WO2008087140A2 - Flüssige formulierungen enthaltend ein carotinoid - Google Patents
Flüssige formulierungen enthaltend ein carotinoid Download PDFInfo
- Publication number
- WO2008087140A2 WO2008087140A2 PCT/EP2008/050401 EP2008050401W WO2008087140A2 WO 2008087140 A2 WO2008087140 A2 WO 2008087140A2 EP 2008050401 W EP2008050401 W EP 2008050401W WO 2008087140 A2 WO2008087140 A2 WO 2008087140A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation according
- alcohol
- glycerol
- carotenoid
- glycol
- 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.)
- Ceased
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/07—Retinol compounds, e.g. vitamin A
-
- A—HUMAN NECESSITIES
- 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
- A23K20/163—Sugars; Polysaccharides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to liquid formulations, processes for their preparation and their use as additives to animal feeds and foods.
- carotenoid primary particles with a particle size in the nanometer range is crucial in order to achieve sufficient bioavailability and color yields.
- the grinding of the carotenoids takes place by means of a colloid mill in aqueous or oily media, whereby a particle size in the nanometer range is achieved.
- EP 1 460 060 A describes the production of lutein suspensions by grinding in an oil. Further, it describes cold water dispersible lutein formulations prepared by dissolving lutein in a water immiscible organic solvent and encapsulating in modified starch in the presence of an emulsifier.
- US 2005/0084462 describes the preparation of a dye mixture for use in food, pharmaceutical and cosmetic products by milling a dye in water in the presence of gum arabic as a carrier and then heating to 30 to 60 0 C.
- US 5,827,539 describes grinding a dispersion of a carotenoid in oil, forming an emulsion with a mixture of starch, sugar and an antioxidant, and finally spray-drying.
- WO 9613178 describes the preparation of stable lycopene concentrates by milling the lycopene in a liquid medium in which the lycopene is substantially insoluble.
- the liquid medium used is glycerol, propylene glycol or ethanol.
- a hydrocolloid is not used.
- WO 96/23429 describes the preparation of oily astaxanthin suspensions with particle sizes ⁇ 2 ⁇ m by grinding astaxanthin, during which an oil is added during or after the grinding.
- the use of protective colloids or emulsifiers is not disclosed. It should be noted that the particles tend to agglomerate. Accordingly, further stabilization by keeping the suspension below the solidification temperature is contemplated.
- WO 93/04598 describes the preparation of a carotenoid composition containing a carotenoid in an oil, a dispersion of a water-dispersible matrix former, for example a sugar, and a stabilizer, for example gelatin or casein and an emulsifier, and optionally a non-oily solvent, such as glycerol.
- a water-dispersible matrix former for example a sugar
- a stabilizer for example gelatin or casein and an emulsifier
- a non-oily solvent such as glycerol.
- the present invention has for its object to provide a liquid carotenoid formulation available that can be easily produced and used by the user without additional effort.
- the present invention therefore provides a liquid formulation comprising at least one carotenoid, at least one hydrophilic protective colloid and at least one water-miscible alcohol.
- carotenoids known, from natural sources or synthetically accessible representatives can be used.
- the known, from natural sources or synthetically accessible representatives can be used. Examples of these are ⁇ -carotene, lycopene, lutein, astaxanthin, zeaxanthin, cryptoxanthin, citranaxanthin, canthaxanthin, echinenone, bixin, ⁇ -apo-4-carotenal, ⁇ -apo-8-carotenal, ⁇ -apo-4-carotenoic acid ester, individually or as a mixture.
- astaxanthin Preference is given to astaxanthin, ⁇ -carotene, ⁇ -apo-8-carotenal, ⁇ -apo-8'-carotenoic acid ethyl ester, canthaxanthin, citranaxanthin, echinenone, lutein, lycopene and zeaxanthin. Particularly preferred are astaxanthin and canthaxanthin and in particular astaxanthin.
- the carotenoids generally have a particle size in the range from 50 nm to 10 .mu.m, preferably 100 nm to 5 .mu.m, particularly preferably 100 nm to 3 .mu.m, 150 nm to 2 .mu.m and in particular 200 nm to 1 .mu.m.
- Suitable hydrophilic protective colloids are water-soluble or swellable colloids. They are preferably protein-based protective colloids, modified starch derivatives and modified cellulose derivatives. Protective colloids based on protein are, in particular, casein, caseinate, bovine, porcine or fish gelatin, in particular acid or basic degraded gelatin having bloom numbers in the range from 0 to 250 and mixtures thereof.
- the modified starch derivatives and cellulose derivatives are, in particular, the esters, for example starch octenylsuccinate.
- Corresponding products are commercially available under the name Purity Gum 2000 from National Starch or Clear Gum CO 01 from Roquette, Hi Cap 100 or Capsul from National Starch.
- modified starches are used as the hydrophilic protective colloid.
- Suitable water-miscible alcohols are monoalcohols and polyalcohols.
- the monoalcohols are alkanols such as methanol, ethanol, isopropanol, etc.
- polyalcohols are used. These are especially dihydric or trihydric alcohols. Examples of these are glycol, propylene glycol, butylene glycol, polyethylene glycol, polypropylene glycol, glycerol, monoesters of glycerol with CrC 5 monocarboxylic acids, or monoethers of glycerol.
- the formulations according to the invention particularly preferably contain glycerol.
- the carotenoids are generally in the formulations according to the invention in one
- the amount of hydrophilic protective colloid is generally in the range of 1 to 40% by weight, preferably 2 to 30% by weight and especially 3 to 25% by weight.
- the weight ratio of carotenoid to hydrophilic protective colloid is generally in the range of 5: 1 to 1: 5, preferably 3: 1 to 1: 3.
- the amount of water-miscible alcohols is generally in the range of 30 to 95 wt .-%, in particular 30 to 90 wt .-% and particularly preferably 35 to 90 wt .-%, based on the total weight of the formulation.
- the formulations according to the invention may contain water in an amount of up to 40% by weight, preferably up to 35% by weight, based on the total weight of the formulation.
- the formulations according to the invention contain no oil.
- stabilizers such as ⁇ -tocopherol, t-butylhydroxytoluene, t-butylhydroxyanisole, ascorbic acid or ethoxyquin.
- the formulations according to the invention may also contain auxiliaries, such as thickeners, hard fats, chelating agents, for example alkali metal or alkaline earth metal salts of citric acid, phytic acid or phosphoric acid and / or emulsifiers.
- auxiliaries such as thickeners, hard fats, chelating agents, for example alkali metal or alkaline earth metal salts of citric acid, phytic acid or phosphoric acid and / or emulsifiers.
- emulsifiers are ascorbyl palmitate, polyglycerol fatty acid esters such as polyglycerol-3-polyricinoleate (PGPR 90), sorbitan fatty acid esters such as sorbitan monostearate (Span 60), PEG (20) sorbitol monooleate, propylene glycol fatty acid esters or phospholipids such as lecithin.
- a dispersion of the carotenoid and the hydrophilic protective colloid is ground in the water-miscible alcohol used. However, part of the alcohol may also be added during milling. Milling is carried out until an average particle size of the carotenoid crystals and of the hydrophilic protective colloid of ⁇ 5 ⁇ m, preferably ⁇ 1 ⁇ m, is reached.
- Conventional devices known to those skilled in the art for example colloid mills, ball mills, such as Dynomill type KDL or Multilab, can be used as the device for grinding.
- formulations according to the invention can be added directly to aqueous or nonaqueous preparations. However, they may also be further diluted with the alcohol used before addition.
- the formulations are suitable, inter alia, as an additive to animal feeds and food preparations or compound feed, as agents for the production of pharmaceutical and cosmetic preparations and for the production of dietary supplement preparations in the human and animal sector.
- the suspensions can preferably be used as a feed additive in animal nutrition, for example by mixing into feed pellets during extrusion or by application or spraying onto feed pellets.
- the use as a feed additive is effected in particular by direct spraying of the According to the invention formulations, for example as a so-called "post-pelleting application.”
- the feed pellets are loaded with the formulations under reduced pressure.
- Typical applications in the food industry are, for example, the vitaminization and coloring of beverages, dairy products such as yoghurt, milk mix drinks or milk ice cream, as well as pudding powders, egg products, baking mixes and confectionery.
- the oily suspensions can be used, for example, for decorative personal care products, for example in the form of a cream, a lotion, as a lipstick or make-up.
- the invention furthermore relates to dietary supplements, animal feeds, foods and pharmaceutical and cosmetic preparations which comprise the formulations according to the invention. Preference is given to animal feed, in particular feed pellets, which are loaded with the formulations.
- dietary supplements as well as pharmaceutical preparations are u.a. Tablets, dragees and preferably hard and soft gelatin capsules to understand which comprise the formulations according to the invention.
- Example 2 Following the procedure described in Example 1, a dispersion of 210.0 g of crystalline ⁇ -carotene, 221, 68 g of Purity Gum 2000 (H 2 O content 5.27%) and 2568.32 g of glycerol was ground. The grinding was carried out at a temperature in the range of 52 to 68 0 C. After 1.5 h, a thin liquid dispersion was obtained in which the ß-carotene had a particle size of 438 nm.
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Food Science & Technology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Animal Husbandry (AREA)
- Nutrition Science (AREA)
- Zoology (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Botany (AREA)
- Mycology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Fodder In General (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009545201A JP5368316B2 (ja) | 2007-01-16 | 2008-01-15 | カロテノイドを含有する液体製剤 |
| EP08707899.4A EP2111125B2 (de) | 2007-01-16 | 2008-01-15 | Flüssige formulierungen enthaltend carotinoide |
| US12/522,554 US8809398B2 (en) | 2007-01-16 | 2008-01-15 | Liquid formulations containing a carotinoid |
| DK08707899.4T DK2111125T4 (en) | 2007-01-16 | 2008-01-15 | LIQUID FORMULATIONS CONTAINING CAROTINOIDS |
| CN2008800024418A CN101583286B (zh) | 2007-01-16 | 2008-01-15 | 含有类胡萝卜素的液体配制剂 |
| AT08707899T ATE501644T1 (de) | 2007-01-16 | 2008-01-15 | Flüssige formulierungen enthaltend carotinoide |
| ES08707899.4T ES2361276T5 (es) | 2007-01-16 | 2008-01-15 | Formulaciones líquidas, que contienen carotenoides |
| DE502008002872T DE502008002872D1 (de) | 2007-01-16 | 2008-01-15 | Flüssige formulierungen enthaltend carotinoide |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07100633 | 2007-01-16 | ||
| EP07100633.2 | 2007-01-16 | ||
| EP07105349.0 | 2007-03-30 | ||
| EP07105349 | 2007-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2008087140A2 true WO2008087140A2 (de) | 2008-07-24 |
| WO2008087140A3 WO2008087140A3 (de) | 2008-09-12 |
Family
ID=39570485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2008/050401 Ceased WO2008087140A2 (de) | 2007-01-16 | 2008-01-15 | Flüssige formulierungen enthaltend ein carotinoid |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8809398B2 (de) |
| EP (1) | EP2111125B2 (de) |
| JP (2) | JP5368316B2 (de) |
| CN (1) | CN101583286B (de) |
| AT (1) | ATE501644T1 (de) |
| CL (1) | CL2008000129A1 (de) |
| DE (1) | DE502008002872D1 (de) |
| DK (1) | DK2111125T4 (de) |
| ES (1) | ES2361276T5 (de) |
| WO (1) | WO2008087140A2 (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010040683A1 (de) * | 2008-10-07 | 2010-04-15 | Basf Se | Gebrauchfertige, stabile emulsion |
| WO2010112406A1 (de) | 2009-03-30 | 2010-10-07 | Basf Se | Gebrauchsfertige, stabile suspension teilamorpher carotinoidpartikel |
| CN102796398A (zh) * | 2012-07-31 | 2012-11-28 | 浙江新维普添加剂有限公司 | 一种用于着色的β-胡萝卜素微胶囊的制备方法 |
| US8809398B2 (en) | 2007-01-16 | 2014-08-19 | Basf Se | Liquid formulations containing a carotinoid |
| US11185093B2 (en) | 2007-11-29 | 2021-11-30 | Christian Köpsel | Pulverulent carotenoid preparation for colouring drinks |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009008019A (es) * | 2007-02-23 | 2009-08-07 | Basf Se | Uso de nanoparticulas carotenoides dispersibles en agua como moduladores de sabor, moduladores de sabor que contiene nanoparticulas carotenoides dispersibles en agua y metodo para modulacion de sabor. |
| DE202008006491U1 (de) * | 2007-02-23 | 2008-08-21 | Basf Se | Verwendung von Azoverbindungen zur Geschmacksmodulation von stofflichen Zusammensetzungen, die mindestens einen High Intensity Sweetener (HIS) enthalten |
| USD806351S1 (en) | 2016-09-06 | 2018-01-02 | Mars, Incorporated | Food product |
| USD805728S1 (en) | 2016-09-06 | 2017-12-26 | Mars, Incorporated | Food product |
| GB201701417D0 (en) | 2017-01-27 | 2017-03-15 | Mars Inc | Pet food |
| CN111714466A (zh) | 2019-03-18 | 2020-09-29 | 浙江医药股份有限公司新昌制药厂 | 一种高生物利用度高稳定性的类胡萝卜素制剂的制备方法 |
| CN115736158A (zh) * | 2022-12-30 | 2023-03-07 | 广州百花香料股份有限公司 | 一种稳定的乳化香精及其制备方法 |
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2008
- 2008-01-15 CN CN2008800024418A patent/CN101583286B/zh active Active
- 2008-01-15 US US12/522,554 patent/US8809398B2/en active Active
- 2008-01-15 DE DE502008002872T patent/DE502008002872D1/de active Active
- 2008-01-15 DK DK08707899.4T patent/DK2111125T4/en active
- 2008-01-15 JP JP2009545201A patent/JP5368316B2/ja active Active
- 2008-01-15 EP EP08707899.4A patent/EP2111125B2/de active Active
- 2008-01-15 WO PCT/EP2008/050401 patent/WO2008087140A2/de not_active Ceased
- 2008-01-15 AT AT08707899T patent/ATE501644T1/de active
- 2008-01-15 ES ES08707899.4T patent/ES2361276T5/es active Active
- 2008-01-16 CL CL200800129A patent/CL2008000129A1/es unknown
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8809398B2 (en) | 2007-01-16 | 2014-08-19 | Basf Se | Liquid formulations containing a carotinoid |
| US11185093B2 (en) | 2007-11-29 | 2021-11-30 | Christian Köpsel | Pulverulent carotenoid preparation for colouring drinks |
| WO2010040683A1 (de) * | 2008-10-07 | 2010-04-15 | Basf Se | Gebrauchfertige, stabile emulsion |
| CN102176833A (zh) * | 2008-10-07 | 2011-09-07 | 巴斯夫欧洲公司 | 即用型稳定乳液 |
| JP2012505155A (ja) * | 2008-10-07 | 2012-03-01 | ビーエーエスエフ ソシエタス・ヨーロピア | すぐ使用できる安定なエマルション |
| US9375387B2 (en) | 2008-10-07 | 2016-06-28 | Basf Se | Ready-to-use, stable emulsion |
| US10004670B2 (en) | 2008-10-07 | 2018-06-26 | Basf Se | Ready-to-use, stable emulsion |
| EP2343986B2 (de) † | 2008-10-07 | 2021-04-21 | Basf Se | Gebrauchfertige, stabile emulsion |
| WO2010112406A1 (de) | 2009-03-30 | 2010-10-07 | Basf Se | Gebrauchsfertige, stabile suspension teilamorpher carotinoidpartikel |
| CN102796398A (zh) * | 2012-07-31 | 2012-11-28 | 浙江新维普添加剂有限公司 | 一种用于着色的β-胡萝卜素微胶囊的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20100120922A1 (en) | 2010-05-13 |
| JP2010515447A (ja) | 2010-05-13 |
| US8809398B2 (en) | 2014-08-19 |
| JP5368316B2 (ja) | 2013-12-18 |
| DE502008002872D1 (de) | 2011-04-28 |
| WO2008087140A3 (de) | 2008-09-12 |
| EP2111125A2 (de) | 2009-10-28 |
| ES2361276T3 (es) | 2011-06-15 |
| EP2111125B2 (de) | 2016-11-16 |
| EP2111125B1 (de) | 2011-03-16 |
| ES2361276T5 (es) | 2017-06-09 |
| DK2111125T4 (en) | 2017-02-27 |
| CN101583286B (zh) | 2013-08-21 |
| DK2111125T3 (da) | 2011-06-20 |
| CN101583286A (zh) | 2009-11-18 |
| CL2008000129A1 (es) | 2008-05-23 |
| JP5841974B2 (ja) | 2016-01-13 |
| ATE501644T1 (de) | 2011-04-15 |
| JP2013240337A (ja) | 2013-12-05 |
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