Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

• TITLE USE OF WATER SOLUBLE LIGNIN AS AN ANTI-UV FILTER
• the present invention relates to the use of a water-soluble lignin obtained by enzymatic treatment, in particular with at least one bilirubin oxidase enzyme, as an anti-UV filter. It also relates to a cosmetic composition comprising such a lignin.
• Sun protection is a major issue in the cosmetics field.
• the stability of these products is imperative to respect in order to preserve their effectiveness and harmlessness.
• Lignin is a natural polymer available in large quantities, particularly from pulp and cellulose processing plants. Unlike polysaccharides, this phenolic polymer has been the subject of little industrial development apart from "lignosulfonate” and energy recovery applications. However, the potential applications of lignin are numerous. Commercial lignins are essentially soluble in organic solvents or alkaline aqueous solutions with a high base concentration (pH >10). Some lignins are chemically modified and functionalized to give lignosulfonates which are soluble in aqueous solvents of neutral, acidic or slightly basic pH, but they still contain many impurities.
• US Patent 10,729,624 describes the use of mixed microcapsules based on lignins soluble in organic solvents and chemical filters as UV filters.
• lignin present in a solvent is dissolved in an aqueous solution of pH equal to 12, then adjusted to a pH of 7-10.
• This lignin is only soluble in an organic medium (fat-soluble) greatly limits the quantity which can be incorporated into sun creams, and makes their formulation more difficult.
• the vast majority of sun protection products are direct oil-in-water (O/W) emulsions in which the dispersed phase (fatty phase) is a minority.
• O/W oil-in-water
• lignin which can be used as such, soluble in an aqueous medium of neutral pH, which is effective in protecting surfaces (for example keratin materials such as the skin but also surface coating supports) from IIV, in particular UVA and/or UVB.
• the present invention solves this problem.
• the inventors show that the water-soluble lignin according to the invention, soluble in water at a pH of between 5 and 10, and dissolved in the continuous aqueous phase, clearly improves the anti-UV performance.
• this water-soluble lignin has greater protection in UVB rays (SPF), but also greater absorbance in UVA rays.
• the water-soluble nature allows this lignin to be used in larger quantities, without compromising the stability of the formula.
• the anti-UV active agents are then better distributed on the keratin materials, after they have been spread.
• this lignin is biosourced, and has a certain interest compared to conventional petrosourced chemical UV filters.
• the present invention therefore relates to the use of a water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH of between 5 and 10, as an anti-UV filter.
• the enzymatic treatment is carried out with at least one bilirubin oxidase enzyme.
• the water-soluble lignin obtained by enzymatic treatment, preferably with at least one bilirubin oxidase enzyme, preferably comprising few or no sulphonate groups, is called “lignin according to the invention” or “water-soluble lignin according to the invention” in the present asked.
• the present invention also relates to a cosmetic composition
• a cosmetic composition comprising: an aqueous phase comprising at least one water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH of between 5 and 10, and an oily phase and/or at least one hydrophilic thickening polymer chosen from cellulose and its derivatives, natural gums, scleroglucans, chitin and chitosan derivatives, carrageenans and gellans.
• the composition according to the invention is substantially free of microcapsules.
• substantially free it is meant that the composition comprises less than 1% by weight relative to the total weight of composition, preferably less than 0.5% by weight, preferably less than 0.3% by weight, preferably less than 0.1% by weight of microcapsules.
• the composition according to the invention is completely free of microcapsules.
• a subject of the present invention is also a non-therapeutic cosmetic process for caring for keratin materials, preferably the skin, comprising the application to said keratin materials, preferably the skin, of a cosmetic composition as described above.
• the water-soluble lignin according to the invention is obtained by enzymatic treatment.
• This enzymatic modification is specific.
• the lignin obtained differs from a soluble lignin obtained by chemical means, by the low presence or the absence of impurities of synthesis by chemical means and the absence of sulphate or sulphonate groups in particular.
• the enzymatic treatment is carried out with at least one bilirubin oxidase enzyme.
• the lignin according to the invention is water-soluble.
• water-soluble it is meant that the lignin according to the invention is soluble in an aqueous solution, preferably in water, at a concentration ranging up to 90% by weight relative to the total weight of solution.
• the solubility of lignin is assessed at room temperature, preferably in an aqueous solution, typically water, by microscopy and by spontaneous re-dissolution of freeze-dried lignin in an aqueous solvent. No precipitate is observed.
• the water-soluble lignin according to the invention is soluble in water at a pH of between 5 and 10, preferably between 6 and 8.
• the water-soluble lignin according to the invention is obtained by a process comprising the following steps: a- mixing the lignin with water preferably comprising a buffering agent, b- preferably, ultrasound treatment of the mixture obtained by end of step a, c- enzymatic treatment of the lignin obtained in a or b, with at least one bilirubin oxidase enzyme, in the presence or absence of a redox mediator, to obtain a soluble lignin in an aqueous medium of higher pH or equal to 5 and less than or equal to 10, preferably between 6 and 8, and d- separation of the water-soluble lignin from the salts of the mixture and any insoluble compounds obtained in c, preferably by dialysis or centrifugation.
• a method making it possible to obtain the water-soluble lignin according to the invention comprises the solubilization of lignin in a solution comprising water, and preferably also a buffering agent (step a).
• the solubilization of lignin takes place in water as sole solvent, and preferably with a buffering agent.
• the lignin is of the kraft type (or alkaline lignin).
• kraft lignin when it is obtained by a kraft process (also known as "kraft pulping" or sulphate process) which is a process of converting wood into paper pulp.
• the kraft process involves treating wood chips with a hot mixture of water, sodium hydroxide, and sodium sulfide, breaking down the wood fibers and separating the lignin and hemicellulose from the cellulose. This technique includes mechanical and chemical steps, in particular called impregnation and cooking.
• the lignin is of the organosol type.
• a buffering agent is chosen from a borate buffer, a sodium phosphate buffer or any other buffer making it possible to maintain a neutral to basic pH.
• the lignin dispersed in the solution preferably undergoes ultrasound treatment (step b), so as to fragment the material into small particles which can better react with the enzymes.
• This enzymatic treatment of lignin comprises bringing the aqueous solution of dispersed lignin into contact with at least one bilirubin oxidase (BOD) enzyme, in the presence or absence of a redox mediator, and obtaining a lignin soluble in a medium with a pH greater than or equal to 6, preferably greater than or equal to 7.
• BOD bilirubin oxidase
• enzymes of the bilirubin oxidase type which are stable and active in an acid medium but also in a medium neutral and basic, make it possible to modify lignin so as to make it soluble at neutral or basic pH (ie at pH 5 to 10).
• these bilirubin oxidases are more active and more stable than laccases at higher temperatures (up to 70°C).
• BOD bilirubin oxidase
• the BOD used in the context of the present invention is a BOD described in international application WO 2012/160517 (BOD E.C. 1.3.3.5. of Magnaporthe oryzae origin).
• the BOD is of bacterial origin.
• the BOD used in the context of the present invention is a BOD described in international application WO 2011/117839 (BOD E.C. 1.3.3.5. of Bacillus pumilus origin).
• bilirubin oxidase is added to the aqueous solution (preferably with a buffering agent) containing lignin, in the presence or absence of a redox mediator, then placed under conditions allowing its enzymatic action on the lignin in order to solubilize it.
• a redox mediator preferably a redox mediator
• bilirubin oxidase is incubated between 20°C and 80°C, preferably with shaking and oxygen supply.
• the enzymatic action takes place for 2 to 48 hours, preferably for 10 to 24 hours.
• redox mediators examples include 2,2-azino-bis-[3-ethylbenzthiazoline-6-sulfonicacid] (ABTS), 2,6-dimethoxyphenol (2,6-DMP), Syringaldazine, bilirubin conjugated or unconjugated, or osmium compounds.
• ABTS 2,2-azino-bis-[3-ethylbenzthiazoline-6-sulfonicacid]
• 2,6-DMP 2,6-dimethoxyphenol
• Syringaldazine bilirubin conjugated or unconjugated
• osmium compounds examples include 2,2-azino-bis-[3-ethylbenzthiazoline-6-sulfonicacid] (ABTS), 2,6-dimethoxyphenol (2,6-DMP), Syringaldazine, bilirubin conjugated or unconjugated, or osmium compounds.
• the lignin obtained after enzymatic treatment in aqueous solvent is separated from the salts and any insoluble compounds, for example by dialysis or centrifugation (step d).
• the insolubles are separated, for example by centrifugation, from the water-soluble lignin.
• Water-soluble lignin is present in the supernatant when centrifugation is used.
• the water-soluble lignin is lyophilized.
• the water-soluble lignin according to the invention is soluble in water at a pH greater than or equal to 5, preferably greater than or equal to 6, preferably greater than or equal to 7, and less than 10, preferably less than 9, preferably less than 8.
• the lignin is soluble over a pH range of 6 to 8.
• the water-soluble lignin according to the present invention comprises few or no sulphonate groups.
• “few sulphonate groups” is meant a maximum mass content of 1% by weight of sulphonate groups relative to the total weight of lignin.
• a small quantity of sulfonate groups advantageously makes it possible to provide the water-soluble lignin with unique properties of interest, in particular a very low transmittance.
• the present invention relates to the use of a water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH of between 5 and 10, as an anti-UV filter.
• a subject of the present invention is also the use of a composition comprising an aqueous phase, said aqueous phase comprising a water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH comprised between 5 and 10, as a filter Sun Creme.
• the enzymatic treatment is carried out with at least one bilirubin oxidase enzyme.
• the water-soluble lignin comprises no or few sulphonate groups.
• the water-soluble lignin according to the invention is dissolved in the aqueous phase of a composition.
• the lignin according to the invention can be used in various materials, in a paint or varnish composition, in a pesticidal composition, in textiles, in concrete or cement compositions, in food films or various coatings. or substrates.
• a paint or varnish composition in a pesticidal composition
• textiles in concrete or cement compositions
• food films in various coatings. or substrates.
• a coating or a substrate when it is incorporated into a composition or a material or a coating or a substrate, it makes it possible, after application or use, to provide said composition or said material or said coating or said substrate with anti-UV properties.
• the subject of the present invention is the use of a water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH of between 5 and 10, as an anti-UV filter in cosmetic compositions, for example of make-up or care compositions.
• the present invention also relates to the use of a water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH between 5 and 10, as a UV filter in a paint or varnish composition, in a pesticide composition, in textiles, in concrete or cement compositions, in food films or in various coatings or substrates .
• the cosmetic composition according to the invention comprises at least one aqueous phase comprising at least one water-soluble lignin obtained by enzymatic treatment, said lignin being soluble in water at a pH of between 5 and 10.
• the enzymatic treatment is carried out with at least one bilirubin oxidase enzyme.
• the water-soluble lignin comprises no or few sulphonate groups.
• this composition comprises an aqueous phase in which the water-soluble lignin according to the invention is dissolved, and an oily phase.
• the composition according to the invention is an emulsion.
• the oily phase is dispersed in the aqueous phase, and a direct emulsion is then obtained (oil-in-water or O/W).
• the aqueous phase can also be dispersed in the oily phase, and an inverse emulsion (water-in-oil or W/O) is then obtained.
• the cosmetic composition according to the invention can also comprise a thickening polymer, to obtain a gelled composition, for example a gel.
• the aqueous phase according to the invention comprises at least water and the water-soluble lignin according to the invention.
• the water-soluble lignin according to the invention is solubilized in water.
• the composition according to the invention comprises at least 50% by weight of water relative to the total weight of composition, preferably at least 60% by weight, preferably at least 70% by weight.
• the composition according to the invention comprises from 50% to 99% by weight of water relative to the total weight of composition, preferably from 65% to 95% by weight, preferably from 70% to 90% by weight .
• the aqueous phase can also comprise at least one additive chosen from preservatives and humectants.
• the preservative can be selected from parabens and benzyl alcohol.
• the humectant can be chosen from polyols, preferably glycerin or sorbitol.
• the composition according to the invention comprises from 55% to 95% by weight of aqueous phase relative to the total weight of composition, preferably from 65% to 90% by weight, preferably from 75% to 90% by weight .
• the composition according to the invention comprises from 1% to 50% by weight of water relative to the total weight of composition, preferably from 5% to 45% by weight .
• the aqueous phase comprises at least one water-soluble lignin according to the invention.
• the water-soluble lignin according to the invention is as defined previously.
• the composition according to the invention comprises at least 1% by weight of water-soluble lignin according to the invention relative to the total weight of composition, preferably at least 1.5% by weight, preferably at least 2% by weight .
• the composition according to the invention comprises from 1% to 30% by weight of water-soluble lignin according to the invention relative to the total weight of composition, preferably from 1.5% to 25% by weight, preferably from 2 % to 20% by weight.
• the aqueous phase according to the invention may comprise at least one hydrophilic thickening polymer chosen from cellulose and its derivatives, natural gums, scleroglucans, chitin and chitosan derivatives, carrageenans and gellans.
• hydrophilic thickening polymer is meant a water-soluble or water-dispersible thickening polymer.
• Said hydrophilic thickening polymer is preferably chosen from: - cellulose and its derivatives, such as carboxymethylcellulose, hydroxymethylcellulose, hydroethylcellulose, hydroxypropylcellulose or hydroxypropylmethylcellulose;
• - natural gums such as xanthan gum, guar gum, gum arabic or locust bean gum;
• composition according to the invention may comprise, in addition to the above thickener, an additional thickener of the carbomer type.
• the composition according to the invention comprises an aqueous phase in which the water-soluble lignin according to the invention is dissolved, and at least one hydrophilic thickening polymer chosen from cellulose and its derivatives, natural gums, scleroglucans, derivatives of chitin and chitosan, carrageenans and gellans.
• at least one hydrophilic thickening polymer chosen from cellulose and its derivatives, natural gums, scleroglucans, derivatives of chitin and chitosan, carrageenans and gellans.
• One such composition is an aqueous gel.
• the hydrophilic thickening polymer is present in an amount ranging from 0.1% to 5% by weight relative to the total weight of composition, preferably from 0.2% to 3% by weight.
• composition according to the invention may comprise an oily phase.
• the oily phase comprises at least one lipophilic compound (i.e. not soluble in water), preferably chosen from oils, waxes, butters and mixtures thereof.
• oil is meant a liquid lipophilic compound at room temperature.
• wax is meant a lipophilic compound which is solid at room temperature.
• “butter” is meant a semi-liquid or semi-solid lipophilic compound at room temperature.
• Oils, waxes and butters are well known in the prior art.
• the composition according to the invention comprises from 5% to 50% by weight of oily phase relative to the total weight of composition, preferably from 10% to 40% by weight, preferably from 15% to 30% by weight .
• the composition according to the invention is in the form of an inverse emulsion, it comprises from 50% to 95% by weight of oily phase relative to the total weight of the composition.
• composition in the form of an emulsion can also comprise at least one surfactant, at least one lipophilic UV screening agent and/or at least one dyestuff.
• composition according to the invention may comprise at least one surfactant.
• the surfactant is chosen from anionic surfactants, nonionic surfactants, amphoteric surfactants and mixtures thereof.
• the composition according to the invention comprises at least one nonionic surfactant.
• composition according to the invention may comprise at least one lipophilic UV screening agent. Said filter is dissolved in the oily phase.
• said UV filter is chosen from mineral UV filters, organic UV filters and mixtures thereof.
• mineral UV screening agent mention may be made of cerium oxide, titanium dioxide (TiO2), zinc oxide or their mixtures, preferably titanium dioxide (TiO2), zinc oxide or their mixtures.
• the mineral UV filter can be functionalized by a surface treatment, for example with a surfactant or else with a metal oxide (in particular silica or alumina), to give it different properties.
• organic UV filter mention may be made of any authorized organic UV filter.
• the organic UV screening agents that can be used according to the present invention are chosen from benzylidene camphor derivatives, benzophenone derivatives, para-aminobenzoic acid and its derivatives, triazine derivatives, dibenzoylmethane derivatives, salicylic derivatives , cinnamic derivatives, p,p-diphenylacrylate derivatives, phenyl benzimidazole derivatives, phenyl benzotriazole derivatives and benzalmalonate derivatives.
• the organic UV filter is chosen from camphor benzalkonium methosulfate, ethylhexyl methoxycinnamate, homosalate, para-aminobenzoic acid, isoamyl p-methoxycinnamate, PEG-25 PABA, ethylhexyl dimethyl PABA ( or padimate O), octocrylene, anisotriazine, polysilicone-15, drometrizole trisiloxane, oxybenzone (or benzophenone-3), terephthalylidene sulfonic acid dicamphre (or ecamsule), benzylidene sulfonic acid dicamphre, polyacrylamidomethyl benzylidene dicamphre, octyl triazone (or ethylhexyl triazone), butyl methoxydibenzoylmethane (BMDBM or avobenz
• the composition according to the invention comprises at least one lipophilic UV screening agent chosen from organic UV screening agents.
• the composition according to the invention comprises at least one lipophilic UV screening agent chosen from mineral UV screening agents, preferably from TiO2 and cerium oxide, advantageously TiO2.
• the water-soluble lignin according to the invention exhibits a synergistic effect with a mineral anti-UV filter of the TiO2 or cerium oxide type, preferably with a mineral anti-UV filter of TiO2 type.
• the UV filter(s) is (are) present in an amount ranging from 1% to 20% by weight relative to the total weight of the composition, preferably 2% to 15% by weight, preferably 5% to 12% by weight.
• composition according to the invention may comprise at least one dyestuff.
• the dyestuff is chosen from pigments, nacres and fat-soluble dyes.
• the pigments are preferably chosen from zirconium or cerium oxides, iron or chromium oxides, in particular red iron oxide, yellow iron oxide, brown iron oxide, iron oxide black, manganese violet, ultramarine blue, curcumin, beta-carotene, chlorophyll, chromium hydrate and ferric blue, and mixtures thereof.
• the nacres are preferably chosen from borosilicates or mica, natural or synthetic, and optionally covered with titanium oxide (TiC>2), iron oxide (Fe20s) (red, yellow or black), oxide chromium (Cr 2 0s) or a mixture of these oxides.
• the fat-soluble dyes are preferably chosen from quinolines, anthraquinones, triarylmethanes, xanthenes, cyanines, phthalocyanines, nitroso, azo and indigoid dyes.
• step a 2g of kraft lignin, purchased from Sigma-Aldrich under the reference (370959) are taken up in 100mL of 50mM borate pH9 buffer (step a).
• step c 5.2 mg of Bacillus pumilus BOD are then added to this solution, then the latter is placed at 60° C. with stirring with a magnetic bar at 100 rpm and bubbling with compressed air at 0.1 L.min - 1 , for 16 hours (step c).
• the solution is then dialyzed in a dialysis tube of 100 mL of 10 kDa, in three baths of 4 L of mQ water, the first of 2 hours, the second of 4 hours and the third for the night (step d).
• the solution is centrifuged for 5 minutes at 1500 rpm.
• the supernatant containing the water-soluble lignin according to the invention is freeze-dried overnight and stored at room temperature.
• a reference sunscreen (P2) used for calibrating in vivo tests for measuring sun protection factors (SPF or Sun Protection Factors - SPF) is used here as a formula base for testing the effectiveness of lignin (see table 1).
• the measurement of the SPF is carried out in vitro using molded PMMA substrates with a roughness Ra ⁇ 4pm (HelioScreen Labs, HELIOPLATE HD6).
• the various formulations are then spread on these polymer supports in accordance with the protocol of the ISO 24443 standard (In vitro determination of UVA photoprotection).
• 1.3 mg/cm 2 of product is then deposited in the form of uniform drops and distributed symmetrically on the substrate.
• the spreading then continues with small circular movements with the index finger for less than 30 seconds before reproducing back and forth horizontal movements.
• the samples are then put in the dark and left to dry for 2 hours. Their transmittance is then measured using a spectrophotometer fitted with an integrating sphere.
• the SPF is finally calculated using the following equation:
• Table 3 shows that the addition of 4% by weight of water-soluble lignin according to the invention makes it possible to more than double the value of the SPF (20.9 to 42.2).
• the SPF increases more with the use of water-soluble lignin according to the invention in the continuous aqueous phase than with an addition of commercial lipophilic lignin in the dispersed fatty phase, which underlines the interest of lignin water soluble.
• Additional formulations of P2 comprising 3% by weight of TiO2 instead of the two organic filters (para-amino benzoic acid and oxybenzone) of P2 (see Table 1), and 2%, 4%, 6% or 8% by weight of water-soluble lignin in the aqueous phase, were carried out.
• They include the titanium dioxide (TiO2) mineral filter.
• the water-soluble lignin according to the invention has several indisputable advantages vis-à-vis in particular fat-soluble commercial lignin: 1 - at equal quantity in the formulas, it always provides a significantly higher SPF than commercial lignin;
• water-soluble lignin facilitates the formulation of sunscreen compositions, because it allows the incorporation of a higher quantity of lignin. In particular, it is possible to exceed 10% by weight, which seems impossible with commercial liposoluble lignin incorporated into the dispersed fatty phase (because this causes stability and texture problems); And
• Example 3 Comparison of the transmittance of the water-soluble lignin according to the invention with a chemically treated water-soluble lignin
• composition P2 according to Table 1 of Example 2 without the two organic screening agents, was mixed with 4% by weight of water-soluble lignin according to the invention relative to the total weight of the composition. Said water-soluble lignin according to the invention was obtained according to Example 1. A composition according to the invention is thus obtained.
• Figure 1 illustrates the transmittance spectra obtained with the P2 composition as it is without the two organic filters (“P2 without filter”, comparative), the comparative composition with chemically treated lignin (“P2 without filter + 4% lignin sulfonated comparison”) and the composition according to the invention with enzymatically treated lignin (“P2 without filter + 4% lignin according to the invention”).
• Enzymatic treatment unlike chemical treatment, thus brings unique properties of interest to water-soluble lignin.
• UV absorbance measurements were carried out on a dispersion of CeC>2 nanoparticles, an enzymatic lignin solution and a mixture of the two in order to evaluate the possible synergy of the mixture.
• Figure 2 is a graph representing the evolution of the absorbance of these three solutions as a function of the wavelength. This graph shows that the mixture of the two active ingredients (CeO2-lignin complexes) has a higher absorbance than the two active ingredients taken separately for the same total concentration of active ingredients of 0.05g/l, thus illustrating a synergistic effect between lignin enzymatic and cerium oxide. This makes it possible to reduce the mass concentration of one of the two constituents.

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• 2021
  • 2021-09-22 FR FR2109967A patent/FR3127127B1/fr active Active
• 2022
  • 2022-09-22 US US18/694,176 patent/US20240390255A1/en active Pending
  • 2022-09-22 WO PCT/EP2022/076393 patent/WO2023046842A1/fr not_active Ceased
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