IP Library Granted Patent US 12674042
Granted Patent B2
US 12674042 · App. 18/038,186 · Granted Jul 7, 2026

Rubber compounds for use in producing vehicle tires

Inventors: Rafaelle Di Ronza (Rome, IT); Yoshihiro Morishita (Tokyo, JP); Anke Blume (Enschede, NL); Rafal Anyszka (Enschede, NL); Maria del Pilar Bernal-Ortega (Enschede, NL)
Assignee: Bridgestone Europe NV/SA
C08K9/08B60C1/0016C08K3/36C08K9/06
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Quick Facts
Patent No.
US 12674042
App. No.
18/038,186
Granted
Jul 7, 2026
Kind
B2
Abstract

The invention provides diene rubber-silica compounds comprising a diene rubber matrix having dispersed therein a silica filler, wherein said silica filler is surface-modified by attachment of a π system-containing moiety which forms a π-π interaction with the diene rubber matrix. In particular, it provides such compounds in which the diene rubber is styrene-butadiene rubber. Such compounds can be vulcanized and are suitable for producing vehicle tire components, such as tire treads.

Claims (46)

1 . A diene rubber-silica compound comprising:

a diene rubber matrix having dispersed therein a silica filler,

the silica filler having a a π system-containing moiety attached to the surface of the silica filler, the x system-containing moiety having π-π interaction with the diene rubber matrix.

2 . The diene rubber-silica compound of claim 1 , wherein the diene rubber comprises styrene-butadiene rubber, or a blend of styrene-butadiene rubber with a butadiene rubber.

3 . The diene rubber-silica compound of claim 1 , wherein the π-π interaction is formed between the π system-containing moiety and a carbon-carbon double bond and/or phenyl ring present in the diene rubber matrix.

4 . The diene rubber-silica compound of claim 1 , wherein there is a substantial absence of any covalent interactions between the silica filler and the diene rubber matrix.

5 . The diene rubber-silica compound of claim 1 , wherein the π system-containing moiety is a compound containing π systems chosen from an aromatic or heteroaromatic ring, a tropylium cation, an allyl group, or an acrolein group, and combinations thereof.

6 . The diene rubber-silica compound of claim 5 , wherein the π system-containing moiety comprises a polyphenyl compound or a synthetic resin containing one or more aromatic rings.

7 . The diene rubber-silica compound of claim 6 , wherein said synthetic resin comprises a phenolic resin, an aromatic hydrocarbon resin, a hydrogenated aromatic hydrocarbon resin, an aliphatic/aromatic hydrocarbon resin, a hydrogenated aliphatic/aromatic hydrocarbon resin, a cycloaliphatic/aromatic hydrocarbon resin, a hydrogenated cycloaliphatic/aromatic hydrocarbon resin, a polyterpene resin, a terpene-phenol resin, a coumarone-indene resin, or a grafted version of any of such resins or any mixture thereof.

8 . The diene rubber-silica compound of claim 1 , wherein said π system-containing moiety is attached to the silica filler via a linking group which forms a bond to the silica filler and a bond to the π system-containing moiety.

9 . The diene rubber-silica compound of claim 8 , wherein the linking group is represented by:

in which

* denotes a point of attachment of the linking group to a surface of the silica filler;

** denotes the point of attachment of the linking group to the π system-containing moiety;

each R is independently selected from —OH, C 1-6 alkoxy and C 1-6 alkyl; and

Z is a C 1-12 alkylene group which may be interrupted by one or more groups selected from —O—, —SiR′ 2 — (in which each R′ is independently —OH, C 1-6 alkoxy, or C 1-6 alkyl), —PR″—, —NR″—, and —OP(O)(OR″)O— (in which R″ is H or C 1-6 alkyl).

10 . The diene rubber-silica compound of claim 8 , wherein the linking group is represented by:

in which

* denotes a point of attachment of the linking group to a surface of the silica filler;

** denotes the point of attachment of the linking group to the π system-containing moiety;

each R is independently selected from —OH, C 1-3 alkoxy and C 1-3 alkyl; and

Z is a C 1-12 alkylene group which may be interrupted by one or more groups selected from —O—, —SiR′ 2 — (in which each R′ is independently —OH, C 1-6 alkoxy or C 1-6 alkyl), —PR″—, —NR″—, and —OP(O)(OR″)O— (in which R″ is H or C 1-3 alkyl).

11 . The diene rubber-silica compound of claim 9 , wherein the linking group is represented by:

in which

* denotes a point of attachment of the linking group to a surface of the silica filler;

** denotes the point of attachment of the linking group to the π system-containing moiety;

m is an integer from 0 to 12;

a is an integer from 0 to 6; and

b is an integer from 0 to 6.

12 . The diene rubber-silica compound of claim 1 further comprising a vulcanizable diene rubber-silica compound.

13 . A vulcanized rubber compound formed by cross-linking a diene rubber-silica compound as claimed in claim 12 .

14 . A vehicle tire, comprising a vehicle tire component made from the diene rubber-silica compound of claim 1 .

15 . A diene rubber-silica compound comprising:

a diene rubber matrix having dispersed therein a silica filler;

a π system-containing moiety attached to the surface of the silica filler and having π-π interaction with the diene rubber matrix,

wherein the π system-containing moiety is a compound containing π systems chosen from an aromatic or heteroaromatic ring, a tropylium cation, an allyl group, or an acrolein group, and combinations thereof.

16 . A diene rubber-silica compound comprising:

a diene rubber matrix having dispersed therein a silica filler;

a π system-containing moiety attached to the surface of the silica filler and having π-π interaction with the diene rubber matrix,

wherein the π system-containing moiety is attached to the silica filler via a linking group which forms a bond to the silica filler and a bond to the x system-containing moiety,

wherein the linking group is represented by:

in which

* denotes a point of attachment of the linking group to a surface of the silica filler;

** denotes the point of attachment of the linking group to the π system-containing moiety;

each R is independently selected from —OH, C 1-6 alkoxy and C 1-6 alkyl; and

Z is a C 1-12 alkylene group which may be interrupted by one or more groups selected from —O—, —SiR′ 2 — (in which each R′ is independently —OH, C 1-6 alkoxy, or C 1-6 alkyl), —PR″—, —NR″—, and —OP(O)(OR″)O— (in which R″ is H or C 1-6 alkyl).