EP4352110A1 - Verfahren zur modifizierung von stärke durch hydrothermische behandlung, durch dieses verfahren erhaltene stärke und verwendungen davon - Google Patents

Verfahren zur modifizierung von stärke durch hydrothermische behandlung, durch dieses verfahren erhaltene stärke und verwendungen davon

Info

Publication number
EP4352110A1
EP4352110A1 EP22735547.6A EP22735547A EP4352110A1 EP 4352110 A1 EP4352110 A1 EP 4352110A1 EP 22735547 A EP22735547 A EP 22735547A EP 4352110 A1 EP4352110 A1 EP 4352110A1
Authority
EP
European Patent Office
Prior art keywords
acid
starch
weight
mixture
gel
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
EP22735547.6A
Other languages
English (en)
French (fr)
Inventor
Alexandra Fregonese
Alexandre EVEILLARD
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.)
Innovi SAS
Original Assignee
Innovi SAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Innovi SAS filed Critical Innovi SAS
Publication of EP4352110A1 publication Critical patent/EP4352110A1/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
    • C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
    • C08L3/02—Starch; Degradation products thereof, e.g. dextrin

Definitions

  • the present invention relates to a process for modifying starch by hydrothermal treatment, the modified starch obtained by this process and its uses.
  • the galenic form of a pharmaceutical composition corresponds to the form given to the latter. It is carefully chosen according to the route of administration, the physico-chemical properties of the active ingredient it contains, the expected action, and the desire to reach a specific site in the body. Other criteria such as patient comfort and age may also be taken into account. Among the most widespread dosage forms, mention may be made of the liquid form and the gel form.
  • liquid forms are that the digestion time is shorter than for solid forms so that they are more quickly absorbed by the body, thus resulting in a rapid and effective release of the active ingredients they contain. contain.
  • they can produce a high amplitude plasma peak sometimes used to allow assimilated molecules to play an effective health role.
  • liquids are not very satiating, they have little effect on the feeling of satiety, and they lead to a reduction in the production of saliva (the mouth time being very short) which can cause hormonal dysfunctions as well as disturbances in the digestive tract. .
  • gel forms are that their residence time in the mouth is longer than that of liquids and therefore the enzymes of saliva have more time to carry out physico-chemical interactions.
  • This pre-digestion phase is more effective.
  • the digestion time is fast because the saliva lowers the viscosity by modifying the rheology of the gel.
  • Its residence time in the stomach is short due to rapid gastric emptying. The molecules of interest are then quickly released in the body and can exercise their properties.
  • the formulation of the gel be chemically compatible with saliva, easily solubilisable with the latter and easily degradable by salivary enzymes, in particular amylase.
  • a first object of the invention relates to a process for modifying starch by hydrothermal treatment comprising the following steps:
  • step (2) heating the mixture obtained in step (1) to a temperature of between 60°C and 120°C preferably for a period of between 5 and 60 minutes with stirring,
  • step (3) cooling the mixture heated in step (2) preferably with stirring to room temperature
  • a second object of the invention relates to the modified starch obtained according to the method as defined above in the form of a gel.
  • a third object relates to a composition
  • a composition comprising:
  • At least one active ingredient preferably in an amount between 0.01 and 90% by weight, more preferably between 1 and 50% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition,
  • At least one additive preferably in an amount between 0.01 and 50% by weight, more preferably between 1 and 40% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition.
  • the invention also relates to the method for preparing the composition as defined above, characterized in that it comprises the following steps:
  • step (3) heating the mixture obtained in step (2) to a temperature of between 60 and 120° C. preferably for a period of between 5 and 60 minutes with stirring, (4) cooling the mixture heated in step (3) preferably with stirring to room temperature, and
  • step (1) the addition of the premix obtained in step (1) during the cooling step (4), preferably when the mixture reaches a temperature between 10°O and 50°O, preferably between 15 'O and 40 q C, more preferably between 20 ' ⁇ and 35 'O, and even more preferably between 25 'O and 30 O, so as to obtain a composition,
  • step (6) optionally adding at least one gelling agent to the composition obtained in step (5).
  • the invention also relates to the use of the modified starch obtained according to the process as defined above, for the preparation of pharmaceutical compositions, food supplement compositions and/or food compositions.
  • a first object of the invention relates to a process for modifying starch by hydrothermal treatment comprising the following steps:
  • step (2) heating the mixture obtained in step (1) to a temperature of between 60°C and 120°C preferably for a period of between 5 and 60 minutes with stirring,
  • step (3) cooling the mixture heated in step (2) preferably with stirring to room temperature
  • “Hydro-thermal treatment” means heat treatment in the presence of water.
  • the method according to the invention makes it possible to obtain a modified starch in the form of a gel.
  • salivary enzymes such as amylase
  • the modified starch obtained according to the process of the invention therefore makes it possible to prepare compositions having improved bioavailability and a higher metabolic outcome compared with existing galenic forms.
  • the method according to the present invention leads to a modification of the structure and organization of the amylose and amylopectin chains of starch and therefore a molecular rearrangement of the latter (the macromolecules of amylose and amylopectin reorganize and adopt a new conformational balance) which leads to a specific gel texture and viscosity while maintaining a high starch concentration. It is both this low viscosity coupled with this starch concentration that will facilitate the subsequent action of the amylase contained in the oral cavity.
  • amylase will rapidly alter the rheology of the resulting modified starch gel by liquefying the specific arrangement of amylose and amylopectin chains. Once swallowed, the gel according to the invention will therefore behave like a liquid.
  • the combined action of the heating temperature and water in the claimed proportions makes it possible to increase the endothermic reactions and therefore to lead to a sufficient modification of the structure and organization of the amylose and amylopectin chains. and molecular rearrangement without burning the starch.
  • This action is also reinforced by the action of the acid, which leads to hydrolysis of the whole, thus reducing the temperature during the heating stage and the duration of the latter. It is these changes in the structure of the starch that will facilitate the subsequent action of amylase.
  • the starch used in step (1) can be a native starch.
  • “native starch” is preferably meant a starch which has not been modified by chemical and/or heat treatment.
  • starch can therefore come from different sources.
  • the starch is selected from the group consisting of corn starch, waxy corn starch, wheat starch, potato starch, pea starch, cassava (tapioca), rice starch, and mixtures thereof, preferably the starch is selected from corn starch, waxy corn starch, or mixtures thereof.
  • the mixture comprises between 55 and 96% by weight of starch, preferably between 60 and 90% by weight, preferably between 65 and 87% by weight and even more preferably between 70 and 77% by weight relative to the total weight of the mixture. or preferably between 55 and 87% by weight and preferably between 55 and 77% by weight relative to the total weight of the mixture.
  • the acid is selected from the group consisting of citric acid, lactic acid, salicylic acid, acid formic acid, acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, paratoluenesulfonic acid, acrylic acid, capric acid, lauric acid, acid tridecyl acid, myristic acid, palmitic acid, stearic acid, behenic acid, ferulic acid, oxalic acid, succinic acid, tartaric acid, malic acid, acid ascorbic acid, and mixtures thereof, more preferably the acid is citric acid.
  • Citric acid can come from lemon juice.
  • the mixture comprises between 3 and 10% by weight of acid, preferably between 4 and 8% by weight, more preferably between 4.5 and 7.5% by weight, and even more preferably between 5 and 7% by weight relative to the total weight of the mixture or preferably between 3 and 5% by weight relative to the total weight of the mixture.
  • the pH of the composition obtained in step (1) is between 1 and 6, preferably between 2 and 5, and even more preferably between 2.5 and 3.5.
  • the mixture comprises between 1 and 35% by weight of water, preferentially between 7 and 25% by weight and even more preferentially between 10 and 20% by weight relative to the total weight of the mixture or preferentially between 10 and 35% by weight and even more preferably between 21 and 35% by weight relative to the total weight of the mixture.
  • the heating step is carried out at a temperature between 60° C. and 120° C., preferably between 70° C. and 110° C. and even more preferably between 80° C. and 100° C. or preferably between 70° C. and 120° C. C and even more preferably between 80 ° C and 120 'O.
  • the heating step is carried out for a period of between 5 and 60 minutes, preferably between 10 and 45 minutes and even more preferably between 20 and 30 minutes or preferably between 5 and 45 minutes and even more preferably between 5 and 30 minutes.
  • the agitation during the heating step is vigorous agitation, preferably of the Turrax® type.
  • vigorous agitation is preferably meant agitation between 1,000 and 10,000 rpm, preferentially between 1,500 and 5,000 rpm and even more preferentially between 2,000 and 3,000 rpm.
  • rpm revolution per minute
  • step (3) the mixture is cooled with stirring to room temperature.
  • room temperature is preferably meant a temperature between 10′O and 50′O, preferably between Id′ ⁇ and 40°C, more preferably between 20′ ⁇ and 35°C, and even more preferably between 25′ ⁇ and 30'W.
  • the stirring during the cooling step is dispersion stirring, preferably of the Turrax® type.
  • a Turrax® type dispersing agitator is a high performance dispersing agitator, preferably a rotor/stator type agitator. Typically, such agitators are used for applications where conventional agitation is not sufficient.
  • the agitation during the cooling step is very vigorous agitation, preferably of the Turrax® type.
  • “Very vigorous agitation” preferably means agitation between 10,000 and 30,000 rpm, preferentially between 15,000 and 28,000 rpm and even more preferentially between 20,000 and 25,000 rpm.
  • dispersion agitation preferably of the Turrax® type, makes it possible to simultaneously agitate, disperse, to homogenize and/or grind any type of mixture including high viscosity mixtures.
  • All the process steps can be carried out under atmospheric pressure. Preferably, no additional pressure is applied when carrying out steps (1) to (4) of the method.
  • the mixture of step (1) does not include other reagents.
  • the mixture prepared in step (1) can consist of 55% and 96% by weight of starch, between 1 and 35% by weight of water, and between 3 and 10% by weight of acid, the percentages being expressed relative to the total weight of the mixture.
  • the method does not include any additional steps.
  • the method according to the invention may consist of steps (1) to (4) as defined previously.
  • the invention also relates to the modified starch obtained according to the process as defined above, characterized in that it is in the form of a gel.
  • the modified starch gel is a physio-absorbable gel.
  • physio-resorbable gel is preferably meant a gel which under physiological conditions (pH, humidity, enzymes, temperature, etc.) breaks down so as to release the compounds it contains.
  • the modified starch gel obtained according to the process as defined above has a viscosity of between 3000 cp (L4 needle speed 200 rpm) and 1200000 cp (L3 needle speed 0.1 rpm), preferably between 250 cp (Aigle L3 speed 50 rpm) and 2500 cp (Aiguille L3 speed 50 rpm).
  • the viscosity of the gel is measured by a viscometer at 25°.
  • the modified starch gel obtained according to the process as defined above has a pH of between 1 and 6, preferably between 2 and 5, and even more preferably between 2.5 and 3.5.
  • the modified starch gel obtained according to the process as defined above has a density of between 0.7 and 1.5, preferably between 0.75 and 1.3, and even more preferably between 0.8 and 1.1.
  • the density of the gel is measured by a densitometer.
  • the invention also relates to a composition
  • a composition comprising:
  • At least one active ingredient preferably in an amount between 0.01 and 90% by weight, more preferably between 1 and 50% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition,
  • At least one additive preferably in an amount between 0.01 and 50% by weight, more preferably between 1 and 40% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition.
  • the total amount of active ingredient is between 0.01 and 90% by weight, more preferably between 1 and 50% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition.
  • the total amount of additives is between 0.01 and 50% by weight, more preferably between 1 and 40% by weight and even more preferably between 5 and 30% by weight relative to the total weight of the composition.
  • composition according to the invention therefore has improved bioavailability and a superior metabolic outcome compared to existing galenic forms.
  • composition according to the invention may also comprise any type of nutrient.
  • composition according to the invention may also comprise water, preferably in an amount sufficient to reach 100% by weight.
  • active ingredients include, but are not limited to, Devil's Claw extracts such as Devil's Claw root extracts, turmeric and its extracts, glucosamine, vitamin b12 (cobalamin), vitamin b9 (acid folate), vitamin b6 such as pyridoxamine, calcium lactate, ashwagandha extracts, Schizandra flower and/or fruit extracts, magnesium chloride, rhodiola extracts such as rhodiola root extracts ( Rhodiola Rosea), melatonin, extracts of Angelica archangelica such as extracts of the root of Angelica archangelica (angelica), extracts of passionflower, extracts of lemon balm and in particular the soluble leaf of lemon balm, and mixtures thereof.
  • the at least one additive is chosen from flavorings, colorants, gelling agents or other texture agents, sugars, sweeteners, preservatives, and mixtures thereof.
  • flavors include, but are not limited to, lemon flavor, mint flavor, blackcurrant flavor, caramel flavor, white tea flavor, anise, licorice flavor, glutamate, and mixtures thereof.
  • colorants include, but are not limited to, natural or synthetic colorants such as, for example, spirulina.
  • gelling agents or other texturizing agents include, but are not limited to, xanthan, alginate, pectins, carrageenans, carob, guar, and mixtures thereof.
  • sugars include, but are not limited to, glucose, fructose, sucrose, maltose, lactose, and mixtures thereof. Powdered sugar can be used.
  • sweeteners include, but are not limited to, sorbitol, mannitol, acesulfame potassium, aspartame, cyclamic acid and its salts such as calcium cyclamate, potassium cyclamate and sodium cyclamate, isomalt such as hydrogenated isomaltulose, saccharin such as potassium saccharin, sodium saccharin or calcium saccharin, sucralose such as trichlorogalactosucrose, alitame, thaumatin, liquorice such as glycyrrhizic acid, neohesperidin dihydrochalcone, steviol glycosides, neotame, aspartame, acesufane or their salts such as aspartame-acesulfame salt, tagatose, polyglycitol syrup, maltitol, lactitol, xylitol, erythritol, and mixtures thereof.
  • preservatives include, but are not limited to, glycerin, potassium sorbate, sodium benzoate, and mixtures thereof.
  • the composition is a pharmaceutical composition, a food supplement composition or a food composition.
  • the invention also relates to a method for preparing the composition as defined above, characterized in that it comprises the following steps:
  • step (3) heating the mixture obtained in step (2) to a temperature of between 60 and 120°C preferably for a period of between 5 and 60 minutes with stirring,
  • step (3) (4) cooling the mixture heated in step (3) preferably with stirring to room temperature
  • step (1) the addition of the premix obtained in step (1) during the cooling step (4), preferably when the mixture reaches a temperature between 1 O' ⁇ and 50 O, preferably between I of ⁇ and 40 q C, more preferentially between 20 'C and 35 'C, and even more preferentially between 25 'C and 30 O, so as to obtain a composition
  • step (6) optionally adding at least one gelling agent to the composition obtained in step (5).
  • the gelling agents are added only during step (6).
  • the invention also relates to the use of the modified starch obtained according to the process as defined above, for the preparation of pharmaceutical compositions, food supplement compositions and/or food compositions.
  • FIG 1 Photograph of the comparative gel (left) and of the gel obtained according to the process of the invention (right)
  • Figure 2 Photograph of the flows of the comparative gel (left) and of the gel obtained according to the process of the invention (right) with an angle of inclination of 45°.
  • Figure 3 Photograph of the comparative gel (left) and of the gel obtained according to the method of the invention (right) after being brought into contact with saliva for 2 minutes at 37°C.
  • Figure 4 Photograph of the flows of the comparative gel (left) and of the gel obtained according to the method of the invention (right) with an angle of inclination of 45° after contact with saliva for 2 minutes at 37 q C .
  • Figure 5 Photograph of the flows of the comparative gel (left) and of the gel obtained according to the method of the invention (right) with an angle of inclination of 75° after contact with saliva for 2 minutes at 37 q C .
  • Example 1 Process for preparing a starch gel
  • a gel according to the invention was prepared as follows:
  • a mixture comprising 60% by weight of starch, 35% by weight of water and 5% by weight of citric acid (the percentages being expressed relative to the total weight of the composition) was prepared.
  • the mixture was then heated at 120 ⁇ for 10 minutes with vigorous stirring at 2000 rpm using the IKA Ultra-Turrax® apparatus.
  • the mixture was then cooled to room temperature with very vigorous stirring at 25,000 rpm using the IKA Ultra-Turrax® apparatus in order to obtain a gel.
  • the gel behaves like a liquid.
  • the comparative gel has physico-chemical properties identical to the gel obtained according to the method of the invention (viscosity, pH, density).
  • the two gels have the same physico-chemical characteristics, their behavior differs after contact with saliva for 2 minutes at 37 q C.
  • the gel obtained according to the method of the invention exhibits perfect and spontaneous miscibility with saliva, whereas the comparative gel does not succeed in mixing correctly with saliva despite the time and the heat and pressure applied.
  • the comparative gel unlike the gel according to the invention
  • the salivary enzymes will have difficulty in initiating the first phases of digestibility.
  • the two gels were each brought into contact with saliva for 2 minutes at 37°O and then exposed to a 45° tilt for 3 seconds.
  • FIG. 4 The photograph of the two gels after having been brought into contact with saliva for 2 minutes at 37° C. followed by an inclination at 45° for 3 seconds is presented in FIG. 4 (comparative gel on the left and gel according to the invention on the right).
  • the comparative gel exhibits almost zero flow without any miscibility with the saliva which flows separately from the comparative gel.
  • the two gels were each brought into contact with saliva for 2 minutes at 37°O and then exposed to a 75° tilt for 3 seconds.
  • FIG. 5 The photograph of the two gels after having been brought into contact with saliva for 2 minutes at 37° C. followed by an inclination at 75° for 3 seconds is presented in FIG. 5 (comparative gel on the left and gel according to the invention on the right).
  • the comparative gel remains en bloc in the upper part, shows no flow and does not dissolve, the saliva dissociates from the gel and flows independently.
  • the gel obtained according to the method of the invention flows homogeneously and at the same speed as human saliva.
  • the gel obtained according to the process of the invention dissolves in a few seconds on contact with the oral cavity and its environment (heat, humidity, pressure exerted between the tongue and the palate, saliva etc.), is compatible with the components of saliva and is sensitive to the action of the enzymes contained in the latter.
  • Example 3 Comparison of a starch gel obtained according to the invention and a starch gel obtained without stirring during the cooling step (comparative)
  • a gel according to the invention was prepared according to the protocol of example 1.
  • the gel obtained according to the process of the invention (on the left) has the desired physico-chemical properties while the comparative gel (on the right) is in an almost solid form (a thick and lumpy paste is obtained) and does not have not the desired physico-chemical properties.
  • Example 4 Compositions comprising the starch gel obtained according to the invention
  • compositions For each of these compositions, a mixture comprising starch, water and citric acid was heated at 120°C for 10 minutes with vigorous stirring at 2000 rpm using the IKA Ultra-Turrax® device. . The mixture was then cooled to room temperature with very vigorous stirring at 25,000 rpm using the IKA Ultra-Turrax® apparatus to obtain a gel.
  • a premix comprising the other constituents (except the gelling agents if present) was then added to the gel obtained previously at 25 ⁇ G with vigorous stirring at 2000 rpm using the IKA Ultra-Turrax® device.
  • the optional gelling agents such as xanthan and alginate were then added to the previous composition at 25 G with vigorous stirring at 2000 rpm using the IKA Ultra-Turrax® device.
  • the starch gel obtained according to the method of the invention facilitates the delivery of the active substances contained in the compositions, participates in the plasma peak necessary for the activity of the principles active ingredients, improves metabolic fate and significantly increases the health potential of ingested substances.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
EP22735547.6A 2021-06-07 2022-06-07 Verfahren zur modifizierung von stärke durch hydrothermische behandlung, durch dieses verfahren erhaltene stärke und verwendungen davon Pending EP4352110A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2105986A FR3123652B1 (fr) 2021-06-07 2021-06-07 Procede de modification d’amidon par traitement hydro-thermique, amidon obtenu par ce procede et ses utilisations
PCT/FR2022/051078 WO2022258919A1 (fr) 2021-06-07 2022-06-07 Procede de modification d'amidon par traitement hydro-thermique, amidon obtenu par ce procede et ses utilisations

Publications (1)

Publication Number Publication Date
EP4352110A1 true EP4352110A1 (de) 2024-04-17

Family

ID=76807848

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22735547.6A Pending EP4352110A1 (de) 2021-06-07 2022-06-07 Verfahren zur modifizierung von stärke durch hydrothermische behandlung, durch dieses verfahren erhaltene stärke und verwendungen davon

Country Status (3)

Country Link
EP (1) EP4352110A1 (de)
FR (1) FR3123652B1 (de)
WO (1) WO2022258919A1 (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10007061A1 (de) * 2000-02-16 2001-09-06 Aventis Cropscience Gmbh Verfahren zur Herstellung von säuremodifizierter Stärke

Also Published As

Publication number Publication date
FR3123652B1 (fr) 2023-06-16
FR3123652A1 (fr) 2022-12-09
WO2022258919A1 (fr) 2022-12-15

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