Cellulose resin and method for producing the same

Patent metadata

Field	Value
Publication number	US-9512238-B2
Application number	US-201414541943-A
Country	US
Kind code	B2
Filing date	Nov 14, 2014
Priority date	Oct 5, 2009
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

A cellulose resin produced by binding cardanol or a derivative thereof to cellulose or a derivative thereof with the use of a cellulose hydroxy group of the cellulose or a derivative thereof and the phenolic hydroxy group of the cardanol or a derivative thereof.

First claim

The invention claimed is:

1. A method for producing a cellulose resin, comprising:
reacting a multifunctional compound comprising a first functional group capable of reacting with a hydroxy group of cellulose and a second functional group capable of reacting with a phenolic hydroxy group of cardanol, with cardanol to form a cardanol derivative, by reacting the second functional group with the phenolic hydroxy group; and
reacting the first functional group derived from the multifunctional compound of the cardanol derivative with a hydroxy group of cellulose or a derivative thereof to bind the cardanol derivative to the cellulose or a derivative thereof,
wherein a cellulose carbon atom to which the cellulose hydroxy group is bound and a cardanol carbon atom to which the phenolic hydroxy group is bound are linked via an organic linking group,
the organic linking group comprises:
a first bond binding to the cellulose carbon atom wherein the first bond is one of an ester bond, an ether bond and a urethane bond, and
a second bond binding to the cardanol carbon atom wherein the second bond is one of an ester bond, an ether bond, and a urethane bond,
wherein when the first bond is an ester bond or a urethane bond, then the second bond is an ester bond, an ether bond, or a urethane bond, and
wherein when the first bond is an ether bond, then the second bond is an ester bond or a urethane bond; and
at least one acyl group selected from a group consisting of an acetyl group, a propionyl group and a butyryl group is added to a cellulose hydroxy group of the cellulose or a derivative thereof.

2. The method for producing a cellulose resin according to claim 1 , wherein the multifunctional compound comprises a hydrocarbon group having 1 to 20 carbon atoms.

3. The method for producing a cellulose resin according to claim 1 , wherein the multifunctional compound comprises a functional group selected from the group consisting of a carboxyl group, a carboxylic halide group, a carboxylic acid anhydride group, an epoxy group, an isocyanate group and a halogen group.

4. The method for producing a cellulose resin according to claim 1 , wherein the multifunctional compound comprises a functional group selected from the group consisting of a carboxyl group, a carboxylic acid anhydride group and a halogen group.

5. The method for producing a cellulose resin according to claim 1 , wherein the multifunctional compound is a compound comprising a carboxylic acid anhydride group, or a compound comprising a carboxyl group and a halogen group.

6. The method for producing a cellulose resin according to claim 1 , wherein:
the multifunctional compound comprises a carboxyl group or a carboxylic acid anhydride group, and
the process further comprises converting a carboxyl group of the cardanol derivative into a carboxylic halide group, after forming the cardanol derivative.

7. The method for producing a cellulose resin according to claim 1 , further comprising hydrogenating an unsaturated bond of the cardanol or a derivative thereof.

8. The method for producing a cellulose resin according to claim 1 , wherein a reactive hydrocarbon compound comprising a functional group capable of reacting with the cellulose hydroxy group is reacted with the cellulose or a derivative thereof, simultaneously or separately with the cardanol derivative, to bind the reactive hydrocarbon compound to the cellulose or a derivative thereof.

9. The method for producing a cellulose resin according to claim 8 , wherein the reactive hydrocarbon compound is a hydrocarbon compound comprising a carboxyl group, a carboxylic halide group or a carboxylic acid anhydride group.

10. The method for producing a cellulose resin according to claim 8 , wherein the reactive hydrocarbon compound is at least one monocarboxylic acid, an acid halide thereof or acid anhydride thereof, the monocarboxylic acid being selected from an aliphatic carboxylic acid, an aromatic carboxylic acid and an alicyclic carboxylic acid.

11. The method according to claim 1 , wherein the first bond is an ester bond and the second bond is an ester bond or an ether bond.

12. The method according to claim 1 , wherein the organic linking group comprises a divalent hydrocarbon group having 1 to 20 carbon atoms.

13. The method according to claim 12 , wherein:
the cellulose carbon atom and the hydrocarbon group are bound via an ester bond as the first bond, and
the cardanol carbon atom and the hydrocarbon group are bound via an ester bond or an ether bond as the second bond.

14. The method according to claim 1 , wherein a number of the cardanol molecules or a derivative thereof added to the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS CD , is 0.1 or more.

15. The method according to claim 1 , wherein a number of the acyl groups added to a cellulose hydroxy group of the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS AC , is 0.5 or more.

16. The method according to claim 1 , wherein a number of the acyl groups added to a cellulose hydroxy group of the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS AC , is 0.5 or more and 2.7 or less.

17. The method according to claim 1 , wherein a number of remaining cellulose hydroxy groups per glucose unit, the number being abbreviated as DS OH , is 0.9 or less.

18. The method according to claim 1 , wherein a sum of the cellulose component and the cardanol component is 50% by mass or more, based on the total amount of the resin.

Assignees

• Iji Masatoshi
• Moon Sungil
• Tanaka Shukichi
• Kai Hiroyuki
• Nec Corp

Inventors

• Iji Masatoshi
• Moon Sungil
• Tanaka Shukichi
• Kai Hiroyuki

Classifications

• C08B13/00

  Preparation of cellulose ether-esters · CPC title

• C08B3/10 Primary

  with five or more carbon-atoms, {e.g. valerate} · CPC title

• C08B3/16

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

• C08B3/22 Primary

  Post-esterification treatments, including purification · CPC title

• C08L1/00

  Compositions of cellulose, modified cellulose or cellulose derivatives · CPC title