Switchable polymers and surfaces with reversibly switchable properties
AssigneeUniversity of Washington through its Center for Commercialization
InventorsShaoyi Jiang, Zhiqiang Cao
Life of this patent
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Abstract
Reversibly switchable polymers, surfaces that include the polymers, and methods for making and using the polymers and surfaces. The switchable polymers are non-fouling in their zwitterionic form and are antimicrobial in their cationic form.
Claims16
A polymer having the formula:
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- A1(=O)—O− is an anionic center, wherein A1 is selected from the group consisting of C, Si, SO, and POH;
- L3 is a third linker that covalently couples the cationic center to the anionic center;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
A polymer having the formula:
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- L3 is a third linker that covalently couples the cationic center to A1;
- A1 is selected from the group consisting of C, Si, SO, and POH;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
A surface of a substrate, wherein the surface comprises a layer of first and second polymers,
- wherein the first polymers have the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- A1(=O)—O− is an anionic center, wherein A1 is selected from the group consisting of C, Si, SO, and POH;
- L3 is a third linker that covalently couples the cationic center to the anionic center;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000, and
- wherein the second polymers have the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- L3 is a third linker that covalently couples the cationic center to A1;
- A1 is selected from the group consisting of C, Si, SO, and POH;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
A method for converting a surface of a substrate from a zwitterionic polymer surface to a cationic polymer surface, comprising contacting a surface of a substrate having a zwitterionic polymer surface with acidic conditions to provide a cationic polymer surface,
- wherein the zwitterionic polymer surface comprises a layer of zwitterionic polymers having the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- A1(=O)—O− is an anionic center, wherein A1 is selected from the group consisting of C, Si, SO, and POH;
- L3 is a third linker that covalently couples the cationic center to the anionic center;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000, and
- wherein the cationic polymer surface comprises a layer of cationic polymers having the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- L3 is a third linker that covalently couples the cationic center to A1;
- A1 is selected from the group consisting of C, Si, SO, and POH;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
A method for converting a surface of a substrate from a cationic polymer surface to a zwitterionic polymer surface, comprising contacting a surface of a substrate having a cationic surface with aqueous or basic conditions to provide a zwitterionic polymer surface,
- wherein the cationic polymer surface comprises a layer of cationic polymers having the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- L3 is a third linker that covalently couples the cationic center to A1;
- A1 is selected from the group consisting of C, Si, SO, and POH;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
- wherein the zwitterionic polymer surface comprises a layer of zwitterionic polymers having the formula
- wherein
- M is a monomeric repeating unit;
- L1 is a first linker that covalently couples the methine carbon to the repeating unit;
- A2 is O, NR3, or S, wherein R3 is selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl;
- R1 and R2 are independently selected from the group consisting of hydrogen, C1-C6 alkyl, and C6-C12 aryl, or taken together with the nitrogen to which they are attached form a cationic center;
- L2 is a second linker that covalently couples the methine carbon to the cationic center;
- A1(=O)—O− is an anionic center, wherein A1 is selected from the group consisting of C, Si, SO, and POH;
- L3 is a third linker that covalently couples the cationic center to the anionic center;
- X− is a counter ion associated with the cationic center;
- Y+ is a counter ion associated with the anionic center;
- and
- n is an integer from 1 to about 10,000.
Dependencies are inferred from the claim text.