WO2016078947A1 - Konzentrierte, niedrigviskose rhamnolipid-zusammensetzungen - Google Patents
Konzentrierte, niedrigviskose rhamnolipid-zusammensetzungen Download PDFInfo
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- WO2016078947A1 WO2016078947A1 PCT/EP2015/076019 EP2015076019W WO2016078947A1 WO 2016078947 A1 WO2016078947 A1 WO 2016078947A1 EP 2015076019 W EP2015076019 W EP 2015076019W WO 2016078947 A1 WO2016078947 A1 WO 2016078947A1
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- WIPO (PCT)
- Prior art keywords
- weight
- rhamnolipids
- rhamnolipid
- composition
- contained
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/06—Ether- or thioether carboxylic acids
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/221—Mono, di- or trisaccharides or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
Definitions
- the invention relates to concentrated rhamnolipid compositions and to processes for their preparation.
- Rhamnolipids are surface active glycolipids and metabolites of certain microorganisms. They have special surfactant properties, such as strong foaming and are interesting for various technical applications. Rhamnolipids can be used both with wild strains and through
- Surfactants incorporated into cosmetic formulations e.g., shampoos, handwash detergents
- household cleaners and dishwashing detergents must be in liquid form at ordinary processing temperatures to ensure processing via piping systems and pumps to the manufacturer of such products.
- the viscosity should be low in order to ensure easy and reliable delivery. At the same time this is nevertheless the highest possible
- Product forms are either solids over different Processes were isolated in more or less pure form (eg removal of a solvent by drying) to pure products, which are marketed in low and medium aqueous concentration (eg to 25 wt.%), Or liquid products in which the main component (n ) derived from the fermentation vegetable oil or degradation products of the vegetable oil is / are. These are therefore rhamnolipid solutions in an oil phase, and the corresponding products have the distinct disadvantage that they only foam very poorly and are therefore of no interest to actual surface-active applications.
- DE4237334A1 furthermore discloses a highly concentrated product form which can be obtained by a particularly simple process for the purification and concentration of rhamnolipids.
- This solid suspensions or pastes are obtained with a high rhamnolipid solids content of 30 to 40 wt .-% and very high viscosity.
- solid dispersions thus obtained are suitable for industrial, large-scale further processing, such as e.g. Preparation of formulations for shampoos and household cleaners unsuitable because they are not suitable for pumping with commonly used pumps due to their high viscosity and inhomogeneity.
- DE102012221519A1 describes a process for obtaining rhamnolipids having excellent foaming properties, in which aqueous rhamnolipid solutions having a pH of 7 and a concentration of about 50% by weight are obtained.
- a disadvantage of this product form is the undesirable, very high viscosity drop on dilution.
- Another disadvantage is the neutrally reduced microbiological stability. It was an object of the invention to provide highly concentrated and low-viscosity rhamnolipid-containing compositions. These should continue to have the lowest possible ionic strength and dilution with water should lead to the least possible viscosity changes. Description of the invention
- Neutralization can be used inorganic and organic bases.
- the present invention therefore relates to aqueous compositions containing high concentrations of rhamnolipids.
- Another object of the invention is a process for the preparation of aqueous compositions containing high concentrations of rhamnolipids.
- An advantage of the present invention is that the ionic strength of the rhamnolipid-containing compositions can be minimized. This allows the formulator appropriate flexibility in adjusting the pH and salinity of the final final formulation.
- compositions have increased microbiological stability.
- Yet another advantage of the present invention is that the compositions are easier to dilute.
- compositions are readily miscible with other surfactants.
- compositions have a reduced tendency to foam due to their high concentration, thus facilitating transport and delivery.
- compositions facilitate easy incorporation of hydrophobic components such as e.g. B. allow oils.
- compositions have a high storage stability.
- compositions do not undergo extreme jumps in viscosity upon dilution with water.
- compositions when manufactured and transported in piping, cause less soiling and, moreover, allow for easier cleaning.
- Yet another advantage of the present invention is that the compositions require less energy to transport for their transport.
- the percentages by weight relate to the total composition, characterized in that the pH of the composition at 25 ° C of 5.5 to ⁇ 7.0, preferably from 5.6 to 6.2, particularly preferably from 5.6 to 6.0, is.
- rhamnolipid in the context of the present invention encompasses rhamnolipids, their protonated forms, and in particular their salts.
- rhamnolipid in connection with the present invention is understood in particular as meaning mixtures of compounds of the general formula (I) and their salts,
- n 1 or 0,
- n 1
- the optically active carbon atoms of the fatty acids are preferably present as R enantiomers (e.g., (R) -3 - ⁇ (R) -3- [2-0- ( ⁇ -L-rhamnopyranosyl) - ⁇ -L-rhamnopyranosyl] oxydecanoyl ⁇ oxydecanoate).
- R enantiomers e.g., (R) -3 - ⁇ (R) -3- [2-0- ( ⁇ -L-rhamnopyranosyl) - ⁇ -L-rhamnopyranosyl] oxydecanoyl ⁇ oxydecanoate.
- the "pH” in the context of the present invention is defined as the value measured for the corresponding composition at 25 ° C after five minutes of stirring with a pH electrode calibrated according to ISO 4319 (1977). All percentages (%) are by mass unless otherwise specified. To determine the content of rhamnolipids in connection with the present invention, only the mass of the rhamnolipid anion, thus "general formula (I) minus one hydrogen" is taken into account.
- the rhamnolipids contained in the formulations according to the invention are present at least partly as salt due to the given pH.
- the cations of the contained rhamnolipid salts are those selected from the group consisting preferably of Li + , Na + , K + , Mg 2+ , Ca 2+ , Al 3+ , ⁇ 4 + , primary ammonium ions , secondary ammonium ions, tertiary ammonium ions and quaternary
- ammonium ions are tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and [(2-hydroxyethyl) trimethylammonium] (choline) and the cations of 2-aminoethanol (ethanolamine, MEA), diethanolamine (DEA), 2,2 ', 2 " Nitrilotriethanol (triethanolamine, TEA), 1-aminopropan-2-ol (monoisopropanolamine), ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 1, 4-diethylenediamine (piperazine),
- Particularly preferred cations are selected from the group comprising, preferably consisting of Na + , K + , NH 4 + and the triethanolammonium cation.
- the total amount of the aforementioned cations preferably makes from 70% to 99%, more preferably from 80% to 90%, by weight of all
- Composition contained cations without FT and H3 ⁇ D + .
- compositions according to the invention contain from 50% to 99% by weight, preferably from 70% to 95% by weight, more preferably from 85% to 90% by weight, of rhamnolipid anions, the Wt .-% on all in the
- composition containing anions without OH " refer.
- the total dry weight contains 40% by weight to 98% by weight, preferably 50% by weight to 95% by weight, particularly preferably 60% by weight to 90% by weight, of rhamnolipids refer the weight percentages to the total solids.
- total dry matter in the context of the present invention is understood to mean that part of the composition according to the invention which remains after the composition according to the invention has been freed, apart from of course water, from the components which are liquid at 25 ° C. and 1 bar.
- at least 60% by weight, preferably at least 80% by weight, particularly preferably at least 95% by weight, of the rhamnolipids are present in dissolved form, the weight percent being based on the
- compositions 51 wt .-% to 95 wt .-%, preferably 70 wt .-% to 90 wt .-%, particularly preferably 75 wt .-% to 85 wt .-%, diRL-C10C10 contain, wherein the percentages by weight refer to the sum of all contained rhamnolipids.
- compositions 0.5 wt .-% to 9 wt .-%, preferably 0.5 wt .-% to 3 wt .-%, particularly preferably 0.5 wt .-% to 2 wt. %, monoRL-C10C10, wherein the percentages by weight refer to the sum of all contained rhamnolipids.
- compositions according to the invention are characterized in that the weight ratio of all di-rhamnolipids present to all mono-rhamnolipids contained is greater than 51:49, in particular greater than 91: 9, preferably greater than 97: 3, particularly preferably greater than 98: 2.
- compositions contain 0.5% to 25% by weight, preferably 5% by weight to 15% by weight, particularly preferably 7% by weight to 12% by weight, of diRL-C 10 C 12, wherein the percentages by weight refer to the sum of all contained rhamnolipids. It is inventively preferred that the compositions 0.1 wt .-% to 5 wt .-%, preferably 0.5 wt .-% to 3 wt .-%, particularly preferably 0.5 wt .-% to 2 wt.
- diRL-C 10 C 12 From 0.5% to 15% by weight, preferably from 3% to 12% by weight, more preferably from 5% to 10% by weight, of diRL-C 10 C 12: 1,
- 0.1 wt .-% to 5 wt .-% preferably 0.5 wt .-% to 3 wt .-%, particularly preferably 0.5 wt .-% to 2 wt .-%, monoRL-C10C12 and
- composition according to the invention contains rhamnolipids of the formula monoRL-CX or diRL-CX in only small amounts.
- composition according to the invention preferably contains
- 0 wt .-% to 5 wt .-% preferably 0 wt .-% to 3 wt .-%, particularly preferably 0 wt .-% to 1 wt .-%, diRLCI O, wherein the weight percent to the sum of all refer to contained rhamnolipids, and the term "0 wt .-%" no detectable amount is to be understood.
- compositions of the invention are substantially free of fatty oil (at 20 ° C liquid acylglycerols) and thus in particular less than 0.5 wt .-%, in particular less than 0.1 wt .-%, particularly preferred no detectable amounts, fatty oil based on the total composition.
- Another object of the present invention is a process for preparing a solution of rhamnolipids comprising the steps a) providing a composition comprising
- Weight percent to the total composition with a pH at 25 ° C of pH 1 to pH 5, preferably from pH 2.5 to 4.0, more preferably from pH 3.0 to pH 3.5
- rhamnolipid content of the total composition to 30% by weight to 70% by weight, preferably 35% by weight to 60% by weight, particularly preferably 40% by weight to 50% by weight, of rhamnolipids,
- weight percentages are based on the total composition.
- compositions according to the invention can be prepared by the process according to the invention.
- the rhamnolipid is preferably at least partially disperse in the composition provided in process step a).
- compositions which have a viscosity of from 3 to 15, preferably from 5 to 10, particularly preferably from 6 to 8 Pas, measured in a rheometer at a shear rate of 10 s -1 .
- a preferred process according to the invention is characterized in that in process step b) the pH is adjusted by adding an organic or inorganic base, preferably in concentrated form.
- an organic or inorganic base preferably in concentrated form.
- base in concentrated form in connection with the present invention, it is understood that the base in the form of a
- Composition is added, which contains at least 60 wt .-%, in particular at least 80 wt .-% base, wherein the percentages by weight relate to the added total composition.
- bases are preferably selected from the group comprising, preferably consisting of alkali metal and alkaline earth metal hydroxides such as NaOH, KOH, Mg (OH) 2 , Ca (OH) 2 ; Al (OH) 3 , NH 4 OH, primary amines, secondary amines, tertiary amines and quaternary amines used.
- alkali metal and alkaline earth metal hydroxides such as NaOH, KOH, Mg (OH) 2 , Ca (OH) 2 ; Al (OH) 3 , NH 4 OH, primary amines, secondary amines, tertiary amines and quaternary amines used.
- Suitable amines are 2-aminoethanol (also
- Triethanolamine Triethanolamine, TEA), 1-aminopropan-2-ol (also monoisopropanolamine), [(2-hydroxyethyl) trimethylammonium] (also choline) ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 1, 4-diethylenediamine (also piperazine), aminoethylpiperazine, aminoethylethanolamine , Tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide,
- Hydroxyethyl) trimethylammonium also choline are preferably used.
- Particularly preferred bases are NaOH, KOH, NH 3 , NH 4 OH and triethanolamine. It is also possible to use mixtures of the abovementioned bases according to the invention.
- Process step b) and / or c) mixing apparatuses such as e.g. Extruders are used.
- a further subject of the present invention are thus salts of at least one rhamnolipid, characterized in that it contains at least one cation, selected from the group comprising, preferably consisting of, Li +, K +, Mg 2+, Ca 2+, Al 3+, NH 4 +, primary ammonium ions, secondary ammonium ions, tertiary
- the salts according to the invention preferably contain at least 50% by weight, preferably at least 70% by weight, particularly preferably at least 95% by weight, of the at least one cation, the percentages by weight being based on the weight of the total salt "rhamnolipid anion plus cation" and refer to the total salt.
- ammonium ions are tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium and [(2-
- Hydroxyethyl) trimethylammonium] (choline) and the cations of 2-aminoethanol (ethanolamine, MEA), diethanolamine (DEA), 2,2 ', 2 "-nitrilotriethanol (triethanolamine, TEA), 1-aminopropan-2-ol (monoisopropanolamine) , Ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, 1, 4-diethylenediamine (piperazine),
- Particularly preferred cations are selected from the group comprising, preferably consisting of Li + , Al 3+ , Nh and the triethanolammonium cation.
- preferred rhamnolipid salts according to the invention have the rhamnolipids mentioned above with regard to mono-, di- and fatty acid content as mentioned above as being preferred in the compositions according to the invention.
- the quantification was carried out by means of HPLC.
- the calibration standard used was the acid form of the various rhamnolipid species, the chromatographic ones Separation was also under acidic conditions. This results in all RL components being quantified into a sample as an acid form.
- aqueous 0.1% TFA trifluoroacetic acid, solution A
- methanol solution B
- the column temperature was 40 ° C.
- the detectors used are the ELSD (detector temperature 60 ° C) and the DAD (diode array, 210 nm).
- the gradient used in the method was:
- the viscosity is measured by means of a rheometer (MCR 302, Anton Paar Germany) in a plate-plate measuring system.
- the top plate had one
- Diameter of 40 mm Diameter of 40 mm, the gap distance was 0.5 mm, measuring temperature was 25 ° C. It was measured in the shear rate range of 0.1 -100 s-1.
- Example 1 Preparation of a highly concentrated RL solution: a fermentation with a Pseudomonas putida strain pBBR1MCS2-Plac-rhlABC-T-Ptac-rhlC-T containing the rhamnolipid biosynthesis genes RhIA, RhIB and RhIC, the preparation of which is described in US2014296168 was carried out.
- a mineral medium M9 was used for the main culture.
- the fermentation was carbon-led via a glucose feed in a 2 liter fermenter.
- the glucose feed is based on the
- Dissolved oxygen signal The dissolved oxygen was regulated at 20% saturation above the stirrer speed.
- the pH is regulated to 7 via a pH electrode and addition of NH 4 SO 4 .
- the defoamer DOW Corning 1500 was metered in if necessary. The fermentation was carried out over 4 days to a dry biomass of 15 g / l.
- Rhamnolipid concentration was determined by HPLC to be 9.8 g / l.
- the fermentation broth was adjusted to a pH of 3.1 by addition of concentrated H2SO4.
- a pasty solid concentrate was obtained with an RL content of 45 wt.% And with a viscosity of> 10,000 mPas.
- Viscosity (Pas, shear rate 10 1 / s) of rhamnolipid compositions as a function of rhamnolipid concentration (% by weight) and pH.
- the formulations indicated by * are according to the invention, since in this case the viscosity is low at high concentration and the viscosity drop when diluting with water is also lowest (compare the respective viscosities at 10% and 20%).
- the partial neutralization was carried out analogously to Example 2, with the exception that instead of KOH a 50 wt.% NaOH solution was used.
- Example 2 The highly concentrated, acidic rhamnolipid suspension obtained in Example 1 was adjusted by addition of water to a rhamnolipid content of 34.6% by weight, which had a pH of 3.18. There were removed 1 13 g of this suspension and with constant stirring, 3.64 g of a 25 wt.% NH4OH solutions were added. This resulted in a complete liquefaction and it turned to a pH of 5.63.
- the resulting rhamnolipid suspension was added by water adjusted to a Rhamnolipidgehalt of 40 wt.% And divided into several parts of 50 g. Then, with constant stirring, 2.28 g monoethanolamine (purity> 99%) were added to one of the parts, which led to liquefaction and clearing of the solution.
- the pH of the resulting solution was 6.0.
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201580062789.6A CN107001403B (zh) | 2014-11-19 | 2015-11-09 | 浓缩的低粘度的鼠李糖脂组合物 |
EP15791601.6A EP3221326B1 (de) | 2014-11-19 | 2015-11-09 | Konzentrierte, niedrigviskose rhamnolipid-zusammensetzungen |
US15/520,157 US10604722B2 (en) | 2014-11-19 | 2015-11-09 | Concentrated, low-viscosity rhamnolipid compositions |
KR1020177013467A KR102368119B1 (ko) | 2014-11-19 | 2015-11-09 | 농축된 저점도 람노리피드 조성물 |
KR1020227005811A KR102473780B1 (ko) | 2014-11-19 | 2015-11-09 | 농축된 저점도 람노리피드 조성물 |
BR112017009374-0A BR112017009374B1 (pt) | 2014-11-19 | 2015-11-09 | Composição e método para preparar uma solução de ramnolipídeos |
JP2017527314A JP7055018B2 (ja) | 2014-11-19 | 2015-11-09 | 低粘度のラムノリピッド濃縮組成物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14193779.7 | 2014-11-19 | ||
EP14193779.7A EP3023431B1 (de) | 2014-11-19 | 2014-11-19 | Konzentrierte, niedrigviskose Rhamnolipid-Zusammensetzungen |
Publications (1)
Publication Number | Publication Date |
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WO2016078947A1 true WO2016078947A1 (de) | 2016-05-26 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2015/076019 WO2016078947A1 (de) | 2014-11-19 | 2015-11-09 | Konzentrierte, niedrigviskose rhamnolipid-zusammensetzungen |
Country Status (8)
Country | Link |
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US (1) | US10604722B2 (de) |
EP (2) | EP3023431B1 (de) |
JP (1) | JP7055018B2 (de) |
KR (2) | KR102473780B1 (de) |
CN (2) | CN107001403B (de) |
BR (1) | BR112017009374B1 (de) |
PL (1) | PL3023431T3 (de) |
WO (1) | WO2016078947A1 (de) |
Families Citing this family (24)
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WO2016115048A1 (en) | 2015-01-12 | 2016-07-21 | Logos Technologies, Llc | Production of rhamnolipid compositions |
WO2017144318A1 (de) | 2016-02-22 | 2017-08-31 | Evonik Degussa Gmbh | Rhamnolipidamide zur haarduftstoff-retention |
EP3419985A1 (de) | 2016-02-22 | 2019-01-02 | Evonik Degussa GmbH | Rhamnolipidester als nichtionische tenside zur kosmetischen anwendung |
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US11851583B2 (en) | 2016-07-19 | 2023-12-26 | Evonik Operations Gmbh | Process for producing porous polyurethane coatings using polyol ester additives |
CN110167347B (zh) | 2016-10-07 | 2022-07-15 | 赢创运营有限公司 | 包含糖脂和防腐剂的组合物 |
JP7271431B2 (ja) | 2017-02-10 | 2023-05-11 | エボニック オペレーションズ ゲーエムベーハー | 少なくとも1種のバイオサーファクタント及びフッ化物を含有するオーラルケア組成物 |
BR112019022453A2 (pt) | 2017-04-27 | 2020-05-12 | Evonik Degussa Gmbh | Composição e uso de uma composição |
CN110997069B (zh) * | 2017-08-24 | 2022-12-30 | 赢创运营有限公司 | 作为乳化剂和分散助剂的鼠李糖脂衍生物 |
MX2020001994A (es) | 2017-08-30 | 2020-09-07 | Evonik Operations Gmbh | Uso de polioleteres para la produccion de revestimientos plasticos porosos. |
BR112020015703A2 (pt) | 2018-02-09 | 2020-12-08 | Evonik Operations Gmbh | Composição, uso e formulação de mistura que compreende glicolipídios |
EP3546589B1 (de) | 2018-03-29 | 2022-08-10 | Evonik Operations GmbH | Verfahren zur herstellung von sphingolipiden |
EP3790949A1 (de) * | 2018-05-11 | 2021-03-17 | Basf Se | Waschmittelzusammensetzung mit rhamnolipiden und/oder mannosylerythritollipiden |
WO2019219303A1 (en) * | 2018-05-17 | 2019-11-21 | Unilever Plc | Cleaning composition |
KR102112570B1 (ko) * | 2019-01-28 | 2020-05-19 | 한국해양과학기술원 | 신규 람노리피드 화합물 및 이의 용도 |
US11918670B2 (en) | 2020-03-11 | 2024-03-05 | Evonik Operations Gmbh | Mixture composition comprising glycolipids and triethyl citrate |
CN115605298A (zh) * | 2020-05-07 | 2023-01-13 | 阿尔芬·埃马尔(De) | 用于使原油液化和/或去除油渣的装置 |
WO2022233700A1 (en) | 2021-05-05 | 2022-11-10 | Evonik Operations Gmbh | Compositions containing at least one biosurfactant and at least one sulfonic or sulfinic acid derivative |
KR20240119067A (ko) | 2021-12-02 | 2024-08-06 | 에보닉 오퍼레이션스 게엠베하 | 글루코리피드들을 포함하는 조성물 |
WO2023161179A1 (en) | 2022-02-24 | 2023-08-31 | Evonik Operations Gmbh | New composition containing liposomes and biosurfactants |
EP4234664A1 (de) | 2022-02-24 | 2023-08-30 | Evonik Operations GmbH | Zusammensetzung mit glucolipiden und enzymen |
EP4234671A1 (de) | 2022-02-24 | 2023-08-30 | Evonik Operations GmbH | Zusammensetzungen mit biotensiden und einer lipase aus stachybotrys chlorohalonata |
WO2024126154A1 (en) | 2022-12-15 | 2024-06-20 | Evonik Operations Gmbh | Composition comprising sophorolipids and rhamnolipids and/or glucolipids |
WO2024132679A1 (en) | 2022-12-21 | 2024-06-27 | Evonik Dr. Straetmans Gmbh | Compositions containing biosurfactants and desferrioxamines |
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Also Published As
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EP3221326A1 (de) | 2017-09-27 |
US20170335238A1 (en) | 2017-11-23 |
BR112017009374B1 (pt) | 2021-07-06 |
CN113024618A (zh) | 2021-06-25 |
KR20220031727A (ko) | 2022-03-11 |
BR112017009374A2 (pt) | 2018-01-30 |
EP3221326B1 (de) | 2024-05-01 |
PL3023431T3 (pl) | 2017-07-31 |
KR102473780B1 (ko) | 2022-12-02 |
US10604722B2 (en) | 2020-03-31 |
CN107001403B (zh) | 2021-03-30 |
KR20170087877A (ko) | 2017-07-31 |
JP2018500293A (ja) | 2018-01-11 |
CN107001403A (zh) | 2017-08-01 |
KR102368119B1 (ko) | 2022-02-25 |
EP3023431B1 (de) | 2017-01-04 |
EP3023431A1 (de) | 2016-05-25 |
JP7055018B2 (ja) | 2022-04-15 |
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