WO2022096286A1 - Procédé de fabrication de particules agglomérées de piroctone olamine - Google Patents

Procédé de fabrication de particules agglomérées de piroctone olamine Download PDF

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Publication number
WO2022096286A1
WO2022096286A1 PCT/EP2021/079299 EP2021079299W WO2022096286A1 WO 2022096286 A1 WO2022096286 A1 WO 2022096286A1 EP 2021079299 W EP2021079299 W EP 2021079299W WO 2022096286 A1 WO2022096286 A1 WO 2022096286A1
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WO
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Prior art keywords
piroctone olamine
solid
binder
crystals
temperature
Prior art date
Application number
PCT/EP2021/079299
Other languages
English (en)
Inventor
Michael DYBALLA
Lisa HITSCHLER
Sven Gebhard
Peter Klug
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Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Publication of WO2022096286A1 publication Critical patent/WO2022096286A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/0275—Containing agglomerated particulates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/60—Particulates further characterized by their structure or composition
    • A61K2800/61—Surface treated
    • A61K2800/62—Coated
    • A61K2800/622—Coated by organic compounds

Definitions

  • the present invention relates to processes for making piroctone olamine agglomerate particles, to piroctone olamine agglomerate particles comprising piroctone olamine and a binder and to personal care products comprising the agglomerate particles.
  • 1-Hydroxy-4-methyl-6-(2,4,4- trimethyl)-pentyl-2(1 H)-pyridone, 2-aminoethanol salt also known as piroctone ethanolamine or piroctone olamine
  • piroctone ethanolamine is an anti-fungal active agent which is effective against the causes of dandruff. It is known to include piroctone olamine in personal care products, such as shampoos.
  • DE 1 795 270 A1 also describes a method of making piroctone olamine.
  • Piroctone olamine exists in the form of crystals which may be added to personal care products.
  • Commercially available piroctone olamine made by processes such as those referred to above typically has primary crystals with a diameter/length (D/l) ratio of about 1 :7 and a median diameter (dso) in the region of about 100 micrometers.
  • the primary crystals are those formed during the crystallization process, but prior to further processing and bulk handling steps. After such further processing and handling in bulk quantities, the crystals may change dimensions. In particular, the primary crystals may fracture and break, such that dso for such bulk quantities may be smaller than dso for primary crystals.
  • Such bulk quantities of piroctone olamine crystals may gather together to form clumps, especially during storage. Clumping phenomena may give rise to difficulties when handling and processing the bulk crystals.
  • a process for making piroctone olamine agglomerate particles comprising: a) Providing piroctone olamine crystals and a binder; b) Mixing the piroctone olamine crystals with the binder to form a blend; c) Chopping the blend to form the piroctone olamine agglomerate particles.
  • the binder comprises material which is liquid at 25 degrees Celsius.
  • the binder comprises material which is solid at 25 degrees Celsius, preferably in the form of particulate, the method further comprising heating the blend to a temperature above the melting temperature of the solid during b).
  • the temperature may advantageously be maintained above the melting temperature of the solid during c) as well.
  • the binder comprises material which is solid at 25 degrees Celsius, the method further comprising providing the binder in a) at a temperature above the melting temperature of the solid.
  • the piroctone olamine crystals may advantageously also be provided in a) at a temperature above the melting temperature of the solid.
  • the piroctone olamine crystals are provided in a) at the same temperature as the binder.
  • the temperature may advantageously be maintained during b) and c) above the melting temperature of the solid.
  • the binder is present in an amount from 1 %wt to 25%wt, preferably from 5%wt to 20%wt of the blend.
  • the binder comprises polyethylene glycol, triethylene glycol, ethylene glycol distearate, triethylene glycol distearate, saturated C12 - C22 fatty acids, saturated C12 - C22 fatty alcohol ethoxylates comprising from 2 to 50 EO (ethylene oxide) groups which are solid at 25 degrees Celsius, saturated C12 - C22 fatty alcohol propoxylates comprising from 2 to 50 PO (propylene oxide) groups which are solid at 25 degrees Celsius, or mixtures thereof.
  • EO ethylene oxide
  • PO propylene oxide
  • the binder comprises polyethylene glycol, especially polyethylene glycol having a mean molecular weight from 500 to 6000 g/mol, preferably from 1000 to 5000 g/mol.
  • the process additionally comprises: d) optionally milling the piroctone olamine agglomerate particles; e) separating, preferably by means of a sieve, piroctone olamine agglomerate particles having a target particle size range.
  • the target particle size range may be a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • an agglomerate particle comprising piroctone olamine crystals and a binder.
  • the agglomerate particle comprises from 1 %wt to 25%wt, preferably from 5%wt to 20%wt of binder.
  • the binder comprises polyethylene glycol, triethylene glycol, ethylene glycol distearate, triethylene glycol distearate, saturated C12 - C22 fatty acids, saturated C12 - C22 fatty alcohol ethoxylates comprising from 2 to 50 EO groups which are solid at 25 degrees Celsius, saturated C12 - C22 fatty alcohol propoxylates comprising from 2 to 50 PO groups which are solid at 25 degrees Celsius, or mixtures thereof.
  • the binder comprises polyethylene glycol, especially polyethylene glycol having a mean molecular weight from 500 to 6000 g/mol, preferably from 1000 to 5000 g/mol.
  • a plurality of the agglomerate particles of the second aspect of the invention having a d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • a personal care composition especially a hair care composition, comprising agglomerate particles of the third or fourth aspects of the invention.
  • the personal care composition is a hair care composition, then it may advantageously be a shampoo or a conditioner.
  • a personal care composition according to the fourth aspect may additionally comprise one or more ingredients common in the field of cosmetology, pharmacy, and dermatology.
  • additional ingredients may include oils, petrolatum, fatty alcohols, silicones, waxes, emulsifiers, co-emulsifiers, cationic polymers, film-formers, superfatting agents, stabilizers, polyols, preservatives, pearlizing agents, opacifiers, dyes, fragrances, solvents, protein derivatives such as gelatin, collagen hydrolysates, natural or synthetic-based polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives and mixtures thereof.
  • a process for making piroctone olamine agglomerate particles comprising: a) Providing piroctone olamine crystals and a solvent in which piroctone olamine is at least very slightly soluble at 25 degrees Celsius; b) Mixing the piroctone olamine crystals with the solvent until piroctone olamine crystals adhere to one another to form piroctone olamine agglomerate particles; c) Separating the solvent from the piroctone olamine agglomerate particles.
  • the solvent comprises water, ethyl acetate, isopropanol or ethanol.
  • separating the solvent in c) comprises evaporating the solvent.
  • the process additionally comprises: d) optionally milling the piroctone olamine agglomerate particles; e) separating, preferably by means of a sieve, piroctone olamine agglomerate particles having a target particle size range.
  • the target particle size range is a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • a process for making piroctone olamine agglomerate particles comprising: a) providing piroctone olamine crystals; b) agitating the piroctone olamine crystals while increasing the temperature to the softening temperature of the piroctone olamine, such that the crystals become tacky; and c) continuing agitation until the tacky crystals form piroctone olamine agglomerate particles.
  • the temperature in b) is increased to less than 126 degrees Celsius. According to another embodiment, the temperature in c) is maintained at the same temperature as the temperature in b).
  • the process additionally comprises: d) optionally milling the piroctone olamine agglomerate particles; e) separating, preferably by means of a sieve, piroctone olamine agglomerate particles having a target particle size range.
  • the target particle size range is a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • chop refers to the supply of physical energy to a material to separate it into discrete parcels and a “chopper” is a device which chops.
  • dso d(50) or D50
  • the median is defined as the diameter for which where half of the population lies below this value. For completeness, 10 percent of the population lies below the d , d(10) or D10 diameter and 90 percent of the population lies below the dgo, d(90) or D90 diameter.
  • very slightly soluble has the meaning given in Table 1 and the phrase “at least very slightly soluble”, as used herein, means that less than 10,000 mass parts of solvent are required to dissolve 1 mass part of piroctone olamine.
  • Relative humidity refers to the ratio (stated as a percent) of the moisture content of air compared to the saturated moisture level at the same temperature and pressure. Relative humidity can be measured with a hygrometer, in particular with a probe hygrometer from VWR® International.
  • min means “minute” or “minutes”.
  • mol means mole.
  • g following a number means “gram” or “grams” and “kg” means “kilogram” or “kilograms”.
  • “comprising” means that other steps and other ingredients can be in addition.
  • Embodiments and aspects described herein may comprise or be combinable with elements, features or components of other embodiments and/or aspects despite not being expressly exemplified in combination, unless an incompatibility is stated. “In at least one embodiment” means that one or more embodiments, optionally all embodiments or a large subset of embodiments, of the present invention has/have the subsequently described feature. “Molecular weight” or “M.Wt.” or “MW” and grammatical equivalents mean the number average molecular weight.
  • Particle Size Distribution Measurement Method for Piroctone Olamine Agglomerate Particles
  • a Horiba LA-950 particle size analyzer was used for measuring the diameter, the volumetric distribution density and the volumetric cumulative distribution of the granules.
  • the analyzer uses a laser diffraction method (ISO 13320:2009, Fraunhofer Diffraction Method) to measure the distribution and is based on the direct proportionality of the intensity of light scattered by a particle, to the diameter. Furthermore, the scattering angle is inversely proportional to the diameter and vice versa.
  • the required amount of powder is placed on a sieve with a mesh size of 1 mm.
  • the powder is sieved with an amplitude of 1 .5 mm for 3 minutes. This sieving step is done to avoid lumps.
  • the required amount of sieved powder was added to the gutter of the dry dispersion unit.
  • Clumping of particles may be regarded as a low degree of flowability.
  • the flowability may be measured.
  • the skilled person would be aware of other ways to characterize clumping.
  • the flowability of a bulk solid may be characterized by its unconfined yield strength, o c , in dependence on consolidation stress, 01, and storage period, t.
  • o c unconfined yield strength
  • ffc Oi / Oc
  • ffc is, i.e., the smaller the ratio of the unconfined yield strength, o c , to the consolidation stress, 01, the better a bulk solid flows.
  • Flow behavior is defined as follows: ffc of less than 1 , not flowing ffc from 1 to less than 2, very cohesive ffc from 2 to less than 4, cohesive ffc from 4 to less than 10, easy flowing ffc of greater than 10, free flowing
  • the parameters 01, o c and ff c may be generated using a ring sheer test using the method defined by Schulze, D (2009) “Pulver und Schuttpository”, 2 nd Edition, Springer, Berlin. This method is merely referred to as one way to characterize flowability in order to demonstrate the effect of the more flowable nature of the granules according to the invention versus piroctone olamine crystals. The skilled person would be aware of other ways to characterize flowability. The invention will now be further described with reference to the accompanying drawings, in which:
  • Figure 1 depicts the yield of piroctone olamine agglomerate particles according to sizerange for Examples 2A, 2B and 2C, below, following agglomeration, milling in a sieve mill at 4mm and then sieving in a target particle size range of 0.2-2mm.
  • Figure 2 illustrates the flowability factor, ff c , following time consolidation at 2kPa and at 3kPa over a period of 20 hours of the product of Examples 1 , 2A, 2B and 2C
  • a polyethylene glycol powder having a mean molecular weight of 1500g/mol PEG 1500.
  • a heatable 5 litre mixer/chopper (AVA Laboratory Mixer HTL-5) was filled to 60% capacity with piroctone olamine crystals and PEG 1500.
  • the PEG 1500 comprised 11 ,5wt% of the total mass.
  • the mixer was turned on and the two components were mixed at a speed from 81 to 115rpm.
  • the chopper was switched on and, while maintaining the temperature at the previous level, chopping was performed for two periods of 30s at 2867.5rpm until piroctone olamine agglomerate particles formed.
  • the ff c value at 2kPa vertical pressure was determined to be 2.21 .
  • the ff c value at 4kPa vertical pressure was determined to be 2.60.
  • Piroctone olamine crystals having a particle size of less than 1 mm; and • Two separate polyethylene glycol powder samples, one having a mean molecular weight of 1500g/mol (PEG 1500), the other having a mean molecular weight of 4000g/mol (PEG 4000).
  • the respective amount of piroctone olamine was added to a heatable 5 litre mixer/chopper (AVA Laboratory Mixer HTL-5) and the temperature was increased to a temperature above the melting range of the respective polyethylene glycol (the temperature was raised to 50 degrees Celsius for for PEG 1500 and 60 degrees Celsius for PEG 4000.
  • the mixer was turned on and, while maintaining the temperature at the previous level, the respective amount of the respective molten polyethylene glycol was poured portionwise into the mixer and mixed with the heated piroctone olamine over a 5 minute period.
  • the chopper was switched on, while maintaining the temperature at the previous level, and chopping was performed for up to 10 minutes until agglomerates formed.
  • the mixer/chopper was turned off when agglomerate formation was complete. Piroctone olamine agglomerate particles were removed from the mixer/chopper at process temperature and cooled to room temperature.
  • piroctone olamine agglomerate particles having a particle size > 4mm were present, then the agglomerate particles were milled in a sieve mill to a particle size below 4mm and then sieved to separate them into a 0.2mm - 2.0mm fraction and the amounts of each fraction were determined.
  • a 5 litre mixer (AVA Laboratory Mixer HTL-5), was filled to 60% capacity with piroctone olamine crystals at 25 degrees Celsius.
  • the mixer was turned on at a speed from 81 ,25rpm and water was dosed into the piroctone olamine crystals to a total of 9.4wt% of the mixture until the mixture stared to cohere.
  • the mixer was switched off and the piroctone olamine agglomerate particles were removed and gently vacuum dried at 40 degrees Celsius and less than 50mbar for 24 hours.
  • the melting range of batches of piroctone olamine crystals was determined using a Kofler Bench onto which the crystals were deposited. The temperature was measured using a surface sensor. Depending upon the particle size distribution and the conditions under which the crystals had been formed, the crystals began to liquify in the range from 98 degrees Celsius to 106 degrees Celsius, although solid components could still be observed in that temperature range. Melting was complete by a temperature of 125-126 degrees Celsius at which point smoke began to form.
  • a 5 litre mixer (AVA Laboratory Mixer HTL-5), was filled to 60% capacity with piroctone olamine crystals at 25 degrees Celsius.
  • the mixer was turned on at a speed from 58.75rpm and heated to raise the temperature of the piroctone olamine crystals into the melting range (see above) so that they become tacky. Mixing was continued, while maintaining the temperature at the previous level, until agglomerates formed.
  • the mixer was switched off and the piroctone olamine agglomerate particles were removed and cooled to room temperature.
  • a process for making piroctone olamine agglomerate particles comprising: a) Providing piroctone olamine crystals and a binder; b) Mixing the piroctone olamine crystals with the binder to form a blend; c) Chopping the blend to form the piroctone olamine agglomerate particles.
  • the binder comprises polyethylene glycol, triethylene glycol, ethylene glycol distearate, triethylene glycol distearate, saturated C12 - C22 fatty acids, saturated C12 - C22 fatty alcohol ethoxylates comprising from 2 to 50 EO groups which are solid at 25 degrees Celsius, saturated C12 - C22 fatty alcohol propoxylates comprising from 2 to 50 PO groups which are solid at 25 degrees Celsius, or mixtures thereof.
  • the binder comprises polyethylene glycol having a mean molecular weight from 500 to 6000 g/mol, preferably from 1000 to 5000 g/mol.
  • any preceding clause comprising: d) optionally milling the piroctone olamine agglomerate particles; e) separating, preferably by means of a sieve, piroctone olamine agglomerate particles having a target particle size range.
  • the target particle size range is a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • An agglomerate particle comprising piroctone olamine crystals and a binder.
  • the agglomerate particle of clause 14 comprising from 1 %wt to 25%wt, preferably from 5%wt to 20%wt of binder.
  • An agglomerate particle comprising piroctone olamine and having a flowability factor, ff c , greater than 2, preferably greater than 4, more preferably greater than 10, wherein: ffc 01 / o c and wherein 01 is the consolidation stress and o c is the unconfined yield strength.
  • a process for making piroctone olamine agglomerate particles comprising: a) Providing piroctone olamine crystals and a solvent in which piroctone olamine is at least very slightly soluble at 25 degrees Celsius; b) Mixing the piroctone olamine crystals with the solvent until piroctone olamine crystals adhere to one another to form piroctone olamine agglomerate particles; c) Separating the solvent from the piroctone olamine agglomerate particles.
  • the solvent comprises water, ethyl acetate, isopropanol or ethanol.
  • the process of clause 22 or 23, wherein separating the solvent in c) comprises evaporating the solvent.
  • any of clauses 22 to 24 additionally comprising: d) optionally milling the piroctone olamine agglomerate particles; e) separating, preferably by means of a sieve, piroctone olamine agglomerate particles having a target particle size range.
  • the target particle size range is a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.
  • a process for making piroctone olamine agglomerate particles comprising: a) providing piroctone olamine crystals; b) agitating the piroctone olamine crystals while increasing the temperature to the softening temperature of the piroctone olamine, such that the crystals become tacky; and c) continuing agitation until the tacky crystals form agglomerate particles.
  • the process of clause 27, wherein the temperature in b) is increased to less than 126 degrees Celsius.
  • the process of any of clauses 27 or 28, wherein the temperature in c) is maintained at the same temperature as the temperature in b).
  • the target particle size range is a target d50 range and wherein the target d50 range is from 0.1 mm to 8mm, preferably from 0.1 mm to 6mm, more preferably from 0.2mm to 2.5mm, more preferably still from 0.2mm to 2mm.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de fabrication de particules agglomérées de piroctone olamine, consistant : a) à utiliser des cristaux de piroctone olamine et un liant ; b) à mélanger les cristaux de piroctone olamine avec le liant pour former un mélange ; c) à broyer le mélange pour former les particules agglomérées de piroctone olamine.
PCT/EP2021/079299 2020-11-05 2021-10-22 Procédé de fabrication de particules agglomérées de piroctone olamine WO2022096286A1 (fr)

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EP20206051.3 2020-11-05
EP20206051 2020-11-05

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795270A1 (de) 1968-08-31 1971-12-30 Hoechst Ag 1-Hydroxy-2-pyridone und Verfahren zu ihrer Herstellung
DE2234009A1 (de) 1972-07-11 1974-01-24 Hoechst Ag Kosmetische zubereitungen
WO1993025074A1 (fr) * 1992-06-16 1993-12-23 E.I. Du Pont De Nemours And Company Compositions agricoles granuleuses se dispersant dans l'eau
US20140303135A1 (en) * 2013-04-04 2014-10-09 The Procter & Gamble Company Personal Care Compositions Having Dried Zinc Pyrithione-Polymer Aggregates
WO2020169544A1 (fr) 2019-02-19 2020-08-27 Clariant International Ltd Recristallisation de piroctone olamine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1795270A1 (de) 1968-08-31 1971-12-30 Hoechst Ag 1-Hydroxy-2-pyridone und Verfahren zu ihrer Herstellung
DE2234009A1 (de) 1972-07-11 1974-01-24 Hoechst Ag Kosmetische zubereitungen
WO1993025074A1 (fr) * 1992-06-16 1993-12-23 E.I. Du Pont De Nemours And Company Compositions agricoles granuleuses se dispersant dans l'eau
US20140303135A1 (en) * 2013-04-04 2014-10-09 The Procter & Gamble Company Personal Care Compositions Having Dried Zinc Pyrithione-Polymer Aggregates
WO2020169544A1 (fr) 2019-02-19 2020-08-27 Clariant International Ltd Recristallisation de piroctone olamine

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SCHULZE, D: "Pulver und Schuttguter", 2009, SPRINGER

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