Functionalized copolymers and use thereof

Patent metadata

Field	Value
Publication number	US-11446613-B2
Application number	US-201716328389-A
Country	US
Kind code	B2
Filing date	Aug 30, 2017
Priority date	Sep 9, 2016
Publication date	Sep 20, 2022
Grant date	Sep 20, 2022

Abstract

An article that includes a functionalized copolymer and the use thereof, particularly in a process for binding biomaterials, such as in a process for separating aggregated proteins from monomeric proteins in a biological solution; wherein the article includes: a) a porous substrate; and b) a copolymer covalently attached to the porous substrate, the copolymer comprising a hydrocarbon backbone and a plurality of pendant groups attached to the hydrocarbon backbone, wherein 1) each of a first plurality of pendant groups comprises: (a) at least one acidic group or salt thereof; and (b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and 2) each of a second plurality of pendant groups comprises: (a) at least one acidic group or salt thereof; and (b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and wherein the first plurality of pendant groups are different than the second plurality of pendant groups; and wherein a mole ratio of the first plurality of pendant groups to the second plurality of pendant groups is in a range of 95:5 to 5:95.

First claim

We claim:

1. An article comprising:
a) a porous substrate; and
b) a copolymer covalently attached to the porous substrate, the copolymer comprising a hydrocarbon backbone and a plurality of pendant groups attached to the hydrocarbon backbone, wherein:
1) each of a first plurality of pendant groups comprises:
(a) at least one acidic group or salt thereof; and
(b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and

2) each of a second plurality of pendant groups comprises:
(a) at least one acidic group or salt thereof; and
(b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and

wherein the first plurality of pendant groups are different than the second plurality of pendant groups; and
wherein a mole ratio of the first plurality of pendant groups to the second plurality of pendant groups is in a range of 95:5 to 5:95.

2. The article of claim 1 wherein the copolymer covalently attached to the porous substrate comprises a reaction product of a monomer composition comprising:
1) A first monomer comprising:
(a) at least one ethylenically unsaturated group;
(b) at least one acidic group or salt thereof; and
(c) a spacer group that directly links the at least one ethylenically unsaturated group and the at least one acidic group or salt thereof by a chain of at least 6 catenated atoms; and

2) a second monomer comprising:
(a) at least one ethylenically unsaturated group;
(b) at least one acidic group or salt thereof; and
(c) a spacer group that directly links the at least one ethylenically unsaturated group and the at least one acidic group by a chain of at least 6 catenated atoms;

wherein the second monomer is different than the first monomer; and
wherein a mole ratio of the first monomer to the second monomer is in a range of 95:5 to 5:95.

3. The article of claim 1 wherein the at least one acidic group or salt thereof of the copolymer covalently bonded to the porous substrate is present at a density of at least 0.01 mmole/gram of filter media.

4. The article of claim 1 wherein the at least one acidic group or salt thereof of the copolymer covalently bonded to the porous substrate is present at a density of up to 0.6 mmole/gram of filter media.

5. The article of claim 2 wherein the at least one ethylenically unsaturated group of the first monomer and/or second monomer is selected from an ethenyl group, a 1-alkylethenyl group, and a combination thereof.

6. The article of claim 1 wherein the spacer group is a catenated heteroatom-containing hydrocarbon group.

7. The article of claim 2 wherein the first monomer is one of a class represented by the following general formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L  (I)

wherein:
R 1 is selected from hydrogen, an alkyl group, a cycloalkyl group, an aryl group, and a combination thereof;
each R 2 is independently selected from a hydrocarbylene group, a heterohydrocarbylene group, and a combination thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, a hydrocarbyl group, a heterohydrocarbyl group, and a combination thereof;
Z is a heterohydrocarbylene group comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is an integer of 0 or 1; and
L is a functional group comprising at least one acidic group or salt thereof.

8. The article of claim 2 wherein the second monomer is one of a class represented by the following general formula:
CH 2 ═CR 1 —C(═O)—X—R 2 —[Z—R 2 ] n -L  (I)

wherein:
R 1 is selected from hydrogen, an alkyl group, a cycloalkyl group, an aryl group, and a combination thereof;
each R 2 is independently selected from a hydrocarbylene group, a heterohydrocarbylene group, and a combination thereof;
X is —O— or —NR 3 —, where R 3 is selected from hydrogen, a hydrocarbyl group, a heterohydrocarbyl group, and a combination thereof;
Z is a heterohydrocarbylene group comprising at least one hydrogen bond donor, at least one hydrogen bond acceptor, or a combination thereof;
n is an integer of 0 or 1; and
L is a functional group comprising at least one acidic group or salt thereof.

9. The article of claim 1 which is a filter element having a contacting surface.

10. The article of claim 1 which is an array of sample containers, wherein each container includes the filter element having a contacting surface.

11. A process for capture or removal of a target biomaterial comprising:
providing a filter element of claim 9 ; and
allowing a biological solution comprising a target biomaterial to contact the contacting surface of the filter element under conditions effective for binding of the target biomaterial.

12. A process for separating aggregated proteins from monomeric proteins in a biological solution, the process comprising:
providing at least one filter element having a contacting surface, wherein the filter element comprises filter media comprising:
a) a porous substrate; and
b) a copolymer covalently attached to the porous substrate, the copolymer comprising a hydrocarbon backbone and a plurality of pendant groups attached to the hydrocarbon backbone, wherein:
1) Each of a first plurality of pendant groups comprises:
(a) at least one acidic group or salt thereof; and
(b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and

2) each of a second plurality of pendant groups comprises:
(a) at least one acidic group or salt thereof; and
(b) a spacer group that directly links the at least one acidic group or salt thereof to the hydrocarbon backbone by a chain of at least 6 catenated atoms; and

wherein the first plurality of pendant groups are different than the second plurality of pendant groups; and
wherein a mole ratio of the first plurality of pendant groups to the second plurality of pendant groups is in a range of 95:5 to 5:95; and

allowing an initial biological solution to contact the contacting surface of the filter element under conditions effective to separate the aggregated proteins from the monomeric proteins such that a final biological solution includes purified monomeric proteins.

13. The process of claim 12 wherein the copolymer covalently attached to the porous substrate comprises a reaction product of a monomer composition comprising
1) A first monomer comprising:
(a) at least one ethylenically unsaturated group;
(b) at least one acidic group or salt thereof; and
(c) a spacer group that directly links the at least one ethylenically unsaturated group and the at least one acidic group or salt thereof by a chain of at least 6 catenated atoms; and

2) a second monomer comprising:
(a) at least one ethylenically unsaturated group;
(b) at least one acidic group or salt thereof; and
(c) a spacer group that directly links the at least one ethylenically unsaturated group and the at least one acidic group or salt thereof by a chain of at least 6 catenated atoms;

wherein the second monomer is different than the first monomer; and
wherein a mole ratio of the first monomer to the second monomer is in a range of 95:5 to 5:95.

14. The process of claim 12 the conditions are effective to recover, in a final solution, at least 70% of the monomeric proteins present in the initial biological solution.

15. The process of claim 12 wherein the conditions are effective to remove at least 10% of the

Assignees

• 3M Innovative Properties Co

Inventors

• Vail Andrew W
• Colak Atan Semra
• Rasmussen Jerald K
• Griesgraber George W
• Bothof Catherine A

Classifications

• B01D71/78

  Graft polymers · CPC title

• C09D133/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title

• B01D71/56

  Polyamides, e.g. polyester-amides · CPC title

• B01D67/0006

  by chemical reactions (in-situ polymerisation, polycondensation, cross-linking or reaction for manufacturing composite membranes B01D69/125) · CPC title

• B01D69/02

  characterised by their properties · CPC title