EP4623032A2 - Colorants méthiniques thermostables - Google Patents

Colorants méthiniques thermostables

Info

Publication number
EP4623032A2
EP4623032A2 EP23808788.6A EP23808788A EP4623032A2 EP 4623032 A2 EP4623032 A2 EP 4623032A2 EP 23808788 A EP23808788 A EP 23808788A EP 4623032 A2 EP4623032 A2 EP 4623032A2
Authority
EP
European Patent Office
Prior art keywords
formula
substituted
amino
methylbenzaldehyde
mol
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
EP23808788.6A
Other languages
German (de)
English (en)
Inventor
Hans-Ulrich Borst
Frank Linke
Sabine Schmauser
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.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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 Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP4623032A2 publication Critical patent/EP4623032A2/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—Dyes
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides

Definitions

  • the present invention relates to substituted 4-amino-6-methylbenzaldehyde derivatives of
  • R 1 and R 2 are the same or different and each represent optionally substituted alkyl
  • R 3 to R 7 are the same or different and each represent hydrogen, halogen, cyano, optionally substituted alkyl or optionally substituted alkoxy, as novel yellow methine dyes, processes for their preparation and their use for coloring plastics.
  • the mass coloring of synthetic polyamides places higher demands on the colorants used than the mass coloring of other plastics.
  • the melting points of synthetic polyamides are significantly higher and the chemical reactivity of the melted polyamides, especially polyamide 6.6, is also significantly greater, so that the heat stability of the colorants used must be extremely good. There are few colorants that meet these high requirements, especially when high light resistance is also required.
  • EP-A 0225553 describes azo color lakes that can be used to color polyamide in yellow shades.
  • the use of Pigment Yellow 192 is also known.
  • EP-A 0074515 discloses nickel azobarbituric acid complexes that can also be used to produce yellow colorations of polyamide. Although these known pigments have good thermal stability, they cannot be used to produce transparent colors for plastics. Pigments can also impair the mechanical properties of the polymers.
  • a well-known soluble yellow dye is Solvent Yellow 93 (C.l. 48160; CAS No. 4702-90-3)), both from the class of methine dyes, but with two 3H-pyrazol-3-one groups in the molecule.
  • JP S61 270747 A describes photopolymerizable compositions with high sensitivity to laser beams and uses 1-cyano-2-(P-dialkylaminophenyl)ethylene derivatives and 1-cyano-4-(P-dialkylaminophenyl)-1,3-butadiene derivatives as photoinitiator or as photoinitiator system.
  • R 1 and R 2 are the same or different and each represent optionally substituted alkyl, and phenylacetonitrile derivatives of the formula (III)
  • the present invention relates to substituted 4-amino-6-methylbenzaldehyde derivatives or dyes of the formula (I) wherein
  • R 1 and R 2 are the same or different and each represent optionally substituted alkyl
  • R 3 to R 7 are the same or different and each represent hydrogen, halogen, cyano, optionally substituted alkyl or optionally substituted alkoxy.
  • the invention also relates to the use of substituted 4-amino-6-methylbenzaldehydes of the formula (II) wherein
  • alkoxy radicals mentioned are in particular methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy, iso-butoxy and tert-butoxy, each of which may be mono- or polysubstituted by identical or different substituents.
  • Halogen in the meaning of R 3 to R 6 stands in particular for fluorine and chlorine.
  • Preferred are substituted 4-amino-6-methylbenzaldehyde derivatives of the formula (I) and their use as thermostable dyes, in which R 1 and R 2 independently of one another represent unsubstituted C 1 -C 4 alkyl or represent C 1 - C 4 alkyl which is substituted by a phenoxy or naphthoxy radical which is optionally mono- or disubstituted by identical or different substitution, and R 3 to R 7 independently of one another represent hydrogen, halogen, cyano, unsubstituted C 1 - C 4 alkyl or C 1 -C 4 alkyl which is mono- to tri-substituted by identical or different substitution by halogen, unsubstituted C 1 -C 4 alkoxy or C 1 -C 4 alkoxy which is mono- to tri-substituted by identical or different substitution by halogen.
  • thermostable dyes in which R 1 is methyl, ethyl, n-propyl or isopropyl, R 2 represents methyl, ethyl, n-propyl or iso-propyl or represents methyl, ethyl, n-propyl or iso-propyl, each of which is monosubstituted by a radical of the formula wherein
  • R 8 is methyl, ethyl, n-propyl, iso-propyl, cyclopentyl, cyclohexyl or phenyl,
  • R 9 represents hydrogen, methoxy or ethoxy
  • R 3 represents hydrogen, fluorine or chlorine
  • R 4 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl
  • R 6 stands for hydrogen
  • R 2 represents methyl or ethyl or represents methyl or ethyl, each of which is monosubstituted by a radical of the formula wherein
  • R 8 is methyl, ethyl, n-propyl, iso-propyl, cyclohexyl or phenyl, and
  • R 3 represents hydrogen, fluorine or chlorine
  • R 4 represents hydrogen, fluorine, chlorine, or trifluoromethyl
  • R 5 represents hydrogen, fluorine, chlorine or methoxy
  • R 6 stands for hydrogen
  • the dyes of formula (I) according to the invention can be used to achieve yellow colourings of plastics, in particular of polyamides, which surprisingly are distinguished by improved light fastness and improved thermal stability compared to the known yellow dyes used for these purposes.
  • the dyes according to the invention make it possible to meet the demand for high-quality yellow dyes that absorb in the short-wave spectral range.
  • the subject matter also relates to the use of the substituted 4-amino-6-methylbenzaldehyde derivatives of the formula (I) for the mass coloring of plastics, whereby mass coloring is understood in particular to mean processes in which the dye is incorporated into the molten plastic mass, in particular with the aid of an extruder, or in which the substituted 4-amino-6-methylbenzaldehyde derivative of the formula (I) is already added to the starting materials for producing the plastic, in particular to the monomers before polymerization.
  • the plastics to be colored can be present individually or in mixtures with one another, as plastic masses or melts.
  • substituted 4-amino-6-methylbenzaldehyde derivatives of the formula (I) according to the invention are surprisingly resistant to polymerization catalysts, in particular peroxides, it is also possible to add them to the monomeric starting materials for the production of plastics, e.g. polymethyl methacrylate (PMMA) and then to polymerize them in the presence of polymerization catalysts.
  • PMMA polymethyl methacrylate
  • these are preferably dissolved in the monomeric components or intimately mixed with them.
  • the substituted 4-amino-6-methylbenzaldehyde derivatives of the formula (I) according to the invention are preferably used for dyeing the plastics mentioned, in particular polyamide, in amounts of 0.0001 to 1 wt.%, in particular 0.01 to 0.5 wt.%, based on the amount of polymer.
  • titanium dioxide By adding pigments that are insoluble in the polymers, especially titanium dioxide, corresponding valuable muted colors can be obtained.
  • titanium dioxide can be present in an amount of 0.01 to 10% by weight, preferably 0.1 to 5% by weight, based on the amount of polymer.
  • the present invention further relates to a process for the mass coloring of plastics, wherein at least one substituted 4-amino-6-methylbenzaldehyde derivative of the formula (I) is dry mixed or ground with at least one plastic, preferably in granulate form, and this mixture is plasticized and homogenized, for example on mixing rollers or in screws.
  • the material pre-colored in this way can then preferably be further processed into bristles, threads, etc. by spinning or by extrusion or injection molding into molded parts.
  • plastic compositions according to the invention very particularly preferably contain at least one polyamide, in particular polyamide 6.6 and/or polyamide 6.
  • thermoplastic in finely distributed form, preferably in the form of granules.
  • the plastic compositions according to the invention preferably contain titanium dioxide in an amount of 0.01 to 10 wt. %, preferably 0.1 to 5 wt. %, based on the amount of thermoplastics.
  • plastic compositions according to the invention can be produced in a known manner, for example by mixing or grinding at least one thermoplastic, preferably in granulate form, with at least one substituted 4-amino-6-methylbenzaldehyde derivative of the formula (I).
  • the present invention further relates to a process for preparing the substituted 4-amino-6-methylbenzaldehyde derivatives of formula (I) according to the invention.
  • the substituted 4-amino-6-methylbenzaldehyde derivatives of the formula (I) according to the invention can be prepared in a manner known per se by reacting at least one substituted 4-amino-6-methylbenzaldehyde of the formula (II) wherein R 1 and R 2 have the general and preferred meanings given for formula (I), with at least one phenylacetonitrile derivative of formula (III) wherein
  • the process according to the invention for preparing the dyes of the formula (I) by reacting substituted 4-amino-6-methylbenzaldehydes of the formula (II) with the phenylacetonitrile derivatives of the formula (III) can be carried out in a manner known per se.
  • the process according to the invention can be carried out in the presence of at least one solvent.
  • Suitable solvents are, for example, those from the series of alcohols and formamides.
  • the process for preparing the dyes (I) according to the invention is preferably carried out in the presence of at least one alcohol from the series methanol, ethanol, propanol, and/or at least one formamide from the series dimethylformamide and diethylformamide, particularly preferably in the presence of methanol and/or dimethylformamide.
  • the process according to the invention can be carried out in the presence of at least one base.
  • Suitable bases are, for example, alkali metal hydroxides and alkali metal alcoholates. Preference is given to using lithium hydroxide, sodium hydroxide, potassium hydroxide and/or potassium tert-butoxide, particularly preferably sodium hydroxide and/or potassium tert-butoxide.
  • the phenylacetonitrile derivatives of formula (III) are known and can be obtained, for example, as commercial products from Alfa Aesar.
  • Compounds of formula (III) preferred for carrying out the process according to the invention are 3-(trifluoromethyl)phenylacetonitrile, 4-methoxyphenylacetonitrile, 2,6-dichlorophenylacetonitrile, 2,4-chlorophenylacetonitrile, 3,4-chlorophenylacetonitrile, 2-fluorophenylacetonitrile, 3-chlorophenylacetonitrile, 3-fluorophenylacetonitrile, 4-chlorophenylacetonitrile and 4-fluorophenylacetonitrile.
  • Preferred formamides are dimethylformamide, diethylformamide and dibutylformamide.
  • Preferred phosphoric acid chloride is phosphorus oxychloride.
  • the process for preparing the compounds (II) is conveniently carried out at ambient pressure, but the reaction can also be carried out in the range from 1000 to 10000 hPa, preferably 10 to 5000 hPa.
  • Ambient pressure is understood to mean an air pressure in the range from about 925 hPa to 1070 hPa.
  • a mixture of dimethylformamide and phosphorus oxychloride is particularly preferably used as the formylation reagent.
  • Example 2 instead of the aldehyde used in Example 1, 16.3 g (0.1 mol) of the aldehyde of formula (II-b) prepared according to Example B) were used and instead of 3-(trifluoromethyl)phenylacetonitrile, 18.6 g (0.1 mol) of 3,4-dichlorophenylacetonitrile were used.
  • Example 2 instead of the aldehyde used in Example 1, 16.3 g (0.1 mol) of the aldehyde of formula (II-b) prepared according to Example B) were used and instead of 3-(trifluoromethyl)phenylacetonitrile, 13.5 g (0.1 mol) of 3-fluorophenylacetonitrile were used.
  • Example 2 instead of the aldehyde used in Example 1, 16.3 g (0.1 mol) of the aldehyde of formula (II-b) prepared according to Example B) were used and instead of 3-(trifluoromethyl)phenylacetonitrile, 15.2 g (0.1 mol) of 4-chlorophenylacetonitrile were used.
  • Example 2 instead of the aldehyde used in Example 1, 16.3 g (0.1 mol) of the aldehyde of formula (II-b) prepared according to Example B) were used and instead of 3-(trifluoromethyl)phenylacetonitrile, 13.5 g (0.1 mol) of 4-fluorophenylacetonitrile were used.
  • step a 310 g (4.24 mol) of dimethylformamide were added dropwise to the organic phase obtained in step a).
  • 160 g (1.04 mol) of phosphorus oxychloride were then added over the course of 3 hours at a temperature of 60 °C.
  • the reaction mixture was then stirred for 5 hours. It was then cooled to 20 °C and 160 g of methanol and 400 g of water were added.
  • a pH of approx. 8 was then adjusted by adding a 50% aqueous sodium hydroxide solution.
  • the reaction mixture was left to stand for 4 hours until phase separation had occurred.
  • the aqueous phase was then separated off. Any remaining water was removed from the organic phase under vacuum at 80 °C and 2000 Pa.
  • a sample was produced at 240 °C with a residence time in the screw of 2.5 minutes.
  • the samples to be determined were coloristically evaluated against this standard sample, which were prepared at a residence time of 5 minutes and temperatures of 240-320 °C. Samples with a total color deviation of DE ⁇ 3.0 were considered stable at the temperature used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne des dérivés de 4-amino-6-méthylbenzaldéhyde substitués de formule (I) dans laquelle R1 et R2 sont identiques ou différents et représentent dans chaque cas alkyle éventuellement substitué, et et R3 bis R7sont identiques ou différents et représentent dans chaque cas hydrogène, halogène, cyano, alkyle éventuellement substitué ou alcoxy éventuellement substitué, comme nouveaux colorants méthiniques jaunes, leur procédé de préparation et leur utilisation pour assurer la coloration de matières plastiques.
EP23808788.6A 2022-11-24 2023-11-17 Colorants méthiniques thermostables Pending EP4623032A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22209278 2022-11-24
PCT/EP2023/082183 WO2024110327A2 (fr) 2022-11-24 2023-11-17 Colorants méthiniques thermostables

Publications (1)

Publication Number Publication Date
EP4623032A2 true EP4623032A2 (fr) 2025-10-01

Family

ID=84361889

Family Applications (1)

Application Number Title Priority Date Filing Date
EP23808788.6A Pending EP4623032A2 (fr) 2022-11-24 2023-11-17 Colorants méthiniques thermostables

Country Status (6)

Country Link
EP (1) EP4623032A2 (fr)
JP (1) JP2025537918A (fr)
KR (1) KR20250113458A (fr)
CN (1) CN120265610A (fr)
MX (1) MX2025005845A (fr)
WO (1) WO2024110327A2 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3215875A1 (de) 1981-09-02 1983-03-17 Bayer Ag, 5090 Leverkusen Azobarbitursaeure-derivate, ihre festen loesungen, einschlussverbindungen und interkalationsverbindungen
JPS61270747A (ja) 1985-05-24 1986-12-01 Toyobo Co Ltd 光重合性組成物
DE3543512A1 (de) 1985-12-10 1987-06-11 Bayer Ag Azofarblacke

Also Published As

Publication number Publication date
WO2024110327A3 (fr) 2024-07-18
KR20250113458A (ko) 2025-07-25
MX2025005845A (es) 2025-06-02
JP2025537918A (ja) 2025-11-20
CN120265610A (zh) 2025-07-04
WO2024110327A2 (fr) 2024-05-30

Similar Documents

Publication Publication Date Title
EP3470467B1 (fr) Colorants methine pour colorer les plastiques
EP3470471B1 (fr) Colorants méthyne
EP3508536B1 (fr) Colorants méthyne pour la teinture dans la masse de polyamides synthetiques
EP0133156B1 (fr) 1,4-Dicétopyrrolo-(3,4-c)-pyrroles
EP3470472B1 (fr) Nouveaux colorants méthyne
EP3247749B1 (fr) Colorants au méthyle jaunes
EP3489229A1 (fr) Nouveaux colorants méthyne
DE10140107B4 (de) Verfahren zur Herstellung von 1-Amino-4-hydroxyanthrachinonen
EP1239009B1 (fr) Procédé pour la préparation de colorants méthines asymétriques
EP4623032A2 (fr) Colorants méthiniques thermostables
WO2024110325A1 (fr) Colorants méthiniques jaunes et leur utilisation pour la coloration des plastiques
EP3489218B1 (fr) Procédé de préparation de phényl amino hydroxyanthraquinones
DE69708905T2 (de) Verfahren zum färben von hochmolekularem organischem material und polycyclische pigmente
WO2024110326A1 (fr) Utilisation de colorants méthines thermostables jaunes pour colorer des matières plastiques
EP0168343A2 (fr) Complexes métalliques, procédé pour leur préparation et leur utilisation pour la coloration de matières organiques à haut poids moléculaire
EP2039728B1 (fr) Mélange de couleur rouge
EP1293538B1 (fr) Procédé de préparation de colorants styryliques
EP0163609A2 (fr) Procédé pour teindre un matériau organique de haut poids moléculaire, composés polycycliques et leur préparation
EP0442846A2 (fr) Composés disazoiques avec groupes ester ou amide alkyliques à longue chaîne
DE2441924C3 (de) Disazopigmentfarbstoffe
DE4433438A1 (de) Massefärben von Kunststoffen
EP0354178A1 (fr) Matières thermoplastiques contenant un pigment de complexe métallique
EP0465421A1 (fr) Composés d'isoindolinone ayant des groupes alkylthioéther à longue chaîne
EP0864566A2 (fr) Procédé pour la préparation d'hydroxynaphtalènes
DE102008023114A1 (de) Rote Farbstoffmischung

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20250624

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)