Composite particles for toner additives
US-2024417537-A1 · Dec 19, 2024 · US
US9487646B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9487646-B2 |
| Application number | US-201113813608-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 6, 2011 |
| Priority date | Aug 6, 2010 |
| Publication date | Nov 8, 2016 |
| Grant date | Nov 8, 2016 |
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A cellulose resin composition containing a cellulose resin produced by binding a cardanol or a derivative thereof to cellulose or a derivative thereof, and a cardanol-modified silicone compound produced by binding cardanol or a derivative thereof to a silicone compound.
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The invention claimed is: 1. A cellulose resin composition comprising: a cellulose resin produced by binding cardanol or a derivative thereof to cellulose or a derivative thereof; and a cardanol-modified silicone compound produced by binding cardanol or a derivative thereof to a silicone compound. 2. The cellulose resin composition according to claim 1 , wherein the silicone compound comprises a functional group, and the cardanol-modified silicone compound is a compound produced by binding the cardanol or a derivative thereof to the silicone compound by use of the functional group of the silicone compound and a phenolic hydroxy group of the cardanol or a derivative thereof. 3. The cellulose resin composition according to claim 2 , wherein the functional group of the silicone compound is selected from the group consisting of an epoxy group, an amino group, a hydroxy group and a carboxyl group. 4. The cellulose resin composition according to claim 3 , wherein in the cardanol-modified silicone compound, a silicon atom to which a group having the functional group is bound and a cardanol carbon atom to which the phenolic hydroxy group is bound are linked via an organic linking group, and the organic linking group comprises a first bond selected from the group consisting of an amide bond, an ester bond, an ether bond and a urethane bond on a side of the silicon atom, and a second bond selected from the group consisting of an ester bond, an ether bond and a urethane bond on a side of the cardanol carbon atom. 5. The cellulose resin composition according to claim 4 , wherein the organic linking group of the cardanol-modified silicone compound comprising the first and second groups further comprises a divalent hydrocarbon group having 1 to 20 carbon atoms. 6. The cellulose resin composition according to claim 1 , wherein a content of the cardanol-modified silicone compound is 1% by mass or more and 20% by mass or less, based on the total amount of the cardanol-modified silicone compound and the cellulose resin. 7. The cellulose resin composition according to claim 1 , wherein the cardanol or a derivative thereof is bound to the cellulose or a derivative thereof by a connection between a hydroxy group of the cellulose or a derivative thereof and a phenolic hydroxy group of the cardanol or a derivative thereof. 8. The cellulose resin composition according to claim 7 , wherein in the cellulose resin, a cellulose carbon atom to which the hydroxy group is bound and a cardanol carbon atom to which the phenolic hydroxy group is bound are linked via an organic linking group, and the organic linking group comprises a first bond binding to the cellulose carbon atom, the first bonding being selected from the group consisting of an ester bond, an ether bond and a urethane bond, and a second bond binding to the cardanol carbon atom, the second bond being selected from the group consisting of an ester bond, an ether bond and a urethane bond. 9. The cellulose resin composition according to claim 8 , wherein the organic linking group of the cellulose resin further comprises a divalent hydrocarbon group having 1 to 20 carbon atoms. 10. The cellulose resin composition according to claim 1 , wherein in the cellulose resin, a number of molecules of the cardanol 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. 11. The cellulose resin composition according to claim 1 , adding a reactive hydrocarbon compound, comprising a functional group capable of reacting with the hydroxy group, to a hydroxy group of the cellulose or a derivative thereof. 12. The cellulose resin composition according to claim 11 , wherein the reactive hydrocarbon compound is a hydrocarbon compound comprising a carboxyl group, a carboxylic halide group or a carboxylic acid anhydride group. 13. The cellulose resin composition according to claim 11 , wherein the reactive hydrocarbon compound comprises at least one monocarboxylic acid, an acid halide thereof or acid anhydride thereof, the monocarboxylic acid being selected from the group consisting of an aliphatic carboxylic acid, an aromatic carboxylic acid and an alicyclic carboxylic acid. 14. The cellulose resin composition according to claim 11 , wherein in the cellulose resin, a number of molecules of the reactive hydrocarbon compound added to the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS XX , is 0.1 or more. 15. The cellulose resin composition according to claim 1 , wherein in the cellulose resin, at least one acyl group selected from the group consisting of an acetyl group, a propionyl group and a butyryl group is added to a cellulose hydroxy group. 16. The cellulose resin composition according to claim 1 , wherein in the cellulose resin, at least one first acyl group selected from the group consisting of an acetyl group, a propionyl group and a butyryl group is added to a cellulose hydroxy group, and a second acyl group derived from at least one monocarboxylic acid selected from the group consisting of an aromatic carboxylic acid and an alicyclic carboxylic acid is added to another cellulose hydroxy group. 17. The cellulose resin composition according to claim 1 , wherein in the cellulose resin, a number of remaining hydroxy groups per glucose unit, the number being abbreviated as DS OH , is 0.9 or less. 18. The cellulose resin composition according to claim 1 , wherein a plant component ratio of the cellulose resin is 50% by mass or more, the ratio being defined as a ratio of a sum of cellulose moiety and cardanol moiety based on the cellulose resin. 19. The cellulose resin composition according to claim 1 , wherein an unsaturated bond of the cardanol or a derivative thereof is hydrogenated. 20. A molding material comprising the resin composition as recited in claim 1 . 21. The cellulose resin composition according to claim 16 , wherein a number of the second acyl groups added to the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS XX , is 0.1 or more. 22. The cellulose resin composition according to claim 1 , wherein in the cellulose resin, a number of molecules of the cardanol or a derivative thereof added to the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS CD , is 0.2 or more and 1.5 or less. 23. The cellulose resin composition according to claim 11 , wherein in the cellulose resin, a number of molecules of the reactive hydrocarbon compound added to the cellulose or a derivative thereof per glucose unit, the number being abbreviated as DS XX , is 0.1 or more and 0.6 or less. 24. The cellulose resin composition according to claim 15 , wherein in the cellulose resin, a number of the acyl group per glucose unit, the number being abbreviated as DS AC , is 0.5 or more and 2.7 or less. 25. The cellulose resin composition according to claim 15 , wherein in the cellulose resin, a number of the acyl group per glucose unit, the number being abbreviated as DS AC , is 0.5 or more and 2.5 or less. 26. The cellulose resin composition according to claim 4 , wherein the organic linking group of the cardanol-modified silicone compound further comprises a divalent hydrocarbon group having 1 to 8 carbon atoms. 27. The cellulose resin composition according to claim 8 , wherein the organic lin
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