• 专利附录
  • 专利说明
  • 权利要求
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    • 专利摘要:
    The present invention relates to a method for preparing a plant extract involving solid-liquid extraction using an aqueous solution containing at least one nonionic amphiphilic compound, preferably agrosourced, in a sufficient concentration.
    公开号:FR3033702A1
    申请号:FR1552248
    申请日:2015-03-18
    公开日:2016-09-23
    发明作者:Mathieu Leti；Anne Mandeau
    申请人:Pierre Fabre Dermo Cosmetique SA；
    IPC主号:
    专利说明:

    [0001] FIELD OF THE INVENTION 1. Field of the Invention The field of the present invention relates to a process for the preparation of a plant extract with a nonionic amphiphilic compound as an adjuvant for the preparation of a plant extract with a non-ionic amphiphilic compound. extraction in an aqueous medium. Solid-liquid extraction is the process of extracting a substance present in a solid, in particular a plant, into a liquid solvent. Maceration, infusion and decoction are traditional solid-liquid extraction methods. Solvents are liquids - at temperature of use - having the property to dissolve, to dilute or to extract other substances without modifying them chemically and without themselves modifying themselves. They are used in large quantities for many other industrial applications (paints, detergents, coatings, phytosanitary products ...) and are traditionally of petrochemical origin. However, the scarcity of oil and stricter regulations on chemicals are forcing alternatives to be more environmentally friendly. Eco-extraction is based on the discovery and design of extraction processes, which, on the one hand, reduce energy consumption, but also on the other hand the use of alternative solvents - agro- solvents - while ensuring safe and quality extracts, usable as ingredients for pharmacy, cosmetics, food processing, fine chemicals and bio-fuels ), Comptes Rendus Chimie, 17, 179- 180). In this context, the improvement of existing processes as well as the design of new processes are the subject of numerous works with the aim of reducing the environmental impact of the extraction stage, leading to the emergence and development of new processes. popularization of technologies such as extraction by ultrasound, microwave, supercritical CO2, flash-relaxation. At the same time, the search for alternative extraction solvents, of non-petrochemical origin, is another avenue for improvement. 35 3033702 2 The agro-solvent market is therefore booming, coming from wood, field crops (amylaceous or sugar) and oleaginous species, leading to terpene derivatives, alcohols (ethanol, butanol, 1,3-propane diol), with furfural derivatives or with methyl esters (Green Formula N ° 08 5 December 2011, pp.28-32). Water is a natural solvent considered as renewable. However, its high polarity does not make it possible to extract certain lipophilic molecules of interest. It is therefore necessary to be able to have new solvents making it possible to extract compounds of different ranges of polarity (range of polarity more and wider, or optimization of the extraction of lipophilic compounds). Some nonionic amphiphilic compounds in aqueous solution allow, in sufficient concentration, the solubilization of lipophilic compounds. Examples of these nonionic amphiphilic compounds are nicotinamide, dimethylisosorbide, alkyl polyglycosides and urea. The potential of these compounds as solubilizing adjuvants for certain lipophilic molecules in aqueous media has been explored (Sanghvi R., Evans D., Yalkowsky S. Stacking complexation by Nicotinamide: A useful way of enhancing drug solubility. (2007) 336: 35-41) .. But the solubilization property is not sufficient to allow the extraction of solutes from a plant matrix. Indeed, in the field of plant extraction, the extraction solvent must penetrate into the plant matrix, destroy the membranes and release the compounds in the impregnating solvent (diffusion phenomena, desorption, dissolution ...), and allowing diffusion of the solute from the matrix to the liquid film surrounding the solid, and transfer to the solvent (limiting step). Depending on the solvent used, the membranes of the plant cells are more or less weakened, which allows or not the release of the compounds they contain. The Applicant has demonstrated that an aqueous solution of nonionic amphiphilic compounds, used in sufficient concentration, allows the extraction of solutes of different polarity ranges, from a plant matrix.
    [0002] The present invention therefore relates to a method for preparing a plant extract involving solid-liquid extraction using an aqueous solution containing at least one nonionic amphiphilic compound, preferably agrosourced, at a minimum hydrotropic concentration. The present invention relates to obtaining, using an aqueous solution of nonionic amphiphilic compounds, either a total extract containing polar, medium polar and lipophilic compounds, or an extract enriched in lipophilic compounds. interest. For the purposes of the present invention, the term "lipophilic compounds" is intended to mean compounds with an octanol / water partition coefficient, also called logP or log kow, positive. According to the present invention, the term "nonionic amphiphilic compound" is intended to mean a compound which is soluble in water in any proportion and has no surfactant property to prevent the formation of micelles. This extraction process is an alternative that makes it possible to substitute for polluting petrochemical organic solvents, such as ethyl acetate, hexane, acetone, etc., since the preferred nonionic amphiphilic compounds can be agrosourced compounds, ie mainly from plant biomass. The process according to the invention uses a plant extraction with the aid of an aqueous solution containing a non-ionic amphiphilic compound preferably agrosourced at a minimum sufficient concentration, i.e. at a minimum hydrotropic concentration. By "hydrotropic minimum concentration" is meant the concentration from which these nonionic amphiphilic compounds begin to form aggregates, i.e. new microenvironments with physical properties different from those observed when the compound is diluted, and different from micellar behavior. This minimum hydrotropic concentration is specific to each nonionic amphiphilic compound and is generally of the order of magnitude of the molarity. It can be determined by several physicochemical methods, such as the measurement of surface tension, conductivity, or dynamic and static scattering of light (Self-association of Nicotinamide in aqueous solution: Light-scattering and vapor pressure osmometry studies (1996) 85 (8): 848853) According to another characteristic of the present invention, the aqueous solution containing said nonionic amphiphilic compound, preferably agrosourced, is the only extraction solvent used. According to an advantageous characteristic of the invention, the solid-liquid extraction is carried out by maceration of the plant in said aqueous solution containing at least one nonionic amphiphilic compound at a minimum hydrotropic concentration, maintained with stirring.
    [0003] By "aqueous solution containing at least one nonionic amphiphilic compound with a minimum hydrotropic concentration" is meant according to the present invention an aqueous solution containing at least one nonionic amphiphilic compound at a concentration greater than or equal to the minimum hydrotropic concentration ( MHC) previously recalled. It is also necessary to take into account the water content that may be present in the plant and to adjust accordingly the concentration of the nonionic amphiphilic compounds to allow their good use in the process according to the present invention. According to another characteristic of the invention, the minimum hydrotropic concentration of the nonionic amphiphilic compound in said aqueous solution is greater than or equal to 0.8 mol / L. Preferably, this concentration is greater than or equal to 1 mol / L. More preferably, this concentration is greater than 1.5 mol / L. According to another characteristic of the invention, said aqueous solution is brought to a temperature ranging from 20 ° C. to reflux for a period that may vary from a few minutes to several hours, depending on the extraction technique used. According to another characteristic of the invention, the ratio between the plant and said aqueous solution, expressed respectively in kilograms and in liters, is between 1 / Set 1/50. According to another characteristic of the invention, the solid extraction liquid is made by any other extraction system well known to those skilled in the art such as a microwave extraction, or under ultrasound, or a countercurrent extraction, etc.).
    [0004] According to an advantageous characteristic of the invention, the extraction is followed by a solid-liquid separation operation, by filtration or centrifugation. According to an advantageous characteristic of the invention, said non-ionic amphiphilic compound, preferably agrosourced, is an alkyl- (poly) glycoside of general formula Alk-O-Zp, in which: - Alk denotes a hydrophobic aliphatic hydrocarbon fragment, saturated or unsaturated, linear or branched chain comprising from 3 to 7 carbon atoms, and - Z represents a hydrophilic glycoside group such as glucose, xylitol and arabinose, and - 1 <p <5>. According to a particular embodiment of the invention, the invention, Alk denotes a linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic hydrocarbon fragment comprising 7 carbon atoms. According to another particular embodiment of the invention, Alk denotes a linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic hydrocarbon fragment comprising 6 carbon atoms. According to yet another particular embodiment of the invention, Alk denotes a linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic hydrocarbon fragment comprising 5 carbon atoms.
    [0005] According to yet another particular embodiment of the invention, Alk denotes a linear or branched, saturated or unsaturated, hydrocarbon-based aliphatic hydrocarbon fragment comprising 4 carbon atoms. According to another characteristic of the invention, the agrosourced nonionic amphiphilic compound is a combination of a ricin-derived fatty alcohol with wheat glucose (without GMO). According to an advantageous characteristic of the invention, said compound is an amyl-glycoside whose amyl hydrophobic fragment corresponds to an alcohol obtained by fermentation of beet or potato starch and whose glycoside fragment originates from cereals.
    [0006] The present invention also relates to the use of an aqueous solution containing at least one nonionic amphiphilic compound, preferably agrobased, at a minimum hydrotropic concentration, as a solid-liquid extraction solvent for plants, preferably as the sole solvent for 'extraction. The above use relates to all of the solvents and plants mentioned in connection with the process of the invention. By "plant" is meant according to the present invention all or part of plant, said plant being dry or fresh, frozen or thawed and whole (unfragmented and unmilled), fragmented or milled. By "part of plants" is meant, in particular, aerial parts such as stems, branches, leaves, fruits, seeds and / or flowers; and / or underground parts such as rhizomes, roots and / or bulbs. In a particular embodiment of the invention, all or part of whole plants (non-fragmented, unmilled) will be used.
    [0007] Among the plants that may be used in the context of the present invention, there may be mentioned, inter alia: the fruits of Physalis peruviana, the fruits of Embelia ribes, the leaves of Myrtus communis, the underground parts and the leaves of Piper spp., Eucalyptus globulus leaves, Garcinia mangostana pericarps, Humulus lupulus female inflorescences, Cinchona sp. bark, Urtica dioica aerial parts, Helichtysum sp. Vanilla sp., Rhizomes of Curcuma spp., Rhizomes of Zingiber officinale. At a certain concentration, the nonionic amphiphilic compounds will allow, unexpectedly, the extraction in water of lipophilic compounds. This minimum hydrotropic concentration is specific to each nonionic amphiphilic compound and is generally of the order of molarity. Preferably, the nonionic amphiphilic compounds are alkylglycosides or alkylpolyglycosides. The nonionic amphiphilic compound useful in the context of the present invention may advantageously be one of the commercial raw materials SEPICLEAR G7® (Company SEPPIC) and APPYCLEANO (Company VVHEATOLEO). It may also be a monomeric rhamnose moiety having an anomeric hydroxyl function substituted with a C 5 alkoxy radical. The extraction conditions (time, concentration of the non-ionic amphiphilic compound, pH, etc.) can vary according to the plant / nonionic amphiphilic compound pair so as to optimize the yield and / or the selectivity of the extraction. Such specific adaptations are within the skill of those skilled in the art making use of his general knowledge in the field of solid-liquid extraction. In general, the process consists of maceration with stirring, at temperatures between 20 ° C and reflux, of dry or fresh plant milled in an aqueous solution containing a nonionic amphiphilic compound at a sufficient minimum hydrotropic concentration. to allow the extraction of lipophilic compounds, generally of the order of magnitude of the molarity. According to a preferred embodiment, in addition to the aqueous solution of nonionic amphiphilic compound, no other solvent is involved in the actual extraction step. The aqueous solution of nonionic amphiphilic compound, used at a specific concentration, is the only solvent involved in the extraction process.
    [0008] In a particular embodiment of the invention, the ratio plant (kg) / solvent (L) is 1/5 to 1/50. Of course, the marc can be re-extracted one or more times to deplete the plant. The extraction can be carried out in a conventional reactor or assisted by any other extraction system well known to those skilled in the art (microwaves, ultrasound, countercurrent extraction, etc.). The extraction time may vary from a few minutes to several hours, depending on the extraction technique used. The extraction can be made from fresh plant homogenized with the nonionic amphiphilic compound taking into account the moisture content of the plant. Extraction is followed by solid / liquid separation by centrifugation and / or filtration. By "centrifugation" is meant the action of separating the compounds of a mixture according to their difference in density by subjecting them to centrifugal force, by means of a centrifugal decanter or any type of centrifuge, in order to get a perfectly clear solution. By "filtration" is meant frontal or tangential filtration, where we can consider the presence of filter aid (perlite type, diatom, etc.). This filtration makes it possible to retain the last solid residues, the goal being to obtain a perfectly clear solution. It can be followed by membrane filtration with a cutoff threshold defined according to the size of the molecules to be considered. It can also be replaced or followed by filtration on resin or silica, in order to enrich the compound of interest, for example by using adsorption resins.
    [0009] In a particular embodiment, the solution obtained after the solid / liquid separation is retained as such or lyophilized, comprising the molecules of interest, as well as the nonionic amphiphilic compound (s), said compounds allowing a better solubilization of the extracted in the finished product. This gives a total extract containing compounds in a wide range of polarities (polar, moderately polar, apolar). The extract thus obtained may also be diluted in a volume of water with or without one or more adjuvants chosen from salts, acids or bases, so as to be at a final concentration of nonionic amphiphilic compound lower than the sufficient concentration previously defined. Thus, it is possible to recover the lipophilic compounds by precipitation and solid / liquid separation such as filtration or centrifugation. An enriched extract of lipophilic compounds is thus obtained. The lipophilic compounds of interest may be flavonoids, phenolic acids, terpenic (mono-, di-, triterpenes) and steroidal compounds, diarylheptanoid derivatives, lignans, coumarins, quinones, anthraquinones, xanthones, phloroglucinols, iridoids, sesquiterpene lactones. alkaloids, sucroesters, polar lipids, etc. They may be in particular kavalactones, myrtucommulones, embelline, quinine and its derivatives, vanillin and its derivatives, α-mangostine, xanthohumol, digalactosyldiacylglycerols, galangin, pinobanksin, cardammonin, curcuminoids, gingerol, shogaol etc. The total extract or lipophilic enriched extract may be diluted, concentrated, dried or preserved as such, by the addition of suitable and authorized preservative in the desired finished product (such as glycols, or sorbic acid). , benzoic acid, citric acid and their salts, etc.) or alcohol (minimum 15 °). For the supply of a dry extract, vacuum drying, lyophilization or atomization technologies can be envisaged. The extract obtained can be dried with or without support and / or solubilized in a liquid carrier.
    [0010] The extracts obtained, liquid, pasty or dry as defined above can be used as is in cosmetic, pharmaceutical or food compositions, intended to be administered topically or orally. The advantages are: in the case where the filtrate is preserved as such or lyophilized, obtaining a total extract containing the molecules in a wide range of polarities, as well as the nonionic amphiphilic compounds, allowing better solubilization of the extract in the finished product. in the case where the lipophilic compounds are purified by precipitation, obtaining an extract enriched in lipophilic compounds obtained by means of an aqueous extraction and of agrosourced substances, alternative to toxic and petrochemical solvents such as hexane, ethyl acetate or acetone.
    [0011] The following examples are given as a non-limiting indication. EXAMPLES Example 1: Extract enriched with Physalis peruviana 100 g of dried and ground physalis fruits are stirred for 2 hours at 40 ° C. with 700 ml of an aqueous 1.5M heptylglucoside solution (SEPICLEAR G7® sold by the company SEPPIC) . After filtration, the filtrate is acidified to pH2 and then diluted with 15 volumes of water. After centrifugation, the pellet is taken up and dried. The enriched extract is obtained with a yield of 2.1% by weight. Example 2: Extract enriched with Physalis peruviana 20 g of dried and ground Physalis fruits are stirred for 2 h at 40 ° C. with 140 ml of an aqueous solution of 0.75M heptylglucoside. After filtration, the filtrate is diluted with 6.6 volumes of water. After centrifugation, the pellet is taken up and dried. The enriched extract is obtained with a yield of 0.64% by mass. EXAMPLE 3 Extract enriched with Physalis peruviana 20 g of dried and ground Physalis fruits are stirred for 2 h at 40 ° C. with 140 ml of an aqueous solution of 3 M heptylglucoside. After filtration, the filtrate is diluted with 22 volumes of water. After centrifugation, the pellet is taken up and dried. The enriched extract is obtained with a yield of 0.98% by mass. Results obtained for the various extracts enriched with Physalis: Extract Yield content in sucroesters According to ex. 1 2.11% 19.5% According to ex. 2 0.64% 16.4% According to ex. 0.98% 16.2% Ethyl acetate (1H, reflux) 2.04% 12.9% Heptane (1H, reflux) 1.04% 3.0% In Examples 1 to 3, the extraction of Physalis fruits by an aqueous solution of heptylglucoside followed by precipitation of the extract by dilution makes it possible to obtain an extract enriched with sucroesters. The sugars of the fruit are extracted but remain in solution during the dilution and do not precipitate. The quality of the extracts obtained is greater than the extracts obtained using petrochemical solvents (ethyl acetate, heptane). EXAMPLE 4 Vanilla Extract 5 kg of dried and ground vanilla beans are extracted for 3 hours at 50 ° C. with 50L of 1.5M aqueous heptylglucoside solution. After filtration under pressure, the marc is rinsed with 25L of the same solution. The filtrate is concentrated to obtain a vanilla extract in the form of a brown-red syrupy solution.
    [0012] Results obtained for vanilla extract: Extract Yield Vanillin content and derivatives According to Ex. 4,800% 0.3% This extract, on heptylglucoside support, contains a significant proportion of vanillin and derivatives, while being pre-formulated so as to facilitate its introduction into the aqueous phase of a cosmetic, nutraceutical or medicinal formula.
    [0013] Example 5: Extract enriched with mangosteen 100 kg of dried and ground pericarp Garcinia mangostana are stirred for 2 hours at 40 ° C with 1000 L of an aqueous solution of 1.5M heptylglucoside. After filtration, the filtrate is acidified to pH = 2 and then diluted with 11 volumes of acidified water at pH = 2. After centrifugation, the pellet is taken up and dried. The extract enriched with xanthones (21.3% expressed in α-mangostine) is obtained with a mass yield of 7.3%. The extract obtained is devoid of tannins. In comparison, the ethanolic extraction at reflux of dried and milled pericarps of Garcinia mangostana with an identical plant / volume ratio of solvent gives a leaner extract of xanthones (19.5% expressed as α-mangostin) but with a yield of higher (27% by mass). The extract obtained contains tannins. In comparison, the hexane extraction at reflux of dried and milled pericarp of Garcinia mangostana with a ratio of plant mass / volume of identical solvent gives a richer xanthone extract (89.1% expressed as α-mangostin) but with a yield of lower (1.2% by mass). The extract obtained is devoid of tannins.
    [0014] The extraction with a 1.5M aqueous heptylglucoside solution thus allows selective extraction of xanthones in comparison with ethanolic extraction. It also allows a higher extraction yield than with hexanic extraction.
    [0015] Example 6: Extract enriched with Piper methysticum 1 kg of dried and ground Piper methysticum subterranean parts are extracted with 700 ml of an aqueous solution of amyl xylosides at 1.5 mol / l for 1 hour and 30 minutes with stirring at room temperature. 40 ° C. After filtration, the filtrate is diluted with 4 volumes of water. After centrifugation, the pellet corresponding to the extract enriched with Kava is obtained with a yield of 6.2%. The extract contains 3.0% kavalactones. In comparison, extraction with ethyl acetate at reflux of dried and ground subterranean parts of Piper methysticum with a plant / volume ratio of the same solvent gives a yield of 8.2%. The extract contains 5.3% of 15 kavalactones. In comparison, the extraction with water at reflux of dried and ground subterranean parts of Piper methysticum with a plant / volume ratio of the same solvent gives a yield of 23.1%. The extract contains 0.25% kavalactones. The three extracts have a different kavalactone composition: The extract obtained by extraction with the aqueous solution of amyl glycosides at 1.5 mol / L is richer in low polar kavalactones (yangonine, demethoxyyangonine, flavokawaines A, B and C). ) that the ethyl acetate extract (44.8% against 35.3% of total kavalactones). On the other hand, the extract obtained by extraction with the aqueous solution of amyl glycosides at 1.5 mol / L is poorer in the more polar kavalactones (methysticin, dihydroxymethysticin, kawaine and marindinine) than the acetate extract. ethyl (55.2% vs. 64.7% total kavalactones). The extract obtained by aqueous extraction contains 1.66% kavalactones and does not contain low polar kavalactones (yangonine, demethoxyyangonine, flavokawaines A, B and C). Extraction with an aqueous solution of amyl glycosides at 1.5 mol / L thus allows selective extraction of the less polar kavalactones for a total yield comparable to extraction with ethyl acetate.
    [0016] Example 7: Capsule Mangosteen extract according to Example 5 200 mg Starch 45 mg Magnesium stearate 2 mg Example 8 Cream vanilla extract according to Example 4 0.5-3% Tribehenin PEG-2 esters -7% lsodecyl neopentanoate 2-9% 10 Glycerin 0.5-10% Glycol palmitate 1-6% Cetyl alcohol 0.5 - 3% Disodium EDTA 0.05-0.25% Preservatives 0.5-3% 15 Perfume 0.2-0.5% Xanthan gum 0.1-0.4% Water qs
    权利要求:
    Claims (17)
    [0001]
    REVENDICATIONS1. A process for preparing a plant extract involving solid-liquid extraction using an aqueous solution containing at least one non-ionic amphiphilic compound, preferably agrosourced, at a minimum hydrotropic concentration.
    [0002]
    2. Method according to claim 1, characterized in that the aqueous solution containing said nonionic amphiphilic compound is the only extraction solvent used.
    [0003]
    3. Method according to one of claims 1 to 2, characterized in that the solid-liquid extraction is carried out by maceration of the plant in said aqueous solution containing at least one nonionic amphiphilic compound, maintained stirring.
    [0004]
    4. Method according to one of claims 1 to 2, characterized in that the solid-liquid extraction is carried out under microwaves, under ultrasound or against the current.
    [0005]
    5. Method according to claim 4, characterized in that the minimum hydrotropic concentration of the nonionic amphiphilic compound in said aqueous solution is of the order of magnitude of the molarity.
    [0006]
    6. Method according to one of claims 1 to 5, characterized in that said aqueous solution is brought to a temperature ranging from 20 ° C to reflux for a period of time may vary from a few minutes to several hours, according to the technique of extraction implemented.
    [0007]
    7. Method according to one of claims 1 to 6, characterized in that the ratio between the plant and said aqueous solution expressed respectively in kilograms and liters, is between 1/5 and 1/50.
    [0008]
    8. Method according to one of claims 1 to 7, characterized in that the extraction is followed by a solid-liquid separation operation, by filtration or centrifugation. 3033702 14
    [0009]
    9. Method according to one of claims 1 to 8, characterized in that said nonionic amphiphilic compound is an alkyl- (poly) glycosides of general formula Alk-O-Zp, wherein: - Alk denotes a hydrophobic aliphatic hydrocarbon fragment saturated or unsaturated, linear or branched chain comprising from 3 to 7 carbon atoms, and - Z represents a hydrophilic glycoside group such as glucose, xylitol and arabinose, and - 1 <p <5
    [0010]
    10. Process according to claim 9, characterized in that the nonionic amphiphilic compound is a combination of a fatty alcohol derived from ricin with wheat glucose (without GMO). 15
    [0011]
    11. Process according to claim 9, characterized in that the said compound is an amyl-glycoside whose hydrophobic amyl moiety corresponds to an alcohol obtained by fermentation of the beet or potato starch and whose glycoside moiety originates from cereals. 20
    [0012]
    12. Method according to one of the preceding claims, characterized in that the plant used is selected from the fruits of Physalis peruviana, the fruits of Embelia ribes, the leaves of Myrtus communis, the underground parts and the leaves of Piper spp. , Eucalyptus globulus leaves, Garcinia mangostana pericarps, Humulus lupulus female inflorescences, Cinchona sp. bark, Urtica dioica aerial parts, Helichtysum sp. aerial parts, Fruits. of Vanilla sp., rhizomes of Curcuma spp., rhizomes of Zingiber officinale.
    [0013]
    13. Method according to one of claims 8 to 12, characterized in that the solution obtained after solid / liquid separation is stored as such or freeze-dried comprising the molecules of interest, as well as the nonionic amphiphilic compounds, said compounds nonionic amphiphiles allowing a better solubilization of the extract in the finished product.
    [0014]
    14. Method according to one of the preceding claims, characterized in that in the extract obtained, the lipophilic compounds are purified by precipitation. 3033702 15
    [0015]
    15. Cosmetic and / or pharmaceutical compositions containing a total or concentrated plant extract of lipophilic compounds obtained by carrying out the method according to one of Claims 1 to 14.
    [0016]
    16. Compositions according to claim 15, characterized in that they are put into a form suitable for topical administration. 10
    [0017]
    17. Compositions according to claim 15, characterized in that they are put into a form suitable for oral administration.
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    同族专利:
    公开号 | 公开日
    BR112017017747A2|2018-04-03|
    CN107404926B|2021-03-16|
    EP3270886B1|2020-10-21|
    CN107404926A|2017-11-28|
    US20170367393A1|2017-12-28|
    JP2018509292A|2018-04-05|
    BR112017017747B1|2021-06-22|
    JP6887954B2|2021-06-16|
    US10299502B2|2019-05-28|
    WO2016146837A1|2016-09-22|
    ES2843640T3|2021-07-19|
    KR20170129132A|2017-11-24|
    FR3033702B1|2018-04-20|
    PT3270886T|2021-01-21|
    EP3270886A1|2018-01-24|
    CA2978505A1|2016-09-22|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
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    优先权:
    申请号 | 申请日 | 专利标题
    FR1552248|2015-03-18|
    FR1552248A|FR3033702B1|2015-03-18|2015-03-18|PROCESS FOR PREPARING PLANT EXTRACT WITH NON-IONIC AMPHIPHILIC COMPOUND AS AQUEOUS EXTRACTION ADJUVANT|FR1552248A| FR3033702B1|2015-03-18|2015-03-18|PROCESS FOR PREPARING PLANT EXTRACT WITH NON-IONIC AMPHIPHILIC COMPOUND AS AQUEOUS EXTRACTION ADJUVANT|
    US15/553,048| US10299502B2|2015-03-18|2016-03-18|Method for producing an extract of a matrix of vegetable origin with a non-ionic amphiphilic compound as extraction adjuvant in an aqueous medium|
    PT167133446T| PT3270886T|2015-03-18|2016-03-18|Method for producing an extract of a matrix of vegetable origin with a non-ionic amphiphilic compound as extraction adjuvant in an aqueous medium|
    CA2978505A| CA2978505A1|2015-03-18|2016-03-18|Method for producing an extract of a matrix of vegetable origin with a non-ionic amphiphilic compound as extraction adjuvant in an aqueous medium|
    BR112017017747-1A| BR112017017747B1|2015-03-18|2016-03-18|PROCESS OF PREPARATION OF A VEGETABLE MATRIX EXTRACT WITH A NON-IONIC AMPHILLIC COMPOUND AS AN AQUEOUS EXTRACTION ADJUVANT|
    PCT/EP2016/056037| WO2016146837A1|2015-03-18|2016-03-18|Method for producing an extract of a matrix of vegetable origin with a non-ionic amphiphilic compound as extraction adjuvant in an aqueous medium|
    JP2017548880A| JP6887954B2|2015-03-18|2016-03-18|A method for producing a plant-derived matrix extract using a nonionic amphipathic compound as an extraction adjuvant in an aqueous medium.|
    ES16713344T| ES2843640T3|2015-03-18|2016-03-18|Procedure for preparing a plant matrix extract with a non-ionic amphiphilic compound as an extraction aid in aqueous medium|
    EP16713344.6A| EP3270886B1|2015-03-18|2016-03-18|Method for producing an extract of a matrix of vegetable origin with a non-ionic amphiphilic compound as extraction adjuvant in an aqueous medium|
    CN201680013093.9A| CN107404926B|2015-03-18|2016-03-18|Method for preparing an extract of a matrix of vegetable origin in an aqueous medium using a non-ionic amphiphilic compound as extraction adjuvant|
    KR1020177025895A| KR20170129132A|2015-03-18|2016-03-18|Method for Producing Extract of Plant Origin Substrate Using Non-ionic Amphipathic Compound as Extraction Adjuvant in Aqueous Media|
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