Silane, rubber mixture containing the silane, vehicle tire comprising the rubber mixture in at least one component, and process for producing the silane

Patent metadata

Field	Value
Publication number	US-11414441-B2
Application number	US-202017594675-A
Country	US
Kind code	B2
Filing date	Mar 25, 2020
Priority date	Apr 26, 2019
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

The invention relates to a silane, to a rubber mixture comprising the silane and to a vehicle tire which comprises the rubber mixture in at least one component, and to a process for producing the silane.The silane of the invention has the following formula I)(R1)oSi—R2—S—R3—S—R3—S—X,  I)which, according to the invention, comprises the —R2—S—R3—S—R3— unit in the spacer group.The rubber mixture of the invention comprises at least one silane of the invention.

First claim

The invention claimed is:

1. A silane of formula I):
(R 1 ) o Si—R 2 —S—R 3 —S—R 3 —S—X  I)

wherein o may be 1, 2 or 3 and the R 1 radicals may be identical or different 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, 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, terminal 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) may be bridged via R 1 radicals;
wherein R 2 and R 3 may be identical or different and are selected from the group consisting of 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;
wherein the X group is a hydrogen atom or a —C(═O)—R 4 group or an —SiR 7 3 group, where R 4 and R 7 are selected from C 1 -C 20 -alkyl groups, C 4 -C 10 -cycloalkyl groups, C 6 -C 20 -aryl groups, C 2 -C 20 -alkenyl groups and C 7 -C 20 -aralkyl groups, and R 7 is additionally 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; and where the silane may also take the form of oligomers formed via hydrolysis and condensation of silanes of the formula I);
wherein the silane modifies the surface of a silica;
wherein a rubber mixture contains the silane; and,
wherein the silane is prepared by a process which comprises at least the following process steps:
a) providing a substance (R 1 ) o Si—R 2 —SH;
b) providing a substance Cl—R 3 —Cl;
c) reacting the substance from step a) with the substance from step b) in the presence of a base to give (R 1 ) o Si—R 2 —S—R 3 —Cl;
d) reacting (R 1 ) o Si—R 2 —S—R 3 —Cl from step c) with a metallic hydrogensulfide (M-S—H) to give (R 1 ) o Si—R 2 —S—R 3 —SH, where M is metal;
e) reacting (R 1 ) o Si—R 2 —S—R 3 —SH from step d) with a further portion of Cl—R 3 —Cl to give (R 1 ) o Si—R 2 —S—R 3 —S—R 3 —Cl;
f) providing a substance M-S-X where the X group is a hydrogen atom or a —C(=0)—R 4 group or an —SiR 7 3 ; group, where R 4 and R 7 are selected from C 1 -C 20 alkyl groups, C 4 —C 10 —cycloalkyl groups, C 6 —C 20 —aryl groups, C 2 —C 20 —alkenyl groups and C 7 —C 20 —aralkyl groups, and R 7 is additionally 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 and M is metal:
g) reacting (R 1 ) o Si—R 2 —S—R 3 —S—R 3 —Cl with M-S—X to give the silane of formula I): (R 1 ) o Si—R 2 —S—R 3 —S—R 3 —S—X;
h) optionally purifying the silane of formula I) obtained in step g),

wherein the two instances of M in steps d) and f) may be identical or different.

2. The silane as claimed in claim 1 , wherein the R 3 radicals are identical and are linear alkylene radicals having 1 to 20 carbon atoms, preferably 2 to 10 carbon atoms, more preferably 4 to 8 carbon atoms.

3. The silane as claimed in claim 1 , wherein the X group is a —C(═O)—R 4 group and wherein R 4 is selected from C 1 -C 20 -alkyl groups.

4. The silane as claimed in claim 1 , wherein the R 1 radicals are identical or different and are alkoxy groups having 1 to 6 carbon atoms or halides.

5. The silane as claimed in claim 1 , wherein the R 2 radical is a linear or branched alkylene group having 2 to 8 carbon atoms.

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

7. A vehicle tire comprising the rubber mixture as claimed in claim 1 in at least one component.

Assignees

• Continental Reifen Deutschland Gmbh

Inventors

• Strohmeier Julian
• Schöffel Julia
• Jacob Andreas
• Jürges Jaana
• Davin Julien
• Dauer David-Raphael

Classifications

• C07F7/1804 Primary

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

• C08L9/06

  Copolymers with styrene · CPC title

• C08K3/36

  Silica · CPC title

• C08K5/548

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

• C08K9/06 Primary

  with silicon-containing compounds · CPC title