WO2004086882A1 - Powderous formulations of fat-soluble active ingredients - Google Patents
Powderous formulations of fat-soluble active ingredients Download PDFInfo
- Publication number
- WO2004086882A1 WO2004086882A1 PCT/EP2004/003110 EP2004003110W WO2004086882A1 WO 2004086882 A1 WO2004086882 A1 WO 2004086882A1 EP 2004003110 W EP2004003110 W EP 2004003110W WO 2004086882 A1 WO2004086882 A1 WO 2004086882A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- protein
- fat
- formulations according
- lupin
- composition
- 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
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/14—Vegetable proteins
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
- A23J1/14—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from leguminous or other vegetable seeds; from press-cake or oil-bearing seeds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/15—Vitamins
- A23L33/155—Vitamins A or D
-
- 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
- A23L33/17—Amino acids, peptides or proteins
- A23L33/185—Vegetable proteins
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
-
- 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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/645—Proteins of vegetable origin; Derivatives or degradation products 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
-
- 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
Definitions
- the present invention is concerned with novel stable powderous formulations comprising a fat-soluble active ingredient, and a process for their preparation.
- novel compositions of this invention can be used as additives for food, beverages, animal feeds, cosmetics or drugs to incorporate said fat-soluble ingredients into such application forms.
- the present invention is concerned with stable powderous formulations comprising a fat-soluble active ingredient in a matrix of a native lupin protein composition.
- the term “native lupin protein” denotes a lupin protein as it is found in natural products such as lupin seeds and has not been modified by hydrolysis.
- the term “domaind” proteins is understood to include lupin proteins which have undergone post-isoelectric precipitation and are generally known as "restructured” proteins, see international patent application WO 99/11143 and references contained therein.
- native lupin protein composition denotes any composition comprising native lupin protein as obtainable from natural lupin protein sources.
- native lupin protein compositions are lupin protein concentrates, which have a protein content of 60 % up to 90 % by weight (hereinafter : wt.-%), generally from 50-96 wt.-%, typically about 65-70 wt.-% of protein; and lupin protein isolates, which term is generally used in the art to define protein preparations containing more than about 90 wt.-% of protein.
- the residual constituents (4-50 wt.-%) of such concentrates and isolates are, besides water and oil, primarily plant fibers.
- lupin concentrates having a protein content of about 60- 90 wt.-%, isolates having a protein content of more than 90 wt.-%, and flours having a protein content of about 40-60 wt.-%,
- Lupine Angustifolius, Lupine Albus oder Lupine Luteus can be used.
- protein compositions derived from Lupine Angustifolius and Lupine Albus are preferred.
- fat-soluble active ingredient denotes any physiologically active ingredient that is soluble in lipids and insoluble or sparingly soluble in water.
- fat-soluble active ingredients are fat-soluble vitamins, viz., vitamin A, D, E and K and derivatives thereof such as vitamin A esters, e.g. vitamin A acetate and palmiate, and vitamin E esters, e.g.
- carotenoids and carotinoid derivatives e.g., are ⁇ - or ⁇ -carotene, 8'-apo- ⁇ -carotenal, 8'-apo- ⁇ -carotenoic acid esters such as the ethyl ester, canthaxanthin, astaxanthin, astaxanthin esters, lycopene, lutein, zeaxanthin or crocetin and their derivatives; polyunsaturated fatty acids, e.g. eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid and and ⁇ -linolenic acid and/or ethylester.
- carotenoids and carotinoid derivatives e.g., are ⁇ - or ⁇ -carotene, 8'-apo- ⁇ -carotenal, 8'-apo- ⁇ -carotenoic acid esters such as the ethyl ester, canthax
- the fat-soluble active ingredient maybe present in the formulation in an amount of from about 0.1 wt.-% to about 80 wt.-%, especially from about 0.5 wt.-% to about 60 wt.-%, based on the total weight of the composition.
- the novel formulations additionally contain a reducing sugar, e.g. glucose, fructose, or xylose in an amount of from about 0.1 wt.-% to about 70 wt.-%, especially from about 1.0 to about 10 wt.-%, based on the total weight of the composition.
- a reducing sugar e.g. glucose, fructose, or xylose in an amount of from about 0.1 wt.-% to about 70 wt.-%, especially from about 1.0 to about 10 wt.-%, based on the total weight of the composition.
- Such formulations can be submitted to heat- treatment to cause cross-linking of the sugar with the protein in a Maillard type reaction.
- Crosslinking can be also achieved by treatment with enzymes like transglutaminase in a manner know per se, see, e.g., US 5,156,956.
- the cross-linked formulations have been found to exhibit increased stability.
- the novel formulations can be obtained by a process which comprises preparing an aqueous emulsion of the fat-soluble active ingredient and the native lupin protein composition, if desired, adding a reducing sugar, converting the emulsion into a dry powder and, if a reducing sugar was added, submitting the dry powder to cross-linking the sugar with the protein by heat treatment or by treatment with a cross-linking enzyme.
- the protein composition is dispersed in water.
- the fat-soluble active ingredient is emulsified, suitably in liquid state, i.e.
- a suspension of the solid active maybe produced by appropriate procedures like milling.
- the emulsion is then, optionally after removal of excess solvent, spray-dried.
- the spray-drying can effected be using conventional technology of spray-drying, spray drying in combination with fluidized-bed granulation (the latter technique commonly known as fiuidized spray drying or FSD), or by a powder-catch technique where sprayed emulsion droplets are caught in a bed of an absorbant such as starch or calcium silicate and subsequently dried.
- the novel formulations may additionally contain other proteins or hydrolyzed proteins that act as protective colloids, e.g. soy proteins or, hydrolyzed soy proteins.
- additional proteins may be present in the formulations of the invention in an amount of from 10-50 wt.-% based on the total amount of protein in the formulation.
- the present invention is concerned with food, beverages, animal feeds, cosmetics and drugs which comprise the novel formulations of the present invention.
- novel formulations of this invention may further contain adjuvants and/or excipients such as one or more of a mono- di-, oligo- or polysaccharide, a triglyceride, a water- soluble antioxidant, a fat-soluble antioxidant, silicic acid, Ca-silicate, Ca-carbonate and water.
- adjuvants and/or excipients such as one or more of a mono- di-, oligo- or polysaccharide, a triglyceride, a water- soluble antioxidant, a fat-soluble antioxidant, silicic acid, Ca-silicate, Ca-carbonate and water.
- Examples of mono- and disaccharides which maybe present in the formulations of the present invention are saccharose, invert sugar, glucose, fructose, lactose and maltose.
- Examples of oligo- or polysaccharides which may be present in the compositions of the present invention are starch, modified starch and starch hydrolysates, such as dextrins and maltodextrins, especially such in the range of 5-65 dextrose equivalents (hereinafter: DE) and glucose syrup, especially such in the range of 20-95 DE.
- DE dextrins and maltodextrins
- glucose syrup especially such in the range of 20-95 DE.
- DE dextrins and maltodextrins
- the triglyceride is suitably a vegetable oil or fat, such as corn oil, sunflower oil, soybean oil, safflower oil, rape seed oil, arachis oil, palm oil, palm kernel oil, cotton seed oil or cocos oil.
- the water-soluble antioxidant may be ascorbic acid and salts thereof, e.g., sodium ascorbate, and the like.
- the fat-soluble antioxidant may be a tocopherol, e.g., dl- ⁇ - tocopherol (i.e., synthetic tocopherol), d- ⁇ -tocopherol (i.e., natural tocopherol), ⁇ - and ⁇ - tocopherol and mixtures thereof; ascorbic acid esters of fatty acids such as ascorbyl palmitate or stearate; butyl hydroxy toluene (BHT); butyl hydroxy anisol (BHA); propyl gallate; or t-butyl hydroxy quinoline; or 6-ethoxy-l,2-dihydroxy-2,2,4-trimethylquinoline (EMQ).
- dl- ⁇ - tocopherol i.e., synthetic tocopherol
- d- ⁇ -tocopherol i.e., natural tocopherol
- the emulsion was then diluted with ca. 25 ml of water and about 300 g of the emulsion was sprayed in a spraying pan in a bed of Ca-silicate at about 5° C by means of a rotating spraying nozzle.
- the so- obtained beadlets are separated from excess Ca-silicate by sieving and dried. There were obtained ca. 100 g of dry powder having a vitamin A content of ca. 850'000 IEA/g.
- Example 3 The vitamin A dry powder obtained in Example 1 is stirred at a temperature of 135 °C for 35 minutes.
- the so-obtained product was insoluble in hot water and had a vitamin A content of ca. 570O00 IEA/g.
- Example 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Mycology (AREA)
- Birds (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Fodder In General (AREA)
- Edible Oils And Fats (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fats And Perfumes (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/551,197 US20060257453A1 (en) | 2003-04-03 | 2004-03-24 | Powderous formulations of fat-soluble active ingredients |
| DE602004025212T DE602004025212D1 (de) | 2003-04-03 | 2004-03-24 | Pulverförmige zusammensetzungen von fettlöslichen substanzen |
| JP2006504839A JP4716982B2 (ja) | 2003-04-03 | 2004-03-24 | 脂溶性活性成分の粉末状配合物 |
| KR1020057018685A KR101109832B1 (ko) | 2003-04-03 | 2004-03-24 | 지용성 활성 성분의 분말 제형 |
| EP04722828A EP1608237B1 (en) | 2003-04-03 | 2004-03-24 | Powderous formulations of fat-soluble active ingredients |
| AT04722828T ATE455471T1 (de) | 2003-04-03 | 2004-03-24 | Pulverförmige zusammensetzungen von fettlöslichen substanzen |
| US13/294,676 US20120059070A1 (en) | 2003-04-03 | 2011-11-11 | Powderous formulations of fat-soluble active ingredients |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03007677.2 | 2003-04-03 | ||
| EP03007677 | 2003-04-03 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/551,197 A-371-Of-International US20060257453A1 (en) | 2003-04-03 | 2004-03-24 | Powderous formulations of fat-soluble active ingredients |
| US13/294,676 Continuation US20120059070A1 (en) | 2003-03-04 | 2011-11-11 | Powderous formulations of fat-soluble active ingredients |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2004086882A1 true WO2004086882A1 (en) | 2004-10-14 |
| WO2004086882A8 WO2004086882A8 (en) | 2004-12-23 |
Family
ID=33104049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2004/003110 Ceased WO2004086882A1 (en) | 2003-04-03 | 2004-03-24 | Powderous formulations of fat-soluble active ingredients |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US20060257453A1 (enExample) |
| EP (1) | EP1608237B1 (enExample) |
| JP (1) | JP4716982B2 (enExample) |
| KR (1) | KR101109832B1 (enExample) |
| CN (2) | CN103181566A (enExample) |
| AT (1) | ATE455471T1 (enExample) |
| DE (1) | DE602004025212D1 (enExample) |
| ES (1) | ES2339661T3 (enExample) |
| WO (1) | WO2004086882A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008089735A1 (de) * | 2007-01-23 | 2008-07-31 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Wasserhaltiges pflanzliches proteinpräparat und verfahren zur herstellung desselben |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010127414A1 (en) * | 2009-05-08 | 2010-11-11 | George Weston Foods Limited | Oil-in-water emulsifier |
| WO2010127415A1 (en) * | 2009-05-08 | 2010-11-11 | George Weston Foods Limited | Water-in-oil emulsifier |
| CA2983465A1 (en) * | 2015-08-14 | 2017-02-23 | Russell W. Day | Ruminal protection of lipids, lipid-bearing materials, and bioactive aliments |
| EP3351118A1 (en) * | 2017-01-20 | 2018-07-25 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Fat-soluble active ingredient composition, microcapsule and uses thereof and process of preparation |
| CN115137018B (zh) * | 2021-03-30 | 2024-03-15 | 新发药业有限公司 | 一种维生素a及其衍生物组合物 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892727A (en) * | 1985-07-24 | 1990-01-09 | Societe Anonyme Dite: L'oreal | Cosmetic or dermopharmaceutical compositions containing a powder of sweet lupine seeds essentially free of alkaloids |
| RU2017434C1 (ru) * | 1991-04-04 | 1994-08-15 | Головченко Владимир Иванович | Диетический пектинобелковый продукт "лювит" |
| WO1999011143A1 (en) * | 1997-09-01 | 1999-03-11 | E.I. Du Pont De Nemours And Company | Functional protein concentrates and isolates |
| EP1106174A1 (en) * | 1999-12-09 | 2001-06-13 | F. Hoffmann-La Roche Ag | Compositions containing fat-soluble vitamins |
| 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 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835592A (en) * | 1957-04-26 | 1958-05-20 | Gen Foods Corp | Flavor |
| US2897118A (en) * | 1957-05-24 | 1959-07-28 | Merck & Co Inc | Stable vitamin a compositions |
| US3549555A (en) * | 1968-10-08 | 1970-12-22 | Ncr Co | Encapsulation of lipophilic liquid-in-hydrophilic liquid emulsions |
| US4395422A (en) * | 1981-04-06 | 1983-07-26 | Basf Wyandotte Corporation | Spray dried vitamin E powder |
| US4670247A (en) * | 1983-07-05 | 1987-06-02 | Hoffman-Laroche Inc. | Process for preparing fat-soluble vitamin active beadlets |
| JPS63186799A (ja) * | 1987-01-29 | 1988-08-02 | 不二製油株式会社 | 油脂粉末の製造方法 |
| JPH0665280B2 (ja) * | 1987-03-04 | 1994-08-24 | 味の素株式会社 | タンパクゲル化剤及びそれを用いるタンパクのゲル化方法 |
| JP2601300B2 (ja) * | 1987-04-06 | 1997-04-16 | 旭化成工業株式会社 | 粉状または粒状油脂およびその製造方法 |
| JPS6418439A (en) * | 1987-07-14 | 1989-01-23 | Nippon Oils & Fats Co Ltd | Powdery fat coated with crosslinked coating and its manufacture |
| US5153177A (en) * | 1991-01-10 | 1992-10-06 | Basf Corporation | Process for incorporating a material in a crosslinked gelatin, and product therefrom |
| DE4141351A1 (de) * | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
| US5853761A (en) * | 1995-02-13 | 1998-12-29 | Fujisawa Pharmaceutical Co., Ltd. | Stabilizing agent for oleaginous, physiologically active substances |
| ES2199450T3 (es) * | 1997-07-15 | 2004-02-16 | Coletica | Particulas, en particular micro- o nanoparticulas de proteinas vegetales reticuladas, su procedimiento de preparacion y composiciones cosmeticas, farmaceuticas o alimentarias que las contienen. |
| FR2766090B1 (fr) * | 1997-07-15 | 1999-10-08 | Coletica | Particules, en particulier micro- ou nanoparticules de proteines vegetales reticulees, leur procede de preparation et compositions cosmetiques, pharmaceutiques ou alimentaires en contenant |
| GB9807256D0 (en) * | 1998-04-03 | 1998-06-03 | Du Pont Uk | Functional protein compositions,emulsions based thereon and processes for their preparation |
| FR2777193B1 (fr) * | 1998-04-14 | 2001-06-08 | Coletica | Particule a groupement hydroxamique chelatante d'ions metalliques et leur utilisation en cosmetique ou en pharmacie |
| DE19838189A1 (de) * | 1998-08-24 | 2000-03-02 | Basf Ag | Stabile pulverförmige Vitamin- und Carotinoid-Zubereitungen und Verfahren zu deren Herstellung |
| JP2000083695A (ja) * | 1998-09-16 | 2000-03-28 | Ajinomoto Co Inc | 低苦味ペプチドの製造法 |
| JP2001078718A (ja) * | 1999-08-27 | 2001-03-27 | Basf Ag | 活性成分調製剤の製造方法、活性成分調製剤及び食品又は飼料 |
| US6328995B1 (en) * | 1999-09-24 | 2001-12-11 | Basf Aktiengesellschaft | Stable vitamin and/or carotenoid products in powder form and process for their production |
| ES2238963T5 (es) * | 1999-12-09 | 2017-04-04 | Dsm Ip Assets B.V. | Composiciones que contienen vitaminas solubles en grasas |
| US6423364B1 (en) * | 2001-02-28 | 2002-07-23 | Protein Technologies International, Inc. | Functional food ingredient |
| GB2375340B (en) * | 2001-05-10 | 2003-09-10 | Croda Int Plc | Gelatin substitute |
| KR100564504B1 (ko) * | 2001-08-23 | 2006-03-29 | 디에스엠 아이피 어셋츠 비.브이. | 안정화된 카로티노이드 조성물 |
-
2004
- 2004-03-24 KR KR1020057018685A patent/KR101109832B1/ko not_active Expired - Fee Related
- 2004-03-24 AT AT04722828T patent/ATE455471T1/de not_active IP Right Cessation
- 2004-03-24 ES ES04722828T patent/ES2339661T3/es not_active Expired - Lifetime
- 2004-03-24 CN CN2013100747960A patent/CN103181566A/zh active Pending
- 2004-03-24 DE DE602004025212T patent/DE602004025212D1/de not_active Expired - Lifetime
- 2004-03-24 JP JP2006504839A patent/JP4716982B2/ja not_active Expired - Fee Related
- 2004-03-24 US US10/551,197 patent/US20060257453A1/en not_active Abandoned
- 2004-03-24 EP EP04722828A patent/EP1608237B1/en not_active Expired - Lifetime
- 2004-03-24 CN CNA2004800092120A patent/CN1809286A/zh active Pending
- 2004-03-24 WO PCT/EP2004/003110 patent/WO2004086882A1/en not_active Ceased
-
2011
- 2011-11-11 US US13/294,676 patent/US20120059070A1/en not_active Abandoned
-
2013
- 2013-05-06 US US13/887,608 patent/US20130253055A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892727A (en) * | 1985-07-24 | 1990-01-09 | Societe Anonyme Dite: L'oreal | Cosmetic or dermopharmaceutical compositions containing a powder of sweet lupine seeds essentially free of alkaloids |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008089735A1 (de) * | 2007-01-23 | 2008-07-31 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Wasserhaltiges pflanzliches proteinpräparat und verfahren zur herstellung desselben |
| EP2112888B1 (de) | 2007-01-23 | 2016-06-22 | Prolupin GmbH | Wasserhaltiges pflanzliches proteinpräparat und verfahren zur herstellung desselben |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101109832B1 (ko) | 2012-02-17 |
| ATE455471T1 (de) | 2010-02-15 |
| US20130253055A1 (en) | 2013-09-26 |
| CN103181566A (zh) | 2013-07-03 |
| DE602004025212D1 (de) | 2010-03-11 |
| JP2006521798A (ja) | 2006-09-28 |
| EP1608237B1 (en) | 2010-01-20 |
| US20120059070A1 (en) | 2012-03-08 |
| KR20050113272A (ko) | 2005-12-01 |
| US20060257453A1 (en) | 2006-11-16 |
| JP4716982B2 (ja) | 2011-07-06 |
| ES2339661T3 (es) | 2010-05-24 |
| WO2004086882A8 (en) | 2004-12-23 |
| CN1809286A (zh) | 2006-07-26 |
| EP1608237A1 (en) | 2005-12-28 |
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