FR2827192A1 - Aqueous composition containing surface-active fermentation products and nonionic surfactant, useful as emulsifier for agrochemical and cosmetic products - Google Patents
Aqueous composition containing surface-active fermentation products and nonionic surfactant, useful as emulsifier for agrochemical and cosmetic products Download PDFInfo
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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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9728—Fungi, e.g. yeasts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- 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
Abstract
Description
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Domaine de l'invention
L'invention se rapporte au domaine des biotechnologies et concerne des préparations aqueuses contenant des agents tensioactifs préparés par voie biotechnologique et des agents tensioactifs non ioniques, un procédé pour leur préparation, l'utilisation spéciale des agents tensioactifs non ioniques comme agents d'extraction ainsi que des mélanges pour la production de préparations agrochimiques ou cosmétiques. Field of the invention
The invention relates to the field of biotechnology and relates to aqueous preparations containing surfactants prepared by biotechnological means and nonionic surfactants, a process for their preparation, the special use of nonionic surfactants as extraction agents as well as mixtures for the production of agrochemical or cosmetic preparations.
Etat de la technique
Par fermentation, on peut transformer la biomasse comme par exemple les graisses et les huiles, les hydrates de carbone, les hydrocarbures et similaires, en substances tensioactives qui sont désignées en résumé comme biodétergents . La séparation de ces substances des bouillons de fermentation se présente cependant souvent comme très coûteuse en temps et d'un coût intensif. Dans une série de cas, l'utilisation d'agents d'extraction organiques, comme par exemple le chlorure de méthylène ou l'acétate d'éthyle, est apparue comme possible, mais cependant elle présente un inconvénient important du fait que ces substances ensuite à nouveau doivent être séparées des biodétergents car leur utilisation conjointe par exemple dans le domaine de la cosmétique est naturellement impossible. Effectivement des traces faibles de composés chlorés ne sont pas même acceptables. Dans le cas des rhamnolipides qui sont produits en tant qu'agents tensioactifs extracellulaires à partir du glucose et de triglycérides naturels, on réussit en raison de leur caractère anionique aussi une séparation par adsorption sur des échangeurs d'ions, cependant un tel procédé étant en tout cas exécutable logiquement à l'échelle du laboratoire
Sous cet angle on doit attirer l'attention sur l'article de Hinze et Pramauro dans Critical Review Anal. Chem. 24 (2), 133-177 (1993), qui expose l'extraction de protéines avec des agents tensioactifs zwitterioniques et l'extraction de chélates métalliques avec des agents tensioactifs non ioniques au point de trouble. Minuth et al. décrivent dans Biotechnol. Bioeng. 55 (2), 342ff (1997) la séparation de la biomasse de systèmes aqueux à deux phases, à l'aide de la centrifugation. State of the art
By fermentation, it is possible to transform the biomass, for example fats and oils, carbohydrates, hydrocarbons and the like, into surfactants which are designated in summary as bio-detergents. The separation of these substances from the fermentation broths, however, often presents itself as very time-consuming and costly. In a series of cases, the use of organic extractants, such as for example methylene chloride or ethyl acetate, has appeared to be possible, but however it has a significant drawback since these substances then again must be separated from bio-detergents because their joint use for example in the field of cosmetics is naturally impossible. Indeed weak traces of chlorinated compounds are not even acceptable. In the case of rhamnolipids which are produced as extracellular surfactants from glucose and natural triglycerides, due to their anionic nature, an adsorption separation on ion exchangers is also successful, however such a process is in any logically executable case on a laboratory scale
From this angle, attention should be drawn to the article by Hinze and Pramauro in Critical Review Anal. Chem. 24 (2), 133-177 (1993), which describes the extraction of proteins with zwitterionic surfactants and the extraction of metal chelates with non-ionic surfactants at the cloud point. Minuth et al. describe in Biotechnol. Bioeng. 55 (2), 342ff (1997) the separation of biomass from two-phase aqueous systems using centrifugation.
Le problème de la présente invention a consisté par conséquent à rendre disponible un procédé amélioré d'extraction en vue du traitement de biodétergents à partir des bouillons de culture, dans le déroulement duquel des mélanges de biodétergents sont obtenus avec les agents d'extraction qui sont utilisables sans autre étape de séparation The problem of the present invention has therefore been to make available an improved extraction process for the treatment of bio-detergents from culture broths, in the course of which mixtures of bio-detergents are obtained with the extractants which are usable without further separation step
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commercialement, en particulier dans le domaine de l'agrochimie ou de la cosmétique. En même temps le procédé devrait se distinguer par le fait qu'il se déroule rapidement et à de basses températures et de cette façon garantit une séparation quantitative des biodétergents. commercially, in particular in the field of agrochemicals or cosmetics. At the same time the process should be distinguished by the fact that it takes place quickly and at low temperatures and in this way guarantees a quantitative separation of the bio-detergents.
Description de l'invention
L'invention a pour objet des préparations aqueuses contenant : a) des produits de fermentation tensioactifs, et b) des agents tensioactifs non ioniques. Description of the invention
The invention relates to aqueous preparations containing: a) surfactant fermentation products, and b) nonionic surfactants.
On a trouvé d'une manière surprenante qu'on peut extraire des bouillons de fermentation tensioactifs rapidement et quantitativement à l'aide d'agents tensioactifs non ioniques, si on effectue l'extraction au point de trouble des agents tensioactifs non ioniques. Les mélanges en résultant peuvent être utilisés sans séparation ou traitement supplémentaire, directement dans le commerce et peuvent trouver une utilisation par exemple en tant qu'agent émulsionnant en agrochimie ou en cosmétique. It has surprisingly been found that surfactant fermentation broths can be extracted quickly and quantitatively using nonionic surfactants if the cloudy extraction of nonionic surfactants is carried out. The resulting mixtures can be used without separation or additional treatment, directly on the market and can find a use for example as an emulsifying agent in agrochemicals or in cosmetics.
Produits de fermentation tensioactifs ( biodétergents )
La transformation de la biomasse en biodétergents par fermentation peut s'effectuer à l'aide d'une multiplicité de micro-organismes complètement différents. Par exemple Candida antartica a une importance pour la production de Mannosyl-érythritol-lipides (MEL). Dans un mode d'exécution préféré de l'invention en ce qui concerne les biodétergents , il s'agit donc de rhamnolipides obtenus par fermentation d'hydrates de carbone avec des graisses et des huiles, et qui répondent à la formule générale (I).
Surfactant fermentation products (bio-detergents)
The transformation of biomass into biodetergents by fermentation can be carried out using a multiplicity of completely different microorganisms. For example Candida antartica is important for the production of Mannosyl-erythritol-lipids (MEL). In a preferred embodiment of the invention as regards the bio-detergents, they are therefore rhamnolipids obtained by fermentation of carbohydrates with fats and oils, and which correspond to the general formula (I) .
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Agents tensioactifs non ioniques
Les agents tensioactifs non ioniques se caractérisent par une propriété de solubilité inverse, c'est-à-dire qu'ils se dissolvent à froid mieux qu'à chaud. Cet effet est à rattacher au fait que les agents tensioactifs non ioniques renferment en général des chaînes d'éther de polyglycol dont les oxygènes de l'éther se présentent hydratés dans l'environnement aqueux par l'intermédiaire de composés à pont hydrogène, ce qui confère à la molécule une polarité élevée et par conséquent une bonne solubilité. Avec l'augmentation de la température les ponts hydrogène sont dissous, à cause de quoi la polarité et la solubilité diminuent et l'agent tensioactif non ionique est précipité de la phase aqueuse. La température à partir de laquelle cette précipitation commence, est typique pour chaque agent tensioactif non ionique et est désignée comme point de trouble . En dessous de cette température il se forme deux phases micellaires, une riche en agent tensioactif et une pauvre en agent tensioactif. Nonionic surfactants
Non-ionic surfactants are characterized by a reverse solubility property, that is to say that they dissolve in cold better than in hot. This effect is to be linked to the fact that nonionic surfactants generally contain polyglycol ether chains in which the ether oxygenates are hydrated in the aqueous environment via hydrogen-bridged compounds, which gives the molecule a high polarity and therefore good solubility. With increasing temperature the hydrogen bridges are dissolved, because of which the polarity and solubility decrease and the nonionic surfactant is precipitated from the aqueous phase. The temperature from which this precipitation begins is typical for each nonionic surfactant and is designated as the cloud point. Below this temperature, two micellar phases are formed, one rich in surfactant and one poor in surfactant.
Dans le sens de l'invention viennent à utilisation de préférence par conséquent des agents tensioactifs non ioniques qui possèdent un point de trouble dans la zone de 20 à 80 et en particulier de 25 à 50 C pour lesquels des espèces naturellement avec des points de trouble particulièrement bas, en particulier dans la zone de la température ambiante, à nouveau sont particulièrement préférées car elles permettent la préparation des mélanges dans des conditions très douces. En règle générale en ce qui concerne les agents tensioactifs non ioniques, il s'agit d'éthers
d'alcool gras et de polyglycol qui en particulier répondent à la formule (II), RIO (CH2CHR20) nH (II) dans laquelle RI représente un reste alkyle et/ou alkenyle linéaire ou ra- mifié, R2 représente de l'hydrogène ou un méthyle et n représente des nombres allant de 1 à 30. In the sense of the invention, therefore, use is preferably made of nonionic surfactants which have a cloud point in the region of 20 to 80 and in particular 25 to 50 ° C. for which species naturally with cloud points particularly low, especially in the area of room temperature, again are particularly preferred because they allow the preparation of mixtures under very mild conditions. Typically for nonionic surfactants, these are ethers
fatty alcohol and polyglycol which in particular correspond to formula (II), RIO (CH2CHR20) nH (II) in which RI represents a linear or branched alkyl and / or alkenyl residue, R2 represents hydrogen or methyl and n represent numbers ranging from 1 to 30.
Des exemples typiques sont les produits d'addition de, en moyenne, 1 à 5 et de préférence de 2 à 3 propylèneglycols et/ou de 1 à 30, de préférence de 5 à 15 mol d'oxyde d'éthylène sur des alcools gras ayant de 6 à 22 et en particulier de 12 à 18 atomes de carbone comme par exemple, l'alcool caproique, l'alcool caprylique, l'alcool caprinique, l'alcool laurique, l'alcool myristique, l'alcool cétylique, l'alcool palmoléique, l'alcool stéarique, l'alcool isostéarique, l'alcool cétéarylique, l'alcool oléique, l'alcool élaidique, l'alcool gadoléique, l'alcool arachique, l'alcool béhénique, Typical examples are the adducts of, on average, 1 to 5 and preferably 2 to 3 propylene glycols and / or 1 to 30, preferably 5 to 15 mol of ethylene oxide on fatty alcohols having from 6 to 22 and in particular from 12 to 18 carbon atoms such as, for example, caproic alcohol, caprylic alcohol, caprinic alcohol, lauric alcohol, myristic alcohol, cetyl alcohol, l palmoleic alcohol, stearic alcohol, isostearic alcohol, cetearyl alcohol, oleic alcohol, elaidic alcohol, gadoleic alcohol, arachic alcohol, behenic alcohol,
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l'alcool érucique, ainsi que leurs mélanges industriels. Les agents tensioactifs non ioniques peuvent être produits d'une manière de la grande industrie connue en soi, ainsi que par addition catalysée par les bases d'oxydes d'alkylène sur les alcools gras correspondants, grâce à quoi des substances ayant une distribution d'homologues conventionnellement large en résultent. De préférence on met en oeuvre cependant des éthers d'alcools gras et de polyglycol ayant une distribution d'homologues restreinte (Narrow-range éthoxylates NRE) car ceux-ci se caractérisent en général par des points de trouble particulièrement bas. erucic alcohol, as well as their industrial mixtures. The nonionic surfactants can be produced in a large industry manner known per se, as well as by addition catalyzed by alkylene oxide bases on the corresponding fatty alcohols, whereby substances having a distribution of conventionally broad counterparts result. Preferably, however, ethers of fatty alcohols and of polyglycol having a restricted homologous distribution (Narrow-range ethoxylates NRE) are used since these are generally characterized by particularly low cloud points.
Leur production s'effectue par alkoxylation des alcools gras en présence de catalyseurs spéciaux connus de la littérature comme par exemple de l'hydrotalcite calcinée. Des exemples typiques sont les NRE
alcools de coco en C12-C18 + 5 OE (Agrimul@ NRE 1205), ou le NRE alcool myristique + 6 OE (Agrimul (D 1406 NRE) qui sont accessibles de la société Cognis Deutschland GmbH, dans le commerce. Their production is carried out by alkoxylation of fatty alcohols in the presence of special catalysts known from the literature such as for example calcined hydrotalcite. Typical examples are the NRE
coconut alcohols in C12-C18 + 5 EO (Agrimul @ NRE 1205), or the NRE myristic alcohol + 6 EO (Agrimul (D 1406 NRE) which are commercially available from Cognis Deutschland GmbH.
Sels d'électrolytes
Dans un autre mode d'exécution préféré de la présente invention les préparations peuvent renfermer en supplément des sels d'électrolytes. En ce qui les concerne il s'agit de préférence de chlorure ou de sulfates de métal alcalin ou de métal alcalino-terreux. Electrolyte salts
In another preferred embodiment of the present invention the preparations may additionally contain electrolyte salts. As far as they are concerned, it is preferably chloride or sulfates of alkali metal or alkaline earth metal.
Préparations tensioactives
Typiquement les préparations conformes à l'invention contiennent, rapporté à la teneur non aqueuse, a) de 10 à 60, de préférence de 20 à 40 % en poids de produits de fer- mentation tensioactifs, b) de 40 à 90, de préférence de 45 à 80 % en poids d'agents tensioactifs non ioniques et c) de 0 à 20, de préférence de 10 à 15 % en poids, de sels d'électrolytes, avec la restriction que les données en quantités se complètent à 100 % en poids. La concentration non aqueuse des préparations peut s'élever ainsi de 10 à 50, de préférence de 20 à 30 % en poids. Surfactant preparations
Typically the preparations according to the invention contain, relative to the nonaqueous content, a) from 10 to 60, preferably from 20 to 40% by weight of surfactant fermentation products, b) from 40 to 90, preferably from 45 to 80% by weight of nonionic surfactants and c) from 0 to 20, preferably from 10 to 15% by weight, of electrolyte salts, with the restriction that the data in quantities complement each other to 100% in weight. The nonaqueous concentration of the preparations can thus rise from 10 to 50, preferably from 20 to 30% by weight.
Procédé d'extraction
Un autre objet de l'invention concerne un procédé de préparation de mélanges à base de produits de fermentation tensioactifs et d'agents tensioactifs non ioniques dans lequel on extrait une solution aqueuse de produits de fermentation tensioactifs avec des agents tensioactifs non ioniques à leur point de trouble et on sépare la phase contenant des agents tensioactifs plus légère ainsi formée de la phase aqueuse plus Extraction process
Another subject of the invention relates to a process for the preparation of mixtures based on surfactant fermentation products and nonionic surfactants in which an aqueous solution of surfactant fermentation products is extracted with nonionic surfactants at their point of cloudy and the lighter surfactant-containing phase is separated from the more aqueous phase
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lourde. Comme déjà explicité, il s'agit en ce qui concerne les produits de fermentation tensioactifs, directement de préférence de bouillons de fermentation. Il s'est avéré avantageux d'ajouter au système de faibles quantités de sels d'électrolytes car ceux-ci favorisent la séparation de phase et en même temps réduisent le point de trouble des agents tensioactifs non ioniques. La séparation consécutive peut s'effectuer par exemple dans un séparateur ou par centrifugation, dans laquelle la phase contenant les tensioactifs forme en règle générale, la phase la plus légère. La phase aqueuse plus lourde ne renferme pratiquement plus aucun constituant tensioactif. Un autre objet de l'invention concerne par conséquent l'utilisation d'agents tensioactifs non ioniques comme agents d'extraction pour des bouillons de fermenteur aqueux, tensioactifs. heavy. As already explained, with regard to the surfactant fermentation products, it is preferably directly fermentation broths. It has been found advantageous to add small amounts of electrolyte salts to the system as these promote phase separation and at the same time reduce the cloud point of nonionic surfactants. The consecutive separation can be carried out for example in a separator or by centrifugation, in which the phase containing the surfactants generally forms the lightest phase. The heavier aqueous phase contains practically no more surfactant component. Another object of the invention therefore relates to the use of nonionic surfactants as extraction agents for aqueous fermenter broths, surfactants.
Possibilité d'utilisation industrielle
Les mélanges aqueux accessibles dans le sens de l'invention possèdent des propriétés tensioactives remarquables et sont en particulier facilement biodégradables ainsi qu'inoffensifs sur le plan toxicologique. Un autre objet de l'invention concerne par conséquent leur utilisation, par exemple comme agents émulsionnants, pour la production de préparations agrochimiques ou cosmétiques dans lesquelles ils peuvent être contenus en quantités allant de 0,1 à 30, de préférence de 1 à 20 et en particulier de 5 à 15 % en poids. Possibility of industrial use
The aqueous mixtures accessible within the meaning of the invention have remarkable surfactant properties and are in particular easily biodegradable as well as toxicologically harmless. Another subject of the invention therefore relates to their use, for example as emulsifying agents, for the production of agrochemical or cosmetic preparations in which they may be contained in amounts ranging from 0.1 to 30, preferably from 1 to 20 and in particular from 5 to 15% by weight.
Exemples Exemple 1
Une solution aqueuse d'un rhamnolipide (JBR 599, Jeneill Biosurfactant Co, Inc) à une concentration de 40 g/1 a été mélangée à 80 g/1 d'alcool de coco en C12-C18 + 5 OE NRE (Agrimul@ 1205 NRE, Cognis). Après addition de 10 % en poids de sel de cuisine et chauffage du système à 50 il se produit en l'espace de quelques minutes une séparation de phase (pH 3,5). La phase tensioactive supérieure a été séparée et étudiée par chromatographie en couche mince en comparaison aux phases aqueuses inférieures. De cette façon on a établi que la phase aqueuse était dépourvue d'agent tensioactif et que l'extraction par conséquent avait été effectuée d'une manière quantitative. Examples Example 1
An aqueous solution of a rhamnolipid (JBR 599, Jeneill Biosurfactant Co, Inc) at a concentration of 40 g / 1 was mixed with 80 g / 1 of coconut alcohol in C12-C18 + 5 OE NRE (Agrimul @ 1205 NRE, Cognis). After adding 10% by weight of cooking salt and heating the system to 50, phase separation (pH 3.5) occurs within a few minutes. The upper surfactant phase was separated and studied by thin layer chromatography in comparison to the lower aqueous phases. In this way it was established that the aqueous phase was devoid of surfactant and that the extraction therefore had been carried out quantitatively.
Exemple 2
Une solution aqueuse d'un rhamnolipide (JBR 599, Jeneill Biosurfactant Co, Inc) à une concentration de 40 g/1 a été mélangée à 70 g/1 d'alcool myristique + 6 OE NRE (Agrimul (D 1406 NRE, Cognis). Example 2
An aqueous solution of a rhamnolipid (JBR 599, Jeneill Biosurfactant Co, Inc) at a concentration of 40 g / 1 was mixed with 70 g / 1 of myristic alcohol + 6 OE NRE (Agrimul (D 1406 NRE, Cognis) .
Après addition de 8 % en poids de sel de cuisine et chauffage du système à After adding 8% by weight of cooking salt and heating the system to
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45 C, il s'est produit en l'espace de quelques minutes une séparation de phase (pH 3,5). La phase tensioactive supérieure a été séparée et étudiée par chromatographie en couche mince en comparaison avec les phases aqueuses inférieures. De cette façon on a établi que la phase aqueuse était dépourvue d'agent tensioactif et que l'extraction par conséquent s'était effectuée d'une manière quantitative. 45 C, phase separation (pH 3.5) occurred within a few minutes. The upper surfactant phase was separated and studied by thin layer chromatography in comparison with the lower aqueous phases. In this way it was established that the aqueous phase was devoid of surfactant and that the extraction therefore was carried out quantitatively.
Claims (14)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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FR0109360A FR2827192B1 (en) | 2001-07-13 | 2001-07-13 | PREPARATIONS CONTAINING NON-IONIC SURFACTANTS AS EXTRACTING AGENTS |
PCT/EP2002/007412 WO2003006146A1 (en) | 2001-07-13 | 2002-07-04 | Aqueous preparations |
EP02764626A EP1406722A1 (en) | 2001-07-13 | 2002-07-04 | Aqueous preparations |
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FR0109360A FR2827192B1 (en) | 2001-07-13 | 2001-07-13 | PREPARATIONS CONTAINING NON-IONIC SURFACTANTS AS EXTRACTING AGENTS |
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FR2827192A1 true FR2827192A1 (en) | 2003-01-17 |
FR2827192B1 FR2827192B1 (en) | 2004-06-04 |
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FR0109360A Expired - Fee Related FR2827192B1 (en) | 2001-07-13 | 2001-07-13 | PREPARATIONS CONTAINING NON-IONIC SURFACTANTS AS EXTRACTING AGENTS |
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EP (1) | EP1406722A1 (en) |
FR (1) | FR2827192B1 (en) |
WO (1) | WO2003006146A1 (en) |
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Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2938383A1 (en) * | 1978-09-26 | 1980-04-10 | Kao Corp | COSMETIC COMPOSITION FOR SKIN AND HAIR TREATMENT |
JPS5658532A (en) * | 1980-07-04 | 1981-05-21 | San Ei Chem Ind Ltd | Production of fat and oil emulsifying liquid |
EP0214531A2 (en) * | 1985-09-04 | 1987-03-18 | SOLVAY ENZYMES, INC. (a Delaware corporation) | Method for the recovery of extracellular enzymes from whole fermentation beer |
EP0271907A2 (en) * | 1986-12-19 | 1988-06-22 | Wintershall Aktiengesellschaft | Homopolysaccharides with a high molecular weight, process for their extracellular preparation and their use, as well as the corresponding fungus strains |
US4943390A (en) * | 1983-11-02 | 1990-07-24 | Petroleum Fermentations N.V. | Bioemulsifier-stabilized hydrocarbosols |
EP0499434A1 (en) * | 1991-02-12 | 1992-08-19 | Unilever Plc | Detergent compositions |
EP0574050A1 (en) * | 1992-05-19 | 1993-12-15 | Gist-Brocades N.V. | Large scale separation and purification of fermentation product |
EP0605308A1 (en) * | 1992-12-30 | 1994-07-06 | Institut Francais Du Petrole | Composition containing a surfactant and glycolipids for decontaminating a polluted medium |
FR2713655A1 (en) * | 1993-12-15 | 1995-06-16 | Inst Francais Du Petrole | Decontaminating porous medium, esp. soil, polluted with hydrocarbon(s) |
WO1996023061A2 (en) * | 1995-01-27 | 1996-08-01 | Genencor International, Inc. | Surfactant-based enzyme extraction process |
DE19628454A1 (en) * | 1996-07-15 | 1998-01-29 | Mfh Marienfelde Gmbh Unternehm | New rhamno-lipid-alginate polymer complexes |
WO1998011127A1 (en) * | 1996-09-11 | 1998-03-19 | Pharmacia & Upjohn Ab | A process for purifying apolipoproteins and a composition for use in the process |
EP0945516A1 (en) * | 1996-10-04 | 1999-09-29 | Consejo Superior De Investigaciones Cientificas | Process for the selective preparation of derivatives of monosaccharides and polyols which are partially acylated |
-
2001
- 2001-07-13 FR FR0109360A patent/FR2827192B1/en not_active Expired - Fee Related
-
2002
- 2002-07-04 EP EP02764626A patent/EP1406722A1/en not_active Withdrawn
- 2002-07-04 WO PCT/EP2002/007412 patent/WO2003006146A1/en not_active Application Discontinuation
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2938383A1 (en) * | 1978-09-26 | 1980-04-10 | Kao Corp | COSMETIC COMPOSITION FOR SKIN AND HAIR TREATMENT |
JPS5658532A (en) * | 1980-07-04 | 1981-05-21 | San Ei Chem Ind Ltd | Production of fat and oil emulsifying liquid |
US4943390A (en) * | 1983-11-02 | 1990-07-24 | Petroleum Fermentations N.V. | Bioemulsifier-stabilized hydrocarbosols |
EP0214531A2 (en) * | 1985-09-04 | 1987-03-18 | SOLVAY ENZYMES, INC. (a Delaware corporation) | Method for the recovery of extracellular enzymes from whole fermentation beer |
EP0271907A2 (en) * | 1986-12-19 | 1988-06-22 | Wintershall Aktiengesellschaft | Homopolysaccharides with a high molecular weight, process for their extracellular preparation and their use, as well as the corresponding fungus strains |
EP0499434A1 (en) * | 1991-02-12 | 1992-08-19 | Unilever Plc | Detergent compositions |
EP0574050A1 (en) * | 1992-05-19 | 1993-12-15 | Gist-Brocades N.V. | Large scale separation and purification of fermentation product |
EP0605308A1 (en) * | 1992-12-30 | 1994-07-06 | Institut Francais Du Petrole | Composition containing a surfactant and glycolipids for decontaminating a polluted medium |
FR2713655A1 (en) * | 1993-12-15 | 1995-06-16 | Inst Francais Du Petrole | Decontaminating porous medium, esp. soil, polluted with hydrocarbon(s) |
WO1996023061A2 (en) * | 1995-01-27 | 1996-08-01 | Genencor International, Inc. | Surfactant-based enzyme extraction process |
DE19628454A1 (en) * | 1996-07-15 | 1998-01-29 | Mfh Marienfelde Gmbh Unternehm | New rhamno-lipid-alginate polymer complexes |
WO1998011127A1 (en) * | 1996-09-11 | 1998-03-19 | Pharmacia & Upjohn Ab | A process for purifying apolipoproteins and a composition for use in the process |
EP0945516A1 (en) * | 1996-10-04 | 1999-09-29 | Consejo Superior De Investigaciones Cientificas | Process for the selective preparation of derivatives of monosaccharides and polyols which are partially acylated |
Non-Patent Citations (5)
Title |
---|
BIOSEPARATION, vol. 9, no. 5, 2000, pages 269 - 276, ISSN: 0923-179X * |
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 2000, RODENBROCK A ET AL: "Extraction of peptide tagged cutinase in detergent-based aqueous two-phase systems.", XP002196693, Database accession no. PREV200100284018 * |
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 26 June 1998 (1998-06-26), PERSSON JOSEFINE ET AL: "Purification of recombinant apolipoprotein A-1Milano expressed in Escherichia coli using aqueous two-phase extraction followed by temperature-induced phase separation.", XP002196694, Database accession no. PREV199800356991 * |
JOURNAL OF CHROMATOGRAPHY B, vol. 711, no. 1-2, 26 June 1998 (1998-06-26), pages 97 - 109, ISSN: 0378-4347 * |
PATENT ABSTRACTS OF JAPAN vol. 005, no. 120 (C - 065) 4 August 1981 (1981-08-04) * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107406867A (en) * | 2015-01-12 | 2017-11-28 | 罗格斯技术有限责任公司 | The preparation of rhamnolipid composition |
CN107406867B (en) * | 2015-01-12 | 2021-06-01 | 斯泰潘公司 | Preparation of rhamnolipid composition |
Also Published As
Publication number | Publication date |
---|---|
FR2827192B1 (en) | 2004-06-04 |
EP1406722A1 (en) | 2004-04-14 |
WO2003006146A1 (en) | 2003-01-23 |
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