MXPA99001754A - Continuous procedure for the preparation of a composition in the form of powder of a carotenoid and preparation in form of dust prepared through such procedimie - Google Patents
Continuous procedure for the preparation of a composition in the form of powder of a carotenoid and preparation in form of dust prepared through such procedimieInfo
- Publication number
- MXPA99001754A MXPA99001754A MXPA/A/1999/001754A MX9901754A MXPA99001754A MX PA99001754 A MXPA99001754 A MX PA99001754A MX 9901754 A MX9901754 A MX 9901754A MX PA99001754 A MXPA99001754 A MX PA99001754A
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- Prior art keywords
- active ingredient
- preparation
- carotenoid
- heat exchanger
- temperature
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Abstract
The present invention relates to a continuous process for the preparation of a powder composition of a carotenoid, retinoid or natural dye, wherein the active ingredient is finely divided, comprising the steps of: a) the formation of a suspension of the active ingredient in an organic solvent immiscible with water, optionally containing an antioxidant and / or an oil, b) introducing the suspension of step a) into a heat exchanger and heating said suspension to a temperature of 100-250 ° C, with which time spent in the heat exchanger remains there, is less than 5 seconds, c) rapid mixing of the solution in stage b) at a temperature within the range of from 20 to 100 ° C, with an aqueous solution of an inflatable colloid, optionally containing a stabilizer, d) the removal of the organic solvent, and e) the conversion of the dispersed n of stage d) in a preparation in the form of pol
Description
POWDER OF A CAROTENOID AND PREPARATION IN FORM OF DUST PREPARED THROUGH SUCH PROCEDURE Description of the Invention The present invention refers to a continuous process for the conversion of carotenoids, retinoids or synthetic dyes, in powder forms that are particularly required for coloring of foodstuffs and animal feed. Various processes have been described for the preparation of powders containing active ingredients with a crystal particle size of less than one micrometer. Most procedures are well suited to batch-based process applications. For example, US Pat. No. 3,998,753, describes a batch-based process for the preparation of carotenoid-containing, water-dispersible powders, wherein the carotenoid has a particle size of less than 1 micrometer. , this procedure comprising
(a) the formation of a solution of a carotenoid and an antioxidant in a volatile solvent, said solvent being selected from the group consisting of halogenated aliphatic hydrocarbons such as chloroform, carbon tetrachloride and methylene chloride; (b) the formation of an aqueous solution of sodium lauryl sulfate, a support composition, soluble in water, such as for example gelatin, a preservative and a stabilizer, and the adjustment of said solution to a pH comprised Approximately between values ranging from 10 to 11 and (c) the formation of an emulsion of the solutions of steps (a) and (b), by mixing process, at high speed and high shear; the elimination of organic solvent REF. 29450 and the drying of the resulting emulsion by spray drying, to obtain the carotenoid powder. In the European Patent Application EP-0065193 Bl, or the corresponding U.S. No. 4,522,743, there is described a continuous process for the preparation of finely divided carotenoid powders, in which the carotenoid has a particle size substantially below 0.5 micrometers. The carotenoid is dissolved in a volatile organic solvent, miscible with water, in less than 10 seconds and at a temperature between 50 and 200 ° C. The carotenoid is precipitated immediately in dispersed colloidal form, from the resulting molecularly dispersed solution, by rapid mixing process with an aqueous solution of an incurable colloid, at a temperature comprised between 0 and 50 * C. The preparation of the carotenoid and the precipitation of the carotenoid are carried out continuously in two mixing chambers. The resulting dispersion is freed of solvent and the dispersing medium in a conventional manner. However, for reasons of economic and ecological nature, this process has the disadvantage that the use of a large amount of solvent is necessary. It is an object of the present invention to provide a process that overcomes the drawbacks described hereinbefore, during the conversion of the active ingredient into finely divided pulverulent form.
It has now been found that it is possible to provide a powdery preparation wherein the active ingredient is finely divided by the use of an organic solvent immiscible with water, in a continuous process. Thus, the present invention relates to a continuous process for the preparation of a composition in powder form of a carotenoid, retinoid or natural dye, wherein the active ingredient is finely divided, this process comprising the steps of: a ) the formation of a suspension of the active ingredient in an organic solvent immiscible with water, which optionally contains an antioxidant and / or an oilb) introducing the suspension of step a) into a heat exchanger and heating said suspension to a temperature of 100-250 ° C, where the residence time of the latter in the heat exchanger is lower of 5 seconds, c) the rapid mixing of the solution of step b) at a temperature ranging from 20 to 100 ° C, with an aqueous solution of a swelling colloid, optionally containing a stabilizer , d) the removal of the organic solvent, and e) the conversion of the dispersion from step d) into a preparation in powder form. The term "finely divided" means, within the scope of the present invention, a particle size of less than 1.5 micrometers, preferably less than 1 micrometer and, most preferably, less than 0.4. micrometers The term "active ingredient" means, within the scope of the present invention, carotenoids, retinoids or natural dyes. Caroteinoids, for the purposes of the present invention, include, in particular, beta-carotene, beta-apo-4-carotenal, beta-apo-8'-carotenal, beta-apo-12'-carotene, beta-acid apo-8'-carotenoic, astaxanthin, canthaxanthin, zeaxanthin, cryptoxanthin, citranaxanthin, lutein, lycopene, torularodin-aldehyde, torularodin-ethyl ester, neuroesporaxon-tin-ethyl ester, zeta-carotene or dehydropylethanoxanthin. Carotenoids from natural sources are also included. Beta-carotene, astaxanthin, canthaxanthin, beta-apo-8'-carotenal and lycopene are preferred; the most preferred is beta-carotene. Natural colorants for the purposes of the present invention, include in particular curcumin, cochineal, carmine, bija, and mixtures thereof. Preferably, the method according to the present invention is carried out using carotenoids. The temperature of step b), preferably, is 120-180 ° C, more preferably, it is 140-170 ° C and, the temperature of step c), is preferably a 50-80 ° C. The residence time in the heat exchanger is preferably 0.5-4 seconds and, more preferably, 1-3 seconds.
The term "organic solvent immiscible with water" means, within the scope of the present invention, an organic solvent having a solubility in water of less than 10%, under atmospheric pressure. Organic solvents not miscible with water, suitable for carrying out the continuous process according to the present invention, are halogenated aliphatic hydrocarbons such as chloroform, carbon tetrachloride and methylene chloride, esters immiscible with water such as for example the dimethyl ester of carbonic acid (dimethyl carbonate), ethyl ester of formic acid (ethyl formate), methyl, ethyl, or isopropyl acetate; or ethers immiscible with water such as for example methyl tert.-butyl ether, and the like. Preferred are dimethyl carbonate, ethyl formate, ethyl or isopropyl acetate, and methyl tert. -butyl ether. The term "inflatable colloids" means, within the scope of the present invention, gelatin, carbohydrates such as for example starch or starch derivatives, dextrin, pectin, gum arabic, octenylbutanedioate amylodextrin (CAPSUL *), milk protein, such as for example casein, and vegetable protein, as well as mixtures of them. Fish gelatin or starch derivatives are preferred. To increase the stability of the carotenoid, it is advantageous to add an antioxidant selected from the group consisting of ascorbic acid, ascorbyl palmitate, dl-alpha tocopherol, mixed tocopherols, lecithin, butylhydroxytoluene, butyl-4-methoxyphenol and combinations of these compounds. The antioxidant can be added to both the matrix solution and the carotenoid solution, or to both solutions. A preferred antioxidant for the carotenoid solution is dl-alpha tocopherol and, for the solution of the aqueous phase, is ascorbyl palmitate. It may be further advantageous to dissolve an oil in the suspension of the carotenoid, preferably corn oil. Reference is now made to the accompanying drawings corresponding to Fig. 1, 'wherein a flow diagram, in a schematic form, suitable for carrying out the method according to the present invention is illustrated. The whole process must be carried out continuously. The flow diagram is explained as follows: An aqueous matrix containing an inflatable colloid and optionally a stabilizer is prepared in the boiler tank 1. A carotenoid suspension is prepared in the selected solvent in the boiler tank 2. The suspension , it may additionally contain an antioxidant and an oil. The carotenoid suspension is introduced, via pump 6, into exchanger 4. The flow rate is adjusted in accordance with the desired residence time that is needed to dissolve the carotenoid in the solvent at a given temperature. In the heat exchanger 4, the carotenoid suspension is heated to a temperature comprised between 100 to 250 ° C, preferably at a temperature of 120 to 180 ° C, more preferably at a temperature of 140. at 170 ° C, and the carotene is dissolved. The heating can be carried out both indirectly through the heat exchanger, and also directly by mixing with the steam 8. The residence time in the heat exchanger is less than 5 seconds, and a preferred form is 1 to 3 seconds. The matrix solution of the boiler tank 1 is introduced into the tank 3 by means of the feed pump 7. The flow depends on the flow rate of the suspension and the required composition of the emulsion. In the boiler tank 3, the carotenoid suspension and the matrix are mixed and emulsified, by using a rotor-stator homogenizer, to obtain the desired particle size of the inner phase, of approximately 150-400 nm. As a result of the mixing process, the temperature is lowered to levels comprised within margins ranging from 20 to 100 ° C. The dispersion obtained passes to the second heat exchanger 5, whereby the dispersion is cooled. The pressure is released to reach the value of the atmospheric pressure by controlling the pressure. The solvent is removed using conventional methods, for example by evaporation. A composition in powder form can be isolated from the resulting dispersion, by conventional methods, for example by spray-drying or by the use of dust collection or collection techniques.
Using the present invention, it is possible to manufacture powders that cover a very wide range of colors. The manner in which the method according to the present invention can be carried out in an easy manner is illustrated by the examples given below. The color intensity was measured in an aqueous solution containing 5 ppm of carotenoids and was provided by the calculated extinction of a 1% solution in a 1 cm cuvette (E 1/1 value). The average particle size was measured by a particle analyzer Coulter Partióle Analizer N4S. The carotenoid content was measured by UV spectroscopy. Example 1 Solvent: ethyl acetate, indirect heat transfer. The matrix shows, was prepared in the boiler 1 tank. In this way, 1.0 kg of ascor-bilo palmitate were dispersed in 27.8 kg of water, at a temperature of 60 ° C. The pH value of this dispersion was adjusted with NaOH (20%) to a value between 7.2-7.6. Next, 3.4 kg of fish gelatin and 7.2 kg of sucrose were added. The resulting mixture was stirred until a clear viscous solution was obtained. 0.75 kg of trans-β-carotene was dispersed in the form of crystals, in the boiler tank 2, in a mixture of 90 g of dl-a-tocopherol, 330 g of corn oil and 7.5 kg of ethyl acetate. The carotene suspension was introduced continuously at a flow rate of 6 kg / h, via the pump 6, into the heat exchanger 4, heated to a temperature of 160 ° C and the carotene was solubilized. The residence time in the heat exchanger was 4 seconds. The matrix solution of the boiler tank 1 was introduced, via the pump 7, with a flow rate of 9.2 kg / h, into the boiler tank 3, and mixed with the carotene solution. The resulting emulsion was cooled in a second heat exchanger 5, at a temperature of 60 ° C and, the pressure, was released until reaching the value of the atmospheric pressure. The ethyl acetate was removed in a thin film evaporator. The resulting emulsion showed a particle size in the interior phase of 225 nm and was dried by spraying process. A powder was obtained with the following specifications: 11.6% carotene content, E 1/1 = 1015,? max. 440-460 nm. The powder was well soluble in cold water with an intense red coloration. Example 2 Solvent: isopropyl acetate, direct heat transfer (steam). 1.25 kg of ascorbyl palmitate were dispersed in 30.9 kg of water at a temperature of 60 ° C, according to example 1. The pH value of this dispersion was adjusted with NaOH (20%) to a value of 7.2-7.6. Next, 5.1 kg of fish gelatin and 7.1 kg of sucrose were added. The resulting mixture was stirred until a clear viscous solution was obtained.
0.75 kg of canthaxanthin was dispersed in the form of crystals in the boiler tank 2, in a mixture of 0.10 kg of dl-a-tocopherol, 0.36 kg of corn oil and 6.25 kg of isopropyl acetate . The canthaxanthin suspension was introduced continuously at a flow rate of 6 kg / h, via pump 6, to the mixing chamber, where the temperature was increased by steam injection, at a temperature of 170 ° C. . Next, the hot canthaxanthin dispersion was passed in a course of time of 2 seconds, through the heat exchanger 4, where the canthaxanthin was solubilized. The matrix solution of the boiler tank 1 was introduced, via the pump 7, with a flow rate of 8.1 kg / h, into the boiler tank 3, and mixed with the canthaxanthin solution. The resulting emulsion was cooled in the heat exchanger 5, at a temperature of 60 ° C and, the pressure, was released until reaching the value of the atmospheric pressure. The isopropyl acetate was removed in a thin film evaporator. The resulting emulsion showed a particle size in the inner phase of 213 nm and was dried by spraying process. A powder was obtained with the following specifications: 12.3% canthaxanthin content, E l / l = 905,? max. 470-485 nm. The powder was well soluble in cold water, with an intense cherry-red color. Example 3 Solvent: isopropyl acetate, direct heat transfer (steam).
.3 kg of fish gelatin, 20.6 kg of sugar and 2.78 kg of ascorbyl palmitate were dissolved in 27.56 kg of water in the boiler tank 1. The pH value of this matrix was adjusted with NaOH (20%) at a value of 7.2-7.6. 6.68 kg of ß-carotene, 0.84 kg of dl-a-tocopherol, and 3.34 kg of corn oil were dispersed in 33.4 kg of isopropyl acetate in the boiler tank 2. The suspension of ß -carotene, was introduced at a flow rate of 25 kg / h, by means of pump 6, to heat exchanger 4, where it was mixed with steam to reach an exit temperature of 160 ° C. The residence time in heat exchanger 4 was 1.0 seconds. The matrix was pumped by means of the feed pump 7, with a flow rate of 34.5 kg / h, into the boiler tank 3, where the dissolved β-carotene was mixed with the matrix and emulsified therein. The emulsion was cooled to a temperature of 60 * C in the heat exchanger 5. The isopropyl acetate was removed from the emulsion by using a vertical evaporator. The resulting emulsion showed a particle size in the inner phase of 220 nm and was dried by spraying process. The final product had a content of ß-carotene of 11.3%; E 1/1: 1159,? max. 440-460 nm. The powder was well soluble in water. The solution had a very intense yellow color.
Example 4 Solvent: isopropyl acetate, direct heat transfer (steam). 9.25 kg of fish gelatin, 18.5 kg of sugar and 2.5 kg of ascorbyl pal itate were dissolved in 30.25 kg of water in the boiler tank 1. The pH value of this matrix was adjusted to NaOH (20%) at a value of 7.2-7.6. 6.0 kg of β-carotene, 0.75 kg of dl-ot-tocopherol, and 3.0 kg of corn oil were dispersed in 30.0 kg of isopropyl acetate in the boiler tank 2. The suspension of β - Oarotene, was introduced at a flow rate of 20 kg / h, by pump 6, in heat exchanger 4, where it was mixed with steam to reach an exit temperature of 158 * C. The residence time in heat exchanger 4 was 1.3 seconds. The matrix was pumped by means of the feed pump 7, with a flow rate of 30.4 kg / h, to the boiler tank 3, where the dissolved β-carotene was mixed with the matrix and emulsified therein. The emulsion was cooled to a temperature of 60 ° C in the heat exchanger 5. The isopropyl acetate was removed from the emulsion by the use of a vertical evaporator The resulting emulsion showed a particle size in the 240 nm inner phase and dried by spraying process The final product had a content of β-carotene of 11.2%, E 1/1: 795,? max 440-460 nm. powder was very soluble in water.The solution, had a very intense red color.
Example 5 Solvent: methylene chloride, direct heat transfer (steam). 9.25 kg of fish gelatin, 18.5 kg of sugar and 2.5 kg of ascorbyl palmitate were dissolved in 30.25 kg of water in the boiler tank 1. The pH value of this matrix was adjusted with NaOH (20%) at a value of 7.2-7.6. 6.0 kg of ß-carotene, 0.75 kg of dl-a-tocopherol, and 3.0 kg of corn oil were dispersed in 30.0 kg of methylene chloride in the boiler tank 2. The suspension of ß -carotene, was introduced at a flow rate of 20 kg / h, by pump 6, into the heat exchanger, where it was mixed with steam to reach an exit temperature of 145 ° C. The residence time in heat exchanger 4 was 1.3 seconds. The matrix was pumped by means of the feed pump 7, with a flow rate of 30.4 kg / h, to the boiler tank 3, where the dissolved β-carotene was mixed with the matrix and emulsified therein. The emulsion was cooled to a temperature of 35 ° C in the heat exchanger 5. The methylene chloride was removed from the emulsion by using a vertical evaporator. The resulting emulsion showed a particle size in the interior phase of 196 nm and was dried by spraying process. The final product had a content of β-carotene of 9.9%, E 1/1: 1120,? M? X. 440-460 n. The powder was well soluble in water. The solution had a very intense yellow color.
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is the conventional one for the manufacture of the objects or products to which it refers.
Claims (10)
- CLAIMS Having developed the invention as above, it is claimed as property contained in the following: 1.- A continuous process for the preparation of a composition in the form of a carotenoid powder, retinoid or natural dye, where the active ingredient is divided Fine-Ente, the prrrFphpñepto is this? The invention also includes the steps of: a) forming a suspension of the active ingredient in an organic solvent immiscible with water, optionally containing an antioxidant and / or an oil, b) introducing the suspension of the ) in a heat exchanger and the heating of said suspension at a temperature of 100-250 ° C, with which the residence time of the latter in the heat exchanger is less than 5 seconds, c) rapid mixing of the solution of step b) at a temperature within a range of 20 to 100 ° C, with an aqueous solution of a swellable colloid, optionally containing a stabilizer, d) removal of the organic solvent, and e) converting the dispersion of step d) into a preparation in powder form.
- 2. A process according to claim 1, characterized in that the active ingredient has a particle size of less than 1.0 micrometer, preferably less than 0.4 raicones.
- 3. A method according to claims 1 or 2, characterized in that the temperature of step b) is 120-180 ° C, preferably 140-170 ° C and the temperature of step c) is 50-80 ° C.
- 4. - A procedure according to any one of claims 1-3, characterized in that the residence time in the heat exchanger is 0.5-4 seconds, preferably 1-3 seconds.
- 5. A process according to any one of claims 1-4, characterized in that the solvent not miscible with water, is dimethyl carbonate, ethyl formate, isopropyl or ethyl acetate, methyl tert.-butyl ether or chloride of methylene.
- 6. A process according to any one of claims 1-5, characterized in that the active ingredient is a carotenoid.
- 7. A process according to claim 6, characterized in that the carotenoid is selected from the group consisting of beta-carotene, beta-apo-4'-carotenal, beta-apo-8'-carotenal, beta-apo- 12'-carotenal, beta-apo-8'-carotene noic acid, astaxanthin, canthaxanthin, zeaxanthin, cryptoxanthin, citronaxanthin, lutein, lycopene, torularodin-aldehyde, toru-larodin-ethylester, neuroesporaxontin-ethyl ester, zeta-carotene or dehydropylethanoxanthin .
- 8. A process according to any one of claims 1-7, characterized in that the inflatable colloid is selected from the group consisting of gelatin, starch or starch derivatives, dextrin, pectin, gum arabic, octenylbutanedioate amylodextrin, protein of milk, vegetable protein, as well as mixtures of them.
- 9. A procedure according to any one of the claims 1-8, characterized in that the antioxidant is selected from the group consisting of ascorbic acid, ascorbyl paltoate, dl-alpha tocopherol, mixed tocopherols, lecithin, butylated hydroxytoluene, butyl-4-methoxy-phenol and combinations of these compounds .
- 10. A process according to any one of claims 1-9, characterized in that the solution of the active ingredient is carried out either indirectly through a heat exchanger, or either directly by steam mixing, and precipitation. of the active ingredient in the inflatable colloid, is carried out continuously in a mixing device connected in series. 11 • "A preparation in the form of a powder, characterized in that it is prepared by a process according to any one of claims 1-10, and that it contains 0.5-25% by weight of an active ingredient.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CH98103113.1 | 1998-02-23 | ||
EP98103113 | 1998-02-23 |
Publications (3)
Publication Number | Publication Date |
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MX9901754A MX9901754A (en) | 2000-02-28 |
MXPA99001754A true MXPA99001754A (en) | 2000-04-24 |
MX224632B MX224632B (en) | 2004-12-03 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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MX9901754A MX224632B (en) | 1998-02-23 | 1999-02-22 | PREPARATION OF A FINALLY SPRAYED CAROTENOID PREPARATION. |
Country Status (16)
Country | Link |
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US (1) | US6406735B2 (en) |
EP (1) | EP0937412B1 (en) |
JP (1) | JP4837812B2 (en) |
KR (1) | KR100695589B1 (en) |
CN (1) | CN1173637C (en) |
AU (1) | AU743535B2 (en) |
BR (1) | BR9900776A8 (en) |
CA (1) | CA2261456A1 (en) |
DE (1) | DE69929641T2 (en) |
ES (1) | ES2257828T3 (en) |
ID (1) | ID23623A (en) |
IN (1) | IN1999CH00212A (en) |
MX (1) | MX224632B (en) |
NO (1) | NO315892B1 (en) |
PH (1) | PH11999000351B1 (en) |
TW (1) | TW565434B (en) |
Families Citing this family (62)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2238963T5 (en) * | 1999-12-09 | 2017-04-04 | Dsm Ip Assets B.V. | Compositions containing fat soluble vitamins |
DE60008299T2 (en) * | 2000-07-13 | 2004-11-25 | Vitatene, S.A. | Process for the preparation of a water-dispersible carotenoid-containing formulation |
US7105176B2 (en) * | 2000-11-29 | 2006-09-12 | Basf Aktiengesellschaft | Production of solid preparations of water-soluble, sparingly water-soluble or water-insoluble active compounds |
DK1213013T3 (en) * | 2000-11-29 | 2007-07-02 | Basf Ag | Process for the preparation of solid compositions of water-soluble, heavily water-soluble or water-insoluble active substances |
DE10064387A1 (en) | 2000-12-21 | 2002-06-27 | Basf Ag | Redispersible dry powder containing oxygen-containing carotenoid, useful e.g. as dye in foods, feed or pharmaceuticals, prepared in presence of partially degraded soya protein as protective colloid |
DE60200619T2 (en) | 2001-01-24 | 2005-06-09 | Kuraray Co., Ltd., Kurashiki | Process for the preparation of a carotenoid emulsion |
DE10104494A1 (en) | 2001-01-31 | 2002-08-01 | Basf Ag | Process for the preparation of dry powders of one or more carotenoids |
AU2002331210B2 (en) * | 2001-08-13 | 2007-07-19 | Dsm Ip Assets B.V. | Compositions comprising sugar beet pectin and carotenoids |
US6811801B2 (en) * | 2001-12-12 | 2004-11-02 | Abbott Laboratories | Methods and compositions for brightening the color of thermally processed nutritionals |
ES2189697B1 (en) * | 2001-12-28 | 2005-02-01 | Antibioticos, S.A.U. | PROCEDURE FOR OBTAINING NEW FORMULATIONS BASED ON LUTEINE. |
AU2003205699B8 (en) † | 2002-02-06 | 2008-06-05 | Dsm Ip Assets B.V. | Astaxanthin esters |
US6936279B2 (en) * | 2002-06-18 | 2005-08-30 | Zeavision Llc | Microcrystalline zeaxanthin with high bioavailability in oily carrier formulations |
EP1405572A1 (en) * | 2002-10-04 | 2004-04-07 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Modified lupin proteins for the preparation of water dispersible product forms of fat soluble compounds |
JPWO2004087645A1 (en) * | 2003-03-28 | 2006-06-29 | 株式会社クラレ | Method for producing carotenoid emulsion |
KR20040098887A (en) * | 2003-05-16 | 2004-11-26 | 주식회사 마린프로덕트테크 | The method for making Astaxanthin water-soluble |
CN100383194C (en) * | 2004-02-17 | 2008-04-23 | 章浩龙 | Preparation method of liquid disperse dye |
DE102004030072A1 (en) * | 2004-06-23 | 2006-01-19 | Basf Ag | Aqueous dispersions of poorly water-soluble or water-insoluble active ingredients and dry powders produced therefrom |
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DE602006019084D1 (en) | 2005-05-23 | 2011-02-03 | Phares Drug Delivery Ag | DIRECT SOLUTION |
DE102005030952A1 (en) | 2005-06-30 | 2007-01-18 | Basf Ag | Process for the preparation of an aqueous suspension and a pulverulent preparation of one or more carotenoids |
EP1903887A1 (en) | 2005-07-20 | 2008-04-02 | DSMIP Assets B.V. | Novel stabilized carotenoid compositions |
ES2279695B1 (en) * | 2005-08-01 | 2008-08-01 | Jesus Antas Pharma, S.A. | NEW SOLID FORMULATIONS OF CAROTENOIDS AND PROCEDURE FOR OBTAINING. |
CN101243032B (en) * | 2005-08-15 | 2012-10-10 | 法雷斯药品研究公司 | Crystal forms of astaxanthin |
EP1886584A1 (en) * | 2006-08-08 | 2008-02-13 | Indena S.P.A. | Stable and bioavailable compositions of isomers of lycopene for skin and hair |
US7435846B2 (en) | 2006-08-18 | 2008-10-14 | Industrial Organica, S.A. De C.V. | Absorption and bioavailability of carotenoids, formulations and applications |
WO2008087140A2 (en) | 2007-01-16 | 2008-07-24 | Basf Se | Liquid formulations containing a carotinoid |
EP1967081A1 (en) * | 2007-03-05 | 2008-09-10 | DSMIP Assets B.V. | Process for the manufacture of a powder containing carotenoids |
WO2008137831A1 (en) * | 2007-05-07 | 2008-11-13 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Water-soluble nanoparticles containing water-insoluble compounds |
HUE043897T2 (en) | 2007-09-25 | 2019-09-30 | Solubest Ltd | Compositions comprising lipophilic active compounds and method for their preparation |
CN101396068B (en) * | 2007-09-27 | 2013-05-01 | 浙江医药股份有限公司新昌制药厂 | Carotenoid preparation and use thereof and feedstuff containing the preparation and preparation method thereof |
CN105077203A (en) | 2007-11-29 | 2015-11-25 | 巴斯夫欧洲公司 | Pulverulent carotenoid preparation for colouring drinks |
KR20100097665A (en) * | 2007-12-05 | 2010-09-03 | 디에스엠 아이피 어셋츠 비.브이. | Pulverous formulation of a fat-soluble active ingredient |
EP2217092A1 (en) * | 2007-12-05 | 2010-08-18 | DSM IP Assets B.V. | Pulverous formulation of a fat-soluble active ingredient |
CN101297691B (en) * | 2008-06-06 | 2011-12-14 | 成都建福化学品有限公司 | Preparation of stable water-soluble carotenoid dry powder |
ES2563640T5 (en) | 2008-10-07 | 2021-11-22 | Basf Se | Stable emulsion, ready to use |
EP2210593A3 (en) | 2009-01-21 | 2011-05-18 | DSM IP Assets B.V. | Tablettable formulations of vitamin A and derivatives thereof |
DK2403361T3 (en) * | 2009-03-04 | 2013-04-08 | Basf Se | Process for the preparation of carotenoid solutions |
ES2400351T3 (en) * | 2009-03-05 | 2013-04-09 | Basf Se | Powder compositions of astaxanthin derivatives |
ES2873502T3 (en) | 2009-03-27 | 2021-11-03 | Bend Res Inc | Spray drying process |
WO2010112406A1 (en) | 2009-03-30 | 2010-10-07 | Basf Se | Ready-to-use, stable suspension of partially amorphous carotenoid particles |
PT2611530T (en) | 2010-09-03 | 2019-05-09 | Bend Res Inc | Spray-drying apparatus and methods of using the same |
PT2611529T (en) | 2010-09-03 | 2019-05-09 | Bend Res Inc | Spray-drying method |
WO2012040502A1 (en) | 2010-09-24 | 2012-03-29 | Bend Research, Inc. | High-temperature spray drying process and apparatus |
US20130317098A1 (en) | 2010-11-26 | 2013-11-28 | Christian Schaefer | Protective hydrocolloid for active ingredients |
US20120157547A1 (en) | 2010-12-21 | 2012-06-21 | Ricardo Montoya-Olvera | Compositions and applications of carotenoids of improved absorption and bioavailability |
US20140364512A9 (en) * | 2012-04-19 | 2014-12-11 | Epc (Beijing) Natural Products Co., Ltd. | Compositions comprising a combination of at least one colorant and at least one polysaccharide |
JP2016533766A (en) * | 2013-09-24 | 2016-11-04 | ディーエスエム アイピー アセッツ ビー.ブイ. | Stable red formulation for coloring beverages and foods |
CA2961473A1 (en) | 2014-09-15 | 2016-03-24 | Sustainable Aquatics, Inc. | Method and apparatus for producing astaxanthin |
EP3212169B1 (en) | 2014-10-31 | 2021-01-13 | Bend Research, Inc. | Process for forming active domains dispersed in a matrix |
KR101700909B1 (en) | 2015-05-29 | 2017-02-14 | 주식회사 마크로케어 | Two-phase reaction system for production of long chain retinyl ester and Preparation Method of ong chain retinyl ester |
US10479906B2 (en) * | 2015-09-18 | 2019-11-19 | Oregon State University | Use of fungal pigments from wood-staining fungi as colorants in wood finishes and paints |
US10835456B2 (en) * | 2016-07-19 | 2020-11-17 | Basf Se | Propyl gallate-containing vitamin preparations |
CN106278977A (en) * | 2016-08-09 | 2017-01-04 | 嘉必优生物技术(武汉)股份有限公司 | The method preparing bata-carotene crystal |
CN106278976A (en) * | 2016-08-09 | 2017-01-04 | 嘉必优生物技术(武汉)股份有限公司 | The method preparing bata-carotene crystal |
CN106278978A (en) * | 2016-08-09 | 2017-01-04 | 嘉必优生物技术(武汉)股份有限公司 | The method preparing bata-carotene crystal |
WO2019068288A1 (en) | 2017-10-04 | 2019-04-11 | Berlimed International Research Gmbh | Product containing active substance and active substance matrix for transdermal active substance delivery and production and use thereof and active substance matrix and production and use thereof |
WO2019207086A1 (en) | 2018-04-27 | 2019-10-31 | Dsm Ip Assets B.V. | Continuous manufacturing of spray-dried powders |
CN112004421A (en) | 2018-04-27 | 2020-11-27 | 帝斯曼知识产权资产管理有限公司 | Mechanism for manufacturing spray-dried powder |
CN112040786A (en) | 2018-04-27 | 2020-12-04 | 帝斯曼知识产权资产管理有限公司 | Method for producing spray-dried powder |
CN111471317B (en) * | 2020-03-26 | 2021-06-04 | 广东省农业科学院蚕业与农产品加工研究所 | Stable corn yellow pigment and preparation method thereof |
CN114287625B (en) * | 2021-12-28 | 2024-04-05 | 大连医诺生物股份有限公司 | Carotenoid preparation and application thereof |
WO2024028398A1 (en) * | 2022-08-05 | 2024-02-08 | Dsm Ip Assets B.V. | Solid formulations comprising beta-carotene |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2861891A (en) * | 1956-12-13 | 1958-11-25 | Hoffmann La Roche | Water dispersible carotenoid compositions and process of making the same |
US3110598A (en) * | 1959-09-08 | 1963-11-12 | Hoffmann La Roche | Process of making a carotenoid preparation |
DE1211911B (en) * | 1959-09-08 | 1966-03-03 | Hoffmann La Roche | Process for the production of a carotenoid preparation particularly suitable for coloring food and feed |
US3316101A (en) * | 1965-08-03 | 1967-04-25 | Hoffmann La Roche | Stabilizing carotenoid compositions |
CH522717A (en) * | 1969-02-07 | 1972-06-30 | Hoffmann La Roche | Dye preparation |
US3790688A (en) * | 1972-03-15 | 1974-02-05 | Us Agriculture | Water dispersible beta-carotene |
US3998753A (en) * | 1974-08-13 | 1976-12-21 | Hoffmann-La Roche Inc. | Water dispersible carotenoid preparations and processes thereof |
DE3119383A1 (en) * | 1981-05-15 | 1982-12-02 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING FINE DISTRIBUTED, POWDERED CAROTINO PREPARATIONS |
DE3610191A1 (en) * | 1986-03-26 | 1987-10-01 | Basf Ag | METHOD FOR PRODUCING FINE-PART, WATER-DISPERSIBLE CAROTINOID PREPARATIONS |
DE3611229A1 (en) * | 1986-04-04 | 1987-10-08 | Basf Ag | METHOD FOR PRODUCING FINE DISTRIBUTED, POWDERED CAROTINOID PREPARATIONS |
DE59003205D1 (en) * | 1989-07-25 | 1993-12-02 | Hoffmann La Roche | Process for the preparation of carotenoid preparations. |
DE19609538A1 (en) * | 1996-03-11 | 1997-09-18 | Basf Ag | Finely divided carotenoid and retinoid suspensions and process for their preparation |
DE19838636A1 (en) * | 1998-08-26 | 2000-03-02 | Basf Ag | Carotenoid formulations containing a mixture of beta-carotene, lycopene and lutein |
-
1999
- 1999-02-11 CA CA002261456A patent/CA2261456A1/en not_active Abandoned
- 1999-02-19 EP EP99103239A patent/EP0937412B1/en not_active Expired - Lifetime
- 1999-02-19 DE DE69929641T patent/DE69929641T2/en not_active Expired - Lifetime
- 1999-02-19 ES ES99103239T patent/ES2257828T3/en not_active Expired - Lifetime
- 1999-02-20 KR KR1019990005665A patent/KR100695589B1/en not_active IP Right Cessation
- 1999-02-22 ID IDP990134D patent/ID23623A/en unknown
- 1999-02-22 MX MX9901754A patent/MX224632B/en active IP Right Grant
- 1999-02-22 AU AU18362/99A patent/AU743535B2/en not_active Ceased
- 1999-02-22 IN IN212CH1999 patent/IN1999CH00212A/en unknown
- 1999-02-22 JP JP04259499A patent/JP4837812B2/en not_active Expired - Fee Related
- 1999-02-22 US US09/255,010 patent/US6406735B2/en not_active Expired - Lifetime
- 1999-02-22 BR BRPI9900776A patent/BR9900776A8/en not_active IP Right Cessation
- 1999-02-22 TW TW088102545A patent/TW565434B/en not_active IP Right Cessation
- 1999-02-23 PH PH11999000351A patent/PH11999000351B1/en unknown
- 1999-02-23 CN CNB991029003A patent/CN1173637C/en not_active Expired - Fee Related
- 1999-02-23 NO NO19990852A patent/NO315892B1/en not_active IP Right Cessation
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