EP4669111A1 - Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one - Google Patents

Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one

Info

Publication number
EP4669111A1
EP4669111A1 EP24707129.3A EP24707129A EP4669111A1 EP 4669111 A1 EP4669111 A1 EP 4669111A1 EP 24707129 A EP24707129 A EP 24707129A EP 4669111 A1 EP4669111 A1 EP 4669111A1
Authority
EP
European Patent Office
Prior art keywords
ppm
guanidine
zinc
range
benzisothiazolin
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
EP24707129.3A
Other languages
German (de)
English (en)
Inventor
Thomas Wunder
Roman Grabbe
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.)
Thor GmbH
Original Assignee
Thor 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 Thor GmbH filed Critical Thor GmbH
Publication of EP4669111A1 publication Critical patent/EP4669111A1/fr
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof

Definitions

  • the present invention relates to a composition which contains (a) guanidine and/or a salt of guanidine and (b) 1,2-benzisothiazolin-3-one, and optionally one or more zinc compounds and/or other biocidal active ingredients.
  • the invention further relates to technical products which contain the composition according to the invention.
  • aqueous ones such as paints, varnishes, emulsions, detergents and cleaning agents and cosmetic products
  • aqueous ones such as paints, varnishes, emulsions, detergents and cleaning agents and cosmetic products
  • These raw materials and the water used as a solvent are often contaminated with germs such as bacteria and fungi. If these products are not preserved during manufacture, they can have high germ counts just one day after production.
  • biocides are the so-called alkylguanidinium salts and also polyguanidinium salts.
  • medium and long-chain guanidines and biguanidines such as cocospropylenediamine-l,5-bis-guanidinium acetate, bis(guanidinooctyl)amine triacetate, poly(hexamethylene-biguanidine) hydrochloride, di(4'-chlorophenyldiguanido)hexane, chlorhexidine digluconate, chlorhexidine diacetate, have an antimicrobial effect.
  • (d2) 0 to 1000 ppm, preferably 1 to 1,000, particularly preferably 1 to 750 ppm of one or more compound(s) selected from sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, N-butyl-1,2-benzisothiazolin-3-one, octylisothiazolinone, bronopol, dibromonitrilopropionamide, iodopropynyl butylcarbamate, and dibromodicyanobutane.
  • compound(s) selected from sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, N-butyl
  • the invention relates to an aqueous composition
  • an aqueous composition comprising:
  • (dl) 1 to 150 ppm, preferably 2 to 100 ppm, particularly preferably 5 to 50 ppm 2-methyl-4-isothiazolin-3-one and (d2) 1 to 100 ppm, preferably 2 to 50 ppm, particularly preferably 5 to 30 ppm 5-chloro-
  • the aqueous composition defined above contains as component:
  • the aqueous composition defined above is an aqueous technical product selected from the group consisting of coatings, paints, varnishes, glazes and plasters, emulsions, latices, polymer dispersions, mineral slurries, pigment pastes and pigment dispersions, detergents and cleaning agents.
  • the invention relates to an aqueous composition containing:
  • the aqueous composition defined above contains as component:
  • the aqueous composition defined above is preferably an aqueous technical product selected from the group consisting of emulsions, latices, polymer dispersions, pigment dispersions, detergents and cleaning agents, particularly preferably it is an aqueous technical product selected from the group consisting of emulsions and latices.
  • composition according to the invention contains as component(s) (d):
  • Phenoxyethanol in an amount in the range of 100 to 10,000 ppm, preferably in an amount in the range of 250 to 7,500 ppm, particularly preferably in an amount in the range of 500 to 5,000 ppm and/or
  • Zinc pyrithione in an amount in the range of 10 to 1000 ppm, preferably in an amount in the range of 20 to 750 ppm, particularly preferably in an amount in the range of 30 to 500 ppm and/or
  • 5-chloro-2-methyl-4-isothiazolin-3-one in an amount in the range of 0.5 to 200 ppm, preferably in an amount in the range of 1 to 100 ppm, particularly preferably in an amount in the range of 2 to 50 ppm and/or
  • 2-methyl-4-isothiazolin-3-one in an amount in the range of 0.5 to 200 ppm, preferably in an amount in the range of 1 to 150 ppm, particularly preferably in an amount in the range of 2 to 100 ppm, and/or
  • N-methyl-l,2-benzisothiazolin-3-one in an amount in the range of 1 to 1000 ppm, preferably in an amount in the range of 2 to 750 ppm, particularly preferably in an amount in the range of 5 to 500 ppm and/or
  • N-butyl-l,2-benzisothiazolin-3-one in an amount in the range of 5 to 2,500 ppm, preferably in an amount in the range of 10 to 2,000 ppm, particularly preferably in an amount in the range of 10 to 1,500 ppm and/or
  • Dibromodicyanobutane in an amount in the range of 1 to 1,000 ppm, preferably in an amount in the range of 5 to 750 ppm, particularly preferably in an amount in the range of 10 to 500 ppm.
  • composition according to the invention which contains components (a) and (b) and optionally also (c), contains the above-mentioned component(s) (d) in the amounts indicated in each case.
  • This makes it possible to achieve a further synergistic increase in the antimicrobial effectiveness of the composition according to the invention, which already contains components (a) and (b) and optionally also (c).
  • the weight ratio of guanidine and/or its salt to phenoxyethanol is in the range from 0.13:1 to 3.6:1, the weight ratio being determined on the basis of the content in relation to the guanidine, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to sodium pyrithione is in the range from 3.6:1 to 180:1, preferably in the range from 3.6:1 to 100:1, particularly preferably in the range from 3.6:1 to 50:1, wherein in determining the weight ratio
  • the content in relation to guanidine is taken as the basis, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to zinc pyrithione is in the range from 3.6:1 to 180:1, preferably in the range from 3.6:1 to 100:1, particularly preferably in the range from 3.6:1 to 50:1, wherein the weight ratio is determined in each case on the basis of the content in relation to the guanidine, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to 5-chloro-2-methylisothiazolin-3-one is in the range from 62:1 to 9270:1, preferably in the range from 62:1 to 500:1, particularly preferably in the range from 62:1 to 300:1, wherein the content in relation to the guanidine is used as the basis for determining the weight ratio, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to 2-methylisothiazolin-3-one is in the range from 10.3:1 to 773:1, preferably in the range from 10.3:1 to 500:1, particularly preferably in the range from 10.3:1 to 300:1, wherein the content in relation to the guanidine is used as the basis for determining the weight ratio, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to N-methyl-1,2-benzisothiazolin-3-one is in the range from 7.8:1 to 618:1, preferably in the range from 7.8:1 to 400:1, particularly preferably in the range from 7.8:1 to 300:1, wherein the weight ratio is determined in each case on the basis of the content in relation to the guanidine, without taking into account any counter ion in the composition.
  • the weight ratio of guanidine and/or its salt to N-butyl-1,2-benzisothiazolin-3-one is in the range of 0.52:1 to 309:1, preferably in the range of 0.52:1 to 200:1, particularly preferably in the range from 0.52:1 to 100:1, wherein the weight ratio is determined on the basis of the content in relation to the guanidine, without taking into account any counterion in the composition.
  • the weight ratio of guanidine and/or its salt to N-octylisothiazolin-3-one is in the range from 1.4:1 to 82:1, preferably in the range from 1.4:1 to 50:1, wherein the weight ratio is determined in each case on the basis of the content in relation to the guanidine, without taking into account any counterion in the composition.
  • the weight ratio of guanidine and/or its salt to bronopol is in the range from 7.8:1 to 824:1, preferably in the range from 7.8:1 to 200:1, particularly preferably in the range from 7.8:1 to 100:1, wherein the weight ratio is determined in each case on the basis of the content in relation to the guanidine, without taking into account any counterion in the composition.
  • the weight ratio of guanidine and/or its salt to 2,2-dibromo-3-nitrilepropionamide is in the range from 7.8:1 to 3090:1, preferably in the range from 7.8:1 to 250:1, particularly preferably in the range from 7.8:1 to 100:1, wherein the content in relation to the guanidine is used as the basis for determining the weight ratio, without taking into account any counterion in the composition.
  • the weight ratio of guanidine and/or its salt to iodopropynyl butylcarbamate is in the range from 0.83:1 to 103:1, preferably in the range from 1:1 to 90:1, particularly preferably in the range from 1:1 to 80:1, wherein the weight ratio is determined in each case based on the content in relation to the guanidine, without taking into account any counter ion, in the composition.
  • the weight ratio of guanidine and/or its salt to dibromodicyanobutane in Range from 0.78:1 to 309:1, preferably in the range from 0.8:1 to 200:1, particularly preferably in the range from 0.8:1 to 100:1, wherein the weight ratio is determined in each case on the basis of the content in relation to the guanidine, without taking into account any counter ion in the composition.
  • component (a), the guanidine and/or its salt and the above-mentioned component(s) (d) are present in the indicated synergistic ratios to one another. This makes it possible to achieve a further synergistic increase in the antimicrobial effectiveness of the composition according to the invention, which already contains components (a) and (b) and optionally also (c).
  • the present invention relates to the use of:
  • the invention further relates to the use of:
  • guanidine and/or at least one salt of guanidine (b) 1 to 1,000 ppm, preferably 10 to 750 ppm, particularly preferably 25 to 500 ppm, 1,2-benzisothiazolin-3-one,
  • (dl) 0 to 10,000 ppm, preferably 100 to 10,000 ppm, particularly preferably 250 to 7,500 ppm, very particularly preferably 500 to 5,000 ppm phenoxyethanol, and
  • (d2) 0 to 1000 ppm, preferably 1 to 1,000, particularly preferably 1 to 750 ppm of one or more compound(s) selected from sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, N-butyl-1,2-benzisothiazolin-3-one, octylisothiazolinone, bronopol, dibromonitrilopropionamide, iodopropynyl butylcarbamate, and dibromodicyanobutane.
  • compound(s) selected from sodium pyrithione, zinc pyrithione, 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, N-methyl-1,2-benzisothiazolin-3-one, N-butyl
  • the present invention further relates to a process for preparing the aqueous compositions according to the invention, comprising mixing the components defined above.
  • the synergism that occurred was numerically represented by calculating the synergy index (SI). The calculation was carried out according to the standard method of F.C. Kull et al., Applied Microbiology, Vol. 9 (1961), p. 538.
  • synergy index has a value of more than 1, this means that antagonism exists. If the synergy index has a value of 1, this means that the effects of the two biocides/compounds are additive. If the synergy index has a value of less than 1, this means that there is synergism between the two biocides/compounds.
  • Example 1 Investigation of the synergistic interaction between guanidine and l,2-benzisothiazolin-3-one (BIT)
  • the optimal synergism i.e. the lowest synergy index (0.67) of a composition of guanidine and BIT is at a ratio of 3090 ppm guanidine to 100 ppm BIT. Synergism can be demonstrated when the weight ratio of guanidine to BIT is in the range of 1.3:1 to 309:1.
  • the detergent was a heavy-duty detergent without preservatives (pH 8.1), and the cleaning agent was an all-purpose cleaner without preservatives (pH 7.6), each also manufactured in the laboratory, without the addition of the usual conventional preservatives.
  • the paint was mixed with specific concentrations of guanidinium hydrochloride and benzisothiazolinone (BIT) - individually and in combination.
  • the detergent and cleaning agent were mixed with specific concentrations of guanidinium hydrochloride and benzisothiazolinone (BIT).
  • the resulting batches of the paint prepared in this way were inoculated with a mixture of various bacteria, and the batches of the detergent and cleaning agent prepared in this way were inoculated with a yeast mixture.
  • the inoculum was added to the respective sample at each inoculation at 2% (v/w) as a fresh cell suspension in a physiological saline solution (0.9% NaCl).
  • the cell count of the added inoculum was 10 9 /ml for the bacterial mixture, Yeast mixture 10 8 /ml, consisting of equal parts of the individual bacterial and yeast strains.
  • the cell suspension of the bacterial mixture was prepared by culturing the individual bacteria for 24 hours at 30 °C in liquid culture on a shaker. Müller-Hinton liquid medium was used as the medium for culturing the bacteria. After cultivation, the individual liquid cultures were centrifuged and the cells resuspended in physiological saline solution. To adjust the mixture to a total cell count of 10 9 /ml, the individual bacterial suspensions were diluted accordingly before combining with saline solution if necessary. The cell count of the inoculation suspension was determined using the chamber counting method.
  • the yeasts were grown on Sabouraud glucose agar for 48 hours at 25 °C and the cell layer was washed off using physiological saline solution (0.9% NaCl). Further steps to adjust the cell count of the inoculation suspension to 10 8 /ml were carried out in the same way as for preparing the bacterial suspension.
  • the samples were inoculated once with the respective cell suspensions (2% v/w) and the development of the bacteria or yeasts was monitored using a semi-quantitative evaluation method.
  • the microbial contamination of the inoculated samples was assessed directly after inoculation on day 1 and after 5 further days of incubation at 30 °C on day 6 (emulsion paint) or after 2 further days of incubation at 30 °C on day 3 (detergent, cleaning agent).
  • an aliquot was taken from each sample after homogenization using a sterile plastic inoculation loop (10 ⁇ l) and spread evenly on agar plates (tryptone soy agar for bacteria, Sabouraud glucose agar for yeasts).
  • the spread agar plates were then incubated for 48 hours at 30 °C (bacteria) or 72 hours at 25 °C (yeasts). After incubation, the bacterial or yeast colonies growing on the agar plates were visually assessed and quantified according to the following scheme:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition qui contient (a) de la guanidine et/ou un sel de guanidine, et (b) de la 1,2-benzisothiazoline-3-one, et éventuellement un ou plusieurs composés de zinc et/ou d'autres substances actives biocides. L'invention concerne également des produits techniques qui contiennent la composition selon l'invention.
EP24707129.3A 2023-02-23 2024-02-16 Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one Pending EP4669111A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23000032 2023-02-23
PCT/EP2024/000013 WO2024175248A1 (fr) 2023-02-23 2024-02-16 Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one

Publications (1)

Publication Number Publication Date
EP4669111A1 true EP4669111A1 (fr) 2025-12-31

Family

ID=85384526

Family Applications (1)

Application Number Title Priority Date Filing Date
EP24707129.3A Pending EP4669111A1 (fr) 2023-02-23 2024-02-16 Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one

Country Status (5)

Country Link
EP (1) EP4669111A1 (fr)
JP (1) JP2026505253A (fr)
KR (1) KR20250153812A (fr)
CN (1) CN120676865A (fr)
WO (1) WO2024175248A1 (fr)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4661503A (en) * 1986-06-16 1987-04-28 Nalco Chemical Company Synergistic biocide of dodecyl guanidine hydrochloride and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one
US5677345A (en) 1996-03-29 1997-10-14 Calgon Corporation Synergistic antimicrobial composition of N- (dichlorofluoromethyl)thio!-N',N'-dimethyl-N-phenylsulfamide and alkylguanidine compounds
EP0900525A1 (fr) 1997-08-20 1999-03-10 Thor Chemie Gmbh Composition biocide synergique
EP0980648A1 (fr) 1998-08-20 2000-02-23 Thor Chemie Gmbh Composition biocide synergique
US9723842B2 (en) * 2006-05-26 2017-08-08 Arch Chemicals, Inc. Isothiazolinone biocides enhanced by zinc ions
CN103619174A (zh) * 2011-05-13 2014-03-05 Isp投资公司 1,2-苯并异噻唑啉-3-酮的水溶液
CN103768642A (zh) * 2012-10-17 2014-05-07 天津市中科健新材料技术有限公司 一种具有清凉抑菌功效的一次性卫生用品
US20210235699A1 (en) * 2018-06-29 2021-08-05 Lonza, Llc Adjuvant Compositions Comprising a Tetramethylguanidine and a 4-Isothiazolin-3-One
CN111364244A (zh) * 2020-03-02 2020-07-03 无锡新友达服装科技有限公司 一种抗菌衬衫
CN112759840A (zh) * 2021-01-25 2021-05-07 孙牡花 一种pp抗菌塑料及其制备方法
CN117098455A (zh) * 2021-03-19 2023-11-21 阿萨达有限责任公司 杀生物组合物和方法

Also Published As

Publication number Publication date
WO2024175248A1 (fr) 2024-08-29
KR20250153812A (ko) 2025-10-27
JP2026505253A (ja) 2026-02-13
CN120676865A (zh) 2025-09-19

Similar Documents

Publication Publication Date Title
DE69033037T2 (de) Synergetische mikrobizide Kombinationen
DE69505727T2 (de) Zusammensetzungen aus 4,5-Dichlor-2-N-Octyl-3-Isothiazolon und bestimmten kommerziellen Bioziden
EP1924145A2 (fr) Composition biocide synergique contenant de l'argent
DE4026756C2 (de) Konservierungsmittel und deren Verwendung
EP3439473B1 (fr) Compositions biocides synergiques contenant de la 5-chloro-2-méthylisothiazolin-3-one
EP2575476A1 (fr) Composition biocide synergique contenant au moins trois composants biocides
EP2213166B1 (fr) Compositions biocides contenant du 2-méthylisothiazolin-3-one et une haloalkylsulfone
DE19842116C2 (de) Verwendung von Derivaten von Methylenbisoxazolidin und dadurch erhaltene Zusammensetzungen
DE60105087T2 (de) Flüssige Biozidzusammensetzung bestehend aus einem Formaldehydaddukt und einer Isothiazolonverbindung
EP3346838A1 (fr) Composition biocide stable au stockage
EP3589126A1 (fr) Compositions biocides synergiques contenant de la 5-chloro-2-méthylisothiazolin-3-one
EP4669111A1 (fr) Compositions contenant de la guanidine et du 1,2-benzisothiazoline-3-one
EP4669110A1 (fr) Produits cosmétiques et produits de nettoyage stabilisés contre une attaque microbienne
WO2024175246A1 (fr) Produit industriel aqueux stabilisé contre la contamination microbienne
EP2157862B1 (fr) Composition biocide contenant du glutaraldehyde et au moins une isothiazolinone
EP1937062B1 (fr) Melange d'agents actifs fabriques a partir d'agents microbicides a base d'o-phenyl-phenol (opp) et d'amines
EP4669108A1 (fr) Compositions synergiques contenant de la guanidine
WO2025125110A1 (fr) Compositions contenant de la guanidine et du carbonate
EP3439476A1 (fr) Compositions biocides synergiques contenant de la 5-chloro-2-méthylisothiazolin-3-one
DE3940783A1 (de) Stabile biozid-zusammensetzung zur industriellen verwendung
WO2026041525A1 (fr) Compositions adhésives aqueuses stabilisées contre des attaques microbiennes
WO2026041529A1 (fr) Compositions aqueuses de produits agrochimiques stabilisées contre des attaques microbiennes
DE69712051T2 (de) Synergistische antimikrobielle Zusammensetzungen
WO2023061620A1 (fr) Procédé de traitement de produits techniques
EP3836787A1 (fr) Compositions biocides stables renfermant de la 1,2-benzisothiazolin-3-one et de la glycérine

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: 20250917

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 ME MK MT NL NO PL PT RO RS SE SI SK SM TR