Amide Activation Approach to the Post-Polymerization Modification of Poly(meth)acrylamides
AssigneeUniversity of Kansas
InventorsAaron J. TEATOR, Kasun WEKASINGHE
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Abstract
Described herein are methods for the post-polymerization modification of a (co)polymer comprising a monomer repeat unit comprising a pendant secondary or tertiary amide moiety (e.g., an acrylamide or a methacrylamide (co)polymer). These methods can comprise activating the pendant secondary or tertiary amide moiety to form a keteniminium ion or a nitrilium ion; and quenching the keteniminium ion or the nitrilium ion with a nucleophile to covalently functionalize the monomer repeat unit. Also provided herein are copolymers prepared by these methods. A. Previous Work B. This Work
Claims23
A method for post-polymerization modification of a (co)polymer comprising a monomer repeat unit comprising a pendant secondary or tertiary amide moiety, the method comprising:
- activating the pendant tertiary amide moiety to form a keteniminium ion or a nitrilium ion;
- and
- quenching the keteniminium ion or a nitrilium ion with a nucleophile to covalently functionalize the monomer repeat unit.
A random copolymer defined by the formula below
- wherein
- R1 and R2 are individually hydrogen or substituted or unsubstituted C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, or R1 and R2 together with the atom to which they are attached form a substituted or unsubstituted cycloalkyl or heterocycloalkyl ring, with the proviso that only one of R1 and R2 can be hydrogen;
- R3 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl group;
- R′ is hydrogen or methyl;
- x is an integer from 1 to 25,000;
- y is an integer from 1 to 500,000;
- and n is an integer from 2 to 525,000.
A method of producing a UV degradable (meth)acrylamide copolymer, the method comprising:
- activating a pendant secondary or tertiary amide moiety present in a (meth)acrylamide (co)polymer to form a keteniminium ion or a nitrilium ion;
- and
- quenching the keteniminium ion or the nitrilium ion with a nucleophile to form a monomer repeat unit is defined by the structure below
- wherein
- R3 is a substituted or unsubstituted aryl or heteroaryl group;
- and
- R′ is hydrogen or methyl.
Dependencies are inferred from the claim text.