MONOMERS, POLYMERS, AND ARTICLES FOR BIOMATERIAL CAPTURE

1 . A monomer represented by the following general Formula (I):

CH 2 ═CR 1 —C(═O)—X—R 2 —Z—X 3 —NR 3 —C(═X 2 )—X 1 —R 4   (I)

wherein:

R 1 is H or —CH 3 ;

R 2 is a (hetero)hydrocarbylene;

X is —O— or —NH—;

X 1 is —O—, —S—, —NH—, or a single bond;

X 2 is —O— or —S—;

X 3 is —O— or —NR 5 —;

R 4 is hydrogen, (hetero)hydrocarbyl, or —N(R 3 ) 2 ;

each R 3 and R 5 is independently hydrogen or a (hetero)hydrocarbyl; and

Z is —C(═O)— or —NH—C(═O)—.

2 . The monomer of claim 1 wherein R 4 is methyl or phenyl.

3 . The monomer of claim 1 wherein X 2 is —O—.

4 . The monomer of claim 1 wherein X 3 is —NR 5 —.

5 . The monomer of any of claim 1 prepared from reaction of an alkenyl azlactone of general Formula (II):

wherein:

R 1 is hydrogen or methyl; and

R 2 is (hetero)hydrocarbylene;

with a nucleophilic group-containing compound of general Formula (IV):

H—X 3 —N(R 3 )—C(═X 2 )—X 1 —R 4   (IV)

wherein:

X 1 is —O—, —S—, —NH—, or a single bond;

X 2 is —O— or —S—;

X 3 is —O— or —NR 5 —;

R 4 is hydrogen, (hetero)hydrocarbyl, or —N(R 3 ) 2 ; and

each R 3 and R 5 is independently hydrogen or (hetero)hydrocarbyl.

6 . The monomer of claim 1 prepared from reaction of an ethylenically unsaturated isocyanate of general Formula (III):

CH 2 ═C(R 1 )—C(═O)—X—R 2 —N═C═O  (III)

wherein:

R 1 is hydrogen or methyl; and

R 2 is (hetero)hydrocarbylene;

with a nucleophilic group-containing compound of general Formula (IV):

H—X 3 —N(R 3 )—C(═X 2 )—X 1 —R 4   (IV)

wherein:

X 1 is —O—, —S—, —NH—, or a single bond;

X 2 is —O— or —S—;

X 3 is —O— or —NR 5 —;

R 4 is hydrogen, (hetero)hydrocarbyl, or —N(R 3 ) 2 ; and

each R 3 and R 5 is independently hydrogen or (hetero)hydrocarbyl.

7 . The monomer of claim 5 wherein the nucleophilic group-containing compound of Formula (IV) is selected from:

(thio)semicarbazides of general Formula (V) R 4 —NH—C(═X 2 )—N(R 3 )—N(R 5 )—H;

(thio)hydrazides of general Formula (VI) R 4 —C(═X 2 )—N(R 3 )—N(R 5 )—H;

(thio)hydroxamic acids of general Formula (VII) R 4 —C(═X 2 )—N(R 3 )—OH;

carbazates of general Formula (VIII) R 4 —O—C(═O)—N(R 3 )—N(R 5 )—H;

dithiocarbazates of general Formula (IX) R 4 —S—C(═S)—N(R 3 )—N(R 5 )—H; and

hydroxy(thio)ureas of general Formula (X) R 4 —NH—C(═X 2 )—N(R 3 )—OH.

8 . A polymer comprising interpolymerized units of at least one monomer of claim 1 .

9 . The polymer of claim 8 which is a copolymer.

10 . The polymer of claim 9 which is a copolymer further comprising interpolymerized units of at least one monomer of the following general Formula (XI):

CH 2 ═CR 11 —C(═O)—X—R 12 —[Z 1 —R 12 ] n -L  (XI)

wherein:

R 11 is selected from hydrogen, alkyl, aryl, and combinations thereof;

each R 12 is independently a (hetero)hydrocarbylene;

X is —O— or —NR 13 —, where R 13 is hydrogen or a (hetero)hydrocarbyl;

Z 1 is a (hetero)hydrocarbylene 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 heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups, and salts thereof.

11 . The polymer of claim 10 comprising 5 wt-% to 75 wt-% interpolymerized units of at least one monomer represented by Formula (I).

12 . A copolymer comprising:

5 wt-% to 75 wt-% interpolymerized units of at least one monomer represented by the following general Formula (XII):

CH 2 ═CR 21 —C(═O)—X 20 —R 22 —Z 20 —X 23 —Y 20   (XII)

wherein:

R 21 is H or —CH 3 ;

R 22 is a (hetero)hydrocarbylene;

X 20 is —O— or —NH—;

X 23 is —O— or —NR 25 —;

Z 20 is —C(═O)— or —NH—C(═O)—;

Y 20 is hydrogen, (hetero)hydrocarbyl, or —NR 23 —C(═X 22 )—X 21 —R 24 ;

X 21 is —O—, —S—, —NH—, or a single bond;

X 22 is —O— or —S—;

R 24 is hydrogen, (hetero)hydrocarbyl, or —N(R 23 ) 2 ; and

each R 23 and R 25 is independently hydrogen or a (hetero)hydrocarbyl; and

25 wt-% to 95 wt-% interpolymerized units of at least one monomer of the following general Formula (XI):

CH 2 ═CR 11 —C(═O)—X—R 12 —[Z 1 —R 12 ] n -L  (XI)

wherein:

R 11 is selected from hydrogen, alkyl, aryl, and combinations thereof;

each R 12 is independently a (hetero)hydrocarbylene;

X is —O— or —NR 13 —, where R 13 is hydrogen or a (hetero)hydrocarbyl;

Z 1 is a (hetero)hydrocarbylene 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 heteroatom-containing group comprising at least one monovalent ligand functional group selected from acidic groups, basic groups, and salts thereof.

13 . The copolymer of claim 12 grafted to a substrate.

14 . An article for biomaterial capture comprising

a porous polymeric substrate; and

borne on the porous substrate, a polymer of claim 8 .

15 . The article of claim 14 wherein the polymer is grafted to the porous substrate.