CA2309486A1

CA2309486A1 - Chelating silicone polymers

Info

Publication number: CA2309486A1
Application number: CA 2309486
Authority: CA
Inventors: Michael A. Brook; Rodica S. Himmeldirk
Original assignee: McMaster University
Current assignee: McMaster University
Priority date: 1999-05-27
Filing date: 2000-05-26
Publication date: 2000-11-27
Anticipated expiration: 2020-05-26
Also published as: CA2309486C

Abstract

Disclosed are silicone polymer based compounds, which include a hydrophobic silicone polymer backbone and a hydrophilic component. The hydrophilic component may act as a chelating agent to bind a metal. The hydrophilic component may be hydrophilic prior to binding with a metal or after binding. Also disclosed are methods of making these compounds. The compounds are useful in a variety of applications.

Claims

1. A silicone polymer comprising a hydrophobic polysiloxane backbone and at least one metal binding site which is covalently bound to the hydrophobic polysiloxane backbone, the at least one metal binding site comprising at least two ligands which are optionally bound to a metal.

2. A silicone polymer of claim 1 wherein at least one of the ligands is hydrophilic either before or after being bound to a metal..

3. The compound of claim 1 wherein at least one of the ligands is selected from the group of ligands consisting of: i) functional alkyl or aryl groups bearing heteroatom-based ligands, ii) functional alkyl or aryl groups bearing heteroatom-based ligands where the ligands possess exchangeable hydrogens and iii) functional alkyl or aryl groups bearing n-ligands.

4. The compound of claim 3 wherein at least one of the ligands comprises exchangeable hydrogen groups.

5. The compound of claim 4 wherein the exchangeable hydrogen groups are selected from the group consisting of OH, NH, SH and PH.

6. The compound of claim 5 wherein the exchangeable hydrogen groups are selected from the group consisting of OH and NH.

7. The compound of claim 6 wherein the metal binding site comprises two or more carboxylic acid groups.

8. The compound of claim 7 wherein the at least one metal binding site comprises a group selected from the group of formulas consisting of:

where W is N, P, or C; X is C, N, O or S; Y is N, O, S, P, or C; t is between 1 and 10;
and m is between 0 and 10.

9. The compound of claim 1 wherein at least one metal binding site is covalently bound to the hydrophobic polysiloxane backbone via a linker which is more stable to hydrolysis than the siloxane linkage in the silicone polymer backbone.

10. The compound of claim 9 wherein the linker is selected from the group of linkers consisting of C, N, O, S, P, amides, esters, thioesters, urethanes, ureas, alkyl, aryl, functional alkyl or functional aryl groups.

11. The compound of claim 10 wherein the linker is selected from the group of linkers consisting of:

where k is between 0 and 10;
R12 is H, alkyl, aryl, functional alkyl or functional aryl, R13 and R14 are independently H, alkyl, aryl, functional alkyl or functional aryl, alkoxy or siloxy, and R3Si is the silicone polymer backbone.

12. The compound of claim 11 wherein the metal binding site is selected from the group consisting of the following formulas:
where W is N, P, or C;
X is C, N, O or S;
Y is N, O, S, P, or C;
n is between 1 and 10;
k and m are between 0 and 10;
R12, R13, and R14 are as defined in claim 11; and R3Si is the silicone polymer backbone.

13. The compound of claim 10 wherein the metal binding site is selected from the group consisting of NTA and succinyl.

14. The compound of claim 13 wherein the polysiloxane backbone is a polydimethylsiloxane.

15. The compound of claim 10 wherein the compound is selected from the group of compounds consisting of SUCC-DMS-A11, SUCC-DMS-A15, SUCC-AMS-A21, SUCC-AMS-132, SUCC-AMS-152, SUCC-AMS-162, NTA-DMS-A11, NTA-DMS-A15, NTA-AMS-21, NTA-AMS-132, NTA-AMS-152, and NTA-AMS-162, and compounds of the following general formulae:

where W is a group of the formula:

where X is O or N; and n and m are independently greater than or equal to 0, with the proviso that the total molecular weight of the compound is between about 500 and 500,000 g/mol.

16. The compound of claim 1 wherein at least one metal binding site comprises ligands selected from the group of ligands consisting of bi, tri, tetra, penta and hexadentate ligands.

17. The compound of claim 1 having a molecular weight of between about 500 and about 500,000 g/mol.

18. The compound of claim 17 having a molecular weight of between about 500 and about 15,000 g/mol.

19. The compound of claim 18 having a molecular weight of between about 1500 and about 15,000 g/mol.

20. The compound of claim 1, wherein the ligand is bound to a metal.

21. The compound of claim 20 wherein the metal is selected from the group of metals consisting of alkali metals, alkaline earth metals, Group 13 elements, transition metals and lanthanides and actinides.

22. The compound of claim 20 wherein the metal is a metal ion.

23. The compound of claim 22 wherein the metal ion is selected from the group of metal ions consisting of Ca2+, Mg2+, Ni2+, Fe3+, Cu2+, and Co2+.

24. The compound of claim 1 having a formula I:
T1-Q n-T2 (I) where n is greater than or equal to 0; and where Q is an internal siloxane group of the formula II:

and, where R4 and R5, for each internal siloxane group, are the same or different, and where R4 and R5 are independently, H with the proviso that both R4 and R5 are not H on the same internal siloxane group, alkoxy, alkyl, aryl, functional alkyl, functional aryl, a metal-binding site comprising at least two ligands optionally bound to a metal, or a group having an internal siloxane group of the formula III:

where r is ~ 0;
R7, and R8, for each internal siloxane group are the same or different, and R6, R7, and R8 are independently H with the proviso that not more than one of R6, R7, and R8 is H on any internal siloxane group, alkoxy, siloxy, alkyl, functional alkyl, aryl, functional aryl, or a metal binding site comprising at least two ligands optionally bound to a metal, T1 is a group of the formula (IV):

T2 is a group of the formula (V):
where, R1, R2, R3, R9, R10, R11, are independently, H with the proviso that each silicon atom has no more than one H, alkoxy, siloxy, alkyl, functional alkyl, aryl, functional aryl, or a metal binding site comprising at least two ligands optionally bound to a metal;
with the proviso that at least one of R1 to R11 is a metal binding site comprising at least two ligands optionally bound to a metal and with the proviso that the molecular weight of the compound is between about 500 and about 500,000 g/mol.

25. The compound of claim 24 having a molecular weight of between about 500 and about 500,000 g/mol.

26. The compound of claim 25 wherein the molecular weight is between about 500 and about 15,000 g/mol.

27. The compound of claim 26 wherein the molecular weight is between about 1500 and about 15,000 g/mol.

28. The compound of claim 27 wherein at least one of R1, R2, R3, R9, R10, R11 is a metal binding site comprising at least two ligands optionally bound to a metal.

29. The compound of claim 28 wherein at least one of R1, R2, R3, and at least one of R9, R10, R11 is a metal binding site comprising at least two ligands optionally bound to a metal.

30. The compound of claim 24, wherein at least one of R4, R5, R6, R7, and R8 is a metal binding site comprising at least two ligands optionally bound to a metal.

31. The compound of claim 30, comprising at least one metal binding site comprising at least two ligands, bound to each siloxane group.

32. The compound of claim 30, comprising at least one metal binding site comprising at least two ligands, bound to one of every 5 to 200 internal siloxane groups.