# US 11,027,996 B1 · Crown ether functionalized substrates

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- Number: US 11,027,996 B1
- Document ID: US11027996B1
- Status: Granted
- Kind: B1
- Application number: 16/255,322
- Filed: 2019-01-23
- Granted: 2021-06-08
- Earliest claimed: 2019-01-23
- Assignees: The United States of America as represented by the Secretary of the Navy
- Applicants: The United States of America, as Represented by the Secretary of the Navy
- Inventors: Gregory Stephen Ostrom; Benjamin G Harvey
- Web page: https://patentgrep.com/patent/US11027996B1

## CPC

- C02F 1/683: {by addition of complex-forming compounds}
- C02F 1/288: {using composite sorbents, e.g. coated, impregnated, multi-layered}
- C09C 1/24: Oxides of iron
- C09C 3/08: Treatment with low-molecular-weight {non-polymer} organic compounds {(C09C3/006, C09C3/048 take precedence)}
- B82Y 25/00: Nanomagnetism, e.g. magnetoimpedance, anisotropic magnetoresistance, giant magnetoresistance or tunneling magnetoresistance
- B82Y 30/00: Nanotechnology for materials or surface science, e.g. nanocomposites
- B82Y 40/00: Manufacture or treatment of nanostructures
- C01P 2002/72: by d-values or two theta-values, e.g. as X-ray diagram
- C01P 2002/82: by IR- or Raman-data
- C01P 2002/88: by thermal analysis data, e.g. TGA, DTA, DSC
- C01P 2004/64: Nanometer sized, i.e. from 1-100 nanometer
- C01P 2006/42: Magnetic properties
- C02F 1/488: {for separation of magnetic materials, e.g. magnetic flocculation}
- C02F 2101/20: Heavy metals or heavy metal compounds
- C02F 2305/08: Nanoparticles or nanotubes
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- C09C: TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES (treatment of materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone C04B14/00, C04B18/00, C04B20/00); PREPARATION OF CARBON BLACK {; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS}
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- C01P: INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS

## Abstract

A method for making crown ether functionalized substrates, which includes modifying crown ether-based molecules by reacting with carboxylic acid functionalize chains. The crown ether-based molecules are then attached to substrates, thereby forming crown ether functionalized substrates.

## Claims

### Claim 1

A method for making crown ether functionalized substrates, comprising:
modifying crown ether-based molecules, wherein carboxylic acid functionalized hydrocarbon chains are reacted with crown ether-based molecules, thereby forming modified crown ether-based molecules; and
attaching the modified crown ether-based molecules to substrates, thereby forming crown ether functionalized substrates.

### Claim 2 (depends on 1)

The method of claim 1, wherein the carboxylic acid functionalized hydrocarbon chain is selected from the group consisting of a diacid chain, a polyacid chain, an aromatic acid chain, and an aliphatic acid chain, and combinations thereof.

### Claim 3 (depends on 2)

The method of claim 2, wherein the carboxylic acid functionalized hydrocarbon chain is added to the crown ether-based molecules in the presence of an acid catalyst selected from the group consisting of P2O5 in methanesulfonic acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid, heterogeneous Lewis acid catalysts, homogeneous Lewis acid catalysts, heterogeneous acid catalysts, heterogeneous Bønsted acids, homogenous Brønsted acids, and combinations thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the crown ether-based molecules are selected from the group consisting of substituted and non-substituted crown ethers containing an aromatic ring system, benzocrown ethers, azocrown ethers, metallacrown ethers, thiocrown ethers, cryptands, and combinations thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the carboxylic acid functionalized hydrocarbon chain includes two terminal carboxylic acid groups and about 4 carbon atoms to about 100 carbon atoms.

### Claim 6 (depends on 1)

The method of claim 1, wherein the carboxylic acid functionalized hydrocarbon chain includes two carboxylic acid groups anywhere on the acid chain.

### Claim 7 (depends on 1)

The method of claim 1, wherein the crown ether-based molecules and the carboxylic acid functionalized hydrocarbon chains are present in a ratio of about 1:1 to about 1:10, respectively.

### Claim 8 (depends on 1)

The method of claim 1, wherein the substrate is solid or porous particles, a solid or porous support, a solid or porous surface, and combinations thereof.

### Claim 9 (depends on 8)

The method of claim 8, wherein the particles have a diameter ranging from about 1 nm to about 500 microns.

### Claim 10 (depends on 9)

The method of claim 9, wherein the particles are selected from the group consisting of magnetic particles, superparamagnetic particles, and combinations thereof.

### Claim 11 (depends on 10)

The method of claim 10, wherein the particles are solid or porous nanoparticles selected from the group consisting of metallic particles, metal oxide particles, mixed metal oxide particles, and combinations thereof, wherein the particles have metals selected from the group consisting of Fe, Co, Ni, Mn, lanthanides, and combinations thereof.

### Claim 12 (depends on 8)

The method of claim 8, wherein the solid support, porous support, solid surface, or porous surface is selected from the group consisting of metals, metal oxides, metalloid oxides, ceramics, polymers, and combinations thereof.

### Claim 13 (depends on 1)

The method of claim 1, wherein attaching the crown ether-based molecules to a substrate includes heating, mixing, sonication, refluxing, altering the pH of a solution that contains both the substrates and the crown ether-based molecules, and combinations thereof.