EP1901836A1 - Systeme emulsifiant, emulsion et leur utilisation - Google Patents

Systeme emulsifiant, emulsion et leur utilisation

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Publication number
EP1901836A1
EP1901836A1 EP06763961A EP06763961A EP1901836A1 EP 1901836 A1 EP1901836 A1 EP 1901836A1 EP 06763961 A EP06763961 A EP 06763961A EP 06763961 A EP06763961 A EP 06763961A EP 1901836 A1 EP1901836 A1 EP 1901836A1
Authority
EP
European Patent Office
Prior art keywords
emulsion
emulsifier
emulsion according
emulsifier system
weight
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Withdrawn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
EP06763961A
Other languages
German (de)
English (en)
Inventor
Helmut Auweter
Heribert Bohn
Christian KÖPSEL
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 EP1901836A1 publication Critical patent/EP1901836A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds

Definitions

  • the present invention relates to an emulsifier system which contains a) an ascorbic acid ester with long-chain fatty acids, b) an ethoxylated sorbitan fatty acid ester and c) a sugar fatty acid ester.
  • the components a), b) and c) give a total of 100 wt .-%.
  • the present invention furthermore relates to an emulsion which contains ⁇ ) a disperse phase comprising a fat-soluble substance ⁇ i), ⁇ ) glycerol or glycerol mixed with water as dispersant and ⁇ ) the emulsifier system according to the invention.
  • the components ⁇ ), ⁇ ), ⁇ ) give a total of 100 wt .-% based on the emulsion.
  • the present invention relates to a process for the preparation of the inventive emulsion and their use in human nutrition, in animal nutrition, in cosmetics or in the pharmaceutical industry. Further embodiments of the present invention can be taken from the claims, the description and the examples. It is understood that the features mentioned above and those yet to be explained of the subject matter according to the invention can be used not only in the particular combination specified, but also in other combinations, without departing from the scope of the invention.
  • German Patent DE 2 363 534 describes the preparation of sugar-containing liquid vitamin and carotenoid preparations.
  • Physiologically acceptable emulsifiers such as lecithin or ascorbyl palmitate, are used for emulsification.
  • a disadvantage of such products is the crystallization tendency of the sugar or sugar alcohol, e.g. during storage of the product at low temperatures. This crystallization tendency leads to undesirable inhomogeneities.
  • the European Patent EP 551 638 has the stabilization of liquid preparations of fat-soluble substances over as long as possible storage period (> 6 months) to the object.
  • the esters of ascorbic acid with long-chain fatty acids are proposed for this purpose as an emulsifier.
  • the emulsions must be stored refrigerated. This can increase transport costs and make handling difficult.
  • Japanese Patent Publication JP 2 000 212 066 discloses the use of polyoxyethylene sorbitan fatty acid esters and of sugar fatty acid esters as emulsifier for emulsions of fat-soluble substances.
  • Japanese Patent JP 08 120 187 discloses the use of sorbitan fatty acid esters and sucrose fatty acid esters as emulsifiers for carotenoid emulsions.
  • Korean Patent KR 20 020 018 518 discloses the use of sucrose fatty acid esters and sorbitan fatty acid esters as an emulsifier for a rotarotide emulsion. Ss-carotene concentrations of up to 3% are achieved.
  • European Patent EP 1 095 986 deals with the task of preventing coagulation of the disperse phase. This object is achieved by providing a method for stabilizing liquid, aqueous preparations of fat-soluble substances.
  • a protective colloid-free oil-in-water emulsion is mixed with a lipid-soluble substance with a protective colloid.
  • This preparation is mixed with an aqueous phase.
  • the protective colloid is a high molecular weight stabilizer. The task of temperature and storage stability is not solved.
  • European Patent EP 361 928 shows an extremely finely divided emulsion with a glycerol / water mixture as a dispersing agent and a fat-soluble drug as a disperse phase.
  • Nonionic stabilizers having a molecular weight of 1,000 or more are used as stabilizers.
  • the mean particle size of the disperse phase is in this case between 10 and 70 nm.
  • One of the objects of the present invention was to provide an emulsifier system which should be as versatile as possible.
  • the emulsifier system should be useful for the preparation of emulsions which are physiologically compatible.
  • the emulsifier system should in particular lead to emulsions having the desired positive properties
  • the emulsion should have a high storage stability, so that storage at room temperature and elevated temperatures up to about 4O 0 C is possible.
  • a further object of the present invention was to improve the stability of an emulsion when introduced into drinks and the storage stability in these beverages.
  • the emulsion should in particular after introduction into drinks or after the Pasteurization step to be stable. It was also desired a high relative color strength and color stability of the emulsion of the invention, as required for example in the beverage industry.
  • the emulsion should be bacteriostatic, especially for applications in the food, feed, cosmetic or pharmaceutical industries.
  • Emulsifiers are auxiliaries for the preparation and stabilization of emulsions.
  • Emulsions are liquid-liquid mixtures. Stabilization is understood as the prevention of segregation of a disperse phase ⁇ ) and of a dispersant ⁇ ) to the thermodynamically stable final state.
  • Disperse phase is related to the present invention for the finely divided phase of the emulsion.
  • the continuous phase of the emulsion is referred to as a dispersant in the context of the present invention.
  • the dispersant used is the emulsifier system according to the invention.
  • the emulsifier system according to the invention contains three emulsifiers.
  • the emulsifier system according to the invention may contain further constituents. All constituents of the emulsifier system according to the invention together give 100% by weight, based on the emulsifier system.
  • As emulsifier a) Ascorbinklareester be used.
  • long-chain alkyl esters such as C 1 - to C 2 O-alkyl esters are used.
  • a preferred embodiment of an emulsifier a) is the ascorbic acid ester with Ci6- to Cm-
  • Alkyl radicals in a particularly preferred embodiment is used as an emulsifier a) ascorbyl palmitate (Ci 6 alkyl esters).
  • One or more different emulsifiers a) may be present in the emulsifier system according to the invention, for example two or three different emulsifiers a).
  • the concentration according to the invention of an ester of ascorbic acid in the emulsifier system is not abandoned.
  • the proportion of an emulsifier a) in the emulsifier system according to the invention can vary within wide limits.
  • An emulsifier a) is preferably present in a concentration of 30 wt .-% to 70 wt .-%, more preferably in a concentration of 40 wt .-% to 60 wt .-% before, wherein the wt .-% information in each case relate to the inventive emulsifier system.
  • the effect of an emulsifier a), in particular of the ascorbyl palmitate as an emulsifier a), can be increased by formation of a salt, as a rule an alkali metal salt, in particular a sodium salt.
  • the ascorbic acid ester is generally added in the 0.5 to 2 molar amount, preferably in the 1 molar amount, of sodium hydroxide solution. Particular preference is given to using a mixture of ester and salt.
  • an emulsifier b) are generally Polyethyienglykol sorbitan fatty acid esters into consideration.
  • An emulsifier b) generally has an HLB value in the range of 10 to 18.
  • Preferred emulsifiers b) have the general chemical structural formula
  • a long-chain alkyl radical is generally a C-to-C 2 O-Al kyl radical, and in particular a Ci6-Cia-alkyl radical.
  • a preferred embodiment is an ethoxylated sorbitan-oleic monoester.
  • An emulsifier b) in a particularly preferred embodiment has the general chemical structural formula
  • the proportion of monoester is generally 55% by weight or more, preferably from 70% by weight to 85% by weight, and more preferably from 75% by weight to 85% by weight.
  • An emulsifier b) is preferably nonionic.
  • One or more different emulsifiers b) may be present in the emulsifier system according to the invention, for example two or three different emulsifiers b).
  • the proportion of an emulsifier b) in the emulsifier system according to the invention can vary within wide limits.
  • An emulsifier b) is preferably in a concentration of 10 wt .-% to 50 wt .-%, more preferably in a concentration of 12.5 wt .-% to 40 wt .-% and in particular in a concentration of 20 wt. % to 30% by weight, the weight percentages in each case referring to the emulsifier system according to the invention.
  • an emulsifier c) are generally sugar fatty acid esters into consideration.
  • An emulsifier c) generally has an HLB value in the range of 10 to 18.
  • sucrose stearate, sucrose palmitate, sucrose myristate, sucrose laurate and sucrose oleate may be considered.
  • the proportion of monoester at 55 wt .-% or more preferably in the range of 70 wt .-% to 85 wt .-%, particularly preferably from 75 wt .-% to 85 wt .-%.
  • Preferred emulsifiers c) have the general chemical structural formula
  • emulsifiers c) there may be one or more different emulsifiers c) in the emulsifier system according to the invention, e.g. two or three different emulsifiers c). Preferably, only one emulsifier c) is used for the emulsifier system according to the invention.
  • an emulsifier c) in the emulsifier system according to the invention can vary within wide limits.
  • An emulsifier c) is preferably in a concentration of 10 wt .-% to 50 wt .-%, particularly preferably in a concentration of
  • One, two or all of the three emulsifiers a), b) and c) are in a particular embodiment of low molecular weight, for example having a molecular weight below 2000 and in particular having a molecular weight below 1000.
  • the emulsifier a) low molecular weight In a particularly preferred Embodiment is the emulsifier a) low molecular weight.
  • the emulsifier system according to the invention in particular facilitates the distribution of the disperse phase ⁇ ).
  • Low molecular weight emulsifiers, in particular an emulsifier a) are distinguished by their rapid attachment to the emulsion produced by mechanical action, for example, in comparison with the high molecular weight stabilizers. However, the low molecular weight emulsifiers can also serve to stabilize the emulsion after the preparation.
  • the emulsifier system according to the invention is characterized in particular by its synergistic effect. Synergy is understood to mean the interaction of different emulsifiers in a coordinated overall performance and, in the context of the present invention, also the resulting overall performance of the emulsifier system according to the invention. This total output is higher than the sum of the individual services.
  • the emulsifier system according to the invention is composed in a preferred embodiment of from 20 wt .-% to 30 wt .-% of an emulsifier b) in the embodiment of an ethoxylated sorbitan n-fatty acid ester of the structural formula
  • the targeted selection and combination of the three emulsifiers a), b) and c) of the emulsifier system according to the invention surprisingly leads to an emulsifier system with which, for example, a surprisingly advantageous emulsion according to the invention described below can be prepared.
  • the emulsifier system according to the invention facilitates preparation of the emulsion, storage of the emulsion and use of the emulsion.
  • An emulsion according to the invention contains a disperse phase ⁇ ), a dispersant ⁇ ) and ⁇ ) an emulsifier system according to the invention. But it may also contain other components. All components of an emulsion according to the invention together give 100% by weight, based on the emulsion.
  • a fat-soluble substance oci) contained in the emulsion according to the invention can basically be any fat-soluble substance.
  • a fat-soluble substance ⁇ -i) is physiologically compatible, ie it is compatible with respect to human and animal physiology. But it is also a plant-physiological compatibility possible.
  • the fat-soluble vitamins A, D, E or K or their derivatives for example vitamin A and vitamin E esters such as retinyl acetate or tocopherol acetate, tocotrienol, vitamin Ki, vitamin K 2 , xanthophyll, and carotenoids, such as canthaxanthin, astaxanthin , Zeaxanthin, lutein, lycopene, apocarotenal and especially ⁇ -carotene.
  • Carotenoids are widely used in nature color pigments, which are contained in many foods in finely divided form and give the food a characteristic color.
  • carotenoids are therefore also of interest as dyes for the food, animal feed and pharmaceutical industries.
  • the colorations achieved by higher-percentage carotenoid emulsions usually cover the range from orange to red.
  • higher-percentage ⁇ -carotene-containing emulsions according to the present invention are distinguished by a brilliant yellow shade, as desired for many foods, and a high color strength.
  • fat-soluble substances ⁇ -t which can be used in the context of the present invention are polyunsaturated fatty acids, such as e.g. Arachidonic acid, docosahexaenoic acid, eicosapentaenoic acid, linoleic acid, linolenic acid, both in free form and as triglyceride, and aroma oils such as orange oil, peppermint oil or citrus oils, for example one having the chemical structural formula
  • any fat-soluble substances ⁇ i) are suitable as a constituent of the emulsion, which play a physiological role in the human or animal organism and are usually processed into emulsions due to their water insolubility.
  • Preferred fat-soluble substances oi) in the context of the present invention are in particular the above-mentioned fat-soluble vitamins, e.g. Vitamin A, D, E and K and their derivatives, xanthophylls and the polyunsaturated fatty acids and ß-carotene. Particularly preferred is ⁇ -carotene.
  • a ⁇ -carotene as a fat-soluble substance od is generally dissolved in oil.
  • the dissolved in oil ß-carotene is generally used together with the oil as a disperse phase.
  • Suitable oils are, for example, all physiologically acceptable oils, in particular peanut oil, sunflower oil, olive oil or other triacylglycerides.
  • the ⁇ -carotene is preferably dissolved in a triacylglyceride having the general chemical structural formula
  • a beta-carotene is generally dissolved in appropriate amounts of oil. This is generally the case with a ratio of oil to beta-carotene of 1 to 3, preferably from 1, 5 to 2.5 and particularly preferably from 1, 8 to 2.2 the case.
  • a fat-soluble substance ⁇ -i) is initially to be understood as a fat-soluble substance. However, it is also possible to combine various fat-soluble substances, for example two or three fat-soluble substances ⁇ -i). It is preferred to use a fat-soluble substance ⁇ -i).
  • a fat-soluble substance ⁇ -i) according to the invention is generally present in amounts of 40% by weight or less, based on the emulsion.
  • the proportion of a fat-soluble substance ⁇ -i) is from 2 to 40% by weight, based on the emulsion.
  • a fat-soluble substance ⁇ i) can also be used in concentrations from 2 wt .-% to 20 wt .-% or from 5 wt .-% to 15 wt .-%, particularly preferably for applications in the beverage industry at 10 wt .-%, wherein the wt .-% information each refer to the emulsion.
  • the average particle size of the disperse phase ⁇ ) of the emulsion according to the invention is generally 500 nm or below, in a further embodiment of the invention the mean particle size of the disperse phase ⁇ ) is from 50 nm to 250 nm. In a preferred embodiment of the invention Particle size of the disperse phase ⁇ ) of 50 nm to 100 nm.
  • the average particle size of an emulsion according to the invention can be determined, for example, via a mass-based weight distribution using a photon correlation spectrometer with a wavelength of 632.8 nm.
  • the dispersant ⁇ ) is generally from 40% by weight to 95% by weight, preferably from 50% by weight to 80% by weight, of the emulsion.
  • the dispersant ß) can only consist of glycerol. However, it may also contain 50% water or less besides the glycerin. Preferably, the glycerol to water ratio is 95: 5 to 85:15. The weight ratio of glycerol and water depends on the properties of the fat-soluble substance ⁇ -i) to be dispersed and on the requirement for a uniform and fine distribution.
  • the emulsifier system ⁇ ) is in particular from 0.2 to 10% by weight of the emulsion. In another embodiment, the emulsifier system ⁇ according to the invention is from 0.3% by weight to 5% by weight, based on the emulsion according to the invention. In a preferred embodiment, the emulsifier system ⁇ ) according to the invention is 0.5 wt .-% to 1, 0 wt .-% based on the emulsion of the invention.
  • the emulsion according to the invention shows in a particular embodiment of the present invention a high stability over a long storage period.
  • An emulsion according to the invention can be for example about up to 2 years at room temperature and in particular at an elevated temperature of about 40 0 C WE sentlichem exclusion of light store. Below room temperature are associated with the present invention, temperatures of 15 0 C to 35 0 C, but to be understood especially from 20 0 C to 30 ° C.
  • An emulsion of the invention generally remains stable over this storage period of up to 2 years. Coalescence of the disperse phase ⁇ ) of an emulsion according to the invention, in particular ring formation, flocculation or color loss, generally does not occur.
  • the emulsion of the invention also displays a high color strength.
  • the relative color strength also referred to as the E 1/1 value
  • the E 1/1 value defines the specific extinction of a 1.0% aqueous emulsion in a 1 cm cuvette at the absorption maximum.
  • a high color intensity is understood in particular to mean a relative color intensity of 180 or more.
  • the relative color strength of the emulsion according to the invention is usually from 180 to 200.
  • the emulsion according to the invention has an advantageous low turbidity, which is desired, for example, in certain foods.
  • the turbidity of an emulsion is generally determined according to ISO 7027 / DIN EN 27027.
  • An emulsion according to the invention generally has a turbidity of from 50 NTU to 1000 NTU, depending on its specific composition. Low haze is generally present at from 50 NTU to 400 NTU, and more preferably from 50 NTU to 200 NTU. A slight turbidity can be achieved with the emulsion according to the invention even at the abovementioned high proportions of a fat-soluble substance ⁇ -i), in particular in the embodiment of ⁇ -carotene.
  • the emulsion according to the invention is distinguished in another embodiment by its good applicability in the beverage industry, i. the positive properties described herein are achievable respectively or in various combinations, in particular in applications, for example in the beverage industry.
  • a concentration of about 5 ppm to 50 ppm ⁇ -carotene, more preferably from about 10 ppm to 25 ppm ⁇ -carotene, and more preferably from 15 ppm to 20 ppm ⁇ -carotene in the ready-to-drink is desired .
  • the ⁇ -carotene concentration in a particularly preferred embodiment is 15 to 18 ppm.
  • High electrolyte contents may be present. High electrolyte contents are achieved especially in critical systems such as concentrates or isotonic drinks, which have a considerable proportion of different salts.
  • a low pH when using the emulsion in the beverage industry, generally a low pH may be present.
  • a low pH means in particular a pH of 6 or below, for example a pH of 2 to 5 and in particular a pH of 2 to 3.
  • pasteurization can be carried out. Under pasteurization is related to of the present invention, for example, a heat treatment of below 100 ° C, preferably 60 0 C to 90 ° C for a period of 60 s to 120 s to understand.
  • protein-free emulsions in particular for the beverage industry, are obtainable in a particular embodiment of the emulsifier system according to the invention.
  • Proteins may generally contain allergens, so that in a particular embodiment the emulsion according to the invention is protein-free.
  • no proteins are used as further possible emulsifiers or stabilizers for this purpose.
  • the emulsion according to the invention is well tolerated and combinable in a further embodiment of the present invention, in particular with the formulations which are typically used in the beverage industry.
  • compatibility is to be understood as meaning a low interaction with the components customarily used in the beverage industry, in particular with the stabilizers used there.
  • the usual formulations of the beverage industry are therefore not or not significantly affected by the inventive emulsion.
  • the emulsion according to the invention can thus be integrated excellently into the formulations of the beverage industry.
  • the components ⁇ ), ⁇ ), ⁇ ) and the optionally possible components give a total of 100% by weight, based on the emulsion.
  • the emulsion according to the invention may contain, in addition to the emulsifier system according to the invention, one or more different, for example two or three, low molecular weight emulsifiers.
  • additional emulsifier e.g. Leci- thin with a proportion of 5 wt .-% to 30 wt .-% based on the emulsion, but especially 10 wt .-% to 20 wt .-% based on the emulsion into consideration.
  • the emulsifier system according to the invention may contain, in addition to the emulsifiers a), b), c) Contain components which are referred to as stabilizers in the context of the present invention.
  • the stabilizers are preferably high molecular weight compounds having a molecular weight of 1,000 or more. They are preferably used when the emulsion according to the invention is added to beverages or other aqueous solutions in order to stabilize the disperse phase in addition to the emulsifier system according to the invention.
  • the preferably high molecular weight stabilizers are thus added, especially when using the emulsion according to the invention, for example by adding the emulsion of the invention to the formulations of the beverage industry.
  • stabilizers are gum arabic, gelatin, casein, caseinate, pectin, dextrin, locust bean gum, guar gum, xanthan, or plant proteins such as soy proteins, which may be hydrolyzed if appropriate, and mixtures thereof.
  • polyvinyl alcohol, polyvinylpyrrolidone, methylcellulose, carboxymethylcellulose, hydroxypropylcellulose and alginates are examples of stabilizers.
  • modified starches come into consideration. Among them are technological, i. physically or chemically prepared starch conversion products.
  • Preferred stabilizers are gelatin such as beef, pork and fish gelatin, vegetable proteins, pectin, casein, caseinate and gum arabic and modified starches. Particularly preferred stabilizers are modified starches.
  • Antioxidants can also be added to the emulsion according to the invention.
  • BHA butylhydroxyanisole
  • BHT butylhydroxytoluene
  • ascorbyl palmitate the scope of the invention not being left out of the amount of ascorbyl palmitate, or gallic acid esters.
  • vitamin C and rosemary extract come into consideration.
  • Antioxidants may be added to the emulsion according to the invention in amounts of from 0.5% by weight to 10% by weight, preferably from 1% by weight to 5% by weight, with the percentages by weight being based on the invention Obtain emulsion.
  • the antioxidative effect of the ascorbyl palmitate can be increased further by adding to the disperse phase ⁇ ) additionally tocopherol.
  • the proportion of tocopherol is preferably 1 wt .-% to 4 wt .-% based on the inventive emulsion.
  • the emulsion according to the invention is distinguished in a further embodiment of the present invention by its bacteriostatic effect. This refers to the prevention of bacterial growth and proliferation without killing the bacteria.
  • the mixing of the components of the emulsion according to the invention can take place immediately before the addition of the emulsion to a foodstuff, to a beverage, to a feed, to a cosmetic or to a pharmaceutical.
  • the emulsion according to the invention can also be initially filled and stored after its preparation in order to give it, as needed, to a food, to a drink, to a feed, to a cosmetic or to a pharmaceutical.
  • an emulsion according to the invention comprises 5% by weight to 15% by weight of a fat-soluble substance ⁇ -i) in the embodiment of ⁇ -carotene, 0.5% by weight to 1% by weight of an emulsifier system according to the invention ⁇ ) in the embodiment with 20% to 30% by weight of an emulsifier b) in the embodiment of an ethoxylated sorbitan fatty acid ester of the structural formula
  • the person skilled in the art is familiar with processes for the preparation of the emulsion according to the invention.
  • the emulsion according to the invention can be prepared, for example, in two steps: Voremulg réelle by emulsifying the fat-soluble substance ⁇ -i) in the dispersant ß) for the preparation of a crude emulsion and
  • the preparation of the emulsion according to the invention is preferably carried out by means of a rotor / stator system and by means of a subsequent emulsification in a high-pressure homogenizer in one passage or in several passages.
  • the fine emulsification may be carried out by one or more times, e.g. pass two or three times the crude emulsion, for example by a high-pressure homogenizer.
  • the homogenization is generally carried out at a pressure of from 200 bar to 1200 bar, preferably from 600 bar to 800 bar.
  • the number of revolutions is generally from 6,000 to 10,000 revolutions per minute, but preferably from 8,000 to 10,000 revolutions per minute.
  • the emulsion according to the invention can be used for a variety of purposes, in particular for coloring, for vitaminization, in particular provitamin A or as an antioxidant in human nutrition, in particular in beverages, more preferably in soft drinks, vitamin juices or sports drinks. Furthermore, a use in animal nutrition, in the cosmetics or in the pharmaceutical industry is possible.
  • the emulsion according to the invention is outstandingly suitable for simple and exact metering for the addition of e.g. from vitamins to liquid food or feed or, in the case of the .beta.-carotene, to the coloring of beverages e.g. of sodas.
  • the present invention also provides a food, a feed, a cosmetic or a pharmaceutical which contains an emulsifier system according to the invention or an emulsion according to the invention.
  • the relative color intensity E 1/1 was measured with the HP 8452A device from the manufacturer Hewlett Packard at a setting of 200 nm to 800 nm.
  • the E1 / 1 value defines the specific extinction of a 1.0% aqueous emulsion in a 1 cm cuvette at the absorption maximum.
  • UV / VIS spectra were measured with a HP8452A manufactured by Hewlett Packard at a setting of 200 nm to 800 nm.
  • the average particle size of an emulsion according to the invention was determined over a mas ⁇ se donatede weight distribution with a photon correlation spectrometer having a wavelength of 632.8 nm.
  • Example 1 The Effect of Emulsifier Systems Compared to the Individual Emulsifiers in Emulsions with ⁇ -Carotene.
  • Disperse phase o ⁇ containing:
  • the emulsions were prepared as follows. The disperse phase cci) was heated to about 170 ° C until the ⁇ -carotene had dissolved on). Then the disperse phase oci) was added to the dispersing agent ⁇ i) and homogenized by means of an Ultra Turraax at 10,000 revolutions per minute for about 15 seconds. The temperature of the emulsion was about 70 0 C. This crude emulsions were then further feinemulgiert in a Microfluidizer manufacturer Micro fluid at 800 bar in three repetitions, in order to achieve small droplets with a narrow size distribution of the disperse phase oti).
  • emulsifier system 2 g of emulsifier ai), 1 g of emulsifier bi) and 1 g of emulsifier ci) were used.
  • the emulsion of the invention was characterized by a very high relative color intensity E 1/1 and by a very brilliant and clear color appearance. It also showed a very good storage life under room temperature at 23 0 C within the observation period of four months. The results are summarized in Table 1.
  • Example 2 Concentrated emulsions with ⁇ -carotene
  • Dispersant ⁇ 2) 36 g of cation exchange water
  • the preparation of the emulsion was carried out according to the method described in Example 1.
  • the ratio of the proportions of the emulsifiers a-i), b-i) and c-i) in the emulsifier system according to the invention was 2: 1: 1.
  • Example 3 Concentrated emulsions with ⁇ -carotene
  • An emulsion according to the invention had the following composition, the weight% being based on the emulsion:
  • Emulsifier bi 0.14% by weight emulsifier c-i) 0.14% by weight
  • the above emulsion according to the invention was tested in sports drinks with the stabilizers xanthan or alternatively with carboxymethylcellulose.
  • the abovementioned emulsion with a content of 12% by weight of carotenoid, based on the emulsion was 15 ppm in a sports drink yellow clear with the composition 2.0 g of stabilizer, 932 g of water, 0.57 g of phosphate salt, 0, 49 g Na citrate 5.5 H 2 O, 0.8 g NaCl, 0.15 g Na benzoate, 0.2 g K-sorbate, 2.5 g citric acid, 61 g sugar and 0.15 g ascorbic acid , Thereafter, a heat treatment of 10 minutes was carried out at 90 ° C.
  • the UV / VIS absorption spectra before and after the heat treatment between 300 nm and 800 nm wavelength are approximately congruent. There was no significant color shift from yellow to yellow.
  • Examples 1 to 3 show that the emulsion according to the invention with the emulsifier system according to the invention is well suited to meet the challenges of the beverage industry.

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Abstract

Système émulsifiant contenant (a) un ester d'acide ascorbique ayant des acides gras à chaîne longue, (b) un ester d'acide gras de sorbitane éthoxylé et (c) un ester d'acide gras de sucre, et émulsions produites à l'aide dudit système.
EP06763961A 2005-07-04 2006-06-29 Systeme emulsifiant, emulsion et leur utilisation Withdrawn EP1901836A1 (fr)

Applications Claiming Priority (2)

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DE102005031464A DE102005031464A1 (de) 2005-07-04 2005-07-04 Emulgatorsystem, Emulsion und deren Verwendung
PCT/EP2006/063665 WO2007003565A1 (fr) 2005-07-04 2006-06-29 Systeme emulsifiant, emulsion et leur utilisation

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JP4866607B2 (ja) * 2005-12-09 2012-02-01 株式会社アイ・ティー・オー 乳化組成物
WO2011073726A1 (fr) * 2009-12-15 2011-06-23 Emultec S.R.L. Nanoémulsion, son procédé de préparation et son utilisation
WO2011103512A1 (fr) * 2010-02-18 2011-08-25 Martek Biosciences Corporation Émulsions d'acide gras sans dha
WO2011103514A1 (fr) * 2010-02-18 2011-08-25 Martek Biosciences Corporation Émulsions de triglycéride dha
US20110200644A1 (en) * 2010-02-18 2011-08-18 Martek Biosciences Corporation DHA Ester Emulsions
AU2011340797B2 (en) * 2010-12-10 2017-08-10 Ns Technologies Pty Ltd Methods for forming miniemulsions and use thereof for delivering bioactive agents
BR112013033292A2 (pt) * 2011-06-30 2016-08-16 Archer Daniels Midland Co “composição emulsificante; produto alimentício; método; método para dispersar um composto seco; e processo para produzir um produto de levedura”.
WO2013021041A1 (fr) * 2011-08-11 2013-02-14 Dsm Ip Assets B.V. Emulsions comprenant de la caroténoïde pour des formulations liquides transparentes et stables vis-à-vis la pasteurisation, en particulier des boissons
CA2881798A1 (fr) 2012-08-26 2014-03-06 Lycored Ltd. Formulation de .beta.-carotene a teinte regulee
WO2014051116A1 (fr) * 2012-09-28 2014-04-03 富士フイルム株式会社 Composition d'émulsion d'huile dans l'eau contenant du lycopène et son procédé de production
EP3005881A1 (fr) * 2014-10-10 2016-04-13 DSM IP Assets B.V. Boissons de couleur stable contenant 8'-apo- -carotene-8'-al
ES2607715B1 (es) * 2015-10-01 2018-01-17 Solutex Na, Lcc Proceso para la preparación y estabilización de emulsiones con omega-3 mediante redes cristalinas isométricas de derivados de celulosa
BR102015025584A2 (pt) * 2015-10-07 2017-05-02 Oxiteno S A Indústria E Comércio Powder emulsifier
CN108324699A (zh) * 2017-01-20 2018-07-27 浙江医药股份有限公司新昌制药厂 稳定的脂溶性活性成分组合物、微囊及其制备方法和应用
EP3351118A1 (fr) * 2017-01-20 2018-07-25 Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory Composition contenant un ingrédient actif et soluble aux matières grasses, microcapsule, ses utilisations et procédé de préparation

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DE4200728A1 (de) * 1992-01-14 1993-07-15 Basf Ag Stabile, fluessige praeparate fettloeslicher substanzen
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US6835408B2 (en) * 1998-11-13 2004-12-28 The Nisshin Oillio Group, Ltd. Oil or fat composition
KR100509116B1 (ko) * 2000-08-28 2005-08-18 닛신 오일리오그룹 가부시키가이샤 거품발생 억제 효과를 갖는 유지 조성물

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US20080207777A1 (en) 2008-08-28
NO20080526L (no) 2008-04-02
DE102005031464A1 (de) 2007-01-18
WO2007003565A1 (fr) 2007-01-11
TW200711663A (en) 2007-04-01
JP2009505809A (ja) 2009-02-12

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