Ortho-substituted triptycene-based diamines, monomers, and polymers, methods of making and uses thereof

Patent metadata

Field	Value
Publication number	US-10619009-B2
Application number	US-201615767033-A
Country	US
Kind code	B2
Filing date	Oct 7, 2016
Priority date	Oct 8, 2015
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

Described herein are ortho-dimethyl-substituted and tetramethyi-substituted triptycene-containing diamine monomers and microporous triptycene-based poiyimides and poiyamides, and methods of making the monomers and polymers.

First claim

We claim at least the following:

1. A substituted triptycene-containing diamine comprising:
a 3,6-dimethyl-2,7-diaminotriptycene derivative having the general formula:

wherein Ar is an unsubstituted or substituted aromatic moiety; or
a 1,3,6,8-tetramethyl-2,7-diaminotriptycene derivative having the general formula:

wherein Ar is an unsubstituted or substituted aromatic moiety.

2. A composition, comprising a triptycene-based polyimide according to Formula 3,

where n is 1 to 10,000, where X is a tetravalent radical having an aromatic ring or an aliphatic ring, and Y is a divalent organic group having a structure according to Formula 5 or 6:

wherein Ar is an unsubstituted or substituted aromatic moiety; or comprising a triptycene-based polyamide of Formula 4

where n is 1 to 10,000, where Z is a divalent radical having an aromatic ring or an aliphatic ring, and Y is a divalent organic group having a formula according to Formula 5 or 6:

wherein Ar is an unsubstituted or substituted aromatic moiety.

3. A composition, comprising a polyimide according to any one of Formulas 7-13

where n is 1 to 10,000, wherein Ar is an unsubstituted or substituted aromatic moiety; or a polyamide according to Formula 14 or 15

wherein n 1 to 10,000.

4. The composition of claim 3 , wherein the composition is a film or membrane for a fluid separation system.

5. The substituted triptycene-containing diamine of claim 1 , wherein the aromatic moiety comprises an aryl group.

6. The substituted triptycene-containing diamine of claim 1 , wherein the aromatic moiety comprises a heteroaryl group.

7. The composition of claim 2 , wherein the tetravalent radical comprises a C5 to C12 ring.

8. The composition of claim 2 , wherein the tetravalent radical comprises a multi ring.

9. The composition of claim 8 , wherein the multi ring comprises an aryl group and a heteroaryl group.

10. The composition of claim 3 , wherein the aromatic moiety comprises an aryl group.

11. The composition of claim 3 , wherein the aromatic moiety comprises an heteroaryl group.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Ghanem Bader Saleh
• Pinnau Ingo

Classifications

• C07C211/61

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C08G73/1007

  from tetracarboxylic acids or derivatives and diamines · CPC title

• C07C2603/90

  containing more than four rings · CPC title

• C08G73/1082

  wholly aromatic in the tetracarboxylic moiety · CPC title

• C08J2379/08

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