IE910191A1 - A non-liquid fatty product containing water and at least one¹polyunsaturated fatty acid and a process for the production¹of same - Google Patents
A non-liquid fatty product containing water and at least one¹polyunsaturated fatty acid and a process for the production¹of sameInfo
- Publication number
- IE910191A1 IE910191A1 IE019191A IE19191A IE910191A1 IE 910191 A1 IE910191 A1 IE 910191A1 IE 019191 A IE019191 A IE 019191A IE 19191 A IE19191 A IE 19191A IE 910191 A1 IE910191 A1 IE 910191A1
- Authority
- IE
- Ireland
- Prior art keywords
- percent
- weight
- fatty
- water
- double bonds
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0092—Mixtures
-
- 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
- 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
- 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
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
-
- 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
- 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
- A23L33/12—Fatty acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Mycology (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
Abstract
A non-liquid fatty product containing an inert gas, at least one polyunsaturated fatty acid, water and optionally an antioxidant and a process for the production of same wherein an inert gas is whipped into an emulsion wherein the oil phase is initially softened by heating which oil phase contains at least 1 percent by weight of a polyunsaturated fatty acid of the n-3 series comprising at least four double bonds or at least 0.5 percent by weight of a polyunsaturated fatty acid of the n-6 series comprising at least three double bonds and wherein the emulsion contains at least 1 percent by weight of oxygen-deficient water. Thus, protection of the fatty product against oxidation is accomplished and at the same time a suitable texture is imparted thereto.
Description
The present Invention relates to a non-liquid fatty product containing an Inert gas, at least one polyunsaturated fatty acid, water, and optionally an antioxidant.
In a known process (Gillies, M.T., Shortenings, Margarines and Food Oils, Noyes Data Corporation, New Jersey, 1974, 333 pp.) for the production of a optionally foamy fatty product of the kind described above (e.g. various types of shortening and whipped margarine) air or an Inert gas 1$ whipped Into a heated liquid fat or liquid water10 1n-o1l emulsion.
Thus, subsequent to suitable cooling and kneading a product having a soft texture at low temperatures (0*C-5*C) Is obtained. Moreover, the whipping of air Into fats for use as shortening serves to impart to the product an opaque, margarine-like appearance. The whipping of air or Inert gas Into margarine is effected 1n order to Improve the frying properties and the organoleptic properties of the margarine and to protect 1t from the formation of mould.
Apart from being used for baking and frying, margarine 1s used as a spread and for this particular purpose It 1s often produced from oils containing polyunsaturated fatty acids which essentially consist of linoleic add comprising two double bonds (18:2 n-6) and which less frequently have a low content of a-11nolen1c add comprls
1ng three double bonds (18:3 n-3).
A disadvantage of the disclosed water-1n-o1l emulsion 1s that oxygen 1$ Introduced Into the fatty product 1n the water phase. Dissolved oxygen 1n the water phase reduces the shelf life of fatty products containing polyunsaturated fatty adds considerably, because polyunsaturated fatty adds having more than two double bonds are vary easily oxidized, and the existing technology does not disclose how to produce a margarine emulsion 1n an oxygen-deficient environment. Thus, up till now, 1t has been Impossible to produce a non-liquid fatty spread having a long shelf life and an Increased content of polyunsaturated fatty adds of the n-3 series comprising at least 4 double bonds or of the n-6 series comprising at least 3 double bonds.
IE 91191
This 1$ unfortunate since a series of tests carried out In the past 20 years or so (Dyerberg, 0., L1nolenate-der1ved Polyunsaturated Fatty Acids and Prevention of Atherosclerosis, Nutrition Reviews, vol. 44, No. 4, 1986, pp 125-134) have shown that a dally Intake of a few grammes of l.a. polyunsaturated fatty adds comprising 5 double bonds (20:5 n-3 and 22:5 n-3), which are mainly present In marine oils, particularly fish oils, and 1n phyto-plankton and algae, reduces the cholesterol content of the blood and the risk of developing heart and vascular disorders by virtue of their conver10 s1on Into the physiologically active prostaglandin E3 (PGEj).
The Intake of linoleic acid (18:2 n-6) alone, which has two double bonds and which Is converted slowly In the organism Into the physiologically active prostaglandins PGEj and PGE2, 1s frequently not sufficient to obtain a corresponding effect because the first step which comprises the conversion of linoleic acid Into ?-11no1en1c add Is catalysed by the enzyme 6-6-desaturase which frequently has low activity In man (Hassam, A.G., The Role of Evening Primrose Oil Nutrition and Disease., On: The Role of Fats In Human Nutrition,
Ellis Horwood Limited, CMcester, 1985, pp 84-100). γ-Llnolenlc add (18:3 n-6), . which 1$ present 1n vegetable oils such as evening primrose oil, borage oil and black-currant seed oil, Is therefore a more efficient precursor In the biosynthesis of PGEj and PGE^ (Gurr, M.O., Role of Fats 1n Food and Nutrition, Elsevier Applied Science
Publishers, London New York, 1984, 170 pp), and this fact has led to a growing interest 1n the use of y-llnolenlc add 1n 1.a. food products.
However, 1t has not been possible to use commercially an amply occurlng raw material, such as fish oil and In particular sand eel oil having a high content (about 15 percent by weight to about 30 percent by weight) of n-3 fatty adds and vegetable oils, such as the above mentioned, having a high content (about 14 percent by weight to about 33 percent by weight) of n-6 fatty adds, In their unhydrogenated state for the sake of the shelf life thereof, and thus the desirable nutritive and wholesome effects thereof have not been fully utilized.
It 1s the object of the present Invention to produce a stable and
IE 91191 physiologically active fatty product of the kind described above.
This object 1s achieved with the fatty product of the Invention, which 1s characterized In that 1t Is a water-1n-o11 emulsion or an oil-1n-water emulsion containing at least 1 percent by weight of oxygen-deficient water and wherein the oil phase contains at least 1 percent by weight of a polyunsaturated fatty add of the n-3 series comprising at least four double bonds and/or at least 0.5 percent by weight of a polyunsaturated fatty acid of the n-6 series comprising at least three double bonds. The water 1s rendered oxygen-deficient by e.g. sparging with Inert gas, boiling out or by naturally contain Ing Inert gas.
By oxygen-deficient Is understood that the amount of dissolved oxygen 1n the used water or water phase for the product of the Invention Is not sufficient to cause any substantial oxidation of the polyunsaturated fatty acids contained In said product.
It 1s surprisingly found that the highly unsaturated fatty acids are stabilized 1n a fatty product wherein the water phase 1s oxygendeficient and Into which Inert gas and optionally a suitable amount of antioxidants have been whipped» thus imparting to the final product a peroxide number according to the IUPAC (2.501) of less than about 1 meq/kg.
Furthermore, the addition of preservatives, such as potassium sorbate, and antioxidants, such as alkyl gallates, ascorbyl fatty acid esters and tocopherols, affords further Improvement of the durability of the products according to the Invention and, add1· tionally, the antioxidants also aid 1n the protection of tho fatty adds against oxidation occurring In the organism.
In one preferred embodiment of the Invention mineral water, which 1s naturally carbonized water, 1$ used for the water phase, which may further contain salt, flavours, milk solids, and thickeners, such as gelatin, alginate, and guar gum. An emulsion Is prepared by adding the water phase to a mixture of heated fats and oils containing an emulsifier, such as a monodlglycerlde of a fatty add or a lec1thlne, and subsequently whipping the emulsion with an Inert gas In an oxygenfree atmosphere. The whipped emulsion, which 1s of margaIE 91191 r1ne type, 1s cooled and packed.
In fatty products of the Invention consisting of a water-ln-oU emulsion the solid fat proportion at the storage temperature of the total fat and oil content is preferably not less than 10 percent by weight In order to obtain a non-Hqu1d product and retain the wh1pped-1n Inert gas. Alternatively the oil phase can be reduced by using a suitable amount of thickener and/or gelling agent to obtain a non-liquid product.
In another preferred embodiment of the Invention an o1l-1n-water emulsion 1s prepared by adding oil to a mixture of Ng-sparged water and emulsifier. Vinegar may finally be added to obtain a mayonnaiselike product, which preferably Is packed 1n air-tight containers.
For products of the Invention consisting of an o1l-1n-water emulsion, such as mayonnaise, wherein the oil raw material 1$ liquid at storage temperature, no solid fat Is necessary 1n order to retain the wh1pped-1n Inert gas.
A preferred content of Inert gas, such as Ng, 1n the fatty product corresponds to 15 percent by volume.
The Invention further relates to a process for the production of a non-liquid fatty product containing an Inert gas, at least one polyunsaturated fatty acid, water and optionally an antioxidant, wherein the Inert gas 1s whipped into an o11-1n-water emulsion or a water1n-o1l emulsion wherein the oil phase comprises a mixture of fatty substances which was Initially softened by heating and wherein the product thus produced Is cooled. The process 1s characterized 1n using a mixture of fatty substances containing at least 1 percent by weight of a polyunsaturated fatty acid of the n-3 series comprising at least four double bonds and/or at least 0.5 percent by weight of a polyunsaturated fatty acid of the n-6 series comprising at least three double bonds and at least 1 percent by weight of oxygendeflclent water.
The products produced 1n the process according to the Invention may be packaged like similar products containing polyunsaturated fatty
IE 91191 adds comprising two double bonds and having a low content of polyunsaturated fatty adds comprising three or more double bonds.
In the following examples the Invention will be described In further detail.
Example—1
A water phase (10 percent by weight of mineral water (naturally carbonized water)), 0.02 percent by weight of flavouring 2807, and antioxidants (propylgallate 100 ppm, ascorbylpalmitate 43 ppm, a-tocopherol 1000 ppm) Is added while stirring to a preheated (40°C-80°C) mixture of 89.6 percent by weight of fat blend (10 parts soya m.p. 41°C, 40 parts soya m.p. 35°C, 30 parts soya oil, and 20 parts fish ¢11), 0.2 percent by weight og soya lecithin, 0.2 percent by weight of OIMODAN PV (mono- and diglyceride emulsifier) and 0.02 percent by weight of flavouring 3090. The water-ln-oll emulsion having a temperature of about 45°C Is then cooled to 4°C by passage through a one-p1pe pilot plant of the Gerstenberg and Agger type. Gaseous nitrogen 1s introduced Into the suction part of the highpressure pump via a distribution nozzle to obtain a final product having a nitrogen content of 15 percent by volume. The product Is filled Into cups Immediately upon the pipe cooler treatment. The final product 1s stored at a maximum temperature of 10°C.
The fatty acid composition of the fish oil Is as follows:
Fall.Y add percent bv weight
14:0 8.0 15:0 0.3 16:0 17.4 16:1 9.5 16:2 0.6 18:0 1.2 18:1 9.1
IE 91191
Fattv add P9r
C 16:4 C 18:2 C 18:3f20:l C 18:4+n-3 0.5 1.9 8.9 3.9 C 22:1 13.3 C 20:4 n-3 0.7 10 C 20:5 n-3 10.5 C 24:1 1.6 C 22:4 0.8 C 22:5 n-3 0.8 15 C 22:6 n-3 9.4
In an accelerated storage experiment this product was stored at 25°C for 4 weeks without developing any off-flavour. The peroxide number was below 1 meq/kg after 4 weeks. In Denmark the accepted maximum period of storage for vegetable oil margarines Is 7 weeks at temperatures below 10°C.
ExamplftJ
A water phase (10 percent by weight of boiled mineral water, 0.02 percent by weight of flavouring 2807, and antioxidants (propylgallate 100 ppm, ascorbylpalmitate 43 ppm, Λ-tocopherol 1000 ppm) 1s added while stirring to a preheated (40°C-80°C) mixture of 89.6 percent by weight of fat blend (10 parts soya m.p. 41°C, 40 parts soya m.p. 35°C, 30 parts soya oil, and 20 parts fish oil), 0.2 percent by weight of soya lecithin, 0.2 percent by weight of DIMODAN PV (mono- and diglyceride emulsifier) and 0.02 percent by weight of flavouring 3090. The water-in-oll emulsion having a temperature of about 45°C 1$ then cooled to 4°C by passage through a one-pipe pilot plant of the Gerstenberg and Agger type. Gaseous nitrogen 1s Introduced Into the suction part of the high-pressure pump via a distribution nozzle to obtain a final product having a nitrogen content of 15 percent by weight. The product 1s filled into airtight plastic cups Immediately upon the pipe cooler treatment. The final product
IE 91191
Is stored at a maximum temperature of 10°C.
The fish oil had the same composition as 1n Example 1.
In an accelerated storage experiment this product was stored at 25°C for 4 weeks without developing any off-flavour. The peroxide number was below 1 meq/kg after 4 weeks. In Denmark the accepted maximum period of storage for vegetable oil margarines Is 7 weeks at temperatures below 10°C.
Examplfi-3
A mayonnaise-type product 1s produced from the following Ingredients:
Ingredients Percent bv weight
Fish on* 10,0 * same composition Rapeseed oil 70,0 as 1n Examples 1 20 Vinegar 1,5 and 2, Egg yolks 4,0-6,0 Thickener 0,3 Salt 0,3 Flavour 0,02 25 Water, preservatives, etc., up to 100
Mineral water Is poured Into a mayonnaise plant, emulsifying turbine, or the like and egg yolks are added. Then the oil Including dispersed thickener, salt, and preservatives are added continuously. Finally vinegar 1s added. The product 1s whipped with Inert gas before being packaged in a1r-t1ght bottles.
In an accelerated storage experiment this product was stored at 25°C for 4 weeks without developing any off-flavour.
Claims (12)
1. A non-liquid fatty product containing an Inert gas, at least one polyunsaturated fatty add, water and optionally an antioxidant, characterized 1n that the fatty product 1$ a water-lnoU emulsion or an o1l-1n-water emulsion containing at least 1 percent by weight of oxygen-deficient water and wherein the oil phase contains at least 1 percent by weight of a polyunsaturated fatty acid of the n-3 series comprising at least four double bonds and/or at least 0.5 percent by weight of a polyunsaturated fatty add of the n-6 series comprising at least 3 double bonds.
2. A fatty product according to claim 1, characterized In that It comprises at least 1 percent by weight of a polyunsaturated fatty add of the n-3 series comprising 5 double bonds, preferably eicosapentaenoic add (10:5 n-3).
3. A fatty product according to claim 1, characterized In that it comprises at least 0.5 percent by weight of e polyunsaturated fatty add of the n-6 series comprising at least three double bonds, preferably γ-Hnolenlc add (18:3 n-6).
4. A fatty product according to cl aim 1, characterized In that 1t contains from about 10 percent by weight to about 85 percent by weight of refined fish oil. 5. Softened by heating and wherein the product thus produced Is cooled, characterized In using a mixture of fatty substances containing at least 1 percent by weight of a polyunsaturated fatty acid of the n-3 series comprising at least four double bonds and/or at least 0.5 percent by weight of a polyunsaturated fatty add of
5. A fatty product according to claim 1, characterized 1n that It comprises a water-ln-dl emulsion 1n which the water phase constitutes from 1 to 80 percent by weight and 1n which the oil phase constitutes from 20 to 99 percent by weight, the oil phase containing at least 10 percent by weight of solid fat. I
6. A fatty product according to claim 1, characterized 1n that It comprises an o1l-1n-water emulsion In which the water phase constitutes from 1 to 80 percent by weight and In which the oil phase constitutes from 20 to 99 percent by weight.
7. A process for the production of a non-11qu1d fatty product conIE 91191 talnlng an Inert gas, at least one polyunsaturated fatty add, water and optionally an antioxidant, wherein the Inert gas 1s whipped Into an o1l-1n-water emulsion or a water-in-oll emulsion wherein the oil phase comprises a mixture of fatty substances which was Initially
8. Process according to claim 7, characterized In using a mixture of fatty substances containing at least 0.5 percent 15 by weight of polyunsaturated fatty adds of the n-6 series comprising at least 3 double bonds, preferably γ-Hnolenlc acid.
9. Process according to claim 7, characterized 1n using a mixture of fatty substances containing from about 10 to 20 about 85 percent by weight of refined fish oil.
10. A non-liquid fatty product according to claim 1, substantially as hereinbefore described and exemplified. 10 the n-6 series comprising at least 3 double bonds and at least 1 percent by weight of oxygen-deficient water.
11. A process according to claim 7 for the production of a non-liquid fatty product, substantially as hereinbefore described and exanplified. JO
12. A non-liquid fatty product, whenever produced by a process claimed in a preceding claim.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK016990A DK164685C (en) | 1990-01-22 | 1990-01-22 | NON-LIQUID FAT PRODUCT CONTAINING WATER AND AT LEAST ONE POLYUM Saturated FAT ACID AND PROCEDURE FOR THE SAME PRODUCTION |
Publications (1)
Publication Number | Publication Date |
---|---|
IE910191A1 true IE910191A1 (en) | 1991-07-31 |
Family
ID=8090551
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE019191A IE910191A1 (en) | 1990-01-22 | 1991-01-21 | A non-liquid fatty product containing water and at least one¹polyunsaturated fatty acid and a process for the production¹of same |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0512032A1 (en) |
AU (1) | AU7214091A (en) |
CA (1) | CA2074356A1 (en) |
DK (1) | DK164685C (en) |
IE (1) | IE910191A1 (en) |
PT (1) | PT96549A (en) |
WO (1) | WO1991010367A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK0612346T3 (en) * | 1991-11-15 | 1995-08-07 | Hoffmann La Roche | Stabilization of marine oils |
US7799365B2 (en) * | 2001-04-06 | 2010-09-21 | Burnbrae Farms Limited | Liquid egg composition including fish oil with omega-3 fatty acid |
US7662421B2 (en) | 2002-03-18 | 2010-02-16 | Q.P. Corporation | Container-packed, oil-in-water type emulsified food product and method for manufacture thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR573718A (en) * | 1922-11-23 | 1924-06-28 | Process for the treatment of fats and oils | |
GB8706711D0 (en) * | 1987-03-20 | 1987-04-23 | Unilever Plc | Edible plastic product |
US4764392A (en) * | 1987-04-01 | 1988-08-16 | Q.P. Corporation | Margarine containing fish oil |
GB8718523D0 (en) * | 1987-08-05 | 1987-09-09 | Unilever Plc | Marine/vegetable oil blend |
FR2623692B1 (en) * | 1987-11-30 | 1991-05-03 | Vernin Jean Gilles | NEW DIETETIC OIL |
DK162621C (en) * | 1989-04-27 | 1992-04-13 | Jon Katborg | FOOD FAT PRODUCT AND PROCEDURE FOR PRODUCING THE SAME |
-
1990
- 1990-01-22 DK DK016990A patent/DK164685C/en active
-
1991
- 1991-01-21 IE IE019191A patent/IE910191A1/en unknown
- 1991-01-22 PT PT96549A patent/PT96549A/en not_active Application Discontinuation
- 1991-01-22 WO PCT/DK1991/000017 patent/WO1991010367A1/en not_active Application Discontinuation
- 1991-01-22 AU AU72140/91A patent/AU7214091A/en not_active Abandoned
- 1991-01-22 CA CA002074356A patent/CA2074356A1/en not_active Abandoned
- 1991-01-22 EP EP91903613A patent/EP0512032A1/en not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
EP0512032A1 (en) | 1992-11-11 |
PT96549A (en) | 1991-10-15 |
AU7214091A (en) | 1991-08-05 |
DK16990D0 (en) | 1990-01-22 |
CA2074356A1 (en) | 1991-07-23 |
DK164685B (en) | 1992-08-03 |
DK164685C (en) | 1992-12-21 |
DK16990A (en) | 1991-07-23 |
WO1991010367A1 (en) | 1991-07-25 |
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