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GB2280449A - "A method for preparing an edible water-in-oil emulsion" - Google Patents

"A method for preparing an edible water-in-oil emulsion" Download PDF

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Publication number
GB2280449A
GB2280449A GB9413405A GB9413405A GB2280449A GB 2280449 A GB2280449 A GB 2280449A GB 9413405 A GB9413405 A GB 9413405A GB 9413405 A GB9413405 A GB 9413405A GB 2280449 A GB2280449 A GB 2280449A
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oil
water
oil emulsion
aqueous phase
emulsion
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GB9413405D0 (en
GB2280449B (en
Inventor
John Maguire
Joseph Patrick Mcauliffe
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CHARLEVILLE RES
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CHARLEVILLE RES
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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/015Reducing calorie content; Reducing fat content, e.g. "halvarines"
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B20/00Preservation of edible oils or fats
    • A23B20/10Preservation of edible oil or fat compositions containing an aqueous phase, e.g. margarines

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Edible Oils And Fats (AREA)

Abstract

A spread is prepared from a water-in-oil emulsion, which is prepared using a margarine process, in which the fat phase of the emulsion comprises fish oil containing an antioxidant blend of ascorbyl palmitate. The aqueous phase of the emulsion is prepared without ingredients or additives which may react with, or act as a catalyst for a reaction with ascorbyl palmitate to at least retard the development of a metallic type off-flavour or fishy taste. The aqueous phase is prepared without one or more of the following ingredients or additives: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.pared

Description

"A method for preparing an edible water-in-oil emulsion" The present invention relates to a method for preparing an edible water-in-oil emulsion containing fish oil and the invention also relates to a water-in-oil emulsion containing fish oil.
Fish oil has very significant and desirable nutritional properties. It is also relatively high in omega-3 polyunsaturated fatty acids, which have been found to play a significant role in the prevention, or at least reduction in the incidence of heart disease. However, fish oil suffers from a serious disadvantage in that it deteriorates at a relatively rapid rate. To arrest the relatively rapid deterioration of fish oil, fish oil is subjected to various processes, such as, for example, refining, deodorising, and other stabilising processes, for example, treating the fish oil with antioxidants and the like. Such processes, while they overcome to a large extent the problem of deterioration of the fish oil, unfortunately, significantly affect the nutritional properties, and in particular, the omega-3 polyunsaturated fatty acids content of the fish oil.In general, such processes tend to destroy the omega-3 polyunsaturated fatty acids. Thus, the beneficial effects of fish oil are effectively eliminated.
Processes for treating fish oil to prevent or to at least retard deterioration of the fish oil, while at the same time minimising the adverse effects on the nutritional properties, and in particular, on the omega-3 polyunsaturated fatty acids content of the fish oil require the addition to the fish oil of an antioxidant or an antioxidant blend. Such an antioxidant or antioxidant blend may comprise ascorbyl palmitate. It has, however, been found that fish oil containing such an antioxidant blend of ascorbyl palmitate when included in the fat phase of an edible water-in-oil emulsion, such as, for example, a spread, causes the spread to develop a metallic type off-flavour which is often described as a fishy taste.
There is therefore a need for a method for preparing an edible water-in-oil emulsion containing fish oil and an antioxidant containing ascorbyl palmitate in which the development of such an off-flavour or fishy taste is avoided, or at least retarded.
There is also a need for such an edible water-in-oil emulsion.
The present invention is directed towards providing such a method and an edible water-in-oil emulsion containing fish oil.
According to the invention there is provided a method for preparing an edible water-in-oil emulsion comprising fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate, wherein the aqueous phase is prepared without ingredients or additives which may react with or act as a catalyst for a reaction with, ascorbyl palmitate to at least retard the development of a metallic type off-flavour or fishy taste. Preferably, the aqueous phase is prepared without any one or more of the following ingredients or additives: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.
In one embodiment of the invention the aqueous phase is prepared with de-ionised water. In another embodiment of the invention, a sequestrant is added to the aqueous phase for binding metal ions in the aqueous phase. Preferably, the sequestrant is selected from any one or more of the following sequestrants: citric acid and/or its salts, phosphate salts, and ethylene diamine tetra-acetic acid and/or its salts.
In another embodiment of the invention the aqueous phase is prepared with water having a relatively low calcium content, and preferably, the water comprises a very low level of calcium.
Preferably, the calcium content of the aqueous phase is less than 20 parts per million of the aqueous phase. Advantageously, the calcium content of the aqueous phase is less than 10 parts per million of the aqueous phase, and ideally, the calcium content of the aqueous phase is less than 5 parts per million of the aqueous phase. It is believed that the presence of calcium in the aqueous phase reduces the effectiveness of the sequestrant, and accordingly, by minimising the calcium content of the aqueous phase, the binding property of the sequestrant for binding metal ions is enhanced.
In another embodiment of the invention the fat phase constitutes up to 82% by weight of the water-in-oil emulsion.
Advantageously, the fat phase constitutes up to 60% by weight of the water-in-oil emulsion, and ideally, the fat phase constitutes approximately 40% by weight of the water-in-oil emulsion.
In one embodiment of the invention the fish oil containing the antioxidant constitutes up to 50% by weight of the water-in-oil emulsion, and preferably, the fish oil containing the antioxidant constitutes up to 40% by weight of the water-in-oil emulsion.
Advantageously, the fish oil containing the antioxidant constitutes up to 30% by weight of the water-in-oil emulsion, and in a preferred embodiment of the invention, the fish oil containing the antioxidant constitutes between 3% and 20% by weight of the water-in-oil emulsion. Ideally, the fish oil containing the antioxidant constitutes approximately 4% by weight of the water-in-oil emulsion.
Preferably, the fish oil is an unhardened fish oil, and in a preferred embodiment of the invention the fish oil is a fish oil sold by Roche Products Limited of Great Britain under the Trade Mark ROPUFA 30.
In another embodiment of the invention the fat phase comprises a vegetable oil, and preferably, a vegetable oil liquid at room temperature.
Preferably, the vegetable oil is selected from any one or more of the following oils: rape seed oil, soya bean oil, sun flower oil, and olive oil.
Advantageously, the fat phase comprises a hard stock oil solid at room temperature. In one embodiment of the invention the hard stock oil is a vegetable oil.
Advantageously, the hard stock oil is selected from any one or more of the following oils: hydrogenated or partly hydrogenated soya bean oil, hydrogenated or partly hydrogenated rape seed oil, hydrogenated or partly hydrogenated palm oil, hydrogenated or partly hydrogenated coconut oil, hydrogenated or partly hydrogenated palm kernel oil, a vegetable oil naturally hard at room temperature, for example, coconut oil, palm kernel oil, palm oil and fractions thereof, animal fats, for example, milk fat, tallow or lard or fractions thereof.
In a further embodiment of the invention the fat phase may also contain an emulsifier, for example, a mono and di glycerides; the fat phase may also contain colouring; flavouring and/or vitamins.
In another embodiment of the invention the aqueous phase may contain lactic acid, proteins and/or flavouring additives.
In one embodiment of the invention the water-in-oil emulsion is prepared using a margarine process.
Additionally, the invention provides an edible water-in-oil emulsion containing fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate wherein the aqueous phase is prepared without additives which may react with, or act as a catalyst for a reaction with ascorbyl palmitate to at least retard the development of a metallic type off-flavour or fishy taste. Preferably, the aqueous phase is prepared without any one or more of the following ingredients: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.
Preferably, the aqueous phase is prepared from de-ionised water, advantageously, the aqueous phase contains a sequestrant for binding metal ions in the aqueous phase, preferably, the sequestrant is selected from any one or more of the following: citric acid, and/or its salts, phosphate salts, and ethylene diamine tetra-acetic acid, and/or its salts.
In one embodiment of the invention the aqueous phase is prepared with water with a relatively low level of calcium and preferably, a very low level of calcium.
In another embodiment of the invention the fat phase constitutes up to 82% by weight of the water-in-oil emulsion, and preferably, the fat phase constitutes up to 60% by weight of the water-in-oil emulsion. Advantageously, the fat phase constitutes approximately 40% by weight of the water-in-oil emulsion.
In one embodiment of the invention the fish oil containing the antioxidant constitutes up to 50% by weight of the water-in-oil emulsion. Advantageously, the fish oil containing the antioxidant constitutes up to 40% by weight of the water-in-oil emulsion. Advantageously, the fish oil containing the antioxidant constitutes up to 30% by weight of the water-in-oil emulsion, and in a preferred embodiment of the invention, the fish oil containing the antioxidant constitutes between 3% and 20% by weight of the water-in-oil emulsion. Ideally, the fish oil containing the antioxidant constitutes approximately 4% by weight of the water-in-oil emulsion.
Additionally, the invention provides a spread prepared from the edible water-in-oil emulsion according to the invention.
Further, the invention provides a spread in which the water-inoil emulsion is prepared by a method according to the invention.
The invention will be more clearly understood from the following description of the following non-limiting examples.
Example 1 A spread is prepared from an edible water-in-oil emulsion, which is prepared from the following ingredients in the proportions by weight set out below: Fat phase refined deodorised rape seed oil 22.6% Hydrogenated soya bean oil 12.9% Dimodan OT (glycerol mono stearate) 0.5% B Carotene 0.003% Fish oil containing an antioxidant blend 4.0% Aqueous Phase De-ionised water 58.66% Sobalg FD 120 (sodium alginate) 1.20% Potassium sorbate 0.10% Citric acid 0.04% The fish oil is an unhardened fish oil containing an antioxidant blend, which antioxidant blend includes ascorbyl palmitate. In this particular embodiment of the invention the fish oil is a fish oil sold by Roche Products Limited of Great Britain under the Trade Mark ROPUFA 30.The refined deodorised rape seed oil is liquid at room temperature, and the hydrogenated soya bean oil is solid at room temperature. The de-ionised water is very low in calcium so that the calcium content of the aqueous phase is less than five parts per million of the aqueous phase.
The spread is prepared using a margarine process. The ingredients of the fat phase including the fish oil are raised to a temperature of approximately 40"C to 45"C in a mixing tank until all the fats have melted and are thoroughly mixed. The ingredients of the aqueous phase are mixed and added to the fat phase in the mixing tank and stirred to form a water-in-oil emulsion. The emulsion is then processed in a scraped surface heat exchanger and ancillary equipment to achieve pasteurisation, and is subsequently cooled and then subjected to texturising or plasticising. The spread is then packed as desired in foil, tubs or other suitable packaging.
Example 2 A spread is prepared from the following ingredients in the proportions by weight set out below using a similar method to that of Example 1: Fat ohase refined deodorised rape seed oil 22.6% Hydrogenated soya bean oil 12.9% Dimodan OT (glycerol mono stearate) 0.5% B Carotene 0.003% Fish oil containing an antioxidant blend 4.0% Aqueous ohase De-ionised water 57.16% Sobalg FD 120 (sodium alginate) 1.2% Potassium sorbate 0.1% Sodium chloride 1.5% Citric acid 0.04% Example 3 A spread is prepared from the following ingredients in the proportions by weight set out below using a similar method to that of Example 1:: Fat phase refined deodorised rape seed oil 33.69% Hydrogenated soya bean oil 19.8% Dimodan OT (glycerol mono stearate) 0.5% B Carotene 0.003% Oil soluble flavour 0.01% Fish oil containing an antioxidant blend 6.0% Aqueous phase De-ionised water 37.75% Water soluble flavour 0.005% Sodium chloride 1.2% Citric acid 0.04% Example 4 A spread is prepared from the following ingredients in the proportions by weight set out below using a similar method to that of Example 1:: Fat Phase refined deodorised rape seed oil 15.5% butterfat (anhydrous) 40.0% Dimodan OT (glycerol mono stearate) 0.5% Fish oil containing an antioxidant blend 4.0% Aqueous ohase De-ionised water 38.46% Sodium chloride 1.5% Citric acid 0.04% Example 5 A spread is prepared from the following ingredients in the proportions by weight set out below using a similar method to that of Example 1: Fat phase refined deodorised rape seed oil 3.6% Hydrogenated soya bean oil 26.0% Dimodan OT (glycerol mono stearate) 0.4% B Carotene 0.003% Fish oil containing an antioxidant blend 50.0% Aqueous phase De-ionised water 19.96% Citric acid 0.04% In Examples 2 to 5, the fish oil is identical to the fish oil used in Example 1.The spreads of Examples 2 to 5 are prepared using the margarine process similar to that described with reference to Example 1, and after texturising and plasticising the spread is packed. In each of Examples 2 to 5, the refined deodorised rape seed oil is liquid at room temperature. The deionised water is very low in calcium so that the calcium content of the aqueous phase is less than five parts per million of aqueous phase. In each of the Examples 2, 3 and 5, the hydrogenated soya bean oil is solid at room temperature. In Example 4, the butterfat is also solid at room temperature. In each of the Examples 2 to 4, a small quantity of sodium chloride is included in the aqueous phase without adverse results.
In all the examples, as can be seen, neither the aqueous phase or the fat phase contain any of the following ingredients or additives: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.
In all the examples, trace metals in the aqueous phase are kept to a minimum.
It has been found that the spreads produced according to the above examples do not develop a metallic type off-flavour nor do they develop a fishy taste. In fact, it has been found that the spreads prepared according to the examples are relatively stable.
Precisely why this is so is not fully understood, however, it is believed that by minimising the metal content of the aqueous phase considerably contributes to the stability of the spreads.
It is believed that metals present in the aqueous phase either react with ascorbyl palmitate and cause the metallic type offflavour, or alternatively, it may be that the metals present in the aqueous phase act as a catalyst for a reaction of the ascorbyl palmitate with other constituents in either the fat or aqueous phases which leads to the metallic type off-flavour.
Accordingly, the use of de-ionised water significantly minimises the metal content of the water. The addition of citric acid to the aqueous phase which acts as a sequestrant for binding any residual metal ions in the aqueous phase further reduces the effect of any remaining metals in the water. It is believed that by keeping the level of calcium in the aqueous phase to a minimum the effectiveness of the sequestrant is increased. It is also believed that by preparing the aqueous phase without whey powder, skimmed milk powder1 sodium caseinate and with relatively low levels only of sodium chloride, also minimises the possibility of a reaction with the ascorbyl palmitate which may lead to the metallic type off-flavour or fishy taste.
While the water-in-oil emulsion has been described in the examples as being a spread, it will be apparent to those skilled in the art that the edible water-in-oil emulsion may be other than a spread, for example, mayonnaise, and the like.
The invention is not limited to the examples hereinbefore described, and it will be readily apparent to those skilled in the art that other edible water-in-oil emulsions may be prepared according to the invention with other ingredients and other proportions of ingredients.

Claims (51)

1. A method for preparing an edible water-in-oil emulsion comprising fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate, wherein the aqueous phase is prepared without ingredients or additives which may react with or act as a catalyst for a reaction with, ascorbyl palmitate to at least retard the development of a metallic type off-flavour or fishy taste.
2. A method as claimed in Claim 1 in which the aqueous phase is prepared without any one or more of the following ingredients or additives: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.
3. A method as claimed in Claim 1 or 2 in which the aqueous phase is prepared with de-ionised water.
4. A method as claimed in any preceding claim in which a sequestrant is added to the aqueous phase for binding metal ions in the aqueous phase.
5. A method as claimed in Claim 4 in which the sequestrant is selected from any one or more of the following sequestrants: citric acid and/or its salts, phosphate salts, and ethylene diamine tetra-acetic acid and/or its salts.
6. A method as claimed in any preceding claim in which the aqueous phase is prepared with water having a relatively low calcium content.
7. A method as claimed in Claim 6 in which the water comprises a very low level of calcium.
8. A method as claimed in Claim 6 or 7 in which the calcium content of the aqueous phase is less than 20 parts per million of the aqueous phase.
9. A method as claimed in Claim 8 in which the calcium content of the aqueous phase is less than 10 parts per million of the aqueous phase.
10. A method as claimed in Claim 9 in which the calcium content of the aqueous phase is less than 5 parts per million of the aqueous phase.
11. A method as claimed in any preceding claim in which the fat phase constitutes up to 82% by weight of the water-in-oil emulsion.
12. A method as claimed in Claim 11 in which the fat phase constitutes up to 60% by weight of the water-in-oil emulsion.
13. A method as claimed in Claim 12 in which the fat phase constitutes approximately 40% by weight of the water-in-oil emulsion.
14. A method as claimed in any preceding claim in which the fish oil containing the antioxidant constitutes up to 50% by weight of the water-in-oil emulsion.
15. A method as claimed in Claim 14 in which the fish oil containing the antioxidant constitutes up to 40% by weight of the water-in-oil emulsion.
16. A method as claimed in Claim 15 in which the fish oil containing the antioxidant constitutes up to 30% by weight of the water-in-oil emulsion.
17. A method as claimed in Claim 16 in which the fish oil containing the antioxidant constitutes between 3% and 20% by weight of the water-in-oil emulsion.
18. A method as claimed in Claim 17 in which the fish oil containing the antioxidant constitutes approximately 4% by weight of the water-in-oil emulsion.
19. A method as claimed in any preceding claim in which the fish oil is an unhardened fish oil.
20. A method as claimed in any preceding claim in which the fish oil is a fish oil sold by Roche Products Limited of Great Britain under the Trade Mark ROPUFA 30.
21. A method as claimed in any preceding claim in which the fat phase comprises a vegetable oil.
22. A method as claimed in Claim 21 in which the vegetable oil is liquid at room temperature.
23. A method as claimed in Claim 21 or 22 in which the vegetable oil is selected from any one or more of the following oils: rape seed oil, soya bean oil, sun flower oil, and olive oil.
24. A method as claimed in any preceding claim in which the fat phase comprises a hard stock oil solid at room temperature.
25. A method as claimed in Claim 24 in which the hard stock oil is a vegetable oil.
26. A method as claimed in Claim 24 or 25 in which the hard stock oil is selected from any one or more of the following oils: hydrogenated or partly hydrogenated soya bean oil, hydrogenated or partly hydrogenated rape seed oil, hydrogenated or partly hydrogenated palm oil, hydrogenated or partly hydrogenated coconut oil, hydrogenated or partly hydrogenated palm kernel oil, a vegetable oil naturally hard at room temperature, for example, coconut oil, palm kernel oil, palm oil and fractions thereof, animal fats, for example, milk fat, tallow or lard or fractions thereof.
27. A method as claimed in any preceding claim in which the fat phase contains an emulsifier.
28. A method as claimed in Claim 27 in which the emulsifier is a mono or di glycerides.
29. A method as claimed in any preceding claim in which the water-in-oil emulsion contains a colouring, a flavouring and/or vitamins.
30. A method as claimed in any preceding claim in which the aqueous phase contains lactic acid, proteins and/or flavouring additives.
31. A method as claimed in any preceding claim in which the water-in-oil emulsion is prepared using a margarine process.
32. A method for preparing an edible water-in-oil emulsion comprising fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate, the method being substantially as described herein with reference to the examples.
33. An edible water-in-oil emulsion containing fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate wherein the aqueous phase is prepared without additives which may react with, or act as a catalyst for a reaction with ascorbyl palmitate to at least retard the development of a metallic type off-flavour or fishy taste.
34. An edible water-in-oil emulsion as claimed in Claim 32 in which the aqueous phase is prepared without any one or more of the following ingredients: whey, whey powder, skimmed milk, skimmed milk powder, butter milk, butter milk powder, whole milk, whole milk powder, and sodium caseinate.
35. An edible water-in-oil emulsion as claimed in Claim 33 or 34 in which the aqueous phase is prepared from de-ionised water.
36. An edible water-in-oil emulsion as claimed in any of Claims 33 to 35 in which the aqueous phase contains a sequestrant for binding metal ions in the aqueous phase.
37. An edible water-in-oil emulsion as claimed in Claim 36 in which the sequestrant is selected from any one or more of the following: citric acid, and/or its salts, phosphate salts, and ethylene diamine tetra-acetic acid, and/or its salts.
38. An edible water-in-oil emulsion as claimed in any of Claims 33 to 37 in which the aqueous phase is prepared with water with a relatively low level of calcium.
39. An edible water-in-oil emulsion as claimed in Claim 38 in which the aqueous phase is prepared with water with a very low level of calcium.
40. An edible water-in-oil emulsion as claimed in any of Claims 33 to 39 in which the fat phase constitutes up to 82% by weight of the water-in-oil emulsion.
41. An edible water-in-oil emulsion as claimed in Claim 40 in which the fat phase constitutes up to 60% by weight of the waterin-oil emulsion.
42. An edible water-in-oil emulsion as claimed in Claim 41 in which the fat phase constitutes approximately 40% by weight of the water-in-oil emulsion.
43. An edible water-in-oil emulsion as claimed in any of Claims 33 to 42 in which the fish oil containing the antioxidant constitutes up to 50% by weight of the water-in-oil emulsion.
44. An edible water-in-oil emulsion as claimed in Claim 43 in which the fish oil containing the antioxidant constitutes up to 40% by weight of the water-in-oil emulsion.
45. An edible water-in-oil emulsion as claimed in Claim 44 in which the fish oil containing the antioxidant constitutes up to 30% by weight of the water-in-oil emulsion.
46. An edible water-in-oil emulsion as claimed in Claim 45 in which the fish oil containing the antioxidant constitutes between 3% and 20% by weight of the water-in-oil emulsion.
47. An edible water-in-oil emulsion as claimed in Claim 46 in which the fish oil containing the antioxidant constitutes approximately 4% by weight of the water-in-oil emulsion.
48. An edible water-in-oil emulsion containing fish oil, the water-in-oil emulsion comprising a fat phase and an aqueous phase, the fat phase comprising fish oil containing an antioxidant including ascorbyl palmitate, the edible water-in-oil emulsion being substantially as described herein with reference to the examples.
49. A spread prepared from the edible water-in-oil emulsion as claimed in any of Claims 33 to 48.
50. A spread as claimed in Claim 49 in which the water-in-oil emulsion is prepared according to the method of any of Claims 1 to 32.
51. A spread substantially as described herein with reference to the examples.
GB9413405A 1993-07-02 1994-07-04 A method for preparing an edible water-in-oil emulsion Expired - Fee Related GB2280449B (en)

Applications Claiming Priority (2)

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IE930497 1993-07-02
PCT/IE1994/000061 WO1996019114A1 (en) 1993-07-02 1994-12-22 A method for preparing an edible water-in-oil emulsion

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GB2280449A true GB2280449A (en) 1995-02-01
GB2280449B GB2280449B (en) 1996-10-02

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WO1996019114A1 (en) * 1993-07-02 1996-06-27 Charleville Research Limited A method for preparing an edible water-in-oil emulsion
EP0743014A1 (en) * 1995-05-19 1996-11-20 Unilever N.V. Edible fat product
WO1997032947A1 (en) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. A product based on olive oil, enriched and supplemented with antioxidants
EP1277408A3 (en) * 2001-07-18 2003-03-12 Gertz, Barbara Use of water-in-oil emulsion for stabilising frying fat under frying conditions
WO2003032750A1 (en) * 2001-10-19 2003-04-24 Vita Power Limited A foodstuff supplement and method of producing same
WO2006043830A1 (en) * 2004-10-22 2006-04-27 Pharmalogica As Food supplement containing fish oil
US20060134178A1 (en) * 2002-11-22 2006-06-22 Nobushige Doisaki Composition containing organic substance having double bond with improved oxidative stability
US20180317523A1 (en) * 2015-04-22 2018-11-08 Basf Se Nanoparticles, nanoemulsions and their formation with mixing chamber micronization

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CN101208012B (en) 2005-04-26 2011-01-12 梅西大学 Lipid encapsulation
NZ603158A (en) 2010-04-26 2013-10-25 Univ Massey Emulsion comprising core lipid coated with nanoemulsion

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996019114A1 (en) * 1993-07-02 1996-06-27 Charleville Research Limited A method for preparing an edible water-in-oil emulsion
EP0743014A1 (en) * 1995-05-19 1996-11-20 Unilever N.V. Edible fat product
US5667837A (en) * 1995-05-19 1997-09-16 Van Den Bergh Foods Co., Division Of Conopco, Inc. Edible fat product
AU686059B2 (en) * 1995-05-19 1998-01-29 Unilever Plc Edible fat product
WO1997032947A1 (en) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. A product based on olive oil, enriched and supplemented with antioxidants
EP1277408A3 (en) * 2001-07-18 2003-03-12 Gertz, Barbara Use of water-in-oil emulsion for stabilising frying fat under frying conditions
WO2003032750A1 (en) * 2001-10-19 2003-04-24 Vita Power Limited A foodstuff supplement and method of producing same
KR100853899B1 (en) 2001-10-19 2008-08-25 비타 파워 리미티드 Food supplements and how to produce them
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WO1996019114A1 (en) 1996-06-27
GB2280449B (en) 1996-10-02

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