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EP1379328A1 - Microcapsules - Google Patents

Microcapsules

Info

Publication number
EP1379328A1
EP1379328A1 EP02712964A EP02712964A EP1379328A1 EP 1379328 A1 EP1379328 A1 EP 1379328A1 EP 02712964 A EP02712964 A EP 02712964A EP 02712964 A EP02712964 A EP 02712964A EP 1379328 A1 EP1379328 A1 EP 1379328A1
Authority
EP
European Patent Office
Prior art keywords
microcapsules
microcapsules according
active substances
anspmch
active substance
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Withdrawn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
EP02712964A
Other languages
German (de)
English (en)
Inventor
Wolfgang Podszun
Joachim Krüger
Joachim Probst
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1379328A1 publication Critical patent/EP1379328A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • 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
    • A01N25/26—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 in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules
    • 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
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

  • the present invention relates to new microcapsules which contain solid active substances as the core, to a process for the preparation of these microcapsules and to their use for applying the active substances contained.
  • Microcapsules are understood to mean particles with a particle size of approximately 1 to 200 ⁇ m and a core-shell structure, the core representing or containing an active substance.
  • Active substances include, for example, pharmaceutical active ingredients, agrochemical active ingredients, flavors, additives,
  • the shell material can be a natural polymer, such as. B. gelatin or gum arabic or a synthetic polymer. Further details of the microencapsulation are described in Kirk-Othmer, "Encyclopedia of Chemical Technology", Fourth Edition, Volume 16, pages 628-651.
  • Microcapsules are already known, the shell of which is preferably made of polyurea and the inside of which is filled with a suspension of solid, biologically active compounds in a non-aqueous liquid (cf.
  • the liquid can cause an undesired effect when used, eg contamination of the treated surfaces with the liquids in agrochemical applications. • The mechanical stability of the microcapsules is reduced by the liquid.
  • a shell made of polyurethane and / or polyurea and a core of at least one solid active substance
  • microcapsules according to the invention can be produced by suspending at least one solid active substance in water
  • microcapsules according to the invention are very suitable for the application of the solid active substances contained for the particular application.
  • microcapsules according to the invention are better suited for applying the solids contained than the constitutionally most similar, known preparations. Above all, it is unexpected that the microcapsules according to the invention, which consist practically only of solid, release the core materials in the manner desired in each case.
  • the microcapsules according to the invention are notable for a number of advantages. They contain a very high proportion of active substances and are mechanically stable. In addition, if these microcapsules are used in agriculture, there is no fear of contamination of the treated areas with undesirable liquids.
  • the shells of the microcapsules according to the invention consist of polyurethane and / or polyurea. These shell materials are derived from water-dispersible polyisocyanates which react with polyol and / or polyamine components. Monomers and. Suitable for producing these shell materials
  • Solid active substances which are contained in the microcapsules according to the invention as core materials are pharmaceutical active substances, agrochemical active substances, flavors, additives, adhesives, leuco dyes and flame retardants which are solid at room temperature.
  • agrochemical substances are understood to mean all substances customary for plant treatment, the melting point of which is above 20 ° C.
  • Fungicides, bactericides, insecticides, acaricides, nematicides, molluscicides, herbicides, plant growth regulators, plant nutrients and repellents are preferably mentioned.
  • fungicides are:
  • Difenoconazole dimethirimol, dimethomo ⁇ h, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
  • Fluquinconazole Fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox, fenhexamide,
  • Iprovalicarb Iprovalicarb, Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
  • Nickel dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
  • PCNB Quintozen
  • quinoxyfen quinoxyfen
  • sulfur and sulfur preparations Tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, Thicyofen, thio Phanat-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, triflumizole, triforine, triticonazole, trifloxystrobin validamycin A, vinclozolin,
  • bactericides are:
  • insecticides examples include acaricides and nematicides.
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
  • Fipronil fluazuron, flucycloxuron, flucythrinate, flufenoxuron, flufenprox,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymetrozin, Pyrach
  • Tebufenozide Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temefos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiacloprid, Thiafenox, Thiamethoxam
  • Thiodicarb Thiofanox, Thiomethon, Thionazin, Thuringiensin, Tralomethrin, Transfluthrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron,
  • molluscicides are metaldehyde and methiocarb.
  • herbicides are:
  • Anilides e.g. Diflufenican and Propanil
  • Aryl carboxylic acids e.g. Dichloropicolinic acid, dicamba and picloram
  • Aryloxyalkanoic acids e.g. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr
  • Aryloxy-phenoxy-alkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl
  • Azinones e.g.
  • Chloridazon and norflurazon Carbamates, e.g. Chlo ⁇ ropham, Desmedipham, Phenmedipham and Propham; Chloroacetanilides, e.g. Alachlor, acetochlor, butachlor, metazachlor, metolochlor, pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, bifenox, fluoroglycofen,
  • Fomesafen, halosafen, lactofen and oxyfluorfen Ureas, e.g. Chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hydroxylamines, e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g.
  • Sulfonylureas e.g. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tri-benuron-methyl
  • Thiol carbamates e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates
  • Triazines e.g.
  • Atrazin cyanazin, simazin, simetryne, terbutryne and terbutylazin; Triazinones, e.g. Hexazinone, metametron and metribuzin; Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane. Furthermore, 4-
  • Chlorcholine chloride and ethephon are examples of plant growth regulators.
  • Examples of plant nutrients are customary inorganic or organic fertilizers for supplying plants with macro and / or micronutrients.
  • repellents are diethyl tolylamide, ethylhexanediol and butopyronoxyl.
  • flame retardants are understood to mean substances with a melting point above 20 ° C. which can be incorporated into plastics and reduce their flammability. Examples include halogen compounds which are solid at temperatures up to 40 ° C. and phosphorus in the red modification.
  • polyisocyanates and polyol and / or polyamine components which are dispersible in water are required as starting materials for producing the shell materials.
  • water-dispersible polyisocyanates are organic polyisocyanates with aliphatic, cycloaliphatic and / or aromatically bound free isocyanate groups which are liquid at room temperature.
  • Polyisocyanates with an (average) NCO functionality of 2 to 5 are preferred. Examples include: m-phenylene diisocyanate, p-phenylene diisocyanate, 2,4-tolylene diisocyanate, 3,3'-dimethyl-4,4'-biphenylene diisocyanate, 4. 4'-methylene bis (2-methylphenyl isocyanate), hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, 4,4'-methylene bis (cyclohexyl isocyanate).
  • hydrophilized polyisocyanates which can be obtained from the above-mentioned polyisocyanates by partial reaction of the NCO groups with ionic or nonionic compounds, for example by reaction with polyethylene oxide.
  • Particularly useful hydrophilic polyisocyanates are disclosed in EP-A 0 959 087. Such hydrophilic
  • Non-hydrophilized polyisocyanates can be emulsified with the aid of polyol components, which are also required as starting materials, or with other surface-active agents.
  • suitable polyol components are polymers which have hydroxyl groups and also carboxylate and / or sulfonate groups. These include, for example, polymers of olefinically unsaturated compounds which contain hydroxyl groups.
  • Polymers containing hydroxyl groups are preferred which have a molecular weight M n (number average) of 500 to 50,000, preferably 1000 to 10,000 and a hydroxyl number of 16.5 to 264, preferably 33 to 165 mg KOH / g polymer, which can be determined by gel permeation chromatography exhibit.
  • M n number average
  • the polyol component also contains carboxylate and / or sulfonate groups, the proportion of these groups being 5 to 500, preferably 25 to 250 milliequivalents / 100 g of polymer.
  • the carboxylate and / or sulfonate groups increase the water solubility or the dispersibility of the polymers.
  • the hydroxyl-containing polymers can be copolymerized with
  • hydroxyl-containing monomers and monomers which contain carboxylic acid groups and / or sulfonic acid groups, the carboxylic acid groups and / or sulfonic acid groups being at least partially neutralized after the polymerization.
  • Preferred monomers containing hydroxyl groups are, for example, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate.
  • monomers with carbon Acid groups are acrylic acid, methacrylic acid, maleic acid and itaconic acid.
  • a suitable monomer with a sulfonic acid group is 2-acrylamido-2-methylpropane sulfonic acid.
  • monomers which can be used in the preparation of the hydroxyl-containing polymers are monomers without functional groups, such as, for example, methyl methacrylate, methyl acrylate, ethyl acrylate, ethyl methacrylate, isopropyl methacrylate,
  • polyamines can be used instead of or preferably in addition to the polyols.
  • Such polyamines are preferably diethylenetriamine or triethylenetetramine.
  • finely divided means that the particles have an average particle size between 1 and 200 ⁇ m, preferably between 2 and 100 ⁇ m.
  • the temperatures can be varied within a certain range when carrying out the method according to the invention.
  • the capsule shell reaction is carried out at room temperature. But it is also possible to work at temperatures between 20 ° C and 100 ° C.
  • a catalyst can also be added to the reaction mixture.
  • suitable catalysts are organic tin compounds, such as dibutyltin dilaurate, or else tertiary amines, such as triethylamine.
  • concentration of catalyst can be varied within a certain range. In general, catalyst is used in amounts between 0.01 and
  • the implementation of the reaction according to the invention generally takes a few hours. It is possible to control the course of the reaction by IR spectroscopic detection of the NCO content.
  • the ratio of polyisocyanate to polyol and / or polyamine component can be varied within a certain range.
  • polyisocyanate and polyol and or polyamine components are used in such amounts that an NCO / OH
  • the total amount of polyisocyanate and polyol and / or polyamine component can also be varied within a certain range in relation to the solid active substance.
  • polyisocyanate and polyol and / or polyamine component are used in such a total amount that the Weight ratio of the components used to form the capsule shells to active substance is between 1: 0.001 and 1: 1, preferably between 1: 0.01 and 1: 0.25.
  • the particle size of the microcapsules according to the invention can be varied within a relatively wide range, depending on the particle size of the active substances used. Accordingly, the particle size of the microcapsules is generally between 1 and 200 ⁇ m, preferably between 2 and 100 ⁇ m. Microcapsules containing agrochemicals as active substances particularly preferably have an average particle size between 2 and 30 ⁇ m.
  • microcapsules according to the invention are obtained as solid particles in aqueous suspension when the method according to the invention is carried out. If it is desired to separate the microcapsules, the capsules can be isolated, for example by filtering or decanting, and, if appropriate, dried after washing.
  • microcapsules according to the invention contain agrochemical active substances, they are eminently suitable for applying these active substances to plants and / or their habitat.
  • the microcapsules according to the invention can be used as such either in solid form or as suspensions, if appropriate after prior dilution with water and, if appropriate, after the addition of formulation auxiliaries.
  • the application is carried out according to customary methods, for example by pouring, spraying, spraying or scattering.
  • microcapsules according to the invention which contain agrochemical active ingredients can be varied within a relatively wide range. It depends on the respective agrochemical active ingredients and their content in the microcapsules.
  • the microcapsules according to the invention, which contain agrochemical active substances, ensure the release of the active components in the desired amount over a longer period of time.
  • Microcapsules according to the invention which contain flame retardants, are easier to incorporate into plastics than non-encapsulated flame retardants.
  • microencapsulated flame retardants according to the invention into plastics, an undesirable influence on the properties of the plastics, for example on a reduction in the mechanical strength, can be largely avoided.
  • the allophanatization reaction is started by adding 0.01 g of zinc (II) -2-ethyl-1-hexanoate.
  • the temperature of the reaction mixture rises to 109 ° C. due to the heat of reaction released.
  • the reaction was carried out by adding 0.01 g
  • a polyacrylate in the form of a secondary dispersion was prepared by reacting the comonomers methacrylic acid 2-hydroxyethyl ester, acrylic acid, methacrylic acid methyl ester and acrylic acid 2-butyl ester according to the process given in EP-B 0 358 979.
  • the dispersion has a solids content of 46%, an OH content of 3.3% with respect to solid resin, an acid number of approx. 21 mg KOH / g solid resin, a pH of 8.0 and a viscosity of approx. 800 mPa- s
  • N-dimethylaminoethanol acts as a neutralizing agent.
  • Example 3 The reaction described in Example 3 was repeated in such a way that no catalyst was added. The reaction time at 50 ° C was 42 hours. After drying, 30.8 g of microencapsulated product which had no phosphine odor was obtained.
  • a slurry of 40 g of thiacloprid in 337 g of deionized water was successively mixed with 17.4 g of the polyol component described in Example 2, 5.4 g of the polyisocyanate described in Example 1 and 8 mg of the catalyst mentioned in Example 3.
  • After setting a stirring speed of 300 RPM the reaction mixture was stirred at room temperature for 18 hours.
  • the microencapsulated product was then isolated by centrifugation, washed thoroughly with water, centrifuged again and then dried at 60 ° C. to constant weight. 35.5 g of powdery, microencapsulated product were obtained.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
  • Fireproofing Substances (AREA)

Abstract

L'invention concerne de nouvelles microcapsules qui comprennent une enveloppe en polyuréthanne et/ou polyurée, ainsi qu'un noyau constitué d'au moins une substance active solide, aucun liquide n'étant présent dans ce noyau. L'invention concerne également un procédé de production de ces nouvelles microcapsules et leur utilisation pour l'administration des substances actives contenues.
EP02712964A 2001-04-10 2002-04-02 Microcapsules Withdrawn EP1379328A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10117784A DE10117784A1 (de) 2001-04-10 2001-04-10 Mikrokapseln
DE10117784 2001-04-10
PCT/EP2002/003617 WO2002083290A1 (fr) 2001-04-10 2002-04-02 Microcapsules

Publications (1)

Publication Number Publication Date
EP1379328A1 true EP1379328A1 (fr) 2004-01-14

Family

ID=7681022

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02712964A Withdrawn EP1379328A1 (fr) 2001-04-10 2002-04-02 Microcapsules

Country Status (9)

Country Link
US (1) US20040115280A1 (fr)
EP (1) EP1379328A1 (fr)
JP (1) JP2004535276A (fr)
CN (1) CN1501837A (fr)
BR (1) BR0208797A (fr)
CA (1) CA2443682A1 (fr)
DE (1) DE10117784A1 (fr)
MX (1) MXPA03009229A (fr)
WO (1) WO2002083290A1 (fr)

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JP2004535276A (ja) 2004-11-25
MXPA03009229A (es) 2004-01-29
DE10117784A1 (de) 2002-10-17
US20040115280A1 (en) 2004-06-17
BR0208797A (pt) 2004-03-09
CA2443682A1 (fr) 2002-10-24
WO2002083290A1 (fr) 2002-10-24

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