EP1684598A2 - Oleaginous composition containing a flowable active ingredient - Google Patents
Oleaginous composition containing a flowable active ingredientInfo
- Publication number
- EP1684598A2 EP1684598A2 EP04818406A EP04818406A EP1684598A2 EP 1684598 A2 EP1684598 A2 EP 1684598A2 EP 04818406 A EP04818406 A EP 04818406A EP 04818406 A EP04818406 A EP 04818406A EP 1684598 A2 EP1684598 A2 EP 1684598A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- premix
- oil
- active ingredient
- weight
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000004480 active ingredient Substances 0.000 title claims abstract description 25
- 230000009969 flowable effect Effects 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 6
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 235000013305 food Nutrition 0.000 claims abstract description 5
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 56
- 239000011668 ascorbic acid Substances 0.000 claims description 28
- 235000010323 ascorbic acid Nutrition 0.000 claims description 28
- 229960005070 ascorbic acid Drugs 0.000 claims description 28
- 239000007765 cera alba Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 6
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 6
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 6
- 229940068977 polysorbate 20 Drugs 0.000 claims description 6
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 4
- 229920000053 polysorbate 80 Polymers 0.000 claims description 4
- 229940068968 polysorbate 80 Drugs 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 235000015173 baked goods and baking mixes Nutrition 0.000 claims description 2
- 235000013332 fish product Nutrition 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- 239000001993 wax Substances 0.000 description 9
- 239000003925 fat Substances 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000013543 active substance Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 229940057917 medium chain triglycerides Drugs 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 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
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 229940073532 candelilla wax Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/22—Ascorbic acid
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/771—Organic compounds containing hetero rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B4/00—Preservation of meat, sausages, fish or fish products
- A23B4/12—Preserving with acids; Acid fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B4/00—Preservation of meat, sausages, fish or fish products
- A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
- A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
- A23B4/20—Organic compounds; Microorganisms; Enzymes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
-
- 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
Definitions
- the invention relates to an oily composition containing, in particular, an antioxidative, flowable active substance, primarily for the preparation of foods, and to a method for producing the composition.
- the composition is added to an oil, which in turn is used to prepare food or ointments and other cosmetics.
- Light oil such as rapeseed oil, sunflower oil, safflower oil or a medium-chain triglyceride such as miglyol can be considered as an oil.
- these oils are admixed with active ingredients which are soluble in the oil, in particular antioxidants such as, for example, EP 13 38 271 with an emulsifier (HLB value between about 9 and 18) and solubilized ascorbic acid.
- Micellated ⁇ -lipoic acid according to DE 101 08 614 A1 can be considered as a further active ingredient.
- the absorption capacity of the oil on the added active ingredient is limited and not sufficient for many applications.
- oil For miglyol, for example, you cannot get past a concentration of pure ascorbic acid in the oil of around 1,200 ppm. If the oil is to be used as an additive (compound) for dough pieces, it is desirable to have a higher concentration of the active ingredient, such as ascorbic acid, in the oil.
- the invention is therefore based on the object of increasing the active substance content in an oil suitable for food preparations or the like
- the viscosity of the composition mentioned above lies between the viscosity of the oil and the viscosity of the active ingredient. This makes it possible to significantly increase the active substance content in the oil.
- the active ingredient is first mixed into the composition with a premix such that the composition has a viscosity which is between the viscosity of the active ingredient and that of the oil; then the composition is added to the oil.
- the invention has the advantage that a significantly higher proportion of the active ingredient can be introduced into the oil than when the active ingredient is added directly to the oil. If the Active ingredient is the ascorbic acid solubilizate mentioned, the proportion of pure ascorbic acid in the oil can be increased to about ten times with the invention.
- fats are suitable as oils, such as fats rich in oil and / or linoleic acid, fish oil or medium-chain triglycerides.
- oils such as fats rich in oil and / or linoleic acid, fish oil or medium-chain triglycerides.
- waxes that consist of fat-like compounds, higher fatty acids and monohydric higher paraffin alcohols (Myricil, Cetyl, Deryl, Melissyl alcohol), such as wool fat (E 913), beeswax or vegetable wax (Carnauba wax, Candelilla wax, sugar cane wax or also
- wool wax and wool fat, artificial waxes or synthetically produced waxes only show the desired viscosity-balancing effect between the solubilisate and the oil at higher concentrations.
- the addition of one of the waxes mentioned to the fat of the premix is generally only few G percent by weight of the premix. For a better dissolution of the wax in the fat, it may be advisable to prepare the premix in mild heat, for example from 40 ° C to about 60 ° C.
- the active substance is added to the oil in the form of a composition which consists of one part of active substance and a multiple of the part of the premix. In the case of the micellized ascorbic acid mentioned, the composition expediently consists of one part of ascorbic acid solubilizate and approximately 9 parts of premix.
- the process according to the invention for producing the composition provides that the active ingredient is stirred with an oily premix which is adjusted so that the viscosity of the composition lies between the viscosity of the active ingredient and the viscosity of the oil.
- the production of the oil according to the invention can be carried out, for example, as follows:
- the viscosity of the individual mixtures at RT (20 ° C.) is measured as the run-out time in seconds in accordance with DIN 53211 using a FORD cup which has a 3 mm outlet nozzle.
- the run-out time of the Miglyol 812 used in the two examples below is 31.5 seconds.
- a premix B 1 which consists of cera alba (CA) and a light, in particular vegetable fat, such as sunflower oil, rapeseed oil or safflower oil, or alternatively of neutral oil (Miglyol 812).
- CA cera alba
- a light, in particular vegetable fat such as sunflower oil, rapeseed oil or safflower oil, or alternatively of neutral oil (Miglyol 812).
- about 97.8% by weight (based on 100% by weight of the premix) of the fat with 2.2% by weight of CA are mixed with one another and heated to about 40 ° to about 60 ° C. and stirred until the cera alba platelets are completely in loosened the fat.
- the mixture is slowly cooled to room temperature with constant stirring.
- the run-time of this premix is 146.5 seconds.
- an ascorbic acid solubilizate A 1 is produced separately, which consists of ascorbic acid, water and polysorbate 20.
- ascorbic acid in 10% by weight (based on 100% by weight of solubilisate) of distilled water is dissolved in the heat (40 ° C. to 60 ° C.) and 10% by weight of Miglyol 812 is added with stirring at the temperature specified.
- 70% by weight of heated polysorbate 20 are introduced and the mixture is stirred until it is clear and homogeneous.
- the expiry time of this ascorbic acid solubilizate is 867.0 seconds.
- the premix B 1 mentioned in Example 1 contains an addition of a glyceride, for example Lamegin DWP 2000 (Cognis), which is a mono- and
- the expiration time of the composition is 85.0 seconds.
- composition About 5% by weight of solubilizate A 3 is mixed with about 95% by weight of premix B 3 until the composition is homogeneous. The composition then again contains about 1% by weight of pure ascorbic acid. Flow time: 179.5 seconds.
- the viscosity of the respective composition lies between the viscosity of the solubilizate and that of the oil to be mixed with the composition. It should be taken into account that the run-down time of A 3 cannot be determined using the method used here because of the viscosity of A 3 at RT, but can be assumed to be at least as long as that of A 1.
- the invention described with reference to the preceding examples has the further advantage that the sediment-free addition of the oil with the composition according to the invention can be carried out at RT.
- the invention is not limited to the specific figures and the starting materials mentioned. If it can be tolerated that the addition of the composition to the oil can also be carried out under mild heat (about 30 ° C. to about 60 ° C.), other premixes, solubilisates and compositions can also be considered, as long as the viscosity of the composition at the chosen one Temperature is between that of the solubilizate and that of the oil.
- One can therefore proceed as follows: About 88.5% by weight (based on the composition 100%) of an oil, which can be a vegetable oil, fish oil or a medium-chain triglyceride, are heated to about 80 ° C. About 1.5% by weight of beeswax (cera alba) is added to the warm oil and stirred. After the wax has dissolved, about 10% by weight of the above-mentioned ascorbic acid solubilizate is added to the warm mixture. Stirring continues until after the heater is turned off the composition has cooled to room temperature.
- an oil which can be a vegetable oil, fish oil or a medium-chain triglyceride
- composition according to the invention remains stable, homogeneous and free of sediment even after prolonged storage (at room temperature or below) and contains about 1% by weight or 10,000 ppm of pure, chemically unchanged ascorbic acid (Vitamin C).
- This ascorbic acid concentration in the oil is approx. 20 times the concentration that has been achieved in oils by derivatized ascorbic acid variants, such as ascorbyl palmitate (previously the only non-phenolic antioxidant variant).
- the invention can also be implemented with an ascorbic acid solubilizate in which polysorbate 20 has been used instead of polysorbate 80.
- the ascorbic acid solubilizate can also be obtained with medium-chain triglycerides, which usually have a substantial content of caprylic acid and capric acid.
- the ascorbic acid solubilizate can also be produced by using polysorbate 20 instead of polysorbate 80, the weight ratios mentioned being able to be essentially maintained. The run-out time of such an ascorbic acid solubilizate produced with polysorbate 20 is measured at 15.5 minutes.
- composition according to the invention can be added to the oil in an amount as required (up to 25% by weight). This means that the proportion of ascorbic acid in the oil can be freely adjusted without the need for further measures (addition of additives or the use of special agitators).
- the composition is suitable for the preservation of oils.
- the composition can be used as the main component (oxidation compound) in the preparation of doughs or dough mixtures from which baked goods are to be produced. It is also recommended to use the composition as an antioxidant additive in the manufacture of fish products, in particular canned fish and as an additive to cosmetics.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Edible Oils And Fats (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
BESCHREIBUNG A 582-1 DESCRIPTION A 582-1
Einen fließfähigen Wirkstoff enthaltende ölige ZusammensetzungAn oily composition containing a flowable active ingredient
Die Erfindung betrifft eine einen insbesondere antioxidativen, fließfähigen Wirkstoff enthaltende ölige Zusammensetzung vornehmlich für die Zubereitung von Lebensmitteln sowie ein Verfahren zur Herstellung der Zusammensetzung.The invention relates to an oily composition containing, in particular, an antioxidative, flowable active substance, primarily for the preparation of foods, and to a method for producing the composition.
Die Zusammensetzung wird einem Öl zugesetzt, das seinerseits der Zubereitung von Lebensmitteln oder von Salben und anderen Kosmetika dient. Als Öl kommen etwa leichtes Pflanzenöl, beispielsweise Rapsöl, Sonnenblumenöl, Distelöl oder auch ein mittelkettiges Triglycerid wie etwa Miglyol in Betracht. Diesen Ölen werden gegen vorzeitiges Altern in dem Öl lösliche Wirkstoffe, insbesondere Antioxidantien wie etwa gemäß EP 13 38 271 mit einem Emulgator (HLB-Wert zwischen etwa 9 und 18) solubilisierte Ascorbinsäure zugesetzt. Als weiterer Wirkstoff kommt micellierte α-Liponsäure gemäß DE 101 08 614 A1 in Betracht. Die Aufnahmefähigkeit des Öles an dem zugesetzten Wirkstoff ist jedoch begrenzt und für viele Anwendungsfälle nicht ausreichend. So kommt man beispielsweise für Miglyol über eine Konzentration an reiner Ascorbinsäure in dem Öl von etwa 1.200 ppm nicht hinaus. Soll das Öl als Zusatz (Compound) für Teiglinge verwendet werden, ist es erwünscht, in dem Öl eine höhere Konzentration an dem Wirkstoff wie etwa Ascorbinsäure zur Verfügung zu haben.The composition is added to an oil, which in turn is used to prepare food or ointments and other cosmetics. Light oil such as rapeseed oil, sunflower oil, safflower oil or a medium-chain triglyceride such as miglyol can be considered as an oil. To prevent premature aging, these oils are admixed with active ingredients which are soluble in the oil, in particular antioxidants such as, for example, EP 13 38 271 with an emulsifier (HLB value between about 9 and 18) and solubilized ascorbic acid. Micellated α-lipoic acid according to DE 101 08 614 A1 can be considered as a further active ingredient. However, the absorption capacity of the oil on the added active ingredient is limited and not sufficient for many applications. For miglyol, for example, you cannot get past a concentration of pure ascorbic acid in the oil of around 1,200 ppm. If the oil is to be used as an additive (compound) for dough pieces, it is desirable to have a higher concentration of the active ingredient, such as ascorbic acid, in the oil.
Der Erfindung liegt daher die Aufgabe zugrunde, den Wirkstoffgehalt in einem für Lebensmittelzubereitungen oder dergleichen geeigneten Öl zu erhöhenThe invention is therefore based on the object of increasing the active substance content in an oil suitable for food preparations or the like
Erfindungsgemäß liegt die Viskosität der eingangs genannten Zusammensetzung zwischen der Viskosität des Öls und der Viskosität des Wirkstoffes. Damit gelingt es, den Wirkstoffgehalt in dem Öl wesentlich zu erhöhen. Dazu wird erfindungsgemäß der Wirkstoff zunächst mit einer solchen Vormischung zu der Zusammensetzung vermischt, dass die Zusammensetzung eine Viskosität aufweist, die zwischen der Viskosität des Wirkstoffes und derjenigen des Öles liegt; sodann wird die Zusammensetzung dem Öl zugegeben. Die Erfindung bringt den Vorteil, dass sich in das Öl ein wesentlich höherer Anteil des Wirkstoffes einbringen lässt, als bei direkter Zugabe des Wirkstoffes zum Öl. Wenn der Wirkstoff das erwähnte Ascorbinsäure-Solubilisat ist, lässt sich der Anteil an reiner Ascorbinsäure im Öl mit der Erfindung auf etwa das Zehnfache steigern.According to the invention, the viscosity of the composition mentioned above lies between the viscosity of the oil and the viscosity of the active ingredient. This makes it possible to significantly increase the active substance content in the oil. For this purpose, according to the invention, the active ingredient is first mixed into the composition with a premix such that the composition has a viscosity which is between the viscosity of the active ingredient and that of the oil; then the composition is added to the oil. The invention has the advantage that a significantly higher proportion of the active ingredient can be introduced into the oil than when the active ingredient is added directly to the oil. If the Active ingredient is the ascorbic acid solubilizate mentioned, the proportion of pure ascorbic acid in the oil can be increased to about ten times with the invention.
Für die Vormischung eignen sich Fette als Öle wie zum Beispiel öl- und/oder linolsäurereiche Fette, Fischöl oder mittelkettige Triglyeride. Diesen werden Wachse, die aus fettähnlichen Verbindungen, aus höheren Fettsäuren und einwertigen höheren Paraffin-Alkoholen (Myricil-, Cetyl-, Deryl-, Melissylalkohol) bestehen, wie Wollfett (E 913), Bienenwachs oder Pflanzenwachs (Carnaubawachs, Candelillawachs, Zuckerrohrwachs oder auch synthetische Wachsen bestehen. Die als Alternative genannten Wachsvarianten wie Wollwachs und Wollfett, künstliche Wachse oder synthetisch hergestellte Wachse zeigen nur bei höherer Konzentration den erwünschten Viskositätsausgleichenden Effekt zwischen dem Solubilisat und dem Öl. Bei Carnaubawachs ist die Homogenität der Mischung nur schwer erreichbar. Im Prozess der Abkühlung bilden sich unterschiedlich große Partikel. Daher erweist sich Gera alba für die Zwecke im Sinne der Erfindung als günstiges Mittel ohne dass die Erfindung auf die Verwendung genau dieses Wachses beschränkt ist. Der Zusatz eines der genannten Wachse zu dem Fett der Vormischung beträgt im allgemeinen nur wenige Gewichtsprozent der Vormischung. Für ein besseres Auflösen des Wachses im Fett kann es sich empfehlen, die Vormischung in leichter Wärme von beispielsweise 40°C bis etwa 60°C anzusetzen. Dem Öl wird der Wirkstoff in Form einer Zusammensetzung zugesetzt, welche aus einem Teil Wirkstoff und einem Mehrfaches des Teiles an Vormischung besteht. Für den Fall der erwähnten micellisierten Ascorbinsäure besteht die Zusammensetzung zweckmäßig aus einem Teil Ascorbinsäuresolubilisat und ungefähr 9 Teilen Vormischung.For premixing, fats are suitable as oils, such as fats rich in oil and / or linoleic acid, fish oil or medium-chain triglycerides. These will be waxes that consist of fat-like compounds, higher fatty acids and monohydric higher paraffin alcohols (Myricil, Cetyl, Deryl, Melissyl alcohol), such as wool fat (E 913), beeswax or vegetable wax (Carnauba wax, Candelilla wax, sugar cane wax or also The wax variants mentioned as alternatives, such as wool wax and wool fat, artificial waxes or synthetically produced waxes, only show the desired viscosity-balancing effect between the solubilisate and the oil at higher concentrations. With carnauba wax, the homogeneity of the mixture is difficult to achieve As cooling occurs, particles of different sizes are formed, which is why Gera alba has proven to be a favorable means for the purposes of the invention without the invention being restricted to the use of precisely this wax. The addition of one of the waxes mentioned to the fat of the premix is generally only few G percent by weight of the premix. For a better dissolution of the wax in the fat, it may be advisable to prepare the premix in mild heat, for example from 40 ° C to about 60 ° C. The active substance is added to the oil in the form of a composition which consists of one part of active substance and a multiple of the part of the premix. In the case of the micellized ascorbic acid mentioned, the composition expediently consists of one part of ascorbic acid solubilizate and approximately 9 parts of premix.
Das erfindungsgemäße Verfahren zur Herstellung der Zusammensetzung sieht vor, dass der Wirkstoff mit einer öligen Vormischung verrührt wird, die so eingestellt wird, daß die Viskosität der Zusammensetzung zwischen der Viskosität des Wirkstoffes und der Viskosität des Öles liegt.The process according to the invention for producing the composition provides that the active ingredient is stirred with an oily premix which is adjusted so that the viscosity of the composition lies between the viscosity of the active ingredient and the viscosity of the oil.
Vorteilhafte Ausgestaltungen der erfindungsgemäßen Zusammensetzung sowie zweckmäßige Verfahrensführungen für die Erfindung sind im Übrigen in den Unteransprüchen angegeben. Zur Herstellung der erfindungsgemäßen Öls kann beispielsweise wie folgt vorgegangen werden: Die Viskosität der einzelnen Mischungen bei RT (20°C) wird als Auslaufzeit in Sekunden nach DIN 53211 mit einem FORD-Becher gemessen, der eine Auslaufdüse von 3 mm aufweist. Die Auslaufzeit des in den beiden nachstehenden Beispielen verwendeten Miglyol 812 beträgt 31 ,5 Sekunden. Beispiel 1 In einem ersten Schritt wird eine Vormischung B 1 hergestellt, welche aus Cera alba (CA) und einem leichten, insbesondere pflanzlichen Fett, wie beispielsweise Sonnenblumenöl, Rapsöl oder Distelöl, oder alternativ aus Neutralöl (Miglyol 812) besteht. Dazu werden etwa 97,8 Gew% (bezogen auf 100 Gew% der Vormischung) des Fettes mit 2,2 Gew% CA miteinander vermischt und auf etwa 40 bis etwa 60 °C erwärmt und gerührt, bis die Cera alba-Plättchen sich vollständig in dem Fett gelöst haben. Das Gemisch wird unter ständigem Rühren langsam auf Raumtemperatur abgekühlt. Die Auslaufzeit dieser Vormischung beträgt 146,5 Sekunden.Advantageous refinements of the composition according to the invention and expedient procedures for the invention are otherwise specified in the subclaims. The production of the oil according to the invention can be carried out, for example, as follows: The viscosity of the individual mixtures at RT (20 ° C.) is measured as the run-out time in seconds in accordance with DIN 53211 using a FORD cup which has a 3 mm outlet nozzle. The run-out time of the Miglyol 812 used in the two examples below is 31.5 seconds. Example 1 In a first step, a premix B 1 is produced which consists of cera alba (CA) and a light, in particular vegetable fat, such as sunflower oil, rapeseed oil or safflower oil, or alternatively of neutral oil (Miglyol 812). For this purpose, about 97.8% by weight (based on 100% by weight of the premix) of the fat with 2.2% by weight of CA are mixed with one another and heated to about 40 ° to about 60 ° C. and stirred until the cera alba platelets are completely in loosened the fat. The mixture is slowly cooled to room temperature with constant stirring. The run-time of this premix is 146.5 seconds.
In einem zweiten Schritt wird separat ein Ascorbinsäure-Solubilisat A 1 hergestellt, welches aus Ascorbinsäure, Wasser und Polysorbat 20 besteht. Dazu werden 10 Gew% Ascorbinsäure in 10 Gew% (bezogen auf 100 Gew% Solubilisat) destilliertem Wasser in der Wärme (40 °C bis 60 °C) aufgelöst und unter Rühren bei der angegebenen Temperatur 10 Gew% Miglyol 812 hinzugegeben. Bei Erreichen der Homogenität der Mischung werden 70 Gew% erwärmtes Polysorbat 20 eingetragen und die Mischung bis zur Klarheit und Homogenität gerührt. Die Auslaufzeit dieses Ascorbinsäuresolubilisats beträgt 867,0 Sekunden.In a second step, an ascorbic acid solubilizate A 1 is produced separately, which consists of ascorbic acid, water and polysorbate 20. For this purpose, 10% by weight of ascorbic acid in 10% by weight (based on 100% by weight of solubilisate) of distilled water is dissolved in the heat (40 ° C. to 60 ° C.) and 10% by weight of Miglyol 812 is added with stirring at the temperature specified. When the homogeneity of the mixture is reached, 70% by weight of heated polysorbate 20 are introduced and the mixture is stirred until it is clear and homogeneous. The expiry time of this ascorbic acid solubilizate is 867.0 seconds.
Sodann werden in einem dritten Schritt 90 Gew% der Vormischung B1 und 10 Gew% des Ascorbinsäure-Solubilisats A1 unter Rühren vermischt, so dass die fertige Zusammensetzung 1 Gew% (= 10.000 ppm) an reiner Ascorbinsäure enthält. Die Auslaufzeit dieser Zusammensetzung beträgt 70,5 Sekunden.Then, in a third step, 90% by weight of the premix B1 and 10% by weight of the ascorbic acid solubilizate A1 are mixed with stirring, so that the finished composition contains 1% by weight (= 10,000 ppm) of pure ascorbic acid. The expiration time of this composition is 70.5 seconds.
Beispiel 2Example 2
Herstellung einer Vormischung B 2:Preparation of a premix B 2:
Die in Beispiel 1 genannte Vormischung B 1 erhält einen Zusatz eines Glycerids, beispielsweise Lamegin DWP 2000 (Cognis), welches ein Mono- undThe premix B 1 mentioned in Example 1 contains an addition of a glyceride, for example Lamegin DWP 2000 (Cognis), which is a mono- and
Diacethylweinsäure-Ester von Mono- und Diglyceriden ist. Im Einzelnen werden zu 70 Gew% (bezogen auf die fertige Vormischung = 100 %) der Vormischung B1 20 Gew% Lamegin zugegeben und zur Homogenität verrührt. Die Auslaufzeit beträgt 78,0 Sekunden.Diacethyltartaric acid ester of mono- and diglycerides. Specifically, 70% by weight (based on the finished premix = 100%) of the premix B1 20% by weight of lamegin were added and stirred to homogeneity. The run-down time is 78.0 seconds.
Die Zusammensetzung wird dann in der Weise erhalten, dass 10 Gew% (bezogen auf die Zusammensetzung = 100 Gew%) des Ascorbinsäure-Solubilisats A1 mit 90 Gew% der Vormischung B2 bis zur Homogenität verrührt werden. Diese Zusammensetzung enthält 1 Gew% (= 10.000 ppm) reine Ascorbinsäure. Die Auslaufzeit der Zusammensetzung beträgt 85,0 Sekunden.The composition is then obtained in such a way that 10% by weight (based on the composition = 100% by weight) of the ascorbic acid solubilizate A1 are mixed with 90% by weight of the premix B2 until homogeneous. This composition contains 1% by weight (= 10,000 ppm) of pure ascorbic acid. The expiration time of the composition is 85.0 seconds.
Beispiel 3Example 3
Vormischung B 3: Zu 96,5 Gew% (bezogen auf die Vormischung = 100 Gew%) Miglyol 812 werden 3,5 Gew% Cera alba bei etwa 40°C bis etwa 60°C gegeben und in der Wärme gerührt, bis sich die Cera alba Plättchen vollständig aufgelöst haben. Das warme Gemisch wird unter ständigem Rühren langsam auf RT abgekühlt. Auslaufzeit: 115,5 Sekunden.Premix B 3: 96.5% by weight (based on the premix = 100% by weight) of Miglyol 812, 3.5% by weight of cera alba are added at about 40 ° C. to about 60 ° C. and stirred in the heat until the Have completely dissolved cera alba platelets. The warm mixture is slowly cooled to RT with constant stirring. Flow time: 115.5 seconds.
Solubilisat A 3: Etwa 20 Gew% (bezogen auf das Solubilisat = 100 Gew%) Ascorbinsäure werden bei etwa 45 °C in etwa 20 Gew% destilliertem Wasser vollständig aufgelöst. Der Lösung werden etwa 60 Gew% Polysorbat 80 unter Rühren und Aufwärmen auf etwa 80 °C zugegeben. Es wird bis zur Klarheit und Homogenität des Solubilisats gerührt.Solubilisate A 3: About 20% by weight (based on the solubilisate = 100% by weight) of ascorbic acid are completely dissolved at about 45 ° C. in about 20% by weight of distilled water. About 60% by weight of polysorbate 80 is added to the solution with stirring and warming up to about 80 ° C. The mixture is stirred until the solubilizate is clear and homogeneous.
Zusammensetzung: Etwa 5 Gew% des Solubilisats A 3 werden mit etwa 95 Gew% der Vormischung B 3 verrührt, bis die Homogenität der Zusammensetzung erreicht ist. Die Zusammensetzung enthält dann wiederum etwa 1 Gew% reine Ascorbinsäure. Auslaufzeit: 179,5 Sekunden.Composition: About 5% by weight of solubilizate A 3 is mixed with about 95% by weight of premix B 3 until the composition is homogeneous. The composition then again contains about 1% by weight of pure ascorbic acid. Flow time: 179.5 seconds.
Beispiel 4Example 4
Vormischung B 4: Etwa 96 Gew% (bezogen auf die Vormischung = 100 %) Miglyol 812 werden in der Wärme (Beispiel 3) mit etwa 4 Gew% Cera alba verrührt, bis sich die Cera alba Plättchen vollständig gelöst haben. Das Gemisch wird unter Rühren langsam auf RT abgekühlt. Die Zusammensetzung wird erhalten, indem etwa 10 Gew% des Solubilisats A 3 mit etwa 90 Gew% der Vormischung B 4 bis zur Homogenität verrührt werden. Die Zusammensetzung enthält insgesamt etwa 2 Gew% reine Ascorbinsäure. Die Auslaufzeit beträgt 131 ,5 Sekunden.Premix B 4: About 96% by weight (based on the premix = 100%) of Miglyol 812 are stirred in the heat (Example 3) with about 4% by weight of cera alba until the cera alba platelets have completely dissolved. The mixture is slowly cooled to RT with stirring. The composition is obtained by stirring about 10% by weight of the solubilizate A 3 with about 90% by weight of the premix B 4 until homogeneous. The composition contains a total of about 2% by weight of pure ascorbic acid. The run-down time is 131.5 seconds.
Aus den vorstehenden Beispielen erkennt man, dass die Viskosität der jeweiligen Zusammensetzung, ausgedrückt in Auslaufzeiten, zwischen der Viskosität des Solubilisats und derjenigen des mit der Zusammensetzung zu versetzenden Öls liegt. Dabei ist zu berücksichtigen, dass die Auslaufzeit von A 3 nach der hier angewandten Methode wegen der Zähflüssigkeit von A 3 bei RT nicht bestimmbar ist, jedoch mindestens so groß angenommen werden kann wie diejenige von A 1.From the above examples it can be seen that the viscosity of the respective composition, expressed in terms of run-out times, lies between the viscosity of the solubilizate and that of the oil to be mixed with the composition. It should be taken into account that the run-down time of A 3 cannot be determined using the method used here because of the viscosity of A 3 at RT, but can be assumed to be at least as long as that of A 1.
Die anhand der vorstehenden Beispiele beschriebene Erfindung hat den weiteren Vorteil, dass das sedimentfreie Versetzen des Öls mit der erfindungsgemäßen Zusammensetzung bei RT durchgeführt werden kann. Die Erfindung ist indes auf die konkreten Zahlenangaben und die erwähnten Ausgangsstoffe nicht beschränkt. Wenn nämlich toleriert werden kann, dass die Zugabe der Zusammensetzung zum Öl auch in leichter Wärme (etwa 30°C bis etwa 60°C) erfolgen kann, kommen auch andere Vormischungen, Solubilisate und Zusammensetzungen in Betracht, solange die Viskosität der Zusammensetzung bei der gewählten Temperatur zwischen derjenigen des Solubilisats und derjenigen des Öls liegt.The invention described with reference to the preceding examples has the further advantage that the sediment-free addition of the oil with the composition according to the invention can be carried out at RT. However, the invention is not limited to the specific figures and the starting materials mentioned. If it can be tolerated that the addition of the composition to the oil can also be carried out under mild heat (about 30 ° C. to about 60 ° C.), other premixes, solubilisates and compositions can also be considered, as long as the viscosity of the composition at the chosen one Temperature is between that of the solubilizate and that of the oil.
Man kann daher auch wie folgt vorgehen: Etwa 88,5 Gew% (bezogen auf die Zusammensetzung = 100 %) eines Öles, das ein Pflanzenöl, Fischöl oder ein mittelkettiges Triglycerid sein kann, werden auf etwa 80 °C erwärmt. Dem warmen Öl werden etwa 1 ,5 Gew% Bienenwachs (cera alba) zugegeben und gerührt. Nach Auflösung des Wachses werden der warmen Mischung etwa 10 Gew% des vorstehend genannten Ascorbinsäure-Solubilisats zugegeben. Das Rühren wird fortgesetzt, bis nach Abschalten der Heizung die Zusammensetzung sich auf Raumtemperatur abgekühlt hat.One can therefore proceed as follows: About 88.5% by weight (based on the composition = 100%) of an oil, which can be a vegetable oil, fish oil or a medium-chain triglyceride, are heated to about 80 ° C. About 1.5% by weight of beeswax (cera alba) is added to the warm oil and stirred. After the wax has dissolved, about 10% by weight of the above-mentioned ascorbic acid solubilizate is added to the warm mixture. Stirring continues until after the heater is turned off the composition has cooled to room temperature.
Diese erfindungsgemäße Zusammensetzung bleibt auch nach längerer Lagerung (bei Raumtemperatur oder darunter) stabil homogen und sedimentfrei und enthält ca. 1 Gew% bzw. 10.000 ppm reine, chemisch unveränderte Ascorbinsäure (Vitamin C). Diese Ascorbinsäure-Konzentration im Öl liegt ca. 20-fach über der Konzentration, welche durch derivatisierte Ascorbinsäure-Varianten, wie z.B. Ascorbyl-Palmitat (bisher einzige nicht phenolische Antioxidans-Variante), in Ölen erreicht worden ist. Die Erfindung lässt sich auch mit einem Ascorbinsäuresolubilisat realisieren, bei welchem statt Polysorbat 80 das Polysorbat 20 eingesetzt worden ist.This composition according to the invention remains stable, homogeneous and free of sediment even after prolonged storage (at room temperature or below) and contains about 1% by weight or 10,000 ppm of pure, chemically unchanged ascorbic acid (Vitamin C). This ascorbic acid concentration in the oil is approx. 20 times the concentration that has been achieved in oils by derivatized ascorbic acid variants, such as ascorbyl palmitate (previously the only non-phenolic antioxidant variant). The invention can also be implemented with an ascorbic acid solubilizate in which polysorbate 20 has been used instead of polysorbate 80.
Statt der vorstehend genannten Triglyceride kann man das Ascorbinsäure- Solubilisat auch mit mittelkettigen Triglyceriden gewinnen, die üblicherweise einen wesentlichen Gehalt an Caprylsäure und Caprinsäure aufweisen. Ferner kann man das Ascorbinsäure-Solubilisat auch durch Verwendung von Polysorbat 20 statt Polysorbat 80 herstellen, wobei die genannten Gewichtsverhältnisse im Wesentlichen beibehalten werden können. Die Auslaufzeit eines solchen mit Polysorbat 20 hergestellten Ascorbinsäure-Solubilisats wird zu 15,5 Minuten gemessen.Instead of the above-mentioned triglycerides, the ascorbic acid solubilizate can also be obtained with medium-chain triglycerides, which usually have a substantial content of caprylic acid and capric acid. Furthermore, the ascorbic acid solubilizate can also be produced by using polysorbate 20 instead of polysorbate 80, the weight ratios mentioned being able to be essentially maintained. The run-out time of such an ascorbic acid solubilizate produced with polysorbate 20 is measured at 15.5 minutes.
Die erfindungsgemäße Zusammensetzung kann dem Öl in einer Menge je nach Bedarf (bis 25 Gew%) zugegeben werden. Damit lässt sich der Anteil an Ascorbinsäure in dem Öl frei einstellen, ohne dass dazu weitere Maßnahmen (Zugabe von Additiven oder der Einsatz besonderer Rührwerke) erforderlich wären.The composition according to the invention can be added to the oil in an amount as required (up to 25% by weight). This means that the proportion of ascorbic acid in the oil can be freely adjusted without the need for further measures (addition of additives or the use of special agitators).
Wie dargelegt, eignet sich die Zusammensetzung zur Konservierung von Ölen. Darüber hinaus kann die Zusammensetzung als Hauptkomponente (Oxidations- Compound) bei der Zubereitung von Teigen oder Teigmischungen Verwendung finden, aus denen Backwaren hergestellt werden sollen. Ferner empfiehlt sich die Verwendung der Zusammensetzung als antioxidativer Zusatz bei der Herstellung von Fischwaren, insbesondere Fischkonserven und als Zusatz zu Kosmetika. As stated, the composition is suitable for the preservation of oils. In addition, the composition can be used as the main component (oxidation compound) in the preparation of doughs or dough mixtures from which baked goods are to be produced. It is also recommended to use the composition as an antioxidant additive in the manufacture of fish products, in particular canned fish and as an additive to cosmetics.
Claims
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| DE10353559 | 2003-11-14 | ||
| PCT/EP2004/012945 WO2005046349A2 (en) | 2003-11-14 | 2004-11-15 | Oleaginous composition containing a flowable active ingredient |
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Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5528950A (en) * | 1978-08-24 | 1980-02-29 | Takasago Corp | Skin cosmetic |
| JPS59204696A (en) * | 1983-05-06 | 1984-11-20 | 三井製薬工業株式会社 | Antioxidant |
| JPH01502189A (en) * | 1986-12-08 | 1989-08-03 | アルセコ・インコーポレイテッド | Storage stable composition for topical administration |
| US4847078A (en) * | 1987-01-14 | 1989-07-11 | Arseco, Inc. | Storage stable topical composition having moisture control agent |
| DK0410236T3 (en) * | 1989-07-25 | 1993-12-13 | Hoffmann La Roche | Process for the preparation of caratenoid preparations |
| US5559149A (en) * | 1990-01-29 | 1996-09-24 | Johnson & Johnson Consumer Products, Inc. | Skin care compositions containing retinoids |
| US5155244A (en) * | 1990-02-28 | 1992-10-13 | Karlshamns Ab | Preparation of antioxidant glyceride derivatives utilizing esterification |
| GB9219524D0 (en) * | 1992-09-15 | 1992-10-28 | Smithkline Beecham Plc | Novel composition |
| RU2115409C1 (en) * | 1996-02-13 | 1998-07-20 | Акционерное общество открытого типа "Уральские самоцветы" | Cream for face care |
| JP3989068B2 (en) * | 1997-12-09 | 2007-10-10 | 辻製油株式会社 | Oil composition with a high content of lysophosphatidylcholine |
| EP0956779A1 (en) * | 1998-05-11 | 1999-11-17 | Vesifact Ag | Foods containing water-insoluble compounds |
| US6103267A (en) * | 1998-07-27 | 2000-08-15 | Sunsmart, Inc. | Stabilized ascorbic acid, composition, and method of use |
| IT1301994B1 (en) * | 1998-08-05 | 2000-07-20 | Jasper Ltd Liability Co | HYALURONIC ACID DERIVATIVES. |
| US6110477A (en) * | 1998-10-30 | 2000-08-29 | Topix Pharmaceuticals Inc. | Stabilization of ascorbic acid, ascorbic acid derivatives and/or extracts containing ascorbic acid for topical use |
| JP2002104958A (en) * | 2000-09-29 | 2002-04-10 | Sumitomo Chem Co Ltd | Lipophilic vitamin preparations |
| NL1017333C2 (en) * | 2001-02-12 | 2002-08-13 | Gent Natural Products Van | Cosmetic resp. pharmaceutical preparation. |
| JP3597478B2 (en) * | 2001-02-19 | 2004-12-08 | 日清オイリオグループ株式会社 | Tocopherol preparation with suppressed flavor deterioration and food and beverage containing the same |
| FR2825277B1 (en) * | 2001-05-30 | 2004-10-15 | Oreal | COSMETIC AND / OR DERMATOLOGICAL AND / OR PHARMACEUTICAL COMPOSITION CONTAINING AT LEAST ONE ENZIME 3, B-HSD IHNIBITOR COMPOUND |
| DE10158447B4 (en) * | 2001-11-30 | 2005-02-10 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Ascorbic Solubilisate |
| EP1344516A1 (en) * | 2002-03-12 | 2003-09-17 | Cognis Iberia, S.L. | Antioxidative composition |
-
2004
- 2004-11-15 US US10/579,246 patent/US20070065470A1/en not_active Abandoned
- 2004-11-15 JP JP2006538821A patent/JP2007511213A/en active Pending
- 2004-11-15 WO PCT/EP2004/012945 patent/WO2005046349A2/en not_active Ceased
- 2004-11-15 EP EP04818406A patent/EP1684598A2/en not_active Withdrawn
- 2004-11-15 RU RU2006120545/13A patent/RU2006120545A/en not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005046349A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2006120545A (en) | 2007-12-27 |
| US20070065470A1 (en) | 2007-03-22 |
| JP2007511213A (en) | 2007-05-10 |
| WO2005046349A2 (en) | 2005-05-26 |
| WO2005046349A3 (en) | 2005-11-10 |
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