Methods to produce polymer nanoparticles and formulations of active ingredients

• US 8,084,397 B2
• Filed: 05/06/2010
• Issued: 12/27/2011
• Est. Priority Date: 09/25/2008
• Status: Active Grant

• Current Assignee: Vive Crop Protection Inc.
• Original Assignee: Vive Nano, Inc.
• Inventors: Li, Fugang, Pham, Hung, Anderson, Darren J.
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): CRAIGO, WILLIAM A
• Application Number:
  US12/775,049
• Publication Number:
  US 20100210465A1
• Time in Patent Office: 600 Days
• Field of Search: None
• US Class Current: 504/206
• 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 organic, neutral, non-ionic agricultural active compound associated with the polymer nanoparticle, wherein the polymer nanoparticle is less than 100 nm in diameter and cross-linked, and wherein the polymer nanoparticle comprises a collapsed water-soluble polyelectrolyte that has a molecular weight of at least about 100,000 Dalton.

2. The composition of claim 1, wherein the polymer nanoparticle is less than 50 nm in size.

3. The composition of claim 1, wherein the polymer nanoparticle comprises multiple collapsed water-soluble polyelectrolyte molecules that each have a molecular weight of at least about 100,000 Dalton.

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

5. The composition of claim 1, wherein the water-soluble polyelectrolyte is selected from the group consisting of poly(acrylic acid), poly(methacrylic acid), poly(styrene sulfonate), chitosan, poly(dimethyldiallylammonium chloride), poly(allylamine hydrochloride), copolymers or graft polymers thereof and combinations thereof.

6. The composition of claim 1, wherein at least a portion of the agricultural active compound is in the interior of the polymer nanoparticle.

7. The composition of claim 1, wherein at least a portion of the agricultural active compound is on the surface of the polymer nanoparticle.

8. The composition of claim 1, wherein the agricultural active compound remains associated with the polymer nanoparticle after being exposed to a solvent.

9. The composition of claim 1 which provides for extended or sustained release after application.

10. The composition of claim 1, wherein the agricultural active compound is released via triggered release.

11. The composition of claim 1, wherein the polymer nanoparticle has a cavity.

12. The composition of claim 1, wherein the polymer nanoparticle has a network structure.

13. The composition of claim 1, wherein the agricultural active compound associated with the polymer nanoparticle has different mobility in soil than it has when not associated with the polymer nanoparticle.

14. The composition of claim 1, wherein the agricultural active compound is hydrophobic.

15. The composition of claim 1, wherein the agricultural active compound is neutral at a pH of between about 5 to about 9.

16. The composition of claim 1, wherein the agricultural active compound is neutral at a pH of between about 6 to about 8.

17. The composition of claim 1, wherein the water-soluble polyelectrolyte has a molecular weight of at least about 250,000 Daltons.

18. The composition of claim 1, wherein the agricultural active compound is selected from the group consisting of acaricides, algicides, avicides, bactericides, fungicides, herbicides, insecticides, miticides, molluscicides, nematicides, rodenticides, virucides, algicides, bird repellents, mating disrupters, plant activators, antifeedants, insect attractants and repellants.

19. The composition of claim 1, wherein the agricultural active compound is a herbicide selected from the group consisting of amino acid synthesis inhibitors, cell membrane disrupters, lipid synthesis inhibitors, pigment inhibitors, seedling growth inhibitors, growth regulators, and photosynthesis inhibitors.