IP Library Granted Patent US 10,070,650
Granted Patent B2
US 10,070,650 · App. 15/479,487 · Granted Sep 11, 2018

Methods to produce polymer nanoparticles and formulations of active ingredients

Inventors: Fugang Li (Richmond Hill, CA); Hung Hoang Pham (Brampton, CA); Darren J. Anderson (Toronto, CA)
Assignee: Vive Crop Protection Inc.
A01N57/20A01N39/04A01N43/40A01N43/50A01N43/54A01N43/68A01N47/36A01N51/00
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Quick Facts
Patent No.
US 10,070,650
App. No.
15/479,487
Granted
Sep 11, 2018
Kind
B2
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 (34)

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 polymer nanoparticle contains a solvent.

2. The composition of claim 1 , wherein the solvent is a hydrophobic solvent.

3. The composition of claim 2 , wherein the hydrophobic solvent is a polar, hydrophobic solvent.

4. The composition of claim 1 , wherein the at least one organic, neutral, non-ionic agricultural active compound is selected from the group consisting of nicotinic acetylcholine receptor agonist insecticides, strobilurin fungicides, sodium channel modulator insecticides, and chloride channel activator insecticides, and combinations thereof.

5. The composition of claim 1 , wherein the at least one organic, neutral, non-ionic agricultural active compound is selected from the group consisting of insecticides, fungicides, herbicides, nematicides, insect attractants, insect repellants, and combinations thereof.

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

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

8. 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.

9. 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.

10. 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.

11. 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.

12. 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 the solvent.

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

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

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

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

17. 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.

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

19. The composition of claim 4 , wherein the nicotinic acetylcholine receptor agonist insecticide is selected from the group consisting of imidacloprid, thiamethoxam, acetamiprid, and combinations thereof.

20. 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 polymer nanoparticle is swollen due to the presence of a hydrophobic solvent, as compared to the polymer nanoparticle without the hydrophobic solvent.

21. The composition of claim 20 , wherein a swelling comparison is conducted based on an average particle size of the polymer nanoparticle determined by a light scattering technique.

22. A composition comprising a polymer nanoparticle, comprising a hydrophobic solvent, 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 the polymer nanoparticle comprises a collapsed, water-soluble polyelectrolyte having a molecular weight of at least about 100,000 Dalton.

23. The composition of claim 22 , wherein the polymer nanoparticle is swollen in comparison to the polymer nanoparticle without the hydrophobic solvent.

24. The composition of claim 23 , wherein a swelling comparison is conducted based on an average particle size of the polymer nanoparticle determined by a light scattering technique.

Assignments (4)
SECURITY INTEREST Recorded Apr 18, 2022
From: VIVE CROP PROTECTION INC.
To: SILICON VALLEY BANK
Reel/Frame 059627/0547 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CANADIAN IMPERIAL BANK OF COMMERCE
To: VIVE CROP PROTECTION INC.
Reel/Frame 059271/0993 →
SECURITY INTEREST Recorded Oct 1, 2019
From: VIVE CROP PROTECTION INC
To: CANADIAN IMPERIAL BANK OF COMMERCE, AS LENDER
Reel/Frame 050582/0102 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2017
From: LI, FUGANG; PHAM, HUNG HOANG; ANDERSON, DARREN J.
To: VIVE CROP PROTECTION INC.
Reel/Frame 041976/0092 →
Continuity (9)
Continuation 15155805 · May 16, 2016
Continuation 14292667 · May 30, 2014
Continuation 13741673 · Jan 15, 2013
Continuation 13299214 · Nov 17, 2011
Continuation 12775049 · May 6, 2010
Continuation PCTIB2009006947 · Sep 25, 2009
Provisional Application 61158483 · Mar 9, 2009
Provisional Application 61100068 · Sep 25, 2008
Related Publication 20170202223A1 · Jul 20, 2017