WO2013079279A1 - Process for the preparation of edible fat-continuous spreads - Google Patents
Process for the preparation of edible fat-continuous spreads Download PDFInfo
- Publication number
- WO2013079279A1 WO2013079279A1 PCT/EP2012/071878 EP2012071878W WO2013079279A1 WO 2013079279 A1 WO2013079279 A1 WO 2013079279A1 EP 2012071878 W EP2012071878 W EP 2012071878W WO 2013079279 A1 WO2013079279 A1 WO 2013079279A1
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- WO
- WIPO (PCT)
- Prior art keywords
- fat
- water
- mixture
- phase
- process according
- Prior art date
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Classifications
-
- 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
- A23D7/04—Working-up
-
- 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
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
Definitions
- the present invention relates to a process for the preparation of fat-continuous spreads comprising the step of subjecting a mixture of fat powder and a water-phase to at least a partial vacuum.
- Edible fat-continuous spreads like e.g. margarine and low fat spreads are well known food products that comprise a continuous fat-phase and a dispersed water-phase.
- Margarine is generally defined as a composition containing at least 80 wt. % of fat and about 20 wt. % of a water-phase. In contrast, emulsions containing less than 80 wt. % fat are generally called spreads.
- margarine and spread are often used interchangeably although in some countries the commercial use of the term margarine is subject to certain regulatory requirements. The main difference between margarine and spread is the amount of fat. For the purpose of the present invention the terms margarine and spread are used interchangeably.
- Margarine may be used for different applications including spreading, (shallow) frying and baking. In the market place margarine is generally sold as one of three principal types, namely hard or stick margarine (generally referred to as wrapper margarine), soft or tub margarine and liquid or pourable margarine.
- the fat-phase of margarine and similar edible fat-continuous spreads comprises a mixture of liquid oil (i.e. fat that is liquid at ambient temperature) and fat which is solid at ambient temperature.
- the liquid oil fraction typically comprises liquid unmodified vegetable oil such as soybean oil, sunflower oil, linseed oil, low erucic rapeseed oil (Canola), corn oil, (maize oil) and blends of vegetable oils.
- the solid fat also called structuring fat or hardstock fat, serves to structure the fat-phase by forming a fat crystal network throughout the continuous oil- phase. It also helps to stabilize the emulsion.
- the droplets of the water-phase are fixed within the spaces of the lattice of solid fat crystals. This prevents coalescence of the droplets and separation of the heavier water-phase from the fat-phase.
- the structuring fat has such properties that it melts or dissolves at in-mouth conditions, otherwise the product may have a heavy and/or waxy mouthfeel.
- the overall organoleptic impression should be smooth and preferable no perceivable grains should be present upon ingestion as this may result in what is generally known as a 'sandy', 'grainy' and/or 'lumpy' mouthfeel.
- Other important aspects of an edible spread are for example hardness, spreadibility and stability (e.g. storage stability and the ability to withstand temperature cycling). Temperature cycling means that the product is subjected to low and high temperatures (e.g. when the consumer takes the product out of the refrigerator and leaves it for some time at the table prior to use). An inadequate stability may for example lead to destabilization of the emulsion, oil exudation and/or uncontrolled crystal growth.
- edible fat-continuous spreads are prepared according to known processes that encompass the following steps:
- a disadvantage of these processes is that the complete composition (including the liquid oil, structuring fat and if present the water-phase) is subjected to a heating step and a cooling step, which requires a lot of energy.
- Another disadvantage of the known processes is that the choice of fats that can practically be used as structuring agent is rather limited. Moreover the amount of saturated fatty acids (SAFA) in the structuring agent is usually relatively high. Also trans fatty acid may be present. Some experts have called for reductions in these fatty acids to improve cardiovascular health.
- SAFA saturated fatty acids
- a low energy density for example products that are low in total fat
- SAFA high energy density
- a good nutritional profile by for example providing essential fatty acids like omega-3 and omega-6.
- edible spreads made using fat powder are prepared according to the following steps:
- the fat-powder is typically not subjected to a temperature above 25 degrees Celsius.
- a commonly used fat powder is micronized fat powder, which is for example obtainable by a Super Critical Melt Micron isation process, as described in J. of Supercritical Fluids 43 (2007) 181 -190 and EP1651338.
- a problem arising from the use of fat-powder is that it may be fluffy and may lead to the incorporation of gas-bubbles into the final spread. The incorporation of gas-bubbles may result in spreads with a poor stability, poor spreading characteristics and the occurrence of free water. Therefore, measures are taken to avoid incorporation of gas into the final spread when using fat-powder to prepare fat-continuous spread, which may be time- consuming and inconvenient. It is an object of the present invention to provide a more convenient and/or cheaper process, preferably with a reduced processing time, for the preparation of low fat edible fat-continuous spreads which are stable.
- step 'b' mixing the mixture prepared at step 'b' to provide a fat-continuous spread, wherein the liquid oil may be added to the mixture at any of steps 'a', 'b', or 'c' or when added in parts in any combination at steps 'a', 'b' and 'c'.
- a slurry is prepared of the fat powder and the liquid oil. Said slurry is then typically degassed by applying a partial vacuum to reduce gas-bubble incorporation into the final product. The presence of gas-bubbles in the final product may lead to spreads with a reduced stability, poor spreading characteristics and the occurrence of free water.
- the fat-continuous spread is prepared by mixing the degassed fat-slurry with the water-phase. In the process according to the invention a mixture of the fat powder and the water-phase is provided and subjected to at least a partial vacuum. Surprisingly it was found that said process has a reduced processing time, allows efficient degassing and that even though the fat powder is provided in a mixture which is water-continuous a stable and edible final spread may result.
- Weight percentage is based on the total weight of the composition unless otherwise stated.
- the terms 'fat' and 'oil' are used interchangeably. Where applicable the prefix 'liquid' or 'solid' is added to indicate if the fat or oil is liquid or solid at ambient temperature as understood by the person skilled in the art.
- the term 'structuring fat' or 'hardstock fat' refers to a fat that is solid at ambient temperature. The ambient temperature is defined as 20 degrees Celsius.
- the process of the present invention uses fat powder comprising structuring fat and does not require the heating and cooling of the whole composition to form the crystal network in the spread.
- Such processes have been described previously in for example EP 1865786 A.
- This process is characterized in that (part of) the structuring fat is pre-crystallized and does not form from the fat phase (comprising the structuring fat and liquid oil) optionally including the aqueous phase as is the case in conventional ways of preparing a spread.
- One of the main advantages of this process is that it requires less energy to make.
- the fat powder comprises structuring fat and preferably comprises at least 80 wt. % of structuring fat, more preferably at least 85 wt. %, even more preferably at least 90 wt. %, even more preferably at least 95 wt. % and even more preferably at least 98 wt. %. Still even more preferably the edible fat powder essentially consists of structuring fat.
- the structuring fat may be a single fat or a mixture of different fats.
- the structuring fat may be of vegetable, animal or marine origin.
- at least 50 wt. % of the structuring fat is of vegetable origin, more preferably at least 60 wt. %, even more preferably at least 70 wt. %, even more preferably at least 80 wt. %, even more preferably at least 90 wt% and even more preferably at least 95 wt. %.
- the structuring fat essentially consists of structuring fat of vegetable origin.
- the structuring fat as present in the edible fat powder preferably has a solid fat content N10 from 50 to 100, N20 from 26 to 95 and N35 from 5 to 60.
- the amount of fat powder used is suitably chosen such that the required structuring (i.e. stable emulsion) is obtained. It will be appreciated that the amount of fat powder depends on the amount of structuring fat in the fat powder and the desired amount of structuring fat on total product. Preferably the amount of structuring fat on total amount of product is 1 to 20 wt. %, more preferably 2 to 15 wt. % and even more preferably 4 to 12 wt. %. Suitable methods to prepare the fat powder include for example Super Critical Melt
- the fat powder used in the process according to the invention is micronized fat powder and more preferably is micronized fat powder obtainable by supercritical melt micronisation. It is important that the fat powder is not subjected to temperatures at which the structuring fat melts as this severely reduces the ability to structure. This temperature depends on the structuring fat used and can routinely be determined for example based on the solid fat content profile (i.e. N-lines) of the structuring fat.
- the fat powder, after production, has not been subjected to temperatures above 25 degrees Celsius. Water-phase
- the water-phase is prepared according to the standard way in accordance with the chosen ingredients.
- the water-phase may comprise ingredients like for example salt, acidifying agent and/or preservative.
- the water-phase may also comprise oil, for example to aid the inclusion of hydrophobic ingredients in the water-phase.
- the water-phase may also comprise proteins like for example dairy protein.
- the water-phase may also comprise commonly known gelling and/or thickening agents and include for example polysaccharides like starches, vegetable gums, pectin and gelling proteins. It has been observed that some gelling agents present in the water-phase, such as gelatin, may phase separate during step 'a' and/or step 'b'.
- the water-phase does not comprise gelling proteins and more preferably does not comprise gelatin. This problem was not observed for typical gelling and/or thickening agents such as those based on physically and/or chemically modified starch.
- the water- phase comprises at least one gelling and/or thickening agent selected from the group consisting of physically and chemically modified starch and more preferably selected from the group consisting of starch which has been subjected to cross-linking using phosphoric acid and tapioca starch which has been subjected to cross-linking using phosphoric acid.
- a water-phase and fat powder may be brought into contact with each other to provide a mixture of the water-phase and the fat powder at step 'a'.
- the temperature of said mixture is equal to or below 25 degrees Celsius.
- Suitable devices include for example a tubular heat exchanger or the like.
- any fat-powder and /or water-phase not provided in the mixture at step 'a' may be suitably added after step 'a' but preferably before or during the mixing step 'c'.
- the average gas-pressure at sea level is about 101 kPa, however, the local atmospheric pressure may vary according to various factors such as height above sea level, temperature and even local weather conditions. Furthermore, the indoor pressure may be maintained at a different level from the outdoor pressure. For example, pressurized rooms are typically used to prevent airborne contaminants entering the room from outside. For the purpose of the present invention ambient pressure is defined as the pressure in the immediate vicinity of (i.e. outside) the enclosure holding the mixture. It will be appreciated that in the process according to the invention the mixture of water-phase and fat powder is suitably enclosed to allow at least a (partial) vacuum to form at step b'. A (partial) vacuum indicates that the gas pressure (of the headspace) inside the enclosure is below the ambient pressure.
- a pressure inside the enclosure of 100 kPa is considered a partial vacuum.
- a pressure inside the enclosure of 90 kPa will be considered a partial vacuum.
- the partial vacuum at step 'b' is at most 70 %, more preferably at most 50 %, even more preferably at most 30 %, even more preferably at most 15 %, even more preferably at most 5 % and still more preferably is at most 0.5 % of the ambient pressure.
- the mixture at step 'b' is subjected to at least a partial vacuum for 1 to 60 minutes, more preferably 3 to 50 minutes, even more preferably 5 to 35 minutes and still more preferably 8 to 15 minutes.
- the mixture of fat powder and water-phase is mixed to provide a water-continuous slurry.
- a water-continuous slurry is formed by dispersing the fat powder in the water-continuous phase.
- the water-continuous slurry may be prepared using standard mixing equipment common in the field of spreads making for such use, like for example obtainable from Esco- Labor. Said mixing of the fat powder and water-phase into a slurry further reduces the degassing time while still allowing a stable spread to be prepared. Addition of liquid oil
- the oil used in the process according to the invention may be a single oil or a mixture of different oils, and may comprise other components.
- at least 50 wt. % of the oil (based on total amount of oil) is of vegetable origin, more preferably at least 60 wt. %, even more preferably at least 70 wt. %, even more preferably at least 80 wt. %, even more preferably at least 90 wt. % and even more preferably at least 95 wt. %.
- the oil essentially consists of oil of vegetable origin.
- the liquid oil fraction preferably comprises unmodified vegetable oil such as soybean oil, sunflower oil, linseed oil, low erucic rapeseed oil (Canola), corn oil (maize oil), olive oil, algae oil and blends of vegetable oils.
- algae are considered vegetables.
- the liquid oil may be added to the mixture of fat powder and water-phase at any of steps 'a', 'b', or 'c' or when added in parts in any combination at steps 'a', 'b' and 'c'. It will be appreciated that this indicates that liquid oil may be suitably added at any time point or time points during the process but should be present at step 'c'. For example, the whole of the liquid oil may be added at step 'a'.
- part of the liquid oil may be added at step 'a' and the remaining part at step 'c'.
- liquid oil may be added between step 'b' and 'c'.
- part of the liquid oil is added to the mixture at steps 'a' or 'b', or in parts at steps 'a' and 'b', to form a water-continuous mixture.
- the liquid oil is added at steps 'a' or 'b', or in parts at steps 'a' and 'b'.
- the addition of part of the liquid oil in said preferred ranges was found to further reduce the processing time and the chance of uncontrolled inversion of the water-continuous mixture before step 'c'.
- the mixture of fat powder and water-phase provided in step 'a' is water-continuous and should remain water-continuous at least up to and during step 'b'. This also applies when liquid oil is present in the mixture.
- the temperature of the mixture comprising fat powder and water-phase is 1 to 15, more preferably 5 to 13 and even more preferably 8 to 1 1 degrees Celsius. It was surprisingly found that maintaining the mixture at said temperature range reduces the chance of uncontrolled inversion of the water-continuous mixture to a fat- continuous mixture.
- the temperature of mixing at step 'c' is such that the temperature of the mixture of the water- phase and the fat powder and the liquid oil is preferably equal to or below 25 degrees Celsius.
- Suitable devices include for example a tubular heat exchanger or the like.
- a temperature at step 'c' of 15 degrees Celsius or higher stimulates the conversion of the water-continuous system to a fat-continuous system in the process according to the invention and further reduces processing time.
- the temperature of the mixture of liquid oil, fat powder and water-phase at step 'c' is from 15 to 25, more preferably 17 to 23 and even more preferably 18 to 21 degrees Celsius.
- the edible fat-continuous spread made according to the process of the invention comprises 5 to 45 wt. %, more preferably 10 to 35 wt. % and even more preferably 15 to 30 wt. % of fat, based on the total weight of the spread.
- the edible fat-continuous spread made according to the process of the invention comprises 55 to 95 wt. %, more preferably 65 to 90 wt. % and even more preferably 70 to 85 wt. % of a water-phase, based on the total weight of the spread.
- the amount of dispersed gas (i.e. gas-bubbles) in a liquid phase is reflected by its apparent density. This is determined by completely filling a cup of a known volume and weight with the mixture and observing the increase in weight. It is important that the cup is completely filled and that excess mixture rising above the rim of the cup is carefully removed. The density of the mixture wherein all gas-bubbles have been removed is taken as a 100 % degassed mixture (i.e. having no gas bubbles).
- the NMR signal (echo height) of the protons of the water in a water -in-oil emulsion are measured using a sequence of 4 radio frequency pulses in the presence (echo height E) and absence (echo height E * ) of two magnetic field gradient pulses as a function of the gradient power.
- the oil protons are suppressed in the first part of the sequence by a relaxation filter.
- a spread with is D3,3 of below 10 micrometer and an e A sigma of below 2.8 is considered to be of good quality and stability.
- the Stevens value indicates a product's hardness or firmness.
- the Stevens value was measured with a Stevens penetrometer (Brookfield LFRA Texture Analyser (LFRA 1500), ex Brookfield Engineering Labs, UK) equipped with a stainless steel probe with a diameter of 6.35 mm and operated in "normal" mode. The probe is pushed into the product at a speed of 2 mm/s, a trigger force of 5 gram from a distance of 10 mm. The force required is read from the digital display and is expressed in grams. The Stevens value was determined at 5 degrees Celsius.
- a flexible palette knife was used to spread a small amount of a spread on fat free paper.
- the resulting spreading screen was evaluated according to a standardized scale.
- a score of 1 represents a homogeneous and smooth product without any defects
- a 2 indicates observable small spreading defects such as slightly inhomogeneous spreading or the presence of some vacuoles
- a 3 indicates clearly observable defects, such as the appearance of free water or coarseness during spreading.
- a score of 4 or 5 refers to unacceptable products, where a 4 indicates a product which still has some spreading properties, but with an unacceptable level of defects.
- a spread with a spreading score of at most 2 is considered to be of good quality and stability.
- #Fat powder was obtained using a supercritical melt micronisation process similar to the process described in Particle formation of ductile materials using the PGSS technology with supercritical carbon dioxide, P.Munuklu, Ph.D. Thesis, Delft University of Technology, 16-12- 2005, Chapter 4, pp. 41-51.
- the fat powder consisted of inES48: an interesterified mixture of 65% dry fractionated palm oil stearin with an Iodine Value of 14 and 35% palm kernel oil.
- Dimodan HP is a molecularly distilled mono/diacylglyceride mixture derived from fully hardened palm oil (90% monoglyceride) ex Danisco.
- Sunlec M is hydrolysed sunflower lecithin.
- Example 1 The mixtures obtained in the process of Example 1 , Example 2 and Comparative A were subsequently treated in a 150 ml double walled stainless steel pin stirrer, thermo-stated at 8°C and operated at 2400 rpm, with two rows of 4 stator and rotor pins to provide the final spreads.
- Stable spreads could be made via the process of Example 2.
- Said spread were characterized by an average drop size (D3,3) of 7.2 micrometer, an e A sigma of 2.6 and a Stevens value of 127 as measured after 3 days of storage at 5 degrees Celsius right after production. After a total of 5 days at 5 degrees Celsius a spreading score of 1-2 and a free water score of 1-2 was observed. Therefore it is concluded that a process wherein fat powder is provided in a water-continuous mixture may result in a stable edible spread.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
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Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2857216A CA2857216C (en) | 2011-11-30 | 2012-11-06 | Process for the preparation of edible fat-continuous spreads |
EP12780504.2A EP2785193B1 (en) | 2011-11-30 | 2012-11-06 | Process for the preparation of edible fat-continuous spreads |
BR112014012879-0A BR112014012879B1 (en) | 2011-11-30 | 2012-11-06 | Process for preparing a spread |
PL12780504T PL2785193T3 (en) | 2011-11-30 | 2012-11-06 | Process for the preparation of edible fat-continuous spreads |
US14/359,133 US11871762B2 (en) | 2011-11-30 | 2012-11-06 | Process for the preparation of edible fat-continuous spreads |
ZA2014/03741A ZA201403741B (en) | 2011-11-30 | 2014-05-22 | Process for the preparation of edible fat-continuous spreads |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11191275.4 | 2011-11-30 | ||
EP11191275 | 2011-11-30 |
Publications (1)
Publication Number | Publication Date |
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WO2013079279A1 true WO2013079279A1 (en) | 2013-06-06 |
Family
ID=47116021
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2012/071878 WO2013079279A1 (en) | 2011-11-30 | 2012-11-06 | Process for the preparation of edible fat-continuous spreads |
Country Status (8)
Country | Link |
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US (1) | US11871762B2 (en) |
EP (1) | EP2785193B1 (en) |
BR (1) | BR112014012879B1 (en) |
CA (1) | CA2857216C (en) |
HU (1) | HUE026561T2 (en) |
PL (1) | PL2785193T3 (en) |
WO (1) | WO2013079279A1 (en) |
ZA (1) | ZA201403741B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11419346B2 (en) | 2014-10-17 | 2022-08-23 | Upfield Europe B.V. | Edible aerated water-in-oil emulsions |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005014158A1 (en) | 2003-07-17 | 2005-02-17 | Unilever N.V. | Process for the preparation of an edible dispersion comprising oil and structuring agent |
WO2006087093A1 (en) * | 2005-02-17 | 2006-08-24 | Unilever N.V. | Process for the preparation of a spreadable dispersion comprising sterol |
WO2010069752A1 (en) | 2008-12-19 | 2010-06-24 | Unilever Nv | Process for the preparation of a fat continuous spread |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2158452B (en) | 1984-05-11 | 1988-01-27 | Unilever Plc | Fat-continuous emulsions and spreads |
GB9405235D0 (en) | 1994-03-17 | 1994-04-27 | St Ivel Ltd | Water-containous spread |
-
2012
- 2012-11-06 HU HUE12780504A patent/HUE026561T2/en unknown
- 2012-11-06 PL PL12780504T patent/PL2785193T3/en unknown
- 2012-11-06 US US14/359,133 patent/US11871762B2/en active Active
- 2012-11-06 BR BR112014012879-0A patent/BR112014012879B1/en not_active IP Right Cessation
- 2012-11-06 WO PCT/EP2012/071878 patent/WO2013079279A1/en active Application Filing
- 2012-11-06 EP EP12780504.2A patent/EP2785193B1/en active Active
- 2012-11-06 CA CA2857216A patent/CA2857216C/en active Active
-
2014
- 2014-05-22 ZA ZA2014/03741A patent/ZA201403741B/en unknown
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005014158A1 (en) | 2003-07-17 | 2005-02-17 | Unilever N.V. | Process for the preparation of an edible dispersion comprising oil and structuring agent |
EP1651338A1 (en) | 2003-07-17 | 2006-05-03 | Unilever N.V. | Process for the preparation of an edible dispersion comprising oil and structuring agent |
WO2006087093A1 (en) * | 2005-02-17 | 2006-08-24 | Unilever N.V. | Process for the preparation of a spreadable dispersion comprising sterol |
WO2006087091A2 (en) * | 2005-02-17 | 2006-08-24 | Unilever N.V. | Process for the preparation of a spreadable dispersion |
EP1865786A2 (en) | 2005-02-17 | 2007-12-19 | Unilever N.V. | Process for the preparation of a spreadable dispersion |
WO2010069752A1 (en) | 2008-12-19 | 2010-06-24 | Unilever Nv | Process for the preparation of a fat continuous spread |
Non-Patent Citations (3)
Title |
---|
"Ullmans Encyclopedia", vol. A 16, pages: 156 - 158 |
J. OF SUPERCRITICAL FLUIDS, vol. 43, 2007, pages 181 - 190 |
P.MUNUKLU: "Ph.D.Thesis", 16 December 2005, DELFT UNIVERSITY OF TECHNOLOGY, pages: 41 - 51 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11419346B2 (en) | 2014-10-17 | 2022-08-23 | Upfield Europe B.V. | Edible aerated water-in-oil emulsions |
Also Published As
Publication number | Publication date |
---|---|
CA2857216A1 (en) | 2013-06-06 |
HUE026561T2 (en) | 2016-06-28 |
US20140342066A1 (en) | 2014-11-20 |
PL2785193T3 (en) | 2016-02-29 |
US11871762B2 (en) | 2024-01-16 |
CA2857216C (en) | 2020-04-14 |
BR112014012879B1 (en) | 2020-03-03 |
BR112014012879A2 (en) | 2017-06-13 |
EP2785193A1 (en) | 2014-10-08 |
ZA201403741B (en) | 2016-02-24 |
EP2785193B1 (en) | 2015-09-09 |
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