N-sulfonylaminocarbonyl containing compounds
View Patent ↗Compounds having two reactive functional groups are described that can be used to provide a connector group between a substrate and an amine-containing material. The first reactive functional group can be used to provide attachment to a surface of a substrate. The second reactive functional group is a N-sulfonylaminocarbonyl group that can be reacted with an amine-containing material, particularly a primary aliphatic amine, to form a carbonylimino-containing connector group. The invention also provides articles and methods for immobilizing amine-containing materials to a substrate.
1. A compound of Formula I:
wherein
X 1 is a substrate-reactive functional group selected from a halocarbonyl, halocarbonyloxy, cyano, mercapto, isocyanato, halosilyl, alkoxysilyl, acyloxysilyl, azido, aziridinyl, tertiary amino, primary aromatic amino, secondary aromatic amino, disulfide, alkyl disulfide, benzotriazolyl, phosphoroamido, or phosphato;
Y 1 is a divalent group comprising at least one heteroalkylene having an oxy group or a —NR d — group, at least one alkylene, or combinations thereof, wherein Y 1 can optionally further comprise an arylene, carbonyl, carbonyloxy, carbonylimino, oxy, —NR d — where R d is hydrogen or alkyl, or combinations thereof;
Z 1 is an alkyl, axyl, or —(CO)R a wherein R a together with R 1 and groups to which they are attached form a five membered heterocyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic group is selected from an optional saturated or unsaturated benzoisothiazole or benzothiazole thereof;
R 1 is an alkyl, fluoroalkyl, chloroalkyl, aryl, NR b R c wherein R b and R c are each an alkyl group, or R 1 together with R a and the groups to which they are attached form the five membered heterocyclic group that can be fused to the optional benzene ring;
r is equal to 1 when X 1 is a monovalent group or equal to 2 when X 1 is a divalent group; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
2. The compound of claim 1 , wherein the compound has a formula
wherein
n is an integer of 1 to 100; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
3. The compound of claim 1 , wherein the compound has a formula
wherein
D is oxygen or NH;
t is an integer of 0 to 12;
k is an integer of 2 to 4;
m is an integer of 1 to 200; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
4. The compound of claim 1 , wherein the compound has a formula
wherein
D is oxygen or NH;
n is an integer of 1 to 100;
m is an integer of 1 to 200;
t is an integer of 0 to 12;
k is an integer of 2 to 4;
L is oxygen or NR d where R d is hydrogen or alkyl; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
5. The compound of claim 1 , wherein the compound is of formula
wherein
D is oxygen or NH;
n is an integer of 1 to 100;
m is an integer of 1 to 200;
t is an integer of 0 to 12;
k is an integer of 2 to 4;
p is an integer of 1 to 10;
L is oxygen or NR d where R d is hydrogen or alkyl; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
6. The compound of claim 1 , wherein the compound is of formula
wherein
D is oxygen or NH;
n is an integer of 1 to 100;
m is an integer of 1 to 200;
t is an integer of 0 to 12;
k is an integer of 2 to 4;
p is an integer of 1 to 10;
L is oxygen or NR d where R d is hydrogen or alkyl;
Ar 1 is an arylene; and
said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
7. The compound of claim 1 , wherein Z 1 is a C 1-10 alkyl and R 1 is a C 1-10 fluoroalkyl.
8. The compound of claim 1 , wherein Z 1 is an aryl and R 1 is a C 1-10 fluoroalkyl.
9. The compound of claim 1 , where the compound is of formula
where X 1 is monovalent or
where X 1 is divalent and said compound is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
10. The compound of claim 1 , wherein the compound is
said compound being unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
11. The compound of claim 1 , wherein the compound is
said compound being unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof.
12. The compound of claim 1 , wherein the compound is
13. The compound of claim 1 , wherein Y 1 comprises at least one heteroalkylene and at least one alkylene.
14. The compound of claim 1 , wherein Y 1 comprises at least one alkylene.
15. The compound of claim 1 , wherein Y 1 comprises at least one heteroalkylene having an oxy group or a —NR d — group.
16. The compound of claim 1 , wherein X 1 is halosilyl, alkoxysilyl, or acloxysily.
17. The compound of claim 1 , wherein X 1 is disulfide or alkyl disulfide.
18. The compound of claim 1 , wherein Z 1 is —(CO)R a wherein R a together with R 1 and groups to which they are attached form a five membered heterocyclic group that is optionally fused to a benzene ring.