# US 10,246,472 B2 · Guanidine-functionalized particles and methods of making and using

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- Number: US 10,246,472 B2
- Document ID: US10246472B2
- Status: Granted
- Kind: B2
- Application number: 15/488,716
- Filed: 2017-04-17
- Published: 2017-08-03
- Granted: 2019-04-02
- Earliest claimed: 2012-12-04
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: George W. Griesgraber; Robert T. Fitzsimons, Jr.; Douglas A. Hanggi; Masayuki Nakamura; Jerald K. Rasmussen
- Web page: https://patentgrep.com/patent/US10246472B2

## CPC

- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- B01D 15/00: Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D 24/00: Filters comprising loose filtering material, i.e. filtering material without any binder between the individual particles or fibres thereof (B01D27/02 takes precedence)
- B01J 20/103: {comprising silica}
- B01J 20/22: comprising organic material
- B01J 20/28004: {Sorbent size or size distribution, e.g. particle size}
- B01J 20/28083: {being in the range 2-50 nm, i.e. mesopores}
- B01J 20/28085: {being more than 50 nm, i.e. macropores}
- B01J 20/286: Phases chemically bonded to a substrate, e.g. to silica or to polymers
- B01J 20/289: bonded via a spacer
- B01J 20/3204: {Inorganic carriers, supports or substrates}
- B01J 20/3219: {involving a particular spacer or linking group, e.g. for attaching an active group}
- B01J 20/3244: {Non-macromolecular compounds}
- B01J 20/3293: {Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers}
- C07F 7/1872: {Preparation; Treatments not provided for in C07F7/20}
- C07F 7/1892: {by reactions not provided for in C07F7/1876 - C07F7/1888}
- C12M 25/16: {Particles; Beads; Granular material; Encapsulation (chemical or physical processes conducted in the presence of fluids and solid particles B01J8/00)}
- G01N 1/405: {by adsorption or absorption}
- B01J 2220/80: Aspects related to sorbents specially adapted for preparative, analytical or investigative chromatography
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C12M: APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; {APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS}
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

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

## Claims

### Claim 1

A method of making a guanidine-functionalized particle, comprising:
reacting O-methylisourea hemisulfate with a linker molecule comprising the formula
(RO)nRa3-nSi—Sm—X
where RO is an alkoxy group comprising one or two carbons, or is an acetoxy group,
where n is 1, 2 or 3,
where Ra is an unreactive group,
where S is a spacer group comprising a backbone with m atoms,
m is from 2-16, inclusive, and
where X is a primary amine that is capable of reacting with the O-methylisourea to form a guanidine group;
and,
reacting at least one of the RO groups of the linker molecule with a hydroxyl group of the particle to form a covalent bond between the linker molecule and the particle.

### Claim 2 (depends on 1)

The method of claim 1 wherein the (RO)nSi moiety comprises a trimethoxysilane moiety.

### Claim 3 (depends on 1)

The method of claim 1 wherein the linker molecule is 3-aminopropyltrimethoxysilane.

### Claim 4 (depends on 1)

The method of claim 1 wherein the (RO)nSi moiety comprises a triethoxysilane moiety.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

The method of claim 1 wherein m=3.

### Claim 7 (depends on 1)

The method of claim 1 wherein the spacer group S comprises at least one hetero atom.

### Claim 8 (depends on 7)

The method of claim 7 wherein the spacer group S comprises at least one secondary amine.

### Claim 9 (depends on 8)

The method of claim 8 wherein the linker molecule is N-(2-aminoethyl)-3-aminopropyltrimethoxysilane.

### Claim 10 (depends on 1)

The method of claim 1 wherein the step of reacting at least one of the RO groups of the linker molecule with a hydroxyl group of the particle to form a covalent bond between the linker molecule and the particle, is performed after the reacting of the O-methylisourea hemisulfate with the linker molecule.

### Claim 11 (depends on 1)

The method of claim 1 wherein the step of reacting at least one of the RO groups of the linker molecule with a hydroxyl group of the particle to form a covalent bond between the linker molecule and the particle, is performed before the reacting of the O-methylisourea hemisulfate with the linker molecule.

### Claim 12 (depends on 1)

The method of claim 1 wherein the particle is an insoluble inorganic porous particle.

### Claim 13 (depends on 12)

The method of claim 12 wherein the particle comprises vitrous SiO2.

### Claim 14 (depends on 13)

The method of claim 13 wherein the particle comprises surface hydroxyl groups.

### Claim 15 (depends on 14)

The method of claim 14 wherein the particle is a silica particle.

### Claim 16 (depends on 15)

The method of claim 15 wherein the particle is a silica gel particle.

### Claim 17 (depends on 16)

The method of claim 16 wherein the silica gel particle comprises a particle size of about 25-100 microns and a pore size of about 60-2000 Angstroms.

### Claim 18 (depends on 1)

The method of claim 1 wherein residual hydroxyl groups are present on a surface of the particle after the reacting of the at least one of the RO groups of the linker molecule with a hydroxyl group of the particle to form a covalent bond between the linker molecule and the particle.

### Claim 19 (depends on 1)

The method of claim 1 wherein the method does not include a step of equilibrating the particle in an atmosphere having a defined relative humidity prior to the reacting of the at least one of the RO groups of the linker molecule with a hydroxyl group of the particle to form a covalent bond between the linker molecule and the particle.