Release of biologically active agents from polymeric composite particles

Patent metadata

Field	Value
Publication number	US-10111424-B2
Application number	US-201414891560-A
Country	US
Kind code	B2
Filing date	May 13, 2014
Priority date	May 17, 2013
Publication date	Oct 30, 2018
Grant date	Oct 30, 2018

Abstract

Polymeric composite particles are provided that can be used for the storage and delivery of various biologically active agent. The polymeric composite particles contain a porous polymeric core and a coating layer around the porous polymeric core. The porous polymeric composite particles typically further include a biologically active agent positioned within the porous polymeric core but not covalently bonded to the porous polymeric core. The biologically active agent can be released from the polymeric composite particle by diffusing out of the porous polymeric core through the coating layer.

First claim

What is claimed is:

1. A polymeric composite particle comprising
a) a porous polymeric core particle comprising a washed and dried polymerized product of a reaction mixture comprising:
i) a first phase comprising either
1) water and a polysaccharide dissolved in the water; or
2) a surfactant and a compound of Formula (I)

wherein n is an integer equal to at least 1, or a mixture thereof; and
ii) a second phase dispersed in the first phase, wherein a volume of the first phase is greater than a volume of the second phase and wherein the second phase comprises
1) a monomer composition comprising a first monomer of Formula (II)

wherein
the monomer of Formula (II) is not miscible with the first phase;
p is an integer is no greater than 30;
R 1 is hydrogen or alkyl; and

2) a poly(propylene glycol) having a weight average molecular weight of at least 500 grams/mole,

wherein the poly(propylene glycol) is removed from the polymerized product to provide the porous polymeric core;
b) a biologically active agent positioned within the porous polymeric core, wherein the biologically active agent is not covalently bonded to the porous polymeric core; and
c) a coating layer around the porous polymeric core particle, wherein the coating layer comprises a thermoplastic polymer, a wax, or a mixture thereof.

2. The polymeric composite particle of claim 1 , wherein the polymeric composite particle has a core-shell configuration with the core being the porous polymeric core particle and the shell being the coating layer.

3. The polymeric composite particle of claim 1 , wherein the first phase comprise water and 10 to 30 weight percent polysaccharide based on a total weight of the first phase.

4. The polymeric composite particle of claim 1 , wherein the first phase comprises the compound of Formula (I) and a nonionic surfactant.

5. The polymeric composite particle of claim 1 , wherein the monomer composition comprises a second monomer of Formula (III)

wherein
R 1 is hydrogen or methyl;
Y is a single bond, alkylene, oxyalkylene, or poly(oxyalkylene); and
R 2 is a carbocyclic group or heterocyclic group.

6. The polymeric composite particle of claim 1 , wherein the monomer composition comprises a second monomer of Formula (VII) or a salt thereof

wherein
R 1 is hydrogen or methyl; and
R 6 is an alkylene.

7. The polymeric composite particle of claim 1 , wherein the biologically active agent comprises a herbicide, insecticide, fungicide, or mixture thereof.

8. The polymeric composite particle of claim 1 , wherein the coating layer comprises a silicone-based thermoplastic polymer, (meth)acrylate-based thermoplastic polymer, olefin-based thermoplastic polymer, styrene-based thermoplastic polymer, or a phenoxy-based resin.

9. The polymeric composite particle of claim 1 , wherein the coating layer comprises an animal wax, vegetable wax, petroleum wax, hydrogenate vegetable oil, or polyethylene.

10. The polymeric composite particle of claim 1 , wherein the polymeric composite particle comprises 20 to 90 weight percent porous polymeric core particle, 0.1 to 40 weight percent biologically active agent, and 10 to 80 weight percent coating layer.

11. A method of delivering a biologically active agent, the method comprising:
providing a polymeric composite particle comprising
a) a porous polymeric core particle comprising a washed and dried polymerized product of a reaction mixture comprising:
i) a first phase comprising either
1) water and a polysaccharide dissolved in the water; or
2) a surfactant and a compound of Formula (I)

ii) a second phase dispersed in the first phase, wherein a volume of the first phase is greater than a volume of the second phase and wherein the second phase comprises
1) a monomer composition comprising a first monomer of Formula (II)

wherein
 the monomer of Formula (II) is not miscible with the first phase;
 p is an integer is no greater than 30;
 R 1 is hydrogen or alkyl; and
2) a poly(propylene glycol) having a weight average molecular weight of at least 500 grams/mole,

wherein the poly(propylene glycol) is removed from the polymerized product to provide the porous polymeric core;
b) a biologically active agent positioned within the porous polymeric core, wherein the biologically active agent is not covalently bonded to the porous polymeric core; and
c) a coating layer around the porous polymeric core particle, wherein the coating layer comprises a thermoplastic polymer, a wax, or a mixture thereof; and

releasing the biologically active agent from the polymeric composite particle by diffusion through the coating layer.

12. The method of claim 11 , wherein the first phase comprise water and 10 to 30 weight percent polysaccharide based on a total weight of the first phase.

13. The method of claim 11 , wherein the first phase comprises the compound of Formula (I) and a nonionic surfactant.

14. The method of claim 11 , wherein providing the polymeric composite particle comprises
forming the porous polymeric core particle;
positioning the biologically active agent within the porous polymeric core particle to form a loaded polymeric particle; and
depositing the coating layer around the loaded polymeric particle.

15. The method of claim 14 , wherein depositing the coating layer comprises
preparing a coating solution or a coating dispersion;
mixing the loaded polymeric particle with the coating solution or coating dispersion to form a slurry; and
drying the slurry, wherein drying comprises spray drying or fluidized bed drying.

Assignees

• 3M Innovative Properties Co

Inventors

• Sahouani Hassan
• Caruso Dailey Mary M
• Heinzen Luke E
• El Hedok Ibrahim A

Classifications

• C08J3/126 Primary

  Polymer particles coated by polymer, e.g. core shell structures · CPC title

• A01N25/26 Primary

  in coated particulate form · CPC title

• B01J13/043

  Drying and spraying · CPC title

• C08J2205/024

  Organogel, i.e. a gel containing an organic composition · CPC title

• C08J9/286

  the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers · CPC title