Polymeric matrices formed from monomers comprising a protected amine group

Patent metadata

Field	Value
Publication number	US-9636643-B2
Application number	US-201414465108-A
Country	US
Kind code	B2
Filing date	Aug 21, 2014
Priority date	Dec 21, 2010
Publication date	May 2, 2017
Grant date	May 2, 2017

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.

First claim

I claim:

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.

Assignees

• Gen Electric

Inventors

• Niu Qingshan Jason

Classifications

• C08G69/32

  from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound · CPC title

• C08G2340/00

  Filter material · CPC title

• C08G69/42

  Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen (C08G69/12, C08G69/32 take precedence) · CPC title

• B01D61/08

  Apparatus therefor · CPC title

• B01D69/125

  In situ manufacturing by polymerisation, polycondensation, cross-linking or chemical reaction · CPC title