WO2000066070A2 - Utilisation pour les soins bucco-dentaires de principes actifs antimicrobiens nanometriques - Google Patents

Utilisation pour les soins bucco-dentaires de principes actifs antimicrobiens nanometriques Download PDF

Info

Publication number
WO2000066070A2
WO2000066070A2 PCT/EP2000/003660 EP0003660W WO0066070A2 WO 2000066070 A2 WO2000066070 A2 WO 2000066070A2 EP 0003660 W EP0003660 W EP 0003660W WO 0066070 A2 WO0066070 A2 WO 0066070A2
Authority
WO
WIPO (PCT)
Prior art keywords
active ingredients
use according
nanoscale
antimicrobial
oral
Prior art date
Application number
PCT/EP2000/003660
Other languages
German (de)
English (en)
Other versions
WO2000066070A3 (fr
Inventor
Christine Schröder
Hans Dolhaine
Peter Wülknitz
Hans Theo Leinen
Dorothea Gregori
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to AU45549/00A priority Critical patent/AU4554900A/en
Publication of WO2000066070A2 publication Critical patent/WO2000066070A2/fr
Publication of WO2000066070A3 publication Critical patent/WO2000066070A3/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • 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
    • 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
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/65—Characterized by the composition of the particulate/core
    • A61K2800/652—The particulate/core comprising organic material

Definitions

  • the invention relates to the use of antimicrobial agents in nanoscale form for the manufacture of oral and / or dental care products.
  • Nanoscale substances are substances whose particle diameter in the direction of the greatest expansion of the particles is less than 1000 nm (nanometers).
  • nanoparticulate is used synonymously with the term “nanoscale”.
  • Nanoscale active ingredients are described in the literature in particular as a means of achieving a controlled release of the active ingredient over a longer period of time.
  • WO 98/14174 discloses nanoparticles for parenteral therapeutic use which consist of a pharmacologically active substance encapsulated in a shell made of a biodegradable polymer.
  • pharmacologically active substances include antibacterial substances such as chloramphenicol and vancomycin and antimicrobial substances such as penicillins and cephalosporins.
  • Application CA 2,111,523 describes disinfectants which, in addition to other constituents, also contain surface-modified nanoparticulate antimicrobial active ingredients.
  • a disinfectant cleaner formulation is given as an example.
  • the application CA 2,111, 522 describes compositions with long-lasting germicidal activity which contain surface-modified nanoparticulate antimicrobial agents. Disinfectants for surface treatment which provide permanent antimicrobial films on the treated surface are described as applications of these compositions.
  • nanoparticulate antimicrobial substances can advantageously be used as active ingredients in the field of oral and dental care.
  • antimicrobial active ingredients both, for. B. in the field of surface disinfection as well as in the field of oral and dental care.
  • the type of application as well as the requirements for the potency, the spectrum of action and the formulation of the active ingredients in the different areas of application are so different that the knowledge gained in one area of application does not imply another area of application in an obvious manner can be transferred.
  • the problem frequently arises with antimicrobial active substances, in particular with poorly water-soluble active substances, that these active substances are difficult to incorporate into formulations for oral and / or dental care and that the formulations obtained show an unsatisfactory antimicrobial effect.
  • Another object of the invention was to provide oral and / or dental care products with an antimicrobial activity sufficient for the application and at the same time a reduced content of antimicrobial active substances.
  • the object was achieved in that the antimicrobial active ingredients in the form of nanoparticles with a particle diameter in the range from 5 to 500 nm, preferably from 10 to 150 nm, are used to produce the oral and / or dental care products.
  • the invention therefore relates to the use of nanoscale antimicrobial active ingredients with a particle diameter in the range from 5 to 500 nm, preferably from 10 to 150 nm, for the production of oral and / or dental care products, in particular toothpastes or toothbrush gels.
  • the antimicrobial active ingredients in nanoparticulate form are not only easier to incorporate into formulations of oral and / or dental care products, but that their effectiveness is also increasing. This means that when used with the same weight, the nanoparticulate active substance produces a stronger antimicrobial effect than the same active substance in a larger particle size.
  • antimicrobial active ingredients in nanoparticulate form is particularly noticeable if the active ingredients themselves are poorly water-soluble or if they are non-basic compounds which, accordingly, are not converted into readily water-soluble salts by the addition of acids can.
  • antimicrobial active substances are preferably to be understood
  • Salicylic acid N-alkylamides where the alkyl radicals contain 1-22 carbon atoms and can be linear or branched and their mixtures.
  • Saiicylic acid N-octylamide and / or salicylic acid N-decylamide are particularly preferred as antimicrobial active substances according to the invention.
  • the nanoscale active substances according to the invention consist of a discrete phase of the active substance, on the surface of which at least one surface-modifying substance is preferably adsorbed.
  • Emulsifiers and / or protective colloids are particularly suitable as surface-modifying substances.
  • the coating of the particles with emulsifiers and / or protective colloids means that there is no subsequent agglomeration of the particles.
  • Suitable emulsifiers are nonionic surfactants 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
  • adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil (6) polyol and in particular polyglycerol esters, such as polyglycerol polyricin oleate, 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 as well as 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), sucrose, alkyl giucosides (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 as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C 12/18 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations.
  • C 8/18 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.
  • 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 preferably 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 emulsifiers are soaps, alkyl benzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerin ether sulfates, hydroxymischlyether ether sulfates, mono (ether) sulfate ethersulfates (mon) and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N-acyl
  • 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 gycinate, for example trimethylammonium glycinate Cocoalkyldimethylammonium glycinate, N-acylamino-propyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethyiimidazolines each having 8 to 18 C atoms in the alkyl or acyl group and the alkyl or acyl group Coconut acylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium gycinate, for example trimethylammonium glycinate Cocoalkyldimethylammonium gly
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8/18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and are capable of forming internal salts.
  • 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 alkyiaminoacetic acid, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12/18 acylsarcosine.
  • quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • anionic emulsifiers are alkyl sulfates, alkyl ether sulfates and monoglyceride (ether) sulfates.
  • the active ingredients and the emulsifiers are used in a weight ratio of 1: 100 to 100: 1, preferably 1:25 to 25: 1 and in particular 1:10 to 10: 1.
  • Emulsifiers which are capable of forming microemulsions are particularly preferred.
  • Suitable protective colloids are, for example, gelatin, casein, gum arabic, lysalbic acid, starch, carboxymethyl cellulose or modified Carboxymethyl cellulose and polymers such as polyvinyl alcohols, polyvinyl pyrrolidones, polyalkylene glycols and polyacrylates.
  • a further subject of the invention is thus the use according to the invention of nanoscale antimicrobial active substances in which the nanoparticles are encased by one or more emulsifiers and / or protective colloids.
  • nanoparticles according to the invention can be produced, for example, by
  • the invention therefore also relates to the use according to the invention of nanoscale antimicrobial active substances which are produced by this process.
  • a suitable organic solvent e.g. alkanes, vegetable oils, ethers, esters, ketones, acetals and the like.
  • the solutions are then added to water or another non-solvent, usually in the presence of a surface-active compound dissolved in them, so that the homogenization of the two immiscible solvents leads to precipitation of the nanoparticles preferably evaporates organic solvents.
  • a surface-active compound e.g. alkanes, vegetable oils, ethers, esters, ketones, acetals and the like.
  • O / W emulsions O / W microemulsions can also be used.
  • the emulsifiers and protective colloids already explained at the beginning can be used as surface-active compounds.
  • GAS process Gas Anti Solvent Recrystallization
  • the process uses a highly compressed gas or supercritical fluid (e.g. carbon dioxide) as a non-solvent for the crystallization of solutes.
  • a highly compressed gas or supercritical fluid e.g. carbon dioxide
  • the compressed gas phase is introduced into the primary solution of the starting materials and absorbed there, which increases the volume of the liquid, the solubility decreases and fine particles are separated out.
  • the PCA method (Precipitation with a Compressed Fluid Anti-Solvent) is similarly suitable.
  • the primary solution of the starting materials is introduced into a supercritical fluid, whereby finely divided droplets form in which diffusion processes take place, so that the finest particles are precipitated.
  • the starting materials are melted by injecting gas (e.g. carbon dioxide or propane). Pressure and temperature reach near or supercritical conditions.
  • the gas phase dissolves in the solid and causes a lowering of the melting temperature, the viscosity and the surface tension. When expanding through a nozzle, cooling effects lead to the formation of very fine particles.
  • gas e.g. carbon dioxide or propane
  • the amount of the nanoscale compounds is chosen so that the concentration of the antimicrobial active ingredients contained in the nanoparticles is usually in the order of 0.001 to 5, preferably 0.01 to 2 and in particular 0.1 to 1% by weight, based on the preparations .
  • the oral and / or dental care products obtainable using the nanoscale antimicrobial active ingredients according to the invention can be in the form of toothpastes, gels, liquid toothpastes, tooth powders, mouthwashes or optionally also as chewing agents, for example chewing gum. However, they are preferably in the form of more or less flowable or plastic toothpastes, such as are used to clean the teeth using a toothbrush. Toothpastes or liquid toothpastes according to the invention contain a polishing agent, usually in an amount of 5 to 50% by weight, and a humectant, usually in an amount of 10 to 60% by weight.
  • Suitable polishing agents are all friction bodies known for toothpastes, such as, for example, silica, aluminum hydroxide, aluminum oxide, calcium pyrophosphate, chalk, dicalcium phosphate dihydrate, sodium aluminum silicates, for example zeolite A, organic polymers, for example polymethacrylate, or mixtures of these friction bodies.
  • a polishing agent which itself has a restorative effect on lesions and open dental tubules, the dicalcium phosphate dihydrate, has proven to be particularly suitable.
  • Dicalcium phosphate dihydrate (CaHPO 4 2H 2 O) occurs naturally as brushite and is commercially available in suitable grain sizes from 1 to 50 ⁇ m.
  • a combination of is suitable as a carrier for the toothpastes according to the invention, which enables the setting of a suitable consistency for dosing from tubes, dispensing containers or flexible bottles on the basis of the combination of polishing agents according to the invention
  • Humectant, binders and water for example, glycerin, sorbitol, xylitol, propylene glycols, polyethylene glycols, in particular those with average molecular weights of 200-800, can be used as humectants.
  • Natural and / or synthetic water-soluble polymers such as alginates, carragheenates, tragacanth, starch and starch ethers, cellulose ethers such as carboxymethyl cellulose (sodium salt), hydroxyethyl cellulose, methyl hydroxypropyl cellulose, guar, acacia gum, agar agar, xanthan gum, for example, serve as consistency regulators (or binders) -Gum, succinoglycan gum, locust bean gum, pectins, water-soluble carboxyvinyl polymers (eg Carbopol ® types), polyvinyl alcohol, polyvinyl pyrrolidone, polyethylene glycols, in particular those with molecular weights of 1,500-1,000,000.
  • carboxymethyl cellulose sodium salt
  • hydroxyethyl cellulose methyl hydroxypropyl cellulose
  • guar acacia gum
  • agar agar xanthan gum
  • xanthan gum for
  • Layered silicates such as Montmorillonite clays, colloidal thickening silicas such as Airgel silicas, pyrogenic silicas or finely ground precipitated silicas.
  • the viscosity of the toothpastes can also be set so low that they can be dosed from a flexible plastic bottle onto the toothbrush as a "liquid tooth cleaning agent" with a viscosity of 2,000 - 40,000 m-Pa-s (25 ° C) penetrate between the bristles but do not drip off the toothbrush.
  • a combination of 0.1 to 1% by weight of xanthan gum and / or carboxymethyl cellulose and 0.01 to 5% by weight of a viscosity-stabilizing additive from the group of the cationic, zwitterionic or ampholytic nitrogen-containing additives is preferably suitable as a binder
  • Surface-active substances are also present in the toothpastes according to the invention to support the cleaning effect and, if desired, also to develop foam during tooth brushing and to stabilize the polishing body dispersion in the carrier in an amount of 0.1 to 5% by weight.
  • Suitable surfactants are, for example, linear sodium alkyl sulfates with 12 to 18 carbon atoms in the alkyl group. These substances also have an enzyme-inhibiting effect on the bacterial metabolism of the plaque.
  • alkali metal salts preferably sodium salts of alkyl polyglycol ether sulfate with 12 to 16 carbon atoms in the linear alkyl group and 2 to 6 glycol ether groups in the molecule, of linear alkane (C-
  • 8) esters of sulfated fatty acid monoglycerides, sulfated fatty acid alkanolamides,
  • Sulfoacetic acid alkyl (C ⁇ 2-C-
  • Zwitterionic, ampholytic and nonionic surfactants are also suitable, for example oxethylates of fatty acid mono- and diglycerides, of fatty acid sorbitan esters and alkyl (oligo) glucosides.
  • Other common toothpaste additives are also suitable, for example oxethylates of fatty acid mono- and diglycerides, of fatty acid sorbitan esters and alkyl (oligo) glucosides.
  • Sweeteners such as Saccharin sodium, sodium cyclamate, sucrose, lactose, maltose, fructose,
  • - flavors such as Peppermint oil, spearmint oil, eucalyptus oil, anise oil, fennel oil, caraway oil, menthyl acetate, cinnamaldehyde, anethole, vanillin, thymol and mixtures of these and other natural and synthetic flavors,
  • - buffer substances such as primary, secondary or tertiary alkali phosphates or citric acid / sodium citrate,
  • the carrier consists essentially of water, ethanol, essential oils, emulsifiers and solubilizers for the rest
  • Aroma components Aroma components, taste corrections (e.g. sweetener) and, if necessary, astringent or invigorating drug extracts and, if necessary, colorants.
  • nanoscale antimicrobial active ingredients are known to those skilled in the art
  • the invention accordingly furthermore relates to oral and / or dental care compositions containing antimicrobial active ingredients, which are characterized in that the antimicrobial active ingredient in the form of nanoparticles with a
  • Example 1 Preparation of nanoscale salicylic acid-N-octylamide 0.5 g of salicylic acid-N-octylamide (mp. About 45 ° C.) were dissolved in 100 g of deionized water and the mixture was heated to about 50 ° C., a two-phase Mixture of water and amide phase formed. The latter was emulsified by adding 8.9 g of alkyl ether sulfate (Texapon® N 70, Henkel KGaA, Düsseldorf) to form a clear mixture. The successive transition of the oil phase into the transparent water / amide / emulsifier mixture can be seen as an indication of the formation of a microemulsion.
  • alkyl ether sulfate Texapon® N 70, Henkel KGaA, Düsseldorf
  • the microemulsion was cooled to ambient temperature and then evaporated to dryness on a rotary evaporator, giving 9.4 g of the salicylic acid-N-octylamide included in the ether sulfate matrix in nanoparticulate form. With ten times the amount of water, the nanoparticles could be processed into a stable and transparent dispersion. In light scattering, the particles showed a maximum with a particle size of 120 nm when numerically weighted.
  • Example 2 Preparation of a nanoscale aqueous salicylic acid-N-octylamide dispersion
  • Polishing clay P10 finely weakly calcined clay (approx. 20% by weight gamma-aluminum oxide approx. 80% by weight alpha-aluminum oxide primary crystal size 0.5 - 1.5 ⁇ m)
  • Example 2 The antimicrobial activity of the nanoscale salicylic acid N-octylamide prepared according to Example 2 was tested in comparison with the salicylic acid N-octylamide known from the prior art and produced according to EP 0262587 using the liquid toothpaste formulations from Examples 7.2 and 7.3. Both formulations contain the same concentration of the active ingredient salicylic acid-N-octylamide. In parallel, the corresponding drug-free formulation from Example 7.4 was also checked as a blank value.
  • toothpastes diluted with water to different extents were added to the same amounts of bacterial suspensions with a defined germ content. After incubation for 72 hours at 37 ° C., a smear was made per culture tube on a solid nutrient medium and the growth was assessed.
  • MIC values were determined in accordance with the above table, whereby MIC (minimum inhibitory concentration) is to be understood as the concentration at which bacterial growth can no longer be detected. MIC values in% by weight toothpaste
  • the bacterial suspension of Streptococcus mutans could not be adjusted to the bacterial count of 10 8 CFU / ml in this test. A direct comparison of the MIC values with the other test strains is therefore not possible. For the inhibition of 10 8 CFU / ml Streptococcus mutans, higher drug concentrations tend to be assumed.
  • the long-term antibacterial effect of salicylic acid N-octylamide was demonstrated in the liquid series of inhibitors.
  • the toothpaste formulation 7.2 with nanoscale salicylic acid N-octylamide showed the greatest inhibitory effect.
  • a concentration of> 10% was required even after the active ingredient-free formulation 7.4 had taken effect for 3 days.
  • the toothpaste with salicylic acid-N-octylamide in the conventional form inhibited Staphylococcus aureus in a concentration of 5% (50 ppm active ingredient).
  • the analog toothpaste with the nanoscale active ingredient however, already showed the same effect in a 1% concentration (10 ppm active ingredient).

Abstract

L'invention concerne l'utilisation de principes actifs antimicrobiens nanomètriques, c'est-à-dire dont le diamètre des particules est compris dans la plage 5-500 nm, pour la production de produits de soins bucco-dentaires, en particulier de dentifrices ou de gels pour le nettoyage des dents. Par rapport aux formes de principes actifs de l'état de la technique, la finesse particulière des particules permet une intégration plus facile de ces principes actifs dans des formulations et l'obtention d'une efficacité accrue.
PCT/EP2000/003660 1999-04-30 2000-04-22 Utilisation pour les soins bucco-dentaires de principes actifs antimicrobiens nanometriques WO2000066070A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45549/00A AU4554900A (en) 1999-04-30 2000-04-22 Utilization of nanoscalar, antimicrobial active ingredients in oral and/or dental hygiene

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999119770 DE19919770A1 (de) 1999-04-30 1999-04-30 Verwendung nanoskaliger antimikrobieller Wirkstoffe in der Mund- und/oder Zahnpflege
DE19919770.9 1999-04-30

Publications (2)

Publication Number Publication Date
WO2000066070A2 true WO2000066070A2 (fr) 2000-11-09
WO2000066070A3 WO2000066070A3 (fr) 2001-04-05

Family

ID=7906461

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/003660 WO2000066070A2 (fr) 1999-04-30 2000-04-22 Utilisation pour les soins bucco-dentaires de principes actifs antimicrobiens nanometriques

Country Status (3)

Country Link
AU (1) AU4554900A (fr)
DE (1) DE19919770A1 (fr)
WO (1) WO2000066070A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049559A2 (fr) * 2000-12-18 2002-06-27 Henkel Kommanditgesellschaft Auf Aktien Substances de taille nanométrique dans des produits d'hygiène
WO2010114538A1 (fr) 2009-04-01 2010-10-07 Colgate-Palmolive Company Dentifrice désensibilisant présentant une absorption d'agent antibactérien pour tissu dentaire

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0000438D0 (en) * 2000-01-11 2000-03-01 Boots Co Plc Dental compositions
DE10018219A1 (de) * 2000-04-12 2001-10-25 Henkel Kgaa Verwendung von N-Octylsalicylsäureamid und/oder N-Decylsalicylsäureamid als antimikrobieller Wirkstoff
DE20112769U1 (de) * 2001-08-07 2002-06-13 Bausemer Olaf Zahnreinigungsset
WO2006092155A1 (fr) * 2005-03-02 2006-09-08 Christoph Cichos Preparation agissant de maniere antimicrobienne destinee a un usage externe
US20090155318A1 (en) 2006-10-31 2009-06-18 Lee Howard W H Process to form nano-sized materials, the compositions and uses thereof

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262587A2 (fr) * 1986-10-02 1988-04-06 Henkel Kommanditgesellschaft auf Aktien Amides de l'acide salicylique, leur procédé de fabrication et leur utilisation
US5290541A (en) * 1992-06-18 1994-03-01 The Procter & Gamble Company Methods for making oral compositions
US5302373A (en) * 1993-06-10 1994-04-12 Church & Dwight Co., Inc. Liquid mouthwash containing a particulate bicarbonate suspension
CA2111523A1 (fr) * 1992-12-16 1994-06-17 Karen Mccue Agents anti-infectieux
WO1994020072A1 (fr) * 1993-03-05 1994-09-15 Pharmacia Ab Particules lipidiques solides, particules d'agents bioactifs et leurs procedes de production et d'utilisation
US5411750A (en) * 1993-04-27 1995-05-02 Church & Dwight Co., Inc. Ultrafine sodium bicarbonate powder
US5455024A (en) * 1993-05-19 1995-10-03 Church & Dwight Co., Inc. Dentifrices containing zinc oxide particles and sodium bicarbonate
WO1995033441A1 (fr) * 1994-06-06 1995-12-14 Block Drug Company, Inc. Soulagement de l'hypersensibilite dentinaire au moyen de particules submicroniques
US5688492A (en) * 1992-05-22 1997-11-18 The Boots Company Plc, Oral hygiene composition
WO1999022703A1 (fr) * 1997-10-31 1999-05-14 Lurident Ltd. Formulations ameliorees de soins personnels
DE19837191A1 (de) * 1998-08-17 2000-02-24 Henkel Kgaa Kosmetische und dermatologische Hautbehandlungsmittel

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2676362B3 (fr) * 1991-05-17 1993-08-13 Oreal Procede pour accroitre l'activite d'au moins un actif dans une composition a usage cosmetique et/ou dermopharmaceutique et composition pour la mise en óoeuvre dudit procede.
GB9126101D0 (en) * 1991-12-09 1992-02-12 Unilever Plc Oral hygiene products
US5616315A (en) * 1994-10-13 1997-04-01 Gillette Canada Inc. Particles including degradable material and anti-microbial agent

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0262587A2 (fr) * 1986-10-02 1988-04-06 Henkel Kommanditgesellschaft auf Aktien Amides de l'acide salicylique, leur procédé de fabrication et leur utilisation
US5688492A (en) * 1992-05-22 1997-11-18 The Boots Company Plc, Oral hygiene composition
US5290541A (en) * 1992-06-18 1994-03-01 The Procter & Gamble Company Methods for making oral compositions
CA2111523A1 (fr) * 1992-12-16 1994-06-17 Karen Mccue Agents anti-infectieux
WO1994020072A1 (fr) * 1993-03-05 1994-09-15 Pharmacia Ab Particules lipidiques solides, particules d'agents bioactifs et leurs procedes de production et d'utilisation
US5411750A (en) * 1993-04-27 1995-05-02 Church & Dwight Co., Inc. Ultrafine sodium bicarbonate powder
US5455024A (en) * 1993-05-19 1995-10-03 Church & Dwight Co., Inc. Dentifrices containing zinc oxide particles and sodium bicarbonate
US5302373A (en) * 1993-06-10 1994-04-12 Church & Dwight Co., Inc. Liquid mouthwash containing a particulate bicarbonate suspension
WO1995033441A1 (fr) * 1994-06-06 1995-12-14 Block Drug Company, Inc. Soulagement de l'hypersensibilite dentinaire au moyen de particules submicroniques
WO1999022703A1 (fr) * 1997-10-31 1999-05-14 Lurident Ltd. Formulations ameliorees de soins personnels
DE19837191A1 (de) * 1998-08-17 2000-02-24 Henkel Kgaa Kosmetische und dermatologische Hautbehandlungsmittel

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002049559A2 (fr) * 2000-12-18 2002-06-27 Henkel Kommanditgesellschaft Auf Aktien Substances de taille nanométrique dans des produits d'hygiène
WO2002049559A3 (fr) * 2000-12-18 2002-09-26 Henkel Kgaa Substances de taille nanométrique dans des produits d'hygiène
WO2010114538A1 (fr) 2009-04-01 2010-10-07 Colgate-Palmolive Company Dentifrice désensibilisant présentant une absorption d'agent antibactérien pour tissu dentaire
US20120020900A1 (en) * 2009-04-01 2012-01-26 Guofeng Xu Densensitizing dentifrice exhibiting dental tissue antibacterial agent uptake
CN102365076A (zh) * 2009-04-01 2012-02-29 高露洁-棕榄公司 显示牙组织抗菌剂吸收的脱敏洁齿剂
AU2009343753B2 (en) * 2009-04-01 2013-03-28 Colgate-Palmolive Company Desensitizing dentifrice exhibiting dental tissue antibacterial agent uptake
TWI396555B (zh) * 2009-04-01 2013-05-21 Colgate Palmolive Co 顯現牙組織抗菌劑吸收之減敏牙劑
US8778312B2 (en) 2009-04-01 2014-07-15 Colgate-Palmolive Company Densensitizing dentifrice exhibiting dental tissue antibacterial agent uptake

Also Published As

Publication number Publication date
DE19919770A1 (de) 2000-11-02
WO2000066070A3 (fr) 2001-04-05
AU4554900A (en) 2000-11-17

Similar Documents

Publication Publication Date Title
EP0252276B1 (fr) Désinfectants et détergents
EP1660015B1 (fr) Solution dentaire et buccale
DE60031511T2 (de) Stabilisierte antimikrobielle systeme und verfahren zur herstellung
WO2005027863A1 (fr) Agents d'hygiene bucco-dentaire
EP1289476B1 (fr) Agents thixotropes pour l'hygiene buccale et dentaire
EP0185971A1 (fr) Application d'alkylglycosides comme potentiateurs dans les agents antiseptiques ainsi que les agents de désinfection et nettoyage avec une activité bactéricide élevée
WO2004080434A1 (fr) Agents de soin bucco-dentaire
WO1991002513A1 (fr) Dentifrice contre la plaque dentaire
WO2008025524A2 (fr) Préparation d'aérosol contenant des pelloïdes
EP3393427B1 (fr) Procédé de réduction de la transpiration
WO1991002511A1 (fr) Dentifrice anti-plaque dentaire
WO2000066070A2 (fr) Utilisation pour les soins bucco-dentaires de principes actifs antimicrobiens nanometriques
DE102017200321A1 (de) Zubereitungen mit partikulären Polyquaternium-6 Polymeren
EP1175200B1 (fr) Utilisation dans des deodorants corporels de principes actifs antimicrobiens nanometriques
EP3221007B1 (fr) Produits de nettoyage et d'hygiène bucco-dentaire pour dents hypersensibles
DE2137857C3 (de) Verfahren zur Herstellung pulvriger transpirationshemmender Komplexverbindungen, dadurch erhaltene Verfahrensprodukte und transpirationshemmende Pulver-Aerosol-Präparate
WO2017016856A1 (fr) Préparation cosmétique réduisant la transpiration
DE2608123A1 (de) Antiperspirationsmittel und verfahren zu dessen herstellung
DE2524364A1 (de) Antitranspirant in aerosolform
WO1991002510A1 (fr) Produits inhibiteurs du tartre pour les soins de la bouche et des dents
DE10051035A1 (de) Zubereitung zur kosmetischen Behandlung der Haut
EP3328504A1 (fr) Antitranspirant
WO2017016861A1 (fr) Antitranspirant
EP3328503A1 (fr) Antitranspirant

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AU BR CA CN CZ HU JP KR MX NO PL SK US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AU BR CA CN CZ HU JP KR MX NO PL SK US

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP