IP Library › Granted Patent US 12,509,546
Granted Patent B2
US 12,509,546 · App. 18/954,867 · Granted Dec 30, 2025

Strong binding metal-chelating resins

Inventors: Barry L. Haymore (Avon, IN); Sara S. Moghaddam (Dripping Springs, TX); Charles B. Little (Austin, TX); Ari K. Kar (Bee Cave, TX)
Assignee: SACHEM, INC.
C08G59/1477C02F1/62
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Quick Facts
Patent No.
US 12,509,546
App. No.
18/954,867
Granted
Dec 30, 2025
Kind
B2
Abstract

A metal-chelating resin includes (a) a compound represented by Formula (I): or a stereoisomeric form thereof or a salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R a , R b , R c and R d 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 (41)

1 . A process for removing one or more metallic components that are contained in an aqueous solution and/or a non-aqueous solution, the process comprising the step of contacting an aqueous solution or a non-aqueous solution containing one or more metallic components with a metal-chelating resin for a time sufficient to reduce the concentration of the one or more metallic components in the aqueous solution and/or the non-aqueous solution, wherein the metal-chelating resin comprises:

(a) a compound represented by Formula (I):

or a stereoisomeric form thereof or a salt thereof, wherein:

R 1 , R 2 , R 3 and R 4 are independently a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety optionally containing a linking group for covalently linking the compound of Formula (I) to an organic polymer resin, 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 a linking group for covalently linking the compound of Formula (I) to an organic polymer resin, a protonated or deprotonated, substituted or unsubstituted phosphonoalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted methylene group or a substituted or unsubstituted ethylene group optionally containing a linking group for covalently linking the compound of Formula (I) to an organic polymer resin, or a protonated or deprotonated, substituted or unsubstituted hydroxyalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted ethylene group or a substituted or unsubstituted propylene group optionally containing a linking group for covalently linking the compound of Formula (I) to an organic polymer resin; and

R a , R b , R c and R d are independently hydrogen, a substituted or unsubstituted hydrocarbyl group of from 1 to about 18 carbon atoms, a halogen, a polar functional group, a linking group for covalently linking the compound of Formula (I) to an organic polymer resin or one of adjacent R a and R c or R a and R d or R b and R c or R b and R d are joined together to form a cis- or trans-cyclopentane moiety or a cis- or trans-cyclohexane moiety; and

wherein at least one linking group for covalently linking the compound of Formula (I) to an organic polymer resin occurs in the compound; and

wherein the at least one linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, and R 5 is independently hydrogen, methyl or ethyl; and

(b) an organic polymer resin having at least one complementary reactive functional group covalently linked with the at least one linking group of the compound represented by Formula (I), wherein the organic polymer resin comprises a styrenic polymer or copolymer, an acrylic polymer or copolymer, or a methacrylic polymer or copolymer.

2 . The process of claim 1 , wherein in the compound represented by Formula (I), one of R 1 and R 2 , and one of R 3 and R 4 are a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety, the other one of R 1 and R 2 ; and the other one of R 3 and R 4 are 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 moiety or a protonated or deprotonated, substituted or unsubstituted phosphonoalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted methylene group or a substituted or unsubstituted ethylene group; and one of R a , R b , R c and R d is a linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

3 . The process of claim 1 , wherein in the compound represented by Formula (I), one of R 1 and R 2 , and one of R 3 and R 4 are a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety, wherein at least one of the protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety contains a linking group; the other one of R 1 and R 2 , and the other one of R 3 and R 4 are 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 or a protonated or deprotonated, substituted or unsubstituted phosphonoalkyl-containing moiety, wherein the alkyl group is a substituted or unsubstituted methylene group or a substituted or unsubstituted ethylene group; and R a , R b , R c and R d are hydrogen.

4 . The process of claim 1 , wherein R 5 is hydrogen and the organic polymer resin comprises a styrenic polymer or copolymer.

5 . The process of claim 1 , wherein R 5 is methyl and the organic polymer resin comprises a styrenic polymer or copolymer.

6 . The process of claim 1 , wherein R 5 is ethyl and the organic polymer resin comprises a styrenic polymer or copolymer.

7 . The process 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):

—CRR L -2-OH—C 6 Y 4   (II)

—CRR L -2-O—C 6 Y 4   (III)

wherein R is independently hydrogen, a linear or branched C 1 to C 4 alkyl moiety, a linear or branched C 1 to C 4 hydroxyalkyl or a linear or branched C 1 to C 4 alkyl moiety containing one or more ether linkages, R L is the linking group for covalently linking the compound of Formula (I) to the organic polymer resin, and Y is hydrogen.

8 . The process of claim 7 , 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):

—CRR L —CO 2 H  (IV)

—CRR L —CO 2 −   (V)

wherein R is independently hydrogen, a linear or branched C 1 to C 4 alkyl moiety, a linear or branched C 1 to C 4 hydroxyalkyl or a linear or branched C 1 to C 4 alkyl moiety containing one or more ether linkages, and R L is another linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

9 . The process of claim 7 , 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):

—CRR L —CRR L —CO 2 H  (VI)

—CRR L —CRR L —CO 2 −   (VII)

wherein R is independently hydrogen, a linear or branched C 1 to C 4 alkyl moiety, a linear or branched C 1 to C 4 hydroxyalkyl or a linear or branched C 1 to C 4 alkyl moiety containing one or more ether linkages, and R L is another linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

10 . The process of claim 7 , wherein the linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, and R 5 is hydrogen.

11 . The process of claim 7 , wherein the linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, and R 5 is methyl.

12 . The process of claim 7 , wherein the linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, and R 5 is ethyl.

13 . The process 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 —(CH 2 ) x —NHR 5 where x is 2 to 6, and R 5 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;

R a , R b , R c and R d are hydrogen.

14 . The process of claim 13 , wherein R 5 is hydrogen.

15 . The process of claim 13 , wherein R 5 is methyl.

16 . The process of claim 13 , wherein R 5 is ethyl.

17 . The process of claim 13 , wherein R′ is independently a protonated or deprotonated, unsubstituted carboxymethyl moiety or a protonated or deprotonated, unsubstituted carboxyethyl moiety.

18 . The process of claim 1 , wherein the one or more metallic components comprise one or more of an iron ion and a copper ion, and wherein the concentration of the one or more metallic components in the aqueous solution and/or the non-aqueous solution are reduced to less than or equal to 10 parts-per-trillion.

19 . The process of claim 1 , wherein R 5 is hydrogen.

20 . The process of claim 1 , wherein R 5 is methyl.

Assignments (2)
SECURITY INTEREST Recorded Aug 4, 2026
From: SACHEM, INC.
To: FIRST BUSINESS SPECIALTY FINANCE, LLC
Reel/Frame 075521/0429 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2024
From: HAYMORE, BARRY L.; MOGHADDAM, SARA S.; LITTLE, CHARLES B.; KAR, ARI K.
To: SACHEM, INC.
Reel/Frame 069358/0910 →
Continuity (3)
Division 17736537 · May 4, 2022
Provisional Application 63183941 · May 4, 2021
Related Publication 20250084203A1 · Mar 13, 2025
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