Noble metal-free hydrosilylatable mixture

Patent metadata

Field	Value
Publication number	US-10730893-B2
Application number	US-201716091026-A
Country	US
Kind code	B2
Filing date	Mar 10, 2017
Priority date	Apr 4, 2016
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

The invention relates to a hydrosilylatable mixture M containing: (A) a compound with at least one hydrogen atom directly bonded to Si, (B) a compound containing at least one carbon-carbon multiple bond, and (C) a compound containing at least one cationic Si(II) group. The invention also relates to a method for hydrosilylating the mixture M.

First claim

The invention claimed is:

1. A hydrosilylatable mixture M comprising:
(A) a compound having at least one hydrogen atom bonded directly to Si,
(B) a compound comprising at least one carbon-carbon multiple bond and
(C) a compound comprising at least one cationic Si(II) moiety,
wherein the compound C is a cationic Si(II) compound of formula IV
([Si(II)Cp] + ) a X a−   (IV)

in which
Cp is a π-bonded cyclopentadienyl radical of formula V, which is substituted by radicals R y ,

R y are monovalent radicals or polyvalent radicals, which are optionally bonded to one another to form one or more fused rings and
X − signifies an a valent anion, which does not react with the cationic silicon(II) under the reaction conditions of hydrosilylation.

2. The hydrosilylable mixture M of claim 1 , wherein at least one compound A has the formula I
R 1 R 2 R 3 Si—H  (I)

wherein the radicals R 1 , R 2 and R 3 each independently are hydrogen, halogen, silyloxy radical, hydrocarbon radical or hydrocarbonoxy radical, wherein individual carbon atoms in each case may be replaced by oxygen atoms, silicon atoms, nitrogen atoms, halogen, sulfur or phosphorus atoms.

3. The hydrosilylable mixture M of claim 1 , wherein compound B is selected from the group consisting of compounds of the formula IIIa
R 4 R 5 C═CR 6 R 7   (IIIa),

of formula IIIb
R 8 C≡CR 9   (IIIb),

and mixtures thereof,
wherein
R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently linear, branched, acyclic or cyclic, saturated or mono- or polyunsaturated C1-C20 hydrocarbon radicals, wherein individual carbon atoms may be replaced by silicon, oxygen, halogen, nitrogen, sulfur or phosphorus.

4. The hydrosilylable mixture M of claim 1 , wherein R a is an unbranched alkyl radical or 2,6-dialkylated phenyl radical.

5. The hydrosilylable mixture M of claim 1 , wherein the molar ratio between compound C and Si—H moieties present in compound A is from 1:10 7 to 1:50.

6. A method for hydrosilylating a mixture M comprising a compound A having at least one silicon-bonded hydrogen atom and a compound B having at least one carbon-carbon multiple bond, comprising:
reacting compound A with compound B in the presence of a compound C as a hydrosilylation catalyst, wherein
the compound C comprises at least one cationic Si(II) moiety, and
the compound C comprises a cationic Si(II) compound of formula IV
([Si(II)Cp] + ) a X a−   (IV)

in which
Cp is a π-bonded cyclopentadienyl radical of formula V, which is substituted by radicals R y ,

R y are monovalent radicals or polyvalent radicals, which are optionally bonded to one another to form one or more fused rings and
X − signifies an a valent anion, which does not react with cationic silicon(II) under the reaction conditions of hydrosilylation.

7. The method of claim 6 , wherein the compound A has the formula I
R 1 R 2 R 3 Si—H  (I)

wherein the radicals R 1 , R 2 and R 3 each independently are hydrogen, halogen, silyloxy radical, hydrocarbon radical or hydrocarbonoxy radical, wherein individual carbon atoms in each case may be replaced by oxygen atoms, silicon atoms, nitrogen atoms, halogen, sulfur or phosphorus atoms.

8. The method of claim 6 , wherein at least one compound B is selected from the group consisting of compounds of the formula IIIa
R 4 R 5 C═CR 6 R 7 ,  (IIIa),

formula IIIb
R 8 C≡CR 9   (IIIb),

and mixtures thereof,
wherein
R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently linear, branched, acyclic or cyclic, saturated or mono- or polyunsaturated C1-C20 hydrocarbon radicals, wherein individual carbon atoms may be replaced by silicon, oxygen, halogen, nitrogen, sulfur or phosphorus.

9. The method of claim 6 , wherein R a is an unbranched alkyl radical or 2,6-dialkylated phenyl radical.

10. The method of claim 6 , wherein the molar ratio between the compound C and the Si—H moieties present in the compound A is from 1:10 7 to 1:50.

Assignees

• Wacker Chemie Ag

Inventors

• Fritz-Langhals Elke
• Jutzi Peter
• Weidner Richard

Classifications

• C07F17/00

  Metallocenes · CPC title

• C07F7/0879 Primary

  Hydrosilylation reactions · CPC title

• B01J31/128 Primary

  Mixtures of organometallic compounds · CPC title

• B01J2231/323

  Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation · CPC title