EP4204467A1 - Polymères contenant du fluor - Google Patents

Polymères contenant du fluor

Info

Publication number
EP4204467A1
EP4204467A1 EP21769084.1A EP21769084A EP4204467A1 EP 4204467 A1 EP4204467 A1 EP 4204467A1 EP 21769084 A EP21769084 A EP 21769084A EP 4204467 A1 EP4204467 A1 EP 4204467A1
Authority
EP
European Patent Office
Prior art keywords
block copolymer
composition
monomer
copolymer according
optionally
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
EP21769084.1A
Other languages
German (de)
English (en)
Inventor
Reiner Friedrich
Gregor Larbig
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.)
Merck Patent GmbH
Original Assignee
Merck Patent 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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP4204467A1 publication Critical patent/EP4204467A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • 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
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • 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
    • C08F2438/00—Living radical polymerisation
    • C08F2438/02—Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]

Definitions

  • the present invention relates to novel fluorine containing block copolymers, compositions comprising the block copolymers, the use of the block copolymers in coating compositions, especially as surface-active additives in coating compositions, to compositions comprising such block copolymers and to products coated with such compositions.
  • Fluorosurfactants are an important constituent in industrial process chemicals. Owing to their persistence and toxicity, however, these materials are problematic for users and the environment. Fluorine-containing surfactants can be employed in a very wide variety of applications and contribute, for example, to improved wetting of surfaces. Thus, they are used, for example, as interface promoter or levelling agent, emulsifier or viscosity reducer in paints, coatings or adhesives.
  • fluorosurfactants are built up from long-chain, perfluorinated alkyl chains (C6-C8) and are regarded as potentially bioaccumulative and toxic. In general, however, fluorosurfactants contain perfluoroalkyl substituents, which are broken down in the environment by biological and other oxidation processes to give perfluoroalkanecarboxylic acids and -sulfonic acids.
  • the present invention relates to block copolymers (hereinafter also shortly referred to as “polymers”) comprising at least one first block A and at least one second block B, wherein block A comprises monomer units derived from at least one monomer of formula (I) and block B comprises monomer units derived from at least one monomer of formula (II) (Rf-CHF-CF 2 -Y-CHRi) m -L-Xi (I)
  • Rf is a perfluorinated alkyl group, preferably a perfluorinated C1-C30 alkyl group, very preferably a perfluorinated C1-C15 alkyl group, that optionally contains one or more hetero atoms,
  • Y is 0 or S
  • R1 is H or an alkyl group, preferably a C1-C6 alkyl group,
  • L is a single bond or a bivalent organic group
  • R2 is an alkyl group, preferably a C1-C20 alkyl group that is straightchain, branched, monocyclic or polycyclic and optionally contains one or more hetero atoms,
  • Xi and X 2 are independently of one another an ethylenically unsaturated group, m is an integer from 1 to 5.
  • Rf is selected from the following groups:
  • Rf is selected from the following groups: CF 3 -(CF 2 )I-2- CF 3 -(CF 2 )I-2-O-
  • Ri is selected from H and C1-C3 Alkyl.
  • L is selected from a single bond and a saturated, branched or not branched, optionally hetero atoms, especially 0 and/or S atoms, and/or functional groups containing, organic group, especially an alkylene group.
  • L is methylene, ethylene or propylene, most preferably methylene.
  • R 2 is a C2-C12 alkyl group that is optionally branched and optionally contains one or more hetero atoms.
  • R 2 is a C2, C3, C4, C5 or C6 alkyl group.
  • Xi and X 2 are independently of one another an acrylate or a methacrylate group.
  • mi is 1 , 2 or 3, particularly preferably 1 or 2.
  • polymers comprising monomer units derived from at least one monomer of formulae (I) and at least one monomer of formula (II) wherein one or more of variables have the preferred meaning.
  • polymers comprising monomer units derived from at least one monomer of formula (I) and at least one monomer of formula (II) wherein all of the variables simultaneously have the preferred meaning.
  • Rf is selected from CF 3 -(CF 2 )I- 2 -, CF 3 -(CF 2 )I- 2 -O-, CF 3 -O-(CF 2 )I- 3 -, CF 3 -O- (CF 2 )I.
  • R1 is H or CH 3 ,
  • R2 is a C2-C12 alkyl group that is straight-chain or branched and optionally contains one or more hetero atoms,
  • L is a C1 -C4 alkylene group that is straight-chain or branched and optionally contains one or more hetero atoms, preferably one or more 0 atoms, and optionally contains a functional group,
  • Xi and X2 are independently of one another an acrylate or a methacrylate group, m is 1 or 2.
  • polymers comprising monomer units derived from at least one monomer selected from the following formulae (la) to (Id), especially (la) to (Ic), and/or (Ila).
  • Rf and R2 have one the meanings given above and below, and R’ and R” are independently of one another H or methyl, and preferably R’ and R” have the same meaning.
  • polymers comprising monomer units derived from at least one monomer selected from formulae (la) to (lb) wherein Rf is selected from the following groups:
  • CF 3 -O-(CF 2 -O)I- 8 -CF 2 - and R’ is H or methyl.
  • the polymers comprise monomer units derived from at least one monomer selected from formulae (la) to (lb) wherein Rf is CF 3 -(CF 2 )I. 2 -
  • CF 3 -O-(CF 2 )I. 3 - or CF 3 -O-(CF 2 )i- 2 -O- and R’ is H or methyl.
  • the polymers comprise monomer units derived from at least one monomer selected from formulae (la) to (lb) wherein Rf is CF 3 -CF 2 -CF 2 -O-, CF 3 -CF 2 -O- or CF 3 -O- and R’ is H or methyl.
  • polymers comprising monomer units derived from at least one monomer selected from formula (Ila) wherein R 2 is a straightchain or branched C2-C12 alkyl group, very preferably a C2, C3, C4, C5 or C6 alkyl group, and R’ is H or methyl.
  • polymers comprising monomer units derived from at least one monomer of formula (Ila) selected from the following subformulae wherein R”” is H or methyl and n is an integer from 1 to 6:
  • the monomers of formulae (I) and (II) can be prepared by simple, standard process steps.
  • monomers of formula (I) can be prepared by reaction of corresponding alcohols with acids or acid anhydrides by methods known to the skilled man in the art.
  • Monomers of formula (II) can be prepared for example by reaction of the corresponding alkyl alcohol with the corresponding (meth)acrylic acid or (meth)acrylic acid derivative.
  • Necessary starting materials are commercially available, can be prepared by known processes from commercially available products or can be prepared analogously by known syntheses,
  • the new polymers may comprise solely monomer units derived from at least one monomer of formulae (I) and at least one monomer of formula (II).
  • the new polymers may comprise a first block A comprising monomer units derived from at least one monomer of formulae (I), a second block B comprising monomer units derived from at least one monomer of formula (II), and a optionally a third block C comprising monomer units derived from at least one functional co-monomer.
  • Such polymers may be represented by formula (III) wherein Ra is a fluorinated group (Rf-CHF-CF2-Y-CHR-i) m -L- as defined for the monomers of formula (I), Rb is an alkyl group R2 as defined for the monomers of formula (II), Rc is a functional group as defined below, R’, R” and R’” denote H or methyl, and x, y and z denote the total number of the respective monomers, wherein x>1 , y>1 , z>0.
  • the functional co-monomer of block C is preferably selected from monomers comprising OH, epoxy, -Si(OMe)3,-Si(OEt)3, CO2H or tertiary amino groups.
  • Especially preferred functional co-monomers are selected from the following monomers, wherein R’” is H or methyl:
  • the polymers consist of monomer units derived from at least one monomer of formula (I) and at least one monomer of formula (II).
  • the block copolymer according to the present invention has a number average molecular weight M n from 1000 to 100,000, more preferably from 2000 to 50,000, very preferably from 3,000 to 30,000 g/mol.
  • Balancing the composition of the co-polymer is key to the end performance of the polymer in the final composition or coating.
  • the synthesis of the block copolymers can be accomplished by standard processes that are known to the person skilled in the art and are described in the literature, preferably by radical polymerisation in solution, in bulk or in emulsion.
  • block copolymers are prepared by a process comprising the following steps
  • (d) optionally isolating the polymer. It is also possible to prepare the blocks A, B and C of the block copolymer in another sequence as shown above, by changing the sequence of steps a, b and c accordingly. For example it is possible to first polymerize the functional co-monomer to form block C, and then copolymerize the resulting polymer with the monomers of formula (I) and (II) in two further steps to form blocks A and B.
  • the synthesis of the blocks A, B and/or C is preferably carried out using controlled polymerization reactions, very preferably controlled (free) radical polymerization.
  • controlled polymerization reactions include, without limitation
  • NMP nitroxide mediated polymerization
  • ATRP Very preferred are ATRP and NMP, most preferred is NMP.
  • Suitable nitroxide initiators are known from prior art and are disclosed for example in W02009/103613 A1 .
  • Preferred nitroxide initiators are selected from the following formulae
  • the polymer may be isolated or used in dispersion or solution.
  • the polymerisation is carried out in the same solvents as the later coating dispersion are used. If the solvent is not suitable, a solvent exchange after polymerisation can be carried out.
  • the polymerisation is carried out as a free radical polymerization under inert atmosphere with a thermally activated initiator like AIBN.
  • the polymers according to the invention may be used for example as coating materials or as additives for conventional coatings.
  • polymers according to the invention comprising two or more blocks of monomer units derived from monomers of formula (I) and (II) or their subformulae, in particular in their preferred variants, provide several advantages, like good water and dirt repellencies and beneficial environmental properties, compared with polymers of the prior art. Thus, they do not degrade either chemically or biologically to form long-chain PFCAs or PFASs.
  • a particular advantage of the polymers according to the invention is that they are readily degradable since they have specific nominal breaking points in the molecule. As a consequence, in the degradation process corresponding low-molecular-weight fragments are formed which are able to enter the atmosphere and can thus be decomposed in the stratosphere under UV light.
  • Hydrofluoroethers of the following structure can be converted into readily volatile and UV-decom posable compounds, for example by hydrolysis and oxidation.
  • the decomposition products can then be washed out of the atmosphere with the rain, transferred into the ground and mineralised there.
  • O Preferred areas of use are, for example, the use of the polymers according to the invention as additives in preparations for surface coating, such as paints, lacquers, protective coatings, special coatings in electronic or semiconductor applications (for example photoresists, top antireflective coatings, bottom antireflective coatings) or in optical applications (for example photographic coatings, coatings of optical elements), in agrochemicals, in polishes and waxes, for example for furniture, floorcoverings and automobiles, in particular in floor polishes, in fire-extinguishing compositions, lubricants, or in photolithographic processes, in particular in immersion photolithography processes, for example in developer solutions, rinse solutions, immersion oils and/or in the photoresists themselves, especially for the production of printed circuits or in additive preparations for corresponding preparations.
  • surface coating such as paints, lacquers, protective coatings, special coatings in electronic or semiconductor applications (for example photoresists, top antireflective coatings, bottom antireflective coatings
  • the polymers according to the invention are usually introduced into correspondingly designed preparations. Usual use concentrations are 0.01 - 30.0%, preferably 0.01 - 10.0% by weight of the polymer according to the invention, based on the entire compositions.
  • the present invention likewise relates to corresponding compositions comprising the polymers according to the invention. Such compositions preferably comprise a solvent which is suitable for the respective application, and optionally further active substances and/or optionally additives.
  • compositions are paint and coating preparations, fire-extinguishing agents, lubricants, washing agents and detergents and de-icers or developer solutions, rinse solutions, immersion oils and photoresists for photolithographic processes, in particular for immersion photolithography processes and in particular for the production of printed circuits, agrochemicals, floor polishes, cosmetic products, cosmetic products or hydrophobicisation agents for textile finishing or glass treatment.
  • Preferred compositions here are paint and coating preparations and printing inks.
  • the present invention also relates to water-based surface-coating formulations which comprise the polymers according to the invention, alone or mixed with additives.
  • surfacecoating formulations based on the following synthetic film formers: polycondensation resins, such as alkyd resins, saturated/unsaturated polyesters, polyamides/imides, silicone resins; phenolic resins; urea resins and melamine resins, polyaddition resins, such as polyurethanes and epoxy resins, polymerisation resins, such as polyolefins, polyvinyl compounds and polyacrylates.
  • the polymers according to the invention are also suitable for use in surface coatings based on natural products and modified natural products. Preference is given to surface coatings based on oils, polysaccharides, such as starch and cellulose, and also based on natural resins, such as cyclic oligoterpenes, polyterpenes and/or shellac.
  • the polymers according to the invention can be used both in physically hardening (thermoplastics) and in crosslinking (elastomers and thermosets) aqueous surface-coating systems.
  • the polymers according to the invention preferably improve the water and/or dirt repellency of the coated surfaces.
  • the present invention relates to all uses mentioned here of polymers to be employed in accordance with the invention.
  • the respective use of polymers for the said purposes is known to the person skilled in the art, and consequently the use of the polymers to be employed in accordance with the invention presents no problems.
  • the present invention particularly relates to the use of the polymers according to the invention and their preferred embodiments described above as and in functional coatings, for example for improving the water and/or dirt repellency of coating formulations, e.g. epoxy, acrylic, and PUR coatings.
  • coating formulations e.g. epoxy, acrylic, and PUR coatings.
  • the coating formulations according to the invention may also comprise solvents, additives, assistants, and fillers as well as non-fluorinated polymers.
  • a solution or dispersion comprising one or more polymers according to the invention can be applied as an additive for conventional coatings, but it also can be beneficial to spin coat the solution or dispersion itself as a thin layer on a substrate.
  • Suitable substrates are for example glass, ceramics, metals, textiles, garment or leather.
  • polymers and coatings comprising such polymers may be beneficial in terms of their eco toxicological profile and at the same time show good water and dirt repellency. Furthermore, polymers and coatings according to the invention may show good processability and/or storage stability.
  • the monomer(s), initiator and solvent are initially introduced into A dry three neck round-bottomed flask. An inert atmosphere is created by alternating vacuum and the entry of argon. The composition is heated to 115°C and stirred for 48 h. For the synthesis of block copolymers the comonomer is added after 24 h and the mixture heated and stirred for another 24 h. The solvent and residual monomers are removed at reduced pressure using a rotary evaporator.
  • Example 1 Synthesis of a non-fluorinated block
  • Polymer 1 (Poly-nBA) is prepared as follows:
  • Polymer 2 (Poly-AMPFE) is prepared as follows:
  • Poly-AFT6:2 is prepared as follows:
  • Polymer 4 (BIc-nBA-AMPFE) is prepared as follows:
  • Example 5 Synthesis of a random copolymer Polymer 5 (Rnd-nBA-AMPFE) is prepared as follows:
  • Polymer 6 (Blc-nBA-AFT6:2) is prepared as follows:
  • Polymer 7 (Rnd-nBA-AFT6:2) is prepared as follows:
  • Example 8 Application Tests The synthesized polymers are tested for their suitability as surface active additive in coating applications. For this purpose the polymers are dispersed in a 2 K-PUR and deposited on drawdown charts. After curing the repellency effect of the respective polymer on water and diiodomethane (DIM) is tested by contact angle measurement.
  • the apparatus used is a drop shape analyzer (DSA100 from Kruess, Germany).
  • the base coat composition is shown in Table 2.
  • the base coat and additive are mixed and homogenised with a magnetic stirrer (MultiReax) for 45 min. After addition of the hardener the mixture is homogenised with magnetic stirrer for another 20 min.
  • MultiReax a magnetic stirrer
  • Table 4 shows the contact angles of water or diiodomethane (DIM) droplets on 2K-PIIR coating with and without polymer additive, and the surface energy calculated therefrom. The measurement is repeated ten times for 2 droplets on different areas of the coated substrate. Table 4
  • block copolymer No. 4 shows higher contact angles of water and DIM than the block copolymers No. 5 of prior art, indicating higher water and dirt repellency.
  • Block copolymer No. 4 thus combines the advantages of higher water and dirt repellency and easier degradability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

La présente invention concerne de nouveaux copolymères séquencés contenant du fluor, des compositions comprenant les copolymères séquencés, l'utilisation des copolymères séquencés dans des compositions de revêtement, en particulier en tant qu'additifs tensioactifs dans des compositions de revêtement, des compositions comprenant de tels copolymères séquencés et des produits revêtus de telles compositions.
EP21769084.1A 2020-08-25 2021-08-23 Polymères contenant du fluor Pending EP4204467A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20192617 2020-08-25
PCT/EP2021/073213 WO2022043234A1 (fr) 2020-08-25 2021-08-23 Polymères contenant du fluor

Publications (1)

Publication Number Publication Date
EP4204467A1 true EP4204467A1 (fr) 2023-07-05

Family

ID=72240352

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21769084.1A Pending EP4204467A1 (fr) 2020-08-25 2021-08-23 Polymères contenant du fluor

Country Status (4)

Country Link
EP (1) EP4204467A1 (fr)
JP (1) JP2023538760A (fr)
CN (1) CN115943189A (fr)
WO (1) WO2022043234A1 (fr)

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4656226A (en) 1985-09-30 1987-04-07 E. I. Du Pont De Nemours And Company Acrylic pigment dispersants made by group transfer polymerization
US5322912A (en) 1992-11-16 1994-06-21 Xerox Corporation Polymerization processes and toner compositions therefrom
US5763548A (en) 1995-03-31 1998-06-09 Carnegie-Mellon University (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization
BR9710219A (pt) 1996-07-10 1999-08-10 Du Pont Processo para a sintese de polímeros agente de transferéncia de cadeia e polímero
EP2247678B1 (fr) 2008-02-22 2011-11-30 Basf Se Agents d'unisson fluorés
JP6959864B2 (ja) 2014-12-19 2021-11-05 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung フッ素化合物
JP2016145304A (ja) * 2015-02-09 2016-08-12 ユニマテック株式会社 重合性不飽和基を有する含フッ素２ブロック共重合体
CN107513127A (zh) * 2016-06-17 2017-12-26 默克专利股份有限公司 含氟聚合物
WO2020160626A1 (fr) * 2019-02-08 2020-08-13 The University Of Queensland Capture de composés carbonés fluorés

Also Published As

Publication number Publication date
WO2022043234A1 (fr) 2022-03-03
CN115943189A (zh) 2023-04-07
JP2023538760A (ja) 2023-09-11

Similar Documents

Publication Publication Date Title
JP7068200B2 (ja) フッ素含有ポリマー
EP2173706B1 (fr) Tensioactifs sulfonates fluorés
JP2010535792A (ja) フッ素化非イオン性界面活性剤
EP1743910A1 (fr) Polymère pour traitement de maçonnerie et agent traitant
TW201809170A (zh) 水性塗料組成物及塗裝物品
EP2576716B1 (fr) Additif polymère fluoré pour revêtements
EP4204467A1 (fr) Polymères contenant du fluor
KR101272841B1 (ko) 이산화탄소 용매를 이용한 초발수 공중합체의 합성과 그 응용
US20100041819A1 (en) Fluorinated surfactants and method of making the same
EP2576715B1 (fr) Additifs de polymère fluoré à base de solvant et utilisation de ceux-ci dans des compositions de revêtement
JP6841238B2 (ja) 水性分散液、その製造方法、水性塗料および塗装物品
JP2010506978A5 (fr)
KR20210109003A (ko) 불소 함유 중합체, 도료 조성물, 도장 물품의 제조 방법 및 도장 물품
WO2024126444A1 (fr) Procédé de production de polymères fluorés
WO2016176264A1 (fr) Additifs d'un complexe d'amine fluoré pour revêtements architecturaux
EP3150684B1 (fr) Composotion pour le traitement de maçonneries

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: 20230222

AK Designated contracting states

Kind code of ref document: A1

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 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)