Solid support with a grafted chain

Patent metadata

Field	Value
Publication number	US-9290580-B2
Application number	US-201514672871-A
Country	US
Kind code	B2
Filing date	Mar 30, 2015
Priority date	Jun 26, 2008
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

Articles that contain a solid support with a grafted chain extending from the solid support, methods of making these articles, and various uses of the articles are described. More specifically, the grafted chain has a functional group that can react with or interact with target compound. Alternatively, the functional group on the grafted chain can react with a modifying agent to provide another group that can react with or interact with the target compound. The grafted chains are attached to the solid support through a ring-opened azlactone group. The articles can be used to purify the target compound or to separate the target compound from other molecules in a sample.

First claim

We claim:

1. An article comprising a modified grafted support of Formula (V)
SS—(CO)—NH—C(R 1 ) 2 —(CH 2 ) p —(CO)-Q-Y 1 -Q-(CO)—CR 2 U 4 —CH 2 —U 3   (V)

wherein
SS comprises a solid support in the form of a membrane, foam, film, sheet, or coating on a substrate;
p is an integer equal to 0 or 1;
each R 1 is each independently selected from alkyl, heteroalkyl, aryl, or aralkyl;
Y 1 is a first linking group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
each Q is independently a divalent group selected from oxy, thio, or —NR 3 — where R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 2 is independently hydrogen or an alkyl;
U 3 comprises at least one divalent monomeric unit of formula CR 2 (Y 2 L-T)-CH 2 —;
Y 2 is a second linking group selected from a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combination thereof;
U 3 includes at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
U 4 is hydrogen or comprises at least one divalent monomeric unit of formula —CR 2 (Y 2 L-T)-CH 2 —;
L is an attachment group formed by reacting group Z 1 with a modifying group A of a modifying agent A-T;
Z 1 is a functional group selected from (1) an acidic group or a salt thereof, (2) an amino group or a salt thereof, (3) a hydroxyl group, (4) an azlactone group or a precursor of the azlactone group, (5) a glycidyl group, or (6) a combination thereof; and
T is a remainder of the modifying agent A-T and is equal to the modifying agent A-T minus the modifying group A.

2. The article of claim 1 , wherein Z 1 is an acidic group and the modifying agent is of formula

wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl.

3. The article of claim 1 , wherein Z 1 is a hydroxyl group and the modifying agent is of formula

wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
X is halo.

4. The article of claim 1 , wherein Z 1 is an amino group and the modifying agent is of formula

wherein
D is oxy, thio, or —NR 3 —;
R 3 is hydrogen, alkyl, heteroalkyl, aryl, or aralkyl;
each R 4 is independently hydrogen, alkyl, heteroalkyl, aryl, or aralkyl; and
X is halo.

5. The article of claim 1 , wherein Z 1 is an azlactone group and the modifying agent is of formula HD-T, wherein D is oxy, thio, or —NR 3 —.

6. The article of claim 1 , wherein Z 1 is a glycidyl group and the modifying agent is of formula T-(CO)—OH or HD-T, wherein D is oxy, thio, or —NR 3 —.

7. The article of claim 1 , wherein the modifying agent is an affinity ligand comprising at least one nucleophilic group.

8. The article of claim 1 , wherein the modifying agent comprises a first group that is nucleophilic and a second group that is basic, acidic, or a salt thereof.

9. The article of claim 1 , wherein the modifying agent comprises a first group that is nucleophilic and a second group that is hydrophobic.

10. The article of claim 1 , wherein the modifying agent comprises a first group that is nucleophilic and a second group that is metal-chelating.

11. The article of claim 1 , wherein the modifying agent is a biomolecule.

12. The article of claim 1 , wherein each Q is oxy.

13. The article of claim 1 , wherein Y 1 is an alkylene.

Assignees

• 3M Innovative Properties Co

Inventors

• Shannon Simon K
• Bothof Catherine A
• Gaddam Babu N
• Rasmussen Jerald K
• Ross Richard B

Classifications

• B01D15/08 Primary

  Selective adsorption, e.g. chromatography · CPC title

• B01J39/165

  Operations & Transport · mapped topic

• B01J20/3255

  comprising a cyclic structure containing at least one of the heteroatoms nitrogen, oxygen or sulfur, e.g. heterocyclic or heteroaromatic structures · CPC title

• B01J2220/58

  Use in a single column · CPC title

• B01D15/3804

  Affinity chromatography · CPC title