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EP1605773A2 - Adsorbat contenant des principes actifs - Google Patents

Adsorbat contenant des principes actifs

Info

Publication number
EP1605773A2
EP1605773A2 EP04717597A EP04717597A EP1605773A2 EP 1605773 A2 EP1605773 A2 EP 1605773A2 EP 04717597 A EP04717597 A EP 04717597A EP 04717597 A EP04717597 A EP 04717597A EP 1605773 A2 EP1605773 A2 EP 1605773A2
Authority
EP
European Patent Office
Prior art keywords
adsorbed
acid
oil
component
stabilizer
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Withdrawn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
EP04717597A
Other languages
German (de)
English (en)
Inventor
Andreas Habich
York Hartleben
Dietmar Weller
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
Application filed by BASF SE filed Critical BASF SE
Priority to DK09152282.1T priority Critical patent/DK2060189T3/da
Priority to DE202004021155U priority patent/DE202004021155U1/de
Priority to EP09152282A priority patent/EP2060189B1/fr
Publication of EP1605773A2 publication Critical patent/EP1605773A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/75—Fixation, conservation, or encapsulation of flavouring agents the flavouring agents being bound to a host by chemical, electrical or like forces, e.g. use of precursors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/77—Use of inorganic solid carriers, e.g. silica
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A23P10/35—Encapsulation of particles, e.g. foodstuff additives with oils, lipids, monoglycerides or diglycerides
    • 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
    • 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
    • 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
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • 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
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • Preparations containing active ingredients are important in a large number of technical applications, examples being foods, animal feeds or cosmetic agents.
  • No. 4,434,187 describes preparations for curing meat which, in addition to the meat treatment agent, contain vitamin E, optionally lecithin and silica particles.
  • the silica particles suitable according to US 4,434,187 have an average particle size of 1.5 to 9 ⁇ m.
  • WO 97/37546 A1 (EP 1 006806) describes free-flowing preparations which contain a mixture of fats and optionally a filler. Silica is mentioned as a filler. The preparations described there are physical mixtures of the fats with the filler and no adsorbates.
  • WO 00/27362 A1 (EP 1 133279) describes dry, free-flowing mixtures of liquid tocopherols which contain corn starch and silica.
  • the silica used has a particle size of 40 - 50 ⁇ m
  • WO 92/13531 A1 (EP 524308) describes preparations with increased bioavailability from vitamin E, a surfactant emulsifier at least one inert carrier.
  • the inert carriers mentioned include microcrystalline cellulose, silicon dioxide, starch.
  • the mixtures of vitamin E and surfactant must have an HLB value of 7 to 14 in order to have the increased bioavailability required according to the invention.
  • US 4,617,294 describes free-flowing granular silica particles with a particle size of 0.14 mm to 0.84 mm and their use as an adsorbent for vitamins. The Ver- The use of stabilizers is not discussed. US Pat. No. 4,617,294 on page 3, lines 44-45 describes that the oil-soluble vitamins can be present in an oil.
  • EP 0 062225 B1 (BASF Corp.) describes spray-dried vitamin E powder based on hydrolyzed gelatin and caseinates, which is produced with 0.5 to 2.0% by weight of silicon dioxide as a spray drying aid or powdering agent.
  • EP 0326 026 B1 (BASF AG) describes vitamin-containing dispersions or emulsions which are converted into granular or powdery solids by conventional drying steps.
  • the preparations can contain flow aids such as silicon dioxide and fillers such as starch and silicates.
  • JP 07-133491 describes solid preparations which contain an oil-soluble substance. They are obtained by applying liquid oil-soluble compounds to silicates and then solidifying them. Spherical particles with a particle size of 20 to 30 ⁇ m are used as suitable silicates (Carplex commercial products from Shionogi & Co.). The preparations obtainable in this way are particularly suitable as low-odor dosage forms for fish oils.
  • the object of the present invention was therefore to provide active substance-containing formulations which are easy to handle and at the same time ensure high stability of the active substances in the preparations. It was an object of the present invention to provide preparations which allow active ingredients to be incorporated into complex substrates, for example in animal feed or premixes or other mixtures for animal feed, without clumping or segregation phenomena or other application or handling disadvantages or caking of the substrate comes while maintaining the stability of the active ingredient. It is of particular interest that the other ingredients of the complex substrate are not influenced by the admixture. It is also important that the active ingredients in the formulations are accessible.
  • a process for the production of adsorbates suitable for human or animal nutrition and cosmetic applications in which a component (A) to be adsorbed is applied to a support (C) using at least one stabilizer (SB), where the average particle size of the carrier (C) is at least 80 with the proviso that if the component (A) to be adsorbed is vitamin E, the mixture of (A) and (B) has an HLB value of less than 7 and with the proviso that if the component (A) to be adsorbed is an oil-soluble vitamin and the stabilizer (B) is a glyceride, the freezing point of the mixture of (A) and (B) is less than or equal to 80 ° C.
  • SB stabilizer
  • Adsorbates for the purposes of the present invention are in particular preparations in which at least 10% by weight, in particular at least 20, preferably at least 30, particularly preferably at least 40, in particular at least 50% by weight, of the substances to be adsorbed (sum of all constituents of the adsorbate without the carrier (C), ie usually at least active ingredient (A) and stabilizer (B)) are present in the inner pore volume of the carrier (C).
  • the internal pore volume of a carrier can be determined as an empty volume according to the DPB (dibutyl phthalate) method DIN 53601.
  • Adsorbates in which at least 60% by weight, preferably at least 70% by weight, in particular at least 80% by weight are present in the inner pore volume of the carrier (C) are particularly preferred.
  • the adsorbates of the present invention are distinguished by better handling and application advantages. Furthermore, the adsorbates are accessible via conventional fluidized bed techniques and mixer techniques.
  • the vitamin-containing preparations described in US Pat. No. 4,617,294 contain no stabilizers in the sense of the present invention and have no increased stability during storage or in complex matrices.
  • the HLB value (hydrophilic lipophilic balance) is a measure of the oil or water solubility of predominantly nonionic surfactants and the stability of emulsions.
  • the HLB value can be determined experimentally using the so-called phenol titration method, by adding 5% phenol solution to the surfactant solution until it becomes cloudy. Substances to be adsorbed (A)
  • component (A) all substances which are suitable for human and / or animal consumption are suitable as component (A) to be adsorbed.
  • component (A) Substances that are used as active ingredients in food, animal feed and / or cosmetic agents are particularly suitable.
  • Suitable components (A) are also cosmetic active ingredients, such as vitamins, panthenol, bisabolol, phytosterols, such as cholesterol, perfume oils and / or collagen.
  • oil-soluble compounds are used as components (A).
  • a stabilizer from the group of the glycerides (b-1) is preferably used as the stabilizer (B).
  • the component (A) to be adsorbed is an oil-soluble compound
  • a stabilizer from the group of the polysaccharides (b-3) is preferably used as the stabilizer (B).
  • a stabilizer from the group of the emulsifiers (b-2) is preferably used as the stabilizer (B).
  • a stabilizer from the group of chelators (b-4) is preferably used as stabilizer (B). If the component (A) to be adsorbed is an oil-soluble compound, at least one stabilizer from the group of the glycerides (b-1) and at least one stabilizer from the group of the emulsifiers (b-2) are preferably used as the stabilizer (B).
  • the component (A) to be adsorbed is an oil-soluble compound
  • at least one stabilizer from the group of glycerides (b-1) and at least one stabilizer from the group of chelators (b-4) are preferably used as stabilizer (B).
  • At least one stabilizer from the group of chelators (b-4) and at least one stabilizer from the group of emulsifiers (b-2) are preferably used as stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • a stabilizer from the group of the polysaccharides is preferably used as the stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • a stabilizer from the group of the glycerides (b-1) is preferably used as the stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • a stabilizer from the group of the emulsifiers (b-2) is preferably used as the stabilizer (B).
  • a stabilizer from the group of chelators (b-4) is preferably used as stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • at least one stabilizer from the group of the glycerides (b-1) and at least one stabilizer from the group of the emulsifiers (b-2) are preferably used as the stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • at least one stabilizer from the group of glycerides (b-1) and at least one stabilizer from the group of chelators (b-4) are preferably used as stabilizer (B).
  • the component (A) to be adsorbed is a water-soluble compound
  • at least one stabilizer from the group of the chelating agents is preferably used as the stabilizer (B).
  • compounds are used as components (A) which are selected from the group consisting of vitamins, carotenoids, xanthophylls, unsaturated fatty acids and lipoic acid.
  • At least one vitamin is used as component (A).
  • Water-soluble vitamins are thiamine (B ⁇ , riboflavin (B 2 ), niacin, biotin, vitamin B 6 (pyridoxine, pyridoxal, pyridoxamine and their 5 ' - phosphoric acid esters), pantothenic acid, folic acid, cobalamin (B 12 ) and vitamin C ( Ascorbic acid and ascorbyl palmitate).
  • Oil-soluble vitamins include vitamin A (retinol, retinal, retinoic acid), calcifole (vitamin D), tocopherols (vitamin E), phylloquinone (vitamin Ki) and menaquinone (vitamin K 2 ).
  • At least one oil-soluble vitamin is used as component (A).
  • vitamins include all compounds that have biological vitamin activity, e.g. As “vitamin A” all retinoids which qualitatively have the biological activity of all-trans-retinol and its esters, examples include vitamin A acetate, vitamin A propionate, vitamin A palmitate or other esters or derivatives of vitamin A. ,
  • vitamin E includes all derivatives of tocol and tocotrienol which qualitatively have the biological activity of .alpha.-tocopherol. Called its .alpha., .Beta. And .gamma. Tocopherol and .alpha., .Beta. And .gamma. Tocotrienol and the corresponding diastereomers , in particular all-rac- tocopherol and the esters, in particular acetates and palmitates.
  • Vitamin E is used as the component (A) to be adsorbed.
  • carotenoids and xanthophylls such as, for example, lycopene, ⁇ -carotene, ⁇ -carotene, astaxanthin, astaxanthin ester, canthaxanthin, citranaxanthin, beta-apo-8'-carotinic acid ethyl ester, beta-apo 8 1 - carotenal, lutein and lutein ester, zeaxanthin or zeaxanthin ester, ß-cryptoxanthin and ß-cryptoxanthin ester, capsanthin or capsanthin ester, capsorubin or
  • components (A) to be adsorbed can be present as mixtures of the substances mentioned.
  • R-COOH where R is a C1 to C22 alkyl radical, linear or branched, with at least one double bond.
  • fatty acid encompasses the salts and esters of the respective acids, in particular the alkali and alkaline earth metal salts, as well as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec. Butyl and tert-butyl esters.
  • the unsaturated fatty acids contain one, two, three, four, five or six double bonds in the acyl residue.
  • the so-called isolate fatty acids should be mentioned, i.e. the double bond is interrupted by a methylene group.
  • Particularly suitable unsaturated fatty acids are the so-called ⁇ -3, ⁇ -6 and ⁇ -9 fatty acids. Examples include those named ⁇ -3 fatty acids ⁇ -linolenic acid, oleic acid, palmitoleic acid and myristoleic acid, ⁇ -6 fatty acids linoleic acid, ⁇ -linolenic acid and arachidonic acid and ⁇ -9 fatty acids oleic acid, erucic acid and nervonic acid.
  • unsaturated fatty acids are the polyunsaturated fatty acids with 22 carbon atoms, so-called eicosapolyenic acids.
  • Fatty acids with conjugated double bonds are also suitable, such as, for example, ⁇ -elaidostearic acid, ⁇ -elaidostearic acid or parinaric acid.
  • polyunsaturated fatty acids are used as components (A), in particular conjugated unsaturated fatty acids.
  • at least one conjugated octadecapolyenoic acid is used as component (A), preferably at least one octadecadienoic acid, octadecatrienoic acid or combinations of these octadecapolyenoic acids.
  • Calendulic acid or punicic acid may be mentioned as octadecatrienic acid.
  • component (A) are conjugated octadecapolyenoic acids, in which 50% of the fatty acid portion is 9-cis, 11-trans or 10-trans, 12-cis octadecadienoic acid.
  • components (A) are conjugated octadecapolyenoic acids in which 60% of the fatty acid portion is 9-cis, 11-trans or 10-trans, 12-cis octadecadienoic acids.
  • components (A) are conjugated octadecapolyenoic acids in which less than 5% of the fatty acid component is 11, 13-octadecadienoic acid isomers, 8,10-octadecadienoic acid isomers, cis, cis-octadecadienoic acid isomers or trans, trans-octadecadienoic acid -Isomers or mixtures of these isomers.
  • components (A) are conjugated octadecapolyenoic acids in which less than 3% of the fatty acid component is 11-, 13-octadecadienoic acid isomers, 8-, 10-octadecadienoic acid isomers, cis, cis-octadecadienoic acid isomers or trans, trans -Octadecadienoic acid isomers or mixtures of these isomers.
  • components (A) are conjugated octadecapolyenoic acids in which less than 1% of the fatty acid component is 11-, 13-octadecadienoic acid isomers, 8-, 10-octadecadienoic acid isomers, cis, cis-octadecadienoic acid isomers or trans, trans -Octadecadienoic acid isomers or mixtures of these isomers.
  • Chelators (b-4) selected from the group consisting of salicylic acid, stearyl citrate, tartaric acid and citric acid are particularly preferred.
  • Emulsifiers (b-2) selected from the group consisting of are particularly preferred - Adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil; such as the products available under the trade name Cremophor (BASF AG).
  • polyglycerol esters e.g. Polyglycerol polyricin oleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable; and
  • Perfume oils are suitable as component (A) to be adsorbed.
  • Mixtures of natural and synthetic fragrances are mentioned as perfume oil ⁇ .
  • Natural fragrances are extracts of flowers (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme) ), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethylphenylglycinate, allylcyclohexyl benzyl salpylatepionate, and
  • the ethers include, for example, benzyl ethyl ether, the aldehydes, for example, the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden flower oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and la-vandula oil.
  • Mandarin oil orange oil, allylamyl glycolate, cyclovertal, lavandin oil, muscatal sage oil, b-damascone, geranium oil bourbon, cyclohexyl salicylate, vertofix asphalt, iso-e-super, fixolide NP, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, rose oxide , Romilat, Irotyl and Floramat used alone or in mixtures.
  • component (A) to be adsorbed is lipoic acid, physiologically acceptable derivatives or salts thereof.
  • lipoic acid denotes 5- (1, 2-dithiolan-3-yl) valeric acid, also called thioctic acid, thioctanoic acid or thioctic acid, of the formula I.
  • optical isomers covered by this formula both as mixtures, e.g. Race- mate, as well as in pure form, e.g. R or S enantiomers included.
  • the preferred isomer is the (R) -5- (1, 2-dithiolan-3-yl) valeric acid of the formula II
  • Lipoic acid mixtures with an (R) -enantiomeric excess (ee) of at least 40% are preferred.
  • the (R) -enantiomeric excess is preferably at least 80%, in particular at least 98%.
  • ee [%] (RS) / (R + S) x 100.
  • R and S are the descriptors of the CIP system for the two enantiomers and represent the absolute configuration at the asymmetric C (5) atom.
  • Lipoic acid derivatives include, in particular, synthetic precursors and metabolites of lipoic acid, that is, above all, dihydroliponic acid. Liponamide, lipoyllysine, di-6,8-bis-norliponic acid and tetranorliponic acid are to be mentioned as further metabolites.
  • Other suitable lipoic acid derivatives are, for example, those described in WO 99/45922 as lipoic acid Re-analogs of formula (I) described esters, thioesters and amides of lipoic acid with amino alcohols, aminothiols or diamines, which are part of the present application by reference. According to the statements on lipoic acid, the respective optical isomers of the derivatives also belong to it.
  • the physiologically acceptable salts of lipoic acids or lipoic acid derivatives are preferably base addition salts.
  • the base addition salts include salts with inorganic bases, for example metal hydroxides or carbonates of alkali, alkaline earth or transition metals, or with organic bases, for example ammonia, basic amino acids such as arginine and lysine, amines, e.g.
  • Salts with inorganic bases e.g. Na, K, Mg, Ca, Zn, Cr and Fe salts.
  • All substances which lead to a delayed breakdown of the active ingredient (A) in the adsorbate are suitable as stabilizers.
  • the reference here is a suitably produced adsorbate without stabilizer.
  • the stabilizers (B) are generally chosen such that the mixture of (B) with the component (A) to be adsorbed at temperatures below 80 ° C, preferably below 60 ° C, especially below 40 ° C, solid.
  • component (A) to be adsorbed is an oil-soluble compound
  • (B) is chosen so that the mixture of (B) with the component (A) to be adsorbed is liquid or low-viscosity at the process temperature.
  • the process temperature is the temperature at which the adsorbates are produced. she is chosen by the expert depending on the components to be adsorbed and the carrier.
  • Particularly suitable stabilizers are compounds which are selected from the group consisting of b-1) glycerides, b-2) emulsifiers, b-3) polysaccharides and / or b-4) chelaxes.
  • mixtures of compounds from the individual classes of stabilizers (B) themselves and mixtures of compounds from different classes can be used.
  • the person skilled in the art selects the stabilizer or the stabilizer mixtures depending on the component (A) to be adsorbed.
  • At least one compound from the class of emulsifiers b-2 it is particularly preferred to use at least one compound from the class of emulsifiers b-2), at least one compound from the class of polysaccharides b-3) and at least one compound from the class of chelators b-4).
  • At least one compound selected from the glyceride class (b-1) is used as the stabilizer (B).
  • At least 2, in particular at least 3, compounds selected from the glyceride class (b-1) are preferably used as stabilizers.
  • glycolide is understood to mean a glycerol esterified with one, two or three carboxylic acid residues (mono-, di- or triglyceride). “Glyceride” is also understood to mean a mixture of different glycerides. The glyceride or the glyceride mixture can contain further additives, e.g. free fatty acids.
  • the glyceride used can be a synthetic or naturally occurring glyceride oil or a derivative thereof. “Glyceride” is also understood to mean synthetic or naturally occurring fatty acid esters and / or oils and fats containing glycerides.
  • glycolide is also understood to mean derivatives derived from glycerol.
  • derivatives in which the fatty acid composition of the naturally occurring non-conjugated or saturated glycerides has not changed significantly are included.
  • Synthetic or natural glycerides are preferred which contain acyl residues with 1 to 22 carbon atoms, preferably with 12 to 18 carbon atoms.
  • Natural oils and fats that are saturated and / or single or multiple are particularly preferred unsaturated acyl radicals containing more than 12, in particular more than 16 carbon atoms and less than 22 carbon atoms, preferably from 18 to 20 carbon atoms.
  • oil or “fat” is understood to mean a fatty acid mixture which contains saturated, unsaturated, straight-chain and / or branched esterified fatty acid (s).
  • the fatty acids usually have 1 to 22, in particular 12 to 18, preferably 12 to 16 G atoms.
  • the oil or fat can contain various other saturated or unsaturated fatty acids.
  • the proportion of the different fatty acids in the oil or fat can fluctuate depending on the manufacturing process.
  • Fatty acid esters are also included in the formulation according to the invention, in particular fatty acid esters which are formed in the production of oil from vegetable material. Examples include C1 to C12 alkyl esters of fatty acids.
  • the fatty acid esters are preferably in the form of glyceride, in particular triglyceride.
  • vegetable or animal starting material e.g. Olive oil, coconut oil, coconut fat, sesame oil, rice germ oil, bamboo oil, bamboo fat, sunflower oil, rapeseed oil, fish oil, soybean oil, palm oil, safflower oil, linseed oil, wheat germ oil, peanut oil, cottonseed oil,
  • vegetable or animal starting material e.g. Olive oil, coconut oil, coconut fat, sesame oil, rice germ oil, bamboo oil, bamboo fat, sunflower oil, rapeseed oil, fish oil, soybean oil, palm oil, safflower oil, linseed oil, wheat germ oil, peanut oil, cottonseed oil,
  • Corn oil, pork fat, beef fat, poultry fat, milk fat, tung oil or shea oil or a derivative or a mixture thereof can be used. Hydrogenated or partially hydrogenated oils and fats can also be used.
  • At least one compound selected from the class of emulsifiers (b-2) is used as stabilizer (B).
  • At least 2, in particular at least 3, compounds selected from the emulsifier class (b-2) are preferably used as stabilizers.
  • emulsifiers are suitable which are suitable for food, animal nutrition and / or cosmetic applications.
  • Suitable emulsifiers are, for example, 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
  • polyol and especially polyglycerol esters such as e.g. 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 and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside Lauryl glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the middle of which Degree of alkoxylation 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 ß ⁇ 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 / i 8 alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside 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 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.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic 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-alkyI-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxylate -hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the coconut acylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • betaines such as the N-alkyI-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinate, for
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C e alkyl or acyl group, have at least one free amino group in the molecule and contain at least one -COOH or -SO 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-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 bis 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Gi 2 / ⁇ 8 -AcyIsarcosine.
  • ampholytic emulsifiers quaternary emulsifiers are also suitable, those of the esterquat type, preferably methylquaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • Glycerophospholipids and glyceroglycolipids can also be used as emulsifiers.
  • Glycerophospholipids such as lecithin (phosphatidylcholine), cardiolipin, phosphatidylglycerol, phosphatidylserine and alkylacylglycerophospholipids such as plasmalogen are preferred here
  • diacylglycerides known as food emulsifiers and their mixtures, such as, for example, the food emulsifiers E 472a, E 472b, E 472 e or E 442. Also suitable are all in “Emulsifiers for Food” ed. G. Schuster, Springer Verlag 1985 on pages 55 to 190. Emulsifiers listed in Table 1 (pages 57-60) are particularly suitable.
  • Emulsifiers with EEC no. E 322 lecithins Emulsifiers with EEC no. E 322 lecithins
  • EO / PO block polymers as are available, for example, under the trade name Pluronic TM PE (BASF Aktiengesellschaft) are particularly preferred.
  • Addition products of 15 to 60 mol of ethylene oxide with castor oil and / or hardened castor oil are particularly preferred; such as products available under the INCI name PEG-40 Hydrogenated Castor Oil.
  • polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimer, as are available under the INCI names Polyglyceryl-3-Distearate or Polyglyceryl-3 Oleates. Mixtures of compounds from several of these classes of substances are also suitable.
  • At least one compound from the class of chelators (b-4) and at least one compound from the class of emulsifiers (b-2) are used as stabilizers (B).
  • At least one compound selected from the class of polysaccharides (b-3) is used as stabilizer (B).
  • At least 2, in particular at least 3, compounds selected from the class of polysaccharides (b-3) are preferably used as stabilizers.
  • polysaccharides different from (C) are used as stabilizers (B).
  • Polysaccharides (synonym glycans) is the collective name for macromolecular carbohydrates, the molecule of which consists of a large number (at least> 10, preferably> 20, in particular> 50) of glycosidically linked monosaccharide molecules (glycose).
  • the polysaccharides which may be mentioned are the homoglycans starch, glycogen, guarane, amylopectin and cellulose, amylose, dextran and the like. Tunicin (polyglucosane, glucane), inulin as the polycondensate of D-fructose (polyfructosan, fructan), chitin, alginic acid. Heteropolysaccharides (heteroglycans) composed of various types of monomer units are also suitable.
  • heteroglycans are pectins, mannans, galactans, xylans and other polyoses, as well as chondroitin sulfates, heparin, hyaluronic acid and other glycosaminoglycans.
  • maltodextrins as are commercially available under the name N-Zorbit M (maltodextrins from tapioca starch, National Starch) are suitable.
  • starch derivatives such as starch octenyl succinate, commercially available under the name HI-CAP 100 from National Starch.
  • At least one compound selected from the class of chelators (b-4) is used as stabilizer (B).
  • At least 2, in particular at least 3, compounds selected from the class of chelators (b-4) are preferably used as stabilizers.
  • Suitable chelators are in principle all compounds approved as chelators for food and animal feed. Examples include: Na, K, Ca salts of acetic acid, citric acid as well as the Na, K, Ca salts of citric acid, citric acid monoisopropyl esters, monoglyceride esters, triethyl esters and monosteary esters of citric acid, EDTA, Na, K- , Ca salts of EDTA, Na, K, Ca salts of gluconic acid, oxystearin, orthophosphoric acid and the Na, K, Ca salts of, orthophosphoric acid, Na salt of pyrophosphoric acid, Na salt triphosphoric acid, Na and Ca salts of hexametaphosphoric acid, Ca salt of phytic acid, sorbitol, tartaric acid, salicylic acid, and the Na salt of thiosulfuric acid.
  • Tartaric acid, salicylic acid and monostearic esters of citric acid are particularly suitable.
  • the weight ratio of stabilizer (B) to adsorbing components (A) is less than or equal to 10, in particular less than or equal to 5, in particular less than or equal to 1, in particular less than or equal to 0.8, particularly less than or equal to 0.5, preferably less is equal to 0.3.
  • a weight ratio of stabilizer (B) to components (A) to be adsorbed is preferably less than or equal to 10, in particular less than or equal to 5 , in particular less than or equal to 1, in particular less than or equal to 0.8.
  • a weight ratio of stabilizer (B) to components (A) to be adsorbed is preferably less than or equal to 0.8, particularly less equal to 0.5, in particular less than or equal to 0.3, preferably less than or equal to 0.1.
  • Suitable carriers (C) are all substances which have an average particle size of at least 80 ⁇ m and which can adsorb the active ingredient (s) and the stabilizer (s).
  • Low molecular weight inorganic salts, kieselguhr, silicic acid and silicic acid derivatives, sugars, dextrins, starch products and cellulose preparations are particularly suitable.
  • the carrier (C) must not show any negative interactions with the components used in the formulation according to the invention and must be used as an auxiliary in the respective uses, e.g. in food, food supplements, animal feed and cosmetic preparations.
  • suitable carriers are: low molecular weight inorganic or organic compounds and high molecular weight organic compounds of natural or synthetic origin.
  • suitable low molecular weight inorganic carriers are salts, such as sodium chloride, calcium carbonate, sodium sulfate and magnesium sulfate, diatomaceous earth or silica or silica derivatives, such as e.g. Silicon dioxide, silicates or silica gels.
  • suitable organic carriers are, in particular, sugars, such as, for. B. glucose, fructose, sucrose and dextrins and starch products.
  • Suitable carriers C) are the polysaccharides mentioned under b-3. If polysaccharides are used as carrier C), it is preferred that as stabilizers B) Polysaccharides different from C) are used, it is particularly preferred that no polysaccharides are used as stabilizers B).
  • Starch and cellulose preparations such as, in particular, corn starch, corn spindle flour, ground rice husks, semolina bran or cereal flours, such as. B. wheat, rye, barley and oatmeal or bran or mixtures thereof.
  • carrier (C) are silicic acid or silicic acid derivatives, e.g. Silicon dioxides, silicates or silica gels with an average particle size of at least 80 ⁇ m as well as their mixtures.
  • silicic acid or silicic acid derivatives e.g. Silicon dioxides, silicates or silica gels with an average particle size of at least 80 ⁇ m as well as their mixtures.
  • Such products are commercially available, e.g. Sipernat® 22 or Sipemat® 2200 (Degussa); Tixosil® 38 X or Tixosil® 68 (Rhodia) or Zeofree 5170 (Huber).
  • Hydrophilic silicas are particularly preferred.
  • the present invention also includes the presence of mixtures of the carriers mentioned.
  • Essential to the invention is the mean particle size of the carrier (C) of at least 80 ⁇ m, preferably at least 100 ⁇ m, preferably at least 200 ⁇ m, in particular at least 300 ⁇ m, preferably at least 400 ⁇ m.
  • the carriers are used whose average particle size is less than 1000 ⁇ m, in particular less than 800 ⁇ m.
  • the mean particle size is given as a [D4.3] value. This can be determined on a Mastersizer S from Malvern Instruments GmbH, serial number 32734-08. To describe the width of the particle size distribution, the D (v, 0.1), D (v, 0.5) and D (v, 0.9) were determined and the average particle size of the distribution [D4.3] was given.
  • the average particle size [D4,3] becomes Mastersizer S Serial No. according to the Mastersizer Reference Handbook, Preliminary Manual Chapter 2, page 22-23, Malvern Instruments Ltd 32734-08, Certificate No P 1261, May 1995.
  • D [4,3] is given as "the volume weighted mean diameter”.
  • the mean particle sizes [D4.3] determined in this way are, for example, for Sipernat ⁇ 22: 136 ⁇ , Sipernat® 2200: 364 ⁇ m, Tixosil® 38 X: 265 ⁇ m, Tixosil® 68: 302 ⁇ m or Zeofree 5170: 287 ⁇ .
  • the carrier (C) can be present in the formulation according to the invention, based on the total weight of the adsorbate, in a proportion of more than 10% by weight, in particular more than 20% by weight, preferably more than 30% by weight.
  • the carrier is usually in a range from 10 to 85% by weight, preferably about 20 to 85% by weight, based on the total weight of the adsorbate. These values refer to the uncoated stabilized adsorbate.
  • the adsorbate is coated.
  • Suitable coating agents are:
  • Polyalkylene glycols especially polyethylene glycols with a number average molecular weight of about 400 to 15,000, e.g. 400 to 10,000; b) polyalkylene oxide polymers or copolymers with a number molecular weight of approximately 4,000 to 20,000, in particular block copolymers of polyoxyethylene and polyoxypropylene; c) substituted polystyrenes, maleic acid derivatives and styrene maleic acid copolymers; d) polyvinylpyrrolidones with a number average molecular weight of about 7,000 to 1,000,000; e) vinyl pyrrolidone-vinyl acetate copolymers with a number average molecular weight of about 30,000 to 100,000; f) polyvinyl alcohol with a number average molecular weight of about
  • Palm oil r) synthetic or semi-synthetic oils, e.g. medium chain triglycerides or mineral oils; s) animal oils such as Herring, sardine and whale oil; t) hardened (hydrogenated or partially hydrogenated) oils / glycerides such as e.g. of the above, especially hydrogenated palm oil, hydrogenated cottonseed oil, hydrogenated soybean oil; u) paint coats such as Terpenes, in particular shellac, tolu balsam, Peru balsam, sandarak, and silicone resins; v) fatty acids, both saturated and mono- and polyunsaturated
  • the coating agents mentioned can also be used in mixtures with one another.
  • suitable polyalkylene glycols a) are: polypropylene glycols and in particular polyethylene glycols of different molecular weights, such as, for. B. PEG 4000 or PEG 6000, available from BASF AG under the trade names Lutrol E 4000 and Lutrol E 6000.
  • Examples of the above polymers b) are: polyethylene oxides and polypropylene oxides, ethylene oxide / propylene oxide mixed polymers and block copolymers, composed of polyethylene oxide and polypropylene oxide blocks, such as, for. B. Polymers available from BASF AG under the trade names Lutrol F68 and Lutrol F127.
  • polymers a) and b) can preferably highly concentrated solutions of up to about 50 wt .-%, such as. B. about 30 to 50 wt .-%, based on the total weight of the solution, can be used advantageously.
  • polyvinylpyrrolidones such as those sold by BASF AG under the trade names Kollidon or Luviskol.
  • highly concentrated solutions with a solids content of about 30 to 40% by weight, based on the total weight of the solution can advantageously be used.
  • polymers e) is a vinylpyrrolidone / vinyl acetate copolymer which is sold by BASF AG under the trade name Kollidon VA64 or Kollicoat SR. Highly concentrated solutions of about 30 to 40% by weight, based on the total weight of the solution, of these copolymers can be used particularly advantageously.
  • Examples of the above polymers f) are: Products such as those sold by Hoechst under the trade name Mowiol. Of these polymers, solutions with a solids content in the range from about 8 to 20% by weight can advantageously be used.
  • Suitable polymers g) are: hydroxypropylmethyl celluloses, such as those used for. B. are sold by Shin Etsu under the trade name Pharmacoat.
  • polymers h) mentioned above are: alkyl (meth) acrylate polymers and copolymers whose alkyl group has 1 to 4 carbon atoms.
  • suitable copolymers are: ethyl acrylate / methyl methacrylate copolymers, which are sold, for example, by BASF AG under the trade names Kollicoat EMM 30D or under the trade name Eutragit NE 30 D by Röhm; as well as methacrylate / ethyl acrylate copolymers, such as those sold by BASF AG under the trade name Kollicoat MAE 30DP or under the trade name Eutragit 30/55 by Röhm.
  • Such copolymers can be processed, for example, as 10 to 40% by weight dispersions according to the invention.
  • examples of the above polymers i) are: polyvinyl acetate dispersions which are stabilized with polyvinylpyrrolidone and are marketed, for example, by BASF AG under the trade name Kollicoat SR 30D (solids content of the dispersion about 20 to 30% by weight).
  • Fats e.g. those of animal, vegetable or synthetic origin;
  • animal fats m include fats from pork, beef and geese, for example beef tallow is suitable.
  • a suitable beef tallow is available under the trade name Edenor NHIT-G (CAS No. 67701-27-3) from Cognis.
  • coating agents are gelatin, e.g. beef, pork, fish.
  • waxes e.g. vegetable waxes, e.g. Candelio wax, carnaubawaehs, rice germ oil wax, japan wax or japan wax substitute (available under the trade name japan wax substitute 2909, Kahl wax refinery) etc .
  • synthetic waxes such as cetyl palmitate (available under the trade name Cutina CP, CAS 95912-87-1 from Cognis), animal waxes, such as e.g. Lanolin, beeswax, shellac wax, walrus and chemically modified waxes such as jojoba wax, sasol wax, montane ester wax.
  • Vegetable oils q e.g. Sunflower, safflower, cottonseed, soybean, corn germ and olive oil, rapeseed, linseed, olive tree, coconut, ( ⁇ ) palm kernel and ( ⁇ ) palm oil; be considered.
  • Suitable palm oils are available, for example, under the trade name Vegeol PR 265 from Aarhus Oliefabrik.
  • Suitable rapeseed (seed) oils are available under the trade name Vegeol PR 267 from Aarhus Oliefabrik.
  • Palm kernel oil is available under the trade name Tefaeid Palmic 90 (CAS No. 57-10-3) from Karlshamns.
  • Semi-synthetic oils r e.g. medium chain triglycerides or mineral oils and / or animal oils s
  • s e.g. Herring, sardine and whale oils
  • hydrogenated vegetable oils t including triglycerides, such as hydrogenated cottonseed, corn, peanut, soybean, palm, palm kernel, Babassu, sunflower and safflower oils are used as coating agents.
  • Preferred hydrogenated vegetable oils include hydrogenated palm oil, cottonseed oil and soybean oil.
  • the most preferred hydrogenated vegetable oil is hydrogenated soy.
  • Other fats and waxes derived from plants and animals are also suitable.
  • the preferred hydrogenated vegetable oils can be in various polymorphic forms, these are the ⁇ , ⁇ and ⁇ ' form.
  • hydrogenated vegetable oils are used which are predominantly in the ⁇ and ß ' form, in particular those which are predominantly in the ⁇ form.
  • the term “predominantly” means that at least 25%, in particular at least 50%, preferably at least 75% of the crystals are in the preferred polymorphic form.
  • hydrogenated soybean oil with a proportion of more than 50%, in particular more than 75%, preferably more than 90% of ⁇ and / or ⁇ 'form is particularly preferred.
  • a highly concentrated, still sprayable liquid such as. B. a to 50 wt .-% aqueous or non-aqueous solution or dispersion of one or more of the coating materials mentioned.
  • Powdery coating materials can also be used.
  • Preferred coating agents include hydrogenated vegetable oils including
  • Triglycerides e.g. hydrogenated cottonseed, corn, peanut, soybean, palm, palm kernel, babassu, sunflower and safflower oils.
  • Preferred hydrogenated vegetable oils include hydrogenated palm oil, cottonseed oil and soybean oil.
  • the most preferred hydrogenated vegetable oil is hydrogenated soybean oil.
  • Other fats and waxes derived from plants and animals are also suitable.
  • the adsorbates may contain further substances, for example antioxidants, preservatives, binders and / or flavorings may be mentioned.
  • Antioxidants are advantageous, for example, in order to protect the double bonds of the fatty acids from oxidation.
  • the general health benefits of antioxidants are well known.
  • ethoxyquin, ascorbic acid, t-butylhydroxytoluene, t-butylhydroxyanisole, ascorbyl palmitate are preferably used as antioxidants in animal nutrition, otherwise gamma and alpha-tocopherols, tocotrienol, rosemary extract, isoflavones and carotenoids and naturally occurring polyphenes are also used.
  • B flavonoids used.
  • antioxidants are used as further substances (E) if oil-soluble compounds are used as components (A) to be adsorbed. Especially if the components to be adsorbed are oil-soluble vitamins and / or unsaturated fatty acids.
  • antioxidants are used as further substances (E) if a compound from the group of glycerides (b-1) is used as stabilizer (B).
  • the formulation according to the invention can contain 0.05 to 10% by weight of antioxidants. It preferably contains 0.1 to 6% by weight of antioxidants, based on the components (A) to be adsorbed.
  • the formulation according to the invention can also contain binders.
  • suitable binders are: Solutions of carbohydrates, such as. As glucose, sucrose, dextrins and the like, sugar alcohols, such as. B. mannitol, or polymer solutions, such as solutions of hydroxypropylmethyl cellulose (HPMC), polyvinylpyrrolidone (PVP), ethoxylated cellulose (EC), ethyl cellulose or propyl cellulose.
  • HPMC hydroxypropylmethyl cellulose
  • PVP polyvinylpyrrolidone
  • EC ethoxylated cellulose
  • the proportion of binder, based on the dry weight of the powdered formulation can be, for example, in the range from about 0 to 20% by weight, such as. B. 1 to 6 wt .-%, based on the components to be adsorbed (A) depending on the type and adhesive properties of the binder used. In the simplest case, heat can also be used for binding.
  • the adsorbates can be produced, for example, as follows: one or more carriers (C) are placed in a mixer or a fluidized bed reactor and the component (A) to be adsorbed and, if appropriate, further substances (E) can be added. In rare cases, the use of stirred fixed beds or moving beds is conceivable.
  • components (A), (B), (C) and other substances (E) can be combined in all conceivable combinations and sequences.
  • the person skilled in the art chooses these depending on the components mentioned.
  • the component (A) to be adsorbed is mixed with a stabilizer (B) and then applied to the carrier (C).
  • B stabilizer
  • C carrier
  • (A) and (B) can be carried out by customary methods depending on the physical state of (A) and (B). Both (A) and (B) can be solid or liquid. They can be dissolved or dispersed in suitable oils or in water or other solvents.
  • the devices required for this are known to the person skilled in the art, e.g. heatable apparatus, preferably with mixing tools, e.g. Stirrers are provided.
  • the required energy input can take place, for example, via heatable container walls, heatable mixing tools and / or mechanical energy input.
  • (B) is present as a solid with a wide variety of particle size distributions or as (aqueous) solutions or dispersions alone or together with other substances, it is advantageous (B) to add (A) with or without water in the desired concentrations and a dispersion therefrom manufacture.
  • (B) is in the form of a powdery solid and (A) is in the form of a liquid
  • (A) in an aqueous protective colloid (eg gelatin) / sugar phase with the addition of (B) and if necessary. other additives are dispersed.
  • the solidification can again take place here by lowering the temperature and / or by removing water.
  • the mixing of (A) and (B) can be carried out gently (simultaneously or downstream for heating) or by intensive energy input.
  • a rotary movement or shaking of the entire apparatus is sufficient in itself.
  • the energy input can also e.g. take place via ultrasonic sonotrodes.
  • the stabilizer (B) is mixed with the carrier (C) and then the component (A) to be adsorbed is applied.
  • Adsorbate production application of (A), preferably in a mixture with (B), to (C) in the mixer
  • the carrier (C) is if necessary. submitted together with aggregates. Plowshares, shovels, snails or the like ensure a more or less intensive product mixing. Classic examples are ploughshare mixers, cone screw mixers or similar devices.
  • a description of mixing processes and mixers can be found, for example, in a technical information from Degussa (-Hüls), T1 1213, "Silicas as Flow Aid and as a Carrier - Suitable Mixing Processes for Powders and Granules". Very flat, box-shaped or trough-shaped designs with one or more screws can also be used. Other designs include high-speed mixers such as the Turbolizer ® Mixer / Coater from Hosokawa Micron BV
  • Mixers operating discontinuously can preferably be used.
  • the carrier material may be presented together with additives.
  • Plowshares, shovels, snails or the like ensure a more or less intensive product mixing.
  • Classic examples are ploughshare mixers, cone screw mixers or similar devices.
  • the product can be mixed by moving the entire container. Examples include tumble mixers, drum mixers or the like.
  • pneumatic mixers see Ullmann's Encyclopedia of Industrial Ghemistry, Sixth Edition, Mixing of Solids).
  • the dosage / addition of component (A) to be adsorbed, in a preferred embodiment in a mixture with stabilizer (B), is optionally carried out together with other substances (E) as a rule. via devices for dripping or spraying. Examples of this are lances, shower heads, single-substance or multi-substance nozzles, in rare cases rotating drip or atomizing devices. In the simplest case, addition is also possible locally as a concentrated jet.
  • the component (A) to be adsorbed, in a preferred embodiment in the form of a mixture with stabilizer (B) can first be introduced into the mixer in order to then give up the carrier (C).
  • the component (A) to be adsorbed, preferably in a mixture with stabilizer (B), can be added at elevated pressure, atmospheric pressure or at atmospheric pressure, preferably at atmospheric pressure and vacuum.
  • the component (A) to be adsorbed may be advantageous to preheat the component (A) to be adsorbed (lowering the viscosity, changing the wetting properties) and to supply or remove heat via the container wall and / or the mixing tools. In some cases it may be necessary to remove water or solvent vapors. This is of particular interest when the component (A) to be adsorbed is introduced in a mixture with stabilizer (B).
  • the person skilled in the art preferably chooses the stabilizer (s) in such a way that a homogeneous mixture of (A) and (B) can be produced, which may also be in the form of a dispersion, for example.
  • the adsorbates are usually produced at temperatures above the melting point of the mixtures.
  • (B) is generally chosen so that the mixture of (B) with the component (A) to be adsorbed is solid and homogeneous at temperatures below 80 ° C., preferably below 60 ° C., in particular below 40 ° C.
  • the mixer containing the carrier may be expedient to evacuate the mixer containing the carrier before adding the active ingredient, and if necessary. cover with protective gas. Depending on the wearer, this must be repeated several times.
  • continuously operating mixers are suitable.
  • Components (A) to be adsorbed, preferably in a mixture with (B), and any further substances (E) and carrier (C) are preferably added at different locations in the mixer.
  • Adsorbates can be produced batchwise or continuously in fluidized beds.
  • the carrier (C) is moved by the possibly hot fluidizing gas.
  • Air or inert gas is suitable as the fluidizing gas. In individual cases, it makes sense to add or remove heat via the tank wall and / or via heat exchanger surfaces immersed in the fluidized bed. Suitable fluidized beds and the necessary peripherals are state of the art.
  • the batchwise or continuous metering and, if appropriate, the preheating of the components (A) to be adsorbed, preferably in a mixture with (B), are carried out by the devices described above, which are known to the person skilled in the art.
  • adsorbates can advantageously be produced by combining a mixer and a fluidized bed.
  • adsorbates contain further substances (E), these can be added together to components (A) and / or mixed with the carrier (C).
  • powdering agents such as talc, silicates or the like in the manufacture of adsorbates in the mixer or immediately thereafter / in front of them in order to avoid sticking.
  • (B) is selected from the group (b-1) and / or (b-2), it is advantageous to mix (A) with (B) (for example by melting) and then apply it to (C). It is particularly preferred to fix the mixture of (A) and (B) in or partially to (C), for example by lowering the temperature. It is advantageous, by choosing the suitable temperatures, to lower the viscosity of the mixture of (A) and (B) to such an extent that the carrier (C) can be loaded sufficiently quickly and completely. This method is particularly advantageous if (B) contains at least one compound from (b-1) and at least one compound from (b-2).
  • the mixture of (A) and (B) can be heated, for example, in upstream separate containers or apparatuses or heated pipelines. If necessary, the supports (C) can also be added preheated.
  • the mixture of (A) and (B) and of (C) can be heated together or separately in the mixer itself. The heating can take place by heat exchange via the container wall or heated mixing elements or by the input of mechanical stirring or mixing energy.
  • the mixture can in turn be cooled in the mixer itself by heat exchange via the tank wall or coolable mixing elements or, in rare cases, by using evaporative or evaporative cooling. Cooling in downstream devices or in the simplest case by heat exchange with the environment during storage is of course also possible.
  • the individual components, (A), mixtures of (A) and (B), (C), or mixtures of (B) and (C) are heated and cooled as required.
  • the methods mentioned have also proven to be particularly advantageous if the stabilizer (B) is selected from the group of the polysaccharides (b-3).
  • Manufacturing coated This can be done directly in the mixer or in downstream equipment. This can be done by adding liquid coating agents as described under (D) or by adding initially solid coating material (D) which melts or softens as a result of wall heating of the apparatus or the shaft or as a result of the mechanical energy input and the adsorbate coats.
  • the adsorbate and the preferably powdery coating material (D) can be placed in the mixer, premixed if necessary, and this occurs as a result of high mechanical energy input in the same or in separate apparatuses (but examples are all the mixers already mentioned slow-running mills and dryers) for coating the adsorbate.
  • adsorbate and / or coating agent change in viscosity, change in wetting properties, influence on the setting properties
  • D coating agent
  • a change in the wetting properties can also be achieved by adding surface-active substances.
  • coating materials serves to provide additional protection for the active ingredient, to delay or accelerate the release of the active ingredient, to strengthen the mechanism of action or to achieve additive effects.
  • the invention includes that powdering agents such as talc, silicates or the like can be added when the coating agent is applied or immediately after / in front of it in order to avoid sticking.
  • Adsorbate production application of (A). preferably in a mixture with (B) on (C) in the fluidized bed
  • the adsorbates can be produced batchwise or continuously in fluidized beds.
  • the particles are moved by the possibly hot or cooled fluidizing gas.
  • the following are e.g. Air or inert gas (e.g. nitrogen) is suitable.
  • air or inert gas e.g. nitrogen
  • it makes sense to add or remove heat via the tank wall and via heat exchanger surfaces immersed in the fluidized bed. Suitable fluidized beds and the necessary peripherals are described in the prior art.
  • discontinuous or continuous dosing and if necessary. preheating of (A), preferably from mixtures of (A) and (B) and optionally further substances (E) and of aggregates is carried out analogously to superiors "described in the mixture have hens.
  • the carrier (C) can be placed in a fluidized bed. This is swirled and loaded with the desired concentration by spraying, dropping, etc. on an aqueous or non-aqueous solution or dispersion or a melt of (A), preferably a mixture of (A) and (B).
  • the adsorbates according to the invention can be produced by combining the mixer and the fluidized bed.
  • the invention furthermore comprises adsorbates which can be obtained by the aforementioned processes.
  • adsorbates are characterized by an increased stability of the components (A) to be adsorbed and at the same time are easy to manufacture on an industrial scale. They can therefore be used in a variety of food technology applications, cosmetic preparations and animal feed preparations. They can be used in particular in complex matrices, such as premixes from the animal feed industry.
  • the adsorbates according to the invention generally have an uncoated loading [defined as% by weight of the components (A) to be adsorbed based on% by weight of carrier (C)] from 0.01 to 10.0, in particular 0.1 to 5 , 0, preferably 0.5 to 2.5.
  • the adsorbates according to the invention generally have an uncoated total loading [defined as the sum of the% by weight of the components (A) and stabilizers (B) based on% by weight of carrier (C)] of 0.02 to 15.0 ; in particular 0.05 to 10, in particular 0.2 to 8.0; preferably 0.2 to 5.0, particularly preferably 0.5 to 2.5.
  • V 1a Loading of carrier silica with CLA in the fluidized bed
  • Tixosil 38 X a silica from Rhodia, was used as the carrier material. 323 g of this silica were heated in a beaker to 70 ° C in a dry sieve tank and then poured into the cone of the laboratory fluidized bed as reference material.
  • the silica in the fluidized bed was uniformly fluidized at an air volume of 10 to 15 m 3 / h and a supply air temperature of 45 to 50 ° C.
  • the CLA methyl ester (396 g) was sprayed onto the silica at a spray pressure of 1 bar by vacuum suction using the top spray method with a 1.0 mm two-component nozzle.
  • the spray duration was approx. 26 min.
  • V 1b coating of the adsorbate obtained in V1a
  • Adsorbates containing CLA methyl ester or CLA ethyl ester are mixed with the piglet feed and stored open at a temperature of 40 ° C and a relative humidity of 70% over a period of 4 weeks in a climatic chamber. After 2 or 4 weeks, the retentions are determined based on the respective initial value.
  • the retention is defined as the active substance content after 14 days compared to the active substance content used.
  • the stability of the CLA-ME (components (A)) in the adsorbates produced according to comparative examples V2a and V2b was determined in the premix test.
  • the premix test showed the following retention after 14 days:
  • component (A) here CLA methyl ester oil, stabilized with 1% ethoxyquin (component E)
  • component (A) here CLA methyl ester oil, stabilized with 1% ethoxyquin
  • component E 1% ethoxyquin
  • Example 2a the desired amount of CLA methyl ester oil (component A), stabilized with 1% ethoxyquin (component E), was mixed with Cremophor CO 40 (component b-2) and with the U-Turrax for 30 seconds at 5000 U. / min predispersed. The water was added and this mixture was emulsified with the U-Turrax for 10 minutes at 8800 rpm. This mixture was filled into a spray gun and sprayed onto the silica in the mixer while stirring. Otherwise, the procedure was as described in Example 1.
  • the Cremophor CO 40 was first mixed with water and this mixture was sprayed onto the silica. Only then was the CLA methyl ester oil, stabilized with 1% ethoxyquin, sprayed onto the silica which had already been pre-loaded with emulsifier and water. Otherwise the procedure was as described in Example 2a.
  • Example 2c the desired amount of CLA methyl ester oil, stabilized with 1% ethoxyquin, was mixed with Cremophor CO 40 and dispersed with the U-Turrax at 10,000 rpm for two minutes. In the absence of additional water, the emulsifier / CLA EQ mixture was sprayed onto the silica using the spray gun. Otherwise, the procedure was as described in Example 2a.
  • Example 5 Stabilized adsorbates containing vitamin E acetate
  • a first step 816 g of vitamin E acetate (feed grade) were heated to 65 ° C in a drying cabinet. 800 g of a silica carrier (Tixosil 38 X ® , Rhodia) were placed in a ploughshare mixer (Loedige type M5 GR).
  • the vitamin E acetate was sprayed onto the silica using a spray gun while stirring at about 350 rpm. The mixture was then stirred for a further 5 minutes at a stirring speed of 600 rpm. A homogeneous, free-flowing powder with the following composition was obtained:
  • Example 5a-c Preparation of stable adsorbates containing vitamin E acetate using stabilizers from the group of the emulsifiers (b-2)
  • Example 5a Cremophor TM GO 32 was used as an emulsifier.
  • 816 g of vitamin E acetate (feed grade) and 40.8 g of Cremophor TM GO 32 were heated to 65 ° C in separate beakers in a drying cabinet, then mixed and mixed with the U-Turrax for 60 seconds at 5500 rpm dispersed. This mixture was filled into a spray gun and sprayed onto the silica in the mixer while stirring. Otherwise, the procedure was as in Comparative Example V5.
  • Example 5b was carried out analogously to example 5a, instead of Cremophor TM GO 32, Cremophor TM GS 32 was used as an emulsifier.
  • Cremophor GS 32 was used as an emulsifier.
  • 816 g of vitamin E acetate feed grade, 40.8 g of Cremophor GS 32 and 40.8 g of water were heated to 65 ° C in separate beakers in a drying cabinet, then mixed and mixed with the U-Turrax for 60 seconds at 5500 U / min dispersed. This mixture was filled into a spray gun and sprayed onto the silica in the mixer while stirring. Otherwise proceed as described in Example 5.
  • Example 5d Preparation of a Stable Adsorbate Containing Vitamin E Acetate Using a Stabilizer from the Group of Glycerides (b-1)
  • a first step 808 g of vitamin E acetate (feed grade) were heated to 80 ° C in the drying tank.
  • 89.8 g of Vegeol PR-269 (50% Vegeol CO 52 S and 50% Palmowar FH) were heated to 80 ° C in the drying cabinet and melted.
  • Vegeol PR-269 was purchased from Aarhus Olie and has a melting point of 60 up to 65 ° C. Both liquids were then poured into a beaker and dispersed with the U-Turrax for two minutes at 5000 rpm.
  • the prepared, liquid mixture of vitamin E acetate feed grade and Vegeol PR-269 was then sprayed onto the silica using a heated spray gun while stirring at about 200 rpm. The mixture was then stirred for a further 5 minutes and then cooled in the mixer and discharge bowl. A free flowing powder was obtained.
  • the standard premix test for vitamin E acetate was carried out under the following conditions: Storage temperature 40 ° C, rel. Air humidity 70%, storage location climate cabinet, packaging PE film bag, closed.
  • the adsorbates stabilized according to the invention show a significantly higher retention of the active ingredient (vitamin E acetate) compared to the non-stabilized adsorbate (V5).

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Abstract

L'invention concerne un procédé pour produire des adsorbats appropriés pour l'alimentation humaine ou animale ainsi que pour des applications cosmétiques. Selon ce procédé, on applique un composant à adsorber (A) sur un support (C) au moyen d'au moins un stabilisant (B), la taille moyenne des particules du support (C) s'élevant à au moins 80 Nm à condition que, si le composant à adsorber (A) est de la vitamine E, le mélange constitué de (A) et de (B) présente un rapport hydrophile-lipophile inférieur à 7 et à condition que, si le composant à adsorber (A) est une vitamine soluble dans l'huile, et le stabilisant (B) est une glycéride, le point de solidification de (A) et de (B) est inférieur ou égal à 80 DEG C. L'invention concerne en outre l'utilisation des adsorbats ainsi obtenus.
EP04717597A 2003-03-14 2004-03-05 Adsorbat contenant des principes actifs Withdrawn EP1605773A2 (fr)

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DK09152282.1T DK2060189T3 (da) 2003-03-14 2004-03-05 Aktivstofholdige adsorbater
DE202004021155U DE202004021155U1 (de) 2003-03-14 2004-03-05 Wirkstoffhaltige Adsorbate
EP09152282A EP2060189B1 (fr) 2003-03-14 2004-03-05 Adsorbats contenant des agents actifs

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DE10311585 2003-03-14
PCT/EP2004/002244 WO2004080199A2 (fr) 2003-03-14 2004-03-05 Adsorbat contenant des principes actifs

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ES2397805T3 (es) 2013-03-11
JP2006523094A (ja) 2006-10-12
TWI311045B (en) 2009-06-21
US8642090B2 (en) 2014-02-04
CA2519014A1 (fr) 2004-09-23
WO2004080199A3 (fr) 2005-03-17
EP2060189A1 (fr) 2009-05-20
US20060008533A1 (en) 2006-01-12
TW200503643A (en) 2005-02-01
DK2060189T3 (da) 2013-01-28
WO2004080199A2 (fr) 2004-09-23
AU2004218838A1 (en) 2004-09-23
DE10311585A1 (de) 2004-09-23
EP2060189B1 (fr) 2012-10-17
CN1747658A (zh) 2006-03-15

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