Post polymerization modification in flow

Patent metadata

Field	Value
Publication number	US-12227615-B2
Application number	US-202217934964-A
Country	US
Kind code	B2
Filing date	Sep 23, 2022
Priority date	May 22, 2020
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

Abstract

Techniques regarding post polymerization modifications to polycarbonate polymers via a flow reactor are provided. For example, one or more embodiments described herein can comprise a cyclic carbonate monomer that can be employed to facilitate polymerization of one or more polycarbonate platforms susceptible to post polymerization modification. For instance, one or more embodiments can regard a cyclic carbonate molecular backbone covalently bonded to an aryl halide functional group via in accordance with a chemical structure selected from the group consisting of:

In the chemical structures, “R 1 ” can be selected from the group consisting of a hydrogen atom and a functional group comprising a first alkyl group; “L” can represent a linkage group, comprising: a second alkyl group and an end group having at least one member selected from the group consisting of an oxygen atom and a nitrogen atom; and “A” can represent the aryl halide functional group.

First claim

What is claimed is:

1. A polymer, comprising:
a polycarbonate molecular backbone covalently bonded to a target functional group via a pendent functional group in accordance with a chemical structure selected from a first group consisting of:

wherein R 1 comprises a first alkyl group,
wherein R 2 is selected from a second group consisting of an alcohol group, a second alkyl group, a benylic alcohol, an allylic alcohol, and a propargylic alcohol,
wherein L is a linkage group comprising an alkyl chain and one or more end groups bonded to the alkyl chain, the one or more end groups selected from a third group consisting of an oxygen atom and a nitrogen atom,
wherein R 3 is the target functional group and selected from a fourth group consisting of a third alkyl group, an aromatic group, a heteroaromatic group, a pendent ether group, a thioether group, a alkyl halide group, a phosphonate group, an epoxide groups, a sulfonate group, a urea group, a thiourea group, a guanidinium group, a carbamate group, an ester group, and a carbonate group,
wherein m is an integer greater than or equal to 2 and less than or equal to 1000,
wherein A 1 is the pendent functional group and comprises an aryl group,
wherein the aryl group has a structure selected from the group consisting of:

wherein X is a halide atom,
wherein Y is an atom selected from a fifth group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, and
wherein n is an integer greater than or equal to 2 and less than or equal to 8.

2. The polymer of claim 1 , wherein the first alkyl group comprises greater than or equal to one carbon atom and less than or equal to three carbon atoms.

3. The polymer of claim 1 , wherein the alkyl chain comprises greater than or equal to one carbon and less than or equal to twenty carbon atoms.

4. The polymer of claim 1 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

5. The polymer of claim 1 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

6. The polymer of claim 1 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

7. The polymer of claim 1 , wherein X is the halide atom of a chemical element selected from the sixth group consisting of: fluorine, chlorine, bromine and iodine.

8. A polymer, comprising:
a polycarbonate molecular backbone covalently bonded to a target functional group via a pendent functional group in accordance with chemical structure:

wherein R 1 is a first alkyl group,
wherein R 2 is selected from a first group consisting of an alcohol group, a second alkyl group, a benylic alcohol, an allylic alcohol, and a propargylic alcohol,
wherein L is a linkage group comprising an alkyl chain and one or more end groups bonded to the alkyl chain, the one or more end groups selected from a second group consisting of an oxygen atom and a nitrogen atom,
wherein R 3 is the target functional group and selected from a third group consisting of a third alkyl group, an aromatic group, a heteroaromatic group, a pendent ether group, a thioether group, a alkyl halide group, a phosphonate group, an epoxide groups, a sulfonate group, a urea group, a thiourea group, a guanidinium group, a carbamate group, an ester group, and a carbonate group,
wherein m is an integer greater than or equal to 2 and less than or equal to 1000,
wherein A 1 is the pendent functional group and comprises an aryl group,
wherein the aryl group has a structure selected from the group consisting of:

wherein X is a halide atom,
wherein Y is an atom selected from a fourth group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, and
wherein n is an integer greater than or equal to 2 and less than or equal to 8.

9. The polymer of claim 8 , wherein the first alkyl group comprises greater than or equal to one carbon atom and less than or equal to three carbon atoms.

10. The polymer of claim 8 , wherein the alkyl chain comprises greater than or equal to one carbon and less than or equal to twenty carbon atoms.

11. The polymer of claim 10 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group.

12. The polymer of claim 10 , wherein X is the halide atom of a chemical element selected from a fifth group consisting of: fluorine, chlorine, bromine and iodine.

13. A polymer, comprising:
a polycarbonate molecular backbone covalently bonded to a target functional group via a pendent functional group in accordance with chemical structure:

wherein R 1 is a first alkyl group,
wherein R 2 is selected from a first group consisting of an alcohol group, a second alkyl group, a benylic alcohol, an allylic alcohol, and a propargylic alcohol,
wherein L is a linkage group comprising an alkyl chain and one or more end groups bonded to the alkyl chain, the one or more end groups, selected from a second group consisting of an oxygen atom and a nitrogen atom,
wherein R 3 is the target functional group and selected from a third group consisting of a third alkyl group, an aromatic group, a heteroaromatic group, a pendent ether group, a thioether group, a alkyl halide group, a phosphonate group, an epoxide groups, a sulfonate group, a urea group, a thiourea group, a guanidinium group, a carbamate group, an ester group, and a carbonate group,
wherein m is an integer greater than or equal to 2 and less than or equal to 1000,
wherein A 1 is the pendent functional group and comprises an aryl group,
wherein the aryl group has a structure selected from the group consisting of:

wherein X is a halide atom,
wherein Y is an atom selected from a fourth group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, and
wherein n is an integer greater than or equal to 2 and less than or equal to 8.

14. The polymer of claim 13 , wherein the first alkyl group comprises greater than or equal to one carbon atom and less than or equal to three carbon atoms.

15. The polymer of claim 13 , wherein the alkyl chain comprises greater than or equal to one carbon and less than or equal to twenty carbon atoms.

16. The polymer of clai

Assignees

• IBM
• Agency Science Tech & Res

Inventors

• Park Nathaniel H
• Piunova Victoria A
• Zubarev Dmitry
• Hedrick James L
• Yang Yi Yan
• Tan Eddy Wei Ping

Classifications

• C07D319/06 Primary

  not condensed with other rings · CPC title

• C08G64/30

  using carbonates · CPC title

• B01J19/24

  Stationary reactors without moving elements inside (B01J19/08, B01J19/26 take precedence; with stationary particles B01J8/02) · CPC title

• B01J2219/00029

  Batch processes · CPC title

• C08G64/1633

  containing halogens · CPC title