Polyether-siloxane block copolymers for the production of polyurethane foams

Patent metadata

Field	Value
Publication number	US-12252588-B2
Application number	US-202117523059-A
Country	US
Kind code	B2
Filing date	Nov 10, 2021
Priority date	Dec 10, 2020
Publication date	Mar 18, 2025
Grant date	Mar 18, 2025

Abstract

A process for preparing polyether-siloxane block copolymers by hydrosilylation of alpha,omega-modified hydrosiloxanes with alpha,omega-modified di(meth)allyl polyethers in the presence of a hydrosilylation catalyst, wherein the reaction is performed in a solvent mixture comprising aromatic solvents, polyethers and alkoxylated alcohol, is described.

First claim

The invention claimed is:

1. A process for preparing polyether-siloxane block copolymers of formula 1

where
a=0 to 100,
b=0 to 100,
c=0 to 100,
a+b+c>3,

d=1 to 100,
n=5-200, and
where the R 1 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms,
and where the R 2 radicals are independently identical or different monovalent aliphatic, saturated or unsaturated hydrocarbon radicals having 1 to 20 carbon atoms or H,
and where the R 3 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms,
and where the R 4 radicals are independently selected from one of the R 5 , R 6 , R 7 radicals or H, where the R 5 radicals conform to the formula 2

and where the R 6 radicals conform to the formula 3

and where the R 7 radicals conform to the formula 4

where the indices a, b and c and the R 2 and R 3 radicals are as defined above,
by hydrosilylation of alpha, omega-modified hydrosiloxanes with alpha, omega-modified di(meth)allyl polyethers in the presence of a hydrosilylation catalyst capable of catalyzing the formation of an SiC bond by addition of an Si—H group onto a (meth)allylic double bond,
wherein the reaction is performed in a solvent mixture comprising toluene and/or alkylbenzene, a polyether of the formula 5

where
g=0 to 75,
h=1 to 100,
i=1 to 100, and
where the R 8 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms, and alkoxylated alcohol of the formula 6

where
j=0 to 30,
k=0 to 20,
1=1 to 20, and
where the R 9 radical is a monovalent aliphatic saturated or unsaturated, linear or branched hydrocarbyl radical having 6-40, carbon atoms,
and where the R 8 radicals are as defined above.

2. The process according to claim 1 , wherein the polyether of the formula 5 and the alkoxylated alcohol of the formula 6 are used in a mass ratio of 1:4 to 4:1.

3. The process according to claim 1 , wherein the aromatic solvent, based on the entire solvent mixture used, comprising toluene and/or alkylbenzene, is used in amounts of >15% by weight.

4. The process according to claim 1 , wherein the sum total of the masses of polyether of the formula 5 and of the alkoxylated alcohol of the formula 6 is in a ratio of 8:2 to 1:4 to the sum total of the masses of the reactants.

5. The process according to claim 1 , wherein the alpha, omega-modified di(meth)allyl polyether is used in such a concentration that the molar ratio of polyether-bound double bonds to siloxane-bound Si—H groups is in the range from 0.95:1.05 to 1.05:0.95.

6. The process according to claim 1 , wherein the hydrosilylation catalyst used for the reaction is selected from the group consisting of platinum catalysts, platinum (0) catalysts, and platinum (0) catalysts in the form of the Karstedt catalyst.

7. The formulation suitable as additive for the production of polyurethane foams, comprising the following components:
(a) polyether-siloxane block copolymers of formula 1

where
a=0 to 100,
b=0 to 100,
c=0 to 100,
d=1 to 100,
n=5-200, and
where the R 1 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms,
and where the R 2 radicals are independently identical or different monovalent aliphatic, saturated or unsaturated hydrocarbon radicals having 1 to 20 carbon atoms or H,
and where the R 3 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms,
and where the R 4 radicals are independently selected from one of the R 5 , R 6 , R 7 radicals or H, where the R 5 radicals conform to the formula 2

and where the R 6 radicals conform to the formula 3

and where the R 7 radicals conform to the formula 4

where the indices a, b and c and the R 2 and R 3 radicals are as defined above,
(b) polyethers of the formula 5

where
g=0 to 75,
h=1 to 100,
i=1 to 100, and
where the R 8 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms,
(c) alkoxylated alcohol of the formula 6

where
j=0 to 30,
k=1 to 20,
l=1 to 20, and
where the R 9 radical is a monovalent aliphatic saturated or unsaturated, linear or branched hydrocarbyl radical having 6-40,
and where the R 8 radicals are as defined above, and
(d) optionally aromatic solvents.

8. The formulation according to claim 7 , wherein components b) and c) are present in a mass ratio of 1:4 to 4:1.

9. The formulation according to claim 7 , wherein the sum total of the masses of b) and c) to a) is in a ratio of 8:2 to 1:4.

10. The formulation according to any of claim 7 , wherein polyether-siloxane block copolymers of formula 1 have a M w (g/mol) of≥60,000, where M w /M n <3.1.

11. The formulation according to claim 7 , wherein the additional component used is at least one pendent polyethersiloxane-based stabilizer having a siloxane chain bearing pendent and/or terminal polyether chains, where the polyether chains may be bonded to the silicone chain via either a silicon-carbon bond (Si—C) or a silicon-oxygen-carbon bond (Si—O—C), or a pendent Si—C-based polyethersiloxanes that conform to the formula 7

where
x=0 to 50,
y=0 to 250,
where the R 9 radicals are independently identical or different monovalent aliphatic or aromatic hydrocarbon radicals having 1 to 20 carbon atoms, and where the R 10 radicals are independently identical or different OH-functional or -terminated, and where the R 11 radicals correspond either to R 9 or R 10 .

12. The formulation according to a process according to claim 1 and subsequent removal of the toluene.

13. A polyurethane foam

Assignees

• Evonik Operations Gmbh

Inventors

• Ferenz Michael
• Klostermann Michael
• Feldmann Kai-Oliver
• Schnell Petra
• Eckhoff Michelle

Classifications

• C08J2375/04

  Polyurethanes · CPC title

• C08J9/0061

  characterized by the use of several polymeric components · CPC title

• C08J9/0042

  containing silicon · CPC title

• C08G2101/00

  Manufacture of cellular products · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title