Silane, rubber mixture containing the silane, and vehicle tire having the rubber mixture in at least one component

Patent metadata

Field	Value
Publication number	US-11384103-B2
Application number	US-201916980039-A
Country	US
Kind code	B2
Filing date	Feb 5, 2019
Priority date	Mar 12, 2018
Publication date	Jul 12, 2022
Grant date	Jul 12, 2022

Abstract

The invention relates to a silane, to a rubber mixture comprising the silane and to a vehicle tire comprising the rubber mixture in at least one component.The inventive silane has the following formula (I):(R1)oSi—R2—X-A-Y—[R7—Y—]m—R7—Sk—R7—[—Y—R7]m—Y-A-X—R2—Si(R1)o,wherein according to the invention it has spacer groups between the respective silyl groups and the Sk moiety, which have an aromatic group A and at least one alkylene group R7 and also the linking units X and Y, wherein the groups X within a molecule may be identical or different from each other and are selected from the groups —HNC(═O)—, —C(═O)NH—, —C(═O)O—, —OC(═O)—, —OC(═O)NH—, —HNC(═O)O—, —R3NC(═O)NR3—, —R3NC(═NR3)NR3—, —R3NC(═S)NR3—, wherein at least one R3 within each group X is a hydrogen atom; and wherein the groups Y within a molecule may be identical or different from each other and are selected from the groups —HNC(═O)—, —C(═O)NH—, —C(═O)O—, —OC(═O)—, —OC(═O)NH—, —HNC(═O)O—, —R4NC(═O)NR4—, —R4NC(═NR4)NR4—, —R4NC(═S)NR4—, wherein at least one R4 within each group Y is a hydrogen atom, and wherein the radicals R7 within a molecule may be identical or different and comprise alkylene radicals having 1 to 20 carbon atoms, which may have cyclic, branched and/or aliphatically unsaturated groups.The inventive rubber mixture comprises at least one inventive silane.

First claim

The invention claimed is:

1. A silane of formula I):
(R 1 ) o Si—R 2 —X-A-Y—[R 7 —Y—] m —R 7 —S k —R 7 —[—Y—R 7 ] m —Y-A-X—R 2 —Si(R 1 ) o ,  I)

wherein o is 1, 2 or 3 and k is an integer greater than or equal to 2 and the radicals R 1 within the silyl groups (R′) o Si— and on both sides of the molecule may be identical or different from each other and are selected from alkoxy groups having 1 to 10 carbon atoms, cycloalkoxy groups having 4 to 10 carbon atoms, phenoxy groups having 6 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, alkynyl groups having 2 to 20 carbon atoms, aralkyl groups having 7 to 20 carbon atoms, halides; or,
alkyl polyether groups —O—(R 6 —O) r —R 5 wherein R 6 are identical or different and are branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic bridging C 1 -C 30 hydrocarbon groups, r is an integer from 1 to 30, and R 5 are unsubstituted or substituted, branched or unbranched, terminal alkyl, alkenyl, aryl or aralkyl groups; or,
two R 1 form a cyclic dialkoxy group having 2 to 10 carbon atoms, in which case o is <3; or,
two or more silanes of formula I) can be bridged via radicals R 1 ; and,
wherein the radicals R 2 within a molecule may be identical or different and are linear or branched alkylene groups having 1 to 20 carbon atoms or cycloalkyl groups having 4 to 12 carbon atoms or aryl groups having 6 to 20 carbon atoms or alkenyl groups having 2 to 20 carbon atoms, alkynyl groups having 2 to 20 carbon atoms or aralkyl groups having 7 to 20 carbon atoms; and
wherein the groups X within a molecule may be identical or different from each other and are selected from the groups
—HNC(═O)—, —C(═O)NH—, —C(═O)O—, —OC(═O)—, —OC(═O)NH—,
—HNC(═O)O—, —R 3 NC(═O)NR 3 —, —R 3 NC(═NR 3 )NR 3 —, —R 3 NC(═S)NR 3 —,
wherein the radicals R 3 within a group X and within a molecule may be identical or different and are selected from a hydrogen atom or as defined for R 1 under the condition that at least one R 3 within each group X is a hydrogen atom; and
wherein the groups A within a molecule may be identical or different from each other and are aromatic groups, and
wherein the radicals R 7 within a molecule may be identical or different and comprise alkylene radicals having 1 to 20 carbon atoms, which may have cyclic, branched and/or aliphatically unsaturated groups; and
wherein the groups Y within a molecule may be identical or different from each other and are selected from the groups
—HNC(═O)—, —C(═O)NH—, —C(═O)O—, —OC(═O)—, —OC(═O)NH—,
—HNC(═O)O—, —R 4 NC(═O)NR 4 —, —R 4 NC(═NR 4 )NR 4 —, NR 4 )NR 4 —, —R 4 NC(═S)NR 4 —,
wherein the radicals R 4 within a group Y and within a molecule may be identical or different and are selected from a hydrogen atom or as defined for R 1 under the condition that at least one R 4 within each group Y is a hydrogen atom; and wherein each m is independently an integer from 0 to 4, and wherein the silane may also be in the form of oligomers that are formed by hydrolysis and condensation of silanes of formula I).

2. The silane as claimed in claim 1 , wherein each m=0.

3. The silane as claimed in claim 1 , wherein the groups X are selected from the groups
—HNC(═O)—, —C(═O)NH—, —OC(═O)NH—, —HNC(═O)O—, —R 3 NC(═O)NR 3 —,
—R 3 NC(═NR 3 )NR 3 —, —R 3 NC(═S)NR 3 —.

4. The silane as claimed in claim 1 , wherein the groups Y are selected from the groups
—HNC(═O)—, —C(═O)NH—, —OC(═O)NH—, —HNC(═O)O—, —R 4 NC(═O)NR 4 —,
—R 4 NC(═NR 4 )NR 4 —, NR 4 )NR 4 —, —R 4 NC(═S)NR 4 —.

5. The silane as claimed in claim 1 , wherein the radicals R 7 are linear or branched alkylene radicals having 1 to 20 carbon atoms, or cycloalkyl groups having 4 to 8 carbon atoms.

6. The silane as claimed in claim 1 , wherein the aromatic groups A are selected from the group consisting of phenylene, naphthylene, pyridyl, pyridazyl, pyrimidyl, pyrazyl, triazyl, quinolyl, pyrrolyl, furanyl, thiophenyl, pyrazolyl, imidazolyl, thiazolyl and oxazolyl radicals and also derivatives of said groups.

7. The silane as claimed in claim 1 , wherein the radicals R 1 are alkyl groups having 1 to 6 carbon atoms or alkoxy groups having 1 to 6 carbon atoms or halides.

8. The silane as claimed in claim 1 , wherein the radicals R 2 are linear or branched alkylene groups having 2 to 8 carbon atoms or cycloalkyl groups having 4 to 8 carbon atoms.

9. The silane as claimed in claim 1 , wherein the silane has the following formula II):

10. The silane as claimed in claim 1 , wherein k is an integer from 2 to 8.

11. The silane as claimed in claim 1 which is mixed with a silica to modify a surface of the silica.

12. The silane as claimed in claim 1 which is mixed with a silica to modify a surface of the silica, and which is mixed in a rubber mixture.

13. A vehicle tire comprising the mixture as claimed in claim 11 in at least one component.

Assignees

• Continental Reifen Deutschland Gmbh

Inventors

• Dauer David-Raphael
• Jacob Andreas
• Strohmeier Julian

Classifications

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title

• B60C1/0016

  Compositions of the tread · CPC title

• C08K9/06

  with silicon-containing compounds · CPC title

• C08K3/36

  Silica · CPC title

• B60C1/00

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title