Oligomeric organosilanes, the production thereof and the use thereof in rubber mixtures

1. An oligomeric organosilane, comprising structural unit A and at least one structural unit selected from structural units B, C and D joined in a linear, branched or cyclic arrangement;

wherein:

Y represents H, F, Cl, Br, I, SCN, SH, —S x —(CH 2 ) n SiRR 1 R 2 or —N(R 8 ) 2 ;

R 8 independently represents H, (C 1 -C 16 ) alkyl, —(CH 2 ) 2 NH 2 , —(CH 2 ) 2 NH—(CH 2 ) 2 NH 2 or —(CH 2 ) 2 N[(CH 2 ) 2 NH 2 ] 2 ;

n represents 1-8;

G represents H, F, Cl, Br, I, SCN, SH, —S x —(CH 2 ) n SiRR 1 R 2 or —N(R 8 ) 2 , such that G is different from Y;

R, R 1 , R 2 , R 3 , R 4 , each independently represent OH, (C 1 -C 16 )alkyl, (C 2 -C 16 )alkenyl, (C 6 -C 14 )aryl, (C 1 -C 4 )alkoxy, an OSiR 1 R 2 R 3 group or an alkyl polyether group —O—(R 5 —O) m —R 6 ;

R 5 independently represents a branched or unbranched, saturated or unsaturated, aliphatic divalent C1-C30 hydrocarbon group;

m on average is 1 to 30;

R 6 represents an unsubstituted or substituted, branched or unbranched C 1 -C 30 alkyl group, C 2 -C 30 alkenyl group, a C 6 -C 14 aryl group, or a C 7 -C 40 aralkyl group;

R 7 represents an alkyl polyether group —O—(R 5 —O) m —R 6 ;

x on statistical average is 1-6; and

z on statistical average is 1-6.

2. The oligomeric organosilane of claim 1 , wherein an molecular weight of the oligomeric organosilane is between 400 and 100,000 g/mol.

3. The oligomeric organosilane of claim 1 , wherein:

the oligomeric organosilane comprises the structural units A and B and C; and

R 7 represents the alkyl polyether group —O—(R 5 —O) m —R 6 .

4. The oligomeric organosilane of claim 3 , wherein;

in structural unit A,

n represents 3, and

Y represents SH;

in structural unit B,

R 1 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 ,

R 2 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 ,

n represents 3, and

z represents 2-4; and

in structural unit C,

R represents phenyl, propyl or octyl, and

R 3 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 .

5. The oligomeric organosilane of claim 1 , wherein:

the oligomeric organosilane comprises the structural units A and B; and

R 7 represents the alkyl polyether group —O—(R 5 —O) m —R 6 .

6. The oligomeric organosilane of 5 , wherein:

in structural unit A,

n represents 3, and

Y represents SH; and

in structural unit B,

R 1 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 ,

R 2 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 ,

n represents 3, and

z represents 2-4.

7. The oligomeric organosilane of claim 1 , wherein:

the oligomeric organosilane comprises the structural units A and D; and

R 7 represents the alkyl polyether group —O—(R 5 —O) m —R 6 .

8. The oligomeric organosilane of claim 7 , wherein:

in structural unit A,

n represents 3, and

Y represents SH; and

in structural unit D,

G represents Cl or NH 2 ,

n represents 3, and

R 4 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 .

9. The oligomeric organosilane of claim 1 , wherein:

the oligomeric organosilane comprises the structural units A and C and D,

R 7 represents the alkyl polyether group —O—(R 5 —O) m —R 6 .

10. The oligomeric organosilane of claim 9 , wherein:

in structural unit A,

n represents 3, and

Y represents SH;

in structural unit C,

R represents phenyl, propyl or octyl, and

R 3 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 ; and

in structural unit D,

G represents Cl or NH 2 ,

R 4 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 , and

n represents 3.

11. The oligomeric organosilane of claim 1 , wherein:

the oligomeric organosilane comprises the structural units A and C; and

R 7 represents the alkyl polyether group —O—(R 5 —O) m —R 6 .

12. The oligomeric organosilane of claim 11 , wherein:

in structural unit A,

n represents 3, and

Y represents SH; and

in structural unit C,

R represents phenyl, propyl or octyl, and

R 3 represents ethoxy or alkyl polyether group —O—(R 5 —O) m —R 6 .

13. A process for preparing the oligomeric organosilane of claim 1 , the process comprising:

oligomerizing/polymerizing the compound of formula I and at least one of the compounds of formulae II-IV:

in the presence of water at temperatures of 0-150° C., to form an intermediate; and

reacting the intermediate with an alkyl polyether alcohol of formula HO—(R 5 —O) m —R 6 , to form the oligomeric organosilane,

wherein:

Y, G, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , n, m, u, x and z are each as defined in claim 1 ; and

R 9 independently represents H, F, Cl, Br, I, or (C 1 -C 16 )alkoxy.

14. The process of claim 13 , wherein the oligomerizing/polymerizing, the reacting, or both, occurs in the presence of a catalyst.

15. The process of claim 14 , wherein:

the oligomerizing/polymerizing occurs in the present of HCl as catalyst; and

the reacting occurs in the present of tetrabutyl orthotitanate as catalyst.

16. The process of claim 13 , wherein the oligomerizing/polymerizing, the reacting, or both, occurs in the presence of a solvent which is ethyl acetate or ethanol.

17. A rubber mixture, comprising the oligomeric organosilane of claim 1 .

18. A tire, profile, cable sheath, hose, drive belt, conveyor belt, tyre cover, shoe sole, gasket ring or damping element comprising the rubber mixture of claim 17 .

19. An oligomeric organosilane obtained by the process of claim 13 .

20. An oligomeric organosilane, comprising structural unit D and at least one structural unit selected from structural units A, B and C, joined in a linear, branched or cyclic arrangement:

wherein:

Y represents H, F, Cl, Br, I, SCN, SH, —S x —(CH 2 ) n SiRR 1 R 2 or —N(R 8 ) 2 ;

R 8 independently represents H, (C 1 -C 16 ) alkyl, —(CH 2 ) 2 NH 2 , —(CH 2 ) 2 NH—(CH 2 ) 2 NH 2 or —(CH 2 ) 2 N[(CH 2 ) 2 NH 2 ] 2 ;

n represents 1-8;

G represents H, F, Cl, Br, I, SCN, SH, —S x —(CH 2 ) n SiRR 1 R 2 or —N(R 8 ) 2 , such that G is different from Y;

R, R 1 , R 2 , R 3 , R 4 , R 7 each independently represent OH, (C 1 -C 16 )alkyl, (C 2 -C 16 )alkenyl, (C 6 -C 14 )aryl, (C 1 -C 4 )alkoxy, an OSiR 1 R 2 R 3 group or an alkyl polyether group —O—(R 5 —O) m —R 6 ;

R 5 independently represents a branched or unbranched, saturated or unsaturated, aliphatic divalent C1-C30 hydrocarbon group;

m on average is 1 to 30;

R 6 represents an unsubstituted or substituted, branched or unbranched C 1 -C 30 alkyl group, C 2 -C 30 alkenyl group, a C 6 -C 14 aryl group, or a C 7 -C 40 aralkyl group;

x on statistical average is 1-6;

z on statistical average is 1-6; and

at least one R, R 1 , R 2 , R 3 , R 4 or R 7 group is an alkyl polyether group —O—(R 5 —O) m —R 6 .

21. A process for preparing the oligomeric organosilane of claim 20 , the process comprising:

oligomerizing/polymerizing the compound of formula IV and at least one of the compounds of formulae I-III:

in the presence of water at temperatures of 0-150° C., to form an intermediate; and

reacting the intermediate with an alkyl polyether alcohol of formula HO—(R 5 —O) m —R 6 , to form the oligomeric organosilane,

wherein:

Y, G, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , n, m, u, x and z are each as defined in claim 20 ; and

R 9 independently represents H, F, Cl, Br, I, or (C 1 -C 16 )alkoxy.