Benzothiazole-containing silanes, method for the preparation and use thereof
The invention relates to benzothiazole-containing silanes of the formula I which are prepared by reacting benzothiazole-containing silanes of the formula II with a compound of formula III R 2 —H (III). The benzothiazole-containing silanes of the formula I can be used in rubber mixtures.
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.