# US 9,040,618 B2 · Rubber composition including a 1,2,4-triazine derivative

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- Number: US 9,040,618 B2
- Document ID: US9040618B2
- Status: Granted
- Kind: B2
- Application number: 14/111,600
- Filed: 2012-04-16
- Published: 2014-04-10
- Granted: 2015-05-26
- Earliest claimed: 2011-04-14
- Assignees: Compagnie Generale Des Etablissements Michelin; Michelin Recherche et Technique S.A.
- Applicants: Anne Veyland; Nicolas Seeboth
- Inventors: Anne Veyland; Nicolas Seeboth
- Web page: https://patentgrep.com/patent/US9040618B2

## CPC

- C08L 9/06: Copolymers with styrene
- C07D 253/07: with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 487/04: Ortho-condensed systems
- C07F 9/6521: Six-membered rings
- C08K 5/0025: {Crosslinking or vulcanising agents; including accelerators}
- C08K 5/34928: {Salts}
- C08K 5/378: containing heterocyclic rings
- C08K 5/5373: containing heterocyclic rings not representing cyclic esters of phosphonic acids
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)

## Abstract

A rubber composition for manufacturing tyres is based on one or more diene elastomers, one or more reinforcing fillers, and a vulcanization system. The vulcanization system includes one or more 1,2,4-triazine compounds chosen from compounds of formula I and compounds of formula II: Certain specific 1,2,4-triazine derivatives are described.

## Claims

### Claim 1

A rubber composition used in manufacturing tyres the composition comprising:
one or more diene elastomers;
one or more reinforcing fillers; and
a vulcanization system, wherein the vulcanization system includes one or more 1,2,4-triazine compounds selected from compounds of formula
where:
R1 and R2 independently represent H, a halogen, a group selected from alkoxy and (C1-C10)alkylthio groups, or a C1-C25 hydrocarbon group selected from a group consisting of linear, branched, or cyclic alkyl groups, aralkyl groups, alkylaryl groups, and aryl groups, R1 and R2 being formable in a ring,
A is selected from
—H,
a group
where:
R′1 is same as R1,
R′2 is same as R2,
x is an integer greater than or equal to 1,
a group
←Sy—R3
where
R3 represents a C1-C18 hydrocarbon group,
y is an integer greater than or equal to 1,
a group
where R6 is a C1-C18 hydrocarbon group,
a group
where R7 is a C1-C18 hydrocarbon group,
a group
where
Y is a C1-C18 hydrocarbon chain;
R8 is a C1-C18 hydrocarbon group,
a group
where
X is a C1-C18 hydrocarbon chain;
R9 and R10 independently represent a C1-C18 hydrocarbon group, and
a group
where
R11 is H or a C1-C18 hydrocarbon group,
Mn+ represents a metal or non-metal cation,
n represents an integer between 1 and 4.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein R1 and R2 independently represent H or a phenyl group.

### Claim 3 (depends on 2)

The composition according to claim 2, wherein R2 represents a phenyl group and R1 represents H.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein A is selected from
the group
the group
←Sy—R3
the group
the group
where x, R′1, R′2, y, R3, X, R9, R10 and R11 are as defined in claim 1.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein the R3 and R6 to R11 groups are independently selected from a group consisting of linear, branched, or cyclic alkyl groups, aryl groups, aralkyl groups, and alkylaryl groups.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the X and Y groups are independently selected from a group consisting of linear, branched, or cyclic alkylene groups, arylene groups, and alkylarylene groups.

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the the Mn+ is a metal cation selected from a group consisting of Zn2+, Cu2+, Na+, K+, and Li+.

### Claim 8 (depends on 1)

The composition according to claim 1, wherein Mn+ is a non-metal cation.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein the 1,2,4-triazine compound or compounds represent from 0.1 to 7 phr (parts by weight per hundred parts of diene elastomer).

### Claim 10 (depends on 1)

The composition according to claim 1, wherein the diene elastomer or elastomers are selected from a group of elastomers consisting of polybutadienes, natural rubber, synthetic polyisoprenes, butadiene copolymers, isoprene copolymers, and mixtures of these elastomers.

### Claim 11 (depends on 1)

The composition according to claim 1, wherein the reinforcing filler or fillers are selected from a group consisting of silica, carbon black, and their mixtures.

### Claim 12 (depends on 1)

The composition according to claim 1, wherein the reinforcing filler or fillers are present at a content of between 20 and 200 phr.

### Claim 13 (depends on 1)

A process for preparing a rubber composition as defined in claim 1, used in manufacturing tyres, the process comprising steps of:
incorporating the reinforcing filler or fillers in the diene elastomer or elastomers during a first stage and kneading thermomechanically, in one or more goes, until a maximum temperature of between 110° C. and 190° C. is reached;
subsequently incorporating, during a second stage, the vulcanization system and kneading up to a maximum temperature of less than 110° C.

### Claim 14 (depends on 13)

The process according to claim 13, wherein, between the kneading thermomechanically and the incorporating of the vulcanization system, a combined product of the kneading thermomechanically is cooled to a temperature of less than or equal to 100° C.

### Claim 15 (depends on 1)

The composition according to claim 1, wherein the composition is used in manufacturing a finished article or a semi-finished product intended for a motor vehicle ground-contact system.

### Claim 16 (depends on 1)

A tyre comprising the rubber composition as defined in claim 1.

### Claim 17 (depends on 1)

A tread comprising the rubber composition as defined in claim 1.

### Claim 18

A 1,2,4-triazine of formula
where:
R1a and R2a independently represent H, a halogen, a group selected from alkoxy and (C1-C10)alkylthio groups, or a C1-C25 hydrocarbon group selected from a group consisting of linear, branched, or cyclic alkyl groups, aralkyl groups, alkylaryl groups, and aryl groups, R1a and R2a being formable in a ring,
Aa is selected from
a group
←Sya—R3a
where
R3a represents a C1-C18 hydrocarbon group that does not include 1,2,4-triazine, wherein a compound of the formula (I′) is not of formula
ya is an integer greater than or equal to 1,
a group
where R6a is a C1-C18 hydrocarbon group other than a substituted phenyl group, wherein, if R6a represents a methyl group, R1a and R2a do not form a ring and R1a and R2a respectively do not represent a methyl and a hydroxyl,
group
where R7a is a C1-C18 hydrocarbon group, wherein, if R7a represents an ethyl group, R1a and R2a do not form a ring,
a group
where
Xa is a C1-C18 hydrocarbon chain, and
R9a and R10a independently represent a C1-C18 hydrocarbon group.

### Claim 19 (depends on 18)

The 1,2,4-triazine according to claim 18, wherein R1a and R2a independently represent H or a phenyl group.

### Claim 20 (depends on 19)

The 1,2,4-triazine according to claim 19, wherein R2a represents a phenyl group and R1a represents H.

### Claim 21 (depends on 18)

The 1,2,4-triazine according to claim 18, wherein Aa is selected from:
the group
←Sya—R3a
and
the group
wherein ya, R3a, Xa, R9a, and R10a are as defined in claim 18.

### Claim 22 (depends on 18)

The 1,2,4-triazine according to claim 18, wherein the R3a, R6a, R7a, and R9a to R10a groups are independently selected from a group consisting of linear, branched, or cyclic alkyl groups, aryl groups, aralkyl groups, and alkylaryl groups.

### Claim 23 (depends on 18)

The 1,2,4-triazine according to claim 18, wherein the Xa group is selected from a group consisting of linear, branched, or cyclic alkylene groups, arylene groups, and alkylarylene groups.