IP Library Granted Patent US 7,799,938
Granted Patent B2
US 7,799,938 · App. 12/213,077 · Granted Sep 21, 2010

Method for the production of (mercaptoorganyl)alkyl polyether silanes

Assignee: Evonik Degussa GmbH
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Quick Facts
Patent No.
US 7,799,938
App. No.
12/213,077
Granted
Sep 21, 2010
Kind
B2
Abstract

The invention relates to a method for producing (mercaptoorganyl)alkyl polyether silanes by reacting dry mercaptization reagents with a (haloorganyl)alkyl polyether silane.

Claims (33)

1. A process for preparing a (mercaptoorganyl)alkyl polyether silane, comprising reacting a dry mercaptation reagent with a (haloorganyl)alkyl polyether silane, wherein said mercaptation reagent has a water content of less than 3% by weight.

2. The process of claim 1 , wherein the reaction between said dry mercaptation reagent and said (haloorganyl)alkyl polyether silane is carried out in a closed vessel, in the absence of air and under an elevated pressure.

3. The process of claim 1 , wherein the reaction between said dry mercaptation reagent and said (haloorganyl)alkyl polyether silane is carried out in a solvent consisting of one or more organic solvents or one or more compressed gases.

4. The process of claim 1 , wherein said (mercaptoorganyl)alkyl polyether silane is a compound of formula I:

(X)(X′)(X″)Si—R I —SH  (I)

wherein:

X is an alkyl polyether group O—(CR II 2 ) w —O—) v Alk where v=1-40, w=1-40, R II are each independently H, a phenyl group or an alkyl group, Alk is a branched or unbranched, saturated or unsaturated, substituted or unsubstituted, aliphatic, aromatic or mixed aliphatic/aromatic monovalent C 1 -C 35 -hydrocarbon group,

X′ is a branched or unbranched alkyl, a branched or unbranched alkoxy, a branched or unbranched alkenyloxy group, a branched or unbranched aryloxy group, a branched or unbranched alkylaryloxy group, a branched or unbranched aralkyloxy group or an X group,

X″ is a branched or unbranched alkyl, a branched or unbranched alkoxy, a branched or unbranched alkenyloxy group, a branched or unbranched aryloxy group, a branched or unbranched alkylaryloxy group, a branched or unbranched aralkyloxy group or an X group,

R I is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C 1 -C 30 hydrocarbon group.

5. The process of claim 1 , wherein said (haloorganyl)alkyl polyether silane is a compound of formula II:

(X)(X′)(X″)Si—R I -Hal  (II)

where R I , X, X′ and X″ are each as defined as for formula I, and Hal is chlorine, bromine, fluorine or iodine.

6. The process of claim 1 , wherein said dry mercaptation reagent is an alkali metal hydrogensulfide or ammonium hydrogensulfide.

7. The process of claim 1 , wherein said dry mercaptation reagent is selected from the group consisting of: lithium hydrogensulfide (LiSH), sodium hydrogensulfide (NaSH), potassium hydrogensulfide (KSH) and cesium hydrogensulfide (CsSH).

8. The process of claim 1 , wherein said dry mercaptation reagent is (NH 4 )SH, NH 3 (Sub)SH, NH 2 (Sub) 2 SH or NH(Sub) 3 SH, wherein Sub is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic monovalent C 1 -C 30 hydrocarbon group.

9. The process of claim 1 , wherein additives are added to the reaction mixture at the start of the reaction and/or during the reaction and/or at the end of the reaction.

10. The process of claim 1 , wherein the molar amount of dry mercaptation reagent used is from 70 mol % to 150 mol % of the molar amount of the (haloorganyl)alkyl polyether silane used.

11. The process of claim 3 , wherein said solvent comprises one or more compounds selected from the group consisting of: an alkane; ether; aromatic solvent; alcohol or carbonyl-containing solvent.

12. The process of claim 4 , wherein said (haloorganyl)alkyl polyether silane is a compound of formula II:

(X)(X′)(X″)Si—R I -Hal  (II)

where R I , X, X′ and X″ are each as defined as for formula I, and Hal is chlorine, bromine, fluorine or iodine.

13. The process of claim 12 , wherein the reaction between said dry mercaptation reagent and said (haloorganyl)alkyl polyether silane is carried out in a closed vessel, in the absence of air and under an elevated pressure.

14. The process of claim 13 , wherein the reaction between said dry mercaptation reagent and said (haloorganyl)alkyl polyether silane is carried out in a solvent consisting of one or more organic solvents or one or more compressed gases.

15. The process of claim 14 , wherein said dry mercaptation reagent is an alkali metal hydrogensulfide or ammonium hydrogensulfide.

16. The process of claim 14 , wherein said dry mercaptation reagent is selected from the group consisting of: lithium hydrogensulfide (LiSH), sodium hydrogensulfide (NaSH), potassium hydrogensulfide (KSH) and cesium hydrogensulfide (CsSH).

17. The process of claim 14 , wherein said dry mercaptation reagent is (NH 4 )SH, NH 3 (Sub)SH, NH 2 (Sub) 2 SH or NH(Sub) 3 SH, wherein Sub is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic monovalent C 1 -C 30 hydrocarbon group.

18. The process of claim 14 , wherein additives are added to the reaction mixture at the start of the reaction and/or during the reaction and/or at the end of the reaction.

19. The process of claim 14 , wherein the molar amount of dry mercaptation reagent used is from 70 mol % to 150 mol % of the molar amount of the (haloorganyl)alkyl polyether silane used.

20. The process of claim 14 , wherein:

a) said dry mercaptation reagent is selected from the group consisting of: lithium hydrogensulfide (LiSH), sodium hydrogensulfide (NaSH), potassium hydrogensulfide (KSH) and cesium hydrogensulfide (CsSH);

b) additives are added to the reaction mixture at the start of the reaction and/or during the reaction and/or at the end of the reaction; and

c) the molar amount of dry mercaptation reagent used is from 70 mol % to 150 mol % of the molar amount of the (haloorganyl)alkyl polyether silane used.

Assignments (2)
CHANGE OF NAME Recorded Feb 1, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051776/0127 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2008
From: KORTH, KARSTEN; LAUR, DIRK; ALBERT, PHILIPP; KIEFER, INGO
To: EVONIK DEGUSSA GMBH
Reel/Frame 021443/0178 →
Priority Claims (1)
DE 10 2005 060 122 · Dec 16, 2005 · national
Continuity (1)
Related Publication 20080319128A1 · Dec 25, 2008