IP Library Granted Patent US 7,423,165
Granted Patent B2
US 7,423,165 · App. 10/872,177 · Granted Sep 9, 2008

Organosilicon compounds

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Quick Facts
Patent No.
US 7,423,165
App. No.
10/872,177
Granted
Sep 9, 2008
Kind
B2
Abstract

Organosilicon compounds of the general formula I are produced by catalytically reacting silanes of the general formula II with alcohols of the general formula R′—OH, with the elimination of R IV OH, wherein the molar ratio of R—OH to R IV OH— groups is at least 1 and R IV OH is removed continuously or discontinuously from the reaction mixture. The organosilicon compounds may be used as coupling agents in filler-reinforced rubber mixtures.

Claims (35)

1. An organosilicon compounds of the formula I

in which R are identical or different and denote an R′O group or C 1 -C 12 -alkyl group,

R′ are identical or different and denote a C 12 -C 24 branched or unbranched single-bond alkyl or alkenyl group, aryl group, aralkyl group or R″′ 3 Si, where R′″ denotes a C 1 -C 30 branched or unbranched alkyl or alkenyl group, aralkyl group or aryl group,

R″ is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic double-bond C 1 -C 30 hydrocarbon group,

X denotes SH where n=1 and m=1, SCN where n=1 and m=1, or S where n=2 and m=1-14, and mixtures thereof.

2. The organosilicon compound according to claim 1 , wherein R is methyl or ethyl.

3. The organosilicon compound according to claim 1 , wherein R″′ is C 1 -C 8 alkyl or alkenyl.

4. The organosilicon compound according to claim 1 , wherein R is one or two alkyl groups.

5. The organosilicon compound according to claim 1 , wherein R″ is CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 (CH 3 ) CH 2 CH(CH 3 ), CH 2 CH(CH 3 ), CH(CH 3 )CH 2 , C(CH 3 ) 2 , CH 2 (C 3 H 5 ), CH 2 CH 2 CH(CH 3 ), CH 2 CH(CH 3 )CH 2 or

6. An inert organic or inorganic carrier supporting thereon the organosilicon compound according to claim 1 .

7. An oligomer or polymer made from an organosilicon compound according to claim 1 .

8. A process for the production of the organosilicon compound according to claim 1 , comprising catalytically reacting a silane of the formula II

wherein R V are identical or different and denote an R IV O—, or C 1 -C 12 -alkyl group, R IV are identical or different and denote a methyl or ethyl group,

with an alcohol of the formula R′—OH

eliminating R IV OH, wherein the molar ratio of R′—OH to R IV O— groups is at least 1 and R IV OH is removed continuously or discontinuously from the reaction mixture.

9. The process according to claim 8 , wherein a pure alcohol or alcohol mixture is used as the alcohol of the formula R′—OH.

10. Process according to claim 8 , wherein a metal-free or metal-containing catalyst is used as catalyst.

11. Process according to claim 10 , wherein a compound of the 3 rd -7 th group, of the 13 th -14 th group and/or of the lanthanide group is used as metal.

12. Process according to claim 11 , wherein a titanium alkoxide is used as metal containing catalyst.

13. Process according to claim 8 , wherein an organic acid is used as catalyst.

14. Process according to claim 8 , wherein the reacting is carried out under the exclusion of moisture and oxygen and under reduced pressure.

15. A vulcanizible rubber mixture, comprising rubber, filler, optionally further rubber auxiliary substances, as well as at least one organosilicon compound according to claim 1 .

16. A vulcanized rubber mixture comprising rubber, a filler and at least one organosilicon compound according to claim 1 .

17. A moulded article made from the rubber mixtures according to claim 16 .

18. An article formed from the vulcanizible rubber mixture of claim 15 in the form of a pneumatic tire, tire tread, cable sheathing, hose, drive belt, conveyor belt, roller covering, tire, shoe sole, sealing ring or damping element.

19. The organosilicon compound according to claim 1 which is:

(C 14 H 29 O/C 16 H 33 O/C 18 H 37 O) 3 SiC 3 H 6 —SH.

20. The inert organic or inorganic carrier according to claim 6 , wherein the organosilicon compound is:

(C 14 H 29 O/C 16 H 33 O/C 18 H 37 O) 3 SiC 3 H 6 —SH.

21. The oligomer or polymer according to claim 7 wherein the organosilicon compound is:

(C 14 H 29 O/C 16 H 33 O )/C 18 H 37 O) 3 SiC 3 H 6 —SH.

22. The vulcanizable rubber mixture according to claim 15 wherein the organosilicon compound is:

(C 14 H 29 O/C 16 H 33 O)/C 18 H 37 O) 3 SiC 3 H 6 —SH.

23. The vulcanized rubber mixture according to claim 16 wherein the organosilicon compound is:

(C 14 H 29 O/C 16 H 33 O/C 18 H 37 O) 3 SiC 3 H 6 —SH.

Assignments (5)
CHANGE OF NAME Recorded Mar 29, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052254/0052 →
CHANGE OF NAME Recorded Feb 23, 2010
From: DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 024006/0127 →
CHANGE ADDRESS Recorded Feb 22, 2010
From: EVONIK DEGUSSA GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 023985/0296 →
CHANGE OF ENTITY Recorded Feb 22, 2010
From: DEGUSSA AG
To: DEGUSSA GMBH
Reel/Frame 023998/0937 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 25, 2004
From: KORTH, KARSTEN; ALBERT, PHILIPP; PIETER, REIMUND; KLOCKMANN, OLIVER; HASSE, ANDRE; DESCHLER, ULRICH; WITZSCHE, SUSANN; KIEFER, INGO
To: DEGUSSA AG
Reel/Frame 015034/0751 →