CA2595281A1 - Process for the preparation of a spreadable dispersion comprising sterol - Google Patents
Process for the preparation of a spreadable dispersion comprising sterol Download PDFInfo
- Publication number
- CA2595281A1 CA2595281A1 CA002595281A CA2595281A CA2595281A1 CA 2595281 A1 CA2595281 A1 CA 2595281A1 CA 002595281 A CA002595281 A CA 002595281A CA 2595281 A CA2595281 A CA 2595281A CA 2595281 A1 CA2595281 A1 CA 2595281A1
- Authority
- CA
- Canada
- Prior art keywords
- dispersion
- structuring agent
- particles
- oil
- fat
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 43
- 230000008569 process Effects 0.000 title claims abstract description 37
- 229930182558 Sterol Natural products 0.000 title claims abstract description 32
- 235000003702 sterols Nutrition 0.000 title claims abstract description 32
- 150000003432 sterols Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000002245 particle Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 239000007787 solid Substances 0.000 claims abstract description 29
- 239000008346 aqueous phase Substances 0.000 claims abstract description 13
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 235000004213 low-fat Nutrition 0.000 claims description 14
- 239000011164 primary particle Substances 0.000 claims description 13
- 239000011163 secondary particle Substances 0.000 claims description 9
- 150000002632 lipids Chemical class 0.000 claims description 6
- 239000007762 w/o emulsion Substances 0.000 claims description 6
- 239000002960 lipid emulsion Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 abstract description 7
- 239000003921 oil Substances 0.000 description 61
- 235000019198 oils Nutrition 0.000 description 59
- 239000012071 phase Substances 0.000 description 45
- 239000003925 fat Substances 0.000 description 40
- 235000019197 fats Nutrition 0.000 description 38
- 239000007789 gas Substances 0.000 description 27
- 239000000839 emulsion Substances 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 8
- 235000013310 margarine Nutrition 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000003264 margarine Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 235000019486 Sunflower oil Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002600 sunflower oil Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000013618 particulate matter Substances 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229960004424 carbon dioxide Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- 239000008107 starch Substances 0.000 description 4
- -1 sterol esters Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- 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 3
- ARYTXMNEANMLMU-UHFFFAOYSA-N 24alpha-methylcholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(C)C(C)C)C1(C)CC2 ARYTXMNEANMLMU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
- 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 3
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 3
- 239000011648 beta-carotene Substances 0.000 description 3
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- 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 3
- 229960002747 betacarotene Drugs 0.000 description 3
- ARYTXMNEANMLMU-ATEDBJNTSA-N campestanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]2(C)CC1 ARYTXMNEANMLMU-ATEDBJNTSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
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- 235000010445 lecithin Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004302 potassium sorbate Substances 0.000 description 3
- 235000010241 potassium sorbate Nutrition 0.000 description 3
- 229940069338 potassium sorbate Drugs 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
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- 238000005245 sintering Methods 0.000 description 3
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- 239000002562 thickening agent Substances 0.000 description 3
- 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 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 description 2
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000000431 campesterol Nutrition 0.000 description 2
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
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- 229930182478 glucoside Natural products 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 239000008240 homogeneous mixture Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
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- 238000012545 processing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
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- 239000011780 sodium chloride Substances 0.000 description 2
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- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- VGSSUFQMXBFFTM-UHFFFAOYSA-N (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol Natural products C1C(O)C2(O)CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 VGSSUFQMXBFFTM-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
- HCXVJBMSMIARIN-UHFFFAOYSA-N stigmasterol Chemical compound C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 HCXVJBMSMIARIN-UHFFFAOYSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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
- A23D7/001—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
- A23D7/005—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
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- 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
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
- A23D9/05—Forming free-flowing pieces
-
- 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
- A23L23/00—Soups; Sauces; Preparation or treatment thereof
- A23L23/10—Soup concentrates, e.g. powders or cakes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
Process for the preparation of a spreadable edible dispersion wherein a mixture of oil and solid structuring agent particles is subjected to stirring and an aqueous phase and/or solid phase is gradually added to the mixture until a dispersion of the desired oil content is obtained, wherein the solid structuring agent particles have a microporous structure of submicron size particles and comprise sterol.
Description
Process for the preparation of a spreadable dispersion comprising sterol Description Field of the invention The present invention relates to a process for the preparation of a spreadable edible dispersion comprising oil and structuring agent, in particular to such dispersions comprising oil and structuring agent as continuous phase and a dispersed phase. The dispersed phase may be an aqueous liquid (thus forming a water-in-oil emulsion) and/or a solid particulate matter (thus forming a suspension).
Background of the invention Edible dispersions comprising oil and structuring agent are well known. Examples of well-known products that substantially consist of such edible dispersions are water-in-oil emulsions, such as for instance margarines and spreads. These edible dispersions typically have an oil phase that is a blend of liquid oil and fat that is solid at normal ambient temperature (20 C). This solid fat, often also designated as hardstock, acts as structuring agent, and its function is to stabilise the dispersion. For a margarine or spread, ideally the structuring agent has such properties that it should have melted or dissolved at mouth temperature, otherwise the product has a heavy, waxy mouthfeel.
Background of the invention Edible dispersions comprising oil and structuring agent are well known. Examples of well-known products that substantially consist of such edible dispersions are water-in-oil emulsions, such as for instance margarines and spreads. These edible dispersions typically have an oil phase that is a blend of liquid oil and fat that is solid at normal ambient temperature (20 C). This solid fat, often also designated as hardstock, acts as structuring agent, and its function is to stabilise the dispersion. For a margarine or spread, ideally the structuring agent has such properties that it should have melted or dissolved at mouth temperature, otherwise the product has a heavy, waxy mouthfeel.
US 2002/0076476 discloses edible oil-in-water emulsions having sensorial properties resembling those of mayonnaise having reduced oil content. This is achieved by using small-sized oil droplets in combination with casein.
EP 1 197 153 relates to aqueous phase dispersions or suspensions comprising high melting lipids having a size of microns or less in combination with a non-sterol emulsifier.
US 6,129,944 relates to products containing microcrystalline plant sterol, a method of production for such products by pulverisation and to the use of said products for producing edible products.
Other known dispersions comprising oil and structuring agent are disclosed in EP-A-775444 and WO 98/47386. Herein the dispersed phase is a dry particulate matter, such as e.g. flour, starch, salt, spices, herbs etc.
Generally, the edible dispersions comprising structuring agent are prepared according to prior art processes that encompass the following steps:
1) mixing/dispersion of the aqueous phase and/or the solid phase and the oil phase, at a temperature where the oil phase, including the structuring agent is liquid;
2) formation of a fat crystal network to stabilise the resulting dispersion and give the product some degree of firmness;
EP 1 197 153 relates to aqueous phase dispersions or suspensions comprising high melting lipids having a size of microns or less in combination with a non-sterol emulsifier.
US 6,129,944 relates to products containing microcrystalline plant sterol, a method of production for such products by pulverisation and to the use of said products for producing edible products.
Other known dispersions comprising oil and structuring agent are disclosed in EP-A-775444 and WO 98/47386. Herein the dispersed phase is a dry particulate matter, such as e.g. flour, starch, salt, spices, herbs etc.
Generally, the edible dispersions comprising structuring agent are prepared according to prior art processes that encompass the following steps:
1) mixing/dispersion of the aqueous phase and/or the solid phase and the oil phase, at a temperature where the oil phase, including the structuring agent is liquid;
2) formation of a fat crystal network to stabilise the resulting dispersion and give the product some degree of firmness;
3) modification of the crystal network to produce the desired firmness and confer plasticity.
In case the dispersion is a low-fat water-in-oil emulsion spread (i.e. with a oil content of 45 wt.% or less), normally in step 1) a oil-in-water emulsion (premix) is formed, which in step 2) is inverted, so that a transition of the emulsion from oil-in-water to water-in oil (inversion) occurs. Inversion has a number of disadvantages: it is difficult to control and rework (i.e.
material that is not packed, but returned to the premix, needs to be reinverted, which may lead to processing complications.
The steps 1)-3) are usually conducted in a process that involves apparatus that allow heating, cooling and mechanical working of the ingredients, such as the churn process or the votator process. The churn process and the votator process are described in Ullmanns Encyclopedia, Fifth Edition, Volume A 16 pages 156-158. Using these techniques excellent dispersions (spreads) having high emulsion stability and good melting properties in the mouth can be prepared.
However, a disadvantage of the known processes is that the process involves a heating step and a cooling step and therefore requires a lot of energy. In a dispersion with for instance 4 wt.% structuring agent the whole weight of the dispersion (100 wt.%) needs to be heated and cooled.
Another disadvantage of the known processes is that the choice of fats that can practically be used as structuring agent is rather limited. If the melting point of the structuring agent is too high the melting properties in the mouth are unsatisfactory. If on the other hand, the melting point is too low, the emulsion stability will be negatively affected. Moreover the amount of saturated fatty acids in the structuring agent is usually relatively high. Saturated fatty acids are a known risk factor for cardiovascular health.
Further disadvantage of the known processes is that the product may deteriorate due to the changes in temperature caused by the heating and cooling step and that heat-sensitive ingredients cannot be incorporated.
Additionally, when low-fat spreads are prepared an inversion step is usually needed, which is difficult to control and has rework problems.
Co-pending application PCT/EP2004/006544 describes edible dispersions, including water-in-oil emulsions, that comprise a structuring agent having a microporous structure of submicron size particles. The water-in-oil emulsion may be a table spread. In the examples pourable emulsions and pourable dispersions were described. The edible dispersions may for instance be prepared by mixing an oil phase with structuring agent particles with a separately prepared water phase.
Summary of the invention It is therefore an object of the invention to provide a process for the preparation of a spreadable dispersion that requires less energy than the known processes. Another object is to provide such a process that allows the use of more types of structuring agent, especially more sorts of hardstock. A further object of the invention is a reduction of the amount of saturated fatty acids in the hardstock.
Still a further object of the invention is to provide a process for the preparation of a dispersion that allows the incorporation of heat-sensitive ingredients and/or that 5 avoids deterioration of the emulsion.
One or more of these objects is attained according to the invention which provides a process for the preparation of a spreadable edible dispersion having a fat content of less than 70 wt.%, wherein a mixture of oil and solid structuring agent particles is subjected to stirring and an aqueous phase is added to the mixture until a dispersion is obtained, wherein the solid structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5pm and further (the solid structuring agent particles) comprise sterols. Gradually is herein defined as not adding the whole solid or aqueous phase at the start of the process, but in two or more portions at different times during the process if conducted batchwise or in two or more places in the process equipment in a continuous process.
With the process according to the invention, products are obtained that have a smaller water droplet size (D3,3 as described herein) and a firmer structure (Stevens value as described herein) than products prepared according to the prior art votator process. The smaller water droplet size leads to increased microbiological stability, so product may be made that need less or no salt and/or preservative.
In case the dispersion is a low-fat water-in-oil emulsion spread (i.e. with a oil content of 45 wt.% or less), normally in step 1) a oil-in-water emulsion (premix) is formed, which in step 2) is inverted, so that a transition of the emulsion from oil-in-water to water-in oil (inversion) occurs. Inversion has a number of disadvantages: it is difficult to control and rework (i.e.
material that is not packed, but returned to the premix, needs to be reinverted, which may lead to processing complications.
The steps 1)-3) are usually conducted in a process that involves apparatus that allow heating, cooling and mechanical working of the ingredients, such as the churn process or the votator process. The churn process and the votator process are described in Ullmanns Encyclopedia, Fifth Edition, Volume A 16 pages 156-158. Using these techniques excellent dispersions (spreads) having high emulsion stability and good melting properties in the mouth can be prepared.
However, a disadvantage of the known processes is that the process involves a heating step and a cooling step and therefore requires a lot of energy. In a dispersion with for instance 4 wt.% structuring agent the whole weight of the dispersion (100 wt.%) needs to be heated and cooled.
Another disadvantage of the known processes is that the choice of fats that can practically be used as structuring agent is rather limited. If the melting point of the structuring agent is too high the melting properties in the mouth are unsatisfactory. If on the other hand, the melting point is too low, the emulsion stability will be negatively affected. Moreover the amount of saturated fatty acids in the structuring agent is usually relatively high. Saturated fatty acids are a known risk factor for cardiovascular health.
Further disadvantage of the known processes is that the product may deteriorate due to the changes in temperature caused by the heating and cooling step and that heat-sensitive ingredients cannot be incorporated.
Additionally, when low-fat spreads are prepared an inversion step is usually needed, which is difficult to control and has rework problems.
Co-pending application PCT/EP2004/006544 describes edible dispersions, including water-in-oil emulsions, that comprise a structuring agent having a microporous structure of submicron size particles. The water-in-oil emulsion may be a table spread. In the examples pourable emulsions and pourable dispersions were described. The edible dispersions may for instance be prepared by mixing an oil phase with structuring agent particles with a separately prepared water phase.
Summary of the invention It is therefore an object of the invention to provide a process for the preparation of a spreadable dispersion that requires less energy than the known processes. Another object is to provide such a process that allows the use of more types of structuring agent, especially more sorts of hardstock. A further object of the invention is a reduction of the amount of saturated fatty acids in the hardstock.
Still a further object of the invention is to provide a process for the preparation of a dispersion that allows the incorporation of heat-sensitive ingredients and/or that 5 avoids deterioration of the emulsion.
One or more of these objects is attained according to the invention which provides a process for the preparation of a spreadable edible dispersion having a fat content of less than 70 wt.%, wherein a mixture of oil and solid structuring agent particles is subjected to stirring and an aqueous phase is added to the mixture until a dispersion is obtained, wherein the solid structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5pm and further (the solid structuring agent particles) comprise sterols. Gradually is herein defined as not adding the whole solid or aqueous phase at the start of the process, but in two or more portions at different times during the process if conducted batchwise or in two or more places in the process equipment in a continuous process.
With the process according to the invention, products are obtained that have a smaller water droplet size (D3,3 as described herein) and a firmer structure (Stevens value as described herein) than products prepared according to the prior art votator process. The smaller water droplet size leads to increased microbiological stability, so product may be made that need less or no salt and/or preservative.
Further according to the invention low fat spreads may be prepared that need no thickener or gelling agent in the water phase. When low-fat spreads are prepared an additional advantage of the process according to the invention is that no inversion is needed.
Contrary to the process described in Co-pending application PCT/EP2004/006544, in the present process the aqueous phase and/or solid phase is gradually added to the mixture until a dispersion of the desired oil content is obtained. This makes the preparation of dispersion having a relatively low oil content, i.e. below 45 wt.%, possible.
Detailed description of the invention According to the invention, an aqueous phase is added to a mixture of oil and solid structuring agent particles which is stirred, until a dispersion is obtained. A dispersion is herein defined as a system in which two or more phases that are insoluble or only slightly soluble are distributed in one another.
The dispersion may be an emulsion, a suspension or foam or any combination thereof, it may be oil continuous, water continuous or bi-continuous. Preferably the dispersion is oil continuous, more preferably an oil continuous emulsion or oil continuous suspension.
Where a solid phase is present in the dispersion according to the invention, it is preferably a solid phase of dry particulate matter.
Contrary to the process described in Co-pending application PCT/EP2004/006544, in the present process the aqueous phase and/or solid phase is gradually added to the mixture until a dispersion of the desired oil content is obtained. This makes the preparation of dispersion having a relatively low oil content, i.e. below 45 wt.%, possible.
Detailed description of the invention According to the invention, an aqueous phase is added to a mixture of oil and solid structuring agent particles which is stirred, until a dispersion is obtained. A dispersion is herein defined as a system in which two or more phases that are insoluble or only slightly soluble are distributed in one another.
The dispersion may be an emulsion, a suspension or foam or any combination thereof, it may be oil continuous, water continuous or bi-continuous. Preferably the dispersion is oil continuous, more preferably an oil continuous emulsion or oil continuous suspension.
Where a solid phase is present in the dispersion according to the invention, it is preferably a solid phase of dry particulate matter.
Where an aqueous phase is present in the dispersion according to the invention, it is preferably a dispersed aqueous phase.
The amounts given will be expressed in wt.% relative to the total weight of the food composition, unless indicated otherwise.
Fat and oil may sometimes be used interchangeably herein, for instance fat phase and oil phase and fat content or oil content may be used to indicate the same.
According to the invention spreadable edible dispersions are provided comprising micronised structuring agent particles wherein said structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5um, wherein the dispersion has a Stevens value, measured at room temperature as defined herein of 30g or more, preferably 50g or more, more preferably 80g or more and most preferably lOOg or more, said dispersion also comprising sterol.
Preferably the fat content of the spreadable dispersion of the invention is from 10-70 wt.%, for example 45 wt.% or less, preferably 33-69.65 wt.%.
Preferably the dispersion is a low-fat water-in-oil emulsion spread having a fat content of 45 wt.% or less, more preferred 33-45 wt.%.
The amounts given will be expressed in wt.% relative to the total weight of the food composition, unless indicated otherwise.
Fat and oil may sometimes be used interchangeably herein, for instance fat phase and oil phase and fat content or oil content may be used to indicate the same.
According to the invention spreadable edible dispersions are provided comprising micronised structuring agent particles wherein said structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5um, wherein the dispersion has a Stevens value, measured at room temperature as defined herein of 30g or more, preferably 50g or more, more preferably 80g or more and most preferably lOOg or more, said dispersion also comprising sterol.
Preferably the fat content of the spreadable dispersion of the invention is from 10-70 wt.%, for example 45 wt.% or less, preferably 33-69.65 wt.%.
Preferably the dispersion is a low-fat water-in-oil emulsion spread having a fat content of 45 wt.% or less, more preferred 33-45 wt.%.
The invention further provides a low-fat water-in-oil emulsion spread comprising sterol, having a fat content of 45 wt.% or less, a Stevens value measured at room temperature as defined herein of 60 g or more and a saturated fat content (SAFA) of 25 wt.% or less. SAFA
content (wt.%) is herein expressed based on the weight of the fat phase.
In a preferred embodiment, the low-fat emulsion spread comprises from 3 to 25 wt.% sterol, more preferred from 7 to 15 wt.% sterol.
Preferably the spreadable edible dispersions according to the invention has a low water droplet size, preferably the water droplet size as defined herein is 10 pm or less, more preferably 5 pm or less.
According to the invention, the dispersion is formed by mixing oil, the solid structuring agent particles comprising sterols, and the other phase or phases of the dispersion, such as for example an aqueous phase, a solid phase and/or a gas phase.
According to the invention, the solid structuring agent particles (also described herein as secondary particles) should have a microporous structure of submicron size particles (also described herein as primary particles) and further they comprise sterol.
The secondary particles are agglomerates of primary particles which have a microporous structure. The size of the primary particles is submicron (that is they have a diameter below 1u).
An example of a microporous structure is shown in figures 6 and 7 of PCT/EP2004/006544. The primary particles typically have the shape as shown in figure 7, in which the platelets with submicron dimensions are the primary particles. The thickness of the platelets should be submicron, preferably the thickness is on average 0.01-0.5pm, more preferably 0.03-0.2pm, even more preferably 0.06-0.12}im.
Equivalent good results were obtained for a secondary particles having a microporous structure of more bubble-like shape, such as shown in figure 10 of PCT/EP2004/006544. In such microporous structure the wall thickness of-the bubbles should be submicron, for instance on average 0.01-0.5um, more preferably 0.03-0.2pm, even more preferably 0.06-0.12pm.
The secondary particles, may, in the course of the preparation of the dispersion, for instance through the force of a mixer, be broken into submicron particles. The resulting submicron particles will form the structuring network of the dispersion.
The structuring agent comprises sterol. Where reference is made to sterol this includes the saturated stanols and esterified derivatives of sterol/stanol or mixtures of any of these.
In this application where reference is made to sterolester, this also includes their saturated derivatives, the stanol esters, and combinations of sterol- and stanol esters.
5 Sterols or phytosterols, also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4,4'-dimethylsterols. In oils they mainly exist as free sterols and sterol esters of fatty acids although sterol glucosides 10 and acylated sterol glucosides are also present. There are three major phytosterols namely beta-sitosterol, stigmasterol and campesterol. Schematic drawings of the components meant are as given in "Influence of Processing on Sterols of Edible Vegetable Oils", S.P. Kochhar; Prog.
Lipid Res. 22: pp. 161-188.
The respective 5 alpha- saturated derivatives such as sitostanol, campestanol and ergostanol and their derivatives are in this specification referred to as stanols.
Preferably the (optionally esterified) sterol or stanol is selected from the group comprising fatty acid ester of (3-sitosterol, (3-sitostanol, campesterol, campestanol, stigmasterol, brassicasterol, brassicastanol or a mixture thereof.
The sterols or stanols are optionally at least partly esterified with a fatty acid. Preferably the sterols or stanols are esterified with one or more C2_22 fatty acids.
For the purpose of the invention the term C2_22 fatty acid refers to any molecule comprising a C2_22 main chain and at least one acid group. Although not preferred within the present context the C2-22 main chain may be partially substituted or side chains may be present. Preferably, however the C2_22 fatty acids are linear molecules comprising one or two acid group(s) as end group(s). Most preferred are linear C8-22 fatty acids as these occur in natural oils.
Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid. Most preferred are myristic acid, lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
When desired a mixture of fatty acids may be used for esterification of the sterols or stanols. For example, it is possible to use a naturally occurring fat or oil as a source of the fatty acid and to carry out the esterification via an interesterification reaction.
The amount of sterol in the structuring agent is preferably from 80 to 100 wt.% on total weight of the structuring agent.
Preferably, the structuring agent comprises edible lipid, more preferably it is edible fat. Edible fats consist predominantly of triglycerides. Typically such edible fats suitable as structuring agent are mixtures of triglycerides, some of which have a melting point higher than room or ambient temperature and therefore contain solids in the form of crystals.
The solid structuring agent, also denoted as hardstock, serves to structure the fat phase and helps to stabilise the dispersion.
For imparting to common margarine a semi-solid, plastic, spreadable consistency this stabilising and structuring functionality plays an important role. The crystals of the solid fat form a network throughout the liquid oil resulting into a structured fat phase. The aqueous phase droplets are fixed within the spaces of the lattice of solid fat crystals. In this way coalescence of the droplets and separation of the heavier aqueous phase from the fat phase is prevented.
The process according to the invention may be executed batch-wise or continuous. Conventional unit operations and apparatus, e.g. mixers, pumps and extruders may be used. A
suitable process flow diagram for a continuous process according to the invention is given in figure 1. Micronised fat may be added to the premix or via the inlet (5), preferably at least part of the micronised fat is added via inlet (5).
Further common ingredients of the fat phase are emulsifiers, such as monoglycerides and lecithin, colouring agents and flavours.
The solid structuring agent particles (secondary particles) preferably have an average particle size (D3,2) of 60 micrometer or less, more preferably the solid structuring agent particles have an average particle size of 30 micrometer or less. The average particle size (D3,2) is determined as indicated in the examples.
Preferably the solid structuring agent particles are prepared using a micronisation process. In the micronisation process the solid structuring agent particles are prepared by preparing a homogeneous mixture of structuring agent and liquified gas or supercritical gas at a pressure of 5-40 MPa and expanding the mixture through an orifice, under such conditions that a spray jet is applied in which the structuring agent is solidified and micronised. The liquified gas or supercritical gas may be any gas that may be used in the preparation of food products, for example carbondioxide, nitrogen, propane, ethane, xenon or other noble gases. Carbondioxide and propane are preferred. Carbondioxide is most preferred.
Advantages of carbondioxide are that it has a mild (31 C) critical temperature, it is non-flammable, nontoxic, environmentally friendly and it may be obtained from existing industrial processes without further contribution to the greenhouse effect. It is fairly miscible with oil and is readily recovered owing to its high volatility at ambient conditions. Finally liquid CO2 is the second least expensive solvent after water.
The temperature of the mixture of structuring agent and liquified gas or supercritical gas is preferably such that the mixture forms a homogeneous mixture. Advantageously, the temperature of the mixture of structuring agent and liquified gas or supercritical gas is below the slip melting point of the structuring agent at atmospheric pressure and above the temperature at which phase separation of the mixture occurs. Under such conditions the smallest micronised particles may be obtained.
The pressure and temperature of the mixture of structuring agent and liquefied or supercritical gas is preferably such that a large amount of the gas may be dissolved in the structuring agent. The amount dissolved will be determined by the phase diagram of the mixture of structuring agent and liquified or supercritical gas. At higher pressures as well as at lower temperatures more gas will dissolve in the structuring agent.
Preferably the temperature and pressure are chosen such that 10 wt.% or more, more preferably 20 wt.% or more or most preferably 30 wt.% or more of gas is dissolved in the liquid phase. The mixture of structuring agent and liquified or supercritical gas may contain additional substances, such as for instance oil. We have found that the addition of oil may reduce sintering of the micronised particles of the structuring agent.
The mixture containing structuring agent and liquefied or supercritical gas is depressurized over a small orifice or nozzle, to break up the mixture into small droplets. The break-up of the mixture into droplets can be assisted e.g.
by internals inside the nozzle before the orifice to generate a whirl, or by passing a gas at a high flow rate near the orifice.
The mixture is depressurized into a volume where the pressure is higher than, equal to or lower than atmospheric pressure.
5 We have found that sintering, agglomeration and ripening of micronised particles of the structuring agent will lead to a reduced performance of the particles for structuring the dispersion.
10 To avoid sintering, agglomeration and/or ripening of the micronised particles, preferably a gas jet is applied in addition to the flow of the spray jet. The additional gas jet is most effective when the gas jet is positioned such that recirculation of material expanded through the orifice 15 is reduced or avoided. Especially advantageous is a position wherein the gas from the gas jet flows essentially tangentially to the flow direction of the spray jet. Most advantageously the gas inlet for the gas jet is positioned behind the exit of the nozzle, see figure 2 of PCT/EP2004/006544. This figure shows that the additional gas inlet (1) behind the exit of the nozzle (2) creates a gas flow (3) tangentially to the flow of the spray jet (4).
A further preferred edible dispersion according to the invention is a dispersion of a solid matter, preferably a dry particulate matter, dispersed in a continuous phase of oil and structuring agent. Preferred material for the dry particulate matter is one or more of flour, starch, salt, herbs (e.g. dried herbs), spices and mixtures thereof.
Preferably in such dispersions, the amount of solid matter is 30-75 wt.%, more preferably 40-65 wt.% based on total weight of the dispersion.
content (wt.%) is herein expressed based on the weight of the fat phase.
In a preferred embodiment, the low-fat emulsion spread comprises from 3 to 25 wt.% sterol, more preferred from 7 to 15 wt.% sterol.
Preferably the spreadable edible dispersions according to the invention has a low water droplet size, preferably the water droplet size as defined herein is 10 pm or less, more preferably 5 pm or less.
According to the invention, the dispersion is formed by mixing oil, the solid structuring agent particles comprising sterols, and the other phase or phases of the dispersion, such as for example an aqueous phase, a solid phase and/or a gas phase.
According to the invention, the solid structuring agent particles (also described herein as secondary particles) should have a microporous structure of submicron size particles (also described herein as primary particles) and further they comprise sterol.
The secondary particles are agglomerates of primary particles which have a microporous structure. The size of the primary particles is submicron (that is they have a diameter below 1u).
An example of a microporous structure is shown in figures 6 and 7 of PCT/EP2004/006544. The primary particles typically have the shape as shown in figure 7, in which the platelets with submicron dimensions are the primary particles. The thickness of the platelets should be submicron, preferably the thickness is on average 0.01-0.5pm, more preferably 0.03-0.2pm, even more preferably 0.06-0.12}im.
Equivalent good results were obtained for a secondary particles having a microporous structure of more bubble-like shape, such as shown in figure 10 of PCT/EP2004/006544. In such microporous structure the wall thickness of-the bubbles should be submicron, for instance on average 0.01-0.5um, more preferably 0.03-0.2pm, even more preferably 0.06-0.12pm.
The secondary particles, may, in the course of the preparation of the dispersion, for instance through the force of a mixer, be broken into submicron particles. The resulting submicron particles will form the structuring network of the dispersion.
The structuring agent comprises sterol. Where reference is made to sterol this includes the saturated stanols and esterified derivatives of sterol/stanol or mixtures of any of these.
In this application where reference is made to sterolester, this also includes their saturated derivatives, the stanol esters, and combinations of sterol- and stanol esters.
5 Sterols or phytosterols, also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 4,4'-dimethylsterols. In oils they mainly exist as free sterols and sterol esters of fatty acids although sterol glucosides 10 and acylated sterol glucosides are also present. There are three major phytosterols namely beta-sitosterol, stigmasterol and campesterol. Schematic drawings of the components meant are as given in "Influence of Processing on Sterols of Edible Vegetable Oils", S.P. Kochhar; Prog.
Lipid Res. 22: pp. 161-188.
The respective 5 alpha- saturated derivatives such as sitostanol, campestanol and ergostanol and their derivatives are in this specification referred to as stanols.
Preferably the (optionally esterified) sterol or stanol is selected from the group comprising fatty acid ester of (3-sitosterol, (3-sitostanol, campesterol, campestanol, stigmasterol, brassicasterol, brassicastanol or a mixture thereof.
The sterols or stanols are optionally at least partly esterified with a fatty acid. Preferably the sterols or stanols are esterified with one or more C2_22 fatty acids.
For the purpose of the invention the term C2_22 fatty acid refers to any molecule comprising a C2_22 main chain and at least one acid group. Although not preferred within the present context the C2-22 main chain may be partially substituted or side chains may be present. Preferably, however the C2_22 fatty acids are linear molecules comprising one or two acid group(s) as end group(s). Most preferred are linear C8-22 fatty acids as these occur in natural oils.
Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, lactic acid, oxalic acid and maleic acid. Most preferred are myristic acid, lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid.
When desired a mixture of fatty acids may be used for esterification of the sterols or stanols. For example, it is possible to use a naturally occurring fat or oil as a source of the fatty acid and to carry out the esterification via an interesterification reaction.
The amount of sterol in the structuring agent is preferably from 80 to 100 wt.% on total weight of the structuring agent.
Preferably, the structuring agent comprises edible lipid, more preferably it is edible fat. Edible fats consist predominantly of triglycerides. Typically such edible fats suitable as structuring agent are mixtures of triglycerides, some of which have a melting point higher than room or ambient temperature and therefore contain solids in the form of crystals.
The solid structuring agent, also denoted as hardstock, serves to structure the fat phase and helps to stabilise the dispersion.
For imparting to common margarine a semi-solid, plastic, spreadable consistency this stabilising and structuring functionality plays an important role. The crystals of the solid fat form a network throughout the liquid oil resulting into a structured fat phase. The aqueous phase droplets are fixed within the spaces of the lattice of solid fat crystals. In this way coalescence of the droplets and separation of the heavier aqueous phase from the fat phase is prevented.
The process according to the invention may be executed batch-wise or continuous. Conventional unit operations and apparatus, e.g. mixers, pumps and extruders may be used. A
suitable process flow diagram for a continuous process according to the invention is given in figure 1. Micronised fat may be added to the premix or via the inlet (5), preferably at least part of the micronised fat is added via inlet (5).
Further common ingredients of the fat phase are emulsifiers, such as monoglycerides and lecithin, colouring agents and flavours.
The solid structuring agent particles (secondary particles) preferably have an average particle size (D3,2) of 60 micrometer or less, more preferably the solid structuring agent particles have an average particle size of 30 micrometer or less. The average particle size (D3,2) is determined as indicated in the examples.
Preferably the solid structuring agent particles are prepared using a micronisation process. In the micronisation process the solid structuring agent particles are prepared by preparing a homogeneous mixture of structuring agent and liquified gas or supercritical gas at a pressure of 5-40 MPa and expanding the mixture through an orifice, under such conditions that a spray jet is applied in which the structuring agent is solidified and micronised. The liquified gas or supercritical gas may be any gas that may be used in the preparation of food products, for example carbondioxide, nitrogen, propane, ethane, xenon or other noble gases. Carbondioxide and propane are preferred. Carbondioxide is most preferred.
Advantages of carbondioxide are that it has a mild (31 C) critical temperature, it is non-flammable, nontoxic, environmentally friendly and it may be obtained from existing industrial processes without further contribution to the greenhouse effect. It is fairly miscible with oil and is readily recovered owing to its high volatility at ambient conditions. Finally liquid CO2 is the second least expensive solvent after water.
The temperature of the mixture of structuring agent and liquified gas or supercritical gas is preferably such that the mixture forms a homogeneous mixture. Advantageously, the temperature of the mixture of structuring agent and liquified gas or supercritical gas is below the slip melting point of the structuring agent at atmospheric pressure and above the temperature at which phase separation of the mixture occurs. Under such conditions the smallest micronised particles may be obtained.
The pressure and temperature of the mixture of structuring agent and liquefied or supercritical gas is preferably such that a large amount of the gas may be dissolved in the structuring agent. The amount dissolved will be determined by the phase diagram of the mixture of structuring agent and liquified or supercritical gas. At higher pressures as well as at lower temperatures more gas will dissolve in the structuring agent.
Preferably the temperature and pressure are chosen such that 10 wt.% or more, more preferably 20 wt.% or more or most preferably 30 wt.% or more of gas is dissolved in the liquid phase. The mixture of structuring agent and liquified or supercritical gas may contain additional substances, such as for instance oil. We have found that the addition of oil may reduce sintering of the micronised particles of the structuring agent.
The mixture containing structuring agent and liquefied or supercritical gas is depressurized over a small orifice or nozzle, to break up the mixture into small droplets. The break-up of the mixture into droplets can be assisted e.g.
by internals inside the nozzle before the orifice to generate a whirl, or by passing a gas at a high flow rate near the orifice.
The mixture is depressurized into a volume where the pressure is higher than, equal to or lower than atmospheric pressure.
5 We have found that sintering, agglomeration and ripening of micronised particles of the structuring agent will lead to a reduced performance of the particles for structuring the dispersion.
10 To avoid sintering, agglomeration and/or ripening of the micronised particles, preferably a gas jet is applied in addition to the flow of the spray jet. The additional gas jet is most effective when the gas jet is positioned such that recirculation of material expanded through the orifice 15 is reduced or avoided. Especially advantageous is a position wherein the gas from the gas jet flows essentially tangentially to the flow direction of the spray jet. Most advantageously the gas inlet for the gas jet is positioned behind the exit of the nozzle, see figure 2 of PCT/EP2004/006544. This figure shows that the additional gas inlet (1) behind the exit of the nozzle (2) creates a gas flow (3) tangentially to the flow of the spray jet (4).
A further preferred edible dispersion according to the invention is a dispersion of a solid matter, preferably a dry particulate matter, dispersed in a continuous phase of oil and structuring agent. Preferred material for the dry particulate matter is one or more of flour, starch, salt, herbs (e.g. dried herbs), spices and mixtures thereof.
Preferably in such dispersions, the amount of solid matter is 30-75 wt.%, more preferably 40-65 wt.% based on total weight of the dispersion.
The amount of structuring agent should be such that a suitably stable dispersion is obtained. When the structuring agent is micronised sterol or a combination of micronised sterol and micronised fat, the amount is preferably 1-20 wt.%, more preferably 4-12 wt.% based on total weight of the dispersion.
Description of the figures Fig. 1 Process flow diagram for a continuous process.
(1) designates a premix vessel, (2) a pump, (3) a high shear mixer, (4) an extruder type mixer and (5) a feed entrance for micronised fat.
Examples General Method to determine slip melting point The slip melting point of structuring agent is determined in accordance with F. Gunstone et al, The Lipid Handbook, second edition, Chapman and Hall, 1995, page 321, Point 6.2.3, Slip point.
Method to determine D3,2 of the particle size distribution of micronised fat particles Low-angle laser light scattering (LALLS, Helos Sympatic) was used to measure the average particle size (D3,2). The fat particles were suspended in water in a quixel flow cuvette with an obscuration factor of 10-20%. The diffraction pattern was measured at 632.8 nm with a lens focus of 100 mm and a measurement range of 0.5-175 pm.
Calculations were bases on the Fraunhofer theory.
A full description of the principle of LALLS is given in ISO 13320-1.
Method to determine D3,3 of water droplet size distribution in an emulsion The water droplet size was measured using a well-known low resolution NMR measurement method. Reference is made to Van den Enden, J.C., Waddington, D., Van Aalst, H., Van Kralingen, C.G., and Packer, K.J., Journal of Colloid and Interface Science 140 (1990) p. 105.
Method to determine oil exudation Oil exudation is determined by measuring the height of the free oil layer that appears on top of the product. This free oil layer is considered a product defect. In order to measure oil exudation, the product is filled into a scaled glass cylinder of 50 ml. The filling height is 185 mm. The filled cylinder is stored in a cabinet at constant temperature (15 C). Height measurements are executed every week, by measuring the height of the exuded oil layer in mm with a ruler. Oil exudation is expressed as the height of the exuded oil layer divided by the original filling height and expressed in %. Shaking of the cylinders should be avoided.
Description of the figures Fig. 1 Process flow diagram for a continuous process.
(1) designates a premix vessel, (2) a pump, (3) a high shear mixer, (4) an extruder type mixer and (5) a feed entrance for micronised fat.
Examples General Method to determine slip melting point The slip melting point of structuring agent is determined in accordance with F. Gunstone et al, The Lipid Handbook, second edition, Chapman and Hall, 1995, page 321, Point 6.2.3, Slip point.
Method to determine D3,2 of the particle size distribution of micronised fat particles Low-angle laser light scattering (LALLS, Helos Sympatic) was used to measure the average particle size (D3,2). The fat particles were suspended in water in a quixel flow cuvette with an obscuration factor of 10-20%. The diffraction pattern was measured at 632.8 nm with a lens focus of 100 mm and a measurement range of 0.5-175 pm.
Calculations were bases on the Fraunhofer theory.
A full description of the principle of LALLS is given in ISO 13320-1.
Method to determine D3,3 of water droplet size distribution in an emulsion The water droplet size was measured using a well-known low resolution NMR measurement method. Reference is made to Van den Enden, J.C., Waddington, D., Van Aalst, H., Van Kralingen, C.G., and Packer, K.J., Journal of Colloid and Interface Science 140 (1990) p. 105.
Method to determine oil exudation Oil exudation is determined by measuring the height of the free oil layer that appears on top of the product. This free oil layer is considered a product defect. In order to measure oil exudation, the product is filled into a scaled glass cylinder of 50 ml. The filling height is 185 mm. The filled cylinder is stored in a cabinet at constant temperature (15 C). Height measurements are executed every week, by measuring the height of the exuded oil layer in mm with a ruler. Oil exudation is expressed as the height of the exuded oil layer divided by the original filling height and expressed in %. Shaking of the cylinders should be avoided.
Stevens value Stevens values give an indication about the firmness of a product. The firmness of all products stored at 5 C for 24 hours was measured at room temperature using a Stevens Texture Analyser (1 mm/sec, 25 mm depth, 4.4. mm probe) and is quoted herein as the Stevens value (in g).
Example 1: Preparation of a spreadable margarine A high-fat spreadable margarine was prepared with the composition shown in table 1:
Table 1: Composition of high-fat spreadable margarine Ingredient Amount (wt.%) Oil phase Sunflower oil 59.68 Micronised fat powder 9.64 comprising steroll Lecithin Bolec ZT 0.32 Emulsifier Hymono 8903 0.20 beta-carotene (0.4 wt.% 0.15 solution in sunflower oil) Water phase Water 29.65 Potassium sorbate 0.08 Sodium chloride 0.28 1Hardstock fat as prepared in example 1 and 2 of EP-A-89082 which was micronised as in example 1 of PCT/EP2004/006544. This hardstock was mixed with 50 wt.%
beta sitbsterol.
The wat-er phase was prepared by adding salt and potassium sorbate to distilled water and adjusting the pH of distilled water from 7.7 to 4.0 using 5 wt.% solution of citric acid in water, and heated for 5 minutes in a bath of 60 C to dissolve the solids. The oil phase was prepared by dissolving the emulsifier ingredients and 0-carotene in the total amount of sunflower oil at 60 C and cooled down to 15 C afterwards. Subsequently the micronised fat powder was added to the oil phase carefully using a spatula and the oil phase was mixed with a kitchen mixer (Philips Essence HR1357/05) for 2 minutes. Then the water phase was added to the oil phase and the resulting mixture was mixed with the mixer for another 5 minutes at ambient temperature. A
droplet size (D3,3) of about 10pm was obtained. The spread was put in a margarine tub and stored at 5 C. Results in table 3.
Example 2: Preparation of a low-fat spread A low-fat (33 wt.% fat) spreadable margarine spread was prepared with the composition shown in table 2:
Table 2: Composition of low-fat spread Ingredient Amount (wt.%) Oil phase Sunflower oil 27.65 Micronised fat powder as 4.59 in example 1 Lecithin Bolec ZT' 0.32 Emulsifier Hymono 8903 0.33 (monoglyceride) Beta-carotene (0.4 wt.o 0.15 solution in sunflower =oil) Water phase Water 66.60 Potassium sorbate 0.08 Sodium chloride 0.28 The micronised fat powder was mixed with half of the oil to obtain a fat powder/oil slurry. The fat/oil slurry was then stirred manually in the remainder of the oil to make the oil phase. In the next step the oil phase (slurry) was put 5 in an EscoLabor device and half of the water phase was added to the oil phase. The EscoLabor vessel was kept at 5 C. The water and oil phase were mixed under vacuum.
The scraper speed was found to be 80% of the maximum 10 rotational speed and power of the Ultra Turrax was found to be optimal at 50% of maximum power. During the mixing of the oil- and water phases the remaining amount of water was added cautiously within 5 minutes. This yielded a homogeneous but very thick fat continuous product after 15 15 minutes. After 15 a droplet size (D3,3) of 3pm was obtained. This low fat spread was evaluated after 4 weeks of storage at 5 C. Results are given in table 3.
Table 3: Stevens values and fat level low-fat micronised 20 fat spread Example Fat level Stevens value M at 5 C (g) Example 1 70 88 Example 2 33 112 Example 3 A spread was produced with a composition as in table 4. A
stable spread resulted. The water phase was made by mixing the salt in distilled water and holding the mixture at room temperature. The fat phase was produced by adding the micronised fat powder to liquid oil using a spatula. The water phase and the oil phase were mixed using a home kitchen mixer.
It was possible to prepare a stable spread without emulsifier and thickener. The long term stability and/or consistency of the spread without emulsifier may be improved by adding a thickener to the water phase, e.g. 1 wt.% starch, a suitable starch type is Resistamyl 310.
Table 4: composition of example 3 Ingredient Amount (wt.%) Oil Phase Sunflower oil 33.87 Micronised fat powder 5.98 as in example 1 Beta-carotene (0.4 0.15 wt.% solution in Sunflower oil) Water phase Water 59.5 Salt 0.5
Example 1: Preparation of a spreadable margarine A high-fat spreadable margarine was prepared with the composition shown in table 1:
Table 1: Composition of high-fat spreadable margarine Ingredient Amount (wt.%) Oil phase Sunflower oil 59.68 Micronised fat powder 9.64 comprising steroll Lecithin Bolec ZT 0.32 Emulsifier Hymono 8903 0.20 beta-carotene (0.4 wt.% 0.15 solution in sunflower oil) Water phase Water 29.65 Potassium sorbate 0.08 Sodium chloride 0.28 1Hardstock fat as prepared in example 1 and 2 of EP-A-89082 which was micronised as in example 1 of PCT/EP2004/006544. This hardstock was mixed with 50 wt.%
beta sitbsterol.
The wat-er phase was prepared by adding salt and potassium sorbate to distilled water and adjusting the pH of distilled water from 7.7 to 4.0 using 5 wt.% solution of citric acid in water, and heated for 5 minutes in a bath of 60 C to dissolve the solids. The oil phase was prepared by dissolving the emulsifier ingredients and 0-carotene in the total amount of sunflower oil at 60 C and cooled down to 15 C afterwards. Subsequently the micronised fat powder was added to the oil phase carefully using a spatula and the oil phase was mixed with a kitchen mixer (Philips Essence HR1357/05) for 2 minutes. Then the water phase was added to the oil phase and the resulting mixture was mixed with the mixer for another 5 minutes at ambient temperature. A
droplet size (D3,3) of about 10pm was obtained. The spread was put in a margarine tub and stored at 5 C. Results in table 3.
Example 2: Preparation of a low-fat spread A low-fat (33 wt.% fat) spreadable margarine spread was prepared with the composition shown in table 2:
Table 2: Composition of low-fat spread Ingredient Amount (wt.%) Oil phase Sunflower oil 27.65 Micronised fat powder as 4.59 in example 1 Lecithin Bolec ZT' 0.32 Emulsifier Hymono 8903 0.33 (monoglyceride) Beta-carotene (0.4 wt.o 0.15 solution in sunflower =oil) Water phase Water 66.60 Potassium sorbate 0.08 Sodium chloride 0.28 The micronised fat powder was mixed with half of the oil to obtain a fat powder/oil slurry. The fat/oil slurry was then stirred manually in the remainder of the oil to make the oil phase. In the next step the oil phase (slurry) was put 5 in an EscoLabor device and half of the water phase was added to the oil phase. The EscoLabor vessel was kept at 5 C. The water and oil phase were mixed under vacuum.
The scraper speed was found to be 80% of the maximum 10 rotational speed and power of the Ultra Turrax was found to be optimal at 50% of maximum power. During the mixing of the oil- and water phases the remaining amount of water was added cautiously within 5 minutes. This yielded a homogeneous but very thick fat continuous product after 15 15 minutes. After 15 a droplet size (D3,3) of 3pm was obtained. This low fat spread was evaluated after 4 weeks of storage at 5 C. Results are given in table 3.
Table 3: Stevens values and fat level low-fat micronised 20 fat spread Example Fat level Stevens value M at 5 C (g) Example 1 70 88 Example 2 33 112 Example 3 A spread was produced with a composition as in table 4. A
stable spread resulted. The water phase was made by mixing the salt in distilled water and holding the mixture at room temperature. The fat phase was produced by adding the micronised fat powder to liquid oil using a spatula. The water phase and the oil phase were mixed using a home kitchen mixer.
It was possible to prepare a stable spread without emulsifier and thickener. The long term stability and/or consistency of the spread without emulsifier may be improved by adding a thickener to the water phase, e.g. 1 wt.% starch, a suitable starch type is Resistamyl 310.
Table 4: composition of example 3 Ingredient Amount (wt.%) Oil Phase Sunflower oil 33.87 Micronised fat powder 5.98 as in example 1 Beta-carotene (0.4 0.15 wt.% solution in Sunflower oil) Water phase Water 59.5 Salt 0.5
Claims (8)
1. Process for the preparation of a spreadable edible dispersion having a fat content of 70 wt.% or less, wherein a mixture of oil and solid structuring agent particles is subjected to stirring and an aqueous phase is added to the mixture until a dispersion is obtained, wherein the solid structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5µm and further the solid structuring agent particles comprise sterol.
2. Process according to claim 1, wherein the solid structuring agent particles additionally comprise edible lipid.
3. Process according to claim 2, wherein the lipid is a fat.
4. Process according to any of claims 1 to 3, wherein the solid structuring agent particles are prepared using a micronisation process.
5. Spreadable edible dispersion having a fat content of 70 wt.% or less comprising micronised structuring agent particles wherein said structuring agent particles, also described as secondary particles, have a microporous structure and said particles are agglomerates of primary particles of submicron size, said primary particles are platelets having an average thickness of 0.01-0.5µm, wherein the dispersion has a Stevens value, measured at room temperature as defined herein of 30g or more, preferably 50g or more, more preferably 80g or more and most preferably 100g or more, said solid structuring agent particles of the dispersion also comprising sterol.
6. Spreadable edible dispersion according to claim 5, wherein the dispersion is a low-fat water-in-oil emulsion spread having a fat content of 45 wt.% or less, more preferred 33-45 wt.%.
7. Low-fat emulsion spread according to claim 5 comprising from 3 to 25 wt.% sterol, more preferred from 7 to 15 wt.% sterol.
8. Spreadable edible dispersion according to any of claims 5-7, wherein the dispersion has a water droplet size as defined herein of 5µm or less.
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
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EP05075393.8 | 2005-02-17 | ||
EP05075384 | 2005-02-17 | ||
EP05075392 | 2005-02-17 | ||
EP05075384.7 | 2005-02-17 | ||
EP05075392.0 | 2005-02-17 | ||
EP05075393 | 2005-02-17 | ||
EP05075391 | 2005-02-17 | ||
EP05075391.2 | 2005-02-17 | ||
PCT/EP2006/000802 WO2006087093A1 (en) | 2005-02-17 | 2006-01-25 | Process for the preparation of a spreadable dispersion comprising sterol |
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CA002597478A Abandoned CA2597478A1 (en) | 2005-02-17 | 2006-01-25 | Granules comprising sterol |
CA2598401A Active CA2598401C (en) | 2005-02-17 | 2006-01-25 | Process for the preparation of a spreadable dispersion |
CA2595381A Active CA2595381C (en) | 2005-02-17 | 2006-01-25 | Fat granules |
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CA002597478A Abandoned CA2597478A1 (en) | 2005-02-17 | 2006-01-25 | Granules comprising sterol |
CA2598401A Active CA2598401C (en) | 2005-02-17 | 2006-01-25 | Process for the preparation of a spreadable dispersion |
CA2595381A Active CA2595381C (en) | 2005-02-17 | 2006-01-25 | Fat granules |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8025913B2 (en) | 2003-07-17 | 2011-09-27 | Conopco Inc. | Process for the preparation of an edible dispersion comprising oil and structuring agent |
PL1865786T5 (en) | 2005-02-17 | 2015-12-31 | Unilever Bcs Europe Bv | Process for the preparation of a spreadable dispersion |
AU2007300463B2 (en) * | 2006-09-27 | 2012-08-16 | Conagra Foods Rdm, Inc. | Seasoning and method for enhancing and potentiating food flavor utilizing microencapsulation |
ATE460849T1 (en) * | 2006-11-17 | 2010-04-15 | Huegli Holding Ag | GRANULAR FOOD CONCENTRATE |
EP2367436B1 (en) * | 2008-12-19 | 2012-10-03 | Unilever NV | Process for the preparation of an edible fat continuous spread |
AU2009328392B2 (en) | 2008-12-19 | 2013-08-22 | Upfield Europe B.V. | Edible fat powders |
WO2010069753A1 (en) * | 2008-12-19 | 2010-06-24 | Unilever Nv | Process for the preparation of an edible fat continuous spread |
US20110311707A1 (en) * | 2008-12-19 | 2011-12-22 | Albert Jan Bezemer | Process for the preparation of an edible fat continuous food product |
EP2367437B1 (en) * | 2008-12-19 | 2014-03-05 | Unilever NV | Process for the preparation of a fat continuous spread |
JP5767317B2 (en) * | 2010-04-30 | 2015-08-19 | ローダース・クロクラーン・ベスローテンフェンノートシャップ | Edible oil composition |
AU2011254858B2 (en) | 2010-05-18 | 2014-03-27 | Upfield Europe B.V. | Edible fat continuous spreads |
WO2011160921A1 (en) | 2010-06-22 | 2011-12-29 | Unilever Nv | Edible fat powders |
CA2820354C (en) | 2010-12-17 | 2019-06-11 | Unilever Plc | Process of compacting a microporous fat powder and compacted fat powder so obtained |
PL2651229T3 (en) | 2010-12-17 | 2015-08-31 | Unilever Bcs Europe Bv | Edible water in oil emulsion |
EP2654444B1 (en) * | 2010-12-22 | 2015-05-06 | Unilever N.V. | Edible fat continuous emulsion comprising plant sterol esters |
CA2828892C (en) | 2011-04-08 | 2016-10-11 | H R D Corporation | High shear application in processing oils |
EP2757891B1 (en) | 2011-09-19 | 2017-06-14 | Unilever N.V. | Process to manufacture edible low-fat water-in-oil emulsions |
WO2013079279A1 (en) * | 2011-11-30 | 2013-06-06 | Unilever N.V. | Process for the preparation of edible fat-continuous spreads |
EP3132685B1 (en) * | 2012-04-27 | 2018-08-29 | General Mills, Inc. | Dough composition |
WO2014044582A1 (en) | 2012-09-21 | 2014-03-27 | Unilever N.V. | Edible water-in-oil emulsion and a process for preparing such emulsion |
PL2897463T3 (en) | 2012-09-21 | 2019-08-30 | Upfield Europe B.V. | Edible water-in-oil emulsions and a process for preparing such emulsions |
HUE027785T2 (en) | 2012-10-08 | 2016-11-28 | Unilever Nv | Process for preparation of a spreadable edible emulsion |
DE102012021545A1 (en) | 2012-10-29 | 2014-04-30 | ETH Zürich | Fat system, e.g. Food fat system, cosmetic fat system, pharmaceutical fat system and product for use in fatty foods, cosmetics or pharmaceuticals |
EP2950660B1 (en) | 2013-01-31 | 2016-04-06 | Unilever N.V. | Process for the manufacture of edible water-in-oil emulsions |
BR112017007489B1 (en) | 2014-10-13 | 2022-02-15 | Upfield Europe B.V. | PROCESS FOR PREPARING AN EDIBLE FAT PASTE AND PROCESS FOR MANUFACTURING A CONTINUOUS EDIBLE OIL EMULSION |
HUE052653T2 (en) | 2014-10-13 | 2021-05-28 | Upfield Europe Bv | Process for preparing a fat slurry and for preparing a spread with said slurry |
EP3217802A1 (en) * | 2014-10-17 | 2017-09-20 | Unilever NV | Edible aerated water-in-oil emulsions |
UA123395C2 (en) | 2015-03-18 | 2021-03-31 | Карджилл, Інкорпорейтед | Low-fat water-in-oil emulsion |
TR201901388T4 (en) * | 2015-05-28 | 2019-02-21 | Unilever Nv | Process for Preparing Oil Slurries and A Process for Preparing Emulsions of These Slurries |
CN105087157B (en) * | 2015-08-18 | 2018-11-13 | 沈阳药科大学 | A kind of process for refining and application thereof of low sterol injection perilla oil |
US20180228190A1 (en) * | 2015-08-25 | 2018-08-16 | Conopco, Inc., D/B/A Unilever | A shaped savoury concentrate article |
EP3629750B1 (en) * | 2017-05-31 | 2023-09-06 | Upfield Europe B.V. | Porous micronised fat powder, a process for preparing such, and a process of using such |
US11510418B2 (en) | 2017-07-24 | 2022-11-29 | Upfield Europe B.V. | Process for mixing liquid edible oil and a melted edible fat |
JP7182630B2 (en) | 2017-11-27 | 2022-12-02 | カーギル インコーポレイテッド | double emulsion |
CA3086394A1 (en) | 2017-12-22 | 2019-06-27 | Unilever Bcs Limited | Hardstock fat composition |
WO2020015807A1 (en) | 2018-07-20 | 2020-01-23 | Pascal Guillet | Micro-foamed, multi-phase fat powder and use of such a fat powder |
US20240057643A1 (en) * | 2022-08-16 | 2024-02-22 | Empirical Innovations, Inc. | Comminuted meat products and apparatuses and methods for producing comminuted meat products |
Family Cites Families (242)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2521242A (en) | 1947-11-06 | 1950-09-05 | Procter & Gamble | Permanently pumpable oleaginous suspension |
US2521219A (en) * | 1947-11-06 | 1950-09-05 | Procter & Gamble | Process for preparing suspensions of solid triglyceride and liquid oil |
US2615160A (en) * | 1949-05-28 | 1952-10-21 | Procter & Gamble | Mixed triglycerides |
US2815286A (en) * | 1955-10-28 | 1957-12-03 | Procter & Gamble | Liquid shortening |
US3120438A (en) * | 1958-11-03 | 1964-02-04 | Dairy Foods Inc | Fat-containing dried dairy product and method of manufacture |
US3170799A (en) * | 1961-11-28 | 1965-02-23 | Reuben O Feuge | Process of preparing stable triglycerides of fat forming acids |
US3270040A (en) * | 1963-06-27 | 1966-08-30 | Betty L Bradshaw | Process of preparing stable triglycerides of fat forming acids |
GB1114674A (en) * | 1963-12-11 | 1968-05-22 | Symington Vending Scotland Ltd | Improvements in or relating to dispensing apparatus for liquids |
US3338720A (en) * | 1964-01-07 | 1967-08-29 | Swift & Co | Fluid margarine emulsion stabilized by hard fat |
DE1492943A1 (en) * | 1964-11-02 | 1969-09-04 | Procter & Gamble | Process for the preparation of an oil-based gel |
US3295986A (en) * | 1964-12-17 | 1967-01-03 | Gen Foods Corp | Powdered fat compositons and process for manufacture |
NO116030B (en) * | 1965-12-01 | 1969-01-13 | Mo Och Domsjoe Ab | |
US3528823A (en) * | 1966-08-04 | 1970-09-15 | Lever Brothers Ltd | Fluid shortening |
US3425643A (en) * | 1966-11-21 | 1969-02-04 | Frank H Lemon | Combined spinning and casting reel |
US3433650A (en) | 1967-01-12 | 1969-03-18 | Gen Foods Corp | Dry soup mix |
LU55603A1 (en) | 1968-03-01 | 1969-02-05 | ||
US3892880A (en) * | 1969-08-19 | 1975-07-01 | Erhard Grolitsch | Method for the manufacture of crystalline, flowable, stable fat powders or mixtures of such fat powders with other powdery materials |
DE2018592C3 (en) * | 1970-04-17 | 1978-03-23 | Windmoeller & Hoelscher, 4540 Lengerich | Device for forming cuboid bag packages |
GB1382573A (en) | 1971-01-06 | 1975-02-05 | Unilever Ltd | Confectioners butter |
DE2253515C3 (en) | 1972-10-28 | 1978-07-06 | Fa. E. Kampffmeyer, 2000 Hamburg | Process for converting molten substances, in particular fats and fat mixtures, into powdered concentrates by spraying |
AR207341A1 (en) * | 1973-03-15 | 1976-09-30 | Fujisawa Pharmaceutical Co | A PROCEDURE FOR THE PREPARATION OF 2-ALKYL-2 OR 3-CEFEM-4-CARBOXYL ACID DERIVATIVES |
US3881005A (en) * | 1973-08-13 | 1975-04-29 | Lilly Co Eli | Pharmaceutical dispersible powder of sitosterols and a method for the preparation thereof |
FR2243653A1 (en) | 1973-09-18 | 1975-04-11 | Midi Salines Est Cie Salins | Incorporation of alkali metal chlorides in media - with oil-based preservative |
CA1081031A (en) | 1975-08-19 | 1980-07-08 | Polak's Frutal Works | Dust-free, free-flowing hydrolyzed proteins |
US4160850A (en) * | 1975-08-25 | 1979-07-10 | General Mills, Inc. | Shelf-stable mix for a spreadable butter-substitute |
GB1537011A (en) | 1976-02-13 | 1978-12-29 | Nestle Sa | Water-dispersible composition and process for its production |
US4021582A (en) | 1976-02-13 | 1977-05-03 | Societe D'assistance Technique Pour Produits Nestle S.A. | Water-dispersible composition and process for production |
US4234606A (en) * | 1978-08-03 | 1980-11-18 | Scm Corporation | Fluid shortening |
US4226894A (en) * | 1978-11-13 | 1980-10-07 | Scm Corporation | Hydrated stable fluent shortening containing solid phase emulsifier components |
US4232052A (en) * | 1979-03-12 | 1980-11-04 | National Starch And Chemical Corporation | Process for powdering high fat foodstuffs |
US4234577A (en) | 1979-03-19 | 1980-11-18 | Z-L Limited Partnership | Ergostadientriols, compositions containing same, and methods of preparing and using same |
US4234696A (en) * | 1979-04-06 | 1980-11-18 | Monsanto Company | 2-Chloroethyl phosphonate compositions |
US4288460A (en) | 1979-05-24 | 1981-09-08 | Balchem Corporation | Non-caking, water-soluble, granular coated food ingredient |
US4385076A (en) * | 1979-06-13 | 1983-05-24 | The Procter & Gamble Company | Fat or oil composition containing microfine particles of flavor enhancer |
EP0021483B1 (en) | 1979-06-13 | 1984-02-08 | THE PROCTER & GAMBLE COMPANY | Flavor-enhancing composition and method of preparation thereof |
US4294862A (en) | 1979-09-19 | 1981-10-13 | Gerhard Wilke | Process for the production of pastry and flaky pastry-like products |
JPS604698B2 (en) * | 1979-12-07 | 1985-02-06 | 森永製菓株式会社 | Method for producing granulated cocoa |
NL8003144A (en) | 1980-05-30 | 1982-01-04 | Unilever Nv | FAT MIXTURE. |
US4341813A (en) | 1980-09-16 | 1982-07-27 | Nabisco Brands, Inc. | Edible fat product II |
NL182122C (en) | 1981-04-03 | 1988-01-18 | Douwe Egberts Tabaksfab | FLAVORED LEAF TEA AND TEA BAG WITH FLAVORED LEAF TEA. |
US4375483A (en) * | 1981-04-23 | 1983-03-01 | The Procter & Gamble Company | Fat composition containing salt, lecithin and hydrophilic silica |
US4388339A (en) | 1981-11-04 | 1983-06-14 | The Procter & Gamble Company | Margarine and method for making same |
US4390561A (en) | 1981-11-04 | 1983-06-28 | The Procter & Gamble Company | Margarine oil product |
US4391838A (en) * | 1981-11-13 | 1983-07-05 | Scm Corporation | Process for continuous fluidization of shortening |
FR2520003B1 (en) | 1982-01-20 | 1985-12-27 | Unilever Nv | FAT MIXTURE FOR MARGARINE WITH REDUCED PULVERULENCE TREND AND METHOD FOR REDUCING THE DEVELOPMENT OF PULVERULENCE IN FAT MIXTURES |
EP0089082B1 (en) † | 1982-03-12 | 1985-07-24 | Unilever N.V. | Margarine fat blend, and a process for producing said fat blend |
US4486457A (en) | 1982-03-12 | 1984-12-04 | Lever Brothers Company | Margarine fat blend, and a process for producing said fat blend |
US4391638A (en) * | 1982-04-22 | 1983-07-05 | J. M. Huber Corporation | Method for reclaiming ink waste |
DE3220916A1 (en) | 1982-06-03 | 1983-12-08 | Alexanderwerk Ag, 5630 Remscheid | Roller press for compacting pulverulent or fine-crystalline materials |
JPS5951742A (en) | 1982-09-16 | 1984-03-26 | Asahi Denka Kogyo Kk | Fluid oil or fat composition for baking |
US4469710A (en) | 1982-10-14 | 1984-09-04 | The Procter & Gamble Company | Pourable solid shortening |
JPS5951742U (en) | 1983-01-27 | 1984-04-05 | ト−ビ化成株式会社 | grain bag |
NL8304133A (en) * | 1983-12-01 | 1985-07-01 | Unilever Nv | WATER-IN-OIL EMULSIONS CONTAINING HYDRATED STARCH GRAINS. |
JPS60145055A (en) * | 1984-01-10 | 1985-07-31 | House Food Ind Co Ltd | Preparation of food containing granular fats and oils |
NL8501878A (en) | 1985-06-28 | 1987-01-16 | Ver Coop Melkind | MILK POWDER; METHOD FOR PREPARING THEREOF PROCESS FOR PREPARING MILK CHOCOLATE. |
DK159907C (en) * | 1986-02-14 | 1991-05-21 | Grindsted Prod As | PROCEDURE FOR THE MANUFACTURING OF ADDITIVES TO USE IN THE PREPARATION OF REASONED BAKERY PRODUCTS AND WHIPPED Desserts |
FI89448C (en) | 1986-03-06 | 1993-10-11 | Unilever Nv | FOERFARANDE FOER FRAMSTAELLNING AV EN BREDNING |
GB8607717D0 (en) | 1986-03-27 | 1986-04-30 | Unilever Plc | Hydratable powders |
JPS62239949A (en) | 1986-04-11 | 1987-10-20 | Snow Brand Milk Prod Co Ltd | Fat-containing milk powder easily dispersible in cold water |
JPS63186799A (en) * | 1987-01-29 | 1988-08-02 | 不二製油株式会社 | Production of powdery oils and fats |
US5302408A (en) | 1987-02-18 | 1994-04-12 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Edible plastified dispersion |
JP2601300B2 (en) | 1987-04-06 | 1997-04-16 | 旭化成工業株式会社 | Powdery or granular fats and oils and their production |
US5387431A (en) * | 1991-10-25 | 1995-02-07 | Fuisz Technologies Ltd. | Saccharide-based matrix |
US4889740A (en) * | 1987-05-22 | 1989-12-26 | Beatrice/Hunt-Wesson, Inc. | Pourable shortening and process for its preparation |
ATE115364T1 (en) | 1987-06-12 | 1994-12-15 | Asahi Denka Kogyo Kk | POWDERED FAT AND PREMIX CONTAINING THESE. |
GB8717960D0 (en) | 1987-07-29 | 1987-09-03 | St Ivel Ltd | Low fat spread |
CA1309954C (en) | 1987-07-29 | 1992-11-10 | Yasuo Yamada | Deaerator for particulates |
GB8802223D0 (en) | 1988-02-02 | 1988-03-02 | St Ivel Ltd | Low fat spread |
JP2624740B2 (en) | 1988-02-05 | 1997-06-25 | 旭電化工業株式会社 | Method for producing emulsion composition for roll-in |
US4952224A (en) | 1989-04-17 | 1990-08-28 | Canadian Oxygen Limited | Method and apparatus for cryogenic crystallization of fats |
JPH0827B2 (en) | 1989-05-13 | 1996-01-10 | 月島食品工業株式会社 | Plastic oil and fat and method for producing the same |
JPH0354198A (en) * | 1989-07-20 | 1991-03-08 | Shin Etsu Chem Co Ltd | Oxide garnet single crystal |
GB8922592D0 (en) | 1989-10-06 | 1989-11-22 | Unilever Plc | Bread improver compositions |
US5130156A (en) * | 1990-01-16 | 1992-07-14 | Henningsen Foods, Inc. | Method for agglomerating food powders |
GB9106011D0 (en) | 1991-03-21 | 1991-05-08 | Unilever Plc | Cream,churned product made therefrom and method of manufacturing them |
PL171695B1 (en) | 1991-11-04 | 1997-06-30 | Fuisz Technologies Ltd | Chewing gum |
US5620734A (en) † | 1992-03-05 | 1997-04-15 | Van Den Bergh Foods Co., Division Of Conopco, Inc. | Spreads and other products including mesomorphic phases |
EP0572051B1 (en) | 1992-04-29 | 1997-05-14 | Unilever N.V. | Liquid bread improvers |
JP2930487B2 (en) | 1992-10-21 | 1999-08-03 | ハウス食品株式会社 | Method for producing granular food |
US5352475A (en) | 1993-01-22 | 1994-10-04 | United Dominion Industries, Inc. | Process for the production of low-calorie spreads |
AU6786594A (en) | 1993-05-11 | 1994-12-12 | University Of North Carolina At Chapel Hill, The | Antisense oligonucleotides which combat aberrant splicing and methods of using the same |
CA2125914A1 (en) * | 1993-06-25 | 1994-12-26 | Pharmacia Corporation | Oil-coated microparticulated gellan gum |
SK279980B6 (en) | 1993-09-14 | 1999-06-11 | Unilever Nv | Glyceride fat, mixture with its content and its use |
US5391382A (en) * | 1994-01-31 | 1995-02-21 | Qualcepts Nutrients, Inc. | Low dust powdered cellulose |
SI9400079B (en) | 1994-02-15 | 2003-02-28 | Dr. Weidner Eckhard, Dipl. Ing. | Method and device for extraction and fractionation of small particles from solutions saturated with gas |
US5447735A (en) * | 1994-06-14 | 1995-09-05 | Miller; Van | Sweet cinnamon or other flavored, fat-based, anhydrous flakes for bakery purposes |
CA2156103A1 (en) | 1994-09-09 | 1996-03-10 | Michael David Erickson | Fat systems and processes for the production of no trans fatty acid containing stick-type margarines and spreads |
HU225666B1 (en) | 1994-11-15 | 2007-05-29 | Unilever Nv | Process for producing of fat blend for margarine and w/o spreads, the process fat blens and fat product comprising thereof |
HU225383B1 (en) | 1994-12-22 | 2006-11-28 | Unilever Nv | Margarine fat blend and plastic w/o emulsion spread comprising this fat blend |
DE69629502T2 (en) | 1995-06-01 | 2004-06-24 | Unilever N.V. | Fat-containing food products |
US6322842B1 (en) * | 1995-06-19 | 2001-11-27 | Van Den Bergh Foods Company, Division Of Conopco, Inc. | Water in oil stick product |
US5916608A (en) * | 1995-07-27 | 1999-06-29 | Van Den Bergh Foods Company, Division Of Conopco, Inc. | Dairy based spread and process of making |
EP0775444B1 (en) | 1995-10-25 | 2001-12-12 | Unilever N.V. | Pourable fat compositions |
DE19543254C1 (en) * | 1995-11-20 | 1997-05-28 | Cpc Maizena Gmbh | Shaped cream substitute and process for its manufacture |
ATE188093T1 (en) | 1995-11-10 | 2000-01-15 | Unilever Nv | EDIBLE SPREAD |
DE69615513T2 (en) | 1995-11-14 | 2002-05-08 | Unilever Nv | Edible spread |
EP0780058B1 (en) | 1995-12-19 | 1999-12-15 | Societe Des Produits Nestle S.A. | Process for producing powdered food products |
EP0796567A1 (en) | 1996-02-07 | 1997-09-24 | Societe Des Produits Nestle S.A. | Granular food product |
US6099887A (en) * | 1996-02-09 | 2000-08-08 | Lbi Acquisition Corp. | Process for preparing an edible laminated dough and edible lamination dispersion therefor |
US5904949A (en) | 1996-05-10 | 1999-05-18 | Van Den Bergh Foods Company, Division Of Conopco, Inc. | Water-in-oil emulsion spread |
DE69732239T2 (en) | 1996-05-10 | 2005-12-22 | Unilever N.V. | LIQUID FAT-CONTAINING COMPOSITION |
US5707670A (en) * | 1996-08-29 | 1998-01-13 | The Procter & Gamble Company | Use of bilayer forming emulsifiers in nutritional compositions comprising divalent mineral salts to minimize off-tastes and interactions with other dietary components |
FI105887B (en) * | 1996-09-27 | 2000-10-31 | Suomen Sokeri Oy | Products containing plant sterol for use in food and therapeutic applications, process for their preparation and their use |
GB9702886D0 (en) | 1996-09-28 | 1997-04-02 | Agglomeration Technology Ltd | Spray crystallised products and processes |
JPH1099037A (en) | 1996-09-30 | 1998-04-21 | Fuji Oil Co Ltd | Manufacture of soybean food material |
US6929816B2 (en) * | 1998-01-21 | 2005-08-16 | Raisio Benecol Ltd. | Fat compositions for use in food |
GB9624916D0 (en) * | 1996-11-29 | 1997-01-15 | Northern Telecom Ltd | Scaleable data network router |
GB2320175B (en) | 1996-12-16 | 2001-02-28 | Dalgety Food Ingredients Ltd | A food preservative and a method of making a food preservative |
US20040076732A1 (en) * | 1997-04-07 | 2004-04-22 | James Cook University | Food grade wax and process for preparing same |
WO1998047386A1 (en) | 1997-04-24 | 1998-10-29 | Unilever N.V. | Pourable fat compositions containing a thickener |
US6423363B1 (en) | 1997-08-22 | 2002-07-23 | Lipton, Division Of Conopco, Inc. | Aqueous dispersion |
ES2222553T3 (en) | 1997-08-22 | 2005-02-01 | Unilever N.V. | FAT-BASED FOOD PRODUCT THAT INCLUDES STEROLS. |
ES2229443T3 (en) * | 1997-08-22 | 2005-04-16 | Unilever N.V. | PROCEDURE FOR THE PRODUCTION OF ESTANOL ESTERES. |
DE69827330T2 (en) * | 1997-08-22 | 2006-02-02 | Unilever N.V. | Stanol ester-containing composition |
US6238926B1 (en) | 1997-09-17 | 2001-05-29 | Cargilll, Incorporated | Partial interesterification of triacylglycerols |
JP3492317B2 (en) | 1997-10-06 | 2004-02-03 | アーダルベルト−ラプス−シュティフツング | Process for producing powdery products from liquid substances or mixed substances |
DE19748069A1 (en) | 1997-10-31 | 1999-05-06 | Messer Griesheim Gmbh | Method and device for cooling and atomizing liquid or pasty substances |
US6020003A (en) * | 1998-02-23 | 2000-02-01 | Basf Corporation | Method of making spray-dried powders with high edible-oil loadings based on non-hydrolyzed gelatin |
US6117478A (en) * | 1998-03-12 | 2000-09-12 | Nestec S.A. | Method of making a reduced fat agglomerated chocolate |
FR2776167B1 (en) | 1998-03-18 | 2000-05-26 | Vedial Sa | WATER-IN-OIL FOOD EMULSION COMPRISING IN THE AQUEOUS PHASE OF PROBIOTIC LIVE BACTERIA, METHODS OF MANUFACTURE |
US6524637B2 (en) * | 1998-03-20 | 2003-02-25 | Danisco A/S | Composition providing a stable suspension of a particulate component |
US6190680B1 (en) * | 1998-04-01 | 2001-02-20 | The Nisshin Oil Mills, Ltd. | Oily composition and process for producing the same |
CA2327096A1 (en) * | 1998-04-01 | 1999-10-07 | Unilever Plc | Process for preparing a spread |
FI111513B (en) | 1998-05-06 | 2003-08-15 | Raisio Benecol Oy | Novel compositions of phytosterol and phytostanol fatty acid esters, products containing them and processes for their preparation |
US6318030B1 (en) | 1998-06-08 | 2001-11-20 | Paul Mains | Double depth crypt vault |
GB9817743D0 (en) | 1998-08-15 | 1998-10-14 | Agglomeration Technology Ltd | Oil product and manufacturing process |
ES2187201T3 (en) | 1998-10-14 | 2003-05-16 | Cognis Deutschland Gmbh | USE OF STEROLES AND STEROLESTERS TO NANOESCALA. |
US6077558A (en) | 1998-12-23 | 2000-06-20 | Bristol-Myers Squibb Company | Elemental nutritional products |
FR2787862B1 (en) | 1998-12-29 | 2001-01-26 | Carboxyque Francaise | METHOD AND DEVICE FOR REGULATED INJECTION OF LIQUID CARBON DIOXIDE INTO A PRESSURIZED LIQUID |
EP1146798A2 (en) | 1999-01-15 | 2001-10-24 | Nutrahealth Ltd. (UK) | Modified food products and beverages, and additives for food and beverages |
DE60004479T2 (en) * | 1999-02-03 | 2004-06-24 | Forbes Medi-Tech Inc., Vancouver | METHOD FOR PRODUCING PHYTOSTEROL OR PHYTOSTANOL MICROPARTICLES |
US6403144B1 (en) | 1999-04-30 | 2002-06-11 | The Procter & Gamble Co. | Food preparation compositions |
CA2375023C (en) | 1999-05-26 | 2009-01-20 | Asahi Denka Kogyo Kabushiki Kaisha | Plant sterol-containing fat composition and method for producing the same |
WO2001000046A1 (en) | 1999-06-25 | 2001-01-04 | Cognis Deutschland Gmbh | Use of nanoscale sterols and sterol esters |
EP1196042B1 (en) * | 1999-07-16 | 2011-08-10 | Unilever N.V. | Pourable fatty dispersions |
WO2001008648A1 (en) † | 1999-07-30 | 2001-02-08 | Stepan Company | Improved cold-mix water-in-oil emulsions comprising quaternary ammonium compounds and process for producing same |
US6616849B1 (en) | 1999-08-25 | 2003-09-09 | Shimadzu Corporation | Method of and system for continuously processing liquid materials, and the product processed thereby |
EP1211955A1 (en) | 1999-08-30 | 2002-06-12 | Ocean Nutrition Canada Ltd. | A nutritional supplement for lowering serum triglyceride and cholesterol levels |
CN1250113C (en) * | 1999-11-05 | 2006-04-12 | 拉伊西奥比尼考有限公司 | Edible fat blends |
EP1101409A3 (en) | 1999-11-16 | 2002-01-02 | Unilever N.V. | Edible fat based flakes |
RU2002118822A (en) | 1999-12-16 | 2004-01-27 | Унилевер Н.В. (NL) | Technological line and method for the production of edible fats |
GB0000159D0 (en) | 2000-01-06 | 2000-02-23 | Boc Group Plc | Processing food products |
WO2001066560A2 (en) | 2000-03-07 | 2001-09-13 | Forbes Medi-Tech Inc. | Novel derivatives comprising phytosterols and/or phytostanols and alpha-lipoic and use thereof in treating or preventing cardiovascular disease, its underlying conditions and other disorders |
GB0005736D0 (en) | 2000-03-09 | 2000-05-03 | G C Hahn Co Ltd | Low fat edible emulsions |
US20020132035A1 (en) * | 2001-01-10 | 2002-09-19 | Dov Tamarkin | Synthetic fat composition |
IL135466A (en) * | 2000-04-04 | 2006-07-05 | Sobhi Basheer | Process for selective alcoholysis of free sterols in fat-based product with an insoluble matrix-immobilized lipase complex |
CN1436047A (en) | 2000-04-14 | 2003-08-13 | 马尔斯公司 | Compositions and methods for improving vascular health |
US6743450B2 (en) * | 2000-04-14 | 2004-06-01 | Mars, Incorporated | Extraction of sterols from cocoa hulls |
MY122480A (en) | 2000-05-29 | 2006-04-29 | Premium Vegetable Oils Sdn Bhd | Trans free hard structural fat for margarine blend and spreads |
HU226354B1 (en) | 2000-06-01 | 2008-09-29 | Magyar Tejgazdasagi Kiserleti | Butter cream with live floka and process for its production |
JP4391673B2 (en) | 2000-08-08 | 2009-12-24 | 花王株式会社 | Oil composition |
US20030165572A1 (en) * | 2000-09-01 | 2003-09-04 | Nicolas Auriou | Water-dispersible encapsulated sterols |
JP3956605B2 (en) * | 2000-10-25 | 2007-08-08 | 株式会社豊田自動織機 | How to unload an object when it is floating |
DE60102484T2 (en) * | 2000-10-27 | 2004-08-19 | Unilever N.V. | EMULSIFIED FOOD COMPOSITION |
CA2443199C (en) | 2000-11-21 | 2010-01-26 | Unilever Plc | Edible water-in-oil emulsion spread containing a vegetable fat phase |
US20020168450A1 (en) * | 2000-11-28 | 2002-11-14 | Jaime Drudis | Melting body |
ITRE20010007U1 (en) | 2001-02-28 | 2002-08-28 | Elett Romeccaniche S I C E S P | PERFECT EQUIPMENT FOR DISASSEMBLY AND ASSEMBLY OF SELF-SUPPORTING TIRES, OF THE SYSTEM PAX TYPE AND SIMILAR. |
GB0105907D0 (en) | 2001-03-09 | 2001-04-25 | Boc Group Plc | Cryogenic processing methods and apparatus |
JP3583380B2 (en) * | 2001-04-26 | 2004-11-04 | 高砂香料工業株式会社 | Coating agents and coating powders |
US20030021877A1 (en) | 2001-06-13 | 2003-01-30 | Cain Frederick William | Micronised fat particles |
GB0120552D0 (en) | 2001-08-23 | 2001-10-17 | Boc Group Plc | Cryogenic crystallisation of solid fats |
WO2003022064A1 (en) * | 2001-09-07 | 2003-03-20 | Cargill Incorporated | Steryl ester compositions |
JP5170930B2 (en) | 2001-11-15 | 2013-03-27 | 株式会社Adeka | Bread dough and bread |
FR2832486A1 (en) * | 2001-11-22 | 2003-05-23 | Atofina | Multilayer tubing useful for making automobile fuel pipes includes a binder layer between a layer of polyamide-polyolefin blend and an inner layer of polyamide containing an electrically conductive filler |
AU2002351809B2 (en) | 2001-11-23 | 2005-11-24 | Upfield Europe B.V. | Water continuous acidified food product |
US7435441B2 (en) | 2002-01-23 | 2008-10-14 | Adeka Corporation | Fat composition |
JP4157765B2 (en) | 2002-02-18 | 2008-10-01 | 花王株式会社 | Powdered oil |
DE10207258B4 (en) * | 2002-02-21 | 2005-12-22 | Tischendorf, Dieter, Dr. | Process for producing candles consisting of vegetable or animal oils or fats |
PL205287B1 (en) | 2002-04-09 | 2010-03-31 | Unilever Nv | Triglyceride fat |
EP1499296B1 (en) | 2002-04-15 | 2012-04-04 | MAP Pharmaceuticals Inc | Formulation of fine particles using liquefied or dense gases |
US20030203854A1 (en) * | 2002-04-23 | 2003-10-30 | Ivo Pischel | Composition for effecting serum cholesterol levels |
CA2486634C (en) | 2002-05-21 | 2012-01-10 | Unilever Plc | Triglyceride fat |
CA2488617A1 (en) | 2002-06-10 | 2003-12-18 | Eugene R. Cooper | Nanoparticulate sterol formulations and sterol combinations |
US20050014158A1 (en) | 2002-06-27 | 2005-01-20 | Adam Gail Isabel Reid | Therapeutic methods for reducing fat deposition and treating associated conditions |
ES2361072T3 (en) | 2002-08-12 | 2011-06-13 | Unilever N.V. | TRIGLICERED FAT. |
KR20050053649A (en) | 2002-10-31 | 2005-06-08 | 닛신 오일리오그룹 가부시키가이샤 | Fat composition for spread |
EP1419811A1 (en) | 2002-11-12 | 2004-05-19 | Inovia Hutzinger & Partner KEG | Stable plant extracts |
DE10253111A1 (en) | 2002-11-13 | 2004-05-27 | Basf Ag | Powdered formulation used e.g. as food additive or pharmaceutical for preventing arteriosclerosis and hyperlipemia, contains phytosterol |
DE10253193A1 (en) | 2002-11-15 | 2004-06-03 | Degussa Ag | Silica or silicates coated with food-grade wax, oil and/or fat, useful as free-flow or anticaking additives for powdered food-grade products |
EP1419698B1 (en) | 2002-11-18 | 2014-08-06 | Unilever N.V. | Particulate creamer comprising fat and method of preparing compositions comprising said creamer |
US7226630B2 (en) * | 2002-11-26 | 2007-06-05 | Kraft Foods Holdings, Inc. | Edible moisture barrier for food and method of use products |
EP1433387A1 (en) * | 2002-12-26 | 2004-06-30 | Adisseo France S.A.S. | Solid granules containing carotenoids |
ZA200505263B (en) | 2003-02-06 | 2006-09-27 | Unilever Plc | Edible omulsion spread |
US7226629B2 (en) * | 2003-02-24 | 2007-06-05 | Kraft Foods Holdings, Inc. | Microwaveable grilled cheese and meat sandwiches and method of preparation |
US20040197446A1 (en) * | 2003-04-01 | 2004-10-07 | Kraft Foods Holdings, Inc. | Edible moisture barrier for food products |
FI20030610A0 (en) | 2003-04-22 | 2003-04-22 | Raisio Benecol Oy | Edible product |
US8025913B2 (en) | 2003-07-17 | 2011-09-27 | Conopco Inc. | Process for the preparation of an edible dispersion comprising oil and structuring agent |
WO2005022603A2 (en) | 2003-09-02 | 2005-03-10 | Integral Technologies, Inc. | Low cost conductive containers manufactured from conductive loaded resin-based materials |
US7329429B2 (en) * | 2003-09-25 | 2008-02-12 | Chimel Mark J | Bars and confectioneries containing cocoa solids having a high cocoa polyphenol content and sterol/stanol esters and processes for their preparation |
PT1677613E (en) | 2003-10-30 | 2012-08-24 | Arla Foods Amba | Stabilisers useful in low fat spread production |
GB0326491D0 (en) | 2003-11-13 | 2003-12-17 | Boc Group Plc | Cooling of liquids |
KR100603974B1 (en) | 2003-12-05 | 2006-07-25 | 김갑식 | Method for preparing nano-scale or amorphous particle using solid fat as a solvent |
BRPI0417889B1 (en) | 2004-01-26 | 2015-09-08 | Unilever Nv | process |
AU2005211158B2 (en) | 2004-01-28 | 2007-08-30 | Unilever Plc | Savoury food composition comprising low-trans triglyceride fat composition |
US20070154557A1 (en) | 2004-01-30 | 2007-07-05 | Veldhuizen Yvonne S J | Particulate comprising phytosterols and food compositions comprising said creamer |
US20050175745A1 (en) | 2004-02-06 | 2005-08-11 | Jerzy Zawistowski | Method of preservation of a food prodcut and composition comprising one or more phytosterols and/or phytostanols useful for this purpose |
US8158184B2 (en) * | 2004-03-08 | 2012-04-17 | Bunge Oils, Inc. | Structured lipid containing compositions and methods with health and nutrition promoting characteristics |
WO2005096955A1 (en) * | 2004-04-07 | 2005-10-20 | Tze Liang Woffles Wu | Surgical thread |
US8075910B2 (en) | 2004-05-20 | 2011-12-13 | Pbm Pharmaceuticals, Inc. | Oral compositions comprising edible oils and vitamins and/or minerals and methods for making oral compositions |
US7618670B2 (en) | 2004-06-14 | 2009-11-17 | Premium Vegetable Oils Sdn. Bhd. | Trans free non-hydrogenated hard structural fat and non-hydrogenated hard palm oil fraction component |
US7736684B2 (en) * | 2004-06-22 | 2010-06-15 | General Mills, Inc. | Viscous fat compositions having low amounts of trans-fat, methods and products |
EP1843665B1 (en) | 2004-07-13 | 2011-05-18 | Fuji Oil Europe | Low-trans fats for confectionery fat compositions with improved texture and crystallisation rate |
FI20041302A0 (en) | 2004-10-08 | 2004-10-08 | Raisio Benecol Oy | Low energy foods |
US20060115553A1 (en) * | 2004-12-01 | 2006-06-01 | Slim-Fast Foods Company, Division Of Conopco, Inc. | Nutrition bar or other food product and process of making |
ZA200705400B (en) | 2004-12-23 | 2008-09-25 | Unilever Plc | Frozen aerated confections |
PL1841327T3 (en) | 2005-01-28 | 2011-05-31 | Unilever Bcs Europe Bv | Edible dispersions comprising oil and structuring agent |
PL1865786T5 (en) * | 2005-02-17 | 2015-12-31 | Unilever Bcs Europe Bv | Process for the preparation of a spreadable dispersion |
EP1731594A1 (en) | 2005-06-09 | 2006-12-13 | Fuji Oil Europe | Non-hydrogenated fat composition and its use |
ITTO20050424A1 (en) | 2005-06-16 | 2006-12-17 | Bf Pharma S P A | USE OF SOYBEAN OIL, PROCEDURE FOR ITS PREPARATION AND SOYA GERM WITH HIGH PURITY |
EP1736059A1 (en) | 2005-06-21 | 2006-12-27 | Fuji Oil Europe | Structuring granular composition |
US20080193638A1 (en) | 2005-08-18 | 2008-08-14 | Mcmaster Alan J | Process and Apparatus for Coating Substrates by Spray Pyrolysis |
WO2007024770A2 (en) | 2005-08-22 | 2007-03-01 | Archer-Daniels-Midland Company | Methods of forming phytosterol-fortified cocoa powder and the product formed therefrom |
PL1917336T3 (en) | 2005-08-23 | 2017-11-30 | Unilever BCS Europe B.V. | Non-hydrogenated hardstock fat |
US7575768B2 (en) | 2005-09-07 | 2009-08-18 | Brandeis University | Dietary supplements and prepared foods containing triglyceride-recrystallized non-esterified phytosterols |
US10757953B2 (en) | 2005-09-26 | 2020-09-01 | Upfield Europe B.V. | Non-hydrogenated hardstock fat |
WO2007039040A1 (en) | 2005-09-30 | 2007-04-12 | Unilever N.V. | Food composition |
EP1815752A1 (en) | 2006-02-02 | 2007-08-08 | Nestec S.A. | Improvement of cold liquid solubility of fat-containing powders |
EP1986503B1 (en) | 2006-02-21 | 2014-12-17 | Unilever N.V. | Non dairy product |
ES2595639T3 (en) | 2006-02-21 | 2017-01-02 | Unilever BCS Europe B.V. | Non-dairy product |
EP2020874A4 (en) | 2006-05-01 | 2015-07-15 | Pharmachem Lab Inc | Composition comprising one or more esterified phytosterols and/or phytostanols into which are solubilized one or more unesterified phytosterols and/or phytostanols, in order to achieve therapeutic and formulation benefits |
US7645473B2 (en) | 2006-06-13 | 2010-01-12 | Loders Croklaan Usa Llc | Fat composition |
US20080089978A1 (en) * | 2006-10-13 | 2008-04-17 | Body Structures, Inc. | Lacteal coated pizzas |
WO2008127827A1 (en) | 2007-03-14 | 2008-10-23 | The Hershey Company | Health bars and compositions for improving mental and physical energy |
WO2008125380A1 (en) | 2007-04-11 | 2008-10-23 | Unilever N.V. | Edible fat continuous spreads |
ATE447329T1 (en) | 2007-07-13 | 2009-11-15 | Unilever Nv | FOODS CONTAINING BACTERIA AND SORBITAN FATTY ACID |
US8586122B2 (en) | 2007-07-26 | 2013-11-19 | Loders Croklaan Usa Llc | Composition suitable for use in baking |
WO2009068651A1 (en) | 2007-11-28 | 2009-06-04 | Dsm Ip Assets B.V. | Lipid emulsion for human consumption |
WO2009102450A1 (en) | 2008-02-14 | 2009-08-20 | Radlo Foods, Llc | Egg products with components recognized for reducing the levels of cholesterol in people and/or improving their health |
EP2123164A1 (en) | 2008-05-23 | 2009-11-25 | Nestec S.A. | Granulated dairy products |
EP2181604A1 (en) | 2008-11-04 | 2010-05-05 | Feyecon Development & Implementation B.V. | Dispersion structuring agent |
WO2010060713A1 (en) | 2008-11-28 | 2010-06-03 | Unilever Nv | Fat containing emulsion comprising palm oil and sorbitan fatty acid ester |
AU2009328392B2 (en) | 2008-12-19 | 2013-08-22 | Upfield Europe B.V. | Edible fat powders |
EP2367437B1 (en) | 2008-12-19 | 2014-03-05 | Unilever NV | Process for the preparation of a fat continuous spread |
WO2010069753A1 (en) | 2008-12-19 | 2010-06-24 | Unilever Nv | Process for the preparation of an edible fat continuous spread |
CA2745973A1 (en) | 2008-12-19 | 2010-06-24 | Unilever Plc | Edible fat powders |
US20110311707A1 (en) | 2008-12-19 | 2011-12-22 | Albert Jan Bezemer | Process for the preparation of an edible fat continuous food product |
EP2367436B1 (en) | 2008-12-19 | 2012-10-03 | Unilever NV | Process for the preparation of an edible fat continuous spread |
US20100159079A1 (en) | 2008-12-24 | 2010-06-24 | Conopco, Inc., D/B/A Unilever | Encapsulate and Food Containing Same |
KR20120080615A (en) | 2009-09-30 | 2012-07-17 | 메사추세츠 인스티튜트 오브 테크놀로지 | Phototriggered nanoparticles for cell and tissue targeting |
US8512794B2 (en) | 2010-05-20 | 2013-08-20 | Perlman Consulting, Llc | Oleate ester phytosterol compositions |
WO2011160921A1 (en) | 2010-06-22 | 2011-12-29 | Unilever Nv | Edible fat powders |
JP5951742B2 (en) | 2014-12-05 | 2016-07-13 | 中国電力株式会社 | Indirect hot wire tool handle |
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