Ligand-functionalized substrates with enhanced binding capacity

Patent metadata

Field	Value
Publication number	US-2018217035-A1
Application number	US-201815936767-A
Country	US
Kind code	A1
Filing date	Mar 27, 2018
Priority date	Oct 3, 2013
Publication date	Aug 2, 2018
Grant date	—

Abstract

An article that can be used for biomaterial capture comprises
(a) a porous substrate; and (b) borne on the porous substrate, a polymer comprising interpolymerized units of at least one monomer consisting of (1) at least one monovalent ethylenically unsaturated group, (2) at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof, and (3) a multivalent spacer group that is directly bonded to the monovalent groups so as to link at least one ethylenically unsaturated group and at least one ligand functional group by a chain of at least six catenated atoms.

First claim

We claim:

1 . An article for biomaterial capture comprising
(a) a porous substrate; and (b) borne on said porous substrate, a polymer comprising interpolymerized units of at least one monomer consisting of (1) at least one monovalent ethylenically unsaturated group, (2) at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof, and (3) a multivalent spacer group that is directly bonded to said monovalent groups so as to link at least one said ethylenically unsaturated group and at least one said ligand functional group by a chain of at least six catenated atoms (c) wherein said monomer is of the formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L

wherein
R 1 is selected from hydrogen, alkyl, cycloalkyl, aryl, and combinations thereof;
each R 2 is independently selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
Z is heterohydrocarbylene comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is 1; and
L is a heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof.

2 . The article of claim 1 , wherein said porous substrate is a porous membrane; and/or wherein said porous substrate is polymeric.

3 . The article of claim 1 wherein said monovalent ethylenically unsaturated group is selected from ethenyl, 1-alkylethenyl, and combinations thereof.

4 . The article of claim 1 or any other of the preceding claims, wherein said monovalent ligand functional group is selected from carboxy, phosphono, phosphato, sulfono, sulfato, boronato, tertiary amino, quaternary amino, and combinations thereof.

5 . The article of claim 1 or any other of the preceding claims, wherein said multivalent spacer group is a catenated heteroatom-containing hydrocarbon group.

6 . The article of claim 5 , wherein said hydrogen bonding moiety is selected from carbonylimino, thiocarbonylimino, iminocarbonylimino, iminothiocarbonylimino, oxycarbonylimino, oxythiocarbonylimino, and combinations thereof.

7 . The article of claim 1 wherein said chain has at least seven catenated atoms.

8 . The article of claim 1 wherein said chain has no more than 50 catenated atoms.

9 . The article of claim 1 wherein said chain has from 8 to 16 catenated atoms.

10 . The article of claim 1 wherein said polymer is grafted to said porous substrate.

11 . An article for biomaterial capture comprising
(a) a porous polymeric membrane; and (b) grafted to said porous polymeric membrane, a polymer comprising interpolymerized units of at least one monomer of the formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L

wherein
R 1 is selected from hydrogen, alkyl, cycloalkyl, aryl, and combinations thereof;
each R 2 is independently selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
Z is heterohydrocarbylene comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is 1; and
L is a heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof.

12 . The article of claim 11 wherein said article comprises at least one filter element.

13 . A process for capture or removal of a target biomaterial comprising
(a) providing at least one article of claim 11 ; and (b) allowing a moving biological solution containing a target biomaterial to impinge upon the upstream surface of said filter element for a time sufficient to effect binding of said target biomaterial.

14 . The process of claim 13 , wherein said target biological species is a protein.

15 . A process for preparing an article for biomaterial capture comprising
(a) providing a porous substrate; and (b) providing said porous substrate with a polymer comprising interpolymerized units of at least one monomer of the formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L

wherein
R 1 is selected from hydrogen, alkyl, cycloalkyl, aryl, and combinations thereof;
each R 2 is independently selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
Z is heterohydrocarbylene comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is 1; and
L is a heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof.

16 . The process of claim 15 , wherein said providing with a polymer comprises free radically polymerizing said monomer in the presence of said porous substrate.

17 . The process of claim 15 , wherein said providing with a polymer results in the grafting of said polymer to said porous substrate.

18 . A free radically polymerizable compound consisting of (a) at least one monovalent ethylenically unsaturated group, (b) at least one monovalent ligand functional group selected from phosphorus-containing acidic groups, boron-containing acidic groups, and salts thereof, and (c) a multivalent spacer group that is directly bonded to the monovalent groups so as to link at least one ethylenically unsaturated group and at least one ligand functional group by a chain of at least six catenated atoms, said monomer of the formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L

wherein
R 1 is selected from hydrogen, alkyl, cycloalkyl, aryl, and combinations thereof;
each R 2 is independently selected from hydrocarbylene, heterohydrocarbylene, and combinations thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, hydrocarbyl, heterohydrocarbyl, and combinations thereof;
Z is heterohydrocarbylene comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is 1; and
L is a heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups other than guanidino, and salts thereof.

19 . The compound of claim 18 , wherein said ligand functional group is selected from phosphono, phosphato, boronato, and combinations thereof.

Assignees

• 3M Innovative Properties Co

Inventors

• Rasmussen Jerald K
• Bothof Catherine A
• Griesgraber George W
• Colak Atan Semra
• Hembre James I
• Fitzsimons Jr Robert T

Classifications

• B01J20/3242

  Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group · CPC title

• B01J20/327

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

• B01D2325/14

  Membrane materials having negatively charged functional groups · CPC title

• C07K1/34

  by filtration, ultrafiltration or reverse osmosis · CPC title

• G01N33/544

  the carrier being organic · CPC title