# US 10,246,405 B2 · Porous diacetylene particles, synthesis method thereof

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- Number: US 10,246,405 B2
- Document ID: US10246405B2
- Status: Granted
- Kind: B2
- Application number: 15/008,167
- Filed: 2016-01-27
- Published: 2016-05-19
- Granted: 2019-04-02
- Earliest claimed: 2011-06-07
- Assignees: Korea University Research and Business Foundation
- Applicants: Korea University Research and Business Foundation
- Inventors: Dong June Ahn; Doo Ho Yang
- Web page: https://patentgrep.com/patent/US10246405B2

## CPC

- C07C 209/00: Preparation of compounds containing amino groups bound to a carbon skeleton
- B01J 19/10: employing sonic or ultrasonic vibrations
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- B82Y 40/00: Manufacture or treatment of nanostructures
- C07C 51/412: {by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part}
- B01J 2219/0877: Liquid
- Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.]
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Provided are a radial porous diacetylene particle, which is synthesized by ion-bonding a diacetylene-containing dicarboxylic acid or diamine monomer represented by Formula 1 with a diamine or dicarboxylic acid monomer represented by Formula 2, and a method of manufacturing the same.

## Claims

### Claim 1

A method of manufacturing a radial porous diacetylene particle, comprising the steps of:
(a) respectively dissolving a diacetylene-containing dicarboxylic acid monomer represented by Formula 1 below and a diamine monomer represented by Formula 2 below in a solvent to prepare a solution including the diacetylene-containing dicarboxylic acid monomer and a solution including the diamine monomer:
G-(A)x-C≡C—C≡C—(B)y-G [Formula 1]
wherein A and B are each independently selected from the group consisting of a substituted or unsubstituted alkyl group of two or more carbon atoms, an ethylene oxide group, an amide group and an ester group, G is COOH, and x and y are each independently an integer of 1 to 20,
Q-(D)m-Z-(E)n-Q [Formula 2]
wherein Z is selected from the group consisting of a benzene group, a pyridine group, a pyrimidine group and a naphthalene group, D and E are each independently a substituted or unsubstituted alkyl group of one or more carbon atoms Q, NH2, and m and n are each independently an integer of 0 to 20;
(b) ultrasonically treating each of the solutions;
(c) maintaining each of the ultrasonically-treated solutions at room temperature; and
(d) mixing the solution including the diacetylene-containing dicarboxylic acid monomer represented by Formula 1 above with the solution including the diamine monomer represented by Formula 2 above to form a radial porous diacetylene particle and then growing the radial porous acetylene particle.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the solvent is at least one selected from the group consisting of tetrahydrofuran (THF), chloroform, toluene, ethanol, isopropanol, and n-hexane.

### Claim 3 (depends on 1)

The method according to claim 1, wherein each of the solution including the diacetylene-containing dicarboxylic acid monomer represented by Formula 1 above and the solution including the diamine monomer represented by Formula 2 above has a concentration of 10 mM˜50 mM.

### Claim 4 (depends on 1)

The method according to claim 1, wherein each of the solution including the diacetylene-containing dicarboxylic acid monomer represented by Formula 1 above and the solution including the diamine monomer represented by Formula 2 above has a concentration of 10 mM˜20 mM.

### Claim 5 (depends on 1)

The method according to claim 1, wherein a mixing temperature of the step (d) is maintained at a temperature of 5˜30° C. for 10 minutes˜1 hour.

### Claim 6 (depends on 1)

The method according to claim 1, wherein a mixing temperature of the step (d) is maintained at a temperature of 10˜25° C. for 10 minutes˜1 hour.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the solution including the diacetylene-containing dicarboxylic acid monomer represented by Formula 1 above and the solution including the diamine monomer represented by Formula 2 above are mixed in a volume ratio of 1:0.2˜5.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the ultrasonic treatment is carried out for 30 minutes by a power of 5˜20 W.