# US 12,180,328 B2 · Strong binding metal-chelating resins

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- Number: US 12,180,328 B2
- Document ID: US12180328B2
- Status: Granted
- Kind: B2
- Application number: 17/736,537
- Filed: 2022-05-04
- Published: 2022-12-01
- Granted: 2024-12-31
- Earliest claimed: 2021-05-04
- Assignees: Sachem, Inc.
- Applicants: Sachem, Inc.
- Inventors: Barry L. Haymore; Sara S. Moghaddam; Charles B. Little; Ari K. Kar
- Web page: https://patentgrep.com/patent/US12180328B2

## CPC

- B01J 45/00: Ion-exchange in which a complex or a chelate is formed; Use of material as complex or chelate forming ion-exchangers; Treatment of material for improving the complex or chelate forming ion-exchange properties (ion-exchange chromatography processes B01D15/36)
- C08G 59/1477: {containing nitrogen}
- B01J 47/016: Modification or after-treatment of ion-exchangers
- C02F 1/42: by ion-exchange (ion-exchange in general B01J)
- C02F 1/62: Heavy metal compounds
- C02F 2101/20: Heavy metals or heavy metal compounds
- C02F 2103/04: for obtaining ultra-pure water
- 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
- 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)

## Abstract

A metal-chelating resin includes (a) a compound represented by Formula (I): or a stereoisomeric form thereof or a salt thereof, wherein R1, R2, R3, R4, Ra, Rb, Rc and Rd are as defined herein; and (b) an organic polymer resin having at least one complementary reactive functional group covalently linked with at least one linking group of the compound represented by Formula (I).

## Claims

### Claim 1

A metal-chelating resin, comprising:
(a) a compound represented by Formula (I):
or a stereoisomeric form thereof or a salt thereof, wherein
one of R1 and R2, and one of R3 and R4 are independently a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety containing at least one linking group for covalently linking the compound of Formula (I) to an organic polymer resin, wherein the at least one linking group is represented by the formula —(CH2)x—NHR5 where x is 2 to 6, and R5 is independently hydrogen, methyl or ethyl, and the other one of R1 and R2, and the other one of R3 and R4 are independently a protonated or deprotonated, substituted or unsubstituted carboxyalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted methylene group or a substituted or unsubstituted ethylene group optionally containing another linking group for covalently linking the compound of Formula (I) to the organic polymer resin; and
Ra, Rb, Rc and Rd are hydrogen; and
(b) an organic polymer resin comprising a styrenic polymer or copolymer having at least one complementary reactive functional group covalently linked with the at least one linking group of the compound represented by Formula (I).

### Claim 2 (depends on 1)

The metal-chelating resin of claim 1, wherein R5 is hydrogen.

### Claim 3 (depends on 1)

The metal-chelating resin of claim 1, wherein R5 is methyl.

### Claim 4 (depends on 1)

The metal-chelating resin of claim 1, wherein R5 is ethyl.

### Claim 5 (depends on 1)

The metal-chelating resin of claim 1, wherein the protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety independently is a moiety represented by the structure of Formula (II) or a moiety represented by the structure of Formula (III):
—CRRL-2-OH—C6Y4 (II)
—CRRL-2-O—C6Y4 (III)
wherein R is independently hydrogen, a linear or branched C1 to C4 alkyl moiety, a linear or branched C1 to C4 hydroxyalkyl or a linear or branched C1 to C4 alkyl moiety containing one or more ether linkages, RL is the linking group for covalently linking the compound of Formula (I) to the organic polymer resin, and Y is hydrogen.

### Claim 6 (depends on 5)

The metal-chelating resin of claim 5, wherein the protonated or deprotonated, substituted or unsubstituted carboxyalkyl-containing moiety independently is a protonated or deprotonated, substituted or unsubstituted carboxymethyl moiety represented by the structure of Formula (IV) or a protonated or deprotonated, substituted or unsubstituted carboxymethyl moiety represented by the structure of Formula (V):
—CRRL—CO2H (IV)
—CRRL—CO2 (V)
wherein R is independently hydrogen, a linear or branched C1 to C4 alkyl moiety, a linear or branched C1 to C4 hydroxyalkyl or a linear or branched C1 to C4 alkyl moiety containing one or more ether linkages, and RL is another linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

### Claim 7 (depends on 5)

The metal-chelating resin of claim 5, wherein the protonated or deprotonated, substituted or unsubstituted carboxyalkyl-containing moiety independently is a protonated or deprotonated, substituted or unsubstituted carboxyethyl moiety represented by the structure of Formula (VI) or a protonated or deprotonated, substituted or unsubstituted carboxyethyl moiety represented by the structure of Formula (VII):
—CRRL—CRRL—CO2H (VI)
—CRRL—CRRL—CO2− (VII)
wherein R is independently hydrogen, a linear or branched C1 to C4 alkyl moiety, a linear or branched C1 to C4 hydroxyalkyl or a linear or branched C1 to Ca alkyl moiety containing one or more ether linkages, and RL is another linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

### Claim 8 (depends on 5)

The metal-chelating resin of claim 5, wherein the linking group is represented by the formula —(CH2)x—NHR5 where x is 2 to 6, and R5 is hydrogen.

### Claim 9 (depends on 5)

The metal-chelating resin of claim 5, wherein the linking group is represented by the formula —(CH2)x—NHR5 where x is 2 to 6, and R5 is methyl.

### Claim 10 (depends on 5)

The metal-chelating resin of claim 5, wherein the linking group is represented by the formula —(CH2)x—NHR5 where x is 2 to 6, and R5 is ethyl.

### Claim 11 (depends on 1)

The metal-chelating resin of claim 1, wherein the compound of Formula (I) is represented by a compound having the structure of Formula (Ia):
wherein:
R″ is independently hydrogen or a linking group for covalently linking the compound of Formula (Ia) to the organic polymer resin, wherein at least one of R″ is a linking group represented by the formula —(CH2)x—NHR5 where x is 2 to 6, and R5 is independently hydrogen, methyl or ethyl;
R′ is independently a protonated or deprotonated, substituted or unsubstituted carboxyalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted methylene group or a substituted or unsubstituted ethylene group optionally containing another linking group for covalently linking the compound of Formula (Ia) to the organic polymer resin;
m and n are independently integers from 1 to 4; and;
Ra, Rb, Rc and Rd are hydrogen.

### Claim 12 (depends on 11)

The metal-chelating resin of claim 11, wherein R3 is hydrogen.

### Claim 13 (depends on 11)

The metal-chelating resin of claim 11, wherein R5 is methyl.

### Claim 14 (depends on 11)

The metal-chelating resin of claim 11, wherein R5 is ethyl.

### Claim 15 (depends on 11)

The metal-chelating resin of claim 11, wherein R′ is independently a protonated or deprotonated, unsubstituted carboxymethyl moiety.

### Claim 16 (depends on 11)

The metal-chelating resin of claim 11, wherein R′ is independently a protonated or deprotonated, unsubstituted carboxyethyl moiety.