Sulfonamide based anion exchange resins

Patent metadata

Field	Value
Publication number	US-12285704-B2
Application number	US-202117354058-A
Country	US
Kind code	B2
Filing date	Jun 22, 2021
Priority date	Nov 1, 2017
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

An ion exchange resin for use as a stationary phase in an ion chromatography column. The ion exchange resin has a negatively charged substrate particle, a positively charged polymer layer bound to the negatively charged substrate particle, a linker, and an ion exchange group. The ion exchange group includes a sulfonamide group and an amine, in which the ion exchange group is coupled to the positively charged polymer layer via the linker. When the sulfonamide is in a neutral form, a positively charged amine group provides retention; while when the sulfonamide is in an anionic form, the sulfonamide anion becomes a counter ion to the positively charged amine group, forming a zwitterion that reduces retention at that site. Accordingly, the retention time is able to be controlled by adjusting the mobile phase pH.

First claim

What is claimed is:

1. An ion exchange resin comprising:
a negatively charged substrate particle;
a positively charged polymer layer bound to the negatively charged substrate particle, in which the positively charged polymer layer includes a linker; and
an ion exchange group including a sulfonamide group and an amine, in which the ion exchange group is coupled to the positively charged polymer layer via the linker;
wherein the positively charged polymer layer comprises:
(a) a structure according to Formula (I):

where n ranges from about 5 to about 150, and R is an alkyl group; or

(b) a structure according to Formula (III):

where n ranges from about 5 to about 150, and R is an alkyl group.

2. The ion exchange resin of claim 1 , in which the amine of the ion exchange group is selected from a group consisting of a secondary amine, a tertiary amine, a quaternary ammonium, and a combination thereof.

3. The ion exchange resin of claim 1 , in which the ion exchange group includes a quaternary ammonium and the ion exchange group is configured to be zwitterionic when the sulfonamide group is in a deprotonated state.

4. The ion exchange resin of claim 1 , in which the negatively charged substrate particle is a polymeric particle and the ion exchange resin is configured to retain the ion exchange group when subjected to eluent having a pH ranging from 0 to 14.

5. The ion exchange resin of claim 1 , in which the negatively charged substrate particle comprises a sulfonated copolymer of an ethylvinylbenzene and a divinylbenzene.

6. The ion exchange resin of claim 5 , in which the negatively charged substrate particle comprises a super macroporous particle.

7. The ion exchange resin of claim 1 , in which the positively charged polymer layer further comprises ether groups and hydroxyl groups.

8. The ion exchange resin of claim 1 , in which the linker includes an aromatic ring.

9. The ion exchange resin of claim 1 wherein the ion exchange group is a first ion exchange group, the sulfonamide group is a first sulfonamide group, and the amine is a first quaternary ammonium group, wherein the ion exchange resin further comprises
a second ion exchange group including a second sulfonamide group and a second quaternary ammonium group, in which the second ion exchange group is coupled to the positively charged polymer layer via the linker, in which the first quaternary ammonium group is different than the second quaternary ammonium group.

10. The ion exchange resin of claim 9 , wherein the first ion exchange group comprises N,N-dimethylaminopropyl methylsulfonamide and the second ion exchange group comprises N,N-diethylaminoethyl methylsulfonamide in a ratio of the first ion exchange group to the second ion exchange group of 1:1.

11. A method of using the ion exchange resin of claim 1 packed in a chromatography column, the method comprising:
flowing an eluent through the chromatography column, in which the eluent comprises carbonate and bicarbonate,
and
separating a sample that includes a trivalent species.

12. The method of claim 11 further comprising:
(a) adjusting a ratio of a carbonate concentration and a bicarbonate concentration so that a carbonate peak does not overlap with an analyte peak; and/or
(b) adjusting a pH value of the eluent so that a first analyte peak does not overlap with second analyte peak.

Assignees

• Dionex Corp
• Hatch Melvin

Inventors

• Hatch Melvin
• Pohl Christopher A
• Jayaraman Manikandan

Classifications

• B01J41/05

  in the strongly basic form · CPC title

• B01D15/361

  Ion-exchange · CPC title

• B01D15/364

  Amphoteric or zwitterionic ion-exchanger · CPC title

• B01J41/14

  obtained by reactions only involving unsaturated carbon-to-carbon bonds · CPC title

• B01J41/20

  Anion exchangers for chromatographic processes · CPC title