# US 8,784,686 B2 · Liquids

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- Number: US 8,784,686 B2
- Document ID: US8784686B2
- Status: Granted
- Kind: B2
- Application number: 10/599,694
- Filed: 2005-04-07
- Published: 2007-08-09
- Granted: 2014-07-22
- Earliest claimed: 2004-04-07
- Assignees: Innovia Films Limited
- Applicants: Adam John Walker
- Inventors: Adam John Walker
- Web page: https://patentgrep.com/patent/US8784686B2

## CPC

- C08K 5/3415: Five-membered rings
- B01J 31/003: {containing enzymes}
- B01J 31/0278: {containing nitrogen as cationic centre}
- C07C 215/08: with only one hydroxy group and one amino group bound to the carbon skeleton
- C07C 215/12: the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
- C07C 215/40: with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
- C07C 217/30: having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C08K 5/19: Quaternary ammonium compounds
- C10N 2020/077: {Ionic Liquids}
- Y02P 20/54: using solvents, e.g. supercritical solvents or ionic liquids
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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

### Claim 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.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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.