Methods to produce polymer nanoparticles and formulations of active ingredients

• US 9,648,871 B2
• Filed: 05/16/2016
• Issued: 05/16/2017
• Est. Priority Date: 09/25/2008
• Status: Active Grant

• Current Assignee: Vive Crop Protection Inc.
• Original Assignee: Vive Crop Protection Inc.
• Inventors: Li, Fugang, Anderson, Darren J., Pham, Hung Hoang
• Primary Examiner(s): Tran, Susan
• Assistant Examiner(s): CRAIGO, WILLIAM A
• Application Number:
  US15/155,805
• Publication Number:
  US 20160255831A1
• Time in Patent Office: 365 Days
• Field of Search: None
• 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;

the polymer nanoparticle comprises a collapsed, water-soluble polyelectrolyte having a molecular weight of at least about 100,000 Dalton; and

the at least one organic, neutral, non-ionic, agricultural active compound is a nicotinic acetylcholine receptor agonist insecticide.

2. The composition of claim 1, wherein the nicotinic acetylcholine receptor agonist insecticide is selected from the group consisting of imidacloprid, thiamethoxam, acetamiprid, and combinations thereof.

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

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

5. A dispersion comprising the composition of claim 1, wherein the at least one organic, neutral, non-ionic agricultural active compound is dispersed at a concentration higher than its solubility in the absence of the polymer nanoparticle.

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

7. The composition of claim 1, wherein at least a portion of the at least one organic, neutral, non-ionic agricultural active compound is in the interior of the polymer nanoparticle.

8. The composition of claim 1, wherein at least a portion of the at least one organic, neutral, non-ionic agricultural active compound is on the surface of the polymer nanoparticle.

9. The composition of claim 1, wherein the at least one organic, neutral, non-ionic agricultural active compound remains associated with the polymer nanoparticle after being exposed to a solvent.

10. The composition of claim 1, wherein the composition is an extended or sustained release composition.

11. The composition of claim 1, wherein the composition is a triggered release composition.

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

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

14. The composition of claim 1, wherein the at least one organic, neutral, non-ionic agricultural active compound associated with the polymer nanoparticle has different mobility in soil than it has when not associated with the polymer nanoparticle.

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