IP Library › Granted Patent US 10,836,923
Granted Patent B2
US 10,836,923 · App. 15/869,224 · Granted Nov 17, 2020

Ionic liquid composition and method for dissolving cellulose using the same

Inventors: Takahiro Aoki (Osaka, JP); Tomoko Kawashima (Osaka, JP); Haruka Kusukame (Kyoto, JP); Yuko Taniike (Osaka, JP)
Assignee: PANASONIC INTELLECTUAL PROPERTY MANAGEMENT CO., LTD.
C09D101/02B05D3/107C07C215/40C07C229/26C07C231/00C08B1/003C08J3/096C08J5/00C08L1/02C09D7/20C08J2301/02
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Quick Facts
Patent No.
US 10,836,923
App. No.
15/869,224
Granted
Nov 17, 2020
Kind
B2
Abstract

The present invention provides an ionic liquid composition containing an ionic liquid and water. The ionic liquid composition does not contain an enzyme capable of hydrolyzing cellulose. The ionic liquid is represented by the following chemical formula (I): [(CH 3 ) 3 N(CH 2 ) 2 OH] + [NH 2 -L-CHNH 2 —COO] − (I); where L is absent or a linker. A molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.87 and not more than 1.14. A weight ratio of the water to the ionic liquid composition is not more than 7.3%. The present invention provides an ionic liquid composition capable of dissolving cellulose without a cellulose-degrading enzyme, namely, an enzyme capable of hydrolyzing cellulose.

Claims (91)

1. A solution in which cellulose has been dissolved in an ionic liquid composition, wherein the ionic liquid composition contains:

an ionic liquid; and

water,

wherein

the ionic liquid composition does not contain an enzyme capable of hydrolyzing cellulose;

the ionic liquid is represented by the following chemical formula (I):

[(CH 3 ) 3 N(CH 2 ) 2 OH] + [NH 2 -L-CHNH 2 —COO] −   (I)

where

L is absent or a linker;

a molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.87 and not more than 1.14; and

a weight ratio of the water to the ionic liquid composition is not more than 7.3%.

2. The solution ionic liquid composition according to claim 1 , wherein

the molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.89 and not more than 1.12.

3. The solution according to claim 1 , wherein

L is —(CH 2 ) n —;

where n is a natural number.

4. The solution according to claim 3 , wherein

n is equal to 3 or 4.

5. The solution according to claim 1 , wherein

the weight ratio of the water to the ionic liquid composition is not less than 1.3%.

6. The solution according to claim 1 , wherein the ionic liquid composition further contains an aprotic polar solvent.

7. The solution according to claim 6 , wherein

the aprotic polar solvent is dimethyl sulfoxide.

8. The solution according to claim 7 , wherein

a weight ratio of the dimethyl sulfoxide to the ionic liquid is not more than 309%.

9. A method for dissolving cellulose, the method comprising:

(a) adding the cellulose to an ionic liquid composition;

wherein

the ionic liquid composition contains an ionic liquid and water;

the ionic liquid composition does not contain an enzyme capable of hydrolyzing cellulose;

the ionic liquid is represented by the following chemical formula (I):

[(CH 3 ) 3 N(CH 2 ) 2 OH] + [NH 2 -L-CHNH 2 —COO] −   (I)

where

L is absent or a linker;

a molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.87 and not more than 1.14; and

a weight ratio of the water to the ionic liquid composition is not more than 7.3%.

10. The method according to claim 9 , wherein

the molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.89 and not more than 1.12.

11. The method according to claim 9 , wherein

L is —(CH 2 ) n —;

where n is a natural number.

12. The method according to claim 11 , wherein

n is equal to 3 or 4.

13. The method according to claim 9 , wherein

the weight ratio of the water to the ionic liquid composition is not less than 1.3%.

14. The method according to claim 9 , wherein the ionic liquid composition further contains

an aprotic polar solvent.

15. The method according to claim 14 , wherein

the aprotic polar solvent is dimethyl sulfoxide.

16. The method according to claim 15 , wherein

a weight ratio of the dimethyl sulfoxide to the ionic liquid is not more than 309%.

17. The method according to claim 9 , further comprising:

(b1) heating the ionic liquid composition to which the cellulose has been added to dissolve the cellulose in the ionic liquid composition after the step (a).

18. The method according to claim 9 , further comprising:

(b2) leaving the ionic liquid composition to which the cellulose has been added at rest to dissolve the cellulose in the ionic liquid composition after the step (a).

19. The method according to claim 9 , further comprising:

(b3) stirring the ionic liquid composition to which the cellulose has been added to dissolve the cellulose in the ionic liquid composition after the step (a).

20. A method for fabricating a cellulose film; the method comprising:

(a) adding cellulose to an ionic liquid composition to prepare a cellulose solution;

(b) applying the cellulose solution on a surface of a substrate to form a film on the surface;

(c) removing the ionic liquid composition from the film using a solvent; and

(d) removing the solvent from the film,

wherein

the ionic liquid composition contains an ionic liquid and water;

the ionic liquid composition does not contain an enzyme capable of hydrolyzing cellulose;

the ionic liquid is represented by the following chemical formula (I):

[(CH 3 ) 3 N(CH 2 ) 2 OH] + [NH 2 -L-CHNH 2 —COO] −   (I)

where

L is absent or a linker;

a molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.87 and not more than 1.14; and

a weight ratio of the water to the ionic liquid composition is not more than 7.3%.

21. The method according to claim 20 , wherein

the molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.89 and not more than 1.12.

22. The method according to claim 20 , wherein

L is —(CH 2 ) n —;

where n is a natural number.

23. The method according to claim 22 , wherein

n is equal to 3 or 4.

24. The method according to claim 20 , wherein

the weight ratio of the water to the ionic liquid composition is not less than 1.3%.

25. The method according to claim 20 , wherein the ionic liquid composition further contains

an aprotic polar solvent.

26. The method according to claim 25 , wherein

the aprotic polar solvent is dimethyl sulfoxide.

27. The method according to claim 26 , wherein

a weight ratio of the dimethyl sulfoxide to the ionic liquid is not more than 309%.

28. A solution in which cellulose has been dissolved in an ionic liquid composition, wherein the ionic liquid is represented by the following chemical formula (I):

[(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] −   (I)

where

L is absent or a linker;

wherein a molar ratio of [(CH 3 ) 3 N(CH 2 ) 2 OH] + to [NH 2 -L-CHNH 2 —COO] − is not less than 0.87 and not more than 1.14.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2018
From: AOKI, TAKAHIRO; KAWASHIMA, TOMOKO; KUSUKAME, HARUKA; TANIIKE, YUKO
To: PANASONIC INTELLECTUAL PROPERTY MANAGEMENT CO., LTD.
Reel/Frame 045263/0823 →
Priority Claims (1)
JP 2017-013884 · Jan 30, 2017 · national
Continuity (1)
Related Publication 20180215942A1 · Aug 2, 2018
Cited By (1)
US 12,338,574