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WO2001032751A1 - Procede de preparation de chitosanes ou de derives de chitosane nanoparticulaires - Google Patents

Procede de preparation de chitosanes ou de derives de chitosane nanoparticulaires Download PDF

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Publication number
WO2001032751A1
WO2001032751A1 PCT/EP2000/010330 EP0010330W WO0132751A1 WO 2001032751 A1 WO2001032751 A1 WO 2001032751A1 EP 0010330 W EP0010330 W EP 0010330W WO 0132751 A1 WO0132751 A1 WO 0132751A1
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WO
WIPO (PCT)
Prior art keywords
chitosan
chitosans
sulfate
acid
nanoparticulate
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2000/010330
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German (de)
English (en)
Inventor
Christian Kropf
Stephan Reil
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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 Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Priority to JP2001535447A priority Critical patent/JP2003514046A/ja
Priority to EP00972819A priority patent/EP1237988A1/fr
Publication of WO2001032751A1 publication Critical patent/WO2001032751A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5192—Processes
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/14—Powdering or granulating by precipitation from solutions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
    • 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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
    • C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Definitions

  • the invention is in the field of nanoparticles and relates to the production of chitosans or chitosan derivatives in nanoparticulate form.
  • chitosan In contrast to most hydrocolloids, which are negatively charged in the range of biological pH values, chitosan is a cationic biopolymer under these conditions.
  • the positively charged chitosan can interact with oppositely charged surfaces and is therefore used, for example, in cosmetic hair and body care products as well as pharmaceutical preparations (cf. Ullmann 's Encyclopedia of Industrial Chemistry, 5th Ed., Vol. A6, Weinheim, Verlag Chemie, 1986, pp. 231-332), where it is used as a moisturizer and film former.
  • chitosans and chitosan derivatives depend considerably on the form in which these substances are present, in particular the particle size and consistency.
  • a typical characteristic of chitosan is its poor solubility in the neutral and alkaline pH range as well as in general in non-aqueous media.
  • Another characteristic is its pronounced tendency to gel even at low concentrations, which makes the handling of chitosan and its use, in particular in cosmetics, problematic in many cases.
  • chitosan is only compatible to a limited extent with other components, for example in cosmetic formulations. There is thus a need for chitosans which are easy to handle and dose, are stable in storage and can be processed and used in formulations better than conventional product qualities.
  • chitosan microspheres loaded with an oil body and described in DE 19712978 are suitable as active substance depots which release the active substance in a time-delayed and controlled manner.
  • the microspheres described there represent beads with a diameter of 0.01 to 6 mm.
  • WO 0047177 discloses that the absorption of chitosans or chitosan derivatives can be significantly increased both by the stratum corneum of the skin and by the keratin fibrils of the hair, if these are in the form of nanoparticles, ie particles with an average diameter in the range from 10 to 300 and preferably 50 to 150 nm.
  • JP-A 09221502 discloses chitosan nanospheres which are produced by emulsifying aqueous chitosan solutions in organic solvents in the presence of quaternary ammonium salts.
  • WO-A 9801162 and WO-A 9801160 describe chitosan nanospheres which consist of complexes of chitosan with nucleic acids and are produced by coacervation techniques.
  • chitosan particles whose size is in the nanometer range, which can be produced without organic solvents and which are not necessarily associated with a specific active ingredient, such as nucleic acids in the case of the two aforementioned WOs -Scripts or ⁇ lkörpem in the case of DE 19712978, or a certain surfactant are preloaded. Furthermore, a manufacturing process for such particles should be technically simple and inexpensive and be feasible in conventional and widespread technical plants.
  • the invention thus relates to processes for the preparation of nanoparticulate chitosans or chitosan derivatives with an average particle diameter in the range from 10 to 1000 nm, preferably from 50 to 200 nm, in which
  • organic solvents does not explicitly include the O- Surface modification agent and, if appropriate, organic acids used in step (a) of the process for dissolving the chitosan or chitosan derivative.
  • Chitosans are biopolymers and belong to the group of hydrocolloids. From a chemical point of view, these are partially deacetylated chitins of different molecular weights.
  • the production of chitosans is based on chitin, preferably the shell remains of crustaceans, which are available in large quantities as cheap raw materials.
  • the chitin is usually first deproteinized by adding bases, demineralized by adding mineral acids and finally deacetylated by adding strong bases, it being possible for the molecular weights to be distributed over a broad spectrum.
  • Appropriate methods are, for example, made from Makromol. Chem. 177, 3589 (1976) or French patent application FR 2701266 A1.
  • Chitosan derivatives in the sense of the present invention are to be understood as those derivatives which are water-soluble at acidic pH values, but are sparingly soluble in water in the neutral range and at alkaline pH values, i.e. H. which have a similar solubility behavior as the chitosans themselves.
  • Such chitosan derivatives are, for example, alkoxylation products of chitosans with ethylene oxide, propylene oxide or mixtures of the two, and also derivatives which contain basic amino groups.
  • a chitosan or chitosan derivative is dissolved in water as a solvent with the addition of an acid.
  • the chitosan or chitosan derivative is dissolved by salt formation with a mineral acid or an organic acid, for example with hydrochloric acid, sulfuric acid, methanesulfonic acid, glycolic acid, lactic acid, salicylic acid, adipic acid or ascorbic acid. Hydrochloric acid, glycolic acid and lactic acid are preferred according to the invention.
  • the order in which the individual components are put together is not critical in the preparation of the solution.
  • the chitosan or chitosan derivative is preferably placed in water and mixed with the amount of acid required to form a solution while stirring.
  • the chitosan or chitosan derivative is preferably dissolved at pH values between 1 and 5.
  • the chitosan or chitosan derivative is introduced into an aqueous acid.
  • the pH of the aqueous solution of the chitosan or chitosan derivative is raised to such an extent by means of an alkalizing agent in the presence of a surface modifying agent that the nanoparticulate chitosan or chitosan derivative is precipitated.
  • Aqueous solutions of hydroxides of alkali or alkaline earth metals or ammonia are preferably used as the alkalizing agent.
  • the precipitation is preferably carried out with mechanical mixing, for example by means of a stirrer.
  • the acidic solution of the chitosan or chitosan derivative is introduced and the alkalizing agent is added, or the procedure is reversed. It is essential to the invention that the acidic solution of the chitosan or chitosan derivative is precipitated in the presence of a surface modifier.
  • the surface modifier can be either in the acidic solution or in the alkalizing agent.
  • the acidic solution of the chitosan or chitosan derivative, the alkalizing agent and the surface modifying agent preferably in the form of aqueous solutions, can also be combined with one another at the same time.
  • Surface modification agents are understood to mean substances which physically adhere to the surface of the finely divided particles, but which do not, or only chemically, react with them to a small extent.
  • 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, detergents, etc.
  • Suitable surface modifiers are, for example, emulsifiers of the nonionic surfactant type from at least one of the following groups:
  • polyglycerol esters e.g. Polyglycerol polyricinoleate, 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 C6 / 22 fatty acids, ricinoleic acid as well as 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, ) and polyglucosides (eg cellulose);
  • - polyalkylene glycols 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 homolog mixtures, the middle of which 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 ⁇ -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 oiigomeric 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, alkyl ether sulfates such as, for example, fatty alcohol ether sulfates, glyceryl ether ether sulfate, sulfate (sulfate ether) sulfate ethersulfate, fatty acid (sulfate ether) sulfate, sulfate ether (sulfate) ether sulfate, sulfate ether (sulfate), sulfate ether (sulfate), sulfate ether (sulfate), sulfate
  • 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 glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyl dimethylammonium glycinate, and 2 -Alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate,
  • fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants. Such surface-active compounds are used under ampholytic surfactants. stood, which in addition to a C ⁇ / i ⁇ -alkyl or acyl group in the molecule contain at least one free amino group and at least one -COOH or -S0 3 H group and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylami- noacetic acids each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine.
  • 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. gum arabic, starch, water-soluble derivatives of water-insoluble polymeric natural substances such.
  • B. cellulose ethers such as methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose or modified carboxymethyl cellulose, hydroxyethyl starch or hydroxypropyl guar, and synthetic water-soluble polymers, such as.
  • the nonionic surfactants are particularly preferred as surface modification agents.
  • the nonionic surfactants of the type of alkyl glycosides, ethoxylated alkyl glycosides and addition products of 10 to 60 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with linear fatty alcohols with 8 to 22 carbon atoms have proven to be particularly effective.
  • the surface modification agents are used in a concentration of 10 to 500, but preferably 50 to 250% by weight, based on the chitosans or chitosan derivatives.
  • a suspension which contains a salt as the neutralization product.
  • Desalination of the product and concentration can be carried out by methods familiar to the person skilled in the art, for example by dialysis and / or centrifugation, dialysis preferably followed by centrifugation.
  • the major part of the water is preferably removed by centrifugation, the supernatant simultaneously being the largest part of the salts formed in the course of the process and the excess surface modification agent not required for covering the surface of the nanoparticles Will get removed.
  • the final removal of the residual moisture is carried out using standard drying processes, particularly preferably freeze-drying.
  • Powders of nanoparticulate chitosans or chitosan derivatives produced in this way typically still contain water contents in the range from 1 to 10% by weight, salt contents in the range from 0 to 3% by weight, and contents of surface modification agents in the range from 1 to 5% by weight. %, each based on the total weight of the nanoparticles.
  • contents of surface modification agent of up to 30% by weight can also result. According to the teaching of the invention, it is thus possible to produce nanoparticles which consist of more than 90% by weight of a chitosan or chitosan derivative.
  • chitosans or chitosan derivatives can be obtained in the form of dry powders which are easy to handle and are stable even after prolonged storage, in particular do not tend to agglomerate or stick. They can be redispersed in water or other solvents using mechanical energy to form nanoparticulate dispersions.
  • WO 9100298 describes a process for the continuous production of microcrystalline chitosan in which, according to the description, chitosan is obtained as a dispersion of particles in a size range between 0.1 and 50 ⁇ m. From this dispersion, a powdery product with particle sizes between 1 and 100 ⁇ m should be obtained by drying. Embodiments that could support this information in the description are not provided. In the exemplary embodiments, only gels with a chitosan content of at most approx. 10% are described as process products.
  • the present invention furthermore relates to nanoparticulate chitosans or chitosan derivatives which are produced by the processes according to the invention described above.
  • the nanoparticulate chitosans or chitosan derivatives produced by the process described in the present invention can be used, for example, for the production of cosmetic and / or pharmaceutical preparations.
  • Such preparations include, for example, hair shampoos, hair lotions, hair sprays, foam baths, creams, lotions or ointments.
  • Additional ingredients in the formulation can be found in cosmetic and / or pharmaceutical Preparations contain adjuvants, as are usually used in such preparations, such as. B.
  • preservatives bactericides, antioxidants, perfumes, foam retardants, dyes, pigments, thickeners, moisturizing and / or moisturizing substances, surfactants, emulsifiers, plasticizers, fats, oils, waxes, silicones, sequestering agents, anionic, cationic, nonionic or amphoteric polymers, Alkalizing or acidifying agents, alcohols, polyols, softeners, light stabilizers, electrolytes or organic solvents.
  • Some fabrics, such as B. emulsifiers can be contained in the preparations on the one hand as an adjuvant, but independently as a surface modification agent of the nanoparticles.
  • the amount of the nanoparticulate chitosans or chitosan derivatives in the cosmetic and / or pharmaceutical preparations is chosen so that the concentration of the chitosans or chitosan derivatives contained in the nanoparticles - d. H. without taking into account the surface modification agents contained in the nanoparticles - is between 0.1 and 20, preferably between 0.5 and 2% by weight, based on the preparations.
  • the invention accordingly furthermore relates to cosmetic and / or pharmaceutical preparations which contain nanoparticulate chitosans or chitosan derivatives produced by the process according to the invention in the concentrations mentioned above.

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Abstract

L'invention concerne un procédé permettant de préparer des chitosanes ou des dérivés de chitosane nanoparticulaires, de diamètres particulaires de l'ordre de 10 à 1.000 nm, selon lequel (a) le chitosane ou le dérivé de chitosane est dissous dans un milieu aqueux acide; (b) le pH de la solution est augmenté en présence d'un agent de modification de surface, jusqu'à ce que le chitosane soit précipité. Ce procédé permet de préparer aisément indépendamment de solvants organiques, des nanoparticules stables à l'agglomération, sous forme dispersée ou sèche.
PCT/EP2000/010330 1999-10-29 2000-10-20 Procede de preparation de chitosanes ou de derives de chitosane nanoparticulaires Ceased WO2001032751A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2001535447A JP2003514046A (ja) 1999-10-29 2000-10-20 ナノ粒子状キトサンまたはキトサン誘導体の製造方法
EP00972819A EP1237988A1 (fr) 1999-10-29 2000-10-20 Procede de preparation de chitosanes ou de derives de chitosane nanoparticulaires

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19952073.9 1999-10-29
DE1999152073 DE19952073A1 (de) 1999-10-29 1999-10-29 Verfahren zur Herstellung von nanopartikulären Chitosanen oder Chitosan-Derivaten

Publications (1)

Publication Number Publication Date
WO2001032751A1 true WO2001032751A1 (fr) 2001-05-10

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PCT/EP2000/010330 Ceased WO2001032751A1 (fr) 1999-10-29 2000-10-20 Procede de preparation de chitosanes ou de derives de chitosane nanoparticulaires

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EP (1) EP1237988A1 (fr)
JP (1) JP2003514046A (fr)
DE (1) DE19952073A1 (fr)
WO (1) WO2001032751A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001070191A1 (fr) * 2000-03-23 2001-09-27 Cognis Deutschland Gmbh & Co. Kg Preparations desodorisantes contenant des chitosanes ou des derives de chitosanes nanometriques
WO2003042251A1 (fr) * 2001-11-09 2003-05-22 The Procter & Gamble Company Compositions a base de chitosane
WO2003066682A1 (fr) * 2002-02-07 2003-08-14 Abbott Laboratories De Costa Rica Ltd Procede de deproteinisation de chitosane
WO2004008863A1 (fr) * 2002-07-23 2004-01-29 The Procter & Gamble Company Compositions de traitement capillaire
WO2004078790A1 (fr) * 2003-03-06 2004-09-16 The Procter & Gamble Company Poudre de chitosan
WO2004087307A1 (fr) * 2003-03-31 2004-10-14 Boris Olegovich Maier Produit a base de chitosane, son procede de preparation, procede de preparation de derives dudit produit a base de chitosane et compositions a base de ceux-ci.
FR2859479A1 (fr) * 2003-09-05 2005-03-11 Oligocaps Lab Granule de chitosan utilisable a des fins dietetiques , alimentaires ou phytosanitaires
FR2888581A1 (fr) * 2005-07-12 2007-01-19 Univ Claude Bernard Lyon Nouveau procede de preparation de nanoparticules de chitine
WO2007018452A3 (fr) * 2005-08-04 2007-04-05 Boris Olegovich Maier Produit a base de chitosane et procede de sa fabrication
US7311050B2 (en) 2005-04-19 2007-12-25 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US7490563B2 (en) 2005-04-19 2009-02-17 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
CN100572399C (zh) * 2006-09-19 2009-12-23 宁波新芝生物科技股份有限公司 一种超微化几丁聚糖产品的加工方法
US7943597B2 (en) 2008-04-08 2011-05-17 Cypress Pharmaceutical, Inc. Phosphate-binding chitosan and uses thereof
WO2011117111A1 (fr) 2010-03-25 2011-09-29 Lenzing Aktiengesellschaft Utilisation d'une fibre cellulosique
US8308075B2 (en) 2005-04-19 2012-11-13 Kamterter Products, Llc Systems for the control and use of fluids and particles
US8524326B2 (en) 2008-01-22 2013-09-03 Lenzing Aktiengesellschaft Process for the treatment of cellulosic molded bodies
US8877907B2 (en) 2010-06-07 2014-11-04 The Johns Hopkins University Molecularly imprinted polymers

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US6916465B2 (en) 2000-03-23 2005-07-12 Cognis Deutschland Gmbh & Co. Kg Deodorizing preparations containing nanosacle chitosans and/or chitosan derivatives
WO2003042251A1 (fr) * 2001-11-09 2003-05-22 The Procter & Gamble Company Compositions a base de chitosane
US6638918B2 (en) 2001-11-09 2003-10-28 The Procter & Gamble Company Chitosan compositions
WO2003066682A1 (fr) * 2002-02-07 2003-08-14 Abbott Laboratories De Costa Rica Ltd Procede de deproteinisation de chitosane
WO2004008863A1 (fr) * 2002-07-23 2004-01-29 The Procter & Gamble Company Compositions de traitement capillaire
WO2004078790A1 (fr) * 2003-03-06 2004-09-16 The Procter & Gamble Company Poudre de chitosan
WO2004087307A1 (fr) * 2003-03-31 2004-10-14 Boris Olegovich Maier Produit a base de chitosane, son procede de preparation, procede de preparation de derives dudit produit a base de chitosane et compositions a base de ceux-ci.
FR2859479A1 (fr) * 2003-09-05 2005-03-11 Oligocaps Lab Granule de chitosan utilisable a des fins dietetiques , alimentaires ou phytosanitaires
WO2005023929A3 (fr) * 2003-09-05 2005-07-14 Oligocaps S A Lab Granule
US7536962B2 (en) 2005-04-19 2009-05-26 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US7546812B2 (en) 2005-04-19 2009-06-16 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US10667457B2 (en) 2005-04-19 2020-06-02 Kamterter Products, Llc Systems for the control and use of fluids and particles
US7311050B2 (en) 2005-04-19 2007-12-25 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US7490563B2 (en) 2005-04-19 2009-02-17 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US7509771B2 (en) 2005-04-19 2009-03-31 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US9820426B1 (en) 2005-04-19 2017-11-21 Kamterter Products, Llc Systems for the control and use of fluids and particles
US8235258B2 (en) 2005-04-19 2012-08-07 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US9148994B1 (en) 2005-04-19 2015-10-06 Kamterter Products, Llc Systems for the control and use of fluids and particles
US8501919B2 (en) 2005-04-19 2013-08-06 Kamterer Products, LLC Systems for the control and use of fluids and particles
US7959089B2 (en) 2005-04-19 2011-06-14 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US8308075B2 (en) 2005-04-19 2012-11-13 Kamterter Products, Llc Systems for the control and use of fluids and particles
US8091272B2 (en) 2005-04-19 2012-01-10 Kamterter Ii, L.L.C. Systems for the control and use of fluids and particles
US8163322B2 (en) 2005-04-19 2012-04-24 Kamterter Products, Llc Method of formulating a seed suspension material
US8197735B2 (en) 2005-04-19 2012-06-12 Kamterter Products, Llc Methods for forming fibers
FR2888581A1 (fr) * 2005-07-12 2007-01-19 Univ Claude Bernard Lyon Nouveau procede de preparation de nanoparticules de chitine
WO2007007014A3 (fr) * 2005-07-12 2007-04-26 Univ Claude Bernard Lyon Nouveau procede de preparation de nanoparticules de chitine
WO2007018452A3 (fr) * 2005-08-04 2007-04-05 Boris Olegovich Maier Produit a base de chitosane et procede de sa fabrication
CN100572399C (zh) * 2006-09-19 2009-12-23 宁波新芝生物科技股份有限公司 一种超微化几丁聚糖产品的加工方法
US8524326B2 (en) 2008-01-22 2013-09-03 Lenzing Aktiengesellschaft Process for the treatment of cellulosic molded bodies
US7943597B2 (en) 2008-04-08 2011-05-17 Cypress Pharmaceutical, Inc. Phosphate-binding chitosan and uses thereof
WO2011117111A1 (fr) 2010-03-25 2011-09-29 Lenzing Aktiengesellschaft Utilisation d'une fibre cellulosique
US8877907B2 (en) 2010-06-07 2014-11-04 The Johns Hopkins University Molecularly imprinted polymers
US9434627B2 (en) 2010-06-07 2016-09-06 The Johns Hopkins University Method for selectively binding and separating phosphate anions

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