EP1526837A1 - Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants - Google Patents

Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants

Info

Publication number
EP1526837A1
EP1526837A1 EP03766189A EP03766189A EP1526837A1 EP 1526837 A1 EP1526837 A1 EP 1526837A1 EP 03766189 A EP03766189 A EP 03766189A EP 03766189 A EP03766189 A EP 03766189A EP 1526837 A1 EP1526837 A1 EP 1526837A1
Authority
EP
European Patent Office
Prior art keywords
ascorbic acid
salts
suspensions
fatty acids
solid particles
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.)
Withdrawn
Application number
EP03766189A
Other languages
German (de)
English (en)
Inventor
Axel Jentzsch
Andreas Habich
Christian KÖPSEL
Andreas Ernst
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 SE
Original Assignee
BASF SE
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
Priority claimed from DE2002133738 external-priority patent/DE10233738A1/de
Priority claimed from DE10303527A external-priority patent/DE10303527A1/de
Application filed by BASF SE filed Critical BASF SE
Publication of EP1526837A1 publication Critical patent/EP1526837A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/10—Shaping or working-up of animal feeding-stuffs by agglomeration; by granulation, e.g. making powders
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A23L33/155—Vitamins A or D
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/41—Retaining or modifying natural colour by use of additives, e.g. optical brighteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/201—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having one or two double bonds, e.g. oleic, linoleic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
    • 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
    • A61K8/04—Dispersions; Emulsions
    • A61K8/044—Suspensions
    • 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
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61K8/67—Vitamins
    • A61K8/678—Tocopherol, i.e. vitamin E
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/34—Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • 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
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to suspensions of salts of ascorbic acid, their production and use as antioxidants in cosmetics, pharmacy and in human and animal nutrition.
  • retinoids The substance class of retinoids is one of the most active substances used in cosmetics and dermatology. They work among other things regulating normal cell growth and influencing the differentiation of epithelial cells. For example, retinoic acids are used to treat acne and retinol in anti-wrinkle creams.
  • retinoids are' but also side set strong one, which is partly due to the high instability of "connections. For this reason, strict precautions must be observed at the 61 manufacturing retinoid-containing preparations. For example, should the production done entirely under protective gas and the finished product can be packaged oxygen-impermeable.
  • EP-A-1 055 720 discloses the stabilization of oxygen-sensitive compounds by using thio compounds or glycoproteins in the absence of oxygen.
  • both water- and fat-soluble antioxidants are used together with chelating agents to stabilize retinoids.
  • EP-A-0 590 029 describes suspensions of ascorbic acid particles in the micrometer range and their use as antioxidants and the like. a. for fats, oils, carotenoids and food.
  • WO 01/67896 describes a process for the production of oily suspensions of solid particles of water-soluble vitamins by grinding these particles to an average particle size of 0.1 to 100 ⁇ .
  • carotenoids are understood to mean the following compounds: ⁇ -carotene, lycopene, lutein, astaxanthin, zeaxanthin, cryptoxanthin, citranaxanthin, canthaxanthin, bixin, ⁇ -apo-4-carotinal, ⁇ -apo-8-carotinal, ⁇ -apo -8-carotinic acid esters, individually or as a mixture.
  • Carotenoids used with preference. are ß-carotene, lycopene, lutein, astaxanthin, zeaxanthin, citranaxanthin and canthaxanthin.
  • the carotenoids can be used in crystalline form or as a formulation — for example as dry powder, in accordance with EP-A-0 065 193.
  • lycopene astaxanthin and canthaxanthin, lycopene, astaxanthin or canthaxanthin-containing dry powders are preferred, for example LycoVit®, Lucantin® Pink or Lucantin® Red (10% lycopene, astaxanthin or canthaxanthin dry) - powder, from BASF AG, Ludwigshafen, Germany) together with the salts of ascorbic acid.
  • retinoids mean vitamin A alcohol - (retinol) and its derivatives, such as vitamin A aldehyde (retinal), vitamin A acid (retinoic acid) and vitamin A ester (e.g. retinyl acetate, retinyl propionate and retinyl palmitate).
  • retinoic acid encompasses both all-trans retinoic acid and 13-cis retinoic acid.
  • retinol and retinal preferably include the all-trans compounds.
  • the preferred retinoid used for the suspensions according to the invention is all-trans retinol, hereinafter referred to as retinol.
  • Unsaturated fatty acids are e.g. B. Undecylenic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicapentaenoic acid, docosahexaenoic acid.
  • ascorbic acid encompasses both L-ascorbic acid and its diastereomeric form, D-ascorbic acid (isoascorbic acid).
  • the salts of L-ascorbic acid are used as the preferred embodiment of the solid particles according to the invention.
  • salts of L-ascorbic acid are alkali or alkaline earth metal salts of L-ascorbic acid such as sodium L-ascorbate, potassium L-ascorbate or calcium L-ascorbate, but also salts of L-ascorbic acid with organic amine compounds such as choline ascorbate or L-carnitine ascorbate.
  • Alkali metal salts of L-ascorbic acid are preferably used, particularly preferably sodium L-ascorbate.
  • ascorbic acid or ascorbate stands for the L-form.
  • salts of ascorbic acid can be used both in crystalline form with a purity of greater than 95%, preferably greater than 98%, particularly preferably greater than 99%, and in formulated form, for example as granules, beads or as a spray-dried powder.
  • the above are preferred. Salts in their crystalline form.
  • Suitable dispersants in which the salts of ascorbic acid are insoluble are generally substances in which the solubility of the ascorbate salts is less than 0.01 g / g of dispersant.
  • these include, for example, fats, oils, waxes and organic solvents such as ethers, petroleum ether, aromatic hydrocarbons such as toluene or xylene, chlorinated hydrocarbons such as dichloromethane or chloroform.
  • dispersants which are preferably used in the context of the present invention and in which the salts of ascorbic acid are insoluble are meant the oils which are suitable for use in cosmetics and in human or animal nutrition.
  • esters of linear C 6 ⁇ C come based on fatty alcohols having 6 to 18, 2 fatty acids with linear C 6 -C 22 -fatty alcohols, esters of branched C 6 -C 3 - Carboxylic acids with linear C 6 -C 22 fatty alcohols, esters of linear C 6 -C 22 fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols, in particular Dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (such as propylene glycol, di erdiol or trimer triol) and / or Guerbet alcohols, triglycericles based on C ⁇ -Cio fatty acids, liquid mono- / di- / trig
  • Finsolv ® TN linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, ring-opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons.
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpol siloxanes, cyclic silicones and - a ino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds which are both liquid and at room temperature can be resinous.
  • Typical examples of fats are glycerides. a. Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, if necessary in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or
  • Partial glycerides in question Partial glycerides in question.
  • Metal salts of fatty acids such as. Magnesium, aluminum and / or zinc stearate can be used.
  • Edible oils are generally all physiologically harmless oils - both vegetable and animal - in question, in particular those oils that are liquid at 20 ° C or those in the suspension at 20 ° C alone or together with other oils Form liquid phase.
  • the esters of medium-chain triglycerides e.g. Delios ® SK from Grünau; n-octanoic acid / n-decanoic acid triglyceride
  • the amount of the above-mentioned oxidation-sensitive substances in the suspensions according to the invention is in the range from 0.1 to 40% by weight, preferably from 0.5 to 20% by weight, particularly preferably from 1 to 15% by weight; %, very particularly preferably in the range from 3 to 12% by weight, the% by weight relating to the total amount of the suspensions.
  • the content of one or more of the abovementioned salts of ascorbic acid is in the range from 1 to 50% by weight, preferably from 5 to 40% by weight, particularly preferably from 10 to 35% by weight, very particularly preferably in the range from 15 to 25% by weight, 5% by weight relating to the total amount of the suspensions.
  • At least one retinoid particularly preferably retinol and
  • D [4, 3] denotes the volume-weighted mean diameter (see manual for Malvern Mastersizer S, Malvern Instruments Ltd., UK).
  • the suspensions according to the invention can additionally contain vitamin E, vitamin E derivatives or mixtures thereof.
  • vitamin E stands for natural or synthetic ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherol as well as for tocotrienol.
  • Vitamin E derivatives are e.g. B. Tocopheryl-C 20 alkanoic acid esters as
  • Vitamin E is used in an amount of 1 to 50% by weight, preferably 2 to 40% by weight, particularly preferably 5 to 30% by weight, very particularly preferably 15 to 25% by weight (% by weight) .-% based on the
  • vitamin E vitamin E derivatives or mixtures thereof as dispersants for the suspensions according to the invention.
  • the percentages by weight refer to the total amount of the suspensions and the sum of the parts by weight A to C is 100%.
  • suspensions according to the invention additionally contain at least one drying agent, at least one thickener and / or at least one surface-active agent.
  • thickeners are polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tylose, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polvacrylates (for example Carbopole ® from Goodrich or Synthalene ® from Sigma), polyacrylic amides, polyvinyl alcohol (PVA) and polyvinyl pyrrole ⁇ lon (PVP) as well as VA / VP copolymers (Luviskol ® , from BASF), polyethylenes, surfactants such as ethoxylated fatty acid eglycerides (including Cremophor ® C0, from BASF), esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohols ethoxylates with a narrow homolog distribution or Alkiy
  • phyllosilicates such as Bentone ® EW (Electnentis Specialties) or Tixogel ® VP (Süd Chemie).
  • Further thickeners are highly disperse silica (Aerosil ® , from Degussa), polyethylene glycols (Lutrol ® , from BASF), stearic acid, trihydroxy-stearin, polyoxyethylene glycerol triricinoleate, triglyceride of C 12 / C ⁇ 4 fatty acids.
  • the amount of thickener in the suspensions according to the invention is in the range from 0.1 to 10% by weight, preferably 0.5 to 8% by weight, particularly preferably 0.7 to 3% by weight, very particularly preferably 0, 8 to 1.5 wt .-%, based on the total amount of suspensions.
  • Polyol and especially polyglycerol esters such as.
  • Partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol),
  • Alkyl glucosides eg methyl glucoside, butyl glucoside, lauryl glucoside
  • polyglucosides eg cellulose
  • 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.
  • Ci 2 / Ci 8 fatty acid monoesters and diesters of additive products of ethylene oxide with glycerol are known from DE-PS 2024051 as refilling agents for cosmetic
  • C 8 / Ci 8 alkyl mono- and oligoglycosides 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 ester 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.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • the second ionic surfactants are those surface-active compounds which carry 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 the cocoalkyldimethylammonium glycinate, N-Ac ⁇ -laminopropyl-N, N-dimethylammoniumglycineate, for example the cocoacylaminopropyldimet.hylammonium glycinate, ⁇ and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group, and the cocoacrylic acid inoethylhydroxyethylcarboxymethylglycinat.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-Ac ⁇ -laminopropyl-N, N-
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a Cs / Ci 8 -alkyl or acyl group, contain at least one free amino group and at least one -COOH or -S0 3 H group in the molecule and to form internal salts are qualified.
  • ampholytic surfactants are N-alkylglycine, N-alkylaminopropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkyl aminopropionic acid and alkylamino acetic acid with each around 8 to 18 C-Ato- men in the alkyl group.
  • ampholytic surfactants are N-coconut alkylaminopropiona, coconut acylaminoethyl laminopropionate and Ci 2 / Ci 8 acyl sarcosine.
  • ampholytic emulsifiers quaternary emulsifiers are also suitable, those of the esterquat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • the amount of surface-active agents in the suspensions according to the invention is in the range from 0.1 to 10% by weight, preferably 0.5 to 8% by weight, particularly preferably 1 to 5% by weight, based on the total amount of the suspensions ,
  • drying agents are compounds selected from the group consisting of alkali and alkaline earth metal sulfates such as sodium, calcium and magnesium sulfate, alkali and alkaline earth metal chlorides such as sodium, calcium and magnesium chloride and silica gel.
  • alkali and alkaline earth metal sulfates such as sodium, calcium and magnesium sulfate
  • alkali and alkaline earth metal chlorides such as sodium, calcium and magnesium chloride and silica gel.
  • CaCl 2 should be mentioned as a particularly preferred desiccant.
  • the amount of desiccant used is generally between 0.1 and 20% by weight, preferably between 0.5 and 15% by weight, particularly preferably between 1.0 and 10% by weight, based on the total amount of the suspension ,
  • the invention also relates to a process for the preparation of the suspensions described at the outset, characterized in that
  • oscidation-sensitive substance being selected from the group consisting of carotenoids, retinoids and unsaturated fatty acids before, during or after grinding to the dispersant or
  • solid particles of one or more salts of ascorbic acid are ground to a mean particle size of 0.01 to 1000 ⁇ m without using a continuous phase and the ground particles are then suspended in a dispersant in which the salts of ascorbic acid are insoluble, where the oxidation-sensitive substance (s) selected from the group consisting of carotenoids, retinoids and unsaturated fatty acids, can give to the dispersant during or after the suspension of the solid ascorbate particles-
  • the grinding according to a) can be carried out in a manner known per se, for. B. done with a ball mill. Depending on the type of mill used, grinding is carried out until the particles have the above-mentioned mean particle size D [4, 3] determined by Fraunhofer diffraction from 0.01 to 1000 ⁇ m, preferably from 0.1 to 500 ⁇ m, particularly preferably from 0, 2 to 200 ⁇ m, very particularly preferably in the range from 0.5 to 50 ⁇ m, in particular 0.5 to 20 ⁇ m.
  • a preferred embodiment of the wet grinding described under a) takes place in the presence of one or more thickeners, the oxidation-sensitive substance (s) being added to the dispersant after the grinding.
  • the suspensions according to the invention can also be prepared according to b) by dry grinding the solid particles of one or more salts of ascorbic acid and then suspending the ground particles in a dispersant in which the salts of ascorbic acid are insoluble.
  • dry grinding is understood to mean grinding without using a continuous phase.
  • the oxidation-sensitive substance (s) selected from the group consisting of carotenoids, retinoids and unsaturated fatty acids can be added to the dispersant before, during or after the suspension of the solid ascorbate particles.
  • a preferred embodiment of the preparation of the suspensions described under b) is such that the oxidation-sensitive substance (s) are already dissolved or dispersed in the dispersant before the ascorbate particles are added.
  • the invention also relates to the use of solid particles of one or more salts of ascorbic acid as antioxidants for substances sensitive to oxidation, selected from the group consisting of carotenoids, retinoids and unsaturated fatty acids in a dispersant in which the salts of ascorbic acid are insoluble.
  • the use according to the invention is advantageously carried out entirely with solid particles of one or more salts of ascorbic acid with an average particle size in the range from 0.01 to 1000 ⁇ m, preferably from 0.1 to 500 ⁇ m, particularly preferably from 0.2 to 200 ⁇ m particularly preferably in the range from 0.5 to 50 ⁇ m, in particular from 0.5 to 20 ⁇ m.
  • ⁇ -tocopherol as an additional, oil-soluble antioxidant.
  • the suspensions of the invention are characterized u. a. characterized in that it is possible to dispense with the use of protective gas during their manufacture, filling and storage, while at the same time ensuring sufficient stability.
  • Sufficient stability in the sense of the invention is understood to mean that at least 90% of the retinoid is found in the preparation after storage for at least 2 weeks at 40 ° C. Furthermore, there are no undesirable color changes when the preparations according to the invention are stored.
  • suspensions according to the invention using solid particles of salts of ascorbic acid in particular using solid sodium ascorbate particles, have advantageous properties.
  • the retinol preparations using solid ascorbic acid particles show a significant decrease in retinol after only two weeks of storage, the recovery rate of retinol is in the presence of the first sodium ascorbate particles - with and without protective gas - over 9 0%.
  • the suspensions are u. a. as an additive for food and animal feed preparations or compound feed, as an agent for the manufacture of pharmaceutical and cosmetic preparations and for the manufacture of nutritional supplements in the human and animal sectors.
  • the suspensions can preferably be used for the production of cosmetic preparations.
  • the suspensions can also preferably be used as a feed additive in animal nutrition, in particular for application or spraying onto feed pellets.
  • a preferred embodiment of the spraying method is that the feed pellets are loaded with the oily suspension under reduced pressure. Examples of this can be found, inter alia, in GB-A-2 232 573 and in EP-A-0 556 883.
  • Typical areas of application in the food sector are, for example, the vitaminization of beverages and dairy products such as
  • the oily suspensions can be used, for example, for vitamin-containing personal care products, for example in the form of a cream, a lotion, as lipsticks or make-up.
  • the invention further relates to food supplements, animal feed, foodstuffs and pharmaceutical and cosmetic preparations containing the oily suspensions of water-soluble vitamins described at the outset.
  • Dietary supplements and pharmaceutical preparations containing the suspension according to the invention include To understand tablets, dragees and preferably hard and soft gelatin capsules.
  • Cosmetic preparations which can contain the suspensions according to the invention are, for example, topically applicable preparations, in particular decorative personal care products such as lipsticks, facial make-up in the form of a cream and lotions.
  • the finely divided suspension emerging from the mill was collected and measured using a particle size measuring device (Malvern Mastersizer). The grinding process was repeated until 90% of the suspended particles had a particle size of less than 10 ⁇ m [D (0.9) ⁇ 10 ⁇ ]. This corresponded to an average particle size D [4 3] of 5.2 ⁇ m.
  • a medium-chain triglyceride Delios® SK from Grünau, Germany
  • the mixture was then poured into a stirrable receiver, from which the suspension was conveyed by means of a peristaltic pump through a continuously operated ball mill (Dyno Mill KDL Spezial).
  • the grinding mill of the ball mill was filled with 400 g glass balls (diameter 800 to 1200 ⁇ m).
  • the fine one-part suspension emerging from the mill was taken up and measured using a particle size measuring device (Malvern Mastersizer).
  • the grinding process was repeated until 90% of the suspended particles had a particle size of less than 20 ⁇ m [D (0.9) ⁇ 20 ⁇ m]. This corresponded to an average particle size D [4, 3] of 10, 9.
  • part of the dispersion was diluted with 10 times the amount of oil used and left to stand for 12 hours. Neither the undiluted nor the diluted dispersion showed any signs of sedimentation over this period.
  • the grinding bowl of the ball mill was filled with 400 g glass balls (diameter 800 to 1200 ⁇ m).
  • the finely divided suspension emerging from the mill was collected and measured using a particle size measuring device (Malvern Mastersi zer).
  • the grinding process was repeated until 90% of the suspended particles had a particle size less than 20 ⁇ m [D (0.9) ⁇ 20 ⁇ m]. This corresponded to an average particle size D [4, 3] of 10, 9 ⁇ m.
  • the finely divided suspension emerging from the mill was collected and measured using a particle size measuring device (Malvern Mastersizer). The milling process was repeated until 90% of the suspended particles had a particle size smaller than 20 ⁇ m [D (0.9) ⁇ 20 ⁇ ]. This corresponded to an average particle size D [4, 3] of 10, 9 ⁇ .
  • a solution of 50 g of all-trans retinol in 285 g of miglyol was then added to the suspension, and stirring was continued with a blade stirrer until a homogeneous suspension was obtained.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Animal Husbandry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Mycology (AREA)
  • Dispersion Chemistry (AREA)
  • Microbiology (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Botany (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fodder In General (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Medicinal Preparation (AREA)

Abstract

Suspensions qui contiennent (A) au moins une substance sensible à l'oxydation choisie dans le groupe constitué par les caroténoïdes, les rétinoïdes et les acides gras insaturés et (B) des particules solides d'un ou de plusieurs sels de l'acide ascorbique, dans un milieu de dispersion dans lequel les sels de l'acide ascorbique sont insolubles.
EP03766189A 2002-07-24 2003-07-16 Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants Withdrawn EP1526837A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE2002133738 DE10233738A1 (de) 2002-07-24 2002-07-24 Suspensionen von Salzen der Ascorbinsäure und ihre Verwendung als Antioxidantien
DE10233738 2002-07-24
DE10303527A DE10303527A1 (de) 2003-01-29 2003-01-29 Suspensionen von Salzen der Ascorbinsäure und ihre Verwendung als Antioxidantien
DE10303527 2003-01-29
PCT/EP2003/007705 WO2004012707A1 (fr) 2002-07-24 2003-07-16 Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants

Publications (1)

Publication Number Publication Date
EP1526837A1 true EP1526837A1 (fr) 2005-05-04

Family

ID=31496729

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03766189A Withdrawn EP1526837A1 (fr) 2002-07-24 2003-07-16 Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants

Country Status (5)

Country Link
US (1) US20060078597A1 (fr)
EP (1) EP1526837A1 (fr)
JP (1) JP2006502127A (fr)
AU (1) AU2003250967B2 (fr)
WO (1) WO2004012707A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004051245A1 (de) * 2004-10-20 2006-04-27 Aquanova German Solubilisate Technologies (Agt) Gmbh Vitamin C-Solubilisat
US20070078180A1 (en) * 2005-10-04 2007-04-05 Kern Dale G Methods and compositions for stabilizing an antioxidant
WO2010086989A1 (fr) 2009-01-29 2010-08-05 日東電工株式会社 Base intra-orale en forme de film et préparation
JP5751868B2 (ja) 2010-03-30 2015-07-22 日東電工株式会社 フィルム状製剤及びその製造方法
WO2012133246A1 (fr) * 2011-03-30 2012-10-04 富士フイルム株式会社 Composition contenant un caroténoïde et procédé pour produire celle-ci
US20130089641A1 (en) * 2011-10-11 2013-04-11 Sunway Biotech Co., Ltd. Soymilk with Additive of Vitamin C, Vitamin C salt or Vitamin C Stereoisomer
JP5841433B2 (ja) * 2012-01-11 2016-01-13 日東電工株式会社 口腔内フィルム状基剤及び製剤
FR2988091B1 (fr) * 2012-03-16 2014-08-15 Innov Ia 3I Compositions pulverulentes d'un complexe entre un acide et un metal et leur procede de preparation
ES2603928T3 (es) * 2012-09-06 2017-03-02 F. Hoffmann-La Roche Ag Composiciones y métodos de estabilidad de matriz mejorada
KR102051058B1 (ko) * 2019-06-11 2019-12-02 제니코스(주) 아스코빅 애씨드 분산물 및 이를 함유하는 화장료 조성물
IL268457B (en) * 2019-08-04 2022-05-01 Omega 3 Galilee Ltd Oil suspension of edible solids and methods of preparation

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2935449A (en) * 1958-04-14 1960-05-03 Pfizer & Co C Stabilized vitamin a compositions
US5230836A (en) * 1991-06-20 1993-07-27 Kalamazoo Holdings, Inc. Low micron-sized ascorbic acid particles, especially a suspension thereof in a medium in which they are insoluble, and the use thereof as an antioxidant for mediums in which the particles remain insoluble
JPH07107938A (ja) * 1993-10-08 1995-04-25 Sanei Gen F F I Inc ドコサヘキサエン酸油含有食品
JP3681200B2 (ja) * 1994-09-07 2005-08-10 ジョンソン・エンド・ジョンソン株式会社 スキンケア組成物用容器
JPH09176679A (ja) * 1995-12-26 1997-07-08 Okawa Shokuhin Kogyo Kk 不飽和脂肪酸粉状体の耐酸化法、不飽和脂肪酸粉状体耐酸化性組成物および機能性食品
US5827539A (en) * 1995-12-28 1998-10-27 Amway Corporation Dry carotenoid-oil powder and process for making same
DE19609477A1 (de) * 1996-03-11 1997-09-18 Basf Ag Stabile wäßrige Solubilisate von Carotinoiden und Vitamine
AU5416998A (en) * 1997-10-14 1999-05-03 Quest International B.V. Preparation for the enhancement of the antioxidant status of cells
BR9803936A (pt) * 1998-09-08 2000-04-04 Cosmeticos Natural Ind Com Processo e composição para aumentar a ação de vitamina a na atividade celular de um indivìduo e uso de vitamina c.
GB9921238D0 (en) * 1999-09-09 1999-11-10 Boots Co Plc Skincare composition
JP2001151664A (ja) * 1999-11-19 2001-06-05 Isehan:Kk レチノイド類を含有する皮膚外用剤
CN1197483C (zh) * 2000-03-17 2005-04-20 巴斯福股份公司 制备水溶性维生素的油性悬浮液的方法
CA2424830C (fr) * 2000-09-11 2011-06-28 Industria E Comercio De Cosmeticos Natura Ltda. Composition contenant du fucose et de la vitamine c et/ou de la vitamine a
US20040043043A1 (en) * 2000-09-20 2004-03-04 Schlyter Jimmy Hirschsprung Preparation of emulsions and concentrates thereof
JP2002138014A (ja) * 2000-10-31 2002-05-14 Noevir Co Ltd 微細エマルション組成物
US7105176B2 (en) * 2000-11-29 2006-09-12 Basf Aktiengesellschaft Production of solid preparations of water-soluble, sparingly water-soluble or water-insoluble active compounds
US20060078580A1 (en) * 2004-10-08 2006-04-13 Mediquest Therapeutics, Inc. Organo-gel formulations for therapeutic applications

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004012707A1 *

Also Published As

Publication number Publication date
WO2004012707A1 (fr) 2004-02-12
US20060078597A1 (en) 2006-04-13
JP2006502127A (ja) 2006-01-19
AU2003250967A1 (en) 2004-02-23
AU2003250967B2 (en) 2009-05-28

Similar Documents

Publication Publication Date Title
EP0845503B1 (fr) Compositions de caroténoides liquides miscibles à l'huile
EP2111125B1 (fr) Formulations liquides comprenant des carotenoides
EP0981969B1 (fr) Composition de caroténoides compenant un mélange de beta-carotène, lycopène et lutéine
EP1898721B1 (fr) Procédé de production d'une suspension aqueuse et d'une préparation pulvérulente d'un ou de plusieurs caroténoïdes
EP1575378B1 (fr) Formulations pulverulentes a base de phytosterols
EP1272059B1 (fr) Procede pour la production de suspensions huileuses de vitamines solubles dans l'eau
EP2188250B1 (fr) Procédé de production de solutions huileuses de dérivés de l'astaxanthine
EP2224823A1 (fr) Préparation pulvérulente de caroténoïde pour la coloration de boissons
DE102005031468A1 (de) Wässrige Suspensionen schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und daraus hergestellte Trockenpulver
DE102004046026A1 (de) Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Carotinoide
EP2403362B1 (fr) Compositions pulvérulentes de dérivés d'astaxanthine ii
WO2004012707A1 (fr) Suspensions de sels de l'acide ascorbique et leur utilisation en tant qu'antioxydants
EP2403364B1 (fr) Procédé de production de solutions de dérivés d'astaxanthine
EP2403359B1 (fr) Composition pulvérulente de dérivés d'astaxanthine i
EP1186292B1 (fr) Pudre sechée des carotinoides avec des noyaux multiples
EP2403363B1 (fr) Formulation de dérivés d'astaxanthine et leur utilisation ii
WO2006000347A1 (fr) Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions
DE10233738A1 (de) Suspensionen von Salzen der Ascorbinsäure und ihre Verwendung als Antioxidantien
DE10303527A1 (de) Suspensionen von Salzen der Ascorbinsäure und ihre Verwendung als Antioxidantien
EP1824452A1 (fr) Dispersions aqueuses d'un melange d'agents actifs difficilement solubles dans l'eau ou insolubles dans l'eau et d'une matiere proteique d'organisme unicellulaire
DE10049137A1 (de) Verfahren zur Herstellung öliger Suspensionen wasserlöslicher Vitamine
DE10013312A1 (de) Verfahren zur Herstellung öliger Suspensionen wasserlöslicher Vitamine
EP2792246A1 (fr) Procédé de fabrication d'une suspension d'astaxanthine

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20050224

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL LT LV MK

17Q First examination report despatched

Effective date: 20060825

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20120201