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

Patent metadata

Field	Value
Publication number	US-9388201-B2
Application number	US-201514711463-A
Country	US
Kind code	B2
Filing date	May 13, 2015
Priority date	May 15, 2014
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

The invention relates to urea-containing silanes of the formula I

which are prepared by, in a first step, reacting an aminosilane of the formula II

with an isocyanate of the formula III

and, in a second step, reacting the product from the first process step with sodium sulphide of the formula IV

Na 2 S  (IV)

or in a first step, reacting an isocyanatosilane of the formula VI

with an amine of the formula VII

and, in a second step, reacting the product from the first process step with sodium sulphide of the formula IV

Na 2 S  (IV).

First claim

What is claimed is:

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 C2-C10 cyclic dialkoxy group, a phenoxy group, a C4-C10 cycloalkoxy group, a C6-C20 aryl group, a C1-C10 alkyl group, a C2-C20 alkenyl group, a C7-C20 aralkyl group or a halogen, and each R is independently a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group.

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 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 ) 2 S,
((EtO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((EtO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S,
((EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S,
((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 ) 2 S,
((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 ) 2 S,
((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 ) 2 S,
((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 ) 2 S,
((MeO) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S,
((MeO) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S or
((MeO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 ) 2 S.

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—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 , wherein, in a first step, an aminosilane of formula II

is reacted with an isocyanate of formula III

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 sulphide of formula (IV)
Na 2 S  (IV).

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

6. The process of claim 4 , wherein the second step is conducted under a protective gas atmosphere.

7. The process of claim 4 , wherein the first step is conducted at temperatures between −78° C. and 100° C.

8. The process of claim 4 , wherein the second step is conducted at temperatures between 20° C. and 150° C.

9. The process of claim 4 , wherein ethanol is used as solvent in the first step.

10. The process of claim 4 , wherein ethanol is used as solvent in the second step.

11. The process of claim 9 , wherein the ethanol is distilled off after the first step.

12. The process of claim 10 , wherein the ethanol is distilled off after the second step.

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

is reacted with an amine of formula VII

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 sodium sulphide of the formula (IV)
Na 2 S  (IV).

14. The process of claim 13 , wherein the amine of formula VII, prior to reaction with the isocyanatosilane of formula VI, is prepared from a hydrochloride salt of a diamine of formula VIII
Cl −+ H 3 N—R—S—S—R—NH 3 + Cl −   (VIII)

by addition of a base.

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

16. The process of claim 13 , wherein the product is dried.

Assignees

• Evonik Industries Ag
• Evonik Degussa Gmbh

Inventors

• Röben Caren
• Moser Ralph
• Mayer Stefanie

Classifications

• C07F7/1892

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title

• C08L91/06

  Waxes · CPC title

• C08K3/22

  of metals · CPC title

• C08L7/00

  Compositions of natural rubber · CPC title

• C08K5/47

  Thiazoles · CPC title