Silane mixtures and processes for preparation thereof

Patent metadata

Field	Value
Publication number	US-11008441-B2
Application number	US-201816201495-A
Country	US
Kind code	B2
Filing date	Nov 27, 2018
Priority date	Nov 28, 2017
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

The silane mixture according to the invention can be prepared by mixing the silanes of the formula I and silanes of the formula II.

First claim

The invention claimed is:

1. A silane mixture comprising a silane of formula I
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) n —S x —(R 4 —S) n —R 3 —Si(R 1 ) y (R 2 ) 3-y   (I)

and a silane of formula II
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) z —S—R 3 —Si(R 1 ) y (R 2 ) 3-y   (II)

wherein R 1 are each independently C1-C10-alkoxy groups, phenoxy groups, C4-C10-cycloalkoxy groups or alkyl polyether groups —O—(R 5 —O) r —R 6 where R 5 are each independently a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group, r is an integer from 1 to 30, and R 6 is an unsubstituted or substituted, branched or unbranched monovalent alkyl, alkenyl, aryl or aralkyl group,
R 2 are each independently C6-C20-aryl groups, C1-C10 alkyl groups, C2-C20 alkenyl groups, C7-C20-aralkyl groups or halogen,
R 3 are each independently branched or unbranched, saturated or unsaturated, aliphatic, aromatic or
mixed aliphatic/aromatic divalent C1-C30 hydrocarbon groups,
R 4 are each independently branched or unbranched, saturated or unsaturated, aliphatic, aromatic or
mixed aliphatic/aromatic divalent C1-C30 hydrocarbon groups, and x is a number from 2 to 10,
n are the same and are 0, 1, 2 or 3, y are each independently 1, 2 or 3, z is 1, 2 or 3, and the molar ratio of silane of the formula I to silane of the formula II is 19:81-81:19.

2. The silane mixture according to claim 1 , wherein n is 0 or 1 and z=1.

3. The silane mixture according to claim 1 , wherein n=1 and z=1.

4. The silane mixture according to claim 1 , wherein x=2.

5. The silane mixture according to claim 3 , wherein the silane of formula I is (EtO) 3 Si—(CH2) 3 —S—(CH 2 ) 6 —S 2 —(CH2) 6 —S—(CH 2 ) 3 —Si(OEt) and the silane of formula is (EtO) 3 Si—(CH 2 ) 3 —S—(CH 2 )—S—(CH 2 ) 3 —Si(OEt) 3 .

6. The silane mixture according to claim 2 , wherein the silane of formula I is
(EtO) 3 Si—(CH 2 ) 3 —S 2 —(CH2) 3 —Si(OEt) 3

and the silane of formula II is
(EtO) 3 Si—(CH 2 ) 3 —S—(CH2) 6 —S—(CH 2 ) 3 —Si(OEt) 3 .

7. The silane mixture according to claim 1 , wherein the silane of the molar ratio of silane of formula I to the silane of formula II is 20:80-65:35.

8. A process for preparing the silane mixture according to claim 1 , comprising:
mixing the silane of formula I
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) n —Sc(R 4 —S)—R 3 —Si(R 1 ) y (R 2 ) 3-y   (I)

with the silane of formula II
(R 1 ) y (R 2 ) 3-y Si—R 3 —(S—R 4 ) z —S—R 3 —Si(R) y (R 2 ) 3-y   (II)

in a molar ratio of 81:19-19:81.

9. The process for preparing the silane mixture according to claim 8 , wherein n is 0 or 1 and z=1.

10. The process for preparing the silane mixture according to claim 8 , wherein n=1 and z=1.

11. The process for preparing the silane mixture according to claim 8 , wherein the molar ratio of the silane of formula I to the silane of formula II is 50:50-70:30.

12. The process for preparing the silane mixture according to claim 9 , that wherein the silane of formula I is
(EtO) 3 Si—(CH2) 3 —S—(CH 2 )6-S 2 —(CH2) 6 —S—(CH 2 ) 3 —Si(OEt) 3 or (EtO) 3 Si—(CH 2 ) 3 —S 2 —(CH2) 3 —Si(OEt) 3

and the silane of formula II is
(EtO) 3 Si—(CH 2 ) 3 —S—(CH2) 6 —S—(CH 2 ) 3 —Si(OEt) 3 .

13. The process for preparing the silane mixture according to claim 3 , reacting a mercaptosilane of formula III
(R 1 ) y (R 2 ) 3-y Si—R 3 —SH  (III)

with a halogen compound of formula IV
Hal-R 4 -Hal  (IV)

Hal is F, CL Br or I in a molar ratio of the mercaptosilane of formula (III) to the halogen compound of formula (IV) of from 34:86-64:36 to obtain a product;
and reacting the product with sodium polysulfide of the formula (V)
Na 2 S x   (V)

where x is as defined above.

14. The process for preparing the silane mixture according to claim 13 , wherein the mercaptosilane of formula III is
(EtO) 3 Si—(CH 2 ) 3 —SH

the halogen compound of formula IV is C—(CH 2 ) 6 —Cl
and the sodium polysulfide of formula V is Na 2 S 2 .

Assignees

• Evonik Operations Gmbh

Inventors

• Roeben Caren
• Moser Ralph
• Koepfer Alexander
• Rosenstingl Sebastian
• Mayer Stefanie
• Hasse Andre
• Forster Frank

Classifications

• C08L9/06

  Copolymers with styrene · CPC title

• C08L9/00

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

• C08K2201/014

  Additives containing two or more different additives of the same subgroup in C08K · CPC title

• C08K5/548 Primary

  containing sulfur {(C08K5/5477 takes precedence)} · CPC title

• C08K3/36

  Silica · CPC title