Ionic Viscoelastics and Viscoelastic Salts

Abstract

One embodiment of the present invention relates to ionic liquids and ionic viscoelastics formed between [1] a small molecule or macromolecule containing two or more cations; and [2] a small molecule or macromolecule containing two or more anions. Another embodiment of the invention is the use of the inventive ionic liquids and ionic viscoelastics, formed between a small molecule or macromolecule containing two or more cations and a small molecule or macromolecule containing two or more anions, to form a crosslinked network. In certain embodiments, the ionic liquids formed can be viscous liquids, viscous liquid formed networks, or viscoelastic networks/gels. In certain embodiments, the ionic material of the invention may be used for a variety of applications including, but not limited to, lubricants, additives, gas separation, liquid separation, membranes, fuel cells, sensors, batteries, coatings, heat storage, liquid crystals, biocompatible fluids, solvents, and electronic materials.

We claim: 
     
         1 . A salt comprising an anionic component and a cationic component, wherein:
 said anionic component is X—[Y] m ;   m is 2, 3, or 4;   X is selected from the group consisting of linear or branched alkanes, linear or branched polyethylene glycols, linear or branched poly(propylene glycol), linear or branched polyethers, linear or branched polyacrylic acids, linear or branched polyamides, and polyether triamines, or a combination thereof;   Y is selected, independently for each occurrence, from the group consisting of -[CO 2 ] −1 , —[SO 3 ] −1 , —[SO 4 ] −2 , —[SbF 5 ] −1 , —[N(CN)] −1 , —[CF 2 S(O) 2 NS(O) 2 CF 3 ] −1 , —[PF 5 ] −1 , —[B(CN) 3 ] −1 , and —[BF 3 ] −1 ;   said cationic component is W—[Z] n ;   n is 2, 3, or 4;   W is selected from the group consisting of linear or branched alkanes, linear or branched polyethylene glycols, linear or branched poly(propylene glycol), linear or branched polyethers, linear or branched polyacrylic acids, linear or branched polyamides, and polyether triamines, or a combination thereof;   Z is selected, independently for each occurrence, from the group consisting of   
       
         
           
           
               
               
           
         
         R is a bond to W or is selected, independently for each occurrence, from the group consisting of hydrogen, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, aryloxy, aryl, heteroaryl, heteroaralkyl, heteroaryloxy, amino, alkylamino, arylamino, heteroarylamino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, phosphonium, carbonyl, carboxyl, silyl, alkylthio, sulfonyl, sulfonamido, ketone, aldehyde, ester, heterocyclyl, trifluoromethyl, and cyano; 
         provided that exactly one R is a bond to W; and 
         any two adjacent R, taken together with the atoms to which they are directly bound, may form a 5-membered, 6-membered, or 7-membered, saturated or unsaturated, carbocyclic or heterocyclic, ring, 
         provided that, when m is 2 or 4, n is 3; and when n is 2 or 4, m is 3. 
       
     
     
         2 . The salt of  claim 1 , wherein Y is —[CO 2 ] −1 . 
     
     
         3 . The salt of  claim 1 , wherein X and W are the same. 
     
     
         4 . The salt of  claim 1 , wherein Z is selected, independently for each occurrence, from the group consisting of 
       
         
           
           
               
               
           
         
       
     
     
         5 . The salt of  claim 1 , wherein R is a bond to W or is selected, independently for each occurrence, from the group consisting of hydrogen or alkyl. 
     
     
         6 . The salt of  claim 1 , wherein said cationic component is W—[Z] 2 . 
     
     
         7 . The salt of  claim 6 , wherein said anionic component is X—[Y] 3 ; X is C(R′)(A-) 3 , C(R′)[(AO) p A-] 3 , C(R′)[(ANH) p A-] 3 , N(A) 3 , N[(AO) p A-] 3 , or N[(ANH) p A-] 3 ; A is, independently for each occurrence, —(CQ 2 ) p -; Q is, independently for each occurrence, hydrogen or methyl; p is, independently for each occurrence, 0-40 inclusive; and R′ is hydrogen, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, aryloxy, aryl, heteroaryl, heteroaralkyl, heteroaryloxy, amino, alkylamino, arylamino, heteroarylamino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, phosphonium, carbonyl, carboxyl, silyl, alkylthio, sulfonyl, sulfonamido, ketone, aldehyde, ester, heterocyclyl, trifluoromethyl, and cyano. 
     
     
         8 . The salt of  claim 6 , wherein W is —CH 2 OCH 2 CH 2 OCH 2 —, —(CH 2 ) 10 —, or poly(acrylonitrile-co-butadiene). 
     
     
         9 . The salt of  claim 6 , wherein W—[Z] 2  is [N(R″) 3 ]—W—[N(R″) 3 ] or [P(R″) 3 ]—W—[P(R″) 3 ]; and R″ is hydrogen, alkyl, aryl, or aralkyl. 
     
     
         10 . The salt of  claim 1 , wherein said cationic component is W—[Z] 3 . 
     
     
         11 . The salt of  claim 10 , wherein said anionic component is X—[Y] 2 ; X is —(CH 2 ) q —, —CH 2 O(CH 2 O) q CH 2 —, —CH 2 O(CH 2 CH 2 O) q CH 2 —, —CH 2 CH 2 O(CH 2 CH 2 CH 2 O) q CH 2 CH 2 —, —CH 2 CH 2 CH 2 O(CH 2 CH 2 CH 2 CH 2 O) q CH 2 CH 2 CH 2 —, —CH 2 NH(CH 2 NH) q CH 2 —, —CH 2 NH(CH 2 CH 2 NH) q CH 2 —, —CH 2 CH 2 NH(CH 2 CH 2 CH 2 NH) q CH 2 CH 2 —, or —CH 2 CH 2 CH 2 NH(CH 2 CH 2 CH 2 CH 2 NH) q CH 2 CH 2 CH 2 —; and q is 0-40 inclusive. 
     
     
         12 . The salt of  claim 10 , wherein said anionic component is X—[Y] 4 ; X is C(ACH 2 —) 4 , C[(AO) p A-] 4 , C[(ANH) p A-] 4 , (-A) 2 N(AO) p AN(A-) 2 , or (-A) 2 N(ANH) p AN(A-) 2 ; A is, independently for each occurrence, —(CQ 2 ) p -; Q is, independently for each occurrence, hydrogen or methyl; and p is, independently for each occurrence, 0-40 inclusive. 
     
     
         13 . The salt of  claim 10 , wherein W is C(R′)(A-) 3 , C(R′)[(AO) p A-] 3 , or N(A-) 3 ; A is, independently for each occurrence, —(CQ 2 ) p -; Q is, independently for each occurrence, hydrogen or methyl; p is, independently for each occurrence, 0-40 inclusive; and R′ is hydrogen or methyl. 
     
     
         14 . The salt of  claim 10 , wherein W—[Z] 3  is [Z]—W—[N(R″) 3 ] 2  or [Z]—W—[P(R″) 3 ] 2 ; and R″ is hydrogen, alkyl, aryl, or aralkyl. 
     
     
         15 . The salt of  claim 1 , wherein said cationic component is W—[Z] 4 . 
     
     
         16 . The salt of  claim 15 , wherein said anionic component is X—[Y] 3 ; X is C(R′)(A-) 3 , C(R′)[(AO) p A-] 3 , C(R′)[(ANH) p A-] 3 , N(A) 3 , N[(AO) p A-] 3 , or N[(ANH) p A-] 3 ; A is, independently for each occurrence, —(CQ 2 ) p -; Q is, independently for each occurrence, hydrogen or methyl; p is, independently for each occurrence, 0-40 inclusive; and R′ is hydrogen, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, aryloxy, aryl, heteroaryl, heteroaralkyl, heteroaryloxy, amino, alkylamino, arylamino, heteroarylamino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, phosphonium, carbonyl, carboxyl, silyl, alkylthio, sulfonyl, sulfonamido, ketone, aldehyde, ester, heterocyclyl, trifluoromethyl, and cyano. 
     
     
         17 . The salt of  claim 15 , wherein W is C(ACH 2 —) 4 , C[(AO) p A-] 4 , C[(ANH) p A-] 4 , (-A) 2 N(AO) p AN(A-) 2 , or (-A) 2 N(ANH) p AN(A-) 2 ; A is, independently for each occurrence, —(CQ 2 ) p -; Q is, independently for each occurrence, hydrogen or methyl; and p is, independently for each occurrence, 0-40 inclusive. 
     
     
         18 . The salt of  claim 15 , wherein W—[Z] 4  is W—[N(R″) 3 ] 4  or W—[P(R″) 3 ] 4 ; and R″ is hydrogen, alkyl, aryl, or aralkyl.