Polymer including Troger'S base and isatin moieties and having intrinsic microporosity

Patent metadata

Field	Value
Publication number	US-10590239-B2
Application number	US-201715573966-A
Country	US
Kind code	B2
Filing date	Jul 31, 2017
Priority date	Sep 12, 2016
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

A polymer comprising a sub-unit represented by Formula I:

wherein:
L is independently selected from at least one arylene group, and a multi-ring moiety, L′ is independently selected from L or is not present, A and A′ are not present or are independently selected from an isatin moiety with the proviso that at least one of A and A′ is selected from an isatin moiety.

First claim

The invention claimed is:

1. A polymer comprising a sub-unit including a Troger's base moiety, wherein the sub-unit is represented by Formula I:

wherein:
L is independently selected from at least one arylene group, and a multi-ring moiety,
L′ is independently selected from L or is not present,
A and A′ are not present or are independently selected from an isatin moiety with the proviso that at least one of A and A′ is selected from an isatin moiety.

2. The polymer of claim 1 wherein at least one of L and L′ are substituted with at least one of: i) a covalent crosslinking bond and ii) a polar functional group capable of reacting to forming a covalent crosslinking bond.

3. The polymer of claim 2 wherein the polar functional group is selected from at least one of: carboxylic acid and sulfonic acid and their corresponding salt or ester, cyanate and hydroxyl.

4. The polymer of claim 1 wherein L is selected from: phenylene, biphenylene, diphenylene ether, napthalene and spirobisindane.

5. The polymer of claim 1 wherein A is represented by Formula I′:

wherein Z is selected from hydrogen, cyanate, hydroxyl, alkyl, arylene, heteroarylene, alkyl ether, nitro, nitrile, carboxylic acid and sulfonic acid and their corresponding salt or ester, and D is selected from hydrogen and alkyl wherein the alkyl group may be unsubstituted or substituted with a hydroxyl, carboxylic acid, sulfonic acid and their corresponding salt or ester.

6. The polymer of claim 1 comprising a repeating unit represented by at least one of Formula II, III and IV:

wherein:
X, Y, X′ and Y′ are independently selected from: A, hydrogen, carboxylic acid and sulfonic acid and their corresponding salt or ester, cyanate and hydroxyl with the proviso that at least one of X, Y, X′ and Y′ is A; and
R 1 , R 2 , R 3 , and R 4 are independently selected from hydrogen, alkyl groups comprising from 1 to 6 carbon atoms, and R 1 and R 2 may collectively form a ketone group or a 9,9′-fluorene group, and R 3 and R 4 may collectively form a ketone group or a 9,9′-fluorene group.

7. The polymer of claim 6 wherein the polymer is crosslinked through at least one of X, X′, Y and Y′.

8. A membrane comprising the polymer of claim 1 .

9. The membrane of claim 8 characterized by having an average pore size of from 0.2 to 20 nm as determined by ASTM F316-03 (2011).

Assignees

• Dow Global Technologies Llc

Inventors

• Hefner Jr Robert E
• Tomlinson Ian A
• Cramm Brian L

Classifications

• C08G73/0694 Primary

  with only two nitrogen atoms in the ring, e.g. polyquinoxalines · CPC title

• B01D71/62

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain · CPC title

• B01D2325/02

  Details relating to pores or porosity of the membranes · CPC title

• C08G73/0273 Primary

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• B01D2325/0281

  Fibril, or microfibril structures · CPC title