Super acids and bases as dehydrocondensation catalysts

Patent metadata

Field	Value
Publication number	US-9901912-B2
Application number	US-201615169941-A
Country	US
Kind code	B2
Filing date	Jun 1, 2016
Priority date	Jun 2, 2015
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

There is provided herein a composition which contains hydride-functionalized siloxane or silane, a hydroxyl-containing compound that does not contain silicon, and a catalytically-effective amount of super acid or super base catalyst selected from the group consisting of a triaza-containing compound which contains only carbon, nitrogen and hydrogen atoms, an atrane compound, a linear or branched compound containing a sulfonyl group and a fluoro group, and combinations thereof. There is also provided a process of making such a composition.

First claim

The invention claimed is:

1. A composition comprising:
(A) a hydride-functionalized siloxane or silane,
(B) a hydroxyl-containing compound that does not contain silicon, and
(C) a catalytically-effective amount of a super acid or super base catalyst selected from the group consisting of (1) a triazabicyclo-containing compound, (2) azaphosphatrane-containing compound, (3) a linear or branched compound selected from the group consisting of a compound containing sulfonic acid group and a fluoro group, a compound containing a sulfonate group and a fluoro group, a compound containing a sulfonimide group and a fluoro group, and combinations thereof.

2. The composition of claim 1 wherein the hydroxyl-containing compound that does not contain silicone is of the formula R—OH wherein R is an organic group containing from 1 to about 20 carbon atoms.

3. The composition of claim 1 wherein the triazabicycio-containing compound is a triazabicycloalkene containing from 3 to 15 carbon atoms.

4. The composition, of claim 1 wherein the triazabicyclo-containing compound is a triazabicycloalkene containing from 4 to 12 carbon atoms.

5. The composition of claim 1 wherein the triazabicyclo-containing compound is a triazabicycloalkene containing from 5 to 8 carbon atoms.

6. The composition of claim 1 wherein the azaphosphatrane-containing compound is an alkylazaphosphatrane wherein the alkyl group contains from 1 to 6 carbon atoms.

7. The composition of claim 1 wherein the compound containing a sulfonic acid group and a fluoro group is a fluorinated alkane sultbnic acid wherein the fluorinated alkane group contains from 1 to 6 carbon atoms.

8. The composition of claim 1 wherein the compound containing a sulfonic acid group and a fluoro group is a fluorinated alkane sulfonic acid selected from the group consisting of trifluoromethanesulfonic acid, pentafluorobutanesulfonic acid, heptafluoropropanesulfonic acid, nonafluorobutanesultunic acid, undecafluoropentanesulfonic acid, tridecafluorohexanesulfonic acid, pentadecafluoroheptasulfonic acid, heptadecafluorooctanesulfonic acid, nonadecafluorononanesulfonic acid and combinations thereof.

9. The composition of claim 1 wherein the compound containing a sulfonate group and fluoro group further comprises an organosilyl group wherein the organo group contains from 1 to 4 carbon atoms and wherein the fluoro group is a fluoroalkane group containing from 1 to 3 carbon atoms.

10. The composition of claim 1 wherein the compound containing a sulfonate group and fluoro group further comprises an organosilyl group and is selected from the group consisting of trimethylsilyltrifluoromethanesulfonic acid, trimethylsilylpentafluoroethanesulfonic acid, trimethylsilylheptafluoropropanesulfonic acid, trimethylsilylundecafluorobutanesulfonic acid, trimethylsilylundecafluoropentanesulfonic acid, trimethylsilyltridecafluorohexanesulfonic acid, trimethylsilylpentadecafluoroheptasulfonic acid, trimethylsilylheptadecafluorooctanesulfonic acid, trimethylsilylnonadecafluorononanesulfonic acid and combinations thereof.

11. The composition of claim 1 wherein the compound containing a sulfonimide group and fluoro group is a bis(fluoroalkyl) sulfonimide compound wherein the fluoroalkyl group contains from 1 to 3 carbon atoms.

12. The composition of claim 1 wherein the compound containing a sulfonimide group and fluoro group is a bis(fluoroalkyl)sulfonimide compound selected from the group consisting of bis(trifluoromethane)sulfonimmide, bis(pentafluoroethane)sulfonimide, bis(heptafluompropane)sulfonimide, bis(nonafluorobutane) sulfonimide, bis(undecafluoropentane)sulfonimide, bis(tridecafluorohexane)sulfonimide, bis(pentadecafluoroheptae)sulfonimide, bis(heptadecafluorooctane)sulfonimide, bis(nonadecafluorononane)sulfonimide and combinations thereof.

13. The composition of claim 11 wherein the bis(fluoroalkyl)sulfonimide compound further comprises a triorganosilyl moiety.

14. The composition of claim 13 wherein the bis(fluoroalkyl)sulfonimide compound further comprising a triorganosilyl moiety is selected from the group consisting of N-trimethylsilylbis(trifluoromethane)sulfonimide,N-trimethylsilyibis(pentafluoroethane)sulfonimide, N-trimethylsilylbis(heptafluoropropane)sulfonimide, N-trimethylsilyibis(nonafluorobutane) sulfonimide, N-trimethylsilybis(undecafluoropentane)sulfonimide, bis(tridecafluorohexane)sulfonimide,N-trimethylsilyibis(pentadecafluoroheptae)sulfonimide, N-trimethylsilylbis(heptadecafluorooctane)sulfonimide, N-trimethylsilylbis(nonadecafluorononane)sulfonimide and combinations thereof.

15. The composition of claim 1 wherein the catalytically-effective amount of a sulfonyl-containing super acid or a super base catalyst is from about 0.5 wt % to about 1.5 wt % based on the total weight of the composition.

16. A catalytic dehydrocondensation process comprising:
reacting the composition of claim 1 .

17. The functionalized siloxane containing a Si—O—C bond formed by the process of claim 16 .

18. A formulation which is an agrochemical formulation, a personal care formulation, a personal care formulation or a coating formulation which comprises the functionalized siloxane of claim 17 .

Assignees

• Momentive Performance Mat Inc

Inventors

• Sivasubramanian Karthikeyan
• Khare Vivek P

Classifications

• C08G77/08 Primary

  characterised by the catalysts used · CPC title

• C07F7/188

  by reactions involving the formation of Si-O linkages · CPC title

• C08K5/3477

  Six-membered rings · CPC title

• C08K5/43

  Compounds containing sulfur bound to nitrogen · CPC title

• C08L83/04

  Polysiloxanes · CPC title