Ligand functional substrates

Patent metadata

Field	Value
Publication number	US-11279731-B2
Application number	US-201816174373-A
Country	US
Kind code	B2
Filing date	Oct 30, 2018
Priority date	Mar 28, 2011
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

A substrate comprising a crosslinked polymer primer layer, and grafted thereto a ligand-functionalized polymer is provided. The grafted polymer has the requisite affinity for binding neutral or negatively charged biomaterials, such as cells, cell debris, bacteria, spores, viruses, nucleic acids, and proteins, at pH's near or below the pI's of the biomaterials.

First claim

The invention claimed is:

1. A ligand functional substrate comprising:
a) a substrate, and
b) a crosslinked ligand-functional alkenyl (co)polymer layer coated on the surface of the substrate, wherein the ligand-functional alkenyl (co)polymer comprises polymerized monomer units of the formula:

wherein
R 1 is H or C 1 -C 4 alkyl;
R 2 is a divalent alkylene having 1 to 20 carbon atoms;
each R 3 is independently H or C 1 -C 4 alkyl;
R 4 is H, C 1 -C 4 alkyl or —N(R 3 ) 2 ;
R 5 is H or C 1 -C 4 alkyl or aryl;
X 1 is —O— or —NR 3 —,
o is 0 or 1, and
n is 1 or 2.

2. The ligand-functional substrate of claim 1 , wherein the ligand-functional alkenyl (co)polymer further comprises polymerized hydrophilic monomer units.

3. The ligand-functional substrate of claim 2 , wherein the ligand-functional alkenyl (co)polymer comprises 1% to about 70% by weight polymerized hydrophilic monomer units, relative to the total monomer weight.

4. The ligand-functional substrate of claim 2 , wherein the ligand-functional alkenyl (co)polymer comprises 5% to about 50% by weight polymerized hydrophilic monomer units, relative to the total monomer weight.

5. The ligand-functional substrate of claim 2 , wherein the hydrophilic monomer units are poly(oxyalkylene) (meth)acrylate monomer units.

6. The ligand-functional substrate of claim 5 , wherein the poly(oxyalkylene) (meth)acrylate monomer units are of the formula:
CH 2 ═CR 1 —C(O)—X 1 —(CH(R 1 )—CH 2 —O) n —R 1 ,

wherein each R 1 is independently H or C 1 -C 4 alkyl, X 1 is—O— or —NR 3 —, where R 3 is H or C 1 -C 4 alkyl and n is 2 to 100.

7. The ligand-functional substrate of claim 1 , wherein the ligand-functional alkenyl (co)polymer further comprises polymerized cationic or anionic monomer units.

8. The ligand-functional substrate of claim 7 , wherein the anionic monomer units are selected from (meth)acryloylsulfonic acids, vinylsulfonic acid, 4-styrenesulfonic acid;
(meth)acrylamidophosphonic acids; (meth)acrylic acid and carboxyalkyl(meth)acrylates.

9. The ligand-functional substrate of claim 7 , wherein the cationic monomer units are selected from amino (meth)acrylates, amino (meth)acrylamides, dialkylaminoalkylamine adducts of alkenylazlactones, and quaternary ammonium salts thereof.

10. The ligand-functional substrate of claim 1 , wherein the crosslinking agent of said crosslinked ligand-functional alkenyl (co)polymer layer is a multifunctional (meth)acryloyl monomer.

11. The ligand-functional substrate of claim 10 , wherein the multifunctional (meth)acryloyl monomer is selected from di(meth)acrylates, tri(meth)acrylates, and tetra(meth)acrylates.

12. The ligand-functional substrate of claim 10 , wherein the multifunctional (meth)acryloyl monomer is selected from ethyleneglycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, poly(ethylene glycol) di(meth)acrylates, polybutadiene di(meth)acrylate, polyurethane di(meth)acrylates, propoxylated glycerin tri(meth)acrylate, methylenebisacrylamide, ethylenebisacrylamide, hexamethylenebisacrylamide, and diacryloylpiperazine.

13. The ligand-functional substrate of claim 10 , wherein the multifunctional (meth)acryloyl monomer is used in amounts of 0.25% to about 5% by weight, relative to the total monomer weight.

14. The ligand-functional substrate of claim 1 , wherein the crosslinked ligand- functional alkenyl (co)polymer layer is of the formula:
-(M Lig ) y -(M Hydrophil ) x (M crosslink ) z -, where
(M Hydrophil) x are hydrophilic monomer units having “x” polymerized monomer units,
(M Lig ) y are ligand functional monomer units having “y” polymerized monomer units,
(M crosslink ) are multifunctional (meth)acryloyl monomer units having “y” polymerized monomer units,
y is 10 to less than 100 wt.% of the monomer units;
x is 0 to 90 wt.% of the monomer units;
z is greater than 0 to 5% wt.% of the monomer units, based on 100 wt.% total monomers.

15. The ligand-functional substrate of claim 1 wherein said ligand-functional alkenyl (co)polymer comprises 5 to 30 wt.% of the ligand functional substrate.

16. The ligand-functional substrate of claim 1 wherein the substrate is a porous substrate selected from porous particles, porous membranes, porous nonwoven webs, and porous fibers.

17. A method of preparing a ligand functional substrate of claim 1 comprising the steps of:
a) providing a substrate,
b) free-radically reacting the substrate with a ligand-functional (meth)acryloyl monomer of the formula:

wherein
R 1 is H or C 1 -C 4 alkyl;
R 2 is a divalent alkylene having 1 to 20 carbon atoms;
each R 3 is independently H or C 1 -C 4 alkyl;
R 4 is H, C 1 -C 4 alkyl or —N(R 3 ) 2 ;
R 5 is H or C 1 -C 4 alkyl or aryl;
X 1 is —O— or —NR 3 —,
o is 0 or 1, and
n is 1 or 2,
in a mixture with a multifunctional (meth)acryloyl monomer.

18. The method of claim 17 further comprising free-radically reacting with a hydrophilic monomer.

Assignees

• 3M Innovative Properties Co

Inventors

• Rasmussen Jerald K
• Bothof Catherine A
• Seshadri Kannan
• Hembre James I
• Fitzsimons Jr Robert T
• Griesgraber George W
• He Yi

Classifications

• B01D67/00931

  by introduction of specific groups after membrane formation, e.g. by grafting · CPC title

• B01D71/56 Primary

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

• G01N33/543 Primary

  with an insoluble carrier for immobilising immunochemicals · CPC title

• C07K1/22 Primary

  Affinity chromatography or related techniques based upon selective absorption processes · CPC title

• B01D2323/385

  involving radiation · CPC title