EP0470148A1 - Fett und verfahren zu dessen herstellung - Google Patents
Fett und verfahren zu dessen herstellungInfo
- Publication number
- EP0470148A1 EP0470148A1 EP90907183A EP90907183A EP0470148A1 EP 0470148 A1 EP0470148 A1 EP 0470148A1 EP 90907183 A EP90907183 A EP 90907183A EP 90907183 A EP90907183 A EP 90907183A EP 0470148 A1 EP0470148 A1 EP 0470148A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- percent
- fatty
- double bonds
- series
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 14
- 239000011261 inert gas Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 235000019197 fats Nutrition 0.000 claims description 19
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 235000021323 fish oil Nutrition 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims description 3
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims description 3
- 229960002733 gamolenic acid Drugs 0.000 claims description 3
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 21
- 239000003925 fat Substances 0.000 description 15
- 235000006708 antioxidants Nutrition 0.000 description 7
- 235000013310 margarine Nutrition 0.000 description 6
- 239000003264 margarine Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 235000016709 nutrition Nutrition 0.000 description 4
- 230000035764 nutrition Effects 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 241001310494 Ammodytes marinus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
- 235000008524 evening primrose extract Nutrition 0.000 description 2
- 239000010475 evening primrose oil Substances 0.000 description 2
- 229940089020 evening primrose oil Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 102100034544 Acyl-CoA 6-desaturase Human genes 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- 108010037138 Linoleoyl-CoA Desaturase Proteins 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000010473 blackcurrant seed oil Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000021324 borage oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940107161 cholesterol Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- -1 fatty acid esters Chemical class 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229940040452 linolenate Drugs 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-M linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O DTOSIQBPPRVQHS-PDBXOOCHSA-M 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-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 OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or 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 OR 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 OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
Definitions
- the present invention relates to a fatty product containing an inert gas, at least one polyunsaturated fatty acid, and at least 10 percent by weight of solid fat and optionally an antioxidant.
- a fat having a soft texture is obtained at low temperatures (0 ⁇ C-5 ⁇ C).
- the whipp- ing of air into fats for use as shortening serves to impart to the product an opaque, margarine-like appearance.
- the whipping of air or inert gas into margarine is effected in order to improve the frying properties and the organoleptic properties of the margarine and to protect it from the formation of mold.
- the fats and oils used are always suitable for baking or frying purposes, i.e. fats which tolerate heating up to about 150 ⁇ C-300 ⁇ C according to the appli ⁇ cation.
- fats containing polyunsaturated fatty acids is much restricted.
- margarine is used as a fatty spread and for this particular purpose it is often produced with a content of polyunsaturated fatty acids which essentially consist of linoleic acid comprising two double bonds (18:2 n-6) and which fre ⁇ quently have a low content of ⁇ -linolenic acid comprising three double bonds (18:3 n-3).
- a disadvantage of the disclosed water-in-oil emulsion is that oxygen is introduced into the fatty product in the water phase. Dissolved oxygen in the water phase reduces the shelf life of fatty products containing polyunsaturated fatty acids considerably, because polyun ⁇ saturated fatty acids having more than two double bonds are very easi ⁇ ly oxidized, and the existing technology does not disclose how to pro- prise a margarine emulsion in an oxygen-free environment.
- polyunsaturated fatty acids comprising 5 double bonds (20:5 n-3 and 22:5 n-3), which are mainly present in marine oils, par ⁇ ticularly fish oils, and in phyto-plankton and algae, reduces the cho- lesterol content of the blood and, accordingly, also reduces the risk of developing heart and vascular disorders by virtue of their conver ⁇ sion into the physiologically active prostaglandin E, (PGE 3 ).
- ⁇ -Linolenic acid (18:3 n-6), which is present in vegetable oils, such as evening primrose oil, borage oil, and black-currant seed oil, is therefore a more effi- cient precursor in the biosynthesis of PGE, and PGE « (Gurr, M.J., Role of Fats in Food and Nutrition, Elsevier Applied Science Publishers, London New York, 1984, 170 pp), and this fact has led to an increasing interest in the use of ⁇ -linolenic acid in i.a. food products.
- an amply occur- ing raw material such as fish oil and in particular sand eel oil hav ⁇ ing a high content (about 15% by weight to about 30% by weight) of n-3 fatty acids and vegetable oils, such as the above mentioned, having a high content (about 14% by weight to about 33% by weight) of n-6 fatty acids in their unhydrogenated state for the sake of the shelf life thereof, and thus the desirable nutritive and wholesome effects there ⁇ of have not been fully utilized.
- the fatty product of the invention which is characterized in that it has a maximum water content of 1 percent by weight and that it further comprises at least 1 percent by weight of polyunsaturated fatty acids of the n-3 series comprising at least four double bonds and/or at least 0.5 percent by weight of polyunsatu ⁇ rated fatty acids of the n-6 series comprising at least three double bonds.
- the highly unsaturated fatty acids are stabilized in a fatty product into which inert gas and a suitable amount of antioxidants have been whipped, thus imparting to the final product a peroxide number according to the IUPAC (2.501) of less than about 1 meq/kg.
- a substantially water-free fat makes it possible to avoid the undesirable effects of oxygen dissolved in the water phase with respect to the durability of a product containing polyunsaturated fat- ty acids.
- the whipped-in inert gas e.g. N « or C0 2 , protects the fats from oxidization since no further 0 2 can be dissolv ⁇ ed in an N 2 ⁇ saturated fat.
- antioxidants such as alkylgallates, as- corbyl fatty acid esters and tocopherols
- the antioxidants affords further improvement of the durability of the products according to the invention and, ad ⁇ ditionally, the antioxidants also aid in the protection of the fatty acids against oxidation occurring in the organism.
- a preferred content of inert gas in the form of N « in the fatty pro ⁇ duct corresponds to a fatty product density of 0,65-0,85 kg/1.
- the requisite amount of whipped-in inert gas increases with increaing amounts of hydrogenated fat in the product.
- the invention further relates to a process for the production of a fatty product wherein an inert gas is whipped into a mixture of fatty substances which was initially softened by heating and which has a maximum water content of 1% and contains at least 10 percent by weight of a solid fat and optionally an antioxidant at room temperature, and wherein the product thus produced is cooled.
- the process is character ⁇ ized in using a mixture of fatty substances containing at least 1 per ⁇ cent by weight of a polyunsaturated fatty acid of the n-3 series com ⁇ prising at least four double bonds or at least 0.5 percent by weight of a polyunsaturated fatty acid of the n-6 series comprising at least three double bonds.
- the products produced in the process according to the invention may be packaged like similar products containing polyunsaturated fatty acids comprising two double bonds and having a low content of polyunsatura ⁇ ted fatty acids comprising three or more double bonds.
- a mixture of fatty substances comprises 10 percent by weight of refined vacuumdeodorized fish oil (sand eel oil), 63 percent by weight of refi- ned vacuumdeodorized rapeseed oil and 17 percent by weight of selecti ⁇ vely hydrogenated palm stearin having the following approximate solid- phase values (pulsated-NMR): 95% at 10°C, 94% at 20'C, 83% at 30*C, 59% at 40 * C, 6% at 50 * C.
- Antioxidants are added to the mixture of fat ⁇ ty substances in the form of propylgallate in an amount of 50 ppm, ascorbylpalmitate in an amount of 22 ppm, and natural tocopherol in an amount of 1,000 ppm.
- Flavours are added in an amount of 100 ppm.
- the mixture of fatty substances (including the antioxidants and fla ⁇ vours) is subsequently heated to 45 ⁇ C for complete melting and is then cooled to 4 ⁇ C by passage through a one-pipe pilot plant of the Gersten- berg & Agger type.
- a nitrogen amount (N 2 ) adjusted so as to impart to the final product a density of 0.65 g/ml is introduced into the suc ⁇ tion part of the high-pressure plant pump via a distribution nozzle which pump is set to yield 20 kgs of product per hour.
- the product is filled into cups immediately upon the pipe cooler treatment without using any dwelling pipes.
- the final product is stored at a maximum temperature of 10°C.
- the fatty acid composition of the fish oil is as follows:
- Tasting of samples produced 2.5 months earlier of the fatty products containing 20 and 30 percent by weight, respectively, of refined fish oil having the fatty acid composition of example 1 showed that the taste and the mouth feel were neutral and that no disagreeable taste or aftertaste could be detected.
- the fatty products tolerate storage at room temperature for at least four hours and, moreover, the taste remains the same for two months at a temperature below lO'C. After storage for two months at a tempe ⁇ rature below 10 * C the peroxide number is still less than about 1 meq/kg.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- General Preparation And Processing Of Foods (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK2032/89 | 1989-04-27 | ||
| DK203289A DK162621C (da) | 1989-04-27 | 1989-04-27 | Skumformigt fedtstofprodukt og fremgangsmaade til fremstilling af samme |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0470148A1 true EP0470148A1 (de) | 1992-02-12 |
Family
ID=8109597
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90907183A Pending EP0470148A1 (de) | 1989-04-27 | 1990-04-24 | Fett und verfahren zu dessen herstellung |
| EP90610027A Expired - Lifetime EP0395569B1 (de) | 1989-04-27 | 1990-04-24 | Fett und Verfahren zu seiner Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90610027A Expired - Lifetime EP0395569B1 (de) | 1989-04-27 | 1990-04-24 | Fett und Verfahren zu seiner Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| EP (2) | EP0470148A1 (de) |
| JP (1) | JPH04505100A (de) |
| AT (1) | ATE83895T1 (de) |
| AU (1) | AU633924B2 (de) |
| CA (1) | CA2053281A1 (de) |
| DE (1) | DE69000689T2 (de) |
| DK (1) | DK162621C (de) |
| PT (1) | PT93888A (de) |
| WO (1) | WO1990012510A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK164685C (da) * | 1990-01-22 | 1992-12-21 | Jon Katborg | Ikke-flydende fedtstofprodukt indeholdende vand og mindst en polyumaettet fedtsyre og fremgangsmaade til fremstilling af samme |
| WO2005122795A1 (en) * | 2004-06-10 | 2005-12-29 | Kellogg Company | Topical application of marine oils to foods |
| BR112012007166A2 (pt) * | 2009-09-30 | 2017-05-02 | Solae Llc | "composição de gordura alimentícia, método de uso de ácido estearidônico para formar uma composição de gordura alimentícia,composições alimentícias, manteiga de nozes e metodo para usar ácido esteardônico para formar uma manteiga de nozes. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR573718A (fr) * | 1922-11-23 | 1924-06-28 | Procédé de traitement des graisses et des huiles | |
| JPS6049097A (ja) * | 1983-08-29 | 1985-03-18 | 日本油脂株式会社 | 粉末油脂 |
| CA1239587A (en) * | 1983-10-24 | 1988-07-26 | David Rubin | Combined fatty acid composition for lowering blood cholestrol and triglyceride levels |
| JPS6158536A (ja) * | 1984-08-31 | 1986-03-25 | Nippon Oil & Fats Co Ltd | 栄養組成物 |
| DE3643848A1 (de) * | 1986-12-22 | 1988-09-01 | Natec Inst Naturwiss | Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendung |
| HU202088B (en) * | 1987-03-18 | 1991-02-28 | Caola Kozmetikai | Method for producing dietetic preparation |
| GB8706711D0 (en) * | 1987-03-20 | 1987-04-23 | Unilever Plc | Edible plastic product |
| GB8718523D0 (en) * | 1987-08-05 | 1987-09-09 | Unilever Plc | Marine/vegetable oil blend |
| FR2623692B1 (fr) * | 1987-11-30 | 1991-05-03 | Vernin Jean Gilles | Nouvelle huile dietetique |
-
1989
- 1989-04-27 DK DK203289A patent/DK162621C/da not_active IP Right Cessation
-
1990
- 1990-04-24 AU AU56306/90A patent/AU633924B2/en not_active Ceased
- 1990-04-24 DE DE9090610027T patent/DE69000689T2/de not_active Expired - Fee Related
- 1990-04-24 JP JP2507159A patent/JPH04505100A/ja active Pending
- 1990-04-24 CA CA002053281A patent/CA2053281A1/en not_active Abandoned
- 1990-04-24 EP EP90907183A patent/EP0470148A1/de active Pending
- 1990-04-24 AT AT90610027T patent/ATE83895T1/de active
- 1990-04-24 WO PCT/DK1990/000107 patent/WO1990012510A1/en not_active Ceased
- 1990-04-24 EP EP90610027A patent/EP0395569B1/de not_active Expired - Lifetime
- 1990-04-26 PT PT93888A patent/PT93888A/pt not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9012510A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0395569A1 (de) | 1990-10-31 |
| JPH04505100A (ja) | 1992-09-10 |
| DK162621B (da) | 1991-11-25 |
| DK162621C (da) | 1992-04-13 |
| CA2053281A1 (en) | 1990-10-28 |
| DK203289A (da) | 1990-10-28 |
| AU633924B2 (en) | 1993-02-11 |
| WO1990012510A1 (en) | 1990-11-01 |
| PT93888A (pt) | 1990-11-20 |
| DE69000689D1 (de) | 1993-02-11 |
| DE69000689T2 (de) | 1993-07-08 |
| EP0395569B1 (de) | 1992-12-30 |
| AU5630690A (en) | 1990-11-16 |
| ATE83895T1 (de) | 1993-01-15 |
| DK203289D0 (da) | 1989-04-27 |
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