IP Library Granted Patent US 10,315,185
Granted Patent B2
US 10,315,185 · App. 15/650,234 · Granted Jun 11, 2019

Polyfunctional sorbent materials

Inventors: Kara Nell (Eugene, OR); Darren W. Johnson (Eugene, OR); Jonathan Pittman (Richland, WA); Wilaiwan Chouyyok (Richland, WA); Raymond Shane Addleman (Richland, WA); Marvin G. Warner (Richland, WA)
Assignees: University of Oregon; Battelle Memorial Institute
B01J20/3042B01J20/103C07C323/25C07C323/29C07F9/3839C07F9/3847C07F9/3865B01J2219/00596C07B2200/11
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Quick Facts
Patent No.
US 10,315,185
App. No.
15/650,234
Granted
Jun 11, 2019
Kind
B2
Abstract

Disclosed herein is a material comprising a functionalized solid support surface, wherein the functionalization comprises a thioalkylene linker bound to the support surface and the thioalkylene linker is coupled to a moiety derived from a ligand, wherein the ligand includes a terminal alkenyl and at least one first functional group configured to bind to at least one predetermined target species.

Claims (24)

1. A material comprising:

wherein A is a solid support surface; R 1 is (—CH 2 —) n ; R 2 is (—CH 2 —) m or (—CH 2 —) a Ph(—CH 2 —) b ; X is selected from —CH(P(═O)(OH) 2 ) 2 , or —N(—CH 2 —COOH) 2 ; and n is 1 to 6; m is 2 to 6; a is 2 to 6; and b is 1 to 6; wherein Ph is a phenylene.

2. The material of claim 1 , further comprising a hydroxy or a thioalkyl directly bound to A.

3. The material of claim 1 , wherein n is 3.

4. The material of claim 1 , wherein R 2 is (—CH 2 —) m and m is 3.

5. The material of claim 1 , wherein R 2 is (—CH 2 —) a Ph(—CH 2 —) b .

6. The material of claim 1 , wherein R 2 is (—CH 2 —) a Ph(—CH 2 —) b and a is 2 and b is 1.

7. The material of claim 3 , wherein X comprises a phosphonic acid moiety or an iminodiacetic acid moiety.

8. The material of claim 1 , wherein A comprises a silica substrate.

9. A material comprising a functionalized solid support surface, wherein the functionalization comprises a thioalkylene linker bound to the support surface and the thioalkylene linker is coupled to a moiety derived from a ligand, wherein the ligand includes a terminal alkenyl and at least one first functional group configured to bind to at least one predetermined target species, and wherein the solid support surface comprises a silica substrate, and wherein the first functional group comprises a phosphonic acid moiety or an iminodiacetic acid moiety.

10. The material of claim 9 , further comprising at least one second functional group bound to the support surface and configured to bind to at least one predetermined target species, wherein the at least one second functional group is selected from a thioalkyl or a hydroxy.

11. The material of claim 9 , wherein the target species are selected from a metal, a metalloid, an oxyanion, a radioactive species, a polar organic compound, or a combination thereof.

12. A method for capturing at least one target species from an aqueous source comprising contacting the aqueous source containing at least one target species with the material of claim 1 and capturing the at least one species onto the material of claim 1 .

13. A method for capturing at least one target species from an aqueous source comprising contacting the aqueous source containing at least one target species with the material of claim 12 and capturing the at least one species onto the material of claim 12 .

14. The method of claim 12 , wherein the target species are selected from a metal, a metalloid, an oxyanion, a radioactive species, a polar organic compound, or a combination thereof.

15. The method of claim 13 , wherein the target species are selected from a metal, a metalloid, an oxyanion, a radioactive species, a polar organic compound, or a combination thereof.

16. The method of claim 12 , wherein the target species is selected from arsenic, selenium, cobalt, silver, cadmium, mercury, thallium, lead, uranium, rare earth element, copper or zinc.

17. A material comprising:

wherein A is a solid support surface; R 1 is ( 13 CH 2 —) n ; R 2 is (—CH 2 —) m or (—CH 2 —) a Ph(—CH 2 —) b ; X comprises a phosphonic acid moiety or an iminodiacetic acid moiety; and n is 1 to 6; m is 2 to 6; a is 2 to 6; and b is 1 to 6; wherein Ph is a phenylene.

18. A material comprising:

wherein A is a solid support surface; R 1 is (—CH 2 —) n ; R 2 is (—CH 2 —) m or (—CH 2 —) a Ph(—CH 2 —) b ; X is a urea, thiourea, phosphinimine, hydroxypyridinoate (HOPO), sulfocatecholamide (CAMS), terephthalimide, carbamoylmethylphosphine oxide (CMPO), phosphine derivative, phosphine oxide derivative, sulfonamide derivative, ethylenediaminetetraacetic acid (EDTA) derivative, dihydroxybenzene, or N-phenyliminodiacetic acid; and n is 1 to 6; m is 2 to 6; a is 2 to 6; and b is 1 to 6; wherein Ph is a phenylene.

19. A material comprising:

wherein A is a solid support surface; R 1 is (—CH 2 —) n ; R 2 is (—CH 2 —) a Ph(—CH 2 —)b; X is a first functional group configured to bind to at least one predetermined target species; and n is 1 to 6; a is 2 to 6; and b is 1 to 6; wherein Ph is a phenylene.

20. A material comprising a functionalized solid support surface, wherein the functionalization comprises a thioalkylene linker bound to the support surface and the thioalkylene linker is coupled to a moiety derived from a ligand, wherein the ligand includes a terminal alkenyl and at least one first functional group configured to bind to at least one predetermined target species, and wherein the solid support surface comprises a silica substrate, and wherein the first functional group is selected from —N(CH 2 CO 2 H) 2 , —NHCONH 2 , —NHCSNH 2 , —SO 2 NH 2 , or —NHCOCH 2 P(═O)R′R″) wherein R′ and R″ are independently lower alkyl or aryl groups.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2019
From: PITTMAN, JONATHAN; CHOUYYOK, WILAIWAN; ADDLEMAN, RAYMOND SHANE; WARNER, MARVIN
To: BATTELLE MEMORIAL INSTITUTE
Reel/Frame 048127/0400 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2019
From: NELL, KARA; JOHNSON, DARREN W.
To: UNIVERSITY OF OREGON
Reel/Frame 048127/0472 →
CONFIRMATORY LICENSE Recorded Aug 16, 2017
From: BATTELLE MEMORIAL INSTITUTE, PACIFIC NORTHWEST DIVISION
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 043306/0972 →
Continuity (2)
Provisional Application 62362510 · Jul 14, 2016
Related Publication 20180015442A1 · Jan 18, 2018