WO1997010050A1 - Surface-active composition - Google Patents
Surface-active composition Download PDFInfo
- Publication number
- WO1997010050A1 WO1997010050A1 PCT/EP1996/003930 EP9603930W WO9710050A1 WO 1997010050 A1 WO1997010050 A1 WO 1997010050A1 EP 9603930 W EP9603930 W EP 9603930W WO 9710050 A1 WO9710050 A1 WO 9710050A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acetone
- extraction
- composition
- residue
- active
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000000605 extraction Methods 0.000 claims abstract description 34
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 29
- 235000007319 Avena orientalis Nutrition 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000839 emulsion Substances 0.000 claims description 19
- 244000075850 Avena orientalis Species 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- -1 aliphatic alcohols Chemical class 0.000 claims description 12
- 235000004213 low-fat Nutrition 0.000 claims description 12
- 235000013339 cereals Nutrition 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- FROLUYNBHPUZQU-IIZJPUEISA-N (2R,3R,4S,5R)-2-(hydroxymethyl)-6-[3-[3-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropoxy]propoxy]oxane-3,4,5-triol Chemical compound OC[C@H]1OC(OCCCOCCCOC2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O FROLUYNBHPUZQU-IIZJPUEISA-N 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 9
- 239000000401 methanolic extract Substances 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 4
- 239000004088 foaming agent Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000003811 acetone extraction Methods 0.000 claims description 3
- 235000013351 cheese Nutrition 0.000 claims description 3
- 235000015036 low fat salad dressings Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 235000015173 baked goods and baking mixes Nutrition 0.000 claims description 2
- 235000008429 bread Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 3
- 238000002386 leaching Methods 0.000 claims 1
- 241000209761 Avena Species 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 17
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000001804 emulsifying effect Effects 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 101710199724 Ornithine aminotransferase 1 Proteins 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- QUZHZFAQJATMCA-UHFFFAOYSA-N Monogalactosyldiglyceride Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCC=CCC)COC1OC(CO)C(O)C(O)C1O QUZHZFAQJATMCA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 235000010958 polyglycerol polyricinoleate Nutrition 0.000 description 2
- 239000003996 polyglycerol polyricinoleate Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- 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
- C09K23/56—Glucosides; Mucilage; Saponins
-
- 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
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/36—Vegetable material
-
- 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
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0056—Spread compositions
-
- 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
- A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/60—Salad dressings; Mayonnaise; Ketchup
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/60—Salad dressings; Mayonnaise; Ketchup
- A23L27/66—Use of milk products or milk derivatives in the preparation of dressings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
-
- 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
Definitions
- the present invention relates to a new, natural surface- active composition, in particular for use as an emulsifier and/or foaming agent in food products and to methods for preparing the same.
- natural means "originating from a natural source”, such as plants.
- W/O emulsions require oil-soluble or lipophilic emulsifiers
- O/W emulsions need water-soluble emulsifiers.
- the latter emulsifiers are quite abundantly available from natural sources, but natural lipophilic emulsifiers are far less widespread.
- W/O emulsifiers Saturated and unsaturated monoglycerides. These can stabilize fairly dilute emulsions but not concentrated emulsions.
- a dilute emulsion is an emulsion with relatively little disperse phase, like margarine, which is a water-in-oil emulsion containing only about 16% water.
- Concentrated emulsions have a large disperse phase content, such as the low fat spreads which contain 40% water or more.
- Other common lipophilic emulsifiers are polyglycerol polyricinoleate esters, also known under the brandname Admul WO TM (E476) , which is very effective in stabilizing concentrated water-in-oil emulsions.
- Admul WOLTM The major drawback of Admul WOLTM is that it is not considered natural.
- Oat oil is produced by extraction of oats with a food permitted extraction liquid, preferably an aliphatic alcohol, particularly isopropanol.
- Oat oil contains oat glycolipids.
- a food permitted extraction liquid preferably an aliphatic alcohol, particularly isopropanol.
- Oat oil contains oat glycolipids.
- said oily substance with surface activity may be obtained in one step from oats employing an extraction with supercritical carbon dioxide and evaporating the extraction liquid, a technique described in Stahl, E., Quirin, K.-W., Gerard, D., Ver Whyte Gase Kunststoff Extratement und Raf filiation, Springer Verlag, Berlin, 1988.
- the invention thus relates to a surface-active, acetone soluble composition obtainable by solvent extraction from cereals.
- the composition may be obtained by a process comprising extracting cereals, preferably oats, as source material using successive extraction steps and employing as extraction liquids A. one or more polar extraction liquids,
- the invention comprises the use of such composition as emulsifier and foaming agent, and foods in which such composition has been incorporated.
- the process of the invention is applicable on cereals in general, but, preferably, oats are used as source material.
- oats are used as source material.
- an emulsifying substance is isolated from oat oil, by treating the oily substance left after drying the methanol extract with a proper extraction liquid, particularly acetone.
- acetone-insoluble material of the extraction as emulsifier, which like Admul WOLTM (76 wt.% of hydroxy fatty acids) is characterized by a considerable amount of hydroxy fatty acids, while the acetone washings remain undiscussed.
- the present invention is based on the surprising finding that it is the acetone- soluble material of the methanol extract (containing little hydroxy fatty acids) which has superior surface activity and shows excellent emulsifying properties.
- the invention comprises the use of any extracting liquid which can substitute acetone in the extraction process, such as mixtures of methanol and dichloromethane, as far as its enables the extraction of the acetone soluble fraction which is essential for the surface activity.
- the acetone extraction usually follows the initial extraction of cereals consisting of one or more successive extractions with a polar extraction liquid, but it may also be the initial cereals extraction step.
- the acetone soluble part may be caravanied by different other substances .
- Preferred polar extraction liquids are aliphatic alcohols, more preferably methanol and isopropanol, and supercritical carbon dioxide.
- the main component of the found surface-active composition has been identified as digalactosyl diglyceride (DGDG) .
- the invention comprises acetone soluble, surface active compositions, obtainable by solvent extraction containing at least 50 wt.% DGDG and, preferably, containing at least 70 wt.% DGDG.
- Other co-extracted components possibly are fatty acid esters of sterol glucoside, hexose glycerides and glycophospholipids .
- Each individual component does not show substantial emulsifying activity when used separately, but compositions containing two or more of them are very effective as emulsifier.
- Admul WOLTM was considered to be an unsurpassed emulsifier for low calorie oil (emulsion of 70% water-in- oil) , low fat salad dressing, low fat cheese (a duplex emulsion of water-in-oil-in-water) and low fat spreads with a high amount (at least 60 wt.%) of dispersed water.
- the invented emulsifier is powerful enough to stabilize even concentrated water-in-oil emulsions.
- the acetone soluble surface active substance was found to equal and in specific cases even to surpass Admul WOL as a stabiliser of 40 wt.% fat W/O emulsions.
- the invention comprises use of the found surface-active composition as defined hereinbefore as an emulsifier, particularly as a lipophilic emulsifier for preparing water-in-oil emulsions and more particularly as a lipophilic emulsifier in low fat products, preferably products selected from the group consisting of low fat cheese, low fat spread, very low fat spread, low calorie oil and low fat salad dressing.
- the invention comprises too food compositions in which a surfactant composition as defined hereinbefore has been incorporated, preferably when the food composition is an emulsion or a bakery product.
- Food compositions preferably contain a maximum of 30 wt.% of fat, more preferably a maximum of 20 wt.% of fat, still more preferably a maximum of 13 wt.% of fat.
- the found composition is used as a foaming agent, suitable in bread making processes.
- Oat oil was prepared according to the procedure as described in several references (Forssel et al. , Fat Sci. Technol . 94, 335 (1992) ; Jayasinghe et al . , J. Dispersion Sci. Techn. 12, 443 (1991) ; PCT/GB88/00321; and EP-0 371 601) .
- One kg of rolled oats was stirred with 2.5 1 of isopropanol at 75°C for 2.5 h. The liquid was decanted and left overnight at room temperature for any solid residue to settle. After filtration of the almost clear supernatant and evaporation of the isopropanol, 75 ml of an oily residue (oat oil) was obtained.
- This oil which contained some undissolved material, was extracted with 300 ml of methanol for 5 h at room temperature, resulting in a three- layer system.
- the bottom layer which had an oily appearance, and the emulsion-like middle layer were discarded.
- From the top layer the methanol was evaporated yielding 13.5 g of viscous lipids of partly crystalline appearance.
- This residue denoted as IPA/MeOH extract, is equivalent to NEFO, the "natural emulsifier from oats", known from PCT/GB88/00321 and EP 0 371 601. It contained 25 wt.% of phospholipids.
- the emulsifying activity of surface active substances was determined as follows: a dispersion of 40 vol .% of water in oil was prepared, containing 1 wt.% of emulsifier, which was either the IPA/MeOH extract or the IPA/MeOH/Acetone extract or Admul WOLTM or Dimodan LSTM. According to Lucassen-Reynders & Kuijpers, Colloids & Surfaces 6_5, 175 (1992)) the drop size of the resulting emulsion, both initially and after one day was measured. These values indicate the emulsifier and stabilizer performance.
- Emulsifier performance is measured by the initial drop size, while stabilization appears from the slow increase of average drop size in a quiescent emulsion during one day. Both the original IPA/MeOH extract and the IPA/MeOH/acetone extract appeared to be soluble in sunflower oil
- the surface active priciple isolated according to example 1 was found to contain at least four components, of which one was identified as digalactosyl diglyceride (DGDG) .
- the other three components produced TLC spots located between the reference substances monogalactosyl diglyceride (MGDG) and DGDG. These were believed to be a sterol glucoside fatty acid ester, a hexose glyceride other than DGDG and a glycophospholipid.
- Admul WOLTM and the insoluble residue of the acetone extraction as referred to in EP 0 371 601 are reported to contain a high amount of hydroxy fatty acids, Admul WOLTM: 76 wt.% on total fatty acid content.
- a two-kg sample of a 40 wt.% fat spread was prepared, employing a Votator consisting of two surface scraped heat exchangers and a pin stirrer, using as ingredients
- Admul WOLTM and "OAT 1" As emulsifiers were used Admul WOLTM and "OAT 1". The ingredients were combined into a water continuous pre- emulsion of 45°C and were subjected to common inversion processing in a Votator system. The "OAT 1" containing spread showed good spreadability, possessed acceptable oral melt and a water distribution which was even better than the Admul WOLTM containing spread, which exhibited some free water.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU69879/96A AU6987996A (en) | 1995-09-14 | 1996-09-09 | Surface-active composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95202493.3 | 1995-09-14 | ||
EP95202493 | 1995-09-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997010050A1 true WO1997010050A1 (en) | 1997-03-20 |
Family
ID=8220637
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/003930 WO1997010050A1 (en) | 1995-09-14 | 1996-09-09 | Surface-active composition |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU6987996A (en) |
WO (1) | WO1997010050A1 (en) |
ZA (1) | ZA967707B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1043016A1 (en) * | 1999-03-30 | 2000-10-11 | Sodic Sa | A plant extract based on glycerides, a method for the preparation of this extract and a cosmetic composition containing the same |
WO2010104444A1 (en) | 2009-03-11 | 2010-09-16 | Swedish Oat Fiber Ab | Method for separating neutral and polar lipids and an oil rich in polar lipids |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2400552A1 (en) * | 1977-08-19 | 1979-03-16 | Larsson Kare | Sepg. polar lipid(s) from non-polar lipid(s) for use as food additives - by mixing with water a lipid mixt. extracted from cereals, and centrifuging |
WO1983003425A1 (en) * | 1982-04-01 | 1983-10-13 | John Phillip Friedrich | Supercritical co2 extraction of lipids from lipid-containing materials |
EP0371601A2 (en) * | 1988-10-29 | 1990-06-06 | Cadbury Schweppes Plc | Surfactant |
EP0590203A1 (en) * | 1992-09-30 | 1994-04-06 | Unilever N.V. | Ultra low fat spread without thickening agent |
WO1995020943A1 (en) * | 1994-02-04 | 1995-08-10 | Scotia Lipidteknik Ab | Oil-in-water emulsions |
-
1996
- 1996-09-09 WO PCT/EP1996/003930 patent/WO1997010050A1/en active Application Filing
- 1996-09-09 AU AU69879/96A patent/AU6987996A/en not_active Abandoned
- 1996-09-12 ZA ZA9607707A patent/ZA967707B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2400552A1 (en) * | 1977-08-19 | 1979-03-16 | Larsson Kare | Sepg. polar lipid(s) from non-polar lipid(s) for use as food additives - by mixing with water a lipid mixt. extracted from cereals, and centrifuging |
WO1983003425A1 (en) * | 1982-04-01 | 1983-10-13 | John Phillip Friedrich | Supercritical co2 extraction of lipids from lipid-containing materials |
EP0371601A2 (en) * | 1988-10-29 | 1990-06-06 | Cadbury Schweppes Plc | Surfactant |
EP0590203A1 (en) * | 1992-09-30 | 1994-04-06 | Unilever N.V. | Ultra low fat spread without thickening agent |
WO1995020943A1 (en) * | 1994-02-04 | 1995-08-10 | Scotia Lipidteknik Ab | Oil-in-water emulsions |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1043016A1 (en) * | 1999-03-30 | 2000-10-11 | Sodic Sa | A plant extract based on glycerides, a method for the preparation of this extract and a cosmetic composition containing the same |
US6576266B1 (en) | 1999-03-30 | 2003-06-10 | Sodic Sa | Plant extract based on glycerides, a method for the preparation of this extract and a cosmetic composition containing the same |
WO2010104444A1 (en) | 2009-03-11 | 2010-09-16 | Swedish Oat Fiber Ab | Method for separating neutral and polar lipids and an oil rich in polar lipids |
US8865923B2 (en) | 2009-03-11 | 2014-10-21 | Swedish Oat Fiber Ab | Method for separating neutral and polar lipids and an oil rich in polar lipids |
EP3816265A1 (en) | 2009-03-11 | 2021-05-05 | Swedish Oat Fiber AB | Method for separating neutral and polar lipids and an oil rich in polar lipids |
Also Published As
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AU6987996A (en) | 1997-04-01 |
ZA967707B (en) | 1998-03-12 |
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