Method of hydrosilylation implementing an organic catalyst derived from germylene

• US 10,442,825 B2
• Filed: 11/12/2015
• Issued: 10/15/2019
• Est. Priority Date: 11/14/2014
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique
• Original Assignee: Bluestar Silicones France SAS
• Inventors: Baceiredo, Antoine, Kato, Tsuyoshi, Mao, Yanli, Berthe, Juliette, Bousquie, Magali
• Primary Examiner(s): Brooks, Clinton A
• Application Number:
  US15/523,727
• Publication Number:
  US 20170313729A1
• Time in Patent Office: 1,433 Days
• Field of Search: None
• CPC Class Codes: B01J 2231/323 Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
• CPC Class Codes: B01J 2531/40 Complexes comprising metals of Group IV (IVA or IVB) as the central metal
• CPC Class Codes: B01J 31/1608 the ligands containing silicon
• CPC Class Codes: B01J 31/187 Amide derivatives thereof
• CPC Class Codes: B01J 31/189 containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
• CPC Class Codes: B01J 31/2226 Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
• CPC Class Codes: C07F 7/0829 Hydrosilylation reactions
• CPC Class Codes: C07F 7/30 Germanium compounds

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.

Claims

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

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

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 R₁ and R₂ 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:

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

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_gU_bSiO<sub>(4−

(g+h))/2</sub> 

 

(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_dU_eSiO<sub>(4−

(d+e))/2</sub> 

 

(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.