Diamines, polyimides, methods of making each, and methods of use

Patent metadata

Field	Value
Publication number	US-11124607-B2
Application number	US-201716304421-A
Country	US
Kind code	B2
Filing date	Jun 2, 2017
Priority date	Jun 7, 2016
Publication date	Sep 21, 2021
Grant date	Sep 21, 2021

Abstract

Aspects of the present disclosure provide for bridgehead-substituted triptycene-based diamines and methods of making bridgehead-substituted triptycene-based diamines.

First claim

We claim at least the following:

1. A composition, comprising:
a monomer having the following structure:

wherein R1 and R2 are independently selected from the group consisting of an aryl group, a linear or branched alkyl group, a halogen and a nitrile group, with the proviso that at least one of R1 and R2 is a halogen and wherein Ar is an unsubstituted aryl group or unsubstituted heteroaryl group.

2. A method of making a monomer comprising:

wherein Ar is an unsubstituted aromatic moiety, wherein R1 and R2 are independently selected from the group consisting of an aryl group, a linear or branched alkyl group, a halogen and a nitrile group, with the proviso that at least one of R1 and R2 is a halogen.

3. A composition comprising: a polymer having the following structure:

wherein X is a tetravalent radical having an aromatic or aliphatic ring, wherein each of R1 and R2 are independently selected from the group consisting of an aryl group, a linear or branched alkyl group, a halogen and a nitrile group, with the proviso that at least one of R1 and R2 is a halogen, and wherein n is 1 to 10,000.

4. The composition of claim 3 , wherein X is:

wherein each R 1 and R 2 , as used for the structures of X, is independently selected from the group consisting of H, a halogen, and an alkyl group.

5. A composition comprising: a polymer having the following structure:

wherein Ar is an unsubstituted aromatic moiety, wherein R 1 and R 2 are independently selected from the group consisting of an aryl group, a linear or branched alkyl group, a halogen and a nitrile group, with the proviso that at least one of R1 and R2 is a halogen and wherein n is 1 to 10,000.

6. A membrane comprising: a polymer of claim 5 .

7. A gas separation system comprising: a membrane of claim 6 .

8. A membrane comprising: a polymer of claim 3 .

9. A gas separation system comprising: a membrane of claim 8 .

10. A method of separating a mixture, comprising:
introducing a fluid mixture to a membrane of claim 7 or 9 , wherein the mixture includes a first fluid component and a second fluid component that is different than the first fluid component; and
separating the first fluid component from the second fluid component; wherein the first component passes through the membrane and the second component does not substantially pass through the membrane.

11. The method of fluid separation of claim 10 , wherein the fluid mixture includes a mixture selected from the group consisting of O 2 /N 2 ; N 2 /CH 4 ; H 2 /N 2 ; H 2 /C 1+ hydrocarbon; He/C 1+ -hydrocarbons; CO 2 /C 1+ hydrocarbons; CO 2 /N 2 ; H 2 S/CH 4 ; H 2 O/CH 4 and olefin/paraffin.

12. The polymer of claim 5 , wherein at least one of R1 and R2 is chloride.

13. The polymer of claim 12 , wherein both R1 and R2 are chloride.

14. The method of claim 10 , wherein both R1 and R2 are a halogen.

15. The method of claim 10 , wherein the membrane comprises a polymer having the following structure:

 wherein n is an integer from 1 to 10,000.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Ghanem Bader Saleh
• Pinnau Ingo

Classifications

• B01D71/64

  Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1053

  with oxygen only in the tetracarboxylic moiety · CPC title

• Y02P20/129

  Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines · CPC title

• C08G73/1064

  containing sulfur · CPC title

• C08G73/1082

  wholly aromatic in the tetracarboxylic moiety · CPC title