METHODS TO PRODUCE POLYMER NANOPARTICLES AND FORMULATIONS OF ACTIVE INGREDIENTS

• US 20170202223A1
• Filed: 04/05/2017
• Published: 07/20/2017
• Est. Priority Date: 09/25/2008
• Status: Active Grant

• Current Assignee: Vive Crop Protection Inc.
• Original Assignee: Vive Crop Protection Inc.
• Inventors: Li, Fugang, Pham, Hung Hoang, Anderson, Darren J.
• Granted Patent: US 10,070,650 B2
• Time in Patent Office: Days
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/50 1,3-Diazoles; Hydrogenated 1,3-diazoles
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/68 with two or three nitrogen atoms directly attached to ring carbon atoms
• CPC Class Codes: A01N 43/70 Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• CPC Class Codes: A01N 51/00 Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C08J 2333/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08J 2339/02 Homopolymers or copolymers of vinylamine
• CPC Class Codes: C08J 3/14 by precipitation from solutions C08J3/122 takes precedence
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08J 3/28 Treatment by wave energy or particle radiation
• CPC Class Codes: C08K 2201/011 Nanostructured additives
• CPC Class Codes: C08K 5/0058 Biocides; macromolecular substances as carriers for biocide material A01N25/10
• CPC Class Codes: C08L 25/18 : Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
• CPC Class Codes: C08L 33/02 : Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 39/02 : Homopolymers or copolymers of vinylamine
• CPC Class Codes: C08L 5/08 : Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 105/08 : Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: Y10T 428/2982 : Particulate matter [e.g., sphere, flake, etc.]

Abstract

The present invention provides a composition including a polymer nanoparticle and at least one agricultural active compound incorporated with the nanoparticle, wherein the nanoparticle are less than 100 nm in diameter, and the polymer includes a polyelectrolyte.

Claims

1. A composition comprising a polymer nanoparticle and at least one agricultural active compound associated with the nanoparticle, wherein the nanoparticle are less than 100 nm in diameter, and the polymer comprises a polyelectrolyte.

2. The composition of claim 1, wherein the agricultural active compound is an organic compound.

3. The composition of claim 1, wherein the agricultural active compound is selected from the group consisting of an acaracide, a fungicide, a bactericide, a herbicide, an antibiotic, an antimicrobial, a nemacide, a rodenticide, an entomopathogen, a pheromone, a chemosterilant, a virus, an attractant, a plant growth regulator, an insect growth regulator, a repellent, a plant nutrient, a phagostimulant, a germicide, and combinations thereof.

4. The composition of claim 1, wherein the nanoparticles are less than 50 nm in size.

5. The composition of claim 1, wherein the nanoparticles are less than 20 nm in size.

6. The composition of claim 1, wherein the polymer comprises multiple polymer molecules.

7. The composition of claim 1, wherein the polymer nanoparticle is crosslinked.

8. The composition of claim 1, wherein the active ingredient is selected from the group consisting of atrazine, neonicitinoids, photosynthesis inhibitors, amino acid synthesis inhibitors, growth regulators, pyrethrins, avermectins, and strobilurins.

9. The nanoparticle of claim 1, wherein the polymer is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly (styrene sulfonate), chitosan, poly (dimethyldiallylammonium chloride), poly (allylamine hydrochloride), or copolymers or graft polymers thereof and combinations thereof.

10. A dispersion comprising the composition of claim 1, wherein the active ingredient is dispersed at a concentration higher than its solubility in the absence of the polymer nanoparticle.

11. A method to make polymer nanoparticles, comprising the steps of:

(a) dissolving a polyelectrolyte into an aqueous solution under solution conditions that render it charged,

(b) adding a species that is oppositely charged under these conditions to cause the polymer to collapse, and

(c) crosslinking the polymer.

12. The method of claim 11, wherein the oppositely charged species is an agricultural active compound.

13. The method of claim 11, wherein the oppositely charged species is removed from the polymer nanoparticle.

14. The method of claim 13, wherein the oppositely charged species is removed from the polymer nanoparticle by pH adjustment, filtration, dialysis, or combinations thereof.

15. The method of claim 13, further comprising the step of associating an active ingredient with the polymer nanoparticle.

16. The method of claim 12, wherein the crosslinking step is accomplished by one of the following:

electromagnetic radiation induced cross-linking, chemically induced cross-linking or thermally induced cross-linking.

17. The method of claim 12, further comprising the step of removing the solvent.

18. The method of claim 17, wherein the solvent is removed by lyophilization, distillation, filtration, extraction, selective solvent removal, dialysis, or evaporation.

19. The method of claim 18, further comprising the step of redispersing the nanoparticles in a suitable solvent.

20. The method of claim 12, wherein the agricultural active compound is selected from the group consisting of an acaracide, a fungicide, a bactericide, a herbicide, an antibiotic, an antimicrobial, a nemacide, a rodenticide, an entomopathogen, a pheromone, a chemosterilant, a virus, an attractant, a plant growth regulator, an insect growth regulator, a repellent, a plant nutrient, a phagostimulant, a germicide, and combinations thereof.