AU2005256662A1 - Use of ether group-containing polymers as solubilizers - Google Patents
Use of ether group-containing polymers as solubilizers Download PDFInfo
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- AU2005256662A1 AU2005256662A1 AU2005256662A AU2005256662A AU2005256662A1 AU 2005256662 A1 AU2005256662 A1 AU 2005256662A1 AU 2005256662 A AU2005256662 A AU 2005256662A AU 2005256662 A AU2005256662 A AU 2005256662A AU 2005256662 A1 AU2005256662 A1 AU 2005256662A1
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- 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
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- 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
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- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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- 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
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- 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
- A61K8/04—Dispersions; Emulsions
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- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
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- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/42—Nitriles
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/30—Nitriles
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F28/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a bond to sulfur
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- 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
- A61K9/10—Dispersions; Emulsions
-
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
Description
I, Dr. Ulrich Fitzner, Attorney at Law, Hauser Ring 10, 40878 Ratingen, Germany, hereby declare that I am conversant with the German and the English languages and certify that to the best of my knowledge and belief the following is a true and correct English translation of the PCT Application filed under No. PCT/EP2005/053123. Signed this 1 9 th day of December 2006 Dr. Ulrich Fitzner BASF/NAE 955/03 PCT 06.27.2005 BASF Aktiengesellschaft Use as solubility promoters of polymers comprising ether groups This patent application claims - the priority of 5 DE 10 2004 031 158.7. The present invention relates to the use as solubility promoters of polymers comprising ether groups, in particular in cosmetics, drugs, foodstuffs, food 10 supplements and animal fodder, very particularly preferably in the preparation of plant protection products, it being possible for the polymers to be obtained by copolymerization of (A) optionally at least one ethylenically 15 unsaturated mono- or dicarboxylic acid or at least one anhydride derived from an ethylenically unsaturated mono- or dicarboxylic acid, (B) at least one hydrophobic monomer exhibiting 20 aromatic functional groups and/or aliphatic functional groups or aromatic and aliphatic functional groups, (C) at least one allyl alcohol alkoxylate, (D) if appropriate, additional monoethylenically 25 unsaturated monomers. The most varied polymers for the most varied applications are known from the state of the art. 30 The use of copolymers of maleic anhydride and optionally a second monomer, for example the styrene, isobutene or vinyl acetate, is disclosed in EP 0 628 085, the copolymers being reacted with alkoxylated alcohols before use in retanning and 35 filling. EP 0 792 377 discloses a process in which tanning and if appropriate also pretanning by aldehydes or other BASF/NAE 955/03 PCT - 2 reactive carbonyl compounds is carried out in the presence of polymers, for example maleic anhydride/alpha-olefin/styrene terpolymers (variant I). 5 US 5 646 225 and US 5 728 777 disclose copolymers of styrene, methacrylic acid and mono- and dipropoxylated allyl alcohol and the use of the copolymers in water based and solvent-based inks (US 5 728 777). 10 US 4 847 410 and US 4 959 156 disclose the preparation of copolymers of allyl alcohol alkoxylates and (meth)acrylic acid and the use thereof as dispersants. Furthermore, EP-A-0 601 536 discloses water-soluble 15 graft copolymers which can be used as dispersants in aqueous inorganic binders. WO 01/96007 discloses water-soluble copolymers which are prepared by copolymerization of (meth)acrylic acid 20 or of maleic acid hemiesters, an alkyl-capped alkoxylated hemiester and optionally a dicarboxylic acid, as well as optionally styrene, and discloses their use as dispersants for pigments, such as, for example, CaCO3. 25 In addition, there are, in the field of active substances, inclusive of the plant protection field, numerous polymers with the most varied application possibilities. Reference may be made, for example, to 30 WO 03/043420. It discloses the use of copolymers as adjuvants in the treatment of plants. The copolymers consist of olefins and/or vinyl ethers, and also of ethylenically unsaturated dicarboxylic acids or dicarboxylic acid derivatives and additional 35 comonomers. Reference may also be made to DE 103 38 437, which discloses the formulation of agricultural active agents BASF/NAE 955/03 PCT - 3 with adjuvants based on block copolymers. Likewise, DE 103 51 004 discloses random radical polymers based on sulfonate-comprising acrylates and 5 their use in active substance formulation; in particular in the plant protection field. In addition, EP 002820951 discloses sustained-release preparations for active substances which are formed 10 from a copolymer consisting of allyl alcohol alkoxylates and maleic anhydride. Finally, it may also be pointed out that US 2 872 369 discloses copolymers which increase the solubility of 15 sparingly soluble components in polar solvents. It is the aim of the present invention henceforth to convert hydrophobic water-soluble active and effect substances, with the help of polymers, into a stable 20 aqueous formulation. Stable is understood as meaning, for the purposes of the invention, that the formulations are stable towards sedimentation and creaming over a time period and 25 temperature range sufficient for the respective use. The term "creaming" is understood to mean, in this connection, the enriching of the dispersed oil drops, which typically are generally lighter, in the upper part of an oil-in-water emulsion. Thus, the stability 30 of an active substance formulation over one or more years is a precondition, for example, for application in plant protection. In order to enhance the action and to increase the bioavailability of sparingly water soluble active and effect substances, these can, in 35 extreme cases, be dissolved with the help of the polymers. Mention may be made, as an example, of the dissolution BASF/NAE 955/03 PCT -4 of active substances in surfactant-like polymer micelles, by what means the active substances are stabilized in molecularly dispersed fashion in the aqueous formulation. The term "molecularly dispersed" 5 means in this connection that no active substance crystals can be detected under a transmission electron microscope. It was accordingly an object of the present invention 10 to make available polymers which can be used as solubility promoters, in particular in cosmetics, drugs, foodstuffs, food supplements and animal fodder, particularly preferably in the preparation of plant protection products. 15 The object according to the invention is achieved by the use as solubility promoters of polymers comprising ether groups, in particular in cosmetics, drugs, foodstuffs, food supplements and animal fodder, very 20 particularly in the preparation of plant protection products, it being possible for the polymers to be obtained by copolymerization of' (A) optionally at least one ethylenically unsaturated mono- or dicarboxylic acid and/or 25 at least one anhydride derived from an ethylenically unsaturated mono- or dicarboxylic acid, (B) at least one hydrophobic monomer exhibiting aromatic functional groups and/or aliphatic 30 functional groups or aromatic and aliphatic functional groups, (C) at least one allyl alcohol alkoxylate, (D) if appropriate, additional monoethylenically unsaturated monomers. 35 The term "solubility promoter" describes frequently surface-active materials which, by their presence, render other compounds, which are virtually insoluble BASF/NAE 955/03 PCT - 5 in a certain solvent, soluble or emulsifiable in this solvent (solubilization). There are solubility promoters which form a molecular compound with the sparingly soluble substance and those which act by 5 micelle formation or even those which give a "latent solvent" its solvating power. Such polymers are already known from DE 103 33 749. However, only the use for the treatment of leather is 10 described in this patent application. Additional employment possibilities are not mentioned. It is henceforth surprising according to the invention that the copolymers described are also suitable as 15 solubility promoters, in particular in cosmetics, drugs, foodstuffs, food supplements and animal fodder, particulary preferably in the preparation of plant protection products. 20 The content of active and/or effect substance can be varied over wide ranges. In particular, the amphiphilic polymer compositions make possible the preparation of "active substance concentrates" which comprise the active substance in an amount of at least 5% by weight, 25 e.g. in an amount of 5 to 50% by weight and in particular in an amount of 5 to 20% by weight, based on the total weight of the composition. The aqueous active substance compositions according to 30 the invention can advantageously be formulated in the form devoid of or low in solvent, i.e. the proportion of organic solvents in the aqueous active substance composition is frequently no more than 10% by weight, in particular no more than 5% by weight and in 35 particular no more than 1% by weight, based on the total weight of the composition. A multitude of different active and effect substances BASF/NAE 955/03 PCT - 6 can be formulated in the aqueous compositions according to the invention. A particular embodiment of the invention relates to the formulation of active substances for plant protection, i.e. of herbicides, 5 fungicides, nematicides, acaricides, insecticides and active substances which regulate plant growth. Examples of fungicidal active substances which can be formulated as aqueous active substance composition 10 according to the invention comprise: Pesticides are known to a person skilled in the art from the literature. The term "pesticide" means here at least one active substance chosen from the group 15 consisting of the insecticides, fungicides, herbicides and/or safeners, growth regulators (see Pesticide Manual, 13th Ed. (2003)), Insecticides 20 e organo(thio)phosphates, such as acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorphos, dicrotophos, dimethoate, disulfoton, 25 ethion, EPN, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, oxydemeton methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos 30 methyl, profenofos, prothiofos, pirimiphos-ethyl, pyraclofos, pyridaphenthion, sulprophos, triazophos, trichlorfon, tetrachlorvinphos or vamidothion; 35 e carbamates, such as alanycarb, benfuracarb, bendiocarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, indoxacarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb BASF/NAE 955/03 PCT -7 or triazamate; e pyrethroids, such as allethrin, bifenthrin, cyfluthrin, cycloprothrin, cyphenothrin, cyper 5 methrin and the alpha, beta, theta and zeta isomers, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda cyhalothrin, imiprothrin, permethrin, prallethrin, pyrethrin I, pyrethrin II, silafluofen, tau 10 fluvalinate, tefluthrin, tetramethrin, tralomethrin, alpha-cypermethrin, transfluthrin, zeta-cypermethrin; e arthropodal growth regulators, such as a) chitin 15 synthesis inhibitors, e.g. benzoylureas, such as chlorfluazuron, cyromazine, diflubenzuron, flucy cloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole or clofentazine; 20 b) ecdysone antagonists, such as halofenozide, methoxyfenozide or tebufenozide; c) :juvenile hormone mimics, such as pyriproxyfen, methoprene or fenoxycarb; d) lipid biosynthesis inhibitors, such as spirodiclofen; 25 * neonicotinoids, such as flonicamid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, niten pyram, nithiazine, acetamiprid or thiacloprid; 30 * pryazole insecticides, such as acetoprole, ethiprole, fipronil, tebufenpyrad, tolfenpyrad and vaniliprole; e furthermore unclassified insecticides, such as 35 abamectin, acequinocyl, acetamipirid, amitraz, azadirachtin, bensutap, bifenazate, cartap, chlor fenapyr, chlordimeform, cyromazine, diafenthiuron, dinetofuran, diofenolan, emamectin, endosulfan, BASF/NAE 955/03 PCT - 8 ethiprole, fenazaquin, fipronil, formetanate, formetanate hydrochloride, gamma-HCH, hydra methylnon, imidacloprid, indoxacarb, isoprocarb, metolcarb, piperonyl butoxide, pyridaben, 5 pymetrozine, spinosad, tebufenpyrad, thiamethoxam, thiocyclam, XMC and xylylcarb, pyridalyl, flonicamid, fluacrypyrim, milbemectin, spiro mesifen, flupyrazofos, NC 512, tolfenpyrad, flubendiamide, bistrifluron, benclothiaz, pyra 10 fluprole, pyriprole, amidoflumet, flufenerim, cyflumetofen, acequinocyl lepimectin, profluthrin, dimefluthrin, metaflumizone, N-R1-2, 2-dihalo-1-R2 cyclopropanecarboxamide 2-(2,6-dichloro-a,a,a trifluoro-p-tolyl)hydrazone, N-Rl-2,2,-di-R3 15 propionamide 2-(2,6-dichloro-a,a,a-trifluoro-p tolyl)hydrazone, Ri being methyl or ethyl, halo being chlorine or bromine, R2 being H (hydrogen) or methyl and R3 being methyl or ethyl, preferably N-ethyl-2,2-dichloro-l-methyl 20 cyclopropanecarboxamide 2-(2,6-dichloro-a, a,a-tri fluoro-p-tolyl)hydrazone, N-ethyl-2,2-dimethyl propionamide 2-(2,6-dichloro-a,a,a-trifluoro-p tolyl)hydrazone, acid of the following formula HN O 0 25 e -O aminoisothiazole of the formula C1 R N N N N-S w 30 in which BASF/NAE 955/03 PCT -9 R -CH 2 0CH 3 or H, and R = -CF 2
CF
2
CF
3 ; 5 anthranilamide of the formula / \Br C1 N N H O/1 N H and an insecticidal active compound of the following 10 formula CF HN C 3 The following list of fungicides shows possible active substances but should not be limited to these: 15 * acylalanines, e.g. benalaxyl, furalaxyl, metalaxyl, ofurace or oxadixyl; e amine derivatives, e.g. aldimorph, dodine, 20 dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine or tridemorph; e anilinopyrimidines, e.g. pyrimethanil, mepanipyrim or cyrodinyl; 25 e antibiotics, e.g. cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin, streptomycin or validamycin A; 30 e azoles, e.g. bitertanol, bromuconazole, BASF/NAE 955/03 PCT - 10 cyazofamid, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, etridiazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fuberidazole, hexaconazole, hymexazol, 5 imazalil, imibenconazole, metconazole, myclobutanil, penconazole, pefurazoate, propi conazole, prochloraz, prothioconazole, sime conazole, tebuconazole, tetraconazole, thiabendazole, triadimefon, triadimenol, 10 triflumizole, triticonazole, 5-chloro-7- (4 methylpiperidin-1-yl) -6- (2,4, 6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, 2-butoxy-6-iodo 3-propylchromen-4-one or 3-(3-bromo-6-fluoro-2 methylindol-1-ylsulfonyl) - [1,2,4] triazole-1 15 sulfonic acid dimethylamide; e dicarboximides, e.g. iprodione, myclozolin, procymidone or vinclozolin; 20 e dithiocarbamates, e.g. ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram or zineb; e heterocyclic compounds, e.g. anilazine, benomyl, 25 boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, ethirimol, dimethirimol, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, octhilinone, 30 picobenzamid, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole, triforine, 3-[5-(4-chlorophenyl) 2,3-dimethylisoxazolidin-3-yl]pyridine or 35 bupirimate; e copper fungicides, e.g. Bordeaux mixture, copper acetate, copper hydroxyide, copper oxychloride or BASF/NAE 955/03 PCT - 11 basic copper sulfate; e nitrophenyl derivatives, e.g. binapacryl, dinocap, dinobuton or nitrophtal-isopropyl; 5 e phenylpyrroles, e.g. fenpiclonil or fludioxonil; e sulfur; 10 e organometallic compounds, e.g. fentin salts; e organophosphorous compounds, e.g. edifenphos, iprobenfos, pyrazophos, tolclofos-methyl, fosetyl, fosetyl-aluminum or phosphorous acid; 15 e other fungicides, e.g. acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezine, diclocymet, diethofencarb, edifenphos, ethaboxam, 20 fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, tolclofos methyl, quintozene, zoxamide, isoprothiolane, 25 probenfos, fluopicolide (picobenzamid), mandipropamid, N-(2-{4-[3-(4-chlorophenyl)prop-2 ynyloxy]-3-methoxyphenyl}ethyl)-2 methylsulfonylamino-3-methylbutyramide, N-(2-{4 [3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxy 30 phenyl}ethyl)-2-ethylsulfonylamino-3 methylbutyramide, furametpyr, thifluzamide, penthiopyrad, fenhexamid, 3,4-dichloroisothiazole 5-carboxylic acid (2-cyanophenyl)amide, flubenthiavalicarb, 3-(4-chlorophenyl)-3-(2 35 isopropoxycarbonylamino-3-methylbutyrylamino) propionic acid methyl ester, {2-chloro-5-[l-(6 methylpyridin-2-ylmethoxyimino)ethyl]benzyl} carbamic acid methyl ester, {2-chloro-5-[l-(3- BASF/NAE 955/03 PCT - 12 methylbenzyloxyimino)ethyl]benzyl}carbamic acid methyl ester, flusulfamide, phthalide or hexachlorobenzene; 5 e amides of the formula o / H3 S N
H
3 C-<\I N H R1, R2 in which X is CHF 2 or CH 3 , and 10
R
1 and R 2 are, independently of one another, halogen, methyl or halomethyl; e strobilurins, e.g. azoxystrobin, dimoxystrobin, 15 enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin; * sulfenic acid derivatives, e.g. captafol, captan, 20 dichlofluanid, folpet or tolylfluanid; e cinnamamides and analogs, e.g. dimethomorph, flumetover or flumorph; 25 e amide fungicides, e.g. cyclofenamid or (Z)-N-[a (cyclopropylmethoxyimino)-2,3-difluoro-6 (difluoromethoxy)benzyl]-2-phenylacetamide. The following list of herbicides demonstrates possible 30 active substances but should not be limited to these: compounds which inhibit the biosynthesis of lipids, e.g. chlorazifop, clodinafop, clofop, cyhalofop, ciclofop, fenoxaprop, fenoxaprop-P, fenthiaprop, BASF/NAE 955/03 PCT - 13 fluazifop, fluazifop-P, haloxyfop, haloxyfop-P, isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P, trifop, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, 5 tepraloxydim, tralkoxydim, butylate, cycloate, di allate, dimepiperate, EPTC, esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb, pebulate, prosulfocarb, sulfallate, thiobencarb, thiocarbazil, tri-allate, vernolate, benfuresate, 10 ethofumesate and bensulide; ALS inhibitors, such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, 15 flazasulfuron, flupyrsulfuron, foramsulfuron, halo sulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tri 20 benuron, trifloxysulfuron, triflusulfuron, trito sulfuron, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, cloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, bispyribac, pyriminobac, propoxycarbazone, 25 flucarbazone, pyribenzoxim, pyriftalid and pyrithiobac; compounds which inhibit photosynthesis, such as atraton, atrazine, ametryn, aziprotryn, cyanazine, cyanatryn, chlorazine, cyprazine, desmetryn, 30 dimethametryn, dipropetryn, eglinazine, ipazine, mesoprazine, methometon, methoprotryne, procyazine, proglinazine, prometon, prometryn, propazine, sebuthylazine, secbumeton, simazine, simeton, simetryn, terbumeton, terbuthylazine and terbutryn; 35 protoporphyrinogen IX oxidase inhibitors, such as acifluorfen, bifenox, chlomethoxyfen, chlornitrofen, ethoxyfen, fluorodifen, fluoroglycofen, fluoronitrofen, BASF/NAE 955/03 PCT - 14 fomesaf en, furyloxyf en, halosaf en, lactof en, nitrof en, nitrofluorfen, oxyfluorfen, fluazolate, pyraflufen, cinidon-ethyl, flumiclorac, flumioxazin, flumipropyn, fluthiacet, thidiazimin, oxadiazon, oxadiargyl, 5 azafenidin, carfentrazone, sulfentrazone, pentoxazone, benzfendizone, butafenacil, pyraclonil, profluazol, flufenpyr, flupropacil, nipyraclofen and etnipromid; herbicides, such as metflurazon, norflurazon, 10 flufenican, diflufenican, picolinafen, beflubutamid, fluridone, flurochloridone, flurtamone, mesotrione, sulcotrione, isoxachlortole, isoxaflutole, benzofenap, pyrazolynate, pyrazoxyfen, benzobicyclon, amitrole, clomazone, aclonifen, 4-(3-trifluoromethylphenoxy)-2 15 (4-trifluoromethylphenyl)pyrimidine and 3-heterocyclyl substituted benzoyl derivatives of the formula (cf. WO-A-96/26202, WO-A-97/41116, WO-A-97/41117 and WO-A-97/41118) R 3 0 R 8 R9 N / 10 12 OH R R R 20 in which the substituents R 8 to R1 3 have the following meanings: 25 R8, R represent hydrogen, halogen, Ci-C 6 -alkyl, Ci-C 6 haloalkyl, C 1
-C
6 -alkoxy, C 1
-C
6 -haloalkoxy, C1-C6 alkylthio, C 1
-C
6 -alkylsulfinyl or C 1
-C
6 -alkylsulfonyl;
R
9 represents a heterocyclic radical from the group 30 consisting of thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 4,5-di hydroisoxazol-3-yl, 4, 5-dihydroisoxazol-4-yl and 4,5-dihydroisoxazol-5-yl, in which the abovementioned radicals can carry one or more substituents, e.g. can 35 be mono-, di-, tri- or tetrasubstituted by halogen, BASF/NAE 955/03 PCT - 15 C 1
-C
4 -alkyl, C 1
-C
4 -alkoxy, C 1
-C
4 -haloalkyl, C 1
-C
4 -halo alkoxy or C 1
-C
4 -alkylthio; R represents hydrogen, halogen or C 1
-C
6 -alkyl; 5
R
12 represents C 1
-C
6 -alkyl; R represents hydrogen or C 1
-C
6 -alkyl. 10 Additional suitable herbicides are EPSP synthase inhibitors, such as glyphosate; glutamine synthase inhibitors, such as glufosinate and bilanafos; 15 DHP synthase inhibitors, such as asulam; mitosis inhibitors, such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, 20 methalpropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, trifluralin, amiprofos-methyl, butamifos, dithiopyr, thiazopyr, propyzamide, tebutam, chlorthal, carbetamide, chlorbufam, chlorpropham and propham; 25 VLCFA inhibitors, such as acetochlor, alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor, dimethenamid, dimethenamid-P, metaza chlor, metolachlor, S-metolachlor, pretilachlor, propa 30 chlor, propisochlor, prynachlor, terbuchlor, thenylchlor, xylachlor, allidochlor, CDEA, epronaz, diphenamid, napropamide, naproanilide, pethoxamid, flufenacet, mefenacet, fentrazamide, anilofos, piperophos, cafenstrole, indanofan and tridiphane; 35 inhibitors for the biosynthesis of cellulose, such as dichlobenil, chlorthiamid, isoxaben and flupoxam; BASF/NAE 955/03 PCT - 16 herbicides, such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen and medinoterb; auxin herbicides, such as clomeprop, 2,4-D, 2,4,5-T, 5 MCPA, MCPA-thioethyl, dichlorprop, dichlorprop-P, mecoprop, mecoprop-P, 2,4-DB, MCPB, chloramben, dicamba, 2,3,6-TBA, tricamba, quinclorac, quinmerac, clopyralid, fluroxypyr, picloram, triclopyr and benazolin; 10 auxin transport inhibitors, such as naptalam and diflufenzopyr; in addition: benzoylprop, flamprop, flamprop-M, 15 bromobutide, chlorflurenol, cinmethylin, methyldymron, etobenzanid, fosamine, metam, pyributicarb, oxazi clomefone, dazomet, triaziflam and methyl bromide. The term "safener" has the following meaning: it is 20 known that, in some cases, better herbicidal tolerance can be achieved by the joint application of herbicides having a specific action with organic active compounds which themselves can exert a herbicidal effect. In these cases, these compounds act as antidote or 25 antagonist and, because they reduce or avert damage to useful plants, are described as "safeners". The following list demonstrates possible safeners but should not be limited to these: 30 benoxacor, cloquintocet, cyometrinil, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, 2,2,5-tri 35 methyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148), 4- (dichloroacetyl) -l-oxa-4 -azaspiro [4.5] decane (AD-67; MON 4660) and oxabetrinil.
BASF/NAE 955/03 PCT - 17 The following list of compounds with a growth regulating effect demonstrates possible active substances but should not be limited to these: 5 1-naphthaleneacetamide, 1-naphthaleneacetic acid, 2-naphthoxyacetic acid, 3-CPA, 4-CPA, ancymidol, anthraquinone, BAP, butifos, tribufos, butralin, chlor flurenol, chlormequat, clofencet, cyclanilide, daminozide, dicamba, dikegulac-sodium, dimethipin, 10 chlorfenethol, etacelasil, ethephon, ethychlozate, fenoprop, 2,4,5-TP, fluoridamid, flurprimidol, flutriafol, gibberellic acid, gibberellin, guazatine, imazalil, indolebutyric acid, indoleacetic acid, karetazan, kinetin, lactidichlor-ethyl, maleic 15 hydrazide, mefluidide, mepiquat chloride, naptalam, paclobutrazol, prohexadione-calcium, quinmerac, sintofen, tetcyclacis, thidiazuron, triiodobenzoic acid, triapenthenol, triazethan, tribufos, trinexapac ethyl and uniconazole. 20 e 2-methoxybenzophenones, such as those disclosed in EP-A 897 904 by the general formula (I), e.g. metrafenone; 25 e 6-aryl-[1,2,4]triazolo[1,5-a]pyrimidines, such as those disclosed, e.g., in WO 98/46608, WO 99/41255 or WO 03/004465, each time by the general formula (I). 30 Examples of herbicides which can be formulated as aqueous active substance composition according to the invention comprise: " 1,3,4-thiadiazoles, such as buthidazole and 35 cyprazole; e amides, such as, allidochlor, benzoylprop-ethyl, bromobutide, chlorthiamid, dimepiperate, BASF/NAE 955/03 PCT - 18 dimethenamid, diphenamid, etobenzanid, flamprop methyl, fosamine, isoxaben, metazachlor, alachlor, acetochlor, metolachlor, monalide, naptalam, pronamide or propanil; 5 " aminophosphoric acids, such as bilanafos, buminafos, glufosinate-ammonium, glyphosate or sulfosate; 10 * aminotriazoles, such as amitrole; e anilides, such as anilofos or mefenacet; e aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 15 clomeprop, dichlorprop, dichlorprop-P, fenoprop, fluroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, naproanilide or triclopyr; * benzoic acids, such as chloramben or dicamba; 20 " benzothiadiazinones, such as bentazon; " bleachers, such as clomazone, diflufenican, fluorochloridone, flupoxam, fluridone, pyrazolate 25 or sulcotrione; " carbamates, such as carbetamide, clorbufam, chlorpropham, desmedipham, phenmedipham or vernolate; 30 * quinolinecarboxylic acids, such as quiriclorac or quinmerac; * dichloropropionic acids, such as dalapon; 35 " dihydrobenzofurans, such as ethofumesate; e dihydrofuran-3-ones, such as flurtamone; BASF/NAE 955/03 PCT - 19 e dinitroanilines, such as benefin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, 5 prodiamine, profluralin or trifluralin; e dinitrophenols, such as bromofenoxim, dinoseb, dinoseb acetate, dinoterb, DNOC or minoterb acetate; 10 * diphenyl ethers, such as acifluorfen-sodium, aclonifen, bifenox, chlornitrofen, difenoxuron, ethoxyfen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, 15 nitrofluorfen or oxyfluorfen; e dipyridyls, such as cyperquat, difenzoquat metilsulfate, diquat or paraquat dichloride; 20 e imidazoles, such as isocarbamid; e imidazolinones, such as imazamethapyr, imazapyr, imazaquin, imazethabenz-methyl, imazethapyr, imazapic or imazamox; 25 e oxadiazoles, such as methazole, oxadiargyl or oxadiazone; e oxiranes, such as tridiphane; 30 * phenols, such as bromoxynil or ioxynil; " phenoxyphenoxypropionates, such as clodinafop, cyhalofop-butyl, diclofop-methyl, fenoxaprop 35 ethyl, fenoxaprop-P-ethyl, fenthiaprop-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, BASF/NAE 955/03 PCT - 20 isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl or quizalofop-tefuryl; e phenylacetic acids, such as chlorfenac; 5 * phenylpropionic acids, such as chlorophenprop methyl; e ppi active substances, such as benzofenap, 10 cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, pyrazoxyfen, sulfentrazone or thidiazimin; e pyrazoles, such as nipyraclofen; 15 * pyridazines, such as chloridazon, maleic hydrazide, norflurazon or pyridate; * pyridinecarboxylic acids, such as clopyralid, 20 dithiopyr, picloram or thiazopyr; e pyrimidyl ethers, such as pyrithiobac-acid, pyrithiobac-sodium, KIH-2023 or KIH-6127; 25 o sulfonamides, such as flumetsulam or metosulam; e triazolecarboxamides, such as triazofenamide; o uracils, such as bromacil, lenacil or terbacil; 30 e furthermore benazolin, benfuresate, bensulide, benzofluor, bentazon, butamifos, cafenstrole, chlorthal-dimethyl, cinmethylin, dichlobenil, endothall, fluorbentranil, mefluidide, 35 perfluidone, piperophos, topramezone and prohexadione-calcium; BASF/NAE 955/03 PCT - 21 e sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron ethyl, chlorsulfuron, cinosulfuron, cyclo sulfamuron, ethametsulfuron-methyl, flazasulfuron, 5 halosulfuron-methyl, imazosulfuron, metsulfuron methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl or 10 tritosulfuron; " plant protection active substances of the cyclohexenone type, such as alloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim and 15 tralkoxydim. Very particularly preferred herbicidal active substances of the cyclohexenone type are: tepraloxydim (cf. AGROW, No. 243, 11.3.95, page 21, caloxydim) and 2-(1-[2-{4-chlorphenoxy}propyloxyimino]butyl)-3 20 hydroxy-5-(2H-tetrahydrothiopyran-3-yl)-2 cyclohexen-1-one, and of the sulfonylurea type: N-(((4-methoxy-6-[trifluoromethyl]-1,3,5-triazin 2-yl)amino)carbonyl)-2-(trifluoromethyl)benzene sulfonamide. 25 Examples of insecticides which can be formulated as aqueous active substance composition according to the invention comprise: 30 e pyrethroids, such as bifenthrin, cyfluthrin, cycloprothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda-cyhalothrin, permethrin, silafluofen, tau-fluvalinate, 35 tefluthrin, tralomethrin,' alpha-cypermethrin or zeta-cypermethrin; BASF/NAE 955/03 PCT - 22 * N-phenylsemicarbazones, such as those disclosed in EP-A 462 456 by the general formula (I), in particular compounds of the general formula (IV) H H I I RN IN 13 R R 5 o in which Ru and R 12 are, independently of one another, hydrogen, halogen, CN, Ci-C 4 alkyl, C 1
-C
4 alkoxy, C 1
-C
4 haloalkyl or Ci-C 4 haloalkoxy and R 13 is Ci-C 4 alkoxy, 10 C 1
-C
4 haloalkyl or C 1
-C
4 haloalkoxy, e.g. compound (IV), in which R 1 is 3-CF 3 and R 2 is 4-CN and R 3 is 4-OCF 3 . Useful growth regulators are, e.g. chlormequat 15 chloride, mepiquat chloride, prohexadione-calcium or the group of the gibberellins. These include, e.g., the gillberellins GA1, GA3, GA4, GA5 and GA7, and the like, and the corresponding exo-16,17-dihydrogibberellins and also the derivatives thereof, e.g. the esters with 20 Ci-C 4 -carboxylic acids. The exo-16,17-dihydro-GA5 13-acetate is preferred according to the invention. A preferred embodiment of the invention relates to the use of the amphiphilic polymer compositions according 25 to the invention in the preparation of aqueous active substance compositions of fungicides, in particular strobilurins, azoles and 6-aryltriazolo[1,5 a]pyrimidines, such as those disclosed, e.g., in WO 98/46608, WO 99/41255 or WO 03/004465, each time by 30 the general formula (I), in particular for active substances of the general formula (V), BASF/NAE 955/03 PCT - 23 (L)n Rx N''N (V) N N XL1 in which: 5 Rx is an NR 4
R"
5 group, or linear or branched
C
1 -Cs-alkyl, if appropriate substituted by halogen, OH, C 1
-C
4 alkoxy, phenyl or C 3
-C
6 cycloalkyl; C 2
-C
6 alkenyl, C 3
-C
6 cycloalkyl, C 3
-C
6 cycloalkenyl, 10 phenyl or naphthyl, it being possible for the 4 last-mentioned radicals to exhibit 1, 2, 3 or 4 substituents chosen from halogen, OH, C 1
-C
4 alkyl,
C
1
-C
4 haloalkoxy, C 1
-C
4 alkoxy and C 1
-C
4 haloalkyl; 15 R1 4 and R 15 are, independently of one another, hydrogen, Ci-C 8 -alkyl, Ci-CB-haloalkyl,
C
3 -Cio-cycloalkyl,
C
3
-C
6 -halocycloalkyl,
C
2
-C
8 -alkenyl, C 4 -Cio-alkadienyl,
C
2
-C
8 -halo alkenyl, C 3
-C
6 -cycloalkenyl, C 2 -CB-halo 20 cycloalkenyl, C 2
-C
8 -alkynyl, C 2 -CB-haloalkynyl or
C
3
-C
6 -cycloalkynyl; R 14 and R 1 5 , together with the nitrogen atom to which they are bonded, form a five- to eight 25 membered heterocyclyl which is bonded via N and can comprise one, two or three additional heteratoms from the group consisting of 0, N and S as ring member and/or can carry one or more substituents from the group consisting of 30 halogen, Ci-C 6 -alkyl, Cl-C 6 -haloalkyl,
C
2
-C
6 -alkenyl, C 2
-C
6 -haloalkenyl, CI-C 6 -alkoxy, Ci
C
6 -haloalkoxy, C 3
-C
6 -alkenyloxy, C 3
-
BASF/NAE 955/03 PCT - 24 C 6 -haloalkenyloxy, (exo) -Ci-C 6 -alkylene and oxy
C
1
-C
3 -alkylenoxy; L is chosen from halogen, cyano, Ci-C 6 -alkyl, 5 Cl-C 4 .haloalkyl, Ci-C 6 -alkoxy, C 1
-C
4 -haloalkoxy and Ci-C 6 -alkoxycarbonyl; Li is halogen, Ci-C 6 -alkyl or Cl-C 6 -haloalkyl and in particular fluorine or chlorine; 10 X is halogen, Ci-C 4 -alkyl, cyano, Ci-C 4 -alkoxy or Ci-C 4 -haloalkyl and preferably halogen or methyl, and in particular chlorine. 15 Examples of compounds of the formula (V) are: 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(4-methylpiperazin-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 20 5-chloro-7-(morpholin-1-yl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(piperidin-1-yl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(morpholin-1-yl)-6-(2,4,6-trifluorophenyl) 25 [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(isopropylamino)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(cyclopentylamino)-6-(2,4,6-trifluoro phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 30 5-chloro-7-(2,2,2-trifluoroethylamino)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(1,1,1-trifluoropropan-2-ylamino)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(3,3-dimethylbut-2-ylamino)-6-(2,4,6 35 trifluorophenyl)-[1,2,4]triazolo[1,5-alpyrimidine, 5-chloro-7-(cyclohexylmethyl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(cyclohexyl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, BASF/NAE 955/03 PCT - 25 5-chloro-7-(2-methylbutan-3-yl)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro-7- (3-methylpropan-1-yl) -6- (2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5 5-chloro-7-(4-methylcyclohexan-1-yl)-6-(2,4,6 trifluorophenyl) -[1,2,4]triazolo[1,5-alpyrimidine, 5-chloro-7- (hexan-3-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro-7- (2-methylbutan-1-yl) -6- (2,4,6 10 trifluorophenyl) -[1,2,4]triazolo[1,5-alpyrimidine, 5-chloro-7-(3-methylbutan-1-yl)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-chloro-7- (1-methylpropan-1-yl) -6- (2,4,6 trifluorophenyl) -[1,2,4]triazolo[l,5-alpyrimidine, 15 5-methyl-7-(4-methylpiperidin-1-yl)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-methyl-7-(4-methylpiperazin-1-yl)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-methyl-7- (iorpholin-1-yl) -6- (2,4,6-trifluorophenyl) 20 [1,2,4]triazolo[1,5-alpyrimidine, 5-methyl-7- (piperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-alpyrimidine, 5-methyl-7- (morpholin-1-yl) -6- (2,4,6-trifluorophenyl') [1,2,4] triazolo [1,5-a] pyrimidine, 25 5-methyl-7- (isopropylamino) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo[1, 5-alpyrimidine, 5-methyl-7- (cyclopentylamino) -6- (2,4,6-trifluoro phenyl)- [1,2,4]triazolo[1,5-alpyrimidine, 5-methyl-7- (2,2,2-trifluoroethylamino) -6- (2,4,6 30 trifluorophenyl) -[1,2,4]triazolo [1,5-a] pyrimidine, 5-methyl-7-(1,1,1-trifluoropropan-2-ylamino)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-methyl-7-(3,3-dimethylbutan-2-ylamino)-6-(2,4,6 trifluorophenyl) -[1,2,4] triazolo[1,5-alpyrimidine, 35 5-methyl-7- (cyclohexylmethyl) -6- (2,4,6 trifluorophenyl) -[1,2,4] triazolo [1,5-a] pyrimidine, 5-methyl-7-(cyclohexyl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, BASF/NAE 955/03 PCT - 26 5-methyl-7-(2-methylbutan-3-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-methyl-7-(3-methylpropan-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5 5-methyl-7-(4-methylcyclohexan-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-methyl-7-(hexan-3-yl)-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[1,5-a]pyrimidine, 5-methyl-7-(2-methylbutan-1-yl)-6-(2,4,6-trifluoro 10 phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine 5-methyl-7-(3-methylbutan-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine and 5-methyl-7-(1-methylpropan-1-yl)-6-(2,4,6 trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine. 15 An additional preferred embodiment of the invention relates to the use of the amphiphilic polymer compositions according to the invention in the preparation of aqueous active substance compositions of 20 insecticides, in particular of arylpyrroles, such as chlorfenapyr, of pyrethroids, such as bifenthrin, cyfluthrin, cycloprothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda-cyhalothrin, permethrin, 25 silafluofen, tau-fluvalinate, tefluthrin, tralomethrin, alpha-cypermethrin or zeta-cypermethrin, of neonicotinoids and of semicarbazones of the formula (IV), or of fipronil. 30 The abovementioned pesticides are used against the appropriate pests. Pests 35 Combating undesirable plant growth means the combating/destruction of plants which grow in places where they are undesirable, e.g. of dicotyledonous plants of the following types: Sinapis, Lepidium, BASF/NAE 955/03 PCT - 27 Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, 5 Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum; Monocotyledonous plants of the following types: 10 Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristyslis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, 15 Agrostis, Alopecurus, Apera. The term "undesirable insect or acarid" describes but is not limited to the following kinds: 20 Lepidoptera, for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, 25 Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha 30 funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, 35 Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia BASF/NAE 955/03 PCT - 28 pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella 5 xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia 10 ni and Zeiraphera canadensis; beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, 15 Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, 20 Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema 25 bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon 30 cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria; 35 Diptera, for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia BASF/NAE 955/03 PCT - 29 anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia 5 platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia 10 antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa; Thysanoptera, for example Frankliniella fusca, 15 Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci; Hymenoptera, for example Athalia rosae, Atta 20 cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta; Heteroptera, for example Acrosternum hilare, Blissus 25 leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta 30 perditor; Homoptera, for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis 35 grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, BASF/NAE 955/03 PCT - 30 Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis 5 plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, 10 Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, 15 Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantii and Viteus vitifolii; Termites (Isoptera), e.g. Calotermes flavicollis, 20 Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis; Orthoptera, e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa 25 gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus 30 maroccanus and Tachycines asynamorus; Arachnoidea, for example Acarina, e.g. from the Argasidae, Ixodidae and Sarcoptidae families, e.g. Amblyomma americanum, Amblyomma variegatum, Argas 35 persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus BASF/NAE 955/03 PCT - 31 gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp., e.g. Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; 5 Tarsonemidae spp., e.g. Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp., e.g. Brevipalpus phoenicis; Tetranychidae spp., e.g. Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius. and 10 Tetranychus urticae, Panonychus ulmi, Panonychus citri and Oligonychus pratensis; Nematodes, in particular nematodes which parasitize plants, e.g. plant root knot nematodes, Meloidogyne 15 hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera 20 species; seed gall nematodes, Anguina species; stem and foliar nematodes, Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring 25 nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; awl nematodes, Dolichodorus species; spiral nematodes, 30 Heliocotylenchus multicinctus and other Helicotylenchus species; sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; 35 needle nematodes, Longidorus elongatus and other Longidorus species; lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus BASF/NAE 955/03 PCT - 32 species; burrowing nematodes, Radopholus similis and other Radopholus species; reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; stubby root nematodes, 5 Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; citrus nematodes, Tylenchulus species; dagger nematodes, Xiphinema 10 species; and rice pathogens, e.g. rice water weevil (Lissorhoptrus oryzaphilus), rice stem borer (Chilo suppresalis) , rice leaf roller, rice leaf beetle, rice 15 leaf miner (Agromyca oryzae), leafhoppers (Nephotettix spp.; especially smaller brown leafhopper, green rice leafhopper), planthoppers (Delphacidae; especially white backed planthopper, brown rice planthopper), stinkbugs. 20 The term "phytopathogenic fungi" describes but is not limited to the following species: Blumeria graminis (powdery mildew) on cereals, Erysiphe 25 cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Uncinula necator on grape vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis on apples, 30 Bipolaris and Drechslera species on cereals, rice and lawns, Septoria nodorum on wheat, Botrytis cinerea on strawberries, vegetables, ornamental plants and grape vines, Mycosphaerella species on bananas, peanuts and cereals, Pseudocercosporella herpotrichoides on wheat 35 and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Pseudoperonospora species on cucurbits and hops, Plasmopara viticola on grape vines, Alternaria species on fruit and BASF/NAE 955/03 PCT - 33 vegetables, and also Fusarium and Verticillium species, Bipolaris and Drechslera species and also Pyricularia oryzae, Corticium sasakii (syn. Rhizoctonia solani) and Cochliobolus miyabeanus on rice plants and, if 5 appropriate, on their seeds, Paecilomyces variotii on materials such as wood. In addition, the amphiphilic polymer compositions according to the invention are suitable for the 10 preparation of aqueous active substance compositions of pharmaceutical active substances and prodrugs. These include benzodiazepines, antihypertensives, vitamins, cytostatics, in particular taxol, anesthetics, neuroleptics, antidepressants, antibiotics, 15 antimycotics, fungicides, chemotherapeutics, urologics, thrombocyte aggregation inhibitors, sulfonamides, spasmolytics, hormones, immunglobulins, sera, thyroid therapeutic agents, psychopharmacological agents, antiparkinsonians and other antihyperkinetic agents, 20 ophthalmics, neuropathy preparations, calcium metabolism regulators, muscle relaxants, narcotics, antilipemics, hepatic therapeutic agents, coronary agents, cardiacs, immunotherapeutics, regulatory peptides and their inhibitors, hypnotics, sedatives, 25 gynecological agents, antigouts, fibrinolytic agents, enzyme preparations and transport proteins, enzyme inhibitors, emetics, circulation-promoting agents, diuretics, diagnostics, corticoids, cholinergics,, bile duct therapeutics, antiasthmatics, broncholytics, beta 30 receptor blockers, calcium antagonists, ACE inhibitors, antiarteriosclerotics, antiinflammatories, anti coagulants, antihypotensives, antihypoglycemics, antihypertonics, antifibrinolytics, antiepileptics, antiemetics, antidotes, antidiabetics, antiarrhythmics, 35 antianemics, antiallergics, anthelmintics, analgesics, analeptics, aldosterone antagonists and slimming agents. Examples of suitable pharmaceutical active substances are in particular the active substances BASF/NAE 955/03 PCT - 34 mentioned in paragraphs 0105 to 0131 of US 2003/0157170. In addition, the amphiphilic polymer compositions 5 according to the invention are suitable for the preparation of aqueous compositions of cosmetic active substances, in particular of cosmetic oils and fats, such as peanut oil, jojoba oil, coconut oil, almond oil, olive oil, palm oil, castor oil, soybean oil or 10 wheat germ oil, essential oils, such as mountain pine oil, lavender oil, rosemary oil, spruce needle oil, pine needle oil, eucalyptus oil, peppermint oil, sage oil, bergamot oil, turpentine oil, Melissa oil, juniper oil, lemon oil, anise oil, cardamom oil, camphor oil, 15 and the like, or for mixtures of these oils. In addition, the amphiphilic polymer compositions according to the invention are suitable for the preparation of aqueous compositions of food 20 supplements, such as water-insoluble vitamins and provitamins, such as vitamin A, vitamin A acetate, vitamin D, vitamin E, tocopherol derivatives, such as tocopherol acetate, and vitamin K. 25 In addition, the amphiphilic polymer compositions according to the invention are suitable for the preparation preferably of aqueous compositions for seed treatment. 30 Examples of formulation types are emulsifiable concentrates, suspensions, soluble concentrates, dispersible concentrates, pastes, pellets, wettable powders, dustable powders (DP) or granules (GR, FG, GG, MG) which can be either soluble or dispersible in 35 water. Standard formulation types for seed treatment are FS (flowable concentrates), LS (solutions), DS (powders for dry treatment), WS (water dispersible powders for slurry treatment), SS (water-soluble BASF/NAE 955/03 PCT - 35 powders SS) and ES (emulsions). The preparation of these formulations and the technology necessary therefor are known to a person skilled in the art (cf. US 3 060 084, EP-A 707 445 (for liquid concentrates), 5 Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 and ff., WO 91/13546, US 4 172 714, US 4 144 050, US 3 920 442, US 5 180 587, US 5 232 701, US 5 208 030, GB 2 095 558, 10 US 3 299 566, Klingman, Weed Control as a Science, John Wiley and Sons Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation Technology, Wiley VCH Verlag GmbH, 15 Weinheim (Federal Republic of Germany) , 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8). 20 The present invention also comprises seeds which have been treated with pesticide-comprising aqueous polymer dispersions. The amounts of pesticides expended in the seed treatment are generally from 0.1 to 10 kg/100 kg of seeds, preferably 1 to 5 kg/100 kg, in particular 1 25 to 2.5 kg/100 kg. In a preferred embodiment according to the invention, use is made of polymers which can be obtained by copolymerization of the following monomers: 30 (A) optionally at least one ethylenically unsaturated mono- or dicarboxylic acid with 3 to 8 carbon atoms and/or at least one anhydride derived from a mono- or dicarboxylic acid with 35 3 to 8 carbon atoms. Examples of ethylenically unsaturated mono- or dicarboxylic acids with 3 to 8 carbon atoms are (meth)acrylic acid, maleic acid, fumaric acid or crotonic acid; BASF/NAE 955/03 PCT - 36 very particular preference is given to acrylic acid. Mention may be made, as anhydrides derived from 5 a mono- or dicarboxylic acid with 3 to 8 carbon atoms, for example, of maleic anhydride, itaconic anhydride, citraconic anhydride or methylenemalonic anhydride, preferably itaconic anhydride and maleic anhydride and . very 10 particularly preferably maleic anhydride. Mixed anhydrides are also possible, for example the mixed anhydride of (meth)acrylic acid and acetic acid. 15 (B) At least one vinylaromatic compound, for example of the general formula (VIII) H R1 5 R (R )k (VIII) 20 in which R 14 and R 15 , independently of one another, are each hydrogen, methyl or ethyl, R 16 is methyl or ethyl and k is an integer from 0 to 2; preferably, R 14 and R 15 are each hydrogen 25 and preferably k = 0. Use is preferably made, as (B), of a methylstyrene and very particularly preferably of styrene. 30 (C) At least one alkoxylated unsaturated ether of the general formula (I) BASF/NAE 955/03 PCT - 37 R 3
R
1 0 OIn R6 (I) in which the variables in formula (I), are 5 defined as follows:
R
1 , R 2 and R 3 are identical or different and are chosen from hydrogen or Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, 10 sec-butyl and tert-butyl, particularly preferably methyl or hydrogen;
R
4 and R5 are each identical or different and are chosen from hydrogen or Ci-C 4 -alkyl, such as methyl, 15 ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, particularly preferably methyl or hydrogen; R6 is chosen from hydrogen, SO 3 M, P0 3
M
2 and preferably 20 organic radicals, such as Ci-C 30 -alkyl, preferably linear or branched, such as methyl, ethyl, n propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, 1, 2-dimethylpropyl, isoamyl, n-hexyl, 25 isohexyl, sec-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, n-hexadecyl, n-octadecyl or n eicosyl; particularly preferably Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl; CO-H (formyl) 30 or CO-Ci-C 20 -alkyl, particularly preferably acetyl, propionyl, n-butyryl, n-stearoyl or n-lauroyl; or
CO-C
6
-C
14 -aryl, such as, for example, a-naphthoyl, P-naphthoyl and preferably benzoyl CO-C 6
H
5
,
BASF/NAE 955/03 PCT - 38 M is alkali metal, in particular sodium or potassium, or NH 4 * or CH 3 , 5 n is an integer from 3 to' 100, preferably from 10 to 40, y is an integer from 0 to 10, preferably 1 to 10 and particularly preferably 1 or 2. 10 Particularly preferably, R 4 and R 5 are each hydrogen. Particularly preferably, R 1 and R 3 are hydrogen, R 2 is chosen from hydrogen or methyl, and y is 1. 15 Optionally, one or more additional monoethylenically unsaturated monomers (D) can be copolymerized. The monomer of monomers (D) which can optionally be 20 copolymerized in the polymers used in the process according to the invention are different from (A). Mention may be made, as preferred monomers (D), of: ethylenically unsaturated C 3
-C
8 -carboxylic acid 25 derivatives of the general formula (II) 0
R
7
OR
9 Ra (II) acrylamides of the formula (III), 30 BASF/NAE 955/03 PCT - 39 0 R9 7/ R 7N R (III) noncyclic amides of the general formula (IVa) and cyclic amides of the general formula (IVb) 5 7 R R7 N R4 (IVa) N (IVb) (CH )' \ 0 Ra8 2)a (CH2)A 5 0
C
1
-C
20 -alkyl vinyl ethers, such as methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl 10 vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether or n-octadecyl vinyl ether; N-vinyl derivatives of nitrogenous aromatic compounds, preferably N-vinylimidazole, 2-methyl-1-vinylimidazole, 15 N-vinyloxazolidone, N-vinyltriazole, 2-vinylpyridine, 4-vinylpyridine, 4-vinylpyridine N-oxide, N vinylimidazoline or N-vinyl-2-methylimidazoline; alkoxylated unsaturated ethers of the general formula 20 (V), R 4 R X 00- R R
*(V)
BASF/NAE 955/03 PCT - 40 esters and amides of the general formula (VI), 0 79 R X R R 8 R9 (VI) 5 unsaturated esters of the general formula (VII) 0 RO R RS (VII) 10 Monomers comprising sulfonate, phosphate or phosphonate groups are furthermore suitable, such as, for example, vinylsulfonic acid and vinylphosphonic acid and compounds of the general formula (IX) 0 R 0
.
0L P0 3
H
2 15 (IX) it being possible for phosphate groups, sulfonate groups or phosphonate groups to be present, if appropriate, partly or completely in the form of alkali 20 metal salts. the variables being defined as follows: BASF/NAE 955/03 PCT - 41 R 7 is chosen from unbranched or branched Ci-Cio-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 5 isopentyl, sec-pentyl, neopentyl, 1,2 dimethylpropyl, isoamyl, n-hexyl, isohexyl, sec hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl; particularly preferably Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec 10 butyl and tert-butyl, and in particular hydrogen;
R
8 is chosen from unbranched or branched Ci-Cio-alkyl, 15 such as methyl, ethyl, n-propyl, isopropyl, n butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, 1,2 dimethylpropyl, isoamyl, n-hexyl, isohexyl, sec hexyl, n-heptyl, n-octyl, n-nonyl or n-decyl; 20 particularly preferably Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec butyl and tert-butyl, in particular methyl 25 and in particular hydrogen;
R
9 are identical or different and are Ci-C 22 -alkyl, branched or unbranched, such as methyl, ethyl, 30 n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, 1,2-dimethylpropyl, isoamyl, n-hexyl, isohexyl, sec-hexyl, n-heptyl, n-octyl, n-nonyl, n decyl, n-dodecyl or n-eicosyl; particularly 35 preferably Ci-C 4 -alkyl, such as methyl, ethyl, n propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, or hydrogen; with the proviso that, in the formula (II), R 9 is not hydrogen; BASF/NAE 955/03 PCT - 42 A 1 is identical or different and is C 2
-C
6 -alkylene, for example -CH 2 -, - CH (CH 3 )-, -(CH 2
)
2 -, - CH 2 - CH (CH 3 )-, - (CH 2 ) 3 -, -CH 2 -CH (C 2 Hs) -, - (CH 2
)
4 -, - (CH 2 ) s-, - (CH 2 ) 6 -, 5 preferably C 1
-C
3 -alkylene; in particular -(CH 2
)
2 -,
-CH
2
-CH(CH
3 )- and -CH 2
-CH(C
2 H)-; x is an integer ranging from 2 to 6, preferably 3 to 5; 10 a is an integer ranging from 0 to 6, preferably ranging from 0 to 2; b is an integer ranging from 1 to 40, preferably 1 to 15 10; m is an integer ranging from 2 to 200, preferably 10 to 40; 20 Rio and R" are identical or different and are chosen from hydrogen or unbranched or branched Ci-Cio alkyl, unbranched and branched Ci-Cio-alkyl being defined as above; 25 X is oxygen or N-R; 12 R is chosen from unbranched or branched Ci-Cio-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, 30 isopentyl, sec-pentyl, neopentyl, 1,2 dimethylpropyl, isoamyl, n-hexyl, isohexyl, sec hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl or n hexyl; and in particular hydrogen or methyl; 35 phenyl. The remaining variables are defined as above.
BASF/NAE 955/03 PCT - 43 Compounds of the formula (III) chosen by way of example are (meth)acrylamides, such as acrylamide, N methylacrylamide, N, N-dimethylacrylamide, N ethylacrylamide, N-propylacrylamide, N-(tert 5 butyl) acrylamide, N- (tert-octyl) acrylamide, N-undecyl acrylamide or the corresponding methacrylamides. Compounds of the formula (IVa) chosen by way of example are N-vinylcarboxamides, such as N-vinylformamide, 10 N-vinyl-N-methylformamide, N-vinylacetamide or N-vinyl-N-methylacetamide; representatives of compounds of the formula (IVb) chosen by way of example are N-vinylpyrrolidone, N-vinyl-4-piperidone and N-vinyl-epsilon-caprolactam. 15 Compounds of the formula (VI) chosen by way of example are (meth)acrylates and (meth)acrylamides, such as N,N-dialkylaminoalkyl (meth)acrylates or N, N-dialkylaminoalkyl (meth) acrylamides; examples are 20 N, N-dimethylaminoethyl acrylate, N, N-dimethylaminoethyl methacrylate, N,N-diethylaminoethyl acrylate, N,N-diethylaminoethyl methacrylate, N,N-dimethyl aminopropyl acrylate, N, N-dimethylaminopropyl meth acrylate, N,N-diethylaminopropyl acrylate, N,N-diethyl 25 aminopropyl methacrylate, 2-(N,N-dimethyl amino) ethylacrylamide, 2- (N,N-dimethylamino) ethyl methacrylamide, 2-(N,N-diethylamino)ethylacrylamide, 2 (N,N-diethylamino)ethylmethacrylamide, 3-(N,N-dimethyl amino) propylacrylamide and 3-(N,N-dimethylamino)propyl 30 methacrylamide. Compounds of the formula (VII) chosen by way of example are vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate or vinyl laurate. 35 Preference is given to the use as monomers (D) of acrylic esters.
BASF/NAE 955/03 PCT - 44 Use is very particularly preferably made, as monomer (D), of methyl acrylate, methyl methacrylate, acrylamide, vinyl n-butyl ether, vinyl isobutyl ether, N-vinylformamide, N-vinylpyrrolidone, 1-vinylimidazole, 5 4-vinylpyridine, vinylphosphonic acid or vinylsulfonic acid. In one embodiment of the present invention, the monomers (A) to (D) are copolymerized as follows: 10 (A) 0 to 50% by weight of at least one ethylenically unsaturated mono- or dicarboxylic acid with 3 to 8 carbon atoms or at least one anhydride derived from a mono- or dicarboxylic acid with 3 to 8 carbon 15 atoms, preferably 5 to 30% by weight, (B) 5 to 80% by weight of at least one hydrophobic monomer, preferably 8 to 50% by weight, 20 (C) 10 to 90% by weight of at least one alkoxylated unsaturated ether of the general formula (I), preferably 40 to 75% by weight, (D) 0 to 20% by weight of at least one additional 25 monomer, preferably 2 to 10% by weight, very particularly preferably 1 to 5% by weight, the monomers being defined as above. 30 The polymers described can be prepared as follows. It is possible to copolymerize the monomers (A), (B), (C) and, if appropriate (D) with one another by solution polymerization, precipitation polymerization or, preferably, under solvent-free conditions by bulk 35 polymerization. In this connection, (A), (B), (C) and, if appropriate, (D) can copolymerize in the form of random copolymers or as block copolymers.
BASF/NAE 955/03 PCT - 45 Pressure and temperature conditions for a copolymerization of (A), (B), (C) and, if appropriate, (D) are generally not critical. The temperatures, for example, range from 60 to 200 0 C, preferably 90 to 5 1600C, and the pressure, for example,. ranges from 1 to 10 bar, preferably 1 to 3 bar. Possible reaction times are, for example, 0.5 hour to 12 hours, although even shorter and longer reaction 10 times can be envisaged. Possible solvents are preferably those solvents which are regarded as inert with regard to anhydrides derived from dicarboxylic acids with 3 to 8 carbon atoms, in 15 particular acetone, tetrahydrofuran or 1,4-dioxane. Aromatic and aliphatic hydrocarbons, for example toluene, ortho-xylene, meta-xylene, para-xylene, ethylbenzene or mixtures of one or more of the abovementioned aromatic hydrocarbons, n-hexane, 20 petroleum ether or isododecane are suitable as precipitants. Mixtures of aromatic and aliphatic hydrocarbons are also suitable. In addition, water can also be used as solvent. 25 Preferably, polymerization is carried out in the form of a bulk polymerization without the addition of solvents. If R' is chosen to be hydrogen, it can be advantageous 30 to add certain amounts, for example 1 to 30% by weight, based on the weight of all monomers, of water and thus to prevent the formation of crosslinked copolymers. Modifiers can be used, for example mercaptoethanol or 35 n-dodecyl mercaptan. Suitable amounts are, for example, 0.1 to 6% by weight, based on the weight of all monomers.
BASF/NAE 955/03 PCT - 46 The copolymerization is advantageously started by initiators, for example peroxides or hydroperoxides. Mention may be made, as peroxides or hydroperoxides, for example, of di(tert-butyl) peroxide, tert-butyl 5 peroctoate, tert-butyl perpivalate, tert-butyl per(2 ethylhexanoate), tert-butyl permaleate, tert-butyl perisobutyrate, benzoyl peroxide, diacetyl peroxide, succinyl peroxide, p-chlorobenzoyl peroxide or dicyclohexyl peroxydicarbonate. The use of redox 10 initiators is also suitable and furthermore azo compounds, such as 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2-methylpropionamidine) dihydrochloride and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile). Generally, these initiators are used in amounts of 0.1 15 to 20% by weight, preferably 0.2 to 15% by weight, calculated with regard to the weight of all monomers. Polymers are obtained by the copolymerization described above. The precipitated polymers may comprise compounds 20 of the general formula (I) and they can be subjected to the purification according to conventional methods, for example reprecipitation or extractive removal of nonreactive monomers. However, the purification can be omitted and the copolymers described above can be used 25 in the mixture with compound (I). If a solvent or precipitant has been used, it is possible to remove this after the copolymerization has ended, for example by distillation. 30 The polydispersity of the polymers described above generally lies between 2 and 10, preferably up to 7, but higher values can be accepted. The K values of the polymers described above come to 6 35 to 100, preferably 10 to 60 (measured according to H. Fikentscher at 25 0 C in, for example, water or tetrahydrofuran and a polymer concentration of 1% by weight).
BASF/NAE 955/03 PCT - 47 The preparation of monomers of the general formula (I) is known per se.
R
3 R4 R 0 O R6 2 R 55 RR 5 (I) If it is desired to prepare derivatives with R 6 equal to -CO-H (formyl) or -CO-C 1
-C
20 -alkyl or -CO-C 6
-C
14 -aryl, the starting material is. advantageously the 10 corresponding derivative with R 6 equal to hydrogen and it is reacted, for example, with mixed anhydrides or symmetrical anhydrides. Particularly preferred anhydrides are acetic anhydride, benzoic anhydride or
H-CO-O-COCH
3 . 15 The invention is described more fully below with reference to the examples. Examples: 20 Various substances with a poor solubility in water were used in order to test the suitability of the polymers according to the invention as solubility promoters.
BASF/NAE 955/03 PCT - 48 Substance Solubility in distilled water (mg/1) Pyrene 0.13 Uvinul T150* (octyl 0.007 triazone) Cl Solvent Red* (colorant) < 0.001 Cinidon-ethyl (herbicide) 0.057 Piroxicam (painkiller) 23 Pyraclostrobin (fungicide) 2.4 Metconazole (fungicide) 15 Table 1 The following measures were taken in order to test the 5 suitability of the polymers as solubility promoters: Process 1: Solid solution 0.5 g of a polymer and 0.1 g of a chosen substance were 10 dissolved in DMF (ca. 20 ml). The mixture was stirred and DMF was completely evaporated so that a liquid dispersion of the organic molecules in the polymer was obtained. A buffered aqueous solution (100 ml, pH 6.8) was added and the mixture was stirred for 24 hours. 15 Stable solutions or dispersions are obtained, i.e. no sedimentation could be observed even after ca. one week. After filtration, the solution was analyzed by means of HPLC (UV detector) and the concentration of the substances was determined. 20 Process 2: Melt emulsification 10 g of active substance melt were stirred into 90 g of aqueous polymer solution at a temperature of 65 0 C 25 comprising 30 g of polymer. Depending on the viscosity of the polymer solution and active substance, a magnetic stirrer or an UltraTurrax was used for the dissolution. The time required up to dissolution BASF/NAE 955/03 PCT - 49 equilibrium depends on the polymer and active substance and can last from seconds to hours. Stable solutions or dispersions are obtained, i.e. no sedimentation could be observed even after ca. one week. 5 Process 3: Phase inversion 10 g of the liquid or solid active substance and 30 g of polymer were dissolved in an organic solvent with a 10 boiling point of less than 100 0 C. Water was then added with stirring and the organic solvent was subsequently removed on a rotary evaporator. As much water was added to give the resulting aqueous formulation an active substance content of 10% and a polymer content of 30%. 15 Stable solutions or dispersions are obtained. Examples of the preparation of the polymers Preparation example 1: Preparation of a terpolymer 20 (Pluriol A10R/acrylic acid/styrene) (1:1:1) 373.5 g (0.75 mol) of Pluriol A01OR and 78 g (0.77 mol) of acetic anhydride were heated to 150 0 C with stirring and maintained at 150 0 C for one hour. Subsequently, 25 54 g (0.75 mol) of acrylic acid, 78.0 g (0.75 mol) of styrene and 10.1 g of di(tert-butyl) peroxide were metered in in five hours. Subsequently, the mixture was heated at 150 0 C for a further half hour. K value = 17 (1% in water) 30 Preparation example 2: Preparation of a terpolymer (Pluriol AlOR/acrylic acid/styrene) (1:1:3) 373.5 g (0.75 mol) of Pluriol A01OR were placed in a 21 35 vessel and heated to 150 0 C under a slight nitrogen stream. After reaching this temperature, 54 g (0.75 mol) of acrylic acid, 234.0 g of styrene and 13.23 g of di(tert-butyl) peroxide were metered in in BASF/NAE 955/03 PCT - 50 five hours. Subsequently, the batch was maintained at 150 0 C for half an hour. K value (1% in water) = 23 GPC in N,N-dimethylacetamide (PMMA standard): 5 Mn = 3100, Mw = 63 000 Formulation examples Formulation example 1: 10 Dissolution results with polymer from preparation example 1 according to process 1: Active substance Solubility in Solubility in the distilled water presence of [mg/l] polymer [mg/l] Uvinul T150* 0.007 2.3 Cinidon-ethyl 0.057 0.5 Pyrene 0.13 7 Piroxicam 23 92 Table 2 15 Formulation example 2: Dissolution results with polymer from preparation example 2 according to process 1: 20 Active substance Solubility in Solubility in the distilled water presence of [mg/l] polymer [mg/l] Uvinul T150* 0.007 79 Cinidon-ethyl 0.057 57 Pyrene 0.13 63 CI Solvent Red® < 0.001 0.2 Piroxicam 23 167 Table 3 BASF/NAE 955/03 PCT - 51 Formulation example 3: Dissolution of pyraclostrobin with polymer from. preparation example 2 according to process 3 5 10 g of the fungicide pyraclostrobin were dissolved in 100 g of THF together with 30 g of polymer from example 2. As much water was then added with stirring (magnetic stirrer) to give, after removal of the 10 organic solvent on a rotary evaporator, the resulting aqueous formulation an active substance content of 10% and a polymer content of 30%. The active substance pyraclostrobin is, at 700C, a 15 satisfactorily fluid melt (viscosity 2200 mPa.s) and can also be formulated according to process 2. The formulation is in both cases homogeneous, is stable towards sedimentation for at least several months and can be diluted with water (tested with demineralized 20 water and water of 100 German hardness) without resulting in sedimentation and crystallization. The polymer/active substance particles are spherical and have a diameter of ca. 30 nm. No active substance 25 crystals can be detected under an electron microscope (TEM). The nanoparticulate fungicidal formulation, which comprised only water, polymer and active substance, was 30 compared, with regard to the biological action, with a commercial formulation of the active substance pyraclostrobin in a greenhouse. For this, the active substance formulations were 35 diluted with faucet water to the desired active substance concentrations (between 4 and 250 ppm). Application on tomato plants was carried out in a spray booth with a volume of 25 ml, which corresponds to an BASF/NAE 955/03 PCT - 52 amount of water conventionally used in practice of ca. 500 1/ha. The standard fungus (phytophthora infestans) was inoculated 7 days after treatment. The test plants were placed in a greenhouse at 18-200C and 5 90% relative humidity. Scoring was carried out 5 days after inoculation by determination of the infestation of the leaves in percent. The results of the biological testing are summarized in 10 the following table (table 4). Table 4: Phytophthora infestans - Infestation [%] on tomatoes after five days as a function of the active substance content 15 Infestation [%] Infestation [%] Amount expended Formulation Commercial [ppm] example 3 product' 250 0 0 63 0 0 16 0 0 4 3 4 1) EC formulation: 23.5% by weight of pyraclostrobin, 4.7% by weight of anionic wetting agent and 20 4.7% by weight of nonionic wetting agent in 67.1% by weight of an aromatic solvent Formulation example 4: 25 Dissolution of pyraclostrobin from preparation example 2 according to process 2 Pyraclostrobin is, at 700C, a satisfactorily fluid melt (viscosity 2200 mPa.s) and was also formulated 30 according to the general method 2 at a temperature of 70 0 C. The active substance composition obtained was BASF/NAE 955/03 PCT - 53 homogeneous, was virtually transparent visually, was stable towards sedimentation for at least several months and could be diluted with water (both with demineralized water and water with a German hardness of 5 100) without sedimentation or crystallization of the active substance occurring. Depending on the active substance/polymer ratio (between 1:2.5 and 1:1), mean diameters of between 30 and 65 nm were measured by dynamic light scattering. No active substance particles 10 could be detected under a transmission electron microscope. The nanoparticulate fungicidal formulation, which comprised only water, polymer and active substance, was 15 compared, with regard to the biological action, with a commercial formulation of the active substance pyraclostrobin in a greenhouse. For this, the active substance formulations were 20 diluted with faucet water to the desired active substance concentrations (between 4 and 250 ppm). Application on tomato plants was carried out in a spray booth with a volume of 25 ml, which corresponds to an amount of water conventionally used in practice of 25 ca. 500 1/ha. The standard fungus (phytophthora infestans) was inoculated 7 days after treatment. The test plants were placed in a greenhouse at 18-200C and 90% relative humidity. Scoring was carried out 5 days after inoculation by determination of the infestation 30 of the leaves in percent. Table 4: Phytophthora infestans - Infestation [%] on tomatoes after five days as a function of the active substance content BASF/NAE 955/03 PCT - 54 Infestation [%] Infestation [%] Amount expended Formulation Commercial [ppm] example 4 product' 250 0 0 63 0 0 16 0 0 4 6 4 1) EC formulation: 23.5% by weight of pyraclostrobin, 5 4.7% by weight of anionic wetting agent and 4.7% by weight of nonionic wetting agent in 67.1% by weight of an aromatic solvent
Claims (10)
1. The use as solubility promoters of polymers comprising amphiphilic polyether groups as 5 solubility promoters, it being possible for the polymers to be obtained by copolymerization of (A) optionally at least one ethylenically unsaturated mono- or dicarboxylic acid or at least one anhydride derived from a mono- or 10 dicarboxylic acid, (B) at least one hydrophobic monomer exhibiting aromatic functional groups or aliphatic functional groups or aromatic and aliphatic functional groups, 15 (C) at least one allyl alcohol alkoxylate, (D) if appropriate, additional monoethylenically unsaturated monomers.
2. The use according to claim 1, 20 the solubility promoters being used in the preparation of cosmetics, drugs, foodstuffs, food supplements and animal fodder.
3. The use according to claim 1, 25 the solubility promoters being used in the preparation of plant protection products.
4. The use according to claim 3, the solubility promoters being used in the 30 treatment of seeds.
5. The use according to claims 1 to 4, wherein the polymer can be obtained by copolymerization of 35 (A) optionally at least one ethylenically unsaturated mono- or dicarboxylic acid with 3 to 8 carbon atoms or at least one anhydride BASF/NAE 955/03 PCT - 56 derived from a mono- or dicarboxylic acid with 3 to 8 carbon atoms, (B) at least one vinylaromatic compound, (C) at least one alkoxylated unsaturated ether of 5 the general formula (I) Ra R R O O R R (I) (D) optionally additional monoethylenically 10 unsaturated monomers, the variables in formula (I) being defined as follows: 1 23 R , R and R 3 are identical or different and are chosen from Ci-C 4 -alkyl or hydrogen; 15 R 4 and R 5 are each identical or different and are chosen from CI-C 4 -alkyl or hydrogen; R is chosen from hydrogen, SO 3 M, P0 3 M 2 , Ci-C 30 -alkyl, CO-H (formyl), CO-Ci-C 20 -alkyl or CO-C 6 -C 14 -aryl, 20 M is alkali metal or NH 4 * or CH 3 , n is an integer from 3 to 100, y is an integer from 0 to 10.
6. The use according to any of claims 1 to 5, 25 wherein .0 to 50% by weight of the component (A), 5 to 80% by weight of the component (B), 10 to 90% by weight of the component (C), 0 to 20% by weight of the component (D), 30 are present in the polymer.
7. The use according to any of claims 1 to 6, wherein (B) is styrene. BASF/NAE 955/03 PCT - 57
8. The use according to any of claims 1 to 7, wherein (A) is (meth) acrylic acid or maleic anhydride. 5
9. The use according to any of claims 1 to 8, wherein (D) is chosen from ethylenically unsaturated C 3 -C 8 -carboxylic acid derivatives of the general formula (II) 10 0 R 7 OR 9 (II) Ra acrylamides of the formula (III), o R 9 R 7 N/ R RS (III) R 8 noncyclic amides of the general formula (IVa) or cyclic amides of the general formula (IVb) 15 7R R 7R7 N-- 4 (Iva) (IVb) R (H)N x a 8 (CH) \(CH 2 ) O R e (C2)x 0 Ci-C 2 0 -alkyl vinyl ethers, N-vinyl derivatives of nitrogenous aromatic 20 compounds, BASF/NAE 955/03 PCT - 58 alkoxylated unsaturated esters of the general formula (V), R 4 R X O R R 8 (V) 5 esters or amides of the general formula (VI) 0 R 7 X R - A,- N \ / Ra R (VI) 10 unsaturated esters of the general formula (VII) 0 RO R R8 (VII) monomers comprising sulfonate, phosphate or 15 phosphonate groups, the variables in the general formulae (II) to (VII) being defined as follows: R7 and R 8 are identical or different and are chosen from hydrogen and Ci-Cio-alkyl, BASF/NAE 955/03 PCT - 59 R 9 are identical or different and are chosen from hydrogen or Ci-C 22 -alkyl, with the proviso that, in formula (II) , R 9 is not hydrogen, 5 A 1 is C 2 -C 6 -alkylene, branched or unbranched, x is an integer ranging from 2 to 100, a is an integer ranging from 0 to 6, m is an integer ranging from 2 to 200, Rio and R 11 are identical or different and are 10 chosen from hydrogen and Ci-Cio-alkyl, X is oxygen or N-R R12 is chosen from hydrogen, C 1 -Cio-alkyl or phenyl, and the remaining variables being defined as 15 above, with the proviso that, in the formula (II), R 9 is not hydrogen.
10. The use according to any of claims 1 to 9, wherein the polymer is metered in as aqueous 20 dispersion or solution.
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|---|---|---|---|
| DE102004031158.7 | 2004-06-28 | ||
| DE102004031158A DE102004031158A1 (en) | 2004-06-28 | 2004-06-28 | Use of polymers containing ether groups as solubilizers |
| PCT/EP2005/053123 WO2006000592A1 (en) | 2004-06-28 | 2005-06-28 | Use of ether group-containing polymers as solubilizers |
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| CN (1) | CN1976581B (en) |
| AU (1) | AU2005256662A1 (en) |
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| DE (1) | DE102004031158A1 (en) |
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| ES (1) | ES2410829T3 (en) |
| IL (1) | IL180007A0 (en) |
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| DE102004031158A1 (en) | 2004-06-28 | 2006-01-19 | Basf Ag | Use of polymers containing ether groups as solubilizers |
| EA200900482A1 (en) | 2006-10-05 | 2009-10-30 | Басф Се | BURNED POLYMERS AND THEIR APPLICATION FOR OBTAINING COMPOSITIONS OF ACTING OR EFFECTIVE SUBSTANCE |
| AU2008274352B2 (en) * | 2007-07-06 | 2014-01-16 | Basf Se | Use of homo- and copolymers for stabilizing active ingredient formulations |
| EP2440041A4 (en) * | 2009-06-12 | 2013-04-17 | Basf Se | Suspension composition and method of preparing the same |
| NZ600951A (en) * | 2010-01-04 | 2014-12-24 | Basf Se | Preservative formulation for cellulose containing materials |
| KR20130061132A (en) * | 2010-04-16 | 2013-06-10 | 발스파 소싱 인코포레이티드 | Coating compositions for packaging articles and methods of coating |
| EP2443923A1 (en) | 2010-10-25 | 2012-04-25 | Basf Se | Composition comprising a pesticide and polycarboxylate ether |
| WO2012049037A1 (en) | 2010-10-11 | 2012-04-19 | Basf Se | Composition comprising a pesticide and a polycarboxylate ether |
| KR102135072B1 (en) | 2011-02-07 | 2020-07-20 | 에스더블유아이엠씨 엘엘씨 | Coating compositions for containers and other articles and methods of coating |
| US9832991B2 (en) | 2011-04-08 | 2017-12-05 | Basf Se | Composition containing a pesticide and a vinylimidazol terpolymer |
| CN104540907B (en) | 2012-08-09 | 2018-04-10 | Swimc有限公司 | Composition and the method using same combination for container and other articles |
| BR112015002731B1 (en) | 2012-08-09 | 2021-11-30 | Swimc Llc | MULTI-LAYER COATING SYSTEM, ITEM, AND, METHOD |
| CN103450407A (en) * | 2013-08-15 | 2013-12-18 | 吉林大学 | Allyl polyoxyethylene ether modified polycarboxylate pesticide dispersing agent and preparation method thereof |
| WO2015160788A1 (en) | 2014-04-14 | 2015-10-22 | Valspar Sourcing, Inc. | Methods of preparing compositions for containers and other articles and methods of using same |
| TWI614275B (en) | 2015-11-03 | 2018-02-11 | Valspar Sourcing Inc | Liquid epoxy resin composition for preparing a polymer |
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| DE102004031158A1 (en) | 2004-06-28 | 2006-01-19 | Basf Ag | Use of polymers containing ether groups as solubilizers |
-
2004
- 2004-06-28 DE DE102004031158A patent/DE102004031158A1/en not_active Withdrawn
-
2005
- 2005-06-28 AU AU2005256662A patent/AU2005256662A1/en not_active Abandoned
- 2005-06-28 CN CN2005800217794A patent/CN1976581B/en not_active Expired - Fee Related
- 2005-06-28 BR BRPI0512667-3A patent/BRPI0512667B1/en not_active IP Right Cessation
- 2005-06-28 ES ES05761142T patent/ES2410829T3/en active Active
- 2005-06-28 WO PCT/EP2005/053123 patent/WO2006000592A1/en active Application Filing
- 2005-06-28 EP EP05761142.8A patent/EP1763300B1/en not_active Not-in-force
- 2005-06-28 PL PL05761142T patent/PL1763300T3/en unknown
- 2005-06-28 EA EA200602263A patent/EA014289B1/en not_active IP Right Cessation
- 2005-06-28 CA CA002570312A patent/CA2570312A1/en not_active Abandoned
-
2006
- 2006-12-12 IL IL180007A patent/IL180007A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1976581B (en) | 2012-11-21 |
| WO2006000592A1 (en) | 2006-01-05 |
| PL1763300T3 (en) | 2013-10-31 |
| ES2410829T3 (en) | 2013-07-03 |
| EA200602263A1 (en) | 2007-10-26 |
| IL180007A0 (en) | 2007-05-15 |
| EP1763300A1 (en) | 2007-03-21 |
| EP1763300B1 (en) | 2013-05-15 |
| CN1976581A (en) | 2007-06-06 |
| EA014289B1 (en) | 2010-10-29 |
| BRPI0512667A (en) | 2008-04-01 |
| BRPI0512667B1 (en) | 2015-07-28 |
| DE102004031158A1 (en) | 2006-01-19 |
| CA2570312A1 (en) | 2006-01-05 |
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Legal Events
| Date | Code | Title | Description |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |