IP Library Granted Patent US 11,021,575
Granted Patent B2
US 11,021,575 · App. 16/458,226 · Granted Jun 1, 2021

Process for producing acetoxy-bearing siloxanes

Inventors: Wilfried Knott (Essen, DE); Horst Dudzik (Essen, DE); Frauke Henning (Essen, DE); Jan Caßens (Datteln, DE)
Assignee: Evonik Operations GmbH
C08G77/392C07F7/0801C08G77/70
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,021,575
App. No.
16/458,226
Granted
Jun 1, 2021
Kind
B2
Abstract

Described is a process for producing trifluoromethanesulfonic acid-acidified, end-equilibrated, acetoxy-bearing siloxanes which comprises reacting cyclic siloxanes, in particular comprising D 4 and/or D 5 , and/or cyclic branched siloxanes of the D/T type with acetic anhydride using trifluoromethanesulfonic acid as catalyst and with addition of acetic acid.

Claims (28)

1. A process for producing trifluoromethanesulfonic acid-acidified, end-equilibrated, acetoxy-bearing siloxanes, wherein the process comprises

reacting cyclic siloxanes, comprising D 4 and/or D 5 ,

and/or mixtures of cyclic branched siloxanes of the D/T type with acetic anhydride

using trifluoromethanesulfonic acid as catalyst and with addition of acetic acid.

2. The process according to claim 1 , wherein the process comprises adding acetic acid in amounts of 0.4 to 3.5 percent by weight, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5

or consisting of acetic anhydride and mixtures of cyclic branched siloxanes of the D/T type

or consisting of cyclic siloxanes comprising D 4 and/or D 5 and mixtures of cyclic branched siloxanes of the D/T type.

3. The process according to claim 2 , wherein the reaction is carried out in a temperature range of from 140° C. to 160° C. and over a duration of from 4 to 8 hours.

4. The process according to claim 1 , wherein mixtures of cyclic branched siloxanes of the D/T type consisting of siloxanes comprising D and T units and whose 29 Si NMR spectroscopy-determinable cumulative proportion of D and T units comprising Si-alkoxy and/or SiOH groups present in a siloxane matrix, and contain at least 5 percent by weight of cyclic siloxanes.

5. The process according to claim 4 , wherein the reaction is carried out in a temperature range of 140° C. to 160° C. and over a duration of from 4 to 8 hours.

6. The process according to claim 1 , wherein mixtures of cyclic branched siloxanes comprising exclusively D and T units whose 29 Si NMR spectroscopy-determinable cumulative proportion of D and T units comprising Si-alkoxy and/or SiOH groups present in a siloxane matrix.

7. The process according to claim 1 , wherein trifluoromethanesulfonic acid is employed in amounts of 0.1 to 1.0 percent by mass, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5 ,

and/or mixtures of cyclic branched siloxanes of the D/T type.

8. The process according to claim 1 , wherein the reaction is carried out in a temperature range of 140° C. to 160° C. and over a duration of 4 to 8 hours.

9. A trifluoromethanesulfonic acid-acidified, end-equilibrated linear α,ω-acetoxy-bearing siloxane produced by a process according to claim 1 , wherein the trifluoromethanesulfonic acid-acidified, end-equilibrated linear α,ω-acetoxy-bearing siloxane have total cycles contents defined as the sum of the content fractions of the cyclic siloxanes comprising D 4 , D 5 and D 6 based on a siloxane matrix and determined by gas chromatography after their derivatization to afford the corresponding linear α,ω-isopropoxysiloxanes of less than 13% by weight.

10. The trifluoromethanesulfonic acid-acidified, end-equilibrated linear α,ω-acetoxy-bearing siloxane of claim 9 wherein the trifluoromethanesulfonic acid-acidified, end-equilibrated linear α,ω-acetoxy-bearing siloxane have total cycles contents defined as the sum of the content fractions of the cyclic siloxanes comprising D 4 , D 5 and D 6 based on a siloxane matrix and determined by gas chromatography after their derivatization to afford the corresponding linear α,ω-isopropoxysiloxanes of less than 12% by weight.

11. A trifluoromethanesulfonic acid-acidified, end-equilibrated branched acetoxy-bearing siloxane produced by a process according to claim 1 , wherein the trifluoromethanesulfonic acid-acidified, end-equilibrated branched acetoxy-bearing siloxane has total cycles contents defined as the sum of the content fractions of the cyclic siloxanes comprising D 4 , D 5 and D 6 based on a siloxane matrix and determined by gas chromatography after their derivatization to afford the corresponding branched isopropoxysiloxanes of less than 8% by weight.

12. The process according to claim 1 , wherein the process comprises adding acetic acid in amounts of 0.5 to 3 percent by weight, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5

or consisting of acetic anhydride and mixtures of cyclic branched siloxanes of the D/T type

or consisting of cyclic siloxanes comprising D 4 and/or D 5 and mixtures of cyclic branched siloxanes of the D/T type.

13. The process according to claim 1 , wherein the process comprises adding acetic acid in amounts of 0.8 to 1.8 percent by weight, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5

or consisting of acetic anhydride and mixtures of cyclic branched siloxanes of the D/T type

or consisting of cyclic siloxanes comprising D 4 and/or D 5 and mixtures of cyclic branched siloxanes of the D/T type.

14. The process according to claim 1 , wherein the process comprises adding acetic acid in amounts of 1.0 to 1.5 percent by weight, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5

or consisting of acetic anhydride and mixtures of cyclic branched siloxanes of the D/T type

or consisting of cyclic siloxanes comprising D 4 and/or D 5 and mixtures of cyclic branched siloxanes of the D/T type.

15. The process according to claim 1 , wherein mixtures of cyclic branched siloxanes of the D/T type consisting of siloxanes comprising D and T units and whose 29 Si NMR spectroscopy-determinable cumulative proportion of D and T units comprising Si-alkoxy and/or SiOH groups present in a siloxane matrix, and which contain at least 5 percent by weight of octamethylcyclotetrasiloxane (D 4 ), decamethylcyclopentasiloxane (D 5 ) or mixtures thereof, are employed.

16. The process according to claim 1 , wherein trifluoromethanesulfonic acid is employed in amounts of 0.1 to 0.3 percent by mass, based on the reaction matrix consisting of acetic anhydride and cyclic siloxanes comprising D 4 and/or D 5 , and/or mixtures of cyclic branched siloxanes of the D/T type.

Assignments (2)
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 9, 2019
From: KNOTT, WILFRIED; DUDZIK, HORST; HENNING, FRAUKE; CASSENS, JAN
To: EVONIK DEGUSSA GMBH
Reel/Frame 050007/0917 →
Priority Claims (1)
EP 18189073 · Aug 15, 2018 · regional
Continuity (1)
Related Publication 20200055991A1 · Feb 20, 2020
Cited By (3)
US 12,460,081 US 12,577,351 US 12,674,030