impairments (in particular by undesirable, bacterially caused odors) and the corresponding prophylaxis.
  • An ⁇ , ⁇ -unsaturated ketone is first prepared by an aldol reaction of a suitable aldehyde with a methyl ketone (J. March, Advanced Organic Chemistry, 4 ed., J. Wiley, New York, 1992, pp. 937-944).
  • the double bond and the keto group are hydrogenated. If necessary, only the double bond can be hydrogenated first and then the keto group can be reduced (J. March, Advanced Organic Chemistry, 4 * 1 ed., J. Wiley, New York, 1992, pp. 771-783; 910-920).
  • a suitable aldehyde is reacted in a Grignard reaction with a methyl magnesium halide (J. March, Advanced Organic Chemistry, 4 lh ed., J. Wiley, New York, 1992, pp. 920-931). If double bonds are present, the corresponding saturated compounds can be obtained by catalytic hydrogenation (Scheme 4).
  • Preparations according to the invention in particular cosmetic, oral hygiene and dermatological preparations, comprise an antibacterially effective amount of a compound of the formula I (the information above regarding the substituents and the preferred compounds correspondingly apply), and at least one further ingredient which is suitable for a z.
  • a compound of the formula I the information above regarding the substituents and the preferred compounds correspondingly apply
  • cosmetic, oral hygiene or dermatological preparation is typical.
  • the preparations according to the invention cannot usually be used as a lubricant for the mechanical processing or processing of materials.
  • the preparations according to the invention generally do not contain any corrosion inhibitor (organic boron compounds), no EP active ingredient (sulfur and phosphorus additives), no defoamer, no formaldehyde releaser and no boric acid
  • the compounds of formula I to be used according to the invention can also be used to prevent the spoilage of organic substances and preparations, in particular the spoilage of cosmetic, dermatological and oral hygiene preparations, by infestation with gram-positive bacteria.
  • the formulation is mixed with an antibacterially effective amount of one or more compounds of the formula I, the statements made above regarding the substituents and the compounds of the formula I to be used with preference apply accordingly.
  • the compounds of the formula I are preferably used in a concentration of 0.05-10% by weight, based on the total mass of the substance or formulation.
  • the secondary alcohols of the formula (I) harmonize with a large number of customary cosmetic auxiliaries and additives, above all because the compounds of the formula (I) have no or only a very slight odor. This applies in particular to the formulations which are customary in deodorant or antiperspirant formulations
  • Perfume ingredients The combination of astringents, predominantly aluminum salts such as aluminum hydroxychloride, with the antimicrobial substances according to the invention of the formula (I) in one and the same composition is also advantageous.
  • One or more antimicrobial compounds of the formula (I) can be used in preparations.
  • the total content of secondary alcohols according to the invention is usually in the range from 0.005 to 50% by weight, preferably in the range from 0.01 to 20% by weight. , particularly preferably 0.1 to 5% by weight of the compounds according to the invention, and very particularly preferably 0.5 to 3% by weight, based on the total weight of the preparation.
  • the compounds of formula (I) are preferably used in cosmetic, oral hygiene or dermatological preparations.
  • the compounds according to the invention can be incorporated without difficulty into common cosmetic, oral hygiene or dermatological preparations, advantageously in pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, toothpastes, mouthwashes, tooth gels, nail care products (e.g. nail polishes, nail polish removers, nail balms) and the like -
  • the compounds according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extrusion products and used in this form and incorporated, for example, in formulations.
  • the properties of the active compounds modified in this way can be modified by so-called "coating” with suitable materials a more targeted release can be further optimized, for which purpose wax-like plastics such as, for example, polyvinyl alcohol are preferably used.
  • the microencapsulation of the active compounds can be carried out, for example, by the so-called coacervation process with the aid of capsule materials, for example made of polyurethane-like substances or soft gelatin
  • Spray drying of an emulsion or dispersion containing the active ingredient can be produced, whereby modified starches, proteins, dextrin and vegetable gums can be used as carriers.
  • Inclusion complexes can e.g. by adding dispersions of the active ingredient and cyclodextrins or urea derivatives in a suitable solvent, e.g. Water.
  • Extrusion products can be obtained by fusing the active ingredients with a suitable waxy substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol,
  • Preparations according to the invention can contain auxiliaries of the kind normally used in cosmetic or therapeutic preparations, for example preservatives, abrasives, antibacterial agents, anti-inflammatory agents, anti-irritants, anti-irritants, antimicrobials, antioxidants, astringents, antiseptics, antistatic agents, binders, buffers, buffers, buffers, buffers.
  • auxiliaries of the kind normally used in cosmetic or therapeutic preparations, for example preservatives, abrasives, antibacterial agents, anti-inflammatory agents, anti-irritants, anti-irritants, antimicrobials, antioxidants, astringents, antiseptics, antistatic agents, binders, buffers, buffers, buffers, buffers, buffers.
  • Carrier materials chelating agents, cell stimulants, cleaning agents, caring agents, surface-active substances, deodorising agents, plasticizers, bactericides, emulsifiers, enzymes, essential oils, film formers, fixatives, foaming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents , moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, optically brightening agents, dirt-repellent agents, friction-reducing agents, lubricants, opacifiers, opaque agents, brighteners, polymers, powders, proteins, abrasives,
  • Silicones skin soothing agents, skin cleansing agents, skin care agents, skin healing agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbing agents, UV filters, suspending agents, thickening agents, vitamins, oils, waxes, fats, Phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, ⁇ -hydroxy acids, polyhydroxy fatty acids, plasticizers, dyes, color-protecting agents, pigments, flavors, flavorings, perfumes, fragrances or other common components of such preparations such as alcohols, polyols, electrolytes, organic solvents or Silikonderivate-
  • Fragrances and flavors that can be combined with the secondary alcohols of the formula (I) in cosmetic, oral hygiene or dermatological preparations can be found, for example, in Bauer, Garbe, Surburg, Common Fragrance and Flavor Materials, Wiley-VCH, 4th ed. , 2001 or in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published.
  • UV absorbers such as Neo Heiiopane ® contain such protection from sunlight.
  • Suitable light stabilizers are, for example, organic UV absorbers from the class of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives,
  • Dibenzoylmethane derivatives diphenylacrylates, 3-imidazol-4-yl-acrylic acid and their esters, benzofuran derivatives, benzylidene malonate derivatives, polymeric UV absorbers, containing one or more organosilicon residues, cinnamic acid derivatives, camphor derivatives, trianilino -s- triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, 2-
  • Phenylbenzimidazole-5-sulfonic acid and its salts anthranilic acid menthyl ester, benzotriazole derivatives.
  • UV absorbers which can advantageously be used in preparations according to the invention, is of course not intended to be limiting: 4-aminobenzoic acid, 4-aminobenzoic acid ethyl ester, 4-dimethylaminobenzoic acid 2-ethylhexyl ester, 4-aminobenzoic acid glycerol ester, salicylic acid homo- menthyl esters (homosalates), salicylic acid 2-ethylhexyl ester,
  • Triethanolamine salicylate 4-isopropylbenzyl salicylate
  • the amount of non-particulate UV absorber (one or more compounds) in preparations according to the invention is preferably 0.001 to 30% by weight.
  • the total amount of filter substances is preferably 0.1 to 30% by weight, particularly preferably 0.2 to 10 % By weight, in particular 0.5 to 8% by weight, based on the total weight of the preparation.
  • particulate UV filters or inorganic pigments can be used, which can optionally be hydrophobized, such as the oxides of titanium (TiO 2 ), zinc (ZnO), iron (Fe 2 O 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (for example MnO), aluminum (Al 2 O 3 ), cerium (for example Ce 2 O 3 ) and / or mixtures thereof.
  • Antioxidants suitable and / or customary for cosmetic and / or dermatological applications can be used in the preparations according to the invention.
  • the antioxidants are advantageously selected from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-camosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ß-carotene, lycopene) and their derivatives, lipoic acid and their derivatives (e.g.
  • amino acids e.g. glycine, histidine, tyrosine, tryptophan
  • imidazoles e.g. urocanic acid
  • peptides such as D, L-carnosine, D-carnosine, L-camosine and their derivatives (e.g. anserine)
  • carotenoids e.g
  • thiols e.g. thioredoxin, glutathione, cysteine, cystine , Cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -lininoyl, chole ⁇ teryl and glyceryl esters
  • Diiauryl thiodipropionate distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (e.g.
  • buthioninsulfoximines homocysteine sulfoximines, buthioninsulfones, penta-, hexa-, heptoximinin
  • very achieve tolerable dosages e.g. pmol to ⁇ mol / kg
  • metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts , Bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g. ⁇ -linolenic acid, linoleic acid, oleic acid), folic acid and their derivatives, ubiquinone and ubiquiole and their derivatives, vitamin C and derivatives (e.g.
  • Ascorbyl palmitate Mg-Ascor byl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as konyferyl benzoate of benzoin, rutinic acid and its derivatives, ferulic acid and its derivatives, butylated hydroxytoluene, Bu- tylhydroxyanisole, nordihydroguajakh resinic acid, nordihydroguajaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g.
  • ZnO, ZnS0 4 selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide), transbenzene and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances mentioned.
  • selenomethionine e.g. stilbene oxide
  • transbenzene and the derivatives suitable according to the invention salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids
  • the amount of the antioxidants (one or more compounds) in preparations according to the invention is preferably 0.001 to 30% by weight, particularly preferably 0.05 to 20% by weight, in particular 1 to 10% by weight, based on the total weight of the preparation ,
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous for their respective concentration to be in the range from 0.001 to 10% by weight, based on the total weight of the preparation , to choose.
  • surface-active substances which can advantageously be used in preparations according to the invention are conventional soaps, for example fatty acid salts of sodium, alkyl sulfates, alkyl ether sulfates, alkane and alkylbenzenesulfonates, sulfoacetates, sulfobetaines, sarcosinates, amidosulfobetaines, sulfosuccinates, sulfosuccinic acid
  • alkyl ether carboxylates protein-fatty acid condensates, alkyl betaines and amidobetaines, fatty acid alkanolamides, polyglycol ether derivatives.
  • the surface-active substance can be present in a concentration between 1% by weight and 50% by weight in the shampooing agent, or in the washing, showering or bathing preparation.
  • Cosmetic and dermatological preparations according to the invention can be in various forms, such as those e.g. are usually used for this type of preparation. So you can e.g. a solution, an emulsion of the type water-in-oil (W / O) or of the type oil-in-water (O / W), or a multiple emulsion, for example of the type water-in-oil-in-water (W / O / W), a gel, a hydro-dispersion, a solid stick or an aerosol
  • the cosmetic or dermatological preparation according to the invention is a solution or lotion
  • the following can be used as solvents: water or aqueous solutions; Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; - Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isoprapanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids; Alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isoprapanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether,
  • Water can also be a component of alcoholic solvents.
  • Preparations according to the invention are often preferably emulsions and contain e.g. the fats, oils, waxes and other fat bodies mentioned, and also water and an emulsifier, as is usually used for such a type of formulation.
  • Preparations according to the invention can be present as gels and then usually contain alcohols of low C number, e.g. Ethanol, isoprapanol, 1,2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • alcohols of low C number e.g. Ethanol, isoprapanol, 1,2-propanediol, glycerol and water or an oil mentioned above in the presence of a thickener which is preferably silicon dioxide or an aluminum silicate in the case of oily-alcoholic gels, and is preferably a polyacrylate in the case of aqueous-alcoholic or alcoholic gels.
  • Cosmetic and dermatological preparations according to the invention can be present as gels which, in addition to at least one compound according to the invention and solvents usually used therefor, also include organic thickening agents, for example gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methyl cellulose, hydroxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose or inorganic Thickeners, for example aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate, are contained.
  • the thickener is in the gel, for example, in an amount between 0.1 and 30% by weight, preferably between 0.5 and 15 % By weight.
  • Preparations according to the invention may be in the form of solid sticks and then contain e.g. natural or synthetic waxes, fatty alcohols or fatty acid esters. Lip care sticks and deodorant sticks (“deodorant sticks”) are preferred.
  • Suitable blowing agents for cosmetic or dermatological preparations according to the invention which can be sprayed from aerosol containers are the customary known volatile, liquefied blowing agents, e.g. Hydrocarbons (propane, butane, isobutane) are suitable, which can be used alone or in a mixture with one another. Compressed air can also be used advantageously.
  • Hydrocarbons propane, butane, isobutane
  • a pH range of 3.5 - 7.5 is advantageous. It is particularly favorable to choose the pH in a range from 4.0 to 6.5.
  • the cosmetic, oral hygiene and / or dermatological preparations according to the invention can be used to treat the skin, hair, teeth and oral mucosa in the sense of dermatological treatment or treatment in the sense of nourishing cosmetics. But they can also be used in make-up products in decorative cosmetics or in oral hygiene.
  • the cosmetic, oral hygiene and / or dermatological formulations according to the invention are applied in a sufficient amount to the skin, teeth, gums and oral mucosa and tongue and / or hair in the manner customary for cosmetics and dermatics.
  • Oral hygiene products in the present invention include the formulations familiar to the person skilled in the art for cleaning and maintaining the oral cavity and the
  • Throat cavity and breath freshening understood are creams, gels, pastes, foams, emulsions, suspensions, areosols, sprays as well as capsules, granules, lozenges, tablets, candies or chewing gums, without this list Dosage forms are limiting with regard to the possible uses. Such formulations serve to clean and care for tooth substance and oral cavity and to refresh the breath. If the secondary alcohols 10 of the formula (I) to be used according to the invention are incorporated into deodorants, these deodorants can be, for example, liquid as an aerosol spray, pump spray, gel, roll-on and the like or as a solid preparation, for example as a stick or powder available.
  • Cosmetic and / or dermal tological preparations which are in the form of a sunscreen are also advantageous. These advantageously additionally contain at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment.
  • Preparations according to the invention for treating the hair are, for example, shampooing agents, preparations which are used when the hair is rinsed or after the shampooing, before or after the permanent wave treatment, before or after the coloring or decolorization of the hair, for preparations for blow-drying or inlaying the hair, preparations for coloring or decoloring, for a hairdressing and treatment lotion, a hair lacquer or around permanent wave products.
  • the preparations are anti-dandruff agents, such as anti-dandruff shampoos.
  • Cosmetic preparations according to the invention which are a shampooing agent or a washing, showering or bathing preparation preferably contain at least one anionic, nonionic or amphoteric surface-active substance or mixtures thereof.
  • This cosmetic or dermatological preparation can also be an aerosol with the auxiliaries usually used for it.
  • a cosmetic preparation according to the invention in the form of a lotion that is not rinsed out, in particular a lotion for inlaying the hair, a lotion that is used for blow-drying the hair, a styling and treatment lotion is generally an aqueous, alcoholic or aqueous-alcoholic Solution and contains at least one cationic, anionic, non-ionic or amphoteric polymer or mixtures thereof.
  • Cosmetic and dermatological preparations according to the invention for the treatment and care of the hair can be present as emulsions which are of the non-ionic or anionic type.
  • non-ionic emulsions contain oils or fatty alcohols, which can be polyethoxylated or polypropoxylated, for example, or also mixtures of the two organic components. This emulmuls
  • Sions may contain cationic surface-active substances.
  • Anionic emulsions are preferably of the soap type and contain at least one ethoxylated or propoxylated organic compound according to the invention with an anionic or non-ionic character.
  • Odor Odorless i) 4- (2,4-Dimethylphenyi) -3-methyl-2-butanol from 2,4-
  • Odor almost odorless, uncharacteristic j) 4- (2,4-dimethylphenyl) -2-butanol from 2,4-dimethylbenzaldehyde
  • the minimum inhibitory concentration (MIC) of the claimed substances was determined in the serial dilution test (H. Brandis, G. Pulverer: Textbook of Medical Microbiology. 6th revised edition, Gustav Fischer Verlag Stuttgart, 1988; page 200ff.) against various cosmetically relevant germs.
  • the test was transferred to the microtiter plate format and the MIC value was used to determine the concentration at which no significant increase in turbidity compared to the controls was observed after 16 hours of incubation at the wavelength of 620 nm.
  • the test is based on the work of Goldberg and Rosenberg (Production of Oral Malodor in an in vitro System, S. Goldberg and. Rosenberg, pp.143 - 150, in: Bad Breath- A multidisciplinary Approach, Eds: D. van Steenberghe, M. Rosenberg, Leuven University Press, 1996) and was adapted for better reproducibility.
  • a sterile liquid medium which is inoculated with fresh morning saliva, is incubated for a few days in a Coy box at 37 "C and then smelled by an inspector panel.
  • Triclosan ® was added in a concentration of 0.05%.
  • the inoculated tubes had the same smell after incubation as the non-inoculated tubes.
  • the minimum active concentration (MWK) will silt up in the present case, at which the formation of bad breath is inhibited.
  • Glycerol monostearate 1.50 1.50 1.50
  • Carbopol 980 (neutralized) 0.30 0.30 0.30 0.30
  • Paraffin oil ad 100.00 ad 100.00 ad 100.00
  • Paraffin oil ad 100.00 ad 100.00 ad 100.00
  • Paraffin oil ad 100.00 ad 100.00 ad 100.00
  • Citric acid 0.30 0.30 0.30 Citric acid 0.30 0.30 0.30
  • the liquid phase obtained by mixing the respective components together is filled into an aerosol container together with a propane-butane mixture (2: 7) in a ratio of 39:61.
  • Sorbitol 70% 29.00 29.00 29.00
  • Titanium dioxide 1.00 1.00 1.00
  • Sorbitol powder 38.00 37.00 35.50
  • Emulsifier / emulsifier 0.30 0.30 0.30 0.30
  • part A all substances except the zinc oxide were heated to 85 ° C. and the zinc oxide was carefully dispersed in the mixture.
  • the components of Part B were mixed, heated to 85 ° C and added to Part A with stirring.
  • Part C was added to the mixture of parts A and B and the mixture was then homogenized using a dispersing tool.

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne l'utilisation du composé de formule (I) en tant que principe actif contre des bactéries à gram positif. Dans ladite formule, m et n désignent indépendamment l'un de l'autre 0 et 1 ; R1 à R6 représentent indépendamment les uns des autres hydrogène ou méthyle, et ; A désigne un groupe phényle, qui est éventuellement substitué par des substituants alkyle en C1-C5 supplémentaires, un groupe norboran-2-yle ou un groupe pinan-3-yle.
PCT/EP2004/051078 2003-07-08 2004-06-09 Alcools secondaires utilises en tant que principes actifs antimicrobiens WO2005004601A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04741770A EP1651037A1 (fr) 2003-07-08 2004-06-09 Alcools secondaires utilises en tant que principes actifs antimicrobiens

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10330697.8 2003-07-08
DE2003130697 DE10330697A1 (de) 2003-07-08 2003-07-08 Sekundäre Alkohole als antimikrobielle Wirkstoffe

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WO2005004601A1 true WO2005004601A1 (fr) 2005-01-20

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EP1738803A1 (fr) * 2005-03-16 2007-01-03 Henkel Kommanditgesellschaft auf Aktien Inhibiteurs des Staphylococcus dans des déodorants et des antitranspirantes
DE102008043586A1 (de) 2007-11-12 2009-05-14 Symrise Gmbh & Co. Kg Riechstoffakkorde zur Bekämpfung der Wahrnehmung von Körpergeruch
EP2133102A1 (fr) 2008-03-19 2009-12-16 Symrise GmbH & Co. KG Tissus réduisant l'odeur
WO2011006689A3 (fr) * 2009-07-16 2012-03-29 Henkel Ag & Co. Kgaa Compositions cosmétiques et dermatologiquement topiques ayant un effet de minimisation ou d'inhibition de la croissance capillaire
EP2662098A1 (fr) 2012-05-10 2013-11-13 Symrise AG Utilisation de certaines liaisons pour modifier des odeurs
US8623340B2 (en) 2009-04-28 2014-01-07 Symrise Ag Omega-cyclohexylalkan-1-oles and use thereof as antimicrobial actives to combat body odor
US8911715B2 (en) 2008-05-30 2014-12-16 Symrise Ag L-menthyl-N-(2-hydroxyphenyl)carbamate
WO2015002095A1 (fr) * 2013-07-02 2015-01-08 花王株式会社 Agent de soulagement d'irritation
EP2966158A1 (fr) 2014-07-07 2016-01-13 Symrise AG Mélanges d'isomères de composés musqués macrocyliques insaturés
EP2966159A1 (fr) 2014-07-07 2016-01-13 Symrise AG Mélanges d'isomères E enrichis de composés musqués macrocycliques insaturées
US20160264910A1 (en) * 2013-11-08 2016-09-15 Firmenich Sa Alcohol with floral odor
WO2020098923A1 (fr) 2018-11-13 2020-05-22 Symrise Ag Ingrédients parfumants présentant une note de muguet
WO2020098901A1 (fr) 2018-11-12 2020-05-22 Symrise Ag Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes
WO2020125993A1 (fr) 2018-12-20 2020-06-25 Symrise Ag Composés alicycliques de parfum musqué
WO2022194957A1 (fr) 2021-03-19 2022-09-22 Firmenich Sa Produits de consommation parfumants antimicrobiens
WO2023213381A1 (fr) 2022-05-03 2023-11-09 Symrise Ag Nouveaux composés de parfum

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US10463891B2 (en) 2008-09-30 2019-11-05 Symrise Ag Extracts of Isochrysis sp.
EP3348255B1 (fr) 2008-12-05 2021-11-10 Symrise AG Extraits de tetraselmis sp. à visée cosmétique ou thérapeutique
EP3045161A1 (fr) 2015-01-18 2016-07-20 Symrise AG Compositions actives comprenant du 1,2-hexanediol et du 1,2-octanediol

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006218A (en) * 1974-07-08 1977-02-01 Johnson & Johnson Potentiated medicaments
WO1993001714A1 (fr) * 1991-07-25 1993-02-04 Henkel Kommanditgesellschaft Auf Aktien Melanges a effet antimicrobien

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006218A (en) * 1974-07-08 1977-02-01 Johnson & Johnson Potentiated medicaments
WO1993001714A1 (fr) * 1991-07-25 1993-02-04 Henkel Kommanditgesellschaft Auf Aktien Melanges a effet antimicrobien

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1738803A1 (fr) * 2005-03-16 2007-01-03 Henkel Kommanditgesellschaft auf Aktien Inhibiteurs des Staphylococcus dans des déodorants et des antitranspirantes
DE102008043586A1 (de) 2007-11-12 2009-05-14 Symrise Gmbh & Co. Kg Riechstoffakkorde zur Bekämpfung der Wahrnehmung von Körpergeruch
EP2133102A1 (fr) 2008-03-19 2009-12-16 Symrise GmbH & Co. KG Tissus réduisant l'odeur
US8852565B2 (en) 2008-03-19 2014-10-07 Symrise Ag Odour-reducing substances
US8911715B2 (en) 2008-05-30 2014-12-16 Symrise Ag L-menthyl-N-(2-hydroxyphenyl)carbamate
US8623340B2 (en) 2009-04-28 2014-01-07 Symrise Ag Omega-cyclohexylalkan-1-oles and use thereof as antimicrobial actives to combat body odor
WO2011006689A3 (fr) * 2009-07-16 2012-03-29 Henkel Ag & Co. Kgaa Compositions cosmétiques et dermatologiquement topiques ayant un effet de minimisation ou d'inhibition de la croissance capillaire
EP2662098A1 (fr) 2012-05-10 2013-11-13 Symrise AG Utilisation de certaines liaisons pour modifier des odeurs
EP2662434A1 (fr) 2012-05-10 2013-11-13 Symrise AG Utilisation de certaines liaisons pour augmenter des odeurs
WO2015002095A1 (fr) * 2013-07-02 2015-01-08 花王株式会社 Agent de soulagement d'irritation
US9982218B2 (en) * 2013-11-08 2018-05-29 Firmenich Sa Alcohol with floral odor
US20160264910A1 (en) * 2013-11-08 2016-09-15 Firmenich Sa Alcohol with floral odor
US10370616B2 (en) 2013-11-08 2019-08-06 Firmenich Sa Alcohol with floral odor
EP2966159A1 (fr) 2014-07-07 2016-01-13 Symrise AG Mélanges d'isomères E enrichis de composés musqués macrocycliques insaturées
WO2016005361A1 (fr) 2014-07-07 2016-01-14 Symrise Ag Mélanges d'isomères enrichis de composés de musc macrocycliques insaturés
WO2016005360A1 (fr) 2014-07-07 2016-01-14 Symrise Ag Mélanges d'isomères e enrichis de composés de musc macrocycliques insaturés
EP2966158A1 (fr) 2014-07-07 2016-01-13 Symrise AG Mélanges d'isomères de composés musqués macrocyliques insaturés
EP4006130A1 (fr) 2014-07-07 2022-06-01 Symrise AG Mélanges isomériques des composés de muscs macrocycliques insaturés
WO2020098901A1 (fr) 2018-11-12 2020-05-22 Symrise Ag Utilisation de dérivés de 1-éthyl-4,4-diméthyl-cyclohexane comme substances odoriférantes
WO2020098923A1 (fr) 2018-11-13 2020-05-22 Symrise Ag Ingrédients parfumants présentant une note de muguet
WO2020125993A1 (fr) 2018-12-20 2020-06-25 Symrise Ag Composés alicycliques de parfum musqué
WO2022194957A1 (fr) 2021-03-19 2022-09-22 Firmenich Sa Produits de consommation parfumants antimicrobiens
WO2023213381A1 (fr) 2022-05-03 2023-11-09 Symrise Ag Nouveaux composés de parfum

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EP1651037A1 (fr) 2006-05-03

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