STRONG BINDING METAL-CHELATING RESINS USING MACROCYCLE MOLECULES

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 and R 3 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, wherein at least one of R 1 , R 2 and R 3 is 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;

R a , R b , R c and R d are independently R or a linking group for covalently linking the compound of Formula (I) to an organic polymer resin or wherein 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;

R is independently hydrogen, a substituted or unsubstituted hydrocarbyl group of from 1 to about 18 carbon atoms, a halogen or a polar functional group;

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

2 . The process of claim 1 , wherein in the compound represented by Formula (I), at least one of R 1 , R 2 and R 3 is a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety containing a linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

3 . The process of claim 2 , wherein the linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, R 5 is independently hydrogen, methyl or ethyl, and the organic polymer resin comprises a styrenic polymer or copolymer, an acrylic polymer or copolymer, or a methacrylic polymer or copolymer.

4 . The process of claim 1 , wherein in the compound represented by Formula (I), at least two of R 1 , R 2 and R 3 is a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety, wherein at least one of the protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moieties contains a linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

5 . The process of claim 3 , wherein the 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 the organic polymer resin comprises a styrenic polymer or copolymer, an acrylic polymer or copolymer, or a methacrylic polymer or copolymer.

6 . The process of claim 1 , wherein in the compound represented by Formula (I), each of R 1 , R 2 and R 3 is a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety, wherein at least one of the protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moieties contains a linking group for covalently linking the compound of Formula (I) to the organic polymer resin.

7 . The process of claim 6 , wherein the 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 the organic polymer resin comprises a styrenic polymer or copolymer, an acrylic polymer or copolymer, or a methacrylic polymer or copolymer.

8 . The process of claim 1 , wherein in the compound represented by Formula (I), each of R 1 , R 2 and R 3 is a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety, 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.

9 . The process of claim 8 , wherein the linking group is represented by the formula —(CH 2 ) x —NHR 5 where x is 2 to 6, R 5 is independently hydrogen, methyl or ethyl, and the organic polymer resin comprises a styrenic polymer or copolymer, an acrylic polymer or copolymer, or a methacrylic polymer or copolymer.

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

11 . The process of claim 1 , wherein the compound of Formula (I) is represented by a structure of Formula (Ib):

or a salt thereof, wherein m, n and p are independently an integer from 1 to 4, A, A′, A″ and R a are independently hydrogen, a substituted or unsubstituted hydrocarbyl group of from 1 to about 18 carbon atoms, a halogen, a polar functional group or a linking group for covalently linking the compound of Formula (Ib) to the organic polymer resin.

12 . The process of claim 11 , wherein at least one of A, A′ and A″ is a linking group for covalently linking the compound of Formula (Ib) to the organic polymer resin, R a is hydrogen, and wherein the linking group is represented by the structure —(CH 2 ) x —NH 2 where x is from 2 to 6.

13 . 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.

14 . The process of claim 13 , 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, methyl or ethyl.

15 . 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 (II):

or a stereoisomeric form thereof or a salt thereof;

wherein

R 1 , R 2 , R 3 and R 4 are independently hydrogen, a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety optionally containing a linking group for covalently linking the compound of Formula (II) 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 (II) 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 (II) 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 (II) to an organic polymer resin, wherein the 2-hydroxybenzyl moiety occurs no more than three times in the compound, and with the proviso that no more than one of R 1 , R 2 , R 3 and R 4 can be hydrogen;

R a , R b , R c and R d are independently R or a linking group for covalently linking the compound of Formula (II) to an organic polymer resin or wherein 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;

R is independently hydrogen, a substituted or unsubstituted hydrocarbyl group of from 1 to about 18 carbon atoms, a halogen, and a polar functional group;

wherein when one of R 1 , R 2 , R 3 and R 4 is not hydrogen then at least one linking group for covalently linking the compound of Formula (II) to an organic polymer resin occurs in the compound; and

(b) an organic polymer resin having at least one complementary reactive functional group covalently linked with the linking group of the compound represented by Formula (II).

16 . The process of claim 15 , wherein one of R 1 , R 2 , R 3 and R 4 is a protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety containing a linking group for covalently linking the compound of Formula (II) to the organic polymer resin.

17 . The process of claim 16 , 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, methyl or ethyl.

18 . The process of claim 15 , wherein the protonated or deprotonated, substituted or unsubstituted 2-hydroxybenzyl moiety independently is a moiety represented by the structure of Formula (III) or a moiety represented by the structure of Formula (IV):

—CRR L —2—OH—C 6 Y 4   (III)

—CRR L —2—O—C 6 Y 4   (IV)

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 (II) to the organic polymer resin, and Y is hydrogen, methyl or ethyl.

19 . The process of claim 18 , 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.

20 . The process of claim 15 , wherein a concentration of the one or more metallic components in the aqueous solution and/or the non-aqueous solution is reduced to less than or equal to 10 parts per trillion.