# US 9,039,826 B2 · Cardanol-modified silane coupling agent, cardanol-modified filler, and cellulose resin composition

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- Number: US 9,039,826 B2
- Document ID: US9039826B2
- Status: Granted
- Kind: B2
- Application number: 13/583,569
- Filed: 2010-12-03
- Published: 2013-02-14
- Granted: 2015-05-26
- Earliest claimed: 2010-03-11
- Assignees: NEC Corporation
- Applicants: Shukichi Tanaka; Masatoshi Iji
- Inventors: Shukichi Tanaka; Masatoshi Iji
- Web page: https://patentgrep.com/patent/US9039826B2

## CPC

- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C08K 5/54: Silicon-containing compounds {(C08K5/0091 takes precedence)}
- C08K 5/5435: containing oxygen in a ring
- C08K 5/5455: containing at least one [IMAGE cpc-sch-C08K-1012.gif] group
- C08K 9/06: with silicon-containing compounds
- C08L 1/02: Cellulose; Modified cellulose
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

An exemplary embodiment provides a cardanol-modified silane coupling agent, which can improve strength and toughness by improving adhesion at an interface between a filler and a cellulose resin when being used as a surface-treatment agent, a resin additive, or the like; a cardanol-modified filler subjected to a surface treatment with the cardanol-modified silane coupling agent; and a cellulose resin composition having excellent toughness. More specifically, the exemplary embodiment provides a cardanol-modified silane coupling agent obtained by reacting cardanol or a derivative thereof with an epoxy silane coupling agent or an isocyanate silane coupling agent; a cardanol-modified filler obtained by subjecting a filler to a surface treatment with the cardanol-modified silane coupling agent; a cellulose resin composition comprising the cardanol-modified filler and a cellulose resin; and a cellulose resin composition comprising the cardanol-modified silane coupling agent, a filler and a cellulose resin.

## Claims

### Claim 1

A cardanol-modified silane coupling agent (C) obtained by reacting cardanol or a derivative thereof (A) with an epoxy silane coupling agent or an isocyanate silane coupling agent (B).

### Claim 2 (depends on 1)

A cardanol-modified filler (D), in which a filler (D0) is subjected to a surface treatment with the cardanol-modified silane coupling agent (C) according to claim 1.

### Claim 3 (depends on 2)

The cardanol-modified filler (D) according to claim 2, wherein the filler (D0) is a glass fiber.

### Claim 4 (depends on 3)

A cellulose resin composition comprising:
the cardanol-modified filler (D) according to claim 3 and
a cellulose resin (E0).

### Claim 5 (depends on 2)

A cellulose resin composition comprising:
the cardanol-modified filler (D) according to claim 2, and
a cellulose resin (E0).

### Claim 6 (depends on 5)

The cellulose resin composition according to claim 5, wherein the cellulose resin (E0) is a cellulose resin (E) in which cellulose or a derivative thereof (F) is bonded to cardanol or a derivative thereof (G) using a cellulose hydroxyl group in the cellulose or the derivative thereof (F) and a phenolic hydroxyl group in the cardanol or the derivative thereof (G).

### Claim 7 (depends on 6)

The cellulose resin composition according to claim 6, wherein in the cellulose resin (E), a cellulose carbon atom to which the cellulose hydroxyl group in the cellulose or the derivative thereof (F) is bonded is linked to a cardanol carbon atom to which the phenolic hydroxyl group in the cardanol or the derivative thereof (G) is bonded via an organic linking group containing a divalent hydrocarbon group.

### Claim 8 (depends on 7)

The cellulose resin composition according to claim 7, wherein in the cellulose resin (E), the cellulose carbon atom is bonded to the divalent hydrocarbon group via any one of an ester bond, an ether bond and a urethane bond; and the cardanol hydrocarbon atom is bonded to the divalent hydrocarbon group via any one of an ester bond, an ether bond and a urethane bond.

### Claim 9 (depends on 8)

The cellulose resin composition according to claim 8, wherein in the cellulose resin (E), a degree of substitution of the cardanol or the derivative thereof (G) per a glucose unit in the cellulose or the derivative thereof (F) is 0.1 or higher.

### Claim 10 (depends on 7)

The cellulose resin composition according to claim 7, wherein in the cellulose resin (E), a degree of substitution of the cardanol or the derivative thereof (G) per a glucose unit in the cellulose or the derivative thereof (F) is 0.1 or higher.

### Claim 11

The cellulose resin composition according to 7, wherein in the cellulose resin (E), an unsaturated bond in the cardanol or the derivative thereof (G) is converted into a saturated bond.

### Claim 12 (depends on 6)

The cellulose resin composition according to claim 6, wherein in the cellulose resin (E), a degree of substitution of the cardanol or the derivative thereof (G) per a glucose unit in the cellulose or the derivative thereof (F) is 0.1 or higher.

### Claim 13 (depends on 6)

The cellulose resin composition according to claim 6, wherein in the cellulose resin (E), an unsaturated bond in the cardanol or the derivative thereof (G) is converted into a saturated bond.

### Claim 14 (depends on 1)

A cellulose resin composition comprising:
the cardanol-modified silane coupling agent (C) according to claim 1,
a filler (D0), and
a cellulose resin (E0).

### Claim 15 (depends on 14)

The cellulose resin composition according to claim 14, wherein the cellulose resin (E0) is a cellulose resin (E) in which cellulose or a derivative thereof (F) is bonded to cardanol or a derivative thereof (G) using a cellulose hydroxyl group in the cellulose or the derivative thereof (F) and a phenolic hydroxyl group in the cardanol or the derivative thereof (G).

### Claim 16 (depends on 15)

The cellulose resin composition according to claim 15, wherein in the cellulose resin (E), a cellulose carbon atom to which the cellulose hydroxyl group in the cellulose or the derivative thereof (F) is bonded is linked to a cardanol carbon atom to which the phenolic hydroxyl group in the cardanol or the derivative thereof (G) is bonded via an organic linking group containing a divalent hydrocarbon group.

### Claim 17 (depends on 16)

The cellulose resin composition according to claim 16, wherein in the cellulose resin (E), the cellulose carbon atom is bonded to the divalent hydrocarbon group via any one of an ester bond, an ether bond and a urethane bond; and the cardanol hydrocarbon atom is bonded to the divalent hydrocarbon group via any one of an ester bond, an ether bond and a urethane bond.

### Claim 18 (depends on 15)

The cellulose resin composition according to claim 15, wherein in the cellulose resin (E), a degree of substitution of the cardanol or the derivative thereof (G) per a glucose unit in the cellulose or the derivative thereof (F) is 0.1 or higher.

### Claim 19 (depends on 15)

The cellulose resin composition according to claim 15, wherein in the cellulose resin (E), an unsaturated bond in the cardanol or the derivative thereof (G) is converted into a saturated bond.

### Claim 20 (depends on 4)

The cardanol-modified filler (D) according to claim 4, wherein the filler (D0) is a glass fiber.
