IP Library Granted Patent US 11,772,055
Granted Patent B2
US 11,772,055 · App. 17/184,273 · Granted Oct 3, 2023

Ligand-modified filter and methods for reducing metals from liquid compositions

Inventors: James Hamzik (North Billerica, MA); Jad A. Jaber (Westford, MA); Nicholas J. Filipancic (Medford, MA); Justin Brewster (North Billerica, MA)
Assignee: ENTEGRIS, INC.
B01D71/58B01D69/12B01D71/26B01D71/36C02F1/44C07C229/16C08F255/02C08F259/08C02F2101/203C02F2101/22C02F2103/346
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Quick Facts
Patent No.
US 11,772,055
App. No.
17/184,273
Granted
Oct 3, 2023
Kind
B2
Abstract

Described are filter materials having polycarboxyl ligands, such as iminodiacetic acid, which are highly effective for filtering metals or metal ions from fluids. The filter materials can be particularly useful to filter various fluid compositions, such as those used for wet etching, removing photoresist, and cleaning steps in microelectronic device manufacturing.

Claims (32)

1. A filter material comprising a polycarboxyl ligand, wherein the filter material is configured to be used in conjunction with a microelectronic fabrication system for providing a metal- or metal ion-depleted liquid composition;

wherein the polycarboxyl ligands are covalently bound to the filter material through at least one linkage which is other than through a carboxyl group;

and wherein the filter material is modified by halogenation or haloalkylation to provide a surface-reactive chemistry for attachment of the polycarboxyl ligands if the filter material is not inherently amine-reactive.

2. The filter material of claim 1 , the polycarboxyl ligand having the partial structure:

wherein x is an integer of from 1 to 6, n is equal to 2 or 3, and z represents either a zero or +1 valence.

3. The filter material of claim 1 , wherein the polycarboxyl ligand is derived from iminodiacetic acid, ethylenediamine tetraacetic acid, 1,2-cyclohexanediamine-N,N,N′,N′-tetraacetic acid, nitriloacetic acid, or iminodisuccinic acid.

4. The filter material of claim 1 , the polycarboxyl ligand having the partial structure:

5. The filter material of claim 1 , wherein the filter material is a porous polymeric filter membrane comprising a polymeric material selected from the group consisting of a polyamide, a polyimide, a polysulfone, a polyether-sulfone, a polyolefin, a halogenated polymer, and a combination thereof.

6. The filter material of claim 5 , wherein the polymeric material is ultra-high molecular weight polyethylene.

7. The filter material of claim 5 , wherein the polymeric material is polytetrafluoroethylene.

8. A composite membrane comprising:

a first filter material and a second filter material, wherein an output facing surface of the first filter material is in contact with an input facing surface of the second filter material, the first filter material or the second filter material comprising polycarboxyl ligands covalently bound to the filter through at least one linkage which is other than through a carboxyl group;

wherein the filter material comprising the polycarboxyl ligands is modified by halogenation or haloalkylation to provide a surface-reactive chemistry for attachment of the polycarboxyl ligands if the filter material is not inherently amine-reactive;

wherein the second filter material is different from the first filter material, and

wherein the composite membrane is configured to be used in conjunction with a microelectronic fabrication system for providing a metal- or metal ion-depleted liquid composition.

9. The composite membrane of claim 8 , the polycarboxyl ligand having the partial structure

wherein x is an integer of from 1 to 6, n is equal to 2 or 3, and z represents either a zero or +1 valence.

10. The composite membrane of claim 8 , the polycarboxyl ligand having the partial structure

11. The composite membrane of claim 8 , wherein the first filter material, the second filter material, or both are a porous polymeric filter membrane comprising a polymeric material selected from the group consisting of a polyamide, a polyimide, a polysulfone, a polyether-sulfone, a polyolefin, a halogenated polymer, and a combination thereof.

12. The composite membrane of claim 8 , wherein the first filter material is a porous polymeric filter membrane and the second filter material is polymeric resin particles.

13. A filter material comprising a porous polymeric filter material comprising ultra-high molecular weight polyethylene, having coated thereon a composition comprising a free-radical reaction product of (i) a polycarboxyl compound having an olefinic group and (ii) at least one monomeric, oligomeric, or polymeric compound having olefinic unsaturation;

wherein the polycarboxyl compounds are covalently bound to the filter through at least one linkage which is other than through a carboxyl group.

14. The filter material of claim 13 , wherein the polycarboxyl compound having an olefinic group is a compound of the formula

15. The filter of claim 13 , wherein the at least one monomeric, oligomeric, or polymeric compound having olefinic unsaturation is chosen from N,N′-methylenebis(acrylamide), triethylene glycol dimethacrylate, triethylene glycol diacrylate, and ethylene glycol divinyl ether.

16. A method of removing one or more metals or metal ions from a liquid composition, the method comprising:

contacting a filter material with a liquid composition comprising one or more metals or metal ions, the filter material comprising polycarboxyl ligands covalently bound to the filter material through at least one linkage which is other than through a carboxyl group, wherein the filter material is modified by halogenation or haloalkylation to provide a surface-reactive chemistry for attachment of the polycarboxyl ligands if the filter material is not inherently amine-reactive,

and

reducing an amount of the one or more metal or metal ions in the liquid composition.

17. The method of claim 16 , the polycarboxyl ligand having the partial structure

wherein x is an integer of from 1 to 6, n is equal to 2 or 3, and z represents either a zero or +1 valence.

18. The method of claim 16 , the polycarboxyl ligand having the partial structure

19. The method of claim 16 , wherein the filter material is a porous polymeric filter membrane comprising a polymeric material selected from the group consisting of a polyamide, a polyimide, a polysulfone, a polyether-sulfone, a polyolefin, a halogenated polymer, and a combination thereof.

Assignments (3)
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.; CMC MATERIALS, INC.; INTERNATIONAL TEST SOLUTIONS, LLC; QED TECHNOLOGIES INTERNATIONAL, INC.
To: TRUIST BANK, AS NOTES COLLATERAL AGENT
Reel/Frame 060613/0072 →
SECURITY INTEREST Recorded Jul 8, 2022
From: ENTEGRIS, INC.; ENTEGRIS GP, INC.; POCO GRAPHITE, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 060614/0980 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2021
From: HAMZIK, JAMES; JABER, JAD A.; FILIPANCIC, NICHOLAS J.; BREWSTER, JUSTIN
To: ENTEGRIS, INC.
Reel/Frame 055395/0643 →
Continuity (2)
Provisional Application 62981351 · Feb 25, 2020
Related Publication 20210260537A1 · Aug 26, 2021