Foamed ionic compounds

US 8,946,442 B2
Filed: 12/21/2010
Issued: 02/03/2015
Est. Priority Date: 12/21/2009
Status: Active Grant

First Claim

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1. An ionic, non-polymeric foam that comprises an ionic compound wherein the ionic compound comprises an anion selected from the group consisting of(a) aminoacetate, ascorbate, benzoate, catecholate, citrate, formate, fumarate, gallate, glycolate, glyoxylate, iminodiacetate, isobutyrate, kojate, lactate, levulinate, oxalate, pivalate, propionate, pyruvate, salicylate, succinamate, succinate, tiglate, and tropolonate;

(b) [CH₃CO₂]⁻, [HSO₄]⁻, [CH₃OSO₃]⁻, [C₂H₅OSO₃]⁻, [AlCl₄]⁻, [CO₃]²⁻, [HCO₃]⁻, [NO₂]⁻, [NO₃]⁻, [SO₄]²⁻, [HSO₃]⁻, [CuCl₂]⁻, Cl⁻, Br⁻, I⁻, SCN⁻;

carborates optionally substituted with alkyl or substituted alkyl groups; and

carboranes optionally substituted with alkylamine, substituted alkylamine, alkyl or substituted alkyl groups;

(c) [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃], [CF₂ICF₂OCF₂CF₂SO₃], [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]₋, [(CF₃CFHCF₂SO₂)₂N]⁻, and F⁻; and

(d) anions represented by the structure of the following formula;

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Abstract

Foams of ionic compounds are described. Methods of making the foams are also provided. The foams are ionic and can be used for catalysis, separations, gas storage, biosensors, electronics, and electrochemical applications.

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19 Claims

1. An ionic, non-polymeric foam that comprises an ionic compound wherein the ionic compound comprises an anion selected from the group consisting of(a) aminoacetate, ascorbate, benzoate, catecholate, citrate, formate, fumarate, gallate, glycolate, glyoxylate, iminodiacetate, isobutyrate, kojate, lactate, levulinate, oxalate, pivalate, propionate, pyruvate, salicylate, succinamate, succinate, tiglate, and tropolonate;
- (b) [CH₃CO₂]⁻, [HSO₄]⁻, [CH₃OSO₃]⁻, [C₂H₅OSO₃]⁻, [AlCl₄]⁻, [CO₃]²⁻, [HCO₃]⁻, [NO₂]⁻, [NO₃]⁻, [SO₄]²⁻, [HSO₃]⁻, [CuCl₂]⁻, Cl⁻, Br⁻, I⁻, SCN⁻;
  
  carborates optionally substituted with alkyl or substituted alkyl groups; and
  
  carboranes optionally substituted with alkylamine, substituted alkylamine, alkyl or substituted alkyl groups;
  
  (c) [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃], [CF₂ICF₂OCF₂CF₂SO₃], [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]₋, [(CF₃CFHCF₂SO₂)₂N]⁻, and F⁻; and
  
  (d) anions represented by the structure of the following formula;
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
- - 2. A foam according to claim 1 wherein the ionic compound further comprises a cation, and the cation is selected from the group consisting of cations represented by the structures of the following formulae:
  - 3. A foam according to claim 1 wherein the anion is selected from one or more members of the group consisting of:
    - [CH₃CO₂]⁻, [HSO₄]⁻, [CH₃OSO₃]⁻, [C₂H₅OSO₃]⁻, [AlCl₄]⁻, [CO₃]²⁻, [HCO₃]⁻, [NO₂]⁻, [NO₃]⁻, [SO₄]²⁻, [HSO₃]⁻, [CuCl₂]⁻, Cl⁻, Br⁻, I⁻, SCN⁻;
      
      carborates optionally substituted with alkyl or substituted alkyl groups; and
      
      carboranes optionally substituted with alkylamine, substituted alkylamine, alkyl or substituted alkyl groups.
  - 4. An article fabricated from a foam according to claim 1.
  - 5. An article according to claim 4 that comprises a gas storage device, a catalyst, a biosensor or electrode, an immobilization support, a separation membrane, or an electrochemical cell component.
  - 6. A foam according to claim 1 wherein the ionic compound is 1-butyl-3-methylimidazolium chloride.
  - 7. A foam according to claim 1 which is electrically conductive.
  - 8. A foam according to claim 1 which is flexible or rigid.
  - 9. A foam according to claim 1 which is a solid state foam.
  - 10. A foam according to claim 1 which is open-cell or closed cell.
  - 11. A foam according to claim 1 which is microcellular or nanocellular.
  - 12. A foam according to claim 1 wherein the ionic compound further comprises a cation, and wherein the cation and anion are selected from the group consisting of:
    - a) imidazolium as the cation, and an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, [CF₃CFHCF₂SO₂)₂N]⁻, and [CH₃OSO₃]⁻;
      
      b) 1-butyl-3-methylimidazolium as the cation, and an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻;
      
      c) 1-propyl-2,3-dimethylimidazolium as the cation, and an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, and [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃], [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻,d) 1-ethyl-3-methylimidazolium as the cation, and an anion selected from the group consisting of [(CF₃CF₂SO₂)₂N]⁻, [PF₆]⁻, and [HCF₂CF₂SO₃]⁵;
      
      e) 1-propyl-3-methylpyridinium as the cation, and an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂)₂N]⁻;
      
      f) 1,2-dimethyl-3-propylimidazolium as the cation, and an anion selected, from the group consisting of [(CF₃SO₂)₃C]⁻ and [(CF₃SO₂)₂N]⁻;
      
      g) 3-methyl-1-propy pyridinium as the cation, and [(CF₃SO₂)₂N]⁻ as the anion;
      
      h) 1-butyl-3-methylpyridinium as the cation, and [(CF₃SO₂)₂N]⁻ as the anion;
      
      i) 1-dodecyl-3-methylimidazolium as the cation, and [HCF₂CF₂SO₃]⁻ as the anion;
      
      j) 1-heptyl-3-methylimidazolium as the cation, and [HCF₂CF₂SO₃]⁻ as the anion;
      
      k) tetradecyl(trihexyl)phosphonium as the cation, and an anion selected from the group consisting of [CF₃CF₂OCFHCF₂SO₃]⁻ and [CF₃OCFHCF₂SO₃]⁻;
      
      l) tributyl(tetradecyl)phosphonium as the cation, and [CF₃HFCCF₂SO₃]⁻ as the anion; and
      
      m) 1,3-dioctylimidazolium or 1-octyl-3-methylimidazolium as the cation, and [I]⁻ as the anion.
  - 13. A foam according to claim 1 wherein an ionic compound comprises a cation, and the cation is selected from the group consisting of:
    - 1,2-dimethylpyridinium,1-methyl-2-ethylpyridinium,1-methyl-2-ethyl-6-methylpyridinium,N-methylpyridinium,1-butyl-2-methylpyridinium,1-butyl-2-ethylpyridinium,1-butyl-2-ethyl-6-methylpyridinium,N-butylpyridinium,1-butyl-4-methylpyridinium,1,3-dimethylimidazolium,1,2,3-trimethylimidazolium,1-n-butyl-3-methylimidazolium,1,3,4,5-tetramethylimidazolium,1,3,4-trimethylimidazolium,2,3-dimethylimidazolium,1-butyl-2,3-dimethylimidazolium,3,4-dimethylimidazolium,2-ethyl-3,4-dimethylimidazolium,3-methyl-2-ethylimidazol,3-butyl-1-methylimidazolium,3-butyl-1-ethylimidazolium,3-butyl-1,2-dimethylimidazolium,1,3-di-n-butylimidazolium,3-butyl-1,4,5-trimethylimidazolium,3-butyl-1,4-dimethylimidazolium,3-butyl-2-methylimidazolium,1,3-dibutyl-2-methylimidazolium,3-butyl-4-methylimidazolium,3-butyl-2-ethyl-4-methylimidazolium and3-butyl-2-ethylimidazolium,1-meth octylimidazolium and1-decyl-3-methylimidazolium cations.
  - 14. A foam according to claim 1 wherein the ionic compound further comprises a cation, and wherein the cation and anion are selected from the group consisting of:
    - d) an imidazolium cation or a fluorinated imidazolium cation; and
      
      an anion, selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻;
      
      e) a 1-ethyl-3-methylimidazolium or a fluorinated 1-ethyl-3-methylimidazolium as the cation, and [(CF₃CF₂SO₂)₂N]⁻ as the anion;
      
      f) a 1-butyl-3-methylimidazolium cation or a fluorinated 1-butyl-3-methylimidazolium cation; and
      
      an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻;
      
      g) a 1-propyl-2,3-dimethylimidazolium cation or a fluorinated 1-propyl-2,3-dimethylimidazolium cation; and
      
      an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻;
      
      h) a 1-propyl-3-methylimidazolium cation or a fluorinated 1-propyl-3-methylimidazolium cation; and
      
      an anion selected from the group consisting of [BF₄]⁻, [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃]⁻, [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]⁻, and [(CF₃CFHCF₂SO₂)₂N]⁻;
      
      i) a 1,2-dimethyl-3-propylimidazolium cation or a fluorinated 1,2-dimethyl-3-propylimidazolium cation; and
      
      an anion selected from the group consisting of [(CF₃SO₂)₃C]⁻ and [(CF₃SO₂)₂N]⁻;
      
      j) a 3-methyl-1-propylpyridinium cation or a fluorinated 3-methy-1-propylpyridinium cation, and [(CF₃SO₂)₂N]⁻ as the anion;
      
      k) a 1-butyl-3-methylpyridinium cation or a fluorinated 1-butyl-3-methylpyridinium cation, and [(CF₃SO₂)₂N]⁻ as the anion;
      
      l) a 1-dodecyl-3-methylimidazolium cation or a fluorinated 1-dodecyl-3-methylimidazolium cation, and [HCF₂CF₉SO₃]⁻ as the anion;
      
      m) a 1-heptyl-3-methylimidazolium cation or a fluorinated 1-heptyl-3-methylimidazolium cation, and [HCF₂CF₉SO₃]⁻ as the anion;
      
      n) a tetradecyl(trihexyl)phosphonium cation or a fluorinated tetradecyl(trihexyl)phosphonium cation, and an anion selected from the group consisting of [CF₃CF₂OCFHCF₂SO₃]⁻ and [CF₃OCFHCF₂SO₃]⁻;
      
      o) a tributyl(tetradecyl)phosphonium cation, or a fluorinated tributyl(tetradecyl)phosphonium cation, and [CF₃HFCCF₂SO₃]⁻ as the anion; and
      
      p) a cation selected from the group consisting of 1,3-dioctylimidazolium, 1-octyl-3-methylimidazolium, fluorinated 1,3-dioctylimidazolium, and fluorinated 1-octyl-3-methylimidazolium ions, and [I]⁻ as the anion.
  - 15. A foam according to claim 1 wherein the anion is selected from the (a) group consisting of aminoacetate, ascorbate, benzoate, catecholate, citrate, formate, fumarate, gallate, glycolate, glyoxylate, iminodiacetate, isobutyrate, kojate, lactate, levulinate, oxalate, pivalate, propionate, pyruvate, salicylate, succinamate, succinate, and tropolonate.
  - 16. A foam according to claim 1 wherein the anion is selected from the group consisting of(d) anions represented by the structure of the following formula:

17. A metastable liquid that comprises a fluorocarbon blowing agent and an ionic compound, wherein the ionic compound comprises an anion selected, from the group consisting of [BF₄]₋
- , [PF₆]⁻, [SbF₆]⁻, [CF₃SO₃]⁻, [HCF₂CF₂SO₃]⁻, [CF₃HFCCF₂SO₃]⁻, [HCClFCF₂SO₃]⁻, [(CF₃SO₂)₂N]⁻, [(CF₃CF₂SO₂)₂N]⁻, [(CF₃SO₂)₃C]⁻, [CF₃CO₂]⁻, [CF₃OCFHCF₂SO₃]⁻, [CF₃CF₂OCFHCF₂SO₃]⁻, [CF₃CFHOCF₂CF₂SO₃]⁻, [CF₂HCF₂OCF₂CF₂SO₃]⁻, [CF₂ICF₂OCF₂CF₂SO₃], [CF₃CF₂OCF₂CF₂SO₃]⁻, [(CF₂HCF₂SO₂)₂N]₋, [(CF₃CFHCF₂SO₂)₂N]⁻, and F⁻.
- View Dependent Claims (18, 19)
- - 18. A liquid according to claim 17 wherein a blowing agent is selected from the group consisting of hydrofluorocarbons and fluoro-olefins.
  - 19. A liquid according to claim 17 wherein a blowing agent is selected from the group consisting of tetrafluoromethane (Freon 14), fluoroform (Freon 23), hexafluoroethane (Freon 116), difluoromethane (HFC-32), 1,1-difluoroethane, 1,1,2,2-tetrafluoroethane (HFC-134), 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1,1-trifluoroethane (HFC-143a), 1,1-difluoroethane (HFC-152a), fluoroethane (HFC-161), pentafluoroethane (HFC-125), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1,1,1,3,3-pentafluorobutane (HFC-365mfc), 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf), and mixtures thereof.

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Current Assignee
Dupont Polymers Inc. (DuPont de Nemours, Inc.)
Original Assignee
E. I. du Pont de Nemours and Company (Corteva, Inc.)
Inventors
Shiflett, Mark Brandon, Yokozeki, Akimichi
Primary Examiner(s)
Saeed, Kamal
Assistant Examiner(s)
Coppins, Janet L

Application Number

US12/974,006
Publication Number

US 20110319633A1
Time in Patent Office

1,505 Days
Field of Search

548/335, 548/146, 548/215, 548/262.2, 548/335.1, 548/356.1, 546/347, 544/139, 544/152, 544/179, 544/180, 544/224, 544/242, 544/336, 562/8, 564/230, 564/281, 564/293
US Class Current

548/335.1
CPC Class Codes

C07D 233/58 with only hydrogen atoms or...

Foamed ionic compounds

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