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

Patent metadata

Field	Value
Publication number	US-2017190842-A1
Application number	US-201515325926-A
Country	US
Kind code	A1
Filing date	Jul 14, 2015
Priority date	Jul 15, 2014
Publication date	Jul 6, 2017
Grant date	—

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

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

wherein R is selected from the following structures:

wherein each R 1 , R 2 , and R 4 are independently selected from the group consisting of: 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

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 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 each of R 1 , R 2 , and R 4 are independently selected from the group consisting of: 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

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 selected from the group consisting of: 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 each R 1 , R 2 , and R 4 are independently selected from the group consisting of: 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 each of R 1 , R 2 , and R 4 are independently selected from the group consisting of: 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 each of R 1 , R 2 , and R 4 are independently selected from the group consisting of: 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 , or 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

• C07C2603/90

  containing more than four rings · CPC title

• B01D2257/7022

  Aliphatic hydrocarbons · CPC title

• C07C213/02

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• B01D2256/12

  Oxygen · CPC title

• B01D2257/504

  Carbon dioxide · CPC title