WO2000071672A1 - Verwendung von mikroemulsionen in fermentationsverfahren - Google Patents

Verwendung von mikroemulsionen in fermentationsverfahren Download PDF

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Publication number
WO2000071672A1
WO2000071672A1 PCT/EP2000/004364 EP0004364W WO0071672A1 WO 2000071672 A1 WO2000071672 A1 WO 2000071672A1 EP 0004364 W EP0004364 W EP 0004364W WO 0071672 A1 WO0071672 A1 WO 0071672A1
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Prior art keywords
weight
acid
emulsions
use according
alcohol
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PCT/EP2000/004364
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German (de)
English (en)
French (fr)
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WO2000071672A8 (de
Inventor
Matthias Wegener
Jean-Pierre Molitor
Christian De Haut
Benoit Abribat
Bent Rogge
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Cognis Deutschland Gmbh
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Priority to MXPA01011818A priority Critical patent/MXPA01011818A/es
Priority to EP00945681A priority patent/EP1180137A1/de
Priority to PL00352059A priority patent/PL352059A1/xx
Priority to KR1020017015012A priority patent/KR20020012580A/ko
Priority to SK1694-2001A priority patent/SK16942001A3/sk
Priority to JP2000620052A priority patent/JP2003500043A/ja
Priority to BR0010873-1A priority patent/BR0010873A/pt
Publication of WO2000071672A1 publication Critical patent/WO2000071672A1/de
Publication of WO2000071672A8 publication Critical patent/WO2000071672A8/de
Priority to NO20015732A priority patent/NO20015732D0/no
Priority to HK02105053.1A priority patent/HK1043478A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/26—Processes using, or culture media containing, hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins

Definitions

  • the present invention relates to the use of microemulsions in fermentation processes.
  • Microbiological processes are increasingly used in the synthesis of complex natural products or other organic compounds, for example antibiotics. It is a matter conversion under anaerobic or aerobic conditions, in which microorganisms, or parts of microorganisms, but especially bacteria or fungi are involved.
  • Various such expressions such as “bioconversion”, “biotransformation” or “fermentation”, which are not always clearly delimited from one another, are used in the art for such processes.
  • the latter expression is also used in the context of the present application for those processes in which microorganisms, preferably bacteria, are used for the conversion or synthesis of chemical compounds.
  • the reaction medium in which the microbiological conversion takes place is of particular importance for the development and optimization of fermentation processes.
  • the reaction medium usually an aqueous solution or dispersion, influences in particular the yield and efficiency of the process.
  • the microorganisms need carbon, nitrogen and certain trace elements in bound form, for example calcium, iron, phosphorus or zinc, in order to enable successful metabolism to the desired products.
  • a certain, usually narrow temperature and pH range must be maintained.
  • a microbial process for the production of alpha-omega-dicarboxylic acids wherein bacteria from the Candida tropicalis strain convert methyl laurate into the desired dicarboxylic acids.
  • the conversion takes place in an aqueous medium at a pH of 6.0 and a temperature of 30 ° C.
  • the medium also contains ethoxylated sorbitan monooleate as an emulsifier, yeast extract, corn steep liquor and inorganic N and P sources.
  • the methyl laurate is then metered into the medium.
  • the document does not indicate the type of emulsion which forms in the fermenter or in which the methyl laurate is added to the medium.
  • EP 0 535 939 A1 discloses a process for the preparation of omega-9 polyunsaturated fatty acids, suitable microorganisms in an aqueous culture medium in the presence of sugars as energy suppliers and inorganic or organic nitrogen sources, and in the presence of fatty acid methyl esters, the desired polyunsaturated Produce fatty acids.
  • the oxygen content in the medium or the fermentation broth plays a decisive role in fermentation processes.
  • Oxygen plays the role of a substrate in aerobic processes.
  • the decisive factor is whether an adequate oxygen transition from the gas to the liquid phase, which contains the microorganisms, can take place for the respective process.
  • An important parameter is the specific exchange area, which is usually determined indirectly via the oxygen transfer coefficient k (cf. Literature Crueger, chapter 5, page 71 ff).
  • the optimum oxygen input is typically set by stirring the fermentation broth, the oxygen or air being mixed with the liquid and the gas exchange thus taking place at the interfaces.
  • the considerable mechanical energy input from vigorous stirring, as Park et al. perform also destroy parts of the culture, thus reducing the yield of the process.
  • the dead microorganisms are also further broken down themselves and can lead to a poisoning of the culture by the degradation products formed, which makes economic production impossible.
  • Goma and Rols G. Goma, JL Rols, Biotech. Let., Vol 13, No. 1, pages 7 to 12, 1991
  • the use of soybean oil in fermentation processes for the production of antibiotics is an improvement of the oxygen transfer coefficient k, which can lead to an increase in the yield of the overall process with the same energy input (stirring).
  • the present invention was based on the object of improving fermentation processes in such a way that, on the one hand, inexpensive carbon sources can be used and, on the other hand, an adequate supply of the microorganisms with oxygen is ensured without an impermissibly high mechanical load on the microorganisms due to stirring.
  • a way should be found to minimize the mechanical energy input in fermentation processes without reducing the yield. An increase in the yield should preferably be possible despite the reduced energy input.
  • O / W emulsions in fermentation processes, these emulsions containing at least water, emulsifiers and an oil phase and the oil phase vegetable or one or more compounds from groups a) the fatty acid alkyl esters and / or b) the triglycerides Contain origin, the emulsions have a droplet size of 1 to 100 nm.
  • the emulsions according to the invention are distinguished in particular by their fine particle size.
  • microemulsions which are defined as macroscopically homogeneous, optically transparent, often low-viscosity, thermodynamically stable mixtures of two immiscible liquids and at least one nonionic or one ionic surfactant, which preferably contains two hydrophobic residues.
  • the formation of a microemulsion results in a situation in which the oil-water interfacial tension approaches zero.
  • the droplet size of the emulsions used according to the invention is 1 to 100 nm.
  • the droplet size is preferably in the range from 10 to 80 nm, in particular in the range from 10 to 30 nm.
  • the fine particle size of the oil droplets leads to a large surface area between the oil and water phases and thus enables rapid contact between the microorganisms contained in the aqueous phase and the oil phase containing the nutrients.
  • the large surface area also simplifies gas exchange, especially of oxygen and CO.
  • the viscosity of the emulsion and thus of the entire fermentation medium is reduced. As a result, it is therefore possible to significantly reduce the stirring speed of the fermentation medium, thereby making it possible to increase the yield of the fermentation process.
  • the microemulsions are metered into the aqueous fermentation medium which contains the microorganisms and, if appropriate, further auxiliaries and additives.
  • the details of this process, in particular the speed and amount of the emulsion added, result from the type of microorganisms and the fermentation process chosen and can be adapted to the specific circumstances by a person skilled in the art.
  • the microemulsions contain an oil phase which contains compounds from the group of the fatty acid alkyl esters a) or the native vegetable oils and their derivatives b).
  • Groups a) and b) are hydrophobic compounds which are insoluble or only slightly soluble in water and which serve both as nutrients and energy suppliers for the Bacteria used in the fermentation process can serve, but they can also be raw materials (substrates) for the products desired by bioconversion.
  • Suitable methyl esters of group a) are derived in particular from saturated, unsaturated, linear or branched fatty acids with a total of 7 to 23 carbon atoms. These are compounds of the formula (I)
  • R 1 is an alkyl radical having 6 to 22 carbon atoms and R 2 is an alkyl radical having 1 to 4 carbon atoms.
  • Methyl and ethyl radicals are preferred.
  • the use of methyl esters as component a) is particularly preferred.
  • the esters of formula (I) or the methyl esters can be obtained in a conventional manner, for example by transesterification of triglycerides with methanol and subsequent distillation.
  • Suitable fatty acids are capronic, heptanoic, caprylic, pearlagon, capric, undecane, lauric, tridecane, myristic, pentadecane, palmitic, heptadecanoic, stearic, nonadecanoic, arachic and behenic acids .
  • Unsaturated representatives are, for example, lauric acid, myristoleic acid, palmitoleic acid, petroselaidic acid, oleic acid, elaidin acid, ricinoleic acid, linoleic acid, linolaidic acid, linolenic acid, arachidone and erucic acid.
  • methyl esters of these acids are also suitable. It is particularly preferred to use those microemulsions which contain methyl esters from the group consisting of methyl oleate, methyl Pamitat, methyl stearate and / or methyl pelargonate. But it is also possible to "use" methyl esters based on natural fatty acid mixtures, such as those from linseed, coconut, palm, palm kernel, olive, castor, beet, sesame, soybean or sunflower oil (in the case of rapeseed oil and sunflower oil, both new and old varieties) can be obtained.
  • natural fatty acid mixtures such as those from linseed, coconut, palm, palm kernel, olive, castor, beet, sesame, soybean or sunflower oil (in the case of rapeseed oil and sunflower oil, both new and old varieties) can be obtained.
  • Suitable group b) compounds are native oils of vegetable origin. These are essentially triglyceride mixtures, with the glycerin being completely esterified with longer-chain fatty acids. Particularly suitable vegetable oils are selected from the group of peanut, coconut, linseed, palm, olive, palm kernel, castor oil, rapeseed, sesame, soybean and sunflower oil. Peanut oil contains on average (based on fatty acid) 54% by weight oleic acid, 24% by weight
  • Linoleic acid 1st% by weight linolenic acid, 1% by weight arachic acid, 10% by weight palmitic acid, and 4% by weight stearic acid.
  • the melting point is 2 to 3 ° C.
  • Linseed oil typically contains 5% by weight palmitin, 4% by weight stearin, 22% by weight oil, 17
  • % By weight of linoleic and 52% by weight of linolenic acid.
  • the iodine number is in the range from 155 to 205,
  • the saponification number is 188 to 196 and the melting point is about - 20 ° C.
  • Coconut oil contains about 0.2 to 1% by weight of hexane, 5 to 8% by weight of octane, 6 to 9 of fatty acids
  • the iodine number is in the range of 7.5 to 9.5, the saponification number is 0.88 to 0.90.
  • the melting point is 20 to 23 ° C.
  • Olive oil mainly contains oleic acid (see clarchem . sublimel. Chem., 39, 112 bis
  • Palm oil contains about 2% by weight myristine, 42% by weight as fatty acid components
  • Palmitic 5% by weight stearic, 41% by weight oleic, 10% by weight linoleic acid. Palm kernel oil is typically composed in relation to the fatty acid spectrum as follows: 9% by weight
  • Capron / Capryl / Caprin 50% by weight laurin, 15% by weight myristine, 7% by weight palmitin, 2
  • % By weight of stearic acid, 15% by weight of oleic acid and 1% by weight of linoleic acid.
  • Rapeseed oil typically contains about 48% by weight erucic acid as a fatty acid component, 15
  • oleic acid 14% by weight of linoleic acid, 8% by weight of linolenic acid, 5% by weight of ionic acid, 3
  • Fatty acid proportions here are erucic acid 0.5% by weight, oleic acid 63% by weight, linoleic acid 20% by weight.
  • Linolenic acid 9% by weight
  • Icosenoic acid 1% by weight
  • Palmitic acid 4% by weight
  • Castor oil consists of 80 to 85% by weight of the glyceride of ricinoleic acid, in addition about 7% by weight of glycerides is oil, 3% by weight of glycerides is linoleic and about 2% by weight of glycerides the palmitic and stearic acid contain.
  • Soybean oil contains 55 to 65% by weight of the total fatty acids of polyunsaturated acids, especially linoleic and linolenic acid.
  • the situation is similar with sunflower oil, whose typical fatty acid spectrum, based on total fatty acid, looks as follows: approx. 1
  • Linoleic acid All of the above information about the fatty acid content in the triglycerides is known to depend on the quality of the raw materials and can therefore fluctuate in number.
  • emulsifiers or emulsifier systems used.
  • Nonionic emulsifiers in particular ethoxylated fatty alcohols and fatty acids, are preferably used as emulsifiers.
  • R 3 is a linear or branched, saturated or unsaturated alkyl radical having 6 to 24 carbon atoms and n is a number from 1 to 50. Those compounds of the formula (II) in which n represents a number from 1 to 35 and in particular from 1 to 15 are particularly preferred. Those compounds of the formula (II) in which R 3 represents an alkyl radical having 16 to 22 carbon atoms are also particularly preferred.
  • the compounds of the formula (II) are obtained in a manner known per se by reacting fatty alcohols with ethylene oxide under pressure, if appropriate in the presence of acidic or basic catalysts.
  • Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolenyl alcohol, linolenyl alcohol, linoleyl alcohol and their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
  • fatty alcohols with 12 to 18 carbon atoms such as, for example, coconut, palm, palm kernel or tallow fatty alcohol, are preferred.
  • R 4 is a linear or branched alkyl radical having 12 to 22 carbon atoms and m is a number from 5 to 50 and preferably 15 to 35.
  • Typical examples are adducts of 20 to 30 moles of ethylene oxide with lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, and gadolic acid mixtures, behenic acid, behenic acid, behenic acid , which occur, for example, in the pressure splitting of natural fats and oils or in the reduction of aldehydes from Roelen's oxosynthesis. Addition products of 20 to 30 moles of ethylene oxide with fatty acids having 16 to 18 carbon atoms are preferably used.
  • Partial glycerides which are also suitable as emulsifiers, preferably follow the formula (IV),
  • CO R 5 is a linear or branched acyl radical having 12 to 22 carbon atoms and x, y and z in total is 0 or is a number from 1 to 50, preferably 15 to 35.
  • Typical examples of partial glycerides suitable for the purposes of the invention are lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride,
  • Monoglycerides or technical mono / diglyceride mixtures with a predominant monoglyceride content of the formula (IV) are preferably used, in which CO R 5 represents a linear acyl radical having 16 to 18 carbon atoms.
  • Other suitable emulsifiers are, for example, nonionic surfactants from one of the following groups:
  • (V) polyol and especially polyglycerol esters such as Polyglycerol polyricinoleate or polyglycerol poly-12-hydroxystearate. Mixtures of compounds from several of these classes of substances are also suitable;
  • VE vascular endothelial fatty acids
  • ricinoleic acid and 12-hydroxystearic acid and glycerol polyglycerol
  • pentaerythritol dipentaerythritol
  • sugar alcohols eg sorbitol
  • polyglucosides eg cellulose
  • the adducts of ethylene oxide and / or of propylene oxide with glycerol monoesters and diesters and sorbitan monoesters and diesters of fatty acids or with castor oil are known, commercially available products Ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out corresponds.
  • alkylglycosides are known nonionic surfactants which follow the formula (V) - R ° O- [G] p (V)
  • R 6 represents an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
  • G represents a sugar radical having 5 or 6 carbon atoms
  • p represents numbers from 1 to 10.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and or alkenyl oligoglucosides.
  • the index number p in the general formula (V) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
  • the alkyl or alkenyl radical R ° can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capro alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 6 can also differ from primary alcohols with 12 to 22, preferably 12 to 14 carbon atoms , derive. Typical examples are lauryl alcohol, Myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol.
  • Oleyl alcohol Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
  • Alkyl oligoglucosides based on hardened Ci 2 / ⁇ 4 coco alcohol with a DP of 1 to 3 are preferred. If alkyl glycosides of the formula (V) are used as emulsifiers, it may be advantageous to add small amounts of polyhydroxycarboxylic acids, preferably citric acid, as formulation auxiliaries use. The polyhydroxy acids are then usually used in amounts of 0.1 to 3.0% by weight, preferably in amounts of 0.1 to 1.0% by weight.
  • the microemulsions used according to the invention preferably contain from 20 to 90% by weight of water, in particular from 30 to 80% by weight and very particularly preferably from 30 to 60% by weight. The remainder to 100% by weight is accounted for by the oil phase as well as emulsifiers and possibly other auxiliaries and additives.
  • the oil phase itself is preferably present in amounts of 10 to 80% by weight, in particular 20 to 70% by weight and in particular 25 to 55% by weight.
  • the oil phase preferably contains only components a) or b) or mixtures of these components. It is particularly preferred to use emulsions which contain the oil and water phase in a weight ratio of 1: 1.
  • the emulsifiers or emulsifier systems are preferably present in amounts of 10 to 50% by weight, in particular in amounts of 15 to 45% by weight and particularly preferably in amounts of 20 to 40% by weight.
  • microemulsions described can be used according to the invention in all kinds of fermentation processes. All of the process designs known to the person skilled in the art, for example batch or fed batch and continuous fermentation, can be used here. All fermenter systems known to the person skilled in the art can also be used. For details, see Crueger, pages 50 to 70.
  • the use of the microemulsions is also not limited to specific microorganisms; rather, the emulsions can be used to produce or convert all compounds known to those skilled in the art by fermentation. In addition to the classic fermentation processes, which are mainly used for the synthesis of antibiotics (see loc.
  • the described emulsions are also suitable for use in - microbial transformations ("bioconversion"), e.g. the transformation of steroids and Sterols, of antibiotics and pesticides or the production of vitamins (see Crueger. Pages 254 to 273).
  • bioconversion e.g. the transformation of steroids and Sterols
  • vitamins see Crueger. Pages 254 to 273.
  • use in fermentation processes for the production of antibiotics for example chefalosporins, tylosin or erythromycin, is preferred.
  • the microemulsions of the aqueous fermentation broth which contains the microorganisms and the nitrogen source and trace elements and optionally other auxiliaries, in particular defoamers, are metered in in a suitable manner.
  • suitable nitrogen sources are: peptone, yeast or malt extract, corn steep liquor, urea or lecithins.
  • the trace elements can be present in the form of inorganic salts, for example sodium or potassium nitrate, ammonium nitrate, ammonium sulfate, iron sulfate etc. It can also be advantageous to add further additives, such as defoamers or nitrogen sources, to the microemulsions themselves.
  • microemulsions were made by mixing the starting materials.
  • the compositions are listed in Table 1.
  • the droplet size was measured with a Malvem Mastersizer 2000.
  • the emulsions are suitable, for example, as the sole nutrient source for fermentation processes and can be added directly to the aqueous fermentation broth.

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PCT/EP2000/004364 1999-05-25 2000-05-16 Verwendung von mikroemulsionen in fermentationsverfahren WO2000071672A1 (de)

Priority Applications (9)

Application Number Priority Date Filing Date Title
MXPA01011818A MXPA01011818A (es) 1999-05-25 2000-05-16 Utilizacion de microemulsiones en procesos de fermentacion.
EP00945681A EP1180137A1 (de) 1999-05-25 2000-05-16 Verwendung von mikroemulsionen in fermentationsverfahren
PL00352059A PL352059A1 (en) 1999-05-25 2000-05-16 Use of microemulsion in fermentation processes
KR1020017015012A KR20020012580A (ko) 1999-05-25 2000-05-16 발효 공정에서의 마이크로에멀션의 용도
SK1694-2001A SK16942001A3 (sk) 1999-05-25 2000-05-16 Použitie emulzií olej vo vode vo fermentačnom procese
JP2000620052A JP2003500043A (ja) 1999-05-25 2000-05-16 発酵プロセスにおけるミクロエマルジョンの使用
BR0010873-1A BR0010873A (pt) 1999-05-25 2000-05-16 Utilização de microemulsões em processos de fermentação
NO20015732A NO20015732D0 (no) 1999-05-25 2001-11-23 Anvendelse av mikroemulsjoner i fermenteringsfremgangsmåter
HK02105053.1A HK1043478A1 (zh) 1999-05-25 2002-07-06 微乳在發酵過程中的應用

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DE19923784.0 1999-05-25
DE19923784A DE19923784A1 (de) 1999-05-25 1999-05-25 Verwendung von Mikroemulsionen in Fermentationsverfahren

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JP (1) JP2003500043A (pt)
KR (1) KR20020012580A (pt)
CN (1) CN1351650A (pt)
AR (1) AR024085A1 (pt)
BR (1) BR0010873A (pt)
CZ (1) CZ20014205A3 (pt)
DE (1) DE19923784A1 (pt)
HK (1) HK1043478A1 (pt)
MX (1) MXPA01011818A (pt)
NO (1) NO20015732D0 (pt)
PL (1) PL352059A1 (pt)
SK (1) SK16942001A3 (pt)
TR (1) TR200102994T2 (pt)
WO (1) WO2000071672A1 (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1648226A2 (en) * 2003-03-11 2006-04-26 Cognis IP Management GmbH Microemulsions as adjuvants for agricultural chemicals

Citations (5)

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Publication number Priority date Publication date Assignee Title
US4871665A (en) * 1985-12-20 1989-10-03 Henkel Kommanditgesellschaft Auf Aktien Process for the preparation of exocellular biopolymers
EP0409314A1 (en) * 1989-07-17 1991-01-23 ENIRICERCHE S.p.A. Stable, single-phased solutions of water-in-oil microemulsions derived from crude oil and allied products and which contain microorganisms and/or parts thereof
US5372943A (en) * 1987-07-24 1994-12-13 Cetus Corporation Lipid microemulsions for culture media
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CZ20014205A3 (cs) 2002-02-13
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TR200102994T2 (tr) 2002-04-22
PL352059A1 (en) 2003-07-28
JP2003500043A (ja) 2003-01-07
KR20020012580A (ko) 2002-02-16
WO2000071672A8 (de) 2001-02-22
DE19923784A1 (de) 2000-11-30
NO20015732D0 (no) 2001-11-23
EP1180137A1 (de) 2002-02-20
AR024085A1 (es) 2002-09-04
MXPA01011818A (es) 2002-04-24
BR0010873A (pt) 2002-02-19
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