EP0235528A1 - Procédé de préparation d'huiles ozonisées stables à partir d'huiles végétales insaturées - Google Patents
Procédé de préparation d'huiles ozonisées stables à partir d'huiles végétales insaturées Download PDFInfo
- Publication number
- EP0235528A1 EP0235528A1 EP87100725A EP87100725A EP0235528A1 EP 0235528 A1 EP0235528 A1 EP 0235528A1 EP 87100725 A EP87100725 A EP 87100725A EP 87100725 A EP87100725 A EP 87100725A EP 0235528 A1 EP0235528 A1 EP 0235528A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- oils
- unsaturated vegetable
- ascorbic acid
- vegetable oils
- 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.)
- Granted
Links
- 239000003921 oil Substances 0.000 title claims abstract description 22
- 235000019198 oils Nutrition 0.000 title claims abstract description 22
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 10
- 239000008158 vegetable oil Substances 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 6
- 235000006708 antioxidants Nutrition 0.000 claims abstract description 6
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 5
- 238000007348 radical reaction Methods 0.000 claims abstract description 4
- 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 15
- 235000010323 ascorbic acid Nutrition 0.000 claims description 13
- 239000011668 ascorbic acid Substances 0.000 claims description 13
- 229960005070 ascorbic acid Drugs 0.000 claims description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 239000004006 olive oil Substances 0.000 claims description 9
- 235000008390 olive oil Nutrition 0.000 claims description 8
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 235000019485 Safflower oil Nutrition 0.000 claims description 4
- 238000006385 ozonation reaction Methods 0.000 claims description 4
- 235000005713 safflower oil Nutrition 0.000 claims description 4
- 239000003813 safflower oil Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019489 Almond oil Nutrition 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 2
- 239000008168 almond oil Substances 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- -1 croton oil Substances 0.000 claims description 2
- 229940117173 croton oil Drugs 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 239000010466 nut oil Substances 0.000 claims description 2
- 235000019488 nut oil Nutrition 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 235000011803 sesame oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- 235000019155 vitamin A Nutrition 0.000 claims description 2
- 239000011719 vitamin A Substances 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229940045997 vitamin a Drugs 0.000 claims description 2
- 239000010497 wheat germ oil Substances 0.000 claims description 2
- 235000008753 Papaver somniferum Nutrition 0.000 claims 1
- 240000001090 Papaver somniferum Species 0.000 claims 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 17
- 229940118019 malondialdehyde Drugs 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 11
- 150000002978 peroxides Chemical class 0.000 description 9
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 6
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 6
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 6
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 1
- DQNVJWKDCCSMLW-UHFFFAOYSA-N 2-methylideneindole Chemical compound C1=CC=CC2=NC(=C)C=C21 DQNVJWKDCCSMLW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 208000005230 Leg Ulcer Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- LNTHITQWFMADLM-UHFFFAOYSA-M gallate Chemical compound OC1=CC(C([O-])=O)=CC(O)=C1O LNTHITQWFMADLM-UHFFFAOYSA-M 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation
Definitions
- the invention relates to a process for the production of stable ozonized oils from unsaturated vegetable oils with removal of physiologically questionable low molecular weight aldehydes and ketones.
- the process according to the invention provides valuable products which are suitable for therapeutic and cosmetic use in humans and animals.
- reaction of ozone with unsaturated fatty acids produces peroxidic products as therapeutically valuable active substances and low-molecular aldehydes and ketones, especially malondialdehyde, as undesirable by-products.
- the peroxidic products are used, for example, in dermatology for fungal diseases, leg ulcers, poorly healing wounds, infected wounds and the like.
- the ketones and aldehydes formed as by-products are therapeutically ineffective and largely physiologically questionable. The latter is particularly true for malondialdehyde, which occurs in considerable quantities when ozonization of unsaturated vegetable oils is complete (see Registry of Toxic Effects of Chemical Substances, U.S. Department of Health and Human Services, 1984).
- the object of the invention is to provide ozonized products from unsaturated vegetable oils which are therapeutically valuable products, are stable for a long time and have the lowest possible content of low molecular weight aldehydes and ketones, in particular malondialdehyde.
- the invention relates to a process for producing stable ozonized oils from unsaturated vegetable oils by introducing an ozone-oxygen mixture into the oil until saturation, which is characterized in that after the ozonization, an extraction treatment in an acidic environment in the presence of a redox system, preferably a biological redox system which is capable of a moderate radical reaction and which carries out in the presence of an artificial or natural antioxidant or reducing agent.
- a redox system preferably a biological redox system which is capable of a moderate radical reaction and which carries out in the presence of an artificial or natural antioxidant or reducing agent.
- unsaturated vegetable oils are olive oil, safflower oil, wheat germ oil, linseed oil, almond oil, nut oil, sunflower oil, poppy seed oil, sesame oil, castor oil, croton oil, soybean oil and palm oil. Olive and safflower oils are preferred. Olive oil is especially preferred.
- the redox system used which is capable of radical reactions, acts in the organism both as an electron acceptor and as an electron donor.
- Preferred examples of redox systems are ascorbic acid, the essentially membrane-associated redox system vitamin E, vitamin A and the biological quinoid / benzoid systems. Ascorbic acid is particularly preferred.
- a pH of 3.5 to 6.5 has proven to be particularly suitable for carrying out the extraction treatment.
- ascorbic acid or citric acid can be used.
- antioxidants or reducing agents are butylated hydroxyanisole, gallate and hydrogen sulfite.
- the ozone-oxygen mixture is produced in compliance with the regulations for the production or filling of medical oxygen.
- the ozone is generated by a silent electrical discharge (absolutely nitrogen-free to avoid the formation of aggressive and reactive nitrogen oxides, especially radicals).
- the ozonization of the oil is carried out with a continuous pass with a gas flow in the range of 1 to 2 liters per minute.
- the ozone concentration used is preferably in the range from 50 to 70 ⁇ g per ml.
- the oil is bubbled through using a cylindrical vessel with the highest possible “water column” with thermostatting at about 20 ° C.
- a continuous flow is important, especially just before the saturation limit, which becomes apparent when the product solidifies at 20 ° C.
- For 12 liters with a total height of the cylindrical vessel of 60 cm and a diameter of approx. 20 cm, a uniform bubbling time of 180 to 300 hours is required, depending on the ozone concentration of the initial ozone-oxygen mixture.
- aqueous extraction solution For the extraction treatment, about 2 to 20, in particular 3 to 10 and preferably about 5 ml of aqueous extraction solution are used per 1 g of ozonized oil.
- the extraction is preferably carried out by shaking for 10 to 60 minutes. The shaking process can be carried out several times to increase the effectiveness. Any excess sulfite still present in the extract can be removed by shaking out the oily phase with 2% aqueous ascorbic acid solution.
- Particularly preferred combinations for the extraction treatment according to the invention are ascorbic acid + butylated hydroxyanisole, citric acid and butylated hydroxyanisole as well as ascorbic acid and hydrogen sulfite.
- the determination is based on the reaction of malondialdehyde with 2-methylindole in alcoholic-hydrochloric acid solution to form a stable, intensely colored complex.
- Determination of malondialdehyde in ozonized oil About 1 g of the solid oil is weighed exactly and warmed to liquefy under an N2 atmosphere (approx. 30 ° C). Since the oil is immiscible with the reagents, 1 ml of distilled H2O are added in addition to 2 ml of methyl indole and stirred with a magnetic stirrer under the N2 atmosphere during the 20 min reaction time to allow a complete reaction of the malondialdehyde. The alcoholic phase is then measured (after the fat has been removed) in comparison with the calibration series that is applied in parallel each time.
- the product obtained has a peroxide number (POZ) of 929 and a malondialdehyde content of 445 ⁇ g / g of oil.
- the extraction treatment removed 85 percent of the malondialdehyde, while the peroxide number only decreased by 5.7 percent.
- the aqueous extract contains no peroxides, while the malondialdehyde has almost completely passed into the aqueous phase.
- Samples of the ozonated olive oil produced according to Example 1 are subjected to different extraction treatments. For this purpose, 1 g ozonized oil is shaken out with various aqueous solutions for 15 minutes. The POZ and malondialdehyde content are then determined. The results are summarized in the table below.
- x) 1 means that the parameter in question has not been determined
- x) 2 excess sulfite was completely removed by shaking the oil with 10 ml H2O (2 g ascorbic acid / 100 ml), whereby the POZ and malondialdehyde content of the ozonated oil did not change significantly: the peroxide number decreased from 876 to 860, the malondialdehyde content from 68 ⁇ g / g to 52 ⁇ g / g.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT87100725T ATE42965T1 (de) | 1986-03-01 | 1987-01-20 | Verfahren zur herstellung von stabilen ozonisierten oelen aus ungesaettigten pflanzenoelen. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3606735A DE3606735C2 (de) | 1986-03-01 | 1986-03-01 | Verfahren zur Herstellung von stabilen ozonisierten Ölen aus ungesättigten Pflanzenölen |
| DE3606735 | 1986-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0235528A1 true EP0235528A1 (fr) | 1987-09-09 |
| EP0235528B1 EP0235528B1 (fr) | 1989-05-10 |
Family
ID=6295281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87100725A Expired EP0235528B1 (fr) | 1986-03-01 | 1987-01-20 | Procédé de préparation d'huiles ozonisées stables à partir d'huiles végétales insaturées |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0235528B1 (fr) |
| AT (1) | ATE42965T1 (fr) |
| DE (1) | DE3606735C2 (fr) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996025409A1 (fr) * | 1995-02-16 | 1996-08-22 | Cosmart Ag | Compositions cosmetiques ou pharmaceutiques contenant une huile vegetale naturelle enrichie en ozonides et utilisations |
| FR2784388A1 (fr) * | 1998-10-07 | 2000-04-14 | Bernard Sonnois | Huile ozonisee obtenue par generateur alimente en oxygene pur - huile saturee en ozone |
| WO2000078699A1 (fr) * | 1999-06-18 | 2000-12-28 | E.I. Du Pont De Nemours | Clivage oxydant d'huiles insaturees et produits obtenues a partir de celles-ci |
| WO2001037829A1 (fr) * | 1999-11-25 | 2001-05-31 | Gomez Moraleda Manuel Antonio | Composition comprenant des huiles ozonisees et/ou autres produits naturels et/ou de synthese ozonises, et son utilisation dans des compositions pharmaceutiques, cosmetiques, dietetiques ou de complements alimentaires utilisees en medecine humaine et veterinaire |
| WO2006021924A1 (fr) * | 2004-08-26 | 2006-03-02 | Pieter Josua Le Roux | Huile therapeutique |
| WO2007046122A3 (fr) * | 2005-10-17 | 2007-06-14 | Biopharma 3M S R L | Huile ozonisee, procede d'elaboration et utilisation dans le domaine medical |
| EP1681338A4 (fr) * | 2003-10-02 | 2008-11-19 | Sun Care Fuels Corp | Modificateur pour carburant biodiesel, carburant et procedes associes |
| WO2010039064A1 (fr) * | 2008-10-03 | 2010-04-08 | Sca Hygiene Products Ab | Lingette comprenant une substance désodorisante |
| RU2462271C1 (ru) * | 2008-10-03 | 2012-09-27 | Ска Хайджин Продактс Аб | Влажная салфетка с дезодорирующим веществом |
| ITUB20155250A1 (it) * | 2015-11-24 | 2017-05-24 | Apuzzo Dario | Nuova composizione nutraceutica, somministrabile per via orale, utile per esercitare una potente stimolazione del metabolismo, in particolare del metabolismo energetico muscolare. |
| IT202000024967A1 (it) * | 2020-10-23 | 2022-04-23 | Giovanni Sandomenico | Fluido ozonizzato a presidio - difesa delle prime vie respiratorie |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10157260B4 (de) * | 2001-11-22 | 2005-12-15 | Pharmoxid Arznei Gmbh + Co. Kg | Streichfähige Salbe mit Ozoniden und Peroxiden von Fettsäuren oder deren Estern |
| DE102012007239A1 (de) | 2012-04-10 | 2013-10-10 | Wolfgang Winkelmann | Pharmazeutische Zusammensetzung enthaltend eine mit Sauerstoff angereicherte ungesättigte Fettsäure und ein organisches Lösungsmittel |
| DE102015001289A1 (de) | 2015-01-29 | 2016-08-04 | Wolfgang Winkelmann | Pharmazeutische Zusammensetzungen und Pflanzenschutzmittel enthaltend mit Sauerstoff angereicherte Pflanzenöle oder Fettsäuren |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2083572A (en) * | 1928-04-25 | 1937-06-15 | Susan M Mckee | Process of treating oil |
| DE1068251B (de) * | 1959-11-05 | Chemische Fabrik Stockhausen S. Oie, Krefeld | Verfahren zur Herstellung von in Wasser löslichen bzw. emiuligierbaren, elektrolytbeständigen Fettungsmijtteln |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5869207A (ja) * | 1981-10-21 | 1983-04-25 | Nippon Petrochem Co Ltd | エポキシ化物の精製方法 |
| EP0117962B1 (fr) * | 1983-01-06 | 1987-09-16 | Marie-Françoise Lepeltier | Procédé de préparation de graisses peroxydées par transformation biologique à faible énergie, produits obtenus par ce procédé, mélanges de ces produits avec des additifs et nouveaux médicaments constitués de ces produits |
-
1986
- 1986-03-01 DE DE3606735A patent/DE3606735C2/de not_active Expired - Fee Related
-
1987
- 1987-01-20 AT AT87100725T patent/ATE42965T1/de not_active IP Right Cessation
- 1987-01-20 EP EP87100725A patent/EP0235528B1/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1068251B (de) * | 1959-11-05 | Chemische Fabrik Stockhausen S. Oie, Krefeld | Verfahren zur Herstellung von in Wasser löslichen bzw. emiuligierbaren, elektrolytbeständigen Fettungsmijtteln | |
| US2083572A (en) * | 1928-04-25 | 1937-06-15 | Susan M Mckee | Process of treating oil |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996025409A1 (fr) * | 1995-02-16 | 1996-08-22 | Cosmart Ag | Compositions cosmetiques ou pharmaceutiques contenant une huile vegetale naturelle enrichie en ozonides et utilisations |
| FR2730636A1 (fr) * | 1995-02-16 | 1996-08-23 | Cosmart Ag | Huile vegetale naturelle enrichie en ozonides, compositions cosmetiques ou pharmaceutiques la contenant et utilisations |
| FR2784388A1 (fr) * | 1998-10-07 | 2000-04-14 | Bernard Sonnois | Huile ozonisee obtenue par generateur alimente en oxygene pur - huile saturee en ozone |
| US6768029B1 (en) | 1999-06-18 | 2004-07-27 | Cambridge Biopolymers Limited | Oxidative cleavage of unsaturated oils and products obtained therefrom |
| WO2000078699A1 (fr) * | 1999-06-18 | 2000-12-28 | E.I. Du Pont De Nemours | Clivage oxydant d'huiles insaturees et produits obtenues a partir de celles-ci |
| WO2001037829A1 (fr) * | 1999-11-25 | 2001-05-31 | Gomez Moraleda Manuel Antonio | Composition comprenant des huiles ozonisees et/ou autres produits naturels et/ou de synthese ozonises, et son utilisation dans des compositions pharmaceutiques, cosmetiques, dietetiques ou de complements alimentaires utilisees en medecine humaine et veterinaire |
| ES2162586A1 (es) * | 1999-11-25 | 2001-12-16 | Moraleda Manuel Gomez | Composicion que comprende aceites ozonizados y/o otros productos naturales y/o sinteticos ozonizados, y su empleo en composiciones farmaceuticas, cosmeticas, dieteticas o de suplementos alimentarios, en los campos humano y veterinario |
| EP1681338A4 (fr) * | 2003-10-02 | 2008-11-19 | Sun Care Fuels Corp | Modificateur pour carburant biodiesel, carburant et procedes associes |
| WO2006021924A1 (fr) * | 2004-08-26 | 2006-03-02 | Pieter Josua Le Roux | Huile therapeutique |
| WO2007046122A3 (fr) * | 2005-10-17 | 2007-06-14 | Biopharma 3M S R L | Huile ozonisee, procede d'elaboration et utilisation dans le domaine medical |
| WO2010039064A1 (fr) * | 2008-10-03 | 2010-04-08 | Sca Hygiene Products Ab | Lingette comprenant une substance désodorisante |
| RU2462271C1 (ru) * | 2008-10-03 | 2012-09-27 | Ска Хайджин Продактс Аб | Влажная салфетка с дезодорирующим веществом |
| ITUB20155250A1 (it) * | 2015-11-24 | 2017-05-24 | Apuzzo Dario | Nuova composizione nutraceutica, somministrabile per via orale, utile per esercitare una potente stimolazione del metabolismo, in particolare del metabolismo energetico muscolare. |
| IT202000024967A1 (it) * | 2020-10-23 | 2022-04-23 | Giovanni Sandomenico | Fluido ozonizzato a presidio - difesa delle prime vie respiratorie |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE42965T1 (de) | 1989-05-15 |
| EP0235528B1 (fr) | 1989-05-10 |
| DE3606735C2 (de) | 1994-11-10 |
| DE3606735A1 (de) | 1987-09-10 |
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