FR3125064B1 - Procédé biologique d’obtention de monomères comprenant une insaturation éthylénique par bioconversion d’un composé biosourcé comprenant au moins une fonction nitrile - Google Patents
Procédé biologique d’obtention de monomères comprenant une insaturation éthylénique par bioconversion d’un composé biosourcé comprenant au moins une fonction nitrile Download PDFInfo
- Publication number
- FR3125064B1 FR3125064B1 FR2107485A FR2107485A FR3125064B1 FR 3125064 B1 FR3125064 B1 FR 3125064B1 FR 2107485 A FR2107485 A FR 2107485A FR 2107485 A FR2107485 A FR 2107485A FR 3125064 B1 FR3125064 B1 FR 3125064B1
- Authority
- FR
- France
- Prior art keywords
- compound
- bioconversion
- biological process
- biosourced
- ethylenic unsaturation
- 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.)
- Active
Links
- 230000031018 biological processes and functions Effects 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 239000000178 monomer Substances 0.000 title abstract 2
- 150000002825 nitriles Chemical group 0.000 title abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- MMOPHTBJNNBLFU-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-piperidin-1-ylpropan-1-one Chemical compound C1=CC(F)=CC=C1C(=O)CCN1CCCCC1 MMOPHTBJNNBLFU-UHFFFAOYSA-N 0.000 abstract 1
- 239000011942 biocatalyst Substances 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2652—Nitrogen containing polymers, e.g. polyacrylamides, polyacrylonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
- C07C57/04—Acrylic acid; Methacrylic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/42—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells
- C09K8/46—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement
- C09K8/467—Compositions for cementing, e.g. for cementing casings into boreholes; Compositions for plugging, e.g. for killing wells containing inorganic binders, e.g. Portland cement containing additives for specific purposes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y305/00—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
- C12Y305/01—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in linear amides (3.5.1)
- C12Y305/01004—Amidase (3.5.1.4)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y402/00—Carbon-oxygen lyases (4.2)
- C12Y402/01—Hydro-lyases (4.2.1)
- C12Y402/01084—Nitrile hydratase (4.2.1.84)
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
- D21H17/45—Nitrogen-containing groups
- D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Materials Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Ceramic Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne un procédé biologique d’obtention d’un monomère MO comprenant une insaturation éthylénique par bioconversion d’un composé CN comprenant au moins une fonction nitrile, ledit composé CN étant au moins en partie d’origine renouvelable et non fossile, ledit procédé biologique comprenant au moins une étape de bioconversion par voie enzymatique du composé CN en présence d’un biocatalyseur comprenant au moins une enzyme.
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2107485A FR3125064B1 (fr) | 2021-07-09 | 2021-07-09 | Procédé biologique d’obtention de monomères comprenant une insaturation éthylénique par bioconversion d’un composé biosourcé comprenant au moins une fonction nitrile |
US18/565,838 US20240263201A1 (en) | 2021-07-09 | 2022-07-08 | Biological method for obtaining monomers comprising an ethylenic unsaturation by bioconversion of a bio-sourced compound comprising at least one nitrile function |
BR112023024089A BR112023024089A2 (pt) | 2021-07-09 | 2022-07-08 | Método biológico para obter um monômero, monômero compreendendo pelo menos uma insaturação etilênica, bio(met)acrilamida obtida pela bioconversão de (met)acrilonitrila, sais de bio(met)acrilato obtidos pela bioconversão de (met)acrilonitrila e (met)acrilamida, polímero, usos de pelo menos um monômero ou de pelo menos uma bio(met)acrilamida ou pelo menos um sal de bio(met)acrilato e do polímero, métodos para a recuperação realçada de óleo e/ou gás pela varredura de uma formação subterrânea, para a fratura hidráulica de reservatórios subterrâneos de óleo e/ou gás, para perfurar e/ou cimentar um poço em uma formação subterrânea, para fabricar uma folha de papel, papelão ou semelhantes, para tratar água municipal e industrial e para tratar uma suspensão de partículas sólidas em água resultante de operações de mineração ou areias betuminosas, e, espessantes para composição cosmética, dermatológica, farmacêutica ou detergente e para composição de pigmento usada na impressão de têxteis |
CN202280039376.6A CN117545847A (zh) | 2021-07-09 | 2022-07-08 | 通过生物转化包含至少一个腈官能团的生物源化合物获得包含烯属不饱和度的单体的生物方法 |
AU2022305832A AU2022305832A1 (en) | 2021-07-09 | 2022-07-08 | Biological method for obtaining monomers comprising an ethylenic unsaturation by bioconversion of a bio-sourced compound comprising at least one nitrile function |
EP22747018.4A EP4367256A2 (fr) | 2021-07-09 | 2022-07-08 | Procédé biologique d'obtention de monomères comprenant une insaturation éthylénique par bioconversion d'un composé bio-sourcé comprenant au moins une fonction nitrile |
PCT/EP2022/069156 WO2023281088A2 (fr) | 2021-07-09 | 2022-07-08 | Procédé biologique d'obtention de monomères comprenant une insaturation éthylénique par bioconversion d'un composé bio-sourcé comprenant au moins une fonction nitrile |
JP2023574535A JP2024524010A (ja) | 2021-07-09 | 2022-07-08 | 少なくとも1つのニトリル官能基を含む生物由来化合物の生物変換によりエチレン性不飽和を含むモノマーを得るための生物学的方法 |
MX2023014390A MX2023014390A (es) | 2021-07-09 | 2022-07-08 | Metodo biologico para la obtencion de monomeros que comprenden una insaturacion etilenica por bioconversion de un compuesto de origen biologico, que comprende al menos una funcion nitrilo. |
CA3219267A CA3219267A1 (fr) | 2021-07-09 | 2022-07-08 | Procede biologique d'obtention de monomeres comprenant une insaturation ethylenique par bioconversion d'un compose bio-source comprenant au moins une fonction nitrile |
KR1020237041501A KR20240033210A (ko) | 2021-07-09 | 2022-07-08 | 적어도 하나의 니트릴 작용기를 포함하는 생물 기원 화합물의 생물전환에 의해 에틸렌성 불포화를 포함하는 단량체를 수득하기 위한 생물학적 방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2107485A FR3125064B1 (fr) | 2021-07-09 | 2021-07-09 | Procédé biologique d’obtention de monomères comprenant une insaturation éthylénique par bioconversion d’un composé biosourcé comprenant au moins une fonction nitrile |
FR2107485 | 2021-07-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
FR3125064A1 FR3125064A1 (fr) | 2023-01-13 |
FR3125064B1 true FR3125064B1 (fr) | 2024-07-12 |
Family
ID=77317144
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR2107485A Active FR3125064B1 (fr) | 2021-07-09 | 2021-07-09 | Procédé biologique d’obtention de monomères comprenant une insaturation éthylénique par bioconversion d’un composé biosourcé comprenant au moins une fonction nitrile |
Country Status (11)
Country | Link |
---|---|
US (1) | US20240263201A1 (fr) |
EP (1) | EP4367256A2 (fr) |
JP (1) | JP2024524010A (fr) |
KR (1) | KR20240033210A (fr) |
CN (1) | CN117545847A (fr) |
AU (1) | AU2022305832A1 (fr) |
BR (1) | BR112023024089A2 (fr) |
CA (1) | CA3219267A1 (fr) |
FR (1) | FR3125064B1 (fr) |
MX (1) | MX2023014390A (fr) |
WO (1) | WO2023281088A2 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3144136A1 (fr) | 2022-12-22 | 2024-06-28 | Snf Sa | Polymere hybride et ses utilisations |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MX67287A (fr) | 1959-02-24 | |||
US4208329A (en) | 1978-07-31 | 1980-06-17 | E. I. Du Pont De Nemours & Co. | Oxazole removed from acrylonitrile as oxazole sulfate |
JP3235966B2 (ja) | 1996-06-20 | 2001-12-04 | 三菱レイヨン株式会社 | ニトリルの精製方法 |
JP3428404B2 (ja) | 1997-10-23 | 2003-07-22 | 三菱レイヨン株式会社 | アミド化合物の製造方法 |
DE19829477A1 (de) | 1998-07-01 | 2000-01-05 | Basf Ag | Verfahren zur Reinigung von Acrylsäure oder Methacrylsäure durch Kristallisation und Destillation |
FR2835531B1 (fr) | 2002-02-06 | 2004-12-03 | Snf Sa | Procede pour la fabrication d'amides en presence d'une nitrile hydratase d'origine microbiologique et nouveau microorganisme |
WO2012164933A1 (fr) | 2011-05-31 | 2012-12-06 | ダイヤニトリックス株式会社 | Nitrile hydratase améliorée |
KR101698709B1 (ko) | 2011-06-07 | 2017-01-20 | 미쯔비시 레이온 가부시끼가이샤 | 개량형 니트릴 히드라타제 |
FR2979821B1 (fr) | 2011-09-13 | 2013-10-25 | Oreal | Procede de traitement cosmetique employant un polymere ethylenique |
US20130274520A1 (en) | 2012-04-11 | 2013-10-17 | The Procter & Gamble Company | Purification Of Bio Based Acrylic Acid To Crude And Glacial Acrylic Acid |
EP2929037B1 (fr) | 2012-12-07 | 2020-09-09 | Global Bioenergies | Procédé de fermentation perfectionné |
BR112015015897A2 (pt) | 2013-01-08 | 2017-07-11 | Shell Int Research | processo para produzir ácido acrílico |
CA2896849A1 (fr) | 2013-01-21 | 2014-07-24 | Total Research & Technology Feluy | Procede de production de bionaphta a partir de melanges complexes de graisses et huiles d'origine naturelle |
FR3024736B1 (fr) | 2014-08-06 | 2016-08-26 | Snf Sas | Utilisation dans des compositions detergentes de polymeres obtenus par polymerisation en emulsion inverse basse concentration avec un faible taux de monomeres neutralises |
CA3116477A1 (fr) * | 2018-10-18 | 2020-04-23 | Basf Se | Procede de production d'acide acrylique ou de sels de celui-ci |
EP3736262A1 (fr) | 2019-05-08 | 2020-11-11 | Basf Se | Procédé de purification d'une solution comprenant un monomère d'acrylamide |
-
2021
- 2021-07-09 FR FR2107485A patent/FR3125064B1/fr active Active
-
2022
- 2022-07-08 CA CA3219267A patent/CA3219267A1/fr active Pending
- 2022-07-08 US US18/565,838 patent/US20240263201A1/en active Pending
- 2022-07-08 EP EP22747018.4A patent/EP4367256A2/fr active Pending
- 2022-07-08 KR KR1020237041501A patent/KR20240033210A/ko unknown
- 2022-07-08 AU AU2022305832A patent/AU2022305832A1/en active Pending
- 2022-07-08 JP JP2023574535A patent/JP2024524010A/ja active Pending
- 2022-07-08 WO PCT/EP2022/069156 patent/WO2023281088A2/fr active Application Filing
- 2022-07-08 CN CN202280039376.6A patent/CN117545847A/zh active Pending
- 2022-07-08 BR BR112023024089A patent/BR112023024089A2/pt unknown
- 2022-07-08 MX MX2023014390A patent/MX2023014390A/es unknown
Also Published As
Publication number | Publication date |
---|---|
WO2023281088A2 (fr) | 2023-01-12 |
MX2023014390A (es) | 2023-12-15 |
BR112023024089A2 (pt) | 2024-02-06 |
EP4367256A2 (fr) | 2024-05-15 |
AU2022305832A1 (en) | 2023-11-16 |
JP2024524010A (ja) | 2024-07-05 |
CA3219267A1 (fr) | 2023-01-12 |
US20240263201A1 (en) | 2024-08-08 |
KR20240033210A (ko) | 2024-03-12 |
CN117545847A (zh) | 2024-02-09 |
FR3125064A1 (fr) | 2023-01-13 |
WO2023281088A3 (fr) | 2023-02-09 |
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