Polyelectrolyte complex films for analytical and membrane separation of chiral compounds

• US 7,365,142 B2
• Filed: 08/07/2006
• Issued: 04/29/2008
• Est. Priority Date: 06/14/2002
• Status: Expired due to Fees

• Current Assignee: Florida State University Research Foundation, Inc. (State University System of Florida)
• Original Assignee: Florida State University Research Foundation, Inc. (State University System of Florida)
• Inventors: Rmaile, Hassan, Schlenoff, Joseph B.
• Primary Examiner(s): CHOI, LING SIU
• Application Number:
  US11/500,085
• Publication Number:
  US 20070037948A1
• Time in Patent Office: 631 Days
• Field of Search: 526/348.1, 526/317.1, 526/303.1, 428/500, 428/515, 428/475.8, 210/198.2, 210/660, 210/654
• US Class Current: 526/348.1
• CPC Class Codes: C07B 57/00 Separation of optically-active compounds
• CPC Class Codes: C08L 25/18 Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
• CPC Class Codes: Y10T 428/31743 Next to addition polymer from unsaturated monomer[s]
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers

Abstract

The present invention is directed to enantioselective polyelectrolyte complex films. Further, said films may be free or isolated membranes, or coatings on substrates such a porous substrates, capillary tubes, chromatographic packing material, and monolithic stationary phases and used to separate chiral compounds. The present invention is also directed to a method for forming such enantioselective polyelectrolyte complex films.

Claims

1. A method of separating or resolving a mixture of enantiomers, the method comprising contacting a solution comprising the enantiomers with a membrane that interacts with the enantiomers in an enantioselective manner and separating the enantiomers by passage through the membrane, the membrane comprising a polyelectrolyte complex film having a thickness between about 10 nm and about 10,000 nm and containing a positively-charged polyelectrolyte and a negatively-charged polyelectrolyte wherein at least one of the polyelectrolytes comprises an enantiomeric excess of chiral repeat units.

2. The method of claim 1 wherein the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte comprise an enantiomeric excess of chiral repeat units.

3. The method of claim 1 wherein both the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte comprise an enantiomeric excess of L-chiral repeat units or both the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte comprise an enantiomeric excess of D-chiral repeat units.

4. The method of claim 1 wherein the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte are selected from the group consisting of linear polyelectrolytes, branched polyelectrolytes, dendritic polyelectrolytes, graft polyelectrolytes, comb polyelectrolytes and copolymers thereof.

5. The method of claim 1 wherein the polyelectrolyte comprising an enantiomeric excess of chiral repeat units is formed from chiral monomer units.

6. The method of claim 1 wherein the positively-charged polyelectrolyte is poly(lysine) and the negatively-charged polyelectrolyte is poly(glutamic acid).

7. The method of claim 1 wherein the polyelectrolyte comprising an enantiomeric excess of a chiral repeat units is the reaction product of a non-chiral polymer and a chiral reagent or a non-chiral reagent which introduces chirality.

8. The method of claim 7 wherein the positively-charged polyelectrolyte is the polyelectrolyte comprising an enantiomeric excess of chiral repeat units and the non-chiral polymer comprises an amine group, a pyridine group, or a benzyl halogen group.

9. The method of claim 7 wherein the chiral reagent or the non-chiral reagent which introduces chirality is selected from the group consisting of a chiral alkyl halide and a chiral aryl halide.

10. The method of claim 7 wherein the negatively-charged polyelectrolyte is the polyelectrolyte comprising an enantiomeric excess of chiral repeat units, the negatively-charged polyelectrolyte comprises a sulfonate group or a carboxylate group.

11. The method of claim 1 wherein the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte is formed from a synthetic monomer and at least one of the polyelectrolytes comprises an enantiomeric excess of chiral repeat units.

12. The method of claim 1 wherein at least one of the negatively-charged polyelectrolyte and the positively-charged polyelectrolyte comprises a chiral cyclodextrin moiety.

13. The method of claim 1 wherein the positively-charged polyelectrolyte and the negatively-charged polyelectrolyte comprise a chiral cyclodextrin moiety.

14. The method of claim 1 wherein at least one of the polyelectrolytes comprises a charged repeat unit selected from the group diallyldimethylammonium, vinylbenzyltrimethylammonium, ionene, acryloxyethyltrimethyl ammonium chloride, methacryloxy (2-hydroxy) propyltrimethyl ammonium chloride, N-alkylvinylpyridinium, allylamine hydrochloride, ethyleneimine, styrenesulfonate, 2-acrylamido-2-methyl-1-propane sulfonate, sulfonated ether ether ketone, ethylenesulfonic acid, methacryloxyethylsulfonic acid, acrylic acid, methacrylic acid, salts thereof, and mixtures thereof.

15. The method of claim 1 wherein at least one of the polyelectrolytes is selected from the group consisting of poly(diallyldimethylammonium chloride), poly (vinylbenzyltrimethylammonium), ionenes, poly(acryloxyethyltrimethyl ammonium chloride), poly (methacryloxy (2-hydroxy) propyltrimethyl ammonium chloride), a poly(N-alkylvinylpyridinium), a poly(N-aryl vinyl pyridinium), poly(allylaminehydrochloride), polyethyleneimine, poly(styrenesulfonic acid), poly(2-acrylamido-2-methyl-1-propane sulfonic acid), sulfonated poly (ether ether ketone), poly (ethylenesulfonic acid), poly (methacryloxyethylsulfonic acid), poly(acrylic acid), poly(methacrylic acid), salts thereof, copolymers thereof, and mixtures thereof.

16. The method of claim 1 wherein at least one of the polyelectrolytes is selected from the group consisting of proteins, polypeptides, enzymes, DNA, RNA, heparin, alginic acid, chondroitin sulfate, chitosan, chitosan sulfate, cellulose sulfate, polysaccharides, dextran sulfate, and carboxymethylcellulose.