Chromatographic separation material

Patent metadata

Field	Value
Publication number	US-9302203-B2
Application number	US-201213560539-A
Country	US
Kind code	B2
Filing date	Jul 27, 2012
Priority date	Jul 20, 2012
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

The chromatographic separation material is a cyclofructan or a derivative of cyclofructan covalently bonded to a cross-linked, organic polymer. The separation material works well in hydrophilic interaction liquid chromatography.

First claim

We claim:

1. A chromatographic separation material comprising:
a cross-linked, organic polymer particle, wherein the cross-linked organic polymer particle is a styrene-based cross-linked polymer and/or a (meth)acrylic-based polymer, and the weight of the cross-linking monomer is more than 10% of the total weight monomers; and
a cyclofructan compound of Formula (I):

wherein:
n is 1-3;
each L is, independently,
OR,
CR 3 ,
NR 2 R,
O—C(═O)—R,
O—C(═O)—NR 2 —R,
NR 3 C(═O)—NR 2 R, or

substituted with R;
each R is, independently,
H,
(C 1 -C 20 )alkyl group optionally substituted with 1-3 R 1 ,
(C 3 -C 20 )cycloalkyl group optionally substituted with 1-3 R 1 ,
(C 5 -C 50 )aryl group optionally substituted with 1-3 R 1 ,
heteroaryl group optionally substituted with 1-3 R 1 ,
(C 1 -C 20 )alkoxy (C 1 -C 20 )alkyl group,
H 2 C═CH—(when L is O—C(═O)—R),
H 2 C═C(CH 3 )—(when L is O—C(═O)—R),
alkylenyl-N═C═O;
arylenyl-N═C═O;
—SO 2 R 5 (when L is OR),
═SO 3 (when L is OR),
(C 5 -C 50 )aryl(C 1 -C 20 ) alkyl group optionally substituted with 1-3 R 1 , or saccharide residue lacking a hydroxy group (when L is OR), or a covalent bond to cross-linked organic polymer;
R 1 is, independently, (C 1 -C 10 )alkyl group optionally substituted with 1-3 R 6 , halo group, hydroxy group, —NR 3 R 4 , —COOR 2 , —COR 2 , nitro group, trihaloalkyl group, or —Si(OR 2 ) 3 ;
R 2 is, independently, H or (C 1 -C 10 )alkyl group;
R 3 is, independently, H or (C 1 -C 10 )alkyl group;
R 4 is, independently, H or (C 1 -C 10 )alkyl group;
R 5 is, independently, (C 1 -C 20 )alkyl group optionally substituted with 1-3 R 1 , (C 5 -C 50 )aryl optionally substituted with 1-3 R 1 , or heteroaryl optionally substituted with 1-3 R 1 ;
R 6 is, independently, halo group, hydroxyl group, —NR 3 R 4 , —COOR 2 , —COR 2 , nitro group, trihaloalkyl group or —Si(OR 2 ) 3 ;
wherein at least one R is a covalent bond to the cross-linked organic polymer particle, and
wherein the chromatographic separation material is selected from the group consisting of:

wherein Polymer is the cross-linked organic polymer particle, CF s is the cyclofructan compound of Formula (I) having 6, 7 or 8 fructose moieties, and IP is isopropyl.

2. The chromatographic separation material of claim 1 , wherein the cross-linked organic polymer particle comprises a specific surface area of 10 to 1200 m 2 /g.

3. The chromatographic separation material of claim 1 , wherein the cross-linked organic polymer particle comprises a pore volume of 0.1 to 3.0 ml/g.

4. A method of chromatographic separation comprising:
providing a stationary phase comprising the chromatographic separation material of claim 1 ; and
contacting the stationary phase with a mobile phase comprising an analyte so as to separate the analyte.

5. The method of claim 4 , wherein the stationary phase is provided by packing the stationary phase in a column.

6. The method of claim 5 , wherein the stationary phase fills the inside void of the column.

7. The method of claim 5 , wherein the stationary phase is packed along the inside walls of the column.

8. The method of claim 4 , wherein the mobile phase comprises a solvent and the analyte is carried in the solvent.

9. The method of claim 4 , wherein the analyte comprises an enantiomeric mixture.

Assignees

• Qiu Haixiao
• Armstrong Daniel W
• Kiyono-Shimobe Mayumi
• Mitsubishi Chem Corp
• Azyp Llc

Inventors

• Qiu Haixiao
• Armstrong Daniel W
• Kiyono-Shimobe Mayumi

Classifications

• B01J2220/54

  Sorbents specially adapted for analytical or investigative chromatography · CPC title

• B01D15/3833 Primary

  Chiral chromatography · CPC title

• B01J20/328

  Polymers on the carrier being further modified · CPC title

• B01J20/3274

  Proteins, nucleic acids, polysaccharides, antibodies or antigens · CPC title

• C08F8/00

  Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C) · CPC title