O-hydroxy-functionalized diamines, polyimides, methods of making each, and methods of use

Patent metadata

Field	Value
Publication number	US-10240001-B2
Application number	US-201515325926-A
Country	US
Kind code	B2
Filing date	Jul 14, 2015
Priority date	Jul 15, 2014
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

Embodiments of the present disclosure provide for an ortho (o)-hydroxy-functionalized diamine, a method of making an o-hydroxy-functionalized diamine, an o-hydroxy-functionalized diamine-based polyimide, a method of making an o-hydroxy-functionalized diamine imide, methods of gas separation, and the like.

First claim

We claim at least the following:

1. A composition, comprising:
an o-hydroxy-functionalized diamine having the following structure:

wherein R is selected from the following structures:

wherein R 1 is H or a substituted or unsubstituted linear alkyl group, wherein each R 2 and R 4 are independently selected from the group consisting of: H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each are substituted or unsubstituted.

2. The composition of claim 1 , wherein R is

and R 1 is H.

3. The composition of claim 1 , wherein R is

4. The composition of claim 1 , wherein R is

5. The composition of claim 1 , wherein R is

6. The composition of claim 1 , wherein R is

7. The composition of claim 1 , wherein R is

8. A composition, comprising:
a polyimide having the following structure:

wherein Ar 3 is an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:

wherein R 1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R 2 and R 4 are independently selected from the group consisting of: H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each are substituted or unsubstituted.

9. The composition of claim 8 , wherein R is

and R 1 is H.

10. The composition of claim 8 , wherein R is

11. The composition of claim 8 , wherein R is

12. The composition of claim 8 , wherein R is

13. The composition of claim 8 , wherein R is

14. The composition of claim 8 , wherein R is

15. A method of making an aromatic diamine, comprising:

wherein A includes acetylation of the bulky starting structures by Friedel-Crafts reaction, wherein B includes transferring the diacetyl intermediate to diester via Baeyer-Villiger oxidation reaction, wherein C includes the hydrolysis of the diester, wherein D includes the nitration of the diphenol intermediate, wherein E includes the reduction of the ortho-diphenol-dinitrol intermediate to the corresponding ortho-hydroxy-functionalized diamine, wherein R is selected from the following structures:

wherein R 1 , R 2 , and R 4 are independently a linear or branched, substituted or unsubstituted alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each is substituted or unsubstituted.

16. A method for making a polyimide, comprising: reacting a dianhydride with an o-hydroxy-functionalized diamine to form a polyimide, wherein the o-hydroxy-functionalized diamine has the following structure:

wherein R is selected from the following structures:

wherein R 1 is H or a substituted or unsubstituted linear alkyl group, wherein each of R 2 and R 4 are independently selected from the group consisting of: H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each are substituted or unsubstituted.

17. A membrane, comprising: a polyimide having the following structure:

wherein Ar 3 is selected from an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:

wherein R 1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R 2 and R 4 are independently selected from the group consisting of: H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each can be substituted or unsubstituted.

18. A method of separating a gas from a gas mixture, comprising: separating a first gas from a first gas mixture containing at least a second gas with a membrane to form a second gas mixture that is enriched in at least one gas component of the first mixture, wherein the membrane includes a polyimide having the following structure:

wherein Ar 3 is selected from an aryl group or a heteroaryl group, wherein x is 1 to 100,000, wherein R is selected from the following structures:

wherein R 1 is H or a substituted or unsubstituted linear alkyl group wherein, each of R 2 and R 4 are independently selected from the group consisting of: H and a linear or branched, substituted or unsubstituted, alkyl group, wherein Ar 2 is selected from the group consisting of: an aryl group and a heteroaryl group where each are substituted or unsubstituted.

19. The method of claim 18 , wherein the first gas is selected from the group consisting of: He, H 2 , CO 2 , H 2 S, H 2 O, O 2 , C 2 H 4 , C 3 H 6 , and a combination thereof, and wherein the second gas is N 2 , Ar, CH 4 , Co, saturated C 2+ hydrocarbons or a combination thereof.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Ma Xiaohua
• Ghanem Bader S
• Pinnau Ingo

Classifications

• C07C215/88

  being formed by at least three rings · CPC title

• C07C2603/97

  containing five-membered rings · CPC title

• C08G73/22

  Polybenzoxazoles · CPC title

• B01D2257/102

  Nitrogen · CPC title

• B01D2256/16

  Hydrogen · CPC title