Post polymerization modification in flow

Patent metadata

Field	Value
Publication number	US-2021363296-A1
Application number	US-202016882028-A
Country	US
Kind code	A1
Filing date	May 22, 2020
Priority date	May 22, 2020
Publication date	Nov 25, 2021
Grant date	—

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, “R1” 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 monomer, comprising:
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:

wherein R 1 is selected from the group consisting of a hydrogen atom and a first alkyl group;
wherein L is 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
wherein A is the aryl halide functional group.

2 . The monomer 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, and wherein the second alkyl group comprises greater than or equal to one carbon atom and less than or equal to twenty carbon atoms.

3 . The monomer of claim 1 , wherein the aryl halide functional group has a structure selected from the group consisting of:

wherein X is a halide atom;
wherein Y is an atom selected from the 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.

4 . The monomer of claim 3 , wherein the cyclic carbonate molecular backbone is covalently bonded to the aryl halide functional group via in accordance with chemical structure:

5 . The monomer of claim 3 , wherein the cyclic carbonate molecular backbone is covalently bonded to the aryl halide functional group via in accordance with chemical structure:

6 . The monomer of claim 3 , wherein the cyclic carbonate molecular backbone is covalently bonded to the aryl halide functional group via in accordance with chemical structure:

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

wherein R 1 is selected from the group consisting of a hydrogen atom and a first alkyl group;
wherein R 2 is a functional group derived from a compound comprising an alcohol group;
wherein L is 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;
wherein A 1 is the pendent functional group and comprises an aryl group;
wherein R 3 is the target functional group; and
wherein m is an integer greater than or equal to 2 and less than or equal to 1000.

8 . The polymer of claim 7 , wherein the first alkyl group comprises greater than or equal to one carbon atom and less than or equal to three carbon atoms, and wherein the second alkyl group comprises greater than or equal to one carbon and less than or equal to twenty carbon atoms.

9 . The polymer of claim 7 , 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 the 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.

10 . The polymer of claim 9 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

11 . The polymer of claim 9 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

12 . The polymer of claim 9 , wherein the polycarbonate molecular backbone is covalently bonded to the target functional group via the pendent functional group in accordance with the chemical structure:

13 . A method comprising:
performing, via a flow reactor, a ring-opening polymerization of a cyclic carbonate monomer to form a polycarbonate polymer characterized by a chemical structure selected from the group consisting of:

wherein R 1 is selected from the group consisting of a hydrogen atom and a first alkyl group;
wherein R 2 is a functional group derived from a compound comprising an alcohol group;
wherein L is 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;
wherein A is an aryl halide group; and
wherein m is an integer greater than or equal to 2 and less than or equal to 1000.

14 . The method of claim 13 , further comprising:
reacting the polycarbonate polymer with a silyl protected thiol compound to form a functionalized polycarbonate polymer, wherein the silyl protected thiol reacts with the aryl halide group via a nucleophilic aromatic substitution of the halide.

15 . The method of claim 14 , wherein the aryl halide group has a structure selected from the group consisting of:

wherein X is a halide atom;
wherein Y is an atom selected from the 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.

16 . The method of claim 15 , wherein the halide atom is fluorine.

17 . The method of claim 14 , wherein the silyl protected thiol compound is characterized by a second chemical structure:

and
wherein R 3 is the functional group.

18 . The method of claim 14 , wherein the reacting the polycarbonate polymer with the silyl protected thiol compound is performed via a batch reaction.

19 . The method of claim 14 , wherein the reacting the polycarbonate polymer with the silyl protected thiol compound is performed in the flow reactor.

20 . The method of claim 14 , further comprising:
supplying an anionic catalyst to the flow reactor to facilitate the ring-opening polymerization.

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

• B01J2219/00795

  Spiral-shaped · CPC title

• B01J2219/00792

  One or more tube-shaped elements · CPC title

• B01J2219/00867

  Microreactors placed in series, on the same or on different supports · CPC title

• B01J19/0093

  Microreactors, e.g. miniaturised or microfabricated reactors (laboratory containers with capillary fluid transport in microfabricated channels or chambers B01L3/5027) · CPC title

• C08G64/0241

  containing nitrogen · CPC title