High purity chromatographic materials comprising an ionizable modifier

Patent metadata

Field	Value
Publication number	US-10150098-B2
Application number	US-201013376497-A
Country	US
Kind code	B2
Filing date	Aug 4, 2010
Priority date	Aug 4, 2009
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The present invention provides novel chromatographic materials, e.g., for chromatographic separations, processes for its preparation and separations devices containing the chromatographic material; separations devices, chromatographic columns and kits comprising the same; and methods for the preparation thereof. The chromatographic materials of the invention are high purity chromatographic materials comprising a chromatographic surface wherein the chromatographic surface comprises a hydrophobic surface group and one or more ionizable modifier

First claim

What is claimed is:

1. A high purity chromatographic material comprising a chromatographic surface wherein the chromatographic surface comprises a hydrophobic surface group and one or more ionizable modifiers with the proviso that when the ionizable modifier does not contain a Zwitterion, the ionizable modifier does not contain a quaternary ammonium ion moiety;
wherein the concentration of ionizable modifier in the high purity chromatographic material of the invention is more than 0.03 μmol/m 2 and less than 0.5 μmol/m 2 of the specific surface area, and the ratio of the hydrophobic surface group : ionizable modifier is from about 4:1 to about 12:1;
and wherein the ionizable modifier is obtained from an ionizable modifying reagent selected from groups having
the formula (II):

wherein
m is an integer from 1-8;
v is 0;
m′ is 0;
Z represents a chemically reactive group, including (but not limited to)

 amine, alkylamine, dialkylamine, isocyanate, acyl chloride, thiocyanate, NHS-ester, carboxylic acid, ester, epoxide, alkyne, alkene, or azide;

Y is an embedded polar functionality;
each occurrence of R 1 independently represents a chemically reactive group on silicon, including (but not limited to) —H, —OH, —OR 6 , dialkylamine, triflate, Br, Cl, I, vinyl, or alkene;
p is an integer from 1-3;
each occurrence of R 1 ′ independently represents F, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 3 -C 18 cycloalkyl, C 1 -C 18 heterocycloalkyl, C 5 -C 18 aryl, C 5 -C 18 aryloxy, or C 1 -C 18 heteroaryl, fluoroalkyl, or fluoroaryl;
each occurrence of R 2 , R 2 ′, R 3 and R 3 ′ independently represents hydrogen;
each occurrence of R 6 independently represents C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 3 -C 18 cycloalkyl, C 1 -C 18 heterocycloalkyl, C 5 -C 18 aryl, C 5 -C 18 aryloxy, or C 1 -C 18 heteroaryl; and
Het is pyridyl.

2. The high purity chromatographic material of claim 1 further comprising a chromatographic core material.

3. The high purity chromatographic material of claim 1 , wherein m is 2 or 3.

4. The high purity chromatographic material of claim 1 , wherein R 1 represents Cl.

5. The high purity chromatographic material of claim 1 , wherein R 1 represents —OH.

6. The high purity chromatographic material of claim 1 , wherein R 1 represents dialkylamino, methoxy or ethoxy.

7. The high purity chromatographic material of claim 1 , wherein R 1 ′ represents methyl.

8. The high purity chromatographic material of claim 1 , wherein R 1 ′ represents ethyl.

9. The high purity chromatographic material of claim 1 , wherein R 1 ′ represents isobutyl.

10. The high purity chromatographic material of claim 1 , wherein R 1 ′ represents isopropyl.

11. The high purity chromatographic material of claim 1 , wherein R 1 ′ represents tert-butyl.

12. The high purity chromatographic material of claim 1 , wherein the ionizable modifying reagent is 2-(2-(trichlorosilyl)ethyl)pyridine,2-(2-(trimethoxy)ethyl)pyridine, 2-(2-(triethoxy)ethyl)pyridine,2-(4-pyridylethyl)triethoxysilane,2-(4-pyridylethyl)trimethoxysilane,2-(4-pyridylethyl)trichlorosilane.

13. A method for preparing a high purity chromatographic material according to claim 2 comprising the steps of:
reacting a chromatographic core with ionizable modifying reagent to obtain a ionizable modified material; and
reacting the resultant ionizable material with a hydrophobic surface modifying group.

14. A method for preparing a chromatographic material according to claim 2 comprising the steps of:
reacting a chromatographic core with hydrophobic surface modifying group to obtain a bonded material; and
reacting the resultant bonded material with an ionizable modifying reagent.

15. A separations device having a stationary phase comprising the high purity chromatographic material of claim 1 .

16. A chromatographic column, comprising
a) a column having a cylindrical interior for accepting a packing material and
b) a packed chromatographic bed comprising the high purity chromatographic material of claim 1 .

17. A kit comprising the high purity chromatographic material of claim 1 , and instructions for use.

18. A chromatographic device, comprising
a) an interior channel for accepting a packing material and
b) a packed chromatographic bed comprising the high purity chromatographic material of claim 1 .

Assignees

• Wyndham Kevin D
• Iraneta Pamela C
• Walter Thomas H
• Waters Technologies Corp

Inventors

• Wyndham Kevin D
• Iraneta Pamela C
• Walter Thomas H

Classifications

• B01J20/3257

  the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such · CPC title

• B01J20/28078

  Pore diameter · CPC title

• B01J20/3289

  Coatings involving more than one layer of same or different nature · CPC title

• B01J20/3293

  Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers · CPC title

• B01J20/29

  Chiral phases · CPC title