# US 10,500,558 B2 · Reflecting spherical microcapsules and methods of their production

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- Number: US 10,500,558 B2
- Document ID: US10500558B2
- Status: Granted
- Kind: B2
- Application number: 15/497,603
- Filed: 2017-04-26
- Published: 2017-08-10
- Granted: 2019-12-10
- Earliest claimed: 2014-11-01
- Assignees: Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
- Applicants: Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
- Inventors: Ingmar Polenz; Huixuan Wu; Jean-Christophe Baret; Eberhard Bodenschatz
- Web page: https://patentgrep.com/patent/US10500558B2

## CPC

- B01J 13/16: Interfacial polymerisation
- C08G 18/6423: {Polyalkylene polyamines; polyethylenimines; Derivatives thereof (polyamides or polyesteramides C08G18/60)}
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08K 3/22: of metals
- C08K 3/36: Silica
- C08K 9/02: Ingredients treated with inorganic substances
- G01N 21/53: within a flowing fluid, e.g. smoke
- C08K 2003/2241: {Titanium dioxide}
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Spherical microcapsules including light reflecting solid integral particles reflecting incoming light in a defined direction for determining the position and orientation of the microcapsule are produced by preparing a first liquid phase containing a first polymerization partner; preparing a second liquid phase containing a second polymerization partner, the first liquid phase not being soluble in the second liquid phase, and the second polymerization partner being configured to polymerize with the first polymerization partner under polymerization conditions; dispersing the solid particles in the first liquid phase; forming droplets of the first liquid phase including at least one solid particle; and immersing the droplets in the second liquid phase under the polymerization conditions. The first polymerization partner and the second polymerization partner polymerize at the surfaces of the droplets forming shells of a polymeric material enclosing the individual droplets, and the light reflecting solid integral particles are fixed to the shells.

## Claims

### Claim 1

A method of producing monodisperse spherical microcapsules comprising a shell and a core, the method comprising:
preparing a first liquid phase containing a first polymerization partner;
preparing a second liquid phase containing a second polymerization partner, the first liquid phase not being soluble in the second liquid phase, and the second polymerization partner being configured to polymerize with the first polymerization partner under interfacial polymerization conditions;
dispersing light reflecting solid integral particles in the first liquid phase;
forming droplets of the first liquid phase including at least one of the light reflecting solid integral particles;
immersing the droplets in the second liquid phase under the interfacial polymerization conditions, wherein the first polymerization partner and the second polymerization partner polymerize at the surfaces of the droplets forming shells of a polymeric material enclosing the individual droplets; and
fixing the light reflecting solid integral particles to the shells;
thereby producing monodisperse spherical microcapsules comprising the core and the shell;
wherein the core comprises 1 to 5 light reflecting solid integral particles per microcapsule; and
wherein the shell comprises the polymeric material.

### Claim 2 (depends on 1)

The method of claim 1, further comprising collecting the droplets enclosed by the shells from the second liquid phase and dispersing the droplets enclosed by the shells in a third liquid phase, the third liquid phase having a refraction index essentially matching a refraction index of the first liquid phase.

### Claim 3 (depends on 2)

The method of claim 2, wherein the first liquid phase is soluble in the third liquid phase.

### Claim 4 (depends on 2)

The method of claim 2, wherein the third liquid phase is water or an aqueous solution.

### Claim 5 (depends on 1)

The method of claim 1, wherein one of the first and second liquid phases is an aqueous phase, whereas the other of the first and second liquid phases is an oleaginous phase.

### Claim 6 (depends on 1)

The method of claim 1, wherein the first liquid phase is an aqueous solution including a hydrogel, or an oleaginous solution including an organogel.

### Claim 7 (depends on 1)

The method of claim 1, wherein the first liquid phase gels or solidifies at temperatures below a gelling or solidification temperature, the polymerization conditions including a temperature above the gelling or solidification temperature.

### Claim 8 (depends on 7)

The method of claim 7, wherein the gelling or solidification temperature is higher than a use temperature of the microcapsules.

### Claim 9 (depends on 1)

The method of claim 1, wherein first liquid phase or the gelled or solidified first liquid phase is transparent for the light to be reflected by the light reflecting solid integral particles.

### Claim 10 (depends on 1)

The method of claim 1, wherein one of the first and second polymerization partners is an amine, and the other of the first and second polymerization partners is an isocyanate compound.

### Claim 11 (depends on 1)

The method of claim 1, wherein the droplets are formed by feeding the first liquid phase including the light reflecting solid integral particles through a spray nozzle into a gaseous phase.

### Claim 12 (depends on 1)

The method of claim 1, wherein the droplets are formed of the first liquid phase including the light reflecting solid integral particles and immersed in the second liquid phase in a microfluidic device, wherein the first liquid phase including the solid parts is fed into a flow of a fourth liquid phase not including the second polymerization partner before adding the second polymerization partner to prepare the second liquid phase including the fourth liquid phase.

### Claim 13 (depends on 1)

The method of claim 1, wherein the shell has a thickness of not more than λ; and wherein λ is a wavelength of light to be reflected by the light reflecting solid integral particles.

### Claim 14 (depends on 1)

The method of claim 1, wherein the monodisperse spherical microcapsules have a diameter in a range of 10 μm to 200 μm.

### Claim 15 (depends on 1)

A plurality of monodisperse spherical microcapsules made by the method of claim 1, wherein each monodisperse spherical microcapsule comprises:
a core;
a shell of a polymeric material enclosing the core; and
at least one light reflecting solid integral particle reflecting incoming light to be reflected by the at least one solid integral particle in a defined direction for determining the position and orientation of the microcapsule, embedded in the core and fixed in its orientation with regard to the shell;
wherein the shell and the core are transparent for the light to be reflected by the at least one light reflecting solid integral particle entering and exiting the microcapsule,
wherein the shell is so thin that it does essentially not deflect the light to be reflected by the at least one light reflecting solid integral particle entering and exiting the microcapsule, and
wherein the core includes a main component of the transparent fluid such that a refraction index of the core essentially matches a refraction index of the transparent fluid.

### Claim 16 (depends on 15)

The plurality of monodisperse spherical microcapsules of claim 15, wherein the shell has a thickness of not more than λ; and wherein λ is a wavelength of light to be reflected by the at least one solid integral particle.

### Claim 17 (depends on 15)

The plurality of monodisperse spherical microcapsules of claim 15, wherein the microcapsules have a diameter in a range of 10 μm to 200 μm.

### Claim 18 (depends on 1)

The method of claim 1, wherein the monodisperse spherical microcapsules have a diameter in a range of 10 μm to 70 μm.

### Claim 19 (depends on 13)

The method of claim 13, wherein the shell has a thickness of not more than λ/2.

### Claim 20 (depends on 16)

The plurality of monodisperse spherical microcapsules of claim 16, wherein the shell has a thickness of not more than λ/2.