Soluble polymers as amine capture agents and methods

A soluble polymer prepared from at least one monomer of the formula:

• ti A-R7—X—C(O)—C(R8)═CH2
• wherein A is selected from the group consisting of functional groups having the following formulas:
• wherein:
• 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 an alkyl, aryl, aralkyl, or —NRaRb wherein Ra and Rb are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
• R4 and R5 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;
• R6 is an alkyl, fluoroalkyl, chloroalkyl, aryl, —NRcRd wherein Rc and Rd are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered cyclic group, or R6 taken together with Re and the groups to which they are attached form the four to eight membered heterocyclic or heterobicyclic group that can be fused to the optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• Z is an alkyl, aryl, or —(CO)Re wherein Re together with R6 and groups to which they are attached form a four to eight membered heterocyclic or heterobicyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic or heterobicyclic group can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• Y1, Y2, and Y3 are each independently a single bond or a divalent group selected from the group consisting of an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NRf— where Rf is hydrogen or alkyl, and combinations thereof;
• X is —N(R9)— or —O—;
• R7 is a divalent group selected from the group consisting of alkylene, heteroalkylene, arylene, heteroarylene, and combinations thereof, wherein the alkylene and heteroalkylene optionally include one or more carbonyls;
• R8 is hydrogen or methyl;
• and
• R9 is hydrogen or a C1-6 alkyl group.

A soluble random polymer having a molecular weight of at least 1000 of the following formula:

• wherein:
• each R″ is independently H or CH3;
• each E is —O— or —NRf—, where Rf is hydrogen or alkyl;
• m′, n′, o′, p′ represent the number of times each moiety is present in the polymer;
• X′, Y′, Z′, and W′ are independently selected from the group consisting of alkyl, aryl, hydroxy ester, alkoxyalkyl, alkoxyaryl, ether, fluoroalkyl, trialkoxysilylalkyl, and N-containing groups;
• at least one of X′, Y′, Z′, or W′ includes the following acylsulfonamide group:
• the polymer includes at least two distinct moieties.

A method of making a soluble polymer, the method comprising polymerizing monomers, wherein at least one monomer is a compound of the formula:

• A-R7—X—C(O)—C(R8)═CH2
• wherein A is selected from the group consisting of functional groups having the following formulas:
• wherein:
• 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 an alkyl, aryl, aralkyl, or —NRaRb wherein Ra and Rb are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered heterocyclic group;
• R4 and R5 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;
• R6 is an alkyl, fluoroalkyl, chloroalkyl, aryl, —NRcRd wherein Rc and Rd are each an alkyl group or taken together with the nitrogen atom to which they are attached form a four to eight membered cyclic group, or R6 taken together with Re and the groups to which they are attached form the four to eight membered heterocyclic or heterobicyclic group that can be fused to the optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• Z is an alkyl, aryl, or —(CO)Re wherein Re together with R6 and groups to which they are attached form a four to eight membered heterocyclic or heterobicyclic group having a nitrogen heteroatom and a sulfur heteroatom, wherein said heterocyclic or heterobicyclic group can be fused to an optional aromatic group, optional saturated or unsaturated cyclic group, or optional saturated or unsaturated bicyclic group;
• Y1, Y2, and Y3 are each independently a single bond or a divalent group selected from the group consisting of an alkylene, heteroalkylene, arylene, carbonyl, carbonyloxy, carbonylimino, oxy, thio, —NRf— where Rf is hydrogen or alkyl, and combinations thereof;
• X is —N(R9)— or —O—;
• R7 is a divalent group selected from the group consisting of alkylene, heteroalkylene, arylene, heteroarylene, and combinations thereof, wherein the alkylene and heteroalkylene optionally include one or more carbonyls;
• R8 is hydrogen or methyl;
• and
• R9 is hydrogen or a C1-6 alkyl group.