IP Library Granted Patent US 7,601,771
Granted Patent B2
US 7,601,771 · App. 10/519,402 · Granted Oct 13, 2009

Polymer compositions containing polymers and ionic liquids

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Quick Facts
Patent No.
US 7,601,771
App. No.
10/519,402
Granted
Oct 13, 2009
Kind
B2
Abstract

The invention relates to a polymer composition which comprises at least one at least semicrystalline polymer having no ionic groups and comprises at least one compound with plasticizing properties, and which comprises having 0.1 to 30% by weight of ionic liquid as plasticizer, and also to the use of this polymer composition, and a process for its preparation.

Claims (33)

1. A polymer composition, which comprises a polymer component comprising at least one at least semicrystalline polymer having no ionic groups, and 0.1 to 30% by weight of at least one ionic liquid, as plasticizer, wherein the semicrystalline polymer is a thermoplastically processable polymer selected from the group consisting of (co)polyamides, (co)polyesters, polyurethanes, polyphenylene ethers, polyolefins, (co)polyetheramides, polyaramides, polyether(ether)ketones, and polyetheresteramides, and the ionic liquid is a salt having a cation of the following structures:

where R1, R2, R3, R4, R5, and R6 are identical or different, and are hydrogen, a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms, a linear or branched aliphatic hydrocarbon radical having from 2 to 20 carbon atoms and having interruption by one or more heteroatoms (oxygen, NH, NCH 3 ), or are a linear or branched aliphatic hydrocarbon radical having from 2 to 20 carbon atoms and having interruption by one or more functionalities, selected from the group —O—C(O)—, —(O)C—O—, NH—C(O)—, —(O)C—NH, —(CH 3 )N—C(O)—, —(O)C—N(CH 3 )—, —S(O) 2 —O—, —O—S(O) 2 —, —S(O) 2 —NH—, —NH—S(O) 2 —, —S(O) 2 —N(CH 3 )—, —N(CH 3 )—S(O) 2 —,or are a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, terminally functionalized by —OH, —NH 2 , or —N(H)CH 3 , or are a polyether of formula —(R 7 —O) n —R 8 , having block or random structure, where R 7 is a linear or branched hydrocarbon radical having from 2 to 4 carbon atoms, n=from 1 to 30, and R 8 is hydrogen, a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms, or a —C(O)—R 9 radical, where R 9 is a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms; and having an anion selected from the group consisting of halide, phosphate, halophosphates, alkylated phosphates, nitrate, sulfate, hydrogensulfate, alkyl sulfates, aryl sulfates, perfluorinated alkyl sulfates, perfluorinated aryl sulfates, sulfonate, alkylsulfonates, arylsulfonates, perfluorinated alkyl- and arylsulfonates, perchlorate, tetrachloroaluminate, tetrafluoroborate, alkylated borates, tosylate, saccharinate, alkyl carboxylates, and bis(perfluoroalkylsulfonyl)amide anions.

2. The polymer composition as claimed in claim 1 , which comprises 0.5 to 25% by weight of ionic liquid.

3. The polymer composition as claimed in claim 1 , wherein the at least semicrystalline polymer comprises at least one crosslinked, or at least one crosslinkable, polymer selected from the group consisting of (co)polyamides, (co)polyesters, polyurethanes, and polyphenylene ethers.

4. The polymer composition as claimed in claim 1 , wherein the polymer is linear or branched.

5. The polymer composition as claimed in claim 1 , which comprises at least one mixture of said at least semicrystalline polymer.

6. The polymer composition as claimed in claim 1 , wherein the ionic liquid contains a halogen-free anion, selected from the group consisting of phosphate, alkyl phosphates, nitrate, sulfate, alkyl sulfates, aryl sulfates, sulfonate, alkylsulfonates, arylsulfonates, alkyl borates, tosylate, saccharinate, and alkyl carboxylates.

7. The polymer composition as claimed in claim 1 , wherein the ionic liquid of the polymer composition comprises more than one anion.

8. The polymer composition as claimed in claim 1 , which has microbicidal properties.

9. The polymer composition as claimed in claim 1 , which has antistatic properties.

10. The polymer composition as claimed in claim 1 , which has a glass transition temperature, measured by differential scanning calorimetry (DSC), which is lower by up to 18K, than that of the polymer component.

11. A process for preparing the polymer composition as claimed in claim 1 ,

said process comprising

first bringing said ionic liquid into contact with said polymeric component of the polymer composition, and then dispersing the ionic liquid in the polymer composition.

12. The process as claimed in claim 11 , wherein the dispersion of the ionic liquid in the polymer composition takes place by means of a mixing process.

13. The process as claimed in claim 11 , wherein the ionic liquid is brought into contact with, and thoroughly mixed with, a molten phase of the polymeric component.

14. The process as claimed in claim 13 , wherein the mixing of the components of the polymer composition is carried out in a single- or twin-screw kneader, the polymeric component being molten.

15. The process as claimed in claim 11 , wherein the ionic liquid is brought into contact with a solid phase of the polymeric component, and thoroughly mixed after melting.

16. The process as claimed in claim 11 , wherein the dispersion of the ionic liquid in the polymer composition takes place by means of diffusion.

17. The process as claimed in claim 16 , wherein the preparation takes place by means of impregnation of polymer powders by an ionic liquid.

18. The process as claimed in claim 11 , wherein at least one polymer and/or one ionic liquid is dissolved in a solvent.

19. The process as claimed in claim 18 , wherein the solvent is removed by a thermal separation process from a precursor of the polymer composition.

20. The process as claimed in claim 18 , wherein the solvent is removed from a precursor of the polymer composition by precipitation of the polymer composition.

21. A process for preparing a hot-melt adhesive, an adhesion promoter, a binder, a filler material, a packaging material, a compatibilizer for preparing polymer blends, an agent modifying viscosity and/or solubility in polymer mixtures or polymer compositions, an unsupported film, a supported film, a coating, a membrane, or a molding, where shaping takes place by means of injection molding, extrusion, or blow molding,

said process comprising contacting the polymer composition of claim 1 with one or more additives.

22. The polymer composition as claimed in claim 1 , wherein the polymer comprises a homopolyamide.

23. The polymer composition as claimed in claim 1 , wherein the polymer comprises an aromatic polyamide.

24. The polymer composition as claimed in claim 1 , wherein the polymer comprises an aliphatic polyamide and/or copolyamide.

25. The polymer composition as claimed in claim 1 , wherein the polymer comprises a homo- and/or copolyester.

26. The polymer composition as claimed in claim 1 , wherein the polymer comprises a copolyester produced from a hydroxycarboxylic acid and/or from a lactone.

27. A polymer composition, which comprises a polymer component comprising at least one at least semicrystalline polymer having no ionic groups, and 0.1 to 30% by weight of at least one ionic liquid, as plasticizer, wherein the semicrystalline polymer is a thermoplastically processable polymer selected from the group consisting of (co)polyamides, (co)polyesters, polyurethanes, polyphenylene ethers, polyolefins, (co)polyetheramides, polyaramides, and polyetheresteramides, and the ionic liquid is a salt having a cation of the following structures:

where R1, R2, R3, R4, R5, and R6 are identical or different, and are hydrogen, a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms, a linear or branched aliphatic hydrocarbon radical having from 2 to 20 carbon atoms and having interruption by one or more heteroatoms (oxygen, NH, NCH 3 ), or are a linear or branched aliphatic hydrocarbon radical having from 2 to 20 carbon atoms and having interruption by one or more functionalities, selected from the group —O—C(O)—, —(O)C—O—, NH—C(O)—, —(O)C—NH, —(CH 3 )N—C(O)—, —(O)C—N(CH 3 )—, —S(O) 2 —O—,—O—S(O) 2 —,

—S(O) 2 —NH—, —NH—S(O) 2 —, —S(O) 2 —N(CH 3 )—, —N(CH 3 )—S(O) 2 —or are a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, terminally functionalized by —OH, —NH 2 , or —N(H)CH 3 , or are a polyether of formula —(R 7 —O) n —R 8 , having block or random structure, where R 7 is a linear or branched hydrocarbon radical having from 2 to 4 carbon atoms, n=from 1 to 30, and R 8 is hydrogen, a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms, or a —C(O)—R 9 radical, where R 9 is a linear or branched aliphatic hydrocarbon radical having from 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon radical having from 5 to 30 carbon atoms, an aromatic hydrocarbon radical having from 6 to 30 carbon atoms, an alkylaryl radical having from 7 to 40 carbon atoms; and having an anion selected from the group consisting of halide, phosphate, halophosphates, alkylated phosphates, nitrate, sulfate, hydrogensulfate, alkyl sulfates, aryl sulfates, perfluorinated alkyl sulfates, perfluorinated aryl sulfates, sulfonate, alkylsulfonates, arylsulfonates, perfluorinated alkyl- and arylsulfonates, perchlorate, tetrachloroaluminate, tetrafluoroborate, alkylated borates, tosylate, saccharinate, alkyl carboxylates, and bis(perfluoroalkylsulfonyl)amide anions.

Assignments (5)
MERGER Recorded Feb 26, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032335/0326 →
CHANGE OF NAME Recorded Feb 22, 2010
From: GOLDSCHMIDT GMBH
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 024016/0789 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S NAME, PREVIOUSLY RECORDED AT REEL 016965, FRAME 0577. Recorded Jan 19, 2006
From: SCHMIDT, FRIEDRICH-GEORG; PETRAT, FRANK-MARTIN; PAWLIK, ANDREAS; HAEGER, HARALD; WEYERSHAUSEN, BERND
To: CREAVIS GESELLSCHAFT FUER TECHNOLOGIE UND INNOVATION MBH
Reel/Frame 017476/0107 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2005
From: CREAVIS GESELLSCHAFT FUER TECHNOLOGIE UND INNOVATION MBH
To: GOLDSCHMIDT GMBH
Reel/Frame 017116/0594 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2005
From: SCHMIDT, FRIEDRICH GEORG; PETRAT, FRANK-MARTIN; PAWLIK, ANDREAS; HAEGER, HARALD; WEYERSHAUSEN, BERND
To: CREAVIS GELLSCHAFT FUER TECHNOLOGIE UND INNOVATION MBH
Reel/Frame 016965/0577 →