Super acids and bases as dehydrocondensation catalysts

Patent metadata

Field	Value
Publication number	US-2016354769-A1
Application number	US-201615169941-A
Country	US
Kind code	A1
Filing date	Jun 1, 2016
Priority date	Jun 2, 2015
Publication date	Dec 8, 2016
Grant date	—

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

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 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.

2 . The composition of claim 1 wherein the hydroxyl-containing compound that does not contain silicone is of the general 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 triaza-containing compound is a triazabicyclo-containing compound.

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

5 . The composition of claim 3 wherein the triazabicyclo-containing compound is a triazabicycloalkene containing from 4 to 12 carbon atoms.

6 . The composition of claim 3 wherein the triazabicyclo-containing compound is a triazabicycloalkene containing from 5 to 8 carbon atoms.

7 . The composition of claim 1 wherein the atrane compound is an azaphosphatrane-containing compound.

8 . The composition of claim 7 wherein the azaphosphatrane-containing compound is an alkylazanphosphatrane wherein the alkyl group contains from 1 to 6 carbon atoms.

9 . The composition of claim 1 wherein the linear or branched compound containing a sulfonyl group and a fluoro group is selected from the group consisting of a compound containing a sulfonic acid group and a fluoro group, a compound containing a sulfonate group and fluoro group, a compound containing a sulfonimide group and fluoro group, and combinations thereof.

10 . The composition of claim 9 wherein the compound containing a sulfonic acid group and a fluoro group is a fluorinated alkane sulfonic acid wherein the fluorinated alkane group contains from 1 to 6 carbon atoms.

11 . The composition of claim 9 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, pentafluoroethanesulfonic acid, heptafluoropropanesulfonic acid, nonafluorobutanesulfonic acid, undecafluoropentanesulfonic acid, tridecafluorohexanesulfonic acid, pentadecafluoroheptasulfonic acid, heptadecafluorooctanesulfonic acid, nonadecafluorononanesulfonic acid and combinations thereof.

12 . The composition of claim 9 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.

13 . The composition of claim 9 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, trimethylsilyinonafluorobutanesulfonic acid, trimethylsilylundecafluoropentanesulfonic acid, trimethylsilyltridecafluorohexanesulfonic acid, trimethylsilylpentadecafluoroheptasulfonic acid, trimethylsilylheptadecafluorooctanesulfonic acid, trimethylsilylnonadecafluorononanesulfonic acid and combinations thereof.

14 . The composition of claim 9 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.

15 . The composition of claim 9 wherein the compound containing a sulfonimide group and fluoro group is a bis(fluoroalkyl)sulfonimide compound selected from the group consisting of bis(trifluoromethane)sulfonimide, bis(pentafluoroethane)sulfonimide, bis(heptafluoropropane)suifonimide, bis(nonafluorobutane) sulfonimide, bis(undecafluoropentane)sulfonimide, bis(tridecafluorohexane)sulfonimide, bis(pentadecafluoroheptae)sulfonimide, bis(heptadecafluorooctane)sulfonimide, bis(nonadecafluorononane)sulfonimide and combinations thereof.

16 . The composition of claim 14 wherein the bis(fluoroalkyl)sulfonimide compound further comprises a triorganosilyl moiety.

17 . The composition of claim 16 wherein the bis(fluoroalkyl)sulfonimide compound further comprising a triorganosilyl moiety is selected from the group consisting of N-trimethylsilylbis(trifluoromethane)sulfonimide, N-trimethylsilylbis(pentafluoroethane)sulfonimide, N-trimethylsilylbis(heptafluoropropane)sulfonimide, N-trimethylsilylbis(nonafluorobutane) suifonimide, N-trimethylsilyibis(undecafluoropentane)sulfonimide, bis(tridecafluorohexane)sulfonimide, N-trimethylsilylbis(pentadecafluoroheptae)sulfonimide, N-trimethylsilylbis(heptadecafluorooctane)sulfonimide, N-trimethylsilylbis(nonadecafluorononane)sulfonimide and combinations thereof.

18 . 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.

19 . A catalytic dehydrocondensation process comprising:
reacting (A) a hydride-functionalized siloxane or silane and (B) a hydroxyl-containing compound that does not contain silicon in the presence of (C) a catalytically-effective amount of a 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.

20 . A functionalized siloxane comprising a Si—O—C bond, wherein said bond is formed by the dehydrocondensation process of claim 19 .

21 . A formulation comprising the functionalized siloxane of claim 20 , wherein the formulation is chosen from an agrochemical formulation, a personal care formulation, a home care formulation or a coating formulation.

Assignees

• Momentive Performance Mat Inc

Inventors

• Sivasubramanian Karthikeyan
• Khare Vivek P

Classifications

• B01J31/0241

  Imines or enamines · CPC title

• B01J31/0222

  comprising sulfonyl groups · CPC title

• B01J2231/40

  Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions · CPC title

• B01J31/0275 Primary

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0269 · CPC title

• C08K5/5399

  Phosphorus bound to nitrogen · CPC title