EP1761246A1 - Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions - Google Patents

Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions

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Publication number
EP1761246A1
EP1761246A1 EP05753798A EP05753798A EP1761246A1 EP 1761246 A1 EP1761246 A1 EP 1761246A1 EP 05753798 A EP05753798 A EP 05753798A EP 05753798 A EP05753798 A EP 05753798A EP 1761246 A1 EP1761246 A1 EP 1761246A1
Authority
EP
European Patent Office
Prior art keywords
water
soluble
insoluble active
sparingly
aqueous
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Withdrawn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
EP05753798A
Other languages
German (de)
English (en)
Inventor
Christian KÖPSEL
Jesper Feldthusen Jensen
Klaus Krämer
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
Publication of EP1761246A1 publication Critical patent/EP1761246A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—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
    • A61K9/146—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 macromolecular compounds

Definitions

  • the present invention relates to aqueous dispersions comprising at least one sparingly water-soluble or water-insoluble active ingredient and rice starch as protective colloid.
  • active ingredients suitable for the food and animal feed sector or for pharmaceutical and cosmetic applications for example fat-soluble vitamins, carotenoids, but also the natural dyes curcumin or carmine, as well as numerous UV filters are only in the form of their water-insolubility and / or their sensitivity to oxidation can be used especially stabilized preparations.
  • the high requirements with regard to bioavailability, coloring properties and dispersibility, in particular in aqueous but also in lipophilic media can only be met by means of special formulations.
  • the preparation of finely divided, powdered carotenoid preparations is carried out by, for example, ⁇ -carotene in a volatile, water-miscible organic solvent at temperatures between 50 0 C and 200 0 C, optionally under elevated pressure, in- within a time of less than 10 seconds.
  • the beta-carotene is precipitated by immediate rapid mixing with an aqueous solution of a protective colloid at from 0 0 C and 5O 0 C aus ⁇ from the obtained molekular ⁇ disperse solution. This gives a colloidally disperse ⁇ -carotene hydrosol with orange-yellow color shade.
  • Subsequent spray-drying of the dispersion provides a free-flowing dry powder which dissolves in water to form a clear, yellow-orange colored dispersion.
  • WO 98/26008 relates to the use of a mixture of low molecular weight and high molecular weight protective colloids for the preparation of redispersible xanthophyll-containing dry powders.
  • the aim of the present invention is now to convert hydrophobic, poorly water-soluble or water-insoluble active and effect substances into stable aqueous dispersions or into stable and readily redispersible dry powders.
  • stable means that the formulations have a duration and temperature range which is adequate for the respective application. oxidation and photostable and sedimentation and Aufrahmstabil are.
  • the object of the invention has been achieved by aqueous dispersions containing at least one sparingly water-soluble or water-insoluble active ingredient and rice starch as protective colloid.
  • aqueous dispersions is to be understood as meaning both aqueous suspensions and emulsions.
  • Preference is given to aqueous suspensions in which the dispersed phase contains at least one sparingly water-soluble or water-insoluble active ingredient as nanoparticulate particles.
  • the dry powders or emulsions prepared from the above aqueous dispersions preferably double emulsions, in particular o / w / o emulsions.
  • the term "sparingly water-soluble organic active ingredients” refers to those compounds whose water solubility is ⁇ 5% by weight ⁇ 1 wt .-%, more preferably ⁇ 0.1 wt .-%, most preferably ⁇ 0.01 wt .-% is.
  • Fat-soluble vitamins such as the K vitamins, vitamin A and derivatives such as vitamin A acetate, vitamin A propionate or vitamin A palmitate, vitamin D 2 and vitamin D 3, and vitamin E and derivatives.
  • vitamin E is natural or synthetic ⁇ -, ⁇ -, ⁇ - or ⁇ -tocopherol, preferably natural or synthetic ⁇ -tocopherol and tocotrienol.
  • Vitamin E derivatives are, for example, ToCOPhilyl C 1 -C 20 -carboxylic esters, such as tocopheryl acetate or tocopheryl palmitate.
  • Polyunsaturated fatty acids e.g. Linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid.
  • Food colors such as curcumin, carmine or chlorophyll.
  • Carotenoids both carotenes and xanthophylls, e.g. ⁇ -carotene, lycopene, lutein, astaxanthin, zeaxanthin, capsanthin, capsorubin, cryptoxanthin, citranaxanthin, canthaxanthin, bixin, ⁇ -apo-4-carotenal, ⁇ -apo-8-carotenal and ⁇ -apo-8-carotenoic acid ethyl ester.
  • ⁇ -carotene e.g. ⁇ -carotene, lycopene, lutein, astaxanthin, zeaxanthin, capsanthin, capsorubin, cryptoxanthin, citranaxanthin, canthaxanthin, bixin, ⁇ -apo-4-carotenal, ⁇ -apo-8-carotenal and ⁇ -apo-8-carotenoic acid ethyl ester.
  • Water-insoluble or sparingly water-soluble organic UV filter substances such as e.g. Compounds from the group of triazines, anilides, benzophenones, triazoles, cinnamamides and the sulfonated benzimidazoles.
  • Preferred active substances are carotenoids, in particular ⁇ -carotene, lycopene, lutein, astaxanthin and canthaxanthin and also vitamin E and from the series of UV filter substances the substance class of the triazines, in particular Uvinul T150.
  • a particularly preferred embodiment of the aqueous dispersions according to the invention is characterized in that they are aqueous suspensions which contain at least one of the abovementioned sparingly water-soluble or water-insoluble active compounds as nanoparticulate particles.
  • the mean particle size of the nanoparticulate particles in the aqueous dispersion is in the range from 0.01 to 100 ⁇ m, preferably in the range of 0.01 to 10 microns, more preferably in the range of 0.01 to 2 microns, most preferably in the range of 0.02 to 1 micron.
  • the amounts of the various components of the dispersions according to the invention, in particular suspensions, are chosen according to the invention such that the preparations comprise from 0.1 to 90% by weight, preferably from 2 to 40% by weight, particularly preferably from 3 to 30% by weight, most preferably 5 to 25 wt .-% of at least one sparingly water-soluble or water-insoluble active ingredient, 0.1 to 99.9 wt .-%, preferably 5 to 70 wt .-% particularly preferably 10 to 60 wt .-%, very particularly preferably 15 to 35 wt .-% rice starch.
  • the percentages by weight in each case relate to the dry mass of the formulation.
  • the preparations may also contain low molecular weight stabilizers such as antioxidants and / or preservatives to protect the active ingredients.
  • Suitable antioxidants or preservatives are, for example, ⁇ -tocopherol, ascorbic acid, tert-butyl-hydroxytoluene, tert-butylhydroxyanisole, lecithin, ethoxyquin, methylparaben, propylparaben, sorbic acid or sodium benzoate.
  • the antioxidants or preservatives may be used in amounts of 0.01 to 50 wt .-%, preferably 0.1 to 30 wt .-%, particularly preferably 0.5 to 20 wt .-%, most preferably 1 to 10 wt. -%, based on the dry matter of the formulation.
  • the dispersions may also comprise plasticizers for increasing the mechanical stability of a dry powder which may be produced therefrom.
  • plasticizers are, for example, sugars and sugar alcohols such as sucrose, glucose, lactose, invert sugar, sorbitol, mannitol, xylitol or glycerol.
  • lactose is used as the plasticizer.
  • the plasticizers may be present in amounts of from 0.1 to 70% by weight, preferably from 10 to 60% by weight, particularly preferably from 20 to 50% by weight, based on the dry weight of the formulation.
  • the dispersions low molecular weight surface-active compounds in a concentration of 0.01 to 70 wt .-%, preferably 0.1 to 50 wt .-%, particularly preferably 0.5 to 20 wt .-%, based on the Dry matter of the formulation.
  • Particularly suitable as such are amphiphilic compounds or mixtures of such compounds.
  • all surfactants with an HLB value of 5 to 20 come into consideration.
  • suitable surface-active substances are esters of long-chain fatty acids with ascorbic acid, mono- and diglycerides of fatty acids and their oxyethylation products, esters of monofatty acid glycerides with acetic acid, citric acid, lactic acid or diacetyltartaric acid, polyglycerol fatty acid esters such as the monostearate of triglycerol, sorbitan fatty acid esters , Propylene glycol fatty acid ester and lecithin. Ascorbyl palmitate is preferably used.
  • a physiologically tolerated oil such as, for example, sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil and cosmetic oils, for example paraffin oil, glyceryl stearate, isopropyl myristate, diisopropyl adipate, cetyl stearyl 2-ethylhexanoate, hydrogenated polyisobutene, Vaseline, caprylic / capric triglycerides, microcrystalline wax, lanolin and stearic acid in a concentration of 0.1 to 500 wt .-%, preferably 10 to 300 wt .-%, particularly preferably 20 to 100 wt .-%, based to use on the one or more used sparingly water-soluble or water-insoluble active ingredients.
  • a physiologically tolerated oil such as, for example, sesame oil, corn oil, cottonseed oil, soybean oil or peanut oil and cosmetic oils, for example paraffin oil, glyceryl stearate, isoprop
  • the invention also provides a process for preparing an aqueous dispersion of at least one sparingly water-soluble or water-insoluble active ingredient by dispersing one or more sparingly water-soluble or water-insoluble active compounds in an aqueous molecular dispersion or colloidal disperse solution of a protective colloid, characterized in that the protective colloid Rice starch used.
  • a preferred embodiment of the process according to the invention is characterized in that the dispersing step is the preparation of a suspension of at least one sparingly water-soluble or water-insoluble active ingredient in an aqueous molecular-disperse or colloidal-disperse solution of rice starch.
  • a particularly preferred embodiment of the process is characterized in that the dispersing, in particular suspending, comprises the following steps:
  • the water-miscible solvents used in stage aO are above all water-immiscible, thermally stable, volatile solvents containing only carbon, hydrogen and oxygen, such as alcohols, ethers, esters, ketones and acetals.
  • solvents wasser ⁇ at least 10% miscible is used having a boiling point below 2OfJ 0 C and / or less than 10 Koh ⁇ lenscher have.
  • Particular preference is given to using methanol, ethanol, n-propanol, isopropanol, 1,2-butanediol-1-methyl ether, 1,2-propanediol-1-n-propyl ether, tetrahydrofuran or acetone.
  • a water-immiscible organic solvent is Sin ⁇ ne of the present invention for an organic solvent having a solubility Wasserlös ⁇ at atmospheric pressure of less than 10%.
  • solvents come u.a. halogenated aliphatic hydrocarbons, e.g. Methylene chloride, chloroform and carbon tetrachloride, carboxylic acid esters such as dimethyl carbonate, diethyl carbonate, propylene carbonate, ethyl formate, methyl, ethyl or isopropyl acetate and ethers such as methyl tert. butyl ether in question.
  • Preferred water-immiscible organic solvents are the following compounds from the group consisting of dimethyl carbonate, propylene carbonate, ethyl formate, ethyl acetate, isopropyl acetate and methyl tert. butyl ether.
  • the particularly preferred solvent for the dispersing / suspending step is at least one water-miscible organic solvent or a mixture of water and at least one water-miscible organic solvent, most preferably isopropanol or acetone.
  • step a) the molecular disperse solution of at least one sparingly water-soluble or water-insoluble active ingredient at temperatures greater than 30 0 C, preferably between 50 ° C and 240 0 C, in particular 100 0 C to 200 0 C, more preferably 140 ° C to 180 ° C, optionally under pressure, produces and immediacy then ver ⁇ in step b) with the aqueous solution of the protective colloid, wherein a mixture temperature of 35 0 C to 120 0 C. established.
  • the solvent component is converted into the aqueous phase and the hydrophobic phase of the active substance (s) is formed as a nanodisperse phase.
  • the invention also provides a process for producing a dry powder containing at least one sparingly water-soluble or water-insoluble one Active substance as nanoparticulate particles, characterized in that the above-described aqueous dispersions, in particular suspensions, are freed from water and dried.
  • the transfer into a dry powder can u.a. by spray drying, spray cooling, freeze drying or drying in a fluidized bed, if appropriate also in the presence of a coating material.
  • Suitable coating agents are u.a. Corn starch, silica or tricalcium phosphate.
  • a preferred embodiment of the o.g. Process is characterized in that the prepared suspension of at least one sparingly water-soluble or water-insoluble active ingredient is ground before being converted into a dry powder.
  • the grinding can be carried out in a manner known per se, e.g. This is carried out according to the type of mill used until the particles have a mean particle size D [4,3] of from 0.1 to 100 ⁇ m, preferably 0.2 to 50 ⁇ m, determined by Fraunhofer diffraction preferably 0.2 to 20 microns, most preferably 0.2 to 5 microns, in particular 0.2 to 0.8 microns.
  • D [4,3] denotes the volume-weighted mean diameter (see Malvern Mastersizer S manual, Malvern Instruments Ltd., UK).
  • a) dissolves at least one sparingly water-soluble or water-insoluble active ingredient in a water-miscible organic solvent or a mixture of water and a water-miscible organic solvent at temperatures greater than 30 ° C.
  • the invention also provides powdered preparations of at least one sparingly water-soluble or water-insoluble active ingredient obtainable by one of the abovementioned processes.
  • the invention likewise provides a process for preparing an oil-miscible preparation in the form of a double dispersion containing at least one sparingly water-soluble or water-insoluble active compound, characterized in that the aqueous dispersions described in the introduction are emulsified in oil.
  • An emulsifier is used to form a water-in-oil emulsion in which the water phase contains protective colloid-stabilized nanoparticles of at least one organic UV filter substance which is sparingly soluble in water or insoluble in water.
  • Suitable emulsifiers are known W / O emulsifiers having an HLB value of less than 10, in particular from 2 to 6 into consideration (see H. P. Fiedler, Lexicon of adjuvants for pharmacy, cosmetics and adjacent areas, 1996, pages 753 ff).
  • Typical representatives of this emulsifier class are partial fatty acid esters of polyhydric alcohols, e.g.
  • the dispersant may be of synthetic, mineral, vegetable or animal origin. Typical representatives are u.a. Sesame oil, maize germ oil, cotton seed oil, soybean oil or peanut oil, esters of medium-chain fatty acids and paraffin oil, glyceryl stearate, isopropyl myristate, diisopropyl adipate, cetylstearyl 2-ethylhexanoate, hydrogenated polyisobutene, vaseline, caprylic / capric triglycerides, microcrystalline wax, lanolin and stearic acid.
  • the amount of the dispersing agent is generally 30 to 95, preferably 50 to 80 wt .-%, based on the total mass of the final emulsion.
  • the emulsification can be carried out continuously or batchwise.
  • the physical stability of the double dispersion system is achieved by a very good fine distribution of the water phase in the oil phase, for example by intensive treatment with a rotor / stator disperser at temperatures of 20 to 80, preferably 40 to 7O 0 C or with a high-pressure homogenizer such as an APV Gaulin or with a high-pressure homogenizer such as the Microfluidizer in the pressure range from 700 to 1000 bar.
  • the achievable mean diameters of the aqueous-disperse phase are less than 500 microns, preferably less than 100 microns, more preferably less than 10 microns, especially less than 1 micron.
  • the invention also provides liquid, oil-miscible preparations of at least one sparingly water-soluble or water-insoluble active ingredient obtainable according to above-mentioned method, characterized in that they are present as a double dispersion onsystems an aqueous-dispersed phase having a particle diameter less than 500 A / m, in the protective colloid-stabilized particles of one or more sparingly water-soluble or water-insoluble active ingredients are present in an oil as dispersing agent.
  • the invention also relates to the use of the o.g. aqueous dispersions as an additive to foods, food supplements, animal feeds, pharma ⁇ ceutical and cosmetic preparations.
  • the invention also relates to the use of the o.g. powdered preparations as an additive to foods, food supplements, animal feeds, pharmaceutical and cosmetic preparations.
  • the invention also relates to the use of the o.g. liquid, miscible with oil ren preparations as an additive to foods, food supplements, animal feeds, pharmaceutical and cosmetic preparations.
  • the resulting molecularly disperse astaxanthin solution immediately entered a further mixing chamber in which 10.4 kg of a aqueous rice starch solution containing, in addition to 108 g of rice starch, 36 g of sucrose at a mixing angle of 90.degree were adjusted to pH 8 by means of sodium hydroxide solution, wherein the astaxanthin precipitated in colloidally disperse form with an average particle size of 144 nm at a temperature of 45 ° C.
  • the dispersion was concentrated and converted in a manner known per se into a free-flowing 10% astaxanthin dry powder having an average particle size of 129 nm.
  • the dry powder dissolved in water again to form a clear, red-colored dispersion, with the color strength of the redispersion only about 10%, based on the original dispersion, decreased.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Fodder In General (AREA)

Abstract

L'invention concerne des dispersions aqueuses et des poudres sèches produites à partir de ces dernières, contenant au moins un principe actif peu soluble dans l'eau ou insoluble dans l'eau ainsi que de l'amidon de riz comme colloïde protecteur.
EP05753798A 2004-06-23 2005-06-17 Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions Withdrawn EP1761246A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004030072A DE102004030072A1 (de) 2004-06-23 2004-06-23 Wässrige Dispersionen schwer wasserlöslicher oder wasserunlöslicher Wirkstoffe und daraus hergestellte Trockenpulver
PCT/EP2005/006547 WO2006000347A1 (fr) 2004-06-23 2005-06-17 Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions

Publications (1)

Publication Number Publication Date
EP1761246A1 true EP1761246A1 (fr) 2007-03-14

Family

ID=34970854

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05753798A Withdrawn EP1761246A1 (fr) 2004-06-23 2005-06-17 Dispersions aqueuses de principes actifs peu solubles dans l'eau et poudres seches produites a partir de ces dispersions

Country Status (8)

Country Link
US (1) US20080026016A1 (fr)
EP (1) EP1761246A1 (fr)
JP (1) JP2008503518A (fr)
CN (1) CN1972669A (fr)
CA (1) CA2570870A1 (fr)
DE (1) DE102004030072A1 (fr)
NO (1) NO20070212L (fr)
WO (1) WO2006000347A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4937732B2 (ja) * 2006-12-27 2012-05-23 フタムラ化学株式会社 色素安定剤
EP2061344B1 (fr) 2007-02-06 2018-08-22 FUJIFILM Corporation Composition de poudre et procédé de production de celle-ci, et composition alimentaire, composition cosmétique et composition pharmaceutique contenant celle-ci
BRPI0810776B1 (pt) * 2007-05-08 2016-07-12 Basf Se uso de uma dispersão aquosa, dispersão aquosa, e, composição cosmética.
KR102142462B1 (ko) * 2014-06-30 2020-08-10 (주)아모레퍼시픽 컬링유지력이 우수한 아이메이크업 화장료 조성물
JP6553864B2 (ja) * 2014-11-19 2019-07-31 Ｊｘｔｇエネルギー株式会社 シールド掘進機用テールシール組成物

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Publication number Priority date Publication date Assignee Title
US3110598A (en) * 1959-09-08 1963-11-12 Hoffmann La Roche Process of making a carotenoid preparation
DE3119383A1 (de) * 1981-05-15 1982-12-02 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von feinverteilten, pulverfoermigen carotinodpraeparaten
US4755397A (en) * 1986-12-24 1988-07-05 National Starch And Chemical Corporation Starch based particulate encapsulation process
DK0410236T3 (da) * 1989-07-25 1993-12-13 Hoffmann La Roche Fremgangsmåde til fremstilling af caratenoidpræparater
DE19642359A1 (de) * 1996-10-14 1998-04-16 Basf Ag Stabile Emulsionen und Trockenpulver von Mischungen fettlöslicher Vitamine, deren Herstellung und Verwendung
DE19651681A1 (de) * 1996-12-12 1998-06-18 Basf Ag Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthopyllen, deren Herstellung und Verwendung
CA2261456A1 (fr) * 1998-02-23 1999-08-23 F. Hoffmann-La Roche Ag Preparation d'un melange carotenoide finement pulverulent

Non-Patent Citations (1)

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Title
See references of WO2006000347A1 *

Also Published As

Publication number Publication date
NO20070212L (no) 2007-01-12
US20080026016A1 (en) 2008-01-31
JP2008503518A (ja) 2008-02-07
DE102004030072A1 (de) 2006-01-19
CA2570870A1 (fr) 2006-01-05
CN1972669A (zh) 2007-05-30
WO2006000347A1 (fr) 2006-01-05

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