Polymeric matrices formed from monomers comprising a protected amine group
View Patent ↗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.
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.