Nanoparticulate active substance formulations
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Abstract
The invention relates to nanoparticulate formulations comprising at least one active compound or compound with a special effect and at least one random radical copolymer. The copolymers are formed from monomers carrying sulfonic acid groups and additional olefinically unsaturated compounds. The formulations are dispersible as nanoparticles in an aqueous medium. The invention includes, in addition, processes for the preparation of the solid and liquid formulations, and their use.
51 Citations
57 Claims
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1-23. -23. (canceled)
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24. An active compound formulation comprising
a) at least one active compound chosen from the group of fungicides b) at least one random radical copolymer formed from the monomers i), ii) and optionally additional monomers, in which i) is at least one olefinically unsaturated sulfonic acid of the formula I in which n is 0 or 10 x is O or NR5 R1 is hydrogen or methyl R2, R3 are, independently of one another, hydrogen or C1-C6-alkyl R5 is hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl, or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, or salts thereof or mixtures of acid and salts, and ii) is at least one olefinically unsaturated monomer of the formula II in which Y is O or NR5, R4 is hydrogen or methyl, R5, R6 are hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, in which at least one olefinically unsaturated monomer ii) corresponds to the formula IIb, in which R6 is alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, and c) optionally additional additives.
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42. A process for the preparation of aqueous dispersions, which comprises bringing an active compound formulation comprising
a) at least one active compound chosen from the group of fungicides b) at least one random radical copolymer formed from the monomers i), ii) and optionally additional monomers, in which i) is at least one olefinically unsaturated sulfonic acid of the formula I in which n is 0 to 10 X is O or NR5 R1 is hydrogen or methyl R2, R3 are, independently of one another, hydrogen or C1-C6-alkyl R5 is hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl, or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, or salts thereof or mixtures of acid and salts, and ii) is at least one olefinically unsaturated monomer of the formula II in which Y is O or NR5, R4 is hydrogen or methyl, R5, R6 are hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, in which at least one olefinically unsaturated monomer ii) corresponds to the formula IIb, in which R6 is alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, and c) optionally additional additives, if appropriate with addition of one or more additives, into contact with an aqueous system and conventionally dispersing.
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44. A process for the preparation of an active compound formulation comprising
a) at least one active compound chosen from the group of fungicides b) at least one random radical copolymer formed from the monomers i), ii) and optionally additional monomers, in which i) is at least one olefinically unsaturated sulfonic acid of the formula I in which n is O to 10 x is O or NR5 R1 is hydrogen or methyl R2, R3 are, independently of one another, hydrogen or C1-C6-alkyl R5 is hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl, or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, or salts thereof or mixtures of acid and salts, and ii) is at least one olefinically unsaturated monomer of the formula II in which Y is O or NR5, R4 is hydrogen or methyl, R5, R6 are hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, in which at least one olefinically unsaturated monomer ii) corresponds to the formula in which R6 is alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, and c) optionally additional additives, which process comprises dissolving the components a) and b) and if appropriate c), and optionally additional additives, separately from one another, in identical or different organic solvents and mixing the solutions with one another or preparing a combined solution of the components a) and b) and if appropriate c), and optionally additional additives, by presenting one of the components dissolved in an organic solvent, adding the additional components and dissolving, and optionally subsequently removing the solvent in a conventional way to the greatest possible extent.
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46. A process for the preparation of an active compound formulation comprising
a) at least one active compound chosen from the group of fungicides b) at least one random radical copolymer formed from the monomers i), ii) and optionally additional monomers, in which i) is at least one olefinically unsaturated sulfonic acid of the formula I in which n is 0 to 10 x is O or NR5 R1 is hydrogen or methyl R2, R3 are, independently of one another, hydrogen or C1-C6-alkyl R5 is hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl, or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, or salts thereof or mixtures of acid and salts, and ii) is at least one olefinically unsaturated monomer of the formula II in which Y is O or NR5, R4 is hydrogen or methyl, R5, R6 are hydrogen, alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, in which at least one olefinically unsaturated monomer ii) corresponds to the formula IIb, in which R6 is alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, aryloxyalkyl, alkoxyaryl, hydroxyalkyl, (di)alkylaminoalkyl, (di)alkylaminoaryl, (di)arylaminoalkyl, alkylarylaminoalkyl or alkylarylaminoaryl, it being possible for the aryl radicals to be substituted, and c) optionally additional additives, which process comprises forming an aqueous solution of the component b), and optionally additional additives, dissolving the components a) and, if appropriate, c), and optionally additional additives, in one or more water-miscible organic solvents, mixing the solutions of the components with one another and obtaining the active compound formulation in dispersed form by introduction of energy, and optionally subsequently removing the solvents in the conventional way to the greatest possible extent.
Specification