IP Library Granted Patent US 8,784,686
Granted Patent B2
US 8,784,686 · App. 10/599,694 · Granted Jul 22, 2014

Liquids

Inventor: Adam John Walker (Lincolnshire, GB)
Assignee: Innovia Films Limited
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Quick Facts
Patent No.
US 8,784,686
App. No.
10/599,694
Granted
Jul 22, 2014
Kind
B2
Abstract

The present invention relates to ionic liquid comprising an anion and a cation wherein the cation is a primary, secondary or tertiary ammonium ion containing a protonated nitrogen atom.

Claims (95)

1. A process for dissolving a polymeric material, the process comprising contacting the polymeric material with an ionic liquid,

the ionic liquid comprising an anion and a cation wherein the cation is a tertiary ammonium ion of the formula (I)

N+HRR′R″  (I)

wherein:

R is an alkyl group substituted with one or more hydroxy groups;

R′ and R″ are independently alkyl or substituted alkyl groups optionally substituted with one or more substituents selected from the group consisting of a nitrogen-containing functional group, an alkoxy group, and a hydroxy group; the nitrogen-containing functional group selected from the group consisting of nitrile, nitro, and amino; the substituted alkyl optionally comprising one or more ether linkages; and

the anion is selected from the group consisting of a nitrate, sulphate, phosphate, carbonate, sulphonate, and carboxylate.

2. The process of claim 1 , wherein the ionic liquid has a melting point below 25° C., a viscosity of less than 500 centipoise, and contains less than 1% water.

3. The process of claim 1 , wherein R of the ionic liquid is a hydroxyalkyl having 1, 2, 3, 4, 5 or 6 C atoms.

4. The process of claim 3 , wherein the hydroxyalkyl has a hydroxyl moiety on its free, terminal carbon.

5. The process of claim 1 , wherein the cation of the ionic liquid is selected from the group consisting of an N,N-dimethylethanolammonium ion, a triethanolammoniumion ion, and an N-butyldiethanolammonium ion.

6. The process of claim 1 , wherein the anion of the ionic liquid is selected from the group consisting of bis(trifluoromethylsulphonyl)imide, formate, butanoate, pentanoate, hexanoate, heptanoate, octanoate, nonanoate, decanoate, glycolate, crotonate, pyruvate, succinate, and phenylacetate.

7. The process of claim 1 , wherein the ionic liquid is selected from the group consisting of:

N-butyldiethanolammonium formate;

N-butyldiethanolammonium acetate;

N-butyldiethanolammonium propanoate;

N-butyldiethanolammonium butanoate;

N-butyldiethanolammonium pentanoate;

N-butyldiethanolammonium hexanoate;

N-butyldiethanolammonium heptanoate;

N-butyldiethanolammonium octanoate;

N-butyldiethanolammonium nonanoate;

N-butyldiethanolammonium decanoate;

N-butyldiethanolammonium benzoate;

N-butyldiethanolammonium benezenedicarboxylate;

N-butyldiethanolammonium benzenetricarboxylate;

N-butyldiethanolammonium benzenetetracarboxylate;

N-butyldiethanolammonium chlorobenzoate;

N-butyldiethanolammonium fluorobenzoate;

N-butyldiethanolammonium pentachlorobenzoate;

N-butyldiethanolammonium pentafluorobenzoate;

N-butyldiethanolammonium glycolate;

N-butyldiethanolammonium pantothenate;

N-butyldiethanolammonium mandelate;

N-butyldiethanolammonium crotonate;

N-butyldiethanolammonium malate;

N-butyldiethanolammonium pyruvate;

N-butyldiethanolammonium succinate;

N-butyldiethanolammonium citrate;

N-butyldiethanolammonium phenylacetate;

N-butyldiethanolammonium oxalate;

N-butyldiethanolammonium bis(trifluoromethylsulphonyl)imide;

N-butyldiethanolammonium carbonate;

N-butyldiethanolammonium hydrogen carbonate;

N-butyldiethanolammonium sulphate;

N-butyldiethanolammonium hydrogen sulphate;

N-butyldiethanolammonium methanesulphonate;

N-butyldiethanolammonium trifluoromethanesulphonate;

N-butyldiethanolammonium ethylenediaminetetraacetate;

N-butyldiethanolammonium hexafluorophosphate;

N-butyldiethanolammonium tetrafluoroborate;

N-butyldiethanolammonium trifluoroacetate;

N-butyldiethanolammonium pentafluoropropanoate;

N-butyldiethanolammonium heptafluorobutanoate;

N,N-dimethylethanolammonium formate;

N,N-dimethylethanolammonium acetate;

N,N-dimethylethanolammonium propanoate;

N,N-dimethylethanolammonium butanoate;

N,N-dimethylethanolammonium pentanoate;

N,N-dimethylethanolammonium hexanoate;

N,N-dimethylethanolammonium heptanoate;

N,N-dimethylethanolammonium octanoate;

N,N-dimethylethanolammonium nonanoate;

N,N-dimethylethanolammonium decanoate;

N,N-dimethylethanolammonium benzoate;

N,N-dimethylethanolammonium benezenedicarboxylate;

N,N-dimethylethanolammonium benzenetricarboxylate;

N,N-dimethylethanolammonium benzenetetracarboxylate;

N,N-dimethylethanolammonium chlorobenzoate;

N,N-dimethylethanolammonium fluorobenzoate;

N,N-dimethylethanolammonium pentachlorobenzoate;

N,N-dimethylethanolammonium pentafluorobenzoate;

N,N-dimethylethanolammonium glycolate;

N,N-dimethylethanolammonium pantothenate;

N,N-dimethylethanolammonium mandelate;

N,N-dimethylethanolammonium crotonate;

N,N-dimethylethanolammonium malate;

N,N-dimethylethanolammonium pyruvate;

N,N-dimethylethanolammonium succinate;

N,N-dimethylethanolammonium citrate;

N,N-dimethylethanolammonium phenylacetate;

N,N-dimethylethanolammonium oxalate;

N,N-dimethylethanolammonium bis(trifluoromethylsulphonyl)imide;

N,N-dimethylethanolammonium carbonate;

N,N-dimethylethanolammonium hydrogen carbonate;

N,N-dimethylethanolammonium sulphate;

N,N-dimethylethanolammonium hydrogen sulphate;

N,N-dimethylethanolammonium methanesulphonate;

N,N-dimethylethanolammonium trifluoromethanesulphonate;

N,N-dimethylethanolammonium ethylenediaminetetraacetate;

N,N-dimethylethanolammonium hexafluorophosphate;

N,N-dimethylethanolammonium tetrafluoroborate;

N,N-dimethylethanolammonium trifluoroacetate;

N,N-dimethylethanolammonium pentafluoropropanoate; and

N,N-dimethylethanolammonium heptafluorobutanoate.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2019
From: INNOVIA FILMS LIMITED
To: FUTAMURA CHEMICAL UK LIMITED
Reel/Frame 049952/0027 →
CHANGE OF NAME Recorded Aug 4, 2019
From: WORN AGAIN FOOTWEAR AND ACCESSORIES LIMITED
To: WORN AGAIN TECHNOLOGIES LIMITED
Reel/Frame 049952/0297 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2019
From: INNOVIA FILMS LTD; FUTAMURA CHEMICAL UK LTD.
To: WORN AGAIN FOOTWEAR AND ACCESSORIES LTD.
Reel/Frame 049952/0302 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2013
From: THE UNIVERSITY OF YORK
To: INNOVIA FILMS LIMITED
Reel/Frame 030821/0317 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2007
From: WALKER, ADAM JOHN
To: THE UNIVERSITY OF YORK
Reel/Frame 018724/0741 →
Priority Claims (1)
GB 0407908.3 · Apr 7, 2004 · national
Continuity (1)
Related Publication 20070185330A1 · Aug 9, 2007