Method of hydrosilylation implementing an organic catalyst derived from germylene

Patent metadata

Field	Value
Publication number	US-10442825-B2
Application number	US-201515523727-A
Country	US
Kind code	B2
Filing date	Nov 12, 2015
Priority date	Nov 14, 2014
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

The present invention concerns a method for the hydrosilylation of an unsaturated compound comprising at least one ketone function, one aldehyde function, one alkene function and/or one alkyne function, with a compound comprising at least one hydrogen-silyl function implementing an organic catalyst of tri-coordinated germanium.

First claim

The invention claimed is:

1. An organic compound (C) represented by Formula 1:

in which
L is an alkoxy group comprising from 1 to 18 carbon atoms,
Y is an alkyl group containing from 1 to 20 carbon atoms or an aryl group containing from 6 to 18 carbon atoms,
the groups R 1 and R 2 , which may be identical or different, represent a hydrogen atom, an alkyl group containing from 1 to 20 carbon atoms, an alkenyl group containing from 2 to 12 carbon atoms, an aryl group containing from 6 to 18 carbon atoms, or R 1 and R 2 together possibly forming a saturated or unsaturated, substituted ring of 5 to 8 atoms, and in the phosphine group

the groups R 3 and R 4 , which may be identical or different, represent a hydrogen atom, a halogen atom, an alkyl or a haloalkyl group containing from 1 to 20 carbon atoms, a cycloalkyl group containing from 3 to 20 carbon atoms, a cycloalkyl-alkyl group containing from 4 to 40 carbon atoms, an aryl group containing from 6 to 18 carbon atoms, an aryl-alkyl group containing from 6 to 38 carbon atoms; R 3 and R 4 also possibly forming, with the atoms to which they are attached, a monocyclic or polycyclic ring consisting of 3 to 20 atoms.

2. The compound as claimed in claim 1 , wherein the phosphine group is represented by the formulae:

in which tBu is the tert-butyl group.

3. The compound as claimed in claim 1 , wherein L is an alkoxy group chosen from methoxy, ethoxy, propoxy and butoxy.

4. The compound as claimed in claim 1 wherein L is an ethoxy group.

5. The compound as claimed in claim 1 , wherein R 1 and R 2 together form a saturated or unsaturated substituted ring of 5 to 8 atoms, in which two of the substituents form a bridge of 1 to 3 atoms on said ring.

6. The compound as claimed in claim 1 , wherein the organic compound (C) of Formula 1 has the following structure:

wherein
Y is 2,6-iPr 2 —C 6 H 3 , and
the phosphine group is represented by the formulae:

in which tBu is the tert-butyl group.

7. The compound as claimed in claim 1 , wherein the organic compound (C) has the following structure:

in which
Y is 2,4,6-trimethyl-C 6 H 2 , and
the phosphine group is represented by the formula:

in which tBu is the tert-butyl group.

8. A product comprising an organic compound (C) as claimed in claim 1 , as a hydrosilylation catalyst.

9. A composition comprising:
at least one unsaturated compound (A) comprising at least one ketone function, aldehyde function, alkene function and/or alkyne function,
at least one compound (B) comprising at least one hydrogenosilyl function, and
a catalyst chosen from the organic compounds (C) as claimed in claim 1 .

10. The composition as claimed in claim 9 , wherein the molar concentration of catalyst in the composition is from 0.5% to 10%, relative to the number of moles of unsaturated compound (A).

11. The composition as claimed in claim 9 , wherein the molar concentration of catalyst in the composition is from 1.5% to 5.5% relative to the number of moles of unsaturated compound (A).

12. The compound as claimed in claim 1 , wherein L is a linear alkoxy group with 1 to 18 carbon atoms.

13. A process for the hydrosilylation of an unsaturated compound (A) comprising at least one ketone function, aldehyde function, alkene function and/or alkyne function, with a compound (B) comprising at least one hydrogenosilyl function, wherein said process comprises catalysing with the organic compound (C) according to claim 1 .

14. The process as claimed in claim 13 , wherein the unsaturated compound (A) comprises one or more alkene or alkyne functions and from 2 to 40 carbon atoms.

15. The process as claimed in claim 13 , wherein compound (B) comprises at least one hydrogenosilyl function chosen from:
a silane or polysilane compound comprising at least one hydrogen atom bonded to a silicon atom,
an organopolysiloxane compound comprising at least one hydrogen atom bonded to a silicon atom, and an organic polymer comprising hydrogenosilyl functions in end positions.

16. The process as claimed in claim 13 , wherein:
the unsaturated compound (A) is chosen from organopolysiloxane compounds comprising units of formula (I):
A g U b SiO (4−(g+h))/2   (I)

in which:
the radicals A, which may be identical or different, represent a linear or branched alkenyl or alkynyl radical containing between 2 and 6 carbon atoms;
the radicals U, which may be identical or different, represent a monovalent radical other than a hydrogen atom,
g and h represent integers, g being 1 or 2, h being 0, 1 or 2 and (g+h) being 1, 2 or 3;

compound (B) comprising at least one hydrogenosilyl function is an organopolysiloxane comprising at least one unit of formula (III):
H d U e SiO (4−(d+e))/2   (III)

in which:
U has the same meaning as above,
d and e represent integers, d being 1 or 2, e being 0, 1 or 2 and (d+e) being 1, 2 or 3.

Assignees

• Bluestar Silicones France
• Centre Nat Rech Scient
• Elkem Silicones France Sas

Inventors

• Baceiredo Antoine
• Kato Tsuyoshi
• Mao Yanli
• Berthe Juliette
• Bousquié Magali

Classifications

• B01J31/187

  Amide derivatives thereof · CPC title

• B01J31/2226

  Anionic ligands, i.e. the overall ligand carries at least one formal negative charge · CPC title

• C07F7/30 Primary

  Germanium compounds · CPC title

• B01J2531/40

  Complexes comprising metals of Group IV (IVA or IVB) as the central metal · CPC title

• B01J31/1608

  the ligands containing silicon · CPC title