IP Library Granted Patent US 11,040,324
Granted Patent B2
US 11,040,324 · App. 15/097,874 · Granted Jun 22, 2021

Polyelectrolyte microcapsules and methods of making the same

Inventors: Daeyeon Lee (Wynnewood, PA); Junsang Doh (Seoul, KR); Miju Kim (Philadelphia, PA); Martin F. Haase (Philadelphia, PA); Gang Duan (Philadelphia, PA)
Assignee: The Trustees of the University of Pennsylvania
B01J13/06A01N25/28A23L27/72A23L33/10A23L33/30A61K8/11A61K8/8147A61K8/84A61K9/5026A61K9/5031A61K9/5089A61K9/5094B01J13/10C11D3/505A61K2800/412A61K2800/56
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Quick Facts
Patent No.
US 11,040,324
App. No.
15/097,874
Granted
Jun 22, 2021
Kind
B2
Abstract

Polyelectrolyte microcapsules, and methods for making and using the polyelectrolyte microcapsules, are described. A method of making polyelectrolyte microcapsules includes forming an “interfacial complexation in emulsion” (ICE), wherein a polyelectrolyte “shell” is formed by complexing two different polyelectrolytes together at an interface between two immiscible fluids. Both hydrophilic and hydrophobic materials can be incorporated into the cores and shells of the polyelectrolyte microcapsules.

Claims (26)

1. A method of making polyelectrolyte microcapsules, comprising:

with a water phase comprising a first polyelectrolyte having a charge dissolved in water, and

an oil phase comprising a second polyelectrolyte dissolved in a hydrophobic organic fluid to produce an oil phase, the second polyelectrolyte having an opposite charge to the charge of the first polyelectrolyte,

the first polyelectrolyte and the second polyelectrolyte being selected from polyamines having at least primary, secondary, tertiary, or quaternary amines, from polybases, and from polyacids,

injecting the water phase, the oil phase, and an outer water phase comprising water into a capillary microfluidic device under such conditions that the injecting gives rise to a water-in-oil-in-water (W/O/W) double emulsion,

the W/O/W double emulsion comprising the water phase as an inner phase, the oil phase as a middle phase, and the outer water phase as an outer phase,

the first and second polyelectrolytes forming polyelectrolyte microcapsules comprising a shell that comprises a polyelectrolyte complex formed of the first and second polyelectrolytes present at interfaces between the inner water phase and the middle oil phase, and

the polyelectrolyte microcapsules being formed following a spontaneous dewetting process whereby the polyelectrolyte microcapsules separate from the middle oil phase.

2. The method of claim 1 , further comprising dissolving the first polyelectrolyte in the water phase and dissolving the second polyelectrolyte in the oil phase prior to forming the W/O/W double emulsion.

3. The method of claim 1 , further comprising adding one or more additives to the water phase and adding one or more additives to the oil phase prior to forming the W/O/W double emulsion, wherein the additives are selected from the group consisting of stabilizing agents, surfactants, pH adjusters and combinations thereof.

4. The method of claim 1 , further comprising adding at least one active ingredient to the inner water phase prior to forming the W/O/W double emulsion.

5. The method of claim 4 , wherein the at least one active ingredient is selected from the group consisting of active pharmaceutical ingredients, herbicides, pesticides, plant nutrients, antioxidants, anti-bacterial agents, fragrances, edible actives, flavorants, vitamins, minerals, and combinations thereof.

6. The method of claim 1 , further comprising adding one or more hydrophobic materials to the oil phase prior to forming the W/O/W double emulsion.

7. The method of claim 6 , wherein the one or more hydrophobic materials comprise one or more nanoparticles.

8. The method of claim 1 , further comprising: forming a complex between a surfactant and the second polyelectrolyte to form a surfactant-modified polyelectrolyte prior to forming the W/O/W double emulsion; and

dissolving the surfactant-modified polyelectrolyte in the oil phase prior to forming the W/O/W double emulsion.

9. The method of claim 1 , further comprising:

dissolving the second polyelectrolyte in an aqueous phase prior to forming the W/O/W double emulsion; and

forming micro-emulsions of the aqueous phase comprising the dissolved second polyelectrolyte within the oil phase prior to forming the W/O/W double emulsion.

10. A pharmaceutical composition comprising a pharmaceutical carrier and a plurality of polyelectrolyte microcapsules in accordance with claim 8 , wherein the polyelectrolyte microcapsules comprise one or more active pharmaceutical ingredients.

11. An agricultural composition comprising an agricultural carrier and a plurality of polyelectrolyte microcapsules in accordance with claim 8 , wherein the polyelectrolyte microcapsules comprise one or more herbicides, pesticides, and/or plant nutrients.

12. A cosmetic composition comprising a cosmetic carrier and a plurality of polyelectrolyte microcapsules in accordance with claim 8 , wherein the polyelectrolyte microcapsules comprise one or more antioxidants, anti-bacterial agents, and/or fragrances.

13. A food product comprising one or more food ingredients and a plurality of polyelectrolyte microcapsules in accordance with claim 8 , wherein the polyelectrolyte microcapsules comprise one or more foodstuffs, flavorants, nutrients, vitamins, and/or minerals.

14. The method of claim 6 , wherein the hydrophobic materials are incorporated into the polyelectrolyte complex.

15. The method of claim 6 , wherein the one or more hydrophobic materials comprise dyes, drugs, and/or conjugated polymers.

16. The method of claim 7 , wherein the one or more nanoparticles include SiO 2 , TiO 2 , Fe 2 O 3 , Al 2 O 3 , gold, and silver.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2019
From: LEE, DAEYEON; DOH, JUNSANG; KIM, MIJU; HAASE, MARTIN F.; DUAN, GANG
To: THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA
Reel/Frame 047948/0329 →
CONFIRMATORY LICENSE Recorded Jun 15, 2016
From: UNIVERSITY OF PENNSYLVANIA
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 039024/0450 →
Continuity (2)
Provisional Application 62146586 · Apr 13, 2015
Related Publication 20160332131A1 · Nov 17, 2016