# US 9,752,008 B2 · Esters of cyclohexane polycarboxylic acids as plasticizers in rubber compounds

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- Number: US 9,752,008 B2
- Document ID: US9752008B2
- Status: Granted
- Kind: B2
- Application number: 13/776,265
- Filed: 2013-02-25
- Published: 2013-08-01
- Granted: 2017-09-05
- Earliest claimed: 2008-09-10
- Assignees: Bridgestone Corporation
- Applicants: Bridgestone Corporation
- Inventors: Terrence E. Hogan; William J. Corsaut
- Web page: https://patentgrep.com/patent/US9752008B2

## CPC

- C08K 5/12: of cyclic polycarboxylic acids
- C08K 3/04: Carbon
- C08K 3/36: Silica
- C08L 9/06: Copolymers with styrene
- C08L 91/06: Waxes
- 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

It has been discovered that the use of a plasticizer, an ester of a cyclohexanepolycarboxylic acid, especially a 1,2-cyclohexanedicarboxylic acid ester, that is environmentally non-toxic, can replace environmentally unfriendly phthalate plasticizers, such as dioctyl phthalates used in vulcanizable rubber compositions, especially for tires, on a one to one weight basis (phr) without sacrificing beneficial rubber properties.

## Claims

### Claim 1

A vulcanizable rubber composition comprising:
(a) a vulcanizable elastomer;
(b) a reinforcing filler comprising a selection from the group consisting of silica, carbon black, and mixtures thereof;
(c) a plasticizer comprising a 1,2-cyclohexanedicarboxylic acid ester; and
(d) a vulcanization agent.

### Claim 2 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the vulcanizable elastomer is selected from the group consisting of: homopolymers of a conjugated diene monomer, and copolymers and terpolymers of the conjugated diene monomers with monovinyl aromatic monomers and trienes.

### Claim 3 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the 1,2-cyclohexane-dicarboxylic acid ester is present in the composition in an amount of about 0.01 to about 100 phr.

### Claim 4 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the amount of the 1,2-cyclohexanedicarboxylic acid ester is about 1 to about 40 phr.

### Claim 5 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the amount of the 1,2-cyclohexanedicarboxylic acid ester is about 0.01 to about 20 phr.

### Claim 6 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the amount of the 1,2-cyclohexanedicarboxylic acid ester is about 5 to about 40 phr.

### Claim 7 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the 1,2-cyclohexane-dicarboxylic acid ester is selected from the group consisting of 1,2-diisobutyl-cyclohexanedicarboxylic acid ester; 1,2-di-(2-ethylhexyl)-cyclohexanedicarboxylic acid ester; 1,2-diisononylcyclohexanedicarboxylic acid ester; 1,2-di-C9-cyclohexane-dicarboxylic acid ester; 1,2-diisopentylcyclohexanedicarboxylic acid; 1,2-diisoheptyl-cyclohexanedicarboxylic acid; 1,2-diisodecylcyclohexane-dicarboxylic acid; 1,2-di-C7-11-cyclohexanedicarboxylic acid; 1,2-di-C9-11-cyclohexanedicarboxylic acid; 1,2-di-C7-9-cyclohexanedicarboxylic acid; and mixtures thereof.

### Claim 8 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the 1,2-cyclohexane-dicarboxylic acid ester comprises 1,2-diisononylcyclohexanedicarboxylic acid ester.

### Claim 9 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the vulcanizable elastomer is selected from the group consisting of natural rubber, synthetic polyisoprene rubber, styrene/butadiene rubber (SBR), polybutadiene, butyl rubber, neoprene, ethylene/propylene rubber, ethylene/propylene diene rubber (EPDM), acrylonitrile/butadiene rubber (NBR), silicone rubber, fluoroelastomers, ethylene acrylic rubber, ethylene vinyl acetate copolymers (EVA), epichlorohydrin rubbers, chlorinated polyethylene rubber, chlorosulfonated polyethylene, rubbers, hydrogenated nitrile rubber, and tetrafluoroethylene/propylene rubber.

### Claim 10 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the vulcanizable rubber composition is not an adhesive.

### Claim 11 (depends on 1)

The vulcanizable rubber composition of claim 1, wherein the vulcanizable elastomer comprises styrene/butadiene rubber (SBR) and the amount of the 1,2-cyclohexanedicarboxylic acid ester is about 5 to about 40 phr.

### Claim 12

A vulcanizable rubber composition comprising:
(a) a vulcanizable elastomer selected from the group consisting of natural rubber, synthetic polyisoprene rubber, styrene/butadiene rubber (SBR), polybutadiene, butyl rubber, ethylene/propylene rubber, ethylene/propylene diene rubber (EPDM), acrylonitrile/butadiene rubber (NBR), and hydrogenated nitrile rubber;
(b) a reinforcing filler comprising silica, carbon black, or mixtures thereof;
(c) about 1 to about 40 phr of a 1,2-cyclohexanedicarboxylic acid ester, selected from the group consisting of 1,2-diisobutyl-cyclohexanedicarboxylic acid ester; 1,2-di-(2-ethylhexyl)-cyclohexanedicarboxylic acid ester; 1,2-diisononylcyclohexanedicarboxylic acid ester; 1,2-di-C9-cyclohexane-dicarboxylic acid ester; 1,2-diisopentylcyclohexanedicarboxylic acid; 1,2-diisoheptyl-cyclohexanedicarboxylic acid; 1,2-diisodecylcyclohexane-dicarboxylic acid; 1,2-di-C7-11-cyclohexanedicarboxylic acid; 1,2-di-C9-11-cyclohexanedicarboxylic acid; 1,2-di-C7-9-cyclohexanedicarboxylic acid; and mixtures thereof; and
(d) a sulfur vulcanization agent.