METHODS TO FORMULATE NEUTRAL ORGANIC COMPOUNDS WITH POLYMER NANOPARTICLES

• US 20170202216A1
• Filed: 04/05/2017
• Published: 07/20/2017
• Est. Priority Date: 03/24/2010
• Status: Abandoned Application

• Current Assignee: Vive Crop Protection Inc.
• Original Assignee: Vive Crop Protection Inc.
• Inventors: Li, Fugang, Pham, Hung Hoang, Anderson, Darren J.
• Application Number:
  US15/479,402
• Publication Number:
  US 20170202216A1
• Time in Patent Office: Days
• CPC Class Codes: A01N 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 37/38 having at least one oxygen or sulfur atom attached to an aromatic ring system
• 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 43/66 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen 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: A01N 59/16 Heavy metals; Compounds thereof
• CPC Class Codes: A23L 27/20 Synthetic spices, flavouring agents or condiments
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C08J 2305/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C08J 2333/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08J 2333/04 esters
• CPC Class Codes: C08J 2339/00 Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
• CPC Class Codes: C08J 2371/02 Polyalkylene oxides
• CPC Class Codes: C08J 3/12 : Powdering or granulating
• CPC Class Codes: C08J 3/20 : Compounding polymers with additives, e.g. colouring
• CPC Class Codes: C08J 5/005 : Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
• CPC Class Codes: C08K 5/0058 : Biocides; macromolecular substances as carriers for biocide material A01N25/10
• CPC Class Codes: C08L 5/08 : Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09B 26/02 : Hydrazone dyes hydrazone-azo dyes C09B56/18
• CPC Class Codes: C09K 11/06 : containing organic luminescent materials
• CPC Class Codes: C09K 2211/1011 : Condensed systems

Abstract

A composition including a collapsed, polymer nanoparticle and at least one organic, neutral compound associated with the nanoparticle, wherein the nanoparticle is less than 100 nm in diameter, and the polymer comprises a water-soluble polyelectrolyte, has a molecular weight of at least about 100,000 Dalton and is cross-linked. The organic, neutral compound is selected from the group consisting of dyes, pigments, colorants, oils, UV-light absorbing molecules, fragrances, flavoring molecules, preservatives, electro-conductive compounds, thermoplastic compounds, adhesion promoters, penetration enhancers, anti-corrosive agents, and combinations thereof.

Claims

1. A composition comprising polymer nanoparticle and at least one organic, neutral, non-ionic compound associated with the polymer nanoparticle,

wherein the polymer nanoparticle is less than 100 nm in diameter, and

the polymer nanoparticle comprises:

multiple, cross-linked, collapsed, water-soluble polyelectrolytes;

each of which comprises a random copolymer with hydrophilic and hydrophobic regions, and has a molecular weight of at least about 100,000 Dalton; and

wherein the organic, neutral, non-ionic compound is selected from the group consisting of dyes, pigments, colorants, oils, UV-light absorbing molecules, fragrances, flavoring molecules, preservatives, electro-conductive compounds, thermoplastic compounds, adhesion promoters, penetration enhancers, anti-corrosive agents, and combinations thereof.

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

4. The composition of claim 1, wherein the polymer nanoparticle is less than 20 nm in size.

6. The composition of claim 1, wherein the organic, neutral, non-ionic compound is hydrophobic.

7. The composition of claim 1, wherein the multiple, cross-linked, collapsed, water-soluble polyelectrolytes are cross-linked by one of the following:

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

8. A dispersion comprising the composition of claim 1, wherein the organic, neutral, non-ionic 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 multiple, cross-linked, collapsed, water-soluble polyelectrolytes comprise poly(acrylic acid), poly(methacrylic acid), poly (styrene sulfonate), chitosan, poly (dimethyldiallylammonium chloride), poly (allylamine hydrochloride), or combinations thereof.

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

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

12. The composition of claim 1, wherein the organic, neutral, non-ionic compound remains associated with the polymer nanoparticle after being exposed to a solvent.

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

14. The composition of claim 1, wherein the organic, neutral, non-ionic compound is released via triggered release.

15. The composition of claim 1, wherein the organic, neutral, non-ionic compound is neutral at a pH of between about 5 to about 9.

16. The composition of claim 1, wherein the organic, neutral, non-ionic compound is neutral at a pH of between about 6 to about 8.

17. The composition of claim 1, wherein the multiple, cross-linked, collapsed, water-soluble polyelectrolytes have a molecular weight of at least about 250,000 Daltons.

19. The composition of claim 1, wherein the organic, neutral, non-ionic compound is not a salt, or ion from a salt.

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

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

22. The composition of claim 1, wherein the polymer nanoparticle is recovered in a dried form and redispersed in a suitable solvent.

2. (canceled)

5. (canceled)

18. (canceled)

23-24. -24. (canceled)

25. A method to associate an organic, neutral compound with polymer nanoparticles comprising the steps of:

(a) dissolving polymer nanoparticles and an organic, neutral compound in a suitable solvent; and

(b) removing the solvent,

wherein the organic, neutral compound is selected from the group consisting of dyes, pigments, colorants, oils, UV-light absorbing molecules, fragrances, flavoring molecules, preservatives, electro-conductive compounds, thermoplastic compounds, adhesion promoters, penetration enhancers, anti-corrosive agents, and combinations thereof,

wherein the polymer nanoparticles are less than 100 nm in diameter, and the polymer nanoparticles comprise multiple, cross-linked, collapsed, a water soluble polyelectrolyte;

each of which comprises a random copolymer with hydrophilic and hydrophobic regions, and has a molecular weight of at least about 100,000 Dalton.

26-58. -58. (canceled)