IP Library Granted Patent US 7,681,741
Granted Patent B2
US 7,681,741 · App. 11/611,644 · Granted Mar 23, 2010

Functional polyarylethers

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Quick Facts
Patent No.
US 7,681,741
App. No.
11/611,644
Granted
Mar 23, 2010
Kind
B2
Abstract

Membranes comprising functional polyarylether having structural units of formula II are useful for hemodialysis and hemofiltration: wherein X is selected from Br, NR 4 R 5 , OOCR 6 , OR 7 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 COOR 5 R 6 and combinations thereof; R 1 , R 2 and R 3 are independently at each occurrence H, X, halo, cyano, nitro, a C 1-C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof; R 4 and R 5 are independently H, a C 1 -C 10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical, or a combination thereof; R 6 is H, a C 2-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof; R 7 is OCH 2 CH 2 (OCH 2 CH 2 ) n OH or OOCCH 2 (OCH 2 CH 2 ) n CH 3; Q is a direct bond, O, S, CH 2 , alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof; Z is a direct bond, O, S, CH 2 , SO, SO 2 , CO, phenylphospinyl oxide, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof; a, b, and c are independently 1 or 2; and m, n and p are independently 0 or 1.

Claims (66)

1. A functional polyarylether comprising structural units of formula II

wherein

X is selected from OOCR 6 , R 7 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 COOR 5 R 6 ,

and combinations thereof;

R 1 , R 2 and R 3 are independently at each occurrence CH 2 X, H, halo, cyano, nitro, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

R 4 and R 5 are independently H, a C 1-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical, or a combination thereof;

R 6 is H, a C 2-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

R 7 is OCH 2 CH 2 (OCH 2 CH 2 ) q OCH 3 or OOCCH 2 (OCH 2 CH 2 ) q OCH 3 ;

Q is a direct bond, O, S, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

Z is a direct bond, O, S, SO, SO 2 , CO, phenylphospinyl oxide, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

a, b, and c are independently 1 or 2;

m, n and p are independently 0 or 1; and

q is 1-8.

2. A functional polyarylether according to claim 1 , wherein Z is SO 2 .

3. A functional polyarylether according to claim 1 , wherein X is NR 4 COR 5 .

4. A functional polyarylether according to claim 1 , wherein X is NR 4 COOR 5 R 6 .

5. A functional polyarylether according to claim 1 , wherein Q is a direct bond.

6. A functional polyarylether according to claim 1 , wherein Q is C(CH 3 ) 2 .

7. A functional polyarylether according to claim 1 , wherein

X is selected from OCH 2 CH 2 (OCH 2 CH 2 ) q OCH 3 , OOCCH 2 (OCH 2 CH 2 ) q OCH 3 ,

and combinations thereof.

8. A functional polyarylether according to claim 1 , wherein

X is OOCCH 3 or

R 1 and R 2 are independently H or CH 3 ; and

Q is a direct bond or C(CH 3 ) 2 .

9. A functional polyarylether according to claim 1 , comprising structural units of formula.

10. A functional polyarylether according to claim 1 , wherein R 1 and R 3 are CH 3 .

11. A functional polyarylether according to claim 1 , wherein R 1 and R 3 are H.

12. A functional polyarylether according to claim 1 , wherein Q is a direct bond.

13. A functional polyarylether according to claim 1 , wherein Q is C(CH 3 ) 2 .

14. A functional polyarylether according to claim 1 , comprising structural units of formula

15. A functional polyarylether according to claim 1 , comprising structural units of formula

16. A functional polyarylether according to claim 1 , comprising structural units of formula

17. A membrane comprising functional polyarylether comprising structural units of formula

wherein

X is selected from OOCR 6 , R 7 , NR 4 COR 5 , NR 4 CONR 5 R 6 ,

NR 4 COOR 5 R 6 ,

and combinations thereof;

R 1 , R 2 and R 3 are independently at each occurrence CH 2 X, H, halo, cyano, nitro, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

R 4 and R 5 are independently H, a C 1-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical, or a combination thereof;

R 6 is H, a C 2-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

R 7 is OCH 2 CH 2 (OCH 2 CH 2 ) q OCH 3 or OOCCH 2 (OCH 2 CH 2 ) q OCH 3 ;

Q is a direct bond, O, S, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

Z is a direct bond, O, S, SO, SO 2 , CO, phenylphospinyl oxide, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

a, b, and c are independently 1 or 2;

m, n and p are independently 0 or 1; and q is 1-8.

18. A separation unit comprising a plurality of hollow fiber membranes, wherein at least one of the plurality of membranes comprises a functional polyarylether according to claim 1 .

19. A hemodialysis apparatus comprising a membrane according to claim 16 .

20. A bioseparation apparatus comprising a membrane according to claim 16 .

21. A process for preparing polyarylether, said process comprising combining a bromopolyarylether and a nucleophile with a copper catalyst under basic conditions;

wherein the bromoarylether comprises structural units of formula

the nucleophile is selected from the group consisting of;

HOOCR 6 ; HR 7 ; HNR 4 COR 5 ; HNR 4 CONR 4 R 5 ,

and combinations thereof;

X is Br;

R 1 , R 2 and R 3 are independently at each occurrence CH 2 X, H, halo, cyano, nitro, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a aromatic radical or a combination thereof;

R 4 and R 5 are independently H, a C 1-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical, or a combination thereof;

R 6 is a C 2-10 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

R 7 is OCH 2 CH 2 (OCH 2 CH 2 ) q OCH 3 or OOCCH 2 (OCH 2 CH 2 ) q OCH 3 ;

Z is a direct bond, O, S, CH 2 , SO, SO 2 , CO, phenylphospinyl oxide, alkenyl, alkynyl, a C 1 -C 12 aliphatic radical, a C 3 -C 12 cycloaliphatic radical, a C 3 -C 12 aromatic radical or a combination thereof;

a, b, and c are independently 1 or 2;

m, n and p are independently 0 or 1; and

q is 1-8.

22. A process according to claim 21 , additionally comprising combining the bromopolyarylether, the nucleophile and the copper catalyst in the presence of a diamine ligand.

23. A process according to claim 22 , wherein the diamine ligand is CH 3 NHCH 2 CH 2 NHCH 3 .

24. A process according to claim 21 , additionally comprising combining the bromopolyarylether, the nucleophile and the copper catalyst in a dioxane solvent.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE TO GENERAL ELECTRIC COMPANY & CORRECT CORRESPONDENCE STREET ADDRESS TO: 1 RESEARCH CIRCLE PREVIOUSLY RECORDED ON REEL 027518 FRAME 0803. ASSIGNOR(S) HEREBY CONFIRMS THE CLARIFICATION OF OWNERSHIP. Recorded Jan 13, 2012
From: GENERAL ELECTRIC COMPANY
To: GENERAL ELECTRIC COMPANY
Reel/Frame 027531/0149 →
CLARIFICATION OF OWNERSHIP Recorded Jan 11, 2012
From: GENERAL ELECTRIC COMPANY
To: GENEFRAL ELECTRIC COMPANY
Reel/Frame 027518/0803 →
SECURITY AGREEMENT Recorded Aug 18, 2008
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021423/0001 →