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

Patent metadata

Field	Value
Publication number	US-10858499-B1
Application number	US-201816622966-A
Country	US
Kind code	B1
Filing date	May 14, 2018
Priority date	Jun 30, 2017
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

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)

(R 1 ) o Si—R 2 —X-A-Y-[A-Y-] m -A-S k -A-[-Y-A] m Y-A-X—R 2 —Si(R 1 ) o ,

wherein, according to the invention, the silane has spacer groups between the respective silyl groups and the S k moiety which have at least two aromatic groups A and 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—, —R 3 NC(═O)NR 3 —, —R 3 NC(═NR 3 )NR 3 —, —R 3 NC(═S)NR 3 —, wherein at least one R 3 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—, —R 4 NC(═O)NR 4 —, —R 4 NC(═NR 4 )NR 4 —, —R 4 NC(═S)NR 4 —, wherein at least one R 4 within each group Y is a hydrogen atom.

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-[A-Y-] m -A-S k -A-[-Y-A] m Y-A-X—R 2 —Si(R 1 ) o ,  I)

wherein o may be 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 1 ) 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 divalent C 1 -C 30 hydrocarbon groups, preferably —CH 2 —CH 2 —, r is an integer from 1 to 30, preferably 3 to 10, and R 5 are unsubstituted or substituted, branched or unbranched, monovalent alkyl, alkenyl, aryl or aralkyl groups, preferably —C 13 H 27 alkyl group
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 alkyl 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 2 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 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 —, —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 2 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 —, and —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 —, and —R 4 NC(═S)NR 4 —.

5. The silane as claimed in claim 1 , wherein the aromatic groups A are selected from the group consisting of phenyl, naphthyl, pyridyl, pyridazyl, pyrimidyl, pyrazyl, triazyl, quinolyl, pyrrole, furan, thiophene, pyrazole, imidazole, thiazole and oxazole radicals.

6. 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.

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

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

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

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

11. A rubber mixture comprising at least the silane as claimed in claim 1 .

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

Assignees

• Continental Reifen Deutschland Gmbh

Inventors

• Jacob Andreas
• Dauer David-Raphael
• Strohmeier Julian
• Schoeffel Julia
• Recker Carla
• Schwekendiek Kirsten
• Mueller Norbert

Classifications

• C07F7/1804

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

• C07F7/081

  comprising at least one atom selected from the elements N, O, halogen, S, Se or Te · CPC title

• C08K5/548 Primary

  containing sulfur {(C08K5/5477 takes precedence)} · CPC title

• B60C1/00

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

• B29B7/7495

  for mixing rubber · CPC title