Ion Exchange Stationary Phases For Analyzing Polyvalent Ions

Abstract

Ion exchange stationary phases are prepared with diprimary diamines for applications such as separating samples that contain polyvalent anions. The ion exchange stationary phase includes a series of condensation polymer reaction products bound to a substrate. The condensation polymer products are formed with diprimary diamines and polyepoxide compounds. The ion exchange stationary phases described herein are capable of separating monovalent and highly polyvalent anions relatively quickly with relatively low eluent concentrations in one chromatographic run.

1 - 21 . (canceled) 
     
     
         22 . An ion exchange stationary phase comprises:
 a) a negatively charged substrate particle;   b) a first condensation polymer reaction product attached to the negatively charged substrate particle, the first condensation polymer reaction product comprises a reaction product of a first diprimary diamine and a first polyepoxide;   c) a second condensation polymer reaction product covalently attached to the first condensation polymer reaction product, the second condensation polymer reaction product comprises a reaction product of an amine group of the first condensation polymer reaction product and two second polyepoxides;   wherein the amine group of the first condensation polymer reaction product includes a positive charge so that the first condensation polymer reaction product is ionically coupled to the negatively charged substrate particle;   d) a third condensation polymer reaction product covalently attached to the second condensation polymer reaction product, the third condensation polymer reaction product comprises a reaction product of a second diprimary diamine and an epoxide group of the second condensation polymer reaction product;   e) a fourth condensation polymer reaction product covalently attached to the third condensation polymer reaction product, the fourth condensation polymer reaction product comprises a reaction product of an amine group of the third condensation polymer reaction product and a third polyepoxide; and   f) a fifth condensation polymer reaction product covalently attached to the fourth condensation polymer reaction product, the fifth condensation polymer reaction product comprises a reaction product of a third diprimary diamine and an epoxide group of the fourth condensation polymer reaction product;   wherein chromatography using the ion exchange stationary phase with a 10 mM KOH eluent concentration elutes phosphate ion earlier than chloride ion;   wherein the first, second, and third diprimary amines independently have the structure:
   H 2 N-L-NH 2    
   or a salt thereof, wherein each L is independently selected from substituted alkyl and unsubstituted alkyl, unsubstituted heteroalkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, and unsubstituted heteroaryl.   
     
     
         23 . The ion exchange stationary phase of  claim 22 , in which the first condensation polymer reaction product comprises a plurality of quaternary amines and a plurality of hydroxyl groups. 
     
     
         24 . The ion exchange stationary phase of  claim 23 , in which the second condensation polymer reaction product comprises a plurality of hydroxyl groups and a plurality of ether groups. 
     
     
         25 . The ion exchange stationary phase of  claim 24 , in which the third condensation polymer reaction product comprises a plurality of quaternary amines. 
     
     
         26 . The ion exchange stationary phase of  claim 25 , in which the fourth condensation polymer reaction product comprises a plurality of hydroxyl groups and a plurality of ether groups. 
     
     
         27 . The ion exchange stationary phase of  claim 26 , in which the fifth condensation polymer reaction product comprises a plurality of primary amines and a plurality of secondary amines. 
     
     
         28 . The ion exchange stationary phase of  claim 22 , in which the negatively charged substrate particle comprises a crosslinked divinylbenzene and ethylvinyl benzene particle, in which at least a surface of the negatively charged substrate particle includes sulfonate groups. 
     
     
         29 . The ion exchange stationary phase of  claim 22 , in which the first polyepoxide compound, second polyepoxide compound, and third polyepoxide compound are each a diepoxide compound. 
     
     
         30 . The ion exchange stationary phase of  claim 29 , in which the diepoxide compound is 1,4-butanediol diglycidyl ether. 
     
     
         31 . The ion exchange stationary phase of  claim 22 , in which the first diprimary diamine, the second diprimary diamine, and the third diprimary diamine are the same 
     
     
         32 . The ion exchange stationary phase of  claim 22 , in which the fifth polymer layer is reacted with a glycidol. 
     
     
         33 . The ion exchange stationary phase of  claim 22 , in which the first polyepoxide comprises an alkyldiol diglycidyl ether. 
     
     
         34 . The ion exchange stationary phase of  claim 22 , in which the substrate particle comprises a copolymer of divinylbenzene and ethylvinylbenzene, in which the substrate particle is a negatively charged particle. 
     
     
         35 . The ion exchange stationary phase of  claim 22 , in which the first diprimary diamine is selected from the group consisting of diaminoethane, diaminopropane, diaminobutane, diaminopentane, diaminohexane, lysine, diaminocyclohexane, diaminotriethylene glycol, and a combination thereof.