Method for producing cellulose derivative, and cellulose derivative

Patent metadata

Field	Value
Publication number	US-2016200836-A1
Application number	US-201414910130-A
Country	US
Kind code	A1
Filing date	Aug 11, 2014
Priority date	Aug 23, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

A method for producing a cellulose derivative, including reacting a mixed acid anhydride having two particular types of acyl groups with cellulose in the presence of a base catalyst in an organic solvent having an electron pair-donating property to form a cellulose derivative with the two types of acyl groups derived from the mixed acid anhydride, the acyl groups being introduced at hydroxy groups in the cellulose.

First claim

What is claimed is:

1 . A method for producing a cellulose derivative, comprising reacting a mixed acid anhydride represented by the following chemical formula (A):

wherein R SH represents an organic group having 1 to 3 carbon atom(s); and R LO represents an organic group having an electron-withdrawing property, with cellulose in the presence of a base catalyst in an organic solvent having an electron pair-donating property to form a cellulose derivative with a first acyl group (—COR SH ) and a second acyl group (—COR LO ) introduced at hydroxy groups in the cellulose.

2 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R LO represents an organic group having a higher electron-withdrawing property than that of R SH .

3 . The method for producing a cellulose derivative according to claim 1 , wherein the reaction is performed further in the presence of an acid anhydride represented by (R SH CO) 2 O.

4 . The method for producing a cellulose derivative according to claim 1 , wherein the organic solvent has a donner number (Dn) of 10 or more.

5 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R SH is a group selected from the group consisting of a methyl group, an ethyl group, a propyl group and an isopropyl group.

6 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R SH is a methyl group.

7 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R LO is:
a group comprising at least one divalent group selected from the group consisting of an ether group (—O—), an ester group (—O—CO—), an amide group (—NH—CO—), a urethane group (—NH—CO—O—) and a carbonate group (—O—CO—O—); a first organic group bonding to the carbonyl carbon in the mixed acid anhydride; and a second organic group linked to the first organic group through the divalent group; or an aryl group.

8 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R LO is a group comprising at least one divalent group being an ether group (—O—); a first organic group bonding to the carbonyl carbon in the mixed acid anhydride; and a second organic group linked to the first organic group through the divalent group (—O—).

9 . The method for producing a cellulose derivative according to claim 7 , wherein, the divalent group is bonding to a carbon atom in the first organic group, the carbon atom bonding to the carbonyl carbon in the mixed acid anhydride.

10 . The method for producing a cellulose derivative according to claim 7 , wherein the first organic group is a methylene group.

11 . The method for producing a cellulose derivative according to claim 7 , wherein the second organic group is a hydrocarbon group having 1 to 24 carbon atom(s).

12 . The method for producing a cellulose derivative according to claim 1 , wherein, in the chemical formula (A), R LO is a hydrogenated cardanoxymethyl group represented by —CH 2 —O—C 6 H 4 —(CH 2 ) 14 CH 3 or —CH 2 —O—C 6 H 10 —(CH 2 ) 14 CH 3 .

13 . The method for producing a cellulose derivative according to claim 1 , wherein the base catalyst is a nitrogen-containing basic organic compound having a tertiary amine structure.

14 . The method for producing a cellulose derivative according to claim 1 , wherein the base catalyst is at least one basic compound selected from the group consisting of an amine-based compound, a pyridine-based compound, an imidazole-based compound and an amidine-based compound.

15 . The method for producing a cellulose derivative according to claim 1 , wherein
a degree of substitution with the second acyl group (—COR LO ) is 0.1 or more; and a total degree of substitution with the first acyl group (—COR SH ) and the second acyl group (—COR LO )(DS SH +DS LO ) is 2 or more.

16 . The method for producing a cellulose derivative according to claim 1 , comprising performing an activation treatment before the reaction is performed, wherein the activation treatment comprises a step of soaking the cellulose in an activation solvent.

17 . The method for producing a cellulose derivative according to claim 16 , wherein acetic acid or dimethylsulfoxide is used as the activation solvent.

18 . A cellulose derivative produced by the method for production according to claim 1 .

19 . A cellulose derivative with a first acyl group and a second acyl group introduced at at least some of hydroxy groups contained in cellulose, wherein
the first acyl group is an acyl group having 2 to 4 carbon atoms; and the second acyl group is an acyl group represented by the following chemical formula (B):
—CO—CH 2 —OR  (B)

wherein —OR represents an organic group having 1 to 24 carbon atom(s) other than a cardanoxy group.

20 . The cellulose derivative according to claim 19 , wherein, in the chemical formula (B), R is an aliphatic hydrocarbon group having 1 to 24 carbon atom(s).

21 . The cellulose derivative according to claim 19 , wherein the first acyl group is an acetyl group or a propionyl group.

22 . The cellulose derivative according to claim 19 , wherein
a degree of substitution with the second acyl group (DS LO ) is 0.1 or more; and a total degree of substitution with the first acyl group and the second acyl group (DS SH +DS LO ) is 2 or more.

23 . A cellulose-based resin composition comprising the cellulose derivative according to claim 18 as a base resin.

24 . A molded object obtained by molding the cellulose-based resin composition according to claim 23 .

Assignees

• Nec Corp

Inventors

• Tanaka Shukichi
• Toyama Kiyohiko
• Iji Masatoshi

Classifications

• C08B1/02

  Rendering cellulose suitable for esterification {(esterification per se, C08B3/00, C08B5/00, C08B7/00 or C08B9/00)} · CPC title

• C08B3/16 Primary

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

• C08L1/14

  Mixed esters, e.g. cellulose acetate-butyrate · CPC title