# US 11,897,971 B2 · Modified natural rubber, rubber composition using same, and method for producing modified natural rubber

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- Number: US 11,897,971 B2
- Document ID: US11897971B2
- Status: Granted
- Kind: B2
- Application number: 17/253,292
- Filed: 2019-10-28
- Published: 2021-09-02
- Granted: 2024-02-13
- Earliest claimed: 2018-11-19
- Assignees: Toyo Tire Corporation
- Applicants: Toyo Tire Corporation
- Inventors: Daiki Nakashima; Pranee Phinyocheep
- Web page: https://patentgrep.com/patent/US11897971B2

## CPC

- C08C 19/22: Incorporating nitrogen atoms into the molecule
- B60C 1/0016: {Compositions of the tread}
- B60C 1/0025: {Compositions of the sidewalls}
- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- C08K 3/013: Fillers, pigments or reinforcing additives
- C08K 3/04: Carbon
- C08K 3/36: Silica
- C08K 5/548: containing sulfur {(C08K5/5477 takes precedence)}
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A modified natural rubber includes a linking structure represented by general formula (C), the linking structure having been formed by allowing polyisoprene, having a structure represented by general formula (A) and/or general formula (B), to bind in the structure to an amino compound having two or more primary amino groups. In the formulae (A) and (B), X represents a hydrogen atom or a methyl group, and Ps represent a polyisoprene unit. In the formula (C), W represents a residue of the amino compound from which amino end groups are removed, and Q represents at least one selected from the group consisting of general formulae (Q-1) to (Q-4), and m represents 2 to 4. In the general formulae (Q-1) to (Q-4), *1 indicates binding to a carbon atom of a polyisoprene unit, and *2 indicates binding to a carbon atom of the residue represented by W.

## Claims

### Claim 1

A modified natural rubber comprising a linking structure represented by the following general formula (C), the linking structure having been formed by allowing polyisoprene, having a structure represented by the following general formula (A) and/or general formula (B), to bind in the structure to an amino group of an amino compound having two or more primary amino groups:
wherein X represents a hydrogen atom or a methyl group, and Ps, which may be the same or different from each other, represent a polyisoprene unit;
W-(Q)m (C)
wherein W represents a residue of the amino compound from which amino end groups are removed, and Q represents at least one selected from the group consisting of the following general formulae (Q-1) to (Q-4), and m represents 2 to 4;
wherein *1 indicates binding to a carbon atom of a polyisoprene unit, and *2 indicates binding to a carbon atom of the residue represented by W.

### Claim 2 (depends on 1)

The modified natural rubber according to claim 1, wherein the linking structure represented by the general formula (C) has at least one formula selected from the group consisting of the following general formulae (C-1) to (C-10):

### Claim 3 (depends on 1)

The modified natural rubber according to claim 1,
having a weight average molecular weight of 1,000,000 to 2,000,000.

### Claim 4 (depends on 2)

The modified natural rubber according to claim 2,
having a weight average molecular weight of 1,000,000 to 2,000,000.

### Claim 5 (depends on 1)

A rubber composition comprising: a rubber component containing the modified natural rubber according to claim 1 in an amount of 10 to 100 parts by mass per 100 parts by mass of the rubber component; and an inorganic filler in an amount of 10 to 150 parts by mass per 100 parts by mass of the rubber component.

### Claim 6 (depends on 2)

A rubber composition comprising: a rubber component containing the modified natural rubber according to claim 2 in an amount of 10 to 100 parts by mass per 100 parts by mass of the rubber component; and an inorganic filler in an amount of 10 to 150 parts by mass per 100 parts by mass of the rubber component.

### Claim 7 (depends on 3)

A rubber composition comprising: a rubber component containing the modified natural rubber according to claim 3 in an amount of 10 to 100 parts by mass per 100 parts by mass of the rubber component; and an inorganic filler in an amount of 10 to 150 parts by mass per 100 parts by mass of the rubber component.

### Claim 8 (depends on 4)

A rubber composition comprising: a rubber component containing the modified natural rubber according to claim 4 in an amount of 10 to 100 parts by mass per 100 parts by mass of the rubber component; and an inorganic filler in an amount of 10 to 150 parts by mass per 100 parts by mass of the rubber component.

### Claim 9 (depends on 5)

A pneumatic tire produced using the rubber composition according to claim 5.

### Claim 10 (depends on 6)

A pneumatic tire produced using the rubber composition according to claim 6.

### Claim 11 (depends on 7)

A pneumatic tire produced using the rubber composition according to claim 7.

### Claim 12 (depends on 8)

A pneumatic tire produced using the rubber composition according to claim 8.