Method of making ligand functionalized substrates
View Patent ↗Ligand functionalized substrates, methods of making ligand functionalized substrates, and methods of using functionalized substrates are disclosed. The ligand functionalized substrate may be described as the grafted reaction product of a substrate and a ligand monomer of the following formula:
1. A ligand-functionalized substrate comprising
a) A base substrate, and grafted thereto
b) a ligand-functional polymer of the formula:
-(M PI )-(M b ) x -(M c ) y -(M d ) z ,
wherein
-(M PI )- represent the residue of grafted photoinitiator monomers;
-(M b ) x represents polymerized ligand monomers, having “x” polymerized monomer units,
where x is at least one, said ligand monomers of the formula:
wherein
R 1 is H or C 1 -C 4 alkyl,
R 2 is a divalent alkylene optionally containing an ester, amide, urethane or urea linking group;
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 , and
X 1 is —O— or —NR 3 —;
-(M c ) y represents polymerized crosslinking monomers, having y polymerized monomer units, where y may be zero or at least one, and
-(M d ) z represents polymerized hydrophilic monomers, having z polymerized monomer units, where z may be zero or at least one.
2. The ligand-functional substrate of claim 1 further comprising said crosslinking monomer -(M c ) wherein said crosslinking monomers -(M c ) has two or more free-radically polymerizable groups.
3. The ligand-functional substrate of claim 2 wherein said crosslinking monomer -(M c )- is of the formula:
[CH 2 ═CH—C(O)—X 1 ] a —R 10 -Q-Z b ,
where Z is an acryloyl or non-acryloyl, ethylenically unsaturated polymerizable group,
X 1 is —O— or —NR 3 , where R 3 is H or C 1 -C 4 alkyl,
Q is a divalent linking group selected from a covalent bond, “—”, —O—, —NR 1 —, —CO 2 — and —CONR 1 —, where R 1 is H or C 1 -C 4 alkyl; and
R 10 is an alkylene group of valence a+b, and optionally containing one or more catenary oxygen atoms and/or one or more hydroxyl groups;
and a and b are each at least one.
4. The ligand-functional substrate of claim 2 wherein the crosslinking monomer -(M c ) comprises a poly(alkylene oxide) compound having at least one acryloyl group and at least one additional ethylenically unsaturated, free-radically polymerizable group.
5. The ligand-functional substrate of claim 2 , wherein the crosslinking monomer -(M c )- is of the formula:
Z-Q-(CH(R 1 )—CH 2 —O) n —C(O)—CH═CH 2 ,
wherein Z is an acryloyl or non-acryloyl, polymerizable ethylenically unsaturated group,
R 1 is a H or a C 1 to C 4 alkyl group, and n is from 2 to 100, and Q is a divalent linking group selected from a covalent bond, “—”, —O—, —NR 1 —, —CO 2 — and —CONR 1 —, where R 1 is H or C 1 -C 4 alkyl.
6. The ligand-functional substrate of claim 1 further comprising one or more additional hydrophilic monomers -(M d ) having a free-radically polymerizable group and a hydrophilic group.
7. The ligand functionalized substrate of claim 6 wherein said hydrophilic monomers -(M d ) 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 from 2 to 100.
8. The ligand functionalized substrate of claim 1 wherein said ligand monomer is the formula:
where
R 1 is H or C 1 -C 4 alkyl,
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 ,
X 1 is —O— or —NR 3 —, where R 3 is H or C 1 -C 4 alkyl,
R 7 and R 8 are each independently is C 1 to C 10 alkylene; and
Z is an ester, amide, urea, or urethane group.
9. The ligand functionalized substrate of claim 1 , wherein the base substrate is selected from a porous membrane, porous non-woven web, or porous fiber.
10. A method of separation comprising contacting a biological sample containing a biological material with the ligand-functional substrate of claim 1 .
11. The method of claim 10 wherein the ligand-functionalized substrate comprises grafted ionic groups that are positively charged at a selected pH of the biological sample to cause electrostatic charge repulsion of positively charged proteins in the biological sample, said biological sample containing positively charged proteins.
12. The method of claim 10 wherein the biological sample comprises negatively charged or neutral viruses, DNA, RNA, and host cell proteins, which bind to the ligand-functionalized substrate.
13. The method of claim 11 wherein the positively charged proteins comprise antibodies.
14. A filter element comprising one or more layers of the ligand-functionalized substrate of claim 1 .
15. The filter element of claim 14 further comprising one or more of an upstream prefilter layer and a downstream support layer.
16. A filter cartridge comprising the filter element of claim 15 .