Benzothiazole-containing silanes, method for the preparation and use thereof

Patent metadata

Field	Value
Publication number	US-11254693-B2
Application number	US-201816606012-A
Country	US
Kind code	B2
Filing date	Apr 25, 2018
Priority date	May 8, 2017
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

The invention relates to benzothiazole-containing silanes of the formula Iwhich are prepared by reacting benzothiazole-containing silanes of the formula IIwith a compound of formula IIIR2—H  (III).The benzothiazole-containing silanes of the formula I can be used in rubber mixtures.

First claim

The invention claimed is:

1. A benzothiazole-containing silane of the formula (I):

wherein:
R 1 is the same or different and is an R 4 O— group with R 4 being H, methyl, ethyl, propyl, C9-C30 branched or unbranched monovalent alkyl, alkenyl, aryl or aralkyl group,
R 2 is an alkyl polyether group —O—(R 5 —O) m —R 6 with R 5 being the same or different and being a branched or unbranched, saturated or unsaturated, aliphatic divalent C1-C30 hydrocarbon group, m is 1 to 30, and R 6 is a branched or unbranched C1-C30-alkyl group,
R 3 is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group, and
x=2-10, and
n=0, 1 or 2.

2. The benzothiazole-containing silane according to claim 1 , wherein R 1 is methoxy or ethoxy.

3. The benzothiazole-containing silane according to claim 1 , wherein R 2 =—O—(CH 2 CH 2 O) 5 —C 13 H 27 .

4. The benzothiazole-containing silane according to claim 1 , wherein:
R 1 =—O—C 2 H 5 ,
R 2 =—O—(CH 2 CH 2 O) 5 —C 13 H 27 ,
R 3 =(CH 2 ) 3 ,
X=2, and
n=2.

5. A process for preparing the benzothiazole-containing silane of claim 1 , comprising:
reacting a benzothiazole-containing silane of the formula (II):

with a compound of formula (III):
R 2 —H  (III),

to obtain the benzothiazole-containing silane,
wherein:
R 1 is the same or different and is an R 4 O— group with R 4 being H, methyl, ethyl, propyl, C9-C30 branched or unbranched monovalent alkyl, alkenyl, aryl or aralkyl group,
R 2 is an alkyl polyether group —O—(R 5 —O) m —R 6 with R 5 being the same or different and being a branched or unbranched, saturated or unsaturated, aliphatic divalent C1-C30 hydrocarbon group, m is 1 to 30, and R 6 is a branched or unbranched C1-C30-alkyl group,
R 3 is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group, and
x=2-10, and
n=0, 1 or 2.

6. The process according to claim 5 , wherein the reaction is conducted in the presence of a catalyst with elimination of R 1 —H.

7. A filled rubber mixture, comprising the benzothiazole-containing silane of claim 1 as a coupling reagent.

8. A rubber mixture, comprising:
(A) a rubber or a mixture of rubbers,
(B) a filler, and
(C) at least one benzothiazole-containing silane of claim 1 .

9. The rubber mixture according to claim 8 , wherein a ratio of the at least one benzothiazole-containing silane to a vulcanization accelerator contained in the rubber mixture is greater than 5.

10. The rubber mixture according to claim 8 , comprising a natural rubber.

Assignees

• Evonik Operations Gmbh

Inventors

• Koepfer Alexander
• Klockmann Oliver
• Kufelt Olga
• Mayer Stefanie
• Roeben Caren
• Rosenstingl Sebastian
• Wehmeier Andre

Classifications

• C08L91/06

  Waxes · CPC title

• C08L91/00

  Compositions of oils, fats or waxes; Compositions of derivatives thereof · CPC title

• C08L21/00

  Compositions of unspecified rubbers · CPC title

• C08L9/06

  Copolymers with styrene · CPC title

• C08L9/00

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title