WO2002050230A1 - Dispersions de materiaux composites nanoparticulaires contenant des substances odorantes - Google Patents

Dispersions de materiaux composites nanoparticulaires contenant des substances odorantes Download PDF

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Publication number
WO2002050230A1
WO2002050230A1 PCT/EP2001/014639 EP0114639W WO0250230A1 WO 2002050230 A1 WO2002050230 A1 WO 2002050230A1 EP 0114639 W EP0114639 W EP 0114639W WO 0250230 A1 WO0250230 A1 WO 0250230A1
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Prior art keywords
preparation
fragrance
dispersion
oil
dispersion according
Prior art date
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PCT/EP2001/014639
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German (de)
English (en)
Inventor
Marcel Roth
Christian Kropf
Christine Schröder
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU2002219178A priority Critical patent/AU2002219178A1/en
Priority to EP01271431A priority patent/EP1349911A1/fr
Publication of WO2002050230A1 publication Critical patent/WO2002050230A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A61L9/014—Deodorant compositions containing sorbent material, e.g. activated carbon
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm

Definitions

  • the invention relates to aqueous dispersions of nanoparticulate composite materials, the composite materials comprising at least one fragrance and an organic carrier and the particles having an average particle diameter in the range from 1 to 500 nm.
  • the fragrance substances contained in them are released slowly from the composite materials.
  • the composite materials are suitable for scenting substrates, especially textiles and keratin fibers.
  • Fragrance substances also known as fragrances
  • fragrances have long been used, for example, in washing, rinsing, cleaning or conditioning agents, as well as in cosmetic preparations.
  • they serve less - as in earlier times - to mask unpleasant smells of the components contained in the above-mentioned agents or preparations, but are primarily used to treat both the products themselves and the objects or agents treated with the agents
  • product identification is also achieved by the consumer via the fragrance of the product or the fragrance transmitted by the product to the object being treated; the promotional promotion of the fragrance makes use of this product identification and is used to promote sales.
  • fragrance note is given a special place in advertising, and thus also in consumer presentation, especially for avivage products.
  • manufacturers of detergents, dishwashing detergents or cleaning agents and also for the manufacturers of cosmetic preparations for a way of fixing fragrance substances on objects treated with such agents on the one hand and thus making it possible to do so at or after can be released during the treatment, but on the other hand also extend the time for the release of the fragrances after the treatment.
  • controlled release of fragrances in a wide variety of preparations in the detergent, dishwashing, cleaning and personal care sector often referred to as "controlled release” or “slow release” is the subject of numerous publications and patent applications.
  • fragrances are of outstanding importance, because - for the reasons mentioned above - both the product, as well as the washing, rinsing, cleaning or finishing agent solution and the objects treated with these agents are intensely and long-lasting fragranced
  • odoriferous substances to carrier materials and then coating them or encapsulating them or encapsulating them in complex form (for example cyclodextrin odorant complexes)
  • complex form for example cyclodextrin odorant complexes
  • chemically binding the odoriferous substances to carrier media the chemical binding being slow split and the Riec material is released.
  • This principle has been implemented, for example, in the esterification of fragrance alcohols, as described in WO 97/30687.
  • the object of the invention was also to provide methods for washing, rinsing, cleaning and finishing as well as for cosmetic treatment of the body, with which a long-lasting fragrance can be applied to the items to be washed, washed or cleaned or to the human body or parts thereof.
  • the invention therefore relates to an aqueous dispersion of a nanoparticulate composite material, the composite material comprising at least one fragrance and an organic carrier and the particles having an average particle diameter in the range from 1 to 500 nm and preferably in the range from 10 to 200 nm.
  • the size specifications are to be understood as the diameter in the direction of the greatest longitudinal expansion of the particles.
  • particles are always obtained with a size that follows a distribution curve.
  • the method of dynamic light scattering known to the person skilled in the art can be used for the experimental determination of the particle size.
  • fragrances also called fragrances, z.
  • Compounds from the class of esters, ethers, aldehydes, ketones, alcohols or hydrocarbons can be used.
  • Fragrances of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate (DMBCA), phenylethyl acetate, benzyl acetate, ethyl methylphenylglycinate, allylcyclohexylpropylate, cyclosilate, methyllateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylateylatey
  • fragrances which together produce an appealing fragrance.
  • Such mixtures are also referred to as perfume oils if they are present as liquids at room temperature.
  • Natural products from plant sources can also be used as fragrances or fragrance mixtures, e.g. B. pine, citrus, jasmine, patchouli, rose or ylang-ylang oil. Also suitable are muscatel sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil and labdanum oil as well as orange blossom oil, neroli oil, orange peel oil and sandalwood oil.
  • a fragrance In order to be perceptible, a fragrance must be volatile, whereby in addition to the nature of the functional groups and the structure of the chemical compound, the molar mass also plays an important role. Most fragrances have molecular weights of up to around 300 daltons, while higher molecular weights are an exception. Due to the different volatility of fragrances, the smell of a perfume or fragrance composed of several fragrances changes during evaporation, whereby the Odor impressions are divided into “top note”, “heart or middle note”("middlenote” or “body”) and “base note”("endnote” or “dry out”).
  • the top note of a perfume or fragrance does not consist solely of volatile compounds, while the base note largely consists of less volatile, ie non-stick fragrances.
  • more volatile fragrances can be bound to certain fixatives, for example, which prevents them from evaporating too quickly.
  • fixatives for example, which prevents them from evaporating too quickly.
  • Adhesive fragrances that can be used as a fragrance in the context of the present invention are, for example, the essential oils such as angelica root oil, aniseed oil, basil oil, bay oil, champaca blossom oil, noble pine cone oil, elemi oil, eucalyptus oil, fennel oil, spruce oil, gum oil oil, gum oil oil, gum oil oil Helichrysumöl, Ho oil, ginger oil, iris oil, cajeput oil, calamus oil, camomile oil, camphor oil Kanagaöl, cardamom oil, cassia oil, pine needle oil, Kopa ⁇ vabalsamöl coriander oil, spearmint oil, caraway oil, Kuminöl, lavender oil, lemongrass oil lime oil, mandarin oil, melissa oil, Moschuskömeröl, myrrh oil, clove oil neroli oil, Niaouli oil, Olibanum oil, Origanum oil, Palmarosa oil, Patchuli oil, Peru balsam oil, Petitgra
  • the higher-boiling or solid odorants of natural or synthetic origin can also be used as adhesive odorants or odorant mixtures in the context of the present invention.
  • These compounds include the compounds mentioned below and mixtures of these: ambrettolide, ambroxan, ⁇ -amylcinnamaldehyde, anethole, anisaldehyde, anisalcohol, anisole, anthranilic acid methyl ester, acetophenone, Benzylacetone, benzaldehyde, ethyl benzoate, benzophenone,
  • the more volatile fragrances include in particular the lower-boiling fragrances of natural or synthetic origin, which can be used alone or in mixtures.
  • Examples of more volatile fragrances are diphenyl oxide, limonene, linalool, linalyl acetate and propionate, melusate, menthol, menthone, methyl-n-heptenone, pinene, phenylacetaldehyde, terpinylacetate, citral, citronellal.
  • fragrance mixtures in particular perfume oils, are preferred.
  • Suitable organic carriers in the context of the invention are, for example, waxes, higher fatty alcohols, fatty alcohol alkoxylates, fatty acid amides, quaternary ammonium compounds and quaternary phosphonium compounds, insofar as these have a melting point of more than 40 ° C and are poorly soluble in water.
  • poor solubility means a solubility of less than 5% by weight, preferably less than 1% by weight, based on the total weight of the solution.
  • waxes are understood to mean natural or synthetic substances which are kneadable at 20 ° C., solid to brittle hard, coarse to fine crystalline, translucent to opaque, but not glassy, melt undecomposed above approx. 40 ° C. and are already are slightly viscous and not stringy just above the melting point.
  • the waxes to be used for the purposes of the invention differ, for example, from resins in that they generally pass between about 50 and 90 ° C., in exceptional cases even up to 200 ° C., into the molten, low-viscosity state and are practically free from ash-forming compounds are.
  • the waxes are divided into the following three groups according to their origin: natural waxes of plant or animal origin, such as Candelilla wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugar cane wax, ouricury wax, montan wax, beeswax, shellac wax, walnut, lanolin (wool wax), pretzel fat, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes, microfax waxes chemically modified waxes (hard waxes), e.g. Montanester waxes, Sasol waxes, hydrogenated jojoba waxes or hydrogenated castor oil as well as synthetic waxes, e.g. Polyalkylene waxes and polyethylene glycol waxes.
  • natural waxes of plant or animal origin such as Candelilla wax, carnauba wax, Japanese wax, esparto grass wax, cork wax, gua
  • Higher fatty alcohols are to be understood as primary aliphatic alcohols of the formula R-OH, in which R represents an aliphatic, linear or branched hydrocarbon radical having 14 to 40 carbon atoms and 0, 1, 2 or 3 double bonds.
  • R represents an aliphatic, linear or branched hydrocarbon radical having 14 to 40 carbon atoms and 0, 1, 2 or 3 double bonds.
  • Typical examples are myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol, lignoceryl alcohol, ceryl alcohol, myricyl alcohol, melissyl alcohol and mixtures thereof.
  • the fatty alcohols can be vegetable, animal or synthetic Be of origin. Synthetic fatty alcohol mixtures which can be used according to the invention are, for. B. in the high pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols. Higher fatty alcohols of vegetable origin are preferred, particularly preferably those with 16 to 18 carbon atoms. Also preferred is cetylstearyl alcohol, which means mixtures of approximately equal parts of cetyl and stearyl alcohol.
  • Fatty alcohol alkoxylates suitable according to the invention are addition products of 2 to 100 moles of ethylene oxide and / or 0 to 20 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms.
  • Quaternary ammonium compounds in the context of the invention are understood to mean, for example, quaternary ammonium compounds of the formulas (I) and (II)
  • R and R 1 is an acyclic alkyl radical having 12 to 24 carbon atoms
  • R 2 is a saturated C 1 -C 4 alkyl or hydroxyalkyl radical
  • R 3 is either R
  • R or R 2 and COR 4 and COR 5 are each is an aliphatic acyl radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds
  • R 6 is H or OH
  • m, n and o can each independently have the value 1, 2 or 3
  • X is either a halide -, Methosulfat-, methophosphate or phosphate ion, and mixtures of these compounds.
  • Compounds which contain alkyl radicals having 16 to 18 carbon atoms are particularly preferred.
  • Examples of cationic compounds of the formula (I) are didecyldimethylammonium chloride, ditallow dimethylammonium chloride or
  • Dihexadecylammonium Dihexadecylammonium.
  • compounds of the formula (II) are methyl N- (2-hydroxyethyl) -N, N-di (tallow acyl oxyethyl) ammonium methosulfate, bis (palmitoyl) ethyl hydroxyethyl methyl ammonium methosulfate or methyl -N, N- bis (acyloxyethyl) -N- (2-hydroxyethyl) ammonium methosulfate.
  • quaternized compounds of formula (II) which have unsaturated alkyl chains
  • R 7 and R 8 each represent a saturated alkyl group with 12 to 18 carbon atoms
  • R 9 represents an alkyl group with 1 to 4 carbon atoms or H
  • Z represents an NH group or oxygen and A is an anion.
  • R 0 represents a C 1-4 alkyl, alkenyl or hydroxyalkyl group
  • R 11 and R 12 are each independently selected a C. 8 28 represents alkyl group and p is a number between 0 and 5.
  • alkylamidoamines in particular fatty acid amidoamines such as the stearylamidopropyldimethylamine available under the name Tego Amid ® S 18, and the so-called "esterquats", such as the methylhydroxyalkyldialkoyloxyalkylammonium methosulfates sold under the trademark Stepantex ® or the products from Cog known under Dehyquart ® Germany ,
  • Organic carriers which are particularly preferred according to the invention are paraffins and quaternary ammonium compounds.
  • the organic carrier substances have melting or softening points above 40 ° C. and below 100 ° C. and are meltable without decomposition.
  • the nanoparticulate composite material can also comprise two or more organic carriers.
  • a substance is suitable as the organic carrier for the composite material which, in the preferred forms of use of the composite material, namely as a constituent of detergents, dishwashing detergents and cleaning agents and cosmetic preparations, is in any case a common ingredient represents.
  • an aqueous dispersion is understood to mean a dispersion whose liquid phase consists of water or a homogeneous mixture of water with one or more non-aqueous polar solvents, such as, for example, ethanol, glycerol, ethylene glycol, propylene glycol or N-methylpyrrolidone.
  • non-aqueous polar solvents such as, for example, ethanol, glycerol, ethylene glycol, propylene glycol or N-methylpyrrolidone.
  • the composite material composed of carrier and fragrance mixture should be sparingly soluble in the liquid phase of the dispersion, with solubility of the constituents of the nanoparticulate composite materials being less than 5% by weight, preferably less than 1% by weight. , based on the total weight of the dispersion, should be understood.
  • nanoparticulate composite materials according to the invention are preferably encased by at least one surface modification agent.
  • Surface modification agents are understood to mean substances which physically adhere to the surface of the nanoparticles, but preferably do not react chemically with them.
  • the individual molecules of the surface modification agents adsorbed on the surface are essentially free of intermolecular bonds with one another.
  • Surface modifiers are to be understood in particular as dispersants. Dispersants are also known to the person skilled in the art, for example, under the terms emulsifiers, protective colloids, wetting agents and detergents.
  • Suitable surface modifiers are, for example, emulsifiers of the nonionic surfactant type from at least one of the following groups:
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricino leat, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
  • partial esters based on linear, branched, unsaturated or saturated C 6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside Lauryl glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the middle of which Degree of alkoxylation the ratio of the amounts of ethylene oxide and / or Propylene oxide and substrate with which the addition reaction is carried out corresponds.
  • C ⁇ / is alkyl mono- and oligoglycosides
  • their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • anionic surfactants and emulsifiers are soaps, alkylbenzenesulfonates, alkanesulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, alkyl ether sulfates, such as fatty alcohol ether sulfates, Glycerol ether, Hydroxymischethersulfate, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates , Mono- and dialkyl-sulfosuccinates, mono- and dialkyl-sulfosuccinamates, sulfotetriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammonium.
  • glycinate N-acylamino-propyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethyl carbox.
  • the fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, apart from a C8 / ⁇ 8 alkyl or - acyl group, contain at least one free amino group and at least one - containing COOH or -SO 3 H group and are capable of forming inner salts .
  • suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid, each with approximately 8 to 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci 2 / ⁇ s-acylsarcosine.
  • ampholytic emulsifiers quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Protective colloids suitable as surface modifiers are e.g. natural water-soluble polymers such as B. gelatin, casein, gum arabic, lysalbic acid, starch, albumin, alginic acid and their alkali and alkaline earth metal salts, water-soluble derivatives of water-insoluble polymeric natural substances such.
  • B. cellulose ethers such as methyl cellulose, hydroxyethyl cellulose,
  • Preferred surface modification agents are nonionic surfactants, in particular alkyl polyglycosides in which the alkyl radical contains between 12 and 16 carbon atoms, fatty alcohol alkoxylates and fatty acid alkanolamides.
  • the organic carrier is a quaternary compound
  • nonionic and / or cationic substances come into consideration as surface modification agents, but not anionic ones such as anionic surfactants.
  • anionic ones such as anionic surfactants.
  • the selection of the surface modification agents suitable for a specific organic carrier is possible by means of simple routine tests.
  • the amount of the surface modifier with respect to the composite material corresponds at least to the amount required to obtain a stable dispersion of nanoparticles of the composite material. This minimum amount can be determined by simple routine tests.
  • the composite material and the surface modification agent are used in a weight ratio of 1:50 to 50: 1, preferably 1: 5 to 10: 1 and in particular 1: 2 to 2: 1 for the production of the nanoparticulate composite material.
  • a mixture of two or more surface modification agents can also be used in the same amount.
  • the dispersions of nanoparticulate composite materials according to the invention can be based on what is known, for example, from EP-B1 0 506 197 for the production of nanoparticulate wax dispersions
  • a melt of the organic carrier is produced with the at least one fragrance, optionally in the presence of a surface modifier,
  • this melt is dispersed in a liquid, preferably water, with which the melt is not miscible, and (c) the temperature is then cooled below the melting point of the mixture of carrier substance, fragrance substance (s) and optionally surface modification agent.
  • the fragrance mixture is first heated together with the organic carrier material until a liquid phase is formed. Then one or more surface modifiers are added and the mixture is mixed until a homogeneous liquid phase is formed. If necessary, this is further heated. Subsequently, water is added to the liquid, water-immiscible mixture with stirring and with the formation of a microemulsion, which water has previously been heated to a temperature which is above the melting temperature of the mixture of fragrance mixture, organic carrier material and optionally surface modifiers. The microemulsion is then slowly cooled until the microemulsified particles solidify, which is expediently carried out with stirring, a stable dispersion of the nanoparticulate composite materials being formed.
  • Another object of the invention is thus a method for producing an aqueous dispersion of a nanoparticulate composite material, wherein the composite material comprises at least one fragrance and an organic carrier and the particles have an average particle diameter in the range from 1 to 500 nm, in which
  • the surface modification agent (s) can be heated from the beginning together with the organic carrier material and the fragrance mixture until a homogeneous liquid phase is formed become.
  • the heated water can be initially introduced and the liquid phase composed of a fragrance mixture, organic carrier material and optionally surface modification agents can be added to the water.
  • fragrance mixtures in which no such evaporation losses occur in the course of the manufacturing process of the composite materials according to the invention that they are undesirably noticeable in the odor profile of the composite materials.
  • mixtures of water and non-aqueous polar solvents such as, for example, ethanol, glycerol, ethylene glycol, propylene glycol or N-methylpyrrolidone, are also suitable according to the invention, provided that the nanoparticulate composite materials are sparingly soluble in these aqueous mixtures, the term sparingly soluble as defined above is.
  • the dispersions of the nanoparticulate composite materials produced by the process according to the invention are distinguished by a high storage stability.
  • the composite material should, if appropriate together with the surface modifying agent, be able according to the above production processes described in water or aqueous mixtures to give stable dispersible nanoparticles, the mean particle diameter of the nanoparticles being in the range from 1 to 500 nm.
  • the usable organic carriers and the additional surface modification agents that may be required can be selected by simple routine tests.
  • the dispersions according to the invention can contain between 1 and 60% by weight of the nanoparticulate composite materials and / or between 0.1 and 10% by weight of the fragrance or fragrance mixture, in each case based on the total weight of the dispersion.
  • fragrance release of the fragrances present in the composite materials according to the invention is significantly delayed compared to the otherwise identical fragrances present. This means that the fragrance released from the composite material lasts much longer. As far as the fragrance intensity is concerned over the course of time, this is much more uniform with the composite materials according to the invention. While the fragrance intensity of the freely available fragrance substances is initially high and then rapidly drops, the fragrance intensity of the composite material according to the invention is initially lower than that of the free fragrance substance, but then remains at a significantly elevated level over a longer period of time.
  • the odoriferous substances in the composite materials according to the invention can be present, for example, in the form of solid solutions, enclosed in small cavities in the carrier material or even partially adsorbed on the particle surface.
  • the fragrance contained in the interior of the particles can be released by diffusion to the surface.
  • the fragrance mixture contained can accordingly be released in a controlled manner from the composite materials according to the invention.
  • the fragrance characteristic of the composite material according to the invention can match or even deviate from that of the free fragrance mixture.
  • the person skilled in the art can always set the desired fragrance impression for the composite material according to the invention.
  • nanoparticulate composite materials can be produced which adhere particularly well to substrates and in particular to the surfaces of substrates.
  • H. have a particularly high substantivity. This is particularly true for textile fibers and keratin fibers, such as. B. human hair, but among surfaces within the meaning of the invention, for example, surfaces of hard substrates such. B. ceramic tiles, glass, floors or furniture surfaces or other objects to understand.
  • nanoparticulate composite materials according to the invention it is thus possible with the nanoparticulate composite materials according to the invention to give substrates and in particular the surface of substrates a long-lasting fragrance.
  • Another object of the present invention is accordingly the use of an aqueous dispersion of a nanoparticulate composite material, the composite material comprising at least one fragrance and an organic carrier and the particles having an average particle diameter in the range from 1 to 500 nm, for scenting a substrate, in particular one Textile, a keratin fiber or a hard surface.
  • the aqueous dispersions of nanoparticulate composite materials according to the invention can be stably incorporated into formulations, even if they contain a high proportion of water, and can thus enable higher concentrations of fragrances to be used than when the free fragrances are used.
  • the invention further comprises the use of an aqueous dispersion of a nanoparticulate composite material, the composite material comprising at least one fragrance and an organic carrier and the particles having an average particle diameter in the range from 1 to 500 nm, in washing, rinsing, cleaning and finishing preparations as well as in cosmetic preparations. It has been found that the task of transferring a long-lasting fragrance to the objects treated with these preparations or to the human body or parts thereof through the use of washing, rinsing, cleaning and finishing preparations as well as cosmetic preparations, can be solved if dispersions of nanoparticulate composite materials according to the present invention are used in the respective preparations.
  • the present invention further provides preparations comprising detergent in addition to the usual constituents of a detergent preparation, detergent in addition to the usual constituents of a detergent preparation, cleaning agent in addition to the usual constituents of a detergent preparation, finishing agent in addition to the usual constituents of a detergent preparation and cosmetic agent in addition to the usual constituents of a cosmetic preparation, an aqueous dispersion of a nanoparticulate composite material, the composite material comprising at least one fragrance and an organic carrier and the particles having an average particle diameter in the range from 1 to 500 nm.
  • Preferred preparations are aqueous preparations.
  • washing, rinsing, cleaning and finishing agent preparations comprise as active substances substances such as surfactants (anionic, non-ionic, cationic and amphoteric surfactants), builder substances (inorganic and organic builder substances), bleaching agents (such as, for example, peroxo bleaching agents and chlorine bleaching agents).
  • active substances such as surfactants (anionic, non-ionic, cationic and amphoteric surfactants), builder substances (inorganic and organic builder substances), bleaching agents (such as, for example, peroxo bleaching agents and chlorine bleaching agents).
  • bleaching agents such as, for example, peroxo bleaching agents and chlorine bleaching agents.
  • washing aids and cleaning aids for which exemplary and non-limiting optical brighteners, UV protection substances, so-called soil repellents, i.e. polymers which counteract re-soiling of fibers or hard surfaces, and silver protection agents.
  • the cosmetic preparations are aqueous preparations which are particularly suitable for the treatment of keratin fibers, in particular human hair, or for the treatment of human skin.
  • the hair treatment agents mentioned are in particular agents for treating human hair.
  • the particularly preferred agents according to the invention include hair washing and hair care products such as hair shampoos, hair rinses and hair treatments.
  • a cosmetic preparation that is also preferred according to the invention is a deodorant spray.
  • the aqueous dispersion of a nanoparticulate composite material according to the invention is preferably used, if appropriate after prior dilution, for. B. with water, mixed or dispersed with the other recipe components in a conventional manner at a temperature below the melting point of the composite material.
  • the dispersions according to the invention are used in such an amount that the nanoparticulate composite material in an amount in the range from 0.01 to 30% by weight, preferably in an amount in the range from 0.1 to 10% by weight. , and in particular an amount in the range from 0.5 to 2% by weight, based on the total weight of the preparation.
  • the preferred use concentration of the nanoparticulate composite material is in the range from 0.1 to 30% by weight, in the case of hair conditioners in the range from 0.1 to 20% by weight, in each case based on the total weight of the preparations.
  • the invention also relates to a method for scenting a substrate, in which the surface of the substrate is coated with an olfactory, ie. H. odorally effective amount of a dispersion according to the invention as described above or a preparation as described above is brought into contact.
  • an olfactory ie. H. odorally effective amount of a dispersion according to the invention as described above or a preparation as described above is brought into contact.
  • the invention also relates to washing processes, in particular for machine washing of laundry, washing processes, in particular for machine dishwashing, cleaning processes, in particular for cleaning surfaces or objects, and also finishing processes, in particular for textiles, in which preparations according to the invention are applied to respective aqueous liquors and treated the substrates with the liquors containing the preparations.
  • the treatment can be done e.g. B. also be done in such a way that the object is sprayed with the preparation or the liquor.
  • the invention also relates to a cosmetic treatment method in which a cosmetic preparation according to the invention is brought into contact with the human body or a part thereof and is treated cosmetically in this way.
  • a perfume oil of the following composition was used for Examples 1-6 according to the invention:
  • Example 1 Production of a nanoparticulate dispersion of a composite material from paraffin and perfume oil
  • Example 2 Production of a nanoparticulate dispersion of a composite material from paraffin and perfume oil
  • Example 3 Production of a nanoparticulate dispersion of a composite material from paraffin and perfume oil
  • Example 4 Production of a nanoparticulate dispersion of a composite material from a quaternary ammonium compound and perfume oil
  • Example 5 Production of a nanoparticulate dispersion of a composite material from a quaternary ammonium compound and perfume oil
  • Comparative Example 6 Production of a nanoparticulate dispersion of a quaternary ammonium compound with an additional content of perfume oil
  • fragrances Herbavert, Dihydromyrcenol, Tetrahydrolinalool and Isobornylacetat then in the steam room were identified by means of a GC-MS coupling and spectrum comparison using a substance library, and quantified in parallel using an FID.
  • the numerical values listed in the following table represent relative Peak areas represent and are a measure of the concentration of the respective fragrance.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des dispersions aqueuses de matériaux composites nanoparticulaires, ces derniers contenant au moins une substance odorante et un support organique et les particules présentant un diamètre moyen compris entre 1 et 500 nm. Les substances odorantes présentes dans les matériaux composites sont libérées progressivement. Ces matériaux composites sont donc adaptés de préférence pour parfumer durablement des substrats, en particulier des textiles et des fibres de kératine.
PCT/EP2001/014639 2000-12-20 2001-12-13 Dispersions de materiaux composites nanoparticulaires contenant des substances odorantes WO2002050230A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2002219178A AU2002219178A1 (en) 2000-12-20 2001-12-13 Dispersions of nanoparticulate fragrance-containing composite materials
EP01271431A EP1349911A1 (fr) 2000-12-20 2001-12-13 Dispersions de materiaux composites nanoparticulaires contenant des substances odorantes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10063428.1 2000-12-20
DE2000163428 DE10063428A1 (de) 2000-12-20 2000-12-20 Dispersionen nanopartikulärer riechstoffhaltiger Kompositmaterialien

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WO2002050230A1 true WO2002050230A1 (fr) 2002-06-27

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AU (1) AU2002219178A1 (fr)
DE (1) DE10063428A1 (fr)
WO (1) WO2002050230A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1477152A1 (fr) * 2003-05-12 2004-11-17 Beiersdorf AG Système d'excipient pour agents actifs cosmétiques ou pharmaceutiques
WO2004098555A1 (fr) * 2003-05-07 2004-11-18 Ifac Gmbh & Co.Kg Compositions permettant une liberation ciblee de parfums et d'aromes
US7316994B2 (en) 2002-11-01 2008-01-08 The Procter & Gamble Company Perfume polymeric particles
FR2954347A1 (fr) * 2009-12-23 2011-06-24 Capsum Formulations parfumantes sous forme de nanodispersion
WO2011077062A1 (fr) * 2009-12-23 2011-06-30 Capsum Formulations parfumantes sous forme de nanodispersion
US8187580B2 (en) 2002-11-01 2012-05-29 The Procter & Gamble Company Polymeric assisted delivery using separate addition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10247583C5 (de) 2002-10-11 2009-04-30 Bell Flavors & Fragrances Duft Und Aroma Gmbh Verfahren zur Herstellung eines festen Riechstoffkonzentrates

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DE2747726A1 (de) * 1976-10-29 1978-05-03 Procter & Gamble Parfuemiertes konditioniermittel fuer gewebe
EP0346034A2 (fr) * 1988-06-06 1989-12-13 Unilever Plc Agents actifs encapsulés par de la cire et procédé à base d'émulsion pour leur production
EP0447318A1 (fr) * 1990-03-16 1991-09-18 L'oreal Composition pour le traitement cosmétique et/ou pharmaceutique des couches supérieures de l'épiderme par application topique sur la peau et procédé de préparation correspondant
EP0466236A1 (fr) * 1990-07-11 1992-01-15 Quest International B.V. Emulsions parfumées structurées dans produits à usage corporel
WO2000068352A1 (fr) * 1999-05-05 2000-11-16 Unilever N.V. Compositions de lessives
EP1146057A1 (fr) * 2000-04-15 2001-10-17 Givaudan SA Nanoparticules polymères contenant des molécules olfactives

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ATE357T1 (de) * 1978-11-17 1981-11-15 Unilever Nv Fluessige mittel zum auftragen von parfuems auf textiloberflaechen.

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2747726A1 (de) * 1976-10-29 1978-05-03 Procter & Gamble Parfuemiertes konditioniermittel fuer gewebe
EP0346034A2 (fr) * 1988-06-06 1989-12-13 Unilever Plc Agents actifs encapsulés par de la cire et procédé à base d'émulsion pour leur production
EP0447318A1 (fr) * 1990-03-16 1991-09-18 L'oreal Composition pour le traitement cosmétique et/ou pharmaceutique des couches supérieures de l'épiderme par application topique sur la peau et procédé de préparation correspondant
EP0466236A1 (fr) * 1990-07-11 1992-01-15 Quest International B.V. Emulsions parfumées structurées dans produits à usage corporel
WO2000068352A1 (fr) * 1999-05-05 2000-11-16 Unilever N.V. Compositions de lessives
EP1146057A1 (fr) * 2000-04-15 2001-10-17 Givaudan SA Nanoparticules polymères contenant des molécules olfactives

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7316994B2 (en) 2002-11-01 2008-01-08 The Procter & Gamble Company Perfume polymeric particles
US8187580B2 (en) 2002-11-01 2012-05-29 The Procter & Gamble Company Polymeric assisted delivery using separate addition
WO2004098555A1 (fr) * 2003-05-07 2004-11-18 Ifac Gmbh & Co.Kg Compositions permettant une liberation ciblee de parfums et d'aromes
US8716214B2 (en) 2003-05-07 2014-05-06 Otc Gmbh Compositions for the targetted release of fragrances and aromas
EP1477152A1 (fr) * 2003-05-12 2004-11-17 Beiersdorf AG Système d'excipient pour agents actifs cosmétiques ou pharmaceutiques
FR2954347A1 (fr) * 2009-12-23 2011-06-24 Capsum Formulations parfumantes sous forme de nanodispersion
WO2011077062A1 (fr) * 2009-12-23 2011-06-30 Capsum Formulations parfumantes sous forme de nanodispersion

Also Published As

Publication number Publication date
DE10063428A1 (de) 2002-07-11
EP1349911A1 (fr) 2003-10-08
AU2002219178A1 (en) 2002-07-01

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