# US 7,745,523 B1 · Coupling compounds and their uses in rubber compositions and tires

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- Number: US 7,745,523 B1
- Document ID: US7745523B1
- Status: Granted
- Kind: B1
- Application number: 12/329,885
- Filed: 2008-12-08
- Published: 2010-06-10
- Granted: 2010-06-29
- Earliest claimed: 2008-12-08
- Assignees: The Goodyear Tire & Rubber Company
- Inventors: Robert Alan Woloszynek
- Web page: https://patentgrep.com/patent/US7745523B1

## CPC

- C07F 5/025: {Boronic and borinic acid compounds}
- B60C 1/0016: {Compositions of the tread}
- C08K 3/013: Fillers, pigments or reinforcing additives
- C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B60C: VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The invention includes coupling compounds, rubber compositions, and tires. The coupling compounds can, for example, be used to couple to silica filler. Rubber compositions can comprise the coupling compound and polymers. Polymers can be homopolymers, copolymers and terpolymers, and can include repeat units provided from conjugated diene monomers. Tires and various parts of tires can be made from those rubber compositions.

## Claims

### Claim 1

A coupling compound
where n can be the same or different and is 2, 3, or 4; R can be the same or different and is alkylene or arylene with from about 1 to about 18 carbons; R1 can be —OH or —OCH2CH2OCH2CH2OCH3; R2 can be the same or different and is bivalent alkylene or arylene with about 1 to about 18 carbons.

### Claim 2 (depends on 1)

The coupling compound of claim 1, wherein R2 is 2,3-dimethyl-2,3-butene, 1,3 propene, or ortho-phenylene.

### Claim 3 (depends on 1)

The coupling compound of claim 1, wherein R is para-phenylene.

### Claim 4 (depends on 1)

The coupling compound of claim 1, wherein R1 is —OH.

### Claim 5 (depends on 1)

The coupling compound of claim 1, wherein the coupling compound is

### Claim 6

A method for producing a coupling compound comprising
(1) mixing SO2Cl2 with
(2) recovering
respectively,
where n can be the same or different and is 2, 3, or 4; R can be the same or different and is alkylene or arylene with from about 1 to about 18 carbons; Rt can be —OH or —OCH2CH2OCH2CH2OCH3; R2 can be the same or different and is bivalent alkylene or arylene with about 1 to about 18 carbons.

### Claim 7 (depends on 6)

The method of claim 6, wherein the mixing of SO2Cl2 is with (R1)2B—R—SH.

### Claim 8 (depends on 6)

The method of claim 6, wherein R2 is 2,3-dimethyl-2,3-butene, 1,3 propene, or ortho-phenylene.

### Claim 9 (depends on 6)

The method of claim 6, wherein R is para-phenylene.

### Claim 10 (depends on 6)

The method of claim 6, wherein R1 is —OH.

### Claim 11 (depends on 1)

A rubber composition comprising the coupling compound of claim 1, a polymer, and a filler.

### Claim 12 (depends on 11)

The rubber composition of claim 11, wherein the polymer comprises a repeat unit provided from a conjugated diene monomer.

### Claim 13 (depends on 11)

The rubber composition of claim 11, wherein the polymer is a homopolymer, a copolymer or a terpolymer.

### Claim 14 (depends on 11)

The rubber composition of claim 11, wherein R2 is 2,3-dimethyl-2,3-butene, 1,3 propene, or ortho-phenylene.

### Claim 15 (depends on 11)

The rubber composition of claim 11, wherein R is para-phenylene.

### Claim 16 (depends on 11)

The rubber composition of claim 11, wherein R1 is —OH.

### Claim 17 (depends on 11)

The rubber composition of claim 11, wherein the filler is selected from the group consisting of amorphous silica, rubber reinforcing carbon black, a combination of silica and carbon black, and clay.

### Claim 18 (depends on 11)

The rubber composition of claim 11, wherein the filler is selected from the group consisting of precipitated silica, fumed silica, calcium silicate, and aluminum silicate.

### Claim 19 (depends on 11)

The rubber composition of claim 11 comprising:
100 parts by weight of a polymer;
10 to 130 phr of a filler; and
a coupling compound from about 1 to about 20 phf.

### Claim 20 (depends on 11)

A tire having a component comprising the rubber composition of claim 11.