IP Library Granted Patent US 9,636,643
Granted Patent B2
US 9,636,643 · App. 14/465,108 · Granted May 2, 2017

Polymeric matrices formed from monomers comprising a protected amine group

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,636,643
App. No.
14/465,108
Granted
May 2, 2017
Kind
B2
Abstract

The present disclosure relates to polymeric matrices composed of protected amine compound residues and membranes composed from such polymeric matrices. In particular, the present disclosure relates to a polymeric matrix comprising amine compound residues, acyl compound residues and protected amine compound residues.

Claims (67)

1. A polymeric matrix, wherein the matrix is composed of:

(i) amine compound residues having at least two amine moieties;

(ii) acyl compound residues having at least two acyl moieties; and

(iii) protected amino compound residues having

(a) at least two amine moieties, or

(b) at least one amine moiety and at least one acyl moiety;

wherein the protected amino compound residue is a residue of the formula (I):

wherein

Ar is an aryl group containing 6-14 carbon atoms, n is 1, 2 or 3, wherein

when n is 1 or 3, R is independently or simultaneously

 and

when n is 2, R is

2. The matrix of claim 1 , wherein at least a portion of the protected amino compound residues comprising at least one amine moiety and at least one acyl moiety comprise a self-polymerized polymer.

3. The matrix of claim 1 , further comprising a substrate to form a membrane and wherein the membrane possesses an A value of at least about 5.0.

4. The matrix of claim 1 , wherein the residues of the formula (I) are residues of the formula (Ia), (Ib) or (Ic):

wherein R′ is

5. The matrix of claim 4 , wherein the residue of the formula (Ia) is:

6. The matrix of claim 4 , wherein the residue of the formula (Ib) is:

7. The matrix of claim 4 , wherein the residue of the formula (Ic) is:

8. The matrix of claim 1 , wherein the amine compound residues comprise an aromatic amine compound residue, an aliphatic amine compound residue, or a cycloaliphatic amine compound residue.

9. The matrix of claim 8 , wherein the aromatic amine compound residue comprises a residue of the formula (II):

wherein Ar is an aryl group containing 6-14 carbon atoms; and

wherein p is 1, 2 or 3.

10. The matrix of claim 9 , wherein the residue of the formula (II) is:

11. The matrix of claim 1 , wherein the acyl compound residue is a residue of the formula (III):

wherein

Ar is an aryl group containing 6-14 carbon atoms;

m is 2, 3 or 4.

12. The matrix of claim 11 , wherein the residue of formula (III) is:

wherein m is 2 or 3.

13. The matrix of claim 12 , wherein the residue of formula (III) is:

14. A polymeric reaction product formed from interfacial polymerization of:

(i) polyamine monomers;

(ii) amine reactive polyacyl monomers; and

(iii) monomers comprising a protected amino group;

wherein the monomers comprising a protected amino group are compounds of the formula (VI):

wherein

Ar is an aryl group containing 6-14 carbon atoms;

Y is a protected amino group;

n is 1, 2 or 3, wherein

when n is 1 or 2, R is Y; and

when n is 3, R is independently or simultaneously Y or —C(O)—X; and

X is a leaving group.

15. The polymeric reaction product of claim 14 , wherein Y is —N═S═O.

16. The polymeric reaction product of claim 14 , wherein the compound of the formula (VI) is:

17. The polymeric reaction product of claim 14 , wherein the compound of the formula (VI) is:

18. The polymeric reaction product of claim 14 , wherein the compound of the formula (VI) is:

19. The polymeric reaction product of claim 14 , wherein the polyamine monomers comprise at least two reactive amino (—NH 2 ) moieties.

20. The polymeric reaction product of claim 19 , wherein the polyamine monomers comprise aromatic polyamine monomers, aliphatic polyamine monomers or cycloaliphatic polyamine monomers.

21. The polymeric reaction product of claim 20 , wherein the aromatic polyamine monomers are compounds of the formula (IX)

wherein Ar is an aryl group containing 6-14 carbon atoms; and

p is 1, 2 or 3.

22. The polymeric reaction product of claim 21 , wherein the aromatic polyamine monomer is:

23. The polymeric reaction product of claim 14 , wherein the amine reactive polyacyl monomers are compounds of the formula (XII):

wherein

Ar is an aryl group containing 6-14 carbon atoms;

X′ is a leaving group;

m is 2, 3 or 4.

24. The polymeric reaction product of claim 23 , wherein the amine reactive polyacyl monomer of the formula (XII) is:

wherein m is 2 or 3; and

X′ is a leaving group.

25. The polymeric reaction product of claim 24 , wherein the amine reactive polyacyl monomers is:

wherein X′ is a leaving group.

26. The polymeric reaction product of claim 25 , wherein X′ is a halogen atom.

27. A combination comprising the polymeric matrix of claim 1 coated on a support material.

28. A composite membrane comprising a polymeric matrix according to claim 1 on a porous support material.

29. The composite membrane of claim 28 that is a reverse osmosis (RO) or nano-filtration (NF) membrane.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2018
From: GENERAL ELECTRIC COMPANY
To: BL TECHNOLOGIES, INC.
Reel/Frame 047502/0065 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 14, 2017
From: NIU, QINGSHAN JASON
To: GENERAL ELECTRIC COMPANY
Reel/Frame 041573/0099 →