Urea-containing silanes, process for preparation thereof and use thereof

1. A urea-containing silane of formula I

where each R 1 is independently selected from the group consisting of a C1-C10 alkoxy group, a C1-C10 alkyl group and each R is a branched or unbranched, saturated, aliphatic, divalent C 1 -C 7 hydrocarbyl group and x is an integer of 4.

2. The urea-containing silane according to claim 1 , wherein the urea-containing silane is

((EtO) 3 Si—CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 ,

((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 ,

((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 or

((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S x/2 ) 2 .

3. The urea-containing silane according to claim 1 , wherein the urea-containing silane is

(EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S 4 —CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —Si(OEt) 3 .

4. A process for preparing the urea-containing silane of claim 1 , comprising reacting a urea-containing disulphide silane of formula II

with sulphur, where R and R 1 are each as defined in claim 1 .

5. The process of claim 4 , wherein the reaction is conducted under a protective gas atmosphere.

6. The process of claim 4 , wherein the reaction is conducted under standard pressure.

7. The process of claim 4 , wherein the reaction is conducted without solvent.

8. A process for preparing the urea-containing silane of claim 1 , wherein, in a first step, an aminosilane of formula III

is reacted with an isocyanate of formula IV

where R and R 1 are each as defined in claim 1 and Hal is F, Cl, Br or I,

and, in a second step, the product from the first step is reacted with a sodium polysulphide of formula (V)

Na 2 S x   (V)

where x is as defined in claim 1 .

9. The process of claim 8 , wherein the first step is conducted under a protective gas atmosphere.

10. The process of claim 8 , wherein the second step is conducted under a protective gas atmosphere.

11. The process of claim 8 , wherein ethanol is used as a solvent in the first step.

12. The process of claim 8 , wherein ethanol is used as a solvent in the second step.

13. A process for preparing the urea-containing silane of claim 1 , wherein, in a first step, an isocyanatosilane of formula VII

is reacted with an amine of formula VIII

where R and R 1 are each as defined in claim 1 and Hal is F, Cl, Br or I,

and, in a second step, the product from the first step is reacted with a sodium polysulphide of the formula V

Na 2 S x   (V)

where x is as defined in claim 1 .

14. The process of claim 13 , wherein the amine of formula VIII, prior to reaction with the isocyanatosilane of the formula VII, is prepared by adding a base to a hydrochloride salt of a diamine of formula IX

Cl −+ H 3 N—R—S—S—R—NH 3 + Cl −   IX.

15. The process of claim 14 , wherein the base is NaOEt.

16. The process of claim 13 , wherein ethanol is used as a solvent in the first step.

17. The process of claim 13 , wherein ethanol is used as a solvent in the second step.