Back to results
US 2009/0214794 A1Published application
Crosslinked polymers with amine binding groups
Assignee3M Innovative Properties Company
InventorsRahul R. Shah, Karl E. Benson, Charles M. Leir, George G.I. Moore
Life of this patent
Estimating the term…
Abstract
Crosslinked polymeric materials are described that contain pendant amine capture groups. The amine capture groups include N-sulfonyldicarboximide groups that can react with amine-containing materials by a ring opening reaction. Reaction mixtures used to prepare the crosslinked polymeric materials, articles containing the crosslinked polymeric materials, methods of making articles, and methods of immobilizing an amine-containing material are also described.
Claims20
A crosslinked polymeric material comprising the reaction product of a reaction mixture comprising:
- a) an amine capture monomer of Formula I
- wherein
- L is an oxy or —NR6—;
- R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
- R3 is hydrogen or methyl;
- R4 is an alkyl, aryl, aralkyl, or —NR5 wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- the amine capture monomer is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- b) a crosslinking monomer comprising at least two (meth)acryloyl groups.
7 more elements
An article comprising
- a substrate;
- and
- a crosslinked polymeric material disposed on a surface of the substrate, the crosslinked polymeric material having a pendant amine capture group comprising a N-sulfonyldicarboximide group and the crosslinked polymeric material being the reaction product of a reaction mixture comprising:
- a) an amine capture monomer of Formula I
- wherein
- L is an oxy or —NR6—;
- R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
- R3 is hydrogen or methyl;
- R4 is an alkyl, aryl, aralkyl, or —NR5 wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- the amine capture monomer is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- b) a crosslinking monomer comprising at least two (meth)acryloyl groups.
10 more elements
A method of immobilizing an amine-containing material to a substrate, the method comprising
- providing a substrate;
- disposing a reaction mixture on a surface of the substrate, the reaction mixture comprising:
- a) an amine capture monomer of Formula I
- wherein
- L is an oxy or —NR6—;
- R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
- R3 is hydrogen or methyl;
- R4 is an alkyl, aryl, aralkyl, or —NR5 wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- the amine capture monomer is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- b) a crosslinking monomer comprising at least two (meth)acryloyl groups;
- curing the reaction mixture to form a crosslinked polymeric material having a pendant amine capture group comprising a N-sulfonyldicarboximide group;
- and
- reacting an amine-containing material with the N-sulfonyldicarboximide group.
12 more elements
A method of making an article, the method comprising
- providing a substrate;
- disposing a reaction mixture on a surface of the substrate, the reaction mixture comprising:
- a) an amine capture monomer of Formula I
- wherein
- L is an oxy or —NR6—;
- R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
- R3 is hydrogen or methyl;
- R4 is an alkyl, aryl, aralkyl, or —NR5 wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- the amine capture monomer is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- b) a crosslinking monomer comprising at least two (meth)acryloyl groups;
- and
- curing the reaction mixture to form a crosslinked polymeric material having a pendant amine capture group comprising a N-sulfonyldicarboximide group.
11 more elements
A polymeric material comprising a pendant group of Formula II
- wherein
- L is an oxy or —NR6—;
- R1 and R2 together with a dicarboximide group to which they are attached form a four to eight membered heterocyclic or heterobicyclic group that can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
- R4 is an alkyl, aryl, aralkyl, or —N(R5)2, wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- an asterisk (*) denotes an attachment site of the pendant group to a backbone of the polymeric material;
- the pendant group of Formula II is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- the polymeric material is crosslinked.
6 more elements
A polymeric material comprising a pendant group of Formula III
- wherein
- L is an oxy or —NR6—;
- R4 is an alkyl, aryl, aralkyl, or —N(R5)2, wherein each R5 is an alkyl group or both R5 groups taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
- R6 is hydrogen, alkyl, aryl, aralkyl, acyl, alkylsulfonyl, or arylsulfonyl;
- R7 is an alkylene having 1 to 5 carbon atoms, aromatic group, saturated or unsaturated cyclic group, saturated or unsaturated bicyclic group, or combination thereof,
- T is equal to a primary amine-containing biological material minus a —NH2 group;
- Y is a single bond or a divalent group comprising an alkylene, heteroalkylene, arylene, or combinations thereof,
- an asterisk (*) denotes an attachment site of the pendant group to a backbone of the polymeric material;
- the pendant group of Formula III is unsubstituted or substituted with a halo, alkyl, alkoxy, or combinations thereof, and
- the polymeric material is crosslinked.
7 more elements
Dependencies are inferred from the claim text.