Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom

Patent metadata

Field	Value
Publication number	US-9834516-B2
Application number	US-53980009-A
Country	US
Kind code	B2
Filing date	Aug 12, 2009
Priority date	Feb 14, 2007
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

This invention relates to novel compositions comprising regioselectively substituted cellulose esters. One aspect of the invention relates to processes for preparing regioselectively substituted cellulose esters from cellulose dissolved in ionic liquids. Another aspect of the invention relates to the utility of regioselectively substituted cellulose esters in applications such as protective and compensation films for liquid crystalline displays.

First claim

That which is claimed is:

1. A compensation film comprising at least one regioselectively substituted cellulose ester having a RDS ratio of C 6 >C 2 >C 3 ; wherein said regioselectively substituted cellulose ester is a mixed cellulose ester having at least two different acyl substituents; wherein said regioselectively substituted cellulose ester has a carbonyl RDS ratio of at least one acyl substituent for C 5 /C 3 or C 6 /C 2 of at least 1.3; wherein said compensation film comprises at least one of the following characteristics:
(i) an R th range from about −380 to about −110 nm,
(ii) an R th range from about −160 to about 0 nm, or
(iii) said regioselectively substituted cellulose ester comprises a regioselectively substituted cellulose benzoate propionate.

2. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS from about 1.5 to about 2.95 of a single acyl substituent.

3. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS from about 1.6 to about 2.9.

4. The compensation film according to claim 1 wherein said compensation film has R th values from about −380 to about −110 nm and said regioselectively substituted cellulose ester has a total DS of about 1.7 to about 2.5.

5. The compensation film according to claim 1 wherein said compensation film has R th values from about −380 to about −110 nm and said regioselectively substituted cellulose ester has a total DS of about 1.7 to about 2.5 and a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05.

6. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS of about 2.6 to about 2.9.

7. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS of about 2.6 to about 2.9 and a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05.

8. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS of about 2.75 to about 2.9.

9. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester has a total DS of about 2.75 to about 2.9 and a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05.

10. The compensation film according to claim 1 wherein said has a total DS from about 1.5 to about 3.0.

11. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester is selected from the group consisting of cellulose benzoate propionate or cellulose benzoate butyrate; wherein said regioselectively substituted cellulose ester has total DS from about 2.0 to about 3.0.

12. The compensation film according to claim 1 wherein said compensation film has a R th range from about −160 to about 0 nm and said regioselectively substituted cellulose ester comprises a regioselectively substituted cellulose acetate propionate having a total DS of about 2.0 to about 3.0, a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05, and a carbonyl RDS ratio for at least one acyl substituent for C 6 /C 3 or C 6 /C 2 of at least about 1.3.

13. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester comprises a regioselectively substituted cellulose benzoate propionate having a total DS of about 2.0 to about 3.0, a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05, and a carbonyl RDS ratio for at least one acyl substituent for C 6 /C 3 or C 6 /C 2 of at least about 1.3.

14. The compensation film according to claim 1 wherein said regioselectively substituted cellulose ester comprises a regioselectively substituted cellulose benzoate propionate having a total DS of about 2.0 to about 3.0, a ring RDS ratio for C 6 /C 3 or C 6 /C 2 of at least 1.05, a carbonyl RDS ratio for at least one acyl substituent for C 6 /C 3 or C 6 /C 2 of at least about 1.3, and the benzoate substituent is located primarily at C 2 or C 3 .

15. The compensation film according to claim 1 wherein the product of the carbonyl RDS ratio for C 6 /C 3 or C 6 /C 2 times the DS of the acyl substituent for said regioselectively substituted cellulose ester is at least 2.5.

16. The compensation film according to claim 1 wherein the carbonyl RDS ratio of at least one acyl substituent for C 6 /C 3 or C 6 /C 2 for said regioselectively substituted cellulose ester is at least 1.3 and the product of the carbonyl RDS ratio for C 6 /C 3 or C 6 /C 2 times the acyl DS for said regioselectively substituted cellulose ester is at least 2.3.

17. A compensation film comprising at least one regioselectively substituted cellulose ester having a RDS ratio of C 6 >C 2 >C 3 ; wherein said compensation film has an R th range from about −400 to about +270 nm; wherein said regioselectively substituted cellulose ester comprises cellulose benzoate propionate or cellulose benzoate butyrate; wherein said regioselectively substituted cellulose ester has a carbonyl RDS ratio of at least one acyl substituent for C 6 /C 3 or C 6 /C 2 of at least 1.3.

18. The compensation film according to claim 17 wherein said compensation film has a R th range from about −380 to about −110 nm.

19. The compensation film according to claim 17 wherein said compensation film has a R th range from about +100 to about +270 nm.

20. The compensation film according to claim 17 wherein said regioselectively substituted cellulose ester comprises cellulose benzoate propionate.

Assignees

• Buchanan Charles Michael
• Buchanan Norma Lindsey
• Hembre Robert Thomas
• Lambert Juanelle Little
• Donelson Michael Eugene
• Gorbunova Maryna Grigorievna
• Kuo Thauming
• Wang Bin
• Eastman Chem Co

Inventors

• Buchanan Charles Michael
• Buchanan Norma Lindsey
• Hembre Robert Thomas
• Lambert Juanelle Little
• Donelson Michael Eugene
• Gorbunova Maryna Grigorievna
• Kuo Thauming
• Wang Bin

Classifications

• G02B1/14

  Protective coatings, e.g. hard coatings · CPC title

• C08B3/28

  by precipitation · CPC title

• C08B3/16

  Preparation of mixed organic cellulose esters {, e.g. cellulose aceto-formate or cellulose aceto-propionate} · CPC title

• C08B3/06 Primary

  Cellulose acetate {, e.g. mono-acetate, di-acetate or tri-acetate} · CPC title

• C07D233/54 Primary

  having two double bonds between ring members or between ring members and non-ring members · CPC title