EP2994224A1 - Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes - Google Patents

Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes

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Publication number
EP2994224A1
EP2994224A1 EP14719746.1A EP14719746A EP2994224A1 EP 2994224 A1 EP2994224 A1 EP 2994224A1 EP 14719746 A EP14719746 A EP 14719746A EP 2994224 A1 EP2994224 A1 EP 2994224A1
Authority
EP
European Patent Office
Prior art keywords
component
polyether
aqueous formulation
units
formulation according
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.)
Withdrawn
Application number
EP14719746.1A
Other languages
German (de)
English (en)
Inventor
Viet Nguyen-Kim
Ann-Kathrin MARGUERRE
Murat Mertoglu
Eve Leonie LEINENBACH
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP14719746.1A priority Critical patent/EP2994224A1/fr
Publication of EP2994224A1 publication Critical patent/EP2994224A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • 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
    • A61K2800/10—General cosmetic use
    • 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
    • A61K2800/49—Solubiliser, Solubilising system

Definitions

  • Solubilizer a mixture of poloxamers with different hydrophobicity
  • the present invention relates to the use of a mixture of
  • the active ingredients are therefore frequently used as micellar systems in which the active ingredient is solubilized by means of surface-active substances.
  • amphiphilic polymers are frequently used as solubilizers. Frequently used polymers are the poloxamers. Poloxamer is the generic name for triblock polyether copolymers of ethylene oxide and propylene oxide units.
  • Poloxamers are triblock polymers that have an A-B-A block structure.
  • US Pat. No. 5,672,564 discloses the use of poloxamers in combination with other surfactants.
  • US 20060013871 discloses the solubility improvement of ibuprofen by coating the ibuprofen with a poloxamer.
  • US-A 201 10008266 or US 20070141 143 describe the use of poloxamers in pharmaceutical formulations.
  • WO 2006002984 discloses liquid pesticide formulations which contain nonionic polyether block copolymers as solubility promoters.
  • US-A 20070015834 discloses mixtures of poloxamers and polyethylene glycol for the formulation of fenofibrate.
  • WO 03/017976 discloses the use of synergistic mixtures of poloxamers as solubilizers for active pharmaceutical ingredients. Specifically described are mixtures of Poloxamer 407 with the block structure (EO) ioi- (PO) s6- (EO) ioi and poloxamer 188 with the block structure (EO) 8o- (PO) 27- (EO) 8o.
  • the poloxamers used therein have higher ethylene oxide levels.
  • PO-rich surfactants alone have a solubilizing effect, but lead in larger concentrations to a strong increase in viscosity of the solution, so that they are unsuitable for aqueous formulations processing technology. In smaller concentrations, however, the solubilizing effect is often not strong enough to be of practical use.
  • y2 is 15 to 35.
  • aqueous active substance formulations containing a sparingly soluble in water active ingredient and a) 2 to 20 wt .-% of a hydroxy-terminated polyether of the block structure (A) (EO) xl '- (PO) y1 - (EO) x1 ", wherein y1 40 is up to 70 and (x1 "+ x1") is 30-60 and (x1 '+ x1 ") / y1 is less than 1 (component A), and
  • y 2 is 15 to 35.
  • the quotient (x1 '+ x1 ") / y1 is greater than ( ⁇ 2' + x2") / y2.
  • the ratio EO: PO of component A should therefore be greater than the ratio EO: PO of component B.
  • pooledly water-soluble active ingredient means according to the invention that at 25 ° C. and 0.1013 MPa the water solubility of the active ingredient is not more than 5 g / l, in particular not more than 1 g / l, especially not more than 0.1 g / l, is.
  • HLB value means hydrophilic-lipophilic balance.
  • the HLB value for nonionic surfactants can be calculated according to the following formula:
  • HLB 20 x (1 - Mi / M), where Mi represents the molecular weight fraction of the lipophilic moiety and M represents the total molecular weight.
  • Mi is the polypropylene oxide (PO) fraction.
  • Poloxamers are hydroxy-terminated triblock copolymers of the block structure ABA, where A is ethylene oxide units (EO) and b is propylene oxide units PO.
  • component A are as triblock copolymers polyethers of the block structure (A) (EO) x1 '- (PO) y1 - (EO) x1 ", where y1 is 40 to 70, preferably 45 to 60, and (x1' + x1" ) Is 30-60, preferably 30-50, and ( ⁇ 1 '+ x1 ") / y1 is less than 1.
  • the ratio of the total content of EO units to PO units is 1: 1 .05 to 1: 2, preferably 1: 1 .05 to 1: 1.
  • the polyethers are hydroxy terminated and have the general formula HO (CH 2 -CH 2 O) x i - (CH (CH 3 ) -CH 2 O) yi- (CH 2 -CH 2 O) xi -H
  • the HLB value can be 6 to 8 ,
  • Suitable polyether triblock copolymers are, for example
  • ⁇ 2 '+ x 2 is 15 to 55, preferably 15 to 35, and (x 2 '+ x 2") 2-50, preferably 10 to 50, is and ( ⁇ 2 '+ x2 ") / y2 is less than 1.
  • x2' x2".
  • the ratio of the total content of EO units to PO units (EO: PO) is 1: 1.1 to 1:14, preferably 1: 1.5 to 1: 8, more preferably 1: 1.5 to 1: 3.
  • the HLB value is 0 to 6, preferably 2 to 6.
  • the polyethers are hydroxy terminated and have the general formula HO (CH 2 -CH 2 O) X 2
  • Suitable components B are, for example
  • the components B are also commercially available, for example under the trade name Pluronic® PE.
  • Poloxamers A particularly preferred the compounds of the formulas HO commercially available as Pluronic® PE types 4300 and 6200 are (CH 2 -CH 2 0) 5 - (CH (CH 3) - CH 2 0) i9- (CH 2 CH 2 0 ) 5 -H and
  • the quantitative ratio of component A to component B may be 1: 1 to 1:10, preferably 1: 2 to 1: 8.
  • the component A can be used in amounts of 2.5 to 15 wt .-%, preferably 5 to 10 wt .-%.
  • the mixture of components A and B is used to solubilize sparingly water-soluble active substances in aqueous formulations.
  • Sparingly soluble active substances may be pharmaceutical, agrochemical or cosmetic active ingredients or dietary supplements or animal feed additives.
  • Pharmaceutical agents can come from all indications.
  • Agrochemically active compounds may be, for example, pesticides such as insecticides, fungicides or herbicides or seed treatment agents.
  • Cosmetic agents may be, for example, sunscreens, cosmetic oils or pigments.
  • Dietary supplements may be fat-soluble vitamins, carotenoids, ubiquinone or oily substances.
  • auxiliaries which are acceptable for the respective application can furthermore be added.
  • Additional additives include: thickeners, other surfactants, stabilizers, antioxidants, biocides, defoaming agents or dyes. Furthermore, organic solvents may additionally be present.
  • the data in% by weight in the tables below relate to the total amount of the aqueous formulation.
  • Components A and B in the amounts indicated below and 2% by weight of active compound were dissolved in water (at 20 ° C. and ambient pressure).
  • the sample was stirred at 20 ° C. for 24 h (magnetic stirrer 500 rpm) and then filtered through a syringe filter (PVDF filter membrane, 0.45 ⁇ m pore size).
  • a syringe filter PVDF filter membrane, 0.45 ⁇ m pore size
  • the active substance is quantified by UV / Vis spectroscopy.
  • the samples were diluted with an organic solvent in which the active ingredient dissolves to at least 10,000 ppm (1% by weight) (ethanol).
  • Component A is a compound having Component A:
  • Pluronic® PE 10400 HO (CH 2 -CH 2 O) 25- (CH (CH 3) -CH 2 O) 5 6- (CH 2 -CH 2 O) 25 -H
  • Components B HO (CH 2 -CH 2 O) 25- (CH (CH 3) -CH 2 O) 5 6- (CH 2 -CH 2 O) 25 -H
  • Components B HO (CH 2 -CH 2 O) 25- (CH (CH 3) -CH 2 O) 5 6- (CH 2 -CH 2 O) 25 -H
  • Pluronic® PE 4300 HO (CH 2 -CH 2 O) 5 - (CH (CH 3) -CH 2 O) i9- (CH 2 -CH 2 O) 5 -H
  • Pluronic® PE 6200 HO (CH 2 -CH 2 O) 5 - (CH (CH 3) -CH 2 O) 30 - (CH 2 -CH 2 O) 5 -H.
  • the solubility of fenofibrate in a 5% by weight aqueous solution of PE 10400 (component A) is 1089 ppm.
  • the solubility of fenofibrate in a 5% by weight aqueous solution of PE 4300 (component B) is 3 ppm.
  • the solubility of fenofibrate in a 5 wt.% Aqueous solution of PE 6200 (component B) is 4 ppm.
  • the solubility of fluxapyroxad in a 5% by weight aqueous solution of PE 10400 (component A) is 710 ppm.
  • the solubility of fluxapyroxad in a 5% by weight aqueous solution of PE 4300 (component B) is 28 ppm.
  • the solubility of fluxapyroxad in a 5% by weight aqueous solution of PE 6200 (component B) is 31 ppm.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polyethers (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention concerne l'utilisation d'un mélange a) d'un polyéther à terminaison hydroxy de la structure en bloc (A) (EO)x1'-(PO)y1 -(EO)x1'', où y1 présente une valeur allant de 40 à 70 et (x1'+x1'') présente une valeur allant de 30 à 60 et (x1' + x1'') / y1 est inférieur à 1 (composant A), et b) d'un polyéther à terminaison hydroxy de la structure en bloc (B) (EO)x2'-(PO)y2 -(EO)x2'', où y2 présente une valeur allant de 15 à 55 et ( x2' + x2'') présente une valeur allant de 2 à 50 et (x2' + x2'') / y2 est inférieur à 1 (composant B), où (x1' + x1'') / y1 > (x2' + x2'') / y2, pour la solubilisation de substances actives difficilement solubles dans l'eau, qui présentent à 25 °C et à 0,1013 MPa, une solubilité dans l'eau ne dépassant pas 5 g/l, dans des formulations aqueuses.
EP14719746.1A 2013-05-06 2014-04-25 Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes Withdrawn EP2994224A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14719746.1A EP2994224A1 (fr) 2013-05-06 2014-04-25 Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13166662 2013-05-06
EP14719746.1A EP2994224A1 (fr) 2013-05-06 2014-04-25 Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes
PCT/EP2014/058435 WO2014180677A1 (fr) 2013-05-06 2014-04-25 Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes

Publications (1)

Publication Number Publication Date
EP2994224A1 true EP2994224A1 (fr) 2016-03-16

Family

ID=48227059

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14719746.1A Withdrawn EP2994224A1 (fr) 2013-05-06 2014-04-25 Formulations aqueuses de substances actives difficilement solubles dans l'eau contenant comme solubilisant, un mélange de poloxamères présentant des hydrophobies différentes

Country Status (6)

Country Link
US (1) US20160074517A1 (fr)
EP (1) EP2994224A1 (fr)
JP (1) JP2016520422A (fr)
CN (1) CN105188901A (fr)
BR (1) BR112015027112A2 (fr)
WO (1) WO2014180677A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015121219A1 (fr) 2014-02-14 2015-08-20 BASF Agro B.V. Concentrat émulsionnable renfermant un pesticide, de l'amide gras et du lactamide
BR112018012002B1 (pt) * 2016-02-01 2021-09-28 Unilever Ip Holdings B.V. Composição de condicionamento de cabelo
CN108210360B (zh) * 2018-02-06 2021-02-12 德之馨（上海）有限公司 一种水溶性美白配方及其制备方法和用途
WO2020118660A1 (fr) * 2018-12-14 2020-06-18 Ecolab Usa Inc. Compositions antimicrobiennes stables contenant de l'iode pour trempage de trayons
US20220347128A1 (en) * 2019-06-20 2022-11-03 3M Innovative Properties Company Antimicrobial solutions
WO2023217394A1 (fr) * 2022-05-13 2023-11-16 Syngenta Crop Protection Ag Formulation comprenant du fludioxonil

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MX9305535A (es) * 1992-09-18 1994-03-31 West Agro Inc Composiciones y concentrados germicidas a base de yodo-detergente, acuosos y estables.
GB0120701D0 (en) * 2001-08-24 2001-10-17 Maelor Pharmaceuticals Ltd Pharmaceutical formulations
US20080193405A1 (en) * 2005-01-28 2008-08-14 Basf Aktiengesellschaft Use of a Water-In-Water Emulsion Polymers in the Form of a Thickener for Cosmetic Preparations
BRPI0708773B1 (pt) * 2006-03-10 2021-10-19 Laboswiss Ag Método para solubilização, dispersão e estabilização de substâncias, produtos manufaturados de acordo com o método, bem como uso dos mesmos
JP5941406B2 (ja) * 2009-07-14 2016-06-29 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機殺有害生物化合物の水性懸濁液を調製するための方法
CN103189409B (zh) * 2010-09-01 2015-11-25 巴斯夫欧洲公司 用于增溶微溶性活性成分的两亲物

Non-Patent Citations (1)

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Title
See references of WO2014180677A1 *

Also Published As

Publication number Publication date
BR112015027112A2 (pt) 2017-07-25
JP2016520422A (ja) 2016-07-14
US20160074517A1 (en) 2016-03-17
WO2014180677A1 (fr) 2014-11-13
CN105188901A (zh) 2015-12-23

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