Contaminant-sequestering coatings and methods of using the same

Patent metadata

Field	Value
Publication number	US-12378138-B2
Application number	US-202217892222-A
Country	US
Kind code	B2
Filing date	Aug 22, 2022
Priority date	Jun 19, 2019
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

Contaminant-sequestering coatings include a network of hydrolyzed silane compounds including (i) a plurality of fluorinated functionalities, and (ii) a plurality of thiol functional groups are provided. The network of hydrolyzed silane compounds includes a fluorinated silane including (a) a hydrophilic polar head region. The polar head region includes one or multiple units of ethylene glycol (EG) functionality, (b) a fluorine-containing region, and (c) an anchor region including a silicon atom. The contaminant-sequestering coatings may sequester one or more per- and polyfluoroalkyl substances (PFAS), heavy metals, biological species, or any combination thereof.

First claim

What is claimed is:

1. A contaminant-sequestering coating, comprising a network of hydrolyzed silane compounds including (i) a plurality of fluorinated functionalities, and (ii) a plurality of thiol functional groups, wherein the network of hydrolyzed silane compounds includes a first group of fluorinated silane compounds and a second group of thiol-functional silane compounds,
wherein the network of hydrolyzed silane compounds includes a fluorinated silane comprising (a) a hydrophilic polar head region, wherein the polar head region comprises one or multiple units of ethylene glycol (EG) functionality, (b) a fluorine-containing region, and (c) an anchor region including a silicon atom.

2. The contaminant-sequestering coating of claim 1 , wherein the network of hydrolyzed silane compounds includes a thiol-functional silane including at least one alkoxy group bonded to a silicon atom.

3. The contaminant-sequestering coating of claim 2 , wherein the thiol-functional silane has a structure according to Formula (1):

wherein
—R 1 , —R 2 , and —R 3 are each a C 1 -C 4 radical,
R 4 is a saturated C 1 -C 20 radical or an unsaturated C 1 -C 20 radical,
X 1 , X 2 , and X 3 are each independently selected from —H or —SH, and

wherein at least one of X 1 , X 2 , and X 3 is —SH.

4. The contaminant-sequestering coating of claim 3 , wherein R 4 includes at least one side chain including one or more thiol functionalities thereon.

5. The contaminant-sequestering coating of claim 3 , wherein R 4 , includes at least one heteroatom selected from oxygen, nitrogen, sulfur, phosphorus, or combinations thereof.

6. The contaminant-sequestering coating of claim 1 , wherein the fluorinated silane comprises a linear C 1 -C 40 perfluorosilane.

7. The contaminant-sequestering coating of claim 1 , wherein the network of hydrolyzed silane compounds includes a first group of fluorinated silane compounds and a second group of fluorinated compounds, and wherein the first group of fluorinated silane compounds includes from about 1.5 to about 5 times more fluorine atoms than the second group of fluorinated compounds.

8. The contaminant-sequestering coating of claim 1 , wherein the network of hydrolyzed silane compounds has a first ratio between a number or fluorine atoms to a number of thiol groups from about 50:1 to about 1:1.

9. The contaminant-sequestering coating of claim 1 , wherein the contaminant-sequestering coating sequesters:
(i) one or more polyfluoroalkyl (PFAS) compounds initially present in a liquid contaminated with an initial quantity of the PFAS compounds, wherein an amount of the one or more PFAS compounds sequestered comprises from about 50% to about 100% by weight of the initial quantity of the PFAS compounds;
(ii) one or more heavy metals initially present in a liquid contaminated with an initial quantity of the heavy metals, wherein an amount of the one or more heavy metals sequestered comprises from about 50% to about 100% by weight of the initial quantity of the heavy metals; or
(iii) both (i) and (ii).

10. A method of functionalizing a substrate surface with contaminant-sequestering functionalities, the method comprising:
(A) covering an inorganic substrate with a liquid composition, the liquid composition comprising (i) a flowable carrier medium; and (ii) a plurality of hydrolyzable silane compounds including a plurality of thiol-functional silane compounds and a plurality of fluorinated silane compounds; wherein the plurality of fluorinated silane compounds comprises (a) a hydrophilic polar head region, wherein the polar head region comprises one or multiple units of ethylene glycol (EG) functionality, (b) a fluorine-containing region, and (c) an anchor region including a silicon atom; and
(B) hydrolyzing the plurality of hydrolyzable silane compounds to form a plurality of hydrolyzed silane compounds and allowing the hydrolyzed silane compounds to condense with each other to form a contaminant-sequestering coating bonded onto the inorganic substrate; wherein the contaminant-sequestering coating comprises a network of the hydrolyzed silane compounds.

11. The method of claim 10 , wherein about 10 to 100% by weight of the plurality of fluorinated silane compounds include (a) a respective hydrophilic polar head region, wherein the respective polar head region comprises one or multiple units of ethylene glycol (EG) functionality, (b) a respective fluorine-containing region, and (c) a respective anchor region including a silicon atom.

12. The method of claim 10 , wherein the plurality of hydrolyzable silane compounds includes from about 20% to about 95% by weight of the plurality of fluorinated silane compounds on a dry basis.

13. A device comprising:
an inorganic substrate; and
a contaminant-sequestering coating bonded to at least a portion of the inorganic substrate,
wherein the contaminant-sequestering coating in a dry and/or solid state comprises a network of hydrolyzed silane compounds including (i) a plurality of fluorinated functionalities, and (ii) a plurality of thiol functional groups, and
wherein the network of hydrolyzed silane compounds includes a fluorinated silane comprising (a) a hydrophilic polar head region, wherein the polar head region comprises one or multiple units of ethylene glycol (EG) functionality, (b) a fluorine-containing region, and (c) an anchor region including a silicon atom.

14. The device of claim 13 , wherein the inorganic substrate comprises a filtration medium, an ion exchange resin, a structured packing material, or a random packing material.

15. A method of removing contaminants from a contaminant-containing liquid, the method comprising:
flowing the contaminant-containing liquid across or through a device, the device comprising:
an inorganic substrate; and
a contaminant-sequestering coating bonded to at least a portion of the inorganic substrate,
wherein the contaminant-sequestering coating in a dry and/or solid state comprises a network of hydrolyzed silane compounds including (i) a plurality of fluorinated functionalities, and (ii) a plurality of thiol functional groups, and
wherein the network of hydrolyzed silane compounds includes a fluorinated silane comprising (a) a hydrophilic polar head region, wherein the polar head region comprises one or multiple units of ethylene glycol (EG) functionality, (b) a fluorine-containing region, and (c) an anchor region including a silicon atom; and

contacting the contaminant-containing liquid with the contaminant-sequestering coating.

16. The method of claim 15 , wherein the contaminant-containing liquid comprises water.

17. The method of claim 15 , wherein contacting the contaminant-containing liquid with the contaminant-sequestering coating comprises flowing the contaminant-containing liquid across or through the device until the contaminant-sequestering coating sequesters (i) from about 50% to about 100% by weight of an initial quantity of one or more polyfluoroalkyl (PFAS) compounds initially present in the contaminant-containing liquid, (ii) from about 50% to about 100% by weight of an initial quantity of one or more heavy metals initially present in contaminant-containing liquid, or (iii) both (i) and (ii).

18. The method of claim 17 , wherein contacting the contaminant-containing liquid with the contaminant-sequestering coating comprises recirculating the contaminant-containing liquid across or through the device until

Assignees

• Univ Johns Hopkins

Inventors

• Hoffman Jr Christopher M
• Xia Zhiyong
• Johnson James K

Classifications

• C02F1/583

  by removing fluoride or fluorine compounds · CPC title

• C02F2101/20

  Heavy metals or heavy metal compounds · CPC title

• C02F2101/36

  containing halogen · CPC title

• C02F1/62

  Heavy metal compounds · CPC title

• C02F1/42

  by ion-exchange (ion-exchange in general B01J) · CPC title