Guanidine-functionalized particles and methods of making and using

Patent metadata

Field	Value
Publication number	US-10450333-B2
Application number	US-201916276907-A
Country	US
Kind code	B2
Filing date	Feb 15, 2019
Priority date	Dec 4, 2012
Publication date	Oct 22, 2019
Grant date	Oct 22, 2019

Abstract

Guanidine-functionalized particles and methods of making and using such particles.

First claim

What is claimed is:

1. A guanidine-functionalized silica gel particle, comprising:
a silica gel particle comprising at least one ligand comprising a guanidine group, the ligand comprising the formula —O n Si—S m -G,
where —O is an oxygen atom that is covalently bonded to the surface of the silica gel particle,
n is 1, 2 or 3,
S is a spacer group comprising a backbone with m atoms,
m is 2-16, inclusive,
G is a guanidine group of the formula NH—C(NH)—NH 2 ,
wherein the guanidine group is charged and comprises an associated counterion and wherein the counterion does not comprise a halogen,
and wherein the silica gel particle comprises a particle size of about 25-100 microns and a pore size of about 60-2000 Angstroms.

2. The particle of claim 1 wherein all m atoms of the backbone of the spacer group S are carbon atoms.

3. The particle of claim 2 wherein m=3.

4. The particle of claim 1 wherein the spacer group S comprises a secondary amine.

5. The particle of claim 1 wherein the guanidine group is the reaction product of a primary amine and O-methylisourea hemisulfate.

6. The particle of claim 1 wherein the ligand is the reaction product of one or more hydroxyl groups of the silica particle with one or more reactive groups of a silane coupling agent moiety of the ligand.

7. The particle of claim 1 wherein the counterion that is associated with the guanidine group is a sulfate ion.

8. The particle of claim 1 wherein the counterion that is associated with the guanidine group is a bisulfate ion.

9. The particle of claim 1 wherein the counterion that is associated with the guanidine group is a hydroxide ion.

10. The particle of claim 1 wherein residual hydroxyl groups are present on the surface of the particle.

11. The particle of claim 1 wherein each ligand has only a single guanidine group.

12. The particle of claim 1 wherein the guanidine group-containing ligands are the only ligands present on the particle.

13. A fluid-purification device comprising a plurality of guanidine-functionalized silica gel particles, each guanidine-functionalized silica gel particle comprising at least one ligand comprising a guanidine group, the ligand comprising the formula —O n Si—S m -G,
where —O is an oxygen atom that is covalently bonded to the surface of the silica gel particle,
n is 1, 2 or 3,
S is a spacer group comprising a backbone with m atoms,
m is 2-16, inclusive,
G is a guanidine group of the formula NH—C(NH)—NH 2 ,
wherein the guanidine group is charged and comprises an associated counterion that does not comprise a halogen,
and wherein the guanidine-functionalized silica gel particles are entrapped within a container that is configured to accept a fluid to be purified and to allow a purified fluid to be removed therefrom.

14. The fluid-purification device of claim 13 wherein the guanidine group is the reaction product of a primary amine and O-methylisourea hemisulfate.

15. The fluid-purification device of claim 13 wherein the silica gel particles comprise a particle size of about 25-100 microns and a pore size of about 60-2000 Angstroms.

16. The fluid-purification device of claim 13 wherein the ligand is the reaction product of one or more hydroxyl groups of the silica particle with one or more reactive groups of a silane coupling agent moiety of the ligand.

17. The fluid-purification device of claim 13 wherein the counterion that is associated with the guanidine group is a sulfate ion.

18. The fluid-purification device of claim 13 wherein the counterion that is associated with the guanidine group is a bisulfate ion.

19. The fluid-purification device of claim 13 wherein the counterion that is associated with the guanidine group is a hydroxide ion.

Assignees

• 3M Innovative Properties Co

Inventors

• Griesgraber George W
• Fitzsimons Jr Robert T
• Hanggi Douglas A
• Nakamura Masayuki
• Rasmussen Jerald K

Classifications

• C07F7/1892

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title

• B01J20/28083

  being in the range 2-50 nm, i.e. mesopores · CPC title

• B01J20/3244

  Non-macromolecular compounds · CPC title

• B01J20/286

  Phases chemically bonded to a substrate, e.g. to silica or to polymers · CPC title

• B01J20/28004

  Sorbent size or size distribution, e.g. particle size · CPC title