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WO2025114127A1 - Composition comprising biosurfactant, ethanol and dye - Google Patents

Composition comprising biosurfactant, ethanol and dye Download PDF

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Publication number
WO2025114127A1
WO2025114127A1 PCT/EP2024/083104 EP2024083104W WO2025114127A1 WO 2025114127 A1 WO2025114127 A1 WO 2025114127A1 EP 2024083104 W EP2024083104 W EP 2024083104W WO 2025114127 A1 WO2025114127 A1 WO 2025114127A1
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WIPO (PCT)
Prior art keywords
composition according
weight
rhamnolipids
composition
fluoride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2024/083104
Other languages
French (fr)
Inventor
Stefan Julian LIEBIG
Nadine TRUCHAN
Jakob Müller
Peter Schwab
Joaquin PEREZ SANCHEZ
Alexandra Trambitas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Operations GmbH
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Publication date
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Publication of WO2025114127A1 publication Critical patent/WO2025114127A1/en
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes
    • A61K2800/432Direct dyes

Definitions

  • composition comprising biosurfactant, ethanol and dye
  • the invention relates to compositions comprising A) at least one biosurfactant, B) ethanol, and C) at least one dye.
  • mouth wash formulations are highly relevant. These liquid products achieve a high surface contact with the oral cavity, can reach not easily accessible areas and are very easy to use.
  • compositions for minimizing colour fading in an oral care composition comprising a) an organic dye-encapsulated silica shell nanoparticle matrix, b) a physiologically stable fluoride ion-providing compound, c) a physiologically stable peroxide species-providing compound in an amount about 1 % to about 20% by weight.
  • EP2617466B1 discloses mouthwash compositions having a pH of from 4.0 to 6.5, containing, based on its weight, a) at least one dye, b) from 65 to 92.5 wt.% water, c) from 0.02 to 1 wt.% fluoride(s), calculated as F; d) ⁇ 1 wt.% ethanol, e) ⁇ 1 wt.% peroxide(s), calculated as 100 % H2O2.
  • the present invention therefore provides a composition comprising A) at least one biosurfactant, B) ethanol, and C) at least one dye.
  • the invention further provides the use of a composition according to the instant invention for cosmetic cleaning of an oral cavity and the use of a biosurfactant for the stabilization of a dye in ethanolic solution.
  • One advantage of the instant invention is the improved color stability of the compositions of the instant invention.
  • Another advantage of the instant invention is the faster processability of the compositions of the instant invention.
  • a further advantage of the present invention is the faster rinseability of the of the compositions of the instant invention.
  • compositions of the instant invention can have an increased activity of comprised peroxide.
  • compositions of the instant invention can enhance the effects of fluoride comprised in the composition.
  • a further advantage of the present invention is the good anti-bacterial properties of the compositions of the instant invention.
  • a further advantage of the present invention is that it allows to reduce the amount of sweetener in the composition.
  • Another advantage of the present invention is that the discolouration of the packaging is reduced.
  • a further advantage of the present invention is that the foaming of the composition is improved.
  • a further advantage of the present invention is that the mildness is improved.
  • Another advantage of the present invention is that they leave behind a smooth and soft feel after washing.
  • Another advantage of the present invention is that the amount of surface-active substances can be reduced.
  • Another advantage of the present invention is that the transparency of the formulation is increased.
  • a further advantage of the present invention is that the compositions induce a reduced staining of teeth.
  • a further advantage of the present invention is an improved taste of the compositions.
  • a further advantage of the present invention is that the compositions reduce dental plaque.
  • a further advantage of the present invention is that the compositions reduce oral malodor.
  • the instant invention provides a composition comprising
  • biosurfactants are understood as meaning all glycolipids produced by fermentation and their salts.
  • biosurfactant also covers glycolipids that are chemically or enzymatically modified after fermentation, as long as structurally a glycolipid remains.
  • Raw materials for producing the biosurfactants that can be used are carbohydrates, in particular sugars such as e.g. glucose and/or lipophilic carbon sources such as fats, oils, partial glycerides, fatty acids, fatty alcohols, long-chain saturated or unsaturated hydrocarbons.
  • sugars such as e.g. glucose and/or lipophilic carbon sources
  • surfactant is understood to mean organic substances having interface-active properties that have the ability to reduce the surface tension of water at 20°C and at a concentration of 0.5% by weight based on the overall composition to below 45 mN/m. Surface tension is determined by the Du Nouy ring method at 20°C.
  • liquid is understood to be liquid at a temperature of 25°C and a pressure of 1013 mbar.
  • Composition according to the instant invention preferably are characterized in that the biosurfactant is selected from rhamnolipids, sophorolipids, glucolipids, cellulose lipids, mannosylerythritol lipids and trehalose lipids, preferably rhamnolipids, sophorolipids and glucolipids, more preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
  • the biosurfactant is selected from rhamnolipids, sophorolipids, glucolipids, cellulose lipids, mannosylerythritol lipids and trehalose lipids, preferably rhamnolipids, sophorolipids and glucolipids, more preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
  • biosurfactants can be produced e.g. as described in EP 0 499 434, US 7,985,722,
  • Suitable biosurfactants can be acquired e.g. from Soliance, France.
  • the composition according to the instant invention preferably is characterized in that said biosurfactant is selected from rhamnolipids, in particular mono-, di- or polyrhamnolipids, glucolipids, in particular mono-, di- or polyglucolipids, and sophorolipids, in particular mono-, di- or polysophorolipids, preferably selected from rhamnolipids and glucolipids, most preferably rhamnolipids.
  • optically active carbon atoms of the fatty acids are preferably present as R-enantiomers (e.g. (R)-3- ⁇ (R)-3-[2-O-(a-L-rhamnopyranosyl)-a-L-rhamnopyranosyl]oxydecanoyl ⁇ oxydecanoate).
  • R-enantiomers e.g. (R)-3- ⁇ (R)-3-[2-O-(a-L-rhamnopyranosyl)-a-L-rhamnopyranosyl]oxydecanoyl ⁇ oxydecanoate.
  • the nomenclature used therefore does not distinguish between “CXCY” and "CYCX”.
  • Rhamnolipids applicable in the context of the instant invention can also be produced by fermentation of Pseudomonas, especially Pseudomonas aeruginosa, which are preferably non genetically modified cells, a technology already disclosed in the eighties, as documented e.g. in EP0282942 and DE4127908.
  • Pseudomonas especially Pseudomonas aeruginosa
  • Rhamnolipids produced in Pseudomonas aeruginosa cells which have been improved for higher rhamnolipid titres by genetical modification can also be used in the context of the instant invention; such cells have for example been disclosed by Lei et al. in Biotechnol Lett. 2020 Jun;42(6):997-1002.
  • Rhamnolipids produced by Pseudomonas aeruginosa are commercially available from Jeneil Biotech Inc., e.g. under the tradename Zonix, from Logos Technologies (technology acquired by Stepan), e.g. under the tradename NatSurFact, from Biotensidion GmbH, e.g. under the tradename Rhapynal, from AGAE technologies, e.g. under the name R90, R95, R95Md, R95Dd, from Locus Bio-Energy Solutions and from Shanghai Yusheng Industry Co. Ltd., e.g. under the tradename Bio- 201 Glycolipids.
  • the present invention provides a composition preferably as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
  • the present invention provides a composition alternatively preferably comprising as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
  • the present invention further provides a composition preferably as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise 56% by weight to 95% by weight, preferably 60% by weight to 80% by weight, particularly preferably 66% by weight to 70% by weight, of diRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • diRL-C10C12:1 0.5% by weight to 15% by weight, preferably 3% by weight to 12% by weight, particularly preferably 5% by weight to 10% by weight, of diRL-C10C12:1, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • diRL-C10C12 0.5 to 25% by weight, preferably 3% by weight to 15% by weight, particularly preferably 5% by weight to 12% by weight, of diRL-C10C12, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • diRL-C8C10 0.1% by weight to 25% by weight, preferably 2% by weight to 10% by weight, particularly preferably 4% by weight to 8% by weight, of diRL-C8C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • the present invention provides a composition alternatively preferably comprising as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
  • the alternatively preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of 10 % by weight to 30 % by weight, preferably 12% by weight to 25 % by weight, particularly preferably 15% by weight to 20% by weight, of diRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • diRL-C10C12 1% by weight to 15% by weight, preferably 2% by weight to 10% by weight, particularly preferably 3% by weight to 8% by weight, of diRL-C10C12, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
  • Rhamnolipids applicable in the context of the instant invention can also be produced by fermentation of Pseudomonas, especially Pseudomonas aeruginosa, which are preferably non genetically modified cells, a technology already disclosed in the eighties, as documented e.g. in EP0282942 and DE4127908.
  • Pseudomonas especially Pseudomonas aeruginosa
  • Rhamnolipids produced in Pseudomonas aeruginosa cells which have been improved for higher rhamnolipid titres by genetical modification can also be used in the context of the instant invention; such cells have for example been disclosed by Lei et al. in Biotechnol Lett. 2020 Jun;42(6):997-1002.
  • Rhamnolipids produced by Pseudomonas aeruginosa are commercially available from Jeneil Biotech Inc., e.g. under the tradename Zonix, from Logos Technologies (technology acquired by Stepan), e.g. under the tradename NatSurFact, from Biotensidion GmbH, e.g. under the tradename Rhapynal, from AGAE technologies, e.g. under the name R90, R95, R95Md, R95Dd, from Locus Bio-Energy Solutions and from Shanghai Yusheng Industry Co. Ltd., e.g. under the tradename Bio- 201 Glycolipids.
  • the term “sophorolipids” preferably is understood as meaning compounds of the general formulae (Ila) and (lib) and salts thereof where
  • R 1SL H or CO-CH3,
  • R 2SL H or CO-CH3,
  • R 3SL a divalent organic moiety which comprises 6 to 32 carbon atoms and which is unsubstituted or substituted by hydroxyl functions, is unbranched and optionally comprises one to three double or triple bonds,
  • Sophorolipids may be used in accordance with the invention in their acid form or their lactone form.
  • Preferred compositions according to the instant invention comprise a sophorolipid in which the ratio by weight of lactone form to acid form is in the range of 20:80 to 80:20, especially preferably in the ranges of 30:70 to 40:60.
  • the nomenclature used thus does not differentiate between “CXCY” and “CYCX”.
  • a preferred composition according to the instant invention is characterized in that it comprises a non-biosurfactant, preferably selected from the group of anionic, cationic, non-ionic, semi-polar, amphoteric and zwitterionic surfactants, preferably selected from the group of anionic and non-ionic surfactants.
  • a non-biosurfactant preferably selected from the group of anionic, cationic, non-ionic, semi-polar, amphoteric and zwitterionic surfactants, preferably selected from the group of anionic and non-ionic surfactants.
  • non-biosurfactant is different from those surfactants of component A).
  • a preferred composition according to the instant invention is characterized in that it comprises a total amount of all surfactants in an amount of from 0.2 wt.-% to 12.0 wt.-%, preferably from 0.5 wt.- % to 8 wt.-%, more preferably from 0.8 wt.-% to 6 wt.-%, where the percentages by weight refer to the total composition.
  • a preferred composition according to the instant invention is characterized in that component B) is comprised in an amount of from 5.0 wt.-% to 50 wt.-%, preferably from 8.0 wt.-% to 40.0 wt.-%, more preferably from 14.0 wt.-% to 30.0 wt.-%, where the percentages by weight refer to the total composition.
  • component C) is selected from the group comprising, preferably consisting of,
  • Cl 42053 also known as Fast Green FCF, Cl 42090, also known as Brilliant Blue FCF, Cl 16035, also known as Food Red 40, Cl 42051, also known as acid blue 3 and patent blue V, indigo based colorants, like for example Cl 73015, Cl 16185, also known as amaranth, Cl 14720, also known as azorubine, acid blue dyes, preferably selected from Cl 42045, also known as acid blue 1 , Cl 42080, also known as acid blue 7, Cl 62070, also known as acid blue 145, acid blue 182, Cl 74200, also known as acid blue 185, Cl 15707, also known as acid blue 193, Cl 42090, also known as C.l. acid blue 9, and Cl 42780, also known as C.l. acid blue 93,
  • Cl 77007 also known as C.l. pigment blue 29, C.l. solvent blue 3 and C.l. reactive blue 116, preferably Cl 42053, also known as Fast Green FCF, Cl 42090, also known as Brilliant Blue FCF, Cl 16035, also known as Food Red 40.
  • Component D) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, xylitol, sorbitol, sucralose, acesulfame, preferably potassium acesulfame, and saccharine, preferably sodium saccharine.
  • a preferred composition according to the instant invention is characterized in that it comprises D) in form of a polyol based sweetener, preferably selected from xylitol, sorbitol and sucralose, in an amount of from 0.2 wt.-% to 12.0 wt.-%, preferably from 0.5 wt.-% to 8 wt.-%, more preferably from 0.8 wt.-% to 6 wt.-%, where the percentages by weight refer to the total composition
  • a preferred composition according to the instant invention is characterized in that it comprises E) at least one fluoride ion providing component.
  • Component E) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, sodium fluoride, potassium fluoride, calcium fluoride, magnesium fluoride, stannous fluoride, stannous monofluorophosphate, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluoro silicate, amine fluorides and copper fluoride.
  • Component D) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, hydrogen peroxide, urea peroxide, calcium peroxide and carbamate peroxide.
  • F in an amount of from 0.05 wt.-% to 3.0 wt.-%, preferably from 0.1 wt.-% to 2.0 wt.-%, more preferably from 0.5 wt.-% to 1.5 wt.-%, where the percentages by weight refer to the total composition.
  • a preferred composition according to the instant invention thus is characterized in that the pH of the composition at 25°C is from 3.0 to 10.5, preferably from 3.5 to 9.0 and particularly preferably from 4.0 to 8.0.
  • pH in connection with the present invention - unless stated otherwise - is defined as the value which is measured for the relevant composition at 25°C after stirring for five minutes using a pH electrode calibrated in accordance with ISO 4316 (1977).
  • a preferred composition according to the instant invention is characterized in that the pH of the composition at 25°C is from 7.4 to 10.5.
  • compositions are characterized in that the pH of the composition at 25°C is from 4.8 to 6.1.
  • Preferred composition according to the instant invention are cosmetic or pharmaceutical formulations, preferably cosmetic formulations. These formulations preferably are selected from mouth washes and mouth rinses.
  • composition according to the instant invention is outstanding in its ability to clean and disinfect surfaces, especially in cosmetic applications.
  • a further aspect of the instant invention is the use of a composition according to the instant invention for cosmetic cleaning of an oral cavity of a subject, preferably a human, especially of teeth.
  • This use is a non-therapeutic use, of course.
  • a further aspect of the instant invention is a composition according to the instant invention for the use of the prophylaxis of caries.
  • Yet a further aspect of the instant invention is the use of a biosurfactant for the stabilization of a dye in ethanolic solution, preferably in fading, especially due to light exposure.
  • the uses according to the instant invention are characterized in that said biosurfactant is selected from the group of rhamnolipids, glucolipids and sophorolipids, preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
  • compositions according to the instant invention and preferred components thereof are analogously preferably used, also in the preferred amounts.
  • T o measure the colours of freshly produced and aged formulations the international colour system was used (CIELAB: L*, a*, b*).
  • a E* gives the difference between the colour of aged samples and formulations after production.
  • Example 1 Mouth rinse according to the invention
  • the given values are weight percentages of active matter referring to the total composition.

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  • Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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Abstract

The invention relates to compositions comprising A) at least one biosurfactant, B) ethanol, and C) at least one dye.

Description

Composition comprising biosurfactant, ethanol and dye
Field of the invention
The invention relates to compositions comprising A) at least one biosurfactant, B) ethanol, and C) at least one dye.
Prior art
In the field of oral care formulations good aesthetic properties and desirable appearance are of high importance.
Besides classical toothpaste formulations mouth wash formulations are highly relevant. These liquid products achieve a high surface contact with the oral cavity, can reach not easily accessible areas and are very easy to use.
Many formulations in this field exhibit ethanol as an ingredient. Coloured mouthwashes help to draw the attention to the specific products and sometimes relate to a specific flavour. It is further known for formulations containing ethanol that the colour of these formulations can fade over time. Different solutions have been presented to counteract the effect of discoloration in the prior art. W02009023393 discloses compositions for minimizing colour fading in an oral care composition comprising a) an organic dye-encapsulated silica shell nanoparticle matrix, b) a physiologically stable fluoride ion-providing compound, c) a physiologically stable peroxide species-providing compound in an amount about 1 % to about 20% by weight.
EP2617466B1 discloses mouthwash compositions having a pH of from 4.0 to 6.5, containing, based on its weight, a) at least one dye, b) from 65 to 92.5 wt.% water, c) from 0.02 to 1 wt.% fluoride(s), calculated as F; d) <1 wt.% ethanol, e) <1 wt.% peroxide(s), calculated as 100 % H2O2.
It is an object of the invention to provide ethanolic compositions comprising at least one dye with improved colour stability.
Description of the invention
Surprisingly it has been found that the incorporation of biosurfactants in coloured compositions can lead to an increased stability of the colour.
The present invention therefore provides a composition comprising A) at least one biosurfactant, B) ethanol, and C) at least one dye. The invention further provides the use of a composition according to the instant invention for cosmetic cleaning of an oral cavity and the use of a biosurfactant for the stabilization of a dye in ethanolic solution.
One advantage of the instant invention is the improved color stability of the compositions of the instant invention.
Another advantage of the instant invention is the faster processability of the compositions of the instant invention.
A further advantage of the present invention is the faster rinseability of the of the compositions of the instant invention.
One advantage of the present invention is that the compositions of the instant invention can have an increased activity of comprised peroxide.
Another advantage of the present invention is that the compositions of the instant invention can enhance the effects of fluoride comprised in the composition.
A further advantage of the present invention is the good anti-bacterial properties of the compositions of the instant invention.
A further advantage of the present invention is that it allows to reduce the amount of sweetener in the composition.
Another advantage of the present invention is that the discolouration of the packaging is reduced.
A further advantage of the present invention is that the foaming of the composition is improved.
A further advantage of the present invention is that the mildness is improved.
Another advantage of the present invention is that they leave behind a smooth and soft feel after washing.
Another advantage of the present invention is that the amount of surface-active substances can be reduced.
Another advantage of the present invention is that the transparency of the formulation is increased. A further advantage of the present invention is that the compositions induce a reduced staining of teeth.
A further advantage of the present invention is an improved taste of the compositions.
A further advantage of the present invention is that the compositions reduce dental plaque.
A further advantage of the present invention is that the compositions reduce oral malodor.
The instant invention provides a composition comprising
A) at least one biosurfactant,
B) ethanol, and
C) at least one dye. Within the context of the present invention, “biosurfactants” are understood as meaning all glycolipids produced by fermentation and their salts. The term “biosurfactant” also covers glycolipids that are chemically or enzymatically modified after fermentation, as long as structurally a glycolipid remains. When determining the amount of biosurfactant only the mass of the biosurfactant is taken into account while disregarding the counter ion of the salt, in case the biosurfactant is present as a salt.
Raw materials for producing the biosurfactants that can be used are carbohydrates, in particular sugars such as e.g. glucose and/or lipophilic carbon sources such as fats, oils, partial glycerides, fatty acids, fatty alcohols, long-chain saturated or unsaturated hydrocarbons.
In the context of the present invention, the terms “surfactant” is understood to mean organic substances having interface-active properties that have the ability to reduce the surface tension of water at 20°C and at a concentration of 0.5% by weight based on the overall composition to below 45 mN/m. Surface tension is determined by the Du Nouy ring method at 20°C.
In the context of the present invention, the terms “liquid” is understood to be liquid at a temperature of 25°C and a pressure of 1013 mbar.
Where average values are stated hereinbelow, then, unless stated otherwise, these are number- averaged average values.
Unless stated otherwise, percentages are data in per cent by weight. The same is true for parts per million (ppm).
Wherever measurement values are stated hereinbelow, then, unless stated otherwise, these have been determined at a temperature of 25°C and a pressure of 1013 mbar.
Composition according to the instant invention preferably are characterized in that the biosurfactant is selected from rhamnolipids, sophorolipids, glucolipids, cellulose lipids, mannosylerythritol lipids and trehalose lipids, preferably rhamnolipids, sophorolipids and glucolipids, more preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
Mixtures of different biosurfactants can be comprised in the composition of the instant invention, of course.
The biosurfactants can be produced e.g. as described in EP 0 499 434, US 7,985,722,
WO 03/006146, DE 19648439, DE 19600743, JP 01 304034, CN 1337439, JP 2006 274233, JP 2006 083238, JP 2006 070231, WO 03/002700, FR 2740779, DE 2939519, US 7.556,654, FR 2855752, EP 1445302, JP 2008 062179 and JP 2007 181789 or the documents cited therein. Suitable biosurfactants can be acquired e.g. from Soliance, France.
Preferably, the composition according to the instant invention preferably is characterized in that said biosurfactant is selected from rhamnolipids, in particular mono-, di- or polyrhamnolipids, glucolipids, in particular mono-, di- or polyglucolipids, and sophorolipids, in particular mono-, di- or polysophorolipids, preferably selected from rhamnolipids and glucolipids, most preferably rhamnolipids. The term "rhamnolipids" in the context of the present invention preferably is understood to mean particularly compounds of the general formula (I) and salts thereof,
Figure imgf000005_0001
Formula (I) where mRL = 2, 1 or 0, preferably 1 or 0, nRL = 1 or 0,
R1RL and R2RL = mutually independently, identical or different, organic residues having 2 to 24, preferably 5 to 13 carbon atoms, in particular optionally branched, optionally substituted, particularly hydroxy-substituted, optionally unsaturated, in particular optionally mono-, bi- or triunsaturated alkyl residues, preferably those selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where o = 1 to 23, preferably 4 to 12. If nRL = 1 , the glycosidic bond between the two rhamnose units is preferably in the a-configuration. The optically active carbon atoms of the fatty acids are preferably present as R-enantiomers (e.g. (R)-3-{(R)-3-[2-O-(a-L-rhamnopyranosyl)-a-L-rhamnopyranosyl]oxydecanoyl}oxydecanoate).
The term "di-rhamnolipid" in the context of the present invention is understood to mean compounds of the general formula (I) or salts thereof, where nRL = 1.
The term "mono-rhamnolipid" in the context of the present invention is understood to mean compounds of the general formula (I) or salts thereof, where nRL = 0.
Distinct rhamnolipids are abbreviated according to the following nomenclature:
"diRL-CXCY" are understood to mean di-rhamnolipids of the general formula (I), in which one of the residues R1RL and R2RL = (CH2)o-CH3 where o = X-4 and the remaining residue R1 or R2 = (CH2)O-CH3 where o = Y-4.
"monoRL-CXCY" are understood to mean mono-rhamnolipids of the general formula (I), in which one of the residues R1RL and R2RL = (CH2)o-CH3 where o = X-4 and the remaining residue R1RL or R2RL = (CH2)O-CH3 where o = Y-4. The nomenclature used therefore does not distinguish between "CXCY" and "CYCX". For rhamnolipids where mRL=0, monoRL-CX or diRL-CX is used accordingly.
If one of the above mentioned indices X and/or Y is provided with ":Z", this signifies that the respective residue R1RL and/or R2RL is equal to an unbranched, unsubstituted hydrocarbon residue having X-3 or Y-3 carbon atoms having Z double bonds.
Methods for preparing the relevant rhamnolipids are disclosed, for example, in EP2786743 and EP2787065.
Rhamnolipids applicable in the context of the instant invention can also be produced by fermentation of Pseudomonas, especially Pseudomonas aeruginosa, which are preferably non genetically modified cells, a technology already disclosed in the eighties, as documented e.g. in EP0282942 and DE4127908. Rhamnolipids produced in Pseudomonas aeruginosa cells which have been improved for higher rhamnolipid titres by genetical modification can also be used in the context of the instant invention; such cells have for example been disclosed by Lei et al. in Biotechnol Lett. 2020 Jun;42(6):997-1002.
Rhamnolipids produced by Pseudomonas aeruginosa are commercially available from Jeneil Biotech Inc., e.g. under the tradename Zonix, from Logos Technologies (technology acquired by Stepan), e.g. under the tradename NatSurFact, from Biotensidion GmbH, e.g. under the tradename Rhapynal, from AGAE technologies, e.g. under the name R90, R95, R95Md, R95Dd, from Locus Bio-Energy Solutions and from Shanghai Yusheng Industry Co. Ltd., e.g. under the tradename Bio- 201 Glycolipids.
The present invention provides a composition preferably as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
51% by weight to 100% by weight, preferably 60% by weight to 95% by weight, particularly preferably 80% by weight to 90% by weight, of mono-rhamnolipids, especially those of formula (I) with nRL=0, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The present invention provides a composition alternatively preferably comprising as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
71% by weight to 100% by weight, preferably 75% by weight to 95% by weight, particularly preferably 80% by weight to 90% by weight, of di-rhamnolipids, especially those of formula (I) with nRL=1 , where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The present invention further provides a composition preferably as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise 56% by weight to 95% by weight, preferably 60% by weight to 80% by weight, particularly preferably 66% by weight to 70% by weight, of diRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
A preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
0.5% by weight to 15% by weight, preferably 3% by weight to 12% by weight, particularly preferably 5% by weight to 10% by weight, of diRL-C10C12:1, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
A further preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
0.5 to 25% by weight, preferably 3% by weight to 15% by weight, particularly preferably 5% by weight to 12% by weight, of diRL-C10C12, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
A preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
0.1% by weight to 25% by weight, preferably 2% by weight to 10% by weight, particularly preferably 4% by weight to 8% by weight, of diRL-C8C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
An even further preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
0.1% by weight to 5% by weight, preferably 0.5% by weight to 3% by weight, particularly preferably
0.5% by weight to 2% by weight, of monoRL-C8C10 and/or, preferably and
0.1% by weight to 5% by weight, preferably 0.5% by weight to 3% by weight, particularly preferably
0.5% by weight to 2% by weight, of monoRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The present invention provides a composition alternatively preferably comprising as said biosurfactant rhamnolipids, characterized in that the rhamnolipids comprise
10% by weight to 30% by weight, preferably 20% by weight to 30% by weight, particularly preferably 25% by weight to 30% by weight, of monoRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The alternatively preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of 10 % by weight to 30 % by weight, preferably 12% by weight to 25 % by weight, particularly preferably 15% by weight to 20% by weight, of diRL-C10C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The alternatively preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
10 % by weight to 30 % by weight, preferably 12% by weight to 25 % by weight, particularly preferably 15% by weight to 20% by weight, of monoRL-C8C10, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The alternatively preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
3% by weight to 25% by weight, preferably 5% by weight to 20% by weight, particularly preferably 10% by weight to 15% by weight, of monoRL-C10C12:1 , where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
The alternatively preferred composition according to the invention is characterized in that the biosurfactant is said rhamnolipids as described above with a content of
1% by weight to 15% by weight, preferably 2% by weight to 10% by weight, particularly preferably 3% by weight to 8% by weight, of diRL-C10C12, where the percentages by weight refer to the sum of all of the rhamnolipids comprised in the liquid composition.
Methods for preparing the relevant rhamnolipids are disclosed, for example, in EP2786743 and EP2787065.
Rhamnolipids applicable in the context of the instant invention can also be produced by fermentation of Pseudomonas, especially Pseudomonas aeruginosa, which are preferably non genetically modified cells, a technology already disclosed in the eighties, as documented e.g. in EP0282942 and DE4127908. Rhamnolipids produced in Pseudomonas aeruginosa cells which have been improved for higher rhamnolipid titres by genetical modification can also be used in the context of the instant invention; such cells have for example been disclosed by Lei et al. in Biotechnol Lett. 2020 Jun;42(6):997-1002.
Rhamnolipids produced by Pseudomonas aeruginosa are commercially available from Jeneil Biotech Inc., e.g. under the tradename Zonix, from Logos Technologies (technology acquired by Stepan), e.g. under the tradename NatSurFact, from Biotensidion GmbH, e.g. under the tradename Rhapynal, from AGAE technologies, e.g. under the name R90, R95, R95Md, R95Dd, from Locus Bio-Energy Solutions and from Shanghai Yusheng Industry Co. Ltd., e.g. under the tradename Bio- 201 Glycolipids. In the context of the present invention, the term “sophorolipids” preferably is understood as meaning compounds of the general formulae (Ila) and (lib) and salts thereof
Figure imgf000009_0001
where
R1SL = H or CO-CH3,
R2SL = H or CO-CH3,
R3SL = a divalent organic moiety which comprises 6 to 32 carbon atoms and which is unsubstituted or substituted by hydroxyl functions, is unbranched and optionally comprises one to three double or triple bonds,
R4SL = H, CH3 or a monovalent organic radical which comprises 2 to 10 carbon atoms and which is unsubstituted or substituted by hydroxyl functions, which is unbranched and which optionally comprises one to three double or triple bonds, and nSL = 1 or 0.
Sophorolipids may be used in accordance with the invention in their acid form or their lactone form. Preferred compositions according to the instant invention comprise a sophorolipid in which the ratio by weight of lactone form to acid form is in the range of 20:80 to 80:20, especially preferably in the ranges of 30:70 to 40:60.
To determine the content of sophorolipids in the acid or lactone form in a formulation, refer to EP1411111 B1 , page 8, paragraph [0053],
In connection with the present invention, the term “glucolipids” preferably is understood as meaning compounds of the general formula (III) and salts thereof,
Figure imgf000010_0001
formula (III) where mGL = 3, 2, 1 or 0, preferably 1 or 0,
R1GL and R2GL = independently of one another identical or different organic radical having 2 to 24 carbon atoms, in particular optionally branched, optionally substituted, in particular hydroxysubstituted, optionally unsaturated, in particular optionally mono-, di- or triunsaturated, alkyl radical, preferably one selected from the group consisting of pentenyl, heptenyl, nonenyl, undecenyl and tridecenyl and (CH2)o-CH3 where 0 = 1 to 23, preferably 4 to 12.
Distinct glucolipids are abbreviated according to the following nomenclature:
“GL-CXCY” is understood as meaning glucolipids of the general formula (III) in which one of the radicals R1GL and R2GL = (CH2)o-CH3 where 0 = X-4 and the remaining radical R1GL or R2GL = (CH2)o- CH3 where 0 = Y-4. The nomenclature used thus does not differentiate between “CXCY” and “CYCX”.
If one of the aforementioned indices X and/or Y is provided with “:Z”, then this means that the respective radical R1GL and/or R2GL = an unbranched, unsubstituted hydrocarbon radical with X-3 or Y-3 carbon atoms having Z double bonds.
Methods for production of glucolipids can be carried out as described in WO2019154970.
A preferred composition according to the instant invention is characterized in that it comprises
A) in an amount of from 0.2 wt.-% to 10.0 wt.-%, preferably from 0.5 wt.-% to 7.0 wt.-%, more preferably from 0.8 wt.-% to 5.0 wt.-%, where the percentages by weight refer to the total composition.
A preferred composition according to the instant invention is characterized in that it comprises a non-biosurfactant, preferably selected from the group of anionic, cationic, non-ionic, semi-polar, amphoteric and zwitterionic surfactants, preferably selected from the group of anionic and non-ionic surfactants.
Obviously the non-biosurfactant is different from those surfactants of component A).
Preferred non-biosurfactants comprised in the composition of the instant invention are selected from sodium lauryl sulfate and poloxameres. Preferably, sodium lauryl sulfate and at least one poloxamere, preferably poloxamer 407, is comprised in a preferred composition according to the instant invention.
A preferred composition according to the instant invention is characterized in that it comprises a total amount of all surfactants in an amount of from 0.2 wt.-% to 12.0 wt.-%, preferably from 0.5 wt.- % to 8 wt.-%, more preferably from 0.8 wt.-% to 6 wt.-%, where the percentages by weight refer to the total composition.
A preferred composition according to the instant invention is characterized in that component B) is comprised in an amount of from 5.0 wt.-% to 50 wt.-%, preferably from 8.0 wt.-% to 40.0 wt.-%, more preferably from 14.0 wt.-% to 30.0 wt.-%, where the percentages by weight refer to the total composition.
A preferred composition according to the instant invention is characterized in that component C) is selected from the group comprising, preferably consisting of,
Cl 42053, also known as Fast Green FCF, Cl 42090, also known as Brilliant Blue FCF, Cl 16035, also known as Food Red 40, Cl 42051, also known as acid blue 3 and patent blue V, indigo based colorants, like for example Cl 73015, Cl 16185, also known as amaranth, Cl 14720, also known as azorubine, acid blue dyes, preferably selected from Cl 42045, also known as acid blue 1 , Cl 42080, also known as acid blue 7, Cl 62070, also known as acid blue 145, acid blue 182, Cl 74200, also known as acid blue 185, Cl 15707, also known as acid blue 193, Cl 42090, also known as C.l. acid blue 9, and Cl 42780, also known as C.l. acid blue 93,
Cl 77007, also known as C.l. pigment blue 29, C.l. solvent blue 3 and C.l. reactive blue 116, preferably Cl 42053, also known as Fast Green FCF, Cl 42090, also known as Brilliant Blue FCF, Cl 16035, also known as Food Red 40.
A preferred composition according to the instant invention is characterized in that it comprises
C) in an amount of from 0.00005 wt.-% to 0.01 wt.-%, preferably from 0.00001 wt.-% to 0.005 wt.-%, more preferably from 0.0002wt.-% to 0.001 wt.-%, where the percentages by weight refer to the total composition.
A preferred composition according to the instant invention is characterized in that it comprises
D) at least one sweetener.
Component D) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, xylitol, sorbitol, sucralose, acesulfame, preferably potassium acesulfame, and saccharine, preferably sodium saccharine.
A preferred composition according to the instant invention is characterized in that it comprises D) in form of a polyol based sweetener, preferably selected from xylitol, sorbitol and sucralose, in an amount of from 0.2 wt.-% to 12.0 wt.-%, preferably from 0.5 wt.-% to 8 wt.-%, more preferably from 0.8 wt.-% to 6 wt.-%, where the percentages by weight refer to the total composition
An alternatively preferred composition according to the instant invention is characterized in that it comprises
D) in form of a dietary, non-polyol based sweetener, preferably selected from acesulfame, preferably potassium acesulfame, and saccharine, preferably sodium saccharine, in an amount of from 0.02 wt.-% to 1.0 wt.-%, preferably from 0.05 wt.-% to 0.8 wt.-%, more preferably from 0.2 wt.- % to 0.5 wt.-%, where the percentages by weight refer to the total composition A preferred composition according to the instant invention is characterized in that it comprises E) at least one fluoride ion providing component.
Component E) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, sodium fluoride, potassium fluoride, calcium fluoride, magnesium fluoride, stannous fluoride, stannous monofluorophosphate, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluoro silicate, amine fluorides and copper fluoride.
A preferred composition according to the instant invention is characterized in that it comprises
E) in an amount to provide from 25 ppm to 5,000 ppm of fluoride ions where the ppm refer to the total composition.
A preferred composition according to the instant invention is characterized in that it comprises
F) at least one orally acceptable peroxide.
Component D) in the composition according to the instant invention is preferably selected from the group comprising, preferably consisting of, hydrogen peroxide, urea peroxide, calcium peroxide and carbamate peroxide.
A preferred composition according to the instant invention is characterized in that it comprises
F) in an amount of from 0.05 wt.-% to 3.0 wt.-%, preferably from 0.1 wt.-% to 2.0 wt.-%, more preferably from 0.5 wt.-% to 1.5 wt.-%, where the percentages by weight refer to the total composition.
The instant invention works well over a broad range of pH. A preferred composition according to the instant invention thus is characterized in that the pH of the composition at 25°C is from 3.0 to 10.5, preferably from 3.5 to 9.0 and particularly preferably from 4.0 to 8.0.
The “pH” in connection with the present invention - unless stated otherwise - is defined as the value which is measured for the relevant composition at 25°C after stirring for five minutes using a pH electrode calibrated in accordance with ISO 4316 (1977).
When, for example, mouth washes are concerned, two different products concepts are available: A basic and an acidic one.
In case, that basic compositions are wished for, a preferred composition according to the instant invention is characterized in that the pH of the composition at 25°C is from 7.4 to 10.5.
In case, that acidic compositions are wished for, an alternatively preferred composition according to the instant invention is characterized in that the pH of the composition at 25°C is from 4.8 to 6.1. Preferred composition according to the instant invention are cosmetic or pharmaceutical formulations, preferably cosmetic formulations. These formulations preferably are selected from mouth washes and mouth rinses.
The composition according to the instant invention is outstanding in its ability to clean and disinfect surfaces, especially in cosmetic applications.
Therefore, a further aspect of the instant invention is the use of a composition according to the instant invention for cosmetic cleaning of an oral cavity of a subject, preferably a human, especially of teeth. This use is a non-therapeutic use, of course.
A further aspect of the instant invention is a composition according to the instant invention for the use of the prophylaxis of caries.
Yet a further aspect of the instant invention is the use of a biosurfactant for the stabilization of a dye in ethanolic solution, preferably in fading, especially due to light exposure.
Preferably the uses according to the instant invention are characterized in that said biosurfactant is selected from the group of rhamnolipids, glucolipids and sophorolipids, preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
In the case of the uses according to the invention, particularly preferred embodiments of the compositions according to the instant invention and preferred components thereof are analogously preferably used, also in the preferred amounts.
The examples adduced hereinafter describe the present invention by way of example, without any intention that the invention, the scope of application of which is apparent from the entirety of the description and the claims, be restricted to the embodiments specified in the examples.
T o measure the colours of freshly produced and aged formulations the international colour system was used (CIELAB: L*, a*, b*). A E* gives the difference between the colour of aged samples and formulations after production.
Figure imgf000014_0001
Example 1: Mouth rinse according to the invention
The given values are weight percentages of active matter referring to the total composition.
Figure imgf000015_0001
Dissolve the flavor in RHEANCE® One. Blend water and ethanol. Add it slowly to the mixture of RHEANCE® One and flavor while stirring. Add the remaining ingredients in the given order. Example 2: Mouth rinse not according to the invention
The given values are weight percentages of active matter referring to the total composition.
Figure imgf000015_0002
Dissolve the flavor inPoloxamer 407. Blend water and ethanol. Add it slowly to the mixture of Poloxamer 407and flavor while stirring. Add the remaining ingredients in the given order. Example 3: Colour stability
After preparation the samples were stored at 25°C in the dark or under UV exposure (sun light). The colour values were measured before and after storage.
Figure imgf000016_0001
As can be seen by the AE-differences, the compositions according to the instant invention suffer from way less colour-fading than the non-inventive ones.

Claims

Claims
1. Composition comprising
A) at least one biosurfactant,
B) ethanol, and
C) at least one dye.
2. Composition according to claim 1 , characterized in that the biosurfactant is selected from rhamnolipids, glucolipids and sophorolipids, preferably rhamnolipids and glucolipids, most preferably rhamnolipids.
3. Composition according to Claim 1 or 2, characterized in that component B) is comprised in an amount of from 5.0 wt.-% to 50 wt.-%, preferably from 8.0 wt.-% to 40.0 wt.-%, more preferably from 14.0 wt.-% to 30.0 wt.-%, where the percentages by weight refer to the total composition.
4. Composition according to at least one of the preceding claims, characterized in that component C) is selected from the group comprising
Cl 42053, Cl 42090, Cl 16035, CI42051, CI73015, CI16185, CI14720, acid blue dyes, preferably selected from Cl 42045, Cl 42080, Cl 62070, acid blue 182, Cl 74200, Cl 15707, Cl 42090 and Cl 42780,
Cl 77007, C.l. solvent blue 3 and C.l. reactive blue 116.
5. Composition according to at least one of the preceding claims, characterized in that it comprises
C) in an amount of from 0.00005 wt.-% to 0.01 wt.-%, preferably from 0.00001 wt.-% to 0.005 wt.-%, more preferably from 0.0002wt.-% to 0.001 wt.-%, where the percentages by weight refer to the total composition.
6. Composition according to at least one of the preceding claims, characterized in that it comprises
D) at least one sweetener.
7 Composition according to claim 6, characterized in that that component D) is selected from the group comprising xylitol, sorbitol, sucralose, acesulfame, preferably potassium acesulfame, and saccharine, preferably sodium saccharine.
8. Composition according to at least one of the preceding claims, characterized in that it comprises E) at least one fluoride ion providing component.
9. Composition according to claim 8, characterized in that that component E) is selected from the group comprising sodium fluoride, potassium fluoride, calcium fluoride, magnesium fluoride, stannous fluoride, stannous monofluorophosphate, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluoro silicate, amine fluorides and copper fluoride.
10. Composition according to claim 8 or 9, characterized in that it comprises
E) in an amount to provide from 25 ppm to 5,000 ppm of fluoride ions where the ppm refer to the total composition.
11. Composition according to at least one of the preceding claims, characterized in that it comprises
F) at least one orally acceptable peroxide, preferably selected from the group comprising hydrogen peroxide, urea peroxide, calcium peroxide and carbamate peroxide.
12. Composition according to claim 11 , characterized in that it comprises
F) in an amount of from 0.3 wt.-% to 6.0 wt.-%, preferably from 0.3 wt.-% to 3.0 wt.-%, more preferably from 1.0 wt.-% to 2.0 wt.-%, where the percentages by weight refer to the total composition.
13. Composition according to at least one of the preceding claims, characterized in that the pH of the composition at 25°C is from 3.0 to 10.5, preferably from 3.5 to 9.0 and particularly preferably from 4.0 to 8.0.
14. Use of a composition according to at least one of the Claims 1 to 13 for cosmetic cleaning of an oral cavity of a subject, preferably a human, especially of teeth.
15. Use of a biosurfactant for the stabilization of a dye in ethanolic solution, preferably in fading, especially due to light exposure.
PCT/EP2024/083104 2023-12-01 2024-11-21 Composition comprising biosurfactant, ethanol and dye Pending WO2025114127A1 (en)

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